JP2005235633A - Organic electroluminescent element and fluoranthene derivative - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescent element with a long light emission life and high luminance, and to provide a fluoranthene derivative suitable for the element. <P>SOLUTION: The organic electroluminescent element has a 1, 2-dihydro-1, 2-diazacyclopenta [cd] fluoranthene derivative and at least one layer containing at least one kind of the 1, 2-dihydro-1, 2-diazacyclopenta [cd] fluoranthene derivative between a pair of electrodes. Therefore, the organic electroluminescent element with the long light emission life and the high luminance and useful as a panel type light source can be obtained. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

The present invention relates to an organic electroluminescent element and a fluoranthene derivative that can be suitably used for the organic electroluminescent element.

Conventionally, an inorganic electroluminescent element has been used as a panel-type light source such as a backlight. However, in order to drive the light emitting element, an alternating high voltage is required. Recently, an organic electroluminescence element (organic electroluminescence element: organic EL element) using an organic material as a light emitting material has been developed (Non-patent Document 1).
An organic electroluminescent 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 and recombined to form an exciton (exington). ) And emits light using light emitted when the exciton is deactivated. The organic electroluminescent element can emit light at a low direct current voltage of several volts to several tens of volts, and various colors (for example, red, blue, green) can be selected by selecting the type of the fluorescent organic compound. ) Can be emitted. The organic electroluminescent element having such characteristics is expected to be applied to various light emitting elements, display elements and the like. However, in general, organic electroluminescent elements have drawbacks such as poor stability and durability.

As a method for improving stability and durability and improving the light emission lifetime, for example, bis (2-methyl-8-quinolinolato) (4-phenylphenolate) aluminum is used as a host compound, an acridone derivative (for example, N-methyl- An organic electroluminescent device using 2-methoxyacridone) as a guest compound has been proposed (Patent Document 1). An organic electroluminescent element using tris (8-quinolinolato) aluminum as a host compound and a quinacridone derivative as a guest compound has also been proposed (Non-Patent Document 2). However, it cannot be said that these light emitting elements also have a sufficient light emission lifetime.
At present, an organic electroluminescent device having a longer emission lifetime is desired.
Appl.Phys.Lett., 51,913 (1987) Appl.Phys.Lett.70,1665 (1997) JP-A-8-67873

An object of the present invention is to provide an organic electroluminescence device that has a long emission lifetime and emits light with high luminance.

In order to solve the above-mentioned problems, the present inventors have intensively studied an organic electroluminescent element and a compound used for the element, and as a result, have completed the present invention. That is, the present invention
<1>: an organic electroluminescent device comprising at least one layer containing at least one 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative between a pair of electrodes,
<2>: 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative represented by the general formula (1) (Chemical formula 1),

[Wherein, R _{1 to} R ₈ each independently represents a hydrogen atom or a substituent, and adjacent groups of R _{1 to} R ₈ may be bonded to each other to form a cyclic structure; Ar ₁ and Ar ₂ represents a substituted or unsubstituted aryl group]
It is about.

  According to the present invention, an organic electroluminescent device excellent in luminous lifetime and luminous efficiency, comprising at least one layer containing at least one 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative, In addition, it is possible to provide a 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative that can be suitably used for an organic electroluminescent device.

  Hereinafter, the present invention will be described in detail.

The organic electroluminescent device of the present invention comprises at least one layer containing at least one 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative between a pair of electrodes. is there.
The 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative according to the present invention is preferably a compound having a skeleton represented by the general formula (1) (Chemical Formula 2),

[Wherein, R _{1 to} R ₈ each independently represents a hydrogen atom or a substituent, and adjacent groups of R _{1 to} R ₈ may be bonded to each other to form a cyclic structure; Ar ₁ and Ar ₂ represents a substituted or unsubstituted aryl group]

In the 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative of the present invention, in the general formula (1), adjacent groups of R _{1 to} R ₈ are bonded to each other to form a cyclic structure. In that case, the structure of the following general formula (1-A)-general formula (1-C) is preferable.

[Wherein R _{1 to} R ₈ , Ar ₁ and Ar ₂ represent the same meaning as in general formula (1), Y _{1 to} Y ₄ represent a hydrogen atom or a substituent, and Y _{1 to} Y ₄ are adjacent to each other. Each group may be bonded to each other to form a cyclic structure.)
Preferred is a structure of the general formula (1) that does not form a cyclic structure, a structure of (1-A) and / or a structure of (1-C), more preferably a general structure that does not form a cyclic structure. It is the structure of Formula (1) and / or (1-C).

In the 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative represented by the general formula (1), R _{1 to} R ₈ each represents a hydrogen atom or a substituent. A halogen atom, a substituted or unsubstituted linear, branched or cyclic alkyl group, a substituted or unsubstituted linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, A substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkyloxy group, a substituted or unsubstituted amino group, a cyano group, a nitro group, a carboxyl group, a substituted or unsubstituted linear, branched or cyclic alkoxycarbonyl group, A substituted or unsubstituted aryloxycarbonyl group, a substituted or unsubstituted linear, branched or cyclic alkylcarbonyloxy group, It represents a substituted or unsubstituted arylcarbonyloxy group, or a substituted or unsubstituted aminocarbonyl group.

  The substituent is preferably a halogen atom, a substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear, branched or cyclic group having 1 to 20 carbon atoms. An alkoxy group, a substituted or unsubstituted aryl group having 2 to 30 carbon atoms (including a heteroaryl group), a substituted or unsubstituted aryloxy group having 2 to 30 carbon atoms (including a heteroaryloxy group), carbon A substituted or unsubstituted aralkyl group having 7 to 20 atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, an unsubstituted amino group, a substituted or unsubstituted straight chain having 1 to 20 carbon atoms A mono- or di-substituted amino group with a branched or cyclic alkyl group, a mono- or di-substituted aryl group having 2 to 30 carbon atoms (including a heteroaryl group) or A substituted amino group, an amino group mono- or di-substituted with a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted linear, branched or cyclic alkoxy group with 2 to 20 carbon atoms Carbonyl group, substituted or unsubstituted aryloxycarbonyl group having 7 to 30 carbon atoms, substituted or unsubstituted linear, branched or cyclic alkylcarbonyloxy group having 2 to 20 carbon atoms, 7 to 30 carbon atoms A substituted or unsubstituted arylcarbonyloxy group, or a mono- or di-substituted aminocarbonyl group substituted with a substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, 2 to 30 carbon atoms A mono- or di-substituted aminocarbonyl group with a substituted or unsubstituted aryl group (including a heteroaryl group),

More preferably, a halogen atom, a substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 15 carbon atoms. A substituted or unsubstituted aryl group having 4 to 25 carbon atoms (including a heteroaryl group), a substituted or unsubstituted aryloxy group having 4 to 25 carbon atoms (including a heteroaryloxy group), and the number of carbon atoms 7 to 15 substituted or unsubstituted aralkyl group, 7 to 15 carbon atom substituted or unsubstituted aralkyloxy group, unsubstituted amino group, 1 to 15 carbon atom substituted or unsubstituted straight chain, branched Or a mono- or di-substituted amino group mono- or di-substituted with a cyclic alkyl group, or a substituted or unsubstituted aryl group having 4 to 25 carbon atoms (including heteroaryl groups). Amino groups, amino groups mono- or di-substituted with substituted or unsubstituted aralkyl groups having 7 to 15 carbon atoms, substituted or unsubstituted linear, branched or cyclic alkoxycarbonyl groups with 2 to 15 carbon atoms Group, substituted or unsubstituted aryloxycarbonyl group having 7 to 25 carbon atoms, substituted or unsubstituted linear, branched or cyclic alkylcarbonyloxy group having 2 to 15 carbon atoms, and having 7 to 25 carbon atoms A substituted or unsubstituted arylcarbonyloxy group, or an aminocarbonyl group mono- or di-substituted with a substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 15 carbon atoms, having 4 to 25 carbon atoms An aminocarbonyl group mono- or di-substituted with a substituted or unsubstituted aryl group (including a heteroaryl group) is represented.

Specific examples of the halogen atom for R _{1 to} R ₈ include halogen atoms such as a fluorine atom, a chlorine atom, and a bromine atom.

Specific examples of the substituted or unsubstituted linear, branched or cyclic alkyl group represented by R _{1 to} R ₈ include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and an isobutyl group. , Sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 2-ethylbutyl Group, n-heptyl group, 1-methylhexyl group, n-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, 1-ethyloctyl group, n-undecyl group, 1-methyldecyl group, n-dodecyl Group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, 1-heptyloctyl group, n-hexadecyl group, n-heptadecyl group, 1-octylnonyl group, n-octadecyl group, 1-nonyldecyl group, 1-decylundecyl group, n-eicosyl group, n-docosyl group, n-tetracosyl group, cyclohexylmethyl group, (1-isopropylcyclohexyl) methyl group, 2-cyclohexylethyl group, bornel group, isobornel group,

1-norbornyl group, 2-norbornanemethyl group, 1-bicyclo [2.2.2] octyl group, 1-adamantyl group, 2-adamantyl group, 3-noradamantyl group, 1-adamantylmethyl group, cyclobutyl group, cyclopentyl Group, 1-methylcyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 3-methylcyclohexyl group, 2-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethyl group Cyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 3,3,5-trimethylcyclohexyl group, 2,6-diisopropylcyclohexyl group, 4-tert -Butylcyclohexyl group, 3-ter t-butylcyclohexyl group, 4-phenylcyclohexyl group, 2-phenylcyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group, cyclododecyl group, cyclotetradecyl group,

Methoxymethyl group, ethoxymethyl group, n-butoxymethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) methyl group, n-octyloxymethyl group, n-decyloxymethyl group, 2-methoxyethyl group 2-ethoxyethyl group, 2-n-propoxyethyl group, 2-isopropoxyethyl group, 2-n-butoxyethyl group, 2-n-pentyloxyethyl group, 2-n-hexyloxyethyl group, 2- (2′-ethylbutyloxy) ethyl group, 2-n-heptyloxyethyl group, 2-n-octyloxyethyl group, 2- (2′-ethylhexyloxy) ethyl group, 2-n-decyloxyethyl group, 2-n-dodecyloxyethyl group, 2-n-tetradecyloxyethyl group, 2-cyclohexyloxyethyl group, 2-methoxypropyl 3-methoxypropyl group, 3-ethoxypropyl group, 3-n-propoxypropyl group, 3-isopropoxypropyl group, 3- (n-butoxy) propyl group, 3- (n-pentyloxy) propyl group, 3 -(N-hexyloxy) propyl group,

