JP2001237076A - Organic electroluminescence element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an organic EL element of high luminosity and of a long-life. SOLUTION: As a composition material of the organic EL element, a specific distyryl-diphenyl-amino-allylene compound expressed with formula [1] is used. (In the formula, Ar1 is an allylene group of substitution or non-substitution which contains 5-42 carbon number; Ar2 and Ar3 are groups independently, respectively expressed with a formula [2]; and Ar4 and Ar5 are allyl groups of substitution or non-substitution each of which contains 6-20 carbon number independently, respectively. Moreover, R6 is a substitution group other than that of hydrogen atom).

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 electroluminescent devices (E)
L element), by applying an electric field,
A self-luminous element utilizing the principle that a fluorescent substance emits light by recombination energy of holes injected from an anode and electrons injected from a cathode.

[0003] Eastman Kodak C.I. W. Ta
ng et al. report on a low-voltage driven organic EL device using a stacked device (for example, CW Tang and SA Va).
nSlyke, Applied Physics L
eters, Vol. 51, pp. 913, published in 1987).
Research on the L element has been actively conducted. Tang et al. Use tris (8-hydroxyquinolinol aluminum) for the light emitting layer and a triphenyldiamine derivative for the hole transport layer. The advantages of the stacked structure include: increasing the efficiency of injecting holes into the light emitting layer; increasing the efficiency of generating excitons generated by recombination by blocking electrons injected from the cathode; And confining excitons.

[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 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.
Regarding materials, various compounds have been developed as materials for organic electroluminescence devices.

[0005] As hole transport materials, 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-8-40995, JP-A-8-40995). No. 8-40997,
JP-A-8-53397, JP-A-8-8712
No. 2).

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

As light emitting materials, chelate complexes such as tris (8-quinolinolato) aluminum complex and the like, luminescent materials such as coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives and the like are known. It has been reported that the color can also emit light in the visible region from blue to red, and realization of a color display element is expected (for example, JP-A-8-239655, JP-A-7-138561, JP-A-3-200889, etc.).

[0008]

Furthermore, in addition to the above compounds, it has been disclosed that diphenylaminoarylene having a styryl group is useful as a constituent material of a high-performance organic electroluminescence device (Japanese Patent Application Laid-Open No. 11-1999). 7
4079, JP-A-11-185961, etc.).

However, in the case of distyryldiarylaminoarylene, when the two aryl groups of the diarylamino group both have a styryl group, the resulting EL device has high chemical stability despite high brightness. There was a shortage. As a result, the emission characteristics and the life characteristics of the EL element may be reduced.

[0010] Therefore, an object of the present invention is to develop an EL device having sufficiently high luminance, suppressing a decrease in light emission characteristics, and having high durability.

[0011]

According to the present invention for achieving the above object, one or more organic thin film layers are provided between an anode and a cathode, and the organic thin film layer has at least a light emitting layer. In the organic electroluminescent device, the light emitting layer comprises a compound represented by the following general formula [1] alone or as a mixture, and the organic electroluminescent device is provided.

[0012]

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(Wherein, Ar₁Is substituted with 5 to 42 carbon atoms
Or an unsubstituted arylene group; Ar_TwoAnd Ar
_ThreeAre each independently a group represented by the following general formula [2]
Yes; Ar _FourAnd Ar_FiveAre each independently 6 to 2 carbon atoms
0 is a substituted or unsubstituted aryl group. Note that Ar
_TwoAnd Ar_ThreeAnd / or Ar_FourAnd Ar_FiveAre rings
It may be formed. )

[0014]

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(Wherein, R _{1 to} R ₁₁ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyl group, Unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group,
Represents a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group. However,
R ₆ is a substituent other than a hydrogen atom. Also, R _{1 to} R
₁₁ may form a ring with two of them. )

According to the present invention, there is provided an organic electroluminescence device comprising at least an anode, a light emitting zone and a cathode, wherein the light emitting zone is formed of one or more organic thin film layers. An organic electroluminescent device, wherein a layer adjacent to and in contact with the anode among the organic thin film layers forming the emission band contains the compound represented by the general formula [1] alone or in a mixture. Is provided.

