JP4059822B2 - Benzofluoranthene compound and organic electroluminescent device containing the benzofluoranthene compound - Google Patents

Description

  The present invention relates to a novel benzofluoranthene compound and an organic electroluminescent device comprising the benzofluoranthene compound.

  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 luminescent material has been developed (for example, see 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. By injecting electrons and holes into the thin film and recombining them, 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 device having such characteristics is expected to be applied to various light emitting devices, display devices and the like. However, in general, the luminance is low, which is not sufficient for practical use.

As a method for improving the light emission luminance, an organic electroluminescent element using tris (8-quinolinolato) aluminum as a host material and a coumarin derivative or a pyran derivative as a guest compound (dopant) has been proposed as a light emitting layer. (Refer nonpatent literature 2). In addition, organic electroluminescent elements using anthracene derivatives as the material of the light emitting layer have been proposed (see, for example, Patent Document 1 and Patent Document 2). Furthermore, an organic electroluminescent element using an anthracene derivative as a guest compound of the light emitting layer has also been proposed (see, for example, Patent Document 3 and Patent Document 4).
In addition, organic electroluminescent devices using a benzofluoranthene derivative as a light emitting material have been reported (for example, Patent Document 5, Patent Document 6, and Patent Document 7). However, it cannot be said that these organic electroluminescent elements also have sufficient life characteristics.
At present, higher brightness and longer life are desired.
Appl.Phys.lett., 51,913 (1987) J. Appl. Phys., 65, 3610 (1989) JP-A-8-12600 JP-A-11-111458 Japanese Patent Laid-Open No. 10-36832 JP-A-10-294179 Japanese Patent Laid-Open No. 10-189247 JP 2002-69044 A JP 2003-26616 A

  An object of the present invention is to provide a novel benzofluoranthene compound. More specifically, for example, it is to provide a benzofluoranthene compound that can be suitably used as a light emitting material of an organic electroluminescent element.

  In order to solve the above-mentioned problems, the present inventors have conducted extensive studies on various benzofluoranthene compounds, particularly benzofluoranthene compounds that can be suitably used as a light-emitting material for organic electroluminescent elements. Obtaining the knowledge that the emission lifetime can be extended by introducing substituted or unsubstituted aryl groups at the 3- and 4-positions of the fluoranthene skeleton (exactly benzo [k] fluoranthene skeleton) It came to complete. That is, the present invention provides <1>: a benzofluoranthene compound represented by the general formula (1),

[In General Formula (1), X _{1 to} X ₁₀ each independently represent a hydrogen atom or a substituent, and Y ₁ and Y ₂ each independently represent a substituted or unsubstituted aryl group]
<2>: The benzofluoranthene compound according to <1>, wherein in formula (1), at least one of Y ₁ and Y ₂ is a substituted or unsubstituted aryl group represented by formula (2).

[In General Formula (2), one of X _{11 to} X ₁₈ represents a bond, the rest independently represents a hydrogen atom or a substituent, and R ₁ and R ₂ each independently represent a hydrogen atom or (Represents a substituent)
<3>: An organic electroluminescence device comprising at least one layer containing at least one benzofluoranthene compound represented by the general formula (1) between a pair of electrodes,
<4>: The organic electroluminescence device according to <3>, wherein the layer containing the benzofluoranthene compound represented by the general formula (1) is a light emitting layer,
<5> The light emitting layer is made of a compound having two or more kinds of light emitting functions, and a benzofluoranthene compound represented by the general formula (1) is used as a guest material of the light emitting layer <4> Organic electroluminescent elements,
<6> The light emitting layer is composed of a compound having two or more kinds of light emitting functions, and a benzofluoranthene compound represented by the general formula (1) is used as a host material of the light emitting layer <4> Organic electroluminescent elements,
<7>: The organic electroluminescent device according to <3>, wherein the layer containing the benzofluoranthene compound represented by the general formula (1) is a hole injection transport layer,
<8>: The organic electroluminescence device according to any one of <3> to <7>, further comprising a hole injection / transport layer between the pair of electrodes.
<9>: The organic electroluminescence device according to any one of <3> to <8>, further comprising an electron injection / transport layer between the pair of electrodes.
It is about.

  According to the present invention, it is possible to provide a novel benzofluoranthene compound and an organic electroluminescence device having a long emission lifetime and excellent durability.

Hereinafter, the present invention will be described in detail.
The benzofluoranthene compound of the present invention is a compound represented by the general formula (1).

[In General Formula (1), X _{1 to} X ₁₀ each independently represent a hydrogen atom or a substituent, and Y ₁ and Y ₂ each independently represent a substituted or unsubstituted aryl group]
In the benzofluoranthene compound represented by the general formula (1), X _{1 to} X ₁₀ each independently represent a hydrogen atom or a substituent, preferably a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or Unsubstituted amino group, ester group, C1-C10 straight chain, branched or cyclic alkylcarbonyl group, C1-C10 straight chain, branched or cyclic alkyl group, C1-C10 straight chain Branched or cyclic alkoxy group, substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, substituted or unsubstituted aryl group having 4 to 20 carbon atoms Or a substituted or unsubstituted aryloxy group having 4 to 20 carbon atoms, and more preferably a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group. Group, a linear, branched or cyclic alkylcarbonyl group having 1 to 8 carbon atoms, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms A substituted or unsubstituted aralkyl group having 7 to 16 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 16 carbon atoms, a substituted or unsubstituted aryl group having 4 to 16 carbon atoms, or a 4 to 16 carbon atom A substituted or unsubstituted aryloxy group is represented.

Moreover, the adjacent groups of X _{1 to} X ₁₀ may form a ring together with the adjacent groups.
Examples of the halogen atom represented by X _{1 to} X ₁₀ include a fluorine atom, a chlorine atom, and a bromine atom.
Examples of the substituted or unsubstituted amino group represented by X _{1 to} X ₁₀ include an amino group, N-methylamino group, N-ethylamino group, Nn-propylamino group, N-isopropylamino group, and Nn-butyl. Amino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, Nn-pentylamino group, N-cyclopentylamino group, Nn-hexylamino group, N-cyclohexyl Amino 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) amino 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-ethylamino group, 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, -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 Group, N-tert-butyl-N-benzylamino group, N-cyclopentyl-N-benzylamino group, N-cyclohexyl-N-benzylamino 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 And a substituted or unsubstituted amino group.
Examples of the ester group for X _{1 to} X ₁₀ include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propyloxycarbonyl group, an isopropyloxycarbonyl group, an n-butyloxycarbonyl group, an isobutyloxycarbonyl group, a tert-butyloxycarbonyl group, n-pentyloxycarbonyl group, cyclopentyloxycarbonyl group, cyclohexyloxycarbonyl group, benzyloxycarbonyl group, phenyloxycarbonyl group, 1-naphthyloxycarbonyl group, 2-naphthyloxycarbonyl group,
Acetyloxy group, ethylcarbonyloxy group, n-propylcarbonyloxy group, n-butylcarbonyloxy group, tert-butylcarbonyloxy group, cyclohexylcarbonyloxy group, benzylcarbonyloxy group, phenylcarbonyloxy group, 1-naphthylcarbonyloxy And ester groups such as a 2-naphthylcarbonyloxy group.
Examples of the linear, branched or cyclic alkylcarbonyl group of X _{1 to} X ₁₀ include a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an isopropylcarbonyl group, an n-butylcarbonyl group, a tert-butylcarbonyl group, n -Linear, branched or cyclic such as pentylcarbonyl group, cyclopentylcarbonyl group, n-hexylcarbonyl group, cyclohexylcarbonyl group, n-heptylcarbonyl group, n-octylcarbonyl group, n-nonylcarbonyl group, n-decylcarbonyl group Can be mentioned.

