Compound

0001The present invention relates to a carbazole compound and a light emitting device using the same. In addition, the light emitting element The present invention relates to a light emitting device, an electronic device, and a lighting device using the above.

0002In recent years, electroluminescence (EL) has been introduced. Research and development of the light emitting element used is being actively carried out. The basic configuration of these light emitting elements is A layer containing a luminescent substance is sandwiched between a pair of electrodes. Applying voltage to this element Therefore, it is possible to obtain light emission from a luminescent substance.

0003Since such a light emitting element is a self-luminous type, the visibility of pixels is higher than that of a liquid crystal display. It has advantages such as no backlight is required, and is suitable as a flat panel display element. It is considered suitable. In addition, such a light emitting element can be made thin and lightweight. This is a big advantage. Another feature is that the response speed is extremely fast.

0004Since these light emitting elements can be formed in the form of a film, surface-like light emission can be easily performed. Obtainable. Therefore, it is possible to form a large-area element using planar light emission. .. This means point light sources such as incandescent lamps and LEDs, or line light such as fluorescent lamps. Since it is a feature that is difficult to obtain from a source, it has high utility value as a surface light source that can be applied to lighting and the like.

0005For light-emitting devices that use electroluminescence, is the luminescent substance an organic compound? It can be roughly classified according to whether it is an inorganic compound, but when an organic compound is used as a luminescent substance, it is emitted. By applying a voltage to the optical element, electrons and holes are generated from the pair of electrodes. It is injected into a layer containing a luminescent organic compound and an electric current flows through it. And those carriers (Den The recombination of children and holes (holes) causes the luminescent organic compound to form an excited state. It forms and emits light when its excited state returns to the ground state. The excited state formed by the organic compound The types of states can be singlet excited state and triplet excited state, from the singlet excited state. The luminescence of is called fluorescence, and the luminescence from the triplet excited state is called phosphorescence.

0006Regarding such a light emitting device, there is a problem depending on the substance in improving the element characteristics. In many cases, device structures have been improved and materials have been developed to overcome these problems. For example, special In License Document 1, a compound having an anthracene skeleton and a carbazole skeleton is used as a light emitting material. Although the light emitting element used is disclosed, it is said that the light emitting element has sufficient reliability. I can't.

0007Further, in Patent Document 2, an anthracene skeleton containing a substituted or unsubstituted phenyl group and A light emitting device using a compound having a carbazole skeleton and excellent carrier transportability is disclosed. ing. The light emitting element is an element having a low drive voltage and high reliability.

<p num="0008"><patcit num="1"><text>WO2005 / 113531 issue</text></patcit><patcit num="2"><text>Japanese Unexamined Patent Publication No. 2009-167175</text></patcit></p>

<p num="0009">When the compound described in Patent Document 2 is applied to an element using a phosphorescent substance, it is included in the compound. Phosphorescence due to insufficient T1 level (triplet excitation energy) of the anthracene skeleton It may be difficult to obtain high luminous efficiency because the excitation energy of the luminescent substance is quenched. Further, when applied to an element using a blue fluorescent substance, high luminous efficiency can be obtained. , Further improvement in efficiency is desired.</p><p num="0010">In view of the above problems, one aspect of the present invention achieves a longer life of the light emitting device and an improvement in luminous efficiency. One of the challenges is to provide new substances that can be used. More specifically, it is suitable for light emitting elements One of the challenges is to provide a novel carbazole compound that can be used.</p>

<p num="0011">One aspect of the present invention is a carbazole compound represented by the following general formula (G1).</p><p num="0012"><chemistry num="1"><img id="000002" he="45" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0013">However, in the general formula (G1), R¹Is an alkyl group with 1 to 12 carbon atoms, substituted or unsubstituted pheni Lu group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted A phenanthryl group, a substituted or unsubstituted triphenylenyl group, or the following general formula (G1- Indicates any one of the substituents represented by 1). Also, in the general formula (G1), R²Is hydrogen, charcoal Alkyl groups with prime numbers 1-12, substituted or unsubstituted phenyl groups, substituted or unsubstituted biphenyls Indicates either a group or a substituent represented by the following general formula (G1-2). Also, general In equation (G1), α³Is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted bif Indicates any one of the enildiyl groups. Also, in the general formula (G1), Ar³Is a replacement or no place Alternate naphthyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted triphenyleneni Indicates any one of the groups.</p><p num="0014"><chemistry num="2"><img id="000003" he="31" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0015">However, in the general formula (G1-1), Ar¹Is an alkyl group with 1 to 12 carbon atoms, substituted or unsubstituted. Phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or Indicates any one of an unsubstituted phenanthryl group and a substituted or unsubstituted triphenylenyl group. Also, in the general formula (G1-1), α¹Is a substituted or unsubstituted phenylene group, or a substituted or substituted phenylene group. Indicates any one of the unsubstituted biphenyldiyl groups. Also, in the general formula (G1-1), n is 0 or 1.</p><p num="0016"><chemistry num="3"><img id="000004" he="31" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0017">However, in the general formula (G1-2), Ar²Is an alkyl group with 1 to 12 carbon atoms, substituted or unsubstituted. Phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or Indicates any one of an unsubstituted phenanthryl group and a substituted or unsubstituted triphenylenyl group. Also, in the general formula (G1-2), α²Is a substituted or unsubstituted phenylene group, or a substituted or substituted phenylene group. Indicates any one of the unsubstituted biphenyldiyl groups.</p><p num="0018">In addition, R in the above general formula (G1)¹Is the following structural formulas (S-1) to (S-5), or It may be any one of the structures represented by the following general formula (G1-1).</p><p num="0019"><chemistry num="4"><img id="000005" he="75" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0020">However, in the general formula (G1-1), Ar¹Is an alkyl group with 1 to 12 carbon atoms, substituted or unsubstituted. Phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or Indicates any one of an unsubstituted phenanthryl group and a substituted or unsubstituted triphenylenyl group. Also, in the general formula (G1-1), α¹Is a substituted or unsubstituted phenylene group, or a substituted or substituted phenylene group. Indicates any one of the unsubstituted biphenyldiyl groups. Also, in the general formula (G1-1), n is 0 or 1.</p><p num="0021">In addition, R in the above general formula (G1)²Is the following structural formulas (S-11) to (S-16), May be any one of the structures represented by the following general formula (G1-2).</p><p num="0022"><chemistry num="5"><img id="000006" he="81" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0023">However, in the general formula (G1-2), Ar²Is an alkyl group with 1 to 12 carbon atoms, substituted or unsubstituted. Phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or Indicates any one of an unsubstituted phenanthryl group and a substituted or unsubstituted triphenylenyl group. Also, in the general formula (G1-2), α²Is a substituted or unsubstituted phenylene group, or a substituted or substituted phenylene group. Indicates any one of the unsubstituted biphenyldiyl groups.</p><p num="0024">In addition, α in the above general formula (G1)³, Α in general formula (G1-1)¹, And general formula (G1- 2) α in²Are independently of the structures represented by the following structural formulas (α-1) to (α-7). It may be any one.</p><p num="0025"><chemistry num="6"><img id="000007" he="83" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0026">In addition, Ar in the above general formula (G1-1)¹And Ar in the general formula (G1-2)²Each Independently, it is one of the structures represented by the following structural formulas (Ar-1) to (Ar-10). You may.</p><p num="0027"><chemistry num="7"><img id="000008" he="128" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0028">Also, Ar in the above general formula (G1)³Is the following structural formulas (Ar-11) to (Ar-15) It may be any one of the structures represented by.</p><p num="0029"><chemistry num="8"><img id="000009" he="94" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0030">Further, another aspect of the present invention is a light emitting device using the above-mentioned carbazole compound.</p><p num="0031">Further, another aspect of the present invention is a light emitting device using the above light emitting element.</p><p num="0032">Further, another aspect of the present invention is a lighting device using the above-mentioned light emitting device.</p><p num="0033">Further, another aspect of the present invention is an electronic device using the above-mentioned light emitting device.</p><p num="0034">The light emitting device in the present specification includes an image display device, a light emitting device, and a light source. .. Also, a connector on the panel, such as FPC (Flexible Printed Ci) rcuit) or TAB (Tape Automated Bonding) tape Or a module with TCP (Tape Carrier Package) attached Module, TAB tape, module with printed wiring board at the end of TCP, or luminescent element An IC (integrated circuit) is directly mounted on the child by the COG (Chip On Glass) method. All modules shall be included in the light emitting device.</p>

<p num="0035">According to one aspect of the present invention, a novel carbazole compound can be provided. The carbazo The compound has a wide bandgap and is useful as a material for a light emitting device. In addition, the said The carbazole compound has a high T1 level and is useful as a material for a light emitting device. further , The carbazole compound has high carrier transport property and is useful as a material for a light emitting device. To.</p><p num="0036">Further, according to one aspect of the present invention, it is possible to provide a light emitting element having high luminous efficiency and long life. Wear. Further, according to one aspect of the present invention, a highly reliable light emitting device to which the light emitting element is applied can be illuminated. Bright devices and electronic devices can be provided.</p>

0037<figref num="1">The figure explaining the light emitting element of one aspect of this invention.</figref><figref num="2">The figure explaining the light emitting element of one aspect of this invention.</figref><figref num="3">The figure explaining the light emitting device of one aspect of this invention.</figref><figref num="4">The figure explaining the light emitting device of one aspect of this invention.</figref><figref num="5">The figure explaining the electronic device of one aspect of this invention.</figref><figref num="6">The figure explaining the lighting apparatus of one aspect of this invention.</figref><figref num="7">NMR chart of PCPN.</figref><figref num="8">NMR chart of 3- (4-bromophenyl) -9-phenyl-9H-carbazole.</figref><figref num="9">MS chart of 3- (4-bromophenyl) -9-phenyl-9H-carbazole.</figref><figref num="10">The figure which shows the absorption spectrum and the emission spectrum of the toluene solution of PCPN.</figref><figref num="11">The figure which shows the absorption spectrum and the emission spectrum of the thin film of PCPN.</figref><figref num="12">NMR chart of PCPPn.</figref><figref num="13">The figure which shows the absorption spectrum and the emission spectrum of the toluene solution of PCPPn.</figref><figref num="14">The figure which shows the absorption spectrum and the emission spectrum of the thin film of PCPPn.</figref><figref num="15">NMR chart of PCzPTp.</figref><figref num="16">The figure which shows the absorption spectrum and the emission spectrum of the toluene solution of PCzPTp.</figref><figref num="17">NMR chart of mPCPPn.</figref><figref num="18">The figure which shows the absorption spectrum and the emission spectrum of the toluene solution of mPCPPn.</figref><figref num="19">The figure which shows the absorption spectrum and the emission spectrum of the thin film of mPCPPn.</figref><figref num="20">NMR chart of mPCzPTp.</figref><figref num="21">The figure which shows the absorption spectrum and the emission spectrum of the toluene solution of mPCzPTp.</figref><figref num="22">The figure which shows the absorption spectrum and the emission spectrum of the thin film of mPCzPTp.</figref><figref num="23">NCPN NMR chart.</figref><figref num="24">The figure which shows the absorption spectrum and the emission spectrum of the toluene solution of NCPN.</figref><figref num="25">The figure which shows the absorption spectrum and the emission spectrum of the thin film of NCPN.</figref><figref num="26">NMR chart of NP2PC.</figref><figref num="27">The figure which shows the absorption spectrum and the emission spectrum of the toluene solution of NP2PC.</figref><figref num="28">The figure which shows the absorption spectrum and the emission spectrum of the thin film of NP2PC.</figref><figref num="29">The figure explaining the light emitting element of an Example.</figref><figref num="30">The figure which shows the emission spectrum of the light emitting element of Example 9 and the comparative light emitting element.</figref><figref num="31">The figure which shows the voltage-luminance characteristic of the light emitting element of Example 9 and the comparative light emitting element.</figref><figref num="32">The figure which shows the luminance-current efficiency characteristic of the light emitting element of Example 9 and the comparative light emitting element.</figref><figref num="33">The figure which shows the luminance-power efficiency characteristic of the light emitting element of Example 9 and the comparative light emitting element.</figref><figref num="34">The figure which shows the result of the reliability test of the light emitting element of Example 9 and the comparative light emitting element.</figref><figref num="35">The figure which shows the emission spectrum of the light emitting element of Example 10 and the comparative light emitting element.</figref><figref num="36">The figure which shows the voltage-luminance characteristic of the light emitting element and the comparative light emitting element of Example 10.</figref><figref num="37">The figure which shows the luminance-current efficiency characteristic of the light emitting element and the comparative light emitting element of Example 10.</figref><figref num="38">The figure which shows the luminance-power efficiency characteristic of the light emitting element and the comparative light emitting element of Example 10.</figref><figref num="39">The figure which shows the result of the reliability test of the light emitting element and the comparative light emitting element of Example 10.</figref><figref num="40">The figure which shows the emission spectrum of the light emitting element of Example 11 and the comparative light emitting element.</figref><figref num="41">The figure which shows the voltage-luminance characteristic of the light emitting element of Example 11 and the comparative light emitting element.</figref><figref num="42">The figure which shows the luminance-current efficiency characteristic of the light emitting element of Example 11 and the comparative light emitting element.</figref><figref num="43">The figure which shows the luminance-power efficiency characteristic of the light emitting element of Example 11 and the comparative light emitting element.</figref><figref num="44">The figure which shows the result of the reliability test of the light emitting element and the comparative light emitting element of Example 11.</figref><figref num="45">The figure which shows the emission spectrum of the light emitting element of Example 12 and the comparative light emitting element.</figref><figref num="46">The figure which shows the voltage-luminance characteristic of the light emitting element and the comparative light emitting element of Example 12.</figref><figref num="47">The figure which shows the luminance-current efficiency characteristic of the light emitting element and the comparative light emitting element of Example 12.</figref><figref num="48">The figure which shows the luminance-power efficiency characteristic of the light emitting element of Example 12 and the comparative light emitting element.</figref><figref num="49">The figure which shows the result of the reliability test of the light emitting element and the comparative light emitting element of Example 12.</figref><figref num="50">The figure which shows the emission spectrum of the light emitting element of Example 13 and the comparative light emitting element.</figref><figref num="51">The figure which shows the voltage-luminance characteristic of the light emitting element of Example 13 and the comparative light emitting element.</figref><figref num="52">The figure which shows the luminance-current efficiency characteristic of the light emitting element of Example 13 and the comparative light emitting element.</figref><figref num="53">The figure which shows the luminance-power efficiency characteristic of the light emitting element of Example 13 and the comparative light emitting element.</figref><figref num="54">The figure which shows the emission spectrum of the light emitting element of Example 14 and the comparative light emitting element.</figref><figref num="55">The figure which shows the voltage-luminance characteristic of the light emitting element and the comparative light emitting element of Example 14.</figref><figref num="56">The figure which shows the luminance-current efficiency characteristic of the light emitting element of Example 14 and the comparative light emitting element.</figref><figref num="57">The figure which shows the luminance-power efficiency characteristic of the light emitting element of Example 14 and the comparative light emitting element.</figref><figref num="58">The figure which shows the result of the reliability test of the light emitting element and the comparative light emitting element of Example 14.</figref><figref num="59">The figure which shows the emission spectrum of the light emitting element of Example 15 and the comparative light emitting element.</figref><figref num="60">The figure which shows the voltage-luminance characteristic of the light emitting element and the comparative light emitting element of Example 15.</figref><figref num="61">The figure which shows the luminance-current efficiency characteristic of the light emitting element and the comparative light emitting element of Example 15.</figref><figref num="62">The figure which shows the structure of the light emitting element of an Example.</figref><figref num="63">The figure which shows the emission spectrum of the light emitting element of Example 16 and the comparative light emitting element.</figref><figref num="64">The figure which shows the voltage-luminance characteristic of the light emitting element of Example 16 and the comparative light emitting element.</figref><figref num="65">The figure which shows the luminance-current efficiency characteristic of the light emitting element of Example 16 and the comparative light emitting element.</figref><figref num="66">The figure which shows the emission spectrum of the light emitting element of Example 17.</figref><figref num="67">The figure which shows the voltage-luminance characteristic of the light emitting element of Example 17.</figref><figref num="68">The figure which shows the luminance-current efficiency characteristic of the light emitting element of Example 17.</figref><figref num="69">The figure which shows the emission spectrum of the light emitting element of Example 18.</figref><figref num="70">The figure which shows the voltage-luminance characteristic of the light emitting element of Example 18.</figref><figref num="71">The figure which shows the luminance-current efficiency characteristic of the light emitting element of Example 18.</figref><figref num="72">The figure which shows the luminance-power efficiency characteristic of the light emitting element of Example 18.</figref><figref num="73">The figure which shows the emission spectrum of the light emitting element of Example 19.</figref><figref num="74">The figure which shows the voltage-luminance characteristic of the light emitting element of Example 19.</figref><figref num="75">The figure which shows the luminance-current efficiency characteristic of the light emitting element of Example 19.</figref><figref num="76">The figure which shows the luminance-power efficiency characteristic of the light emitting element of Example 19.</figref><figref num="77">The figure which shows the result of the reliability test of the light emitting element of Example 19.</figref><figref num="78">The figure which shows the emission spectrum of the light emitting element of Example 20 and the comparative light emitting element.</figref><figref num="79">The figure which shows the voltage-luminance characteristic of the light emitting element and the comparative light emitting element of Example 20.</figref><figref num="80">The figure which shows the luminance-current efficiency characteristic of the light emitting element and the comparative light emitting element of Example 20.</figref><figref num="81">The figure which shows the luminance-power efficiency characteristic of the light emitting element and the comparative light emitting element of Example 20.</figref><figref num="82">NMR chart of Cl-PPn2.</figref><figref num="83">NMR chart of Pn2BPPC.</figref><figref num="84">The figure which shows the absorption spectrum and the emission spectrum of the toluene solution of Pn2BPPC.</figref><figref num="85">The figure which shows the absorption spectrum and the emission spectrum of the thin film of Pn2BPPC.</figref><figref num="86">NMR chart of PCPCl2.</figref><figref num="87">NMR chart of Pn2PPC.</figref><figref num="88">The figure which shows the absorption spectrum and the emission spectrum of the toluene solution of Pn2PPC.</figref><figref num="89">The figure which shows the absorption spectrum and the emission spectrum of the thin film of Pn2PPC.</figref>

0038Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is as follows. Not limited to the description, the form and details thereof are described without departing from the spirit and scope of the present invention. Those skilled in the art will easily understand that various changes can be made. Therefore, the present invention is as follows. It is not construed as being limited to the description of the embodiment shown in.

0039(Embodiment 1) In the present embodiment, the carbazole compound according to one aspect of the present invention will be described.

0040The carbazole compound according to one aspect of the present invention is a carbazole represented by the following general formula (G1). It is a compound.

0041<chemistry num="9"><img id="000010" he="45" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0042However, in the general formula (G1), R¹Is an alkyl group with 1 to 12 carbon atoms, substituted or unsubstituted pheni Lu group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted A phenanthryl group, a substituted or unsubstituted triphenylenyl group, or the following general formula (G1- Indicates any one of the substituents represented by 1). Also, in the general formula (G1), R²Is hydrogen, charcoal Alkyl groups with prime numbers 1-12, substituted or unsubstituted phenyl groups, substituted or unsubstituted biphenyls Indicates either a group or a substituent represented by the following general formula (G1-2). Also, general In equation (G1), α³Is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted bif Indicates any one of the enildiyl groups. Also, in the general formula (G1), Ar³Is a replacement or no place Alternate naphthyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted triphenyleneni Indicates any one of the groups.

0043<chemistry num="10"><img id="000011" he="31" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0044However, in the general formula (G1-1), Ar¹Is an alkyl group with 1 to 12 carbon atoms, substituted or unsubstituted. Phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or Indicates any one of an unsubstituted phenanthryl group and a substituted or unsubstituted triphenylenyl group. Also, in the general formula (G1-1), α¹Is a substituted or unsubstituted phenylene group, or a substituted or substituted phenylene group. Indicates any one of the unsubstituted biphenyldiyl groups. Also, in the general formula (G1-1), n is 0 or 1.

0045<chemistry num="11"><img id="000012" he="31" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0046However, in the general formula (G1-2), Ar²Is an alkyl group with 1 to 12 carbon atoms, substituted or unsubstituted. Phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or Indicates any one of an unsubstituted phenanthryl group and a substituted or unsubstituted triphenylenyl group. Also, in the general formula (G1-2), α²Is a substituted or unsubstituted phenylene group, or a substituted or substituted phenylene group. Indicates any one of the unsubstituted biphenyldiyl groups.

0047The substituent in the general formula (G1) (specifically, R¹, R², Ar³, And α³) To In each case, the HOMO level of the compound in which the bond of the substituent is substituted with hydrogen is deep (absolute value). (Large) Substituents shall be used. Specifically, the substituent that binds to the general formula (G1) The HOMO level of the compound in which the bond is replaced with hydrogen is preferably -5.5 eV or less. Thereby, the carbazole compound of the present embodiment represented by the general formula (G1) is obtained by HOM. It can be a compound with a deep O level.

0048Further, the substituent in the general formula (G1) (specifically, R¹, R², Ar³, And α³) To In each case, the band gap (Bg) of the compound in which the bond of the substituent is substituted with hydrogen is wide. In addition, a substituent having a high T1 level shall be used. Specifically, the setting in the general formula (G1) The bandgap of the compound in which the bond of the substituent is replaced with hydrogen is 2.7 eV or more (fluorescent blue d). Energy or higher, more preferably 3.0 eV or higher, T1 level 1.8 eV or higher (phosphorescent red) It is preferable that the energy is equal to or higher than the energy of. As a result, the real expression expressed by the general formula (G1) A carbazole compound in the form of an application, a compound with a wide bandgap and a high T1 level. Can be. Therefore, the carbazole compound of the present embodiment is adjacent to the light emitting layer. When used as a host material for a layer or light emitting layer, from a luminescent material with high excitation energy It is thought that the light emitting element can be made to shine more efficiently without depriving the excitation energy. Is done. When the carbazole compound of the present embodiment is used as a luminescent substance, it has a short wavelength (blue). Purple to blue) light can be obtained.

0049Also, if it has a wide bandgap, even if the material has a deep HOMO level, it is a shallow LU. The MO level can be maintained. Therefore, the carbazole compound of the present embodiment emits light. When applied to the hole transport layer of a device, it suppresses the escape of electrons from the adjacent light emitting layer and suppresses the escape of electrons to the light emitting layer. It is considered that the carrier recombination in the above can be efficiently performed.

0050Therefore, a substituent (specifically, R) that binds to the general formula (G1).¹, R², Ar³, And α³In each of), the LUMO level of the compound in which the bond of the substituent is substituted with hydrogen is shallow (). Substituents (with a small absolute value) shall be used. Specifically, the position to be combined with the general formula (G1) The LUMO level of the compound in which the bond of the substituent is replaced with hydrogen is preferably -2.5 eV or higher. Good.

0051R above¹, R², Α³, And Ar³HOMO level, LUM even if has additional substituents Considering the O level and bandgap, the substituents are independent of each other and have 1 to 12 carbon atoms. Alkyl group, phenyl group, biphenyl group, naphthyl group, phenanthryl group, or tri Any of the phenylenyl groups is preferred.

0052In particular, Ar, which is part of the substituents attached to the 3-position (and 6-position) of the carbazole skeleton.³(And Ar²) Is like a naphthyl group, a phenanthryl group, or a triphenylenyl group. , It is preferable to use a fused ring. This is because these fused rings are excellent in carrier transportability. In particular, it is preferably a naphthyl group or a phenanthryl group. In addition, it has a high molecular weight and has thermal properties. In terms of improvement, it is preferable to use a phenanthryl group or a triphenylenyl group. In addition, it should be noted. Naphthalene is a two-ring condensed ring with a small conjugation, so the bandgap is wide and the T1 level is high. Phenanthrene and triphenylene are fused rings with three or more rings, but the same three fused rings are used. Compared to trasen and 4-ring tetracene, helicopter instead of polyacene structure (condensed ring is linear) Since it is a combination of a sen structure and a helicene structure (bent condensed ring), it is a band gear. Wide range and high T1 level.

0053Also, the carbazole skeleton and Ar³(And Ar²) And α³(And α²) By sandwiching the reelen, Ar from the carbazole skeleton³(And Ar²) The conjugate spreads It is preferable because it has a leprosy structure. Especially meta and ortho (for example, 1st and 3rd for phenylene) When allylene is bonded at the 1st and 2nd positions), the conjugation is more difficult to spread, and the bandgi It is preferable because it is thought that the cap will spread. Also, if it is bonded to the para position, it has thermophysical characteristics. It is considered to have excellent carrier transportability (high Tg). Also α³(And α²) Is , The phenyl skeleton and the biphenyl skeleton should not be a factor that increases the conjugation by itself. Use an arylene group with a small conjugation.

0054Substituent Ar in the general formula (G1)¹, Ar²And Ar³Substituents attached to each Is preferable because it is easily dissolved in a solvent. In particular, methyl groups and tert -Butyl groups are preferable because they are considered to have excellent solubility. Also, it is connected to the general formula (G1). Matching substituents Ar¹, Ar²And Ar³Has a substituent such as an alkyl group or an aryl group In this case, the structure of the carbazole compound of the present embodiment becomes more three-dimensional. Therefore, more conclusion It is thought that it is difficult to crystallize and it is possible to suppress concentration quenching due to stacking of molecules. This is preferable.

0055In addition, the substituent R that binds to the general formula (G1)²If is other than hydrogen, the substituent R²And substituent α³-Ar³Is the same, which is preferable because the synthesis becomes simpler. Also, the substituent R²Replace with Group α³-Ar³If they are the same, the molecular weight is increased, so that the thermophysical properties are also improved, which is preferable. Na Oh, substituent R²When is hydrogen, the bandgap is wider than when it is not hydrogen. 1 It is preferable because the level is high.

0056Specific examples of the substituents to be applied are shown below.

0057In the general formula (G1), R¹Specifically, as the substituent represented by, for example, the following structure Formulas (S-1) to (S-5), or the following general formula (G1-1) and the like can be mentioned.

0058<chemistry num="12"><img id="000013" he="74" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0059However, in the general formula (G1-1), Ar¹Is an alkyl group with 1 to 12 carbon atoms, substituted or unsubstituted. Phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or Indicates any one of an unsubstituted phenanthryl group and a substituted or unsubstituted triphenylenyl group. Also, in the general formula (G1-1), α¹Is a substituted or unsubstituted phenylene group, or a substituted or substituted phenylene group. Indicates any one of the unsubstituted biphenyldiyl groups. Also, in the general formula (G1-1), n is 0 or 1.

0060Also, in the general formula (G1), R²Specifically, as the substituent represented by, for example, below The structural formulas (S-11) to (S-16), or the following general formulas (G1-2), etc. can be mentioned. To.

0061<chemistry num="13"><img id="000014" he="82" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0062However, in the general formula (G1-2), Ar²Is an alkyl group with 1 to 12 carbon atoms, substituted or unsubstituted. Phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or Indicates any one of an unsubstituted phenanthryl group and a substituted or unsubstituted triphenylenyl group. Also, in the general formula (G1-2), α²Is a substituted or unsubstituted phenylene group, or a substituted or substituted phenylene group. Indicates any one of the unsubstituted biphenyldiyl groups.

0063Also, α in the general formula (G1)³, Α in general formula (G1-1)¹, Or the general formula (G1- 2) α in²Specifically, as the substituent represented by, the following structural formulas (α-1) to (α-7) ) Etc. can be mentioned.

0064<chemistry num="14"><img id="000015" he="83" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0065Also, Ar in the general formula (G1-1)¹, Or Ar in the general formula (G1-2)²Represented by Specific examples of the substituents include the following structural formulas (Ar-1) to (Ar-10). To.

0066<chemistry num="15"><img id="000016" he="129" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0067Also, Ar in the general formula (G1)³Specifically, as the substituent represented by, the following structural formula (A) r-11) to (Ar-15) and the like can be mentioned.

0068<chemistry num="16"><img id="000017" he="93" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0069Specific examples of the carbazole compound represented by the general formula (G1) include structural formulas (100) to structure. Formulation (131), Structural Formula (140) ~ Structural Formula (151), Structural Formula (160) ~ Structural Formula (1) 83) and carbazole compounds represented by structural formulas (190) to (197). Can be However, the present invention is not limited to these.

0070<chemistry num="17"><img id="000018" he="176" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0071<chemistry num="18"><img id="000019" he="175" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0072<chemistry num="19"><img id="000020" he="177" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0073<chemistry num="20"><img id="000021" he="181" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0074<chemistry num="21"><img id="000022" he="182" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0075<chemistry num="22"><img id="000023" he="182" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

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0079<chemistry num="26"><img id="000027" he="189" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0080<chemistry num="27"><img id="000028" he="195" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0081<chemistry num="28"><img id="000029" he="202" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0082<chemistry num="29"><img id="000030" he="186" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0083<chemistry num="30"><img id="000031" he="82" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0084As a method for synthesizing the carbazole compound of the present embodiment, various reactions can be applied. .. For example, it is synthesized by performing the synthesis reaction shown in the following synthesis methods 1 to 3. Can be done. In the reaction scheme shown below, reference numerals (R) not particularly explained.¹, R², α³, Ar³) Can be taken into consideration in the explanation of the above general formula (G1).

0085&lt;Synthesis method 1&gt; First, as shown in the reaction scheme (A-1), with the halogenated carbazole compound (a1) By coupling with an arylboron compound (a2), a carbazole compound (a) 3) is synthesized.

0086<chemistry num="31"><img id="000032" he="36" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0087In addition, X¹Represents halogen. X¹Is preferably bromine because of its high reactivity. Or iodine. B¹Represents boronic acid or dialkoxyboron.

0088The coupling reaction of the reaction scheme (A-1) has various reaction conditions, one of which is an example. As a result, a synthetic method using a metal catalyst can be applied in the presence of a base.