3- (2'-ethylbutoxy) propyl group, 3- (n-octyloxy) propyl group, 3- (2'-ethylhexyloxy) propyl group, 3- (n-decyloxy) propyl group, 3- (n- Dodecyloxy) propyl group, 3- (n-tetradecyloxy) propyl group, 3-cyclohexyloxypropyl group, 4-methoxybutyl group, 4-ethoxybutyl group, 4-n-propoxybutyl group, 4-isopropoxybutyl Group, 4-n-butoxybutyl group, 4-n-hexyloxybutyl group, 4-n-octyloxybutyl group, 4-n-decyloxybutyl group, 4-n-dodecyloxybutyl group, 5-methoxypentyl Group, 5-ethoxypentyl group, 5-n-propoxypentyl group, 6-ethoxyhexyl group, 6-isopropoxyhexyl group, 6-n Butoxyhexyl group, 6-n-hexyloxyhexyl group, 6-n-decyloxyhexyl group, 4-methoxycyclohexyl group, 7-ethoxyheptyl group, 7-isopropoxyheptyl group, 8-methoxyoctyl group, 10-methoxy Decyl group, 10-n-butoxydecyl group, 12-ethoxydodecyl group, 12-isopropoxide decyl group, tetrahydrofurfuryl group,

2- (2′-methoxyethoxy) ethyl group, 2- (2′-ethoxyethoxy) ethyl group, 2- (2′-n-butoxyethoxy) ethyl group, 3- (2′-ethoxyethoxy) propyl group, 2-allyloxyethyl group, 2- (4′-pentenyloxy) ethyl group, 3-allyloxypropyl group, 3- (2′-hexenyloxy) propyl group, 3- (2′-heptenyloxy) propyl group, 3 -(1'-cyclohexenyloxy) propyl group, 4-allyloxybutyl group,

Benzyloxymethyl group, 2-benzyloxyethyl group, 2-phenethyloxyethyl group, 2- (4′-methylbenzyloxy) ethyl group, 2- (2′-methylbenzyloxy) ethyl group, 2- (4 ′) -Fluorobenzyloxy) ethyl group, 2- (4'-chlorobenzyloxy) ethyl group, 3-benzyloxypropyl group, 3- (4'-methoxybenzyloxy) propyl group, 4-benzyloxybutyl group, 2- (Benzyloxymethoxy) ethyl group, 2- (4′-methylbenzyloxymethoxy) ethyl group,

Phenyloxymethyl group, 4-methylphenyloxymethyl group, 3-methylphenyloxymethyl group, 2-methylphenyloxymethyl group, 4-methoxyphenyloxymethyl group, 4-fluorophenyloxymethyl group, 4-chlorophenyloxymethyl group Group, 2-chlorophenyloxymethyl group, 2-phenyloxyethyl group, 2- (4′-methylphenyloxy) ethyl group, 2- (4′-ethylphenyloxy) ethyl group, 2- (4′-methoxyphenyl) Oxy) ethyl group, 2- (4′-chlorophenyloxy) ethyl group, 2- (4′-bromophenyloxy) ethyl group, 2- (1′-naphthyloxy) ethyl group, 2- (2′-naphthyloxy) ) Ethyl group, 3-phenyloxypropyl group, 3- (2′-naphthyloxy) propyl group, 4-phenyloxy Sibutyl group, 4- (2′-ethylphenyloxy) butyl group, 5- (4′-tert-butylphenyloxy) pentyl group, 6- (2′-chlorophenyloxy) hexyl group, 8-phenyloxyoctyl group, 10-phenyloxydecyl group, 10- (3′-chlorophenyloxy) decyl group, 2- (2′-phenyloxyethoxy) ethyl group, 3- (2′-phenyloxyethoxy) propyl group, 4- (2
'-Phenyloxyethoxy) butyl group,

n-butylthiomethyl group, n-hexylthiomethyl group, 2-methylthioethyl group, 2-ethylthioethyl group, 2-n-butylthioethyl group, 2-n-hexylthioethyl group, 2-n-octyl Thioethyl group, 2-n-decylthioethyl group, 3-methylthiopropyl group, 3-ethylthiopropyl group, 3-n-butylthiopropyl group, 4-ethylthiobutyl group, 4-n-propylthiobutyl group 4-n-butylthiobutyl group, 5-ethylthiopentyl group, 6-methylthiohexyl group, 6-ethylthiohexyl group, 6-n-butylthiohexyl group, 8-methylthiooctyl group, 2- (2 ′ -Methoxyethylthio) ethyl group, 4- (3'-ethoxypropylthio) butyl group, 2- (2'-ethylthioethylthio) ethyl group, 2-allylthioethyl group, 2- N-dithioethyl group, 3- (4′-methylbenzylthio) propyl group, 4-benzylthiobutyl group, 2- (2′-benzyloxyethylthio) ethyl group, 3- (3′-benzylthiopropylthio) propyl group ,
2-phenylthioethyl group, 2- (4′-methoxyphenylthio) ethyl group, 2- (2′-phenyloxyethylthio) ethyl group, 3- (2′-phenylthioethylthio) propyl group,

Fluoromethyl group, 3-fluoropropyl group, 6-fluorohexyl group, 8-fluorooctyl group, difluoromethyl group, trifluoromethyl group, 1,1-dihydro-perfluoroethyl group, 1,1-dihydro-perfluoro -N-propyl group, 1,1,3-trihydro-perfluoro-n-propyl group, 1,1-dihydro-perfluoro-n-butyl group, 1,1-dihydro-perfluoro-n-pentyl group, 1,1-dihydro-perfluoro-n-hexyl group, 6-fluorohexyl group, 4-fluorocyclohexyl group, 1,1-dihydro-perfluoro-n-octyl group, 1,1-dihydro-perfluoro-n -Decyl group, 1,1-dihydro-perfluoro-n-dodecyl group, 1,1-dihydro-perfluoro-n-tetradecyl group, 1 1-dihydro-perfluoro-n-hexadecyl group, perfluoro-n-hexyl group, dichloromethyl group, 2-chloroethyl group, 3-chloropropyl group, 4-chlorocyclohexyl group, 7-chloroheptyl group, 8-chloro Octyl group, 2,2,2-trichloroethyl group,

2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 3-hydroxybutyl group, 4-hydroxybutyl group, 6-hydroxyhexyl group, 5-hydroxyheptyl group, 8-hydroxyoctyl group, 10- Examples thereof include a substituted or unsubstituted linear, branched or cyclic alkyl group such as a hydroxydecyl group, a 12-hydroxydodecyl group and a 2-hydroxycyclohexyl group.

Specific examples of the substituted or unsubstituted linear, branched or cyclic alkoxy group represented by R _{1 to} R ₈ include a form in which an oxygen atom is bonded to the above substituted or unsubstituted linear, branched or cyclic alkyl group. The alkoxy group represented can be mentioned.

Specific examples of the substituted or unsubstituted aryl group of R _{1 to} R ₈ include, for example, a phenyl group, 1-naphthyl group, 2-naphthyl group, 2-anthracenyl group, 9-anthracenyl group, 9-methyl-10- Anthracenyl group, 9-phenyl-10-anthracenyl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 9-methyl-10-phenanthryl group, 9-phenyl- 10-phenanthryl group, 1-methyl-9-phenanthryl group, 1-phenyl-9-phenanthryl group, 2-methyl-9-phenanthryl group, 2-phenyl-9-phenanthryl group, 1,8-dimethyl-9-phenanthryl Group, 1,8-diphenyl-9-phenanthryl group, 2-chloro-9-phenanthryl 2-fluoro-9-phenanthryl group, 2,7-dichloro-9-phenanthryl group, 2,7-dimethyl-9-phenanthryl group, 2,7-diphenyl-9-phenanthryl group, 2,7,9-trimethyl A -10-phenanthryl group, a 2,7,9-triphenyl-10-phenanthryl group,
2-quinolinyl group, 4-quinolinyl group, 1-pyrenyl group, 2-pyrenyl group, 1-phenyl-2-pyrenyl group, 1-methyl-2-pyrenyl group, 2-phenyl-1-pyrenyl group, 2-methyl- 1-pyrenyl group, 4,5-dimethyl-1-pyrenyl group, 6-phenyl-1-pyrenyl group, 6-methyl-1-pyrenyl group, 6-tert-butyl-1-pyrenyl group, 6-cyclohexyl-1 -Pyrenyl group, 7-phenyl-1-pyrenyl group, 7-methyl-1-pyrenyl group, 7-phenyl-2-pyrenyl group, 7-methyl-2-pyrenyl group,

7-tert-butyl-2-pyrenyl group, 1,8-diphenyl-2-pyrenyl group, 1,8-dimethyl-2-pyrenyl group, 5,9-dicyclohexyl-2-pyrenyl group, 3,6-diphenyl- 1-pyrenyl group, 3,6-dimethyl-1-pyrenyl group, 3,6-di-tert-butyl-1-pyrenyl group, 8-methyl-1-pyrenyl group, 8-tert-butyl-1-pyrenyl group 8-phenyl-1-pyrenyl group, 9-phenyl-1-pyrenyl group, 9-phenyl-2-pyrenyl group, 9-methyl-2-pyrenyl group, 10-phenyl-1-pyrenyl group, 10-methyl- 1-pyrenyl group, 10-phenyl-2-pyrenyl group, 10-methyl-2-pyrenyl group, 9-methyl-1-pyrenyl group, 3,6,8-trimethyl-1-pyrenyl group, 3,6,8 -Triphenyl-1-pyrenyl group, 3, -Dimethyl-8-phenyl-1-pyrenyl group, 9,10-dimethyl-1-pyrenyl group, 9,10-diphenyl-1-pyrenyl group, 4,9-dimethyl-1-pyrenyl group, 4,9-diphenyl -1-pyrenyl group, 9,5-dimethyl-2-pyrenyl group, 4,5,9,10-trimethyl-2-pyrenyl group, 9H-fluoren-2-yl group, 9-methyl-9H-fluorene-2 -Yl group, 9,9-dimethyl-9H-fluoren-2-yl group, 9,9-diethyl-9H-fluoren-2-yl group, 9,9-dibenzyl-9H-2-fluoren-2-yl group 9,9-diphenyl-9H-fluoren-2-yl group, 7,9,9-trimethyl-9H-fluoren-2-yl group, 7-phenyl-9,9-dimethyl-9H-fluoren-2-yl group Group, 7-N-ca Rubazolyl-9,9-dimethyl-9H-fluoren-2-yl group, 7-N, N-dimethylamino 9,9-dimethyl-9H-fluoren-2-yl group,

