JP3285085B2 - Organic electroluminescent device - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence device having excellent light emission characteristics.

[0002]

2. Description of the Related Art Organic electroluminescence (EL)
The element is a self-luminous element utilizing the principle that a fluorescent substance emits light by the recombination energy of holes injected from an anode and electrons injected from a cathode when an electric field is applied. C. W. Tang et al. Report on a low-voltage driven organic EL device using a stacked device (CW Tang, S.M.
A. VanSlyke, Applied Physics Letters
s), vol. 51, p. 913, 1987), research on organic EL devices using organic materials as constituent materials has been actively conducted. Tang et al. Use tris (8-hydroxyquinolinol aluminum) for the light emitting layer and a triphenyldiamine derivative for the hole transport layer. The advantages of the stacked structure include: increasing the efficiency of injecting holes into the light emitting layer; increasing the efficiency of generating excitons generated by recombination by blocking electrons injected from the cathode; And confining excitons. As in this example, the element structure of the organic EL element is a two-layer type of a hole transporting (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. Are well known. In such a laminated structure element, in order to increase the recombination efficiency of injected holes and electrons, the element structure and the forming method are devised.

[0003] As the hole transporting material, 4,4 ', 4 "-tris (3-methylphenylphenylamino) triphenylamine or N, N'-diphenyl-N, N'-bis ( 3-methylphenyl)-
Triphenylamine derivatives such as [1,1'-biphenyl] -4,4'-diamine and aromatic diamine derivatives are well known (for example, JP-A-8-20771,
JP-A-8-40995, JP-A-8-40997, JP-A-8-53397, JP-A-8-871
No. 22, etc.).

As the electron transporting material, oxadiazole derivatives, triazole derivatives and the like are well known.

As light-emitting materials, light-emitting materials such as chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives and oxadiazole derivatives are known. It has been reported that the color can also emit light in the visible region from blue to red, and realization of a color display element is expected (for example, JP-A-8-239655, JP-A-7-138561, JP-A-3-200289, etc.).

[0006]

Recently, an organic EL device having a high luminance and a long life has been disclosed or reported, but is not necessarily sufficient. Therefore, there is a strong demand for the development of materials exhibiting high performance. The purpose of the present invention is
An object of the present invention is to provide a high-luminance light-emitting organic EL device.

[0007]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, an organic EL device manufactured using a specific perylene compound as a light emitting material emits light with higher luminance than before. I found something. Further, it was found that the material has a high carrier transporting property, and an organic EL device manufactured using the material as a hole transporting material or an electron transporting material, and a mixture of the material with another hole transporting material or an electron transporting material. Organic E prepared using thin film
The present inventors have found that the L element emits light with higher luminance than the conventional one, and have reached the present invention.

That is, the present invention provides an organic electroluminescent device having one or more organic thin film layers including a light emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers has a general formula (1):

[0009]

Embedded image (Wherein R ^{1 to} R ¹² each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl Group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group,
Represents a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryloxy group . However, at least one of the general formula R ¹ ~R ¹² (2):

[0010]

Embedded image (In the formula (2), R ^{13 to} R ²³ each independently represent a hydrogen atom,
Halogen atom, hydroxyl group, substituted or unsubstituted amino group (excluding diarylamino group), nitro group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cyclo group Alkyl 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,
A substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted styryl group (provided that R ^{13 to} R ¹⁷ are not
) Represents a carboxyl group. R ^{13 to} R ²³ may form a ring with two of them. Also, R ²⁴
To R ²⁸ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, —NAr ¹ Ar ² (Ar ¹ and Ar ² each independently represent an aryl group having 6 to 20 carbon atoms, and the aryl group has a substituent. Or a substituted or unsubstituted diarylamino group, nitro group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group represented by A substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group,
Represents a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group. R ^{24 to} R ²⁸ may form a ring with two of them. ) Is a diarylamino group having a styryl substituent. The present invention relates to an organic electroluminescent device comprising the perylene compound represented by the formula (1) alone or in a mixture.

Further, the present invention provides the organic thin film layer,
It has at least a light emitting layer and a hole transport layer, and the light emitting layer has a general formula
An organic electroluminescent device comprising the compound represented by (1) alone or as a mixture.

Further, the present invention provides the organic thin film layer,
An organic electroluminescent device having at least a hole transport layer, wherein the layer contains the compound represented by the general formula (1) alone or as a mixture.

