JP2003092187A - Organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent element having an excellent luminous efficiency, a long light emitting life, and excellent durability. SOLUTION: The organic electroluminescent element having at least one layer comprising at least one kind of compounds represented by the general formula (1), the layer being sandwiched between a pair of electrodes. (in the formula, Ar1 to Ar4 independently represent a substituted or unsubstituted aryl group, a pair of Ar1 and Ar2 and a pair of Ar3 and Ar4 may form a nitrogen- containing heterocycle together with a bonding nitrogen atom, and m represents 0 or 1).

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an organic electroluminescent 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 ,
913 (1987)]. The organic electroluminescent device has a structure in which a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode,
An element that emits light by using light emitted when electrons and holes (holes) are injected into the thin film and recombined to generate excitons (excitons), and the excitons are deactivated. is there. The organic electroluminescent device is capable of emitting light at a direct current low voltage of about several V to several tens of V, and by selecting the type of fluorescent organic compound, various colors (for example, red, blue, green) can be obtained. ) Is possible. Organic electroluminescent devices having such characteristics include various light emitting devices,
It is expected to be applied to display devices. However,
Generally, organic electroluminescent devices have drawbacks such as poor stability and durability. Furthermore, from the viewpoint of low energy consumption, further improvement in luminous efficiency is required.

It has been proposed to use 4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] biphenyl as a hole injecting and transporting material [Jpn.
J. Appl. Phys., 27 , L269 (1988)]. However, an organic electroluminescent device using this compound as a hole injecting and transporting material has drawbacks such as poor stability and durability.
Further, as the hole injecting and transporting material, for example, 2- [4′-
[N-phenyl-N- (4 "-methylphenyl) amino] phenyl] -3,4,5-triphenylthiophene, 2,5-bis [4 '-[N-phenyl-N- (3"
It has been proposed to use -methylphenyl) amino] phenyl] -3,4-diphenylthiophene (JP-A-10-125468). Organic electroluminescent devices using these amine compounds of thiophene derivatives, for example, as hole injecting and transporting materials have improved stability and durability, but further improvement in luminous efficiency is required. At present, a further improved organic electroluminescent device is desired.

[0004]

An object of the present invention is to provide an organic electroluminescent device having improved luminous efficiency.

[0005]

Means for Solving the Problems The present inventors have completed the present invention as a result of extensive studies on organic electroluminescent elements. That is, the present invention is an organic electroluminescent device having at least one layer containing at least one compound represented by the following general formula (1) sandwiched between a pair of electrodes, represented by the general formula (1). An organic electroluminescent device as described above, wherein the layer containing the compound is a hole injecting and transporting layer, and an organic electroluminescent device as described above, wherein the layer containing the compound represented by the general formula (1) is a light emitting layer. Further, a light emitting layer is further provided between the electrodes of
The organic electroluminescent element according to any one of the above, and the organic electroluminescent element according to any one of the above 1 to 4, which further has an electron injecting and transporting layer between a pair of electrodes.

[0006]

[Chemical 2] (In the formula, Ar _{1 to} Ar ₄ each independently represent a substituted or unsubstituted aryl, and further, Ar ₁ and Ar ₂ and A
r ₃ and Ar ₄ represent that a nitrogen-containing heterocycle may be formed together with the bonded nitrogen atom, and m represents 0 or 1.)

[0007]

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

[0008]

[Chemical 3] (In the formula, Ar _{1 to} Ar ₄ each independently represent a substituted or unsubstituted aryl, and further, Ar ₁ and Ar ₂ and A
r ₃ and Ar ₄ represent that a nitrogen-containing heterocycle may be formed together with the bonded nitrogen atom, and m represents 0 or 1.)

In the general formula (1), Ar _{1 to} Ar ₄ each independently represent a substituted or unsubstituted aryl group.
The aryl group is, for example, a carbocyclic aromatic group such as a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group or a fluorenyl group, for example, a heterocyclic aromatic group such as a furyl group, a thienyl group or a pyridyl group. Represents

Ar _{1 to} Ar ₄ are preferably unsubstituted or as a substituent, for example, a total number of carbon atoms which may be mono- or polysubstituted with a halogen atom, an alkyl group, an alkoxy group, or an aryl group. It is a 6-26 carbocyclic aromatic group or a heterocyclic aromatic group having a total carbon number of 3 to 26, and more preferably an unsubstituted or substituted group, for example, a halogen atom or a carbon number of 1 to 14 Alkyl group, C1-14 alkoxy group, or C6
-10 is a carbocyclic aromatic group having 6 to 20 carbon atoms or a heterocyclic aromatic group having 3 to 20 carbon atoms, which may be mono- or poly-substituted with an aryl group. Unsubstituted or as a substituent, for example, mono- or polysubstituted with a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms. Is a carbocyclic aromatic group having 6 to 16 total carbon atoms.

Specific examples of the substituted or unsubstituted aryl group in Ar _{1 to} Ar ₄ include, for example, a 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, 2-neopentylphenyl group Group, 4-te
rt-pentylphenyl group, 4-n-hexylphenyl group, 4- (2'-ethylbutyl) phenyl group, 4-n-
Heptylphenyl group, 4-n-octylphenyl group, 4
-(2'-ethylhexyl) phenyl group, 4-tert-octylphenyl group, 4-n-decylphenyl group, 4-n
-Dodecylphenyl group, 4-n-tetradecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4- (4'-methylcyclohexyl) phenyl group, 4- (4'-tert-butylcyclohexyl)
Phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group,

2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,
5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,4-diethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group,
3,4,5-trimethylphenyl group, 2,6-diethylphenyl group, 2,5-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-propoxyphenyl group, 3-n -Propoxyphenyl group, 4-isopropoxyphenyl group, 2-
Isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-
Isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 4-neopentyloxyphenyl group, 2
-Neopentyloxyphenyl group, 4-n-hexyloxyphenyl group, 2- (2'-ethylbutyl) oxyphenyl group, 4-n-octyloxyphenyl group, 4-n
-Decyloxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-tetradecyloxyphenyl group, 4
-Cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group,

2-methyl-4-methoxyphenyl group, 2
-Methyl-5-methoxyphenyl group, 3-methyl-4-
Methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 3-ethyl-5-methoxyphenyl group, 2-methoxy-4-methylphenyl group, 3-methoxy-4-methylphenyl group, 2,4-dimethoxyphenyl Base, 2, 5
-Dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 3,5
-Di-n-butoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2-methoxy-6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl 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, 2,3
-Difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, 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, 2-methyl-
3-chlorophenyl group, 2-methyl-4-chlorophenyl group, 3-chloro-4-methylphenyl group, 3-methyl-4-chlorophenyl group, 2-chloro-4,6-dimethylphenyl group, 2-methoxy-4 -Fluorophenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-4-ethoxyphenyl group, 2-fluoro-6-methoxyphenyl group, 3-fluoro-4-ethoxyphenyl group, 3-chloro-4 -Methoxyphenyl group, 2-methoxy-5-chlorophenyl group, 3-methoxy-6-chlorophenyl group, 5-chloro-2,4-dimethoxyphenyl 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'-n-dodecylphenyl) phenyl group, 3-
(4'-methylphenyl) phenyl group, 2- (4'-methylphenyl) phenyl group, 2- (4'-ethylphenyl) phenyl group, 4- (4'-methoxyphenyl) phenyl group, 4- (3 '-Methoxyphenyl) phenyl group,
4- (4'-ethoxyphenyl) phenyl group, 4-
(4'-n-butoxyphenyl) phenyl group, 4-
(4'-n-hexyloxyphenyl) phenyl group, 4
A-(4'-n-octyloxyphenyl) phenyl group,
4- (4'-n-decyloxyphenyl) phenyl group,
3- (4'-methoxyphenyl) phenyl group, 2-
(4'-methoxyphenyl) phenyl group, 2- (2'-
Methoxyphenyl) phenyl group, 4- (4'-fluorophenyl) phenyl group, 4- (4'-chlorophenyl)
Phenyl group, 4- (3'-fluorophenyl) phenyl group, 4- (2'-fluorophenyl) phenyl group, 2-
(4'-Fluorophenyl) phenyl group, 3-methyl-
4-phenylphenyl group, 4-methyl-3-phenylphenyl group, 4-methyl-2-phenylphenyl group, 5-
Methyl-2-phenylphenyl group, 6-methyl-3-phenylphenyl group, 2-ethyl-4-phenylphenyl group, 4-ethyl-2-phenylphenyl group, 2-methoxy-4-phenylphenyl group, 3- Methoxy-4-phenylphenyl group, 4-methoxy-2-phenylphenyl group, 4-fluoro-2-phenylphenyl group, 3-fluoro-4-phenylphenyl group, 3-fluoro-2-phenylphenyl group, 5- Fluoro-2-phenylphenyl group, 2,4-diphenylphenyl group, 2-phenyl-
4- (4'-methylphenyl) phenyl group, 3,4-diphenylphenyl group, 3,5-diphenylphenyl group,