Specific examples of the linear, branched or cyclic alkyl group represented by X _{1 to} X ₁₀ include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert- Butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 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, isobornyl group, 1-norbornyl group, 2-norbornanemethyl Group, 1-bicyclo [2.2.2] octyl group, 1-adamantyl group, 3-noradamantyl group, 1-adamantylmethyl group, cyclobutyl group, cyclopentyl group, 1-methylcyclopentyl group, cyclohexyl group, 4-methyl Cyclohexyl group, 3-methylcycl Hexyl group, 2-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl 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-tert-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-propyloxyethyl group, 2-isopropyloxyethyl group, 2-n-butyloxyethyl 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-methyl Xylpropyl group, 3-methoxypropyl group, 3-ethoxypropyl group, 3-n-propyloxypropyl group, 3-isopropyloxypropyl group, 3- (n-butyloxy) propyl group, 3- (n-pentyloxy) propyl Group, 3- (n-hexyloxy) propyl group, 3- (2′-ethylbutyloxy) 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-propyloxybutyl group, 4-isopropyloxybutyl group, 4-n-butyloxybutyl 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- Propyloxypentyl group, 6-ethoxyhexyl group, 6-isopropyloxyhexyl group, 6-n-butyloxyhexyl group, 6-n-hexyloxyhexyl group, 6-n-decyloxyhexyl group, 4-methoxycyclohexyl group 7-ethoxyheptyl group, 7-isopropyloxyheptyl group, 8-methoxyoctyl group, 10-methoxydecyl group, 10-n-butyloxydecyl group, 12-ethoxydodecyl group, 12-isopropyloxidedecyl group, tetrahydrofur Furyl group,

  2- (2′-methoxyethoxy) ethyl group, 2- (2′-ethoxyethoxy) ethyl group, 2- (2′-n-butyloxyethoxy) 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- Enyloxybutyl 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, trifluoromethyl group, 1,1-dihydro-perfluoroethyl group, 1,1-dihydro-perfluoro-n-propyl 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-per Fluoro-n-hexadecyl group, perfluoro-n-hexyl group, dichloromethyl group, 2-chloroethyl group, 3-chloropropyl group, 4-chlorocyclohexyl group, 7-chloroheptyl group, 8-chlorooctyl 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 linear, branched or cyclic alkyl groups such as a hydroxydecyl group, 12-hydroxydodecyl group, and 2-hydroxycyclohexyl group.

Specific examples of the linear, branched or cyclic alkoxy group of X _{1 to} X ₁₀ include, for example, a linear, branched or cyclic alkoxy group derived from the above linear, branched or cyclic alkyl group. Can do.

Specific examples of the substituted or unsubstituted aralkyl group of X _{1 to} X ₁₀ include 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-ethylbenzyl 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-octyl group Benzyl 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-decyloxy Benzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group,
3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-isobutyloxymethylbenzyl 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 substituted or unsubstituted aralkyl groups such as a group, 2-chlorobenzyl group, 3,4-dichlorobenzyl group, 2-furfuryl group, diphenylmethyl group, 1-naphthylmethyl group, and 2-naphthylmethyl group. .

Specific examples of the substituted or unsubstituted aralkyloxy group of X _{1 to} X ₁₀ include a substituted or unsubstituted aralkyloxy group derived from the above substituted or unsubstituted aralkyl group.

Specific examples of the substituted or unsubstituted aryl group represented by X _{1 to} X ₁₀ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-anthracenyl group, a 9-anthracenyl group, a fluorenyl group, a 4-quinolyl group, 5-pyridyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 2-pyrimidyl group, 4-pyrimidine group, 5-pyrimidyl group, 2-pyridazinyl group, 2-pyrazinyl group, 3-furyl group, 2-furyl group, 3-thienyl group, 2-thienyl group, 2-oxazolyl group, 2-thiazolyl group, 2-benzoxazolyl group, 2-benzothiazolyl group, 2-benzimidazolyl group,
4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 2-sec-butylphenyl group, 4-tert-butylphenyl group, 3-tert-butylphenyl Group, 2-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4-n-heptylphenyl group, 4 -N-octylphenyl group, 4- (2'-ethylhexyl) phenyl group, 4-tert-octylphenyl group, 4-n-nonylphenyl group, 4 n-decylphenyl group, 4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 4-n-hexadecylphenyl group, 4-n-octadecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl Group, 4- (4′-tert-butylcyclohexyl) phenyl group, 4- (4′-methylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4-ethyl-1-naphthyl group, 6 -N-butyl-2-naphthyl group,

2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2, 3,5-trimethylphenyl group, 3,4,5-trimethylphenyl group, 2,4-diethylphenyl group, 2,3,6-trimethylphenyl group, 2,4,6-trimethylphenyl group, 2,6- Diethylphenyl group, 2,6-diisopropylphenyl group, 2,6-diisobutylphenyl group, 2,4-di-tert-butylphenyl group, 2,5-di-tert-butylphenyl group, 3,5-di- tert-butylphenyl group, 2,4-dineopentylphenyl group, 2,5-di-tert-pentylphenyl group, 4,6-di-tert-butyl-2-methylphenyl group, 5-tert-butyl- 2 Methylphenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 2,3,5,6-tetramethyl-phenyl group,
5-indanyl group, 1,2,3,4-tetrahydro-5-naphthyl group, 1,2,3,4-tetrahydro-6-naphthyl group,

4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 2-ethoxyphenyl group, 3-n-propyloxyphenyl group, 4-isopropyloxyphenyl group, 2-isopropyloxy Phenyl group, 4-n-butyloxyphenyl group, 4-isobutyloxyphenyl group, 2-isobutyloxyphenyl group, 2-sec-butyloxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl Group, 2-isopentyloxyphenyl group, 2-neopentyloxyphenyl group, 4-n-hexyloxyphenyl group, 2- (2′-ethylbutyloxy) phenyl group, 4-n-octyloxyphenyl group, 4 -N-decyloxyphenyl group, 4-n-dodecyloxyphenyl group, 4 n- tetradecyloxyphenyl group, 4-n- hexadecyl oxyphenyl group, 4-n- octadecyloxyphenyl group, 4-cyclohexyloxy-phenyl group, 2-cyclohexyloxy-phenyl group,
2-methoxy-1-naphthyl group, 4-methoxy-1-naphthyl group, 4-n-butyloxy-1-naphthyl group, 5-ethoxy-1-naphthyl group, 6-ethoxy-2-naphthyl group, 6-n -Butyloxy-2-naphthyl group, 6-n-hexyloxy-2-naphthyl group, 7-methoxy-2-naphthyl group, 7-n-butyloxy-2-naphthyl group,