Furthermore, the present invention provides that the organic thin film layer has at least an electron transport layer and a hole transport layer, and the electron transport layer contains the compound represented by the general formula (1) alone or as a mixture. This is an organic electroluminescent element characterized by the following.

[0014]

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 (1).

R ^{1 to} R ¹² each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group. A substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, Represents an unsubstituted aryloxy group. R ^{1 to} R ¹² may form a ring with two of them.

Examples of the halogen atom include fluorine, chlorine, bromine and iodine. A substituted or unsubstituted amino group is represented by -NX ¹ X ² , wherein X ¹ and X ² each independently represent a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s- Butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxy Isobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3
-Trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 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-dibromo t-butyl group, 1,2,3-tribromo Propyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3
-Diiodoisopropyl group, 2,3-diiodo-tert-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-diamino t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group,
A cyanoisobutyl group, a 1,2-dicyanoethyl group,
1,3-dicyanoisopropyl group, 2,3-dicyano t
-Butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro t-butyl group, 1,2,3-trinitropropyl group,
Phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1
-Phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl 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, p-terphenyl-3-yl, p-terphenyl-2-yl, 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-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl Group, 3-pyridinyl group, 4-pyridinyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7
-Indolyl group, 1-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl 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, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 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, 1-phenanthridinyl group, 2-phenanthine Lysinyl 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-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group Group, 1,7-phenanthrolin-6-yl group, 1,7-
Phenanthroline-8-yl group, 1,7-phenanthroline-9-yl group, 1,7-phenanthroline-10-
Yl group, 1,8-phenanthrolin-2-yl group, 1,
8-phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl group, 1,8-phenanthroline-5
-Yl group, 1,8-phenanthrolin-6-yl group,
1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group, 1,9-phenanthrolin-2-yl Group, 1,9-phenanthrolin-3-yl group, 1,9-
Phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group, 1, 9
-Phenanthroline-8-yl group, 1,9-phenanthroline-10-yl group, 1,10-phenanthroline-
2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group, 1,1
0-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-phenanthroline-3
-Yl group, 2,9-phenanthrolin-4-yl group,
2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group Group, 2,9-phenanthrolin-10-yl group, 2,8
-Phenanthroline-1-yl group, 2,8-phenanthrolin-3-yl group, 2,8-phenanthroline-4-
Yl group, 2,8-phenanthrolin-5-yl group, 2,
8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthroline-9
An -yl group, a 2,8-phenanthroline-10-yl group,
2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group, 2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group Group, 2,7-phenanthrolin-6-yl group, 2,7-
Phenanthroline-8-yl group, 2,7-phenanthroline-9-yl group, 2,7-phenanthroline-10-
Yl group, 1-phenazinyl group, 2-phenazinyl group, 1
-Phenothiazinyl group, 2-phenothiazinyl group, 3-
Phenothiazinyl group, 4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group,
2-oxadiazolyl group, 5-oxadiazolyl group, 3
-Furazanyl group, 2-thienyl group, 3-thienyl group, 2
-Methylpyrrole-1-yl group, 2-methylpyrrole-
3-yl group, 2-methylpyrrole-4-yl group, 2-methylpyrrole-5-yl group, 3-methylpyrrole-1-
Yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3- (2-
Phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group,
2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-
Examples thereof include a butyl 1-indolyl group, a 2-t-butyl 3-indolyl group, and a 4-t-butyl 3-indolyl group.

Examples of the substituted or unsubstituted alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group and a t-butyl group.
Butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 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-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-dibromo t-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-diamino t-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-dicyano-t-butyl group,
1,2,3-tricyanopropyl group, nitromethyl group,
1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro t-butyl group, 1,2,3-trinitro And a propyl group.

Examples of the substituted or unsubstituted alkenyl group include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butanedienyl, and
-Methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group , 1-phenyl-1-
Butenyl and 3-phenyl-1-butenyl.

Examples of the substituted or unsubstituted cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and a 4-methylcyclohexyl group.

A substituted or unsubstituted alkoxy group is represented by-
A group represented by OY, wherein Y is methyl, ethyl, propyl, isopropyl, n-butyl, 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-dibromo t-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-
Diamino t-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
-Dicyano t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitro Isopropyl group, 2,
Examples include a 3-dinitro t-butyl group and a 1,2,3-trinitropropyl group.

Examples of the substituted or unsubstituted aromatic hydrocarbon group include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, and 1-phenanthryl. , 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl 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-p-terphenyl-4-yl group and the like.