0089The case where the Suzuki-Miyaura reaction is used in the reaction scheme (A-1) is shown. Metal catalyst A palladium catalyst can be used as the palladium catalyst, and a palladium complex can be used as the palladium catalyst. A mixture of the ligands can be used. The palladium complex is paradiacetate. Umm (II), Tetrakis (Triphenylphosphine) Palladium (0), Bis (Truffle) Enylphosphine) Palladium (II) dichloride and the like. Also as a ligand Is tri (ortho-tolyl) phosphine, triphenylphosphine, tricyclohexi Sylphosphine and the like can be mentioned. As a substance that can be used as a base, nato Examples include organic bases such as lithium tert-butoxide and inorganic bases such as potassium carbonate. To. In addition, the reaction is preferably carried out in a solution, and as a solvent that can be used, Mixed solvent of ruen and water, mixed solvent of alcohol and water such as toluene and ethanol, xylene And water mixed solvent, alcohol and water mixed solvent such as xylene and ethanol, benzene and water Mixed solvent, mixed solvent of alcohol and water such as benzene and ethanol, ethylene glycol di Examples thereof include a mixed solvent of water and ethers such as methyl ether. However, it can be used The catalysts, bases, and solvents that can be used are not limited to these. Also in the reaction scheme (A-1) Instead of the arylboron compound (a2), arylaluminum and aryldi Luconium, aryl zinc, aryl tin compounds and the like may be used. Also the reaction is nitrogen It is preferably performed in an inert atmosphere such as plain or argon.

0090In addition, in the reaction scheme (A-1), the halogen group X of compound (a1)¹And the compound (a2 ) Boron compound group B¹Although the case of reacting with is shown, the compound (a1) is a boron compound. , Compound (a2) as a halide (reactive group X¹And B¹(Reverse) Coupling The above carbazole compound (a3) can also be obtained.

0091Next, as shown in the reaction scheme (A-2), the carbazole compound (a3) is halogenated. By doing so, a halogenated carbazole compound (a4) is synthesized.

0092<chemistry num="32"><img id="000033" he="39" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0093In addition, X²Represents halogen. X²Is preferably bromine because of its high reactivity. Or iodine.

0094The halogenation reaction in the reaction scheme (A-2) has various reaction conditions, for example. A reaction using a halogenating agent under a polar solvent can be used. As a halogenating agent N-Bromosuccinate imide (NBS), N-iodosuccinate imide (NIS), Bromine, Yo U-element, potassium iodide and the like can be used. When bromide is used as a halogenating agent, It is preferable because it can be synthesized at a lower cost. In addition, when iodide is used as a halogenating agent, it is raw. In the compound (iodide), the iodine-substituted portion has high activity. Therefore, it occurred When the reaction using a compound (iodide) as a raw material is carried out, the reaction proceeds more easily, which is preferable.

0095Next, as shown in the reaction scheme (A-3), the halogenated carbazole compound (a4) is added. Reacting a compound activated by reacting with a metal catalyst with a boron compound Then, the carbazolyl boron compound (a5) is synthesized.

0096<chemistry num="33"><img id="000034" he="42" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0097In addition, X²Represents halogen. X²Is preferably bromine because of its high reactivity. Or iodine. Also, B²Represents boronic acid or dialkoxyboron.

0098One of the activations of the halogenated carbazole compound (a4) in the reaction scheme (A-3). As an example, a reaction of lithiolysis with an alkyllithium reagent can be used. Alkyl Lithium reagents include n-butyllithium, tert-butyllithium, and methyllithium. And so on. Hydrochloric acid or the like can be used as the acid. As a solvent, diethyl A Ethers such as ter and tetrahydrofuran (THF) can be used, and a dehydration solvent can be used. Use. Boron compounds that can be used include trimethyl borate and triethyl borate. Le etc. can be mentioned.

0099Then, as shown in the reaction scheme (A-4), the carbazolyl boron compound (a5) and the di Halogenated carbazo by coupling with an aryl halide compound (a6) The compound (a7) is obtained.

0100<chemistry num="34"><img id="000035" he="47" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0101In addition, X³, And X⁴Represents halogen. X³And X⁴Because of their high reactivity, each , Preferably represents bromine, more preferably represents iodine. B²And X³And specifically react If you want to, X³Is X⁴It is preferable to use a halogen having a higher reactivity than that. Na Oh, in halogen, bromine is more reactive than chlorine, and iodine is more reactive than bromine. high. B²Represents boronic acid or dialkoxyboron.

0102The coupling reaction of the reaction scheme (A-4) has various reaction conditions, one of which is , A synthetic method using a metal catalyst can be applied in the presence of a base. Specifically, the reaction It can be done in the same way as scheme (A-1), and it is possible to take into consideration the above description.

0103In addition, in the reaction scheme (A-4), the halogen group X of compound (a6)³And the compound (a5 ) Boron compound group B²Although the case of reacting with is shown, the compound (a5) is a boron compound. , Compound (a6) as a halide (reactive group X³And B²(Reverse) Coupling Even if it is allowed to do so, the above-mentioned carbazole compound (a7) can be obtained. In this case, the compound ( a6) Halogen group X to prevent reaction between each other³Halogen group X⁴More reactive than It is necessary to apply a halogen group.

0104Next, as shown in the reaction scheme (A-5), with the halogenated carbazole compound (a7) By coupling with the arylboron compound (a8), it is represented by the above general formula (G1). The carbazole compound to be obtained can be obtained.

0105<chemistry num="35"><img id="000036" he="48" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0106In addition, X⁴Represents halogen. X⁴Is preferably bromine because of its high reactivity. Or iodine. Also, B³Represents boronic acid or dialkoxyboron.

0107The coupling reaction of the reaction scheme (A-5) has various reaction conditions, one of which is an example. As a result, a synthetic method using a metal catalyst can be applied in the presence of a base. In particular , It can be carried out in the same way as the reaction scheme (A-1), and it is possible to take into consideration the above description. To.

0108In addition, in the reaction scheme (A-5), the halogen group X of compound (a7)⁴And the compound (a8 ) Boron compound group B³Although the case of reacting with is shown, the compound (a7) is a boron compound. , Compound (a8) as a halide (reactive group X⁴And B³(Reverse) Coupling Even if it is allowed to do so, a carbazole compound represented by the above general formula (G1) can be obtained.

0109Further, in the above-mentioned reaction schemes (A-1) to (A-5), the substituent -R²The carbazole Substituent-α after compounding to the 3-position of the skeleton³-Ar³To the 6th position of its carbazole skeleton An example of matching is shown. However, the present embodiment is not limited to the above reaction, and the substituent-α³-Ar³Substituent-R²Is compounded, but the carba represented by the above general formula (G1) Zol compounds can be synthesized.

0110Substituent-R²And substituents-α³-Ar³If and have the same skeleton, each is carbazo The reaction of simultaneously compounding the 3rd and 6th positions of the skeleton is preferable because it is simpler.

0111Further, regarding the synthesis method of the carbazole compound of the present embodiment, which is different from the synthesis method 1, the synthesis method is described below. 2 is shown.

0112&lt;Synthesis method 2&gt; As shown in the reaction scheme (B-1), the halogenated carbazole compound (a4) and ally By coupling with the ruboron compound (a9), it is represented by the above general formula (G1). Carbazole compounds can be synthesized.

0113<chemistry num="36"><img id="000037" he="53" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0114In addition, X²Represents halogen. X²Is preferably bromine because of its high reactivity. Or iodine. B⁴Represents boronic acid or dialkoxyboron.

0115The coupling reaction of the reaction scheme (B-1) has various reaction conditions, for example. , A synthetic method using a metal catalyst can be applied in the presence of a base. Specifically, the reaction It can be done in the same way as scheme (A-1), and it is possible to take into consideration the above description.

0116In addition, in the reaction scheme (B-1), the halogen group X of compound (a4)²And the compound (a9 ) Boron compound group B⁴Although the case of reacting with is shown, the compound (a4) is a boron compound. , Compound (a9) as a halide (reactive group X²And B⁴(Reverse) Coupling Even if it is allowed to do so, the carbazole compound represented by the above general formula (G1) can be synthesized.

0117In addition, in the reaction scheme (B-1), the substituent -R²To the 3-position of the carbazole skeleton After that, the substituent -α³-Ar³Is combined with the 6-position of the carbazole skeleton. Shi However, the present embodiment is not limited to the above reaction, and the substituent-α³-Ar³Placed after combining Substituent-R²Even if the above is combined, the carbazole compound represented by the above general formula (G1) is synthesized. Can be

0118Also, substituent -R²And substituents-α³-Ar³If and have the same skeleton, each is carbazo The reaction of simultaneously compounding the 3rd and 6th positions of the skeleton is preferable because it is simpler.

0119Further, regarding the synthesis method of the carbazole compound of the present embodiment, which is different from the synthesis method 1 and the synthesis method 2. Synthesis method 3 is shown below.

0120&lt;Synthesis method 3&gt; As shown in the reaction scheme (C-1), the carbazole compound (a10) and the halogenated ant By coupling with the compound (a11), it is represented by the above general formula (G1). Lubazole compounds can be synthesized.

0121<chemistry num="37"><img id="000038" he="47" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry>

0122In addition, X⁵Represents halogen. X⁵Is preferably bromine because of its high reactivity. Or iodine.

0123In the reaction scheme (C-1), an aryl compound having a halogen group and a carbazole There are various reaction conditions for the coupling reaction with the 9th position of, but as an example, in the presence of a base. A synthetic method using a metal catalyst can be applied.

0124When using the Buchwald-Hartwig reaction in the reaction scheme (C-1) I will show you. A palladium catalyst can be used as the metal catalyst, and the palladium catalyst can be used. Can use a mixture of a palladium complex and its ligand. As a palladium complex , Bis (dibenzylideneacetone) Palladium (0), Palladium acetate (II), etc. Be done. The ligands include tri (tert-butyl) phosphine and tri (n-hex). Syl) phosphine, tricyclohexylphosphine, 1,1-bis (diphenylphos) Fino) Ferrocene (abbreviation: DPPF) and the like. It can also be used as a base Possible substances include organic bases such as sodium tert-butoxide and potassium carbonate. Inorganic bases and the like can be mentioned. Moreover, this reaction is preferably carried out in a solution. Examples of the solvent that can be used include toluene, xylene, benzene and the like. However However, the catalysts and their ligands, bases, and solvents that can be used are not limited to these. There is no. The reaction is preferably carried out in an inert atmosphere such as nitrogen or argon.

0125In addition, the case where the Ullmann reaction is used in the reaction scheme (C-1) is shown. metal A copper catalyst can be used as the catalyst, and copper (I) iodide or copper (II) acetate can be mentioned. Is done. In addition, as a substance that can be used as a base, an inorganic base such as potassium carbonate is used. Can be mentioned. Further, this reaction is preferably carried out in a solution, and with a solvent that can be used. As a result, 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) pyrimidinone ( DMPU), toluene, xylene, benzene and the like. However, it can be used The catalysts, bases, and solvents are not limited to these. Also, this reaction is nitrogen or argon. It is preferable to carry out in an inert atmosphere.

0126In the Ullmann reaction, the target product in a shorter time and higher yield when the reaction temperature is 100 ° C or higher. Therefore, it is preferable to use a solvent having a high boiling point such as DMPU or xylene. Also , The reaction temperature is more preferably higher than 150 ° C, so DMPU is more preferable. Use.

0127Substituent-R²And substituent-α³-Ar³To the 3rd and 6th positions of the carbazole skeleton The reaction is described in the above reaction schemes (A-1) to (A-5) or the reaction scheme (B-1). It can be carried out in the same manner as the reaction, and the details can be taken into consideration in the above description.

0128As described above, the carbazole compound of the present embodiment can be synthesized.

0129The carbazole compound of this embodiment has a deep (large absolute value) HOMO level. Therefore, it has excellent hole injection into the light emitting layer. Further, the carbazole compound of the present embodiment is an acid. It is electrochemically stable against chemistry. Therefore, the carbazole compound of the present embodiment can be used. It can be suitably used as a material for the hole transport layer of an optical device. In addition, the cal of the present embodiment Composite material made by mixing a bazole compound (electron donor) and an electron acceptor (acceptor) Can be used as the hole injection layer of the light emitting device. The electron acceptor and electron donor are At least, it may be one that transfers and receives electrons with the assistance of an electric field.

0130Further, the carbazole compound of the present embodiment has a shallow (small absolute value) LUMO level. Therefore, by using it as a material for the hole transport layer of the light emitting element, the movement of electrons to the anode can be prevented. Can be locked (ie, act as an electronic block material). Therefore, the real thing It is possible to improve the efficiency of the light emitting device by using the carbazole compound in the form of the application.

0131Further, since the carbazole compound of the present embodiment has a wide bandgap, it is a light emitting layer. Suppresses energy transfer from the light emitting layer even when applied to the hole transport layer adjacent to Can be Therefore, the high efficiency of the light emitting device using the carbazole compound of the present embodiment It is possible to extend the life of the light emitting element as well as to improve the life.

0132Further, since the carbazole compound shown in the present embodiment exhibits fluorescence, it can emit light at a short wavelength. Noh. Therefore, by using the carbazole compound of the present embodiment as a light emitting material, Blue-purple to blue light emission can be obtained.

0133Further, the carbazole compound of the present embodiment is used as a host material for a light emitting layer in a light emitting device. Is also suitable. That is, in the layer composed of the carbazole compound of the present embodiment, the said Luminescent substances with a bandgap smaller than that of carbazole compounds (hereinafter referred to as dopants) (Also described) can be added to obtain light emission from the dopant. At this time, the present embodiment Carbazole compound has a wide bandgap, so it emits light at relatively short wavelengths such as blue. Even if a fluorescent dopant having the above is used, it is possible to efficiently obtain light emission from the dopant. Wear. In other words, it can be used as a host material for fluorescent compounds in the visible region. Well If the dopant is a phosphorescent compound, the host material has a T1 level higher than that of the dopant. It is preferable to use a substance having a high value. The carbazole compound of the present embodiment has a high T1 level. Since it is a mild substance, it can be used as a host material for phosphorescent compounds in the visible range from at least green to long wavelengths. Can be used.

0134Further, the carbazole compound shown in this embodiment absorbs in the visible region (about 380 to 750 nm). Since the amount is small, the transmittance of visible light is high when a thin film is formed. Therefore, it is used for light emitting elements. However, it is difficult to absorb the luminescence energy, and an element having a high external quantum yield can be obtained.

0135This embodiment can be used in combination with other embodiments as appropriate.

0136(Embodiment 2) In the present embodiment, as one aspect of the present invention, the carbazole compound described in the first embodiment A light emitting device using the above will be described with reference to FIG.

0137The light emitting element of the present embodiment sandwiches an EL layer having at least a light emitting layer between a pair of electrodes. Is formed. The EL layer may have a plurality of layers in addition to the light emitting layer. The plurality of layers are electrodes. Carriers are formed so that a light emitting region is formed away from the electrode, that is, at a portion away from the electrode. From substances with high carrier injectability and substances with high carrier transport so that It is a combination of layers that are laminated. The plurality of layers include, for example, hole injection. It may have a layer, a hole transport layer, an electron transport layer, an electron injection layer, and the like.

0138In the light emitting device of the present embodiment shown in FIG. 1 (A), the first electrode 101 and the second electrode 1 An EL layer 102 is provided between the pair of electrodes of 03. In addition, the EL layer 102 is a hole injection. Insertion layer 111, hole transport layer 112, light emitting layer 113, electron transport layer 114, electron injection layer 115 Have. In the light emitting element shown in the present embodiment, the first light emitting element provided on the substrate 100. The electrode 101 of 1 functions as an anode, and the second electrode 103 functions as a cathode.

0139The substrate 100 is used as a support for a light emitting element. The substrate 100 includes, for example, glass. Quartz, plastic, etc. can be used. Further, a flexible substrate may be used. Yes A flexible substrate is a bendable (flexible) substrate, for example, polycarbonate. -Plastic substrates made of bonate, polyarylate, and polyether sulfone, etc. I can get rid of it. Also, films (polypropylene, polyester, vinyl, polyvinyl fluoride) , Vinyl chloride, etc.), inorganic vapor deposition film, etc. can also be used. Luminescent element Anything other than these may be used as long as it functions as a support in the process of producing the child.

0140As the first electrode 101, a metal or alloy having a large work function (specifically, 4.0 eV or more) , Conductive compounds, and mixtures thereof. Specifically, for example , Indium Tin Oxide (ITO), Silicon Young Indium oxide-tin oxide, indium oxide-zinc oxide, tattoo containing silicon oxide Examples thereof include indium oxide (IWZO) containing zinc and zinc oxide. these The conductive metal oxide film is usually formed by sputtering, but a sol-gel method or the like is applied. You may make it. For example, indium oxide-zinc oxide is 1 relative to indium oxide. Formed by sputtering using a target with ~ 20 wt% zinc oxide added Can be done. Indium oxide (IWZO) containing tungsten oxide and zinc oxide. ) Is 0.5 ~ 5wt% of tungsten oxide and 0.1 ~ of zinc oxide with respect to indium oxide. It can be formed by a sputtering method using a target containing 1 wt%. This Besides, gold, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, pa Examples thereof include radium and nitrides of metallic materials (for example, titanium nitride).

0141However, of the EL layer 102, the layer formed in contact with the first electrode 101 is organicized, which will be described later. When formed using a composite material made up of a mixture of a compound and an electron acceptor (acceptor) The substances used for the first electrode 101 are various metals, alloys, regardless of the size of the work function. Conductive compounds and mixtures thereof can be used. For example, aluminum Alloys containing silver and aluminum (for example, Al-Si) and the like can also be used.

0142In the EL layer 102 formed on the first electrode 101, the hole injection layer 111 and the hole transport layer 112, at least one of the light emitting layers 113 is carbazole, which is one aspect of the present invention. Formed containing a compound. A known substance can be used for a part of the EL layer 102, which is low. Either a molecular compound or a polymer compound can be used. The EL layer 102 The substances to be formed include not only organic compounds but also inorganic compounds as a part. It shall also include the result.

0143The hole injection layer 111 is a layer containing a substance having a high hole injection property. As a substance with high hole injection For example, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, Ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalate By using metal oxides such as compounds, silver oxides, tungsten oxides, and manganese oxides Wear. Also, phthalocyanine (abbreviation: H)₂Pc), copper (II) phthalocyanine (abbreviation: C) Phthalocyanine compounds such as uPc) can be used.

0144In addition, 4,4', 4''-tris (N, N-diphenylamino), which is a low-molecular-weight organic compound, ) Triphenylamine (abbreviation: TDATA), 4,4', 4''-Tris [N- (3-me) Tylphenyl) -N-Phenylamino] Triphenylamine (abbreviation: MTDATA), 4 , 4'-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl Le (abbreviation: DPAB), 4,4'-bis (N- {4- [N'-(3-methylphenyl)-) N'-Phenylamino] Phenyl} -N-Phenylamino) Biphenyl (abbreviation: DNTP) D), 1,3,5-Tris [N- (4-diphenylaminophenyl) -N-phenylami No] Benzene (abbreviation: DPA3B), 3- [N- (9-phenylcarbazole-3-yl) ) -N-Phenylamino] -9-Phenylcarbazole (abbreviation: PCzPCA1), 3, 6-Bis [N- (9-Phenylcarbazole-3-yl) -N-Phenylamino] -9- Phenylcarbazole (abbreviation: PCzPCA2), 3- [N- (1-naphthyl) -N- ( 9-Phenylcarbazole-3-yl) amino] -9-Phenylcarbazole (abbreviation: P) Aromatic amine compounds such as CzPCN1) can be used.

0145Furthermore, polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. .. For example, poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltrif) Enilamine) (abbreviation: PVTPA), poly [N- (4- {N'-[4- (4-dipheni) Luamino) phenyl] phenyl-N'-phenylamino} phenyl) methacrylamide] (Abbreviation: PTPDMA), Poly [N, N'-bis (4-butylphenyl) -N, N'-bi Polymer compounds such as su (phenyl) benzidine] (abbreviation: Poly-TPD) can be mentioned. To. Also, poly (3,4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (PEDOT / PSS), Polyaniline / Poly (Styrene Sulfonic Acid) (PAni / PS) A polymer compound to which an acid such as S) is added can be used.

0146Further, as the hole injection layer 111, an organic compound and an electron acceptor (acceptor) are mixed. You may use the composite material. Such composites are converted into organic compounds by electron acceptors. Since holes are generated, it is excellent in hole injection property and hole transport property. In this case, the organic compound , It is preferable that the material is excellent in transporting generated holes (substance having high hole transporting property).

0147Organic compounds used in composite materials include aromatic amine compounds, carbazole derivatives, and aromatics. Various compounds such as group hydrocarbons and polymer compounds (oligomers, dendrimers, polymers, etc.) Things can be used. As an organic compound used for a composite material, it has high hole transportability. It is preferably an organic compound. Specifically, 10^-6cm²Hole movement above / Vs It is preferably a substance having a degree. However, even if it is a substance that transports holes more than electrons. For example, other than these may be used. In the following, organicization that can be used for composite materials List the compound concretely.

0148Since the carbazole compound according to one aspect of the present invention is an organic compound having high hole transportability, it is a composite. It can be preferably used as a material. In addition, organic compounds that can be used in composite materials For example, TDATA, MTDATA, DPAB, DNTPD, DPA3B, P CzPCA1, PCzPCA2, PCzPCN1, 4,4'-bis [N- (1-naphthyl) )-N-Phenylamino] Biphenyl (abbreviation: NPB or α-NPD), N, N'-bis (3-Methylphenyl) -N, N'-diphenyl- [1,1'-biphenyl] -4,4' -Diamine (abbreviation: TPD), 4-Phenyl-4'-(9-Phenylfluorene-9-a) Aromatic amine compounds such as triphenylamine (abbreviation: BPAFLP) and 4,4'- Di (N-carbazolyl) biphenyl (abbreviation: CBP), 1,3,5-tris [4- (N-) Carbazole) Phenyl] Benzene (abbreviation: TCPB), 9- [4- (10-Phenyl-) 9-Phenyl) -9H-carbazole (abbreviation: CzPA), 9-Phenyl- 3- [4- (10-Phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation) : PCzPA), 1,4-bis [4- (N-carbazolyl) phenyl] -2,3,5,6 -Carbazole derivatives such as tetraphenylbenzene can be used.

0149In addition, 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t- BuDNA), 2-tert-butyl-9,10-di (1-naphthyl) anthracene, 9 , 10-bis (3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 2-t ert-Butyl-9,10-bis (4-phenylphenyl) anthracene (abbreviation: tB) uDBA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 9,10- Diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: DPAnth) Abbreviation: t-BuAnth), 9,10-bis (4-methyl-1-naphthyl) anthracene (Abbreviation: DMNA), 9,10-bis [2- (1-naphthyl) phenyl] -2-tert -Butyl anthracene, 9,10-bis [2- (1-naphthyl) phenyl] anthracene , 2,3,6,7-Tetramethyl-9,10-di (1-naphthyl) anthracene and other fragrances Group hydrocarbon compounds can be used.

0150In addition, 2,3,6,7-tetramethyl-9,10-di (2-naphthyl) anthracene, 9,9'-Biantril, 10,10'-Diphenyl-9,9'-Biantril, 10, 10'-Bis (2-Phenylphenyl) -9,9'-Biantril, 10,10'-Bis [(2,3,4,5,6-Phenyl) Phenyl]-9,9'-Biantril, Ann Trasen, Tetracene, Rubrene, Perylene, 2,5,8,11-Tetra (tert-Bu) Chill) Perylene, pentacene, coronene, 4,4'-bis (2,2-diphenylvinyl) Biphenyl (abbreviation: DPVBi), 9,10-bis [4- (2,2-diphenylvinyl)) It is possible to use aromatic hydrocarbon compounds such as phenyl] anthracene (abbreviation: DPVPA). it can.

0151In addition, as an electron acceptor, 7,7,8,8-tetracyano-2,3,5,6-tetraf Luolokinodimethane (abbreviation: F)₄-TCNQ), organic compounds such as chloranil, and transition metals Oxides can be mentioned. In addition, metals belonging to Group 4 to Group 8 in the Periodic Table of the Elements Oxides can be mentioned. Specifically, vanadium oxide, niobium oxide, tanta oxide Lu, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, renium oxide are electric It is preferable because it has high child receptivity. Above all, molybdenum oxide is stable in the atmosphere and absorbs It is preferable because it has low wettability and is easy to handle.

0152In addition, the above-mentioned polymer compounds such as PVK, PVTPA, PTPDMA, and Poly-TPD And the above-mentioned electron acceptor may be used to form a composite material and used for the hole injection layer 111.

0153The hole transport layer 112 is a layer containing a substance having a high hole transport property. Carbazo according to one aspect of the present invention The compound is a substance having a high hole transport property, and is suitably used as a material for the hole transport layer 112. Can be

0154The light emitting layer 113 is a layer containing a light emitting substance. As the luminescent substance, for example, it emits fluorescence. A fluorescent compound or a phosphorescent compound that emits phosphorescence can be used.

0155Since the carbazole compound according to one aspect of the present invention is a material exhibiting blue-purple to blue fluorescence, it is a luminescent substance. It can also be used as.

0156In addition, as a fluorescent substance that can be used for the light emitting layer 113, for example, a bluish emission is emitted. As a light material, N, N'-bis [4- (9H-carbazole-9-yl) phenyl] -N , N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4- (9H -Carbazole-9-yl) -4'-(10-Phenyl-9-anthryl) Triphenyl Amine (abbreviation: YGAPA), 4- (10-Phenyl-9-anthril) -4'-(9-) Phenyl-9H-carbazole-3-yl) triphenylamine (abbreviation: PCBAPA) And so on. In addition, as a greenish luminescent material, N- (9,10-diphenyl-2-) Anthril) -N, 9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCA) PA), N- [9,10-bis (1,1'-biphenyl-2-yl) -2-anthril] -N, 9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N- (9,10-diphenyl-2-anthril) -N, N', N'-triphenyl-1, 4-Phenylenediamine (abbreviation: 2DPAPA), N- [9,10-bis (1,1'-bi) Phenyl-2-yl) -2-anthril] -N, N', N'-triphenyl-1,4-phenyl Enilegenamine (abbreviation: 2DPABPhA), N- [9,10-bis (1,1'-biff) Enyl-2-yl)]-N- [4- (9H-carbazole-9-yl) phenyl] -N- Phenylanthracene-2-amine (abbreviation: 2YGABPhA), N, N, 9-trife Nylanthracene-9-amine (abbreviation: DPhAPhA) and the like can be mentioned. Also yellow As a luminescent material of the system, rubrene, 5,12-bis (1,1'-biphenyl-4-yl)- Examples include 6,11-diphenyltetracene (abbreviation: BPT). Also, reddish emission As a light material, N, N, N', N'-Tetrakis (4-methylphenyl) Tetracene-5 , 11-Diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N, N, N', N '-Tetrakis (4-Methylphenyl) Asenaft [1,2-a] Fluoranthene-3, Examples include 10-diamine (abbreviation: p-mPhAFD).

0157Further, as a phosphorescent compound that can be used for the light emitting layer 113, for example, blue-based light emission As a material, bis [2- (4', 6'-difluorophenyl) pyridinato-N, C^2’] Iridium (III) Tetrakis (1-pyrazolyl) Borato (abbreviation: FIr6), Bis [2- (4', 6'-difluorophenyl) pyridinato-N, C^2’] Iridium (II I) Picolinate (abbreviation: F Irpic), Bis {2- [3', 5'-Bis (Trifluo) Lomethyl) Phenyl] Pyridinato-N, C^2’} Iridium (III) picolinate (abbreviation) Name: Ir (CF)₃ppy)₂(pic)), Bis [2- (4', 6'-difluoropheni) Le) Pirijinato-N, C^2’] Iridium (III) Acetylacetoneate (abbreviation: FI) r (acac)) and the like. In addition, as a greenish luminescent material, Tris (2-fe) Nilpiridinato-N, C^2’) Iridium (III) (abbreviation: Ir (ppy)₃),Screw (2-Phenylpyridinato-N, C^2’) Iridium (III) Acetylacetoneate ( Abbreviation: Ir (ppy)₂(acac)), bis (1,2-diphenyl-1H-benzoimi) Dazorat) Iridium (III) Acetylacetoneate (abbreviation: Ir (pbi))₂(ac ac)), bis (benzo [h] quinolinato) iridium (III) acetylacetonate (Abbreviation: Ir (bzq)₂(acac))), Tris (benzo [h] quinolinato) illizi Umm (III) (abbreviation: Ir (bzq)₃) And so on. Also, a yellowish luminescent material As bis (2,4-diphenyl-1,3-oxazolato-N, C^2’)iridium( III) Acetylacetoneate (abbreviation: Ir (dpo))₂(acac)), Bis [2-( 4'-Perfluorophenylphenyl) pyridinato] iridium (III) acetylace Tonert (abbreviation: Ir (p-PF-ph)₂(acac)), bis (2-phenylbenzo Thiazorat-N, C^2’) Iridium (III) Acetylacetoneate (abbreviation: Ir (b) t)₂(acac)), (acetylacetonato) bis [2,3-bis (4-fluorofe) Nil) -5-methylpyrazinato] Iridium (III) (abbreviation: Ir (Fdppr-Me) )₂(acac)), (acetylacetonato) bis {2- (4-methoxyphenyl) -3 , 5-Dimethylpyrazinato} Iridium (III) (abbreviation: Ir (dmmoppr))₂( acac)) etc. can be mentioned. In addition, as an orange-based luminescent material, Tris (2-phenyl) Kinolinato-N, C^2’) Iridium (III) (abbreviation: Ir (pq)₃), Bis (2- Phenylquinolinato-N, C^2’) Iridium (III) Acetylacetoneate (abbreviation: Ir (pq)₂(acac)), (acetylacetonato) bis (3,5-dimethyl-2- Phenylpyrazinato) Iridium (III) (abbreviation: Ir (mppr-Me)₂(aca c)), (Acetylacetonato) bis (5-isopropyl-3-methyl-2-phenylpi) Radinato) Iridium (III) (abbreviation: Ir (mppr-iPr))₂(acac)) Which can be mentioned. In addition, as a red-based luminescent material, bis [2- (2'-benzo [4,5- α] thienyl) pyridinat-N, C^3’] Iridium (III) Acetylacetoneate ( Abbreviation: Ir (btp)₂(acac)), Bis (1-Phenylisoquinolinato-N, C²^’) Iridium (III) Acetylacetoneate (abbreviation: Ir (piq))₂(acac) ), (Acetylacetonato) bis [2,3-bis (4-fluorophenyl) quinoxalina G] Iridium (III) (abbreviation: Ir (Fdpq)₂(acac)), (Acetylacetone Tonato) Bis (2,3,5-triphenylpyrazinato) Iridium (III) (abbreviation: I) r (tppr)₂(acac)), (Zipivaloyl metanato) Bis (2,3,5-truffle) Enilpyrazinato) Iridium (III) (abbreviation: Ir (tppr))₂dpm), 2,3 , 7,8,12,13,17,18-Octaethyl-21H, 23H-Porphyrin Platinum Examples thereof include organometallic complexes such as (II) (abbreviation: PtOEP). Also, Tris (Acetyl) Acetylacetone) (monophenanthroline) Terbium (III) (abbreviation: Tb (acac)₃(Phen)), Tris (1,3-diphenyl-1,3-propanedionat) (Monof) Enantroline) Europium (III) (abbreviation: Eu (DBM)₃(Phen)), G Squirrel [1- (2-tenoyl) -3,3,3-trifluoroacetonato] (monophenant) Lorin) Europium (III) (abbreviation: Eu (TTA))₃(Phen)) etc. rare earth gold Genus complexes are phosphorescent because they emit light from rare earth metal ions (electronic transitions between different multiplicities). It can be used as a sex compound.

