JP2001176664A - Organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic EL element having a high intensity. SOLUTION: As a composition material of the organic EL element, a benzo perilene compound shown by a formula (1) is used. In the formula, R1 to R12 are respectively and independently, a hydrogen atom, a halogen atom, and a hydroxyl group, an amino group of substitution or non-substitution, a nitro group, cyano group, an alkyl group of substitution or non-substitution, an alkenyl group of substitution or non-substitution, a styril group of substitution or non- substitution, a cyclo-alkyl group of substitution or non-substitution, an alkoxy group of substitution or non-substitution, an aromatic hydrocarbon group of substitution or non-substitution, aromatic hydrocyclic compound group of substitution or non-substitution, an aralkyl group of substitution or non-substitution, an allyloxy group of substitution or non-substitution. A ring may be formed by two of R1 to R12. However, at least one of R1 to R12 is a steric hindrance group which suppresses an association of molecules.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

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

[0002]

2. Description of the Related Art An organic electroluminescent device (hereinafter simply referred to as an "organic EL device") is a device that applies an electric field to recombine energy of holes injected from an anode and electrons injected from a cathode. Is a self-luminous element utilizing the principle that a fluorescent substance emits light.

[0003] Eastman Kodak C.I. W. Ta
ng et al. report on a low-voltage driven organic EL device using a stacked device (CW Tang, SA VanSlyk).
e, Applied Physics Letters (Applied
Physics Letters), 51, 913
(1987, p. 1987), researches on organic EL elements using organic materials as constituent materials have 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.

[0004] As in this example, the element structure of the organic EL element has a two-layer structure of a hole transporting (injecting) layer and an electron transporting light emitting layer, or a hole transporting (injecting) layer, a light emitting layer, and an electron transporting (electron transporting) layer. Injection) layers 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.

[0005] As a 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-8-8
No. 7122).

[0006] Oxadiazole derivatives, triazole derivatives and the like are well known as electron transporting materials. Further, 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. Also, it has been reported that light emission in the visible region from blue to red can be obtained, and realization of a color display element is expected (for example, see JP-A-8-23).
9655, JP-A-7-138561, JP-A-3-200889, etc.).

As described above, various high-luminance and long-life organic EL devices have been disclosed or reported, but are not necessarily satisfactory. The present inventors disclosed in Japanese Patent Laid-Open No. 11-1
As disclosed in Japanese Patent No. 44869, it has been disclosed that an organic EL device which emits light with high luminance can be obtained by using a specific perylene compound. However, in some perylene compounds, due to formation of an intermolecular association state, sufficient performance may not be obtained in some cases. Dye materials used in other organic electroluminescent devices also disperse at a high concentration and form an association state between molecules in a solid formed by the dye alone, thereby causing concentration quenching and In many cases, a phenomenon in which the emission intensity of the so-called dye was significantly reduced was observed.

[0008]

SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and has as its object to provide a high-luminance organic EL device in which concentration quenching is suppressed.

[0009]

Means for Solving the Problems The inventors of the present invention have made intensive studies to solve the above-mentioned problems, and as a result, a compound in which a sterically hindered group that suppresses formation of an associated state is introduced into a specific perylene derivative as a luminescent material. It was found that the organic EL device manufactured using the device emits light with higher luminance than the conventional organic EL device. 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. The present inventors have found that an organic EL device manufactured using a thin film emits light at a higher luminance than in the past, and have reached the present invention.

According to the present invention, there is provided an organic EL 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):

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 styryl 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 an unsubstituted aralkyl group or a substituted or unsubstituted aryloxy group, and R ^{1 to} R ¹² may form a ring with two of them, provided that R ^{1 to} R ¹² At least one is -N
And a diarylamino group represented by Ar ¹ Ar ² (Ar ¹ and Ar ² represent a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group). Further, at least one of R ^{1 to} R ¹² which is not a diarylamino group is a sterically hindered group which suppresses formation of an association state between molecules. The present invention provides an organic EL device comprising the perylene compound represented by the formula (1) alone or in a mixture.

A second aspect of the present invention is an organic EL 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 (2):

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 styryl 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 an unsubstituted aralkyl group or a substituted or unsubstituted aryloxy group, and R ^{1 to} R ¹² may form a ring with two of them, provided that R ^{1 to} R ¹² At least one is -N
Ar ¹ Ar ² (Ar ¹ and Ar ² represent a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, provided that at least one of Ar ¹ and Ar ² is substituted Or an unsubstituted styryl group as a substituent.). At least one of R ^{1 to} R ¹² , which is not a diarylamino group, is a sterically hindered group that suppresses the formation of an intermolecular association state. The present invention provides an organic EL device comprising the perylene compound represented by the formula (1) alone or in a mixture.

