JP2003081969A - Organic electroluminescent element and novel thiophene - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent element that emits light of high intensity with excellent luminous efficiency. SOLUTION: The organic electroluminescent element has at least one layer including at least one of the compound represented by general formula (1) [wherein R1 -R3 are each H, an alkyl, an aryl or an aralkyl; Y is H or a group represented by formula (a) (wherein R4 -R6 are each H, an alkyl, an aryl or an aralkyl); Z1 and Z2 are each H, a halogen, an alkyl, an alkoxy, substituted or unsubstituted amino, an aryl or aralkyl] sandwitched between a pair of electrodes.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an organic electroluminescent device and a novel compound which can be preferably used in the light emitting device.

[0002]

2. Description of the Related Art Conventionally, an inorganic electroluminescent device has been used as a panel type light source such as a backlight, but a high AC voltage is required to drive the light emitting device. Recently, an organic electroluminescence device (organic electroluminescence device: organic EL device) using an organic material as a light emitting material has been developed [Appl. Phys. Lett., 51, 91.
3 (1987)]. An organic electroluminescence device has a structure in which a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode, and electrons and holes are injected into the thin film to recombine to generate excitons. This is an element that emits light by using the light emitted when (excitons) are generated and the excitons are deactivated. The organic electroluminescence device can emit light at a direct current low voltage of about several V to several tens of V, and various colors (for example, red, blue, green) can be obtained by selecting the kind of the fluorescent organic compound. Can emit light. The organic electroluminescent device having such characteristics is expected to be applied to various light emitting devices, display devices and the like. However, the emission brightness is generally low, which is not practically sufficient.

As a method for improving the luminescence brightness, for example, an organic electroluminescent device using a light emitting layer using tris (8-quinolinolato) aluminum as a host compound, a coumarin derivative, and a pyran derivative as a guest compound (dopant) has been proposed. [J. Appl. Phys., 65, 3610 (198
9)]. Further, as the light emitting layer, for example, bis (2-methyl-8-quinolinolate) (4-phenylphenolate)
An organic electroluminescence device using aluminum as a host compound and an acridone derivative (for example, N-methyl-2-methoxyacridone) as a guest compound has been proposed (Japanese Patent Laid-Open No. 8-67873). However, it is hard to say that these light emitting elements also have sufficient light emission luminance. At present, an organic electroluminescent device that emits light with higher brightness is desired.

The general formula (1) relating to the organic electric field element of the present invention
Of the compounds represented by the following formula (A) or formula (B), those disclosed in JP-A-63-158558 as charge transporting substances for electrophotographic photoreceptors, There is no report on an organic electroluminescent device in the publication.

[0005]

[Chemical 4]

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide an organic electroluminescent device which has excellent luminous efficiency and emits light with high brightness. Furthermore, it is to provide a novel compound which can be suitably used for the light emitting device.

[0007]

Means for Solving the Problems The inventors of the present invention have completed the present invention as a result of extensive studies on organic electroluminescent elements. That is, the present invention provides an organic electroluminescent device comprising a pair of electrodes, at least one layer containing at least one compound represented by the general formula (1) being sandwiched between the pair of electrodes.

[0008]

[Chemical 5]

[Wherein R _{1 to} R ₃ each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, and Y Represents a hydrogen atom or a group represented by the general formula (a),

[0010]

[Chemical 6]

(In the formula, R _{4 to} R ₆ each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group.) Z ₁ and Z ₂ are a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted Alternatively, it represents an unsubstituted aralkyl group. ]

The layer containing the compound represented by the general formula (1) further contains a luminescent organic metal complex, and the organic electroluminescent device described above is represented by the general formula (1). The layer containing the compound described above further contains a triarylamine derivative, and the layer containing the compound represented by the general formula (1) is a light emitting layer. The organic electroluminescent device according to any one of 1 to 3, wherein the layer containing the compound represented by the general formula (1) is a hole injecting and transporting layer, between the pair of electrodes, Furthermore, the organic electroluminescent device according to 1), which further comprises a hole injecting and transporting layer, the organic electroluminescent device according to 1), further comprising an electron injecting and transporting layer between a pair of electrodes, represented by the following general formula (1a): The compound represented,

[0013]

[Chemical 7]

(Wherein R _{1 to} R ₆ each independently represents a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, and Z 1 ₁ and Z ₂ are a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted It represents an unsubstituted aralkyl group.).

[0015]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below. The organic electroluminescent element of the present invention comprises at least one layer containing at least one compound represented by the general formula (1) between a pair of electrodes.

[0016]

[Chemical 8]

[Wherein R _{1 to} R ₃ each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, and Y Represents a hydrogen atom or a group represented by the general formula (a),

[0018]

[Chemical 9]

(In the formula, R _{4 to} R ₆ each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group.) Z ₁ and Z ₂ are a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted Alternatively, it represents an unsubstituted aralkyl group. ]

In the compound represented by the general formula (1),
R _{1 to} R ₃ are each independently a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group,
Alternatively, it represents a substituted or unsubstituted aralkyl group.

In the present invention, examples of the aromatic component in the aryl group and the aralkyl group include carbocyclic aromatic compounds such as benzene, naphthalene and anthracene,
Or, it represents a group derived from a heterocyclic aromatic group such as furan, thiophene or pyridine.

Further, in the compound represented by the general formula (1), the aryl group and aralkyl group of R _{1 to} R ₃ may have a substituent, and a halogen atom and a carbon number of 1 to 20.
Linear, branched or cyclic alkyl group having 1 to 20 carbon atoms
Linear, branched or cyclic alkoxy group having 1 to 2 carbon atoms
N-monosubstituted amino group of 0, N, N- having 2 to 40 carbon atoms
It may be mono- or polysubstituted with a substituent such as a di-substituted amino group, an aryl group having 3 to 25 carbon atoms, or an aralkyl group having 5 to 16 carbon atoms.

R _{1 to} R ₃ are preferably a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbocyclic aromatic group having 6 to 30 carbon atoms, A substituted or unsubstituted heterocyclic aromatic group having 3 to 25 carbon atoms,
Alternatively, it is a substituted or unsubstituted aralkyl group having 5 to 16 carbon atoms, more preferably a hydrogen atom or 1 to 1 carbon atoms.
0 straight-chain, branched or cyclic alkyl group, having 6 to 2 carbon atoms
5 substituted or unsubstituted carbocyclic aromatic groups, having 4 to 4 carbon atoms
A substituted or unsubstituted heterocyclic aromatic group having 12 or a substituted or unsubstituted aralkyl group having 7 to 12 carbon atoms, more preferably a hydrogen atom, a straight chain, branched or cyclic group having 1 to 8 carbon atoms. Is an alkyl group, a substituted or unsubstituted carbocyclic aromatic group having 6 to 22 carbon atoms, or a substituted or unsubstituted heterocyclic aromatic group having 4 to 10 carbon atoms.

Specific examples of R _{1 to} R ₃ include hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group,
n-butyl group, isobutyl group, sec-butyl group, tert-
Butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, cyclopentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, cyclohexyl group, n-heptyl group, 1-methylhexyl group, cyclohexylmethyl group, 4-tert-butylcyclohexyl group, n-heptyl group, cycloheptyl group, n-octyl group, cyclooctyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group,
2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group,
3,5,5-trimethylhexyl group, n-decyl group, n
-Undecyl group, 1-methyldecyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-
Tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-
Linear, branched or cyclic alkyl group such as eicosyl group,

Phenyl group, 4-methylphenyl group, 3-
Methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4- n-butylphenyl group, 4-isobutylphenyl group, 4-sec
-Butylphenyl group, 2-sec-butylphenyl group, 4
-Tert-butylphenyl group, 3-tert-butylphenyl group, 2-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-neopentylphenyl group, 4-tert-pentyl group Phenyl group, 4-
n-hexylphenyl group, 4- (2'-ethylbutyl)
Phenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4- (2'-ethylhexyl) phenyl group, 4-n-nonylphenyl group, 4-n-decylphenyl group, 4-n- Undecylphenyl group, 4-n-dodecylphenyl group, 4-n-tetradecylphenyl group,
4-cyclohexylphenyl group, 4- (4'-methylcyclohexyl) phenyl group, 4- (4'-tert-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 2,3-dimethylphenyl group Group, 2,4-dimethylphenyl group, 2,5
-Dimethylphenyl group, 2,6-dimethylphenyl group,
3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 3,4,5-trimethylphenyl group, 2,3
5,6-tetramethylphenyl group, 2,4-diethylphenyl group, 2,6-diethylphenyl group, 2,5-diisopropylphenyl group, 2,6-diisopropylphenyl group, 2,6-diisobutylphenyl group, 2 , 4-di-
tert-butylphenyl group, 2,5-di-tert-butylphenyl group, 4,6-di-tert-butyl-2-methylphenyl group, 5-tert-butyl-2-methylphenyl group, 4
-Tert-butyl-2,6-dimethylphenyl group

4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propyloxyphenyl group, 3- n-propyloxyphenyl group, 4-isopropyloxyphenyl group, 2-isopropyloxyphenyl group, 4-n-
Butyloxyphenyl group, 4-isobutyloxyphenyl group, 2-sec-butyloxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 4-neopentyl Oxyphenyl group, 2-neopentyloxyphenyl group, 4-n-hexyloxyphenyl group, 4-
(2'-Ethylbutyl) oxyphenyl group, 4-n-heptyloxyphenyl group, 4-n-octyloxyphenyl group, 4-n-nonyloxyphenyl group, 4-n-decyloxyphenyl group, 4-n- Undecyloxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-
Tetradecyloxyphenyl group, 4-cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group, 2,3-dimethoxyphenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 3,4
-Dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 2-methoxy-4
-Methylphenyl group, 2-methoxy-5-methylphenyl group, 2-methyl-4-methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group,

4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 4- (4'-methylphenyl) phenyl group, 4- (3'-methylphenyl) phenyl group, 4- (4 ' -Ethylphenyl) phenyl group, 4- (4'-isopropylphenyl) phenyl group, 4- (4'-tert-butylphenyl) phenyl group,
4- (4'-n-hexylphenyl) phenyl group, 4-
(4'-n-octylphenyl) phenyl group, 4-
(4'-methoxyphenyl) phenyl group, 4- (4'-
n-butyloxyphenyl) phenyl group, 2- (2'-
Methoxyphenyl) phenyl group, 4- (4'-chlorophenyl) phenyl group, 3-methyl-4-phenylphenyl group, 3-methoxy-4-phenylphenyl group,