The substituted or unsubstituted aromatic heterocyclic group includes 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, Indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1
-Isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3 -Benzofuranyl group, 4-benzofuranyl group, 5
-Benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzo Furanyl 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-
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
-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-phenanthroline-2-yl group, 1,7-phenanthroline-3
-Yl group, 1,7-phenanthrolin-4-yl group,
1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group Group, 1,7-phenanthrolin-10-yl group, 1,8
-Phenanthroline-2-yl group, 1,8-phenanthrolin-3-yl group, 1,8-phenanthroline-4-
Yl group, 1,8-phenanthrolin-5-yl group, 1,
8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthroline-9
-Yl group, 1,8-phenanthrolin-10-yl group,
1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl Group, 1,9-phenanthrolin-6-yl group, 1,9-
Phenanthroline-7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phenanthroline-10-
An yl group, a 1,10-phenanthrolin-2-yl group,
1,10-phenanthrolin-3-yl group, 1,10-
Phenanthroline-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phenanthroline-1-
Yl group, 2,9-phenanthrolin-3-yl group, 2,
9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthroline-6
-Yl group, 2,9-phenanthrolin-7-yl group,
2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl Group, 2,8-phenanthrolin-4-yl group, 2,8-
Phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2, 8
-Phenanthroline-10-yl group, 2,7-phenanthrolin-1-yl group, 2,7-phenanthroline-3
-Yl group, 2,7-phenanthrolin-4-yl group,
2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl group Group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, -Phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group,
4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrole- 3-yl group, 2-methylpyrrole-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group,
3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-
t-butylpyrrole-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl Group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t-butyl 3-indolyl group,
4-t-butyl 3-indolyl group, and the like.

The substituted or unsubstituted aralkyl group includes benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthyl Methyl group, 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-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-
Pyrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromo Benzyl 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, p-cyanobenzyl group, m-cyanobenzyl group,
Examples thereof include an o-cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group, a 1-chloro-2-phenylisopropyl group, and the like.

The substituted or unsubstituted aryloxy group is represented by —OZ, where Z is a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group,
2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl 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-p-terphenyl-4-yl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4
-Pyridinyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 3
-Isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl 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-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, 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-phenanthroline-2-yl Group, 1,7-phenanthrolin-3-yl group, 1,7-
Phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthroline-8-yl group, 1, 7
-Phenanthroline-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthroline-2
-Yl group, 1,8-phenanthrolin-3-yl group,
1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group Group, 1,8-phenanthrolin-9-yl group, 1,8-
Phenanthroline-10-yl group, 1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3-
Yl group, 1,9-phenanthrolin-4-yl group, 1,
9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthroline-7
-Yl group, 1,9-phenanthroline-8-yl group,
1,9-phenanthrolin-10-yl group, 1,10-
Phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthroline-4
-Yl group, 1,10-phenanthrolin-5-yl group,
2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group Group, 2,9-phenanthrolin-6-yl group, 2,9-
Phenanthroline-7-yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10-
Yl group, 2,8-phenanthrolin-1-yl group, 2,
8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthroline-5
-Yl group, 2,8-phenanthrolin-6-yl group,
2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl Group, 2,7-phenanthrolin-3-yl group, 2,7-
Phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2, 7
-Phenanthroline-9-yl group, 2,7-phenanthroline-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group , 4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl Group, 3-flazanyl group, 2-thienyl group, 3-
Thienyl group, 2-methylpyrrole-1-yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrole-4-yl
Yl group, 2-methylpyrrole-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrole-5-yl Yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-
Indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t-butyl 3-indolyl group , 4-t-butyl 3-indolyl group and the like.

R ^{13 to} R ²³ each independently represent a hydrogen atom, the halogen atom, the hydroxyl group, the substituted or unsubstituted amino group (excluding the diarylamino group),
A nitro group, a cyano group, the substituted or unsubstituted alkyl group, the substituted or unsubstituted alkenyl group, the substituted or unsubstituted cycloalkyl group, the substituted or unsubstituted alkoxy group, the substituted group Or an unsubstituted aromatic hydrocarbon group, the above-mentioned substituted or unsubstituted aromatic heterocyclic group, the above-mentioned substituted or unsubstituted aralkyl group, the above-mentioned substituted or unsubstituted aryloxy group, substituted or unsubstituted alkoxy Represents a carbonyl group, a substituted or unsubstituted styryl group, or a carboxyl group. R ^{13 to} R ²³ may form a ring with two of them.

A substituted or unsubstituted alkoxycarbonyl group is represented by --COOY, wherein Y represents a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-group.
-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-dibromo t-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-
Diamino t-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
-Dicyano t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitro Isopropyl group, 2,
Examples include a 3-dinitro t-butyl group and a 1,2,3-trinitropropyl group.