7-N, N-diphenylamino-9,9-dimethyl-9H-fluoren-2-yl group, 4-pyridinyl group, 3-pyridinyl group, 2-pyridinyl group, 5-phenyl-2-pyridinyl group, 2- Phenyl-4-pyridinyl group, 3-furanyl group, 2-furanyl group, 5-phenyl-2-furanyl group, 3-thienyl group, 2-thienyl group, 5-phenyl-2-thienyl group, 2-oxazolyl group, 2-thiazolyl group, 5-phenyl-2-oxazolyl group, 5-phenyl-2-thiazolyl group, 2-oxadiazolyl group, 2-thiadiazolyl group, 5-phenyl-2-oxadiazolyl group, 5-phenyl-2-thiadiazolyl group 5- (1′-naphthyl) -2-oxadiazolyl group, 5- (1′-naphthyl) -2-thiadiazolyl group, 2-benzoxazolyl group, 2- Nzochiazoriru group, 2-benzimidazolyl group, 2-dibenzo benzoxazolyl group, 3-dibenzo benzoxazolyl group, 2-dibenzothiazolyl group, 3-dibenzothiazolyl 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-tertbutylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 2-neopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4- ( 2'-ethylbutyl) phenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4- (2'-ethylhexyl) phenyl , 4-tert-octylphenyl group, 4-n-decyl phenyl group,

4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4- (4'-methylcyclohexyl) phenyl group, 4- (4'-tert-butyl) (Cyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4-ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group, 2,4-dimethylphenyl group, 3,4-dimethyl Phenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,4-diethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 3,4 , 5-trimethylphenyl group, 2,6-diethylphenyl group, 2,5-diisopropylphenyl group, 2,6-diisobutylpheny Group, 2,4-di-tert-butylphenyl group, 2,5-di-tert-butylphenyl group, 4,6-di-tert-butyl-2-methylphenyl group, 5-tert-butyl-2 -Methylphenyl group, 4-tert-butyl-2,6-dimethylphenyl group,

4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl Group, 4-isopropoxyphenyl group, 3-isopropoxyphenyl group, 2-isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n- Pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 4-neopentyloxyphenyl group, 2-nepentyloxyphenyl group, 4-n-hexyloxyphenyl group, 2- (2 '-Ethylbutyloxy) phenyl group, 4-n-octyloxyphenyl group, 4-n- Siloxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-tetradecyloxyphenyl group, 4-cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group, 2-methoxy-1-naphthyl group, 4-methoxy -1-naphthyl group, 4-n-butoxy-1-naphthyl group, 5-ethoxy-1-naphthyl group, 6-methoxy-2-naphthyl group, 6-ethoxy-2-naphthyl group, 6-n-butoxy- 2-naphthyl group, 6-n-hexyloxy-2-naphthyl group, 7-methoxy-2-naphthyl group, 7-n-butoxy-2-naphthyl group, 2-methyl-4-methoxyphenyl group, 2-methyl -5-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 3-ethyl-5-methoxyphenyl group, 2-methoxy-4-methylphenyl 3-methoxy-4-methylphenyl group,

2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 3 , 5-Di-n-butoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2-methoxy-6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4-phenylphenyl group, 3- Phenylphenyl group, 2-phenylphenyl group, 4- (4'-methylphenyl) phenyl group, 4- (3'-methylphenyl) phenyl group, 4-phenyl-2-methylphenyl group, 4-phenyl-3- Methylphenyl group, 2- (2′-phenylphenyl) phenyl group, 3- (3′-phenylphenyl) phenyl group, 4- (4′-phenylphenyl) Enyl group, 4- (4′-methoxyphenyl) phenyl group, 4- (4′-n-butoxyphenyl) phenyl group, 2- (2′-methoxyphenyl) phenyl group, 4- (4′-chlorophenyl) phenyl Group, 3-methyl-4-phenylphenyl group, 3-methoxy-4-phenylphenyl group, 2-phenoxyphenyl group, 3-phenoxyphenyl group, 4-phenoxyphenyl group, 4-fluorophenyl group, 3-fluorophenyl Group, 2-fluorophenyl group, 4-chlorophenyl group, 3-chlorophenyl group, 2-chlorophenyl group, 4-bromophenyl group, 3-bromophenyl group, 2-bromophenyl group, 4-chloro-1-naphthyl group, 4-chloro-2-naphthyl group, 6-bromo-2-naphthyl group, 2,3-difluorophenyl group, 2,5-difur Rofeniru group, 2,6-difluorophenyl group,

3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group 2,5-dibromophenyl group, 2,4,6-trichlorophenyl group, 2,4-dichloro-1-naphthyl group, 1,6-dichloro-2-naphthyl 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-4-methylphenyl group, 2-chloro-5- Tilphenyl group, 2-chloro-6-methylphenyl group, 2-methyl-3-chlorophenyl group, 2-methyl-3-chlorophenyl group, 2-methyl-4-chlorophenyl group, 3-methyl-4-chlorophenyl group, 2 -Chloro-4,6-dimethylphenyl group, 2-methoxy-4-fluorophenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-4-ethoxyphenyl group, 2-fluoro-6-methoxyphenyl group 3-fluoro-4-ethoxyphenyl group, 3-chloro-4-methoxyphenyl group, 2-methoxy-5-chlorophenyl group, 3-methoxy-6-chlorophenyl group,

5-chloro-2,4-dimethoxyphenyl group, 4-aminophenyl group, 4-N-methylaminophenyl group, 3-N-methylaminophenyl group, 4-N-ethylaminophenyl group, 3-N-ethyl Aminophenyl group, 4-N-isopropylaminophenyl group, 4-Nn-propylaminophenyl group, 4-N, N-dimethylaminophenyl group, 3-N, N-dimethylaminophenyl group, 4-N, N-diethylaminophenyl group, 3-N-diethylaminophenyl group, 4-N, N-diisopropylaminophenyl group, 4-N, N-di-n-propylamino group, 4-N, N-di-n-butyl Aminophenyl group, 4-N, N-diisobutylaminophenyl group, 4-N, N-dibenzylaminophenyl group, 4-N, N-diphenylaminophenyl group, 3 N, N-diphenylaminophenyl group, 4-N-phenyl-N- (1′-naphthyl) aminophenyl group, 4-N-phenyl-N- (2′-naphthyl) aminophenyl group, 4-N, N -Di (1'-naphthyl) aminophenyl group and 4-N, N-di (2'-naphthyl) aminophenyl group can be exemplified.

Specific examples of the substituted or unsubstituted aryloxy group for R _{1 to} R ₈ include an aryloxy group represented by an oxygen atom bonded to the above substituted or unsubstituted aryl group.

Specific examples of the substituted or unsubstituted aralkyl group of R _{1 to} R ₈ include, for example, benzyl group, α-methylbenzyl group, α-ethylbenzyl group, phenethyl group, α-methylphenethyl group, β-methylphenethyl group. , Α, α-dimethylbenzyl group, α, α-dimethylphenethyl group, 4-methylphenethyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl group, 4-ethylbenzyl group, 2-ethyl Benzyl group, 4-isopropylbenzyl group, 4-tert-butylbenzyl group, 2-tert-butylbenzyl group, 4-tert-pentylbenzyl group, 4-cyclohexylbenzyl group, 4-n-octylbenzyl group, 4-tert -Octylbenzyl group, 4-allylbenzyl group, 4-benzylbenzyl group, 4-phenethylbenzyl group, 4-phenylbenzyl group 4- (4′-methylphenyl) benzyl group, 4-methoxybenzyl group, 2-methoxybenzyl group, 2-ethoxybenzyl group, 4-n-butoxybenzyl group, 4-n-heptyloxybenzyl group, 4-n -Decyloxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-isobutoxymethylbenzyl group, 4 -Allyloxybenzyl group, 4-vinyloxymethylbenzyl group, 4-benzyloxybenzyl group, 4-phenethyloxybenzyl group, 4-phenyloxybenzyl group, 3-phenyloxybenzyl group,

4-hydroxybenzyl group, 3-hydroxybenzyl group, 2-hydroxybenzyl group, 4-hydroxy-3-methoxybenzyl group, 4-fluorobenzyl group, 2-fluorobenzyl group, 4-chlorobenzyl group, 3-chlorobenzyl And an aralkyl group such as a group, 2-chlorobenzyl group, 3,4-dichlorobenzyl group, 2-furfuryl group, diphenylmethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group.

Specific examples of the substituted or unsubstituted aralkyloxy group of R _{1 to} R ₈ include an aralkyloxy group represented by a form in which an oxygen atom is bonded to the above substituted or unsubstituted aralkyl group. .

Specific examples of the substituted or unsubstituted amino group of R _{1 to} R ₈ include, for example, an amino group, an N-methylamino group, an N-ethylamino group, an Nn-propylamino group, an N-isopropylamino group, Nn-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, Nn-pentylamino group, N-cyclopentylamino group, Nn-hexylamino Group, N-cyclohexylamino group, N-benzylamino group, N-phenethylamino group, N-phenylamino group, N- (1-naphthyl) amino group, N- (2-naphthyl) amino group, N- (4 -Phenylphenyl) amino group, N- (3-phenylphenyl) amino group, N- (2-phenylphenyl) amino group, N- (4-methylphenyl) amino group, N- (2-methylphenyl) Nyl) amino group, N- (2-anthranyl) amino group, N- (9-anthranyl) amino group, N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-propylamino Group, N, N-di-isopropylamino group, N, N-di-n-butylamino group, N, N-di-isobutylamino group, N, N-di-sec-butylamino group, N, N- Di-n-pentylamino group, N, N-dicyclopentylamino group, N, N-dicyclohexylamino group, N, N-dibenzylamino group, N, N-diphenethylamino group, N-methyl-N-ethyl An amino group, an N-methyl-Nn-propylamino group,

N-methyl-N-isopropylamino group, N-methyl-Nn-butylamino group, N-methyl-N-tert-butylamino group, N-methyl-N-cyclopentylamino group, N-methyl-N- Cyclohexylamino group, N-methyl-N-benzylamino group, N-methyl-N-phenethylamino group, N-ethyl-N-tert-butylamino group, N-ethyl-N-cyclohexylamino group, N-ethyl- N-benzylamino group, N-isopropyl-N-cyclopentylamino group, N-isopropyl-N-cyclohexylamino group, N-isopropyl-N-benzylamino group, N-tert-butyl-N-cyclohexylamino group, N- tert-butyl-N-benzylamino group, N-cyclopentyl-N-benzylamino group, N-cyclohexyl-N-benzylamino group, -Methyl-N-phenylamino group, N-ethyl-N-phenylamino group, N-cyclohexyl-N-phenylamino group, N, N-diphenylamino group, N, N-di (1-naphthyl) amino group, N, N-di (2-naphthyl) amino group, N, N-di (4-phenylphenyl) amino group, N, N- (4-methylphenyl) amino group, N, N-di (3-methylphenyl) ) Amino group, N-phenyl-N- (1-naphthyl) amino group, N-phenyl-N- (2-naphthyl) amino group, N-phenyl-N- (4-phenylphenyl) amino group, N-phenyl -N- (4-methylphenyl) amino group, N- (1-naphthyl) -N- (4'-phenylphenyl) amino group, N-phenyl-N- (4-tert-butylphenyl) amino group, N -Phenyl-N- (3-tert -Butylphenyl) group.

