JP2001176665A - Organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic EL element having a high intensity. SOLUTION: As a composition substance of the organic EL element, a benzo perilene compound shown by a formula (1) is used. In the formula, R1 to R14 are respectively and independently, a hydrogen atom, a halogen atom, and a hydroxyl group, an amino group of substitution or non-substitution, a nitro group, cyano group, an alkyl group of substitution or non-substitution, an alkenyl group of substitution or non-substitution, a styril group of substitution or non- substitution, a cyclo-alkyl group of substitution or non-substitution, an alkoxy group of substitution or non-substitution, an aromatic hydrocarbon group of substitution or non-substitution, aromatic hydrocyclic compound group of substitution or non-substitution, an aralkyl group of substitution or non-substitution, an allyloxy group of substitution or non-substitution. A ring may be formed by two of R1 to R14. However, at least one of R1 to R14 is a steric hindrance group which suppresses an association of molecules.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device having excellent light emission characteristics.

[0002]

2. Description of the Related Art An organic electroluminescent device (hereinafter abbreviated as an organic EL device) has a fluorescent property due to the recombination energy of holes injected from an anode and electrons injected from a cathode when an electric field is applied. A self-luminous element utilizing the principle of light emission from a substance. Eastman Kodak C.I. W. Tang et al. Report on a low-voltage driven organic EL device using a stacked device (CW Tang, SAV)
anSlyke, Applied Physics Letters (A
Applied Physics Letters), 5
1, pp. 913, 1987), research on organic EL elements using organic materials as constituent materials has been actively conducted. Tang et al. Use tris (8-hydroxyquinolinol aluminum) for the light emitting layer and a triphenyldiamine derivative for the hole transport layer. The advantages of the stacked structure include: increasing the efficiency of injecting holes into the light emitting layer; increasing the efficiency of generating excitons generated by recombination by blocking electrons injected from the cathode; And confining excitons.
As in this example, the element structure of the organic EL element is a two-layer type of a hole transporting (injection) layer and an electron transporting light emitting layer, or a hole transporting (injection) layer, a light emitting layer, and an electron transporting (injection) layer. Are well known. In such a stacked structure element, in order to increase the recombination efficiency of injected holes and electrons,
The device structure and the formation method are devised.

[0003] As the hole transporting material, 4,4 ', 4 "-tris (3-methylphenylphenylamino) triphenylamine and N, N'-diphenyl-N, N'-bis which are starburst molecules are used. (3-methylphenyl)-
Triphenylamine derivatives such as [1,1'-biphenyl] -4,4'-diamine and aromatic diamine derivatives are well known (for example, JP-A-8-20771,
JP-A-8-40995, JP-A-8-40997, JP-A-8-53397, JP-A-8-8
No. 7122). Oxadiazole derivatives, triazole derivatives and the like are well known as electron transporting materials. Further, as the light emitting material, a light emitting material such as a chelate complex such as a tris (8-quinolinolate) aluminum complex, a coumarin derivative, a tetraphenylbutadiene derivative, a bisstyrylarylene derivative, and an oxadiazole derivative are known. It has been reported that the color can emit light in the visible region from blue to red, and realization of a color display element is expected (for example,
JP-A-8-239655, JP-A-7-13856
No. 1, JP-A-3-200889, etc.).

As described above, various high-luminance, long-life organic EL devices have been disclosed or reported, but are not necessarily satisfactory. The present inventors have disclosed in Japanese Patent Application Laid-Open
As disclosed in Japanese Patent No. 185961, the use of a specific benzoperylene compound can provide an organic EL device exhibiting high-luminance emission. However, in some benzoperylene compounds, since a state of association between molecules is formed, a phenomenon called concentration quenching, in which the emission intensity of the dye is significantly reduced, may be observed. Also, in the case of dye materials used in other organic EL devices, there are many cases where high-concentration dispersion or concentration quenching is observed in a solid formed by the dye alone, in which the molecules are associated with each other. Was.

[0005]

SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and has as its object to provide a high-luminance organic EL device by using a compound in which concentration quenching is suppressed.

[0006]

Means for Solving the Problems The present inventors have conducted intensive studies in order to solve the above-mentioned problems, and as a result, have found that a compound in which a sterically hindered group that suppresses the formation of an associated state has been introduced into a specific benzoperylene derivative. It has been found that an organic EL device manufactured using a light emitting material emits light with higher luminance than before. Further, the material has a high carrier transporting property, and the material is an organic EL device manufactured as a hole transporting material or an electron transporting material; and
An organic EL device manufactured using a mixed thin film with another hole transporting material or an electron transporting material has been found to emit light with higher brightness than ever before, and the present invention has been achieved.

According to the present invention, there is provided an organic EL device having one or more organic thin film layers including a light emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers has a general formula ( 1):

Embedded image

(Wherein R ^{1 to} R ¹⁴ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, Unsubstituted alkenyl group, substituted or unsubstituted styryl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocycle A ring group, a substituted or unsubstituted aralkyl group or a substituted or unsubstituted aryloxy group, and two of R ^{1 to} R ¹⁴ may form a ring, provided that R ¹ at least one to R ¹⁴ are inhibiting sterically hindered group association state formation of intermolecular benzo perylene compound represented by.), including alone or in a mixture Providing an organic EL element, characterized in that.

A second aspect of the present invention is an organic EL device having one or more organic thin film layers including a light emitting layer between a cathode and an anode.
In the device, at least one of the organic thin film layers has a general formula (2):

Embedded image

(Wherein R¹~ R¹⁴Are each independently water
Elemental atom, halogen atom, hydroxyl group, substituted or
Unsubstituted amino, nitro, cyano, substituted or
Unsubstituted alkyl group, substituted or unsubstituted alkenyl
Group, substituted or unsubstituted styryl group, substituted or unsubstituted
Substituted cycloalkyl group, substituted or unsubstituted alcohol
Xyl group, substituted or unsubstituted aromatic hydrocarbon group, substituted
Or unsubstituted aromatic heterocyclic group, substituted or unsubstituted
Aralkyl group, substituted or unsubstituted aryloxy
Represents a group. Also R¹~ R¹⁴Is a ring in two of them
May be formed. Where R¹~ R¹⁴At least
One is -NAr.¹Ar^Two(Ar¹, Ar ^TwoIs a replacement
Or unsubstituted aromatic hydrocarbon group, or substituted or unsubstituted
Which represents a substituted aromatic heterocyclic group)
No group. In addition, R which is not a diarylamino group¹~ R
¹⁴At least one suppresses formation of an association state between molecules.
Sterically hindered groups. Benzoperylene compound represented by)
Organic substances characterized in that they contain substances alone or in mixtures
An EL element is provided.