A third aspect of the present invention is the organic compound according to the first or second aspect.
In the EL device, there is provided an organic EL device having at least a light emitting layer as the organic thin film layer, wherein the light emitting layer contains the compound represented by the general formula (1) or (2) alone or as a mixture. I do.

A fourth aspect of the present invention is the organic compound according to the first or second aspect.
In the EL device, the organic thin film layer has at least a hole transport layer, and the hole transport layer contains the compound represented by the general formula (1) or (2) alone or as a mixture. Provide EL devices.

A fifth aspect of the present invention is the organic compound according to the first or second aspect.
In the EL device, the organic thin film layer has at least an electron transport layer, and the electron transport layer contains the compound represented by the general formula (1) or (2) alone or as a mixture. I will provide a.

According to a sixth aspect, in the organic EL device according to any one of the first to fifth aspects, the general formula (1) or (2)
Is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted Provided is an organic EL device, which is a substituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryloxy group.

[0016]

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) or (2). 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, 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 Represents an aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group. Also,
R ^{1 to} R ¹² may form a ring with two of them. However, at least one of R ^{1 to} R ¹² is -NA
^{r 1 Ar 2 (Ar 1,} Ar 2 represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group) diarylamino group represented by. Also,
In the general formula (2), at least one of Ar ¹ and Ar ² has a substituted or unsubstituted styryl group as a substituent. In addition, R ^{1 to} R ¹² which are not diarylamino groups
At least one is a sterically hindered group that suppresses formation of an associated state of the molecule.

The halogen atom includes fluorine, chlorine, bromine and iodine.

The substituted or unsubstituted amino group is --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 group, an isobutyl 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-tricia Propyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 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 group, p-terphenyl-3-
Yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, 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-quinoxa 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-phen Nanthridinyl 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-phenanthroline-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, 1,7-phenanthrolin-10-yl group Group, 1,8-phenanthrolin-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
Phenanthroline-7-yl group, 1,8-phenanthroline-9-yl group, 1,8-phenanthroline-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 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, 1,10-
Phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2, 9
-Phenanthroline-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenanthroline-7-
Yl group, 2,9-phenanthroline-8-yl group, 2,
9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthroline-
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 Group, 2,8-phenanthrolin-10-yl group, 2,7
-Phenanthroline-1-yl group, 2,7-phenanthrolin-3-yl group, 2,7-phenanthroline-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
An -yl group, a 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-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-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
-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- And a 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-tricia Propyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3
-Dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group and the like.

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, a 4-methylcyclohexyl group, a 1-adamantyl group and a 2-adamantyl 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, 1,2,2 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-dicyano Isopropyl 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, cyclopropyl group, cyclobutyl group,
Examples thereof include a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 1-adamantyl group, and a 2-adamantyl 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 a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, 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.

A 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.

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,
-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, 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, 3-diaminoisopropyl group, 2,
3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group,
-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
-A trinitropropyl group and the like.

Examples of the substituted or unsubstituted styryl group include a styryl group, a 2,2-diphenylvinyl group, and a substituent such as a halogen atom, a hydroxyl group, or --NAr.
³ Ar ⁴ (Ar ³ and Ar ⁴ each independently have 6 to 20 carbon atoms)
And the aryl group may have a substituent. A) a substituted or unsubstituted 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 or unsubstituted aromatic hydrocarbon group, the substituted or unsubstituted aromatic heterocyclic group, the substituted or unsubstituted aralkyl group, the substituted Or an unsubstituted aryloxy group, a substituted styryl group having a substituted or unsubstituted alkoxycarbonyl group, a carboxyl group, or the like, or a 2,2-diphenylvinyl group. As the aryl group having 6 to 20 carbon atoms represented by Ar ³ and Ar ⁴ , a phenyl group, a naphthyl group, an anthryl group,
Examples include a phenanthryl group, a naphthacenyl group and a pyrenyl group. 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, the above-mentioned substituted or unsubstituted group. A 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 And the above-mentioned substituted or unsubstituted aryloxy groups, the above-mentioned substituted or unsubstituted alkoxycarbonyl groups, and carboxyl groups.

In R ^{1 to} R ¹² , a ring-forming 2
Examples of the valent group include a tetramethylene group, a pentamethylene group, a hexamethylene group, and 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.