Specific examples of the substituted or unsubstituted linear, branched or cyclic alkoxycarbonyl group represented by R _{1 to} R ₈ include methoxycarbonyl group, ethoxycarbonyl group, n-propyloxycarbonyl group, isopropyloxycarbonyl group, n-butyl. Oxycarbonyl group, isobutyloxycarbonyl group, tert-butyloxycarbonyl group, n-pentyloxycarbonyl group, n-hexyloxycarbonyl group, n-heptyloxycarbonyl group, n-octyloxycarbonyl group, n-nonyloxycarbonyl group , N-decyloxycarbonyl group, cyclopentyloxycarbonyl group, and cyclohexyloxycarbonyl group.

Specific examples of the substituted or unsubstituted aryloxycarbonyl group for R _{1 to} R ₈ include a phenyloxycarbonyl group, a 1-naphthyloxycarbonyl group, a 2-naphthyloxycarbonyl group, a 4-methylphenyloxycarbonyl group, 4- Examples thereof include a phenylphenyloxycarbonyl group and a 2-phenylphenyloxycarbonyl group.

Specific examples of the substituted or unsubstituted linear, branched or cyclic alkylcarbonyloxy group for R _{1 to} R ₈ include a methylcarbonyloxy group, an ethylcarbonyloxy group, an n-propylcarbonyloxy group, an isopropylcarbonyloxy group, n-butylcarbonyloxy group, isobutylcarbonyloxy group, n-pentylcarbonyloxy group, n-hexylcarbonyloxy group, n-heptylcarbonyloxy group, n-octylcarbonyloxy group, n-nonylcarbonyloxy group, n-decyl Examples thereof include a carbonyloxy group, a cyclopentylcarbonyloxy group, and a cyclohexylcarbonyloxy group.

Specific examples of the substituted or unsubstituted arylcarbonyloxy group for R _{1 to} R ₈ include a phenylcarbonyloxy group, a 1-naphthylcarbonyloxy group, a 2-naphthylcarbonyloxy group, a 4-methylphenylcarbonyloxy group, 4- Examples thereof include a phenylphenylcarbonyloxy group and a 2-phenylphenylcarbonyloxy group.

Specific examples of the substituted or unsubstituted aminocarbonyl group for R _{1 to} R ₈ include aminocarbonyl group, N-methylaminocarbonyl group, N-ethylaminocarbonyl group, Nn-propylaminocarbonyl group, N-isopropyl. Aminocarbonyl group, Nn-butylaminocarbonyl group, N-isobutylaminocarbonyl group, Nn-hexylaminocarbonyl group, N-cyclohexylcarbonyl group, Nn-octylaminocarbonyl group, N-benzylaminocarbonyl group N-phenylaminocarbonyl group, N, N-dimethylaminocarbonyl group, N, N-diethylaminocarbonyl group, N-methyl-N-ethylaminocarbonyl group, N-methyl-N-cyclohexylaminocarbonyl group, N, N A diisopropylaminocarbonyl group, N, -Di-n-hexylaminocarbonyl group, N, N-di-n-octylaminocarbonyl group, N, N-dicyclohexylcarbonyl group, N, N-dibenzylaminocarbonyl group, N, N-diphenylaminocarbonyl group Can be mentioned.

In addition, R _{1 to} R ₈ adjacent groups may be bonded to each other to form a cyclic structure. Here, examples of the cyclic structure include carbocyclic aromatic rings, heterocyclic aromatic rings, carbocyclic aliphatic rings and / or heterocyclic aliphatic rings, and these cyclic structures are substituted. It may have a group or may be unsubstituted. Preferred are carbocyclic aromatic rings and / or heterocyclic aromatic rings, and more preferred are carbocyclic aromatic rings.

In the 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative represented by the general formula (1), Ar ₁ and Ar ₂ represent a substituted or unsubstituted aryl group. Ar ₁ and Ar ₂ are preferably a substituted or unsubstituted aryl group having 2 to 30 carbon atoms (including a heteroaryl group), more preferably a substituted or unsubstituted aryl group having 4 to 25 carbon atoms. A group (including a heteroaryl group).
Specific examples of Ar ₁ and Ar ₂ include the substituted or unsubstituted aryl groups listed as specific examples of the substituted or unsubstituted aryl group of R _{1 to} R ₈ .

In the 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative represented by the general formulas (1-A) to (1-C) of the present invention, Y _{1 to} Y ₄ are hydrogen atoms. or represents a substituent, examples of the substituent groups include the substituent groups listed as the substituents of R ₁ to R _8.

Moreover, the adjacent groups of Y _{1 to} Y ₄ may be bonded to each other to form a cyclic structure. Here, the cyclic structure has the same meaning as the cyclic structure that can be formed by bonding adjacent groups of R _{1 to} R ₈ to each other.

  Specific examples of the 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative of the present invention include, for example, the compounds shown below (Chemical Formula 4 to Chemical Formula 19). It is not limited to the specific example.

  In the specific examples, when isomers are present due to the rotation hindrance of the substituent, either one of these isomers or a mixture of isomers can be suitably used.

  The 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative of the present invention can be produced, for example, according to the following steps.

  Production of 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative represented by the general formula (1) -1 (Chemical Formula 20)

[Wherein R _{1 to} R ₈ , Ar ₁ and Ar ₂ represent the same meaning as in general formula (1), and L ₁ and L ₂ represent a leaving group such as a halogen atom]
That is, the halogenated fluoranthene derivative represented by the general formula (A) is mixed with a hydrazine derivative represented by the general formula (B) as a palladium catalyst [for example, palladium acetate / di-tert-butylphenylphosphine, palladium acetate / tricyclohexyl. Phosphine, palladium acetate / tri-tert-butylphosphine, tris (dibenzylideneacetone) dipalladium / di-tert-butyl-o-biphenylphosphine] and bases (eg sodium carbonate, potassium carbonate, tert-butoxy sodium, tert- By reacting in the presence of potassium butoxy), a 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative represented by the general formula (1) can be produced.

  Production of 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative represented by the general formula (1) -2 (Chemical Formula 21)

[Wherein R _{1 to} R ₈ , Ar ₁ and Ar ₂ represent the same meaning as in general formula (1), and L ₁ , L ₂ and L ₃ represent a leaving group such as a halogen atom]
Alternatively, when Ar ₁ and Ar ₂ are introduced sequentially, a hydrazine derivative represented by the general formula (C) is added to a palladium catalyst [for example, a halogenated fluoranthene derivative represented by the general formula (A)] Palladium acetate / di-tert-butylphenylphosphine, palladium acetate / tricyclohexylphosphine, palladium acetate / tri-tert-butylphosphine, tris (dibenzylideneacetone) dipalladium / di-tert-butyl-o-biphenylphosphine] and By reacting in the presence of a base (for example, sodium carbonate, potassium carbonate, tert-butoxy sodium, tert-butoxy potassium), an intermediate represented by the general formula (D) is obtained, and then the general formula (E) An intermediate represented by the general formula (D) and a palladium catalyst [e.g. Palladium acetate / di-tert-butylphenylphosphine, palladium acetate / tricyclohexylphosphine, palladium acetate / tri-tert-butylphosphine, tris (dibenzylideneacetone) dipalladium / di-tert-butyl-o-biphenylphosphine] By reacting in the presence, a 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative represented by the general formula (1) can be produced.

  The organic electroluminescent device of the present invention comprises at least one layer containing at least one 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative between a pair of electrodes. . Here, the organic electroluminescent element is usually formed by sandwiching at least one light emitting layer containing at least one organic light emitting component between a pair of electrodes.

In the organic electroluminescent device of the present invention, the 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative is preferably contained in the light emitting layer or the charge injection / transport layer, and contained in the light emitting layer. More preferably.
Here, the charge injection transport layer represents a hole injection transport layer and an electron injection transport layer.
The configuration of the organic electroluminescent device of the present invention is not particularly limited. For example, (EL-1) anode / hole injection transport layer / light emitting layer / electron injection transport layer / cathode type device (FIG. 1). ), (EL-2) anode / hole injection transport layer / light emitting layer / cathode type device (FIG. 2), (EL-3) anode / light emitting layer / electron injection transport layer / cathode type device (FIG. 3), EL-4) Anode / light emitting layer / cathode type element (FIG. 4), and the like. Further, an EL (EL-5) anode / hole injection / transport layer / electron injection / transport layer / light-emitting layer / electron injection / transport layer / cathode-type device (FIG. 5) in which the light-emitting layer is sandwiched between electron injection / transport layers. You can also. The (EL-4) type element structure includes an element of a type in which a light emitting component is sandwiched between a pair of electrodes as a light emitting layer, (EL-6) a hole injection transport component as a light emitting layer, A device of a type in which a light emitting component and an electron injection component are mixed and sandwiched between a pair of electrodes (FIG. 6), (EL-7) a layer in which a hole injection transport component and a light emitting component are mixed as a light emitting layer Type element sandwiched between a pair of electrodes in a form (FIG. 7), (EL-8) type element sandwiched between a pair of electrodes in a single layer form in which a light emitting component and an electron injection component are mixed as a light emitting layer Any of (FIG. 8) may be sufficient.

