JP2003261472A - Organic electroluminescent element and new hydrocarbon compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescent element excellent in luminous efficiency and emitting light with high intensity and to obtain a new organic hydrocarbon compound for the same. <P>SOLUTION: This invention comprises the organic electroluminescent element comprising at least one layer which contains at least one compound expressed by formula (1), between a pair of electrodes and the compound expressed by formula (1). (In formula (1), Ar is a (substituted) anthryl group, Z<SB>1</SB>, Z<SB>2</SB>and Z<SB>3</SB>are each H, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a (substituted) aryl group or a (substituted) aralkyl group). <P>COPYRIGHT: (C)2003,JPO

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 electroluminescent device (organic electroluminescence device: organic EL device) using an organic material as a light emitting material has been developed [Appl.Phys.Lett., 51,913 (19
87)]. The 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 low DC voltage of about several V to several tens of V, and various colors (for example, red, blue, green) can be obtained by selecting the type 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 light emission 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.

[0004]

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.

[0005]

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 electrodes.

[0007]

[Chemical 3]

(In the formula, Ar represents a substituted or unsubstituted anthryl group, and Z ₁ , Z ₂ and Z ₃ are hydrogen atoms, halogen atoms, linear, branched or cyclic alkyl groups, linear, branched or cyclic. Represents an alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group.)

The layer containing the compound represented by the general formula (1) further contains a luminescent organometallic complex, and the organic electroluminescent element 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) having a hole injecting and transporting layer, the organic electroluminescent device according to 1) further having an electron injecting and transporting layer between a pair of electrodes, represented by the following general formula (1): Hydrocarbon compounds represented,

[0010]

[Chemical 4]

(In the formula, Ar represents a substituted or unsubstituted anthryl group, and Z ₁ , Z ₂ and Z ₃ are hydrogen atoms, halogen atoms, linear, branched or cyclic alkyl groups, linear, branched or cyclic groups. Represents an alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group.

[0012]

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.

[0013]

[Chemical 5]

(In the formula, Ar represents a substituted or unsubstituted anthryl group, Z ₁ , Z ₂ and Z ₃ are a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic group. Represents an alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group.) In the compound represented by the general formula (1), Ar represents a substituted or unsubstituted anthryl group. Ar is a substituted or unsubstituted 1-anthryl group, a substituted or unsubstituted 2-
It is an anthryl group or a substituted or unsubstituted 9-anthryl group, preferably a substituted or unsubstituted 9-anthryl group.

When Ar has a substituent, examples of the substituent include a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted amino group and a substituted group. Alternatively, an unsubstituted aryl group, or a substituted or unsubstituted aralkyl group can be used.

In the present invention, the aryl group means a carbocyclic aromatic group such as a phenyl group, a naphthyl group and an anthryl group, and a heterocyclic aromatic group such as a furyl group, a thienyl group and a pyridyl group. Represents a group.

When Ar has a substituent, specific examples of the substituent include halogen atoms such as fluorine atom, chlorine atom and bromine atom, methyl group, ethyl group, n-propyl group, isopropyl group and 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 , A linear, branched or cyclic alkyl group such as n-octadecyl group and n-eicosyl 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. Group, 3,3-dimethylbutyloxy 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- Linear, branched or cyclic alkoxy groups such as octadecyloxy group and n-eicosyloxy group

Amino group, N-methylamino group, N-ethylamino group, Nn-butylamino group, N-cyclohexylamino group, Nn-octylamino group, Nn-decylamino group, N-benzyl Amino 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-butylamino 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-Nn-butylamino group, N-methyl-N-phenyl Amino group, N-n-butyl-N-phenylamino group, N, N-diphenylamino group, N, N-di (3methylphenyl) 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- A 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-
Substituted or unsubstituted amino group such as (4-phenylphenyl) amino 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, 1-naphthyl group, 2-naphthyl group, 1,2,3,4-tetrahydro-5-naphthyl group, 1,2,3,4-tetrahydro-6- Naphthyl group, 4-ethyl-1-naphthyl group, 6-
n-butyl-2-naphthyl group, 1-anthryl group, 2-
Anthryl group, 9-anthryl group, 10-phenyl-9
-Anthryl group, 10- (4'-methylphenyl) -9
-Anthryl group, 10- (2 ', 4'-dimethylphenyl) -9-anthryl group, 10- (2'-phenylphenyl) -9-anthryl group, 10- (3'-phenylphenyl) -9-anthryl group Group, 10- (4'-phenylphenyl) -9-anthryl group, 3,6-di-tert
-Butyl-10-phenyl-9-anthryl group, 10-
(1'-naphthyl) -9-anthryl group, 10- (2 '
-Naphthyl) -9-anthryl group, 9,10-diphenyl-1-anthryl group, 9,10-diphenyl-2-anthryl group, 9,10-di (4'-methylphenyl)-
1-anthryl group, 9,10-di (4'-methylphenyl) -2-anthryl group, 9,10-di (1'-naphthyl) -2-anthryl group, 9,10-di (2'-naphthyl) ) -2-anthryl group, 9,10-di (2′-phenylphenyl) -2-anthryl group, 9,10-di (3 ′)
-Phenylphenyl) -2-anthryl group, 9,10-
Di (4'-phenylphenyl) -2-anthryl group, 6
-Tert-butyl-9,10-diphenyl-2-anthryl group, 5-indanyl 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, 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,

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-
Amino-2-naphthyl group,

4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 3,5-diphenylphenyl 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, 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-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, 2,4
-Dichloro-1-naphthyl group, 1,6-dichloro-2-
Naphthyl 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- A substituted or unsubstituted carbocyclic aromatic group such as methoxy-6-chlorophenyl group, 5-chloro-2,4-dimethoxyphenyl 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),
Z ₁ , Z ₂ and Z ₃ 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 aryl group, or a substituted or unsubstituted aralkyl group.