Examples of the substituted or unsubstituted styryl group include a styryl group, a 2,2-diphenylvinyl group,
As a substituent of terminal phenyl groups, halogen atom, a hydroxyl ^{group, -NAr 1 Ar 2 (Ar 1} , Ar 2 each independently represents an aryl group having 6 to 20 carbon atoms, the aryl group has a substituent Or a substituted or unsubstituted diarylamino group, a nitro group, a cyano group, the above-mentioned substituted or unsubstituted alkyl group, the above-mentioned substituted or unsubstituted alkenyl group, the above-mentioned substituted or unsubstituted group. A substituted cycloalkyl group, the substituted or unsubstituted alkoxy group, the substituted or unsubstituted aromatic hydrocarbon group, the substituted or unsubstituted aromatic heterocyclic group, the substituted or unsubstituted aralkyl Group having the above-mentioned substituted or unsubstituted aryloxy group, the aforementioned substituted or unsubstituted alkoxycarbonyl group, carboxyl group, etc. A styryl group, and a substituted 2,2-diphenyl vinyl group and the like.

The aryl group having 6 to 20 carbon atoms includes a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a naphthacenyl group, a pyrenyl group and the like.

Examples of the substituent of the aryl group include a halogen atom, a hydroxyl group, a nitro group, a cyano group, the above-mentioned substituted or unsubstituted alkyl group, the above-mentioned substituted or unsubstituted alkenyl group, and the above-mentioned substituted group. Or an unsubstituted cycloalkyl group, the substituted or unsubstituted alkoxy group, the substituted or unsubstituted aromatic hydrocarbon group, the substituted or unsubstituted aromatic heterocyclic group, the substituted or unsubstituted group Aralkyl group, the above-mentioned substituted or unsubstituted aryloxy group, the above-mentioned substituted or unsubstituted alkoxycarbonyl group, carboxyl group and the like.

R ^{24 to} R ²⁸ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group or the above-mentioned —NAr ¹ Ar
² (Ar ¹ and Ar ² each independently represent an aryl group having 6 to 20 carbon atoms, and the aryl group may have a substituent.) A nitro group, a cyano group, the substituted or unsubstituted alkyl group, the substituted or unsubstituted alkenyl group, the substituted or unsubstituted cycloalkyl group, the substituted or unsubstituted alkoxy group, the substituted group Or an unsubstituted aromatic hydrocarbon group, the above-mentioned substituted or unsubstituted aromatic heterocyclic group, the above-mentioned substituted or unsubstituted aralkyl group, the above-mentioned substituted or unsubstituted aryloxy group, the above-mentioned substituted or unsubstituted Represents an alkoxycarbonyl group or a carboxyl group. The R ²⁴ ~R ²⁸
May form a ring with two of them.

Examples of the divalent group forming a ring in R ^{1 to} R ²⁸ include a tetramethylene group, a pentamethylene group,
Hexamethylene group, diphenylmethane-2,2'-diyl group, diphenylethane-3,3'-diyl group, diphenylpropane-4,4'-diyl group, 1,3-butadiene-1,4-diyl group and the like. No.

The following are examples of compounds of the present invention, but the present invention is not limited to these.

[0034]

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[0035]

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[0036]

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[0037]

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[0038]

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[0039]

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[0040]

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[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

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[0047]

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[0048]

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[0049]

Embedded image The element structure of the organic EL element according to the present invention is a structure in which one or more organic layers are laminated between electrodes, and examples thereof include an anode, a light emitting layer, a cathode, an anode, and a hole transport as shown in FIGS. Layer, light emitting layer, electron transport layer, cathode, anode, hole transport layer, light emitting layer, and cathode structure. The compound in the present invention may be used in any of the above organic layers, and may be doped into other hole transporting materials, light emitting materials, and electron transporting materials.

The hole transporting material used in the present invention is not particularly limited, and any compound which is generally used as a hole transporting agent may be used. For example, the following bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane [01], N, N′-diphenyl-N, N′-bis (3-methylphenyl) -1,1′-biphenyl −4
4'-diamine [02], N, N'-diphenyl-N-
N-bis (1-naphthyl) -1,1'-biphenyl)-
Triphenyldiamines such as 4,4'-diamine [03], and starburst-type molecules ([04] to [06], etc.)
And the like.

