Diacenaphtho[1,2-b:1',2'-k]chrysene derivative

The present invention relates to a novel skeleton, diacenaft [1,2-b: 1', 2'-k] chrysene derivatives.

The organic light emitting element sandwiches a thin film containing a fluorescent organic compound between an anode and a cathode, and injects electrons and holes (holes) from each electrode to generate an exciter of the fluorescent compound, and this excitation is performed. It is an element that utilizes the light emitted when the child returns to the base state.

Recent advances in organic light-emitting devices have been remarkable, and their features are high brightness at low applied voltage, versatility of light-emitting wavelengths, high-speed responsiveness, thin and lightweight light-emitting devices, which makes them possible for a wide range of applications. Suggests sex.

However, at present, higher brightness optical output or higher conversion efficiency is required. In addition, there are still many problems in terms of durability such as changes over time due to long-term use and deterioration due to atmospheric gas containing oxygen and humidity.

Furthermore, when considering application to a full-color display or the like, the color purity is good and high-efficiency light emission is required, but these problems are not yet sufficient. Further, there is a demand for an organic light emitting device having particularly high color purity, luminous efficiency, and durability, and a material for realizing the organic light emitting device.

There are examples shown in Patent Documents 1 to 4 as materials for the light emitting layer in order to improve the luminous efficiency of the light emitting layer, but none of the materials is sufficient for practical use, and development of a new material with a high quantum yield is required. ing.<patcit num="1"><text>Japanese Unexamined Patent Publication No. 1-289907</text></patcit><patcit num="2"><text>Japanese Unexamined Patent Publication No. 2-247278</text></patcit><patcit num="3"><text>Japanese Unexamined Patent Publication No. 8-113576</text></patcit><patcit num="4"><text>Japanese Unexamined Patent Publication No. 11-12205</text></patcit>

<p> The organic compound described in the above patent document and the organic light emitting device containing the organic compound have room for improvement from the viewpoint of practical use.</p><p> Specifically, for practical use, higher brightness optical output or higher conversion efficiency is required. In addition, it is necessary to improve durability such as aging due to long-term use and deterioration due to atmospheric gas containing oxygen and humidity.</p><p> Furthermore, when considering application to a full-color display or the like, the required organic light emitting device requires good color purity and high efficiency blue light emission, but these problems are not yet sufficient.</p><p> Therefore, there is a particular demand for organic light emitting devices having high color purity, luminous efficiency, and durability, and materials for realizing them.</p><p> The present invention has been made to solve the problems of the prior art as described above. That is, an object of the present invention is to provide a novel organic compound suitable for use in a blue light emitting device more specifically.</p>

<p> The present inventors have completed the present invention as a result of studies for solving the above-mentioned problems.</p><p> That is, the present invention provides a diacenaft [1,2-b: 1', 2'-k] chrysene derivative having a skeleton represented by the following formula.</p><p><chemistry num="1"><img file="JP2010143879A_D0001.tif" /></chemistry></p>

<p> The compound of the present invention, that is, a diacenaft [1,2-b: 1', 2'-k] chrysene derivative, has high efficiency and high brightness emission performance. And the organic light emitting element having it can realize high efficiency and high brightness light emission. In addition, a durable organic light emitting element can be realized.</p>

Hereinafter, the compound of the present invention will be described in detail.

The skeleton of the diacenaft [1,2-b: 1', 2'-k] chrysene derivative according to the present invention is novel.

The skeleton of the diacenaft [1,2-b: 1', 2'-k] chrysene derivative is shown below.

<chemistry num="2"><img file="JP2010143879A_D0002.tif" /></chemistry>

More specifically, the diacenaft [1,2-b: 1', 2'-k] chrysene derivative according to the present invention is represented by the following general formula (1).

<chemistry num="3"><img file="JP2010143879A_D0003.tif" /></chemistry>

R₁To R₂₀Are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocycle. Represents a group.

In addition, specific examples of the substituents of the compound in the above general formula (1) are shown below.

Here, in the formula (1), as the alkyl group of the substituted or unsubstituted alkyl group, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, 1 -Adamanthyl group, 2-adamantyl group, etc. can be mentioned, but of course, they are not limited to these.

Here, in the formula (1), as the alkoxy group of the substituted or unsubstituted alkoxy group, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, a phenoxy group, a 4-tershalbutylphenoxy group, a benzyloxy group. Groups, thienyloxy groups and the like can be mentioned, but of course the group is not limited thereto.