Further, in the compound represented by the general formula (1), the aryl group and aralkyl group of Z ₁ , Z ₂ and Z ₃ may have a substituent, and a halogen atom and a carbon number of 1 to 16 A straight chain, branched or cyclic alkyl group, a straight chain, branched or cyclic alkoxy group having 1 to 16 carbon atoms, an N-monosubstituted amino group having 1 to 20 carbon atoms, and 2 to 40 carbon atoms
May be mono- or poly-substituted with a substituent such as N, N-disubstituted amino group, aryl group having 3 to 25 carbon atoms, or aralkyl group having 5 to 16 carbon atoms.

Z ₁ , Z ₂ and Z ₃ are preferably hydrogen atom, halogen atom, straight chain, branched or cyclic alkyl group having 1 to 16 carbon atoms, straight chain, branched or cyclic group having 1 to 16 carbon atoms. Alkoxy group, substituted or unsubstituted carbocyclic aromatic group having 6 to 25 carbon atoms, substituted or unsubstituted heterocyclic aromatic group having 3 to 25 carbon atoms, or 5 to 16 carbon atoms
Is a substituted or unsubstituted aralkyl group, more preferably a hydrogen atom, a halogen atom, a straight chain, branched or cyclic alkyl group having 1 to 10 carbon atoms, a straight chain, branched or cyclic group having 1 to 10 carbon atoms. An alkoxy group, a substituted amino group having 1 to 20 carbon atoms, a substituted or unsubstituted carbocyclic aromatic group having 6 to 12 carbon atoms, a substituted or unsubstituted heterocyclic aromatic group having 4 to 12 carbon atoms, or , A substituted or unsubstituted aralkyl group having 7 to 12 carbon atoms, and more preferably
Hydrogen atom, halogen atom, linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms, substituted or unsubstituted carbon having 6 to 10 carbon atoms Cyclic aromatic group, substituted or unsubstituted heterocyclic aromatic group having 4 to 10 carbon atoms, or 7 to 10 carbon atoms
Is a substituted or unsubstituted aralkyl group.

Specific examples of the groups Z ₁ , Z ₂ and Z ₃ include a hydrogen atom and a halogen atom, a straight chain, branched or cyclic alkyl group which is a specific example of the substituent when Ar has a substituent. Group, linear, branched or cyclic alkoxy group, substituted or unsubstituted carbocyclic aromatic group, substituted or unsubstituted heterocyclic aromatic group, and substituted or unsubstituted aralkyl group, and the like. it can.

The organic electroluminescent device of the present invention is characterized by using at least one compound represented by the general formula (1). 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-24 and B-1 to
The compounds of B-24, C-1 to C-24 and D-1 to D-18 can be mentioned, but the present invention is not limited thereto.

[0034]

[Chemical 6]

[0035]

[Chemical 7]

[0036]

[Chemical 8]

[0037]

[Chemical 9]

[0038]

[Chemical 10]

[0039]

[Chemical 11]

[0040]

[Chemical 12]

[0041]

[Chemical 13]

[0042]

[Chemical 14]

[0043]

[Chemical 15]

[0044]

[Chemical 16]

[0045]

[Chemical 17]

[0046]

[Chemical 18]

[0047]

[Chemical 19]

[0048]

[Chemical 20]

[0049]

[Chemical 21]

[0050]

[Chemical formula 22]

[0051]

[Chemical formula 23]

[0052]

[Chemical formula 24]

[0053]

[Chemical 25]

[0054]

[Chemical formula 26]

[0055]

[Chemical 27]

[0056]

[Chemical 28]

[0057]

[Chemical 29]

[0058]

[Chemical 30]

[0059]

[Chemical 31]

[0060]

[Chemical 32]

[0061]

[Chemical 33]

[0062]

[Chemical 34]

[0063]

[Chemical 35]

The compound represented by the general formula (1) according to the present invention can be produced, for example, by the following method. That is, for example, a compound represented by the following general formula (2) is combined with a compound represented by the following general formula (3), for example, a palladium compound [eg, tetrakis (triphenylphosphine) palladium, bis (triphenyl) [Phosphine) palladium dichloride] and a base (eg, sodium carbonate, sodium hydrogen carbonate, triethylamine) [eg, Chem. Rev.,
The method described in 95 , 2457 (1995) can be referred to].

[0065]

[Chemical 36]

[In the above formula, Ar, Z ₁ , Z ₂ and Z ₃ are
It has the same meaning as in the case of the general formula (1) and X ₁ represents a halogen atom.] In the general formula (2), X ₁ represents a halogen atom, preferably a chlorine atom, a bromine atom or an iodine atom.

Further, for example, a compound represented by the following general formula (4) can be prepared by combining a compound represented by the following general formula (3) and a compound represented by the following general formula (5) with a palladium compound [ For example, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride] and a base (eg, sodium carbonate, sodium hydrogen carbonate, triethylamine) are reacted [eg, Chem. Rev., 95 . , 245
The method described in 7 (1995) can be referred to] to produce a compound in which Z ₃ is an aryl group in the general formula (1).

