JP3156679B2 - Organic electroluminescence 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 based on 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. Eastman Kodak C.I. W. Tan
g et al. report on a low voltage driven organic EL device using a stacked device (CWTang, SAVanSlyke, Applied Physics Letters, 51, 9)
13, p. 1987, etc.), organic EL devices using organic materials as constituent materials have been actively studied. 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 transport (injection) layer and an electron transporting light emitting layer, or a hole transporting (injection) layer, a light emitting layer, and an electron transporting (injection) The three-layer type and the like 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 and N, N'-diphenyl-N, N'-bis ( 3-methylphenyl)-[1,
Triphenylamine derivatives such as 1'-biphenyl] -4,4'-diamine and aromatic diamine derivatives are well known (for example, JP-A-8-20771, JP-A-8-20771).
JP-A-40995, JP-A-8-40997, JP-A-8-54397, JP-A-8-87122, and the like. Oxadiazole derivatives, triazole derivatives and the like are well known as electron transporting materials.

As light emitting materials, there are known light emitting materials such as chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, and oxadiazole derivatives. 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.).

[0005]

Recently, high-luminance, long-life organic EL devices have been disclosed or reported.
Still not necessarily enough. Therefore, there is a strong demand for the development of materials exhibiting high performance. An object of the present invention is to provide a high-luminance organic EL device.

[0006]

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 dibenzoperylene compound as a light emitting material.
The device has been found to emit light with higher luminance than before. Further, it was found that the material has high carrier transportability, and an organic EL device manufactured using the material as a hole transport material, and a mixed thin film of the material and another hole transport material or an electron transport material were used. It has been found that the organic EL device manufactured by the method described above emits light of higher luminance than before, and the present invention has been achieved.

Further, among the above-mentioned dibenzoperylene compounds, it has been found that an organic EL device produced by using one having a diarylamino group as a substituent can emit light of particularly high luminance, and the present invention has been achieved. In addition, among the dibenzoperylene compounds having a diarylamino group as a substituent, an organic EL element manufactured using one having an aryl group having a styryl group as a substituent can emit light with particularly high luminance. Invented the invention.

That is, the present invention provides the following (A) to (L)
The organic electroluminescence element of the above is provided.

(A) In an organic electroluminescence device having one or more organic thin film layers including a light emitting layer between an anode and a cathode, at least one of the organic thin film layers is represented by the following general formula (1). An organic electroluminescent device comprising the dibenzoperylene compound used alone or in a mixture.

Embedded image [Wherein, R ^{1 to} R ¹⁶ 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 group; Alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group Represents a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group. R1 to R8 and R
9 to R16 may form a ring with two of each . ]

(B) The organic electroluminescence of (A), wherein 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) alone or in a mixture. element.

(C) 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) alone or in a mixture. Organic electroluminescence element.

(D) At least an electron transport layer is provided as the organic thin film layer, and the electron transport layer contains the compound represented by the general formula (1) alone or in a mixture. Electroluminescence element.

(E) In an organic electroluminescence device having one or more organic thin film layers including a light emitting layer between an anode and a cathode, at least one of the organic thin film layers is represented by the general formula (1). At least one of R ^{1 to} R ¹⁶ among the dibenzoperylene compounds is —NAr ¹ A
a compound which is a diarylamino group represented by r 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); Or, an organic electroluminescent device comprising a mixture.

(F) The organic thin-film layer has at least a light-emitting layer, and the light-emitting layer is formed of a dibenzoperylene compound represented by the general formula (1) in which at least one of R ^{1 to} R ¹⁶ is -NAr. ¹ is a diarylamino group represented by 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). The organic electroluminescence device according to (E), which is contained alone or in a mixture.

(G) The organic thin film layer has at least a hole transport layer, and the hole transport layer is at least ^one of R ^{1 to} R ¹⁶ among the dibenzoperylene compounds represented by the general formula (1). one of ^{-NAr 1 Ar 2 (Ar 1,} Ar 2 each independently represent an aryl group having 6 to 20 carbon atoms, the aryl group may have a substituent.) diarylamino group represented by (E) The organic electroluminescent device according to (E), wherein the compound is a single compound or a mixture.