1-naphthyl group, 2-naphthyl group, 2-methyl-1-naphthyl group, 4-methyl-1-naphthyl group,
4-ethyl-1-naphthyl group, 4-n-butyl-1-naphthyl group, 4-n-hexyl-1-naphthyl group, 4-n
-Decyl-1-naphthyl group, 5-methyl-1-naphthyl group, 1-methyl-2-naphthyl group, 6-methyl-2-naphthyl group, 6-ethyl-2-naphthyl group, 6-n-butyl- 2-naphthyl group, 6-n-octyl-2-naphthyl group, 2-methoxy-1-naphthyl group, 4-methoxy-1
-Naphthyl group, 4-n-butoxy-1-naphthyl group, 5
-Ethoxy-1-naphthyl group, 6-methoxy-2-naphthyl group, 6-ethoxy-2-naphthyl group, 6-n-butoxy-2-naphthyl group, 6-n-hexyloxy-2-
Naphthyl group, 7-methoxy-2-naphthyl group, 7-n-
Butoxy-2-naphthyl group, 4-phenyl-1-naphthyl group, 6-phenyl-2-naphthyl group, 4-fluoro-
1-naphthyl group, 2-fluoro-1-naphthyl group, 4-
Chloro-1-naphthyl group, 4-chloro-2-naphthyl group, 6-chloro-2-naphthyl group, 6-bromo-2-naphthyl group, 2,4-dichloro-1-naphthyl group, 1,6
-Dichloro-2-naphthyl group,

1-anthryl group, 2-anthryl group, 9
-Anthryl group, 6-methyl-2-anthryl group, 6-
tert-butyl-2-anthryl group, 10-methyl-9-
Anthryl group, 10-ethyl-9-anthryl group, 10
-N-hexyl-9-anthryl group, 5-phenyl-1
-Anthryl group, 6-phenyl-2-anthryl group, 1
0-phenyl-9-anthryl group, 10- (4′-methylphenyl) -9-anthryl group,

1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 9-phenanthryl group,
3-methyl-1-phenanthryl group, 5-methyl-1-
Phenanthryl group, 6-tert-butyl-1-phenanthryl group, 6-methyl-2-phenanthryl group, 1-methyl-9-phenanthryl group, 8-methyl-9-phenanthryl group, 2-methyl-9-phenanthryl group, 2-ethyl-9-phenanthryl group, 3-methyl-9-phenanthryl group, 3-n-butyl-9-phenanthryl group,
6-methyl-9-phenanthryl group, 10-methyl-9
-Phenanthryl group, 2,3-dimethyl-9-phenanthryl group, 3,6-dimethyl-9-phenanthryl group,
1-methoxy-9-phenanthryl group, 2-methoxy-
9-phenanthryl group, 3-methoxy-9-phenanthryl group, 10-methoxy-9-phenanthryl group, 3-
Methoxy-7-methyl-9-phenanthryl group, 3-phenyl-1-phenanthryl group, 6-phenyl-1-phenanthryl group, 2- (4′-methylphenyl) -9-
Phenanthryl group, 3-phenyl-9-phenanthryl group, 1-chloro-9-phenanthryl group, 3-fluoro-9-phenanthryl group, 7-chloro-9-phenanthryl group,

2-fluorenyl group, 9-methyl-2-fluorenyl group, 9-ethyl-2-fluorenyl group, 9-
Isopropyl-2-fluorenyl group, 9-n-octyl-2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-diethyl-2-fluorenyl group,
9,9-di-n-propyl-2-fluorenyl group, 9,
9-di-n-butyl-2-fluorenyl group, 9,9-di-n-hexyl-2-fluorenyl group, 7-methyl-
9,9-Dimethyl-2-fluorenyl group, 7-tert-butyl-9,9-dimethyl-2-fluorenyl group, 9-phenyl-2-fluorenyl group, 7-phenyl-9,9-
Dimethyl-2-fluorenyl group, 7- (4'-methylphenyl) -9,9-dimethyl-2-fluorenyl group, 7
-(4'-tert-butylphenyl) -9,9-dimethyl-2-fluorenyl group, 7-ethoxy-9,9-dimethyl-2-fluorenyl group, 7-chloro-9,9-dimethyl-2-fluorenyl Group, 9,9-diphenyl-2-fluorenyl group, 9-phenyl-9-methyl-2-fluorenyl group, 9- (4′-methylphenyl) -9-n-hexyl-2-fluorenyl group,

4-quinolyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-ethyl-4-pyridyl group, 4-phenyl-2-pyridyl group, 2-phenyl-4
-Pyridyl group, 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 2-thiazolyl group, 2-benzoxazolyl group, 2-benzothiazolyl group, 2-benzimidazolyl group, etc. However, the present invention is not limited to these.

In the compound represented by the general formula (1),
Further, Ar ₁ and Ar ₂ and Ar ₃ and Ar ₄ may form a nitrogen-containing heterocycle together with the bonded nitrogen atom,
Preferably, -NAr ₁ Ar ₂ and -NAr ₃ Ar ₄ are
It may form a substituted or unsubstituted -N-carbazolyyl group, a substituted or unsubstituted -N-phenoxaziniyl group, or a substituted or unsubstituted -N-phenothiaziniyl group, and preferably The substituent or the substituent may be mono- or polysubstituted with a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms. A good -N-carbazolyyl group, a -N-phenoxaziniyl group, or a -N-phenothiaziniyl group,
More preferably, as the unsubstituted or substituted group, for example, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a monosubstituted or polysubstituted with an aryl group having 6 to 10 carbon atoms. Optionally substituted -N
-Carbazoliyl group, -N-phenoxaziniyl group, or -N-phenothiaziniyl group, and more preferably, unsubstituted -N-carbazolyyl group and unsubstituted-
It is an N-phenoxaziniyl group or an unsubstituted -N-phenothiaziniyl group.

--NAr ₁ Ar ₂ and --NAr ₃ Ar ₄ may form a nitrogen-containing heterocycle, and specific examples thereof include --N-carbazolyyl group, 2-methyl-N-carbazolyyl group, 3 -Methyl-N-carbazolyl group, 4
-Methyl-N-carbazolyyl group, 3-n-butyl-N
-Carbazolyyl group, 3-n-hexyl-N-carbazolyyl group, 3-n-octyl-N-carbazolyyl group,
3-n-decyl-N-carbazolyyl group, 3,6-dimethyl-N-carbazolyyl group, 2-methoxy-N-carbazolyyl group, 3-methoxy-N-carbazolyyl group,
3-ethoxy-N-carbazolyyl group, 3-isopropoxy-N-carbazolyyl group, 3-n-butoxy-N-
Carbazolyyl group, 3-n-octyloxy-N-carbazolyyl group, 3-n-decyloxy-N-carbazolyyl group, 3-phenyl-N-carbazolyyl group, 3-
(4'-methylphenyl) -N-carbazolyyl group, 3
-(4'-tert-butylphenyl) -N-carbazoliyl group, 3-chloro-N-carbazolyyl group, -N-phenoxaziniyl group, -N-phenothiaziniyl group, 2-
A methyl-N-phenothiazinyl group etc. can be mentioned.

In the compound represented by the general formula (1),
m represents 0 or 1.