[0017]

BEST MODE FOR CARRYING OUT THE INVENTION The styryl group of the distyryldiarylaminoarylene compound used in the organic EL device of the present invention has a substituent at the β-position. That is, in the general formula [2], R ₆ is a substituent other than a hydrogen atom.
As a result, when both of the two aryl groups of the diarylamino group have a styryl group, that is, Ar ₂ and Ar ₃
Is a substituent represented by the general formula [2], the compound represented by the general formula [1] has sufficient chemical stability.

Although the reason for this is not clear, the hydrogen at the β-position of the styryl group is liable to cause a chemical reaction or the like. By substituting this hydrogen with chemically stable R ₆ , the hydrogen atom represented by the general formula [1] is obtained. It is speculated that this is because it is possible to suppress the compound to be deteriorated due to a chemical reaction or the like.

As a result, the obtained EL device has a sufficiently high luminance, a reduction in the light emission characteristics is suppressed, and a high durability is realized.

It is preferable that R ₆ is an aryl group having 6 to 20 carbon atoms for reasons such as excellent chemical stability.

For the same reason, R ₆ is preferably a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group.

Further, in the present invention, at least Ar
Both ₂ and Ar ₃ are the substituents represented by the general formula [2], but considering the symmetry of the general formula [1], at least both Ar ₄ and Ar ₅ have the general formula [2] And may be a substituent represented by

Further, in addition to Ar ₂ and Ar ₃ , Ar ₄ and Ar ₅ are each independently represented by the general formula [2] because of easy manufacturing and excellent characteristics of the obtained EL element. In some cases. That is, in some cases, all of Ar _{2 to} Ar ₅ may be independently a group represented by the general formula [2].

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

Ar ₁ is not particularly limited as long as it is a substituted or unsubstituted arylene group having 5 to 42 carbon atoms. Examples of such a compound include naphthyl group, anthranyl group, perylenylene group and 1: 2 Benzoperylenylene group, 1: 2: 7: 8 dibenzoperylenenylene group, 1:
2:11:12 dibenzoperylenylene group, terrylenenylene group, pentasenylene group, bisanthrenylene group,
10 ′-(9,9′-bianthryl) ylene group, 4,
4 ′-(1,1′-binaphthyl) ylene group, 4,10 ′
A-(1,9'-naphthylanthryl) ylene group, a divalent group represented by the following general formula [3],

[0026]

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(Wherein, Ar _{6 to} Ar ₈ each independently represent a naphthyl group or an anthranyl group), aromatic hydrocarbons such as phenanthrene, pyrene, biphenyl and terphenyl, or condensed polycyclic hydrocarbons, carbazole, Pyrrole, thiophene, furan, imidazole, pyrazole, isothiazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, furazan, thianthrene, isobenzofuran, phenoxazine, indolizine, indole, isoindole, 1H-indazole, purine, quinoline, Isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline,
The hydrogen atom of a heterocyclic compound such as pteridine, carbazole, β-carbazoline, phenanthridine, acridine, perimidine, phenanthroline, phenazine, phenothiazine, phenoxazine or a fused heterocyclic compound is represented by 2
Excluded divalent groups and their derivatives.

Examples of the aryl group having 6 to 20 carbon atoms include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a naphthacenyl group and a pyrenyl 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-tert-butyl group, 1,2,3-tricyano 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, 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.

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, 3-diiodoisopropyl group, 2,3-
T-butyl diiodo, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 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
-A trinitropropyl group and the like.

Examples of the substituted or unsubstituted aromatic hydrocarbon group include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 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. Can be

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

The substituted or unsubstituted aralkyl group includes benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthyl Methyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-
α-naphthylisopropyl group, β-naphthylmethyl group,
1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-
Pyrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromo Benzyl group, o
-Bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-amino Benzyl 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.