(H) The organic thin film layer has at least an electron transporting layer, and the electron transporting layer has at least one of R ^{1 to} R ¹⁶ among the dibenzoperylene compounds represented by the general formula (1). —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.) The organic electroluminescent device according to (E), comprising the compound alone or in a mixture.

(I) In an organic electroluminescence device having one or more organic thin film layers including a light emitting layer between an anode and a cathode, at least one of the organic thin film layers is represented by the general formula (1). At least one of R ^{1 to} R ¹⁶ among the dibenzoperylene compounds is —NAr ¹ A
r ² is a diarylamino group represented by r 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); An organic electroluminescent device comprising a compound in which at least one of ¹ and Ar ² has a substituted or unsubstituted styryl group as a substituent, alone or in a mixture.

(J) The organic thin-film layer has at least a light-emitting layer, and the light-emitting layer is formed of a dibenzoperylene compound represented by the general formula (1) in which at least one of R ^{1 to} R ¹⁶ is -NAr. A diarylamino group represented by 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); (I) wherein at least one of Ar ¹ and Ar ² contains a compound having a substituted or unsubstituted styryl group as a substituent, alone or in a mixture.
Organic electroluminescence element.

(K) The organic thin film layer has at least a hole transport layer, and the hole transport layer is at least ^one of R ^{1 to} R ¹⁶ among the dibenzoperylene compounds represented by the general formula (1). one of ^{-NAr 1 Ar 2 (Ar 1,} Ar 2 each independently represent an aryl group having 6 to 20 carbon atoms, the aryl group may have a substituent.) diarylamino group represented by Wherein at least one of Ar ¹ and Ar ² contains a compound having a substituted or unsubstituted styryl group as a substituent, singly or as a mixture.

(L) The organic thin film layer has at least an electron transporting layer, and the electron transporting layer is formed of at least one of R ^{1 to} R ¹⁶ among the dibenzoperylene compounds represented by the general formula (1). A diarylamino group represented by —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.) And (I) an organic electroluminescent device according to (I), wherein at least one of Ar ¹ and Ar ² contains a compound having a substituted or unsubstituted styryl group as a substituent, alone or in a mixture.

[0021]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
The dibenzoperylene compound used in the present invention is a compound having a structure represented by the general formula (1). Equation (1)
In the formula, R ^{1 to} R ¹⁶ 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 Unsubstituted alkenyl group, 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, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted Represents a substituted alkoxycarbonyl group or a carboxyl group. R1 to R8 and R9 to R16 are each 2
Together may form a ring.

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

The substituted or unsubstituted amino group is represented by -NX ¹ X ^2, and examples of 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, s-butyl group, isobutyl group, t-
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-trinitropropyl group,

Phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl , 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 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′-
A methylbiphenylyl group, a 4 "-t-butyl-p-terphenyl-4-yl group,

2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-indolyl, 3-indolyl, 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, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5
-Benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzo Furanyl group, 7-isobenzofuranyl group,

2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-quinolyl 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-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,

A 1,7-phenanthrolin-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 Group, 1,7-phenanthroline-8-yl group, 1,7-
Phenanthroline-9-yl group, 1,7-phenanthroline-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-phenanthroline-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-phenanthrolin-8-yl group, 1, 9
A phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a 1,10-phenanthrolin-3-yl group,

1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9
-Phenanthroline-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthroline-4-
Yl group, 2,9-phenanthrolin-5-yl group, 2,
9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group, 2,9-phenanthroline-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 Group, 2,8-phenanthrolin-6-yl group, 2,8-
Phenanthroline-7-yl group, 2,8-phenanthroline-9-yl group, 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-phenanthroline-5
-Yl group, 2,7-phenanthrolin-6-yl group,
2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-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
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 And a 4-t-butyl-3-indolyl group.

Examples of the substituted or unsubstituted alkyl group include methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl and the like.
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
-A 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,
Examples thereof include a 1,2,3-trinitropropyl group.