A third aspect of the present invention is an organic EL device having one or more organic thin film layers including a light emitting layer between a cathode and an anode.
In the L element, at least one of the organic thin film layers includes:
General formula (3):

Embedded image

(Where R¹~ R¹⁴Are each independently water
Elemental atom, halogen atom, hydroxyl group, substituted or
Unsubstituted amino, nitro, cyano, substituted or
Unsubstituted alkyl group, substituted or unsubstituted alkenyl
Group, substituted or unsubstituted styryl group, substituted or unsubstituted
Substituted cycloalkyl group, substituted or unsubstituted alcohol
Xyl group, substituted or unsubstituted aromatic hydrocarbon group, substituted
Or unsubstituted aromatic heterocyclic group, substituted or unsubstituted
Aralkyl group, substituted or unsubstituted aryloxy
Represents a group. Also R¹~ R¹⁴Is a ring in two of them
May be formed. Where R¹~ R¹⁴At least
One is -NAr.¹Ar^Two(Ar¹, Ar ^TwoIs a replacement
Or unsubstituted aromatic hydrocarbon group, or substituted or unsubstituted
Represents a substituted aromatic heterocyclic group. Where Ar¹, Ar^TwoHorse
At least one of which is a substituted or unsubstituted styryl group
As a substituent. A) diarylamino represented by
Group. In addition, R which is not a diarylamino group¹~ R¹⁴
At least one suppresses formation of an intermolecular association state
It is a sterically hindered group. Benzoperylene compound represented by)
, Alone or in a mixture.
An L element is provided.

According to a fourth aspect of the present invention, in the organic EL device according to any one of the first to third aspects, the organic thin-film layer has at least a light-emitting layer, and the light-emitting layer has a general formula (1):
An organic EL device comprising the compound represented by (2) or (3) alone or as a mixture.

According to a fifth aspect of the present invention, in the organic EL device according to any one of the first to third aspects, at least a hole transport layer is provided as the organic thin film layer, and the hole transport layer has a general formula
An organic EL device comprising the compound represented by (1), (2) or (3) alone or as a mixture.

According to a sixth aspect of the present invention, in the organic EL device according to any one of the first to third aspects, the organic thin film layer has at least an electron transporting layer, and the electron transporting layer has a general formula (1) An organic EL device comprising the compound represented by formula (2) or (3) alone or as a mixture.

A seventh aspect of the present invention relates to the organic EL device according to any one of the first to sixth aspects, wherein the general formula (1):
The steric hindrance group of the compound represented by (2) or (3) is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic group Provided is an organic EL device, which is a hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryloxy group.

[0017]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
The compound according to the present invention is a compound having a structure represented by the general formula (1), (2) or (3). R ^{1 to} R
¹⁴ is each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group,
Cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted It represents a substituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, and a carboxyl group. R ^{1 to} R ¹⁴ may form a ring with two of them. However, at least one of R ^{1 to} R ¹⁴ is a sterically hindered group that suppresses formation of an intermolecular association state.

In the general formula (2), at least one of R ^{1 to} R ¹⁴ which is not a sterically hindered group is represented by —NAr ¹ Ar ²
(Ar ¹ and Ar ² represent a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group). In the general formula (3), at least one of Ar ¹ and Ar ² is selected.
One has a substituted or unsubstituted styryl group as a substituent.

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

A substituted or unsubstituted amino group is represented by -NX
Is represented as ¹ X ^2, as the X ^1, X ^2, each independently, a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, n- butyl group, s- butyl group, isobutyl group, t
-Butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-
Hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-tri Hydroxypropyl group, chloromethyl group, 1-chloroethyl group,
2-chloroethyl group, 2-chloroisobutyl group, 1,2
-Dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromo Isobutyl group,
1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3
-Tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl Group, 1,
2,3-triiodopropyl group, aminomethyl group, 1-
Aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group,
1,2,3-triaminopropyl group, cyanomethyl group,
1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricia Propyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3
-Dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group,
1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 4-styrylphenyl group, 1-pyrenyl group,
2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p
-Terphenyl-4-yl group, p-terphenyl-3-
Yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m
-Terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p-
(2-phenylpropyl) phenyl group, 3-methyl-2-
Naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group,
4 ''-t-butyl-p-terphenyl-4-yl group, 2
-Pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 2
-Indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6
-Isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1 -Isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl Group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl Group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxa Group, 1-carbazolyl group,
2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phen Nanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-
Acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,
7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthroline-4
-Yl group, 1,7-phenanthrolin-5-yl group,
1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group Group, 1,8-phenanthrolin-2-yl group, 1,8-
Phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1, 8
Phenanthroline-7-yl group, 1,8-phenanthroline-9-yl group, 1,8-phenanthroline-10
-Yl group, 1,9-phenanthrolin-2-yl group,
1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group Group, 1,9-phenanthrolin-7-yl group, 1,9-
Phenanthroline-8-yl group, 1,9-phenanthroline-10-yl group, 1,10-phenanthroline-2
-Yl group, 1,10-phenanthrolin-3-yl group,
1,10-phenanthrolin-4-yl group, 1,10-
Phenanthrolin-5-yl group, 2,9 phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9 −
Phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group, 2, 9
-Phenanthroline-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthroline-3
-Yl group, 2,8-phenanthrolin-4-yl group,
2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group Group, 2,8-phenanthrolin-10-yl group, 2,7
-Phenanthroline-1-yl group, 2,7-phenanthrolin-3-yl group, 2,7-phenanthroline-4-
Yl group, 2,7-phenanthrolin-5-yl group, 2,
7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthroline-9
An -yl group, a 2,7-phenanthroline-10-yl group,
1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4 -Phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrole-1 -Yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrole-2 -Yl group, 3-methylpyrrole-4-yl group, 3-methylpyrrole-5-yl group,
2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1
-Indolyl group, 4-methyl-1-indolyl group, 2-
Methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t-butyl 3-indolyl group, 4-t- And a butyl 3-indolyl group.

Examples of the substituted or unsubstituted alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group and a t-butyl group.
Butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxy Ethyl group,
1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-
Chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group,
2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group,
1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo t-butyl group, 1,2,3-
Tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group , 1,
2,3-triiodopropyl group, aminomethyl group, 1-
Aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group,
1,2,3-triaminopropyl group, cyanomethyl group,
1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricia Propyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3
-Dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group and the like.

The substituted or unsubstituted alkenyl group includes vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butanedienyl, 1
-Methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group , 1-phenyl-1-
Butenyl and 3-phenyl-1-butenyl.

Examples of the substituted or unsubstituted cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 1-adamantyl group and a 2-adamantyl group.

A substituted or unsubstituted alkoxy group is represented by-
A group represented by OY, wherein Y is methyl, ethyl, propyl, isopropyl, n-butyl, s
-Butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2
-Hydroxyethyl group, 2-hydroxyisobutyl group,
1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl Group, 2
-Chloroisobutyl group, 1,2-dichloroethyl group,
1,3-dichloroisopropyl group, 2,3-dichloro-
t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 3-diiodoisopropyl group, 2,3-
Diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 3-diaminoisopropyl group, 2,
3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group,
-Cyanoethyl group, 2-cyanoisobutyl group, 1,2-
Dicyanoethyl group, 1,3-dicyanoisopropyl group,
2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group,
1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3
-Trinitropropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 1-adamantyl, 2-adamantyl and the like.