The substituted or unsubstituted aryloxy group is represented by —OZ, where Z is a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group. , 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4
-Phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group , 4
-Biphenylyl group, p-terphenyl-4-yl group,
p-terphenyl-3-yl group, p-terphenyl-2
-Yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,
o-tolyl group, m-tolyl group, p-tolyl group, pt-
Butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1
-Naphthyl group, 4-methyl-1-anthryl group, 4′-
Methylbiphenylyl group, 4 ''-t-butyl-p-terphenyl-4-yl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group , 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 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-phenanthroline-6
-Yl group, 1,7-phenanthrolin-8-yl group,
1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl 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-phenanthrolin-7-yl group, 1,8-phenanthroline-9-yl group, 1, 8
-Phenanthroline-10-yl group, 1,9-phenanthrolin-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-phenanthrolin-7-yl group, 1,9-phenanthrolin-8-yl group Group, 1,9-phenanthrolin-10-yl group, 1,1
A 0-phenanthrolin-2-yl group, a 1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a 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, 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-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group Group, 2,8-phenanthroline-7-yl group, 2,8-
Phenanthroline-9-yl group, 2,8-phenanthroline-10-yl group, 2,7-phenanthroline-1-
Yl group, 2,7-phenanthrolin-3-yl group, 2,
7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthroline-6
-Yl group, 2,7-phenanthrolin-8-yl group,
2,7-phenanthrolin-9-yl 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, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 2- An oxazolyl group, a 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-methylpyrrol-3-yl group, 2-methylpyrrole-4-yl group, 2-methylpyrrole-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-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,
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, 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-trinitropropyl group and the like.

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

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 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-tri Hydroxypropyl 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-bromo Isobutyl 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.

Further, specific examples of the compound represented by the general formula [1] include the following compounds (1) to (30), but are not limited thereto.

[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

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[0047]

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[0048]

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[0049]

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[0050]

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The element structure of the organic EL element of the present invention is a structure in which one or more organic thin film layers are laminated between electrodes. For example, as shown in FIG. 2, a structure in which a light emitting layer 4 and a cathode 6 are laminated; as shown in FIG. 2, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron transport layer 5, and a cathode 6 are laminated on a substrate 1. Structure; FIG. 3
As shown in FIG. 4, a structure in which an anode 2, a hole transport layer 3, a light emitting layer 4, and a cathode 6 are laminated on a substrate 1;
An anode 2, a light emitting layer 4, an electron transport layer 5, a cathode 6
Are laminated.

The compound represented by the general formula [1] used in the present invention may be used in any of the above-mentioned organic thin film layers, and may be doped into other hole transporting materials, luminescent materials, electron transporting materials and the like. It is also possible to make it.

More specifically, a structure in which 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. be able to. In this case, sufficient hole transport efficiency can be realized.

The organic thin film layer has at least an electron transport layer, and examples of the structure include a structure in which the electron transport layer contains the compound represented by the general formula [1] alone or as a mixture. In this case, sufficient electron transport efficiency can be realized.

Further, the luminescent layer containing the compound represented by the general formula [1] alone or as a mixture may have a structure in contact with the anode. In this case, since a hole transport layer is not required, the manufacturing process can be simplified and productivity can be improved.

The hole transporting material used in the present invention is not particularly limited, and a compound usually used as a hole transporting agent can be used.

For example, the following bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane (31):
N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine (32), N, N'-diphenyl-NN-bis (1 −
Triphenyldiamines such as naphthyl) -1,1′-biphenyl) -4,4′-diamine (33); and starburst molecules ((34) to (36)).

[0058]

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[0059]

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The electron transporting material used in the present invention is not particularly limited, and a compound usually used as an electron transporting material can be used.

For example, 2- (4-biphenylyl) -5
(4-t-butylphenyl) -1,3,4-oxadiazole (37), bis {2- (4-t-butylphenyl) -1,3,4-oxadiazole} -m-phenylene ( Oxadiazole derivatives such as 38) and triazole derivatives ((39) and (40)).

[0062]

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Further, quinolinol-based metal complexes represented by the general formulas [4], [5] and [6] can also be used.

[0064]

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(Wherein Q represents a substituted or unsubstituted hydroxyquinoline derivative or a substituted or unsubstituted benzoquinoline derivative; M represents a metal atom; and n represents the valence of the metal atom.)

