Organic electroluminescent element

Description: TECHNICAL FIELD [Detailed description of the invention]

【0001】

[Technical field to which the invention belongs]

The present invention relates to an organic electroluminescence device having excellent light emitting characteristics.

【0002】

[Conventional technology]

An organic electroluminescence (EL) device is a self-luminous device that utilizes the principle that a fluorescent substance emits light by the recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field. ..

【0003】

Since the report of low-voltage drive organic EL devices using stacked elements by CWTang et al. Of Eastman Kodak (CWTang, SAVanSlyke, Applied Physics Letters, Vol. 51, p. 913, 1987, etc.) Research on organic EL devices whose constituent materials are organic materials is being actively conducted.

【0004】

Tang et al. Use tris (8-hydroxyquinolinol aluminum) as the light emitting layer and a triphenyldiamine derivative as the hole transport layer. The advantages of the laminated structure are that it increases the efficiency of hole injection into the light emitting layer, that it blocks the electrons injected from the cathode and increases the efficiency of excitons generated by recombination, and that it is generated in the light emitting layer. Confinement of excitons and the like can be mentioned.

【0005】

As in this example, the element structure of the organic EL device is a two-layer type consisting of a hole transport (injection) layer and an electron transporting light emitting layer, or a hole transporting (injection) layer, a light emitting layer, and an electron transporting (injection) layer. The three-layer type of is well known.

【0006】

In such a laminated structure element, the element structure and the forming method have been devised in order to increase the recombination efficiency of the injected holes and electrons.

【0007】

As hole transporting materials, starburst molecules 4,4', 4'"-tris (3-methylphenylphenylamino) triphenylamine and N, N'-diphenyl-N, N'-bis (3-) Triphenylamine derivatives such as methylphenyl)-[1,1'-biphenyl] -4,4'-diamine and aromatic diamine derivatives are well known (for example, JP-A-8-20771, JP-A-8. -40995, Japanese Patent Application Laid-Open No. 8-40997, Japanese Patent Application Laid-Open No. 8-543397, Japanese Patent Application Laid-Open No. 8-87122, etc.).

【0008】

Oxadiazole derivatives, triazole derivatives and the like are well known as electron-transporting materials.

【0009】

Further, as a light emitting material, a chelate complex such as a tris (8-quinolinolate) aluminum complex, a coumarin derivative, a tetraphenylbutadiene derivative, a bisstyrylarylene derivative, an oxadiazole derivative and the like are known, and their light emitting colors It has been reported that light emission in the visible region from blue to red can be obtained, and the realization of a color display element is expected (for example, Japanese Patent Application Laid-Open No. 8-239655, Japanese Patent Application Laid-Open No. 7-138561, Special Publication No. Kaihei 3-200289, etc.).

【0010】

Further, in Japanese Patent Application Laid-Open No. 9-289081, pyrromethene-BF as a light emitting material₂The complex is disclosed.

【0011】

[Problems to be Solved by the Invention]

Recently, high-brightness, long-life organic EL devices have been disclosed or reported, but they are not always sufficient. Therefore, there is a strong demand for the development of materials that exhibit high performance. An object of the present invention is to provide a high-luminance organic EL device.

【0012】

[Means for solving problems]

As a result of diligent studies to solve the above problems, the present inventors have found that an organic EL device manufactured by using a specific pyrromethene metal complex compound as a light emitting material emits light with higher brightness than before.

【0013】

Further, it was found that the material has high carrier transportability, and an organic EL device prepared by using the material as a hole transport material or an electron transport material, and a mixture of the material with another hole transport material or an electron transport material. We have found that an organic EL device manufactured using a thin film exhibits higher brightness emission than before, and have reached the present invention.

【0014】

That is, according to the present invention, in an organic electroluminescent device having one layer or a plurality of organic thin film layers including a light emitting layer between a cathode and an anode, at least one layer of the organic thin film layer has a general formula [Chemical formula 2] :. [Chemical 2]

<img file="JP2000208262A_D0001.tif" />(In the formula, M represents an n-valent metal ion. N is one of 1, 2, or 3. R.¹~ R⁷Are independently hydrogen atom, halogen atom, hydroxyl group, substituted or unsubstituted amino group, nitro group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl. Group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted Alternatively, it represents an unsubstituted alkoxycarbonyl group or a carboxyl group. Also R¹~ R⁷May form a ring with two of them. ) Is an organic electroluminescence device containing a pyrromethene metal complex compound alone or as a mixture.

【0015】

Further, the present invention is an organic electroluminescence device characterized in that the organic thin film layer has at least a light emitting layer, and the light emitting layer contains a compound represented by the general formula [Chemical Formula 2] alone or as a mixture.

【0016】

Further, the present invention is an organic electroluminescence device characterized in that the organic thin film layer has at least a hole transport layer, and the light emitting layer contains a compound represented by the general formula [Chemical Formula 2] alone or as a mixture. is there.

【0017】

Further, the present invention is an organic electroluminescence device characterized in that the organic thin film layer has at least an electron transport layer, and the light emitting layer contains a compound represented by the general formula [Chemical Formula 2] alone or as a mixture. ..

【0018】

BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail. The compound according to the present invention is a compound having a structure represented by the general formula [Chemical Formula 2]. (In the formula, M represents an n-valent metal ion. N consists of 1, 2, or 3. R¹~ R⁷Are independently hydrogen atom, halogen atom, hydroxyl group, substituted or unsubstituted amino group, nitro group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl. Group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted Alternatively, it represents an unsubstituted alkoxycarbonyl group or a carboxyl group. Also R¹~ R⁷May form a ring with two of them.

【0019】

Metals that can be used for M showing n-valent metal ions include aluminum, beryllium, bismuth, cadmium, cerium, cobalt, copper, iron, gallium, germanium, mercury, indium, lanthanum, magnesium, molybdenum, niobium, and antimony. , Scandium, tin, tantalum, thorium, titanium, uranium, tungsten, zirconium, vanadium, zinc, silver, gold, platinum, chromium, manganese, yttrium, nickel, palladium, lead, selenium, tellurium, tarium, calcium, strontium, barium , Neodium, Europium, and Erbium, but are not limited to these.

【0020】

R¹~ R⁷Are independently hydrogen atom, halogen atom, hydroxyl group, substituted or unsubstituted amino group, nitro group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl. Group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted Alternatively, it represents an unsubstituted alkoxycarbonyl group or a carboxyl group. Also R¹~ R⁷May form a ring with two of them.

【0021】

Examples of the halogen atom include fluorine, chlorine, bromine and iodine.