  2,3-dimethoxyphenyl 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-butyloxyphenyl group, 2-methoxy-4-methylphenyl group, 2-methoxy-5-methylphenyl group, 2-methyl-4-methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 3-ethyl-5-methoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2-methoxy-6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group,

  4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 3-chlorophenyl group, 2-chlorophenyl group, 4-bromophenyl group, 2-bromophenyl group, 4-chloro-1 -Naphthyl group, 4-chloro-2-naphthyl group, 6-bromo-2-naphthyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6- Difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2,6-dichlorophenyl group, 3, 4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,5-dibromophenyl group, 2,4,6-trichloroph Group, 2,3,6-bromophenyl group, 3,4,5-trifluorophenyl 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, 4-fluoro-2-methylphenyl group, 5-fluoro-2-methylphenyl group, 2-chloro-4-methylphenyl group, 2-chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group, 3-chloro-2-methylphenyl group, 4-chloro-2-methylphenyl group, 4-chloro-3-methylphenyl group, 2-chloro-4,6-dimethylphenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-6-methoxyphenyl Group, 3-fluoro-4-ethoxyphenyl group, 5-chloro-2-methoxyphenyl group, 6-chloro-3-methoxyphenyl group, 5-chloro-2,4- Methoxyphenyl group, 2-chloro-4-nitrophenyl group, 4-chloro-2-nitrophenyl group,
4-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 2-trifluoromethylphenyl group, 3,5-bis (trifluoromethyl) phenyl group,
4-trifluoromethyloxyphenyl group,

4-allylphenyl group, 2-allylphenyl group, 2-isopropenylphenyl group, 4-benzylphenyl group, 2-benzylphenyl group, 4- (4′-methylbenzyl) phenyl group, 4-cumylphenyl group, 4- (4′-methoxycumyl) phenyl group,
4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 4- (4′-methylphenyl) phenyl group, 4- (4′-ethylphenyl) phenyl group, 4- (4′-isopropylphenyl) ) Phenyl group, 4- (4′-tert-butylphenyl) phenyl group, 4- (4′-n-hexylphenyl) phenyl group, 4- (4′-n-octylphenyl) phenyl group,
4- (4′-methoxyphenyl) phenyl group, 4- (4′-ethoxyphenyl) phenyl group, 4- (4′-n-butoxyphenyl) phenyl group, 2- (2′-methoxyphenyl) phenyl group, 4- (4′-fluorophenyl) phenyl group, 4- (4′-chlorophenyl) phenyl group, 3-methyl-4-phenyl group, 2-methoxy-5-phenylphenyl group, 3-methoxy-4-phenylphenyl Group,

4-methoxymethylphenyl group, 4-ethoxymethylphenyl group, 4-n-butyloxymethylphenyl group, 3-methoxymethylphenyl group, 4- (2′-methoxyethyl) phenyl group, 4- (2′-ethoxy) Ethyloxy) phenyl group, 4- (2′-n-butyloxyethyloxy) phenyl group, 4- (3′-ethoxypropyloxy) phenyl group, 4-vinyloxyphenyl group, 4-allyloxyphenyl group, 3 -Allyloxyphenyl group, 4- (4'-pentenyloxy) phenyl group, 4-allyloxy-1-naphthyl group,
4-allyloxymethylphenyl group, 4- (2′-allyloxyethyloxy) phenyl group,

  4-benzyloxyphenyl group, 2-benzyloxyphenyl group, 4-phenethyloxyphenyl group, 4- (4′-chlorobenzyloxy) phenyl group, 4- (4′-methylbenzyloxy) phenyl group, 4- ( 4′-methoxybenzyloxy) phenyl group, 4- (3′-ethoxybenzyloxy) phenyl group, 4-benzyloxy-1-naphthyl group, 5- (4′-methylbenzyloxy) -1-naphthyl group, 6 -Benzyloxy-2-naphthyl group, 6- (4'-methylbenzyloxy) -2-naphthyl group, 7-benzyloxy-2-naphthyl group, 4- (benzyloxymethyl) phenyl group, 4- (2 ' -Benzyloxyethyloxy) phenyl group,

4-phenyloxyphenyl group, 3-phenyloxyphenyl group, 2-phenyloxyphenyl group, 4- (4′-methylphenyloxy) phenyl group, 4- (4′-methoxyphenyloxy) phenyl group, 4- ( 4′-chlorophenyloxy) phenyl group, 4-phenyloxy-1-naphthyl group, 6-phenyloxy-2-naphthyl group, 7-phenyloxy-2-naphthyl group, 4-phenyloxymethylphenyl group, 4- ( 2′-phenyloxyethoxy) phenyl group, 4- [2 ′-(4′-methylphenyloxy) ethoxy] phenyl group, 4- [2 ′-(4′-methoxyphenyloxy) ethoxy] phenyl group, 4- [2 ′-(4′-chlorophenyloxy) ethoxy] phenyl group,
4-acetylphenyl group, 3-acetylphenyl group, 2-acetylphenyl group, 4-ethylcarbonylphenyl group, 2-ethylcarbonylphenyl group, 4-n-butylcarbonylphenyl group, 4-n-hexylcarbonylphenyl group, 4-n-octylcarbonylphenyl group, 4-cyclohexylcarbonylphenyl group, 4-acetyl-1-naphthyl group, 6-acetyl-2-naphthyl group, 6-n-butylcarbonyl-2-naphthyl group, 4-allylcarbonyl Phenyl group, 4-benzylcarbonylphenyl group, 4- (4′-methylbenzyl) carbonylphenyl group, 4-phenylcarbonylphenyl group, 4- (4′-methylphenyl) carbonylphenyl group, 4- (4′-chlorophenyl) ) Carbonylphenyl group, 4-phenylcarbonyl-1-na Methyl group,

  4-methoxycarbonylphenyl group, 2-methoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4-n-propyloxycarbonylphenyl group, 4-n-butyloxycarbonylphenyl group, 4- n-hexyloxycarbonylphenyl group, 4-n-decyloxycarbonylphenyl group, 4-cyclohexyloxycarbonylphenyl group, 4-ethoxycarbonyl-1-naphthyl group, 6-methoxycarbonyl-2-naphthyl group, 6-n- Butyloxycarbonyl-2-naphthyl group, 4-allyloxycarbonylphenyl group, 4-benzyloxycarbonylphenyl group, 4- (4′-chlorobenzyl) oxycarbonylphenyl group, 4-phenethyloxycarbonylphenyl group, 6-ben Ruoxycarbonyl-2-naphthyl group, 4-phenyloxycarbonylphenyl group, 4- (4'-ethylphenyl) oxycarbonylphenyl group, 4- (4'-chlorophenyl) oxycarbonylphenyl group, 4- (4'- Ethoxyphenyl) oxycarbonylphenyl group, 6-phenyloxycarbonyl-2-naphthyl group,