[0066]

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(Wherein Q represents a substituted or unsubstituted hydroxyquinoline derivative or a substituted or unsubstituted benzoquinoline derivative; L is a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted A cycloalkyl group or an aryl group which may contain a substituted or unsubstituted nitrogen atom; M represents a metal atom;
Represents the valence of the metal atom. )

[0068]

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(In the formula, Q represents a substituted or unsubstituted hydroxyquinoline derivative or a substituted or unsubstituted benzoquinoline derivative; M represents a metal atom; and n represents the valence of the metal atom.)

Specific examples of the general formula [4] include the following compounds (41) to (46).

[0071]

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[0072]

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Similarly, specific examples of the general formula [5] include the following compounds (47) to (52).

[0074]

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[0075]

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The following compounds (53) to (55) are specific examples of the general formula [6].

[0077]

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In the case where the emission band is constituted by a plurality of organic thin film layers, the compound represented by the general formula [1] used in the present invention is used for a layer in contact with the anode, and further between this layer and the cathode. A light emitting layer can be provided. In this case, the compounds used in the present invention shown in the compounds (1) to (30) may be combined to form a plurality of layers.

Further, between the layer in contact with the anode and the cathode, the compound (5) was added to the electron transporting material represented by the compounds (37) to (55).
Even if a light emitting layer obtained by mixing 6) to (59) is inserted, or a light emitting layer made of an electron transporting light emitting material such as the compound (60) is inserted, a light emitting band is formed from a plurality of light emitting layers. Good.

[0080]

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The anode of the organic thin film EL element has a role of injecting holes into the emission band, and has a function of 4.5 eV.
It is effective to have the above work function. Specific examples of the anode material for realizing such characteristics include indium tin oxide alloy (ITO), tin oxide (NESA),
Gold, silver, platinum, copper and the like.

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 band. The cathode material for realizing such characteristics is not particularly limited, but specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-
Lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.

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 layers, such as the light-emitting layer, the hole transport layer, and the electron transport layer, containing the compound represented by the general formula [1] used in the organic EL device of the present invention are formed by vacuum evaporation, molecular beam evaporation (MBE).
Method) or a known method such as a dipping method of a solution dissolved in a solvent, a spin coating method, a casting method, a bar coating method, and a roll coating method.

The thickness of each organic layer constituting 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. And the efficiency becomes poor.
The range of m to 1 μm is preferred.

[0085]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the present invention is limited thereto.

(Synthesis Example) Synthesis of compound (8) 3,3'-Dimethylnaphthidine, 4- (di-p-tolylvinyl) bromobenzene, copper powder and potassium carbonate were placed in an Erlenmeyer flask purged with argon, Stirred at C for 30 hours. After completion of the reaction, the reaction mixture was diluted with toluene and filtered by suction to remove inorganic salts. The organic phase was washed once with water, dried over magnesium sulfate, separated and purified by silica gel chromatography using a mixed solvent of toluene and ligroin (volume ratio 1: 2), and a reprecipitation method using a mixed solvent of toluene and ethanol. Was used to synthesize a yellow powder of 4,4′-bis (di- (4- (di-p-tolylvinyl) phenylamino) -3,3′-binaphthyl (8). (M / z = 1440) was confirmed, and it was confirmed that it was a target compound.

The compound (8) thus obtained was
An example in which the light-emitting layer is used is shown in Example 4 below.

Examples in which a compound represented by the general formula [1] other than the compound (8) was used as a light emitting layer (Examples 1 to 5)
3, 5, 6, 9-11, 14, 15), an example in which a thin film mixed with a hole transport material is used as a light emitting layer (Examples 7 and 8), and a thin film mixed with an electron transport material is used as a light emitting layer The following are examples (Examples 12 and 13).

(Example 1) An organic thin film EL device having the cross-sectional structure shown in FIG. 1 was manufactured in the following procedure.