  The organic electroluminescent device of the present invention is not limited to these device configurations, and each type of device can be provided with a plurality of hole injection / transport layers, light emitting layers, and electron injection / transport layers. Further, in each type of device, the hole injection / transport layer is disposed between the light emitting layer, the hole injection / transport component and the light emitting component mixed layer and / or the light emitting layer and the electron injection / transport layer between the light emitting component and the light emitting component. And a mixed layer of electron injecting and transporting components can be provided.

  A preferred organic electroluminescent element is an (EL-1) type element, an (EL-2) type element, an (EL-5) type element, an (EL-6) type element or an (EL-7) type element. More preferably, it is an (EL-1) type element, an (EL-2) type element or an (EL-7) type element.

  Hereinafter, the components of the organic electroluminescence device of the present invention will be described in detail. As an example, (EL-1) anode / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode type device shown in FIG. 1 will be described.

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

The organic electroluminescent element of the present invention is preferably supported by the substrate 1, and the substrate is not particularly limited, but a transparent or translucent substrate is preferable, and the material is soda lime glass, Examples thereof include glass such as borosilicate glass and transparent polymers such as polyester, polycarbonate, polysulfone, polyethersulfone, polyacrylate, polymethyl methacrylate, polypropylene, and polyethylene. Further, a substrate made of a translucent plastic sheet, quartz, transparent ceramics, or a composite sheet in which these are combined can also be used. Furthermore, for example, a color filter film, a color conversion film, and a dielectric reflection film can be combined with the substrate to control the emission color.

As the anode 2, it is preferable to use a metal, an alloy or a conductive compound having a relatively large work function as an electrode material. Examples of the electrode material used for the anode include gold, platinum, silver, copper, cobalt, nickel, palladium, vanadium, tungsten, indium oxide (In ₂ O ₃ ), tin oxide (SnO ₂ ), zinc oxide, ITO ( Indium tin oxide (Indium Tin Oxide), polythiophene, polypyrrole, etc. can be mentioned. These electrode materials may be used alone or in combination. For the anode, these electrode materials can be formed on the substrate by a method such as vapor deposition or sputtering.
Further, the anode may have a single layer structure or a multilayer structure. The sheet electrical resistance of the anode is preferably set to several hundred Ω or less, more preferably about 5 to 50 Ω.
The thickness of the anode is generally about 5 to 1000 nm, more preferably about 10 to 500 nm, although it depends on the material of the electrode material used.

The hole injection transport 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 of the electroluminescent device of the present invention is a compound having a hole injecting and transporting function (for example, phthalocyanine derivatives, triarylamine derivatives, triarylmethane derivatives, oxazole derivatives, hydrazone derivatives, stilbene derivatives, pyrazoline derivatives, Polysilane derivatives, polyphenylene vinylene and derivatives thereof, polythiophene and derivatives thereof, poly-N-vinylcarbazole, polytriarylamine derivatives and the like).
These compounds having a hole injecting and transporting function may be used alone or in combination.

  Specific examples of the triarylamine derivative having a hole injecting and transporting function include, for example, 4,4′-bis [N-phenyl-N- (4 ″ -methylphenyl) amino] -1,1′-biphenyl, 4 , 4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] -1,1′-biphenyl, 4,4′-bis [N-phenyl-N- (3 ″ -methoxyphenyl) amino ] -1,1′-biphenyl, 4,4′-bis [N-phenyl-N- (1 ″ -naphthyl) amino] -1,1′-biphenyl, 3,3′-dimethyl-4,4′- Bis [N-phenyl-N- (3 ″ -methylphenyl) amino] -1,1′-biphenyl, 1,1-bis [4 ′-[N, N-di (4 ″ -methylphenyl) amino] phenyl ] Cyclohexane, 9,10-bis [N- (4'-methylphen Nyl) -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 -Carbazolyl) Trifeni Amine, 4,4 ', 4 "-tris [N, N-bis (4"'-tert-butylbiphenyl-4 ""-yl) amino] triphenylamine, 1,3,5-tris [N- ( 4'-diphenylaminophenyl) -N-phenylamino] benzene.

In the organic electroluminescent device of the present invention, 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative can be used for the hole injecting and transporting layer.
In the case where a 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative and a compound having a hole injection function are used in combination, 1,2-dihydro-1,2-diaza occupying in the hole injection transport layer -Content of a cyclopenta [cd] fluoranthene derivative becomes like this. Preferably it is 0.1 mass% or more, More preferably, it is 0.5-99.9 mass%, More preferably, it is 3-97 mass%.

The light emitting layer 4 is a layer containing a compound having a function of injecting holes and electrons, a function of transporting them, and a function of generating excitons by recombination of holes and electrons.
The light-emitting layer can be formed using at least one 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative and / or other compound having a light-emitting function.

  Examples of compounds having a light emitting function other than 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivatives include, for example, acridone derivatives, quinacridone derivatives, diketopyrrolopyrrole derivatives, polycyclic aromatic compounds [for example, Rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis ( 9'-ethynylanthcenyl) benzene, 4,4'-bis (9 "-ethynylanthracenyl) biphenyl, dibenzo [f, f] diindeno [1,2,3-cd: 1 ', 2', 3 '-lm] perylene derivatives], triarylamine derivatives (eg, hole injection transporter) Can be mentioned), organometallic complexes [eg tris (8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, 2- (2′-hydroxyphenyl) benzo] Zinc salt of thiazole, zinc salt of 4-hydroxyacridine, zinc salt of 3-hydroxyflavone,

Beryllium salt of 5-hydroxyflavone, aluminum salt of 5-hydroxyflavone], stilbene derivatives [for example, 1,1,4,4-tetraphenyl-1,3-butadiene, 4,4′-bis (2,2- Diphenylvinyl) biphenyl, 4,4′-bis [(1,1,2-triphenyl) ethenyl] biphenyl], coumarin derivatives (eg, coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 106, coumarin 138, Coumarin 151, Coumarin 152, Coumarin 153, Coumarin 307, Coumarin 311, Coumarin 314, Coumarin 334, Coumarin 338, Coumarin 343, Coumarin 500), pyran derivatives (eg DCM1, DCM2), oxazone derivatives (eg Nile Red), Benzothiazole derivatives, benzoo Sazole 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 Examples include vinylene and derivatives thereof, polyterphenylene vinylene and derivatives thereof, polynaphthylene vinylene and derivatives thereof, and polythienylene vinylene and derivatives thereof.

  Compounds having a light emitting function other than 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivatives include acridone derivatives, quinacridone derivatives, polycyclic aromatic compounds, triarylamine derivatives, organometallic complexes, and stilbenes. Derivatives are preferred, and polycyclic aromatic compounds and organometallic complexes are more preferred.

  The organic electroluminescent element of the present invention preferably contains a 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative in the light emitting layer.

1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative and 1,2,
-1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative occupying in the light emitting layer when a compound having a light emitting function other than dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative is used in combination Is preferably adjusted to 0.001 to 99.999 mass%.
The light emitting layer can also be formed from a host compound and a guest compound (dopant) as described in J. Appl. Phys., 65 , 3610 (1989), and Japanese Patent Application Laid-Open No. 5-214332.
The 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative can be used as a host compound in the light-emitting layer, and can also be used as a guest compound. In the case where a light emitting layer is formed using a 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative as a host compound, examples of the guest compound include compounds having other light emitting functions described above. Of these, polycyclic aromatic compounds are preferred.

When forming a light-emitting layer using a 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative as a host compound, the 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative The guest compound is preferably used in an amount of 0.001 to 40% by mass, more preferably 0.01 to 30% by mass, and still more preferably 0.1 to 20% by mass. A dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative as a guest compound, and at least one compound having a light emitting function other than the 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative Can also be used to form.
When the 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative is used as a guest compound in combination with another compound having a light emitting function, 1,2-dihydro-1,2- occupying the light emitting layer The diaza-cyclopenta [cd] fluoranthene derivative is preferably 0.001 to 40% by mass, more preferably 0.01 to 30% by mass, and still more preferably 0.1 to 20% by mass.

  When a light-emitting layer is formed using a 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative as a guest compound, the host compound may be a polycyclic aromatic compound, a triarylamine derivative, an organic metal Complexes and stilbene derivatives are preferred, and polycyclic aromatic compounds and organometallic complexes are more preferred.

The electron injection / transport layer 5 is a layer containing a compound having a function of facilitating injection of electrons from the cathode and / or a function of transporting injected electrons.
Examples of the compound having an electron injecting function used in the electron injecting and transporting layer include organometallic complexes, oxadiazole derivatives, triazole derivatives, triazine derivatives, perylene derivatives, quinoline derivatives, quinoxaline derivatives, diphenylquinone derivatives, nitro-substituted fluorenones. Derivatives, thiopyrandioxide derivatives and the like. Examples of the organometallic complex include an organoaluminum complex such as tris (8-quinolinolato) aluminum, an organic beryllium complex such as bis (10-benzo [h] quinolinolato) beryllium, a beryllium salt of 5-hydroxyflavone, 5- Examples thereof include an aluminum salt of hydroxyflavone. An organoaluminum complex is preferable, and an organoaluminum complex having a substituted or unsubstituted 8-quinolinolato ligand is more preferable. Examples of the organoaluminum complex having a substituted or unsubstituted 8-quinolylate ligand include compounds represented by general formula (a) to general formula (c).

(Q) ₃ -Al (a)
(Wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand)
(Q) ₂ -Al-OL '(b)
(Wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand, OL ′ represents an aryloxy ligand, and L ′ represents an aryl group having 6 to 24 carbon atoms)
(Q) _2- Al-O-Al- (Q) ₂ (c)
(Wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand)
Specific examples of the organoaluminum complex having a substituted or unsubstituted 8-quinolinolato 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-methylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (3-methylphenolate) ) Aluminum, bis (2-methyl-8-quinolinolato) (4-methylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) ) (3-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (4-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (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- Quinolinolate) (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-quinolinolato) (2,4,6-triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,4,6- Trimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,4,5,6- Tetramethyl phenolate) aluminum, bis (2-methyl-8-quinolinolato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinolato) (2-naphtholato) aluminum,

Bis (2,4-dimethyl-8-quinolinolato) (2-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3-phenylphenolato) aluminum, bis (2,4-dimethyl- 8-quinolinolato) (4-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3,5-dimethylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3 , 5-di-tert-butylphenolate) 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, bi (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum.