Examples of the substituted or unsubstituted aromatic hydrocarbon group include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2 -Phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9
-Phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-
Pyrenyl group, 4-pyrenyl group, 2-biphenylyl group,
3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl Group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p-
(2-phenylpropyl) phenyl group, 3-methyl-2-
Naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group,
4 ''-t-butyl-p-terphenyl-4-yl group and the like.

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

The substituted or unsubstituted aralkyl group includes benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthyl Methyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-
α-naphthylisopropyl group, β-naphthylmethyl group,
1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-
Pyrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromo Benzyl group,
o-bromobenzyl group, p-iodobenzyl group, m-
Iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl Group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group,
Examples thereof include an o-cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group, a 1-chloro-2-phenylisopropyl group, and the like.

A substituted or unsubstituted aryloxy group is represented by —OZ, where Z is a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group,
2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1
-Pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-
Biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl -4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p -(2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, 4 ″ -t -Butyl-p-terphenyl-4-yl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4
-Pyridinyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 3
-Isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5 -Benzofuranyl group, 6-benzofuranyl group, 7
-Benzofuranyl group, 1-isobenzofuranyl group, 3-
Isobenzofuranyl group, 4-isobenzofuranyl group, 5
-Isobenzofuranyl group, 6-isobenzofuranyl group,
7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3- Isoquinolyl group, 4-isoquinolyl group, 5
-Isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group,
5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 1-phenanthridinyl group,
2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9- Phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthroline-2-yl Group, 1,7-phenanthrolin-3-yl group, 1,7-
Phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthroline-8-yl group, 1, 7
-Phenanthroline-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthroline-2
-Yl group, 1,8-phenanthrolin-3-yl group,
1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group Group, 1,8-phenanthrolin-9-yl group, 1,8-
Phenanthroline-10-yl group, 1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3-
Yl group, 1,9-phenanthrolin-4-yl group, 1,
9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthroline-7
-Yl group, 1,9-phenanthroline-8-yl group,
1,9-phenanthrolin-10-yl group, 1,10-
Phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthroline-4
-Yl group, 1,10-phenanthrolin-5-yl group,
2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group Group, 2,9-phenanthrolin-6-yl group, 2,9-
Phenanthroline-7-yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10-
Yl group, 2,8-phenanthrolin-1-yl group, 2,
8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthroline-5
-Yl group, 2,8-phenanthrolin-6-yl group,
2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl Group, 2,7-phenanthrolin-3-yl group, 2,7-
Phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2, 7
-Phenanthroline-9-yl group, 2,7-phenanthroline-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group , 4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl Group, 3-flazanyl group, 2-thienyl group, 3-
Thienyl group, 2-methylpyrrole-1-yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrole-4-yl
Yl group, 2-methylpyrrole-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrole-5-yl Yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-
Indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t-butyl 3-indolyl group , 4-t-butyl 3-indolyl group and the like.

A substituted or unsubstituted alkoxycarbonyl group is represented by —COOY, wherein Y represents a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group,
s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group,
2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, Chloromethyl group, 1-chloroethyl group, 2-chloroethyl group,
2-chloroisobutyl group, 1,2-dichloroethyl group,
1,3-dichloroisopropyl group, 2,3-dichloro-
t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 3-diiodoisopropyl group, 2,3-
Diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 3-diaminoisopropyl group, 2,
3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group,
-Cyanoethyl group, 2-cyanoisobutyl group, 1,2-
Dicyanoethyl group, 1,3-dicyanoisopropyl group,
2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group,
1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3
-A trinitropropyl group and the like.

Examples of the substituted or unsubstituted styryl group include a styryl group, 2,2-diphenylvinyl group, and a halogen atom, a hydroxyl group, -NAr.
³ Ar ⁴ (Ar ³ and Ar ⁴ each independently have 6 to 2 carbon atoms)
Represents an aryl group of 0, and the aryl group may have a substituent. A) a substituted or unsubstituted diarylamino group, a nitro group, a cyano group, the substituted or unsubstituted alkyl group, the substituted or unsubstituted alkenyl group, the substituted or unsubstituted cycloalkyl group The substituted or unsubstituted alkoxy group, the substituted or unsubstituted aromatic hydrocarbon group, the substituted or unsubstituted aromatic heterocyclic group, the substituted or unsubstituted aralkyl group, the substituted Or an unsubstituted aryloxy group, a substituted styryl group having a substituted or unsubstituted alkoxycarbonyl group, a carboxyl group, or the like, or a 2,2-diphenylvinyl group.

The aryl group having 6 to 20 carbon atoms represented by Ar ³ and Ar ⁴ includes a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a naphthacenyl group, a pyrenyl group and the like. Examples of the substituent of the aryl group include a halogen atom, a hydroxyl group, a nitro group,
A cyano group, the substituted or unsubstituted alkyl group, the substituted or unsubstituted alkenyl group, the substituted or unsubstituted cycloalkyl group, the substituted or unsubstituted alkoxy group, the substituted or unsubstituted group Aromatic hydrocarbon group, the substituted or unsubstituted aromatic heterocyclic group, the substituted or unsubstituted aralkyl group, the substituted or unsubstituted aryloxy group, the substituted or unsubstituted alkoxycarbonyl Group, carboxyl group and the like.

In R ^{1 to} R ¹⁴ , a ring-forming 2
Examples of the valent group include a tetramethylene group, a pentamethylene group, a hexamethylene group, and diphenylmethane-2,2'-
Diyl group, diphenylethane-3,3'-diyl group, diphenylpropane-4,4'-diyl group, 1,3-butadiene-1,4-diyl group and the like.