As the sterically hindered group which suppresses the formation of an association state, any substituent can be used as long as it has a sufficient bulk to inhibit the approach between molecules. . For example, the aforementioned substituted or unsubstituted alkyl group, the aforementioned substituted or unsubstituted cycloalkyl group, the aforementioned substituted or unsubstituted alkoxy group, the aforementioned substituted or unsubstituted aromatic hydrocarbon group, the aforementioned substituted or unsubstituted aromatic hydrocarbon group, An unsubstituted aromatic heterocyclic group, the above-mentioned substituted or unsubstituted aralkyl group, and the above-mentioned substituted or unsubstituted aryloxy group are mentioned. Among them, preferred examples are an isopropyl group, a t-butyl group, 3-dibromo-t-butyl group, 2,3-diiodo-t-butyl group, t-butoxy group, 2,3-dibromo-t-butoxy group, 2,3-diiodo-t-butoxy group, 2-methylbutane -2-yl group, 2-methylbutan-2-yloxy group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl Group, norbornan-1-yl group, norbornan-2-yl group, norbornan-7-yl group, norbornan-1-yloxy group, norbornan-2-yloxy group, norbornan-7-yloxy group, bornan-2-yl Group, bornan-2-yloxy group, tricyclo [5.3.2.04,9] dodecane-1-yl group, tricyclo [5.3.2.04,
9] dodecane-2-yl group, tricyclo [5.3.2.
04,9] dodecane-3-yl group, tricyclo [5.
3.2.04,9] dodecane-10-yl group, tricyclo [5.3.2.04,9] dodecane-11-yl group,
Tricyclo [5.3.2.04,9] dodecane-1-yloxy group, tricyclo [5.3.2.04,9] dodecan-2-yloxy group, tricyclo [5.3.2.0
4,9] dodecane-3-yloxy group, tricyclo [5.3.2.04,9] dodecane-10-yloxy group, tricyclo [5.3.2.04,9] dodecane-1
1-yloxy group, p-cyclophanyl group, 1-adamantyl group, 2-adamantyl group, 1-adamantyloxy group, 2-adamantyloxy group, phenyl group, tolyl group, 9-fluorenyl group, 2,2-dimethyl -1-propyl group, cyclopropylmethyl group, cyclobutylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group, 4-methylcyclohexylmethyl group, norbornane-1-ylmethyl group, norbornan-2-ylmethyl group, norbornan-7-ylmethyl Group, tricyclo [5.3.2.4,9] dodecane-1-ylmethyl group, tricyclo [5.3.2.04,9] dodecane-2
-Ylmethyl group, tricyclo [5.3.2.04,9]
Dodecane-3-ylmethyl group, tricyclo [5.3.
2.04,9] dodecane-10-ylmethyl group, tricyclo [5.3.2.04,9] dodecane-11-ylmethyl group, p-cyclophanemethyl group, 1-adamantylmethyl group, 2-adamantylmethyl group , Benzyl group, 4
-Methylbenzyl group, 1-naphthyloxy group, 1-naphthylmethyl group, 9-anthrylmethyl group, 9-anthryloxy group, triphenylmethyl group, 2,2,2-triphenylethyl group, 9- Fluorenyl group, 9-fluorenyloxy group, 9,9′-spirobifluorene-4-
An yl group, a 9,9′-spirobifluoren-3-yl group,
9,9′-spirobifluoren-4-ylmethyl group,
9,9′-spirobifluoren-3-ylmethyl group,
9,9′-spirobifluoren-4-yloxy group,
9,9′-spirobifluoren-3-yloxy group, tris (2,2-dimethylpropyl) methyl group, tris (2,2-dimethylpropyl) methyloxy group, 2,
2,2-tris (2,2-dimethylpropyl) ethyl group, bicyclo [3,2,1] octan-1-yl group, bicyclo [3,2,1] octan-2-yl group, bicyclo [3, 2,1] octan-3-yl group, bicyclo [3,
2,1] octan-7-yl group, bicyclo [3,2,
1] octane-8-yl group, bicyclo [3,2,1] octan-1-yloxy group, bicyclo [3,2,1] octan-2-yloxy group, bicyclo [3,2,1] octane-3 -Yloxy group, bicyclo [3,2,1] octan-7-yloxy group, bicyclo [3,2,1] octan-8-yloxy group, bicyclo [3,2,1] octan-1-ylmethyl group, bicyclo [3,2,1] octan-2-ylmethyl group, bicyclo [3,2,1] octan-3-ylmethyl group, bicyclo [3,2,1] octan-7-ylmethyl group, bicyclo [3,2, 1] octane-8-ylmethyl group and the like.

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

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[0032]

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[0033]

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[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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The element structure of the organic EL element according to the present invention is a structure in which one or more organic layers are stacked between the electrodes.
FIG. 4 shows a structure including a cathode, a structure including an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode illustrated in FIG. 2; and a structure including an anode, a hole transport layer, a light emitting layer, and a cathode illustrated in FIG. The structure includes an anode, a light-emitting layer, an electron transporting layer, and a cathode as shown. The compound in the present invention may be used in any of the above organic layers, and can 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 (26), N, N′-diphenyl-N, N′-bis (3-methylphenyl) -1,1′-biphenyl −4
4'-diamine (27), N, N'-diphenyl-N-
N-bis (1-naphthyl) -1,1'-biphenyl)-
Triphenyldiamines such as 4,4'-diamine (28) and star burst type molecules ((29) to (31))
And the like.