A compound having an electron injection function may be used alone or in combination.
In the organic electroluminescent device of the present invention, a 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative can be used for the electron injecting and transporting layer.
When a 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative and a compound having an electron injection function are used in combination, 1,2-dihydro-1,2-diaza-cyclopent occupying in the electron injection transport layer The content of the [cd] fluoranthene derivative is preferably 0.1% by mass or more, more preferably 0.5 to 99.9% by mass, and further preferably 3 to 97% by mass.

In the organic electroluminescence device of the present invention, a metal fluoride such as LiF or MgF, lithium acetate, lithium propionate, lithium benzoate, etc. is further provided between the electron injection transport layer and the cathode for the purpose of increasing the electron injection efficiency. It is also possible to form an intermediate layer of a lithium salt of the organic compound.
As the cathode 6, it is preferable to use a metal, an alloy or a 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, yttrium, and aluminum. , Aluminum-lithium alloys, aluminum-calcium alloys, aluminum-magnesium alloys, and graphite thin films. These electrode materials may be used alone or in combination.

For the cathode, these electrode materials can be formed on the electron injecting and transporting layer by, for example, vapor deposition, sputtering, ion vapor deposition, ion plating, or cluster ion beam.
The cathode may have a single layer structure or a multilayer structure. The sheet electrical resistance of the cathode is preferably several hundred Ω or less. The thickness of the cathode is usually 5 to 1000 nm, preferably 10 to 500 nm, although it depends on the electrode material used. In order to efficiently extract light emitted from the organic electroluminescent device of the present invention, at least one of the anode and the cathode is preferably transparent or translucent, and generally has a transmittance of emitted light of 70% or more. It is preferable to set the material and thickness of the anode or cathode.

  The organic electroluminescent device of the present invention may contain a singlet oxygen quencher in at least one of the hole injection transport layer, the light emitting layer, and the electron injection transport layer. Although it does not specifically limit as a singlet oxygen quencher, For example, rubrene, a nickel complex, diphenylisobenzofuran is mentioned, Preferably it is rubrene.

The layer containing the singlet oxygen quencher is not particularly limited, but is preferably a light emitting layer or a hole injection transport layer, and more preferably a hole injection transport layer. When a singlet oxygen quencher is contained in the hole injecting and transporting layer, it may be uniformly contained in the hole injecting and transporting layer, and a layer adjacent to the hole injecting and transporting layer (for example, a light emitting layer, a light emitting function). May be contained in the vicinity of the electron injecting and transporting layer).
As content of a singlet oxygen quencher, 0.01-50 mass% of the total quantity which comprises the layer (for example, hole injection transport layer) to contain, Preferably, 0.05-30 mass%, more Preferably, it is 0.1-20 mass%.

The formation method of the hole injection transport layer, the light emitting layer, and the electron injection transport layer is not particularly limited. For example, a vacuum deposition method, an ionization deposition method, a solution coating method (for example, a spin coating method, a casting method, A dip coat method, a bar coat method, a roll coat method, a Langmuir-Blodget method, an ink jet method) can be used. When forming each layer such as a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer by a vacuum deposition method, the conditions for vacuum deposition are not particularly limited, but a vacuum of about 10 ⁻³ Pa or less is usually used. Below, it is preferable to carry out at a boating temperature (deposition source temperature) of about 50 to 500 ° C., a substrate temperature of about −50 to 300 ° C., and a deposition rate of about 0.005 to 50 nm / sec. In this case, each layer such as a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer is preferably formed continuously under vacuum. It becomes possible to manufacture an organic electroluminescent element excellent in various characteristics by forming continuously. When each layer such as hole injection transport layer, light emitting layer, electron injection transport layer, etc. is formed using a plurality of compounds by vacuum deposition, the temperature of each boat containing the compounds is individually controlled and co-evaporated. It is preferable to do.

When each layer is formed by a solution coating method, the component forming each layer or the component and a binder resin are dissolved or dispersed in a solvent to obtain a coating solution. Examples of the solvent include organic solvents (hydrocarbon solvents such as hexane, octane, decane, toluene, xylene, ethylbenzene, and 1-methylnaphthalene, ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, dichloromethane, and chloroform. , Halogenated hydrocarbon solvents such as tetrachloromethane, dichloroethane, trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene, chlorotoluene, ester solvents such as ethyl acetate, butyl acetate, amyl acetate, ethyl lactate, methanol, propanol, butanol Alcohol solvents such as pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve, ethylene glycol, dibutyl ether, tetrahydro Ether solvents such as ethylene, dioxane, dimethoxyethane, anisole, N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide And polar solvents) and water. A solvent may be used independently and may be used together.
When the components of the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer are dispersed in a solvent, for example, a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer or the like is used as a dispersion method. Can be used.

Examples of binder resins that can be used for each layer such as a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer include poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethyl methacrylate, poly Methyl acrylate, polyether, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide, polyethersulfone, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polyphenylene vinylene and derivatives thereof, polyfluorene and derivatives thereof, Examples thereof include polymer compounds such as polythienylene vinylene and its derivatives. Binder resins may be used alone or in combination. Although the density | concentration of a coating liquid is not specifically limited, It can set to the density | concentration range suitable for producing desired thickness with the apply | coating method to implement, Usually, 0.1-50 mass%, Preferably 1 to 30% by mass. When a binder resin is used, the amount used is not particularly limited, but it is usually based on the total amount of components and binder resin that form each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer. The binder resin is used so that the content of the binder resin is 5 to 99.9% by mass, preferably 10 to 99% by mass (relative to the total amount of each component when a single-layer element is formed).
The thickness of each layer such as the hole injection transport layer, the light emitting layer, and the electron injection transport layer is not particularly limited, but is usually 5 nm to 5 μm.

The organic electroluminescent device of the present invention produced under the above conditions is provided with a protective layer (sealing layer) for the purpose of preventing contact with oxygen, moisture, etc. For example, it can be protected by enclosing it in paraffin, liquid paraffin, silicon oil, fluorocarbon oil, zeolite-containing fluorocarbon oil). Examples of the material used for the protective layer include organic polymer materials (for example, fluorine resin, epoxy resin, silicone resin, epoxy silicone resin, polystyrene, polyester, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, Polyphenylene oxide), inorganic materials (eg diamond thin films, amorphous silica, electrically insulating glass, silicon nitride / silicon oxide mixtures, metal oxides, metal nitrides, metal carbides, metal sulfides), and photo-curing Resins can be mentioned. The material used for the protective layer may be used alone or in combination. The protective layer may have a single layer structure or a multilayer structure.
Moreover, the organic electroluminescent element of this invention can also provide a metal oxide film (for example, aluminum oxide film) and a metal fluoride film as a protective film in an electrode.

The organic electroluminescent element of the present invention can also be provided with an interface layer (intermediate layer) on the surface of the anode. Examples of the material for the interface layer include organic phosphorus compounds, polysilanes, aromatic amine derivatives, and phthalocyanine derivatives.
Furthermore, the surface of an electrode, for example, an anode, can be used by treating the surface with acid, ammonia / hydrogen peroxide, UV / ozone or oxygen plasma.

  The organic electroluminescent element of the present invention can be usually used as a DC drive type element, but can also be used as an AC drive type element. Further, the organic electroluminescence device of the present invention may be a segment type, a passive drive type such as a simple matrix drive type, or an active drive type such as a TFT (thin film transistor) type or an MIM (metal-insulator-metal) type. It may be. The driving voltage is usually 2 to 30V. The organic electroluminescent element of the present invention includes a panel-type light source (for example, a backlight for a clock, a liquid crystal panel, etc.), various light-emitting elements (for example, an alternative to a light-emitting element such as an LED), and various display elements [for example, information display Element (PC monitor, mobile phone / mobile terminal display element)], illumination, various signs, various sensors, etc.

  EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further in detail, this invention is not limited to a following example.

Production of exemplary compound A-1 3,4-dibromofluoranthene 3.60 g (0.010 mol), N, N′-diphenylhydrazine 2.02 g (0.011 mol), tert-butoxy sodium 2.12 g ( 0.022 mol), 22 mg of palladium acetate and 30 ml of mixed xylene were added with 67 mg of di-tert-butylphenylphosphine under an argon stream, heated to 110 ° C., and stirred at the same temperature for 6 hours. It was. Thereafter, the reaction mixture was cooled to room temperature, insoluble matters were filtered off, and the filtrate was washed with water. The mixed xylene was distilled off from the organic phase under reduced pressure, the residue was purified by silica gel column chromatography, and further recrystallized from cyclohexane to obtain 2.8 g of the target compound of exemplary compound A-1 as orange crystals. .
Further, this compound was purified by sublimation at 290 ° C. and 2.0 × 10 ⁻⁴ Pa.

Production of Exemplified Compound A-2 3,4-dibromofluoranthene 3.60 g (0.010 mol), N-phenylhydrazine 1.19 g (0.011 mol), tert-butoxy sodium 2.12 g (0.022 mol) Mol), 22 mg of palladium acetate and 30 ml of mixed xylene, 67 mg of di-tert-butylphenylphosphine was added under an argon stream, heated to 110 ° C., and heated and stirred at the same temperature for 8 hours. Thereafter, the reaction mixture was cooled to room temperature, insoluble matters were filtered off, and the filtrate was washed with water. The mixed xylene was distilled off from the organic phase under reduced pressure, the residue was recrystallized from toluene / isopropanol, and 2.1 g of 1-N-phenyl-1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene was obtained. Obtained. Next, 1.53 g (0.005 mol) of 1-N-phenyl-1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene, 1.27 g (0.005 mol) of 1-iodonaphthalene, To a mixture of 0.58 g (0.006 mol) of tert-butyl sodium, 5.6 mg of palladium acetate and 20 ml of mixed xylene, 17 mg of di-tert-butylphenylphosphine was added under an argon stream and heated to 110 ° C. The mixture was heated and stirred at the same temperature for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, insoluble matters were filtered off, and the filtrate was washed with water. The mixed xylene was distilled off from the organic phase under reduced pressure, the residue was purified by silica gel column chromatography, and further recrystallized from toluene / n-hexane to obtain 1.24 g of the compound of exemplary compound A-2 as orange crystals. .
Further, this compound was purified by sublimation under the conditions of 300 ° C. and 1.5 × 10 ⁻⁴ Pa.