4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 3-chlorophenyl group, 2-chlorophenyl group,
4-bromophenyl group, 2-bromophenyl group, 4-trifluoromethylphenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group Base,
3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 3,4
-Dichlorophenyl group, 3,5-dichlorophenyl group,
2,5-dibromophenyl group, 2,4,6-trichlorophenyl group, 2-fluoro-4-methylphenyl group, 2
-Fluoro-5-methylphenyl group, 3-fluoro-2
-Methylphenyl group, 3-fluoro-4-methylphenyl group, 2-methyl-4-fluorophenyl group, 2-methyl-5-fluorophenyl group, 3-methyl-4-fluorophenyl group, 2-chloro-4 -Methylphenyl group, 2
-Chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group, 3-chloro-4-methylphenyl group,
2-methyl-3-chlorophenyl group, 2-methyl-4-
Chlorophenyl group, 3-methyl-4-chlorophenyl group, 2-chloro-4,6-dimethylphenyl group, 2-methoxy-4-fluorophenyl group, 3-methoxy-4-
Fluorophenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-4-ethoxyphenyl group, 2-
Fluoro-6-methoxyphenyl group, 3-fluoro-4
-Methoxyphenyl group, 3-fluoro-4-ethoxyphenyl group, 2-chloro-4-methoxyphenyl group, 3-
Chloro-4-methoxyphenyl group, 2-methoxy-5-
Chlorophenyl group, 3-methoxy-4-chlorophenyl group, 3-methoxy-6-chlorophenyl group, 5-chloro-2,4-dimethoxyphenyl group,

1-naphthyl group, 2-naphthyl group, 4-methyl-1-naphthyl group, 4-ethyl-1-naphthyl group,
6-n-butyl-2-naphthyl group, 6-tert-butyl-
2-naphthyl group, 7-ethyl-2-naphthyl group, 1,6
-Dimethyl-2-naphthyl group, 2-methoxy-1-naphthyl group, 4-methoxy-1-naphthyl group, 4-n-butyloxy-1-naphthyl group, 5-ethoxy-1-naphthyl group, 6-methoxy- 2-naphthyl group, 6-ethoxy-
2-naphthyl group, 6-n-butyloxy-2-naphthyl group, 6-n-hexyloxy-2-naphthyl group, 7-methoxy-2-naphthyl group, 7-n-butyloxy-2-
Naphthyl group, 6-fluoro-2-naphthyl group, 6-chloro-2-naphthyl group, 2,4-dichloro-1-naphthyl group, 1,6-dichloro-2-naphthyl group, 1,2,3,
4-tetrahydro-5-naphthyl group, 1,2,3,4-
Tetrahydro-6-naphthyl group, 5-indanyl group, 1
-Anthryl group, 2-anthryl group, 9-anthryl group, 10-fluoro-9-anthryl group, 9,10-difluoro-1-anthryl group, 10-methyl-9-anthryl group, 9,10-dimethyl-2 Anthryl group, 1
0-ethoxy-9-anthryl group, 10-phenyl-9
-Anthryl group, 2-fluorenyl group, 3-fluorenyl group, 7-methyl-2-fluorenyl group, 9-methyl-
2-fluorenyl group, 9-ethyl-2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-
Diethyl-2-fluorenyl group, 9-phenyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9-methyl-9-phenyl-2-fluorenyl group,
9-ethyl-9-phenyl-2-fluorenyl group,

4-aminophenyl group, N-methyl-4-
Aminophenyl group, N-ethyl-4-aminophenyl group, Nn-butyl-4-aminophenyl group, N-cyclohexyl-4-aminophenyl group, Nn-octyl-4-aminophenyl group, N- n-decyl-4-aminophenyl group, N-benzyl-4-aminophenyl group, N
-Phenyl-4-aminophenyl group, N- (3'-methylphenyl) -4-aminophenyl group, N- (4'-methylphenyl) -4-aminophenyl group, N- (4'-
n-butylphenyl) -4-aminophenyl group, N-
(4'-methoxyphenyl) -4-aminophenyl group,
N- (3'-fluorophenyl) -4-aminophenyl group, N- (4'-chlorophenyl) -4-aminophenyl group, N- (1'-naphthyl) -4-aminophenyl group, N- (2 '-Naphthyl) -4-aminophenyl group,
N, N-dimethyl-4-aminophenyl group, N, N-diethyl-4-aminophenyl group, N, N-di-n-butyl-4-aminophenyl group, N, N-di-n-hexyl- 4-aminophenyl group, N, N-di-n-octyl-
4-aminophenyl group, N, N-di-n-decyl-4-
Aminophenyl group, N, N-di-n-dodecyl-4-aminophenyl group, N-methyl-N-ethyl-4-aminophenyl group, N-ethyl-Nn-butyl-4-aminophenyl group, N-methyl-N-phenyl-4-aminophenyl group, Nn-butyl-N-phenyl-4-aminophenyl group, N, N-diphenyl-4-aminophenyl group, N, N-di (3 ' -Methylphenyl) -4-aminophenyl group, N, N-di (4'-methylphenyl) -4
-Aminophenyl group, N, N-di (4'-ethylphenyl) -4-aminophenyl group, N, N-di (4'-tert
-Butylphenyl) -4-aminophenyl group, N, N-
Di (4'-n-hexylphenyl) -4-aminophenyl group, N, N-di (4'-methoxyphenyl) -4-aminophenyl group, N, N-di (4'-ethoxyphenyl) -4 -Aminophenyl group, N, N-di (4'-n-
Butyloxyphenyl) -4-aminophenyl group, N,
N-di (4'-n-hexyloxyphenyl) -4-aminophenyl group, N, N-di (1'-naphthyl) -4-
Aminophenyl group, N, N-di (2'-naphthyl) -4
-Aminophenyl group, N-phenyl-N- (3'-methylphenyl) -4-aminophenyl group, N-phenyl-
N- (4'-methylphenyl) -4-aminophenyl group, N-phenyl-N- (4'-octylphenyl)-
4-aminophenyl group, N-phenyl-N- (4'-methoxyphenyl) -4-aminophenyl group, N-phenyl-N- (4'-ethoxyphenyl) -4-aminophenyl group, N-phenyl- N- (4'-n-hexyloxyphenyl) -4-aminophenyl group, N-phenyl-
N- (4'-fluorophenyl) -4-aminophenyl group, N-phenyl-N- (1'-naphthyl) -4-aminophenyl group, N-phenyl-N- (2'-naphthyl)
-4-aminophenyl group, N-phenyl-N- (4'-
Phenylphenyl) -4-aminophenyl group, N, N-
Diphenyl-4-amino-1-naphthyl group, N, N-di (3′-methylphenyl) -4-amino-1-naphthyl group, N, N-di (4′-methylphenyl) -4-amino- 1-naphthyl group, N, N-di (4'-ethylphenyl) -4-amino-1-naphthyl group, N, N-di (4 '
-Tert-butylphenyl) -4-amino-1-naphthyl group, N, N-di (4'-n-hexylphenyl) -4-
Amino-1-naphthyl group, N, N-di (4′-methoxyphenyl) -4-amino-1-naphthyl group, N, N-di (4′-ethoxyphenyl) -4-amino-1-naphthyl group , N, N-di (4'-n-butyloxyphenyl)
-4-amino-1-naphthyl group, N, N-di (4'-n
-Hexyloxyphenyl) -4-amino-1-naphthyl group, N, N-di (1'-naphthyl) -4-amino-1
-Naphthyl group, N, N-di (2'-naphthyl) -4-amino-1-naphthyl group, N-phenyl-N- (3'-methylphenyl) -4-amino-1-naphthyl group, N- Phenyl-N- (4'-methylphenyl) -4-amino-
1-naphthyl group, N-phenyl-N- (4'-octylphenyl) -4-amino-1-naphthyl group, N-phenyl-N- (4'-methoxyphenyl) -4-amino-1
-Naphthyl group, N-phenyl-N- (4'-ethoxyphenyl) -4-amino-1-naphthyl group, N-phenyl-N- (4'-n-hexyloxyphenyl) -4-amino-1- Naphthyl group, N-phenyl-N- (4'-fluorophenyl) -4-amino-1-naphthyl group, N-
Phenyl-N- (1'-naphthyl) -4-amino-1-
Naphthyl group, N-phenyl-N- (2'-naphthyl)-
4-amino-1-naphthyl group, N-phenyl-N-
(4′-phenylphenyl) -4-amino-1-naphthyl group, N, N-diphenyl-6-amino-2-naphthyl group, N, N-di (3′-methylphenyl) -6-amino-2 -Naphthyl group, N, N-di (4'-methylphenyl) -6-amino-2-naphthyl group, N, N-di (4 '
-Ethylphenyl) -6-amino-2-naphthyl group,
N, N-di (4'-tert-butylphenyl) -6-amino-2-naphthyl group, N, N-di (4'-n-hexylphenyl) -6-amino-2-naphthyl group, N, N-di (4'-methoxyphenyl) -6-amino-2-naphthyl group, N, N-di (4'-ethoxyphenyl) -6-amino-2-naphthyl group, N, N-di (4 ' -N-butyloxyphenyl) -6-amino-2-naphthyl group, N,
N-di (4'-n-hexyloxyphenyl) -6-amino-2-naphthyl group, N, N-di (1'-naphthyl)
-6-amino-2-naphthyl group, N, N-di (2'-naphthyl) -6-amino-2-naphthyl group, N-phenyl-N- (3'-methylphenyl) -6-amino-2 -Naphthyl group, N-phenyl-N- (4'-methylphenyl) -6-amino-2-naphthyl group, N-phenyl-N
-(4'-octylphenyl) -6-amino-2-naphthyl group, N-phenyl-N- (4'-methoxyphenyl) -6-amino-2-naphthyl group, N-phenyl-N
-(4'-ethoxyphenyl) -6-amino-2-naphthyl group, N-phenyl-N- (4'-n-hexyloxyphenyl) -6-amino-2-naphthyl group, N-phenyl-N- (4'-Fluorophenyl) -6-amino-
2-naphthyl group, N-phenyl-N- (1'-naphthyl) -6-amino-2-naphthyl group, N-phenyl-N
-(2'-naphthyl) -6-amino-2-naphthyl group,
N-phenyl-N- (4'-phenylphenyl) -6-
A substituted or unsubstituted carbocyclic aromatic group such as amino-2-naphthyl group,

4-quinolyl group, 3-quinolyl group, 4-methyl-2-quinolyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 4-methyl-2-pyridyl group, 5
-Methyl-2-pyridyl group, 6-methyl-2-pyridyl group, 6-fluoro-3-pyridyl group, 6-methoxy-3
-Pyridyl group, 6-methoxy-2-pyridyl group, 3-furyl group, 2-furyl group, 3-thienyl group, 2-thienyl group, 4-methyl-3-thienyl group, 5-methyl-2-thienyl group A substituted or unsubstituted heterocyclic aromatic group such as a 3-methyl-2-thienyl group, a 2-oxazolyl group, a 2-thiazolyl group, a 2-benzoxazolyl group, a 2-benzothiazolyl group, and a 2-benzimidazolyl group. ,

Benzyl group, phenethyl group, α-methylbenzyl group, α, α-dimethylbenzyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, furfuryl group, 2-
Methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 4-ethylbenzyl group, 4-isopropylbenzyl group, 4-tert-butylbenzyl group, 4-n-hexylbenzyl group, 4-n-nonylbenzyl group Base, 3, 4
-Dimethylbenzyl group, 3-methoxybenzyl group, 4-
Methoxybenzyl group, 4-ethoxybenzyl group, 4-n
-Butyloxybenzyl group, 4-n-hexyloxybenzyl group, 4-n-nonyloxybenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 4-chlorobenzyl group, etc. Alternatively, there may be mentioned an unsubstituted aralkyl group and the like.