Specific examples of the compound represented by the general formula (1) according to the present invention include the following compounds, but the present invention is not limited thereto. Exemplary Compound (Group A) A-1.3- [4 '-(N, N-diphenylamino) phenyl] -2,4,5-triphenylthiophene A-2.3- [4'-[N-phenyl -N- (4 "-methylphenyl) amino] phenyl] -2,4,5-triphenylthiophene A-3.3- [4 '-[N-phenyl-N- (3" -methylphenyl) amino] Phenyl] -2,4,5-triphenylthiophene A-4.3- [4 '-[N-phenyl-N- (2 "-methylphenyl) amino] phenyl] -2,4,5-triphenylthiophene A-5.3- [4 '-[N-phenyl-N- (4 "-ethylphenyl) amino] phenyl] -2,4,5-triphenylthiophene A-6.3- [4'-[N -Phenyl-N- (4 "-te
rt-Butylphenyl) amino] phenyl] -2,4,5
-Triphenylthiophene A-7.3- [4 '-[N- (3 "-methylphenyl)
-N- (4 "'-methylphenyl) amino] phenyl]
-2,4,5-Triphenylthiophene A-8.3- [4 '-[N- (4 "-methylphenyl)
-N- (4 "'-cyclohexylphenyl) amino] phenyl] -2,4,5-triphenylthiophene A-9.3- [4'-[N, N-di (4" -methylphenyl) amino] Phenyl] -2,4,5-triphenylthiophene A-10.3- [4 '-[N, N-di (3 "-methylphenyl) amino] phenyl] -2,4,5-triphenylthiophene A -11.3- [4 '-[N, N-di (4 "-ethylphenyl) amino] phenyl] -2,4,5-triphenylthiophene A-12.3- [4'-[N, N -Di (4 "-tert-butylphenyl) amino] phenyl] -2,4,5-triphenylthiophene A-13.3- [4 '-[N, N-di (4" -n-octylphenyl)] Amino] phenyl] -2,4,5-triphenylthiophene A-14.3- [4'- [N-phenyl-N- (2 ",
4 "-dimethylphenyl) amino] phenyl] -2,
4,5-Triphenylthiophene A-15.3- [4 '-[N-phenyl-N- (3 ",
4 "-dimethylphenyl) amino] phenyl] -2,
4,5-Triphenylthiophene A-16.3- [4 '-[N, N-di (2 ", 5" -diisopropylphenyl) amino] phenyl] -2,4
5-Triphenylthiophene A-17.3- [4 '-[N, N-di (3 ", 5" -dimethylphenyl) amino] phenyl] -2,4,5-triphenylthiophene A-18.3 -[4 '-[N-phenyl-N- (4 "-
Methoxyphenyl) amino] phenyl] -2,4,5-
Triphenylthiophene A-19.3- [4 '-[N-phenyl-N- (3 "-
Methoxyphenyl) amino] phenyl] -2,4,5-
Triphenylthiophene A-20.3- [4 '-[N-phenyl-N- (2 "-
Methoxyphenyl) amino] phenyl] -2,4,5-
Triphenylthiophene A-21.3- [4 '-[N-phenyl-N- (4 "-
n-butoxyphenyl) amino] phenyl] -2,4
5-Triphenylthiophene A-22.3- [4 '-[N- (3 "-methylphenyl) -N- (4"'-n-hexyloxyphenyl) amino] phenyl] -2,4,5- Triphenylthiophene A-23.3- [4 '-[N- (3 "-methoxyphenyl) -N- (4"'-methoxyphenyl) amino] phenyl] -2,4,5-triphenylthiophene A- 24.3- [4 '-[N, N-di (3 "-methoxyphenyl) amino] phenyl] -2,4,5-triphenylthiophene A-25.3- [4'-[N, N- Di (4 "-ethoxyphenyl) amino] phenyl] -2,4,5-triphenylthiophene A-26.3- [4 '-[N-phenyl-N- (2",
4 "-dimethoxyphenyl) amino] phenyl] -2,
4,5-Triphenylthiophene A-27.3- [4 '-[N-phenyl-N- (3 ",
4 "-dimethoxyphenyl) amino] phenyl] -2,
4,5-triphenylthiophene A-28.3- [4 '-[N-phenyl-N- (3 ",
4 ", 5" -trimethoxyphenyl) amino] phenyl] -2,4,5-triphenylthiophene A-29.3- [4 '-[N, N-di (2 "-methoxy-4" -ethoxy Phenyl) amino] phenyl] -2,
4,5-Triphenylthiophene A-30.3- [4 '-[N-phenyl-N- (3 "-
Ethyl-5 "-methoxyphenyl) amino] phenyl]
-2,4,5-Triphenylthiophene A-31.3- [4 '-[N, N-di (3 "-methyl-
5 "-methoxyphenyl) amino] phenyl] -2,
4,5-Triphenylthiophene A-32.3- [4 '-[N-phenyl-N- (4 "-
Fluorophenyl) amino] phenyl] -2,4,5-
Triphenylthiophene A-33.3- [4 '-[N-phenyl-N- (3 "-
Fluorophenyl) amino] phenyl] -2,4,5-
Triphenylthiophene A-34.3- [4 '-[N-phenyl-N- (2 "-
Chlorophenyl) amino] phenyl] -2,4,5-triphenylthiophene A-35.3- [4 '-[N, N-di (4 "-fluorophenyl) amino] phenyl] -2,4,5- Triphenylthiophene A-36.3- [4 ′-[N, N-di (2 ″ -fluoro-4 ″ -methylphenyl) amino] phenyl] -2,
4,5-Triphenylthiophene A-37.3- [4 '-[N, N-di (2 "-fluoro-4" -ethoxyphenyl) amino] phenyl] -2,
4,5-Triphenylthiophene A-38.3- [4 '-[N, N-di (3 "-methyl-
4 "-fluorophenyl) amino] phenyl] -2,
4,5-Triphenylthiophene A-39.3- [4 '-[N-phenyl-N- (4 "-
Phenylphenyl) amino] phenyl] -2,4,5-
Triphenylthiophene A-40.3- [4 '-[N-phenyl-N- (2 "-
Phenylphenyl) amino] phenyl] -2,4,5-
Triphenylthiophene A-41.3- [4 '-[N-phenyl-N- (4 "-
[3 "'-Methylphenyl] phenyl) amino] phenyl] -2,4,5-triphenylthiophene A-42.3- [4'-[N- (3" -phenylphenyl) -N- (4 "'-Phenylphenyl) amino] phenyl] -2,4,5-triphenylthiophene A-43.3- [4'-[N, N-di (4 "-phenylphenyl) amino] phenyl] -2,4 , 5-Triphenylthiophene A-44.3- [4 '-[N-phenyl-N- (1 "-
Naphthyl) amino] phenyl] -2,4,5-triphenylthiophene A-45.3- [4 '-[N-phenyl-N- (2 "-
Naphthyl) amino] phenyl] -2,4,5-triphenylthiophene A-46.3- [4 '-[N- (1 "-naphthyl) -N
-(2 "'-naphthyl) amino] phenyl] -2,4
5-Triphenylthiophene A-47.3- [4 '-[N- (4 "-phenylphenyl) -N- (1"'-naphthyl) amino] phenyl]-
2,4,5-Triphenylthiophene A-48.3- [4 '-[N, N-di (1 "-naphthyl) amino] phenyl] -2,4,5-triphenylthiophene A-49.3 -[4 '-[N, N-di (2 "-naphthyl) amino] phenyl] -2,4,5-triphenylthiophene A-50.3- [4'-[N-phenyl-N- (9 "-
Anthryl) amino] phenyl] -2,4,5-triphenylthiophene A-51.3- [4 '-[N-phenyl-N- (10 "
-Phenyl-9 "-anthryl) amino] phenyl]-
2,4,5-Triphenylthiophene A-52.3- [4 '-[N-phenyl-N- (9 "-
Phenanthryl) amino] phenyl] -2,4,5-triphenylthiophene A-53.3- [4 '-[N- (3 "-methylphenyl) -N- (9"'-phenanthryl) amino] phenyl] -2,4,5-triphenylthiophene A-54.3- [4 '-[N-phenyl-N- (9 ",
9 "-dimethyl-2" -fluorenyl) amino] phenyl] -2,4,5-triphenylthiophene A-55.3- [4 '-[N- (4 "-methylphenyl) -N- (9"', 9 "'-Dimethyl-2"'-fluorenyl) amino] phenyl] -2,4,5-triphenylthiophene A-56.3- [4'-N, N-di (9 ", 9"- Dimethyl-2 "-fluorenyl) amino] phenyl] -2,
4,5-Triphenylthiophene A-57.3- [4'-N, N-di (9 ", 9" -diethyl-2 "-fluorenyl) amino] phenyl] -2,
4,5-Triphenylthiophene A-58.3- [4 '-[N-phenyl-N- (2 "-
Pyridyl) amino] phenyl] -2,4,5-triphenylthiophene A-59.3- [4 '-[N-carbazolyyl] phenyl] -2,4,5-triphenylthiophene A-60.3- [ 4 '-[N-phenoxaziniyl] phenyl] -2,4,5-triphenylthiophene A-61.3- [4'-[N-phenothiaziniyl] phenyl] -2,4,5-tri Phenylthiophene