[0051]

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The electron transporting material used in the present invention is not particularly limited, and any compound which is generally used as an electron transporting material may be used. For example, 2- (4-biphenylyl) -5- (4-t-butylphenyl) -1,
3,4-oxadiazole [07], bis {2- (4-
oxadiazole derivatives such as t-butylphenyl) -1,3,4-oxadiazole {-m-phenylene [08], triazole derivatives ([09], [10], etc.);
And quinolinol-based metal complexes ([11] to [14], etc.).

[0053]

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The anode of the organic thin film EL element has a role of injecting holes into the hole transport layer, and it is effective that the anode has 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, and copper. As the cathode, a material having a small work function is preferable for the purpose of injecting electrons into the electron transport band or the light emitting layer. The cathode material is not particularly limited, but specifically, indium, aluminum, magnesium, a magnesium-indium alloy, a magnesium-aluminum alloy, an aluminum-lithium alloy, an aluminum-scandium-lithium alloy, a magnesium-silver alloy, or the like can be used.

The method for forming each layer of the organic EL device of the present invention is not particularly limited. A conventionally known formation method such as a vacuum evaporation method and a spin coating method can be used. The organic thin film layer containing the compound represented by the general formula (1) used in the organic EL device of the present invention may be formed by vacuum evaporation, molecular beam evaporation (MBE), dipping of a solution dissolved in a solvent, spinning, or the like. It can be formed by a known method such as a coating method, a casting method, a bar coating method, and a roll coating method.

The thickness of each organic layer of the organic EL device of the present invention is not particularly limited. In general, if the thickness is too small, defects such as pinholes are likely to occur. Is usually worse, several nm to 1
The range of μm is preferred.

Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist of the present invention.

[0058]

EXAMPLES First, synthetic examples (Synthetic Examples 1 to 5) of the above-mentioned compound of the present invention will be described.

Synthesis Example 1 Compound (3) (3- (N- (4
-(4-methylphenylvinyl) phenyl) -Np-
Synthesis of tolylamino) perylene) 3-bromoperylene, N-phenyl-p-toluidine,
Potassium carbonate, copper powder and nitrobenzene were placed in a reaction vessel and stirred at 200 ° C. for 40 hours. After completion of the reaction, nitrobenzene was distilled off under reduced pressure, chloroform was added, and the mixture was filtered.
Inorganic substances were removed. After the filtrate was concentrated, it was purified according to a conventional method to obtain 3-N-phenyl-NP-tolylaminoperylene. The obtained 3-N-phenyl-Np-tolylaminoperylene was dissolved in toluene, phosphorus oxychloride was added, and the mixture was stirred at room temperature, and N-methylformanilide was added dropwise.
Stirred at 50 ° C. for 5 hours. After completion of the reaction, the mixture was poured into cold water, and the organic layer was washed with water, dried, and concentrated under reduced pressure. Thereafter, purification was performed according to a conventional method to obtain 3- (Np-formylphenyl-N-tolylamino) perylene. The obtained 3-
(Np-formylphenyl-N-tolylamino) perylene, p-methylbenzylphosphonic acid diethyl ester and sodium hydride were reacted in dimethyl sulfoxide for 24 hours. The reaction solution was poured into ice water, extracted with chloroform, dried and concentrated under reduced pressure. Thereafter, purification was performed according to a conventional method to obtain the desired compound (3).

Synthesis Example 2 Compound (4) (3- (N- (4
Synthesis of-(phenylvinyl) phenyl) -N-p-tolylamino) perylene) Compound (4) was prepared in the same manner as in Synthesis Example 1 except that benzylphosphonic acid diethyl ester was used instead of p-methylbenzylphosphonic acid diethyl ester. Obtained.

Synthesis Example 3 Compound (5) (3,10-bis (N-4- (4-methylphenylvinyl) phenyl-N
Synthesis of -p-tolylamino) perylene) 3,10-dibromoperylene, N- (4- (4-methylphenylvinyl) phenyl) -p-toluidine, potassium carbonate, copper powder and nitrobenzene are placed in a reaction vessel,
Stirred at 200 ° C. for 40 hours. After completion of the reaction, nitrobenzene was distilled off under reduced pressure, chloroform was added, and the mixture was filtered to remove inorganic substances. After the filtrate was concentrated, it was purified according to a conventional method to obtain a compound (5).