In the compound represented by the general formula (1),
Y represents a hydrogen atom or a group represented by the general formula (a).

[0034]

[Chemical 10]

(In the formula, R _{4 to} R ₆ each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group.)

In the group represented by the general formula (a), R ₄
To R ₆ each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group.

In the group represented by the general formula (a), the aryl group and aralkyl group represented by R _{4 to} R ₆ may have a substituent, and a halogen atom or a straight chain having 1 to 16 carbon atoms. A branched or cyclic alkyl group, a linear or branched or cyclic alkoxy group having 1 to 16 carbon atoms, and a carbon number of 1 to 20
Of N-mono-substituted amino group, C2-C40 N, N-di-substituted amino group, C3-C25 aryl group, or C5-C16 aralkyl group. It may be polysubstituted.

R _{4 to} R ₆ are preferably a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbocyclic aromatic group having 6 to 30 carbon atoms, A substituted or unsubstituted heterocyclic aromatic group having 3 to 25 carbon atoms,
Alternatively, it is a substituted or unsubstituted aralkyl group having 5 to 16 carbon atoms, more preferably a hydrogen atom or 1 to 1 carbon atoms.
0 straight-chain, branched or cyclic alkyl group, having 6 to 2 carbon atoms
5 substituted or unsubstituted carbocyclic aromatic groups, having 4 to 4 carbon atoms
A substituted or unsubstituted heterocyclic aromatic group having 12 or a substituted or unsubstituted aralkyl group having 7 to 12 carbon atoms, more preferably a hydrogen atom, a straight chain, branched or cyclic group having 1 to 8 carbon atoms. Is an alkyl group, a substituted or unsubstituted carbocyclic aromatic group having 6 to 22 carbon atoms, or a substituted or unsubstituted heterocyclic aromatic group having 4 to 10 carbon atoms.

Specific examples of R _{4 to} R ₆ include, for example, hydrogen atom, linear, branched or cyclic alkyl groups mentioned as specific examples of R _{1 to} R ₃ , and substituted or unsubstituted carbocyclic aromatic groups. Group, a substituted or unsubstituted heterocyclic aromatic group, a substituted or unsubstituted aralkyl group, and the like.

In the compound represented by the general formula (1),
Z ₁ and Z ₂ are a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted Alternatively, it represents an unsubstituted aralkyl group.

Further, in the compound represented by the general formula (1), the aryl group and aralkyl group of Z ₁ and Z ₂ may have a substituent, and a halogen atom and a carbon number of 1 to
16 straight-chain, branched or cyclic alkyl groups, 1 to 1 carbon atoms
16 linear, branched or cyclic alkoxy groups, 3 carbon atoms
An aryl group having 25 to 25 carbon atoms, an aralkyl group having 5 to 16 carbon atoms,
N-monosubstituted amino group having 1 to 20 carbon atoms, 2 to 4 carbon atoms
It may be mono- or poly-substituted with a substituent such as 0 N, N-disubstituted amino group.

Further, in the compound represented by the general formula (1), the amino groups of Z ₁ and Z ₂ may have a substituent, and are an alkyl group having 1 to 20 carbon atoms and 3 to 3 carbon atoms. 20
May be mono-substituted or di-substituted with a substituent such as the aryl group or the C 4-20 aralkyl group.

Z ₁ and Z ₂ are preferably hydrogen atoms,
Halogen atom, linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted carbocyclic aromatic group having 6 to 25 carbon atoms Group, substituted or unsubstituted heterocyclic aromatic group having 3 to 25 carbon atoms, substituted or unsubstituted aralkyl group having 5 to 16 carbon atoms, unsubstituted amino group, or substituted amino group having 1 to 24 carbon atoms More preferably, it is a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 10 carbon atoms, and 6 to 6 carbon atoms. A substituted or unsubstituted carbocyclic aromatic group having 12 carbon atoms, a substituted or unsubstituted heterocyclic aromatic group having 4 to 12 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 12 carbon atoms, or 1 carbon atom ~ 20 substituted amino groups

More preferably, a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms, and 6 to 10 carbon atoms. A substituted or unsubstituted carbocyclic aromatic group, a substituted or unsubstituted heterocyclic aromatic group having 4 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 10 carbon atoms, or 1 to 1 carbon atoms. 20 is a substituted amino group.

Specific examples of the Z ₁ and Z ₂ groups include a halogen atom such as a hydrogen atom, a fluorine atom, a chlorine atom and a bromine atom, for example, a straight chain, a branched chain or a straight chain which is mentioned as a specific example of R _{1 to} R _3. Cyclic alkyl group, methoxy group, ethoxy group,
n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, cyclopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group Group, 2-ethylbutyloxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy group, n-undecyloxy group, n
-Dodecyloxy group, n-tridecyloxy group, n-tetradecyloxy group, n-pentadecyloxy group, n-
Hexadecyloxy group, n-heptadecyloxy group, n
-A straight-chain, branched or cyclic alkoxy group such as octadecyloxy group and n-eicosyloxy group,

For example, a substituted or unsubstituted carbocyclic aromatic group and a substituted or unsubstituted heterocyclic aromatic group, a substituted or unsubstituted aralkyl group, an amino group, which are mentioned as specific examples of R _{1 to} R ₃ , N-methylamino group, N-ethylamino group, Nn-butylamino group, N-cyclohexylamino group, Nn-octylamino group, Nn-decylamino group, N-benzylamino group, N- Phenylamino group, N- (3-methylphenyl) amino group, N- (4-
Methylphenyl) amino group, N- (4-n-butylphenyl) amino group, N- (4-methoxyphenyl) amino group, N- (3-fluorophenyl) amino group, N- (4
-Chlorophenyl) amino group, N- (1-naphthyl) amino group, N- (2-naphthyl) amino group, N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-butyl Amino group, N, N-di-n-hexylamino group, N, N-di-n-octylamino group, N, N-di-n-decylamino group, N, N-di-n-dodecylamino group, N-methyl-N-ethylamino group, N-ethyl-
N-n-butylamino group, N-methyl-N-phenylamino group, N-n-butyl-N-phenylamino group, N,
N-diphenylamino group, N, N-di (3-methylphenyl) amino group, N, N-di (4-methylphenyl) amino group, N, N-di (4-ethylphenyl) amino group,
N, N-di (4-tert-butylphenyl) amino group,
N, N-di (4-n-hexylphenyl) amino group,
N, N-di (4-methoxyphenyl) amino group, N, N
-Di (4-ethoxyphenyl) amino group, N, N-di (4-n-butyloxyphenyl) amino group, N, N-
Di (4-n-hexyloxyphenyl) amino group, N,
N-di (1-naphthyl) amino group, N, N-di (2-naphthyl) amino group, N-phenyl-N- (3-methylphenyl) amino group, N-phenyl-N- (4-methylphenyl) ) Amino group, N-phenyl-N- (4-octylphenyl) amino group, N-phenyl-N- (4-methoxyphenyl) amino group, N-phenyl-N- (4-ethoxyphenyl) amino group, N -Phenyl-N- (4-n
-Hexyloxyphenyl) amino group, N-phenyl-
N- (4-fluorophenyl) amino group, N-phenyl-N- (1-naphthyl) amino group, N-phenyl-N-
(2-naphthyl) amino group, N-phenyl-N- (4-
Examples thereof include a substituted or unsubstituted amino group such as phenylphenyl) amino group.

The organic electroluminescent device of the present invention is characterized in that at least one compound represented by the general formula (1) is used. For example, the compound represented by the general formula (1) is used as a light emitting component. When used in a light emitting layer, it is possible to provide an organic electroluminescent device which emits blue to blue green light which has not been hitherto available and which has high brightness and excellent durability.

Further, by forming a light emitting layer in combination with other light emitting components, it is possible to provide an organic electroluminescent device which emits white light with high brightness and excellent durability.

Specific examples of the compound represented by the general formula (1) according to the present invention include the following A-1 to A-18 and B-1 to
B-18, C-1 to C-21, D-1 to D-18, E-
1 to E-24, F-1 to F-24, G-1 to G-21,
H-1 to H-18, I-1 to I-24, J-1 to J-1
8, K-1 to K-18, L-1 to L-21, M-1 to M
-18, N-1 to N-24, O-1 to O-24, P-1
To P-21, Q-1 to Q-18 and R-1 to R-24
However, the present invention is not limited thereto.

[0050]

[Chemical 11]

[0051]

[Chemical 12]

[0052]

[Chemical 13]

[0053]

[Chemical 14]

[0054]

[Chemical 15]

[0055]

[Chemical 16]

[0056]

[Chemical 17]

[0057]

[Chemical 18]

[0058]

[Chemical 19]

[0059]

[Chemical 20]

[0060]

[Chemical 21]

[0061]

[Chemical formula 22]

[0062]

[Chemical formula 23]

[0063]

[Chemical formula 24]

[0064]

[Chemical 25]

[0065]

[Chemical formula 26]

[0066]

[Chemical 27]

[0067]

[Chemical 28]

[0068]

[Chemical 29]

[0069]

[Chemical 30]

[0070]

[Chemical 31]

[0071]

[Chemical 32]

[0072]

[Chemical 33]

[0073]

[Chemical 34]

[0074]

[Chemical 35]

[0075]

[Chemical 36]

[0076]

[Chemical 37]

[0077]

[Chemical 38]

[0078]

[Chemical Formula 39]

[0079]

[Chemical 40]

[0080]

[Chemical 41]

[0081]

[Chemical 42]

[0082]

[Chemical 43]

[0083]

[Chemical 44]

[0084]

[Chemical formula 45]

[0085]

[Chemical formula 46]

[0086]

[Chemical 47]

[0087]

[Chemical 48]

[0088]

[Chemical 49]

[0089]

[Chemical 50]

[0090]

[Chemical 51]

[0091]

[Chemical 52]

[0092]

[Chemical 53]

[0093]

[Chemical 54]

[0094]

[Chemical 55]

[0095]

[Chemical 56]

[0096]

[Chemical 57]

[0097]

[Chemical 58]

[0098]

[Chemical 59]

[0099]

[Chemical 60]

[0100]

[Chemical formula 61]

[0101]

[Chemical formula 62]

[0102]

[Chemical formula 63]

[0103]

[Chemical 64]

[0104]

[Chemical 65]

[0105]

[Chemical formula 66]

[0106]

[Chemical formula 67]

[0107]

[Chemical 68]

[0108]

[Chemical 69]

[0109]

[Chemical 70]

[0110]

[Chemical 71]

[0111]

[Chemical 72]

[0112]

[Chemical formula 73]

[0113]

[Chemical 74]

[0114]

[Chemical 75]

[0115]

[Chemical 76]

[0116]

[Chemical 77]

[0117]

[Chemical 78]