[0041]

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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 (32), bis {2- (4-
Oxadiazole derivatives such as t-butylphenyl) -1,3,4-oxadiazole {-m-phenylene (33), and triazole derivatives ((34), (35)
Quinolinol-based metal complexes ((36) to (39))
Etc.).

[0043]

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The anode of the organic thin film EL element plays 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) or (2) used in the organic EL device of the present invention may be formed by vacuum evaporation, molecular beam evaporation (MBE), or a solution dissolved in a solvent. It can be formed by a known method such as a dipping method, a spin 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. However, if the thickness is too small, defects such as pinholes are likely to occur. Conversely, if the thickness is too large, a high applied voltage is required. Usually, the range of several nm to 1 μm is preferable because efficiency is deteriorated.

[0047]

The present invention will be described in detail below with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist. (Synthesis Example 1) Synthesis of compound (3) (1,7-di- (2-adamantyloxy) -3,9-bis (di-p-tolylamino) perylene). 1,7-Di- (2-adamantyloxy) -3,9-dibromoperylene, di-p-tolylamine, potassium carbonate, copper powder and nitrobenzene were placed in a reaction vessel, and 20
Stirred at 0 ° 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 formed according to a conventional method to obtain the desired compound (3).

Synthesis Example 2 Compound (4) (1,7-di-
(2-adamantyloxy) -3,9-bis (Np-
Synthesis of Tolyl-N-4- (4-methylphenylvinyl) phenylamino) perylene). Except that N- (4- (4-methylphenylvinyl) phenyl) -p-toluidine was used instead of di-p-tolylamine, the target compound (4) was obtained in the same manner as in Synthesis Example 1.

(Synthesis Example 3) Compound (5) (1,7-di-
(2-adamantyloxy) -3,9-bis (Np-
Synthesis of tolyl-N-4- (2,2-di-p-tolylvinyl) phenylamino) perylene). Instead of di-p-tolylamine, N- (4- (2,2-
Except that di-p-tolylvinyl) phenyl) -p-toluidine was used, the target compound (5) was obtained in the same manner as in Synthesis Example 1.

Synthesis Example 4 Compound (6) (1,7-di-
Synthesis of 1-adamantyl-3,9-bis (di-p-tolylamino) perylene). 1,7-di-1-adamantyl- in place of 1,6,7,12-tetraphenoxy-3,9-dibromoperylene
Except that 3,9-dibromoperylene was used, the target compound (6) was obtained in the same manner as in Synthesis Example 1.

(Synthesis Example 5) Compound (7) (1,7-di-
1-adamantyl-3,9-bis (Np-tolyl-N
-4- (4-methylphenylvinyl) phenylamino)
Synthesis of perylene). 1,7-di-1-adamantyl- in place of 1,6,7,12-tetraphenoxy-3,9-dibromoperylene
Except that 3,9-dibromoperylene was used, the target compound (7) was obtained in the same manner as in Synthesis Example 2.

(Synthesis Example 6) Compound (8) (1,7-di-
1-adamantyl-3,9-bis (Np-tolyl-N
Synthesis of 4- (2,2-di-p-tolylvinyl) phenylamino) perylene). 1,7-di-1-adamantyl- in place of 1,6,7,12-tetraphenoxy-3,9-dibromoperylene
Except that 3,9-dibromoperylene was used, the target compound (8) was obtained in the same manner as in Synthesis Example 3.

Synthesis Example 7 Synthesis of compound (18) (1,7-di-t-butoxy-3,9-bis (di-p-tolylamino) perylene). 1,7-di-t-butoxy-3 instead of 1,6,7,12-tetraphenoxy-3,9-dibromoperylene
Except that 9-dibromoperylene was used, the target compound (18) was obtained in the same manner as in Synthesis Example 1.

(Synthesis Example 8) Compound (19) (1,7-di-tert-butoxy-3,9-bis (Np-tolyl-N-
Synthesis of 4- (4-methylphenylvinyl) phenylamino) perylene). 1,7-di-t-butoxy-3 instead of 1,6,7,12-tetraphenoxy-3,9-dibromoperylene
Except that 9-dibromoperylene was used, the target compound (19) was obtained in the same manner as in Synthesis Example 2.

Synthesis Example 9 Compound (20) (1,7-di-t-butoxy-3,9-bis (Np-tolyl-N-
Synthesis of 4- (2,2-di-p-tolylvinyl) phenylamino) perylene). 1,7-di-t-butoxy-3 instead of 1,6,7,12-tetraphenoxy-3,9-dibromoperylene
Except that 9-dibromoperylene was used, the target compound (20) was obtained in the same manner as in Synthesis Example 3.