The device is composed of an anode / a light emitting layer / a cathode.
ing. Sputter ITO on a glass substrate
To form a film with a sheet resistance of 20Ω / □
did. Compound (2) is vacuum-deposited thereon as a light emitting layer
It was formed to a thickness of 40 nm by a method. Next, magnesium as a cathode
-Organic EL by forming 200nm silver alloy by vacuum evaporation
An element was manufactured. When a DC voltage of 5 V is applied to this element,
Roller, 200 cd / m ^TwoBlue light emission was obtained. Also,
The maximum luminous efficiency was 0.5 lm / W.

(Example 2) An organic EL device was manufactured in the same manner as in Example 1 except that the compound (6) was used as a light emitting material. When a DC voltage of 5 V was applied to this device, red light emission of 210 cd / m ² was obtained. The maximum luminous efficiency was 0.6 lm / W.

Example 3 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 (2). Next, a magnesium-silver alloy was formed as a cathode to a thickness of 200 nm by a vacuum evaporation method to produce an organic EL device. When a DC voltage of 5 V was applied to this element,
Blue light emission of 180 cd / m ² was obtained. The maximum luminous efficiency was 0.5 lm / W.

Example 4 FIG. 2 shows a cross-sectional structure of an element used in Example 4. The device has an anode / hole transport layer / light-emitting layer /
It is composed of an electron transport layer / cathode. Sheet resistance is 20Ω by sputtering ITO on glass substrate
/ □ to form an anode. A compound (33) was formed thereon as a hole transporting layer by vacuum evaporation to a thickness of 50 nm.
Formed. Next, a compound (8) was formed to a thickness of 40 nm by a vacuum evaporation method as a light-emitting layer. Next, a compound (39) was formed to a thickness of 20 nm by a vacuum evaporation method as an electron transporting layer. Next, a magnesium-silver alloy was formed as a cathode to a thickness of 200 nm by a vacuum evaporation method to produce an organic EL device. When a DC voltage of 10 V was applied to this element, 13,000 cd
/ M ² blue light emission was obtained. The maximum luminous efficiency was 4.0 lm / W.

Example 5 Compound (1) was used as a light emitting material.
The same operation as in Example 4 was carried out except that 7) was used, and the organic E
An L element was produced. When a DC voltage of 10 V was applied to this device, red light emission of 10,000 cd / m ² was obtained. The maximum luminous efficiency was 4.8 lm / W.

Example 6 The compound (3) was used as a hole transport layer.
An organic EL device was prepared in the same manner as in Example 4 except that the compound (38) was used as the electron transport layer in 1). When a DC voltage of 10 V was applied to this element, 1
Blue light emission of 3,000 cd / m ² was obtained. The maximum luminous efficiency was 4.5 lm / W.

(Embodiment 7) FIG. 4 shows a sectional structure of an element used in Embodiment 7. The device consists of anode / light-emitting layer / electron transport layer /
It is composed of a cathode. ITO was formed on a glass substrate by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. A thin film of 50 nm was formed thereon as a light emitting layer by co-evaporating the compound (33) and the compound (1) at a mass ratio of 1:10. Next, the compound (39) was formed to a thickness of 50 nm by a vacuum evaporation method as an electron transporting layer.

Next, magnesium-silver alloy was used as a cathode.
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 device, blue light emission of 5,000 cd / m ² was obtained. The maximum luminous efficiency was 2.5 lm / W.

Example 8 An organic EL device was manufactured in the same manner as in Example 7, except that the compound (21) was used instead of the compound (1). Apply a DC voltage of 10 V to this element.
Upon application, red light emission of 7,200 cd / m ² was obtained. The maximum luminous efficiency was 2.4 lm / W.

(Example 9) An ITO was formed on a glass substrate by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. A compound (2) was formed thereon as a light emitting layer by a vacuum deposition method to a thickness of 80 nm, and a compound (38) was formed thereon as an electron transport layer by a vacuum deposition method to a thickness of 50 nm. Next, a magnesium-silver alloy of 200 was used as a cathode.
to form an EL device. When a DC voltage of 10 V was applied to this device, blue light emission of 8,000 cd / m ² was obtained. The maximum luminous efficiency is 4.2 lm / W
Met.