[0118]

[Chemical 79]

[0119]

[Chemical 80]

[0120]

[Chemical 81]

[0121]

[Chemical formula 82]

[0122]

[Chemical 83]

[0123]

[Chemical 84]

[0124]

[Chemical 85]

[0125]

[Chemical 86]

[0126]

[Chemical 87]

[0127]

[Chemical 88]

[0128]

[Chemical 89]

[0129]

[Chemical 90]

[0130]

[Chemical Formula 91]

[0131]

[Chemical Formula 92]

[0132]

[Chemical formula 93]

[0133]

[Chemical 94]

[0134]

[Chemical 95]

[0135]

[Chemical 96]

[0136]

[Chemical 97]

[0137]

[Chemical 98]

[0138]

[Chemical 99]

[0139]

[Chemical 100]

[0140]

[Chemical 101]

[0141]

[Chemical 102]

[0142]

[Chemical 103]

[0143]

[Chemical 104]

[0144]

[Chemical 105]

[0145]

[Chemical formula 106]

[0146]

[Chemical formula 107]

[0147]

[Chemical 108]

[0148]

[Chemical 109]

[0149]

[Chemical 110]

[0150]

[Chemical 111]

[0151]

[Chemical 112]

[0152]

[Chemical 113]

[0153]

[Chemical 114]

[0154]

[Chemical 115]

[0155]

[Chemical formula 116]

[0156]

[Chemical 117]

[0157]

[Chemical 118]

[0158]

[Chemical formula 119]

[0159]

[Chemical 120]

[0160]

[Chemical 121]

[0161]

[Chemical formula 122]

[0162]

[Chemical 123]

The compound represented by the general formula (1) according to the present invention can be produced, for example, by the following method.

The compound represented by the general formula (1) according to the present invention can be produced, for example, by the following method. That is, by reacting a carbonyl compound represented by the following general formula (2) with a phosphonic acid derivative represented by the following general formula (3) in the presence of a base, in the general formula (1), Y is a hydrogen atom. Certain compounds can be made.

[0165]

[Chemical formula 124] [In the formula, R _{1 to} R ₃ , Z ₁ and Z ₂ have the same meanings as in the case of the general formula (1), and R represents an alkyl group having 1 to 4 carbon atoms or a phenyl group. ]

Further, for example, by reacting a carbonyl compound represented by the following general formula (4) with a phosphonic acid derivative represented by the following general formulas (3) and (5) in the presence of a base. , In the general formula (1), Y
Is the general formula (a)

[0167]

[Chemical 125] (In the formula, R _{4 to} R ₆ are each independently a hydrogen atom, a straight chain,
It represents a branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group. ) The compound which is a group represented by these can be manufactured.

[0168]

[Chemical formula 126] [In the formula, R _{1 to} R ₆ , Z ₁ and Z ₂ have the same meanings as in the case of the general formula (1), and R represents an alkyl group having 1 to 4 carbon atoms or a phenyl group. ]

The compound represented by the general formula (2) is obtained, for example, by reacting a compound represented by the following general formula (6) and a carboxylic acid halide represented by the following general formula (7) in the presence of aluminum chloride. It can be produced by reacting with (for example, J. Polym. Sci. Polym. Chem.
Ed., 23, 1787 (1985)).

The compound represented by the general formula (4) includes, for example, a compound represented by the following general formula (6) and a carboxylic acid halide represented by the following general formula (7) and the following general formula (8). Can be produced, for example, by reacting in the presence of aluminum chloride (for example, J. Polym. Sci. Polym. Chem. Ed., 23, 1787 (198
See the method described in 5)).

[0171]

[Chemical 127] [In the formula, R₁, R_Four, Z₁And Z₂Is the field of general formula (1)
X has the same meaning as ₁And X₂Represents a halogen atom
You ]

In the general formula (7) and the general formula (8), X ₁ and X ₂ represent a halogen atom, and preferably,
Represents a chlorine atom, a bromine atom, and an iodine atom.

The phosphonic acid derivatives represented by the general formula (3) and the general formula (5) are obtained by, for example, converting the compounds represented by the general formula (9) and the general formula (10) below into the general formula (11) below. It can be produced by reacting with a trialkoxyphosphine represented by the formula (1).

[0174]

[Chemical 128] [In formula, R < ₂ >, R < ₃ >, R < ₅ > and R < ₆ > represent the same meaning as the case of General formula (1), R represents a C1-C4 alkyl group or a phenyl group, and X < ₃ > and X ₄ represents a halogen atom. ]

In the general formula (9) and the general formula (10), X ₃ and X ₄ represent a halogen atom, and preferably,
Represents a chlorine atom, a bromine atom, and an iodine atom.

The compound represented by the general formula (6) can be produced, for example, by reacting a benzyl chloride derivative with sulfur (for example, J. Polym. Sc).
i. Polym. Chem. Ed., 22, 2189 (1984)).

The compound represented by the general formula (1) according to the present invention is produced in a form in which it is solvated with a solvent (eg, an aromatic hydrocarbon solvent such as toluene) optionally used. However, the compound represented by the general formula (1) according to the present invention includes such a solvate. Of course, it also includes a non-solvate containing no solvent.

In the organic electroluminescence device of the present invention, not only the non-solvate of the compound represented by the general formula (1) of the present invention but also such a solvate can be used.

When the compound represented by the general formula (1) according to the present invention is used in an organic electroluminescence device, a purification method such as a recrystallization method, a column chromatography method, a sublimation purification method,
Alternatively, it is preferable to use a compound with increased purity by combining these methods.

The organic electroluminescence device generally comprises at least one light emitting layer containing at least one kind of light emitting component sandwiched between a pair of electrodes. Considering the respective function levels of hole injection and hole transport, electron injection and electron transport of the compound used for the light emitting layer, the hole injection transport layer and / or the electron containing a hole injection transport component may be added as desired. An electron injecting and transporting layer containing an injecting and transporting component can also be provided.

For example, when the compound used for the light emitting layer has a good hole injecting function, a hole transporting function and / or an electron injecting function, and an electron transporting function, the light emitting layer is a hole injecting and transporting layer and / or an electron. It is possible to have a structure of a device that also serves as an injecting and transporting layer. Of course, in some cases, a device of a type (one-layer device) in which neither the hole injecting / transporting layer nor the electron injecting / transporting layer is provided may be used.

Each of the hole injecting / transporting layer, the electron injecting / transporting layer and the light emitting layer may have a single layer structure or a multi-layer structure. The layers may be formed by separately providing a layer having an injection function (hole injection layer and electron injection layer) and a layer having a transport function (hole transport layer and electron transport layer) in each layer.

In the organic electroluminescent device of the present invention, the compound represented by the general formula (1) according to the present invention is preferably used as a hole injecting / transporting component, a light emitting component or an electron injecting / transporting component. More preferably, it is used as a transport component or a light emitting component, and particularly preferably as a light emitting component.

In the organic electroluminescent device of the present invention, the compound represented by the general formula (1) according to the present invention may be used alone or in combination.

The constitution of the organic electroluminescent element of the present invention is not particularly limited, and includes, for example, (A) anode /
Hole injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type element (FIG. 1), (B) anode / hole injecting / transporting layer / light emitting layer / cathode type element (FIG. 2), (C) anode / light emitting Layer / electron injection / transport layer / cathode type element (FIG. 3), (D) anode / light emitting layer / cathode type element (FIG. 4) and the like. Further, it is an element of a type in which a light emitting layer is sandwiched between electron injecting and transporting layers (E).
Anode / hole injecting / transporting layer / electron injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type element (FIG. 5) can also be used.
The (D) type element structure includes an element of a type in which a light emitting component is sandwiched between a pair of electrodes in a single layer form, and further, for example, (F) a hole injecting and transporting component, light emission Element (FIG. 6) of a type in which a component and an electron injecting and transporting component are mixed and sandwiched between a pair of electrodes, and (G) a pair of electrodes in a single layer form in which a hole injecting and transporting component and a light emitting component are mixed. There are an element of a type sandwiched between them (FIG. 7) and an element of a type sandwiched between a pair of electrodes in a single layer form (H) in which a luminescent component and an electron injecting and transporting component are mixed (FIG. 8).

The organic electroluminescence device of the present invention is not limited to these device constitutions, and a plurality of hole injecting and transporting layers, light emitting layers and electron injecting and transporting layers may be provided in each type of device. You can In each type of device, between the hole injecting and transporting layer and the light emitting layer,
A mixed layer of the hole injecting and transporting component and the light emitting component and / or a mixed layer of the light emitting and electron injecting and transporting components may be provided between the light emitting layer and the electron injecting and transporting layer.

A more preferable structure of the organic electroluminescent element is as follows.
(A) type element, (B) type element, (C) type element, (E) type element, (F) type element, (G) type element or (H) type element, and more preferably (A) ) Type element, (B) type element, (C) type element, (F) type element, or (H) type element.

FIG. 1 shows the organic electroluminescent device of the present invention.
(A) Anode / hole injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type element shown in FIG.

In FIG. 1, 1 is a substrate, 2 is an anode, 3 is a hole injecting and transporting layer, 4 is a light emitting layer, 5 is an electron injecting and transporting layer, and 6
Is a cathode and 7 is a power supply.

The organic electroluminescent element of the present invention is preferably supported on the substrate 1. The substrate is not particularly limited, but is preferably transparent or translucent, for example, a glass plate, Transparent plastic sheet (eg polyester, polycarbonate, polysulfone, polymethylmethacrylate, polypropylene,
Examples thereof include a sheet made of polyethylene or the like), a semitransparent plastic sheet, quartz, transparent ceramics, or a composite sheet obtained by combining these. Further, the substrate can be combined with, for example, a color filter film, a color conversion film, or a dielectric reflection film to control the emission color.

For the anode 2, it is preferable to use a metal, an alloy or an electrically conductive compound having a relatively large work function as an electrode material.

Examples of the electrode material used for the anode include gold, platinum, silver, copper, cobalt, nickel, palladium, vanadium, tungsten, tin oxide, zinc oxide, and I.
Examples thereof include TO (indium tin oxide), polythiophene, polypyrrole and the like. These electrode substances may be used alone or in combination.

The anode can be formed on the substrate by using these electrode substances by a method such as a vapor deposition method or a sputtering method. The anode may have a single layer structure or a multilayer structure.

The sheet electric resistance of the anode is preferably set to several hundred Ω / □ or less, more preferably about 5 to 50 Ω / □.

Although the thickness of the anode depends on the material of the electrode substance used, it is generally set to about 5 to 1000 nm, more preferably about 10 to 500 nm.

The hole injecting and transporting layer 3 is a layer containing a compound having a function of facilitating the injection of holes from the anode and a function of transporting the injected holes.

The hole injecting and transporting layer is formed of the compound represented by the general formula (1) according to the present invention and / or another compound having a hole injecting and transporting function (eg, phthalocyanine derivative, triarylmethane derivative, triaryl). At least one of an amine derivative, an oxazole derivative, a hydrazone derivative, a stilbene derivative, a pyrazoline derivative, a polysilane derivative, a polyphenylene vinylene and its derivative, a polythiophene and its derivative, a poly-N-vinylcarbazole derivative, and the like) can be used.