【0022】

Substituted or unsubstituted amino groups are -NX¹X²Expressed as X¹, X²Hydrogen atom, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n -Heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3 -Dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3 -Dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromo Ethyl group, 1,3-dibromoisopropyl group, 2,3-dibromot-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group , 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2- Aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diaminot-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyanot-butyl group, 1,2,3-tricyano Propyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitrot-butyl group, 1, 2,3-trinitropropyl group, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthril group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-Phenyltril group, 9-Phenyltril group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 4-styrylphenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl Group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4 -Il group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2- Phenylpropyl) Phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenylyl group, 4''-t-butyl-p -Phenyl-4-yl group, 2-pyrrolill group, 3-pyrrolill group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 2-indrill group, 3-indrill group, 4-indrill group Group, 5-Indrill Group, 6-Indrill Group, 7-Indrill Group, 1-Isoindrill Group, 3-Isoindrill Group, 4-Isoindrill Group, 5-Isoindrill Group, 6-Isoindrill Group, 7-Isoindrill Group, 2-Frill Group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuran Nyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-aSoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4- Carbazoleyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group , 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-Phenanthlorin-2-yl group, 1,7-Phenancelorin-3-yl group, 1,7-Phenancelorin-4-yl group, 1,7-Phenancelorin-5-yl group Group, 1,7-phenanthlorin-6-yl group, 1,7-phenanthroline-8-yl group, 1,7-phenanthroline-9-yl group, 1,7-phenanthroline-10 -Il group, 1,8-phenanthroline-2-yl group, 1,8-phenanthroline-3-yl group, 1,8-phenanthroline-4-yl group, 1,8-phenanthroline -5-yl group, 1,8-phenanthroline-6-yl group, 1,8-phenanthroline-7-yl group, 1,8-phenanthroline-9-yl group, 1,8-fe Nanthroline-10-yl group, 1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3-yl group, 1,9-phenanthroline-4-yl group, 1,9 -Phenance lorin-5-yl group, 1,9-phenanthroline-6-yl group, 1,9-phenanthroline-7-yl group, 1,9-phenanthroline-8-yl group, 1 , 9-Phenancelorin-10-yl group, 1,10-phenanthroline-2-yl group, 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-4-yl group , 1,10-Phenancelorin-5-yl group, 2,9-Phenancelorin-1-yl group, 2,9-Phenancelorin-3-yl group, 2,9-Phenancelorin-4-yl group, 2,9-phenanthroline-5-yl group, 2,9-phenanthroline-6-yl group, 2,9-phenanthroline-7-yl group, 2,9-Phenancelorin-8-yl group, 2,9-phenanthlorin-10-yl group, 2,8-phenanthlorin-1-yl group, 2,8-phenanthlorin-3-yl group Group, 2,8-phenanthroline-4-yl group, 2,8-phenanthroline-5-yl group, 2,8-phenanthroline-6-yl group, 2,8-phenanthroline-7 -Il Group, 2,8-Phenance Lorin-9-Il Group, 2,8-Phenance Lorin-10-Il Group, 2,7-Phenance Lorin-1-Il Group, 2,7-Phenance Lorin -3-yl group, 2,7-phenanthroline-4-yl group, 2,7-phenanthroline-5-yl group, 2,7-phenanthroline-6-yl group, 2,7-fe Nanthroline-8-yl group, 2,7-phenanthroline-9-yl group, 2,7-Phenanthlorin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazine group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 1-phenoxadinyl group, 2-Phenoxazinyl group, 3-Phenoxazinyl group, 4-Phenoxazinyl group, 2-Oxazolyl group, 4-Oxazolyl group, 5-Oxazolyl group, 2-Oxaziazolyl group, 5-Oxaziazolyl group, 3-Frazanyl group, 2-Thienyl group, 3-Thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrole-4-yl group, 2-methylpyrrole-5-yl group, 3-methylpyrrole- 1-Il group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrole-5-yl group, 2-t-butylpyrrol-4-yl group, 3-( 2-Phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indrill group, 4-methyl-1-indrill group, 2-methyl-3-indrill group, 4-methyl-3-indrill group, 2- Examples thereof include t-butyl 1-indrill group, 4-t-butyl 1-indrill group, 2-t-butyl 3-indrill group, 4-t-butyl 3-indrill group and the like.

【0023】

Substituted or unsubstituted alkyl groups include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, and the like. n-Heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2, 3-Dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1, 3-Dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2- Dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromot-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl Group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2 -Aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diaminot-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group , 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyanot-butyl group, 1,2,3-trisia Nopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitrot-butyl group, 1 , 2,3-Trinitropropyl group and the like.

【0024】

Substituted or unsubstituted alkenyl groups include vinyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butandienyl group, 1-methylvinyl group, styryl group, 2,2. -Diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3 , 3-Diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl group, 3-phenyl-1-butenyl group and the like.

【0025】

Examples of the substituted or unsubstituted cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group and the like. The substituted or unsubstituted alkoxy group is a group represented by -OY, and Y is a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, or t-. Butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxy Ethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloro Isobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2- Bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromot-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1 -Iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo t-butyl group, 1,2,3-triiodopropyl Group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diaminot-butyl group, 1,2,3-Triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3- Dicyanot-butyl group, 1,2,

【0026】

Examples of substituted or unsubstituted aromatic hydrocarbon groups are phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2- Phenanthryl group, 3-phenanthril group, 4-phenanthril group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2- Biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl -4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p-( 2-Phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenylyl group, 4 "-t-butyl- Examples thereof include a p-terphenyl-4-yl group.