  4-acetyloxyphenyl group, 3-acetyloxyphenyl group, 2-acetyloxyphenyl group, 4-ethylcarbonyloxyphenyl group, 2-ethylcarbonyloxyphenyl group, 4-n-propylcarbonyloxyphenyl group, 4-n -Pentylcarbonyloxyphenyl group, 4-n-octylcarbonyloxyphenyl group, 4-cyclohexylcarbonyloxyphenyl group, 3-cyclohexylcarbonyloxyphenyl group, 4-acetyloxy-1-naphthyl group, 4-n-butylcarbonyloxy -1-naphthyl group, 5-acetyloxy-1-naphthyl group, 6-ethylcarbonyloxy-2-naphthyl group, 7-acetyloxy-2-naphthyl group, 4-allylcarbonyloxyphenyl group, 4-benzylcarbonyloxy Phenyl group 4- phenethyl carbonyl oxyphenyl group, 6-benzyloxy carbonyloxy-2-naphthyl group,

  4-phenylcarbonyloxyphenyl group, 4- (4′-methylphenyl) carbonyloxyphenyl group, 4- (2′-methylphenyl) carbonyloxyphenyl group, 4- (4′-chlorophenyl) carbonyloxyphenyl group, 4 -(2'-chlorophenyl) carbonyloxyphenyl group, 4-phenylcarbonyloxy-1-naphthyl group, 6-phenylcarbonyloxy-2-naphthyl group, 7-phenylcarbonyloxy-2-naphthyl group,

4-methylthiophenyl group, 2-methylthiophenyl group, 2-ethylthiophenyl group, 3-ethylthiophenyl group, 4-n-propylthiophenyl group, 2-isopropylthiophenyl group, 4-n-butylthiophenyl group 2-isobutylthiophenyl group, 2-neopentylphenyl group, 4-n-hexylthiophenyl group, 4-n-octylthiophenyl group, 4-cyclohexylthiophenyl group,
4-benzylthiophenyl group, 3-benzylthiophenyl group, 2-benzylthiophenyl group, 4- (4′-chlorobenzylthio) phenyl group, 4-phenylthiophenyl group, 3-phenylthiophenyl group, 2- Phenylthiophenyl group, 4- (4'-methylphenylthio) phenyl group, 4- (3'-methylphenylthio) phenyl group, 4- (4'-methoxyphenylthio) phenyl group, 4- (4'- Chlorophenylthio) phenyl group, 2-ethylthio-1-naphthyl group, 4-methylthio-1-naphthyl group, 6-ethylthio-2-naphthyl group, 6-phenylthio-2-naphthyl group,

  4-nitrophenyl group, 3-nitrophenyl group, 2-nitrophenyl group, 3,5-dinitrophenyl group, 4-nitro-1-naphthyl group, 4-formylphenyl group, 3-formylphenyl group, 2-formyl Phenyl group, 4-formyl-1-naphthyl group, 1-formyl-2-naphthyl group,

4-pyrrolidinophenyl group, 4-piperidinophenyl group, 4-morpholinophenyl group, 4- (N-ethylpiperazino) phenyl group, 4-pyrrolidino-1-naphthyl group,
4-aminophenyl group, 3-aminophenyl group, 2-aminophenyl group,
4- (N-methylamino) phenyl group, 3- (N-methylamino) phenyl group, 4- (N-ethylamino) phenyl group, 2- (N-isopropylamino) phenyl group, 4- (Nn) -Butylamino) phenyl group, 2- (Nn-butylamino) phenyl group, 4- (Nn-octylamino) phenyl group, 4- (Nn-dodecylamino) phenyl group, 4- (N -Benzylamino) phenyl group, 4- (N-phenylamino) phenyl group, 2- (N-phenylamino) phenyl group,

  4- (N, N-dimethylamino) phenyl group, 3- (N, N-dimethylamino) phenyl group, 4- (N, N-diethylamino) phenyl group, 2- (N, N-dimethylamino) phenyl group 2- (N, N-diethylamino) phenyl group, 4- (N, N-di-n-butylamino) phenyl group, 4- (N, N-di-n-hexylamino) phenyl group, 4- (N N-cyclohexyl-N-methylamino) phenyl group, 4- (N, N-diethylamino) -1-naphthyl group, 4- (N-benzyl-N-phenylamino) phenyl group, 4- (N, N-diphenyl) Amino) phenyl group, 4- [N-phenyl-N- (4-methylphenyl) amino] phenyl group, 4- [N, N-di (3′-methylphenyl) amino] phenyl group, 4- [N, N-di (4′-methyl) Yl) amino] phenyl group, 4- [N, N-di (4'-methoxyphenyl) amino] phenyl group, 2-(N, N-diphenylamino) phenyl group,

  4-hydroxyphenyl group, 3-hydroxyphenyl group, 2-hydroxyphenyl group, 4-methyl-3-hydroxyphenyl group, 6-methyl-3-hydroxyphenyl group, 2-hydroxy-1-naphthyl group, 8-hydroxy -1-naphthyl group, 4-hydroxy-1-naphthyl group, 1-hydroxy-2-naphthyl group, 6-hydroxy-2-naphthyl group, 4-cyanophenyl group, 2-cyanophenyl group, 4-cyano-1 -A substituted or unsubstituted aryl group such as a naphthyl group and a 6-cyano-2-naphthyl group can be exemplified.

Specific examples of the substituted or unsubstituted aryloxy group represented by X _{1 to} X ₁₀ include a substituted or unsubstituted aryloxy group derived from the above aryl group.

In General Formula (1), Y ₁ and Y ₂ each independently represent a substituted or unsubstituted aryl group, preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, more preferably 6 carbon atoms. Represents a substituted or unsubstituted aryl group of ˜25.

Specific examples of the substituted or unsubstituted aryl group represented by Y ₁ and Y ₂ include the substituted or unsubstituted aryl groups listed as specific examples of the substituted or unsubstituted aryl group represented by X _{1 to} X _10. it can.

In the benzofluoranthene compound represented by the general formula (1), at least one of the substituted or unsubstituted aryl groups represented by Y ₁ and Y _{2 is} a substituted or unsubstituted aryl group represented by the general formula (2) It is preferable that it is the benzofluoranthene compound which is.

[In General Formula (2), one of X _{11 to} X ₁₈ represents a bond, the rest independently represents a hydrogen atom or a substituent, and R ₁ and R ₂ each independently represent a hydrogen atom or (Represents a substituent)
In the substituted or unsubstituted aryl group represented by the general formula (2), one of X _{11 to} X ₁₈ represents a bond, and the rest each independently represents a hydrogen atom or a substituent, Hydrogen atom, halogen atom, cyano group, nitro group, substituted or unsubstituted amino group, ester group, straight chain, branched or cyclic alkylcarbonyl group having 1 to 10 carbon atoms, straight chain or branched chain having 1 to 10 carbon atoms Or a cyclic alkyl group, a linear, branched or cyclic alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, and a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms. Represents a substituted or unsubstituted aryl group having 4 to 20 carbon atoms or a substituted or unsubstituted aryloxy group having 4 to 20 carbon atoms, more preferably a hydrogen atom, a halogen atom, Group, nitro group, substituted or unsubstituted amino group, linear, branched or cyclic alkylcarbonyl group having 1 to 8 carbon atoms, linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, carbon number 1 -8 linear, branched or cyclic alkoxy group, substituted or unsubstituted aralkyl group having 7 to 16 carbon atoms, substituted or unsubstituted aralkyloxy group having 7 to 16 carbon atoms, substituted or unsubstituted 4 to 16 carbon atoms, An unsubstituted aryl group or a substituted or unsubstituted aryloxy group having 4 to 16 carbon atoms is represented.