As the sterically hindered group which suppresses the formation of an associated state, any substituent can be used as long as it has a sufficient bulk to prevent the molecules from approaching each other. . For example, the aforementioned substituted or unsubstituted alkyl group, the aforementioned substituted or unsubstituted cycloalkyl group, the aforementioned substituted or unsubstituted alkoxy group, the aforementioned substituted or unsubstituted aromatic hydrocarbon group, the aforementioned substituted or unsubstituted aromatic hydrocarbon group, The substituted aromatic heterocyclic group, the above-mentioned substituted or unsubstituted aralkyl group, and the above-mentioned substituted or unsubstituted aryloxy group are mentioned. Among them, preferred examples are isopropyl group, t-butyl group and 2,3. -Dibromo-t-butyl group, 2,3-diiodo-t-butyl group, t-butoxy group, 2,3-dibromo-t-butoxy group, 2,3-diiodo-t-butoxy group, 2-methylbutane- 2-yl group, 2-methylbutan-2-yloxy group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl Group, norbornan-1-yl group, norbornan-2-yl group, norbornan-7-yl group, norbornan-1-yloxy group, norbornan-2-yloxy group, norbornan-7-yloxy group, bornan-2-yl group , Bornan-2-yloxy group, tricyclo [5.3.2.04,9] dodecane-1-yl group, tricyclo [5.3.2.04,
9] dodecane-2-yl group, tricyclo [5.3.2.
04,9] dodecane-3-yl group, tricyclo [5.
3.2.04,9] dodecane-10-yl group, tricyclo [5.3.2.04,9] dodecane-11-yl group,
Tricyclo [5.3.2.04,9] dodecane-1-yloxy group, tricyclo [5.3.2.04,9] dodecan-2-yloxy group, tricyclo [5.3.2.0
4,9] dodecane-3-yloxy group, tricyclo [5.3.2.04,9] dodecane-10-yloxy group, tricyclo [5.3.2.04,9] dodecane-1
1-yloxy group, p-cyclophanyl group, 1-adamantyl group, 2-adamantyl group, 1-adamantyloxy group, 2-adamantyloxy group, phenyl group, tolyl group, 9-fluorenyl group, 2,2-dimethyl -1-propyl group, cyclopropylmethyl group, cyclobutylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group, 4-methylcyclohexylmethyl group, norbornane-1-ylmethyl group, norbornan-2-ylmethyl group, norbornan-7-ylmethyl Group, tricyclo [5.3.2.4,9] dodecane-1-ylmethyl group, tricyclo [5.3.2.04,9] dodecane-2
-Ylmethyl group, tricyclo [5.3.2.04,9]
Dodecane-3-ylmethyl group, tricyclo [5.3.
2.04,9] dodecane-10-ylmethyl group, tricyclo [5.3.2.04,9] dodecane-11-ylmethyl group, p-cyclophanemethyl group, 1-adamantylmethyl group, 2-adamantylmethyl group Phenyloxy, benzyl, 4-methylbenzyl, 1-naphthyloxy, 1-naphthylmethyl, 9-anthrylmethyl, 9-anthryloxy, triphenylmethyl, 2,2 2-triphenylethyl group, 9-fluorenyl group, 9-fluorenyloxy group, 9,9′-spirobifluoren-4-yl group, 9,9′-spirobifluoren-3-yl group, 9, 9'-spirobifluorene-4
-Ylmethyl group, 9,9′-spirobifluorene-3-
Ylmethyl group, 9,9′-spirobifluoren-4-yloxy group, 9,9′-spirobifluoren-3-yloxy group, tris (2,2-dimethylpropyl) methyl group, tris (2,2-dimethyl Propyl) methyloxy group, 2,2,2-tris (2,2-dimethylpropyl)
Ethyl group, bicyclo [3,2,1] octan-1-yl group, bicyclo [3,2,1] octan-2-yl group, bicyclo [3,2,1] octan-3-yl group, bicyclo [ 3,2,1] octan-7-yl group, bicyclo [3,
2,1] octan-8-yl group, bicyclo [3,2,
1] octane-1-yloxy group, bicyclo [3,2,
1] octane-2-yloxy group, bicyclo [3,2,
1] octane-3-yloxy group, bicyclo [3,2,
1] octane-7-yloxy group, bicyclo [3,2,
1] octane-8-yloxy group, bicyclo [3,2,
1] octane-1-ylmethyl group, bicyclo [3,2,
1] octane-2-ylmethyl group, bicyclo [3,2,
1] octane-3-ylmethyl group, bicyclo [3,2,
1] octane-7-ylmethyl group, bicyclo [3,2,
1] octane-8-ylmethyl group and the like.

Examples of the compounds of the present invention are shown below, but the present invention is not limited to these.

Embedded image

[0035]

Embedded image

[0036]

Embedded image

[0037]

Embedded image

[0038]

Embedded image

[0039]

Embedded image

[0040]

Embedded image

[0041]

Embedded image

[0042]

Embedded image

[0043]

Embedded image

[0044]

Embedded image

[0045]

Embedded image

[0046]

Embedded image

[0047]

Embedded image

[0048]

Embedded image

[0049]

Embedded image

[0050]

Embedded image

[0051]

Embedded image

[0052]

Embedded image

[0053]

Embedded image

[0054]

Embedded image

[0055]

Embedded image

[0056]

Embedded image

[0057]

Embedded image

[0058]

Embedded image

[0059]

Embedded image

The element structure of the organic EL element according to the present invention is a structure in which one or more organic layers are laminated between electrodes, for example, a structure comprising an anode, a light emitting layer and a cathode as shown in FIG. 4, a structure including an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode as shown in FIG. 2, a structure including an anode, a hole transport layer, a light emitting layer, and a cathode as shown in FIG. Examples of the structure include an anode, a light-emitting layer, an electron transporting layer, and a cathode as shown. The compound in the present invention may be used in any of the above organic layers, and may be doped into other hole transporting materials, light emitting materials, and electron transporting materials.

The hole transport material used in the present invention is not particularly limited, and any compound which is generally used as a hole transport material may be used. For example, the following bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane (30), N, N′-diphenyl-N, N′-bis (3-methylphenyl) -1,1′-biphenyl −4
4'-diamine (31), N, N'-diphenyl-N-
N-bis (1-naphthyl) -1,1'-biphenyl)-
Triphenyldiamines such as 4,4'-diamine (32) and star burst type molecules ((33) to (35))
And the like.

[0062]

Embedded image

Embedded image

The electron transporting material used in the present invention is not particularly limited, and any compound which is usually used as an electron transporting material may be used. For example, 2- (4-biphenylyl) -5- (4-t-butylphenyl) -1,
3,4-oxadiazole (36), bis {2- (4-
Oxadiazole derivatives such as t-butylphenyl) -1,3,4-oxadiazole {-m-phenylene (37) and triazole derivatives ((38), (39)
Quinolinol-based metal complexes ((40) to (43))
Etc.).

[0064]

Embedded image

The anode of the organic thin film EL element plays a role of injecting holes into the hole transport layer, and it is effective that the anode has a work function of 4.5 eV or more. Specific examples of the anode material used in the present invention include indium tin oxide alloy (ITO), tin oxide (NESA), gold, silver, platinum, and copper. As the cathode, a material having a small work function is preferable for the purpose of injecting electrons into the electron transport band or the light emitting layer. The cathode material is not particularly limited, but specifically, indium, aluminum, magnesium, a magnesium-indium alloy, a magnesium-aluminum alloy, an aluminum-lithium alloy, an aluminum-scandium-lithium alloy, a magnesium-silver alloy, or the like can be used.