Here, in the formula (1), as the amino group of the substituted or unsubstituted amino group, N-methylamino group, N-ethylamino group, N, N-dimethylamino group, N, N-diethylamino group, N-methyl -N-Ethylamino group, N-benzylamino group, N-methyl-N-benzylamino group, N, N-dibenzylamino group, Anilino group, N, N-diphenylamino group, N, N-dinaphthylamino Group, N, N-difluorenylamino group, N-phenyl-N-tolylamino group, N, N-ditrilamino group, N-methyl-N-phenylamino group, N, N-dianisolylamino group, N- Mesityl-N-phenylamino group, N, N-dimethylamino group, N-phenyl-N- (4-tershaributylphenyl) amino group, N-phenyl-N- (4-trifluoromethylphenyl) amino group, etc. These are, of course, not limited to these.

Here, in the formula (1), examples of the aryl group of the substituted or unsubstituted aryl group include a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group and the like, but of course, they are limited to these. It's not a thing.

Here, in the formula (1), examples of the heterocyclic group of the substituted or unsubstituted heterocyclic group include a pyridyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinyl group, a phenanthrolyl group and the like. Of course, it is not limited to these.

In the formula (1), as the substituent contained in the above-mentioned substituent, that is, an alkyl group, an alkoxy group, an amino group, an aryl group, or a heterocyclic group, Alkyl groups such as methyl group, ethyl group, propyl group, Aralkyl groups such as benzyl groups, Aryl groups such as phenyl group and biphenyl group, Heterocyclic groups such as pyridyl group and pyrrolyl group, Amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditrilamino group, Alkoxy groups such as methoxyl group, ethoxyl group, propoxyl group, phenoxyl group, Examples include, but are not limited to, cyano groups, halogen atoms such as fluorine, chlorine, bromine, and iodine.

Specific examples of the compound in the above general formula (1) are shown below. However, the present invention is not limited to these.

<chemistry num="4"><img file="JP2010143879A_D0004.tif" /></chemistry>

<chemistry num="5"><img file="JP2010143879A_D0005.tif" /></chemistry>

<chemistry num="6"><img file="JP2010143879A_D0006.tif" /></chemistry>

<chemistry num="7"><img file="JP2010143879A_D0007.tif" /></chemistry>

<chemistry num="8"><img file="JP2010143879A_D0008.tif" /></chemistry>

Hereinafter, the compound of the present invention will be described in more detail.

Generally, in order to increase the luminous efficiency of an organic light emitting device, it is desired that the emission quantum yield of the emission center material itself is large.

Then, as a result of studies by the present inventors, it was found that the compound represented by the general formula (1) has a high quantum yield in a dilute solution. Therefore, when the compound represented by the general formula (1) is used for the organic light emitting device, it can be said that high luminous efficiency can be expected.

The organic compound of the present invention is a derivative having a diacenaft [1,2-b: 1', 2'-k] chrysene skeleton.

When using an organic compound as a light emitting material, a high quantum yield of the material itself is important. for that purpose First, the oscillator strength is high Secondly, there are few vibrating parts of the skeleton related to light emission. Can be given. The present inventors consider that it is important that both of these two conditions are satisfied.

Regarding the first, it is important to increase the symmetry of the skeleton involved in the emission of molecules. However, it may not emit light at all under the forbidden transition conditions peculiar to highly symmetric molecules. Further, by extending the conjugate in the same direction, the moment of the molecule is increased and the oscillator strength is improved.

Regarding the second, since the skeleton involved in light emission does not have a rotating structure, it is possible to suppress a decrease in quantum yield due to vibration due to rotation.

FIG. 5 shows the X-axis and the Y-axis orthogonal to the skeleton and moment of the diacenaft [1,2-b: 1', 2'-k] chrysene derivative according to the present invention.

This will be described with reference to FIG.

At the first point above, it can be said that the skeleton has a large moment in the X-axis direction and obtains high oscillator strength. Also, the targetness is good. In the second point above, since the main skeleton does not have a rotation axis, the quantum yield does not decrease due to vibration deactivation, and it can be said that the skeleton is suitable as a light emitting material.

In addition, the diacenaft [1,2-b: 1', 2'-k] chrysene derivative has high flatness, and excimer formation is likely to occur if it is unsubstituted. Therefore, it is preferable to introduce a substituent in order to prevent the formation of excimers, and the position where the substituent is introduced is not particularly limited, but the 7,9,10,17,19,20 positions near the central skeleton are located. Are suitable.

The following general formula shows the substitution positions of diacenaft [1,2-b: 1', 2'-k] chrysene derivatives in the skeleton numerically.

<chemistry num="9"><img file="JP2010143879A_D0009.tif" /></chemistry>

As described above, the diacenaft [1,2-b: 1', 2'-k] chrysene derivative according to the present invention has a property that the skeleton itself has a high oscillator strength and a property that there are few vibrating parts of the skeleton related to light emission. It is equipped.

In addition, this diacenaft [1,2-b: 1', 2'-k] chrysene derivative has a novel skeleton itself, and it is considered that it has high efficiency and high brightness emission performance due to these properties.