(Group B) B-1.3,4-bis [4 '-(N, N-diphenylamino) phenyl] -2,5-diphenylthiophene B-2.3,4-bis [4'- [N-phenyl-N-
(4 "-Methylphenyl) amino] phenyl] -2,5
-Diphenylthiophene B-3.3,4-bis [4 '-[N-phenyl-N-
(3 "-Methylphenyl) amino] phenyl] -2,5
-Diphenylthiophene B-4.3,4-bis [4 '-[N-phenyl-N-
(2 "-Methylphenyl) amino] phenyl] -2,5
-Diphenylthiophene B-5.3,4-bis [4 '-[N-phenyl-N-
(4 "-Ethylphenyl) amino] phenyl] -2,5
-Diphenylthiophene B-6.3,4-bis [4 '-[N-phenyl-N-
(4 "-tert-butylphenyl) amino] phenyl]-
2,5-Diphenylthiophene B-7.3,4-bis [4 '-[N- (3 "-methylphenyl) -N- (4"'-methylphenyl) amino] phenyl] -2,5-diphenyl Thiophene B-8.3,4-Bis [4 '-[N- (3 "-methylphenyl) -N- (4"'-tert-butylphenyl) amino] phenyl] -2,5-diphenylthiophene B- 9.3,4-Bis [4 '-[N, N-di (4 "-methylphenyl) amino] phenyl] -2,5-diphenylthiophene B-10.3,4-bis [4'-[N , N-di (3 "-
Methylphenyl) amino] phenyl] -2,5-diphenylthiophene B-11.3,4-bis [4 '-[N, N-di (4 "-
Ethylphenyl) amino] phenyl] -2,5-diphenylthiophene B-12.3,4-bis [4 '-[N, N-di (4 "-
tert-Butylphenyl) amino] phenyl] -2,5-
Diphenylthiophene B-13.3,4-bis [4 '-[N, N-di (4 "-
n-octylphenyl) amino] phenyl] -2,5-
Diphenylthiophene B-14.3,4-bis [4 '-[N-phenyl-N-
(2 ", 4" -Dimethylphenyl) amino] phenyl]
-2,5-Diphenylthiophene B-15.3,4-bis [4 '-[N-phenyl-N-
(3 ", 4" -dimethylphenyl) amino] phenyl]
-2,5-Diphenylthiophene B-16.3,4-bis [4 '-[N, N-di (3 ",
5 "-dimethylphenyl) amino] phenyl] -2,5
-Diphenylthiophene B-17.3- [4 '-(N, N-diphenylamino)
Phenyl] -4- [4 "-[N ', N'-di (3"'-methylphenyl) amino] phenyl] -2,5-diphenylthiophene B-18.3- [4 '-[N, N -Di (3 "'-methylphenyl) amino] phenyl] -4- [4"-[N',
N'-di (4 ""-methylphenyl) amino] phenyl] -2,5-diphenylthiophene B-19.3- [4 '-(N, N-diphenylamino)
Phenyl] -4- [4 "-[N'-phenyl-N'-
(3 "'-methylphenyl) amino] phenyl] -2,
5-Diphenylthiophene B-20.3- [4 '-(N, N-diphenylamino)
Phenyl] -4- [4 "-[N'-phenyl-N'-
(3 "', 5"'-Dimethylphenyl) amino] phenyl] -2,5-diphenylthiophene B-21.3- [4 '-[N-phenyl-N- (4 "'
-Methylphenyl) amino] phenyl] -4- [4 "-
[N'-phenyl-N '-(3 ""-methylphenyl)
Amino] phenyl] -2,5-diphenylthiophene B-22.3,4-bis [4 '-[N-phenyl-N-
(4 "-methoxyphenyl) amino] phenyl] -2,
5-Diphenylthiophene B-23.3,4-bis [4 '-[N-phenyl-N-
(3 "-methoxyphenyl) amino] phenyl] -2,
5-diphenylthiophene B-24.3,4-bis [4 '-[N-phenyl-N-
(2 "-methoxyphenyl) amino] phenyl] -2,
5-diphenylthiophene B-25.3,4-bis [4 '-[N-phenyl-N-
(4 "-n-butoxyphenyl) amino] phenyl]-
2,5-Diphenylthiophene B-26.3,4-bis [4 '-[N- (3 "-methylphenyl) -N- (4"'-n-hexyloxyphenyl) amino] phenyl] -2, 5-Diphenylthiophene B-27.3,4-bis [4 '-[N- (3 "-methoxyphenyl) -N- (4"'-methoxyphenyl) amino] phenyl] -2,5-diphenylthiophene B-28.3,4-bis [4 '-[N, N-di (4 "-
Ethoxyphenyl) amino] phenyl] -2,5-diphenylthiophene B-29.3,4-bis [4 '-[N, N-di (3 "-
Methoxyphenyl) amino] phenyl] -2,5-diphenylthiophene B-30.3,4-bis [4 '-[N-phenyl-N-
(2 ", 4" -Dimethoxyphenyl) amino] phenyl] -2,5-diphenylthiophene B-31.3,4-bis [4 '-[N-phenyl-N-
(3 ", 4" -dimethoxyphenyl) amino] phenyl] -2,5-diphenylthiophene B-32.3,4-bis [4 '-[N-phenyl-N-
(2 "-Methyl-4" -methoxyphenyl) amino] phenyl] -2,5-diphenylthiophene B-33.3,4-bis [4 '-[N-phenyl-N-
(3 "-Ethyl-5" -methoxyphenyl) amino] phenyl] -2,5-diphenylthiophene B-34.3,4-bis [4 '-[N, N-di (3 "-
Methyl-5 "-methoxyphenyl) amino] phenyl]
-2,5-Diphenylthiophene B-35.3- [4 '-(N, N-diphenylamino)
Phenyl] -4- [4 "-[N ', N'-di (4"'-
Cyclohexyloxyphenyl) amino] phenyl]-
2,5-Diphenylthiophene B-36.3- [4 '-[N, N-di (3 "'-methylphenyl) amino] phenyl] -4- [4"-[N ',
N'-di (4 ""-methoxyphenyl) amino] phenyl] -2,5-diphenylthiophene B-37.3- [4 '-(N, N-diphenylamino)
Phenyl] -4- [4 "-[N'-phenyl-N'-
(2 "'-Methyl-4"'-methoxyphenyl) amino] phenyl] -2,5-diphenylthiophene B-38.3- [4 '-[N-phenyl-N- (3 "'
-Methylphenyl) amino] phenyl] -4- [4 "-
[N'-phenyl-N '-(3 ""-ethoxyphenyl) amino] phenyl] -2,5-diphenylthiophene B-39.3,4-bis [4'-[N-phenyl-N-
(4 "-fluorophenyl) amino] phenyl] -2,
5-Diphenylthiophene B-40.3,4-bis [4 '-[N-phenyl-N-
(3 "-fluorophenyl) amino] phenyl] -2,
5-Diphenylthiophene B-41.3,4-bis [4 '-[N-phenyl-N-
(3 "-chlorophenyl) amino] phenyl] -2,5
-Diphenylthiophene B-42.3,4-bis [4 '-[N, N-di (3 "-
Fluorophenyl) amino] phenyl] -2,5-diphenylthiophene B-43.3,4-bis [4 '-[N, N-di (3 "-
Chloro-4 "-methoxyphenyl) amino] phenyl]
-2,5-Diphenylthiophene B-44.3,4-bis [4 '-[N, N-di (3 "-
Methyl-4 "-fluorophenyl) amino] phenyl]
-2,5-Diphenylthiophene B-45.3,4-bis [4 '-[N, N-di (2 "-
Methoxy-4 ″ -fluorophenyl) amino] phenyl] -2,5-diphenylthiophene B-46.3- [4 ′-(N, N-diphenylamino)
Phenyl] -4- [4 "-[N ', N'-di (4"'-
Fluorophenyl) amino] phenyl] -2,5-diphenylthiophene B-47.3- [4 '-[N, N-di (3 "'-methylphenyl) amino] phenyl] -4- [4"-[ N ',
N'-di (3 ""-chlorophenyl) amino] phenyl] -2,5-diphenylthiophene B-48.3- [4 '-[N, N-di (4 "'-methoxyphenyl) amino] phenyl] -4- [4 "-[
N ', N'-di (3 ""-fluorophenyl) amino]
Phenyl] -2,5-diphenylthiophene B-49.3- [4 '-[N-phenyl-N- (4 "'
-Methylphenyl) amino] phenyl] -4- [4 "-
[N'-phenyl-N'-di (3 ""-chlorophenyl) amino] phenyl] -2,5-diphenylthiophene B-50.3,4-bis [4 '-[N-phenyl-N-
(4 "-phenylphenyl) amino] phenyl] -2,
5-Diphenylthiophene B-51.3,4-bis [4 '-[N-phenyl-N-
(2 "-phenylphenyl) amino] phenyl] -2,
5-diphenylthiophene B-52.3,4-bis [4 '-[N, N-di (4 "-
Phenylphenyl) amino] phenyl] -2,5-diphenylthiophene B-53.3- [4 '-[N, N-di (4 "'-methylphenyl) amino] phenyl] -4- [4"-[ N'-
Phenyl-N '-(4 ""-phenylphenyl) amino] phenyl] -2,5-diphenylthiophene B-54.3,4-bis [4'-[N-phenyl-N-
(1 "-naphthyl) amino] phenyl] -2,5-diphenylthiophene B-55.3,4-bis [4 '-[N- (4" -methylphenyl) -N- (1 "'-naphthyl) Amino] phenyl] -2,5-diphenylthiophene B-56.3,4-bis [4 '-[N-phenyl-N-
(2 "-naphthyl) amino] phenyl] -2,5-diphenylthiophene B-57.3,4-bis [4 '-[N, N- (1" -naphthyl) amino] phenyl] -2,5- Diphenylthiophene B-58.3,4-bis [4 '-[N, N- (2 "-naphthyl) amino] phenyl] -2,5-diphenylthiophene B-59.3,4-bis [4'- [N- (1 "-naphthyl) -N- (2"'-naphthyl) amino] phenyl]-
2,5-Diphenylthiophene B-60.3- [4 '-[N-phenyl-N- (1 "'
-Naphthyl) amino] phenyl] -4- [4 "-[N '
-Phenyl-N '-(2 ""-naphthyl) amino] phenyl] -2,5-diphenylthiophene B-61.3- [4'-[N-phenyl-N- (1 "'
-Naphthyl) amino] phenyl] -4- [4 "-[N '
-Phenyl-N '-(4 ""-phenylphenyl) amino] phenyl] -2,5-diphenylthiophene B-62.3,4-bis [4'-[N-phenyl-N-
(9 "-anthryl) amino] phenyl] -2,5-diphenylthiophene B-63.3,4-bis [4 '-[N-phenyl-N-
(9 "-phenanthryl) amino] phenyl] -2,5
-Diphenylthiophene B-64.3,4-bis [4 '-[N- (3 "-methylphenyl) -N- (9"'-phenanthryl) amino] phenyl] -2,5-diphenylthiophene B-65 3- [4 '-(N, N-diphenyl) aminophenyl] -4- [4 "-[N'-phenyl-N'-
(9 "'-phenanthryl) amino] phenyl] -2,
5-Diphenylthiophene B-66.3- [4 '-(N-phenyl-N- (1 "'
-Naphthyl) aminophenyl) -4- [4 "-[N'-
Phenyl-N '-(9 ""-phenanthryl) amino]
Phenyl] -2,5-diphenylthiophene B-67.3,4-bis [4 '-[N-phenyl-N-
(9 ", 9" -Dimethyl-2 "-fluorenyl) amino] phenyl] -2,5-diphenylthiophene B-68.3,4-bis [4 '-[N- (4" -methylphenyl) -N -(9 "', 9"'-dimethyl-2 "'-fluorenyl) amino] phenyl] -2,5-diphenylthiophene B-69.3,4-bis [4'-[N, N-di (9 ",
9 "-dimethyl-2" -fluorenyl) amino] phenyl] -2,5-diphenylthiophene B-70.3- [4 '-(N, N-diphenyl) aminophenyl] -4- [4 "-[N '-Phenyl-N'-
(9 "', 9"'-dimethyl-2 "'-fluorenyl)
Amino] phenyl] -2,5-diphenylthiophene B-71.3- [4 '-(N, N-diphenyl) aminophenyl] -4- [4 "-[N'N'-di (9"',
9 "'-dimethyl-2"'-fluorenyl) amino] phenyl] -2,5-diphenylthiophene B-72.3- [4 '-[N, N-di (4 "'-methylphenyl) amino] phenyl ] -4- [4 "-[N '
N'-di (9 "", 9 ""-dimethyl-2 ""-fluorenyl) amino] phenyl] -2,5-diphenylthiophene B-73.3,4-bis [4 '-[N- (4 "-Methylphenyl) -N- (3"'-furyl) amino] phenyl]
-2,5-Diphenylthiophene B-74.3,4-bis [4 '-(N-carbazolyyl) phenyl] -2,5-diphenylthiophene B-75.3- [4'-(N-phenoxaziniyl ) Phenyl] -4- [4 "-(N ', N'-diphenyl) aminophenyl] -2,5-diphenylthiophene B-76.3- [4'-(N-carbazolyyl) phenyl] -4- [] 4 "-[N'-phenyl-N '-(1"'
-Naphthyl) amino] phenyl] -2,5-diphenylthiophene