The method of forming each layer of the organic EL device of the present invention is not particularly limited. For example, a conventionally known forming method by a vacuum deposition method, a spin coating method, or the like can be used. The organic thin film layer containing the compound represented by the general formula (1), (2) or (3) used in the organic EL device of the present invention may be formed by a vacuum evaporation method or a molecular beam evaporation method (MBE).
Method) or a known method such as a dipping method of a solution dissolved in a solvent, a spin coating method, a casting method, a bar coating method, and a roll coating method.

The thickness of each organic layer of the organic EL device of the present invention is not particularly limited. However, if the thickness is too small, defects such as pinholes are likely to occur. Conversely, if the thickness is too large, a high applied voltage is required. Usually, the range of several nm to 1 μm is preferable because efficiency is deteriorated.

[0068]

The present invention will be described in detail below with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist. (Synthesis Example 1) Compound (4) (t-butylbenzo [a]
Synthesis of perylene). According to a conventional method, t-butyl-7,14-dioxo-7,14
-Dihydrobenzo [a] perylene was treated with zinc powder in pyridine and then with 80% acetic acid. Purification was performed according to a conventional method to obtain the desired compound (4).

Synthesis Example 2 Compound (5) (bis-di-
p-tolylamino-t-butylbenzo [a] perylene)
Synthesis of Compound (4) was dissolved in dimethylformamide, and 2 equivalents of N-bromosuccinimide was added at room temperature and stirring was continued. After completion of the reaction, the reaction solution was washed with water and purified according to a conventional method to obtain dibromo-t-butylbenzo [a] perylene. This was placed in a reaction vessel along with di-p-tolylamine, potassium carbonate, copper powder and nitrobenzene,
Stirred at 40 ° C. for 40 hours. After completion of the reaction, nitrobenzene was distilled off under reduced pressure, chloroform was added, and the mixture was filtered to remove inorganic substances. After the filtrate was concentrated, it was formed according to a conventional method to obtain the desired compound (5).

Synthesis Example 3 Compound (6) (bis (N-
Synthesis of p-tolyl-N-4- (4-methylphenylvinyl) phenylamino) -t-butylbenzo [a] perylene). Except that N- (4- (4-methylphenylvinyl) phenyl) -p-toluidine was used instead of di-p-tolylamine, the target compound (6) was obtained in the same manner as in Synthesis Example 2.

(Synthesis Example 4) Compound (7) (bis (N-
Synthesis of p-tolyl-N-4- (2,2-di-p-tolylvinyl) phenylamino) -t-butylbenzo [a] perylene). Instead of di-p-tolylamine, N- (4- (2,2-
Except that di-p-tolylvinyl) phenyl) -p-toluidine was used, the target compound (7) was obtained in the same manner as in Synthesis Example 2.

(Synthesis Example 5) Synthesis of compound (9) (1-adamantylbenzo [a] perylene). 1-adamantyl- in place of t-butyl-7,14-dioxo-7,14-dihydrobenzo [a] perylene
7,14-dioxo-7,14-dihydrobenzo [a]
Except for using perylene, the target compound (9) was obtained in the same manner as in Synthesis Example 1.

Synthesis Example 6 Synthesis of compound (10) (bis-di-p-tolylamino- (1-adamantyl) benzo [a] perylene). The target compound (10) was obtained in the same manner as in Synthesis Example 2 except that the compound (9) was used instead of the compound (4).

Synthesis Example 7 Compound (11) (bis (N
-P-tolyl-N-4- (4-methylphenylvinyl)
Phenylamino)-(1-adamantyl) benzo [a]
Synthesis of perylene). Except that N- (4- (4-methylphenylvinyl) phenyl) -p-toluidine was used instead of di-p-tolylamine, the target compound (11) was obtained in the same manner as in Synthesis Example 6.

(Synthesis Example 8) Compound (12) (bis (N
Synthesis of -p-tolyl-N-4- (2,2-di-p-tolylvinyl) phenylamino)-(1-adamantyl) benzo [a] perylene). Instead of di-p-tolylamine, N- (4- (2,2-
Except that di-p-tolylvinyl) phenyl) -p-toluidine was used, the target compound (12) was obtained in the same manner as in Synthesis Example 6.

Synthesis Example 9 Compound (20) (Np-
Synthesis of Tolyl-N-4- (4-methylphenylvinyl) phenylamino-t-butylbenzo [a] perylene). Compound (4) was dissolved in dimethylformamide, 1 equivalent of N-bromosuccinimide was added at room temperature, and stirring was continued. After completion of the reaction, the reaction solution was washed with water and purified according to a conventional method to obtain bromo-t-butylbenzo [a] perylene. This is converted to N- (4- (4-methylphenylvinyl)
Phenyl) -p-toluidine, potassium carbonate, copper powder and nitrobenzene into a reaction vessel at 200 ° C.
Stirred for 0 hours. After completion of the reaction, nitrobenzene was distilled off under reduced pressure, chloroform was added, and the mixture was filtered to remove inorganic substances.
After the filtrate was concentrated, it was formed according to a conventional method to obtain the desired compound (20).

(Synthesis Example 10) Synthesis of compound (14) (phenoxybenzo [a] perylene). Phenoxy-7,14 instead of t-butyl-7,14-dioxo-7,14-dihydrobenzo [a] perylene
In the same manner as in Synthesis Example 1 except that -dioxo-7,14-dihydrobenzo [a] perylene was used, the target compound (1
4) was obtained.

Synthesis Example 11 Compound (18) ((N-
p-tolyl-N-4- (4-methylphenylvinyl) phenylamino-phenyloxybenzo [a] perylene)
Synthesis of The target compound (18) was obtained in the same manner as in Synthesis Example 9 except that the compound (14) was used instead of the compound (4).

Synthesis Example 12 Compound (26) (di-t
-Butoxybenzo [a] perylene). Di-tert-butoxy-in place of t-butyl-7,14-dioxo-7,14-dihydrobenzo [a] perylene
7,14-dioxo-7,14-dihydrobenzo [a]
A target compound (26) was obtained in the same manner as in Synthesis Example 1 except that perylene was used.

Synthesis Example 13 Compound (29) (bis (Np-tolyl-N-4- (2,2-di-p-tolylvinyl) phenylamino) -di-t-butoxybenzo [a] perylene ) Synthesis. The target compound (29) was obtained in the same manner as in Synthesis Example 4 except that the compound (26) was used instead of the compound (4).

Examples in which the compound of the present invention was used in a light emitting layer (Examples 1 to 26, Examples 31 to 34, Examples 39 to 34)
41), an example in which a thin film mixed with a hole transport material is used for a light emitting layer (Examples 27 to 30), and an example in which a thin film mixed with an electron transport material is used in a light emitting layer (Examples 35 to 38, Example 42) ), Examples used in the hole transport layer (Examples 43 to 44), examples used in the electron transport layer (Examples 45 to 46), and Comparative Examples.