A compound having a hole injecting and transporting function is
They may be used alone or in combination.

Other compounds having a hole injecting and transporting function used in the present invention are preferably triarylamine derivatives, polythiophenes and their derivatives, and poly-N-vinylcarbazole derivatives.

Examples of triarylamine derivatives include:
4,4′-bis [N-phenyl-N- (4 ″ -methylphenyl) amino] biphenyl, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl, 4,4′-bis [N-phenyl-N- (3 ″ -methoxyphenyl) amino] biphenyl, 4,4′-bis [N-phenyl-N- (1 ″ -naphthyl) amino] biphenyl, 3 , 3′-Dimethyl-4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl, 9,10-bis (N, N-diphenyl-4′-aminophenyl) anthracene , 1,1-bis [4'-
[N, N-di (4 ″ -methylphenyl) amino] phenyl] cyclohexane, 9,10-bis [N- (4′-methylphenyl) -N- (4 ″ -n-butylphenyl) amino] Phenanthrene, 3,8-bis (N, N-diphenylamino) -6-phenylphenanthridine, 4-methyl-N, N-bis [4 '', 4 '''-bis[N', N ''
-Di (4-methylphenyl) amino] biphenyl-4-
Il] aniline, N, N'-bis [4- (diphenylamino) phenyl] -N, N'-diphenyl-1,3-diaminobenzene, N, N'-bis [4- (diphenylamino) phenyl]- N, N′-diphenyl-1,4-diaminobenzene, 5,5 ″ -bis [4- (bis [4-methylphenyl] amino) phenyl] -2,2 ′: 5 ′,
2 ″ -terthiophene, 1,3,5-tris (diphenylamino) benzene, 4,4 ′, 4 ″ -tris (N-carbazolyyl) triphenylamine, 4,4 ′, 4 ″-
Tris [N- (3 ′ ″-methylphenyl) -N-phenylamino] triphenylamine, 4,4 ′, 4 ″ -tris [N, N-bis (4 ″ ′-tert-butylbiphenyl-
4 ""-yl) amino] triphenylamine, 1,3
5-tris [N- (4'-diphenylaminophenyl)
Examples include -N-phenylamino] benzene.

When the compound represented by the general formula (1) according to the present invention is used in combination with another compound having a hole injecting and transporting function, the general formula (1) according to the present invention in the hole injecting and transporting layer is used. The ratio of the compound represented by is preferably 0.1
Adjust to about 40% by mass.

The light emitting layer 4 has a function of injecting holes and electrons,
It is a layer containing a compound having a function of transporting them and a function of generating excitons by recombination of holes and electrons.

The light emitting layer is a compound represented by the general formula (1) according to the present invention and / or another compound having a light emitting function, for example, acridone derivative, quinacridone derivative, diketopyrrolopyrrole derivative, polycyclic aromatic compound. , Triarylamine derivatives, organometallic complexes, stilbene derivatives, coumarin derivatives, pyran derivatives, oxazone derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamic acid ester derivatives, poly-N-vinylcarbazole and Derivatives thereof, polythiophene and derivatives thereof, polyphenylene and derivatives thereof, polyfluorene and derivatives thereof, polyphenylene vinylene and derivatives thereof, polybiphenylene vinylene and derivatives thereof, polyterphenylene vinylene And derivatives thereof, poly naphthylene vinylene and its derivatives, can be formed by at least one and polythienylenevinylene and derivatives thereof.

Examples of polycyclic aromatic compounds are rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclohexadiene,
9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9′-anthrylethynyl) benzene, 4,4′-bis (9 ″ -anthrylethynyl) biphenyl, etc. Can be mentioned.

Examples of the triarylamine derivative include:
Examples of the compound having a hole injecting / transporting function include the compounds described above.

Examples of the organometallic complex include tris (8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, zinc salt of 2- (2'-hydroxyphenyl) benzoxazole and 2- (2'-. Hydroxyphenyl) benzothiazole zinc salt, 4-hydroxyacridine zinc salt, 3-hydroxyflavone zinc salt, 5-hydroxyflavone beryllium salt, 5
Examples thereof include aluminum salts of hydroxyflavone.

As the stilbene derivative, 1,1,4
4-tetraphenyl-1,3-butadiene, 4,4'-
Bis (2 ″, 2 ″ -diphenylethenyl) biphenyl,
4,4'-bis [(1 '', 2 '', 2 ''-triphenyl)
Ethenyl] biphenyl, 1,4-bis [2 '-(N, N
-Diphenyl-4 "-aminophenyl) ethenyl] benzene, 4,4'-bis [2"-(N, N-diphenyl-4 "'-aminophenyl) ethenyl] biphenyl and the like can be mentioned.

The coumarin derivatives include coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 10
6, coumarin 138, coumarin 151, coumarin 15
2, coumarin 153, coumarin 307, coumarin 31
1, coumarin 314, coumarin 334, coumarin 33
8, coumarin 343, coumarin 500 and the like.

Preferred examples of pyran derivatives are DCM1,
DCM2 and the like, and a preferable example of the oxazone derivative is Nile red and the like.

In the organic electroluminescent element of the present invention, the light emitting layer preferably contains the compound represented by the general formula (1) according to the present invention.

When the compound represented by the general formula (1) according to the present invention is used in combination with another compound having a light emitting function, the compound represented by the general formula (1) according to the present invention in the light emitting layer is used. The proportion is preferably adjusted to about 0.001 to 99.999% by mass, more preferably about 0.01 to 99.99% by mass, and further preferably about 0.1 to 99.9% by mass.

The electron injection / transport layer 5 is a layer containing a compound having a function of facilitating the injection of electrons from the cathode and a function of transporting the injected electrons.

The electron injecting and transporting layer may be a compound represented by the general formula (1) according to the present invention and / or another compound having an electron injecting and transporting function, for example, tris (8-quinolinolato) aluminum, bis (10-). Benzo [h] quinolinolate) beryllium, beryllium salt of 5-hydroxyflavone, aluminum salt of 5-hydroxyflavone, and the like organometallic complex; 1,3-bis [5 ′-(p-tert
-Butylphenyl) -1,3,4-oxadiazole-
2'-yl] benzene and other oxadiazole derivatives;
[For example, 3- (4'-tert-butylphenyl) -4
-Phenyl-5- (4 ''-biphenyl) -1,2,4-
At least one triazole derivative such as triazole; a triazine derivative, a perylene derivative, a quinoline derivative, a quinoxaline derivative, a diphenylquinone derivative, a nitro-substituted fluorenone derivative, a thiopyrandioxide derivative, or the like can be used.

The compound having an electron injecting and transporting function is
They may be used alone or in combination.

As the other compound having an electron injecting and transporting function used in the present invention, an organoaluminum complex is preferable, and an organoaluminum complex having a substituted or unsubstituted 8-quinolinolato ligand is more preferable.

Examples of the organoaluminum complex having a substituted or unsubstituted 8-quinolinolato ligand include:
Examples thereof include the light-emitting organoaluminum complexes represented by the general formulas (i) to (iii).

(Q) ₃ -Al (i) (wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand) (Q) ₂ -Al-OL (ii) (wherein Q represents Represents a substituted 8-quinolinolato ligand, O
-L is a phenolate ligand, L represents a C6-C24 hydrocarbon group containing a phenyl moiety.) (Q) _2- Al-O-Al- (Q) ₂ (iii) (wherein Q represents a substituted 8-quinolinolate ligand)

Specific examples of the organoaluminum complex having a substituted or unsubstituted 8-quinolinolate ligand include:
For example, tris (8-quinolinolato) aluminum,
Tris (4-methyl-8-quinolinolato) aluminum, tris (5-methyl-8-quinolinolato) aluminum, tris (3,4-dimethyl-8-quinolinolato) aluminum, tris (4,5-dimethyl-8-quinolinolato) Aluminum, tris (4,6-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-8-quinolinolato) (phenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-
Methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate)
(4-Methylphenolate) aluminum, bis (2-
Methyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenolato) aluminum,
Bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum, bis (2-methyl-8)
-Quinolinolate) (2,3-dimethylphenolate)
Aluminum, bis (2-methyl-8-quinolinolato) (2,6-dimethylphenolate) aluminum,
Bis (2-methyl-8-quinolinolato) (3,4-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,5-dimethylphenolate) aluminum, bis (2-methyl-8-) Quinolinolato) (3,5-di-tert-butylphenolate) aluminum, bis (2-methyl-8-quinolinolato)
(2,6-diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-
Triphenylphenolate) aluminum, bis (2-
Methyl-8-quinolinolate) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl-8)
-Quinolinolate) (2,4,5,6-tetramethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinolate) (2-naphtholate ) Aluminum, bis (2,4-dimethyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolato)
(3-Phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenylphenolate Aluminum), bis (2,4-dimethyl-8-quinolinolate) (3,5-di-tert-butylphenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) aluminum-μ-oxo-
Bis (2-methyl-8-quinolinolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2,4-dimethyl-8)
-Quinolinolato) aluminum, bis (2-methyl-)
4-Ethyl-8-quinolinolato) aluminum-μ-
Oxo-bis (2-methyl-4-ethyl-8-quinolinolato) aluminum, bis (2-methyl-4-methoxy-8-quinolinolato) aluminum-μ-oxo-
Bis (2-methyl-4-methoxy-8-quinolinolato) aluminum, bis (2-methyl-5-cyano-8)
-Quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-cyano-8-quinolinolato) aluminum, bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum-μ-oxo-bis (2 -Methyl-5-trifluoromethyl-8-quinolinolato) aluminum and the like.

When the compound represented by the general formula (1) according to the present invention is used in combination with another compound having an electron injecting and transporting function, it is represented by the general formula (1) according to the present invention in the electron injecting and transporting layer. The ratio of the compound to be prepared is preferably 0.1.
Adjust to about 40% by mass.

For the cathode 6, it is preferable to use a metal, an alloy or an electrically conductive compound having a relatively small work function as an electrode substance.

Examples of the electrode material used for the cathode include lithium, lithium-indium alloy, sodium, sodium-potassium alloy, calcium, magnesium, magnesium-silver alloy, magnesium-indium alloy, indium, ruthenium, titanium, manganese, Examples thereof include yttrium, aluminum, aluminum-lithium alloy, aluminum-calcium alloy, aluminum-magnesium alloy, and graphite thin film. These electrode substances may be used alone or in combination.

The cathode may be formed on the electron injecting and transporting layer using any of these electrode materials by a method such as a vapor deposition method, a sputtering method, an ionization vapor deposition method, an ion plating method or a cluster ion beam method. You can

The cathode may have a single-layer structure or a multi-layer structure. The sheet electrical resistance of the cathode is preferably set to several hundreds Ω / □ or less.

The thickness of the cathode depends on the material of the electrode material used, but is generally set to about 5 to 1000 nm, more preferably about 10 to 500 nm.