Production Example of Exemplified Compound A-17 In Example 2, instead of using 1.27 g (0.005 mol) of 1-iodonaphthalene, 1.29 g (0.005 mol) of 9-bromophenanthrene was used. According to the operation described in Example 2, 1.32 g of the compound of exemplary compound A-17 was obtained as orange crystals.
Further, this compound was purified by sublimation under conditions of 320 ° C. and 2.0 × 10 ⁻⁴ Pa.

Production of Exemplified Compound A-21 In Example 1, instead of using 3.60 g (0.010 mol) of 3,4-dibromofluoranthene, 3,4-dibromo-7,10-diphenylfluoranthene 5 Except that 0.12 g (0.010 mol) was used, according to the procedure described in Example 1, 3.22 g of the compound of exemplary compound A-21 was obtained as orange crystals.
Further, this compound was purified by sublimation under conditions of 350 ° C. and 2.0 × 10 ⁻⁴ Pa.

Preparation of Exemplified Compound B-13 In Example 1, instead of using 3.60 g (0.010 mol) of 3,4-dibromofluoranthene and 2.02 g (0.011 mol) of N, N′-diphenylhydrazine 7,8-dibromo-1,4-diphenylbenzo [a] acethrylene 5.62 g (0.010 mol) and N, N′-di (1′-naphthyl) hydrazine 3.12 g (0.011) The compound of Exemplified Compound B-13 was obtained as orange crystals by the procedure described in Example 1, except that (mol) was used.
Further, this compound was purified by sublimation under conditions of 390 ° C. and 1.4 × 10 ⁻⁴ Pa.

Production of Exemplified Compound D-1 In Example 1, instead of using 3.60 g (0.010 mol) of 3,4-dibromofluoranthene, 4.10 g of 3,4-dibromobenzo [k] fluoranthene (0 (0.010 mol) was used, and 2.84 g of the compound of exemplary compound D-1 was obtained as orange crystals according to the procedure described in Example 1.
Further, this compound was purified by sublimation under conditions of 340 ° C. and 1.4 × 10 ⁻⁴ Pa.

Preparation of Exemplified Compound D-5 In Example 1, instead of using 3.60 g (0.010 mol) of 3,4-dibromofluoranthene and 2.02 g (0.011 mol) of N, N′-diphenylhydrazine 3,4-dibromobenzo [k] fluoranthene 4.10 g (0.010 mol) and N, N
Except that 3.70 g (0.011 mol) of '-di (4'-phenylphenyl) hydrazine was used, 3.42 g of the compound of exemplary compound D-5 was obtained as orange crystals according to the procedure described in Example 1. .
Further, this compound was purified by sublimation under conditions of 380 ° C. and 2.2 × 10 ⁻⁴ Pa.

Production of Exemplified Compound D-19 In Example 2, instead of using 3.60 g (0.010 mol) of 3,4-dibromofluoranthene and 1.27 g (0.005 mol) of 1-iodonaphthalene, 3 , 4-dibromobenzo [k] fluoranthene 4.10 g (0.010 mol) and 4-phenoxyiodobenzene 1.48 g (0.005 mol) were used according to the procedure described in Example 2 except that 1.26 g of D-19 compound was obtained as orange crystals.
Further, this compound was purified by sublimation under conditions of 360 ° C. and 2.0 × 10 ⁻⁴ Pa.

Production of Exemplified Compound D-21 In Example 1, instead of using 3.60 g (0.010 mol) of 3,4-dibromofluoranthene, 3,4-dibromo-7,12-diphenylbenzo [k] Except that 5.62 g (0.010 mol) of fluoranthene was used, 3.18 g of the compound of Exemplified Compound D-21 was obtained as orange crystals in accordance with the procedure described in Example 1.
Further, this compound was purified by sublimation under conditions of 390 ° C. and 1.8 × 10 ⁻⁴ Pa.

Preparation of Exemplified Compound D-26 In Example 1, instead of using 3.60 g (0.010 mol) of 3,4-dibromofluoranthene, 7- (biphenyl-2′-yl) -3,4- Except that 6.38 g (0.010 mol) of dibromo-12-phenylbenzo [k] fluoranthene was used, 3.09 g of the compound of Exemplified Compound D-26 was obtained according to the procedure described in Example 1.
Further, this compound was purified by sublimation under conditions of 410 ° C. and 1.8 × 10 ⁻⁴ Pa.

Production of Exemplified Compound D-31 In Example 2, instead of using 3.60 g (0.010 mol) of 3,4-dibromofluoranthene and 1.27 g (0.005 mol) of 1-iodonaphthalene, 7 6.38 g (0.010 mol) of-(biphenyl-2'-yl) -3,4-dibromo-12-phenylbenzo [k] fluoranthene and 1.29 g (0.005 mol) of 9-bromophenanthrene were used. Except for the above, according to the procedure described in Example 2, 1.36 g of the compound of Exemplified Compound D-31 was obtained as orange crystals.
Further, this compound was purified by sublimation at 420 ° C. and 1.2 × 10 ⁻⁴ Pa.

Production of Exemplified Compound D-33 In Example 1, instead of using 3.60 g (0.010 mol) of 3,4-dibromofluoranthene, 3,4-dibromo-7,8,11,12-tetra Except that 7.14 g (0.010 mol) of phenylbenzo [k] fluoranthene was used, Example D-33 was converted to 3.7 as orange crystals according to the procedure described in Example 1.
2 g was obtained.
Further, this compound was purified by sublimation under conditions of 450 ° C. and 1.5 × 10 ⁻⁴ Pa.

Production of Organic Electroluminescent Device A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, and then fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 1.0 × 10 ⁻⁴ Pa. First, N, N′-diphenyl-N, N′-di (1 ″ -naphthyl) -4,4′-diamino-1,1′-biphenyl is deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec. A hole injecting and transporting layer was formed by vapor deposition to a thickness of 75 nm, and then a compound of Tris (8-quinolinol) aluminum and exemplary compound A-21 was deposited on the hole injecting and transporting layer at a deposition rate of 0.2 nm / Co-evaporated to a thickness of 40 nm in sec (mass ratio 93: 7) to form a light emitting layer, and further, tris (8-quinolinol) aluminum was deposited to a thickness of 25 nm at a deposition rate of 0.2 nm / sec. An electron injecting and transporting layer was formed, and magnesium and silver were co-deposited as a cathode at a deposition rate of 1.0 nm / sec to a thickness of 200 nm (mass ratio 9: 1). 100nm thickness at 0nm / sec The organic electroluminescence device was fabricated by vapor deposition, and the deposition was carried out while maintaining the reduced pressure state of the deposition tank.DC voltage was applied to the fabricated organic electroluminescence device, and room temperature was 10 mA in a dry atmosphere. / cm was continuously allowed driven at a constant current density of ^2. the initial, 5.6 V, green luminescence of luminance 650 cd / ^{m 2} was identified. half life of the luminance was 7500 hours.

: Preparation of organic electroluminescent device In Example 13, the procedure described in Example 13 was used except that instead of using the compound of Exemplified Compound A-21 in forming the light emitting layer, Exemplified Compound A-2 was used. According to the above, an organic electroluminescent device was manufactured, and a DC voltage was applied to the manufactured device, and the device was continuously driven at a constant current density of 10 mA / cm ² in a room temperature dry atmosphere. The results are summarized in Table 1.

: Preparation of organic electroluminescent element In Example 13, the compound of Exemplified Compound A-17 was used instead of the compound of Illustrated Compound A-21 in the formation of the light emitting layer. According to the operation, an organic electroluminescence device was produced, and a DC voltage was applied to the produced device, and the device was continuously driven at a constant current density of 10 mA / cm ² in a room temperature dry atmosphere. The results are summarized in Table 1.

: Preparation of organic electroluminescent element In Example 13, the compound of Exemplified Compound B-13 was used instead of the compound of Illustrated Compound A-21 in the formation of the light emitting layer. According to the operation, an organic electroluminescence device was produced, and a DC voltage was applied to the produced device, and the device was continuously driven at a constant current density of 10 mA / cm ² in a room temperature dry atmosphere. The results are summarized in Table 1.

: Preparation of organic electroluminescent element In Example 13, the compound of Exemplified Compound D-19 was used instead of the compound of Illustrated Compound A-21 in forming the light emitting layer. According to the operation, an organic electroluminescence device was produced, a DC voltage was applied to the produced device, and it was continuously driven at a constant current density of 10 mA / cm ² in a room temperature dry atmosphere. The results are summarized in Table 1.

: Preparation of organic electroluminescent element In Example 13, the compound of Exemplified Compound D-26 was used instead of the compound of Illustrated Compound A-21 in forming the light emitting layer. According to the operation, an organic electroluminescence device was produced, and a DC voltage was applied to the produced device, and the device was continuously driven at a constant current density of 10 mA / cm ² in a room temperature dry atmosphere. The results are summarized in Table 1.

: Preparation of organic electroluminescent element In Example 13, the compound of Exemplified Compound D-31 was used instead of the compound of Illustrated Compound A-21 in forming the light emitting layer. According to the operation, an organic electroluminescence device was produced, and a DC voltage was applied to the produced device, and the device was continuously driven at a constant current density of 10 mA / cm ² in a room temperature dry atmosphere. The results are summarized in Table 1.

Comparative Example 1:
In Example 13, in the formation of the light emitting layer, organic compounds were prepared according to the procedure described in Example 13 except that N, N-dimethylquinacridone was used at a mass ratio of 99: 1 instead of using Exemplified Compound A-21. An electroluminescent element was produced. Green light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

Comparative Example 2:
In Example 13, when the light emitting layer was formed, an organic electroluminescent element was produced according to the procedure described in Example 13 except that Coumarin-6 was used instead of Example Compound A-21. Green light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

From Table 1, it can be seen that the organic electroluminescence device of the present invention has higher emission luminance (higher luminous efficiency) and longer emission life than the organic electroluminescence device of the comparative example.