Synthesis Example 4 Compound (12) (3- (N-4)
Synthesis of-(4-methylphenylvinyl) phenyl-N-p-tolylamino) -9- (N-p-tolyl-N-phenylamino) perylene) Using 3,9-dibromoperylene instead of 3-bromoperylene Other than that, the compound (12) was prepared in the same manner as in Synthesis Example 1.
I got

Synthesis Example 5 Compound (13) (3,9-bis (N-4- (4-methylphenylvinyl) phenyl-N
Synthesis of -p-tolylamino) perylene) Compound (13) was obtained in the same manner as in Synthesis Example 3 except that 3,9-dibromoperylene was used instead of 3,10-dibromoperylene.

Hereinafter, the compound of the present invention was added to the light-emitting layer (1 to 1).
4) (19-22), a thin film mixed with a hole transport material is a light emitting layer (15-18), a thin film mixed with an electron transport material is a light emitting layer (23-27), and a hole transport layer (28-29). And an example in which the electron transport layer (30) is used.

Example 1 FIG. 1 shows a cross-sectional structure of an element used in Example 1. Hereinafter, a procedure for manufacturing the organic thin film EL device used in Example 1 of the present invention will be described. The device is composed of an anode / a light emitting layer / a cathode. ITO is formed on a glass substrate by sputtering so that the sheet resistance becomes 20Ω / □,
The anode was used. A compound (3) having a thickness of 40 nm was formed thereon as a light emitting layer by a vacuum evaporation method. Next, a magnesium-silver alloy was formed to a thickness of 200 nm as a cathode by a vacuum evaporation method to produce an organic EL device. When a DC voltage of 5 V was applied to this device, light emission of 1020 cd / m ² was obtained.

Example 2 Example 1 was repeated except that the compound (4) was used as a luminescent material.
The same operation as described above was performed to produce an organic EL device. When a DC voltage of 5 V was applied to this device, light emission of 980 cd / m ² was obtained.

Example 3 Example 1 was repeated except that the compound (5) was used as a luminescent material.
The same operation as described above was performed to produce an organic EL device. When a DC voltage of 5 V was applied to this element, 1360 cd / m ²
Was obtained.

Example 4 An organic EL device was manufactured in the same manner as in Example 1 except that the compound (12) was used as a light emitting material. When a DC voltage of 5 V was applied to this element, 1210 cd / m
² luminescence was obtained.

Example 5 An organic EL device was manufactured in the same manner as in Example 1 except that the compound (13) was used as a light emitting material. When a DC voltage of 5 V was applied to this element, 1300 cd / m
² luminescence was obtained.

Example 6 An ITO was formed on a glass substrate by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. A 40 nm light emitting layer was formed thereon by a spin coating method using a chloroform solution of the compound (13). Next, a magnesium-silver alloy was used as a cathode by vacuum evaporation for 20 minutes.
An organic EL device was fabricated by forming the film to a thickness of 0 nm. When a DC voltage of 5 V was applied to this device, light emission of 410 cd / m ² was obtained.

Example 7 FIG. 2 shows a cross-sectional structure of the device used in Example 7. The device was composed of an anode / a hole transport layer / a light emitting layer / an electron transport layer / a cathode. ITO is formed on a glass substrate by sputtering so that the sheet resistance becomes 20Ω / □,
The anode was used. N, N'-diphenyl-N, N'-bis (3-methylphenyl)-is formed thereon as a hole transport layer.
[1,1′-biphenyl] -4,4′-diamine [0
2] was formed to a thickness of 50 nm by a vacuum evaporation method. Next, as a light emitting layer, the compound (3) was formed to a thickness of 40 nm by a vacuum evaporation method. Next, 2- (4-biphenylyl) is used as an electron transport layer.
-5- (4-t-butylphenyl) -1,3,4-oxadiazole [07] was formed to a thickness of 20 nm by a vacuum evaporation method. Next, a magnesium-silver alloy was formed as a cathode to a thickness of 200 nm by a vacuum evaporation method to produce an organic EL device.
When a DC voltage of 10 V was applied to this element, 3400
Light emission of cd / m ² was obtained.

Example 8 Example 7 was repeated except that the compound (4) was used as the luminescent material.
The same operation as described above was performed to produce an organic EL device. When a DC voltage of 10 V was applied to this element, 3350 cd / m
² luminescence was obtained.

Example 9 Example 7 was repeated except that the compound (5) was used as a luminescent material.
The same operation as described above was performed to produce an organic EL device. When a DC voltage of 10 V was applied to this element, it was 5300 cd / m
² luminescence was obtained.

Example 10 An organic EL device was manufactured in the same manner as in Example 7, except that the compound (12) was used as the light emitting material. When a DC voltage of 10 V was applied to this element, 4430 cd /
m ² emission was obtained.