0158Moreover, a polymer compound can be used as a luminescent substance. Specifically, a blue light emitting material As a fee, poly (9,9-dioctylfluorene-2,7-jiil) (abbreviation: PFO), Poly [(9,9-Dioctyl Fluorene-2,7-Diyl) -co- (2,5-Dimetoki) Sibenzene-1,4-diyl)] (abbreviation: PF-DMOP), poly {(9,9-diocti) Rufluolene-2,7-diyl) -co- [N, N'-di- (p-butylphenyl) -1 , 4-Diaminobenzene]} (abbreviation: TAB-PFH) and the like. Also, greenish As luminescent materials, poly (p-phenylene vinylene) (abbreviation: PPV), poly [(9,9) -Dihexyl fluorene-2,7-diyl) -alt-co- (benzo [2,1,3] chi Asiasol-4,7-Diyl)] (abbreviation: PFBT), Poly [(9,9-Dioctyl-) 2,7-Dibinylene Fluorenylene) -alt-co- (2-Methoxy-5- (2-Echi) Luhexyloxy) -1,4-phenylene)] and the like. Also, orange to red emission As an optical material, poly [2-methoxy-5- (2'-ethylhexoxy) -1,4-phenyl Lembinilen] (abbreviation: MEH-PPV), poly (3-butylthiophene-2,5-dii) Le) (abbreviation: R4-PAT), poly {[9,9-dihexyl-2,7-bis (1-cyano) Vinylene) Fluolenilen] -alt-co- [2,5-bis (N, N'-diphenyla) Mino) -1,4-phenylene]}, poly {[2-methoxy-5- (2-ethylhexyloki) Shi) -1,4-bis (1-cyanovinylene phenylene)] -alt-co- [2,5-bi Su (N, N'-diphenylamino) -1,4-phenylene]} (abbreviation: CN-PPV-D PD) and the like.

0159As the light emitting layer 113, the above-mentioned light emitting substance (guest material) is used as another substance (host material). ) May be dispersed. Various host materials can be used. , The lowest empty orbital level (LUMO level) is higher than the luminescent material, and the highest occupied orbital level (HOM) It is preferable to use a substance having a low O level).

0160The carbazole compound according to one aspect of the present invention is a substance having a wide bandgap (high S1 level). Therefore, it can be suitably used as a host material for the light emitting layer 113.

0161When the luminescent substance is a phosphorescent compound, the host material has a higher T1 level than the luminescent substance. It is preferable to use a good substance.

0162Since the carbazole compound according to one aspect of the present invention is a substance having a high T1 level, it is a phosphorescent substance. It can also be suitably used as a host material for.

0163Other applicable host materials include, specifically, tris (8-quinolinolato) al. Minium (III) (abbreviation: Alq), Tris (4-methyl-8-quinolinolato) aluminum Nium (III) (abbreviation: Almq₃), Bis (10-Hydroxybenzo [h] quinolina G) Beryllium (II) (abbreviation: BeBq₂), Bis (2-methyl-8-quinolinolato) (4-Phenylphenorato) Aluminum (III) (abbreviation: BAlq), Bis (8-ki) Norinorat) Zinc (II) (abbreviation: Znq), Bis [2- (2-benzoxazolyl) fu Enorato] Zinc (II) (abbreviation: ZnPBO), Bis [2- (2-benzothiazolyl) fu Enorato] Metal complexes such as zinc (II) (abbreviation: ZnBTZ), 2- (4-biphenylyl) ) -5- (4-tert-Butylphenyl) -1,3,4-oxadiazole (abbreviation: P) BD), 1,3-bis [5- (p-tert-butylphenyl) -1,3,4-oxadi Azole-2-yl] Benzene (abbreviation: OXD-7), 3- (4-biphenylyl) -4- Phenyl-5- (4-tert-butylphenyl) -1,2,4-triazole (abbreviation: abbreviation: TAZ), 2,2', 2''-(1,3,5-benzenetriyl) Tris (1-phenyl) -1H-benzimidazole) (abbreviation: TPBI), vasophenanthroline (abbreviation: BP) Heterocyclic compounds such as hen) and vasocuproin (abbreviation: BCP) and 9- [4- (10) -Phenyl-9-anthryl) Phenyl] -9H-carbazole (abbreviation: CzPA), 3 , 6-Diphenyl-9- [4- (10-Phenyl-9-Anthryl) Phenyl] -9H- Carbazole (abbreviation: DPCzPA), 9,10-bis (3,5-diphenylphenyl) Anthracene (abbreviation: DPPA), 9,10-di (2-naphthyl) anthracene (abbreviation: abbreviation: DNA), 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,9'-Biantril (abbreviation: BANT), 9,9'-(Stillbe) N-3,3'-Diyl) Diphenanthrene (abbreviation: DPNS), 9,9'-(Stilbene) -4,4'-Zyle) Diphenanthrene (abbreviation: DPNS2), 3,3', 3''-(Bee) Nzen-1,3,5-triyl) tripylene (abbreviation: TPB3), 9,10-diphenyl Anthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylc Condensed aromatic compounds such as lysene, N, N-diphenyl-9- [4- (10-phenyl-9) -Anthryl) Phenyl] -9H-carbazole-3-amine (abbreviation: CzA1PA), 4- (10-Phenyl-9-anthril) triphenylamine (abbreviation: DPhPA), N , 9-Diphenyl-N- [4- (10-Phenyl-9-Anthryl) Phenyl] -9H- Carbazole-3-amine (abbreviation: PCAPA), N, 9-diphenyl-N- {4- [4 -(10-Phenyl-9-anthryl) Phenyl] Phenyl} -9H-Carbazole-3 -Amine (abbreviation: PCAPBA), N- (9,10-diphenyl-2-anthril)-N , 9-Diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), NPB ( Or α-NPD), TPD, DFLDPBi, BSPB and other aromatic amine compounds Can be used.

0164In addition, a plurality of types of host materials can be used. For example, ruble to suppress crystallization A substance that suppresses crystallization may be further added. Also, energy for guest materials NPB, Alq, etc. may be further added for more efficient movement.

0165Crystallization of the light emitting layer 113 is suppressed by having the guest material dispersed in the host material. Can be controlled. In addition, suppressing concentration quenching due to the high concentration of guest material Can be done.

0166The electron transport layer 114 is a layer containing a substance having a high electron transport property. As a substance with high electron transportability For example, Tris (8-quinolinolato) aluminum (abbreviation: Alq), Tris (4) -Methyl-8-Kinolinolato) Aluminum (abbreviation: Almq)₃), Bis (10-hydro Xybenzo [h] quinolinato) Beryllium (abbreviation: BeBq)₂), Bis (2-methyl-8 -Kinolinolato) (4-Phenylphenorato) Aluminum (abbreviation: BAlq), etc. Examples thereof include a metal complex having a nolin skeleton or a benzoquinoline skeleton. In addition, other screws [2- (2-Hydroxyphenyl) benzoxazolate] Zinc (abbreviation: Zn (BOX))₂), Bis [2- (2-Hydroxyphenyl) benzothiazolate] Zinc (abbreviation: Zn (BT) Z)₂) And other oxazole-based and thiazole-based ligand-bearing metal complexes should also be used. Can be done. In addition to metal complexes, 2- (4-biphenylyl) -5- (4-tert -Butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD) and 1,3-bis [5- (p-tert-butylphenyl) -1,3,4-oxadiazole-2-yl] Benzene (abbreviation: OXD-7), 3- (4-biphenylyl) -4-phenyl-5- (4-) tert-Butylphenyl) -1,2,4-triazole (abbreviation: TAZ), vasofena Also use ntroline (abbreviation: BPhen), bassocuproin (abbreviation: BCP), etc. Can be done. The substances mentioned here are mainly 10^-6cm²Objects with electron mobility of / Vs or higher Quality. Further, the electron transport layer is not limited to a single layer, but has two or more layers made of the above substances. It may be laminated.

0167The electron injection layer 115 is a layer containing a substance having a high electron injection property. The electron injection layer 115 has a Tium, cesium, calcium, lithium fluoride, cesium fluoride, calcium fluoride, Using alkali metals such as lithium oxide, alkaline earth metals, or compounds thereof Can be In addition, rare earth metal compounds such as erbium fluoride can be used. To. Further, the substance constituting the electron transport layer 114 described above can also be used.

0168Alternatively, a compound formed by mixing an organic compound and an electron donor (donor) in the electron injection layer 115. A mixed material may be used. In such composite materials, electrons are transferred to organic compounds by electron donors. Since it is generated, it is excellent in electron injection and electron transport. In this case, as an organic compound , It is preferable that the material is excellent in transporting generated electrons, and specifically, for example, as described above. Substances (metal complexes, heteroaromatic compounds, etc.) constituting the electron transport layer 114 can be used. To. The electron donor may be any substance that exhibits electron donating property to the organic compound. concrete Alkaline metals, alkaline earth metals and rare earth metals are preferable, and lithium, cesium, etc. Examples include magnesium, calcium, erbium, ytterbium and the like. Also, Arca Metalloid oxides and alkaline earth metal oxides are preferable, and lithium oxides and calcium oxides are preferable. , Barium oxide and the like. Also, use a Lewis base such as magnesium oxide. You can also do it. Also, use an organic compound such as tetrathiafulvalene (abbreviation: TTF). You can also do it.

0169The hole injection layer 111, the hole transport layer 112, the light emitting layer 113, and the electron transport layer 114 described above. , The electron injection layer 115 includes a vapor deposition method (including a vacuum vapor deposition method), an inkjet method, and a coating method, respectively. It can be formed by a method such as cloth method.

0170The second electrode 103 has a small work function when the second electrode 103 functions as a cathode (favorable). Using metals, alloys, conductive compounds, and mixtures thereof, etc. It is preferable to form. Specifically, elements belonging to Group 1 or Group 2 of the Periodic Table of the Elements. That is, alkali metals such as lithium and cesium, and magnesium, calcium, and stron. Alkaline earth metals such as tium and alloys containing them (for example, Mg-Ag, Al-Li) ), Europium, ytterbium and other rare earth metals and alloys containing them, as well as alumini Umm, silver, etc. can be used.

0171However, of the EL layer 102, the layer formed in contact with the second electrode 103 is the above-mentioned organicization. When using a composite material consisting of a mixture of a compound and an electron donor (donor), the work function is large. Oxidized indies containing aluminum, silver, ITO, silicon or silicon oxide, small or small Various conductive materials such as um-tin oxide can be used.

0172When forming the second electrode 103, a vacuum vapor deposition method or a sputtering method should be used. Can be done. When using silver paste, use the coating method or inkjet method. Can be used.

0173The above-mentioned light emitting element has a potential difference generated between the first electrode 101 and the second electrode 103. An electric current flows, and holes and electrons are recombined in the EL layer 102 to emit light. Soshi This light emission passes through either or both of the first electrode 101 and the second electrode 103. Is taken out. Therefore, either the first electrode 101 or the second electrode 103 , Or both are electrodes that are translucent to visible light.

0174The structure of the layer provided between the first electrode 101 and the second electrode 103 is as described above. Not limited to. To prevent quenching caused by the proximity of the light emitting region to the metal, Emission region where holes and electrons recombine at a site distant from the electrode 101 of 1 and the electrode 103 of the second Any structure other than the above may be used as long as the configuration is provided with a region.

0175That is, the laminated structure of the layers is not particularly limited, and is a substance having high electron transport property and hole transport property. High substance, highly electron-injectable substance, highly hole-injectable substance, bipolar (electron and hole) A layer made of a substance with high transportability, or a hole blocking material, etc., can be freely assembled with the light emitting layer. It may be configured by matching.

0176The light emitting element shown in FIG. 1 (B) is a first electrode 101 and a second electrode on the substrate 100. An EL layer 102 is provided between the pair of electrodes 103. The EL layer 102 is a hole injection layer. It has 111, a hole transport layer 112, a light emitting layer 113, an electron transport layer 114, and an electron injection layer 115. ing. The light emitting element in FIG. 1 (B) has a second electric power functioning as a cathode on the substrate 100. Electron injection layer 115, electron transport layer 114, which are laminated on the pole 103 and the second electrode 103 in order. A light emitting layer 113, a hole transport layer 112, a hole injection layer 111, and an anode provided on the layer 111. It is composed of a first electrode 101 that functions as a function.

0177Further, the carbazole compound according to one aspect of the present invention has a deep HOMO level and a shallow LUMO level. Also, the band gap is wide. Therefore, the carrier transport layer (hole transport layer, It can be suitably used as an electron transport layer, a hole block layer, etc.). That's why it's highly effective A rational element can be obtained.

0178Hereinafter, a specific method for forming the light emitting element will be shown.

0179The light emitting element of this embodiment has a structure in which an EL layer is sandwiched between a pair of electrodes. electrode( (1st electrode and 2nd electrode), and EL layer are droplet ejection method (inkjet method), spinco It may be formed by a wet method such as a printing method or a printing method, and may be formed by a vacuum deposition method, a CVD method, or sputtering. It may be formed by using a dry method such as a ring method. Formed under atmospheric pressure using the wet method Because it can be formed by a simple device and process, the process is simplified and productivity is achieved. Has the effect of improving. The dry method, on the other hand, is a solution because the material does not need to be dissolved. A poorly soluble material can also be used, and there is a wide range of material choices.

0180All the thin films constituting the light emitting element may be formed by a wet method. In this case, the wet method is required The light emitting element can be manufactured only with the necessary equipment. In addition, stacking until the light emitting layer is formed The wet method may be used to form the functional layer and the first electrode to be laminated on the light emitting layer by the dry method. I. Further, the second electrode and the functional layer before forming the light emitting layer are formed by a dry method, and the light emitting layer, The functional layer and the first electrode to be laminated on the light emitting layer may be formed by a wet method. of course , The present embodiment is not limited to this, and depends on the material used, the required film thickness, and the interface state. A wet method and a dry method can be appropriately selected and combined to produce a light emitting device.

0181As described above, a light emitting device can be produced using the carbazole compound according to one aspect of the present invention. it can. In one aspect of the present invention, a light emitting device having high luminous efficiency can be realized. Also, A light emitting element having a long life can be realized.

0182In addition, a light emitting device (image display device) using the light emitting element of one aspect of the present invention thus obtained. Vise) can achieve low power consumption.

0183In addition, using the light emitting element shown in this embodiment, a passive matrix type light emitting device or a thin light emitting device can be used. Active matrix type in which the drive of the light emitting element is controlled by a film transistor (TFT) Light emitting device can be manufactured.

0184This embodiment can be used in combination with other embodiments as appropriate.

0185(Embodiment 3) In this embodiment, a light emitting element having a structure in which a plurality of light emitting units are laminated (hereinafter, referred to as a laminated element). ) Will be described with reference to FIG. This light emitting element has a first electrode and a second electrode. It is a light emitting element having a plurality of light emitting units between the two.

0186In FIG. 2A, a first light emitting uni is located between the first electrode 301 and the second electrode 303. The 311 and the second light emitting unit 312 are laminated. In the present embodiment, the first Electrode 301 is an electrode that functions as an anode, and the second electrode 303 functions as a cathode. It is an electrode. The same as in the second embodiment is applied to the first electrode 301 and the second electrode 303. Can be Also, the first light emitting unit 311 and the second light emitting unit 312 have the same structure. It may be made or have a different configuration. In addition, the first light emitting unit 311 and the second emission The optical unit 312 may have the same configuration as that of the second embodiment. Either one may have a different configuration.

0187Further, between the first light emitting unit 311 and the second light emitting unit 312, a charge generation layer 31 3 is provided. The charge generation layer 313 has a voltage on the first electrode 301 and the second electrode 303. Is applied, electrons are injected into one light emitting unit and holes are injected into the other light emitting unit. Has a function to enter. In the case of this embodiment, the first electrode 301 is replaced by the second electrode 303. When a voltage is applied so that the potential becomes high, the first light emitting unit from the charge generation layer 313 Electrons are injected into 311 and holes are injected into the second light emitting unit 312.

0188The charge generation layer 313 has translucency with respect to visible light from the viewpoint of light extraction efficiency. Is preferable. Further, the charge generation layer 313 is formed from the first electrode 301 and the second electrode 303. Works even with low conductivity.

0189The charge generation layer 313 contains an organic compound having a high hole transport property and an electron acceptor. Even if it is configured, it contains an organic compound with high electron transportability and an electron donor (donor). There may be. Moreover, both of these configurations may be laminated. In addition, electron acceptors and The electron donor may be at least one that transfers and receives electrons with the assistance of an electric field.

0190In the case where an electron acceptor is added to an organic compound having high hole transportability, hole transport As the highly rechargeable organic compound, the carbazole compound according to one aspect of the present invention can be used. Wear. In addition, NPB, TPD, TDATA, MTDATA, 4,4'-bis [N-( Spiro-9,9'-bifluoren-2-yl) -N-phenylamino] biphenyl (abbreviation) Aromatic amine compounds such as: BSPB) can be used. The substances mentioned here are Mainly 10^-6cm²It is a substance with hole mobility of / Vs or more. However, holes rather than electrons A substance other than the above may be used as long as it is an organic compound having high transportability.

0191In addition, as an electron acceptor, 7,7,8,8-tetracyano-2,3,5,6-tetraf Luolokinodimethane (abbreviation: F)₄-TCNQ), chloranil, etc. can be mentioned. Well In addition, transition metal oxides can be mentioned. In addition, in the 4th to 8th groups in the periodic table of elements The oxide of the metal to which it belongs can be mentioned. Specifically, vanadium oxide, niobium oxide, Tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, resin oxide Nium is preferable because it has high electron acceptability. Especially, molybdenum oxide is stable in the atmosphere. It is preferable because it has low hygroscopicity and is easy to handle.

0192On the other hand, in the case where an electron donor is added to an organic compound having high electron transport property, Examples of organic compounds having high electron transport properties include Alq and Almq.₃, BeBq₂, BA A metal complex having a quinoline skeleton or a benzoquinoline skeleton such as lq can be used. To. Also, Zn (BOX)₂, Zn (BTZ)₂Oxazole-based, thiazole-based arrangements such as A metal complex having a position can also be used. In addition to metal complexes, PBD and OXD-7, TAZ, BPhen, BCP, etc. can also be used. Substances mentioned here Is mainly 10^-6cm²It is a substance with electron mobility of / Vs or more. In addition, than holes A substance other than the above may be used as long as it is an organic compound having high electron transportability.

0193The electron donor includes an alkali metal, an alkaline earth metal, a rare earth metal, or an elemental circumference. Metals belonging to Group 13 in the timetable and their oxides, carbonates, etc. can be used. Specifically, lithium, cesium, magnesium, calcium, ytterbium, indi It is preferable to use um, lithium oxide, cesium carbonate and the like. Also, Tetratianaf An organic compound such as Tassen may be used as an electron donor.

0194By forming the charge generation layer 313 using the above-mentioned material, the EL layers are laminated. It is possible to suppress an increase in the drive voltage in such a case.

0195In the present embodiment, a light emitting element having two light emitting units has been described, but similarly, As shown in Fig. 2 (B), a light emitting element in which three or more light emitting units are stacked can also be applied. It is possible. A plurality of light emitting units between a pair of electrodes like the light emitting element according to the present embodiment. By partitioning and arranging with a charge generation layer, it emits light with high brightness while keeping the current density low. A long-life element can be realized.

0196In addition, by making the emission color of each light emitting unit different, the light emitting element as a whole , It is possible to obtain light emission of a desired color. For example, in a light emitting element having two light emitting units Then, the emission color of the first light emitting unit and the emission color of the second light emitting unit have a complementary color relationship. By doing so, it is also possible to obtain a light emitting element that emits white light as a whole. The complementary color refers to the relationship between colors that become achromatic when mixed. In other words, in the complementary color relationship White luminescence can be obtained by mixing light obtained from a substance that emits a certain color. Also, The same applies to a light emitting element having three light emitting units, for example, the first light emitting unit. The emission color of the light emission unit is red, the emission color of the second emission unit is green, and the emission color of the third emission unit When the emission color of the light emitting element is blue, white light emission can be obtained as the entire light emitting element.

0197It should be noted that this embodiment can be appropriately combined with other embodiments.

0198(Embodiment 4) In the present embodiment, FIG. 3 is used for a light emitting device having a light emitting element according to one aspect of the present invention. explain. Note that FIG. 3 (A) is a top view showing the light emitting device, and FIG. 3 (B) is FIG. 3 (A). It is sectional drawing cut by B and CD.

0199In FIG. 3 (A), 401 shown by the dotted line is the drive circuit section (source side drive circuit), 402. Is a pixel unit, and 403 is a drive circuit unit (gate side drive circuit). Also, 404 is a sealing substrate, 405 is a sealing material, and the inside surrounded by the sealing material 405 is a space.

0200The routing wiring 408 is input to the source side drive circuit 401 and the gate side drive circuit 403. FPC (Flexible Pre) that is a wiring for transmitting the signal to be input and serves as an external input terminal. Video signal, clock signal, start signal, reset signal, etc. from 409 To receive. In addition, although only FPC is shown here, this FPC has a print distribution. A wire board (PWB) may be attached. The light emitting device in the present specification is a light emitting device. It shall include not only the main body but also the state where the FPC or PWB is attached to it.

0201Next, the cross-sectional structure will be described with reference to FIG. 3 (B). Drive circuit section on the element board 410 And the pixel part is formed, but here, with the source side drive circuit 401 which is a drive circuit part , One pixel in the pixel unit 402 is shown.

0202The source side drive circuit 401 is an n-channel type TFT423 and a p-channel type TFT424. A CMOS circuit is formed by combining with. In addition, the drive circuit is a seed formed by TFT. It may be formed by various CMOS circuits, MIMO circuits or MIMO circuits. In addition, the form of this implementation In the state, the driver integrated type in which the drive circuit is formed on the board is shown, but it is not always necessary. , The drive circuit can be formed on the outside instead of on the substrate.

0203In addition, the pixel unit 402 includes a switching TFT 411, a current control TFT 412, and the like. It is formed by a plurality of pixels including a first electrode 413 electrically connected to the rain. Na Insulation 414 is formed over the end of the first electrode 413. Here, positive type It is formed by using the photosensitive acrylic resin film of.

0204Further, in order to improve the covering property, the upper end portion or the lower end portion of the insulator 414 has a curvature. Make sure that a curved surface is formed. For example, positive photosensitive acrylic as a material for insulation 414. Has a radius of curvature (0.2 μm to 3 μm) only at the upper end of the insulator 414. It is preferable to have a curved surface. Also, as an insulator 414, it is etched by irradiating light. Negative type that becomes insoluble in solution, or positive that becomes soluble in etchant by irradiation with light Any of the types can be used.

0205An EL layer 416 and a second electrode 417 are formed on the first electrode 413, respectively. To. Here, the material used for the first electrode 413 that functions as an anode has a large work function. It is desirable to use a key material. For example, ITO film, or indium tin containing silicon. Oxide film, indium oxide film containing 2 to 20 wt% zinc oxide, titanium nitride film, chromium film , Tungsten film, Zn film, Pt film, etc., as well as titanium nitride film and aluminum Lamination with a film as a component, a titanium nitride film, a film containing aluminum as a main component, and a titanium nitride film A three-layer structure or the like can be used. In addition, if it is a laminated structure, the resistance as wiring is low. , Good ohmic contact can be made.

0206Further, the EL layer 416 is a droplet ejection method such as a vapor deposition method using a vapor deposition mask or an inkjet method. , Printing method, spin coating method and the like. EL layer 416 is implemented It contains the carbazole compound shown in Form 1. In addition, other materials constituting the EL layer 416 The agent may be a low molecular weight material, an oligomer, a dendrimer, or a high molecular weight material.

0207Further, a material formed on the EL layer 416 and used for the second electrode 417 that functions as a cathode. Materials with a small work function (Al, Mg, Li, Ca, or alloys or compounds thereof) , Mg-Ag, Mg-In, Al-Li, etc.) is preferably used. EL layer 41 In order for the light generated in 6 to pass through the second electrode 417, the film thickness should be set as the second electrode 417. Thin metal thin film and transparent conductive film (ITO, indium tin oxide containing 2 to 20 wt% zinc oxide Product with indium oxide containing um, silicon or silicon oxide-tin oxide, zinc oxide, etc.) It is better to use layers.

0208Furthermore, by bonding the sealing substrate 404 to the element substrate 410 with the sealing material 405, the element is made. Light emitting element 4 in space 407 surrounded by child substrate 410, sealing substrate 404, and sealing material 405. It has a structure equipped with 18. The space 407 is filled with a filler. In addition to the case where an inert gas (nitrogen, argon, etc.) is filled, the place where it is filled with the sealing material 405. There is also a case.

0209It is preferable to use an epoxy resin for the sealing material 405. Also, these materials It is desirable that the material is as impermeable to water and oxygen as possible. Also, on the sealing board 404 In addition to glass and quartz substrates, FRP (Fiberglass-Rein) is used as the material. forced Plastics), PVF (Polyvinyl Fluoride), Polyester or Can use a plastic substrate made of acrylic or the like.

0210As described above, an active matrix type light emitting device having the light emitting element of one aspect of the present invention. You can get a place.

0211Further, the light emitting element of one aspect of the present invention includes all of the above-mentioned active matrix type light emitting devices. It can also be used for a passive matrix type light emitting device. FIG. 4 shows an aspect of the present invention. A perspective view and a cross-sectional view of a passive matrix type light emitting device using an optical element are shown. In addition, Fig. 4 (A) is a perspective view showing the light emitting device, and FIG. 4 (B) is a cross-sectional view of FIG. 4 (A) cut by XY. is there.

0212In FIG. 4, the EL layer 5 is located between the first electrode 502 and the second electrode 503 on the substrate 501. 04 is provided. The end of the first electrode 502 is covered with an insulating layer 505. And , A partition layer 506 is provided on the insulating layer 505. The side wall of the partition wall layer 506 is on the substrate surface. It has an inclination such that the distance between one side wall and the other side wall becomes narrower as it gets closer. One The cross section of the partition wall layer 506 in the short side direction is trapezoidal, and the bottom side (the plane direction of the insulating layer 505). The side facing the same direction and in contact with the insulating layer 505 is the upper side (similar to the surface direction of the insulating layer 505). It is shorter than the side that faces the direction of and does not contact the insulating layer 505). In this way, the partition layer 506 is installed. By doing so, it is possible to prevent defects in the light emitting element due to crosstalk or the like.

0213From the above, a passive matrix type light emitting device having the light emitting element of one aspect of the present invention is obtained. be able to.

0214The light emitting device (active matrix type, passive matrix type) shown in the present embodiment. ) Are all formed by using the light emitting element of one aspect of the present invention, and therefore have low power consumption. A light emitting device can be obtained.

0215It should be noted that this embodiment can be appropriately combined with other embodiments.

0216(Embodiment 5) In the present embodiment, various electric devices completed by using a light emitting device which is an aspect to which the present invention is applied. An example of a slave device and a lighting fixture will be described with reference to FIGS. 5 and 6.

0217As an electronic device to which a light emitting device is applied, for example, a television device (television or television) (Also called a receiver), monitors for computers, digital cameras, digital videos Cameras, digital photo frames, mobile phones (also called mobile phones and mobile phone devices), mobile phones Band-type game machines, mobile information terminals, sound playback devices, large game machines such as pachinko machines, etc. Be done. Specific examples of these electronic devices and lighting fixtures are shown in FIG.

0218FIG. 5 (A) shows the television device 7100. Television device 7100 The display unit 7103 is incorporated in the housing 7101. Display video on display 7103 The light emitting device can be used for the display unit 7103. Also here Shows a configuration in which the housing 7101 is supported by the stand 7105.

0219The operation of the television device 7100 is performed by the operation switch provided in the housing 7101 and the separate remote control. It can be done by the controller 7110. Operation keys provided in the remote control device 7110 With 7109, you can control the channel and volume, and it will be displayed on the display 7103. You can operate the video. In addition, the remote controller 7110 is equipped with the remote controller. A display unit 7107 for displaying information output from the 7110 may be provided.

0220The television device 7100 is configured to include a receiver, a modem, and the like. To the receiver Can receive more general television broadcasts, and can be wired or wireless via a modem One-way (sender to recipient) or two-way (sending) by connecting to a communication network It is also possible to perform information communication between believers and recipients, or between recipients, etc.).

0221Figure 5 (B) shows a computer, which includes the main unit 7201, housing 7202, display unit 7203, and keys. Includes board 7204, external connection port 7205, pointing device 7206, etc. A computer is manufactured by using a light emitting device for its display unit 7203.

0222Figure 5 (C) shows a portable game machine, which consists of two housings, a housing 7301 and a housing 7302. It is connected so that it can be opened and closed by the connecting part 7303. Display unit 7 on the housing 7301 The 304 is incorporated, and the display 7305 is incorporated in the housing 7302. Also, Figure 5 In addition, the portable game machine shown in (C) includes a speaker unit 7306, a recording medium insertion unit 7307, and the like. LED lamp 7308, input means (operation key 7309, connection terminal 7310, sensor 731 1 (force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemistry Matter, voice, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, Includes a function to measure odor or infrared rays), microphone 7312), etc. To. Of course, the configuration of the portable game machine is not limited to the above, and at least the display unit 730. It suffices to use a light emitting device for both or one of 4 and the display unit 7305, and other accessories. It is possible to have a configuration in which equipment is appropriately provided. The portable game machine shown in Fig. 5 (C) is a recording medium. A function to read the program or data recorded on the body and display it on the display unit, or other equipment It has a function to share information by wirelessly communicating with a band-type gaming machine. In addition, the carrying that is shown in Fig. 5 (C) The functions of the band-type gaming machine are not limited to this, and can have various functions.