[0068]

[Chemical 37]

[In the above formula, Ar, Z₁, And Z₂Is general
It has the same meaning as in the case of formula (1), and Z ₃Is an aryl group
Represent, X₁And X₂Represents a halogen atom) In the general formula (4), X₁And X₂Is a halogen atom
Represents, preferably a chlorine atom, a bromine atom, an iodine atom
Represent

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 (for example, an aromatic hydrocarbon solvent such as toluene) optionally used. However, in the present invention, 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 electroluminescent 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 electroluminescent element is usually formed by sandwiching at least one light emitting layer containing at least one kind of light emitting component 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 in 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 and transporting layer, the electron injecting and transporting layer, and the light emitting layer may have a single-layer structure or a multi-layered structure. The layers 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) 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 element 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 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 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 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. 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 device 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, 6 is a cathode, and 7 is a power source.

The electroluminescent device of the present invention is preferably supported on the substrate 1. The substrate is not particularly limited, but it is preferably transparent or translucent, for example, a glass plate or a transparent plate. Plastic sheet (eg polyester, polycarbonate, polysulfone, polymethylmethacrylate, polypropylene, polyethylene, etc. sheet), translucent plastic sheet,
Examples thereof include those made of quartz, transparent ceramics, or a composite sheet combining these. Further, on the substrate, for example, a color filter film, a color conversion film,
It is also possible to control the emission color by combining a dielectric reflection film.

As 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 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 hundreds Ω / □ or less, more preferably about 5 to 50Ω / □. The thickness of the anode depends on the material of the electrode material used, but in general,
5 to 1000 nm, more preferably 10 to 500
Set to about 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) according to the present invention and / or another compound having a hole injecting and transporting function (for example, a phthalocyanine derivative, a triarylmethane derivative, a triarylamine derivative, At least one of 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. The compounds having a hole injecting and transporting function 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, 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
Examples include-(4'-diphenylaminophenyl) -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 occupied. The ratio of the compound represented by is preferably 0.1
It is adjusted to about 99.9% 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 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 triarylamine derivatives 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, 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
Examples include -diphenyl-4 "-aminophenyl) ethenyl] benzene and 4,4'-bis [2"-(N, N-diphenyl-4 "'-aminophenyl) ethenyl] biphenyl.

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, it is preferable that the light emitting layer 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 0.001 to 99.999% by weight, more preferably 0.01 to 99.99% by weight, and further preferably 0.1 to 99.9% by weight.

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, such as 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 compounds having an electron injecting and transporting function 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-quinolinolate 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 complex represented by the general formula (a) to the general formula (c).

(Q) ₃ -Al (a) (wherein Q represents a substituted or unsubstituted 8-quinolinolato ligand) (Q) ₂ -Al-OL (b) (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 (c) (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 and another compound having an electron injecting and transporting function are used in combination, the compound represented by the general formula (1) according to the present invention in the electron injecting and transporting layer is represented. The ratio of the compound to be prepared is preferably 0.1.
It is adjusted to about 40% by weight.

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 material.

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 should 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 or a cluster ion beam method. You can Further, the cathode may have a single-layer structure or a multi-layer structure. The sheet electrical resistance of the cathode is
It is preferably set to several hundred Ω / □ or less.

The thickness of the cathode depends on the material of the electrode substance used, but is generally set to about 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 preferably transparent or semitransparent, and generally, the transmittance of the emitted light is 70% or more. It is more preferable to set the material and thickness of the anode.

Further, in the organic electroluminescent element of the present invention, at least one layer thereof 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. . 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 weight, preferably 0.0 to 50% by weight based on the total amount of the layer (for example, the hole injecting and transporting layer) to be contained.
5 to 30% by weight, more preferably 0.1 to 20% by weight
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 vacuum vapor deposition, ionization vapor deposition, solution coating (eg spin coating, casting 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 vapor deposition 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, each layer such as the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is 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 deposition 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 organic solvents are hexane, octane, decane, toluene, xylene, ethylbenzene, 1
-Hydrocarbon solvent such as methylnaphthalene; ketone solvent such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone; halogen such as dichloromethane, chloroform, tetrachloromethane, dichloroethane, trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene, chlorotoluene Ester solvents such as ethyl acetate, butyl acetate and amyl acetate; alcohol solvents such as methanol, propanol, butanol, pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve and ethylene glycol; dibutyl ether , Ether solvents such as tetrahydrofuran, dioxane, and anisole; N, N-dimethylformamide, N, N-dimethyl Acetamide, 1-methyl-2-pyrrolidone, 1-methyl-2-imidazolidinone, a polar solvent such as dimethyl sulfoxide and the like.

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 them 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% by weight. %, Preferably a solution concentration of about 1 to 30% by weight. In addition, when a binder resin is used, the amount used is not particularly limited, but in general, the amount of each component (in the case of forming a single-layer type element, the total amount of each component is not limited). ), About 5 to 99.9% by weight, preferably 10 to 9
About 9.9% by weight, more preferably 15 to 90% by weight
Set to a degree.

The thickness of the hole injecting / transporting layer, the light emitting layer, and the electron injecting / transporting layer is not particularly limited, but generally, it is 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 inorganic materials include diamond thin films, amorphous silica, electrically insulating glass, metal oxides, metal nitrides, metal carbonides, and metal sulfides.