Example 1 FIG. 1 shows a cross-sectional structure of an organic EL device according to Example 1. The organic EL device according to the present embodiment includes a glass substrate 1, an anode 2 and a cathode 6 formed on the glass substrate 1, and a light emitting layer 4 interposed between the anode 2 and the cathode 6. The organic E according to Example 1 is described below.
The procedure for manufacturing the L element will be described. Sheet resistance is set to 2 by sputtering ITO on a glass substrate 1.
An anode 2 was formed so as to have a film thickness of 0 Ω / □. The compound (4) was formed thereon as the light emitting layer 4 by a vacuum evaporation method. A 200 nm thick magnesium-silver alloy was formed thereon as a cathode 6 by vacuum evaporation.
An organic EL device was manufactured. When a DC voltage of 5 V was applied to this organic EL device, light emission of 150 cd / m ² was obtained.

Example 2 Compound (5) as a luminescent material
The same operation as in Example 1 was performed except that organic E was used.
An L element was produced. A DC voltage of 5 V is applied to this organic EL element.
Upon application, light emission of 210 cd / m ² was obtained.

(Example 3) Compound (6) as a luminescent material
The same operation as in Example 1 was performed except that organic E was used.
An L element was produced. A DC voltage of 5 V is applied to this organic EL element.
Upon application, light emission of 250 cd / m ² was obtained.

Example 4 Compound (7) as a luminescent material
The same operation as in Example 1 was performed except that organic E was used.
An L element was produced. A DC voltage of 5 V is applied to this organic EL element.
Upon application, light emission of 290 cd / m ² was obtained.

Example 5 Compound (9) as a luminescent material
The same operation as in Example 1 was performed except that organic E was used.
An L element was produced. A DC voltage of 5 V is applied to this organic EL element.
Upon application, light emission of 170 cd / m ² was obtained.

Example 6 Compound (1) was used as a luminescent material.
An organic EL device was manufactured in the same manner as in Example 1 except that 0) was used. When a DC voltage of 5 V was applied to this organic EL device, light emission of 200 cd / m ² was obtained.

Example 7 The compound (1) was used as a luminescent material.
An organic EL device was manufactured in the same manner as in Example 1 except that 1) was used. When a DC voltage of 5 V was applied to this organic EL device, light emission of 240 cd / m ² was obtained.

Example 8 Compound (1) was used as a light emitting material.
An organic EL device was manufactured in the same manner as in Example 1, except that 2) was used. When a DC voltage of 5 V was applied to this organic EL device, light emission of 280 cd / m ² was obtained.

Example 9 The compound (1) was used as a light emitting material.
An organic EL device was manufactured by performing the same operation as in Example 1 except that 4) was used. When a DC voltage of 5 V was applied to this organic EL device, light emission of 160 cd / m ² was obtained.

Example 10 Compound (1) was used as a light emitting material.
An organic EL device was produced in the same manner as in Example 1 except that 8) was used. When a DC voltage of 5 V was applied to this organic EL device, light emission of 200 cd / m ² was obtained.

Example 11 Compound (2) was used as a light emitting material.
An organic EL device was manufactured in the same manner as in Example 1 except that 0) was used. When a DC voltage of 5 V was applied to this organic EL device, light emission of 190 cd / m ² was obtained.

(Example 12) Organic EL according to Example 12
The cross-sectional structure of the device is the same as that of the organic E according to Example 1 (see FIG.
The sectional structure is the same as that of the L element. Hereinafter, a procedure for manufacturing the organic EL device according to Example 12 will be described. An anode 2 was formed on a glass substrate 1 by sputtering ITO so that the sheet resistance was 20 Ω / □. The light emitting layer 4 having a thickness of 40 nm was formed thereon as a light emitting layer 4 by a spin coating method using a chloroform solution of the compound (7). A 200 nm-thick magnesium-silver alloy was formed thereon as a cathode 6 by a vacuum evaporation method to produce an organic EL device. When a DC voltage of 5 V was applied to this organic EL device, light emission of 80 cd / m ² was obtained.

(Example 13) Organic EL according to Example 13
FIG. 2 shows a cross-sectional structure of the element. Organic EL according to the present embodiment
The device includes a glass substrate 1, an anode 2 and a cathode 6 formed on the glass substrate 1, a hole transport layer 3, a light emitting layer 4, and an electron transport layer 5 sandwiched between the anode 2 and the cathode 6. Consists of Hereinafter, a procedure for manufacturing the organic EL device according to the present example will be described. An anode 2 was formed on a glass substrate 1 by sputtering ITO so that the sheet resistance was 20 Ω / □. Further, as a hole transport layer 3, N, N'-diphenyl-N, N'-bis (3-methylphenyl)-[1,1'-biphenyl]-
4,4'-diamine (31) was deposited by vacuum evaporation method for 50 n.
m was formed. On top of that, the compound (4)
Was formed to a thickness of 40 nm by a vacuum evaporation method. On top of that, 2- (4-biphenylyl) -5- (4-
(t-butylphenyl) -1,3,4-oxadiazole (36) was formed to a thickness of 20 nm by a vacuum evaporation method. A 200 nm-thick magnesium-silver alloy was formed thereon as a cathode 6 by a vacuum evaporation method to produce an organic EL device. When a DC voltage of 10 V was applied to this organic EL device, light emission of 900 cd / m ² was obtained.

(Example 14) An organic EL device was manufactured in the same manner as in Example 13, except that the compound (5) was used as a light emitting material. When a DC voltage of 10 V was applied to this organic EL device, light emission of 2600 cd / m ² was obtained.

(Example 15) An organic EL device was manufactured in the same manner as in Example 13, except that the compound (6) was used as the light emitting material. When a DC voltage of 10 V was applied to this organic EL device, light emission of 3100 cd / m ² was obtained.

Example 16 An organic EL device was manufactured in the same manner as in Example 13, except that the compound (7) was used as a light emitting material. When a DC voltage of 10 V was applied to this organic EL device, light emission of 3700 cd / m ² was obtained.

Example 17 An organic EL device was manufactured in the same manner as in Example 13, except that the compound (9) was used as the light emitting material. When a DC voltage of 10 V was applied to this organic EL device, light emission of 930 cd / m ² was obtained.

Example 18 Compound (1) was used as a luminescent material.
Except that 0) was used, the same operation as in Example 13 was performed,
An organic EL device was manufactured. When a DC voltage of 10 V was applied to this organic EL device, light emission of 2,300 cd / m ² was obtained.

Example 19 The compound (1) was used as a luminescent material.
The same operation as in Example 13 was performed except that 1) was used, and
An organic EL device was manufactured. When a DC voltage of 10 V was applied to this organic EL device, light emission of 2,980 cd / m ² was obtained.

Example 20 The compound (1) was used as a light emitting material.
The same operation as in Example 13 was performed except that 2) was used, and
An organic EL device was manufactured. When a DC voltage of 10 V was applied to this organic EL device, light emission of 3600 cd / m ² was obtained.