It is preferable that at least one of the anode and the cathode is transparent or semi-transparent in order to efficiently extract the light emitted from the organic electroluminescent device.
The material of the electrode so that the transmittance of the emitted light is 70% or more,
It is more preferable to set the thickness.

In the organic electroluminescent element of the present invention, a singlet oxygen quencher may be contained in at least one layer.

The singlet oxygen quencher is not particularly limited, and examples thereof include rubrene, nickel complex, diphenylisobenzofuran and the like, and rubrene is particularly preferable.

The layer containing the singlet oxygen quencher is not particularly limited, but is preferably a light emitting layer or a hole injecting / transporting layer, and more preferably a hole injecting / transporting layer. . For example, when the hole injecting and transporting layer contains a singlet quencher, it may be uniformly contained in the hole injecting and transporting layer. It may be contained near the electron injecting and transporting layer (having a function).

The content of the singlet oxygen quencher is 0.01 to 50% by mass, preferably 0.0 to 50% by mass of the total amount constituting the layer (for example, the hole injecting and transporting layer) to be contained.
5 to 30% by mass, more preferably 0.1 to 20% by mass
Is.

The method for forming the hole injecting / transporting layer, the light emitting layer, and the electron injecting / transporting layer is not particularly limited, and examples thereof include a vacuum vapor deposition method, an ionization vapor deposition method, a solution coating method (eg, spin coating method, casting method). Method, dip coating method,
It can be prepared by forming a thin film by a bar coating method, a roll coating method, a Langmuir-Brosette method, an inkjet method, or the like.

When each layer is formed by the vacuum evaporation method,
The conditions for vacuum deposition are not particularly limited, but may be 10
^It may be carried out under a vacuum of about ^-3 Pa, a boat temperature (deposition source temperature) of about 50 to 600 ° C, a substrate temperature of about -50 to 300 ° C, and a deposition rate of about 0.005 to 50 nm / sec. preferable.

In this case, the respective layers such as the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer are continuously formed under vacuum to manufacture an organic electroluminescent device having further excellent characteristics. You can

When each layer such as the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is formed by a plurality of compounds by the vacuum evaporation method, the temperature of each boat containing the compounds is individually controlled, Co-deposition is preferred.

When each layer is formed by the solution coating method,
The component forming each layer or the component and the binder resin are dissolved or dispersed in a solvent to prepare a coating liquid.

Examples of the binder resin that can be used in each of the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer include
Poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethyl acrylate, polymethyl methacrylate, polyether, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide, polyether sulfone, Polymer compounds such as polyaniline and its derivatives, polythiophene and its derivatives, polyphenylene vinylene and its derivatives, polyfluorene and its derivatives, polythienylene vinylene and its derivatives can be mentioned.
The binder resin may be used alone, or
You may use together two or more.

When each layer is formed by the solution coating method,
The component forming each layer or the component and the binder resin are dissolved or dispersed in an appropriate organic solvent and / or water to prepare a coating solution, and a thin film can be formed by various coating methods.

Examples of the organic solvent include hexane, octane, decane, toluene, xylene, ethylbenzene, 1
Hydrocarbon solvents such as methylnaphthalene; acetone,
Ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; halogenated hydrocarbon solvents such as dichloromethane, chloroform, tetrachloromethane, dichloroethane, trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene, chlorotoluene; ethyl acetate, butyl acetate, Ester solvents such as amyl acetate; methanol, propanol, butanol, pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve,
Alcohol solvents such as ethylene glycol; ether solvents such as dibutyl ether, tetrahydrofuran, dioxane, anisole; N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-
Examples include polar solvents such as pyrrolidone, 1-methyl-2-imidazolidinone, and dimethyl sulfoxide.

The method of dispersion is not particularly limited, but for example, a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer or the like can be used to disperse the particles into fine particles.

The concentration of the coating liquid is not particularly limited, and can be set within a concentration range suitable for producing a desired thickness depending on the coating method to be carried out, and generally 0.1 to 50 mass. %, And preferably a solution concentration of about 1 to 30% by mass.

When a binder resin is used, the amount of the binder resin used is not particularly limited, but in general, for each component forming each layer (in the case of forming a one-layer type element, each 5 to 99.
It is set to about 9% by mass, preferably about 10 to 99.9% by mass, and more preferably about 15 to 90% by mass.

The thickness of the hole injecting / transporting layer, the light emitting layer, and the electron injecting / transporting layer is not particularly limited, but it is generally preferably set to about 5 nm to 5 μm.

A protective layer (sealing layer) may be provided on the manufactured element for the purpose of preventing contact with oxygen or moisture.
In addition, the element is, for example, paraffin, liquid paraffin,
It can be enclosed and protected in an inert substance such as silicone oil, fluorocarbon oil, or zeolite-containing fluorocarbon oil.

The material used for the protective layer is, for example,
Examples thereof include organic polymer materials, inorganic materials, and photocurable resins. The materials used for the protective layer may be used alone or in combination. The protective layer may have a monolayer structure or a multilayer structure.

Examples of organic polymer materials include fluorinated resins, epoxy resins, silicone resins, epoxysilicone resins, polystyrene, polyesters, polycarbonates, polyamides, polyimides, polyamideimides, polyparaxylene, polyethylene and polyphenylene oxide. be able to.

Examples of the inorganic material include diamond thin film, amorphous silica, electrically insulating glass, metal oxide, metal nitride, metal carbonide, metal sulfide and the like.

A metal oxide film (for example, an aluminum oxide film) or a metal fluoride film can be provided on the electrode as a protective layer.

Further, for example, an interface layer (intermediate layer) made of, for example, an organic phosphorus compound, polysilane, an aromatic amine derivative or a phthalocyanine derivative can be provided on the surface of the anode.

Further, the electrode, for example, the anode, can be used by treating the surface thereof with, for example, acid, ammonia / hydrogen peroxide or plasma.

The organic electroluminescence device of the present invention is generally used as a DC drive type device, but can also be used as an AC drive type device. Further, the organic electroluminescent element of the present invention may be a passive drive type such as a segment type or a simple matrix drive type, or an active drive type such as a TFT (thin film transistor) type or a MIM (metal-insulator-metal) type. May be The drive voltage is generally about 2 to 30V.

The organic electroluminescent element of the present invention can be used, for example, in a panel type light source, various light emitting elements, various display elements, various markers, various sensors and the like.

[0251]

EXAMPLES The present invention will be described in more detail with reference to production examples and examples, but the present invention is not limited to these examples.

(Production Example 1) Synthesis of Exemplified Compound A-1 A mixture of 2750 g of benzyl chloride and 417 g of sulfur was stirred under reflux for 30 hours, and then the reaction solution was added to 12
It was cooled to 0 ° C. and charged with 1500 ml of toluene. Cool to room temperature, collect the precipitate by filtration, wash with toluene,
2,3,4,5-Tetraphenylthiophene 1080g
Got 2,3,4,5-tetraphenylthiophene 3
A mixture of 8.9 g, acetyl chloride 7.85 g and nitrobenzene 500 g was added at room temperature to anhydrous aluminum chloride 13.33 g and nitrobenzene 50 g.
Was added dropwise over 2 hours. After stirring at the same temperature for 4 hours, the mixture was discharged into ice water and extracted with toluene. After washing the organic layer with water, the solvent was distilled off, and the residue was subjected to silica gel column chromatography (eluent: dichloromethane / n-
Hexane). The solvent was distilled off under reduced pressure to give 2-
22.8 g of (4'-acetylphenyl) -3,4,5-triphenylthiophene was obtained. A mixture of 1.52 g of benzyl chloride and 1.99 g of triethyl phosphite was stirred at 200 ° C. for 1 hour and then cooled to room temperature to obtain diethyl phenylmethylphosphonate.
N, N-dimethylformamide 10g and sodium methoxide 0.59g were charged here, and it cooled at 0 degreeC. After adding a mixture of 4.31 g of 2- (4′-acetylphenyl) -3,4,5-triphenylthiophene and 10 g of N, N-dimethylformamide dropwise, the mixture was stirred at the same temperature for 3 hours. It was discharged into water and extracted with chloroform. After washing the organic layer with water, the solvent was distilled off, and the residue was treated by silica gel column chromatography (eluent: dichloromethane / n-hexane). The solvent was distilled off under reduced pressure to obtain 1.45 g of the compound of Exemplified Compound No. A-1 as a yellow solid.

(Production Examples 2 to 50) According to the formulas shown below,
In Production Example 1, 2- (4′-acetylphenyl)-
Instead of using 3,4,5-triphenylthiophene, various 2,3,4,5-tetraphenylthiophene derivatives (2) were used, and instead of using diethyl phenylmethylphosphonate, various According to the method described in Production Example 1, except that the diethyl phosphonate derivative (3) was used, various 2- (4′-substituted phenyl) -3,
A 4,5-triphenylthiophene derivative (1) was produced. In Table 1, R _{1 to} R ₃ , Z ₁ and Z ₂ in the following formulas and the produced compounds are shown by exemplary compound numbers.

[0254]

[Chemical formula 129]

[0255]

[Table 1]

[0256]

[Table 2]

[0257]

[Table 3]

[0258]

[Table 4]

Production Example 51 Synthesis of Exemplified Compound J-1 2,3,4,5-tetraphenylthiophene 38.9
g, 15.70 g of acetyl chloride and 500 g of nitrobenzene, a solution of 26.66 g of anhydrous aluminum chloride and 100 g of nitrobenzene was added dropwise at room temperature over 2 hours. After stirring at the same temperature for 4 hours, the mixture was discharged into ice water and extracted with toluene. After washing the organic layer with water, the solvent was distilled off, and the residue was treated by silica gel column chromatography (eluent: dichloromethane / n-hexane). The solvent was distilled off under reduced pressure to give 2,5-
27.4 g of bis (4'-acetylphenyl) -3,4-diphenylthiophene was obtained. Benzyl chloride 3.
A mixture of 04 g and triethyl phosphite (3.98 g) was stirred at 200 ° C. for 1 hour and then cooled to room temperature to obtain diethyl phenylmethylphosphonate. N, N-dimethylformamide 10g and sodium methoxide 1.18g were charged here, and it cooled at 0 degreeC.
After adding a mixture of 4.73 g of 2,5-bis (4′-acetylphenyl) -3,4-diphenylthiophene and 10 g of N, N-dimethylformamide dropwise, the mixture was stirred at the same temperature for 3 hours. It was discharged into water and extracted with chloroform. After washing the organic layer with water, the solvent was distilled off, and the residue was treated by silica gel column chromatography (eluent: dichloromethane / n-hexane). The solvent was distilled off under reduced pressure to obtain 1.53 g of the compound of Exemplified Compound No. J-1 as a yellow solid.