【0027】

Substituted or unsubstituted aromatic heterocyclic groups include 1-pyrrolyl group, 2-pyrrolill group, 3-pyrrolill group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group and 1-indrill. Group, 2-Indrill Group, 3-Indrill Group, 4-Indrill Group, 5-Indrill Group, 6-Indrill Group, 7-Indrill Group, 1-Isoindrill Group, 2-Isoindrill Group, 3-Isoindrill Group, 4-Isoindrill Group Group, 5-isoindrill group, 6-isoindrill group, 7-isoindrill group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl Group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-iso Benzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-fe Nanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acrydinyl group Group, 4-acrydinyl group, 9-acrydinyl group, 1,7-phenanthroline-2-yl group, 1,7-phenanthroline-3-yl group, 1,7-phenanthroline-4-yl group , 1,7-Phenance Lorin-5-Il Group, 1,7-Phenance Lorin-6-Il Group, 1,7-Phenanthlorin-8-yl group, 1,7-Phenancelorin-9-yl group, 1,7-Phenancelorin-10-yl group, 1,8-Phenancelorin-2-yl group, 1,8-Phenancelorin-3-yl group, 1,8-phenanthroline-4-yl group, 1,8-phenanthlorin-5-yl group, 1,8-phenanthroline-6-yl group Group, 1,8-Phenance Lorin-7-Il Group, 1,8-Phenance Lorin-9-Il Group, 1,8-Phenance Lorin-10-Il Group, 1,9-Phenance Lorin-2 -Il group, 1,9-phenanthlorin-3-yl group, 1,9-phenanthroline-4-yl group, 1,9-phenanthroline-5-yl group, 1,9-phenanthroline -6-yl group, 1,9-phenanthlorin-7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phenanthlorin-10-yl group, 1,10-fe Nanthroline-2-yl group, 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-4-yl group, 1,10-phenanthroline-5-yl group, 2,9 -Phenance lorin-1-yl group, 2,9-phenanthroline-3-yl group, 2,9-phenanthroline-4-yl group, 2,9-phenanthroline-5-yl group, 2 , 9-Phenance Lorin-6-Il Group, 2,9-Phenance Lorin-7-Il Group, 2,9-Phenance Lorin-8-Il Group, 2,9-Phenance Lorin-10-Il Group , 2,8-Phenanthlorin-1-yl group, 2,8-Phenancelorin-3-yl group, 2,8-Phenancelorin-4-yl group, 2,8-Phenancelorin-5- Il Group, 2,8-Phenance Lorin-6-Il Group, 2,8-Phenance Lorin-7-Il Group, 2,8-Phenance Lorin-9-Il Group, 2,8-Phenance Lorin- 10-yl group, 2,7-phenanthlorin-1-yl group, 2,7-phenanthroline-3-yl group, 2,7-phenanthlorin-4-yl group, 2,7-phenance Lorin-5-yl group, 2,7-phenance Lorin-6-yl group, 2,7-Phenancelorin-8-yl group, 2,7-phenanthroline-9-yl group, 2,7-phenanthroline-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-pheno Thiadynyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxadinyl group, 2-phenoxadinyl group, 3-phenoxadinyl group, 4-phenoxadinyl group, 10-phenoxadinyl group Group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-frazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrole-1-yl Group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrole-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrole-2-yl group Group, 3-methylpyrrol-4-yl group, 3-methylpyrrole-5-yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2 -Methyl-1-indrill group, 4-methyl-1-indrill group, 2-methyl-3-indrill group, 4-methyl-3-indrill group, 2-t-butyl 1-indrill group, 4-t-butyl Examples thereof include a 1-indolyl group, a 2-t-butyl 3-indrill group, a 4-t-butyl 3-indrill group, and the like.7-Phenanthlorin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazine group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group , 1-phenoxadinyl group, 2-phenoxadinyl group, 3-phenoxadinyl group, 4-phenoxadinyl group, 10-phenoxadinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group , 3-Frazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrole-4-yl group, 2-methylpyrrole -5-yl group, 3-methylpyrrole-1-yl group, 3-methylpyrrole-2-yl group, 3-methylpyrrole-4-yl group, 3-methylpyrrole-5-yl group, 2-t- Butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indrill group, 4-methyl-1-indrill group, 2-methyl-3-indrill group, 4-Methyl-3-indrill group, 2-t-butyl 1-indrill group, 4-t-butyl 1-indrill group, 2-t-butyl 3-indrill group, 4-t-butyl 3-indrill group, etc. Can be mentioned.7-Phenanthlorin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazine group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group , 1-phenoxadinyl group, 2-phenoxadinyl group, 3-phenoxadinyl group, 4-phenoxadinyl group, 10-phenoxadinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group , 3-Frazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrole-4-yl group, 2-methylpyrrole -5-yl group, 3-methylpyrrole-1-yl group, 3-methylpyrrole-2-yl group, 3-methylpyrrole-4-yl group, 3-methylpyrrole-5-yl group, 2-t- Butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indrill group, 4-methyl-1-indrill group, 2-methyl-3-indrill group, 4-Methyl-3-indrill group, 2-t-butyl 1-indrill group, 4-t-butyl 1-indrill group, 2-t-butyl 3-indrill group, 4-t-butyl 3-indrill group, etc. Can be mentioned.

【0028】

Substituted or unsubstituted aralkyl groups include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, and the like. 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β- Naftyl ethyl group, 1-β-naphthyl isopropyl group, 2-β-naphthyl isopropyl group, 1-pyrrolyl methyl group, 2- (1-pyrrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methyl Benzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group , O-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m -Nitrobenzyl group, o-nitrobenzyl group, Examples thereof include a p-cyanobenzyl group, an m-cyanobenzyl group, an o-cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group and a 1-chloro-2-phenylisopropyl group.

【0029】

Substituted or unsubstituted aryloxy groups are represented as -OZ, where Z is phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl. Group, 2-Phenyltril Group, 3-Phenyltril Group, 4-Phenyltril Group, 9-Phenyltril Group, 1-Naphthalsenyl Group, 2-Naphthalsenyl Group, 9-Naphthalsenyl Group, 1-Phenyl Group, 2-Pyrenyl Group, 4-Pyrenyl Group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group , P- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenylyl group, 4 "- t-butyl-p-terphenyl-4-yl group, 2-pyrrolill group, 3-pyrrolill group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 2-indrill group, 3-indrill Group, 4-Indrill Group, 5-Indrill Group, 6-Indrill Group, 7-Indrill Group, 1-Isoindrill Group, 3-Isoindrill Group, 4-Isoindrill Group, 5-Isoindrill Group, 6-Isoindrill Group, 7-Isoindrill Group Group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isokiNoryl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3- Carbazoleyl group, 4-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7- Phenance lydinyl group, 8-phenanth lydinyl group, 9-phenanth lydinyl group, 10-phenanth lydinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acrydinyl group, 1,7-phenanthroline-2-yl group, 1,7-phenanthroline-3-yl group, 1,7-phenanthroline-4-yl group, 1,7-phenance Lorin-5-yl group, 1,7-phenanthroline-6-yl group, 1,7-phenanthroline-8-yl group, 1,7-phenanthroline-9-yl group, 1,7- Phenanthuroline-10-yl group, 1,8-phenanthroline-2-yl group, 1,8-phenanthroline-3-yl group, 1,8-phenanthroline-4-yl group, 1, 8-Phenance Lorin-5-Il Group, 1,8-Phenance Lorin-6-Il Group, 1,8-Phenance Lorin-7-Il Group, 1,8-Phenance Lorin-9-Il Group, 1,8-Phenancelorin-10-yl group, 1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3-yl group, 1,9-phenanthroline-4-yl group Group, 1,9-phenanthroline-5-yl group, 1,9-phenanthroline-6-yl group, 1,9-phenanthroline-7-yl group, 1,9-phenanthroline-8 -Il group, 1,9-phenanthroline-10-yl group, 1,10-phenanthroline-2-yl group, 1,10-phenanthroline-3-yl group, 1,10-phenanthroline -4-yl group, 1,10-phenanthroline-5-yl group, 2,9-phenanthroline-1-yl group, 2,9-Phenancelorin-3-yl group, 2,9-phenanthroline-4-yl group, 2,9-phenanthroline-5-yl group, 2,9-phenanthroline-6-yl group, 2,9-Phenancelorin-7-yl group, 2,9-phenanthlorin-8-yl group, 2,9-phenanthlorin-10-yl group, 2,8-phenanthlorin-1-yl group Group, 2,8-phenanthroline-3-yl group, 2,8-phenanthroline-4-yl group, 2,8-phenanthroline-5-yl group, 2,8-phenanthroline-6 -Il Group, 2,8-Phenance Lorin-7-Il Group, 2,8-Phenance Lorin-9-Il Group, 2,8-Phenance Lorin-10-Il Group, 2,7-Phenance Lorin -1-yl group, 2,7-phenanthroline-3-yl group, 2,7-phenanthroline-4-yl group, 2,7-phenanthroline-5-yl group, 2,7-fe Nanthroline-6-yl group, 2,7-phenanthroline-8-yl group, 2,7-phenanthroline-9-yl group, 2,7-Phenanthlorin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazine group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 1-phenoxadinyl group, 2-Phenoxazinyl group, 3-Phenoxazinyl group, 4-Phenoxazinyl group, 2-Oxazolyl group, 4-Oxazolyl group, 5-Oxazolyl group, 2-Oxaziazolyl group, 5-Oxaziazolyl group, 3-Frazanyl group, 2-Thienyl group, 3-Thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrole-4-yl group, 2-methylpyrrole-5-yl group, 3-methylpyrrole- 1-Il group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrole-5-yl group, 2-t-butylpyrrol-4-yl group, 3-( 2-Phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indrill group, 4-methyl-1-indrill group, 2-methyl-3-indrill group, 4-methyl-3-indrill group, 2- Examples thereof include t-butyl 1-indrill group, 4-t-butyl 1-indrill group, 2-t-butyl 3-indrill group, 4-t-butyl 3-indrill group and the like.