Specific examples of the halogen atoms represented by X _{11 to} X ₁₈ include the halogen atoms exemplified in the specific examples of the halogen atoms represented by X _{1 to} X ₁₀ .

Specific examples of the substituted or unsubstituted amino group represented by X _{11 to} X ₁₈ include the substituted or unsubstituted amino groups listed as specific examples of the substituted or unsubstituted amino group represented by X _{1 to} X _10. .
Specific examples of the ester group of X _{11 to} X ₁₈ include the ester groups mentioned as specific examples of the ester group of X _{1 to} X ₁₀ .

Linear X ₁₁ to X _18, specific examples of the alkyl group branched or cyclic listed as specific examples of straight-chain, branched or cyclic alkyl group of X ₁ to X _10, a straight-chain, branched or cyclic Can be mentioned.

Specific examples of the linear, branched or cyclic alkyl group represented by X _{11 to} X ₁₈ include the linear, branched or cyclic alkyl groups exemplified as specific examples of the linear, branched or cyclic alkyl group represented by X _{1 to} X ₁₀ . An alkyl group can be mentioned.
Specific examples of the linear, branched or cyclic alkoxy group of X _{11 to} X ₁₈ include a linear, branched or cyclic alkoxy group derived from a linear, branched or cyclic alkyl group of X _{1 to} X _10. Can be raised.
Specific examples of the substituted or unsubstituted aralkyl group represented by X _{11 to} X ₁₈ include the substituted or unsubstituted aralkyl groups listed as specific examples of the substituted or unsubstituted aralkyl group represented by X _{1 to} X ₁₀ .
Specific examples of the substituted or unsubstituted aralkyloxy group represented by X _{11 to} X ₁₈ include a substituted or unsubstituted aralkyloxy group derived from the substituted or unsubstituted aralkyl group represented by X _{1 to} X _10. .
Specific examples of the substituted or unsubstituted aryl group represented by X _{11 to} X ₁₈ include the substituted or unsubstituted aryl groups listed as specific examples of the substituted or unsubstituted aryl group represented by X _{1 to} X _10. it can.
Specific examples of the substituted or unsubstituted aryloxy group represented by X _{11 to} X ₁₈ include a substituted or unsubstituted aryloxy group derived from the substituted or unsubstituted aryl group represented by X _{1 to} X _10. .

In the substituted or unsubstituted aryl group represented by the general formula (2), R ₁ and R ₂ represent a hydrogen atom or a substituent, preferably a hydrogen atom, a linear, branched or cyclic group having 1 to 10 carbon atoms. An alkyl group, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 4 to 20 carbon atoms.

Specific examples of the linear, branched or cyclic alkyl group represented by R ₁ and R ₂ include the linear, branched or cyclic examples exemplified as the linear, branched or cyclic alkyl group represented by X _{1 to} X ₁₀ . An alkyl group can be mentioned.
Specific examples of the substituted or unsubstituted aralkyl group represented by R ₁ and R ₂ include the substituted or unsubstituted aralkyl groups listed as specific examples of the substituted or unsubstituted aralkyl group represented by X _{1 to} X _10. it can.
Specific examples of the substituted or unsubstituted aryl group represented by R ₁ and R ₂ include the substituted or unsubstituted aryl groups listed as specific examples of the substituted or unsubstituted aryl group represented by X _{1 to} X _10. it can.

Specific examples of the substituted or unsubstituted aryl group represented by the general formula (2) include, for example,
9H-fluoren-2-yl group, 7-methyl-9H-fluoren-2-yl group, 7-tert-butyl-9H-fluoren-2-yl group, 7-cyclohexyl-9H-fluoren-2-yl group, 7-phenyl-9H-fluoren-2-yl group, 9-methyl-9H-fluoren-2-yl group, 7-methyl-9H-fluoren-2-yl group, 7-phenyl-9H-fluoren-2-yl group Group, 7-tert-butyl-9H-fluoren-2-yl group, 9-ethyl-9H-fluoren-2-yl group, 9-n-propyl-9H-fluoren-2-yl group, 9-cyclohexyl-9H -Fluoren-2-yl group, 9-phenyl-9H-fluoren-2-yl group, 9,9-dimethyl-9H-fluoren-2-yl group, 7-methyl-9,9-dimethyl-9H-fluorene- 2-yl group, 7-phenyl-9,9-dimethyl-9H-fluoren-2-yl group, 7-cyclohexyl-9,9-dimethyl-9H-fluoren-2-yl group, 7-tert-butyl-9 , 9-dimethyl-9H-fluoren-2-yl group, 7-cyano-9,9-dimethyl-9H-fluoren-2-yl group, 7-chloro-9,9-dimethyl-9H-fluoren-2-yl group Group, 7-N, N-dimethylamino-9,9-dimethyl-9H-fluoren-2-yl group, 7-N, N-diethylamino-9,9-diethyl-9H-fluoren-2-yl group, 7 -N, N-dimethylamino-9,9-dicyclohexyl-9H-fluoren-2-yl group, 9,9-diethyl-9H-fluoren-2-yl group, 9,9-di-n-propyl-9H- Fluoren-2-yl group, , 9-Diisopropyl-9H-fluoren-2-yl group, 9,9-di-n-butyl-9H-fluoren-2-yl group, 9,9-di-n-hexyl-9H-fluoren-2- Yl group, 9,9-di-n-octyl-9H-fluoren-2-yl group, 9,9-dicyclopentyl-9H-fluoren-2-yl group, 9,9-dicyclohexyl-9H-fluorene-2- Yl group, 9,9-dibenzyl-9H-fluoren-2-yl group, 9,9-diphenyl-9H-fluoren-2-yl group, 7-methyl-9,9-diphenyl-9H-fluoren-2-yl Group, 7-phenyl-9,9-diphenyl-9H-fluoren-2-yl group, 7-tert-butyl-9,9-diphenyl-9H-fluoren-2-yl group, 7-cyclohexyl-9,9- Diphenyl-9 -Fluoren-2-yl group, 9,9- (4'-N, N-dimethylaminophenyl) -9H-fluoren-2-yl group, 9,9- (4'-methoxyphenyl) -9H-fluorene- 2-yl group, 9,9- (4′-phenoxyphenyl) -9H-fluoren-2-yl group, 9,9- (4′-n-propyloxyphenyl) -9H-fluoren-2-yl group, 9,9- (4′-cyclohexyloxyphenyl) -9H-fluoren-2-yl group, 9,9- [4 ′-(1 ″ -adamantyloxy) phenyl] -9H-fluoren-2-yl group, 9 , 9-dimethyl-9H-fluoren-1-yl group and 9,9-dimethyl-9H-fluoren-3-yl group.

  Specific examples of the benzofluoranthene compound represented by the general formula (1) according to the present invention include the following compounds (Chemical Formula 7 to Chemical Formula 19), but the present invention is limited to these. Is not to be done.

本発明の一般式（１）で表されるベンゾフルオランテン化合物は、例えば、以下に示す工程により製造することができる。

The benzofluoranthene compound represented by the general formula (1) of the present invention can be produced, for example, by the steps shown below.