Examples of the substituted or unsubstituted alkenyl groups include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butanedienyl, and
-Methylvinyl group, styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2- Phenylallyl group, 3
-Phenylallyl group, 3,3-diphenylallyl group,
Examples thereof include a 1,2-dimethylallyl group, a 1-phenyl-1-butenyl group, and a 3-phenyl-1-butenyl group.

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.

The substituted or unsubstituted alkoxy group is --OY
And examples of Y include methyl, ethyl, propyl, isopropyl, n-butyl, and 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-dinitroisopropyl group, 2,3-dinitro-t-butyl group,
Examples thereof include 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. .

Examples of the substituted or unsubstituted aromatic heterocyclic group include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 3-pyridinyl, and 4-pyridinyl. , 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 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, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl 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,

A 1,7-phenanthrolin-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 Group, 1,7-phenanthroline-8-yl group, 1,7-
Phenanthroline-9-yl group, 1,7-phenanthroline-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-phenanthroline-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-phenanthrolin-8-yl group, 1, 9
A phenanthroline-10-yl group,

1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,1
0-phenanthrolin-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-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl Group, 2,9-phenanthroline-8-yl group, 2,9-
Phenanthroline-10-yl group, 2,8-phenanthroline-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-phenanthroline-7
An -yl group, a 2,8-phenanthroline-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-
A phenanthrolin-6-yl group, a 2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a 2,7-phenanthrolin-10-yl group,

1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 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-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 And a 4-t-butyl-3-indolyl group.

Examples of the substituted or unsubstituted aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α -Naphthylmethyl 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, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group, and the like.

A substituted or unsubstituted aryloxy group is represented by-
OZ, examples of Z include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl,
-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 A 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, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzo Furanyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group,

2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 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-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,

A 1,7-phenanthrolin-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 Group, 1,7-phenanthroline-8-yl group, 1,7-
Phenanthroline-9-yl group, 1,7-phenanthroline-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-phenanthroline-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-phenanthrolin-8-yl group, 1, 9
A phenanthroline-10-yl group,

1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,1
0-phenanthrolin-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-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl Group, 2,9-phenanthroline-8-yl group, 2,9-
Phenanthroline-10-yl group, 2,8-phenanthroline-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-phenanthroline-7
An -yl group, a 2,8-phenanthroline-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-
A phenanthrolin-6-yl group, a 2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a 2,7-phenanthrolin-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
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 And a 4-t-butyl-3-indolyl group.

A substituted or unsubstituted alkoxycarbonyl group is represented by --COOY, and examples of Y include 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-dinitroisopropyl group, 2,3-dinitro-t-butyl group,
Examples thereof include a 1,2,3-trinitropropyl group.

Examples of the divalent group forming a ring include:
Tetramethylene group, pentamethylene group, hexamethylene group, diphenylmethane-2,2'-diyl group, diphenylethane-3,3'-diyl group, diphenylpropane-
4,4'-diyl group and the like.

In the compound represented by the general formula (1),
At least one of R ^{1 to} R ¹⁶ is —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).

In this case, the aryl group having 6 to 20 carbon atoms includes 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, the above-mentioned substituted or unsubstituted amino group, nitro group, cyano group, the above-mentioned substituted or unsubstituted alkyl group, and the above-mentioned substituted or unsubstituted alkyl group. A substituted 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 heterocycle Groups, the above-mentioned substituted or unsubstituted aralkyl groups, the above-mentioned substituted or unsubstituted aryloxy groups, the above-mentioned substituted or unsubstituted alkoxycarbonyl groups, and carboxyl groups.

It is preferable that at least one of Ar ¹ and Ar ² has a substituted or unsubstituted styryl group as a substituent. In this case, examples of the styryl group which Ar ¹ and Ar ² have as a substituent include an unsubstituted styryl group, 2,2-diphenylvinyl group, and a halogen atom, a hydroxyl group as a substituent of a terminal phenyl group. , The substituted or unsubstituted amino group, nitro group, 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 group A hydrocarbon group, the substituted or unsubstituted aromatic heterocyclic group, the substituted or unsubstituted aralkyl group, the substituted or unsubstituted aryloxy group,
A substituted styryl group having a substituted or unsubstituted alkoxycarbonyl group, a carboxyl group, or the like;
-Diphenylvinyl group and the like.