【0030】

Substituted or unsubstituted alkoxycarbonyl groups are represented as -COOY, and Y is methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n. -Pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1 , 3-Dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1 , 2-Dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2 -Bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromot-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2- Aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diaminot-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-Cyanoethyl group, 2-Cyanoethyl group, 2-Cyanoisobutyl group, 1,2-Dicyanoethyl group, 1,3-Dicyanoisopropyl group, 2,3-Dicyanot-butyl group, 1,2,3-Tricyano Propyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitrot-butyl group, 1, Examples include 2,3-trinitropropyl groups.

【0031】

Examples of divalent groups forming a ring include tetramethylene group, pentamethylene group, hexamethylene group, diphenylmethane-2,2'-diyl group, diphenylethane-3,3'-diyl group and diphenylpropane-. Examples thereof include a 4,4'-diyl group and a 1,3-butadiene-1,4-diyl group.

【0032】

Examples of the compound according to the present invention are given by the chemical formulas shown in [Chemical Formula 3] to [Chemical Formula 10] below, but the present invention is not limited thereto.

[Chemical 3]

<img file="JP2000208262A_D0002.tif" />[Chemical 4]

<img file="JP2000208262A_D0003.tif" />[Chemical 5]

<img file="JP2000208262A_D0004.tif" />[Chemical 6]

<img file="JP2000208262A_D0005.tif" />[Chemical 7]

<img file="JP2000208262A_D0006.tif" />[Chemical 8]

<img file="JP2000208262A_D0007.tif" />[Chemical 9]

<img file="JP2000208262A_D0008.tif" />[Chemical 10]

<img file="JP2000208262A_D0009.tif" />【0033】

The element structure of the organic EL device in the present invention is a structure in which one or more organic layers are laminated between electrodes, and examples thereof are shown in FIGS. 1 to 4.

【0034】

The element structure shown in FIG. 1 includes an anode 2, a light emitting layer 4, and a cathode 6 provided on the substrate 1.

【0035】

The device structure shown in FIG. 2 includes an anode 2, a hole transport layer 3, a light emitting layer 4, an electron transport layer 5, and a cathode 6 provided on the substrate 1.

【0036】

The device structure shown in FIG. 3 includes an anode 2, a hole transport layer 3, a light emitting layer 4, and a cathode 6 provided on the substrate 1.

【0037】

The device structure shown in FIG. 4 includes an anode 2, a light emitting layer 4, an electron transporting layer 5, and a cathode 6 provided on the substrate 1. Here, the hole transport layer 3, the light emitting layer 4, and the electron transport layer 5 correspond to the organic layer.

【0038】

The compound in the present invention may be used for any of the above organic layers, and can be doped with other hole transporting materials, light emitting materials, and electron transporting materials.

【0039】

The hole transporting material used in the present invention is not particularly limited, and any compound usually used as a hole transporting agent may be used. For example, the following bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane [chemical 11], N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'- Tris such as biphenyl-4,4'-diamine [chemical 12], N, N'-diphenyl-NN-bis (1-naphthyl) -1,1'-biphenyl) -4,4'-diamine [chemical 13] Examples thereof include phenyldiamines and starburst type molecules ([Chemical 14] to [Chemical 16], etc.).

[Chemical 11]

<img file="JP2000208262A_D0010.tif" />[Chemical 12]

<img file="JP2000208262A_D0011.tif" />[Chemical 13]

<img file="JP2000208262A_D0012.tif" />[Chemical 14]

<img file="JP2000208262A_D0013.tif" />[Chemical 15]

<img file="JP2000208262A_D0014.tif" />[Chemical 16]

<img file="JP2000208262A_D0015.tif" />【0040】

The electron transporting material used in the present invention is not particularly limited, and any compound usually used as an electron transporting material may be used. For example, 2- (4-biphenylyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazole [chemical 17], bis {2- (4-t-butylphenyl), as shown below. ) -1,3,4-Oxadiazole} -m-Phenylene [Chemical 18], etc. Oxadiazole derivatives, triazole derivatives ([Chemical 19], [Chemical 20], etc.), quinolinol-based metal complexes ([] 21] to [24], etc.).

[Chemical 17]

<img file="JP2000208262A_D0016.tif" />[Chemical 18]

<img file="JP2000208262A_D0017.tif" />[Chemical 19]

<img file="JP2000208262A_D0018.tif" />[Chemical 20]

<img file="JP2000208262A_D0019.tif" />[Chemical 21]

<img file="JP2000208262A_D0020.tif" />[Chemical 22]

<img file="JP2000208262A_D0021.tif" />[Chemical 23]

<img file="JP2000208262A_D0022.tif" />[Chemical 24]

<img file="JP2000208262A_D0023.tif" />【0041】

The anode 2 of the organic thin film EL element plays a role of injecting holes into the hole transport layer 3 or the light emitting layer 4, and it is effective to have a work function of 4.5 eV or more. Specific examples of the anode material used in the present invention include indium tin oxide alloy (ITO), tin oxide (NESA), gold, silver, platinum, copper and the like.