The compound represented by the general formula (1) according to the present invention can be produced by a method known per se.
That is, for example, a compound represented by the general formula (2):
The compound represented by the general formula (3), the compound represented by the general formula (4), the compound represented by the general formula (5), and the compound represented by the general formula (6) are replaced with copper compounds (for example, , Copper metal, copper chloride) in the presence of (Ullmann reaction).

[0028]

[Chemical 4] [In the above formula, X _{1 to} X ₄ represent a halogen atom, and Ar _{1 to} A 4
r ₄ and m have the same meaning as in formula (1)]

In addition, for example, a compound represented by the general formula (7), a compound represented by the general formula (8), and a compound represented by the general formula (9) are mixed with a copper compound (for example, metallic copper). , Copper chloride) in the presence of (Ullmann reaction).

[0030]

[Chemical 5] [In the above formula, X ₅ and X ₆ represent a halogen atom, and Ar _{1 to} A
r ₄ and m have the same meaning as in formula (1)]

In the general formulas (3) to (7), X _{1 to} X ₆
Represents a halogen atom, preferably a chlorine atom, a bromine atom or an iodine atom, and more preferably a bromine atom or an iodine atom.

The organic electroluminescent device usually 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, hole transporting function and / or electron injecting function, and electron transporting function, the light emitting layer has a hole injecting and transporting layer and / or an electron injecting and transporting layer. It is also possible to have a structure of a type of device that also serves as a device. Of course, in some cases, it is possible to have a structure of a type element (one-layer type element) in which neither the hole injecting and transporting layer nor the electron injecting and transporting layer is provided. Each of the hole injecting and transporting layer, the electron injecting and transporting layer, and the light emitting layer may have a single-layer structure or a multi-layer structure,
The hole injecting and transporting layer and the electron injecting and transporting layer may be formed by separately providing a layer having an injection function and a layer having a transport function in each layer.

In the organic electroluminescent device of the present invention, the compound represented by the general formula (1) is preferably used as a hole injecting and transporting component and / or a light emitting component, and more preferably as a hole injecting and transporting component. preferable. In the organic electroluminescent device of the present invention, the compound represented by the general formula (1) may be used alone or in combination.

The structure 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, of course, 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, a light emitting component and An element of a type in which an electron injecting and transporting component is mixed and sandwiched between a pair of electrodes (FIG. 6), and (G) a single layer form in which a hole injecting and transporting component and a light emitting component are mixed between a pair of electrodes. There are a sandwiched type element (FIG. 7) and a sandwiched type element (FIG. 8) in a single layer form in which a luminescent component and an electron injecting and transporting component are mixed.

The organic electroluminescent device of the present invention is not limited to these device configurations, 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. it can. Further, in each type of device, a light emitting component is provided 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 between the light emitting layer and the electron injecting and transporting layer. It is also possible to provide a mixed layer of the electron injecting and transporting component. More preferable configurations of the organic electroluminescent element are (A) type element, (B) type element, (E)
Type element, (F) type element or (G) type element, and more preferably (A) type element, (B) type element or (G) type element.

As the organic electroluminescent element of the present invention, for example, (A) anode / hole injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type element shown in FIG. 1 will be described.
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, 6 is a cathode,
Reference numeral 7 indicates a power source.

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 substance. As the electrode material used for the anode, for example, gold, platinum, silver, copper, cobalt, nickel,
Examples thereof include palladium, vanadium, tungsten, tin oxide, zinc oxide, ITO (indium tin oxide), polythiophene, polypyrrole and the like. These electrode substances may be used alone or in combination. The anode can be formed of these electrode substances on the substrate 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 electrical resistance of the anode is preferably several hundred Ω / □
Below, more preferably, it is set to about 5 to 50 Ω / □. The thickness of the anode depends on the material of the electrode substance used, but is generally about 5 to 1000 nm, and more preferably,
It is set to 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 a compound represented by the general formula (1) and / or another compound having a hole injecting and transporting function (for example, a phthalocyanine derivative, a triarylmethane derivative, a triarylamine derivative, an oxazole derivative,
Hydrazone derivative, stilbene derivative, pyrazoline derivative, polysilane derivative, polyphenylene vinylene and its derivative, polythiophene and its derivative, poly-
(N-vinylcarbazole derivative, etc.) can be used. The compounds having a hole injecting and transporting function may be used alone or in combination. In the organic electroluminescent element of the present invention, it is preferable that the hole injecting and transporting layer contains the compound represented by the general formula (1).

Other compounds having a hole injecting and transporting function used in the present invention include triarylamine derivatives (for example, 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, 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-yl] 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)
-N-phenylamino] benzene), polythiophene and its derivatives, and poly-N-vinylcarbazole derivatives are more preferable.