Example 11 An organic EL device was manufactured in the same manner as in Example 7, except that the compound (13) was used as the light emitting material. When a DC voltage of 10 V was applied to this element, 5740 cd /
m ² emission was obtained.

Example 12 N, N'-diphenyl-NN-bis (1-naphthyl) -1,1'-biphenyl) -4,4 as a hole transport layer
'-Diamine [03] as an electron transporting layer
An organic EL device was produced in the same manner as in Example 11, except that (4-t-butylphenyl) -1,3,4-oxadiazole} -m-phenylene [08] was used. When a DC voltage of 10 V was applied to this element, 6230c
Light emission of d / m ² was obtained.

Example 13 [04] was used as a hole transport layer, and compound (5) was used as a light emitting layer.
Example 7 except that [11] was used as the electron transport layer.
The same operation as described above was performed to produce an organic EL device. When a DC voltage of 10 V was applied to this element, 5580 cd / m
² luminescence was obtained.

Example 14 [05] was used as the hole transport layer, and the compound (1) was used as the light emitting layer.
3) was performed in the same manner as in Example 7, except that [12] was used as the electron transporting layer, to produce an organic EL device. When a DC voltage of 10 V was applied to this element, 5370 cd
/ M ² was obtained.

Example 15 As a light emitting layer, N, N'-diphenyl-NN-bis (1
-Naphthyl) -1,1'-biphenyl) -4,4'-diamine [03] and compound (3) were co-evaporated at a weight ratio of 1:10 to form a thin film of 50 nm. The same operation as in Example 7 was performed to produce an organic EL device. When a DC voltage of 10 V was applied to this element, 4250 cd
/ M ² was obtained.

Example 16 An organic EL device was manufactured in the same manner as in Example 15, except that the compound (4) was used instead of the compound (3).
When a DC voltage of 10 V was applied to this element, 4030
Light emission of cd / m ² was obtained.

Example 17 An organic EL device was manufactured in the same manner as in Example 15, except that the compound (12) was used instead of the compound (3). When a DC voltage of 10 V was applied to this element, 53
Light emission of 70 cd / m ² was obtained.

Example 18 An organic EL device was manufactured in the same manner as in Example 15 except that the compound (13) was used instead of the compound (3). When a DC voltage of 10 V was applied to this element, 67
Light emission of 10 cd / m ² was obtained.

Example 19 FIG. 3 shows a cross-sectional structure of the device used in Example 19. The device is composed of an anode / a hole transport layer / a light emitting layer / a cathode. ITO was formed on a glass substrate by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. N, N'-diphenyl- is formed thereon as a hole transport layer.
N-N-bis (1-naphthyl) -1,1'-biphenyl) -4,4'-diamine [03] was obtained by vacuum evaporation at 5
0 nm was formed. Next, as a light-emitting layer, a film formed by vacuum co-evaporation of the compound (3) was formed to a thickness of 40 nm. Next, a magnesium-silver alloy was formed to a thickness of 200 nm as a cathode to produce an EL element. When a DC voltage of 10 V was applied to this device, light emission of 2370 cd / m ² was obtained.

Example 20 An organic EL device was manufactured in the same manner as in Example 19 except that the compound (5) was used instead of the compound (3).
When a DC voltage of 10 V was applied to this element, 3040
Light emission of cd / m ² was obtained.

Example 21 An organic EL device was manufactured in the same manner as in Example 19 except that the compound (12) was used instead of the compound (3). When a DC voltage of 10 V was applied to this device, 28
Emission of 80 cd / m ² was obtained.

Example 22 An organic EL device was manufactured in the same manner as in Example 19 except that the compound (13) was used instead of the compound (3). When a DC voltage of 10 V was applied to this element, 31
Light emission of 10 cd / m ² was obtained.

Example 23 An organic EL device was prepared in the same manner as in Example 19, except that a film formed by vacuum co-evaporation of [11] and the compound (3) at a weight ratio of 20: 1 was formed to a thickness of 50 nm. Was prepared.
When a DC voltage of 10 V was applied to this element, 1870
Light emission of cd / m ² was obtained.

Example 24 An organic EL device was manufactured in the same manner as in Example 23 except that the compound (5) was used instead of the compound (3).
When a DC voltage of 10 V was applied to this element, 2230
Light emission of cd / m ² was obtained.

Example 25 An organic EL device was manufactured in the same manner as in Example 23 except that the compound (12) was used instead of the compound (3). When a DC voltage of 10 V was applied to this element, 20
Light emission of 60 cd / m ² was obtained.