0223FIG. 5 (D) shows an example of a mobile phone. Mobile phone 7400 is in housing 7401 In addition to the built-in display 7402, operation buttons 7403, external connection port 7404, speed It is equipped with a mosquito 7405 and a microphone 7406. The mobile phone 7400 is equipped with a light emitting device. It is made by using the device for the display unit 7402.

0224The mobile phone 7400 shown in Fig. 5 (D) provides information by touching the display unit 7402 with a finger or the like. Can be entered. Also, operations such as making a phone call or composing an email can be performed. This can be done by touching the display unit 7402 with a finger or the like.

0225The screen of the display unit 7402 mainly has three modes. The first is a table that mainly displays images. It is a display mode, and the second is an input mode mainly for inputting information such as characters. The third is the display It is a display + input mode in which two modes, mode and input mode, are mixed.

0226For example, when making a call or composing an email, enter characters on the display 7402. The main character input mode may be set, and the characters displayed on the screen may be input. in this case , It is preferable to display the keyboard or number button on most of the screen of the display unit 7402. Castanopsis.

0227In addition, a sensor that detects the inclination of the gyro, accelerometer, etc. is installed inside the mobile phone 7400. By providing a detection device to have, the orientation (vertical or horizontal) of the mobile phone 7400 can be determined and the table can be used. The screen display of the display 7402 can be automatically switched.

0228To switch the screen mode, touch the display unit 7402 or operate the housing 7401. It is done by operating button 7403. Also, for the type of image displayed on the display unit 7402 Therefore, it is possible to switch. For example, the image signal displayed on the display is a moving image. Switch to display mode for data and input mode for text data.

0229In addition, in the input mode, the signal detected by the optical sensor of the display unit 7402 is detected and displayed. If there is no input by touch operation of part 7402 for a certain period of time, the screen mode is input mode. It may be controlled to switch to the display mode from.

0230The display unit 7402 can also function as an image sensor. For example, display unit 74 You can authenticate yourself by touching 02 with your palm or finger and taking an image of your palm print, fingerprint, etc. Well In addition, a backlight that emits near-infrared light on the display unit or a light source for sensing that emits near-infrared light. Can also be used to image finger veins, palmar veins, and the like.

0231Figure 5 (E) shows a tabletop lighting fixture, which includes a lighting unit 7501, an umbrella 7502, and a variable arm 7503. Includes stanchions 7504, pedestal 7505, and power supply 7506. The tabletop lighting fixture illuminates the light emitting device. It is manufactured by using it for the bright part 7501. The lighting fixtures are fixed to the ceiling. Alternatively, wall-mounted lighting fixtures and the like are also included.

0232FIG. 6 shows an example in which the light emitting device is used as the indoor lighting device 801. Larger area of light emitting device It can also be used as a large-area lighting device. In addition, roll type lighting It can also be used as a bright device 802. As shown in FIG. 6, the indoor lighting device 80 In the room equipped with 1, the desktop lighting fixture 803 described in FIG. 5 (E) may be used together.

0233As described above, an electronic device or a lighting fixture can be obtained by applying a light emitting device. Luminous equipment The range of application of the device is extremely wide, and it can be applied to electronic devices in all fields.

0234The configurations shown in the present embodiment are appropriately assembled from the configurations shown in the first to fourth embodiments. It can be used together.

<p num="0235">In this embodiment, 3- [4- (1-Nafuchi) represented by the structural formula (100) in the first embodiment Le) -Phenyl] -9-Phenyl-9H-Carbazole (abbreviation: PCPN) Example 1 and Synthesis Example 2 are shown.</p><p num="0236"><chemistry num="38"><img id="000039" he="63" wi="170" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0237">&lt;Synthesis example 1&gt; In a 200 mL three-necked flask, 5.0 g of 3-bromo-9-phenyl-9H-carbazole (15.5 mmol), 4- (1-naphthyl) -phenylboronic acid 4.2 g (17.1 m) mol), palladium (II) acetate 38.4 mg (0.2 mmol), tris (2-methi) Ruphenyl) Phosphine 104 mg (0.3 mmol), toluene 50 mL, ethanol Remove the mixture of 5 mL and 30 mL of 2 mol / L potassium carbonate aqueous solution with stirring under reduced pressure. After airing, the mixture was heated and stirred at 85 ° C for 9 hours under a nitrogen atmosphere to react.</p><p num="0238">After the reaction, 500 mL of toluene was added to this reaction mixture, and the organic layer of this mixture was floridied. Le (Wako Pure Chemical Industries, Ltd., Catalog No .: 540-00135), Alumina (Merck, Neutral), through Celite (Wako Pure Chemical Industries, Ltd., Catalog No .: 531-16855) And filtered. The obtained filtrate was washed with water, and magnesium sulfate was added to adsorb the water. This suspension was filtered to obtain a filtrate. The obtained filtrate is concentrated and silica gel column chromatograph Purification by Raffy was performed. At this time, as a developing solvent for chromatography, Torue A mixed solvent of hexane and hexane (toluene: hexane = 1: 4) was used. Obtained fraction Was concentrated, methanol was added, ultrasonic waves were applied, and then recrystallized. The white color of the target product was obtained. The powder was obtained in a yield of 6.24 g and a yield of 90%. The reaction scheme of the above synthesis example 1 is as follows (F1- Shown in 1).</p><p num="0239"><chemistry num="39"><img id="000040" he="90" wi="170" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0240">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex Sun = 10: 10), the target product is 0.42, 3-bromo-9-phenyl-9H-carbazo Le was 0.58.</p><p num="0241">The compound obtained in Synthesis Example 1 was measured by nuclear magnetic resonance spectroscopy (NMR). Measured below Indicates data.</p><p num="0242">¹1 H NMR (CDCl₃, 300MHz): δ (ppm) = 7.30-7.35 (m, 1H), 7.44-7.67 (m, 14H), 7.76 (dd, J = 8.7Hz, 1.8 Hz, 1H), 7.84-7.95 (m, 4H), 8.04 (d, J = 7.8,1H), 8.23 (d, J = 7.8,1H), 8.46 (d, J = 1.5,1H).</p><p num="0243">Also,¹The 1 H NMR chart is shown in FIGS. 7 (A) and 7 (B). Note that Fig. 7 (B) shows Fig. 7 ( It is a chart which expanded the range of 7.0ppm to 9.0ppm in A). Measurement From the constant results, the target product 3- [4- (1-naphthyl) -phenyl] -9-phenyl-9 It was confirmed that H-carbazole (abbreviation: PCPN) was obtained.</p><p num="0244">&lt;Synthesis example 2&gt; This synthesis example shows a synthesis example of PCPN different from the above synthesis example 1.</p><p num="0245">[Step 1: Synthesis of 3- (4-Bromophenyl) -9-phenyl-9H-carbazole Law] In a 300 mL three-necked flask, 14 g (50 mmol) of 4-bromoiodobenzene, 9- Phenyl-9H-carbazole-3-boronic acid 14g (50 mmol), palladium acetate (II) 110 mg (0.5 mmol), tri (o-tolyl) phosphine 300 mg (1) .0 mmol), 50 mL of toluene, 10 mL of ethanol, 2 mol / L potassium carbonate water A mixture of 25 mL of solution was degassed with stirring under reduced pressure and then under a nitrogen atmosphere at 80 ° C. 6 The mixture was heated and stirred for a period of time and reacted.</p><p num="0246">After the reaction, 200 mL of toluene was added to this reaction mixture, and this suspension was added to Florisil and Cera. It was filtered through it. Wash the obtained filtrate with water, add magnesium sulfate to absorb water. I dressed it. This suspension was filtered to obtain a filtrate. The obtained filtrate is concentrated and silica gel column Purification by chromatography was performed. At this time, it is used as a developing solvent for chromatography. Then, a mixed solvent of toluene and hexane (toluene: hexane = 1: 4) was used. Obtained After concentrating the fraction, adding hexane and applying ultrasonic waves, it was recrystallized. A white powder of the product was obtained with a yield of 15 g and a yield of 75%. The reaction scheme of step 1 above is as follows ( Shown in F1-2).</p><p num="0247"><chemistry num="40"><img id="000041" he="83" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0248">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex For sun = 10: 10), the target product was 0.32 and 4-bromoiodobenzene was 0.74.</p><p num="0249">The compound obtained in step 1 above was measured by nuclear magnetic resonance spectroscopy (NMR). Measured below Show the data.¹1 H NMR (CDCl₃, 300MHz): δ (ppm) = 7.24-7.32 (m, 1H), 7.40-7.64 (m, 13H), 8.17 (d, J = 7.2Hz, 1H), 8.29 (s, 1H).</p><p num="0250">Also,¹The 1 H NMR chart is shown in FIGS. 8 (A) and 8 (B). Note that FIG. 8 (B) is shown in FIG. 8 (B). It is a chart which expanded the range from 7.0ppm to 8.5ppm in A). Measurement From the results, the target product, 3- (4-bromophenyl) -9-phenyl-9H-carbazo. It was confirmed that the product was obtained.</p><p num="0251">The molecular weight of the above compound is determined by the GC-MS detector (manufactured by Thermo Fisher, ITQ11). 00 Ion trap type GCMS system). The chart is shown in Figure 9. molecule Detects peaks mainly in quantity 397.13 (mode is EI +), and from the measurement results, the purpose The product 3- (4-bromophenyl) -9-phenyl-9H-carbazole was obtained. I confirmed that.</p><p num="0252">[Step 2: 3- [4- (1-Phenyl) -Phenyl] -9-Phenyl-9H-Carba Synthesis method of sol (abbreviation: PCPN)] To 50 mL three-necked flask 3- (4-Bromophenyl) -9-Phenyl-9H-Carbazo 2.4 g (5.0 mmol) of naphthalene-1-boronic acid 1.1 g (5.5 mmo) l), Palladium acetate (II) 20 mg (0.1 mmol), tri (o-tolyl) phos 36 mg (0.1 mmol) of fins, 10 mL of toluene, 1.5 mL of ethanol, 2 m A mixture of 5 mL of ol / L potassium carbonate aqueous solution was degassed with stirring under reduced pressure, and then nitrogen. In an atmosphere, the mixture was heated and stirred at 90 ° C for 14 hours to react.</p><p num="0253">After the reaction, 200 mL of toluene was added to this reaction mixture, and the organic layer of this mixture was floridied. Filtered through all, alumina and Celite. Wash the obtained filtrate with water and use magnesium sulfate. Moisture was adsorbed. This suspension was filtered to obtain a filtrate. Concentrate the obtained filtrate , Purified by silica gel column chromatography. At this time, the chromatograph Toluene and hexane mixed solvent (toluene: hexane = 1: 4) Was used. The obtained fraction is concentrated, acetone and methanol are added, and ultrasonic waves are applied. After that, when it was recrystallized, the white powder of the target product was obtained in a yield of 2.3 g and a yield of 86%. the above The reaction scheme of step 2 is shown below (F1-3).</p><p num="0254"><chemistry num="41"><img id="000042" he="85" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0255">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex Sun = 10: 10), the target product is 0.57, 3- (4-bromophenyl) -9-phenyl- 9H-carbazole was 0.65.</p><p num="0256">In addition, the compound obtained in Synthesis Example 2 by nuclear magnetic resonance spectroscopy (NMR) is the target product. 3- [4- (1-naphthyl) -phenyl] -9-phenyl-9H-carbazole (abbreviation) : PCPN) was confirmed.</p><p num="0257">The absorption spectrum of the toluene solution of PCPN is shown in FIG. 10 (A), and the emission spectrum is shown in FIG. Shown in 10 (B). In addition, the absorption spectrum of the PCPN thin film is shown in Fig. 11 (A). The couture is shown in Figure 11 (B). Ultraviolet visible spectrophotometer (JASCO Corporation) for measurement of absorption spectrum Made by Co., Ltd., V550 type) was used. Fluorometer Co., Ltd. Hamamatsu Co., Ltd. for measuring emission spectrum Photonics FS920) was used. The solution is placed in a quartz cell and the thin film is deposited on a quartz substrate. A sample was prepared and measured. Absorption spectrum torr in quartz cell for solution The absorption spectrum measured by adding only the enzyme, and the spectrum of the quartz substrate for the thin film. The absorption spectrum minus each is shown. In FIGS. 10 and 11, the horizontal axis is the wavelength (nm). , The vertical axis represents the strength (arbitrary unit). In the case of toluene solution, absorption pee around 300 nm The maximum emission wavelength was 384 nm (excitation wavelength 320 nm). Also, of thin film In some cases, an absorption peak is seen near 322 nm, and the maximum emission wavelength is 398 nm (excitation wavelength). It was 324 nm).</p><p num="0258">From the absorption spectrum, the PCPN shown in this example is a material with almost no absorption in the visible region. I found out. Moreover, from the emission spectrum, it was found that the emission was bluish purple.</p>

<p num="0259">In this embodiment, 3- [4- (9-phenanthroline) represented by the structural formula (102) in the first embodiment Trill) -Phenyl] -9-Phenyl-9H-Carbazole (abbreviation: PCPPn) manufactured Here is an example of how to do it.</p><p num="0260"><chemistry num="42"><img id="000043" he="66" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0261">[Step 1: 4- (9-Phenyl-9H-carbazole-3-yl) Phenylboronic acid Synthesis method] In a 300 mL three-necked flask, 3- (4-bromo) obtained by the above reaction scheme (F1-2) Add 8.0 g (20 mmol) of phenyl) -9-phenyl-9H-carbazole, and hula After replacing the atmosphere in the sco with nitrogen, dehydrated tetrahydrofuran (abbreviation: THF) 100m L was added to make it -78 ° C. 1.65 mol / L n-butyllithium hex in this mixture 15 mL (24 mmol) of the sun solution was added dropwise, and the mixture was stirred for 2 hours. Boric acid to this mixture Methyl 3.4 mL (30 mmol) was added and stirred at -78 ° C for 2 hours and at room temperature for 18 hours. .. After the reaction, 1M dilute hydrochloric acid was added to the reaction solution until it became acidic, and the mixture was stirred for 7 hours. This is vinegar The mixture was extracted with ethyl acid acid, and the obtained organic layer was washed with saturated brine. After cleaning, the organic layer is covered with sulfuric acid mug. Moisture was adsorbed by adding nesium. The suspension is filtered, the resulting filtrate is concentrated and hexed. After adding sun and applying ultrasonic waves, recrystallization revealed the desired white powder with a yield of 6.4 g. Obtained at a rate of 88%. The reaction scheme of step 1 above is shown in (F2-1) below.</p><p num="0262"><chemistry num="43"><img id="000044" he="52" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0263">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex For sun = 10: 10), the target is 0 (origin) and 3- (4-bromophenyl) -9-fu. Enil-9H-carbazole was 0.53. In addition, ethyl acetate was used as the developing solvent. The Rf value in Ricagel thin layer chromatography (TLC) was 0.72 for the target product, and 3-( 4-Bromophenyl) -9-Phenyl-9H-carbazole was 0.93.</p><p num="0264">[Step 2: 3- [4- (9-Phenyl) -Phenyl] -9-Phenyl-9H- Synthesis method of carbazole (abbreviation: PCPPn)] 9-Phenyl-9H-carbazole-3-yl-phenyl-4 into a 200 mL three-necked flask -1.5 g (5.0 mmol) of boronic acid, 3.2 g (11) of 9-bromophenanthrene mmol), palladium (II) acetate in 11 mg (0.1 mmol), tri (o-tolyl) ) Phosphine 30 mg (0.1 mmol), toluene 30 mL, ethanol 3 mL, 2 A mixture of 5 mL of a mol / L potassium carbonate aqueous solution was degassed with stirring under reduced pressure, and then nitrogen was nitrogened. The mixture was heated and stirred at 90 ° C for 6 hours under a plain atmosphere to react.</p><p num="0265">After the reaction, 200 mL of toluene was added to this reaction mixture, and the organic layer of this mixture was floridied. Filtered through all, alumina and Celite. Wash the obtained filtrate with water and use magnesium sulfate. Moisture was adsorbed. This suspension was filtered to obtain a filtrate. Concentrate the obtained filtrate , Purified by silica gel column chromatography. At this time, the chromatograph A mixed solvent of toluene and hexane (torr) as a developing solvent for en: hexane = 1: 4) Was used. The obtained fraction is concentrated, acetone and methanol are added, and ultrasonic waves are applied. After that, when it was recrystallized, the white powder of the target product was obtained in a yield of 2.2 g and a yield of 75%. Ste The reaction scheme of P2 is shown below (F2-2).<chemistry num="44"><img id="000045" he="98" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0266">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex For Sun = 10: 10), the target product was 0.33 and 9-bromophenanthrene was 0.70.</p><p num="0267">In addition, the obtained compound was measured by nuclear magnetic resonance (NMR). The measurement data is shown below. I will.¹1 H NMR (CDCl₃, 300MHz): δ (ppm) = 7.30-7.35 (m, 1H), 7.43-7.78 (m, 16H), 7.86-7.93 (m, 3H), 8.0 1 (dd, J = 0.9Hz, 7.8Hz, 1H), 8.23 (d, J = 7.8Hz, 1H) ), 8.47 (d, J = 1.5Hz, 1H), 8.74 (d, J = 8.1Hz, 1H), 8.80 (d, J = 7.8Hz, 1H).</p><p num="0268">Also,¹The 1 H NMR charts are shown in FIGS. 12 (A) and 12 (B). Note that Fig. 12 (B) is a diagram. It is a chart showing the expanded range from 7.0ppm to 9.0ppm in 12 (A). To. From the measurement results, it was confirmed that the target product, PCPPn (abbreviation), was obtained.</p><p num="0269">In addition, the absorption spectrum of the toluene solution of PCPPn is shown in FIG. 13 (A), and the emission spectrum is shown. It is shown in FIG. 13 (B). In addition, the absorption spectrum of the thin film of PCPPn is shown in Fig. 14 (A). The spectrum is shown in FIG. 14 (B). Ultraviolet-visible spectrophotometer (Japan) for measurement of absorption spectrum V550 type) manufactured by Spectroscopy Co., Ltd. was used. Fluorometer Co., Ltd. for measuring emission spectrum Hamamatsu Photonics FS920) was used. The solution is placed in a quartz cell and the thin film is steamed on a quartz substrate. I put it on and made a sample and measured it. Absorption spectrum in quartz cell for solution The absorption spectrum measured by adding only toluene, and the spectrum of the quartz substrate for the thin film. The absorption spectrum obtained by subtracting each is shown. In FIGS. 13 and 14, the horizontal axis is the wavelength (n). m), the vertical axis represents the strength (arbitrary unit). In the case of toluene solution, it absorbs around 300 nm A peak was observed, and the maximum emission wavelength was 383 nm (excitation wavelength 300 nm). Also thin In the case of the membrane, an absorption peak is seen near 321 nm, and the maximum emission wavelength is 410 nm (excitation). The wavelength was 331 nm).</p><p num="0270">From the absorption spectrum, PCPPn shown in this example is a material with almost no absorption in the visible region. It turned out that there was. Moreover, from the emission spectrum, it was found that the emission was bluish purple.</p><p num="0271">In addition, the glass transition temperature (Tg) was investigated using a differential scanning calorimetry device (DSC). It was. From the measurement results, the glass transition temperature was 114 ° C. Thus, the high glass transition temperature It showed the degree and was found to have good heat resistance. In addition, peaks representing crystallization were detected. It turned out that it is a substance that is difficult to crystallize.</p>

<p num="0272">In this embodiment, 9-phenyl-3- [4] represented by the structural formula (105) in the first embodiment. -(Triphenylene-2-yl) -Phenyl] -9H-carbazole (abbreviation: PCzPT) An example of manufacturing p) is shown.</p><p num="0273"><chemistry num="45"><img id="000046" he="81" wi="170" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0274">In a 100 mL three-necked flask, 0.5 g (2.0 mmol) of 2-bromotriphenylene, 4- (9-Phenyl-9H-carbazole-3-yl) -Phenylboronic acid 3.3g (9) .2 mmol), palladium (II) acetate 20 mg (0.1 mmol), tri (o-tri) Lu) Phosphine 60 mg (0.2 mmol), toluene 20 mL, ethanol 2 mL, 2 After degassing a 7.5 mL mixture of mol / L potassium carbonate aqueous solution with stirring under reduced pressure. The reaction was carried out by heating and stirring at 85 ° C. for 16 hours under a nitrogen atmosphere.</p><p num="0275">After the reaction, 500 mL of toluene was added to this reaction mixture, and the organic layer of this mixture was floridied. Filtered through all, alumina and Celite. Wash the obtained filtrate with water and use magnesium sulfate. Moisture was adsorbed. This suspension was filtered to obtain a filtrate. Concentrate the obtained filtrate , Purified by silica gel column chromatography. At this time, the chromatograph Toluene was used as the developing solvent for ee. The resulting fraction is concentrated and methanol Was added and ultrasonic waves were applied, and then recrystallized to obtain the desired white powder. The above synthesis method The reaction scheme of is shown in (F3-1) below.</p><p num="0276"><chemistry num="46"><img id="000047" he="112" wi="168" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0277">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex Sun = 10: 10) had 0.21 as the target and 0.46 as 2-bromotriphenylene.</p><p num="0278">In addition, the obtained compound was measured by nuclear magnetic resonance (NMR). The measurement data is shown below. I will.¹1 H NMR (CDCl₃, 300MHz): δ (ppm) = 7.31-7.36 (m, 1H), 7.45-7.53 (m, 4H), 7.61-7.78 (m, 9H), 7.89 -8.01 (m, 5H), 8.24 (d, J = 7.5Hz, 1H), 8.46 (d, J = 1.5Hz, 1H), 8.67-8.82 (m, 5H), 8.95 (d, J = 2.1Hz , 1H).</p><p num="0279">Also,¹The 1 H NMR chart is shown in FIGS. 15 (A) and 15 (B). Note that Fig. 15 (B) is a diagram. It is a chart showing the expanded range from 7.0ppm to 9.5ppm in 15 (A). To. From the measurement results, it was confirmed that the target product, PCzPTp, was obtained.</p><p num="0280">The absorption spectrum of the toluene solution of PCzPTp is shown in Fig. 16 (A). Is shown in FIG. 16 (B). Ultraviolet visible spectrophotometer (JASCO Corporation) for measurement of absorption spectrum Made by the company, V550 type) was used. Fluorometer Co., Ltd. Hamamatsu Hotoni Co., Ltd. for measuring emission spectrum FS920) manufactured by Kusu was used. The solution was placed in a quartz cell for measurement. Absorption spectrum Is the absorption spectrum obtained by subtracting the absorption spectrum measured by putting only toluene in the quartz cell. Is shown. In FIG. 16, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary unit). True In the case of the solution, an absorption peak is seen near 325 nm, and the maximum emission wavelength is 385 nm ( The excitation wavelength was 347 nm.</p><p num="0281">From the absorption spectrum, PCzPTp shown in this example is a material with almost no absorption in the visible region. It turned out that there was. Moreover, from the emission spectrum, it was found that the emission was bluish purple.</p>

<p num="0282">In this embodiment, 3- [3- (9-phena) represented by the structural formula (108) in the first embodiment Toril) -Phenyl] -9-Phenyl-9H-Carbazole (abbreviation: mPCPPn) An example of manufacturing is shown.</p><p num="0283"><chemistry num="47"><img id="000048" he="58" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0284">[Step 1: Synthesis of 3- (3-Bromophenyl) -9-Phenyl-9H-carbazole Law] In a 500 mL three-necked flask, 3-bromoiodobenzene 31 g (110 mmol), 9 -Phenyl-9H-carbazole-3-boronic acid 29g (100 mmol), paradiacetate Umm (II) 22 mg (0.1 mmol), tri (o-tolyl) phosphine 60 mg (1) .2 mmol), 100 mL of toluene, 10 mL of ethanol, 2 mol / L potassium carbonate A mixture of 50 mL of aqueous solution was degassed with stirring under reduced pressure, and then at 80 ° C under a nitrogen atmosphere. The mixture was heated and stirred for 2.5 hours and reacted.</p><p num="0285">After the reaction, 200 mL of toluene was added to this reaction mixture, and this suspension was added to Florisil and Cera. It was filtered through it. Wash the obtained filtrate with water, add magnesium sulfate to absorb water. I dressed it. This suspension was filtered to obtain a filtrate. The obtained filtrate is concentrated, and toluene and methano are added. After applying ultrasonic waves to the powder, it was recrystallized, and the yield of the target white powder was 22 g. It was obtained in a yield of 54%. The reaction scheme of step 1 above is shown in (F4-1) below.</p><p num="0286"><chemistry num="48"><img id="000049" he="97" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0287">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex For sun = 10: 10), the target product was 0.29 and 3-bromoiodobenzene was 0.67.</p><p num="0288">[Step 2: 3- [3- (9-Phenyl) -Phenyl] -9-Phenyl-9H- Synthesis method of carbazole (abbreviation: mPCPPn)] In a 200 mL three-necked flask, 3- (3-bromophenyl) -9-phenyl-9H-cal Bazole 3.0 g (7.5 mmol), phenanthrene-9-boronic acid 1.8 g (8.2) 9 mmol), palladium (II) acetate 19 mg (0.1 mmol), tris (2-methi) Ruphenyl) Phosphine 76 mg (0.2 mmol), toluene 70 mL, ethanol 7 A mixture of mL and 20 mL of a 2 mol / L potassium carbonate aqueous solution is degassed with stirring under reduced pressure. After that, the mixture was heated and stirred at 100 ° C. for 5 hours under a nitrogen atmosphere to react.</p><p num="0289">After the reaction, 500 mL of toluene was added to this reaction mixture, and the organic layer of this mixture was floridied. Filtered through all, alumina and Celite. Wash the obtained filtrate with water and use magnesium sulfate. Moisture was adsorbed. This suspension was filtered to obtain a filtrate. Concentrate the obtained filtrate , Purified by silica gel column chromatography. At this time, the chromatograph Toluene and hexane mixed solvent (toluene: hexane = 2: 3) Was used. The obtained fraction is concentrated, hexane is added, ultrasonic waves are applied, and then reconnection is performed. When crystallized, the target white powder was obtained in a yield of 2.76 g and a yield of 74%. Step 2 above The reaction scheme of is shown in (F4-2) below.</p><p num="0290"><chemistry num="49"><img id="000050" he="95" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0291">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex Sun = 1:10), the target product is 0.25, 3- (3-bromophenyl) -9-phenyl- 9H-carbazole was 0.58.</p><p num="0292">In addition, the obtained compound was measured by nuclear magnetic resonance (NMR). The measurement data is shown below. I will.¹1 H NMR (CDCl₃, 300MHz): δ (ppm) = 7.28-7.32 (m, 1H), 7.42-7.76 (m, 15H), 7.81-7.84 (m, 2H), 7.9 2-7.95 (m, 2H), 8.06 (d, J = 8.1Hz, 1H), 8.18 (d, J) = 7.8Hz, 1H), 8.44 (d, J = 1.5Hz, 1H), 8.76 (d, J = 8) .1Hz, 1H), 8.81 (d, J = 8.7Hz, 1H).</p><p num="0293">Also,¹The 1 H NMR charts are shown in FIGS. 17 (A) and 17 (B). Note that FIG. 17 (B) is a diagram. It is a chart showing the expanded range from 6.5ppm to 9.0ppm in 17 (A). To. From the measurement results, it was confirmed that the target mPCPPn was obtained.</p><p num="0294">The absorption spectrum of the toluene solution of mPCPPn is shown in Fig. 18 (A). Is shown in FIG. 18 (B). In addition, the absorption spectrum of the thin film of mPCPPn is shown in Fig. 19 (A). The emission spectrum is shown in FIG. 19 (B). Ultraviolet-visible spectrophotometer (ultraviolet-visible spectrophotometer) for measurement of absorption spectrum A V550 type manufactured by JASCO Corporation was used. Fluorometer ((( FS920) manufactured by Hamamatsu Photonics Co., Ltd. was used. The solution is placed in a quartz cell, and the thin film is a quartz substrate. A sample was prepared by vapor deposition on the surface and measured. Absorption spectrum is quartz for solution The absorption spectrum measured by adding only toluene to the film, and the spectrum of the quartz substrate for the thin film. The absorption spectrum obtained by subtracting the torr is shown. In FIGS. 18 and 19, the horizontal axis is the wavelength. (nm), vertical axis represents intensity (arbitrary unit). In the case of toluene solution, it absorbs around 298 nm A peak of yield was observed, and the maximum emission wavelength was 363 nm (excitation wavelength 311 nm). Also In the case of a thin film, an absorption peak is seen around 350 nm, and the maximum emission wavelength is 389 nm ( The excitation wavelength was 353 nm).</p><p num="0295">From the absorption spectrum, mPCPPn shown in this example is a material with almost no absorption in the visible region. It turned out to be. Moreover, from the emission spectrum, it was found that the emission was bluish purple.</p><p num="0296">In addition, the glass transition temperature (Tg) was investigated using a differential scanning calorimetry device (DSC). It was. From the measurement results, the glass transition temperature was 109 ° C. Thus, the high glass transition temperature It showed the degree and was found to have good heat resistance. In addition, peaks representing crystallization were detected. It turned out that it is a substance that is difficult to crystallize.</p>