Example 21 The compound (2) was used as a light emitting material.
The same operation as in Example 13 was performed except that 6) was used, and
An organic EL device was manufactured. When a DC voltage of 10 V was applied to this organic EL element, light emission of 670 cd / m ² was obtained.

Example 22 Compound (2) was used as a light emitting material.
The same operation as in Example 13 was performed except that 9) was used, and
An organic EL device was manufactured. When a DC voltage of 10 V was applied to this organic EL device, light emission of 1,830 cd / m ² was obtained.

Example 23 The compound (2) was used as a light emitting material.
Except that 0) was used, the same operation as in Example 13 was performed,
An organic EL device was manufactured. When a DC voltage of 10 V was applied to this organic EL device, light emission of 1910 cd / m ² was obtained.

(Example 24) As a hole transport material, N,
N'-diphenyl-NN-bis (1-naphthyl)-
(1,1′-biphenyl) -4,4′-diamine (32)
And bis {2- (4-t-butylphenyl) -1,3,4-oxadiazole} -m as an electron transport material.
-An organic EL device was produced in the same manner as in Example 13, except that phenylene (37) was used. This organic E
When a DC voltage of 10 V is applied to the L element, 850 cd
/ M ² was obtained.

(Example 25) A star bust type molecule (33) was used as a hole transporting material, and a compound (7) was used as a luminescent material.
Is converted to a quinolinol-based metal complex (4
Except that 0) was used, the same operation as in Example 13 was performed,
An organic EL device was manufactured. When a DC voltage of 10 V was applied to this organic EL device, light emission of 4320 cd / m ² was obtained.

(Example 26) A star bust type molecule (34) was used as a hole transport material, and a compound (20) was used as a luminescent material.
Is converted to a quinolinol-based metal complex (4
The same operation as in Example 13 was performed except that 1) was used, and
An organic EL device was manufactured. When a DC voltage of 10 V was applied to this organic EL device, light emission of 2060 cd / m ² was obtained.

(Example 27) As the light emitting layer 4, N, N
'-Diphenyl-NN-bis (1-naphthyl) -1,
Same as Example 13 except that a thin film produced by co-evaporating 1'-biphenyl) -4,4'-diamine (32) and compound (6) at a weight ratio of 1:10 was formed to a thickness of 50 nm. The operation was performed to produce an organic EL device. When a DC voltage of 10 V was applied to this organic EL device, 3470 cd /
m ² emission was obtained.

Example 28 An organic EL device was produced in the same manner as in Example 27, except that the compound (10) was used instead of the compound (6). When a DC voltage of 10 V was applied to the organic EL device, 2510 cd / m ²
Was obtained.

Example 29 An organic EL device was manufactured in the same manner as in Example 27 except that the compound (12) was used instead of the compound (6). When a DC voltage of 10 V was applied to this organic EL device, 3720 cd / m ²
Was obtained.

Example 30 An organic EL device was manufactured in the same manner as in Example 27 except that the compound (18) was used instead of the compound (6). When a DC voltage of 10 V was applied to the organic EL device, 2010 cd / m ²
Was obtained.

(Example 31) Organic EL according to Example 31
FIG. 3 shows a cross-sectional structure of the element. Organic EL according to the present embodiment
The device includes a glass substrate 1, an anode 2 and a cathode 6 formed on the glass substrate 1, and a hole transport layer 3 and a light emitting layer 4 interposed between the anode 2 and the cathode 6. Less than,
A procedure for manufacturing the organic EL device according to this embodiment will be described. An anode 2 was formed on a glass substrate 1 by sputtering ITO so that the sheet resistance was 20 Ω / □. On top of this, N,
N'-diphenyl-NN-bis (1-naphthyl)-
(1,1′-biphenyl) -4,4′-diamine (32)
Was formed to a thickness of 50 nm by a vacuum evaporation method. On top of this, a compound (5) was formed as a light emitting layer 4 by vacuum co-evaporation to form a 40 n layer.
m was formed. In addition, magnesium-
An organic EL element was manufactured by forming a silver alloy to a thickness of 200 nm. When a DC voltage of 10 V was applied to this organic EL element, light emission of 1770 cd / m ² was obtained.

Example 32 An organic EL device was manufactured in the same manner as in Example 31, except that the compound (4) was used instead of the compound (5). When a DC voltage of 10 V was applied to this organic EL device, light emission of 820 cd / m ² was obtained.

Example 33 An organic EL device was manufactured in the same manner as in Example 31, except that the compound (11) was used instead of the compound (5). When a DC voltage of 10 V was applied to this organic EL device, 2270 cd / m ²
Was obtained.

Example 34 An organic EL device was produced in the same manner as in Example 31, except that the compound (18) was used instead of the compound (5). When a DC voltage of 10 V was applied to this organic EL device, 1540 cd / m ²
Was obtained.

(Example 35) The quinolinol metal complex (40) and the compound (6) were used as the light emitting layer 4 in a weight ratio of 20:
An organic EL device was produced in the same manner as in Example 31, except that a thin film produced by vacuum co-evaporation in Step 1 was formed to a thickness of 50 nm. When a DC voltage of 10 V was applied to this organic EL device, light emission of 2360 cd / m ² was obtained.

Example 36 An organic EL device was manufactured in the same manner as in Example 35 except that the compound (9) was used instead of the compound (6). When a DC voltage of 10 V was applied to this organic EL device, light emission of 790 cd / m ² was obtained.

Example 37 An organic EL device was prepared in the same manner as in Example 35 except that the compound (12) was used instead of the compound (6). When a DC voltage of 10 V was applied to the organic EL device, 3020 cd / m ²
Was obtained.

Example 38 An organic EL device was produced in the same manner as in Example 35 except that the compound (29) was used instead of the compound (6). When a DC voltage of 10 V was applied to this organic EL device, 1870 cd / m ²
Was obtained.

(Example 39) Organic EL according to Example 39
FIG. 4 shows a cross-sectional structure of the element. Organic EL according to the present embodiment
The device includes a glass substrate 1, anodes 2 and 6 formed on the glass substrate 1, a light emitting layer 4 and an electron transport layer 5 sandwiched between the anode 2 and the cathode 6. Hereinafter, a procedure for manufacturing the organic EL device according to the present example will be described. An anode 2 was formed on a glass substrate 1 by sputtering ITO so that the sheet resistance was 20 Ω / □. A compound (4) having a thickness of 50 nm was formed thereon as the light emitting layer 4 by a vacuum evaporation method. A triazole derivative (38) was formed thereon as the electron transporting layer 5 to a thickness of 50 nm by a vacuum evaporation method. A 200 nm thick magnesium-silver alloy was formed thereon as the cathode 6 to form an organic
An L element was produced. Apply a DC voltage of 10 to this organic EL element.
When V was applied, light emission of 990 cd / m ² was obtained.