Specific examples of the dibenzoperylene compound used in the present invention are shown below, but the compound is not limited thereto.

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The device structure of the organic EL device according to the present invention is as follows.
It has a structure in which one or more organic layers are laminated between electrodes, and examples thereof include a structure including an anode 2, a light emitting layer 4, and a cathode 6 as shown in FIG. 1, an anode 2, as shown in FIG. A structure including the hole transport layer 3, the light emitting layer 4, the electron transport layer 5, and the cathode 6, a structure including the anode 2, the hole transport layer 3, the light emitting layer 4, and the cathode 6 as shown in FIG. 3, and FIG. Such a structure including the anode 2, the light-emitting layer 4, the electron transport layer 5, and the cathode 6 is exemplified. 1 to 4, reference numeral 1 denotes a substrate. The above-mentioned dibenzoperylene compound may be used for any of the above-mentioned 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 material may be used. Specific examples of the hole transport material include, 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 [0
2], triphenyldiamines such as N, N′-diphenyl-NN-bis (1-naphthyl) -1,1′-biphenyl) -4,4′-diamine [03], and starburst-type molecules ([04] to [06], etc.).

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The electron transport material used in the present invention is not particularly limited, and any compound which is generally used as an electron transport material may be used. Specific examples of the electron transporting material include, for example, 2- (4-biphenylyl) -5- (4
-T-butylphenyl) -1,3,4-oxadiazole [07], bis {2- (4-t-butylphenyl)-
1,3,4-oxadiazole {-m-phenylene [0
8] and the like, triazole derivatives (eg, [09] and [10]), and quinolinol-based metal complexes (eg, [11] to [14]).

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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 (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, and for example, a conventionally known formation method by a vacuum deposition method, a spin coating method, or the like can be used. The general formula (1) used in the organic EL device of the present invention.
The organic thin film layer containing the compound represented by the following formulas can be prepared by vacuum evaporation, molecular beam evaporation (MBE), dipping of a solution dissolved in a solvent, spin coating, casting, bar coating, roll coating, etc. It can be formed by a known method using a 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.

[0065]

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 (2): (Dibenzo [a, o] perylene) Hydrochloric acid was added to an anthrone acetic acid solution, zinc was added thereto, and the mixture was refluxed. Then, it is purified according to a conventional method, and 9,9'-
Got a Bianthrill. This was added little by little to the molten liquid of aluminum chloride and sodium chloride, the resulting reaction mixture was poured into dilute hydrochloric acid, and the solid was collected by filtration. The obtained solid is purified according to a conventional method to obtain the desired dibenzo [a,
o] Perylene was obtained.

Synthesis Example 2 Compound (3): (7- (di-
Synthesis of p-tolylamino) dibenzo [a, o] perylene) Dibenzo [a, o] perylene was dissolved in carbon tetrachloride, 1 mol equivalent of bromine was added thereto while cooling, and the mixture was reacted for 4 hours to form a bromide. Purification according to the procedure yielded 7-bromodibenzo [a, o] perylene. Di-p-tolylamine, potassium carbonate, and copper powder were added to 7-bromodibenzo [a, o] perylene thus obtained, and reacted at 200 ° C. for 30 hours. After diluting the reaction solution with water, the reaction product was extracted with chloroform. Thereafter, purification was performed according to a conventional method to obtain the desired compound (3).

Synthesis Example 3 Compound (4): (7,16-
(Bis (di-p-tolylamino)) dibenzo [a, o]
Synthesis of perylene) Dibenzo [a, o] perylene was dissolved in carbon tetrachloride, 2 mol equivalents of bromine was added thereto while cooling, and the mixture was reacted to form a bromide. The resulting bromide was purified according to a conventional method to obtain 7,16-dibromodibenzo [ [a, o] perylene was obtained. 7,16 thus obtained
-Dibromodibenzo [a, o] perylene, 2 molar equivalents of di-p-tolylamine, potassium carbonate, copper powder were added,
The reaction was performed at 200 ° C. for 30 hours. After diluting the reaction solution with water, the reaction product was extracted with chloroform. Thereafter, purification was performed according to a conventional method to obtain the desired compound (4).