  Production of a benzofluoranthene compound represented by the general formula (1) (Chemical Formula 20).

[Wherein, X _{1 to} X ₁₀ , Y ₁ and Y ₂ represent the same meaning as in general formula (1), and L ₁ and L ₂ represent a halogen atom, an arylsulfonyloxy group, a trifluoromethanesulfonyloxy group, etc. (Represents a radical)
That is, a benzofluoranthene derivative represented by the general formula (A) and a boronic acid derivative are converted into a palladium catalyst [for example, tetrakis (triphenylphosphine) palladium, palladium acetate / tri-tert-butylphosphine] and a base (for example, The benzofluoranthene compound (1) represented by the general formula (1) can be produced by reacting in the presence of an organic base such as triethylamine or pyridine, or an inorganic base such as sodium carbonate or potassium carbonate.

  The benzofluoranthene derivative represented by the general formula (A) can be produced according to the production method shown below (Chemical Formula 21).

[Wherein, X _{1 to} X ₁₀ represent the same meaning as in general formula (1), and L ₁ and L ₂ represent a leaving group such as a halogen atom, an arylsulfonyloxy group, and a trifluoromethanesulfonyloxy group]
That is, the isobenzofuran derivative represented by the general formula (B) and the acenaphthylene derivative represented by the general formula (C) are heated to form a pyran derivative by Diels-Alder reaction, and then treated with hydrobromic acid and acetic acid. By carrying out the aromatization, the benzofluoranthene derivative represented by the general formula (A) can be produced.

  Next, the organic electroluminescent element of the present invention will be described. The organic electroluminescent element of the present invention comprises at least one layer containing at least one benzofluoranthene compound represented by the general formula (1) between a pair of electrodes. An organic electroluminescent element is usually formed by sandwiching at least one light emitting layer containing at least one light emitting component between a pair of electrodes. A hole injection / transport layer and / or an electron injection containing a hole injection component as desired, considering the functional level of the hole injection and hole transport, electron injection and electron transport of the compound used in the light emitting layer. An electron injecting and transporting layer containing a transporting component can also be provided.

  For example, when the hole injection function, the hole transport function and / or the electron injection function, and the electron transport function of the compound used in the light emitting layer are good, the light emitting layer is a hole injection transport layer and / or an electron injection transport layer. As a type of element configuration that also serves as a single layer type element configuration. Further, when the light emitting layer is poor in the hole injection function and / or the hole transport function, a two-layer device configuration in which a hole injection transport layer is provided on the anode side of the light emitting layer, the light emitting layer has an electron injection function and / or Alternatively, when the electron transport function is poor, a two-layer device structure in which an electron injecting and transporting layer is provided on the cathode side of the light emitting layer can be obtained. Furthermore, a three-layer device configuration in which the light emitting layer is sandwiched between a hole injection transport layer and an electron injection transport layer can be used.

  In addition, each of the hole injecting and transporting layer, the electron injecting and transporting layer, and the light emitting layer may have a single layer structure or a multilayer structure, and the hole injecting and transporting layer and the electron injecting and transporting layer The layer having an injection function and the layer having a transport function can be separately provided.

  In the organic electroluminescent device of the present invention, the benzofluoranthene compound represented by the general formula (1) is preferably used as a constituent component of the hole injection transport layer and / or the luminescent layer. It is more preferable to use as.

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

  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 is formed of a benzofluoranthene compound represented by the general formula (1) or another compound having a hole-injecting and transporting function (for example, phthalocyanine derivatives, triarylamine derivatives, triarylmethane derivatives, oxazoles) Derivatives, hydrazone derivatives, stilbene derivatives, pyrazoline derivatives, polysilane derivatives, polyphenylene vinylene and derivatives thereof, polythiophene and derivatives thereof, poly-N-vinylcarbazole and the like).
The compounds having a hole injecting and transporting function may be used alone or in combination.

  The organic electroluminescent element of the present invention preferably contains a benzofluoranthene compound represented by the general formula (1) in the hole injecting and transporting layer. Examples of the compound having a hole injecting and transporting function other than the benzofluoranthene compound represented by the general formula (1) of the present invention that can be used in the organic electroluminescence device of the present invention include triarylamine derivatives (for example, 4,4′-bis [N-phenyl-N- (4 ″ -methylphenyl) amino] biphenyl, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl, 4, 4′-bis [N-phenyl-N- (3 ″ -methoxyphenyl) amino] biphenyl, 4,4′-bis [N-phenyl-N- (1 ″ -naphthyl) amino] biphenyl, 3,3′- Dimethyl-4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl, 1,1-bis [4 ′-[N, N-di (4 ″ -methylphenyl) amino] Phenyl Cyclohexane, 9,10-bis [N- (4′-methylphenyl) -N- (4 ″ -n-butylphenyl) amino] phenanthrene, 3,8-bis (N, N-diphenylamino) -6-phenyl Phenanthridine, 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 (N , N-diphenylamino) Zen, 4,4 ′, 4 ″ -tris (N-carbazolyl) triphenylamine, 4,4 ′, 4 ″ -tris [N, N-bis (4 ″ ′-tert-butylbiphenyl-4 ″ ″-yl) ) Amino] triphenylamine, 1,3,5-tris (4′-N, N-diphenylaminophenyl) benzene, and the like, polythiophene and derivatives thereof, and poly-N-vinylcarbazole and derivatives thereof are more preferable.

  When the benzofluoranthene compound represented by the general formula (1) and another compound having a hole injection function are used in combination, the benzofluoranthene represented by the general formula (1) in the hole injection transport layer The content of the compound is preferably 0.1% by weight or more, more preferably 0.5 to 99.9% by weight, and still more preferably 3 to 97% by weight.

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 has at least one compound having a light emitting function other than the benzofluoranthene compound represented by the general formula (1) using the benzofluoranthene compound represented by the general formula (1) as a host material. And a compound having a light emitting function other than the benzofluoranthene compound represented by the general formula (1) as at least one kind of host material is represented by the general formula (1). It can also be formed using a benzofluoranthene compound as a guest material.
Examples of the compound having a light emitting function (guest material / host material) other than the benzofluoranthene compound represented by the general formula (1) include an acridone derivative, a quinacridone derivative, a diketopyrrolopyrrole derivative, and a polycyclic aromatic compound. [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 transport) The compounds described above can be mentioned as the compound having the ability), organometallic complexes [for example, tris (8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, 2- (2′-hydroxyphenyl)] Zinc salt of benzothiazole, 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 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, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamic acid ester derivatives, poly-N-vinylcarbazole and derivatives thereof, polythiophene and derivatives thereof, polyphenylene and derivatives thereof, polyfluorene and derivatives thereof, Polyphenylene vinylene and its derivatives, polybiphenylene vinylene and its derivatives, polyterphenylene vinylene and its derivatives, polynaphthylene vinyl Examples include len and its derivatives, polythienylene vinylene and its derivatives, and the like. Compounds having a light emitting function other than the benzofluoranthene compound represented by the general formula (1) (guest material / host material) include acridone derivatives, quinacridone derivatives, polycyclic aromatic compounds, triarylamine derivatives, organometallics Complexes and stilbene derivatives are preferred, and polycyclic aromatic compounds and organometallic complexes are more preferred.
When the benzofluoranthene compound represented by the general formula (1) is used as a host material in combination with another compound having a light emitting function (guest material), the benzo represented by the general formula (1) in the light emitting layer The content of the fluoranthene compound is preferably 99.9 to 80% by weight, and more preferably 99 to 90% by weight.