The diacenaft [1,2-b: 1', 2'-k] chrysene derivative represented by the general formula [1] is described in, for example, J.Org.Chem.1952,17,845-54, J.Org.Chem. With reference to 2006,71,5921-5929, J.Org.Chem.2003,68,883-887, Chem.Commun.,2005,21722174, synthesize as the following synthetic routes 1, 2, 3 and 4. be able to. For the substituents that replace the skeleton of the diacenaft [1,2-b: 1', 2'-k] chrysen derivative, the hydrogen atom is replaced with another substituent such as an alkyl group, a halogen atom, or a phenyl group. It can be introduced by synthesizing.

<chemistry num="10"><img file="JP2010143879A_D0010.tif" /></chemistry>

<chemistry num="11"><img file="JP2010143879A_D0011.tif" /></chemistry>

<chemistry num="12"><img file="JP2010143879A_D0012.tif" /></chemistry>

<chemistry num="13"><img file="JP2010143879A_D0013.tif" /></chemistry>

The synthetic compounds obtained by Synthesis Examples 2 to 8 are shown in the table below.

Based on Synthesis Example 1, by replacing B1 and B2 shown in Synthesis Example 1 with the compounds shown in the following table, synthetic compounds can be obtained from each Synthesis Example. The table below also shows B1 and B2 used in Synthesis Example 1.

<chemistry num="14"><img file="JP2010143879A_D0014.tif" /></chemistry>

Synthesis examples 9 to 16 are summarized in the table below. In Synthesis Examples 9 to 16, a synthetic compound is obtained by replacing C1, C2, C3, and C4 described in the synthetic route 2 or 4 with the compounds described in the following table based on the synthetic route 2 or 4. It shows that can be done.

The synthetic routes 2 and 4 are the same synthetic compounds except that the synthetic routes are different.

<chemistry num="15"><img file="JP2010143879A_D0015.tif" /></chemistry>

Synthesis Examples 17 to 22 are summarized in the table below. Synthesis Examples 17 to 22 show that a synthetic compound can be obtained by replacing D1 and D2 described in the above synthetic route 3 with the compounds described in the following table based on the above synthetic route 3. ..

<chemistry num="16"><img file="JP2010143879A_D0016.tif" /></chemistry>

Next, an organic light emitting device having the diacenaft [1,2-b: 1', 2'-k] chrysene derivative according to the present invention will be described.

The organic light emitting device according to the present embodiment has a pair of electrodes, an anode and a cathode, and an organic compound layer arranged between them. This organic compound layer is a diacenaft [1,2-b: 1', 2'-k] chrysene derivative having a skeleton represented by the above formula or diacenaft [1,2-b:: represented by the general formula (1). It has a 1', 2'-k] chrysene derivative.

An organic light emitting device is an element in which a light emitting material, which is an organic compound arranged between a pair of electrodes, emits light.

When one layer of the organic compound layer is a light emitting layer, the light emitting layer may be composed of only the organic compound according to the present invention, or may have a part of the organic compound according to the present invention.

When the light emitting layer may partially contain the organic compound according to the present invention, the organic compound according to the present invention may be a main component or a sub component of the light emitting layer.

Here, as the main component and the sub-component, for all the compounds constituting the light emitting layer, for example, those having a large weight or molar number are referred to as a main component, and those having a small number are referred to as sub-components.

The material that is the main component can also be called the host material.

The material which is a sub-component can be called a dopant (guest) material, a light emitting assist material, and a charge injection material.

When the organic compound according to the present invention is used as a guest material, the concentration of the guest material with respect to the host material is preferably 0.01 wt% or more and 20 wt% or less, and more preferably 0.5 wt% or more and 10 wt% or less. Further, by changing the concentration of the guest material in either of the above two ranges, it is possible to make the emission wavelength of the light emitted from the light emitting layer longer in the range of 5 nm or more and 20 nm or less than the wavelength of the solution. ..

When the above light emitting layer is composed of a carrier transportable host material and a guest material, the main process leading to light emission consists of the following several processes. 1. Transport of electrons and holes within the light emitting layer. 2. Exciton generation of host material. 3. Transfer of excitation energy between molecules of host materials. 4. Excitation energy transfer from host material to guest material.

The desired energy transfer and luminescence in each process occur in various deactivation processes and competitions.

Needless to say, in order to increase the luminous efficiency of the organic light emitting element, the emission quantum yield of the emission center material (for example, guest material) itself is large. However, how efficiently energy transfer between the host material and the host material or between the host material and the guest material can be made is also a big issue. The cause of the luminescence deterioration due to energization is not clear at present, but it is assumed that it is at least related to the environmental change of the luminescence center material itself or its peripheral molecules.