Synthesis Example 4 Compound (5): (7- (N-
4- (4-methylphenylvinyl) phenyl-Np-
Synthesis of (tolylamino) -16- (N-phenyl-NP-tolylamino) dibenzo [a, o] perylene) The same method as in Synthesis Example 3 except that phenyl-p-tolylamine is used instead of di-p-tolylamine. As a result,
16- (Bis (N-phenyl-Np-tolylamino)) dibenzo [a, o] perylene was obtained. 7,16-
(Bis (N-phenyl-Np-tolylamino)) dibenzo [a, o] perylene was dissolved in toluene, and 1 molar equivalent of phosphorus oxychloride was added thereto, followed by stirring at room temperature. N-methylformanilide was added dropwise thereto, and the mixture was stirred at 50 ° C for 5 hours. After completion of the reaction, the mixture was slowly poured into cold water, transferred to a separating funnel, and washed several times with water until the toluene layer became neutral. After drying over magnesium sulfate and distilling off the solvent, the residue was purified according to a conventional method to give 7- (Np-formylphenyl-Np-tolylamino) -16- (N-phenyl-Np-tolylamino). ) Dibenzo [a, o] perylene was obtained. The resulting 7- (Np-formylphenyl-N
-P-tolylamino) -16- (N-phenyl-Np
-Tolylamino) dibenzo [a, o] perylene, p-methylbenzylphosphonic acid diethyl ester and sodium hydride were reacted in dimethyl sulfoxide for one day.
After the reaction solution was poured into ice water, the reaction product was extracted with chloroform. Thereafter, purification was carried out according to a conventional method to obtain the desired compound (5).

Synthesis Example 5 Compound (6): (7- (N-
4- (4-methylphenylvinyl) phenyl-Np-
Synthesis of Tolylamino) dibenzo [a, o] perylene) Instead of 7,16-dibromodibenzo [a, o] perylene, 8-bromodibenzo [a, o] perylene was used, and 1 molar equivalent of phenyl-p-tolylamine was used. Except for using it, the target compound (6) was obtained in the same manner as in Synthesis Example 4.

(Synthesis Example 6) Compound (7): (7,16-
Synthesis of bis (N-4- (4-methylphenylvinyl) phenyl-N-p-tolylamino) dibenzo [a, o] perylene) Except for using 2 molar equivalents of phosphorus oxychloride, the same procedure as in Synthesis Example 4 was used. Thus, the desired compound (7) was obtained.

Hereinafter, the compound of the present invention was added to the light emitting layer (1 to 1).
4) A light-emitting layer (15 to 1)
7) The light emitting layer (18 to 2)
0), hole transport layer (21-22), electron transport layer (23)
The following shows an example of using the above.

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 anode 2 / light-emitting layer 4 / cathode 6. ITO was formed on the glass substrate 1 by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. A compound (2) was applied thereon as a light emitting layer by vacuum evaporation to a thickness of 40 n.
m was formed. 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 element, 40
Light emission of cd / m ² was obtained.

Example 2 Compound (3) as a luminescent material
Except that organic E was used.
An L element was produced. When a DC voltage of 5 V was applied to this device, light emission of 90 cd / m ² was obtained.

Example 3 Compound (4) as a luminescent material
Except that organic E was used.
An L element was produced. When a DC voltage of 5 V was applied to this device, light emission of 130 cd / m ² was obtained.

Example 4 Compound (5) as a luminescent material
Except that organic E was used.
An L element was produced. When a DC voltage of 5 V was applied to this device, light emission of 170 cd / m ² was obtained.

Example 5 Compound (6) as a luminescent material
Except that organic E was used.
An L element was produced. When a DC voltage of 5 V was applied to this device, light emission of 150 cd / m ² was obtained.