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.

[0130]

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 Production of Exemplified Compound A-1 9- (4′-iodophenyl) -9-phenylfluorene 4.44 g, anthracene-9-ylboric acid 2.22
g, 2.12 g of sodium carbonate and 0.35 g of tetrakis (triphenylphosphine) palladium were heated under reflux in toluene (100 ml) and water (50 ml) for 5 hours. After toluene was distilled off from the reaction mixture, the precipitated solid was filtered. This solid was processed by silica gel column chromatography (eluent: toluene).
After toluene was distilled off under reduced pressure, the residue was recrystallized from toluene to obtain 3.75 g of the compound of Exemplified compound A-1 as pale yellow crystals.

(Production Example 2) Production of Exemplified Compound A-2 In Production Example 1, anthracene-9-ylboric acid 2.
Instead of 22 g, 10-phenylanthracene-9-
4.57 g of the compound of Exemplified Compound No. A-2 was obtained as pale yellow crystals according to the procedure described in Production Example 1 except that 2.98 g of irboric acid was used.

Production Example 3 Production of Exemplified Compound A-5 In Production Example 1, anthracene-9-ylboric acid 2.
Production Example 1 except that 3.74 g of 9,10-diphenylanthracen-2-ylboric acid was used instead of 22 g.
According to the operation described in (4), 4.79 g of the compound of Exemplified Compound No. A-5 was obtained as pale yellow crystals.

(Production Example 4) Production of Exemplified Compound A-13 In Production Example 1, anthracene-9-ylboric acid 2.
Instead of 22 g, 10- (2'-phenylphenyl)
Exemplified Compound No. A-according to the procedure described in Production Example 1 except that 3.74 g of anthracene-9-ylboric acid was used.
5.05 g of the compound of 13 was obtained as pale yellow crystals.

Production Example 5 Production of Exemplified Compound A-14 In Production Example 1, anthracene-9-ylboric acid was added.
Instead of 22 g, 10- (N, N-diphenyl-4 ′)
-Aminophenyl) anthracene-9-ylboric acid 4.
According to the procedure described in Production Example 1, except that 65 g was used,
5.46 g of the compound of Exemplified Compound No. A-14 was obtained as pale yellow crystals.

(Production Example 6) Production of Exemplified Compound A-17 In Production Example 1, anthracene-9-ylboric acid 2.
The compound of Exemplified Compound No. A-17 was converted into pale yellow crystals according to the procedure described in Production Example 1 except that 9-N, N-diphenylanthracene-9-ylboric acid (3.89 g) was used instead of 22 g. Obtained 5.22 g.

Production Example 7 Production of Exemplified Compound B-2 9,9-Bis (4′-iodophenyl) fluorene 5.
70 g, 10.98 g of 10-phenylanthracene-9-ylboric acid, 1.21 g of phenylboric acid, 4.24 g of sodium carbonate and 0.7 g of tetrakis (triphenylphosphine) palladium in toluene (100 ml) and water (50 ml). The mixture was heated under reflux for 5 hours. After toluene was distilled off from the reaction mixture, the precipitated solid was filtered. This solid was processed by silica gel column chromatography (eluent: toluene). After distilling off toluene under reduced pressure, the residue was recrystallized from toluene to give Exemplified Compound B.
The compound of -2 was obtained as pale yellow crystals (2.56 g).

Production Example 8 Production of Exemplified Compound B-5 In Production Example 7, 10-phenylanthracene-9-
Exemplified Compound No. B was prepared according to the procedure described in Production Example 7 except that 3.74 g of 9,10-diphenylanthracene-2-ylboric acid was used instead of 2.98 g of ilboric acid.
2.53 g of the compound of -5 was obtained as pale yellow crystals.

Production Example 9 Production of Exemplified Compound B-14 In Production Example 7, 10-phenylanthracene-9-
Instead of 2.98 g of ilboric acid, 10- (N, N-diphenyl-4′-aminophenyl) anthracene-9-
3.01 g of the compound of Exemplified Compound No. B-14 was obtained as pale yellow crystals according to the procedure described in Production Example 7 except that 4.65 g of irboric acid was used.

Production Example 10 Production of Exemplified Compound B-17 In Production Example 7, 10-phenylanthracene-9-
Instead of 2.98 g of ilboric acid, 10- (N, N-diphenyl-4′-aminophenyl) anthracene-9-
Exemplified Compound No. B-17 was prepared according to the procedure described in Production Example 7 except that 4.65 g of ilboric acid was used in place of 1.21 g of phenylboric acid and N, N-diphenyl-4-aminophenylboric acid was 2.98. 3.44 g of the compound was obtained as pale yellow crystals.

Production Example 11 Production of Exemplified Compound B-18 In Production Example 7, 10-phenylanthracene-9-
Exemplified Compound No. B was prepared according to the procedure described in Preparation Example 7 except that 5.56 g of 9,10-bis (N, N-diphenylamino) anthracene-2-ylboric acid was used instead of 2.98 g of ilboric acid. The compound of -18 was obtained as pale yellow crystals (3.62 g).