Therefore, the present inventors have conducted various studies, and an element using the compound represented by the general formula (1) of the present invention as a host material or a guest material of a light emitting layer, particularly a guest material, has high efficiency and high brightness. It has a light output and has been found to be extremely durable.

Next, the organic light emitting device according to the present embodiment will be described in detail.

The organic light emitting element according to the present embodiment is an organic light emitting element composed of a pair of electrodes composed of an anode and a cathode and an organic compound layer arranged between the pair of electrodes, in which the organic compound layer is diacenaft [1, It has a derivative having a 2-b: 1', 2'-k] chrysene skeleton or a diacenaft [1,2-b: 1', 2'-k] chrysene derivative represented by the general formula (1).

A compound layer other than the organic compound layer may be provided between the pair of electrodes.

Two or more compound layers including the organic compound layer may be provided between the pair of electrodes. Such a case will be referred to as a multi-layer organic light emitting device.

The first to fifth are shown below as preferable examples of the multilayer type organic light emitting element.

As an example of the first multilayer type organic light emitting device, a configuration in which (anode / light emitting layer / cathode) are sequentially provided on a substrate may be mentioned. The organic light emitting device used here is useful when it has a single hole transporting ability, an electron transporting ability, and a light emitting property by itself, or when a compound having each property is mixed and used. ..

As an example of the second multilayer type organic light emitting device, a configuration in which (anode / hole transport layer / electron transport layer / cathode) are sequentially provided on a substrate may be mentioned. In this case, the luminescent material uses a material having either hole-transporting property, electron-transporting property, or both functions for each layer, and is combined with a simple hole-transporting substance or electron-transporting substance having no luminescence. It is useful when using it. Further, in this case, the light emitting layer is composed of either a hole transport layer or an electron transport layer.

As an example of the third multilayer organic light emitting device, a configuration in which (anode / hole transport layer / light emitting layer / electron transport layer / cathode) are sequentially provided on a substrate may be mentioned. It separates the functions of carrier transport and luminescence. Then, it can be used in a timely combination with a compound having each property of hole transportability, electron transportability, and luminescence. Further, the degree of freedom in material selection is extremely increased, and various compounds having different emission wavelengths can be used, so that the emission hue can be diversified. Further, it is possible to effectively confine each carrier or exciton in the central light emitting layer to improve the luminous efficiency.

As an example of the fourth multilayer type organic light emitting device, a configuration in which (anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode) are sequentially provided on a substrate may be mentioned. This is effective in improving the adhesion between the anode and the hole transport layer or improving the injection property of the hole, and is effective in lowering the voltage.

As an example of the fifth multilayer organic light emitting device, a configuration in which (anode / hole transport layer / light emitting layer / hole / exciton blocking layer / electron transport layer / cathode) are sequentially provided on a substrate may be mentioned. This is a configuration in which a layer (hole / exciton blocking layer) that prevents holes or excitons from exiting to the cathode side is inserted between the light emitting layer and the electron transport layer. By using a compound having a very high ionization potential as a hole / exciton blocking layer, it is an effective configuration for improving luminous efficiency.

The light emitting region containing the compound represented by the general formula (1) in the present invention refers to the region of the above light emitting layer.

However, the first to fifth multilayer type examples are only very basic element configurations, and the configuration of the organic light emitting device using the compound according to the present invention is not limited to these. For example, various layer configurations can be taken, such as providing an insulating layer at the interface between the electrode and the organic layer, providing an adhesive layer or an interference layer, and the electron transport layer or the hole transport layer being composed of two layers having different ionization potentials. ..

The compound represented by the general formula (1) used in the present invention can be used in any of the forms of the first to fifth examples.

In the organic light emitting device according to the present embodiment, the layer containing the organic compound contains at least one organic compound represented by the general formula (1) used in the present invention, and is particularly used as a guest material for the light emitting layer. Is preferable.

The organic compound according to the present invention may be used as a host material for the light emitting layer.

The organic compound according to the present invention may be used for each layer other than the light emitting layer, that is, any of a hole injection layer, a hole transport layer, a hole exciton blocking layer, an electron transport layer, or an electron injection layer.

Here, in addition to the organic compound of the present invention, conventionally known low-molecular-weight and high-molecular-weight hole-transporting compounds, luminescent compounds, electron-transporting compounds and the like can be used together, if necessary.

Examples of these compounds are given below.

As the hole injection transportable material, a material having high hole mobility is preferable so that holes can be easily injected from the anode and the injected holes can be transported to the light emitting layer. Examples of low-molecular-weight and high-molecular-weight materials having hole injection and transport performance include triarylamine derivatives, phenylenediamine derivatives, stillben derivatives, phthalocyanine derivatives, porphyrin derivatives, poly (vinylcarbazole), poly (thiophene), and other highly conductive materials. Molecules can be mentioned, but of course not limited to these.