Synthesis Example 10 Compound (24) (1,7-
Di-t-butoxy-3- (Np-tolyl-N-4-
(4-methylphenylvinyl) phenylamino) perylene). Except that 1,7-di-t-butoxy-3-bromoperylene was used instead of 1,7-di-t-butoxy-3,9-dibromoperylene, the target compound ( 24) was obtained.

Hereinafter, examples (Examples 1 to 22, Examples 27 to 30, and Examples 35 to 3) in which the compound of the present invention was used in the light emitting layer
7) Examples in which a mixed thin film with a hole transport material is used for the light emitting layer (Examples 23 to 26), and examples in which a mixed thin film with an electron transport material is used in the light emitting layer (Examples 31 to 34, Example 38) ), Examples used in the hole transport layer (Examples 39 to 40), examples used in the electron transport layer (Example 41), and comparative examples.

Example 1 FIG. 1 shows a sectional structure of an organic EL device according to Example 1. The organic EL device according to the present embodiment
It comprises a glass substrate 1, an anode 2 and a cathode 6 formed on the glass substrate 1, and a light emitting layer 4 sandwiched between the anode 2 and the cathode 6.

Hereinafter, a procedure for manufacturing the organic thin film EL device according to Example 1 will be described. An ITO was formed on a glass substrate 1 by sputtering so that the sheet resistance was 20 Ω / □. As a light emitting layer 4 thereon,
Compound (3) was formed to a thickness of 40 nm by a vacuum evaporation method. Next, a magnesium-silver alloy was formed as a cathode 6 by vacuum evaporation.
The organic EL device was formed by forming the layer to a thickness of 00 nm.

When a DC voltage of 5 V was applied to this organic EL device, light emission of 430 cd / m ² was obtained.

Example 2 The same operation as in Example 1 was carried out except that Compound (4) was used as the light-emitting material.
An organic EL device was manufactured. When a DC voltage of 5 V was applied to this organic EL device, light emission of 510 cd / m ² was obtained.

Example 3 The same operation as in Example 1 was carried out except that the compound (5) was used as the light emitting material.
An organic EL device was manufactured. When a DC voltage of 5 V was applied to this organic EL device, light emission of 560 cd / m ² was obtained.

Example 4 The same operation as in Example 1 was carried out except that the compound (6) was used as the light-emitting material.
An organic EL device was manufactured. When a DC voltage of 5 V was applied to this organic EL device, light emission of 400 cd / m ² was obtained.

Example 5 The same operation as in Example 1 was carried out except that the compound (7) was used as the light emitting material.
An organic EL device was manufactured. When a DC voltage of 5 V was applied to this organic EL device, light emission of 460 cd / m ² was obtained.

Example 6 The same operation as in Example 1 was carried out except that the compound (8) was used as the luminescent material.
An organic EL device was manufactured. When a DC voltage of 5 V was applied to this organic EL device, light emission of 520 cd / m ² was obtained.

Example 7 Compound (1) was used as a luminescent material.
An organic EL device was manufactured in the same manner as in Example 1 except that 8) was used. Apply a DC voltage of 5 to this organic EL element.
When V was applied, light emission of 430 cd / m ² was obtained.

Example 8 The compound (1) was used as a luminescent material.
An organic EL device was produced in the same manner as in Example 1 except that 9) was used. Apply a DC voltage of 5 to this organic EL element.
When V was applied, light emission of 510 cd / m ² was obtained.

Example 9 The compound (2) was used as a light emitting material.
An organic EL device was manufactured in the same manner as in Example 1, except that 0) was used. Apply a DC voltage of 5 to this organic EL element.
When V was applied, light emission of 580 cd / m ² was obtained.

Example 10 The cross-sectional structure of the organic EL device according to Example 10 is the same as the cross-sectional structure of the organic EL device according to Example 1 (see FIG. 1). Hereinafter, a procedure for manufacturing the organic EL device according to Example 10 will be described.

An ITO film is formed on the glass substrate 1 by sputtering so that the sheet resistance becomes 20 Ω / □.
Anode 2 was obtained. The light emitting layer 4 having a thickness of 40 nm was formed thereon by spin coating using a chloroform solution of the compound (5). Next, a magnesium-silver alloy was formed as a cathode 6 to a thickness of 200 nm by a vacuum evaporation method to produce an organic EL device. When a DC voltage of 5 V was applied to this organic EL device, light emission of 160 cd / m ² was obtained.

(Embodiment 11) FIG. 2 shows a cross-sectional structure of an organic EL device according to Embodiment 11. The organic EL device according to this embodiment includes a glass substrate 1 and an anode 2 formed on the glass substrate 1.
And a cathode 6, and a hole transport layer 3, a light emitting layer 4, and an electron transport layer 5 sandwiched between the anode 2 and the cathode 6.