Example 6 Compound (7) as a luminescent material
Except that organic E was used.
An L element was produced. When a DC voltage of 5 V was applied to this device, light emission of 210 cd / m ² was obtained.

(Example 7) 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 (7). Next, a 200 nm thick magnesium-silver alloy was formed 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 110 cd / m ² was obtained.

(Embodiment 8) FIG. 2 shows a cross-sectional structure of an element used in Embodiment 8. The device is composed of anode 2 / hole transport layer 3 / light emitting layer 4 / electron transport layer 5 / cathode 6. ITO was formed on the glass substrate 1 by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. N, N′-diphenyl-N,
N'-bis (3-methylphenyl)-[1,1'-biphenyl] -4,4'-diamine [02] was formed to a thickness of 50 nm by a vacuum evaporation method. Next, as a light emitting layer, the compound (2) was formed to a thickness of 40 nm by a vacuum evaporation method. Next, 2- (4-biphenylyl) -5- (4-
(t-butylphenyl) -1,3,4-oxadiazole [07] was formed to a thickness of 20 nm by a vacuum evaporation method. Next, as a cathode, a magnesium-silver alloy was formed 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, 280 cd / m ²
Was obtained.

Example 9 Compound (3) as a luminescent material
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 1350 cd / m ² was obtained.

Example 10 The same operation as in Example 8 was carried out except that the compound (4) was used as the light-emitting material.
An organic EL device was manufactured. Apply a DC voltage of 10 V to this element.
Upon application, light emission of 1810 cd / m ² was obtained.

Example 11 The same operation as in Example 8 was carried out except that the compound (5) was used as the light emitting material.
An organic EL device was manufactured. Apply a DC voltage of 10 V to this element.
Upon application, light emission of 2480 cd / m ² was obtained.

Example 12 The same operation as in Example 8 was carried out except that the compound (6) was used as the light emitting material.
An organic EL device was manufactured. Apply a DC voltage of 10 V to this element.
Upon application, light emission of 2260 cd / m ² was obtained.

Example 13 The same operation as in Example 8 was carried out except that the compound (7) was used as the light emitting material.
An organic EL device was manufactured. Apply a DC voltage of 10 V to this element.
Upon application, light emission of 2140 cd / m ² was obtained.

(Example 14) N, N 'was used as the hole transport layer.
-Diphenyl-NN-bis (1-naphthyl) -1,
1′-biphenyl) -4,4′-diamine [03] is used as an electron transporting layer for bis {2- (4-t-butylphenyl)
An organic EL device was manufactured in the same manner as in Example 9, except that -1,3,4-oxadiazole} -m-phenylene [08] was used. DC voltage is applied to this element by 1
When 0 V was applied, light emission of 1670 cd / m ² was obtained.

Example 15 The same operation as in Example 8 was performed except that the compound [04] was used as the hole transport layer, the compound (4) was used as the light emitting layer, and the compound [11] was used as the electron transport layer. Then, an organic EL device was produced. When a DC voltage of 10 V was applied to this device, light emission of 2190 cd / m ² was obtained.

Example 16 The same operation as in Example 8 was carried out except that the compound [05] was used as the hole transport layer, the compound (7) was used as the light emitting layer, and the compound [12] was used as the electron transport layer. Then, an organic EL device was produced. When a DC voltage of 10 V was applied to this device, light emission of 3970 cd / m ² was obtained.

(Embodiment 17) FIG. 4 shows a cross-sectional structure of the device used in Embodiment 17. The device is composed of anode 2 / light-emitting layer 4 / electron transport layer 5 / cathode 6. Glass substrate 1
Sheet resistance is 20 by sputtering ITO on top
A film was formed so as to have an impedance of Ω / □, and used as an anode. Further, N, N′-diphenyl-NN-bis (1-naphthyl) -1,1′-biphenyl) -4,4′-diamine [03] and compound (3) were used as a light emitting layer at a ratio of 1:10. A thin film produced by co-evaporation at a weight ratio of 50 nm was formed. Next, a compound [09] was formed to a thickness of 50 nm by a vacuum evaporation method as an electron transporting layer. Next, a magnesium-silver alloy was used as a cathode for 2 hours.
The organic EL device was formed by forming the layer to a thickness of 00 nm. When a DC voltage of 10 V was applied to this device, light emission of 890 cd / m ² was obtained.