Mainly, as the host material, in addition to the compound which is the table or the derivative of the table, a condensed ring compound (for example, fluorene derivative, naphthalene derivative, anthracene derivative, pyrene derivative, carbazole derivative, quinoxalin derivative, quinoline derivative, etc.), tris (8) -Includes, but is not limited to, organic aluminum complexes such as quinolinolate) aluminum, organic zinc complexes, and polymer derivatives such as triphenylamine derivatives, poly (fluorene) derivatives, and poly (phenylene) derivatives. ..

<chemistry num="17"><img file="JP2010143879A_D0017.tif" /></chemistry>

The electron-injection-transporting material can be arbitrarily selected from those that can easily inject electrons from the cathode and can transport the injected electrons to the light-emitting layer. It is selected in consideration of the balance of. Examples of the material having electron injection transport performance include, but are of course limited to, oxadiazole derivative, oxazol derivative, pyrazine derivative, triazole derivative, triazine derivative, quinoline derivative, quinoxalin derivative, phenanthroline derivative, organic aluminum complex and the like. It's not a thing.

As the anode material, a material having a work function as large as possible is preferable. For example, a single metal such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten or an alloy thereof, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide, etc. Metal oxides can be used. In addition, conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used. These electrode substances may be used alone or in combination of two or more. Further, the anode may have a single-layer structure or a multi-layer structure.

On the other hand, as the cathode material, a material having a small work function is preferable. For example, alkali metals such as lithium, alkaline earth metals such as calcium, and simple metals such as aluminum, titanium, manganese, silver, lead, and chromium can be mentioned. Alternatively, an alloy in which these metal simple substances are combined can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium and the like can be used. It is also possible to use metal oxides such as indium tin oxide (ITO). These electrode substances may be used alone or in combination of two or more. Further, the cathode may have a single-layer structure or a multi-layer structure.

The substrate used in the organic light emitting element of the present embodiment is not particularly limited, but an opaque substrate such as a metal substrate and a ceramic substrate, and a transparent substrate such as glass, quartz, and a plastic sheet are used. It is also possible to control the color development light by using a color filter film, a fluorescence color conversion filter film, a dielectric reflection film, or the like on the substrate.

A protective layer or a sealing layer may be provided on the manufactured device for the purpose of preventing contact with oxygen, moisture, or the like. Examples of the protective layer include an inorganic material film such as a diamond thin film, a metal oxide and a metal nitride, a polymer film such as a fluororesin, polyethylene, a silicone resin and a polystyrene resin, and a photocurable resin. Further, the device itself can be packaged with a suitable sealing resin by coating with glass, a gas permeable film, a metal or the like.

In the organic light emitting device according to the present embodiment, the layer containing the organic compound of the present invention and the layer composed of other organic compounds are formed by the methods shown below. Generally, a thin film is formed by a vacuum vapor deposition method, an ionization vapor deposition method, sputtering, plasma, or a known coating method (for example, spin coating, dipping, casting method, LB method, inkjet method, etc.) by dissolving in a suitable solvent. Here, when a layer is formed by a vacuum vapor deposition method, a solution coating method, or the like, crystallization or the like is unlikely to occur and the stability over time is excellent. Further, when the film is formed by the coating method, the film can be formed by combining with an appropriate binder resin.

Examples of the binder resin include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, urea resin and the like. .. Further, these binder resins may be used alone as a homopolymer or a copolymer, or may be used as a mixture of two or more. Further, if necessary, known additives such as plasticizers, antioxidants, and ultraviolet absorbers may be used in combination.

The organic light emitting device according to this embodiment can be applied to products that require energy saving and high brightness. Examples of applications include display devices / lighting devices, light sources for printers, and backlights for liquid crystal display devices.

As a display device, an energy-saving, highly visible, and lightweight flat panel display becomes possible. The display device can be used as an image display device such as a PC, a television, or an advertising medium. Alternatively, the display device may be used as a display unit of an image pickup device such as a digital still camera or a digital video camera.

Alternatively, the display device may be used as an electrophotographic image forming device, that is, an operation display unit of a laser beam printer, a copying machine, or the like.

Further, it can be used as an electrophotographic image forming apparatus, that is, a light source used when exposing a latent image to a photoconductor such as a laser beam printer or a copying machine. A latent image can be formed by arranging a plurality of independently addressable organic light emitting elements in an array (for example, linear) and performing desired exposure on the photosensitive drum. By using the organic light emitting element according to the present embodiment, it is possible to reduce the space required for arranging the light source, the polycon mirror, various optical lenses, and the like.

Energy saving effect can be expected for lighting equipment and backlights. Further, the organic light emitting device according to the present embodiment can be used as a flat light source.