Example 40 An organic EL device was manufactured in the same manner as in Example 39 except that the compound (10) was used instead of the compound (4). When a DC voltage of 10 V was applied to the organic EL device, 2020 cd / m ²
Was obtained.

Example 41 An organic EL device was manufactured in the same manner as in Example 39, except that the compound (6) was used instead of the compound (4). When a DC voltage of 10 V was applied to this organic EL device, light emission of 2600 cd / m ² was obtained.

(Example 42) As the hole transport layer 3, N,
Using N'-diphenyl-N, N'-bis (3-methylphenyl)-[1,1'-biphenyl] -4,4'-diamine (31), a quinolinol-based metal complex (42) and a compound (11) ) Was carried out in a vacuum co-evaporation at a weight ratio of 20: 1 to form the light-emitting layer 4, and the same operation as in Example 31 was carried out to produce an organic EL device. When a DC voltage of 10 V was applied to this organic EL device, light emission of 2250 cd / m ² was obtained.

Example 43 An organic EL device was prepared in the same manner as in Example 13 except that the compound (7) was used as the hole transport layer 3 and the quinolinol-based metal complex (42) was used as the light emitting layer 4. An element was manufactured. When a DC voltage of 10 V was applied to this organic EL element, light emission of 1970 cd / m ² was obtained.

Example 44 An organic EL device was manufactured in the same manner as in Example 43 except that the compound (10) was used as the hole transporting layer 3. When a DC voltage of 10 V was applied to this organic EL device, light emission of 1630 cd / m ² was obtained.

Example 45 An organic EL device was manufactured by performing the same operation as in Example 13 except that the compound (4) was used as the electron transport layer 5 and the quinolinol-based metal complex (40) was used as the light emitting layer 4. Produced. When a DC voltage of 10 V was applied to this organic EL element, light emission of 730 cd / m ² was obtained.

Example 46 An organic EL device was manufactured in the same manner as in Example 44, except that the compound (7) was used instead of the compound (4). When a DC voltage of 10 V was applied to this organic EL device, light emission of 690 cd / m ² was obtained.

(Comparative Example 1) A light-emitting layer 4 was formed using bis- (di-p-tolylamino) benzoperylene.
The same operation as in Example 13 was performed to manufacture an organic EL device. When a DC voltage of 10 V was applied to this organic EL device, light emission of 1800 cd / m ² was obtained.

(Comparative Example 2) As the light emitting layer 4, (4- (4
Example 13 except that -methylphenylvinyl) phenyl-p-tolylamino) benzo [a] perylene was used.
The same operation as described above was performed to produce an organic EL device. When a DC voltage of 10 V was applied to the organic EL element, 200
Light emission of 0 cd / m ² was obtained.

[0130]

As described above, in the organic EL device according to the present invention, the compound represented by the general formula (1), (2) or (3) is used as a constituent material of the organic thin film. As a result, light emission with higher luminance than before can be obtained, and the effect of the present invention is great.

[Brief description of the drawings]

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

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

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

FIG. 4 is a cross-sectional view of an example of the organic EL device according to the present invention.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 1 Substrate 2 Anode 3 Hole transport layer 4 Light emitting layer 5 Electron transport layer 6 Cathode

Continuation of the front page (72) Inventor Hiroshi Tada 5-7-1 Shiba, Minato-ku, Tokyo NEC Corporation (72) Inventor Yukiko Morioka 5-7-1 Shiba, Minato-ku, Tokyo NEC Corporation In-house (72) Inventor Atsushi Oda 5-7-1 Shiba, Minato-ku, Tokyo F-term within NEC Corporation (reference) 3K007 AB02 AB06 CA01 CB01 CB03 DA00 DB03 EB00 FA01

Claims (7)

[Claims] 1. An organic electroluminescent device having one or more organic thin-film layers including a light-emitting layer between a cathode and an anode, wherein at least one of the organic thin-film layers has a general formula (1): 1) (Wherein, R ^{1 to} R ¹⁴ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl Group, substituted or unsubstituted styryl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted Or an unsubstituted aralkyl group or a substituted or unsubstituted aryloxy group, and R ^{1 to} R ¹⁴ may form a ring with two of them, provided that R ^{1 to} R ¹⁴ At least one of which is a sterically hindered group that suppresses the formation of an association state between molecules.) The organic electro-luminescent element that. 2. An organic electroluminescent device having one or more organic thin film layers including a light emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers has a general formula (2): 2] (Wherein, R ^{1 to} R ¹⁴ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl Group, substituted or unsubstituted styryl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted Or an unsubstituted aralkyl group or a substituted or unsubstituted aryloxy group, and R ^{1 to} R ¹⁴ may form a ring with two of them, provided that at least ^{one of} R ^{1 to} R ¹⁴ One is -N
Ar ¹ is a diarylamino group represented by Ar ² (Ar ¹ and Ar ^{2 each} represent a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group).
Further, at least one of R ^{1 to} R ¹⁴ which is not a diarylamino group is a sterically hindered group which suppresses formation of an associated state between molecules. An organic electroluminescent device comprising the benzoperylene compound represented by the formula (1) alone or in a mixture. 3. An organic electroluminescent device having one or more organic thin film layers including a light emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers has a general formula (3): 3] (Wherein, R ^{1 to} R ¹⁴ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl Group, substituted or unsubstituted styryl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted Or an unsubstituted aralkyl group or a substituted or unsubstituted aryloxy group, and R ^{1 to} R ¹⁴ may form a ring with two of them, provided that R ^{1 to} R ¹⁴ At least one is-
NAr ¹ Ar ² (Ar ¹ and Ar ² represent a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, provided that at least one of Ar ¹ and Ar ² is , A substituted or unsubstituted styryl group as a substituent.). Further, at least one of R ^{1 to} R ¹⁴ which is not a diarylamino group is a sterically hindered group which suppresses formation of an associated state between molecules. An organic electroluminescent device comprising the benzoperylene compound represented by the formula (1) alone or in a mixture. 4. The organic thin-film layer has at least a light-emitting layer, and the light-emitting layer contains the compound represented by the general formula (1), (2) or (3) alone or as a mixture. The organic electroluminescent device according to any one of claims 1 to 3, wherein: 5. The organic thin film layer has at least a hole transporting layer, wherein the hole transporting layer has the general formula (1), (2),
4. The organic electroluminescent device according to claim 1, wherein the compound represented by (3) is contained alone or as a mixture. 6. The organic thin film layer has at least an electron transporting layer, and the electron transporting layer has the general formula (1), (2),
4. The organic electroluminescent device according to claim 1, wherein the compound represented by (3) is contained alone or as a mixture. 7. The general formula (1), (2) or (3)
Is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted The organic electroluminescent device according to any one of claims 1 to 6, wherein the organic electroluminescent device is a substituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryloxy group.