An ITO film is formed on the glass substrate 1 by sputtering so that the sheet resistance becomes 20 Ω / □.
Anode 2 was obtained. N, N ′ is formed thereon as a hole transport layer 3.
-Diphenyl-N, N'-bis (3-methylphenyl)
-[1,1'-biphenyl] -4,4'-diamine (2
7) was formed to a thickness of 50 nm by a vacuum evaporation method. Next, compound (3) was formed to a thickness of 40 nm as a light emitting layer 4 by a vacuum evaporation method. Next, as the electron transport layer 5, 2- (4-biphenylyl) -5- (4-t-butylphenyl) -1,3,4-
Oxadiazole (32) was formed to a thickness of 20 nm by a vacuum evaporation method. Next, a magnesium-silver alloy was formed to a thickness of 200 nm as a cathode 6 by a vacuum evaporation method to produce an organic EL device. When a DC voltage of 10 V was applied to this organic EL device, light emission of 2,300 cd / m ² was obtained.

Example 12 An organic EL device was manufactured in the same manner as in Example 11, except that the compound (4) was used as the light emitting material. When a DC voltage of 10 V was applied to this organic EL device, light emission of 3010 cd / m ² was obtained.

Example 13 An organic EL device was manufactured in the same manner as in Example 11, except that the compound (5) was used as the light emitting material. When a DC voltage of 10 V was applied to this organic EL device, light emission of 4100 cd / m ² was obtained.

Example 14 An organic EL device was manufactured in the same manner as in Example 11, except that the compound (6) was used as the light emitting material. When a DC voltage of 10 V was applied to this organic EL device, light emission of 2130 cd / m ² was obtained.

(Example 15) An organic EL device was manufactured in the same manner as in Example 11, except that the compound (7) was used as the light emitting material. When a DC voltage of 10 V was applied to this organic EL device, light emission of 3100 cd / m ² was obtained.

Example 16 An organic EL device was manufactured in the same manner as in Example 11, except that the compound (8) was used as the light emitting material. When a DC voltage of 10 V was applied to this organic EL device, light emission of 4320 cd / m ² was obtained.

Example 17 An organic EL device was manufactured in the same manner as in Example 11, except that the compound (24) was used as the light emitting material. When a DC voltage of 10 V was applied to this organic EL device, light emission of 2450 cd / m ² was obtained.

Example 18 An organic EL device was manufactured in the same manner as in Example 11, except that the compound (19) was used as the light emitting material. When a DC voltage of 10 V was applied to this organic EL device, light emission of 2,970 cd / m ² was obtained.

Example 19 An organic EL device was manufactured in the same manner as in Example 11, except that the compound (20) was used as the light emitting material. When a DC voltage of 10 V was applied to this organic EL device, light emission of 4330 cd / m ² was obtained.

(Example 20) As the hole transport layer 3, N, N
'-Diphenyl-NN-bis (1-naphthyl) -1,
1′-biphenyl) -4,4′-diamine (28)
The same operation as in Example 11 was performed, except that bis {2- (4-t-butylphenyl) -1,3,4-oxadiazole} -m-phenylene (33) was used as the electron transport layer 5, An organic EL device was manufactured. When a DC voltage of 10 V was applied to this organic EL device, light emission of 5120 cd / m ² was obtained.

(Example 21) A star bust type molecule (29) was used as the hole transport layer 3 and a compound (5) was used as the light emitting layer 4
As a quinolinol-based metal complex (3
An organic EL device was manufactured in the same manner as in Example 11, except that 6) was used. Apply a DC voltage of 1 to this organic EL element.
When 0 V was applied, light emission of 4580 cd / m ² was obtained.

Example 22 The star transport type molecule (30) was used as the hole transport layer 3 and the compound (2) was used as the light emitting layer 4
0) was performed in the same manner as in Example 11 except that a quinolinol-based metal complex (37) was used as the electron transporting layer 5 to produce an organic EL device. When a DC voltage of 10 V was applied to this organic EL device, light emission of 5130 cd / m ² was obtained.

(Example 23) N, N'-
Diphenyl-NN-bis (1-naphthyl) -1,1 '
-Biphenyl) -4,4'-diamine (28) and compound (5) were co-evaporated at a weight ratio of 1:10 to form a thin film having a thickness of 50 nm. An EL device was manufactured. When a DC voltage of 10 V was applied to this organic EL device, light emission of 4250 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 (4) was used instead of the compound (5). When a DC voltage of 10 V was applied to this organic EL device, light emission of 3280 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 (18) was used instead of the compound (5). When a DC voltage of 10 V was applied to this organic EL device, light emission of 4370 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 (20) was used instead of the compound (5). When a DC voltage of 10 V was applied to this organic EL device, light emission of 5,400 cd / m ² was obtained.