Further, it is also possible to control the color-developed light by providing a color filter film, a fluorescence color conversion filter film, a dielectric reflection film, or the like on the substrate supporting the organic light emitting element according to the present embodiment. Further, a thin film transistor (TFT) can be provided on the substrate, and an organic light emitting element can be connected to the thin film transistor (TFT) to control light emission and non-light emission. It is also possible to arrange a plurality of organic light emitting elements in a matrix, that is, arrange them in the in-plane direction to use as a lighting device.

Next, a display device using the organic light emitting element according to the present embodiment will be described. This display device is characterized by comprising an organic light emitting element according to the present embodiment and a means for supplying an electric signal to the organic light emitting element according to the present embodiment. Hereinafter, the display device according to the present embodiment will be described in detail with reference to the drawings, taking the active matrix method as an example.

FIG. 1 schematically shows a configuration example of a display device including an organic light emitting element according to the present embodiment, which is one form of the display device, and a means for supplying an electric signal to the organic light emitting element according to the present embodiment. It is a figure which shows.

FIG. 2 is a diagram schematically showing a pixel circuit connected to a pixel, a signal line connected to the pixel circuit, and a current supply line.

The means for supplying an electric signal to the organic light emitting element according to the present embodiment refers to the scanning signal driver 11, the information signal driver 12, the current supply source 13 in FIG. 1, and the pixel circuit 15 in FIG.

In the display device 1 of FIG. 1, a scanning signal driver 11, an information signal driver 12, and a current supply source 13 are arranged, and are connected to a gate selection line G, an information signal line I, and a current supply line C, respectively. A pixel circuit 15 is arranged at the intersection of the gate selection line G and the information signal line I (Fig. 2). The pixel 14 composed of the organic light emitting element according to the present embodiment is provided corresponding to each of the pixel circuits 15. Pixel 14 is an organic light emitting element. Therefore, in this figure, an organic light emitting element is shown as a light emitting point. In this figure, the upper electrode of the organic light emitting element may be common to the upper electrode of another organic light emitting element. Of course, the upper electrode may be provided individually for each light emitting element.

The scanning signal driver 11 sequentially selects the gate selection lines G1, G2, G3 ... Gn, and in synchronization with this, the image signal from the information signal driver 12 is any of the information signal lines I1, I2, I3 ... In. It is applied to the pixel circuit 15 via a screwdriver.

Next, the operation of the pixels will be described. FIG. 3 is a circuit diagram showing a circuit constituting one pixel arranged in the display device of FIG. In FIG. 3, the second thin film transistor (TFT2) 23 controls the current for causing the organic light emitting element 24 to emit light. In the pixel circuit 2 of FIG. 3, when the selection signal is applied to the gate selection line Gi, the first thin film transistor (TFT1) 21 is turned on and the capacitor (C) is turned on._add) 22 is supplied with the image signal Ii to determine the gate voltage of the second thin film transistor (TFT2) 23. A current is supplied to the organic light emitting element 24 from the current supply line Ci according to the gate voltage of the second thin film transistor (TFT2) (23). Here, the gate potential of the second thin film transistor (TFT2) 23 is the capacitor (C) until the first thin film transistor (TFT1) 21 is selected for scanning next._add) Holds at 22. Therefore, the current continues to flow through the organic light emitting element 24 until the next scan is performed. As a result, the organic light emitting element 24 can always emit light during one frame period.

Although not shown, the organic light emitting element according to the present embodiment can also be used in a voltage writing type display device in which the thin film transistor controls the voltage between the electrodes of the organic light emitting element 24.

FIG. 4 is a schematic view showing an example of the cross-sectional structure of the TFT substrate used in the display device of FIG. The details of the structure will be described below while showing an example of the manufacturing process of the TFT substrate.

When manufacturing the display device 3 of FIG. 4, first, a moisture-proof film 32 for protecting a member (TFT or an organic layer) formed on the upper portion is coated on a substrate 31 such as glass. As a material constituting the moisture-proof film 32, silicon oxide or a composite of silicon oxide and silicon nitride is used. Next, by forming a film of a metal such as Cr by sputtering, the gate electrode 33 is formed by patterning it into a predetermined circuit shape.

Subsequently, silicon oxide or the like is formed into a film by a plasma CVD method, a catalytic chemical vapor deposition method (cat-CVD method), or the like, and patterned to form a gate insulating film 34. Next, a silicon film is formed by a plasma CVD method or the like (in some cases, annealed at a temperature of 290 ° C or higher), and the semiconductor layer 35 is formed by patterning according to the circuit shape.

Further, the TFT element 38 is manufactured by providing the drain electrode 36 and the source electrode 37 on the semiconductor film 35, and a circuit as shown in FIG. 3 is formed. Next, an insulating film 39 is formed on the upper part of the TFT element 38. Next, the contact hole (through hole) 310 is formed so that the anode 311 for the organic light emitting element made of metal and the source electrode 37 are connected to each other.