【0042】

Further, as the cathode 6, a material having a small work function is preferable for the purpose of injecting electrons into the electron transport layer 5 or the light emitting layer 4. The cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.

【0043】

The method for forming each layer of the organic EL device of the present invention is not particularly limited. A conventionally known forming method such as a vacuum vapor deposition method or a spin coating method can be used. The organic thin film layer containing the compound represented by the general formula [Chemical Formula 2] used in the organic EL device of the present invention is a vacuum vapor deposition method, a molecular beam epitaxy method (MBE method), a dipping method of a solution dissolved in a solvent, or a spin. It can be formed by a known method according to a coating method such as a coating method, a casting method, a bar coating method, or a roll coating method.

【0044】

The film thickness of each organic layer of the organic EL device of the present invention is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if it is too thick, a high applied voltage is required and efficiency deteriorates. Therefore, the film thickness is usually preferably in the range of several nm or more and 1 μm or less.

【0045】

Hereinafter, the present invention will be described in detail based on examples, but the present invention is not limited to the following examples as long as the gist of the present invention is not exceeded.

【0046】

(Synthesis example 1) Synthesis of 5-phenyl-4 and 6-dipyrine. Trifluoroacetic acid was added to a toluene solution of benzoaldehyde and pyrrole, and the mixture was refluxed for 3 hours. The obtained reaction solution was washed with an aqueous sodium carbonate solution and then dried. This was purified according to a conventional method to obtain 5-phenyldipyrromethane. The dipyrromethane thus obtained was made into a chloroform solution, 2,3-dichloro-5, 6-dicyano-1, and 4-quinone were added, and the mixture was stirred at room temperature. The reaction mixture was concentrated and purified by column chromatography to obtain the desired 5-phenyl-4 and 6-dipyrin.

【0047】

(Synthesis Example 2) Synthesis of 5-p-cyanophenyl-4,6-dipyrin. The desired 5-p-cyanophenyl-4 and 6-dipyrine were obtained by the same method as in Synthesis Example 1 except that 4-cyanobenzaldehyde was used instead of benzaldehyde.

【0048】

(Synthesis Example 3) Synthesis of 2,3,7,8-tetramethyl-5-phenyl-4,6-dipyrin. The target 2,3,7,8-tetramethyl-5-phenyl-4,6-dipyrrole was obtained by the same method as in Synthesis Example 1 except that 3,4-dimethylpyrrole was used instead of pyrrole.

【0049】

(Synthesis Example 4) Synthesis of 2,3,7,8-tetramethyl-5-p-cyanophenyl-4,6-dipyrin. The desired 2,3,7,8-tetramethyl-5-p-cyanophenyl-4,6-dipyrrole was obtained by the same method as in Synthesis Example 2 except that 3,4-dimethylpyrrole was used instead of pyrrole. It was.

【0050】

(Synthesis Example 5) Synthesis of a compound represented by the chemical formula [Chemical Formula 3] (tri (5-phenyl-4,6-dipyrine) aluminum complex). Aluminum chloride was added to a toluene solution of 5-phenyl-4 and 6-dipyrin, and the mixture was refluxed for 8 hours. The reaction mixture was concentrated and then purified by column chromatography using silica gel to obtain the desired compound represented by the chemical formula [Chemical Formula 3].

【0051】

(Synthesis Example 6) Synthesis of a compound represented by the chemical formula [Chemical Formula 4] (tri (5-p-cyanophenyl-4,6-dipyrin) aluminum complex). It is represented by the target chemical formula [Chemical formula 4] by the same method as in Synthesis Example 5, except that 5-p-cyanophenyl-4, 6-dipyrin is used instead of 5-phenyl-4, 6-dipyrin. The compound was obtained.

【0052】

(Synthesis Example 7) Synthesis of a compound represented by the chemical formula [Chemical Formula 5] (tri (2,3,7,8-tetramethyl-5-phenyl-4,6-dipyrine) aluminum complex). The target chemical formula is the same as in Synthesis Example 5, except that 2,3,7,8-tetramethyl-5-phenyl-4,6-dipyrin is used instead of 5-phenyl-4,6-dipyrin. The compound represented by [Chemical formula 5] was obtained.

【0053】

(Synthesis Example 8) Synthesis of a compound represented by the chemical formula [Chemical formula 6] (tri (2,3,7,8-tetramethyl-5-p-cyanophenyl-4,6-dipyrine) aluminum complex). By the same method as in Synthesis Example 5, except that 2,3,7,8-tetramethyl-5-p-cyanophenyl-4,6-dipyrin is used instead of 5-phenyl-4,6-dipyrin. A compound represented by the desired chemical formula [Chemical formula 6] was obtained.

【0054】

(Synthesis Example 9) Synthesis of a compound (di (5-phenyl-4, 6-dipyrin) zinc complex) represented by the chemical formula [Chemical Formula 7]. Zinc acetate was added to a methanol solution of 5-phenyl-4 and 6-dipyrin, and the mixture was refluxed for 4 hours. The reaction mixture was concentrated and then purified by column chromatography using silica gel to obtain the desired compound represented by the chemical formula [Chemical Formula 7].

【0055】

(Synthesis Example 10) Synthesis of a compound represented by the chemical formula [Chemical Formula 8] (di (5-p-cyanophenyl-4,6-dipyrin) zinc complex). It is represented by the target chemical formula [Chemical formula 8] by the same method as in Synthesis Example 9, except that 5-p-cyanophenyl-4, 6-dipyrin is used instead of 5-phenyl-4, 6-dipyrin. The compound was obtained.

【0056】

(Synthesis Example 11) Synthesis of a compound represented by the chemical formula [Chemical Formula 9] (di (2, 3, 7, 8-tetramethyl-5-phenyl-4, 6-dipyrin) zinc complex). The target chemical formula is the same as in Synthesis Example 9, except that 2,3,7,8-tetramethyl-5-phenyl-4,6-dipyrin is used instead of 5-phenyl-4,6-dipyrin. The compound represented by [Chemical formula 9] was obtained.

【0057】

(Synthesis Example 12) Synthesis of a compound represented by the chemical formula [Chemical formula 10] (di (2, 3, 7, 8-tetramethyl-5-p-cyanophenyl-4, 6-dipyrin) zinc complex). By the same method as in Synthesis Example 5, except that 2,3,7,8-tetramethyl-5-p-cyanophenyl-4,6-dipyrin is used instead of 5-phenyl-4,6-dipyrin. A compound represented by the desired chemical formula [Chemical Formula 10] was obtained.

【0058】

Hereinafter, Examples of Examples 1 to 25 and Examples 31 to 34 using the compound of the present invention as a light emitting layer are shown. Further, Examples 26 to 30 show examples in which a mixed thin film of the compound of the present invention and a hole transporting material is used as a light emitting layer. In addition, examples of using a mixed thin film of the compound of the present invention and an electron transporting material as a light emitting layer are described below in Examples 35 to 39, and Examples of using the compound of the present invention as a hole transporting layer. Will be shown in Examples 40 to 41 described below, and Examples 42 to 43 described below in Examples of the use as the electron transport layer.