<p num="0297">In this embodiment, 9-phenyl-3- [3-] represented by the structural formula (111) in the first embodiment. (Triphenylene-2-yl) -Phenyl] -9H-carbazole (abbreviation: mPCzPT) An example of manufacturing p) is shown.</p><p num="0298"><chemistry num="50"><img id="000051" he="66" wi="170" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0299">3- (4-Bromophenyl) -9-phenyl-9H-carbazo in a 50 mL three-necked flask 0.7 g (1.8 mmol) of ol and 0.5 g (1.8 mmol) of triphenylene-2-boronic acid mmol), palladium (II) acetate 4.1 mg (18 μmol), tri (o-tolyl) ) Phosphine 28 mg (92 μmol), toluene 6.9 mL, ethanol 2.3 mL , 2 mol / L potassium carbonate aqueous solution 1.9 mL mixture was degassed with stirring under reduced pressure. After that, the mixture was heated and stirred at 80 ° C. for 3 hours in a nitrogen atmosphere to react.</p><p num="0300">After the reaction, the aqueous layer of the obtained suspension was extracted with toluene. The resulting extraction solution and the previous suspension Combine with the organic layer of the solution, wash with saturated brine, and add magnesium sulfate to the obtained solution. Moisture was adsorbed. The suspension was filtered off by natural filtration and the filtrate was concentrated to give an oil. The oil was purified by silica gel column chromatography. Column chromatograph Fee first uses toluene: hexane = 1: 9 as the developing solvent, and then toluene: hexane = This was done by using 1: 6 as the developing solvent. The resulting fraction is concentrated and oily I got something. When toluene and hexane were added to this oil and recrystallized, the target white was obtained. A colored solid was obtained with a yield of 0.9 g and a yield of 90%. The reaction scheme of the above synthesis method is as follows (F5-1) ).</p><p num="0301"><chemistry num="51"><img id="000052" he="94" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0302">In addition, the obtained compound was measured by nuclear magnetic resonance (NMR). The measurement data is shown below. I will.¹1 H NMR (CDCl₃, 300MHz): δ (ppm) = 7.30-7.54 (m, 5H), 7.60-7.80 (m, 12H), 8.01 (dd, J = 8.4Hz, 1.5 Hz, 1H), 8.14 (s, 1H), 8.23 (d, J = 7.8Hz, 1H), 8.4 7 (d, J = 2.1Hz, 1H), 8.67-8.80 (m, 5H), 8.95 (d, J) = 1.5Hz, 1H).</p><p num="0303">Also,¹The 1 H NMR chart is shown in FIGS. 20 (A) and 20 (B). Note that Fig. 20 (B) is a diagram. It is a chart showing the expanded range from 7.0ppm to 9.0ppm in 20 (A). To. From the measurement results, it was confirmed that the target mPCzPTp was obtained.</p><p num="0304">In addition, the absorption spectrum of the toluene solution of mPCzPTp is shown in Fig. 21 (A). This is shown in Fig. 21 (B). In addition, the absorption spectrum of the thin film of mPCzPTp is shown in Fig. 22 (A). The emission spectrum is shown in FIG. 22 (B). Ultraviolet-visible spectrophotometry for measurement of absorption spectrum A meter (manufactured by JASCO Corporation, V550 type) was used. Fluorometer for measuring emission spectrum (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) was used. Put the solution in a quartz cell and the thin film is quartz A sample was prepared by vapor deposition on a substrate and measured. Absorption spectrum is stone for solution The absorption spectrum measured by putting only toluene in the English cell, and the quartz substrate for the thin film. The absorption spectrum after subtracting each spectrum is shown. In FIGS. 21 and 22, the horizontal axis is Wavelength (nm), vertical axis represents intensity (arbitrary unit). Around 290 nm in the case of toluene solution Absorption peak was observed in, and the maximum emission wavelength was 381 nm (excitation wavelength 290 nm). In the case of a thin film, an absorption peak is seen near 277 nm, and the maximum emission wavelength is 397 n. It was m (excitation wavelength 306 nm).</p><p num="0305">From the absorption spectrum, mPCzPTp shown in this example is a material with almost no absorption in the visible region. It turned out to be a fee. In addition, it was found from the emission spectrum that it emits bluish purple light. ..</p>

<p num="0306">In this embodiment, 9- (1-naphthyl) -3 represented by the structural formula (120) in the first embodiment. -Manufactures [4- (1-naphthyl) -phenyl] -9H-carbazole (abbreviation: NCPN) Here is an example of how to do it.</p><p num="0307"><chemistry num="52"><img id="000053" he="67" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0308">[Step 1: Synthesis of 3-bromo-9- (1-naphthyl) -9H-carbazole] In a 200 mL Erlenmeyer flask, 5.9 g of 9- (1-naphthyl) -9H-carbazole ( After dissolving in a mixed solvent of 20 mmol), 50 mL of toluene and 70 mL of ethyl acetate, here Add 3.6 g (20 mmol) of N-bromosuccinimide (abbreviation; NBS) to 36:00 The mixture was stirred at room temperature for a while. After completion of the reaction, the mixture is washed with water and magnesium sulfate is added. Moisture was adsorbed. The suspension was filtered and the resulting filtrate was concentrated and recovered. Target white A colored powder was obtained with a yield of 7.4 g and a yield of 99%. The reaction scheme of step 1 above is described below (F6). Shown in -1).</p><p num="0309"><chemistry num="53"><img id="000054" he="46" wi="141" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0310">[Step 2: 9- (1-naphthyl) -3- [4- (1-naphthyl) -phenyl] -9H -Synthesis of carbazole (abbreviation: NCPN)] 3-Bromo-9- (1-naphthyl) -9H-carbazole in a 200 mL three-necked flask 5.0 g (13 mmol), 4- (1-naphthyl) phenylboronic acid 3.7 g (15 mm) ol), Palladium acetate (II) 34 mg (0.2 mmol), Tris (2-methylfe) Nyl) Phosphine 91 mg (0.3 mmol), toluene 50 mL, ethanol 5 mL, After degassing a mixture of 30 mL of a 2 mol / L potassium carbonate aqueous solution with stirring under reduced pressure. , The mixture was heated and stirred at 100 ° C for 1 hour under a nitrogen atmosphere to react. In addition, 4- (1-Naphuchi Lu) Phenylboronic acid 334 mg (1.35 mmol), palladium (II) acetate 15. 0 mg (0.07 mmol), tris (2-methylphenyl) phosphine 45 mg (0. 15 mmol) was added, and the mixture was heated and stirred at 100 ° C. for 6 hours under a nitrogen atmosphere to react.</p><p num="0311">After the reaction, 500 mL of toluene was added to this reaction mixture, and the organic layer of this mixture was floridied. Filtered through all, alumina and Celite. Wash the obtained filtrate with water and use magnesium sulfate. Moisture was adsorbed. This suspension was filtered to obtain a filtrate. Concentrate the obtained filtrate , Purified by silica gel column chromatography. At this time, the chromatograph Toluene and hexane mixed solvent (toluene: hexane = 1: 4) Was used. The obtained fraction is concentrated, hexane is added, ultrasonic waves are applied, and then reconnection is performed. When crystallized, the target white powder was obtained in a yield of 5.4 g and a yield of 82%. Of step 2 above The reaction scheme is shown below (F6-2).</p><p num="0312"><chemistry num="54"><img id="000055" he="101" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0313">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex Sun = 10), the target product is 0.25, 3-bromo-9- (1-naphthyl) -9H-ca Lubazole was 0.53.</p><p num="0314">In addition, the obtained compound was measured by nuclear magnetic resonance (NMR). The measurement data is shown below. I will.¹1 H NMR (CDCl3,300MHz): δ (ppm) = 7.04 (dd, J = 6. 3Hz, 1.5Hz, 1H), 7.11 (d, J = 8.4Hz, 1H), 7.30-7. 70 (m, 14H), 7.83-7.94 (m, 4H), 8.02-8.07 (m, 3H) ) 8.28 (dd, J = 6.3Hz, 2.4Hz, 1H), 8.52 (d, J = 1.5H) z, 1H).</p><p num="0315">Also,¹The 1 H NMR chart is shown in FIGS. 23 (A) and 23 (B). Note that Fig. 23 (B) is a diagram. It is a chart showing the expanded range from 6.0ppm to 9.0ppm in 23 (A). To. From the measurement results, it was confirmed that the target NCPN was obtained.</p><p num="0316">The absorption spectrum of the toluene solution of NCPN is shown in FIG. 24 (A), and the emission spectrum is shown in FIG. Shown in 24 (B). In addition, the absorption spectrum of the NCPN thin film is shown in Fig. 25 (A). The couture is shown in Figure 25 (B). Ultraviolet visible spectrophotometer (JASCO Corporation) for measurement of absorption spectrum Made by Co., Ltd., V550 type) was used. Fluorometer Co., Ltd. Hamamatsu Co., Ltd. for measuring emission spectrum Photonics FS920) was used. The solution is placed in a quartz cell and the thin film is deposited on a quartz substrate. A sample was prepared and measured. Absorption spectrum torr in quartz cell for solution The absorption spectrum measured by adding only the enzyme, and the spectrum of the quartz substrate for the thin film. The absorption spectrum minus each is shown. In FIGS. 24 and 25, the horizontal axis is the wavelength (nm). , The vertical axis represents the strength (arbitrary unit). In the case of toluene solution, absorption pee around 300 nm The maximum emission wavelength was 388 nm (excitation wavelength 300 nm). Also, of thin film In some cases, an absorption peak is seen near 322 nm, and the maximum emission wavelength is 397 nm (excitation wavelength). It was 328 nm).</p><p num="0317">From the absorption spectrum, the NCPN shown in this example is a material with almost no absorption in the visible region. I found out. Moreover, from the emission spectrum, it was found that the emission was bluish purple.</p>

<p num="0318">In this embodiment, the 3,6-bis- [4- (1) represented by the structural formula (112) in the first embodiment -Naftyl) -Phenyl] -9-Phenyl-9H-carbazole (abbreviation: NP2PC) An example of manufacturing is shown.</p><p num="0319"><chemistry num="55"><img id="000056" he="67" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0320">3,6-Dibromo-9-phenyl-9H-carbazole 2 in a 200 mL three-necked flask .0g (5.0 mmol), 4- (1-naphthyl) phenylboronic acid 2.7g (11mm) ol), palladium (II) acetate 100 mg (0.5 mmol), tri (o-tolyl) e Sphin 41 mg (0.1 mmol), toluene 20 mL, ethanol 2 mL, 2 mol After degassing a mixture of 30 mL of / L potassium carbonate aqueous solution with stirring under reduced pressure, a nitrogen atmosphere The mixture was heated and stirred at 85 ° C for 13 hours under ambient air to react.</p><p num="0321">After the reaction, 150 mL of toluene was added to this reaction mixture, and the organic layer of this mixture was floridied. Filtered through all, alumina and Celite. Wash the obtained filtrate with water and use magnesium sulfate. Moisture was adsorbed. This suspension was filtered to obtain a filtrate. Concentrate the obtained filtrate , Purified by silica gel column chromatography. At this time, the chromatograph Toluene and hexane mixed solvent (toluene: hexane = 1: 4) Was used. The obtained fraction is concentrated, acetone and methanol are added, and ultrasonic waves are applied. After that, when it was recrystallized, the white powder of the target product was obtained in a yield of 2.2 g and a yield of 69%. the above The reaction scheme of the synthetic method is shown in (F7-1) below.</p><p num="0322"><chemistry num="56"><img id="000057" he="114" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0323">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex Sun = 10: 10), the target product is 0.25, 3,6-dibromo-9-phenyl-9H-cal Bazole was 0.58.</p><p num="0324">In addition, the obtained compound was measured by nuclear magnetic resonance (NMR). The measurement data is shown below. I will.¹1 H NMR (CDCl₃, 300MHz): δ (ppm) = 7.45-7.68 (m, 19H), 8.02 (dd, J = 2.1Hz, 9.0Hz, 2H), 7.87-7.95 (m, 8H), 8.05 (d, J = 7.8Hz, 2H) 8.55 (d, J = 1.5Hz, 2H).</p><p num="0325">Also,¹The 1 H NMR chart is shown in FIGS. 26 (A) and 26 (B). Note that Fig. 26 (B) is a diagram. It is a chart showing the expanded range from 7.0ppm to 9.0ppm in 26 (A). To. From the measurement results, it was confirmed that the target product, NP2PC, was obtained.</p><p num="0326">In addition, the absorption spectrum of the toluene solution of NP2PC is shown in Fig. 27 (A), and the emission spectrum is shown. It is shown in FIG. 27 (B). In addition, the absorption spectrum of the thin film of NP2PC is shown in Fig. 28 (A). The spectrum is shown in FIG. 28 (B). Ultraviolet-visible spectrophotometer (Japan) for measurement of absorption spectrum V550 type) manufactured by Spectroscopy Co., Ltd. was used. Fluorometer Co., Ltd. for measuring emission spectrum Hamamatsu Photonics FS920) was used. The solution is placed in a quartz cell and the thin film is steamed on a quartz substrate. I put it on and made a sample and measured it. Absorption spectrum in quartz cell for solution The absorption spectrum measured by adding only toluene, and the spectrum of the quartz substrate for the thin film. The absorption spectrum obtained by subtracting each is shown. In FIGS. 27 and 28, the horizontal axis is the wavelength (n). m), the vertical axis represents the strength (arbitrary unit). In the case of toluene solution, it absorbs around 314 nm A peak was observed, and the maximum emission wavelength was 392 nm (excitation wavelength 310 nm). Also thin In the case of the membrane, an absorption peak is seen near 314 nm, and the maximum emission wavelength is 404 nm (excitation). The wavelength was 315 nm).</p><p num="0327">From the absorption spectrum, the NP2PC shown in this example is a material with almost no absorption in the visible region. It turned out that there was. Moreover, from the emission spectrum, it was found that the emission was bluish purple.</p><p num="0328">In addition, the thermophysical properties were investigated using a differential scanning calorimetry device (DSC). From the measurement result , The melting point was 269 ° C. In addition, no peaks indicating glass transition or crystallization were detected, and the crystals It turned out to be a substance that is difficult to convert.</p>

<p num="0329">In this example, it was synthesized in Example 1 and Example 2, and Examples 4 to 7. For each of the carbazole compounds according to one aspect of the present invention, the maximum coverage in the thin film state. Occupied orbital level (HOMO level), lowest empty orbital level (LUMO level) and bandgap ( The result of measuring Bg) is shown.</p><p num="0330">In this example, the measurement was performed as follows. The value of the HOMO level is the light in the atmosphere The value of the ionization potential measured by electron spectroscopy (manufactured by RIKEN Keiki Co., Ltd., AC-2) is a negative value. Obtained by converting to. In addition, the LUMO level values are thin as shown in the above examples. Using the data of the absorption spectrum of the membrane, the absorption edge is calculated from the Tauc plot assuming a direct transition. To find and add the absorption edge to the HOMO level value as an optical energy gap. Got more.</p><p num="0331">PCPN, PCPPn, mPCPPn, mPCzPTp, NCPN obtained by measurement , And the HOMO and LUMO levels of NP2PC are shown in Table 1 below.</p><p num="0332"><tables num="1"><img id="000058" he="39" wi="121" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0333">From Table 1, PCPN, PCPPn, m, which are carbazole compounds according to one aspect of the present invention. PCPPn, mPCzPTp, NCPN, and NP2PC have relatively deep HOMO levels. It was confirmed that it had a shallow LUMO level and a wide bandgap.</p>

<p num="0334">In this embodiment, the manufacturing method of the light emitting device according to the present invention and the measurement results of the device characteristics are compared. It is shown together with the measurement result of the light emitting element.</p><p num="0335">Below, FIG. 29 shows a method for manufacturing the light emitting element 1, the light emitting element 2, and the comparative light emitting element 1 of this embodiment. Will be described with reference to. The structural formulas of the organic compounds used in this example are shown below.</p><p num="0336"><chemistry num="57"><img id="000059" he="128" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0337">(Light emitting element 1) First, indium tin oxide (ITSO) containing silicon oxide is sprinkled on the glass substrate 1100. A film was formed by the tattering method to form the first electrode 1101. The film thickness is 110 nm. The electrode area was 2 mm × 2 mm. In this embodiment, the first electrode 1101 is positive. Used as a pole.</p><p num="0338">Next, the first electrode 1101 is shaped so that the surface on which the first electrode 1101 is formed faces downward. The formed substrate 1100 is fixed to the substrate holder provided in the vacuum vapor deposition apparatus, and 10^-4P After depressurizing to about a, 3- [4- (1) synthesized in Example 1 was placed on the first electrode 1101. -Naftyl) -Phenyl] -9-Phenyl-9H-carbazole (abbreviation: PCPN) and acid The hole injection layer 1111 was formed by co-depositing molybdenum (VI). The film thickness is , 50 nm, and the ratio of PCPN to molybdenum oxide (VI) is 4: 2 by weight (= PC) PN: molybdenum oxide) was adjusted. The co-deposited method is in one processing room. , A vapor deposition method in which vapor deposition is performed simultaneously from a plurality of evaporation sources.</p><p num="0339">Next, PCPN was formed on the hole injection layer 1111 so as to have a film thickness of 10 nm, and the holes were transplanted. A feed layer 1112 was formed.</p><p num="0340">In addition, 9- [4- (N-carbazolyl) phenyl] -10-phenylanthracene (abbreviation) Name: CzPA), and N, N'-bis [4- (9-Phenyl-9H-Fluorene-9-a) Le) Phenyl] -N, N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6FLP) APrn) was co-deposited to form a light emitting layer 1113 on the hole transport layer 1112. Where C The weight ratio of zPA and 1,6FLPA Prn is 1: 0.05 (= CzPA: 1,6FLP) It was adjusted to be APrn). The film thickness of the light emitting layer 1113 was set to 30 nm.</p><p num="0341">Next, CzPA was formed on the light emitting layer 1113 so as to have a film thickness of 10 nm, and the first electron transfer was performed. A feed layer 1114a was formed.</p><p num="0342">After that, bassophenanthroline (abbreviation: BPhen) was placed on the first electron transport layer 1114a. A second electron transport layer 1114b was formed by forming a film so as to have a film thickness of 15 nm.</p><p num="0343">In addition, lithium fluoride (LiF) was applied on the second electron transport layer 1114b with a film thickness of 1 nm. It was vapor-deposited to form an electron injection layer 1115.</p><p num="0344">Finally, a 200 nm film of aluminum as a second electrode 1103 that acts as a cathode. The light emitting element 1 of this embodiment was produced by thin-film deposition so as to be thick.</p><p num="0345">In the above-mentioned vapor deposition process, the resistance heating method was used for all the vapor deposition.</p><p num="0346">(Light emitting element 2) The light emitting element 2 is the same as the above-mentioned light emitting element 1 except for the hole injection layer 1111 and the hole transport layer 1112. Formed in the same way.</p><p num="0347">In the light emitting element 2, the hole injection layer 1111 is mounted on the first electrode 1101 in the second embodiment. Formed 3- [4- (9-Phenyl) -Phenyl] -9-Phenyl-9H-Carbazo It was formed by co-depositing all (abbreviation: PCPPn) and molybdenum oxide (VI). That The film thickness is 50 nm, and the ratio of PCPPn to molybdenum oxide (VI) is 4: 2 by weight. It was adjusted to (= PCPPn: molybdenum oxide).</p><p num="0348">Next, PCPPn was formed on the hole injection layer 1111 so as to have a film thickness of 10 nm, and holes were formed. A transport layer 1112 was formed.</p><p num="0349">(Comparative light emitting element 1) The comparative light emitting device 1 is the above-mentioned light emitting device except for the hole injection layer 1111 and the hole transport layer 1112. Formed in the same way as 1.</p><p num="0350">In the comparative light emitting device 1, the hole injection layer 1111 is placed on the first electrode 1101 with 9- [4- (9-Phenylcarbazole-3-yl) Phenyl] -10-Phenylanthracene (abbreviation) Name: PCzPA) and molybdenum oxide (VI) were co-deposited. The film thickness is At 50 nm, the ratio of PCzPA to molybdenum oxide (VI) is 4: 2 by weight (= PC). zPA: Molybdenum oxide) was adjusted.</p><p num="0351">Next, PCzPA was formed on the hole injection layer 1111 so as to have a film thickness of 10 nm, and holes were formed. A transport layer 1112 was formed.</p><p num="0352">Table 2 shows the element structures of the light emitting element 1, the light emitting element 2, and the comparative light emitting element 1 obtained as described above. ..</p><p num="0353"><tables num="2"><img id="000060" he="58" wi="146" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0354">Place the light emitting element 1, the light emitting element 2 and the comparative light emitting element 1 in a glove box having a nitrogen atmosphere. After performing the work of sealing the light emitting elements so that they are not exposed to the atmosphere, each light emitting element The operating characteristics were measured. The measurement was performed at room temperature (atmosphere maintained at 25 ° C). ..</p><p num="0355">The light emitting element 1, the light emitting element 2, and the comparative light emitting element 1 were formed on the same substrate. Also, In the above three light emitting elements, except for the hole injection layer and the hole transport layer, they are formed at the same time and have operational characteristics. The measurements are being performed at the same time.</p><p num="0356">In the light emitting element 1, the light emitting element 2, and the comparative light emitting element 1, the brightness is 1000 cd / m.²Near time Voltage (V), current density (mA / cm)²), CIE chromatic coordinates (x, y), brightness, (cd / m²), Current efficiency (cd / A), Power efficiency (lm / W), External quantum efficiency (%) in Table 3. Shown.</p><p num="0357"><tables num="3"><img id="000061" he="27" wi="142" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0358">The emission spectra of the light emitting element 1, the light emitting element 2, and the comparative light emitting element 1 are shown in FIG. Figure 30 The horizontal axis represents the wavelength (nm) and the vertical axis represents the emission intensity (arbitrary unit). Also, the light emitting element 1 , The voltage-luminance characteristics of the light emitting element 2 and the comparative light emitting element 1 are shown in Fig. 31, and the brightness-current efficiency characteristics are shown in Fig. 3. 2. The brightness-power efficiency characteristics are shown in Fig. 33, respectively. In Fig. 31, the vertical axis is the brightness (cd / m).²), Voltage (V) is shown on the horizontal axis, current efficiency (cd / A) is shown on the vertical axis, and brightness (brightness) is shown on the horizontal axis in FIG. cd / m²) Is shown. In Fig. 33, the vertical axis is power efficiency (lm / W) and the horizontal axis is brightness (c). d / m²) Is shown.</p><p num="0359">From FIG. 30, the emission spectra of the light emitting element 1, the light emitting element 2, and the comparative light emitting element 1 are all shown. It has a peak near 470 nm. Also, from the CIE chromaticity coordinates in Table 3, the light emitting element 1 , Light emitting element 2 and comparative light emitting element 1 are observed to emit blue light derived from 1,6 FLPA Prn. It was found that all the elements had a good carrier balance.</p><p num="0360">Further, from FIGS. 31 to 33 and Table 3, the light emitting element 1 and the light emitting element 2 are compared with each other. It is a light emitting element that can be driven at the same low voltage as the above and has higher efficiency than the comparative light emitting element 1. I understood it.</p><p num="0361">This is because the band gap of PCzPA used for the comparative light emitting element 1 is 2.92 eV. Energy transfer from the light emitting layer when used as a hole transport layer in contact with the light emitting layer (live in the light emitting layer) The movement of excitons formed) can occur, whereas the holes in the light emitting element 1 and the light emitting element 2 of this embodiment can occur. The PCPN and PCPPn applied to the injection layer and the hole transport layer have band gaps, respectively. Is as wide as 3.48eV and 3.53eV, so energy transfer from the light emitting layer is unlikely to occur. It is thought that this is the case.</p><p num="0362">The LUMO level of PCzPA is -2.77eV, which is due to electron leakage from the light emitting layer. Carrier loss can occur, whereas PCPN and PCPPn are LUMO quasi, respectively. Since the position is shallow at -2.29eV and -2.25eV, electron leakage from the light emitting layer is unlikely to occur. .. Therefore, it is considered that high efficiency was obtained in the light emitting element 1 and the light emitting element 2. Also, PC The HOMO level of zPA is -5.69 eV, which is the host material of the adjacent light emitting layer, Cz. It is equivalent to the PA HOMO level of -5.70 eV and has good hole injection properties. PCP N and PCPPn also had deep HOMO levels of -5.77eV and -5.78eV, respectively. Therefore, the hole injection property is also good. In addition, all the elements have the same low drive voltage. Therefore, it was found that the carrier movement was good in all the elements.</p><p num="0363">PCzPA is one of the materials with excellent hole transportability and long life.</p><p num="0364">Moreover, the reliability test of the manufactured light emitting element 1, light emitting element 2 and comparative light emitting element 1 was performed. Trust In the sex test, the initial brightness was 5000 cd / m.²Set to these elements under constant current density conditions The brightness was measured after a certain period of time. The results obtained by the reliability test It is shown in FIG. In FIG. 34, the horizontal axis is the energization time (hour), and the vertical axis is each time. It represents the ratio of brightness to initial brightness, that is, normalized brightness (%).</p><p num="0365">From FIG. 34, the light emitting element 1, the light emitting element 2, and the comparative light emitting element 1 have the same brightness over time. It can be seen that the decrease is unlikely to occur and the life is long. Light emitting element 1, light emitting element 2 and comparative firing The optical element maintained a brightness of 52% of the initial brightness even after being driven for 210 hours.</p><p num="0366">Based on the above, the carbazole compound according to one aspect of the present invention can be used for the hole injection layer and the hole transport layer. It was shown that an element with high luminous efficiency can be realized. This is the carba of one aspect of the invention The LUMO level of the sol compound is sufficiently shallow, and the escape of electrons from the light emitting layer is suppressed. it is conceivable that. In addition, the HOMO level was sufficiently deep, and the hole injection property into the light emitting layer was good. It is thought that this is the case. In addition, the bandgap is wide enough and the efficiency due to the energy transfer of excitons It is considered that the decrease was suppressed.</p><p num="0367">Further, by using the carbazole compound of one aspect of the present invention in the hole injection layer and the hole transport layer, It was shown that a light emitting device with a low drive voltage can be realized.</p><p num="0368">Further, by using the carbazole compound of one aspect of the present invention in the hole injection layer and the hole transport layer, It has been shown that a long-life light emitting device can be realized.</p>

<p num="0369">In this embodiment, the manufacturing method of the light emitting device according to the present invention and the measurement results of the device characteristics are compared. It is shown together with the measurement result of the light emitting element.</p><p num="0370">Hereinafter, a method for manufacturing the light emitting element 3, the light emitting element 4, and the comparative light emitting element 2 of this embodiment will be described. .. The element structure of the light emitting device produced in this embodiment is the same as that in FIG. 29. In addition, this implementation Since the organic compound used in the example is the same as in Example 9, the description is omitted.</p><p num="0371">(Light emitting element 3) The light emitting device 3 is the light emitting device of Example 9 except for the hole injection layer 1111 and the hole transport layer 1112. Formed in the same way as 1.</p><p num="0372">In the light emitting element 3, the hole injection layer 1111 is placed on the first electrode 1101 with molybdenum oxide. The hole injection layer 1111 was formed by depositing (VI) with a film thickness of 10 nm.</p><p num="0373">Next, the PCPN synthesized in Example 1 has a film thickness of 30 nm on the hole injection layer 1111. The hole transport layer 1112 was formed by forming a film.</p><p num="0374">(Light emitting element 4) The light emitting element 4 was formed in the same manner as the light emitting element 3 except for the hole transport layer 1112.</p><p num="0375">In the light emitting device 4, the hole transport layer 1112 contains the PCPPn synthesized in Example 2 at 30 nm. The film was formed so as to have the same film thickness as.</p><p num="0376">(Comparative light emitting element 2) The comparative light emitting device 2 was formed in the same manner as the light emitting device 3 except for the hole transport layer 1112.</p><p num="0377">In the comparative light emitting device 2, the hole transport layer 1112 has a PCzPA film thickness of 30 nm. The film was formed.</p><p num="0378">Table 4 shows the element structures of the light emitting element 3, the light emitting element 4, and the comparative light emitting element 2 obtained as described above. ..</p><p num="0379"><tables num="4"><img id="000062" he="60" wi="151" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0380">Place the light emitting element 3, the light emitting element 4, and the comparative light emitting element 2 in a glove box having a nitrogen atmosphere. After performing the work of sealing the light emitting elements so that they are not exposed to the atmosphere, each light emitting element The operating characteristics were measured. The measurement was performed at room temperature (atmosphere maintained at 25 ° C). ..</p><p num="0381">The light emitting element 3, the light emitting element 4, and the comparative light emitting element 2 were formed on the same substrate. Also above In the above three light emitting elements, except for the hole transport layer, they are formed at the same time, and the measurement of operating characteristics is performed at the same time. I'm working on it.</p><p num="0382">In the light emitting element 3, the light emitting element 4, and the comparative light emitting element 2, the brightness is 1000 cd / m.²Near time Voltage (V), current density (mA / cm)²), CIE chromatic coordinates (x, y), brightness, (cd / m²), Current efficiency (cd / A), Power efficiency (lm / W), External quantum efficiency (%) in Table 5. Shown.</p><p num="0383"><tables num="5"><img id="000063" he="28" wi="142" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0384">The emission spectra of the light emitting element 3, the light emitting element 4, and the comparative light emitting element 2 are shown in FIG. 35. Figure 35 The horizontal axis represents the wavelength (nm) and the vertical axis represents the emission intensity (arbitrary unit). In addition, the light emitting element 3 , The voltage-luminance characteristics of the light emitting element 4 and the comparative light emitting element 2 are shown in Fig. 36, and the brightness-current efficiency characteristics are shown in Fig. 3. 7. Luminance-power efficiency characteristics are shown in Fig. 38, respectively. In Fig. 36, the vertical axis is the brightness (cd / m).²), Voltage (V) is shown on the horizontal axis, current efficiency (cd / A) is shown on the vertical axis, and brightness (brightness) is shown on the horizontal axis in FIG. 37. cd / m²) Is shown. In Fig. 38, the vertical axis is power efficiency (lm / W) and the horizontal axis is brightness (c). d / m²) Is shown.</p><p num="0385">From FIG. 35, the emission spectra of the light emitting element 3, the light emitting element 4, and the comparative light emitting element 2 are all shown. It has a peak near 470 nm. Also, from the CIE chromaticity coordinates in Table 5, the light emitting element 3 , Light emitting element 4 and comparative light emitting element 2 are observed to emit blue light derived from 1,6 FLPA Prn. It was found that all the elements had a good carrier balance.</p><p num="0386">Further, from FIGS. 36 to 38 and Table 5, the light emitting element 3 and the light emitting element 4 are compared with each other. It was found to be a more efficient light emitting device. This is the PCz used for the comparative light emitting element 2. Applicable to the hole transport layer of the light emitting element 3 and the light emitting element 4 of this embodiment rather than the band gap of PA. The bandgap of PCPN and PCPPn is wide, and energy transfer from the light emitting layer is possible. It is thought that it is unlikely to occur. Also, the LUMO levels of PCPN and PCPPn are shallow enough. , It is probable that the loss of electrons was suppressed.</p><p num="0387">Moreover, the reliability test of the manufactured light emitting element 3, light emitting element 4, and comparative light emitting element 2 was performed. Trust In the sex test, the initial brightness was 5000 cd / m.²Set to these elements under constant current density conditions The brightness was measured after a certain period of time. The results obtained by the reliability test It is shown in FIG. In FIG. 39, the horizontal axis is the energization time (hour), and the vertical axis is each time. It represents the ratio of brightness to initial brightness, that is, normalized brightness (%).</p><p num="0388">From FIG. 39, the light emitting element 3, the light emitting element 4, and the comparative light emitting element 2 have the same brightness over time. It can be seen that the decrease is unlikely to occur and the life is long. The light emitting element 3 is driven for 150 hours. However, the brightness of 60% of the initial brightness is maintained, and the light emitting element 4 has the initial brightness even after being driven for 150 hours. The brightness of the comparative light emitting element 2 is maintained at 56%, and the brightness of the comparative light emitting element 2 is 54% of the initial brightness even after being driven for 150 hours. I kept the degree.</p><p num="0389">In this example, a single film of molybdenum oxide is used as the hole injection layer, and the force of one aspect of the present invention is used. Compared with Example 9 in which a mixed material of a rubazole compound and molybdenum oxide was used as a hole injection layer. In comparison, the drive voltage increased slightly as a whole. From this, the carbazo according to one aspect of the present invention. When a mixed material of a compound and molybdenum oxide is used as the hole injection layer, the hole injection property becomes higher. It was suggested that a good device was obtained.</p><p num="0390">Based on the above, the carbazole compound according to one aspect of the present invention can be used for the hole injection layer and the hole transport layer. It was shown that an element with high luminous efficiency can be realized. This is the carba of one aspect of the invention The LUMO level of the sol compound is sufficiently shallow, and the escape of electrons from the light emitting layer is suppressed. it is conceivable that. In addition, the HOMO level was sufficiently deep, and the hole injection property into the light emitting layer was good. It is thought that this is the case. In addition, the bandgap is wide enough and the efficiency due to the energy transfer of excitons It is probable that the decrease was suppressed.</p><p num="0391">Further, by using the carbazole compound of one aspect of the present invention in the hole injection layer and the hole transport layer, It has been shown that a long-life light emitting device can be realized.</p><p num="0392">In addition, good characteristics can be obtained even in a light emitting device in which the hole injection layer is a single layer of molybdenum oxide. It was shown to be. By forming the hole injection layer with a composite material, the anode film It is more preferable because it can prevent a short circuit of the light emitting element due to quality.</p>