Production Example 12 Production of Exemplified Compound C-2 9,9-bis (4′-iodophenyl) fluorene 5.
70 g, 10.96 g of 10-phenylanthracene-9-ylboric acid, 4.24 g of sodium carbonate and 0.7 g of tetrakis (triphenylphosphine) palladium were heated to reflux in toluene (100 ml) and water (50 ml) for 5 hours. After toluene was distilled off from the reaction mixture, the precipitated solid was filtered. This solid was processed by silica gel column chromatography (eluent: toluene). After toluene was distilled off under reduced pressure, the residue was recrystallized from toluene to obtain 6.58 g of the compound of Exemplified Compound C-2 as pale yellow crystals.

Production Example 13 Production of Exemplified Compound C-4 In Production Example 12, 10-phenylanthracene-9 was used.
10- (2'-methylphenyl) anthracene-9-ylboric acid 6.24 instead of 5.96 g of ylboric acid
5. According to the procedure described in Production Example 12 except that g was used, the compound of Exemplified Compound No. C-4 was obtained as pale yellow crystals.
47 g was obtained.

Production Example 14 Production of Exemplified Compound C-5 In Production Example 12, 10-phenylanthracene-9 was used.
-Compound of Exemplified Compound No. C-5 was pale yellow according to the procedure described in Production Example 12 except that 7.48 g of 9,10-diphenylanthracene-2-ylboric acid was used instead of 5.96 g of ylboric acid. 7.51 g was obtained as a crystal of.

Production Example 15 Production of Exemplified Compound C-7 In Production Example 12, 10-phenylanthracene-9 was used.
-Compound of Exemplified Compound No. C-7 according to the procedure described in Production Example 12 except that 6.96 g of 10- (2'-naphthyl) anthracene-9-ylboric acid was used instead of 5.96 g of ylboric acid. 7.21g as pale yellow crystals
Obtained.

Production Example 16 Production of Exemplified Compound C-13 In Production Example 12, 10-phenylanthracene-9 was used.
-10- (2'-phenylphenyl) anthracene-9-ylboric acid 7.4 instead of 5.96 g of ylboric acid
According to the procedure described in Production Example 12, except that 8 g was used,
7.80 g of the compound of Exemplified Compound No. C-13 was obtained as pale yellow crystals.

Production Example 17 Production of Exemplified Compound C-14 In Production Example 12, 10-phenylanthracene-9 was used.
-Instead of 5.96 g of ylboric acid, 10- (N, N-
Diphenyl-4'-aminophenyl) anthracene-9
-By following the procedure described in Production Example 12 except that 9.31 g of ylboric acid was used, 8.80 g of the compound of Exemplified Compound No. C-14 was obtained as pale yellow crystals.

Production Example 18 Production of Exemplified Compound C-17 In Production Example 12, 10-phenylanthracene-9 was used.
-Instead of 5.96 g of ylboric acid, 10- (N, N-
Diphenylamino) anthracene-9-ylboric acid 7.
According to the procedure described in Production Example 12 except that 79 g was used, 7.94 g of the compound of Exemplified Compound No. C-17 was obtained as pale yellow crystals.

Production Example 19 Production of Exemplified Compound D-3 9,9-Bis (4′-iodophenyl) fluorene 5.
70 g, 10-phenylanthracene-9-ylboric acid 2.98 g, 9,10-diphenylanthracene-2-
Irboric acid 3.74 g, sodium carbonate 4.24 g and tetrakis (triphenylphosphine) palladium 0.7 g were added to toluene (100 ml) and water (50 m).
Heated to reflux in 1) for 5 hours. After toluene was distilled off from the reaction mixture, the precipitated solid was filtered. This solid was processed by silica gel column chromatography (eluent: toluene). After toluene was distilled off under reduced pressure, the residue was recrystallized from toluene to obtain 3.41 g of the compound of Exemplified Compound D-3 as pale yellow crystals.

Production Example 20 Production of Exemplified Compound D-5 In Production Example 19, 10-phenylanthracene-9 was used.
-Instead of 2.98 g of ylboric acid, 10- (N, N-
Diphenylamino) anthracene-9-ylboric acid 3.
According to the procedure described in Production Example 19 except that 89 g was used, 3.66 g of the compound of Exemplified Compound No. D-5 was obtained as pale yellow crystals.

Production Example 21 Production of Exemplified Compound D-14 In Production Example 19, 10-phenylanthracene-9 was used.
-Instead of 2.98 g of ylboric acid, 10- (N, N-
Diphenyl-4-aminophenyl) anthracene-9-
Irroboric acid 4.65 g was replaced by 9,1 instead of 9,10-diphenylanthracen-2-ylboric acid 3.74 g.
0-bis (N, N-diphenylamino) anthracene-
Production Example 19 except that 5.56 g of 2-ylboric acid was used.
According to the operation described in (4), 4.62 g of the compound of Exemplified Compound No. D-14 was obtained as pale yellow crystals.

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 ⁻⁴ Pa. First, on the ITO transparent electrode,
Deposition rate of 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was 0.2 nm / s.
Ec was vapor-deposited to a thickness of 75 nm 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 were further deposited thereon from different vapor deposition sources at a vapor deposition rate of 0.2 nm / sec at 50 nm. Co-deposition (weight ratio 100: 0.5) was performed to the thickness to form a light emitting layer. Next, tris (8-quinolinolato) aluminum is vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 50 nm,
The electron injecting and transporting layer was used. Further, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight 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, 56
A current of mA / cm ² flowed. Blue-green light emission with a luminance of 2380 cd / m ² was confirmed.