: Preparation of organic electroluminescence device A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was ultrasonically cleaned using a neutral detergent, Semicoclean (manufactured by Furuuchi Chemical), ultrapure, acetone, and ethanol. The substrate was dried with nitrogen gas, further UV / ozone irradiated, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 1 × 10 ⁻⁴ Pa.
First, N, N'-diphenyl-N, N'-di (1 "-naphthyl)-on an ITO transparent electrode
4,4′-Diamino-1,1′-biphenyl was deposited at a deposition rate of 0.2 nm / sec to a thickness of 75 nm to form a hole injecting and transporting layer. Next, the compound of Exemplified Compound D-26 is deposited on the hole injecting and transporting layer at a deposition rate of 0.2 nm / sec to 40 nm to form a light emitting layer, and further tris (8-quinolinol) aluminum is deposited. Vapor deposition was performed at a thickness of 25 nm at 0.2 nm / sec to form an electron injecting and transporting layer. On top of that, magnesium and silver were co-deposited as a cathode to a thickness of 200 nm at a deposition rate of 1.0 nm / sec (mass ratio 9: 1) to form a cathode, and further silver was deposited at a deposition rate of 1.0 nm / sec to 100 nm. Vapor deposited to a thickness of In addition, vapor deposition was implemented, maintaining the pressure reduction state of a vapor deposition tank. A DC voltage was applied to the produced organic electroluminescent device, and the organic electroluminescent device was continuously driven at a constant current density of 10 mA / cm ² in a room temperature dry atmosphere. Initially, yellow-green light emission of 5.9 V and luminance of 960 cd / m ² was observed. The half life of luminance was 7800 hours.

: Preparation of organic electroluminescence device A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, and then poly [N, N′-di (4 ″ -n-hexylphenyl) -N, N ′-(4 ″) on the ITO transparent electrode. A toluene solution of “-phenylene) -4,4′-diamino-1,1′-biphenyl] was applied by spin coating to a thickness of 50 nm to form a first hole injection transport layer, and 110 ° C. for 1 hour. Dried. Next, this substrate was fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 2 × 10 ⁻⁴ Pa. On the first hole injection transport layer, N, N′-diphenyl-N, N′-di (1 ″ -naphthyl) -4,4′-diamino-1,1′-biphenyl was deposited at a deposition rate of 0.2 nm / The second hole injecting and transporting layer was formed at a thickness of 25 nm in sec. Next, the compound of Exemplified Compound D-33 and rubrene were mixed at a deposition rate of 0.2 nm / sec to a thickness of 40 nm. A light-emitting layer was formed by vapor deposition (mass ratio 96: 4), and tris (8-quinolinolato) aluminum was vapor-deposited to a thickness of 25 nm at a vapor deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. After depositing LiF to a thickness of 3 nm at a deposition rate of 0.2 nm / sec, aluminum was deposited to a thickness of 200 nm at a deposition rate of 1.0 nm / sec. The produced organic electroluminescent element A DC voltage was applied to the element, and the element was continuously driven at a constant current density of 10 mA / cm ^{2 in} a dry atmosphere at room temperature, and yellow light emission of 5.5 V and a luminance of 1200 cd / m ² was initially observed. The half life was 6400 hours.

A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. This substrate was dried using nitrogen gas, further UV / ozone cleaned, fixed to a substrate holder of a vapor deposition apparatus, and the vapor deposition tank was depressurized to 2 × 10 ⁻⁴ Pa. First, 4,4 ′, 4 ″ -tris [N- (3 ″ ′-methylphenyl) -N-phenylamino] triphenylamine is deposited on the ITO transparent electrode at a deposition rate of 0.2 nm / sec and a thickness of 50 nm. Then, a first hole injection transport layer was formed. Next, N, N, N ′, N′-tetra (1 ″ -naphthyl) -4,4′-diamino-1,1′-biphenyl was deposited to a thickness of 25 nm at a deposition rate of 0.2 nm / sec. A second hole injecting and transporting layer was formed, and then 9,10-diphenylanthracene and the compound of Exemplified Compound A-17 were simultaneously applied from different vapor deposition sources to a thickness of 40 nm at a vapor deposition rate of 0.2 nm / sec. Evaporation (mass ratio 90:10) was performed to form a light emitting layer, and then tris (8-quinolinolato) aluminum was vapor deposited at a deposition rate of 0.2 nm / sec to a thickness of 25 nm to form an electron injection transport layer. Further, magnesium and silver were co-deposited at a deposition rate of 1.0 nm / sec to a thickness of 200 nm as a cathode (mass ratio 9: 1), and silver was further deposited at a deposition rate of 1.0 nm / sec to 100 nm. Thickness An organic electroluminescent device was prepared by applying a direct current voltage to the produced organic electroluminescent device and dried at room temperature in a dry atmosphere at 10 mA / cm.
^It was continuously driven at a constant current density of ² . Initially, green light emission of 6.4 V and luminance of 940 cd / m ² was observed. The half life of luminance was 9000 hours.

: Preparation of organic electroluminescence device A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried using nitrogen gas, further UV / ozone cleaned, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 1 × 10 ⁻⁴ Pa.
First, N, N′-diphenyl-N, N ′-(1 ″ -naphthyl) -4,4′-diamino-1,1′-biphenyl and the compound of Exemplified Compound D-26 are different on the ITO transparent electrode. A hole injection / transport layer was formed by co-evaporation (mass ratio 90:10) to a thickness of 75 nm from a vapor deposition source at a vapor deposition rate of 0.2 nm / sec, followed by 9,10-di (2′-). Naphthyl) anthracene and Exemplified Compound D-33 were co-deposited from different deposition sources to a thickness of 40 nm at a deposition rate of 0.2 nm / sec (mass ratio 95: 5) to form a light-emitting layer. (8-quinolinolato) aluminum was vapor-deposited at a deposition rate of 0.2 nm / sec to a thickness of 25 nm to form an electron injecting and transporting layer, and magnesium and silver as a cathode were further deposited at a deposition rate of 1.0 nm / sec to 200 nm. Thickness Co-evaporation was performed (mass ratio 9: 1), and silver was deposited to a thickness of 100 nm at a deposition rate of 1.0 nm / sec to produce an organic electroluminescent element. A DC voltage was applied to the produced organic electroluminescent device, and it was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere, with an initial value of 5.8 V and luminance of 1100 cd / m ² . Green light emission was confirmed, and the luminance half-life was 9500 hours.

A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried using nitrogen gas, further UV / ozone cleaned, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 1 × 10 ⁻⁴ Pa.
First, N, N′-diphenyl-N, N ′-(1 ″ -naphthyl) -4,4′-diamino-1,1′-biphenyl is deposited on an ITO transparent electrode at a deposition rate of 0.2 nm / sec to 75 nm. Next, 9,10-di (2′-naphthyl) anthracene and Exemplified Compound B-13 were deposited thereon from different vapor deposition sources at a deposition rate of 0.2 nm / min. Then, a light-emitting layer was formed by co-evaporation to a thickness of 40 nm in sec (mass ratio 98: 2), and then tris (8-quinolinolato) aluminum and exemplary compound A-21 were deposited thereon from different deposition sources at a deposition rate of 0. Co-deposited to a thickness of 25 nm at a rate of 2 nm / sec (mass ratio 95: 5) to form an electron injecting and transporting layer, and further magnesium and silver as a cathode on the layer to a thickness of 200 nm at a deposition rate of 1.0 nm / sec. Co-evaporation ( In addition, an organic electroluminescent device was produced by depositing silver to a thickness of 100 nm at a deposition rate of 1.0 nm / sec, and performing the deposition while keeping the vacuum state of the deposition tank. A DC voltage was applied to the produced organic electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere, and initially green light emission of 5.8 V and a luminance of 920 cd / m ^2. The luminance half-life was 9300 hours.

: Preparation of organic electroluminescence device A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried using nitrogen gas and further UV / ozone cleaned. Next, polymethylmethacrylate (weight average molecular weight 25000), compound of exemplary compound A-21, compound of exemplary compound D-26, tris (8-quinolinolate) on an ITO transparent electrode in a nitrogen gas atmosphere
A 100 nm light emitting layer was formed by spin coating using a 3 wt% dehydrated dichloroethane solution containing aluminum in a weight ratio of 100: 50: 0.5: 10, respectively. Next, the glass substrate having the light emitting layer was fixed to a substrate holder of a vapor deposition apparatus, and the vapor deposition layer was decompressed to 1 × 10 ⁻⁴ Pa. On the light emitting layer, magnesium and silver were co-deposited as a cathode at a deposition rate of 1.0 nm / sec to a thickness of 200 nm (weight ratio 9: 1), and silver was further deposited at a deposition rate of 1.0 nm / sec at 100 nm. The organic electroluminescent element was produced by vapor deposition to a thickness. When a DC voltage of 15 V was applied to the produced organic electroluminescent element in a dry atmosphere, a current of 86 mA / cm ² flowed. Green light emission with a luminance of 910 cd / m ² was confirmed. The half life of luminance was 740 hours.

  INDUSTRIAL APPLICABILITY According to the present invention, an organic electroluminescent device having a long emission lifetime, excellent durability, and high luminous efficiency, and 1,2-dihydro-1,2-diaza-cyclopenta [cd] that can be suitably used for the organic electroluminescent device. It has become possible to provide fluoranthene derivatives.

It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element.

Explanation of symbols

1: Substrate 2: Anode 3: Hole injection / transport layer 3a: Hole injection / transport component 4: Light emitting layer 4a: Light emission component 5: Electron injection / transport layer 5 ″: Electron injection / transport layer 5a: Electron injection / transport component 6: Cathode 7: Power supply

Claims (8)

An organic electroluminescence device comprising at least one layer containing at least one 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative between a pair of electrodes. The organic electroluminescent device according to claim 1, wherein the layer containing at least one 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative is a light emitting layer. The organic electroluminescent device according to claim 1, wherein the layer containing at least one 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative is a charge injection transport layer. The organic electroluminescent device according to claim 1, wherein the layer containing at least one 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative is a light emitting layer and a charge injection transport layer. The organic electroluminescent element according to any one of claims 1 to 4, further comprising a hole injecting and transporting layer between the pair of electrodes. The organic electroluminescent element according to claim 1, further comprising an electron injecting and transporting layer between the pair of electrodes. The organic electroluminescent device according to any one of claims 1 to 6, wherein the 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative is represented by the general formula (1) (Chemical formula 1).

[Wherein, R _{1 to} R ₈ each independently represents a hydrogen atom or a substituent, and adjacent groups of R _{1 to} R ₈ may be bonded to each other to form a cyclic structure; Ar ₁ and Ar ₂ represents a substituted or unsubstituted aryl group] 1,2-dihydro-1,2-diaza-cyclopenta [cd] fluoranthene derivative represented by the general formula (1) (Chemical formula 2).

[Wherein, R _{1 to} R ₈ each independently represents a hydrogen atom or a substituent, and adjacent groups of R _{1 to} R ₈ may be bonded to each other to form a cyclic structure; Ar ₁ and Ar ₂ represents a substituted or unsubstituted aryl group]

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