When the compound represented by the general formula (1) and another compound having a hole injecting and transporting function are used in combination, the proportion of the compound represented by the general formula (1) in the hole injecting and transporting layer is , Preferably 0.1% by weight or more, more preferably
0.1 to 99.9% by weight, more preferably 1 to
It is adjusted to about 99% by weight, particularly preferably about 5 to 95% by weight.

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 includes the compound represented by the general formula (1) and / or another compound having a light emitting function (eg, acridone derivative, quinacridone derivative, diketopyrrolopyrrole derivative, polycyclic aromatic compound [eg, rubrene, anthracene. , Tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9'- Ethynylanthracenyl) benzene, 4,4'-bis (9 "-ethynylanthracenyl) biphenyl], triarylamine derivatives [eg, the compounds described above can be mentioned as the compound having a hole injecting and transporting function] , Organometallic complexes [eg Tris 8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, zinc salt of 2- (2′-hydroxyphenyl) benzoxazole, zinc salt of 2- (2′-hydroxyphenyl) benzothiazole, 4- Zinc salt of hydroxyacridine, zinc salt of 3-hydroxyflavone, beryllium salt of 5-hydroxyflavone, aluminum salt of 5-hydroxyflavone], stilbene derivative [eg 1,
1,4,4-tetraphenyl-1,3-butadiene,
4,4'-bis (2,2-diphenylvinyl) biphenyl, 4,4'-bis [(1,1,2-triphenyl) ethenyl] biphenyl],

Coumarin derivative [for example, 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], pyran derivative [eg DCM1, DCM2], oxazone derivative [eg Nile red], benzothiazole derivative,
Benzoxazole derivative, benzimidazole derivative, pyrazine derivative, cinnamic acid ester derivative, 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, polynaphthylene vinylene and Its derivatives, polythienylene vinylene and its derivatives, etc.)
Can be formed using at least one kind.

In the organic electroluminescent device of the present invention, it is preferable that the light emitting layer contains a compound represented by the general formula (1). When the compound represented by the general formula (1) is used in combination with another compound having a light emitting function, the proportion of the compound represented by the general formula (1) in the light emitting layer is preferably 0.001 to 99. It is adjusted to about 0.999% by weight.

As the other compound having a light emitting function used in the present invention, a polycyclic aromatic compound and a light emitting organometallic complex are more preferable. For example, J. Appl. Phys., 65 , 36
10 (1989), JP-A-5-214332, the light emitting layer may be composed of a host compound and a guest compound (dopant). The compound represented by the general formula (1) can be used as a host compound to form a light emitting layer, and can also be used as a guest compound to form a light emitting layer. When the compound represented by the general formula (1) is used as a host compound to form the light emitting layer, the guest compound may be, for example, a compound having the other light emitting function described above, and among them, a polycyclic aromatic compound. Is preferred. In this case, with respect to the compound represented by the general formula (1), another compound having a light emitting function, preferably 0.
001 to 40% by weight, more preferably 0.01 to
The amount used is about 30% by weight, more preferably about 0.1 to 20% by weight.

The polycyclic aromatic compound used in combination with the compound represented by the general formula (1) is not particularly limited, but for example, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene,
Tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9'-ethynylanthracenyl) benzene, 4,4'-bis Examples thereof include (9 ″ -ethynylanthracenyl) biphenyl. Of course, the polycyclic aromatic compounds may be used alone or in combination.

When the compound represented by the general formula (1) is used as the guest compound to form the light emitting layer, the host compound is preferably a light emitting organometallic complex. In this case, the compound represented by the general formula (1) is preferably added in an amount of about 0.001 to 40% by weight, more preferably about 0.01 to 30% by weight, based on the luminescent organometallic complex. Preferably, about 0.1 to 20% by weight is used.

The light-emitting organometallic complex used in combination with the compound represented by the general formula (1) is not particularly limited, but a light-emitting organoaluminum complex is preferable, and substituted or unsubstituted 8-quinolinolate coordination. A luminescent organic aluminum complex having a child is more preferable. Examples of preferable luminescent organic metal complexes include luminescent organic aluminum complexes represented by the general formulas (a) to (c).

(Q) 3 -Al (a) (In the formula, Q represents a substituted or unsubstituted 8-quinolinolate ligand) (Q) 2 -Al-OL (b) (In the formula, Q Represents a substituted 8-quinolinolato ligand, O
-L is a phenolate ligand and L represents a hydrocarbon group having a phenyl moiety and having 6 to 24 carbon atoms) (Q) 2-Al-O-Al- (Q) 2 (c) (wherein Q represents a substituted 8-quinolinolate ligand)

Specific examples of the luminescent organometallic complex 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-quinolinolate)
(Phenolato) aluminum, bis (2-methyl-8)
-Quinolinolate) (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-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenolate) 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-quinolinoleate) (3,5-di-te
rt-Butylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (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
-Naphtholate) aluminum, bis (2-methyl-8)
-Quinolinolato) (2-naphtholate) aluminum, bis (2,4-dimethyl-8-quinolinolato)
(2-Phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) (4-phenylphenolato) aluminum Bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-di-tert-butylphenolate) aluminum ,

Bis (2-methyl-8-quinolinolate)
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. Of course, the luminescent organometallic complex may be used alone or in combination.

The electron injecting and transporting 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. Examples of the compound having an electron injecting / transporting function used in the electron injecting / transporting layer include, for example, organometallic complexes [eg, tris (8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, 5-hydroxyflavone. Beryllium salt, aluminum salt of 5-hydroxyflavone], and oxadiazole derivative [eg, 1,3-bis]
[5 '-(p-tert-butylphenyl) -1,3,4-
Oxadiazol-2′-yl] benzene], triazole derivative [for example, 3- (4′-tert-butylphenyl) -4-phenyl-5- (4 ″ -biphenyl) -1,
2,4-triazole], a triazine derivative, a perylene derivative, a quinoline derivative, a quinoxaline derivative, a diphenylquinone derivative, a nitro-substituted fluorenone derivative, and a thiopyrandioxide derivative. The compounds having an electron injecting and transporting function may be used alone or in combination.

As 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,
Examples thereof include manganese, 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 can be formed on the electron injecting and transporting layer by using these electrode materials by a method such as a vapor deposition method, a sputtering method, an ionization vapor deposition method, an ion plating method, a cluster ion beam method or the like. . Further, the cathode may have a single-layer structure or a multi-layer structure. The sheet electric resistance of the cathode is several hundred Ω.
It is preferably set to / □ or less. Although the thickness of the cathode depends on the material of the electrode material used, it is generally 5 to 1000.
nm, more preferably about 10 to 500 nm. In order to efficiently extract the light emitted from the organic electroluminescent device, at least one of the anode and the cathode is
It is preferably transparent or translucent, and it is generally more preferable to set the material and thickness of the anode so that the transmittance of emitted light is 70% or more.

In the organic electroluminescent device of the present invention, at least one layer may contain a singlet oxygen quencher. The singlet oxygen quencher is not particularly limited, for example, rubrene,
Examples thereof include a nickel complex and diphenylisobenzofuran, 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.
Incidentally, for example, when the hole injecting and transporting layer contains a singlet oxygen quencher, it may be uniformly contained in the hole injecting and transporting layer, and a layer adjacent to the hole injecting and transporting layer (for example, a light emitting layer, It may be contained near the electron injecting and transporting layer having a light emitting function). The content of the singlet oxygen quencher is 0.01 to 50% by weight, preferably 0.0 to 50% by weight based on the total amount of the layer (for example, the hole injecting and transporting layer) contained.
5 to 30% by weight, more preferably 0.1 to 20% by weight
Is.

The method for forming the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is not particularly limited, and examples thereof include a vacuum vapor deposition method, an ionization vapor deposition method, a solution coating method (for example, a spin coating method, a cast method). Method, dip coating method,
It can be produced by forming a thin film by a bar coating method, a roll coating method, a Langmuir-Brosette method, an inkjet method, or the like. By the vacuum evaporation method,
When forming each layer, the conditions of vacuum vapor deposition are not particularly limited, but under a vacuum of about 10 ⁻⁵ Torr or less,
~ 600 ℃ boat temperature (deposition source temperature), -50 ~
At a substrate temperature of about 300 ° C, 0.005 to 50 nm / se
It is preferable to carry out at a vapor deposition rate of about c. 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, whereby an organic electroluminescent device having further excellent various characteristics can be manufactured.
When each layer such as a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer is formed by using a plurality of compounds by a vacuum deposition method, co-evaporation is performed by individually controlling the temperature of each boat containing the compounds. It is preferable.

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,
Polymethylmethacrylate, polyether, polycarbonate, polyamide, polyimide, polyamideimide,
Polyparaxylene, polyethylene, polyethylene ether, polypropylene ether, polyphenylene oxide, polyether sulfone, polyaniline and its derivatives, polythiophene and its derivatives, polyphenylene vinylene and its derivatives, polyfluorene and its derivatives, polythienylene vinylene and its derivatives, etc. A high molecular compound is mentioned. The binder resins may be used alone or in combination.