(Examples 2 to 21) In Example 1, instead of using the compound of Exemplified compound A-1 in forming the light emitting layer, the compound of Exemplified compound No. A-2 (Example 2), Exemplified compound No. A-5 compound (Example 3), Exemplified compound No. A-13 compound (Example 4), Exemplified compound No. A-14 compound (Example 5), Exemplified compound No. A-17 compound (Example) Example 6), Exemplified Compound No. B-2
Compound (Example 7), compound of Exemplified Compound No. B-5 (Example 8), compound of Exemplified Compound No. B-14 (Example 9), compound of Exemplified Compound No. B-17 (Example 1)
0), the compound of Exemplified Compound No. B-18 (Example 1
1), a compound of Exemplified Compound No. C-2 (Example 1
2), a compound of Exemplified Compound No. C-4 (Example 13),
Exemplified Compound No. C-5 compound (Example 14), Exemplified Compound No. C-7 compound (Example 15), Exemplified Compound No. C-13 compound (Example 16), Exemplified Compound No. C
-14 compound (Example 17), exemplified compound number C-1
7 compound (Example 18), exemplified compound No. D-3 compound (Example 19), exemplified compound No. D-5 compound (Example 20), exemplified compound No. D-14 compound (Example 21) An organic electroluminescence device was produced by the method described in Example 1 except that was used. For each element,
When a DC voltage of 12 V was applied in a dry atmosphere, blue to blue-green light emission was confirmed. Further study its characteristics,
The results are shown in (Table 1).

COMPARATIVE EXAMPLE 1 In Example 1, bis (2-methyl-8-quinolinolate) (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 1).

(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 1).

[0156]

[Table 1]

Example 22 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, 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 ^-4 Pa. First, on the ITO transparent electrode,
4,4 ', 4 "-tris [N- (3'"-methylphenyl) -N-phenylamino] triphenylamine was evaporated at a deposition rate of 0.1 nm / sec to a thickness of 50 nm, and A hole injecting and transporting layer was formed, and 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 (weight ratio 100: 5.0) to form a light emitting layer which also serves as a second hole injecting and transporting layer, and then tris (8-
Quinolinolato) aluminum, vapor deposition rate 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 (weight 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. The prepared organic electroluminescent device was subjected to 15
When a DC voltage of V was applied, a current of 59 mA / cm ² flowed. Blue-green light emission with a luminance of 2580 cd / m ² was confirmed.

(Examples 23 to 42) In Example 22, instead of using the compound of Exemplified compound A-1 in forming the light emitting layer, the compound of Exemplified compound No. A-2 (Example 23) and Exemplified compound were used. No. A-5 compound (Example 24), Exemplified compound No. A-13 compound (Example 2)
5), the compound of Exemplified Compound No. A-14 (Example 2
6), the compound of Exemplified Compound No. A-17 (Example 2
7), a compound of Exemplified Compound No. B-2 (Example 28),
Compound of Exemplified Compound No. B-5 (Example 29), Compound of Exemplified Compound No. B-14 (Example 30), Compound of Exemplified Compound No. B-17 (Example 31), Compound of Exemplified Compound No. B-18 (Example 32), Exemplified compound number C
-2 compound (Example 33), exemplified compound No. C-4 compound (Example 34), exemplified compound No. C-5 compound (Example 35), exemplified compound No. C-7 compound (Example 36) ), The compound of Exemplified Compound No. C-13 (Example 3
7), the compound of Exemplified Compound No. C-14 (Example 3
8), the compound of Exemplified Compound No. C-17 (Example 3
9), a compound of Exemplified Compound No. D-3 (Example 40),
An organic electroluminescent device was produced by the method described in Example 22, except that the compound of Exemplified compound number D-5 (Example 41) and the compound of Exemplified compound number D-14 (Example 42) were used. 15V for each element in a dry atmosphere
When a DC voltage of No. 2 was applied, blue to blue-green light emission was confirmed. Further, its characteristics were examined, and the results are shown in (Table 2).

[0159]

[Table 2]

Example 43 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 ^-4 Pa. First, on the ITO transparent electrode,
Vapor deposition rate of 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was 0.2 nm / se.
It was vapor-deposited with c to a thickness of 75 nm to form a hole injecting and transporting layer.
Then, bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum and the compound of Exemplified Compound No. A-2 were further deposited thereon from different deposition sources at a deposition rate of 0.2 nm / sec at 50 nm. Co-deposition (weight ratio 100: 2.0) was performed to the thickness to form a light emitting layer. Then 1,3
-Bis [5 '-(4 "-tert-butylphenyl)-
1 ′, 3 ′, 4′-oxadiazol-2′-yl] benzene 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. On top of that, magnesium and silver are deposited at a deposition rate of 0.2 nm / sec for 200
co-deposited to a thickness of nm (weight ratio 10: 1) to form a cathode,
An organic electroluminescent device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 58 mA / cm ² flowed. Brightness 2680 cd
A blue-green light emission of / m ² was confirmed.

Example 44 In Example 43, 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 (8-quinolinolato) aluminum and the compound of Exemplified Compound No. B-2 were co-deposited to a thickness of 50 nm (weight ratio 100: 4.0) to form a light emitting layer, but in Example 43. An organic electroluminescent device was produced by the method described.
When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 59 mA / cm ² flowed. Blue-green light emission with a luminance of 2870 cd / m ² was confirmed.