(Preparation Examples 52 to 100) In accordance with the formulas shown below, instead of using 2,5-bis (4′-acetylphenyl) -3,4-diphenylthiophene in Preparation Example 51, various 2,2 Production Example except that the 3,4,5-tetraphenylthiophene derivative (4) was used, and various diethyl phosphonate derivatives (3) and (5) were used in place of diethyl phenylmethylphosphonate derivative According to the method described in 51, various 2,5-
A bis (4′-substituted phenyl) -3,4-diphenylthiophene derivative (1) was produced. In Table 2, R _{1 to} R ₆ , Z ₁ and Z ₂ in the following formulas and the produced compounds are shown by exemplary compound numbers.

[0261]

[Chemical 130]

[0262]

[Table 5]

[0263]

[Table 6]

[0264]

[Table 7]

[0265]

[Table 8]

[0266]

[Table 9]

[0267]

[Table 10]

Example 1 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on the substrate holder of the vapor deposition apparatus, and then the vapor deposition tank was moved to 4
The pressure was reduced to × 10 ^-3 Pa.

First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec for 75 n.
It was vapor-deposited to a thickness of m to form a hole injecting and transporting layer. Then bis (2-methyl-8-quinolinolate) (4
-Phenylphenolato) aluminum and the compound of Exemplified Compound No. A-1 from different vapor deposition sources at a vapor deposition rate of 0.
Co-deposition at a thickness of 2 nm / sec and a thickness of 50 nm (mass ratio 10
0: 0.5) to obtain a light emitting layer.

Next, tris (8-quinolinolato) aluminum was vapor-deposited at a vapor deposition rate of 0.2 nm / sec. To a thickness of 50 nm to form an electron injecting and transporting layer.

Further, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (mass ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 54 mA / c.
An electric current of m ² flowed. Blue-green light emission with a luminance of 2420 cd / m ² was confirmed.

(Examples 2 to 100) In Example 1,
In forming the light emitting layer, an organic electroluminescent device was produced by the method described in Example 1 except that each exemplified compound shown in Table 3 was used instead of the compound of exemplified compound A-1. Each element is exposed to 12
When a DC voltage of V was applied, blue to blue-green light emission was confirmed. Further, its characteristics were examined, and the results are shown in Table 3.

COMPARATIVE EXAMPLE 1 In Example 1, bis (2-methyl-8-quinolinolato) (4-) was used in the formation of the light emitting layer without using the compound of Exemplified Compound No. A-1.
Phenylphenolate) aluminum only 5
Example 1 except that the light emitting layer was formed by vapor deposition to a thickness of 0 nm.
An organic electroluminescence device was produced by the method described in 1. When a DC voltage of 12 V was applied to this element in a dry atmosphere, blue light emission was confirmed. Further, its characteristics were examined, and the results are shown in Table 3.

Comparative Example 2 Example 2 was repeated except that N-methyl-2-methoxyacridone was used instead of the compound of Exemplified Compound No. A-1 in the formation of the light emitting layer in Example 1. An organic electroluminescence device was produced by the method described in 1. Apply 12V to this device in a dry atmosphere.
When a DC voltage of 3 was applied, blue light emission was confirmed. Further, its characteristics were examined, and the results are shown in Table 3.

[0276]

[Table 11]

[0277]

[Table 12]

[0278]

[Table 13]

Example 101 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa.

First, on the ITO transparent electrode, 4, 4 ',
The deposition rate of 4 ″ -tris [N- (3 ′ ″-methylphenyl) -N-phenylamino] triphenylamine was 0.1 n.
It was vapor-deposited at a thickness of 50 nm at m / sec to form a first hole injecting and transporting layer.

Then, 4,4'-bis [N-phenyl-
N- (1 ″ -naphthyl) amino] biphenyl and the compound of Exemplified Compound No. A-1 were co-evaporated from different vapor deposition sources at a vapor deposition rate of 0.2 nm / sec to a thickness of 20 nm (mass ratio 1
00: 5.0) to form a light emitting layer which also serves as the second hole injecting and transporting layer.

Then, tris (8-quinolinolato) aluminum was vapor-deposited thereon at a vapor deposition rate of 0.2 nm / sec. To a thickness of 50 nm to form an electron injecting and transporting layer.

Further, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec. To a thickness of 200 nm (mass ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank.

When a direct current voltage of 15 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 59 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2580 cd / m ² was confirmed.

Examples 102 to 153 Example 101 is the same as Example 101 except that each Exemplified compound shown in Table 4 was used instead of the compound of Exemplified compound A-1 in the formation of the light emitting layer. An organic electroluminescence device was produced by the method described in 1. When a DC voltage of 15 V was applied to each element in a dry atmosphere, blue to blue-green light emission was confirmed. Further, its characteristics were examined, and the results are shown in Table 4.

[0286]

[Table 14]

[0287]

[Table 15]

Example 154 A glass substrate having a 200 nm thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on an ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. It was used as a hole injecting and transporting layer.

Then, on top of that, bis (2-methyl-8)
-Quinolinolate) (4-phenylphenolate) aluminum and the compound of Exemplified Compound No. A-2 were co-evaporated from different vapor deposition sources at a vapor deposition rate of 0.2 nm / sec to a thickness of 50 nm (mass ratio 100: 2.0. ), And it was set as the light emitting layer.

Next, 1,3-bis [5 '-(4''-tert
-Butylphenyl) -1 ', 3', 4'-oxadiazol-2'-yl] benzene, vapor deposition rate 0.2 nm /
It was vapor-deposited to have a thickness of 50 nm for sec to form an electron injecting and transporting layer.

Further, magnesium and silver were co-deposited at a vapor deposition rate of 0.2 nm / sec. To a thickness of 200 nm (mass ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 58 mA / cm 2.
^Two currents flowed. Blue-green light emission with a luminance of 2680 cd / m ² was confirmed.

Example 155 In Example 154, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified compound A-2 in forming the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and the compound of Exemplified Compound No. B-1,
Co-deposited to a thickness of 50 nm (mass ratio 100: 4.0),
An organic electroluminescent device was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 59 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2970 cd / m ² was confirmed.

Example 156 In Example 154, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in forming the light emitting layer. (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and a compound of Exemplified Compound No. C-7 were used to co-evaporate to a thickness of 50 nm (mass ratio 100 : 3.0), and an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 56 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2780 cd / m ² was confirmed.

Example 157 In Example 154, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 in forming the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and a compound of Exemplified Compound No. C-9,
Co-deposited to a thickness of 50 nm (mass ratio 100: 4.0),
An organic electroluminescent device was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescence device in a dry atmosphere, it was 58 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2790 cd / m ² was confirmed.

Example 158 In Example 154, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in the formation of the light emitting layer. (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. D-18 were used to co-evaporate to a thickness of 50 nm (mass ratio 100 : 3.0), and an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 58 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2890 cd / m ² was confirmed.

Example 159 In Example 154, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 in forming the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and a compound of Exemplified Compound No. F-1,
Co-deposited to a thickness of 50 nm (mass ratio 100: 4.0),
An organic electroluminescent device was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescence device in a dry atmosphere, it was 56 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2720 cd / m ² was confirmed.

Example 160 In Example 154, a bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and a compound of Exemplified Compound A-2 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in forming the light emitting layer. (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and a compound of Exemplified Compound No. G-19 were used to co-evaporate to a thickness of 50 nm (mass ratio 100 : 3.0), and an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 57 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2680 cd / m ² was confirmed.

Example 161 In Example 154, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 in the formation of the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and the compound of Exemplified Compound No. H-18, coevaporation was performed to a thickness of 50 nm (mass ratio 100: 4.0).
Then, an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 56 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2770 cd / m ² was confirmed.

Example 162 In Example 154, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in the formation of the light emitting layer. (2-Methyl-8-quinolinolato) aluminum- [mu] -oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. I-1 were used to co-evaporate to a thickness of 50 nm (mass ratio 100 : 3.0), and an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescence device in a dry atmosphere, it was 58 mA / cm 2.
^Two currents flowed. Blue-green light emission with a luminance of 2860 cd / m ² was confirmed.

Example 163 In Example 154, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 in forming the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and a compound of Exemplified Compound No. J-11, co-evaporation to a thickness of 50 nm (mass ratio 100: 4.0).
Then, an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was found to be 56 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2670 cd / m ² was confirmed.

Example 164 In Example 154, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in the formation of the light emitting layer. (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and a compound of Exemplified Compound No. K-17 were used to co-evaporate to a thickness of 50 nm (mass ratio 100 : 3.0), and an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 57 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2720 cd / m ² was confirmed.

Example 165 In Example 154, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 in forming the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and a compound of Exemplified Compound No. L-18, co-evaporation was performed to a thickness of 50 nm (mass ratio 100: 4.0).
Then, an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 57 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2700 cd / m ² was confirmed.

Example 166 In Example 154, a bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and a compound of Exemplified Compound A-2 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in forming the light emitting layer. (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and a compound of Exemplified Compound No. M-1 were used to co-evaporate to a thickness of 50 nm (mass ratio 100 : 3.0), and an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent element in a dry atmosphere, it was 57 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2810 cd / m ² was confirmed.

Example 167 In Example 154, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 in forming the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and a compound of Exemplified Compound No. N-13, co-evaporation to a thickness of 50 nm (mass ratio 100: 4.0).
Then, an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 57 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2760 cd / m ² was confirmed.

Example 168 In Example 154, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 were used instead of the compound of Example 154 in the formation of the light emitting layer. (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. O-1 were used to co-evaporate to a thickness of 50 nm (mass ratio 100 : 3.0), and an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 56 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2,620 cd / m ² was confirmed.

Example 169 In Example 154, tris instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 in forming the light emitting layer. Using (8-quinolinolato) aluminum and a compound of Exemplified Compound No. P-19, co-evaporation was performed to a thickness of 50 nm (mass ratio 100: 4.0).
Then, an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 57 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2830 cd / m ² was confirmed.

Example 170 In Example 154, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in the formation of the light emitting layer. (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and a compound of Exemplified Compound No. Q-9 were used to co-evaporate to a thickness of 50 nm (mass ratio 100 : 3.0), and an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 56 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2680 cd / m ² was confirmed.

Example 171 In Example 154, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-2 were used in Example 154 instead of the compound of Example 154. (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. R-1 were used to co-evaporate to a thickness of 50 nm (mass ratio 100 : 3.0), and an organic electroluminescent element was produced by the method described in Example 154 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescence device in a dry atmosphere, it was 58 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2880 cd / m ² was confirmed.

Example 172 A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was ultrasonically cleaned with a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa.

First, 4,4′-bis [N-phenyl-N- (1 ″ -naphthyl) amino] biphenyl was vapor-deposited on an ITO transparent electrode at a vapor deposition rate of 0.2 nm / sec to a thickness of 75 nm. The hole injecting and transporting layer.

Then, in addition thereto, Exemplified Compound No. A-1
And 1,4-bis [2 ′-(N, N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene from different vapor deposition sources at a deposition rate of 0.2 nm / sec and a thickness of 50 nm. It vapor-deposited (mass ratio 100: 5.0) and it was set as the light emitting layer.

Next, tris (8-quinolinolato) aluminum was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injecting and transporting layer.

Further, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (mass ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 61 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 3280 cd / m ² was confirmed.