When each layer is formed by the solution coating method,
The component forming each layer or the component and the binder resin, etc., a suitable organic solvent (for example, hexane, octane,
Decane, toluene, xylene, ethylbenzene, hydrocarbon solvents such as 1-methylnaphthalene, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, ketone solvents such as cyclohexanone, for example, dichloromethane, chloroform, tetrachloromethane, dichloroethane, trichloroethane, Tetrachloroethane, chlorobenzene, dichlorobenzene, halogenated hydrocarbon solvents such as chlorotoluene, for example, ethyl acetate, butyl acetate, ester solvents such as amyl acetate, for example, methanol, ethanol, propanol, butanol, pentanol, hexanol, Alcoholic solvents such as cyclohexanol, methyl cellosolve, ethyl cellosolve, ethylene glycol, etc., such as dibutyl ether, tetrahydrofuran, dioxy Down, ether solvents anisole, for example, N, N-dimethylformamide, N, N-
Dimethylacetamide, 1-methyl-2-pyrrolidone,
A polar solvent such as 1,3-dimethyl-2-imidazolidinone or dimethylsulfoxide) and / or water may be dissolved or dispersed into a coating solution to form a thin film by various coating methods. .

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 performed, and generally, about 0.1 to 50% by weight, The solution concentration is preferably about 1 to 30% by weight. In addition, when a binder resin is used, the amount used is not particularly limited, but generally, with respect to the components forming each layer (in the case of forming a one-layer type element, the total amount of each component is ), 5 to 99.9% by weight
The amount is preferably set to about 10 to 99% by weight, more preferably about 15 to 90% by weight.

The film thickness of the hole injecting / transporting layer, the light emitting layer, and the electron injecting / transporting layer is not particularly limited, but is generally preferably set to about 5 nm to 5 μm.
In addition, a protective layer (sealing layer) is provided for the purpose of preventing contact with oxygen, water, or the like of the manufactured element, and the element is formed of, for example, paraffin, liquid paraffin, silicon oil, fluorocarbon oil, zeolite. It can be encapsulated and protected in an inert material such as contained fluorocarbon oil.

The material used for the protective layer is, for example,
Organic polymer materials (for example, fluorinated resin, epoxy resin, silicone resin, epoxy silicone resin, polystyrene, polyester, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide), inorganic materials (for example, diamond) Examples include thin films, amorphous silica, electrically insulating glass, metal oxides, metal nitrides, metal carbonides, metal sulfides), and photocurable resins. They may be used, or a plurality of them may be used in combination. The protective layer may have a monolayer structure or a multilayer structure.

Further, for example, a metal oxide film (for example, an aluminum oxide film) or a metal fluoride film can be provided on the electrode as a protective film. Also, for example, on the surface of the anode,
For example, an interface layer (intermediate layer) composed of an organic phosphorus compound, polysilane, an aromatic amine derivative, a phthalocyanine derivative (for example, copper phthalocyanine), and carbon can be provided. Furthermore, the electrode, e.g., the anode, has its surface
For example, it can be used after being treated with acid, ammonia / hydrogen peroxide, or plasma.

The organic electroluminescent element of the present invention is generally used as a direct-current driving type element, but can also be used as a pulse-driving type or alternating-current driving type element.
The applied voltage is generally about 2 to 30V. The organic electroluminescent device of the present invention can be used for, for example, a panel type light source, various light emitting devices, various display devices, various markers, various sensors, and the like.

[0065]

The present invention will be described in more detail with reference to the following examples, but of course the present invention is not limited thereto.

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 a substrate holder of a vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. First, on an ITO transparent electrode, 3- [4 '-[N-phenyl-N- (4 "-methylphenyl) amino] phenyl]-
A compound of 2,4,5-triphenylthiophene (Exemplified compound No. A-2) was added at a deposition rate of 0.2 nm / sec to 75
It was vapor-deposited to a thickness of nm to form a hole injecting and transporting layer. Then
Then, tris (8-quinolinolato) aluminum was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 50 nm to obtain a light-emitting layer which also functions as an electron injecting and transporting layer. On top of that, magnesium and silver are deposited at a deposition rate of 0.2 as a cathode.
Co-deposition at a thickness of 200 nm at nm / sec (weight ratio 10:
The organic electroluminescent element was produced by using 1) as a cathode. still,
The vapor deposition was carried out while maintaining the reduced pressure state of the vapor deposition tank. A direct current voltage was applied to the produced organic electroluminescent device, and it was continuously driven at 50 ° C. in a dry atmosphere at a constant current density of 10 mA / cm ² . Initially, a green light emission of 6.5 V and a luminance of 520 cd / m ² was confirmed. The half-life of brightness was 650 hours.

Examples 2 to 25 In Example 1, instead of using the compound of Exemplified Compound No. A-2 in forming the hole injecting and transporting layer, the compound of Exemplified Compound No. A-9 (Example 2), Compound of Exemplified Compound No. A-15 (Example 3), Exemplified Compound No. A-
Compound No. 18 (Example 4), Compound No. A-27 (Example 5), Compound No. A-39 (Example 6), Compound No. A-44 (Example 7) , A compound of Exemplified Compound No. A-49 (Example 8), a compound of Exemplified Compound No. A-52 (Example 9),
Exemplified Compound No. A-56 compound (Example 10), Exemplified Compound No. B-3 compound (Example 11), Exemplified Compound No. B-6 compound (Example 12), Exemplified Compound No. B
-11 compound (Example 13), exemplified compound number B-1
9 compound (Example 14), exemplified compound number B-22 compound (Example 15), exemplified compound number B-33 compound (Example 16), exemplified compound number B-40 compound (Example 17) , A compound of Exemplified Compound No. B-50 (Example 18), a compound of Exemplified Compound No. B-54 (Example 19), a compound of Exemplified Compound No. B-57 (Example 2)
0), the compound of Exemplified Compound No. B-61 (Example 2
1), the compound of Exemplified Compound No. B-63 (Example 2
2), a compound of Exemplified Compound No. B-67 (Example 2
3), the compound of Exemplified Compound No. B-70 (Example 2
4), a compound of Exemplified Compound No. B-76 (Example 25)
An organic electroluminescence device was produced by the method described in Example 1 except that was used. Green light emission was confirmed from each element. Further, its characteristics were examined, and the results are shown in (Table 1).

Comparative Examples 1 and 2 In Example 1, instead of using the compound of Exemplified Compound No. A-2 in the formation of the hole injecting and transporting layer, 2-
[4 '-[N-phenyl-N- (4 "-methylphenyl) amino] phenyl] -3,4,5-triphenylthiophene (Comparative Example 1), 2,5-bis [4'-[N- An organic electroluminescent device was produced by the method described in Example 1 except that phenyl-N- (3 ″ -methylphenyl) amino] phenyl] -3,4-diphenylthiophene (Comparative Example 2) was used. Green light emission was confirmed from each element. Further, its characteristics were examined, and the results are shown in (Table 1).

[0069]

[Table 1]

[0070]

Example 26 Glass with ITO transparent electrode (anode) of 200 nm thickness
Substrate with a neutral detergent, acetone, and ethanol.
Sonicated. Dry the substrate with nitrogen gas,
After UV / ozone cleaning, the substrate holder of vapor deposition equipment
After fixing to, vapor deposition tank 3 × 10^-6The pressure was reduced to Torr. Well
On the ITO transparent electrode, poly (thiophene-2,5-
Diil) with a deposition rate of 0.1 nm / sec and a thickness of 20 nm
Then, a first hole injecting and transporting layer was formed by vapor deposition. Then an example
Compound No. B-2 was vapor-deposited at a rate of 0.2 nm / se
The second hole injecting and transporting layer is formed by vapor deposition with a thickness of 55 nm by c.
It was Then, on top of that, tris (8-quinolinolano)
G) Aluminum is deposited at a deposition rate of 0.2 nm / sec.
and a light emitting layer that also functions as an electron injecting and transporting layer.
did. Furthermore, the deposition rate of magnesium and silver on it
Co-deposition at a thickness of 200 nm at 0.2 nm / sec (weight ratio
10: 1) is used as a cathode to prepare an organic electroluminescence device.
It was In addition, vapor deposition should be performed while maintaining the reduced pressure in the vapor deposition tank.
It was Apply a DC voltage to the fabricated organic electroluminescent device and dry it.
10mA / cm in dry atmosphere ²Continuously driven with a constant current density of
Let Initially 6.5V, brightness 670 cd / m²Green
Color emission was confirmed. The half-life of brightness is 1250 hours
there were.