In this case, the host material may be used alone or in combination. When a plurality of host materials are used in combination, the host material of the benzofluoranthene compound represented by the general formula (1) of the present invention The ratio to the whole is preferably 99 to 10% by weight, more preferably 90 to 20% by weight.
Further, when the benzofluoranthene compound represented by the general formula (1) is used as a guest material in combination with another compound having a light emitting function (host material), it is represented by the general formula (1) occupied in the light emitting layer. The content of the benzofluoranthene compound is preferably 0.1 to 20% by weight, more preferably 1 to 10% by weight.

  In this case, the guest material may be used alone or in combination, and when a plurality of guest materials are used in combination, the entire guest material of the benzofluoranthene compound represented by the general formula (1) of the present invention The proportion of the amount is preferably 99 to 10% by weight, more preferably 90 to 0% by weight.

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 organoaluminum complexes such as tris (8-quinolinolato) aluminum, organic beryllium complexes such as bis (10-benzo [h] quinolinolato) beryllium, beryllium salts 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-quinolinolate ligand include compounds represented by general formulas (a) to (c).

(Q) ₃ -Al (a)
(Wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand)
(Q) ₂ -Al-OL '(b)
(In the formula, Q represents a substituted or unsubstituted 8-quinolinolate ligand, OL ′ represents a phenolate ligand, and L ′ represents a hydrocarbon group having 6 to 24 carbon atoms having a phenyl group. )
(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-quinolinolate) ( , 6-Dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,4-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,5-dimethylphenolate) aluminum Bis (2-methyl-8-quinolinolato) (3,5-di-tert-butylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,6-diphenylphenolato) aluminum, bis (2 -Methyl-8-quinolinolato) (2,4,6-triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,4,6-trimethylphenolato) aluminum, bis (2-methyl- 8-quinolinolato) (2,4,5,6-tetramethylphenolate) aluminum, bi (2-methyl-8-quinolinolato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinolato) (2-naphtholato) aluminum, bis (2,4-dimethyl-8-quinolinolato) (2-phenyl) Phenolate) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolato) (4-phenylphenolate) aluminum, bis (2 , 4-dimethyl-8-quinolinolato) (3,5-dimethylphenolate) 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.
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 extract light emitted from the organic electroluminescent device of the present invention with high efficiency, 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. Thus, 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).
The content of the singlet oxygen quencher is 0.01 to 50% by weight, preferably 0.05 to 30% by weight, based on the total amount constituting the layer to be contained (for example, hole injection transport layer). Preferably, it is 0.1 to 20% by weight.

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 ⁻⁵ Torr 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 the hole injecting and transporting layer, the light emitting layer, and the 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 a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer 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, 1-methylnaphthalene, ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, dichloromethane, chloroform, and the like. , 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 in 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. The concentration of the coating solution is not particularly limited, but can be set to a concentration range suitable for producing a desired thickness by the coating method to be carried out, usually 0.1 to 50% by weight, preferably 1 to 30% by weight. 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. It is used such that the content of the binder resin is 5 to 99.9% by weight, preferably 10 to 99% by weight (relative to the total amount of each component in the case of forming a single-layer element).

The film pressure of each layer such as the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is not particularly limited, but is usually 5 nm to 5 μm.
In addition, 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, silicone 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 (for example, diamond thin film, amorphous silica, electrically insulating glass, metal oxide, metal nitride, metal carbide, metal sulfide), and photocurable resin. 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.
In the organic electroluminescent element of the present invention, an interface layer (intermediate layer) may be provided 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, or 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 a MIM (metal-insulator-metal) type. It may be. The driving voltage is usually 2 to 30V. The organic electroluminescent element of the present invention is 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, an alternative to illumination (incandescent lamp / fluorescent lamp)). It can be used for various display elements [for example, information display elements (personal computer monitors, mobile phone / mobile terminal display elements)], various signs, various sensors, and the like.

  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 Exemplified Compound 2 3,4-dibromo-7,12-diphenylbenzo [k] fluoranthene 5.62 g (0.01 mol), phenylboronic acid 2.44 g (0.02 mol), sodium carbonate 4.24 g, toluene 30 g Then, 150 mg of tetrakis (triphenylphosphine) palladium was added to a mixture consisting of 40 g of water under an argon stream, heated to 100 ° C., and heated and stirred at the same temperature for 8 hours. The reaction mixture was cooled to room temperature, the toluene phase was separated, washed with water, and toluene was distilled off from the toluene phase under reduced pressure. The residue was purified by silica gel column chromatography and further sludged twice with a mixed solvent of isopropanol / acetonitrile to obtain 3.6 g of the target compound of Exemplified Compound 2 as pale yellow crystals. Further, this compound was purified by sublimation at 370 ° C. and 1.5 × 10 ⁻⁴ Pa.

Preparation of Exemplified Compound 25 In Example 1, instead of using 3,4-dibromo-7,12-diphenylbenzo [k] fluoranthene (5.62 g, 0.01 mol) and phenylboronic acid (2.44 g, 0.02 mol) Except that 7.14 g (0.01 mol) of 3,4-dibromo-7,9,10,12-tetraphenylbenzo [k] fluoranthene and 3.98 g (0.02 mol) of 4-phenylphenylboronic acid were used. In accordance with the operation described in Example 1, 3.8 g of the compound of Exemplified Compound 25 was obtained as pale yellow crystals. Further, this compound was purified by sublimation at 400 ° C. and 2.0 × 10 ⁻⁴ Pa.

Production of Exemplified Compound 51 In Example 1, instead of using 2.44 g (0.02 mol) of phenylboronic acid, 4.76 g (0.02 mol) of 9,9-dimethyl-9H-fluorene-2-boronic acid was used. Except that it was used, 2.6 g of the compound of Exemplified Compound 51 was obtained as pale yellow crystals according to the procedure described in Example 1. Further, this compound was purified by sublimation at 380 ° C. and 1.7 × 10 ⁻⁴ Pa.

Production of Exemplified Compound 53 In Example 1, instead of using 5.62 g (0.01 mol) of 3,4-dibromo-7,12-diphenylbenzo [k] fluoranthene and 2.44 g (0.02 mol) of phenylboronic acid 3,4-dibromo-7-phenyl-12- (2′-phenylphenyl) benzo [k] fluoranthene 6.38 g (0.01 mol) and 9,9-dimethyl-9H-fluorene-2-boronic acid 4 Except that 0.76 g (0.02 mol) was used, 4.1 g of the compound of Exemplified Compound 53 was obtained as pale yellow crystals according to the procedure described in Example 1. Further, this compound was purified by sublimation at 400 ° C. and 1.4 × 10 ⁻⁴ Pa.