<p num="0393">In this embodiment, the manufacturing method of the light emitting device according to the present invention and the measurement results of the device characteristics are compared. It is shown together with the measurement result of the light emitting element.</p><p num="0394">The manufacturing method of the light emitting element 5 and the comparative light emitting element 3 of this embodiment will be described below. In addition, the real The element structure of the light emitting device produced in the example is the same as that in FIG. 29. In addition, the presence used in this example Since the machine compound is the same as in Example 9, the description thereof will be omitted.</p><p num="0395">(Light emitting element 5) The light emitting device 5 is the light emitting device of Example 9 except for the hole injection layer 1111 and the hole transport layer 1112. Formed in the same way as 1.</p><p num="0396">In the light emitting device 5, the hole injection layer 1111 is mounted on the first electrode 1101 in the sixth embodiment. Formed 9- (1-naphthyl) -3- [4- (1-naphthyl) -phenyl] -9H-carba It was formed by co-depositing sol (abbreviation: NCPN) and molybdenum oxide (VI). That The film thickness is 50 nm, and the ratio of NCPN to molybdenum oxide (VI) is 4: 2 by weight ( = NCPN: molybdenum oxide).</p><p num="0397">Next, NCPN was formed on the hole injection layer 1111 so as to have a film thickness of 10 nm, and the holes were transplanted. A feed layer 1112 was formed.</p><p num="0398">(Comparative light emitting element 3) The comparative light emitting element 3 in this embodiment has the same configuration as the comparative light emitting element 1 in the ninth embodiment. It was.</p><p num="0399">Table 6 shows the element structures of the light emitting element 5 and the comparative light emitting element 3 obtained as described above.</p><p num="0400"><tables num="6"><img id="000064" he="46" wi="144" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0401">The light emitting element 5 and the comparative light emitting element 3 are placed in a glove box having a nitrogen atmosphere. After performing the work of sealing so that it is not exposed to the atmosphere, the operating characteristics of each light emitting element I made a measurement. The measurement was performed at room temperature (atmosphere maintained at 25 ° C).</p><p num="0402">The light emitting element 5 and the comparative light emitting element 3 were formed on the same substrate. In addition, the above two light emission In the device, except for the hole injection layer and the hole transport layer, they are formed at the same time, and the operation characteristics are measured at the same time. You are operating.</p><p num="0403">In the light emitting element 5 and the comparative light emitting element 3, the brightness is 1000 cd / m.²Voltage in the vicinity (V) , Current density (mA / cm)²), CIE chromaticity coordinates (x, y), brightness, (cd / m)²), Current Table 7 shows efficiency (cd / A), power efficiency (lm / W), and external quantum efficiency (%).</p><p num="0404"><tables num="7"><img id="000065" he="24" wi="139" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0405">The emission spectra of the light emitting element 5 and the comparative light emitting element 3 are shown in FIG. In FIG. 40, horizontal The axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In addition, the light emitting element 5 and the comparative light emission The voltage-luminance characteristic of element 3 is shown in Fig. 41, the brightness-current efficiency characteristic is shown in Fig. 42, and the brightness-power efficiency characteristic is shown in Fig. 42. Are shown in FIG. 43, respectively. In Fig. 41, the vertical axis is the brightness (cd / m).²), Voltage (V) is shown on the horizontal axis However, in Fig. 42, the vertical axis is current efficiency (cd / A) and the horizontal axis is brightness (cd / m).²) Is shown. Also , In Fig. 43, the vertical axis is power efficiency (lm / W) and the horizontal axis is brightness (cd / m).²) Is shown.</p><p num="0406">From FIG. 40, the emission spectra of the light emitting element 5 and the comparative light emitting element 3 are both with 470 nm. It has a peak nearby. Also, from the CIE chromaticity coordinates in Table 7, the light emitting element 5 and comparative light emission Blue light emission derived from 1,6 FLPA Prn was observed in element 3, and all elements were carried. It turned out that the balance was good.</p><p num="0407">Further, from FIGS. 41 to 43 and Table 7, the light emitting element 5 has higher efficiency than the comparative light emitting element 3. It turned out to be a light emitting element. This is the bandgi of PCzPA used for the comparative light emitting element 3. The NCPN applied to the hole injection layer and hole transport layer of the light emitting device 5 of this example rather than the cap. This is thought to be because the band gap is wide and energy transfer from the light emitting layer is unlikely to occur. Well In addition, it is considered that the LUMO level of NCPN was sufficiently shallow and the electron escape was suppressed.</p><p num="0408">Further, from FIGS. 41 to 43 and Table 7, the light emitting element 5 and the comparative light emitting element 3 are driven by a low voltage. It turned out to be movable.</p><p num="0409">Moreover, the reliability test of the manufactured light emitting element 5 and the comparative light emitting element 3 was performed. Reliability test is the first Periodic brightness 5000 cd / m²Set to, and drive these elements under constant current density conditions, or The brightness was measured every time the time passed. The results obtained by the reliability test are shown in FIG. .. In FIG. 44, the horizontal axis is the energization time (hour), and the vertical axis is the initial brightness at each time. It represents the ratio of brightness to degree, that is, normalized brightness (%).</p><p num="0410">From FIG. 44, the light emitting element 5 and the comparative light emitting element 3 are less likely to decrease in brightness with the passage of time. , It turns out that it has a long life. The light emitting element 5 is 62% of the initial brightness even after being driven for 130 hours. The comparative light emitting element 3 maintains the brightness of 57% of the initial brightness even after being driven for 130 hours. Was.</p><p num="0411">Based on the above, the carbazole compound according to one aspect of the present invention can be used for the hole injection layer and the hole transport layer. It was shown that an element with high luminous efficiency can be realized. This is the carba of one aspect of the invention The LUMO level of the sol compound is sufficiently shallow, and the escape of electrons from the light emitting layer is suppressed. it is conceivable that. In addition, the HOMO level was sufficiently deep, and the hole injection property into the light emitting layer was good. It is thought that this is the case. In addition, the bandgap is wide enough and the efficiency due to the energy transfer of excitons It is probable that the decrease was suppressed.</p><p num="0412">Further, by using the carbazole compound of one aspect of the present invention in the hole injection layer and the hole transport layer, It was shown that a light emitting device with a low drive voltage can be realized.</p><p num="0413">Further, by using the carbazole compound of one aspect of the present invention in the hole injection layer and the hole transport layer, It has been shown that a long-life light emitting device can be realized.</p>

<p num="0414">In this embodiment, the manufacturing method of the light emitting device according to the present invention and the measurement results of the device characteristics are compared. It is shown together with the measurement result of the light emitting element.</p><p num="0415">The manufacturing method of the light emitting element 6 and the comparative light emitting element 4 of this embodiment will be described below. In addition, the real The element structure of the light emitting device produced in the example is the same as that in FIG. 29. In addition, the presence used in this example Since the machine compound is the same as in Example 9, the description thereof will be omitted.</p><p num="0416">(Light emitting element 6) The light emitting device 6 is the light emitting device of Example 9 except for the hole injection layer 1111 and the hole transport layer 1112. Formed in the same way as 1.</p><p num="0417">In the light emitting element 6, the hole injection layer 1111 is mounted on the first electrode 1101 in the seventh embodiment. Formed 3,6-bis- [4- (1-naphthyl) -phenyl] -9-phenyl-9H-cal It was formed by co-depositing bazole (abbreviation: NP2PC) and molybdenum oxide (VI). The film thickness is 50 nm, and the ratio of NP2PC to molybdenum oxide (VI) is 4 by weight. It was adjusted to be: 2 (= NP2PC: molybdenum oxide).</p><p num="0418">Next, NP2PC was formed on the hole injection layer 1111 so as to have a film thickness of 10 nm, and holes were formed. A transport layer 1112 was formed.</p><p num="0419">(Comparative light emitting element 4) The comparative light emitting element 4 in this embodiment has the same configuration as the comparative light emitting element 1 in the ninth embodiment. It was.</p><p num="0420">Table 8 shows the element structures of the light emitting element 6 and the comparative light emitting element 4 obtained as described above.</p><p num="0421"><tables num="8"><img id="000066" he="49" wi="150" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0422">The light emitting element 6 and the comparative light emitting element 4 are placed in a glove box having a nitrogen atmosphere. After performing the work of sealing so that it is not exposed to the atmosphere, the operating characteristics of each light emitting element I made a measurement. The measurement was performed at room temperature (atmosphere maintained at 25 ° C).</p><p num="0423">The light emitting element 6 and the comparative light emitting element 4 were formed on the same substrate. In addition, the above two light emission In the device, except for the hole injection layer and the hole transport layer, they are formed at the same time, and the operation characteristics are measured at the same time. You are operating.</p><p num="0424">In the light emitting element 6 and the comparative light emitting element 4, the brightness is 1000 cd / m.²Voltage in the vicinity (V) , Current density (mA / cm)²), CIE chromaticity coordinates (x, y), brightness, (cd / m)²), Current Table 9 shows efficiency (cd / A), power efficiency (lm / W), and external quantum efficiency (%).</p><p num="0425"><tables num="9"><img id="000067" he="24" wi="141" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0426">The emission spectra of the light emitting element 6 and the comparative light emitting element 4 are shown in FIG. 45. In FIG. 45, horizontal The axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In addition, the light emitting element 6 and comparative light emission The voltage-luminance characteristic of element 4 is shown in Fig. 46, the brightness-current efficiency characteristic is shown in Fig. 47, and the brightness-power efficiency characteristic is shown in Fig. 47. Are shown in FIG. 48, respectively. In Fig. 46, the vertical axis is the brightness (cd / m).²), Voltage (V) is shown on the horizontal axis However, in Fig. 47, the vertical axis is current efficiency (cd / A) and the horizontal axis is brightness (cd / m).²) Is shown. Also , In Fig. 48, the vertical axis is power efficiency (lm / W) and the horizontal axis is brightness (cd / m).²) Is shown.</p><p num="0427">From FIG. 45, the emission spectra of the light emitting element 6 and the comparative light emitting element 4 are both with 470 nm. It has a peak nearby. Also, from the CIE chromaticity coordinates in Table 9, the light emitting element 6 and comparative light emission Blue light emission derived from 1,6 FLPA Prn was observed in element 4, and all elements were carried. It turned out that the balance was good.</p><p num="0428">Further, from FIGS. 46 to 48 and Table 9, the light emitting element 6 has higher efficiency than the comparative light emitting element 4. It turned out to be a light emitting element. This is the bandgi of PCzPA used for the comparative light emitting element 4. NP2PC applied to the hole injection layer and hole transport layer of the light emitting device 6 of this example rather than the cap. It is considered that this is because the band gap is wide and energy transfer from the light emitting layer is unlikely to occur. It is also probable that the LUMO level of NP2PC was sufficiently shallow to suppress the loss of electrons. ..</p><p num="0429">Further, from FIGS. 46 to 48 and Table 9, the light emitting element 6 and the comparative light emitting element 4 are driven by a low voltage. It turned out to be movable.</p><p num="0430">Moreover, the reliability test of the manufactured light emitting element 6 and the comparative light emitting element 4 was performed. Reliability test is the first Periodic brightness 5000 cd / m²Set to, and drive these elements under constant current density conditions, or The brightness was measured every time the time passed. The results obtained by the reliability test are shown in Fig. 49. .. In FIG. 49, the horizontal axis is the energization time (hour), and the vertical axis is the initial brightness at each time. It represents the ratio of brightness to degree, that is, normalized brightness (%).</p><p num="0431">From FIG. 49, the light emitting element 6 and the comparative light emitting element 4 are less likely to decrease in brightness with the passage of time. , It turns out that it has a long life. The light emitting element 6 is 63% of the initial brightness even after being driven for 130 hours. The comparative light emitting element 4 maintains the brightness of 57% of the initial brightness even after being driven for 130 hours. Was.</p><p num="0432">Based on the above, the carbazole compound according to one aspect of the present invention can be used for the hole injection layer and the hole transport layer. It was shown that an element with high luminous efficiency can be realized. This is the carba of one aspect of the invention The LUMO level of the sol compound is sufficiently shallow, and the escape of electrons from the light emitting layer is suppressed. it is conceivable that. In addition, the HOMO level was sufficiently deep, and the hole injection property into the light emitting layer was good. It is thought that this is the case. In addition, the bandgap is wide enough and the efficiency due to the energy transfer of excitons It is probable that the decrease was suppressed.</p><p num="0433">Further, by using the carbazole compound of one aspect of the present invention in the hole injection layer and the hole transport layer, It was shown that a light emitting device with a low drive voltage can be realized.</p><p num="0434">Further, by using the carbazole compound of one aspect of the present invention in the hole injection layer and the hole transport layer, It has been shown that a long-life light emitting device can be realized.</p>

<p num="0435">In this embodiment, the manufacturing method of the light emitting device according to the present invention and the measurement results of the device characteristics are compared. It is shown together with the measurement result of the light emitting element.</p><p num="0436">The manufacturing method of the light emitting element 7 and the comparative light emitting element 5 of this embodiment will be described below. In addition, this implementation The element structure of the light emitting device produced in the example is the same as that in FIG. 29. In addition, the organic used in this example Since the compound is the same as in Example 9, the description is omitted.</p><p num="0437">(Light emitting element 7) The light emitting device 7 is the light emitting device of Example 9 except for the hole injection layer 1111 and the hole transport layer 1112. Formed in the same way as 1.</p><p num="0438">In the light emitting element 7, the hole injection layer 1111 is mounted on the first electrode 1101 in the fourth embodiment. Formed 3- [3- (9-Phenyl) -Phenyl] -9-Phenyl-9H-Carbazo It was formed by co-depositing all (abbreviation: mPCPPn) and molybdenum oxide (VI). So The film thickness is 50 nm, and the ratio of mPCPPn to molybdenum oxide (VI) is 4 by weight. It was adjusted to: 2 (= mPCPPn: molybdenum oxide).</p><p num="0439">Next, mPCPPn was formed on the hole injection layer 1111 so as to have a film thickness of 10 nm. A pore transport layer 1112 was formed.</p><p num="0440">(Comparative light emitting element 5) The comparative light emitting element 5 in this embodiment has the same configuration as the comparative light emitting element 1 in the ninth embodiment. It was.</p><p num="0441">Table 10 shows the element structures of the light emitting element 7 and the comparative light emitting element 5 obtained as described above.</p><p num="0442"><tables num="10"><img id="000068" he="47" wi="146" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0443">The light emitting element 7 and the comparative light emitting element 5 are placed in a glove box having a nitrogen atmosphere. After performing the work of sealing so that it is not exposed to the atmosphere, the operating characteristics of each light emitting element I made a measurement. The measurement was performed at room temperature (atmosphere maintained at 25 ° C).</p><p num="0444">The light emitting element 7 and the comparative light emitting element 5 were formed on the same substrate. In addition, the above two light emission In the device, except for the hole injection layer and the hole transport layer, they are formed at the same time, and the operation characteristics are measured at the same time. You are operating.</p><p num="0445">In the light emitting element 7 and the comparative light emitting element 5, the brightness is 1000 cd / m.²Voltage in the vicinity (V) , Current density (mA / cm)²), CIE chromaticity coordinates (x, y), brightness, (cd / m)²), Current Table 11 shows efficiency (cd / A), power efficiency (lm / W), and external quantum efficiency (%).</p><p num="0446"><tables num="11"><img id="000069" he="25" wi="142" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0447">The emission spectra of the light emitting element 7 and the comparative light emitting element 5 are shown in FIG. In FIG. 50, horizontal The axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In addition, the light emitting element 7 and comparative light emission The voltage-luminance characteristic of element 5 is shown in Fig. 51, the brightness-current efficiency characteristic is shown in Fig. 52, and the brightness-power efficiency characteristic is shown in Fig. 52. Are shown in FIG. 53, respectively. In Fig. 51, the vertical axis is the brightness (cd / m).²), Voltage (V) is shown on the horizontal axis However, in FIG. 52, the vertical axis is the current efficiency (cd / A) and the horizontal axis is the brightness (cd / m).²) Is shown. Also , In Fig. 53, the vertical axis is power efficiency (lm / W) and the horizontal axis is brightness (cd / m).²) Is shown.</p><p num="0448">From FIG. 50, the emission spectra of the light emitting element 7 and the comparative light emitting element 5 are both with 470 nm. It has a peak nearby. Also, from the CIE chromaticity coordinates in Table 11, the light emitting element 7 and the comparative output Blue light emission derived from 1,6 FLPA Prn was observed in the optical element 5, and all the elements were capable. It turned out that the rear balance was good.</p><p num="0449">Further, from FIGS. 51 to 53 and Table 11, the light emitting element 7 has higher efficiency than the comparative light emitting element 5. It turned out to be a light emitting element of. This is the band of PCzPA used for the comparative light emitting device 5. The mPCP applied to the hole injection layer and the hole transport layer of the light emitting device 7 of this example rather than the gap. It is thought that this is because the band gap of Pn is wide and energy transfer from the light emitting layer is unlikely to occur. To. Also, it is considered that the LUMO level of mPCPPn is sufficiently shallow and the electron escape is suppressed. available.</p><p num="0450">Further, from FIGS. 51 to 53 and Table 11, the light emitting element 7 and the comparative light emitting element 5 have a low voltage. It turned out to be driveable.</p><p num="0451">Based on the above, the carbazole compound according to one aspect of the present invention can be used for the hole injection layer and the hole transport layer. It was shown that an element with high luminous efficiency can be realized. This is the carba of one aspect of the invention The LUMO level of the sol compound is sufficiently shallow, and the escape of electrons from the light emitting layer is suppressed. it is conceivable that. In addition, the HOMO level was sufficiently deep, and the hole injection property into the light emitting layer was good. It is thought that this is the case. In addition, the bandgap is wide enough and the efficiency due to the energy transfer of excitons It is probable that the decrease was suppressed.</p><p num="0452">Further, by using the carbazole compound of one aspect of the present invention in the hole injection layer and the hole transport layer, It was shown that a light emitting device with a low drive voltage can be realized.</p>

<p num="0453">In this embodiment, the manufacturing method of the light emitting device according to the present invention and the measurement results of the device characteristics are compared. It is shown together with the measurement result of the light emitting element.</p><p num="0454">The manufacturing method of the light emitting element 8 and the comparative light emitting element 6 of this embodiment will be described below. In addition, this implementation The element structure of the light emitting device produced in the example is the same as that in FIG. 29. In addition, the organic used in this example The structural formula of the compound is shown below. The description of organic compounds whose structural formulas have already been shown is omitted. Abbreviate.</p><p num="0455"><chemistry num="58"><img id="000070" he="32" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0456">(Light emitting element 8) The light emitting element 8 is formed in the same manner as the light emitting element 7 of the thirteenth embodiment except for the first electron transport layer 1114a. Made.</p><p num="0457">In the light emitting element 8, tris (8-quinolinolato) aluminum is placed on the light emitting layer 1113. (III) (abbreviation: Alq) is formed to have a film thickness of 10 nm, and the first electron transport layer 11 It was set to 14a.</p><p num="0458">(Comparative light emitting element 6) The comparative light emitting device 6 in this embodiment is the same as in Example 9 except for the first electron transport layer 1114a. The configuration was the same as that of the comparative light emitting element 1.</p><p num="0459">In the comparative light emitting element 6, Alq is formed on the light emitting layer 1113 so as to have a film thickness of 10 nm. The film was formed to form the first electron transport layer 1114a.</p><p num="0460">Table 12 shows the element structures of the light emitting element 8 and the comparative light emitting element 6 obtained as described above.</p><p num="0461"><tables num="12"><img id="000071" he="50" wi="150" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0462">The light emitting element 8 and the comparative light emitting element 6 are placed in a glove box having a nitrogen atmosphere. After performing the work of sealing so that it is not exposed to the atmosphere, the operating characteristics of each light emitting element I made a measurement. The measurement was performed at room temperature (atmosphere maintained at 25 ° C).</p><p num="0463">The light emitting element 8 and the comparative light emitting element 6 were formed on the same substrate. In addition, the above two light emission In the device, except for the hole injection layer and the hole transport layer, they are formed at the same time, and the operation characteristics are measured at the same time. You are operating.</p><p num="0464">In the light emitting element 8 and the comparative light emitting element 6, the brightness is 1000 cd / m.²Voltage in the vicinity (V) , Current density (mA / cm)²), CIE chromaticity coordinates (x, y), brightness, (cd / m)²), Current Table 13 shows efficiency (cd / A), power efficiency (lm / W), and external quantum efficiency (%).</p><p num="0465"><tables num="13"><img id="000072" he="24" wi="142" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0466">The emission spectra of the light emitting element 8 and the comparative light emitting element 6 are shown in FIG. 54. In FIG. 54, horizontal The axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In addition, the light emitting element 8 and comparative light emission The voltage-luminance characteristic of element 6 is shown in Fig. 55, the brightness-current efficiency characteristic is shown in Fig. 56, and the brightness-power efficiency characteristic is shown in Fig. 56. Are shown in FIG. 57, respectively. In Fig. 55, the vertical axis is the brightness (cd / m).²), Voltage (V) is shown on the horizontal axis However, in Fig. 56, the vertical axis is current efficiency (cd / A) and the horizontal axis is brightness (cd / m).²) Is shown. Also , In Fig. 57, the vertical axis is power efficiency (lm / W) and the horizontal axis is brightness (cd / m).²) Is shown.</p><p num="0467">From FIG. 54, the emission spectra of the light emitting element 8 and the comparative light emitting element 6 are both with 470 nm. It has a peak nearby. Also, from the CIE chromaticity coordinates in Table 13, the light emitting element 8 and the comparative output Blue light emission derived from 1,6 FLPA Prn was observed in the optical element 6, and all the elements were capable. It turned out that the rear balance was good.</p><p num="0468">Further, from FIGS. 55 to 57 and Table 13, the light emitting element 8 has higher efficiency than the comparative light emitting element 6. It turned out to be a light emitting element of. This is the band of PCzPA used for the comparative light emitting element 6. The mPCP applied to the hole injection layer and the hole transport layer of the light emitting device 8 of this example rather than the gap. It is thought that this is because the band gap of Pn is wide and energy transfer from the light emitting layer is unlikely to occur. To. Also, it is thought that the LUMO level of mPCPPn was sufficiently shallow and the electron escape was suppressed. Be done.</p><p num="0469">Further, from FIGS. 55 to 57 and Table 13, the light emitting element 8 and the comparative light emitting element 6 have a low voltage. It turned out to be driveable.</p><p num="0470">Moreover, the reliability test of the manufactured light emitting element 8 and the comparative light emitting element 6 was performed. Reliability test is the first Periodic brightness 5000 cd / m²Set to, and drive these elements under constant current density conditions, or The brightness was measured every time the time passed. The results obtained by the reliability test are shown in Fig. 58. .. In FIG. 58, the horizontal axis is the energization time (hour), and the vertical axis is the initial brightness at each time. It represents the ratio of brightness to degree, that is, normalized brightness (%).</p><p num="0471">From FIG. 58, the light emitting element 8 and the comparative light emitting element 6 are less likely to decrease in brightness with the passage of time. , It turns out that it has a long life. The light emitting element 8 has 83% of the initial brightness even after being driven for 70 hours. Keeping the brightness, the comparative light emitting element 6 keeps the brightness of 81% of the initial brightness even after driving for 70 hours. There was.</p><p num="0472">Based on the above, the carbazole compound according to one aspect of the present invention can be used for the hole injection layer and the hole transport layer. It was shown that an element with high luminous efficiency can be realized. This is the carba of one aspect of the invention The LUMO level of the sol compound is sufficiently shallow, and the escape of electrons from the light emitting layer is suppressed. it is conceivable that. In addition, the HOMO level was sufficiently deep, and the hole injection property into the light emitting layer was good. It is thought that this is the case. In addition, the bandgap is wide enough and the efficiency due to the energy transfer of excitons It is probable that the decrease was suppressed.</p><p num="0473">Further, by using the carbazole compound of one aspect of the present invention in the hole injection layer and the hole transport layer, It was shown that a light emitting device with a low drive voltage can be realized.</p><p num="0474">Further, by using the carbazole compound of one aspect of the present invention in the hole injection layer and the hole transport layer, It has been shown that a long-life light emitting device can be realized.</p>

<p num="0475">In this embodiment, the manufacturing method of the light emitting device according to the present invention and the measurement results of the device characteristics are compared. It is shown together with the measurement result of the light emitting element.</p><p num="0476">The manufacturing method of the light emitting element 9 and the comparative light emitting element 7 of this embodiment will be described below. In addition, this implementation The element structure of the light emitting device produced in the example is the same as that in FIG. 29. In addition, the organic used in this example The structural formula of the compound is shown below. The description of organic compounds whose structural formulas have already been shown is omitted. Abbreviate.</p><p num="0477"><chemistry num="59"><img id="000073" he="54" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0478">(Light emitting element 9) The light emitting element 9 includes a hole injection layer 1111, a hole transport layer 1112, a light emitting layer 1113, and a first electron. Except for the transport layer 1114a, it was produced in the same manner as the light emitting device 1 of Example 9.</p><p num="0479">In the light emitting element 9, the hole injection layer 1111 is mounted on the first electrode 1101 in the fifth embodiment. 9-Phenyl-3- [3- (triphenylene-2-yl) -phenyl] -9H-ka Formed by co-depositing rubazole (abbreviation: mPCzPTp) and molybdenum oxide (VI) did. The film thickness is 50 nm, and the ratio of mPCzPTp to molybdenum oxide (VI) is The weight ratio was adjusted to 4: 2 (= mPCzPTp: molybdenum oxide).</p><p num="0480">Next, mPCzPTp was formed on the hole injection layer 1111 so as to have a film thickness of 10 nm. A hole transport layer 1112 was formed.</p><p num="0481">In addition, 4- [3- (triphenylene-2-yl) phenyl] dibenzothiophene (abbreviation) : mDBTPTp-II), and Tris (2-Phenylpyridinato-N, C2') Illizi Umm (III) (abbreviation: Ir (ppy)₃) Is co-deposited and a light emitting layer is placed on the hole transport layer 1112. Formed 1113. Here, mDBTPTp-II and Ir (ppy)₃Weight ratio of 1: 0.06 (= mDBTPTp-II: Ir (ppy)₃) Was adjusted. Well The film thickness of the light emitting layer 1113 was set to 40 nm.</p><p num="0482">Next, Alq is formed on the light emitting layer 1113 so as to have a film thickness of 15 nm, and the first electron transport is performed. Layer 1114a was formed.</p><p num="0483">(Comparative light emitting element 7) The comparative light emitting device 7 in this embodiment includes a light emitting layer 1113 and a first electron transporting layer 1114a or later. The outside has the same configuration as that of the comparative light emitting element 1 in Example 9.</p><p num="0484">In the comparative light emitting device 7, the light emitting layer 1113 and the first electron transporting layer 1114a are generated as described above. It has the same configuration as the optical element 9.</p><p num="0485">Table 14 shows the element structures of the light emitting element 9 and the comparative light emitting element 7 obtained as described above.</p><p num="0486"><tables num="14"><img id="000074" he="47" wi="146" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0487">The light emitting element 9 and the comparative light emitting element 7 are placed in a glove box having a nitrogen atmosphere. After performing the work of sealing so that it is not exposed to the atmosphere, the operating characteristics of each light emitting element I made a measurement. The measurement was performed at room temperature (atmosphere maintained at 25 ° C).</p><p num="0488">The light emitting element 9 and the comparative light emitting element 7 were formed on the same substrate. In addition, the above two light emission In the device, except for the hole injection layer and the hole transport layer, they are formed at the same time, and the operation characteristics are measured at the same time. You are operating.</p><p num="0489">In the light emitting element 9 and the comparative light emitting element 7, the brightness is 1000 cd / m.²Voltage in the vicinity (V) , Current density (mA / cm)²), CIE chromaticity coordinates (x, y), brightness, (cd / m)²), Current Table 15 shows efficiency (cd / A), power efficiency (lm / W), and external quantum efficiency (%).</p><p num="0490"><tables num="15"><img id="000075" he="26" wi="142" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0491">The emission spectra of the light emitting element 9 and the comparative light emitting element 7 are shown in FIG. 59. In FIG. 59, horizontal The axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In addition, the light emitting element 9 and comparative light emission The voltage-luminance characteristic of the element 7 is shown in FIG. 60, and the luminance-current efficiency characteristic is shown in FIG. 61, respectively. Figure 60 Then the vertical axis is the brightness (cd / m)²), The horizontal axis shows the voltage (V), and in FIG. 61, the vertical axis shows the current efficiency. (cd / A), brightness on the horizontal axis (cd / m)²) Is shown.</p><p num="0492">From FIG. 59, the emission spectra of the light emitting element 9 and the comparative light emitting element 7 are both with 520 nm. It has a peak nearby. Also, from the CIE chromaticity coordinates in Table 15, the light emitting element 9 and the comparative output The optical element 7 is Ir (ppy).₃Green phosphorescence is observed from the above, and all the elements are key. It turned out that the charia balance was good.</p><p num="0493">Further, from FIGS. 60, 61 and 15, the light emitting element 9 emits higher efficiency than the comparative light emitting element 7. It turned out to be an optical element. This is the band gear of PCzPA used for the comparative light emitting element 7. MPCzPT applied to the hole injection layer and hole transport layer of the light emitting device 9 of this example This is thought to be because the bandgap of p is wide and energy transfer from the light emitting layer is unlikely to occur. .. Also, it is considered that the LUMO level of mPCzPTp is sufficiently shallow and the electron escape is suppressed. available.</p><p num="0494">Further, from FIGS. 60, 61 and 15, the light emitting element 9 and the comparative light emitting element 7 are driven by a low voltage. It turned out to be possible.</p><p num="0495">Based on the above, the carbazole compound according to one aspect of the present invention can be used for the hole injection layer and the hole transport layer. It was shown that an element with high luminous efficiency can be realized. This is the carba of one aspect of the invention The LUMO level of the sol compound is sufficiently shallow, and the escape of electrons from the light emitting layer is suppressed. it is conceivable that. In addition, the HOMO level was sufficiently deep, and the hole injection property into the light emitting layer was good. It is thought that this is the case. In addition, the bandgap is wide enough and the efficiency due to the energy transfer of excitons It is probable that the decrease was suppressed.</p><p num="0496">Further, by using the carbazole compound of one aspect of the present invention in the hole injection layer and the hole transport layer, It was shown that a light emitting device with a low drive voltage can be realized.</p>