Example 27 FIG. 3 shows a cross-sectional structure of an organic EL device according to Example 27. The organic EL device according to the present embodiment includes a glass substrate 1, an anode 2 and a cathode 6 formed on the glass substrate 1, a hole transport layer 3 and a light emitting layer sandwiched between the anode 2 and the cathode 6. 4

Hereinafter, a procedure for fabricating the organic EL device according to this embodiment will be described. An ITO was formed on a glass substrate 1 by sputtering so that the sheet resistance was 20 Ω / □. As a hole transport layer 3 thereon,
N, N'-diphenyl-NN-bis (1-naphthyl)
-1,1'-biphenyl) -4,4'-diamine (2
8) was formed to a thickness of 50 nm by a vacuum evaporation method. Next, as the light emitting layer 4, a film obtained by co-evaporating the compound (3) in a vacuum is formed to a thickness of 40 nm.
Formed. Next, magnesium-silver alloy 2 was used as cathode 6.
An EL element was fabricated by forming the layer to a thickness of 00 nm. When a DC voltage of 10 V was applied to this organic EL device, 1670 cd / m
² luminescence was obtained.

Example 28 An organic EL device was manufactured in the same manner as in Example 27 except that the compound (5) was used instead of the compound (3). When a DC voltage of 10 V was applied to this organic EL device, light emission of 2960 cd / m ² was obtained.

Example 29 An organic EL device was manufactured in the same manner as in Example 27 except that the compound (7) was used instead of the compound (3). When a DC voltage of 10 V was applied to this organic EL device, light emission of 1980 cd / m ² was obtained.

Example 30 An organic EL device was produced in the same manner as in Example 27 except that the compound (20) was used instead of the compound (3). When a DC voltage of 10 V was applied to this organic EL device, light emission of 3150 cd / m ² was obtained.

(Example 31) As the light emitting layer 4, a quinolinol-based metal complex (36) and a compound (3) were used in a ratio of 20: 1.
An organic EL device was manufactured in the same manner as in Example 27, except that a film co-deposited by vacuum was formed at a weight ratio of 50 nm. When a DC voltage of 10 V was applied to this organic EL device, light emission of 2360 cd / m ² was obtained.

Example 32 An organic EL device was manufactured in the same manner as in Example 31, except that the compound (5) was used instead of the compound (3). When a DC voltage of 10 V was applied to this organic EL device, light emission of 3060 cd / m ² was obtained.

Example 33 An organic EL device was manufactured in the same manner as in Example 31, except that the compound (19) was used instead of the compound (3). When a DC voltage of 10 V was applied to this organic EL device, light emission of 2610 cd / m ² was obtained.

Example 34 An organic EL device was manufactured in the same manner as in Example 31, except that the compound (8) was used instead of the compound (3). When a DC voltage of 10 V was applied to this organic EL device, light emission of 3110 cd / m ² was obtained.

(Example 35) FIG. 4 shows a sectional structure of an organic EL device according to Example 35. The organic EL device according to the present embodiment includes a glass substrate 1, an anode 2 and a cathode 6 formed on the glass substrate 1, a light emitting layer 4 and an electron transport layer 5 sandwiched between the anode 2 and the cathode 6. Consists of

Hereinafter, a procedure for manufacturing the organic EL device according to this embodiment will be described. An ITO was formed on a glass substrate 1 by sputtering so that the sheet resistance was 20 Ω / □. A compound (5) having a thickness of 50 nm was formed thereon as a light emitting layer 4 by a vacuum evaporation method. Next, as the electron transport layer 5, a triazole derivative (34) was formed to a thickness of 50 nm by a vacuum evaporation method. Next, a 200 nm-thick magnesium-silver alloy was formed as the cathode 6 to produce an organic EL device. When a DC voltage of 10 V was applied to this organic EL device, light emission of 1790 cd / m ² was obtained.

Example 36 An organic EL device was manufactured in the same manner as in Example 35 except that the compound (8) was used instead of the compound (5). When a DC voltage of 10 V was applied to this organic EL device, light emission of 1910 cd / m ² was obtained.

Example 37 An organic EL device was manufactured in the same manner as in Example 35 except that the compound (19) was used instead of the compound (5). When a DC voltage of 10 V was applied to this organic EL device, light emission of 1610 cd / m ² was obtained.

(Example 38) As the hole transport layer 3, N,
N'-diphenyl-N, N'-bis (3-methylphenyl)-[1,1'-biphenyl] -4,4'-diamine (27) is used as the luminescent layer 4 as a quinolinol-based metal complex (38). An organic EL device was produced in the same manner as in Example 27, except that a film produced by vacuum co-evaporation of the compound and the compound (19) at a weight ratio of 20: 1 was used. When a DC voltage of 10 V was applied to the organic EL device, 2430 cd /
m ² emission was obtained.