Example 45 In Example 43, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and Exemplified Compound A-2 in the formation of the light emitting layer in Example 43, , Screw (2
-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-2, 50
An organic electroluminescent element was produced by the method described in Example 43 except that the light emitting layer was formed by co-evaporation to a thickness of nm (weight ratio 100: 3.0). In the produced organic electroluminescent element,
When a DC voltage of 12 V was applied in a dry atmosphere, it was 5
A current of 9 mA / cm ² flowed. Blue-green light emission with a luminance of 2880 cd / m ² was confirmed.

Example 46 In Example 43, 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 in Example 43. , Tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-5 were co-evaporated to a thickness of 50 nm (weight ratio 100: 4.0) to form a light emitting layer, but in Example 43. An organic electroluminescent device was produced by the method described.
When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 56 mA / cm ² flowed. Blue-green light emission with a luminance of 2730 cd / m ² was confirmed.

Example 47 In Example 43, 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 in Example 43. , Screw (2
-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-13 were used to give 5
An organic electroluminescence device was produced by the method described in Example 43 except that the light emitting layer was formed by co-evaporation to a thickness of 0 nm (weight ratio 100: 3.0). When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 57 mA / cm ² flowed. Brightness 2780 cd
A blue-green light emission of / m ² was confirmed.

Example 48 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, 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 ^-4 Pa. First, on the ITO transparent electrode,
4,4′-bis [N-phenyl-N- (1 ″ -naphthyl) amino] biphenyl was vapor-deposited to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec to form a hole injecting and transporting layer. Above, the compound of Exemplified Compound No. A-2 and 1,4
-Bis [2 '-(N, N-diphenyl-4 "-aminophenyl) ethenyl] benzene was co-evaporated from different evaporation sources at a deposition rate of 0.2 nm / sec to a thickness of 50 nm (weight ratio 100: 5. .0) to form a light emitting layer, and then tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.
It was vapor-deposited at a thickness of 50 nm at 2 nm / sec 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 (weight 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. The prepared organic electroluminescent device was placed in a dry atmosphere for 1
When a DC voltage of 2 V was applied, a current of 62 mA / cm ² flowed. Blue-green light emission with a luminance of 3180 cd / m ² was confirmed.

Example 49 In Example 48, the compound of Exemplified Compound No. A-2 and 1,4-bis [2 ′-(N, N-diphenyl-4 ″ -aminophenyl) were used in the formation of the light emitting layer. Instead of using ethenyl] benzene, the compound of Exemplified Compound No. A-5 and 4,4′-bis
[2 ″-(N, N-diphenyl-4 ′ ″-aminophenyl) ethenyl] biphenyl was co-deposited to a thickness of 50 nm (weight ratio 100: 4.0), except that a light emitting layer was formed. An organic electroluminescent device was produced by the method described in Example 48. 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 50 In Example 48, the compound of Exemplified Compound No. A-2 and 1,4-bis [2 ′-(N, N-diphenyl-4 ″ -aminophenyl) were used in the formation of the light emitting layer. Instead of using ethenyl] benzene, the compound of Exemplified Compound No. B-2 and 1,4-bis [2 ′-(N, N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene were used, and the thickness was 50 nm. An organic electroluminescence device was produced by the method described in Example 48 except that the light emitting layer was formed by co-evaporation (weight ratio 100: 7.0). When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 63 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 3460 cd / m ² was confirmed.

Example 51 In Example 48, the compound of Exemplified Compound No. A-2 and 1,4-bis [2 ′-(N, N-diphenyl-4 ″ -aminophenyl) were used in the formation of the light emitting layer. Instead of using ethenyl] benzene, the compound of Exemplified Compound No. C-2 and 4,4′-bis
[2 ″-(N, N-diphenyl-4 ′ ″-aminophenyl) ethenyl] biphenyl was co-deposited to a thickness of 50 nm (weight ratio 100: 10.0), except that a light emitting layer was formed. An organic electroluminescent device was produced by the method described in Example 48. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, 60 mA / cm 2 was obtained.
^Two currents flowed. Blue-green light emission with a luminance of 3170 cd / m ² was confirmed.

Example 52 In Example 48, the compound of Exemplified Compound No. A-2 and 1,4-bis [2 ′-(N, N-diphenyl-4 ″ -aminophenyl) were used in the formation of the light emitting layer. Instead of using ethenyl] benzene, the compound of Exemplified Compound No. C-5 and 1,4-bis [2 ′-(N, N-diphenyl-4 ″ -aminophenyl) ethenyl] benzene were used, and the thickness was 50 nm. An organic electroluminescence device was produced by the method described in Example 48 except that the light emitting layer was formed by co-evaporation (weight ratio 100: 7.0). When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 62 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 3110 cd / m ² was confirmed.

(Example 53) In Example 48, the compound of Exemplified Compound No. A-2 and 1,4-bis [2 '-(N, N-diphenyl-4 "-aminophenyl) were used in the formation of the light emitting layer. Instead of using ethenyl] benzene, the compound of Exemplified Compound No. C-13 and 4,4′-bis [2 ″-(N, N-diphenyl-4 ″ ′-aminophenyl) ethenyl] biphenyl were used, An organic electroluminescent element was produced by the method described in Example 48 except that the light emitting layer was formed by co-evaporating to a thickness of 50 nm (weight ratio 100: 10.0). 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 3150 cd / m ² was confirmed.