【0059】

(Example 1) Fig. 1 shows the cross-sectional structure of the element used in Example 1. The procedure for manufacturing the organic thin film EL device used in Example 1 of the present invention will be described below. The element is composed of an anode 2 / a light emitting layer 4 / a cathode 6 formed on the substrate 1. ITO was formed on the glass substrate 1 by sputtering so that the sheet resistance was 20 Ω / , and used as the anode 2. A compound represented by the chemical formula [Chemical Formula 3] was formed on the anode 2 as a light emitting layer 4 by a vacuum vapor deposition method to a thickness of 40 nm. Next, a magnesium-silver alloy was formed on the light emitting layer 4 as a cathode 6 by a vacuum vapor deposition method to a thickness of 200 nm to prepare an organic EL device. When a DC voltage of 5V was applied to this element, it was 400cd / m.²Luminescence was obtained.

【0060】

(Example 2) An organic EL device was produced by performing the same operation as in Example 1 except that a compound represented by the chemical formula [Chemical Formula 4] was used as the light emitting material. When a DC voltage of 5V was applied to this element, it was 370cd / m.²Luminescence was obtained.

【0061】

(Example 3) An organic EL device was produced by performing the same operation as in Example 1 except that a compound represented by the chemical formula [Chemical Formula 5] was used as the light emitting material. When a DC voltage of 5V was applied to this element, it was 650cd / m.²Luminescence was obtained.

【0062】

(Example 4) An organic EL device was produced by performing the same operation as in Example 1 except that a compound represented by the chemical formula [Chemical formula 6] was used as the light emitting material. When a DC voltage of 5V was applied to this element, it was 540cd / m.²Luminescence was obtained.

【0063】

(Example 5) An organic EL device was produced by performing the same operation as in Example 1 except that a compound represented by the chemical formula [Chemical Formula 7] was used as the light emitting material. When a DC voltage of 5V was applied to this element, 350cd / m²Luminescence was obtained.

【0064】

(Example 6) An organic EL device was produced by performing the same operation as in Example 1 except that a compound represented by the chemical formula [Chemical Formula 8] was used as the light emitting material. When a DC voltage of 5V was applied to this element, it was 300 cd / m.²Luminescence was obtained.

【0065】

(Example 7) An organic EL device was produced by performing the same operation as in Example 1 except that a compound represented by the chemical formula [Chemical Formula 9] was used as the light emitting material. When a DC voltage of 5V was applied to this element, it was 380cd / m.²Luminescence was obtained.

【0066】

(Example 8) An organic EL device was produced by performing the same operation as in Example 1 except that a compound represented by the chemical formula [Chemical Formula 10] was used as the light emitting material. When a DC voltage of 5V was applied to this element, it was 310 cd / m.²Luminescence was obtained.

【0067】

(Example 9) As shown in FIG. 1, the cross-sectional structure of the element used in Example 9 is composed of an anode 2 / light emitting layer 4 / cathode 6 formed on the substrate 1. The procedure for manufacturing the organic thin film EL device used in Example 9 in the present invention will be described below. ITO was formed on the glass substrate 1 by sputtering so that the sheet resistance was 20 Ω / , and used as the anode 2. A light emitting layer 4 having a layer thickness of 40 nm was formed on the spin coating method using a chloroform solution of the compound represented by the chemical formula [Chemical Formula 7]. Next, a magnesium-silver alloy was formed on the light emitting layer 4 as a cathode 6 to a thickness of 200 nm by a vacuum vapor deposition method to prepare an organic EL device. When a DC voltage of 5V was applied to this element, it was 120 cd / m.²Luminescence was obtained.

【0068】

(Example 10) An organic EL device was produced in the same manner as in Example 9 except that the compound represented by the chemical formula [Chemical Formula 9] was used instead of the compound represented by the chemical formula [Chemical Formula 7]. When a DC voltage of 5V was applied to this element, it was 130 cd / m.²Luminescence was obtained.

【0069】

(Example 11) FIG. 2 shows the cross-sectional structure of the element used in Example 11. The device is composed of an anode 2 / hole transport layer 3 / light emitting layer 4 / electron transport layer 5 / cathode 6 formed on the substrate 1. The procedure for manufacturing the organic thin film EL device used in Example 11 in the present invention will be described below. ITO was formed on the glass substrate 1 by sputtering so that the sheet resistance was 20 Ω / , and used as the anode 2. N, N'-diphenyl-N, N'-bis (3-methylphenyl)-[1,1'-biphenyl] represented by the chemical formula [Chemical Formula 3] as a hole transport layer 3 on the anode 2. -4,4'-diamine was formed to a thickness of 50 nm by vacuum deposition. Next, a compound represented by the chemical formula [Chemical Formula 3] was formed on the hole transport layer 3 as a light emitting layer 4 by a vacuum vapor deposition method to a thickness of 40 nm. Next, on the light emitting layer 4, the electron transport layer 5 is represented by the chemical formula [Chemical formula 17], 2- (4-biphenylyl) -5- (4-t-butylphenyl) -1,3,4-. Oxadiazole was formed to a thickness of 20 nm by vacuum deposition. Next, a magnesium-silver alloy was formed on the electron transport layer 5 as the cathode 6 to a thickness of 200 nm by a vacuum vapor deposition method to prepare an organic EL device. When a DC voltage of 10V was applied to this element, it was 2370cd / m.²Luminescence was obtained.

【0070】

(Example 12) An organic EL device was produced by performing the same operation as in Example 11 except that a compound represented by the chemical formula [Chemical Formula 4] was used as the light emitting material. When a DC voltage of 10V was applied to this element, it was 1860cd / m.²Luminescence was obtained.

【0071】

(Example 13) An organic EL device was produced by performing the same operation as in Example 11 except that a compound represented by the chemical formula [Chemical Formula 5] was used as the light emitting material. When a DC voltage of 10V was applied to this element, 2510cd / m²Luminescence was obtained.

【0072】

(Example 14) An organic EL device was produced by performing the same operation as in Example 11 except that a compound represented by the chemical formula [Chemical formula 6] was used as the light emitting material. When a DC voltage of 10V was applied to this element, it was 1970 cd / m.²Luminescence was obtained.

【0073】

(Example 15) An organic EL device was produced by performing the same operation as in Example 11 except that a compound represented by the chemical formula [Chemical Formula 7] was used as the light emitting material. When a DC voltage of 10V was applied to this element, it was 1260cd / m.²Luminescence was obtained.

【0074】

(Example 16) An organic EL device was produced by performing the same operation as in Example 11 except that a compound represented by the chemical formula [Chemical Formula 8] was used as the light emitting material. When a DC voltage of 10V was applied to this element, it was 1070cd / m.²Luminescence was obtained.