<p num="0497">In this embodiment, the manufacturing method of the light emitting device according to the present invention and the measurement results of the device characteristics are compared. It is shown together with the measurement result of the light emitting element.</p><p num="0498">The manufacturing method of the light emitting element 10 and the comparative light emitting element 8 of this embodiment will be described below. Also, the real thing The element structure of the light emitting element produced in the example is shown in FIG. The organic compound used in this example Since the material is the same as that of the previous embodiment, the description thereof will be omitted.</p><p num="0499">(Light emitting element 10) The light emitting element 10 was produced in the same manner as the light emitting element 9 of Example 15 except for the light emitting layer 1113.</p><p num="0500">In the light emitting element 10, the light emitting layer 1113 is the first light emitting layer 1 from the first electrode 1101 side. It was formed by laminating 113a and the second light emitting layer 1113b.</p><p num="0501">The first light emitting layer 1113a contains mPCzPTp and tris (2-phenyl) synthesized in Example 5. Pyrizinato-N, C2') Iridium (III) (abbreviation: Ir (ppy)₃) And co-deposited Was formed. Here, mPCzPTp and Ir (ppy)₃Weight ratio is 1: 0.06 (= mPCzPTp: Ir (ppy)₃) Was adjusted. In addition, the first light emitting layer 1 The film thickness of 113a was 20 nm.</p><p num="0502">Then 4- [3- (triphenylene-2-yl) phenyl] dibenzothiophene (abbreviation) : mDBTPTp-II) and Ir (ppy)₃First light emitting layer 1113 A second light emitting layer 1113b was formed on a. Here, mDBTPTp-II and Ir (p) py)₃Weight ratio is 1: 0.06 (= mDBTPTp-II: Ir (ppy)₃) Tona Adjusted to. The film thickness of the second light emitting layer 1113b was set to 20 nm.</p><p num="0503">(Comparative light emitting element 8) The comparative light emitting device 8 in this embodiment is a comparative light emitting device 8 in Example 15, except for the light emitting layer 1113. The configuration is the same as that of the optical element 7.</p><p num="0504">In the comparative light emitting element 8, the light emitting layer 1113 has the same configuration as the above-mentioned light emitting element 10.</p><p num="0505">Table 16 shows the element structures of the light emitting element 10 and the comparative light emitting element 8 obtained as described above.</p><p num="0506"><tables num="16"><img id="000076" he="65" wi="166" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0507">The light emitting element 10 and the comparative light emitting element 8 are placed in a glove box having a nitrogen atmosphere. After performing the work of sealing the child so that it is not exposed to the atmosphere, the operating characteristics of each light emitting element The measurement was carried out. The measurement was performed at room temperature (atmosphere maintained at 25 ° C).</p><p num="0508">The light emitting element 10 and the comparative light emitting element 8 were formed on the same substrate. In addition, the above two departures In the optical device, except for the hole injection layer and the hole transport layer, they are formed at the same time, and the operation characteristics are measured at the same time. Is operating.</p><p num="0509">In the light emitting element 10 and the comparative light emitting element 8, the brightness is 1000 cd / m.²Near voltage (V) ), Current density (mA / cm)²), CIE chromaticity coordinates (x, y), brightness, (cd / m)²), Den Table 17 shows the flow efficiency (cd / A), power efficiency (lm / W), and external quantum efficiency (%).</p><p num="0510"><tables num="17"><img id="000077" he="24" wi="147" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0511">The emission spectra of the light emitting element 10 and the comparative light emitting element 8 are shown in FIG. 63. In FIG. 63, The horizontal axis represents the wavelength (nm), and the vertical axis represents the emission intensity (arbitrary unit). Also, the light emitting element 10 and comparison The voltage-luminance characteristics of the light emitting element 8 are shown in FIG. 64, and the luminance-current efficiency characteristics are shown in FIG. 65, respectively. Figure At 64, the vertical axis is the brightness (cd / m)²), The horizontal axis shows the voltage (V), and in Fig. 65, the vertical axis shows the current. Efficiency (cd / A), brightness on the horizontal axis (cd / m)²) Is shown.</p><p num="0512">From FIG. 63, the emission spectra of the light emitting element 10 and the comparative light emitting element 8 are both 515 nm. It has a peak in the vicinity. Also, from the CIE chromaticity coordinates in Table 17, the light emitting element 10 and the ratio The light emitting element 8 is Ir (ppy).₃Green phosphorescence from the above was observed, and any element It was also found that the carrier balance was good. Further, the light emitting element 10 and the ratio of this embodiment The light emitting device 8 is a carba according to an aspect of the present invention as a host material for a green phosphorescent compound. A sol compound is applied, and the T1 level of the carbazole compound according to one aspect of the present invention is ten. It was confirmed to be relatively high (at least the T1 level higher than that of the green phosphorescent compound). ..</p><p num="0513">Further, from FIGS. 64, 65 and 17, the light emitting element 10 has higher efficiency than the comparative light emitting element 8. It turned out to be a light emitting element. This is the bandgi of PCzPA used for the comparative light emitting element 8. MPCz applied to the hole injection layer and hole transport layer of the light emitting device 10 of this example rather than the cap. It is thought that this is because the band gap of PTp is wide and energy transfer from the light emitting layer is unlikely to occur. Is done. Also, the LUMO level of mPCzPTp is shallow enough to suppress the escape of electrons. Conceivable.</p><p num="0514">Further, from FIGS. 64, 65 and 17, the light emitting element 10 and the comparative light emitting element 8 are driven by a low voltage. It turned out to be movable.</p><p num="0515">Based on the above, the carbazole compound according to one aspect of the present invention can be used for the hole injection layer and the hole transport layer. It was shown that an element with high luminous efficiency can be realized. This is the carba of one aspect of the invention The LUMO level of the sol compound is sufficiently shallow, and the escape of electrons from the light emitting layer is suppressed. it is conceivable that. In addition, the HOMO level was sufficiently deep, and the hole injection property into the light emitting layer was good. It is thought that this is the case. In addition, the bandgap is wide enough and the efficiency due to the energy transfer of excitons It is probable that the decrease was suppressed.</p><p num="0516">Further, the carbazole compound according to one aspect of the present invention is applied to the hole injection layer, the hole transport layer and the light emitting layer. It has been shown that a light emitting device having a low drive voltage can be realized by using the device.</p><p num="0517">Further, since the carbazole compound according to one aspect of the present invention has a wide bandgap, it is phosphorescent. It has been shown to be suitable as a host material for luminescent materials.</p>

<p num="0518">In this embodiment, a method for manufacturing a light emitting device according to one aspect of the present invention and a measurement result of device characteristics are shown.</p><p num="0519">The method of manufacturing the light emitting element 11 of this embodiment will be described below. In addition, the light emission produced in this example The element structure of the element is shown in FIG. The structural formulas of the organic compounds used in this example are shown below. Shown. The structural formula shown in the previous embodiment will be omitted.</p><p num="0520"><chemistry num="60"><img id="000078" he="49" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0521">(Light emitting element 11) In the light emitting element 11, the first electrode 1101, the electron injection layer 1115, and the second electrode 11 03 was produced in the same manner as the light emitting element 1 of Example 9.</p><p num="0522">In the light emitting element 11, 4-phenyl-4'-(9-phenylful) is placed on the first electrode 1101. Oren-9-yl) triphenylamine (abbreviation: BPAFLP) and molybdenum oxide (VI) ) Was co-deposited to form the hole injection layer 1111. The film thickness is 50 nm, and B The ratio of PAFLP to molybdenum oxide (VI) is 4: 2 by weight (= BPAFLP: oxidation). It was adjusted to be molybdenum). The co-evaporation method is a method of steaming a plurality of steamers in one processing chamber. This is a thin-film deposition method in which vapor deposition is performed simultaneously from the source.</p><p num="0523">Next, BPAFLP was formed on the hole injection layer 1111 so as to have a film thickness of 10 nm, and the positive film was formed. A pore transport layer 1112 was formed.</p><p num="0524">The light emitting layer 1113 is composed of mPCzPTp and tris (2-phenylpyridina) synthesized in Example 5. To-N, C2') Iridium (III) (abbreviation: Ir (ppy)₃) And co-deposited did. Here, mPCzPTp and Ir (ppy)₃The weight ratio of is 1: 0.08 (= mP) CzPTp: Ir (ppy)₃) Was adjusted. Also, the film thickness of the light emitting layer 1113 is It was set to 40 nm.</p><p num="0525">Next, mPCzPTp is deposited to form a first electron transport layer 1114a on the light emitting layer 1113. Formed. The film thickness of the first electron transport layer 1114a was set to 10 nm.</p><p num="0526">After that, bassophenanthroline (abbreviation: BPhen) was placed on the first electron transport layer 1114a. A second electron transport layer 1114b was formed by forming a film so as to have a film thickness of 20 nm.</p><p num="0527">Table 18 shows the element structure of the light emitting element 11 obtained as described above.</p><p num="0528"><tables num="18"><img id="000079" he="50" wi="161" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0529">The light emitting element 11 is placed in a glove box having a nitrogen atmosphere, and the light emitting element is not exposed to the atmosphere. After performing the sealing work, the operating characteristics of the light emitting element were measured. In addition, measurement The setting was performed at room temperature (atmosphere maintained at 25 ° C).</p><p num="0530">In the light emitting element 11, the brightness is 1000 cd / m.²Voltage (V) and current density (mA) in the vicinity /cm²), CIE chromaticity coordinates (x, y), brightness, (cd / m)²), Current efficiency (cd / A) , Power efficiency (lm / W) and external quantum efficiency (%) are shown in Table 19.</p><p num="0531"><tables num="19"><img id="000080" he="21" wi="146" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0532">The emission spectrum of the light emitting element 11 is shown in FIG. In FIG. 66, the horizontal axis is the wavelength (nm). , The vertical axis represents the emission intensity (arbitrary unit). In addition, the voltage-luminance characteristics of the light emitting element 11 are shown in FIG. 67. The brightness-current efficiency characteristics are shown in FIG. 68, respectively. In FIG. 67, the vertical axis is the brightness (cd / m).²),side The axis shows the voltage (V), and in FIG. 68, the vertical axis shows the current efficiency (cd / A) and the horizontal axis shows the brightness (cd /). m²) Is shown.</p><p num="0533">From FIG. 66, the light emitting device 11 has a peak near 515 nm. Also, C in Table 19 From the IE chromaticity coordinates, the light emitting element 11 is Ir (ppy).₃You can see the green phosphorescence derived from It was measured and found to have a good career balance. Further, the light emitting element 11 of this embodiment Is a carbazole compound according to an aspect of the present invention as a host material for a green phosphorescent compound. The T1 level of the carbazole compound according to one aspect of the present invention is sufficiently high (low). At least it has a higher T1 level than the green phosphorescent compound).</p><p num="0534">Further, the light emitting device 11 of the present embodiment is a carbazo according to one aspect of the present invention as an electron transporting material. The carbazole compound according to one aspect of the present invention has good electron transportability. It turned out to be a good material.</p><p num="0535">Further, from FIGS. 67, 68 and 19, it can be seen that the light emitting element 11 is a highly efficient light emitting element. all right.</p><p num="0536">From the above, by applying the carbazole compound of one aspect of the present invention as a material for a light emitting device, , It was shown that the light emitting element can be a highly efficient light emitting element. In addition, the present invention Since the carbazole compound of one embodiment has a wide bandgap, it is a phosphorescent material. It has been shown to be suitable as a strike material.</p>

<p num="0537">In this embodiment, a method for manufacturing a light emitting device according to one aspect of the present invention and a measurement result of device characteristics are shown.</p><p num="0538">The manufacturing method of the light emitting element 12 and the light emitting element 13 of this embodiment will be described below. In addition, this implementation The element structure of the light emitting device produced in the example is the same as that in FIG. 29. In addition, the organic used in this example The structural formula of the compound is shown below. The description of organic compounds whose structural formulas have already been shown is omitted. Abbreviate.</p><p num="0539"><chemistry num="61"><img id="000081" he="55" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0540">(Light emitting element 12) The light emitting element 12 has a first electrode 1101, an electron injection layer 1115, and a second electrode 1103. , The same as the light emitting device 1 of Example 9.</p><p num="0541">In the light emitting element 12, 3- [4- (1-na) synthesized in Example 1 was placed on the first electrode 1101. Futyl) -Phenyl] -9-Phenyl-9H-carbazole (abbreviation: PCPN) and oxide The hole injection layer 1111 was formed by co-depositing ribden (VI). Its film thickness is 4 At 0 nm, the ratio of PCPN to molybdenum oxide (VI) is 4: 2 by weight (= PCPN). : Molybdenum oxide). The co-evaporation method is a combination of two methods in one processing room. This is a thin-film deposition method in which vapor deposition is performed simultaneously from a number of evaporation sources.</p><p num="0542">Next, PCPN was formed on the hole injection layer 1111 so as to have a film thickness of 20 nm, and the holes were transplanted. A feed layer 1112 was formed.</p><p num="0543">The light emitting layer 1113 is composed of 2- [3- (dibenzothiophen-4-yl) phenyl] dibenzo [ f, h] Quinoxaline (abbreviation: 2mDBTPDBq-II) and (Dipivaloylmethanato) Bis (3,5-dimethyl-2-phenylpyrazinato) Iridium (III) (abbreviation: Ir (mppr-Me)₂It was formed by co-depositing with dpm). Where 2mDBTPDBq- II and Ir (mppr-Me)₂The weight ratio of dpm is 1: 0.05 (= 2mDBTPD) Bq-II: Ir (mppr-Me)₂It was adjusted to be dpm). Also, the light emitting layer 1 The film thickness of 113 was 30 nm.</p><p num="0544">Next, 2mDBTPDBq-II was vapor-deposited, and the first electron transport layer 1 was deposited on the light emitting layer 1113. Formed 114a. The film thickness of the first electron transport layer 1114a was set to 10 nm.</p><p num="0545">After that, bassophenanthroline (abbreviation: BPhen) was placed on the first electron transport layer 1114a. A second electron transport layer 1114b was formed by forming a film so as to have a film thickness of 20 nm.</p><p num="0546">(Light emitting element 13) The light emitting element 13 was manufactured in the same manner as the above-mentioned light emitting element 12 except for the light emitting layer 1113.</p><p num="0547">In the light emitting element 13, the light emitting layer 1113 includes 2mDBTPDBq-II, PCPN, and Ir (mppr-Me)₂It was formed by co-depositing with dpm. Where 2mDBTPDBq -II, PCPN, and Ir (mppr-Me)₂The weight ratio of dpm is 0.7: 0.3: 0.05 (= 2mDBTPDBq-II: PCPN: Ir (mppr-Me)₂dpm) It was adjusted to be. The film thickness of the light emitting layer 1113 was set to 30 nm.</p><p num="0548">Table 20 shows the element structures of the light emitting element 12 and the light emitting element 13 obtained as described above.</p><p num="0549"><tables num="20"><img id="000082" he="75" wi="166" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0550">The light emitting element 12 and the light emitting element 13 are placed in a glove box having a nitrogen atmosphere. After performing the work of sealing so that it is not exposed to the atmosphere, the operating characteristics of each light emitting element I made a measurement. The measurement was performed at room temperature (atmosphere maintained at 25 ° C).</p><p num="0551">The light emitting element 12 and the light emitting element 13 were formed on the same substrate. In addition, the above two light emission In the element, except for the light emitting layer 1113, they are formed at the same time, and the measurement of the operating characteristics is performed at the same time. ing.</p><p num="0552">In the light emitting element 12 and the light emitting element 13, the brightness is 1000 cd / m.²Voltage in the vicinity (V) , Current density (mA / cm)²), CIE chromaticity coordinates (x, y), brightness, (cd / m)²), Current Table 21 shows efficiency (cd / A), power efficiency (lm / W), and external quantum efficiency (%).</p><p num="0553"><tables num="21"><img id="000083" he="26" wi="141" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0554">The emission spectra of the light emitting element 12 and the light emitting element 13 are shown in FIG. 69. In FIG. 69, horizontal The axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In addition, the light emitting element 12 and the light emitting element The voltage-brightness characteristics of the child 13 are shown in Fig. 70, the brightness-current efficiency characteristics are shown in Fig. 71, and the brightness-power efficiency characteristics are shown in Fig. 71. Are shown in FIG. 72, respectively. In Fig. 70, the vertical axis is the brightness (cd / m).²), Voltage (V) is shown on the horizontal axis However, in Fig. 71, the vertical axis is current efficiency (cd / A) and the horizontal axis is brightness (cd / m).²) Is shown. Also , In Fig. 72, the vertical axis is power efficiency (lm / W) and the horizontal axis is brightness (cd / m).²) Is shown.</p><p num="0555">From FIG. 69, the light emitting element 12 and the light emitting element 13 have a peak near 580 nm. Also, from the CIE chromaticity coordinates in Table 21, the light emitting element 12 and the light emitting element 13 are Ir (mpp). r-Me)₂Orange phosphorescence from dpm is observed, and the carrier balance is good. It turned out to be good. Further, the light emitting element 13 of this embodiment is an orange phosphorescent compound. The carbazole compound according to one aspect of the present invention is applied as the host material of the present invention. The T1 level of the carbazole compound according to one embodiment is sufficiently high (at least orange phosphorus). It was confirmed that the T1 level is higher than that of photocompounds). Also, all elements are equally low. It turned out to be the drive voltage.</p><p num="0556">Further, from FIGS. 70, 71, 72 and 21, the light emitting element 12 and the light emitting element 13 are highly effective. It turned out to be a rate light emitting element.</p><p num="0557">From the above, by applying the carbazole compound of one aspect of the present invention as a material for a light emitting device, , It was shown that the light emitting element can be a highly efficient light emitting element. In addition, the present invention Since the carbazole compound of one embodiment has a wide bandgap, it is a phosphorescent material. It has been shown to be suitable as a strike material.</p><p num="0558">Further, the carbazole compound according to one aspect of the present invention is applied to the hole injection layer, the hole transport layer and the light emitting layer. It has been shown that a light emitting device having a low drive voltage can be realized by using the device.</p><p num="0559">(Reference example) An example of the method for synthesizing the material for the light emitting device used in this embodiment is shown below.</p><p num="0560">&lt;Synthesis example of 2mDBTPDBq-II&gt; 2- [3- (Dibenzothiophen-4-yl) phenyl] dibenzo [f, h] quinoxari (Abbreviation: 2mDBTPDBq-II) synthesis method will be explained. Synthetic scheme ( Shown in R-1).</p><p num="0561"><chemistry num="62"><img id="000084" he="68" wi="167" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0562">2-Chlorodibenzo [f, h] quinoxaline 5.3 g (20 mmol) in a 2 L three-necked flask ), 3- (Dibenzothiophen-4-yl) Phenylboronic acid 6.1 g (20 mmol) , Tetrakis (triphenylphosphine) palladium (0) 460 mg (0.4 mmol) ), 300 mL of toluene, 20 mL of ethanol, 20 mL of 2M potassium carbonate aqueous solution I got it. The mixture was degassed by stirring under reduced pressure and the inside of the flask was replaced with nitrogen. this The mixture was stirred at 100 ° C. for 7.5 hours under a nitrogen stream. After cooling to room temperature, the resulting mixture The mixture was filtered to give a white filter. After rinsing the obtained filter well in the order of water and ethanol , Dried. The obtained solid is dissolved in about 600 mL of warm toluene, and Celite and Floridi The mixture was suction-filtered through a mixture to obtain a colorless and transparent filtrate. The obtained filtrate is concentrated and silica gel is used. Purified by lamb chromatography. Chromatography uses toluene at a temperature of about 40 ° C. It was used as a developing solvent. Acetone / ethanol is added to the solid obtained here and ultrasonic waves are applied. After irradiation, the resulting suspension was collected by filtration and dried, and the yield of the target white powder was 7.8. It was obtained in 5 g and a yield of 80%.</p><p num="0563">The above-mentioned object was a material that was relatively soluble in warm toluene, but easily precipitated when cooled. It was. In addition, it was sparingly soluble in other organic solvents such as acetone and ethanol. Therefore, this melting Taking advantage of the difference in decomposability, it was possible to synthesize in good yield by a simple method as described above. concrete After the reaction is completed, the temperature is returned to room temperature and the precipitated solid is collected by filtration to simplify most of the impurities. I was able to remove it from the stool. In addition, warm column chromatography using warm toluene as a developing solvent Therefore, it was possible to easily purify the target product, which is easily precipitated.</p><p num="0564">4.0 g of the obtained white powder was sublimated and purified by the train sublimation method. Sublimation purification Heats the white powder at 300 ° C under the conditions of pressure 5.0 Pa and argon flow rate 5 mL / min. I went. After sublimation purification, 3.5 g of the target white powder was obtained in a yield of 88%.</p><p num="0565">By nuclear magnetic resonance spectroscopy (NMR), this compound is the object of interest 2- [3- (dibenzothio) Fen-4-yl) Phenyl] Dibenzo [f, h] Quinoxaline (abbreviation: 2mDBTPD) It was confirmed that it was Bq-II).</p><p num="0566">Of the obtained substance¹The 1 H NMR data is shown below.¹1 H NMR (CDCl₃, 300MHz): δ (ppm) = 7.45-7.52 (m, 2H), 7.59-7.65 (m, 2H), 7.71-7.91 (m, 7H), 8.20 -8.25 (m, 2H), 8.41 (d, J = 7.8Hz, 1H), 8.65 (d, J = 7.5Hz, 2H), 8.77-8.78 (m, 1H), 9.23 (dd, J = 7.2H) z, 1.5Hz, 1H), 9.42 (dd, J = 7.8Hz, 1.5Hz, 1H), 9. 48 (s, 1H).</p><p num="0567">&lt;Ir (mppr-Me)₂dpm synthesis example&gt; (Dipivaloylmethanato) Bis (3,5-dimethyl-2-phenylpyrazinato) Iridium Mu (III) (abbreviation: Ir (mppr-Me)₂The synthesis method of dpm) will be described. The synthesis scheme is shown in (R-2).</p><p num="0568"><chemistry num="63"><img id="000085" he="96" wi="170" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0569">20 mL of 2-ethoxyethanol and 1.55 g of dinuclear complex di-μ-chloro-bis [bi] Su (3,5-dimethyl-2-phenylpyrazinato) iridium (III)] (abbreviation: [I r (mppr-Me)₂Cl]₂), 0.8 ml dipivaloyl methane and 1.38 g Sodium carbonate is mixed and irradiated with microwaves for 30 minutes under argon bubbling. I made it correspond. After the reaction, the reaction solution was allowed to cool to room temperature and water was added. This mixed solution is mixed with an organic layer and water. The liquid was separated into layers, and the aqueous layer was extracted with dichloromethane. Combine the organic layer and the extract solution and wash with water. It was purified and dried over anhydrous magnesium sulfate. After drying, it is naturally filtered to concentrate and dry the filtrate. It was. By recrystallizing this solid with a mixed solvent of dichloromethane and ethanol, a red powder can be obtained. It was obtained in a yield of 67%. In addition, microwave irradiation is performed by a microwave synthesizer (CEM Dis). cover) was used.</p><p num="0570">By nuclear magnetic resonance spectroscopy (NMR), the organometallic complex [Ir ( mppr-Me)₂I confirmed that it was dpm].</p><p num="0571">Obtained¹The 1 H NMR data is shown below.¹H-NMR.δ (CDCl₃): 0.90 (s, 1H), 2.59 (s, 6H), 3. 04 (s, 6H), 5.49 (s, 1H), 6.32 (dd, 2H), 6.70 (dt, dt, 2H), 6.88 (dt, 2H), 7.86 (d, 2H), 8.19 (s, 2H).</p>

<p num="0572">In this embodiment, a method for manufacturing a light emitting device according to one aspect of the present invention and a measurement result of device characteristics are shown.</p><p num="0573">The method of manufacturing the light emitting element 14 to the light emitting element 17 of this embodiment will be described below. The element structure of the light emitting device produced in FIG. 29 is the same as that in FIG. 29. In addition, the organication used in this example The structural formula of the mixture is shown below. The description is omitted for organic compounds whose structural formulas have already been shown. To do.</p><p num="0574"><chemistry num="64"><img id="000086" he="79" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0575">(Light emitting element 14) The light emitting element 14 was produced in the same manner as the light emitting element 12 of Example 18 except for the light emitting layer 1113.</p><p num="0576">In the light emitting device 14, the light emitting layer 1113 is 2- [3- (dibenzothiophen-4-yl). ) Phenyl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTPDBq-II), 4, 4'-di (1-naphthyl) -4''-(9-phenyl-9H-carbazole-3-a) Le) Triphenylamine (abbreviation: PCBNBB) and (dipivaloylmethanato) bis (3) , 5-Dimethyl-2-phenylpyrazinato) Iridium (III) (abbreviation: Ir (mpp) r-Me)₂It was formed by co-depositing with dpm). Here, 2mDBTPDBq-II, P CBNBB and Ir (mppr-Me)₂The weight ratio of dpm is 0.8: 0.2: 0.05 (= 2mDBTPDBq-II: PCBNBB: Ir (mppr-Me)₂dpm) Adjusted to. The film thickness of the light emitting layer 1113 was set to 40 nm.</p><p num="0577">(Light emitting element 15) The light emitting element 15 includes the above-mentioned light emitting element 1 except for the hole injection layer 1111 and the hole transport layer 1112. It was prepared in the same manner as in 4.</p><p num="0578">In the light emitting element 15, the hole injection layer 1111 is placed on the first electrode 1101 in the second embodiment. Synthesized 3- [4- (9-Phenyl) -Phenyl] -9-Phenyl-9H-Carba It was formed by co-depositing sol (abbreviation: PCPPn) and molybdenum oxide (VI). So The film thickness is 40 nm, and the ratio of PCPPn to molybdenum oxide (VI) is 4: by weight. It was adjusted to 2 (= PCPPn: molybdenum oxide).</p><p num="0579">Next, PCPPn was formed on the hole injection layer 1111 so as to have a film thickness of 20 nm, and holes were formed. A transport layer 1112 was formed.</p><p num="0580">(Light emitting element 16) The light emitting element 16 was manufactured in the same manner as the above-mentioned light emitting element 14 except for the hole injection layer 1111.</p><p num="0581">In the light emitting device 16, the hole injection layer 1111 is placed on the first electrode 1101 with 9- [4- ( 9-Phenylcarbazole-3-yl) phenyl] -10-Phenylanthracene (abbreviation) : PCzPA) and molybdenum oxide (VI) were co-deposited. Its film thickness is 4 At 0 nm, the ratio of PCzPA to molybdenum oxide (VI) is 4: 2 by weight (= PCz). PA: Molybdenum oxide) was adjusted.</p><p num="0582">(Light emitting element 17) The light emitting element 17 was manufactured in the same manner as the above-mentioned light emitting element 15 except for the hole injection layer 1111. Departure The hole injection layer 1111 of the optical element 17 was produced in the same manner as the light emitting element 16 described above.</p><p num="0583">Table 22 shows the element structures of the light emitting elements 14 to 17 obtained as described above.</p><p num="0584"><tables num="22"><img id="000087" he="122" wi="165" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0585">The light emitting elements 14 to 17 are placed in a glove box having a nitrogen atmosphere. After performing the work of sealing so that it is not exposed to the atmosphere, the operating characteristics of each light emitting element I made a measurement. The measurement was performed at room temperature (atmosphere maintained at 25 ° C).</p><p num="0586">The light emitting element 14 to the light emitting element 17 were formed on the same substrate. In addition, the above four light emission In the device, except for the hole injection layer 1111 and the hole transport layer 1112, they are formed at the same time, and The operating characteristics are measured at the same time.</p><p num="0587">In the light emitting element 14 to the light emitting element 17, the brightness is 1000 cd / m.²Voltage in the vicinity (V) , Current density (mA / cm)²), CIE chromaticity coordinates (x, y), brightness, (cd / m)²), Current Table 23 shows efficiency (cd / A), power efficiency (lm / W), and external quantum efficiency (%).</p><p num="0588"><tables num="23"><img id="000088" he="27" wi="121" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0589">The emission spectra of the light emitting elements 14 to 17 are shown in FIG. 73. In FIG. 73, horizontal The axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In addition, the light emitting element 14 to the light emitting element The voltage-luminance characteristics of the child 17 are shown in Fig. 74, the brightness-current efficiency characteristics are shown in Fig. 75, and the brightness-power efficiency characteristics are shown in Fig. 75. Are shown in FIG. 76, respectively. In Fig. 74, the vertical axis is the brightness (cd / m).²), Voltage (V) is shown on the horizontal axis However, in Fig. 75, the vertical axis is current efficiency (cd / A) and the horizontal axis is brightness (cd / m).²) Is shown. Also , In Figure 76, the vertical axis is power efficiency (lm / W) and the horizontal axis is brightness (cd / m).²) Is shown.</p><p num="0590">From FIG. 73, the light emitting element 14 to the light emitting element 17 have a peak near 580 nm. Also, from the CIE chromaticity coordinates in Table 23, the light emitting elements 14 to 17 are Ir (mpp). r-Me)₂Orange phosphorescence from dpm is observed, and the carrier balance is good. It turned out to be good.</p><p num="0591">Further, from FIGS. 74, 75, 76 and 23, the light emitting elements 14 to 17 are highly effective. It turned out to be a rate light emitting element.</p><p num="0592">Further, a layer containing the carbazole compound according to one aspect of the present invention was applied to the hole injection layer 1111. The light emitting element 14 and the light emitting element 15 have higher efficiency than the light emitting element 16 and the light emitting element 17. It turned out to show. It was also found that all the elements had the same low drive voltage.</p><p num="0593">Moreover, the reliability test of the manufactured light emitting element 14 and the ultimate light emitting element 17 was carried out. Reliability test is the first Periodic brightness 5000 cd / m²Set to, and drive these elements under constant current density conditions, or The brightness was measured every time the time passed. The results obtained by the reliability test are shown in Fig. 77. .. In FIG. 77, the horizontal axis is the energization time (hour), and the vertical axis is the initial brightness at each time. It represents the ratio of brightness to degree, that is, normalized brightness (%).</p><p num="0594">From FIG. 77, it is difficult for the light emitting element 14 and the light emitting element 17 to decrease in brightness with the passage of time. , It turns out that it has a long life. The light emitting element 14 has an initial brightness of 87 even after being driven for 190 hours. The brightness of% is maintained, and the light emitting element 15 maintains the brightness of 83% of the initial brightness even after being driven for 190 hours. The light emitting element 16 maintains 81% of the initial brightness even after being driven for 190 hours, and the light emitting element The 17 maintained a brightness of 79% of the initial brightness even after being driven for 190 hours.</p><p num="0595">From the above, by applying the carbazole compound of one aspect of the present invention as a material for a light emitting device, , It was shown that the light emitting element can be a highly efficient light emitting element.</p><p num="0596">Further, by using the carbazole compound of one aspect of the present invention in the hole injection layer and the hole transport layer, It was shown that a light emitting device with a low drive voltage can be realized.</p><p num="0597">Further, by using the carbazole compound of one aspect of the present invention in the hole injection layer and the hole transport layer, It has been shown that a long-life light emitting device can be realized.</p>