Example 54 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 (weight average molecular weight: 150,000), compound of Exemplified Compound No. A-2, coumarin 6 ["3- (2'-benzothiazolyl) -7-diethylaminocoumarin" ( Green emission component)], and DCM-1 [“4- (dicyanomethylene) -2-methyl-6- (4′-dimethylaminostyryl) -4H-pyran” (orange emission component)], respectively. Using a 3% by weight dichloroethane solution contained in a weight ratio of 100: 5: 3: 2, a 400 nm light emitting layer was formed by a dip coating method.
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 4 × 10 ⁻⁴ Pa. Furthermore, 3- (4'-tert-butylphenyl) -4-phenyl-5- (4 "-phenylphenyl) -1,2,4-triazole was deposited on the light emitting layer at a deposition rate of 0.2.
After vapor deposition to a thickness of 20 nm at nm / sec, tris (8-quinolinolato) aluminum is further deposited thereon.
Evaporate to a thickness of 30 nm at an evaporation rate of 0.2 nm / sec,
The electron injecting and transporting layer was used. Further, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. When a direct current voltage of 12 V was applied to the produced organic electroluminescent element in a dry atmosphere, it was 74 m.
A current of A / cm ² flowed. White light emission with a luminance of 1480 cd / m ² was confirmed.

(Examples 55 to 61) Instead of using the compound of Exemplified Compound No. A-2 in Example 54, the compound of Exemplified Compound No. A-5 (Example 55) and Exemplified Compound No. A-17 were used. Compound (Example 56), Compound of Exemplified Compound No. B-14 (Example 57), Compound of Exemplified Compound No. C-2 (Example 58), Exemplified Compound No. C
-5 compound (Example 59), exemplified compound No. C-14
The organic electroluminescent element was produced by the method described in Example 54 except that the compound of Example No. 60 (Example 60) and the compound of Exemplified Compound No. D-5 (Example 61) were used. 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 3).

[0173]

[Table 3]

Example 62 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 ^-4 Pa. First, the compound of Exemplified Compound No. A-17 was vapor-deposited on the ITO transparent electrode at a deposition rate of 0.2 nm /
It was vapor-deposited to have a thickness of 75 nm for sec to form a hole injecting and transporting layer. Then, on top of that, 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 a light-emitting layer which also served as an electron injecting and transporting layer.
On top of that, magnesium and silver are deposited at a deposition rate of 0.2.
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. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 57 mA / cm ² flowed. Green light emission with a brightness of 2960 cd / m ² was confirmed.

Example 63 In Example 62, the compound of Exemplified Compound No. B-18 was used instead of the compound of Exemplified Compound No. A-17 in forming the hole injecting and transporting layer. An organic electroluminescent device was produced by the method described in Example 62. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 56 mA / cm ² flowed. Brightness 2740c
Green light emission of d / m ² was confirmed.

(Example 64) In Example 62, except that the compound of Exemplified Compound No. C-14 was used instead of the compound of Exemplified Compound No. A-17 in forming the hole injecting and transporting layer, An organic electroluminescent device was produced by the method described in Example 62. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 59 mA / cm ² flowed. Brightness 2890c
Green light emission of d / m ² was confirmed.

(Example 65) In Example 62, except that the compound of Exemplified Compound No. C-17 was used instead of the compound of Exemplified Compound No. A-17 in forming the hole injecting and transporting layer, An organic electroluminescent device was produced by the method described in Example 62. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 57 mA / cm ² flowed. Brightness 2760c
Green light emission of d / m ² was confirmed.

(Example 66) In Example 62, except that the compound of Exemplified Compound No. D-5 was used instead of the compound of Exemplified Compound No. A-17 in forming the hole injecting and transporting layer. An organic electroluminescent device was produced by the method described in Example 62. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 55 mA / cm ² flowed. Brightness 2640 cd
A green emission of / m ² was confirmed.

(Example 67) In Example 62, except that the compound of Exemplified Compound No. D-14 was used instead of the compound of Exemplified Compound No. A-17 in forming the hole injecting and transporting layer. An organic electroluminescent device was produced by the method described in Example 62. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 57 mA / cm ² flowed. Brightness 2720c
Green light emission of d / m ² was confirmed.

[0180]

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: light emitting layer 4 ′: light emitting layer (a layer in which a light emitting component and a hole injecting and transporting component are mixed) 4 ″: a light emitting layer (a light emitting component and an electron injecting and transporting component Mixed layer) 4 ''': Light emitting layer (layer in which light emitting component, hole injecting and transporting component and electron injecting and transporting component are mixed) 5: Electron injecting and transporting layer 6: Cathode 7: Power supply

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) C09K 11/06 690 C09K 11/06 690 H05B 33/14 H05B 33/14 B 33/22 33/22 D ( 72) Inventor Yoshiyuki Toya Mitsui Chemicals Co., Ltd. 580-32 Nagaura, Sodegaura City, Chiba Prefecture (72) Inventor Masakatsu Nakatsuka 580-32 Nagaura, Sodegaura City, Chiba Mitsui Chemicals Co., Ltd. F Term (reference) 3K007 AB02 AB03 BB02 BB03 CA01 CA02 CA06 CB04 DA01 DB03 FA01 4H006 AA01 AA03 AB91

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, Ar represents a substituted or unsubstituted anthryl group, Z ₁ , Z ₂ and Z ₃ are a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group. , Represents 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 device 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 hydrocarbon compound represented by the following general formula (1). [Chemical 2] (In the formula, Ar represents a substituted or unsubstituted anthryl group, Z ₁ , Z ₂ and Z ₃ are a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group. , Represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group.)