Example 10 An organic EL device was manufactured in the same manner as in Example 9, except that the compound (18) was used instead of the compound (2). Apply a DC voltage of 10 to this element.
Upon application of V, red light emission of 9,200 cd / m ² was obtained. The maximum luminous efficiency was 2.4 lm / W.

Example 11 An organic EL device was produced in the same manner as in Example 9, except that the compound (23) was used instead of the compound (2) and the compound (39) was used as an electron transporting layer. When a DC voltage of 10 V was applied to this element,
Red light emission of 9,200 cd / m ² was obtained. The maximum luminous efficiency was 2.8 lm / W.

Example 12 FIG. 3 shows a cross-sectional structure of an element used in Example 12. The device is composed of an anode / a hole transport layer / a light emitting layer / a cathode. ITO on glass substrate
Was formed by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. A compound (33) was formed thereon as a hole transport layer by vacuum evaporation at a thickness of 50 nm.
Next, a 50 nm film was formed as a light-emitting layer by vacuum co-evaporation of the compound (41) and the compound (2) at a mass ratio of 20: 1. Next, a magnesium-silver alloy of 200 nm was used as a cathode.
Thus, an EL device was manufactured. DC voltage is applied to this element by 1
When 0 V was applied, blue light emission of 5,500 cd / m ² was obtained. The maximum luminous efficiency was 2.2 lm / W.

Example 13 As a light emitting layer, compound (4
An organic EL device was produced in the same manner as in Example 12, except that a 50 nm film obtained by vacuum co-evaporation of 1) and the compound (14) at a mass ratio of 20: 1 was used. When a DC voltage of 10 V was applied to this device, blue light emission of 6,000 cd / m ² was obtained. The maximum luminous efficiency is 2.1 lm /
W.

Example 14 An ITO was formed on a glass substrate by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. A compound (33) was formed thereon as a hole transport layer by vacuum evaporation at a thickness of 50 nm. A compound (2) was formed thereon as a light emitting layer by vacuum evaporation to a thickness of 40 n.
m and then a magnesium-silver alloy of 20
An EL element was fabricated by forming the layer to a thickness of 0 nm. When a DC voltage of 10 V was applied to this device, blue light emission of 4,000 cd / m ² was obtained. The maximum luminous efficiency is 1.3 lm /
W.

Example 15 An organic EL device was manufactured in the same manner as in Example 14, except that the compound (31) was used as the hole transport layer and the compound (4) was used as the light emitting layer. When a DC voltage of 10 V was applied to this element, 4,100
Red light emission of cd / m ² was obtained. The maximum luminous efficiency was 1.2 lm / W.

As described above, when the organic luminescent devices obtained in Examples 1 to 15 were continuously driven at an initial luminance of 100 cd / m ² , the half life of luminance was 5,000 hours or more in all the devices.

[0108]

As described above, in the organic electroluminescence device of the present invention, high-luminance EL light emission can be obtained, and a decrease in light emission characteristics and a decrease in life characteristics are suppressed, and a long life is realized. .

[Brief description of the drawings]

FIG. 1 is a schematic cross-sectional view showing one example of an organic electroluminescence device of the present invention.

FIG. 2 is a schematic cross-sectional view illustrating another example of the organic electroluminescence element of the present invention.

FIG. 3 is a schematic sectional view showing another example of the organic electroluminescence element of the present invention.

FIG. 4 is a schematic sectional view showing another example of the organic electroluminescence element 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 Within Electric Corporation (72) Inventor Atsushi Oda 5-7-1 Shiba, Minato-ku, Tokyo NEC Corporation F Term (reference) 3K007 AB02 AB03 AB04 AB11 CA01 CB01 DA01 DB03 EB00

Claims (11)