【0075】

(Example 17) An organic EL device was produced by performing the same operation as in Example 11 except that a compound represented by the chemical formula [Chemical Formula 9] was used as the light emitting material. When a DC voltage of 10V was applied to this element, it was 1380cd / m.²Luminescence was obtained.

【0076】

(Example 18) An organic EL device was produced by performing the same operation as in Example 11 except that a compound represented by the chemical formula [Chemical Formula 10] was used as the light emitting material. When a DC voltage of 10V was applied to this element, 1110cd / m²Luminescence was obtained.

【0077】

(Example 19) As the hole transport layer 3, N, N'-diphenyl-NN-bis (1-naphthyl) -1,1'-biphenyl) -4,4'represented by the chemical formula [Chemical formula 13] -Except for using the compound bis {2- (4-t-butylphenyl) -1,3,4-oxadiazole} -m-phenylene represented by the chemical formula [Chemical formula 18] as the electron transport layer 5 with diamine. Made an organic EL element by performing the same operation as in Example 11. When a DC voltage of 10V was applied to this element, it was 2240cd / m.²Luminescence was obtained.

【0078】

(Example 20) As the hole transport layer 3, the compound represented by the chemical formula [Chemical formula 14] is used as the light emitting layer 4, and the compound represented by the chemical formula [Chemical formula 4] is used as the electron transport layer 5. An organic EL device was produced by performing the same operation as in Example 11 except that the compound represented by 21] was used. When a DC voltage of 10V was applied to this element, it was 1680cd / m.²Luminescence was obtained.

【0079】

(Example 21) A compound represented by the chemical formula [Chemical formula 15] as the hole transport layer 3, a compound represented by the chemical formula [Chemical formula 5] as the light emitting layer 4, and a chemical formula [Chemical formula 22] as the electron transport layer 5. ], The same operation as in Example 11 was carried out to prepare an organic EL device. When a DC voltage of 10V was applied to this element, it was 2520 cd / m.²Luminescence was obtained.

【0080】

(Example 22) FIG. 4 shows the cross-sectional structure of the element used in Example 22. The element is composed of an anode 2 / a light emitting layer 4 / an electron transport layer 5 / a cathode 6 formed on the substrate 1. The procedure for manufacturing the organic thin film EL device used in Example 22 of the present invention will be described below. ITO was formed on the glass substrate 1 by sputtering so that the sheet resistance was 20 Ω / , and used as the anode 2. On the anode 2, a compound represented by the chemical formula [Chemical Formula 3] was formed as a light emitting layer 4 to a thickness of 40 nm by a vacuum vapor deposition method. Next, a compound represented by the chemical formula [Chemical Formula 19] was formed on the light emitting layer 4 as an electron transport layer 5 by a vacuum vapor deposition method to a thickness of 50 nm. Next, a magnesium-silver alloy was formed on the electron transport layer 5 as a cathode 6 to a thickness of 200 nm to fabricate an EL device. When a DC voltage of 10V was applied to this element, it was 1090cd / m.²Luminescence was obtained.

【0081】

(Example 23) The same operation as in Example 22 was performed except that the compound represented by the chemical formula [Chemical Formula 4] was used for the light emitting layer 4 instead of the compound represented by the chemical formula [Chemical Formula 3], and the organic EL was performed. The element was manufactured. When a DC voltage of 10V was applied to this element, it was 960cd / m.²Luminescence was obtained.

【0082】

(Example 24) The same operation as in Example 22 is performed except that the compound represented by the chemical formula [Chemical formula 5] is used instead of the compound represented by the chemical formula [Chemical formula 5] in the light emitting layer 4. The organic EL element was manufactured. When a DC voltage of 10V was applied to this element, 1220cd / m²Luminescence was obtained.

【0083】

(Example 25) The same operation as in Example 22 was performed except that the compound represented by the chemical formula [Chemical formula 6] was used for the light emitting layer 4 instead of the compound represented by the chemical formula [Chemical formula 3], and the organic EL was performed. The element was manufactured. When a DC voltage of 10V was applied to this element, it was 1020cd / m.²Luminescence was obtained.

【0084】

(Example 26) As the light emitting layer 4, N, N'-diphenyl-NN-bis (1-naphthyl) -1,1'-biphenyl) -4,4'-diamine represented by the chemical formula [Chemical formula 13] The organic EL device is operated in the same manner as in Example 22 except that a thin film prepared by co-depositing the compound represented by the chemical formula [Chemical Formula 3] at a weight ratio of 1:10 is formed to a thickness of 50 nm. Was produced. When a DC voltage of 10V was applied to this element, it was 1290 cd / m.²Luminescence was obtained.

【0085】

(Example 27) An organic EL device is operated in the same manner as in Example 26 except that the compound represented by the chemical formula [Chemical Formula 4] is used for the light emitting layer 4 instead of the compound represented by the chemical formula [Chemical Formula 3]. Was produced. When a DC voltage of 10V was applied to this element, it was 1060cd / m.²Luminescence was obtained.

【0086】

(Example 28) An organic EL device is operated in the same manner as in Example 26 except that the compound represented by the chemical formula [Chemical formula 5] is used for the light emitting layer 4 instead of the compound represented by the chemical formula [Chemical formula 3]. Was produced. When a DC voltage of 10V was applied to this element, it was 1450 cd / m.²Luminescence was obtained.

【0087】

(Example 29) An organic EL device is operated in the same manner as in Example 26 except that the compound represented by the chemical formula [Chemical formula 6] is used for the light emitting layer 4 instead of the compound represented by the chemical formula [Chemical formula 3]. Was produced. When a DC voltage of 10V was applied to this element, it was 1170 cd / m.²Luminescence was obtained.

【0088】

(Example 30) FIG. 4 shows the cross-sectional structure of the element used in Example 30. The element is composed of an anode 2 / a light emitting layer 4 / an electron transport layer 5 / a cathode 6 formed on the substrate 1. The procedure for manufacturing the organic thin film EL device used in Example 30 of the present invention will be described below. ITO was formed on the glass substrate 1 by sputtering so that the sheet resistance was 20 Ω / , and used as the anode 2. On the anode 2, the compound represented by the chemical formula [Chemical formula 6] and the N, N'-diphenyl-NN-bis (1-naphthyl) -1,1'-biphenyl represented by the chemical formula [Chemical formula 13]) A light emitting layer 4 having a thickness of 40 nm was formed by a spin coating method using a chloroform solution containing -4,4'-diamine in a molar ratio of 1:10. Next, an electron transport layer 5 having a thickness of 50 nm is formed on the light emitting layer 4 by a vacuum deposition method using a compound represented by the chemical formula [Chemical Formula 11], and magnesium-silver as a cathode 6 is formed on the electron transport layer 5. An organic EL device was manufactured by forming an alloy to a thickness of 200 nm by a vacuum vapor deposition method. When a DC voltage of 10V was applied to this element, it was 730cd / m.²Luminescence was obtained.