Example 39 The compound (3) was used as the hole transport layer 3 and the quinolinol-based metal complex (3
An organic EL device was manufactured in the same manner as in Example 11, except that 8) was used. Apply a DC voltage of 1 to this organic EL element.
When 0 V was applied, light emission of 1630 cd / m ² was obtained.

Example 40 An organic EL device was manufactured in the same manner as in Example 39 except that the compound (20) was used as the hole transport layer 3. When a DC voltage of 10 V was applied to this organic EL device, light emission of 1970 cd / m ² was obtained.

Example 41 An organic EL device was manufactured by performing the same operation as in Example 11 except that the compound (6) was used as the electron transport layer 5 and the quinolinol-based metal complex (36) was used as the light emitting layer 4. Produced. When a DC voltage of 10 V was applied to this organic EL device, light emission of 810 cd / m ² was obtained.

(Comparative Example 1) Except that 3,9-bis (di-p-tolylamino) perylene was used as the light emitting layer 4,
The same operation as in Example 11 was performed to manufacture an organic EL device. When a DC voltage of 10 V was applied to this organic EL device, light emission of 1600 cd / m ² was obtained.

Comparative Example 2 As the light emitting layer 4, 3,9-bis (N-4- (4-methylphenylvinyl) phenyl-
An organic EL device was prepared in the same manner as in Example 11, except that (Np-tolylamino) perylene was used.
When a DC voltage of 10 V was applied to the organic EL device, 2
Light emission of 000 cd / m ² was obtained.

[0107]

As described above, in the organic EL device of the present invention, the compound represented by the general formula (1) or (2) is used as the constituent material of the organic thin film.
High-luminance light emission can be obtained as compared with the related art, 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 according to Example 1 of the present invention.

FIG. 2 is a sectional view of an organic EL device according to Example 11 of the present invention.

FIG. 3 is a sectional view of an organic EL device according to Example 27 of the present invention.

FIG. 4 is a sectional view of an organic EL device according to Example 35 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

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Hiroshi Tada 5-7-1 Shiba, Minato-ku, Tokyo Inside NEC Corporation (72) Inventor Yukiko Morioka 5-7-1 Shiba, Minato-ku, Tokyo Japan Electric Company (72) Inventor Atsushi Oda 5-7-1 Shiba, Minato-ku, Tokyo NEC Corporation F-term (reference) 3K007 AB02 CA01 CB01 CB03 DA00 DA01 DB03 EB00 FA01

Claims (6)

[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): 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 styryl 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 an unsubstituted aralkyl group or a substituted or unsubstituted aryloxy group, and R ^{1 to} R ¹² may form a ring with two of them, provided that R ^{1 to} R ¹² At least one is -N
And a diarylamino group represented by Ar ¹ Ar ² (Ar ¹ and Ar ² represent a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group). Further, at least one of R ^{1 to} R ¹² which is not a diarylamino group is a sterically hindered group which suppresses formation of an associated state between molecules. An organic electroluminescent device comprising the perylene compound represented by the formula (1) alone or in a mixture. 2. 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 (2): 2] (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 styryl 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 an unsubstituted aralkyl group or a substituted or unsubstituted aryloxy group, and R ^{1 to} R ¹² may form a ring with two of them, provided that R ^{1 to} R ¹² At least one is -N
Ar ¹ Ar ² (Ar ¹ and Ar ² represent a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, provided that at least one of Ar ¹ and Ar ² is substituted Or an unsubstituted styryl group as a substituent.). Further, at least one of R ^{1 to} R ¹² which is not a diarylamino group is a sterically hindered group which suppresses formation of an association state between molecules. )
An organic electroluminescent device comprising the perylene compound represented by the formula (1) alone or as a mixture. 3. The organic thin-film layer has at least a light-emitting layer, and the light-emitting layer contains the compound represented by the general formula (1) or (2) alone or as a mixture. 3. The organic electroluminescent device according to 2. 4. The organic thin film layer has at least a hole transport layer, and the hole transport layer contains the compound represented by the general formula (1) or (2) alone or as a mixture. The organic electroluminescent device according to claim 1. 5. The organic thin film layer has at least an electron transport layer, and the electron transport layer contains the compound represented by the general formula (1) or (2) alone or as a mixture. 3. The organic electroluminescent device according to 1 or 2. 6. A compound represented by the general formula (1) or (2), wherein the sterically hindered group is a substituted or unsubstituted alkyl 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, or a substituted or unsubstituted aryloxy group.
5. The organic electroluminescent device according to any one of 5.