Example 26 An organic EL device was manufactured in the same manner as in Example 23 except that the compound (13) was used instead of the compound (3). When a DC voltage of 10 V was applied to this element, 20
Light emission of 30 cd / m ² was obtained.

Example 27 N, N'-diphenyl-N, N'-bis (3-methylphenyl)-[1,1'-biphenyl] as a hole transport layer
-4,4'-diamine [02] was used as a light emitting layer [1
3] and the compound (13) in a weight ratio of 20: 1, and an organic EL device was produced in the same manner as in Example 19 except that a film produced by vacuum co-evaporation was used. When a DC voltage of 10 V was applied to this device, light emission of 2160 cd / m ² was obtained. Example 28 Compound (3) was used as a hole transport layer, and [1] was used as a light emitting layer.
3], except that organic E was used.
An L element was produced. When a DC voltage of 10 V was applied to this device, light emission of 1760 cd / m ² was obtained.

Example 29 An organic EL device was manufactured in the same manner as in Example 28 except that the compound (13) was used as the hole transporting material.
When a DC voltage of 10 V was applied to this element, 1970
Light emission of cd / m ² was obtained.

Example 30 An organic EL device was manufactured in the same manner as in Example 7, except that the compound (3) was used as the electron transport layer and [11] was used as the light emitting layer. Apply a DC voltage of 10 V to this element.
Upon application, light emission of 760 cd / m ² was obtained.

[0094]

As described above, when the compound of the present invention is used as a constituent material of an organic EL device, light emission with higher luminance than before can be obtained, and the effect of the present invention is great.

[Brief description of the drawings]

FIG. 1 is a sectional view of an organic EL device of the present invention.

FIG. 2 is a cross-sectional view of the organic EL device of the present invention.

FIG. 3 is a cross-sectional view of the organic EL device of the present invention.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 1 Substrate 2 Anode 3 Hole transport layer 4 Light emitting layer 5 Electron transport layer 6 Cathode

Continuation of front page (72) Inventor Atsushi Oda 5-7-1 Shiba, Minato-ku, Tokyo NEC Corporation (56) References JP-A-9-268284 (JP, A) JP-A-10-251633 ( JP, A) JP-A-2000-113984 (JP, A) JP-A-2000-58261 (JP, A) JP-A-11-185961 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) ) H05B 33/14 H05B 33/22 C09K 11/06 CA (STN) REGISTRY (STN)

Claims (5)

(57) [Claims] 1. An organic electroluminescent device having one or more organic thin film layers including a light emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers has a general formula (1): (Wherein R ^{1 to} R ¹² each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl Group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group,
Represents a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryloxy group . However the at least one formula of R ¹ ~R ¹² (2): ## STR2 ## (In the formula (2), R ^{13 to} R ²³ each independently represent a hydrogen atom,
Halogen atom, hydroxyl group, substituted or unsubstituted amino group (excluding diarylamino group), nitro group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cyclo group Alkyl 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,
A substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted styryl group (provided that R ^{13 to} R ¹⁷ are not
) Represents a carboxyl group. R ^{13 to} R ²³ may form a ring with two of them. Also, R ²⁴
To R ²⁸ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, —NAr ¹ Ar ² (Ar ¹ and Ar ² each independently represent an aryl group having 6 to 20 carbon atoms, and the aryl group has a substituent. Or a substituted or unsubstituted diarylamino group, nitro group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group represented by A substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group,
Represents a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group. R ^{24 to} R ²⁸ may form a ring with two of them. ) Is a diarylamino group having a styryl substituent. An organic electroluminescent device comprising the perylene compound represented by the formula (1) alone or in a mixture. 2. The group represented by the general formula (2) is a nitrogen atom
One of the two phenyl groups bonded to
A styryl group only at the p-position (the styryl group has a substituent
May be represented by the general formula (1):
Being at least one of R ^{1 to} R ¹²
The organic electroluminescent device according to claim 1, wherein
Element. 3. The organic thin film layer has at least a light emitting layer and a hole transport layer, and the light emitting layer contains the compound represented by the general formula (1) alone or as a mixture. The organic electroluminescent device according to the above. 4. The organic material according to claim 1, wherein the organic thin film layer has at least a hole transport layer, and this layer contains the compound represented by the general formula (1) alone or as a mixture. Electroluminescence element. 5. The organic thin film layer has at least an electron transport layer and a hole transport layer, wherein the electron transport layer has a general formula (1)
The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (1) is contained alone or as a mixture.