Example 18 An organic EL device was manufactured in the same manner as in Example 17, except that the compound (4) was used instead of the compound (3). When a DC voltage of 10 V was applied to this device, light emission of 1,260 cd / m ² was obtained.

Example 19 An organic EL device was manufactured in the same manner as in Example 17, except that the compound (7) was used instead of the compound (3). When a DC voltage of 10 V was applied to this device, light emission of 1,820 cd / m ² was obtained.

Example 20 An ITO was formed on a glass substrate by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. Compound (7) and N,
N'-diphenyl-NN-bis (1-naphthyl)-
A 40 nm light emitting layer was formed by a spin coating method using a chloroform solution containing (1,1′-biphenyl) -4,4′-diamine [03] at a molar ratio of 1:10. Next, the compound [10] was used to form 50 nm by vacuum evaporation.
Was formed thereon, and a magnesium-silver alloy was formed thereon 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 device, light emission of 930 cd / m ² was obtained.

Example 21 FIG. 3 shows a cross-sectional structure of the device used in Example 21. The device was composed of anode 2 / hole transport layer 3 /
It is composed of a light emitting layer 4 and a cathode 6. Glass substrate 1
Sheet resistance is 20 by sputtering ITO on top
A film was formed so as to have an impedance of Ω / □, and used as an anode. N, N'-diphenyl-NN-bis (1
-Naphthyl) -1,1'-biphenyl) -4,4'-diamine [03] was formed to a thickness of 50 nm by a vacuum evaporation method. Next, compound [11] and compound (2) were used as a light emitting layer in 2
A 50 nm film was formed by vacuum co-evaporation at a weight ratio of 0: 1. Next, a magnesium-silver alloy of 200 n was used as a cathode.
m was formed to produce an organic EL device. When a DC voltage of 10 V was applied to this device, light emission of 820 cd / m ² was obtained.

Example 22 The compound [1] was used as a light emitting layer.
An organic EL device was produced in the same manner as in Example 21, except that a 50 nm film obtained by vacuum co-evaporation of 1] and the compound (3) at a weight ratio of 20: 1 was used. When a DC voltage of 10 V was applied to this device, light emission of 1320 cd / m ² was obtained.

(Example 23) N, N 'as a hole transport layer
-Diphenyl-N, N'-bis (3-methylphenyl)
-[1,1′-biphenyl] -4,4′-diamine [0
2], except that a film prepared by vacuum co-evaporation of compound [13] and compound (7) at a weight ratio of 20: 1 was used as the light emitting layer, and the same operation as in Example 21 was performed. An element was manufactured. When a DC voltage of 10 V was applied to this device, light emission of 1580 cd / m ² was obtained.

Example 24 An organic EL device was manufactured in the same manner as in Example 8, except that the compound (5) was used as the hole transport layer and the compound [13] was used as the light emitting layer. When a DC voltage of 10 V was applied to this element, 6
Light emission of 90 cd / m ² was obtained.

Example 25 An organic EL device was manufactured in the same manner as in Example 24 except that the compound (7) was used as the hole transporting material. DC voltage is applied to this element by 1
When 0 V was applied, light emission of 970 cd / m ² was obtained.

(Example 25) An organic EL device was manufactured in the same manner as in Example 8, except that the compound (2) was used as the electron transporting layer and the compound [11] was used as the light emitting layer. When a DC voltage of 10 V was applied to this element,
Light emission of 90 cd / m ² was obtained.

[0099]

As described above, the organic EL of the present invention is used.
By using a specific dibenzoperylene compound as a constituent material, the device can emit light with higher luminance than before, and the effect of the present invention is great.

[Brief description of the drawings]

FIG. 1 is a cross-sectional view of an example of an organic EL device according to the present invention.