Example 27 Glass with ITO transparent electrode (anode) of 200 nm thickness
Substrate with a neutral detergent, acetone, and ethanol.
Sonicated. Dry the substrate with nitrogen gas,
After UV / ozone cleaning, the substrate holder of vapor deposition equipment
After fixing to, vapor deposition tank 3 × 10^-6The pressure was reduced to Torr. Well
On the ITO transparent electrode, 4,4 ', 4 "-tris [N
-(3 "'-methylphenyl) -N-phenylamino] to
Liphenylamine was deposited at a deposition rate of 0.1 nm / sec at 50
It vapor-deposited to a thickness of nm to form a first hole injecting and transporting layer. Next
Then, the compound of Exemplified Compound No. 7 and rubrene were
20 nm thickness from the source at a deposition rate of 0.2 nm / sec
Co-evaporated (weight ratio 10: 1) to form a second hole injecting and transporting layer.
It was also used as a light emitting layer. Then, on top of that, Tris (8-
Quinolinolato) aluminum vapor deposition rate 0.2 nm /
It is vapor-deposited to a thickness of 50 nm in sec and used as an electron injection transport layer.
It was Further, magnesium and silver are vapor-deposited at a deposition rate of 0.
Co-deposition at a thickness of 200 nm at 2 nm / sec (weight ratio 1
The organic electroluminescent element was produced by using 0: 1) as a cathode.
The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank.
A direct current voltage was applied to the produced organic electroluminescent device to dry it.
10mA / cm under ambient air ²Driven continuously at a constant current density of
It was Initially, 6.1V, brightness 660 cd / m²The yellow
Was confirmed to be emitted. Luminance half-life is 1350 hours
It was.

Example 28 Glass with ITO transparent electrode (anode) of 200 nm thickness
Substrate with a neutral detergent, acetone, and ethanol.
Sonicated. Dry the substrate with nitrogen gas,
After UV / ozone cleaning, the substrate holder of vapor deposition equipment
After fixing to, vapor deposition tank 3 × 10^-6The pressure was reduced to Torr. Well
On the ITO transparent electrode, poly (thiophene-2,5-
Diil) with a deposition rate of 0.1 nm / sec and a thickness of 20 nm
Then, a first hole injecting and transporting layer was formed by vapor deposition. Atmospheric vapor deposition tank
After returning to pressure reduction, the vapor deposition tank is again set to 3 × 10.^-6Decompress to Torr
It was Then, the compound of Exemplified Compound No. A-59 and deca
Clen from different evaporation sources, deposition rate 0.2nm / se
Co-deposited to a thickness of 55 nm with c (weight ratio 10: 0.5)
As a result, the light emitting layer also served as the second hole injecting and transporting layer. Decompression
While maintaining the state, then on top of it, tris (8-quino
Linoleate) Aluminum vapor deposition rate 0.2nm / sec
Was evaporated to a thickness of 50 nm to form an electron injecting and transporting layer. Decrease
While maintaining the pressure state, further on it, magnesium
Silver is deposited to a thickness of 200 nm at a deposition rate of 0.2 nm / sec.
Co-evaporation (weight ratio 10: 1) is used as the cathode and organic electroluminescence
A device was produced. DC voltage applied to the fabricated organic electroluminescent device
Applied in a dry atmosphere at 10 mA / cm ²Constant current density
It was driven continuously. Initially 6.2V, brightness 640c
d / m²The emission of green light was confirmed. Brightness half-life is 1
It was 550 hours.

Example 29 Glass with ITO transparent electrode (anode) of 200 nm thickness
Substrate with a neutral detergent, acetone, and ethanol.
Sonicated. Dry the substrate with nitrogen gas,
After UV / ozone cleaning, the substrate holder of vapor deposition equipment
After fixing to, vapor deposition tank 3 × 10^-6The pressure was reduced to Torr. Well
No, the compound of Exemplified Compound No. B-21 was formed on the ITO transparent electrode.
Compound to a thickness of 20 nm at a deposition rate of 0.1 nm / sec.
It was vapor-deposited to form a first hole injecting and transporting layer. Then, the compound
Compound No. A-43 and rubrene are different evaporation sources.
Co-evaporate to a thickness of 55 nm at a deposition rate of 0.2 nm / sec.
(Weight ratio 10: 1) to serve as the second hole injecting and transporting layer.
The light emitting layer was used. Furthermore, on top of that, tris (8-quinoli
Nolato) aluminum at a deposition rate of 0.2 nm / sec
It vapor-deposited to a thickness of 50 nm to form an electron injecting and transporting layer. Furthermore
On top of that, magnesium and silver are deposited at a deposition rate of 0.2 nm.
Co-evaporated to a thickness of 200 nm in 10 sec / sec (weight ratio 10: 1)
As a cathode, an organic electroluminescence device was produced. Evaporation
Was carried out while maintaining the vacuum state of the vapor deposition tank. Made
Applying a DC voltage to the organic electroluminescent device, and in a dry atmosphere,
10 mA / cm ²It was continuously driven at a constant current density of. Early on
Is 6.1 V, brightness 650 cd / m²The yellow emission of
It has been certified. The half-life of brightness was 1600 hours.

Example 30 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 and further UV / ozone washed. Next, on the ITO transparent electrode, polycarbonate (weight average molecular weight 50,000),
And a compound of Exemplified Compound No. A-50 in a weight ratio of 100:
Using a 3% by weight dichloroethane solution contained in a ratio of 50, a hole injecting and transporting layer having a thickness of 40 nm was formed by a dip coating method. Next, after fixing the glass substrate having the hole injecting and transporting layer to the substrate holder of the vapor deposition apparatus, the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. Next, 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 obtain a light emitting layer which also serves as an electron injecting and transporting layer. Furthermore, on the light emitting layer,
200 for magnesium and silver at a deposition rate of 0.2 nm / sec
co-deposited to a thickness of nm (weight ratio 10: 1) to form a cathode,
An organic electroluminescent device was produced. When a DC voltage of 10 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 95 mA / cm ² flowed. Brightness 1200 cd
A green emission of / m ² was confirmed. Luminance half-life is 28
It was 0 hours.

Example 31 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 and further UV / ozone washed. Next, polymethylmethacrylate (weight average molecular weight 250
00), compound of Exemplified Compound No. B-26, tris (8
-Quinolinolato) aluminium, each in a weight ratio of 1
100% by a dip coating method using a 3% by weight dichloroethane solution contained in a ratio of 00: 50: 0.5.
nm emission layer was formed. Next, after fixing the glass substrate having this light emitting layer to the substrate holder of the vapor deposition apparatus, the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. Further, magnesium and silver are deposited on the light emitting layer at a deposition rate of 0.2 nm / sec.
An organic electroluminescent device was produced by co-evaporating to a thickness of 00 nm (weight ratio 10: 1) to form a cathode. When a DC voltage of 15 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 80 mA / cm ² flowed. Brightness 700c
Green light emission of d / m ² was confirmed. Brightness half-life is 3
It was 50 hours.

[0077]

According to the present invention, it has become possible to provide an organic electroluminescent device having high luminous efficiency, long emission life and excellent durability.

[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 injection transport layer 3a: hole injecting and transporting component 4: Light emitting layer 4a: luminous component 5: Electron injection transport layer 5 ": electron injection transport layer 5a: electron injection transport component 6: Cathode 7: Power supply

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Yoshimitsu Tanabe             Mitsui Chemicals Co., Ltd. 580-32 Nagaura, Sodegaura City, Chiba Prefecture             Inside the company (72) Inventor Yoshiyuki Toya             Mitsui Chemicals Co., Ltd. 580-32 Nagaura, Sodegaura City, Chiba Prefecture             Inside the company F term (reference) 3K007 AB03 AB04 AB11 CA01 CB01                       DA01 DB03 EB00

Claims (5)

[Claims] 1. An organic electroluminescence device comprising at least one layer containing at least one compound represented by the general formula (1) sandwiched between a pair of electrodes. [Chemical 1] (In the formula, Ar _{1 to} Ar ₄ each independently represent a substituted or unsubstituted aryl, and further, Ar ₁ and Ar ₂ and A
r ₃ and Ar ₄ represent that a nitrogen-containing heterocycle may be formed together with the bonded nitrogen atom, and m represents 0 or 1.) 2. The organic electroluminescent device according to claim 1, wherein the layer containing the compound represented by the general formula (1) is a hole injecting and transporting layer. 3. The organic electroluminescent device according to claim 1, wherein the layer containing the compound represented by the general formula (1) is a light emitting layer. 4. The organic electroluminescent device according to claim 1, further comprising a light emitting layer between the pair of electrodes. 5. The organic electroluminescent device according to claim 1, further comprising an electron injecting and transporting layer between the pair of electrodes.