The display device 3 can be obtained by sequentially laminating a multilayer or single-layer organic layer 312 and a cathode 313 on the anode 311. At this time, a first protective layer 314 or a second protective layer 315 may be provided in order to prevent deterioration of the organic light emitting element. By driving the display device using the organic light emitting element according to the present embodiment, it is possible to perform stable display even for a long time display with good image quality.

The above display device is not particularly limited to the switching element, and can be easily applied to a single crystal silicon substrate, a MIM element, an a-Si type, or the like.

An organic light emitting display panel can be obtained by sequentially laminating a multilayer or single layer organic light emitting layer / cathode layer on the ITO electrode. By driving the display panel using the organic compound according to the present embodiment, it is possible to perform stable display even for a long time display with good image quality.

Further, regarding the light extraction direction of the element, either a bottom emission configuration (a configuration in which light is extracted from the substrate side) or a top emission (a configuration in which light is extracted from the opposite side of the substrate) is possible.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto.

&lt;Example 1&gt;

<chemistry num="18"><img file="JP2010143879A_D0018.tif" /></chemistry>

Chloral hydrate 11.82 g (110 mmol), sodium sulfate 113.6 g (800 mmol), and 400 ml of water were placed in a 500 ml eggplant flask and heated to 40 ° C. 1,5-Diaminonaphthalene, 7.91 g (50 mmole), water 60 ml, 12N hydrochloric acid 8.75 ml in a 100 ml eggplant flask, hydroxylamine hydrochloride 22.9 g (330 mmol), water 100 ml in a 200 ml eggplant flask. After that, it is added while stirring vigorously in sequence. After charging, stirring was performed at 80 ° C. for 1 hour. After cooling, the precipitate was filtered, washed with water, and dried to obtain a black powder. This black powder was gradually added to a 100 ml eggplant flask heated to 30 ml of concentrated sulfuric acid and 60 ° C. so that the internal temperature did not rise. Then, stirring was performed for 30 minutes. After cooling, the mixture was emptied into 200 g of ice, the precipitate was filtered, washed with warm water, and dried to obtain 8 g of black powder.

<chemistry num="19"><img file="JP2010143879A_D0019.tif" /></chemistry>

5.3 g of black powder and 80 ml of a 10% potassium hydroxide aqueous solution were placed in a 300 ml eggplant flask and heated to 40 ° C. After slowly dropping 23 ml of 30% hydrogen peroxide solution, the mixture was stirred at 80 ° C. for 1 hour. After cooling, the pH was adjusted to 4 with hydrochloric acid, and the precipitate was filtered and washed with water to obtain 1.5 g of black powder.

<chemistry num="20"><img file="JP2010143879A_D0020.tif" /></chemistry>

246 mg of black powder, 712 mg (2 mmol) of E1 and 50 ml of toluene were put into a 200 ml eggplant flask and heated to 80 ° C. After slowly dropping 234 mg (2 mmol) of isoamyl nitrite, the mixture was stirred at 110 ° C. for 3 hours. After cooling, it was washed with 100 ml of water x 2 times. The organic layer was washed with saturated brine, dried over magnesium sulfate, and then the solution was filtered and concentrated to give a brown liquid. This was purified by column chromatography (toluene / heptane = 1: 1) and then recrystallized from chloroform / methanol to obtain 20 mg (yield 1.2%) of compound A3 in yellow crystals.

In addition, the structure of this compound was confirmed by NMR measurement.

¹1 H NMR (CDCl₃, 500MHz) σ (ppm): 7.98 (d, 2H, J = 9.5Hz), 7.70-7.62 (m, 20H), 7.52 (d, 4H, J = 7.0Hz), 7.51-7.20 (m, 6H), 6.50 (d, 2H, J = 7.0Hz), 6.31 (d, 2H, J = 7.5Hz). Exemplified compound A3, 1 × 10^-5The emission spectrum of the toluene solution at mol / l was a spectrum having the maximum intensity at 459 nm as a result of measuring photoluminescence at an excitation wavelength of 350 nm using a Hitachi F-4500.

&lt;Example 2&gt;

<chemistry num="21"><img file="JP2010143879A_D0021.tif" /></chemistry>

Chrysene 550 mg (2 mmol), E2 50 mg (0.1 mmol), 4,4'-di-tert-butyl-2,2'-bipyridine 54 mg (0.2 mmol), E3 559 mg (2.2 mmol), cyclohexane 10 ml in a 50 ml eggplant flask It was charged and stirred at 80 ° C for 10 hours. After cooling, the organic layer was washed with saturated brine, dried over magnesium sulfate, and the solution was filtered and concentrated to obtain a brown liquid. This was purified by column chromatography (toluene) and then recrystallized from methanol / heptane to obtain 350 mg (yield 55%) of a mixture of white crystals.