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

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

FIG. 4 is a sectional view of an example of the organic EL device according to 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 Continuation of the front page (72) Inventor Atsushi Oda 5-7-1 Shiba, Minato-ku, Tokyo Within NEC Corporation (56) References JP-A-11-144868 (JP, A) (58) Survey Field (Int. Cl. ⁷ , DB name) C09K 11/06 CA (STN) REGISTRY (STN)

Claims (12)

(57) [Claims] 1. An organic electroluminescence device having one or more organic thin-film layers including a light-emitting layer between an anode and a cathode, wherein at least one of the organic thin-film layers has the following general formula (1): 1) [Wherein, R ^{1 to} R ¹⁶ 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 group; Alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group Represents a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group. R1 to R8 and R
9 to R16 may form a ring with two of each . An organic electroluminescent device comprising the dibenzoperylene compound represented by the formula [1] alone or in a mixture. 2. The organic electroluminescent device according to claim 1, wherein 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) alone or in a mixture. Luminescent element. 3. 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) alone or in a mixture. Organic electroluminescence element. 4. The method according to claim 1, wherein 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) alone or in a mixture. Organic electroluminescent element. R ¹ of 5. A compound represented by the general formula (1) to
At least one of R ¹⁶ is —NAr ¹ Ar ² (A
r ¹ and Ar ² each independently represent an aryl group having 6 to 20 carbon atoms, and the aryl group may have a substituent. 2. The organic electroluminescent device according to claim 1, wherein the organic electroluminescent device is a diarylamino group represented by the formula: Wherein R ¹ of the compound represented by the general formula (1) to
At least one of R ¹⁶ is —NAr ¹ Ar ² (A
r ¹ and Ar ² each independently represent an aryl group having 6 to 20 carbon atoms, and the aryl group may have a substituent. 3. The organic electroluminescent device according to claim 2, wherein the organic electroluminescent device is a diarylamino group represented by the formula: R ¹ of 7. A compound represented by the general formula (1) to
At least one of R ¹⁶ is —NAr ¹ Ar ² (A
r ¹ and Ar ² each independently represent an aryl group having 6 to 20 carbon atoms, and the aryl group may have a substituent. 4. The organic electroluminescent device according to claim 3, wherein the organic electroluminescent device is a diarylamino group represented by the formula: R ¹ in 8. The compound represented by the general formula (1) to
At least one of R ¹⁶ is —NAr ¹ Ar ² (A
r ¹ and Ar ² each independently represent an aryl group having 6 to 20 carbon atoms, and the aryl group may have a substituent. 5. The organic electroluminescent device according to claim 4, wherein the organic electroluminescent device is a diarylamino group represented by the formula: 9. R ¹ of the compound represented by the general formula (1) to
At least one of R ¹⁶ is —NAr ¹ Ar ² (A
r ¹ and Ar ² each independently represent an aryl group having 6 to 20 carbon atoms, and the aryl group may have a substituent. Is a diarylamino group represented by Ar ¹ ,
6. The method according to claim 5, wherein at least one of Ar ² has a substituted or unsubstituted styryl group as a substituent.
3. The organic electroluminescent device according to 1.). R ¹ in 10. A compound represented by the general formula (1)
At least one of R ¹⁶ to R ¹⁶ is —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. Is a diarylamino group represented by Ar ¹ ,
7. The method according to claim 6, wherein at least one of Ar ² has a substituted or unsubstituted styryl group as a substituent.
3. The organic electroluminescent device according to 1.). 11. R ¹ of the compound represented by the general formula (1)
At least one of R ¹⁶ to R ¹⁶ is —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. Is a diarylamino group represented by Ar ¹ ,
8. At least one of Ar ² has a substituted or unsubstituted styryl group as a substituent.
3. The organic electroluminescent device according to 1.). R ¹ in 12. The compound represented by the general formula (1)
At least one of R ¹⁶ to R ¹⁶ is —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. Is a diarylamino group represented by Ar ¹ ,
9. At least one of Ar ² has a substituted or unsubstituted styryl group as a substituent.
3. The organic electroluminescent device according to 1.).