【0089】

(Example 31) Fig. 3 shows the cross-sectional structure of the element used in Example 31. The element is composed of an anode 2 / hole transport layer 3 / light emitting layer 4 / cathode 6 formed on the substrate 1. The procedure for manufacturing the organic thin film EL device used in Example 31 of the present invention will be described below. ITO was formed on the glass substrate 1 by sputtering so that the sheet resistance was 20 Ω / , and used as the anode 2. N, N'-diphenyl-NN-bis (1-naphthyl) -1,1'-biphenyl) -4,4'represented by the chemical formula [Chemical formula 13] as the hole transport layer 3 on the anode 2. A film made of -diamine was formed to a thickness of 50 nm by a vacuum deposition method. Next, on the hole transport layer 3, a film in which a compound represented by the chemical formula [Chemical Formula 3] was vacuum-deposited as a light emitting layer 4 was formed to a thickness of 40 nm. Next, an EL device was manufactured by forming a magnesium-silver alloy layer as a cathode 6 on the light emitting layer 4 to a thickness of 200 nm. When a DC voltage of 10V was applied to this element, 1820cd / m²Luminescence was obtained.

【0090】

(Example 32) As the light emitting layer 4, the same operation as in Example 31 is performed except that the compound represented by the chemical formula [Chemical formula 4] is used instead of the compound represented by the chemical formula [Chemical formula 3]. The element was manufactured. When a DC voltage of 10 V was applied to this element, it was 1560 cd / m.²Luminescence was obtained.

【0091】

(Example 33) As the light emitting layer 4, the same operation as in Example 31 is performed except that the compound represented by the chemical formula [Chemical formula 5] is used instead of the compound represented by the chemical formula [Chemical formula 3]. The element was manufactured. When a DC voltage of 10V was applied to this element, it was 2020 cd / m.²Luminescence was obtained.

【0092】

(Example 34) Organic EL is subjected to the same operation as in Example 31 except that the compound represented by the chemical formula [Chemical formula 6] is used instead of the compound represented by the chemical formula [Chemical formula 3] as the light emitting layer 4. The element was manufactured. When a DC voltage of 10V was applied to this element, it was 1760cd / m.²Luminescence was obtained.

【0093】

(Example 35) As the light emitting layer 4, a film obtained by vacuum co-depositing a compound represented by the chemical formula [Chemical Formula 21] and a compound represented by the chemical formula [Chemical Formula 3] at a weight ratio of 20: 1 is 50 nm thick. An organic EL device was produced by performing the same operation as in Example 31 except that it was formed in a vacuum. When a DC voltage of 10V was applied to this element, it was 2190 cd / m.²Luminescence was obtained.

【0094】

(Example 36) As the light emitting layer 4, a film obtained by vacuum co-depositing a compound represented by the chemical formula [Chemical Formula 21] and a compound represented by the chemical formula [Chemical Formula 4] at a weight ratio of 20: 1 is 50 nm thick. An organic EL device was produced by performing the same operation as in Example 31 except that it was formed in a vacuum. When a DC voltage of 10V was applied to this element, it was 1960cd / m.²Luminescence was obtained.

【0095】

(Example 37) As the light emitting layer 4, a film obtained by vacuum co-depositing a compound represented by the chemical formula [Chemical Formula 21] and a compound represented by the chemical formula [Chemical Formula 5] at a weight ratio of 20: 1 is 50 nm thick. An organic EL device was produced by performing the same operation as in Example 31 except that it was formed in a vacuum. When a DC voltage of 10V was applied to this element, it was 2320 cd / m.²Luminescence was obtained.

【0096】

(Example 38) As the light emitting layer 4, a film obtained by vacuum co-depositing a compound represented by the chemical formula [Chemical Formula 21] and a compound represented by the chemical formula [Chemical Formula 6] at a weight ratio of 20: 1 is 50 nm thick. An organic EL device was produced by performing the same operation as in Example 31 except that it was formed in a vacuum. When a DC voltage of 10V was applied to this element, it was 2030 cd / m.²Luminescence was obtained.

【0097】

(Example 39) As the hole transport layer 3, N, N'-diphenyl-N, N'-bis (3-methylphenyl)-[1,1'-biphenyl] represented by the chemical formula [Chemical formula 12]. Using -4,4'-diamine as the light emitting layer 4, the compound represented by the chemical formula [Chemical Formula 23] and the compound represented by the chemical formula [Chemical Formula 6] are vacuum co-deposited at a weight ratio of 20: 1. An organic EL element was produced by performing the same operation as in Example 31 except that the produced film was used. When a DC voltage of 10V was applied to this element, it was 2080 cd / m.²Luminescence was obtained.

【0098】

(Example 40) Except for using a compound represented by the chemical formula [Chemical Formula 3] as the hole transporting material contained in the hole transporting layer 3 and a compound represented by the chemical formula [Chemical Formula 23] as the light emitting layer 4. , An organic EL device was produced by performing the same operation as in Example 11. When a DC voltage of 10V was applied to this element, 240cd / m²Luminescence was obtained.

【0099】

(Example 41) An organic EL device was produced by performing the same operation as in Example 40 except that a compound represented by the chemical formula [Chemical Formula 5] was used as the hole transport material contained in the hole transport layer 3. When a DC voltage of 10V was applied to this element, it was 270cd / m.²Luminescence was obtained.

【0100】

(Example 42) The same operation as in Example 11 except that the compound represented by the chemical formula [Chemical Formula 3] is used as the electron transport layer 5 and the compound represented by the chemical formula [Chemical Formula 21] is used as the light emitting layer 4. To produce an organic EL device. When a DC voltage of 10V was applied to this element, it was 760cd / m.²Luminescence was obtained.

【0101】

(Example 43) An organic EL device was produced by performing the same operation as in Example 42 except that the compound represented by the chemical formula [Chemical Formula 4] was used as the electron transport layer 5. When a DC voltage of 10V was applied to this element, it was 890cd / m.²Luminescence was obtained.

【0102】

[Effect of the invention]

As described above, by using the compound of the present invention as a constituent material of the organic EL device, high-luminance light emission can be obtained as compared with the conventional case, and the effect of the present invention is great.

[Simple explanation of drawings]

[Figure 1]

It is sectional drawing of the element of this invention.

[Figure 2]

It is sectional drawing of the element of this invention.

[Fig. 3]

It is sectional drawing of the element of this invention.

[Fig. 4]

It is sectional drawing of the element of this invention.

[Explanation of symbols]

1 board 2 Anode 3 hole transport layer 4 light emitting layer 5 Electron transport layer 6 Cathode