<chemistry num="22"><img file="JP2010143879A_D0022.tif" /></chemistry>

White crystal mixture 144 mg (0.3 mmol), 1,8-diiodonaphthalene 228 mg (0.6 mmol), Pd₂(dba)₃ 62 mg (0.06 mmol), 67 mg (0.24 mmol) of tricyclohexylphosphine, 0.5 ml of DBU, and 5 ml of dimethylformamide were placed in a 10 ml eggplant flask, and the mixture was stirred at 160 ° C. for 5 hours. After cooling, the organic layer was washed with saturated brine, dried over magnesium sulfate, and the solution was filtered and concentrated to obtain a brown liquid. This was purified by column chromatography (chloroform / heptane) and then recrystallized from methanol / heptane to obtain 50 mg (yield 10%) of compound A1 in yellow crystals.

Exemplified compound A3, 1 × 10^-5The emission spectrum of the toluene solution at mol / l was a spectrum having the maximum intensity at 440 nm as a result of measuring photoluminescence at an excitation wavelength of 350 nm using a Hitachi F-4500.

&lt;Example 3&gt; [Synthesis of Exemplified Compound A1] It was synthesized in the same manner except that the raw material chrysene used in Example 2 was changed to E4.

<chemistry num="23"><img file="JP2010143879A_D0023.tif" /></chemistry>

Exemplified compound A3, 1 × 10^-5The emission spectrum of the toluene solution at mol / l was a spectrum having the maximum intensity at 455 nm as a result of measuring photoluminescence at an excitation wavelength of 350 nm using a Hitachi F-4500.

&lt;Example 4&gt; [Synthesis of Exemplified Compound A1] It was synthesized in the same manner except that the raw material chrysene used in Example 2 was changed to E5.

<chemistry num="24"><img file="JP2010143879A_D0024.tif" /></chemistry>

Exemplified compound A3, 1 × 10^-5The emission spectrum of the toluene solution at mol / l was a spectrum having the maximum intensity at 450 nm as a result of measuring photoluminescence at an excitation wavelength of 350 nm using a Hitachi F-4500.

&lt;Examples 5 to 20&gt; In this embodiment, the elements shown in the fifth example of the multi-layer organic light emitting device (anode / hole injection layer / hole transport layer / light emitting layer / hole exciton blocking layer / electron transport layer / cathode) are used. A 100 nm ITO was patterned on a glass substrate. The following organic layer and electrode layer are placed on the ITO substrate.^-5Vacuum vapor deposition is performed by resistance heating in the vacuum chamber of Pa to continuously form a film, and the facing electrode area is 3 mm.²I tried to become. Hall transport layer (30 nm) F-1 Emitting layer (30 nm) Host F-2, Guest: Exemplified compound (5% by weight) Whole Exciton Blocking Layer (10nm) F-3 Electron transport layer (30nm) F-4 Metal electrode layer 1 (1 nm) LiF Metal electrode layer 2 (100 nm) Al

<chemistry num="25"><img file="JP2010143879A_D0025.tif" /></chemistry>

As for the characteristics of the EL element, the current-voltage characteristics were measured with a Hewlett-Packard Co., Ltd. micro ammeter 4140B, and the emission brightness was measured with a Topcon Co., Ltd. BM7.

The table below summarizes the guest compounds and host compounds of the organic light emitting devices obtained in Examples 5 to 23, the luminous efficiency of the organic light emitting devices, and the applied voltage.

<tables num="1"><img file="JP2010143879A_D0026.tif" /></tables>

<figref num="1">It is a figure which shows typically the organic light emitting element which concerns on this embodiment, and the means which supplies an electric signal to the organic light emitting element which concerns on this embodiment.</figref><figref num="2">It is a figure which shows typically the pixel circuit connected to a pixel, the signal line connected to a pixel circuit, and the current supply line.</figref><figref num="3">It is a figure which shows the pixel circuit.</figref><figref num="4">It is sectional drawing which shows the organic light emitting element and the TFT under it.</figref><figref num="5">It is a figure which shows the X-axis and Y-axis which shows the skeleton of the diasenaft [1,2-b: 1', 2'-k] chrysene derivative and the direction of moment.</figref>

Code description

1 Display device 2,15 pixel circuit 11 Scanning signal driver 12 Information signal driver 13 Current source 14 pixels 21 First Thin Film Transistor (TFT) 22 Condenser (C_add) 23 Second thin film transistor (TFT) 31 board 32 Moisture proof layer 33 Gate electrode 34 Gate insulating film 35 Semiconductor film 36 Drain electrode 37 Source electrode 38 TFT element 39 Insulation film 310 Contact hole (through hole) 311 Anode 312 Organic layer 313 Cathode 314 First protective layer 315 Second protective layer