<p num="0598">In this embodiment, the method for manufacturing the light emitting device according to the present invention and the measurement results of the device characteristics are compared and generated. It is shown together with the measurement result of the optical element.</p><p num="0599">Hereinafter, a method for manufacturing the light emitting element 18, the light emitting element 19, and the comparative light emitting element 9 of this embodiment will be described. To. The element structure of the light emitting device produced in this embodiment is the same as that in FIG. 62. Also, the real thing Since the organic compound used in the examples is an organic compound whose structural formula has already been shown, the description thereof will be omitted.</p><p num="0600">(Light emitting element 18) In the light emitting element 18, the hole injection layer 1111, the hole transport layer 1112, and the light emitting layer 1113 and above. The outside was produced in the same manner as the light emitting element 8 of Example 14.</p><p num="0601">In the light emitting device 18, the hole injection layer 1111 is mounted on the first electrode 1101 in the first embodiment. It was formed by co-depositing the formed PCPN and molybdenum oxide (VI). Its film thickness is 5 At 0 nm, the ratio of PCPN to molybdenum oxide (VI) is 4: 2 by weight (= PCPN). : Molybdenum oxide).</p><p num="0602">Next, PCPN was formed on the hole injection layer 1111 so as to have a film thickness of 10 nm, and the holes were transplanted. A feed layer 1112 was formed.</p><p num="0603">In the light emitting element 18, the light emitting layer 1113 is the first light emitting layer 1 from the first electrode 1101 side. It was formed by laminating 113a and the second light emitting layer 1113b.</p><p num="0604">The first light emitting layer 1113a was formed by co-depositing PCPN and 1,6FLPA Prn. .. Here, the weight ratio of PCPN and 1,6FLPA Prn is 1: 0.05 (= PCPN:). It was adjusted to 1,6 FLPA Prn). The film thickness of the first light emitting layer 1113a is It was set to 10 nm.</p><p num="0605">The second light emitting layer 1113b is formed by co-depositing CzPA and 1,6FLPA Prn. It was done. Here, the weight ratio of CzPA and 1,6FLPA Prn is 1: 0.05 (= Cz). PA: 1,6FLPA Prn) was adjusted. Also, of the second light emitting layer 1113b The film thickness was 25 nm.</p><p num="0606">(Light emitting element 19) In the light emitting element 19, the hole injection layer 1111, the hole transport layer 1112, and the first light emitting layer 1 Except for 113a, it was manufactured in the same manner as the above-mentioned light emitting element 18.</p><p num="0607">In the light emitting device 19, the hole injection layer 1111 is mounted on the first electrode 1101 in the second embodiment. It was formed by co-depositing the formed PCPPn and molybdenum oxide (VI). The film thickness is At 50 nm, the ratio of PCPPn to molybdenum oxide (VI) is 4: 2 by weight (= PC). PPn: molybdenum oxide) was adjusted.</p><p num="0608">Next, PCPPn was formed on the hole injection layer 1111 so as to have a film thickness of 10 nm, and holes were formed. A transport layer 1112 was formed.</p><p num="0609">In the light emitting element 19, the first light emitting layer 1113a is PCPPn and 1,6FLPA Prn. And were co-deposited to form. Here, the weight ratio of PCPPn and 1,6 FLPA Prn is 1: Adjusted to 0.05 (= PCPPn: 1,6FLPA Prn). Also the first The film thickness of the light emitting layer 1113a was 10 nm.</p><p num="0610">(Comparative light emitting element 9) In the comparative light emitting device 9, the hole injection layer 1111, the hole transport layer 1112, and the first light emitting layer Except for 1113a, it was manufactured in the same manner as the above-mentioned light emitting element 18.</p><p num="0611">In the comparative light emitting device 9, the hole injection layer 1111 is placed on the first electrode 1101 with PCzPA. And molybdenum oxide (VI) were co-deposited. The film thickness is 50 nm, and P The ratio of CzPA to molybdenum oxide (VI) is 4: 2 by weight (= PCzPA: molybdenum oxide). Butene) was adjusted to be.</p><p num="0612">Next, PCzPA was formed on the hole injection layer 1111 so as to have a film thickness of 10 nm, and holes were formed. A transport layer 1112 was formed.</p><p num="0613">In the comparative light emitting element 9, the first light emitting layer 1113a is PCzPA and 1,6FLPA Pr. It was formed by co-depositing with n. Here, the weight ratio of PCzPA and 1,6FLPA Prn is 1. Adjusted to: 0.05 (= PCzPA: 1,6FLPA Prn). Also, the first The film thickness of the light emitting layer 1113a was set to 10 nm.</p><p num="0614">Table 24 shows the element structures of the light emitting element 18, the light emitting element 19, and the comparative light emitting element 9 obtained as described above. Shown in.</p><p num="0615"><tables num="24"><img id="000089" he="89" wi="166" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0616">The light emitting element 18, the light emitting element 19, and the comparative light emitting element 9 are placed in a glove box having a nitrogen atmosphere. After performing the work of sealing the light emitting element so that it is not exposed to the atmosphere, each light emitting element The operating characteristics of the child were measured. The measurement is performed at room temperature (atmosphere maintained at 25 ° C). It was.</p><p num="0617">The light emitting element 18, the light emitting element 19, and the comparative light emitting element 9 were formed on the same substrate. Also , The hole injection layer 1111 and the hole transport layer 1112 and the first emission in the above three light emitting devices. Except for the optical layer 1113a, they are formed at the same time, and the operating characteristics are measured at the same time.</p><p num="0618">In the light emitting element 18, the light emitting element 19, and the comparative light emitting element 9, the brightness is 1000 cd / m.²near Voltage (V), current density (mA / cm) at²), CIE chromatic coordinates (x, y), brightness, (c d / m²), Current efficiency (cd / A), Power efficiency (lm / W), External quantum efficiency (%) Shown in 25.</p><p num="0619"><tables num="25"><img id="000090" he="27" wi="142" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></tables></p><p num="0620">The emission spectra of the light emitting element 18, the light emitting element 19, and the comparative light emitting element 9 are shown in FIG. 78. Figure In 78, the horizontal axis represents the wavelength (nm) and the vertical axis represents the emission intensity (arbitrary unit). Also, luminescent elements Figure 79 shows the voltage-luminance characteristics of the child 18, the light emitting element 19 and the comparative light emitting element 9. The characteristics are shown in Fig. 80, and the brightness-power efficiency characteristics are shown in Fig. 81. In Fig. 79, the vertical axis is the brightness (c). d / m²), Voltage (V) on the horizontal axis, current efficiency (cd / A) on the vertical axis, and horizontal axis in Fig. 80. Brightness (cd / m)²) Is shown. In FIG. 81, the vertical axis is the power efficiency (lm / W) and the horizontal axis is the horizontal axis. Brightness (cd / m)²) Is shown.</p><p num="0621">From FIG. 78, the light emitting element 18, the light emitting element 19, and the comparative light emitting element 9 all have 470 nm. It has a peak nearby. Also, from the CIE chromaticity coordinates in Table 25, the light emitting element 18 and the light emitting element Blue emission derived from 1,6 FLPA Prn was observed in the child 19 and the comparative light emitting element 9. It was found that the career balance was good. Further, the light emitting element 18 and light emitting of this embodiment The element 19 is a carbazo according to an aspect of the present invention as a host material for a blue fluorescent compound. The S1 level of the carbazole compound according to one aspect of the present invention is sufficiently applied. It was confirmed to be high (at least the S1 level higher than that of the blue fluorescent compound).</p><p num="0622">In particular, the carbazole compound according to one aspect of the present invention was applied to the first light emitting layer 1113a. The light emitting element 18 and the light emitting element 19 have higher efficiency than the comparative light emitting element 9. .. This indicates that the S1 level of the carbazole compound according to one aspect of the present invention is sufficiently high. ing.</p><p num="0623">Further, from FIGS. 79 to 81 and Table 25, the light emitting element 18 and the light emitting element 19 are comparatively light emitting. A light emitting element that can be driven at the same low voltage as the element 9 and has higher efficiency than the comparative light emitting element 9. It turned out to be. This is a book applied to the light emitting element 18 and the light emitting element 19 of this embodiment. The bandgap of the carbazole compound of one aspect of the invention is the PCz used in the comparative light emitting device 9. Since it is wider than the band gap of PA, it is used as a material for the hole transport layer in contact with the light emitting layer. In this case, it is considered that the energy transfer from the light emitting layer can be effectively suppressed. Also, the real thing Of the carbazole compound of one aspect of the present invention applied to the light emitting device 18 and the light emitting device 19 of the example. The LUMO level is shallower than the LUMO level of PCzPA used for the comparative light emitting device 9 (absolute value). Is small), so carrier loss due to electron leakage from the light emitting layer can be suppressed. .. Further, the carba of one aspect of the present invention applied to the light emitting element 18 and the light emitting element 19 of the present embodiment. The HOMO level of the sol compound is higher than the HOMO level of PCzPA used in the comparative light emitting device 9. Since it is deep (the absolute value is large), it is possible to effectively inject holes into the light emitting layer.</p><p num="0624">In addition, since all the elements have the same low drive voltage, the carrier movement is good for all the elements. It turned out to be good. This is a carrier of the carbazole compound according to one aspect of the present invention. It shows that it has excellent transportability.</p><p num="0625">From the above, by applying the carbazole compound of one aspect of the present invention as a material for a light emitting device, , It was shown that the light emitting element can be a highly efficient light emitting element. In addition, the present invention The carbazole compound of one embodiment can be applied as a host material for a blue fluorescent material. It has been shown.</p>

<p num="0626">In this embodiment, in the general formula (G1), R¹Is a phenyl group, and R²Is hydrogen, α³As a biphenyldiyl group having a phenanthrenyl group as a substituent, Ar³Phenanthroline 9-Phenyl-9H-3-, which is a carbazole compound of one aspect of the present invention using a tolenyl group. {4- [3,5-di (phenanthrene-9-yl) phenyl] phenyl} carbazole ( Abbreviation: Pn2BPPC) is shown as an example of manufacturing.</p><p num="0627"><chemistry num="65"><img id="000091" he="91" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0628">[Step 1: 9- [3-Chloro-5- (phenanthrene-9-yl) phenyl] Fena Synthesis method of Tren (abbreviation: Cl-PPn2)] 2.90 g of 1,3-dibromo-5-chlorobenzene in a 200 ml three-necked flask (10) .7 mmol), 9-phenanthrene boronic acid 5.0 g (22.5 mmol), paraacetate Zium (II) 50.6 mg (0.23 mmol), tri (o-tolyl) phosphine 20 7 mg (0.68 mmol), 70 mL of toluene, 7 mL of ethanol, 2 mol / L carbonic acid A mixture of 20 mL of potassium aqueous solution was degassed with stirring under reduced pressure, and then under a nitrogen atmosphere. The mixture was heated and stirred at 85 ° C for 6 hours to react. In addition, palladium (II) acetate (II) 50.6 mg ( 0.23 mmol), tri (o-tolyl) phosphine 207 mg (0.68 mmol) Add to the mixture, heat and stir at 85 ° C for 7.5 hours under a nitrogen atmosphere, then at 110 ° C 7. The mixture was heated and stirred for 5 hours to react.</p><p num="0629">After the reaction, 300 mL of toluene was added to this reaction mixture, and the organic layer of this mixture was floridied. Le (Wako Pure Chemical Industries, Ltd., Catalog No .: 540-00135), Alumina (Merck, Neutral), through Celite (Wako Pure Chemical Industries, Ltd., Catalog No .: 531-16855) And filtered. The obtained filtrate was washed with water, and magnesium sulfate was added to adsorb the water. This suspension was filtered to obtain a filtrate. The obtained filtrate is concentrated and silica gel column chromatograph Purification by Raffy was performed. At this time, as a developing solvent for chromatography, Torue A mixed solvent of hexane and hexane (toluene: hexane = 1: 5) was used. Obtained fraction Toluene and hexane were added, ultrasonic waves were applied, and then recrystallized. A white powder of the product was obtained with a yield of 3.11 g and a yield of 63%. The reaction scheme of the above synthesis method is as follows ( Shown in F8-1).</p><p num="0630"><chemistry num="66"><img id="000092" he="79" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0631">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex Sun = 10: 10) had an object of 0.25.</p><p num="0632">The compound obtained in step 1 above was measured by nuclear magnetic resonance spectroscopy (NMR). Measured below Show the data.¹1 H NMR (CDCl₃, 300MHz): δ (ppm) = 7.59-7.73 (m, 11H), 7.79 (s, 2H), 7.92 (d, J = 7.81Hz, 2H), 8.06 (d, J = 8.30Hz, 2H), 8.73 (d, J = 8.30Hz, 2H), 8.79 (d, J = 8.30Hz, 2H).</p><p num="0633">Also,¹The 1 H NMR chart is shown in FIGS. 82 (A) and 82 (B). Note that FIG. 82 (B) is a diagram. Chart showing the expanded range from 7.00ppm to 9.00ppm in 82 (A) Is. From the measurement results, the target 9- [3-chloro-5- (phenanthrene-9-a) It was confirmed that [Phenyl] phenanthrene (abbreviation: Cl-PPn2) was obtained.</p><p num="0634">[Step 2: 9-Phenyl-9H-3- {4- [3,5-di (phenanthrene-9-a) Le) Phenyl] Phenyl] Carbazole (abbreviation: Pn2BPPC) synthesis method] In a 200 mL three-necked flask, 9- [3-chloro-5- (phenanthrene-9-yl) flask Enil] Phenanthrene 1.04 g (2.87 mmol), 3- (9-Phenyl-9H- Carbazole) Phenyl-4-boronic acid 2.00 g (4.31 mmol), bis (diben) Dilidene Acetone) Palladium (0) 49.5 mg (0.09 mmol), 2'-(disi Clohexylphosphino) Acetophenone Ethylene Ketal 91.8 mg (0.24 mm) ol), cesium fluoride (I) 1.31 g (8.61 mmol), xylene 30 ml The mixture was heated and stirred at 150 ° C. for 12 hours under a nitrogen atmosphere to react.</p><p num="0635">After the reaction, 500 ml of toluene was added to this reaction mixture, and this mixture was added to alumina (Merck, Merck, Neutral), through Celite (Wako Pure Chemical Industries, Ltd., Catalog No .: 531-16855) And filtered. The obtained filtrate is concentrated and purified by silica gel column chromatography. went. At this time, a mixed solution of toluene and hexane was used as a developing solvent for chromatography. A medium (toluene: hexane = 1: 5) was used. The resulting fraction is concentrated and hexane After applying ultrasonic waves, the white powder of the target product was yielded at a yield of 1.9 g and recrystallized. Obtained at a rate of 89%. The reaction scheme of the above synthetic method is shown below (F8-2).</p><p num="0636"><chemistry num="67"><img id="000093" he="134" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0637">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex Sun = 10: 10), the target was 0.29.</p><p num="0638">The compound obtained in step 2 above was measured by nuclear magnetic resonance spectroscopy (NMR). Measured below Show the data.¹1 H NMR (CDCl₃, 300MHz): δ (ppm) = 7.43 (d, J = 3.4) Hz, 2H), 7.46-7.50 (m, 2H), 7.60-7.99 (m, 25H), 8.19-8.23 (m, 3H), 8.41 (d, J = 0.98Hz, 1H), 8.76 (d, J = 8.30Hz, 2H), 8.82 (d, J = 7.32Hz, 2H).</p><p num="0639">Also,¹The 1 H NMR chart is shown in FIGS. 83 (A) and 83 (B). Note that Fig. 83 (B) is a diagram. Chart showing the expanded range from 7.00ppm to 9.00ppm in 83 (A) Is. From the measurement results, the target product, 9-phenyl-9H-3- {4- [3,5-di (Fu) Enantren-9-yl) Phenyl] Phenyl} Carbazole (abbreviation: Pn2BPPC) Was obtained.</p><p num="0640">In this example, the phenanthrene compound having chlorine as a reactive group is carbazo. An example of coupling with a compound is shown, but the present invention is not limited to this, and iodine can be used as a reactive group. Alternatively, a phenanthrene compound having bromine may be used. Applicable to step 2 above The enantrene compound can be represented by, for example, the following general formula (I1). In addition, the following one The phenanthrene compound represented by the general formula (I1) has bromine or iodine as a reactive group. In this case, Pn2BPPC (abbreviation) can be synthesized by the same reaction as in step 2 above. .. Also, during step 1, phenanthrene-9-boronic acid was added to benzene trihalogenated. If you want to make a specific 2: 1 reaction, the halogen that reacts with these boronic acids is X. It is preferably more reactive than halogen. Therefore, if the X of benzene is chlorine, The halogens at the 3- and 5-positions are preferably bromine or iodine. Similarly, the X of benzene is In the case of bromine, the halogen at the 3- and 5-positions is preferably iodine.</p><p num="0641"><chemistry num="68"><img id="000094" he="55" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0642">However, in the general formula (I1), X represents chlorine, bromine or iodine.</p><p num="0643">The absorption spectrum of the synthesized Pn2BPPC toluene solution is shown in Fig. 84 (A). The torr is shown in Fig. 84 (B). In addition, the absorption spectrum of the thin film of Pn2BPPC is shown in Fig. 85 (A). ), The emission spectrum is shown in FIG. 85 (B). Ultraviolet-visible spectroscopic light for measurement of absorption spectrum A meter (manufactured by JASCO Corporation, V550 type) was used. Fluorescence intensity for measurement of emission spectrum A total (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) was used. Put the solution in a quartz cell and the thin film is stone A sample was prepared by vapor deposition on a British substrate and measured. Absorption spectrum for solution The absorption spectrum measured by putting only toluene in the quartz cell, and for the thin film, the quartz substrate The absorption spectrum obtained by subtracting the spectra is shown. Horizontal axis in FIGS. 84 and 85 Represents wavelength (nm) and vertical axis represents intensity (arbitrary unit). With 303 nm in the case of toluene solution An absorption peak was observed nearby, and the maximum emission wavelength was 388 nm (excitation wavelength 340 nm). .. In the case of a thin film, an absorption peak is seen near 306 nm, and the maximum emission wavelength is 417. It was nm (excitation wavelength 306 nm).</p><p num="0644">From the absorption spectrum, Pn2BPPC shown in this example is a material with almost no absorption in the visible region. It turned out to be a fee. In addition, it was found from the emission spectrum that it emits bluish purple light. ..</p><p num="0645">In this embodiment, in Pn2BPPC (abbreviation) of the general formula (G1), α³Biphenyl group Is attached at the para position to the 3-position of carbazole (4-biphenyltriyl group). , The reliability becomes good, which is preferable.</p>

<p num="0646">In this embodiment, 9-phenyl-9H-3- represented by the structural formula (197) in the first embodiment [3,5-di (phenanthrene-9-yl) phenyl] Carbazole (abbreviation: Pn2PP) A synthetic example for producing C) is shown.</p><p num="0647"><chemistry num="69"><img id="000095" he="81" wi="170" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0648">[Step 1: 3- (3,5-dichlorophenyl) -9-phenyl-9H-carbazole (Abbreviation: PCPCl₂) Synthesis method] In a 200 ml three-necked flask, 3- (9-phenyl-9H-carbazole) boronic acid 5. 0 g (22.1 mmol), 1-bromo-3,5-dichlorobenzene 7.63 g (26. 6 mmol), palladium (II) acetate 58.4 mg (0.26 mmol), tri (o- Trill) Phosphine 237 mg (0.78 mmol), toluene 98 mL, ethanol 1 Remove the mixture of 0 mL and 32 mL of 2 mol / L potassium carbonate aqueous solution with stirring under reduced pressure. After airing, the mixture was heated and stirred at 80 ° C. for 7 hours under a nitrogen atmosphere to react.</p><p num="0649">After the reaction, 500 ml of toluene is added to this reaction solution, and the organic layer of this mixed solution is floridi Filtered through all, alumina and Celite. Wash the obtained filtrate with water and use magnesium sulfate. Moisture was adsorbed. This suspension was filtered to obtain a filtrate. Concentrate the obtained filtrate , Purified by silica gel column chromatography. Chromatography exhibition at this time A mixed solvent of toluene and hexane (toluene: hexane = 10: 10) is used as the open solvent. It was. The obtained fraction was concentrated, hexane was added, ultrasonic waves were applied, and then recrystallized. Around that time, the white powder of the target product was obtained with a yield of 9.09 and a yield of 100%. Reaction ski of the above synthetic method The system is shown below (F9-1).</p><p num="0650"><chemistry num="70"><img id="000096" he="99" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0651">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex Sun = 10: 10), the target was 0.43.</p><p num="0652">The compound obtained in step 1 above was measured by nuclear magnetic resonance spectroscopy (NMR). Measured below Show the data.¹1 H NMR (CDCl₃, 300MHz): δ (ppm) = 7.26-7.34 (m, 2H), 7.40-7.53 (m, 4H), 7.57-7.67 (m, 7H), 8.20 (d, J = 7.81Hz, 1H), 8.31 (d, J = 0.98Hz, 1H).</p><p num="0653">Also,¹The 1 H NMR chart is shown in FIGS. 86 (A) and 86 (B). Note that Fig. 86 (B) is a diagram. Chart showing the expanded range from 7.00ppm to 8.50ppm in 86 (A) Is. From the measurement results, the target 3- (3,5-dichlorophenyl) -9-phenyl -9H-carbazole (abbreviation: PCPCl)₂) Was obtained.</p><p num="0654">[Step 2: 9-Phenyl-9H-3- [3,5-di (phenanthrene-9-yl) hu Enil] Synthesis method of carbazole (abbreviation: Pn2PPC)] 9-Phenanthrene Boronic Acid 4.29g (19.3mmo) in a 200mL three-necked flask l), 3- (3,5-dichlorophenyl) -9-phenyl-9H-carbazole 3.0g (7.73 mmol), bis (dibenzylideneacetone) palladium (0) 86.3 mg (0.15 mmol), 2'-(dicyclohexylphosphino) acetophenone ethylene Ketal 166 mg (0.46 mmol), cesium fluoride (I) 6.98 g (46 mm) ol), a mixture of 30 ml of xylene was heated and stirred at 120 ° C for 10 hours under a nitrogen atmosphere, and then I made it correspond. In addition, 9-phenanthrene boronic acid 858 mg (3.87 mmol), bi Su (dibenzylideneacetone) palladium (0) 86.3 mg (0.15 mmol), 2 '-(Dicyclohexylphosphino) acetophenone ethylene ketal 166 mg (0. 46 mmol) was added, and the mixture was heated and stirred at 120 ° C. for 8 hours to react.</p><p num="0655">After the reaction, 500 mL of toluene was added to this reaction mixture, and the organic layer of this mixture was made of alumina. Filtered through Celite. Wash the obtained filtrate with water, add magnesium sulfate, and add water. Was adsorbed. This suspension was filtered to obtain a filtrate. The obtained filtrate is concentrated and silica gel is used. Purification by lamb chromatography was performed. At this time, the developing solvent for chromatography As a mixture, a mixed solvent of toluene and hexane (toluene: hexane = 1: 5) was used. Obtained When the obtained fraction was concentrated, the target white powder was obtained in a yield of 0.93 g and a yield of 18%. Obtained. The reaction scheme of the above synthetic method is shown below (F9-2).</p><p num="0656"><chemistry num="71"><img id="000097" he="114" wi="169" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0657">Rf value by silica gel thin layer chromatography (TLC) (developing solvent ethyl acetate: hex Sun = 10: 10), the target was 0.18.</p><p num="0658">The compound obtained in step 2 above was measured by nuclear magnetic resonance spectroscopy (NMR). Measured below Show the data.¹1 H NMR (CDCl₃, 300MHz): δ (ppm) = 7.41-7.643 (d , J = 3.4Hz, 2H), 7.48-7.51 (d, J = 8.30Hz, 2H), 7. 60-8.05 (m, 20H), 8.15-8.18 (d, J = 9.3Hz, 2H), 8 .41 (d, J = 0.98Hz, 1H), 8.79 (dd, J = 8.3Hz, 18.6H) z, 4H).</p><p num="0659">Also,¹The 1 H NMR chart is shown in FIGS. 87 (A) and 87 (B). Note that FIG. 87 (B) is a diagram. Chart showing the expanded range from 7.00ppm to 9.00ppm in 87 (A) Is. From the measurement results, the target product, 9-phenyl-9H-3- [3,5-di (phenanthroline)) Tren-9-yl) phenyl] carbazole (abbreviation: Pn2PPC) was obtained. I acknowledged.</p><p num="0660">In this example, a carbazole compound having chlorine as a reactive group is used as a phenanthrene. An example of coupling with a len compound has been shown, but the present invention is not limited to this, and iodine is used as a reactive group. Alternatively, a carbazole compound having bromine may be used. Cal applicable to step 2 above The bazole compound can be represented by, for example, the following general formula (I2). The following general formula When the carbazole compound represented by (I2) has bromine or iodine as a reactive group, Pn2PPC can be synthesized by the same reaction as in step 2 above. Also, step 1 Medium, 9-Phenyl-9H-carbazole-3-boronic acid against benzene trihalogenated If you want to make a 1: 1 specific reaction, the halogen that reacts with these boronic acids is X. It is preferably more reactive than halogen. Therefore, the X of benzene at the 1st and 3rd positions is a salt. In the case of elementary, the halogen at the 5-position is preferably bromine or iodine. Also benzene When X is bromine, the halogen at the 5-position is preferably iodine.</p><p num="0661"><chemistry num="72"><img id="000098" he="64" wi="170" file="JP2017193572A_D0001.tif" img-format="tif" img-content="drawing" /></chemistry></p><p num="0662">However, in the general formula (I2), X represents chlorine, bromine or iodine.</p><p num="0663">The absorption spectrum of the synthesized Pn2PPC toluene solution is shown in Fig. 88 (A). This is shown in Fig. 88 (B). The absorption spectrum of the thin film of Pn2PPC is shown in Fig. 89 (A). , The emission spectrum is shown in FIG. 89 (B). Ultraviolet-visible spectrophotometer for measurement of absorption spectrum (JASCO Corporation, V550 type) was used. Fluorometer (fluorometer) for measuring emission spectrum FS920) manufactured by Hamamatsu Photonics Co., Ltd. was used. The solution is placed in a quartz cell, and the thin film is a quartz group. A sample was prepared by vapor deposition on a plate and measured. Absorption spectrum is quartz for solution The absorption spectrum measured by putting only toluene in the cell, and the spectrum of the quartz substrate for the thin film The absorption spectrum after subtracting the couture is shown. In FIGS. 88 and 89, the horizontal axis is the wave. The length (nm) and the vertical axis represent the intensity (arbitrary unit). In the case of toluene solution, around 298 nm An absorption peak was observed, and the maximum emission wavelength was 381 nm (excitation wavelength 311 nm). Well In the case of a thin film, an absorption peak is seen near 303 nm, and the maximum emission wavelength is 409 nm. (Excitation wavelength 304 nm).</p><p num="0664">From the absorption spectrum, the Pn2PPC shown in this example is a material with almost no absorption in the visible region. It turned out to be. Moreover, from the emission spectrum, it was found that the emission was bluish purple.</p>

0665100 boards 101 First electrode 102 EL layer 103 Second electrode 111 Hole injection layer 112 Hole transport layer 113 Light emitting layer 114 Electron transport layer 115 electron injection layer 301 First electrode 303 Second electrode 311 Luminescent unit 312 Luminescent unit 313 Charge generation layer