Example 173 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. B-17 and 4,4′-bis [2 ″-(N, N-diphenyl-4 ″) Using'-aminophenyl) ethenyl] biphenyl, co-evaporation to a thickness of 50 nm (mass ratio 100: 4.
0) Then, an organic electroluminescent element was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 59 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2980 cd / m ² was confirmed.

Example 174 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. C-1 and 1,4-bis [2 ′-(N, N-diphenyl-
4 ″ -aminophenyl) ethenyl] benzene,
Co-deposited to a thickness of 50 nm (mass ratio 100: 7.0),
An organic electroluminescent element was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 61 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 3160 cd / m ² was confirmed.

Example 175 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. E-1 and 4,4′-bis [2 ″-(N, N-diphenyl-4 ″) Using'-aminophenyl) ethenyl] biphenyl, co-evaporation to a thickness of 50 nm (mass ratio 100: 5.
0) Then, an organic electroluminescent element was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescence device in a dry atmosphere, it was 58 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 3080 cd / m ² was confirmed.

Example 176 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. F-9 and 1,4-bis [2 ′-(N, N-diphenyl-
4 ″ -aminophenyl) ethenyl] benzene,
Co-deposited to a thickness of 50 nm (mass ratio 100: 3.0),
An organic electroluminescent element was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescence device in a dry atmosphere, it was 58 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2960 cd / m ² was confirmed.

Example 177 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. I-9 and 4,4′-bis [2 ″-(N, N-diphenyl-4 ″) Using'-aminophenyl) ethenyl] biphenyl, co-evaporation to a thickness of 50 nm (mass ratio 100: 5.
0) Then, an organic electroluminescent element was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescence device in a dry atmosphere, it was 58 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2880 cd / m ² was confirmed.

Example 178 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. K-9 and 1,4-bis [2 ′-(N, N-diphenyl-
4 ″ -aminophenyl) ethenyl] benzene,
Co-deposited to a thickness of 50 nm (mass ratio 100: 6.0),
An organic electroluminescent element was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescence device in a dry atmosphere, it was 60 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 3110 cd / m ² was confirmed.

Example 179 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. L-19 and 4,4′-bis [2 ″-(N, N-diphenyl-4 ″) Using'-aminophenyl) ethenyl] biphenyl, co-evaporation to a thickness of 50 nm (mass ratio 100: 5.
0) Then, an organic electroluminescent element was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescence device in a dry atmosphere, it was 57 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2980 cd / m ² was confirmed.

Example 180 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. N-8 and 1,4-bis [2 ′-(N, N-diphenyl-
4 ″ -aminophenyl) ethenyl] benzene,
Co-deposition to a thickness of 50 nm (mass ratio 100: 10.0)
Then, an organic electroluminescent element was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 58 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 3120 cd / m ² was confirmed.

Example 181 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. O-21 and 4,4′-bis [2 ″-(N, N-diphenyl-4 ″) Using'-aminophenyl) ethenyl] biphenyl, co-evaporation to a thickness of 50 nm (mass ratio 100: 5.
0) Then, an organic electroluminescent element was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescence device in a dry atmosphere, it was 57 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2820 cd / m ² was confirmed.

Example 182 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. R-1 and 1,4-bis [2 ′-(N, N-diphenyl-
4 ″ -aminophenyl) ethenyl] benzene,
Co-deposited to a thickness of 50 nm (mass ratio 100: 6.0),
An organic electroluminescent element was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescence device in a dry atmosphere, it was 60 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 3220 cd / m ² was confirmed.

Example 183 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. E-1 and Exemplified Compound No. C-14 were co-deposited to a thickness of 50 nm (mass ratio 100 : 5.0), and an organic electroluminescent device was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 59 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 3130 cd / m ² was confirmed.

Example 184 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. N-1 and Exemplified Compound No. C-7 were co-deposited to a thickness of 50 nm (mass ratio 100 : 7.0), and an organic electroluminescent device was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescence device in a dry atmosphere, it was 58 mA / cm.
^Two currents flowed. Blue-green light emission with a brightness of 2920 cd / m ² was confirmed.

Example 185 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. N-8 and Exemplified Compound No. L-7 were co-deposited to a thickness of 50 nm (mass ratio 100 : 4.0), and an organic electroluminescent device was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 59 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 3130 cd / m ² was confirmed.

Example 186 In Example 172, the compound of Exemplified Compound No. A-1 and 1,4-bis [2 ′-(N,
Instead of using N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene, the compound of Exemplified Compound No. N-1 and Exemplified Compound No. L-15 were co-deposited to a thickness of 50 nm (mass ratio 100 : 7.0), and an organic electroluminescent device was produced by the method described in Example 172 except that the light emitting layer was used.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 59 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 3220 cd / m ² was confirmed.

Example 187 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned with a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas and further UV / ozone washed.

Next, on the ITO transparent electrode, poly-N-vinylcarbazole (mass average molecular weight 150,000), compound of exemplary compound No. A-8, coumarin 6 ["3-
(2'-benzothiazolyl) -7-diethylaminocoumarin "(green luminescent component)], and DCM-1 [" 4
-(Dicyanomethylene) -2-methyl-6- (4'-dimethylaminostyryl) -4H-pyran "(orange luminescent component)] in a mass ratio of 100: 5: 3: 2, respectively.
Using a 3% by mass dichloroethane solution contained at a ratio of 1, a light emitting layer having a thickness of 400 nm was formed by a dip coating method.

Next, a glass substrate having this light emitting layer was prepared.
After fixing to the substrate holder of the vapor deposition equipment, the vapor deposition tank is set to 4 x 1
The pressure was reduced to 0 ⁻⁴ Pa.

Furthermore, 3- (4'-tert.
-Butylphenyl) -4-phenyl-5- (4 ''-phenylphenyl) -1,2,4-triazole was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 20 nm, and then further deposited thereon. Tris (8-quinolinolato) aluminum was vapor-deposited to a thickness of 30 nm at a vapor deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer.

Further, magnesium and silver were co-evaporated at a vapor deposition rate of 0.2 nm / sec. To a thickness of 200 nm (mass ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 74 mA / cm.
^Two currents flowed. White light emission with a luminance of 1480 cd / m ² was confirmed.

Examples 188 to 196 By the method described in Example 187, except that in Example 187, instead of using the compound of Exemplified Compound No. A-8, each exemplified compound shown in Table 5 was used. An organic electroluminescent device was produced. When a direct current voltage of 12 V was applied to each element in a dry atmosphere, white light emission was observed. Further, its characteristics were examined, and the results are shown in Table 5.

[0367]

[Table 16]

Example 197 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. First, a compound of Exemplified Compound No. A-13 was vapor-deposited on an ITO transparent electrode at a vapor deposition rate of 0.2 nm / sec to a thickness of 75 nm to form a hole injecting and transporting layer.

Then, tris (8-quinolinolato) aluminum was deposited thereon at a deposition rate of 0.2 nm / sec for 5 minutes.
It was vapor-deposited to a thickness of 0 nm to form a light emitting layer which also serves as an electron injecting and transporting layer.

Further, magnesium and silver were co-deposited at a vapor deposition rate of 0.2 nm / sec. To a thickness of 200 nm (mass ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank.

When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 57 mA / cm.
^Two currents flowed. Green light emission with a brightness of 2960 cd / m ² was confirmed.

Examples 198 to 215 In Examples 197, except that each exemplary compound shown in Table 6 was used in place of the compound of Exemplary Compound No. A-13 in the formation of the hole injecting and transporting layer. An organic electroluminescent device was produced by the method described in Example 197. When a direct current voltage of 12 V was applied to each element in a dry atmosphere, white light emission was observed. Further, its characteristics were examined, and the results are shown in Table 6.

[0373]

[Table 17]

[0374]

According to the present invention, it is possible to provide an organic electroluminescent device having excellent emission brightness. Furthermore, it has become possible to provide a compound suitable for the light emitting device.

[Brief description of drawings]

FIG. 1 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 2 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 3 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 4 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 5 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 6 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 7 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 8 is a schematic structural diagram of an example of an organic electroluminescent device.

[Explanation of symbols]

1: Substrate 2: Anode 3: Hole injecting and transporting layer 4: Emitting layer 4 ': Emitting layer (layer in which light emitting component and hole injecting and transporting component are mixed) 4'': Light emitting layer (light emitting component and electron injecting and transporting component) Mixed layer) 4 ″ ′: light emitting layer (layer in which light emitting component, hole injecting / transporting component and electron injecting / transporting component are mixed) 5: electron injecting / transporting layer 6: cathode 7: power supply

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) C09K 11/06 655 C09K 11/06 655 690 690 H05B 33/14 H05B 33/14 B 33/22 33/22 BD (72) Inventor Yoshimitsu Tanabe Mitsui Chemicals Co., Ltd. 580-32 Nagaura, Sodegaura City, Chiba Prefecture (72) Inventor Yoshiyuki Toya 580-32 Nagaura, Sodegaura City, Chiba Mitsui Chemicals Co., Ltd. (72) Inventor Masakatsu Nakatsuka 580-32 Nagaura, Sodegaura-shi, Chiba Mitsui Chemicals Co., Ltd. F-term within the company (reference) 3K007 AB02 AB03 DB03 4C023 BA07 DA07

Claims (8)

[Claims] 1. An organic electroluminescent device comprising a pair of electrodes and at least one layer containing at least one compound represented by the general formula (1) sandwiched between the pair of electrodes. [Chemical 1] [In the formula, R _{1 to} R ₃ are each independently a hydrogen atom, a straight chain,
Represents a branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, Y represents a hydrogen atom or a group represented by the general formula (a), and (In the formula, R _{4 to} R ₆ are each independently a hydrogen atom, a straight chain,
It represents a branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group. ) Z ₁ and Z ₂ are a hydrogen atom, a halogen atom, a straight chain,
It represents a branched or cyclic alkyl group, a straight chain, branched or cyclic alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group. ] 2. The organic electroluminescent element according to claim 1, wherein the layer containing the compound represented by the general formula (1) further contains a light emitting organometallic complex. 3. The organic electroluminescent element according to claim 1, wherein the layer containing the compound represented by the general formula (1) further contains a triarylamine derivative. 4. The organic electroluminescent element according to claim 1, wherein the layer containing the compound represented by the general formula (1) is a light emitting layer. 5. The organic electroluminescent element according to claim 1, wherein the layer containing the compound represented by the general formula (1) is a hole injecting and transporting layer. 6. The organic electroluminescence device according to claim 1, further comprising a hole injecting and transporting layer between the pair of electrodes. 7. The organic electroluminescent device according to claim 1, further comprising an electron injecting and transporting layer between the pair of electrodes. 8. A thiophene compound represented by the following general formula (1a): [Chemical 3] (In the formula, R _{1 to} R ₆ are each independently a hydrogen atom, a straight chain,
Represents a branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, wherein Z ₁ and Z ₂ are a hydrogen atom, a halogen atom, a straight chain, a branched or cyclic alkyl group, a straight chain Represents a branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted amino group. )