[Claims] 1. One or more layers between an anode and a cathode
Having an organic thin film layer, wherein the organic thin film layer is at least a light emitting layer.
In an organic electroluminescent element having
The light emitting layer comprises a compound represented by the following general formula [1],
Organic, characterized by comprising itself or as a mixture
Electroluminescence element. Embedded image(Wherein, Ar₁Is substituted or unsubstituted having 5 to 42 carbon atoms
An arylene group of Ar;_TwoAnd Ar_ThreeIs German
A group represented by the following general formula [2]; Ar _Fouras well as
Ar_FiveAre each independently substituted with 6 to 20 carbon atoms or
It is an unsubstituted aryl group. Note that Ar_TwoAnd Ar_ThreeLine
// Ar_FourAnd Ar_FiveMay form a ring with each other
No. )(Where R₁~ R₁₁Is independently a hydrogen atom, a halo
Gen atom, hydroxyl group, substituted or unsubstituted
Group, cyano group, nitro group, substituted or unsubstituted
Killed group, substituted or unsubstituted alkenyl group,
Or unsubstituted cycloalkyl group, substituted or unsubstituted
Alkoxy group, substituted or unsubstituted aromatic hydrocarbon
Group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted
Is an unsubstituted aralkyl group, a substituted or unsubstituted aryl
Roxy group, substituted or unsubstituted alkoxycarbonyl
Represents a carboxyl group or a carboxyl group. Where R₆Is hydrogen
It is a substituent other than an atom. Also, R₁~ R₁₁Are those
And two of them may form a ring. ) 2. The organic electroluminescent device according to claim 1, wherein Ar ₄ and Ar ₅ are each independently a group represented by the general formula [2]. 3. The organic electroluminescent device according to claim 1, wherein R ₆ is an aryl group having 6 to 20 carbon atoms. 4. The organic electroluminescent device according to claim 1, wherein R ₆ is a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group. 5. The organic thin film layer has at least a hole transport layer, and the hole transport layer comprises the compound represented by the general formula [1] alone or in a mixture. Item 5. The organic electroluminescence device according to any one of Items 1 to 4. 6. The organic thin film layer has at least an electron transporting layer, and the electron transporting layer contains the compound represented by the general formula [1] alone or in a mixture. 5. The organic electroluminescent device according to any one of items 1 to 4, 7. The organic electroluminescence device according to claim 1, wherein the light emitting layer is in contact with the anode. 8. At least an anode, an emission zone and a cathode
The emission band comprises one or more organic thin films
Organic electroluminescent devices formed from layers
Wherein the luminescent zone is adjacent to the anode and forms the luminescent zone
Of the organic thin film layer to be in contact with the anode is represented by the following general formula
Containing the compound represented by [1] alone or in a mixture
Organic electroluminescent element characterized by becoming
Child. Embedded image(Wherein, Ar₁Is substituted or unsubstituted having 5 to 42 carbon atoms
An arylene group of Ar;_TwoAnd Ar_ThreeIs German
A group represented by the following general formula [2]; Ar _Fouras well as
Ar_FiveAre each independently substituted with 6 to 20 carbon atoms or
It is an unsubstituted aryl group. Note that Ar_TwoAnd Ar_ThreeLine
// Ar_FourAnd Ar_FiveMay form a ring with each other
No. )(Where R₁~ R₁₁Is independently a hydrogen atom, a halo
Gen atom, hydroxyl group, substituted or unsubstituted
Group, cyano group, nitro group, substituted or unsubstituted
Killed group, substituted or unsubstituted alkenyl group,
Or unsubstituted cycloalkyl group, substituted or unsubstituted
Alkoxy group, substituted or unsubstituted aromatic hydrocarbon
Group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted
Is an unsubstituted aralkyl group, a substituted or unsubstituted aryl
Roxy group, substituted or unsubstituted alkoxycarbonyl
Represents a carboxyl group or a carboxyl group. Where R₆Is hydrogen
It is a substituent other than an atom. Also, R₁~ R₁₁Are those
And two of them may form a ring. ) 9. The organic electroluminescent device according to claim 8, wherein Ar ₄ and Ar ₅ are each independently a group represented by the general formula [2]. 10. The organic electroluminescent device according to claim 8, wherein R ₆ is an aryl group having 6 to 20 carbon atoms. 11. The organic electroluminescent device according to claim 8, wherein R ₆ is a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group.