Production of Exemplary Compound 54 In Example 1, instead of using 2.44 g of phenylboronic acid, 9.94 g (0.02 mol) of 9,9-dicyclopentyl-9H-fluoren-2-ylboronic acid was used. In accordance with the procedure described in Example 1, 3.7 g of the compound of Exemplary Compound 54 was obtained as pale yellow crystals. Further, this compound was purified by sublimation at 420 ° C. and 1.8 × 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, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis (N-phenyl-N-1 ″ -naphthylamino) -1,1′-biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, a hole injection transport layer was formed on the hole injection transport layer, and the compound of Exemplified Compound 2 and 4,4′-bis [2 ″-(4 ″ ′-N, N— Diphenylaminophenyl) vinyl] biphenyl was deposited at a deposition rate of 2.0 nm / sec and 0.02 to 0.1 nm / sec to a thickness of 40 nm to form a light emitting layer. Further, tris (8 -Quinolinolato) Aluminum was vapor deposited at a deposition rate of 0.2 nm / sec to a thickness of 15 nm to form an electron injecting and transporting layer, and further, magnesium and silver as a cathode were deposited at 200 nm at a deposition rate of 0.2 nm / sec. Thickness of An organic electroluminescence device was produced by co-evaporation (weight ratio 10: 1) to produce a cathode, and the deposition was carried out while maintaining the reduced pressure state of the vapor deposition tank. The voltage was applied and continuously driven at a constant current density of 10 mA / cm ² at room temperature in a dry atmosphere.In the initial stage, the voltage value was 5.1 V, and blue light emission with a luminance of 960 cd / m ² was confirmed. The half life of the luminance was 2000 hours.

In Example 6, an organic electroluminescent device was prepared according to the procedure described in Example 6 except that the compound of Illustrative Example Compound 25 was used instead of the compound of Illustrative Compound 2 when forming the light emitting layer. . Further, in the same manner as in Example 6, a direct current voltage was applied to the device, the characteristics of the device were measured, and the results are shown in Table 1 (Table 1).

In Example 6, an organic electroluminescent device was prepared according to the procedure described in Example 6 except that the compound of Exemplified Compound 51 was used instead of the compound of Illustrated Compound 2 in forming the light emitting layer. Further, a direct current voltage was applied to the device in the same manner as in Example 6 to measure the characteristics of the device, and the results are shown in Table 1 (Table 1).

In Example 6, an organic electroluminescent device was prepared according to the procedure described in Example 6 except that the compound of Exemplified Compound 53 was used instead of the compound of Illustrated Compound 2 in forming the light emitting layer. Further, a direct current voltage was applied to the device in the same manner as in Example 6 to measure the characteristics of the device, and the results are shown in Table 1 (Table 1).

In Example 6, an organic electroluminescent device was prepared according to the procedure described in Example 6 except that the compound of Exemplary Compound 54 was used instead of the compound of Exemplary Compound 2 in forming the light emitting layer. Further, a direct current voltage was applied to the device in the same manner as in Example 6 to measure the characteristics of the device, and the results are shown in Table 1 (Table 1).

Comparative Example 1:
In Example 6, instead of using the compound of Illustrative Compound 2 in the formation of the light emitting layer, except that 4,4′-bis (2 ″, 2 ″ -diphenylvinyl) biphenyl was used, the method described in Example 6 was used. According to the operation, an organic electroluminescent device was produced. The characteristics of blue light emission confirmed from the device were further investigated, and the results are shown in Table 1 (Table 1).

Comparative Example 2:
In Example 6, an organic electroluminescent device was produced according to the procedure described in Example 6 except that 9,10-diphenylanthracene was used instead of using the compound of Illustrative Compound 2 when forming the light emitting layer. The characteristics of blue light emission confirmed from the device were further investigated, and the results are shown in Table 1 (Table 1).

Comparative Example 3:
In Example 6, the procedure described in Example 6 was used except that 9,10-bis (3 ′, 5′-diphenylphenyl) anthracene was used instead of using the compound of Exemplary Compound 2 in forming the light emitting layer. According to the above, an organic electroluminescent element was produced. The characteristics of blue light emission confirmed from the device were further investigated, and the results are shown in Table 1 (Table 1).

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 a nitrogen gas, was further subjected to UV / ozone cleaning, it was fixed to a substrate holder of the vapor deposition apparatus, followed by vacuum vapor deposition tank 1.2 × 10- ⁶ Torr.
On the ITO transparent electrode, 1,3,5-tris (4′-N ′, N′-diphenylaminophenyl) benzene was deposited at a deposition rate of 0.1 nm / sec to a thickness of 20 nm to form a first hole. An injection transport layer was formed. Next, 4,4 ′-[N-phenyl-N- (1′-naphthyl) amino] -1,1′-biphenyl was deposited to a thickness of 50 nm at a deposition rate of 0.2 nm / sec, and the second hole An injection transport layer was formed. Next, the compound of exemplary compound 2 and the compound (DP) represented by the following formula are deposited on the hole injecting and transporting layer to a thickness of 40 nm at a deposition rate of 0.2 nm / sec and 0.02 nm / sec, respectively. Then, a light emitting layer was formed. Further, tris (8-quinolinolato) aluminum was deposited on the light emitting layer to a thickness of 50 nm at a deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. Furthermore, aluminum and lithium were co-deposited as a cathode at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form an organic electroluminescent device. 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 electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere. Initially, red light emission of 5.2 V and luminance of 1200 cd / m ² was confirmed. The half life of the brightness was 7000 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 a nitrogen gas, was further subjected to UV / ozone cleaning, was fixed to a substrate holder of the vapor deposition apparatus, followed by vacuum vapor deposition tank 1.2 × 10- ⁶ Torr.
On the ITO transparent electrode, 1,3,5-tris (4′-N ′, N′-diphenylaminophenyl) benzene was deposited at a deposition rate of 0.1 nm / sec to a thickness of 20 nm to form a first hole. An injection transport layer was formed. Next, 4,4 ′-[N-phenyl-N- (1′-naphthyl) amino] -1,1′-biphenyl was deposited to a thickness of 50 nm at a deposition rate of 0.2 nm / sec, and the second hole An injection transport layer was formed. Next, 9,10-diphenylanthracene and Exemplified Compound 51 are deposited on the hole injecting and transporting layer at a deposition rate of 0.2 nm / sec and 0.02 nm / sec to a thickness of 40 nm to form a light emitting layer. Furthermore, tris (8-quinolinolato) aluminum was deposited on the light emitting layer at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injecting and transporting layer. Furthermore, aluminum and lithium were co-deposited as a cathode at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form an organic electroluminescent device. 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 electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere. Initially, blue light emission of 5.8 V and luminance of 1300 cd / m ² was confirmed. The half life of the brightness was 4000 hours.

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 UV / ozone cleaned, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr.
First, poly (thiophene-2,5-diyl) was deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / sec to a thickness of 20 nm to form a first hole injection transport layer. Next, 4,4′-bis [N-phenyl-N- (1′-naphthyl) amino] -1,1′-biphenyl was deposited to a thickness of 55 nm at a deposition rate of 0.2 nm / sec. A hole injection transport layer was formed. Next, 4,4′-bis (2 ″, 2 ″ -diphenylvinyl) -1,1′-biphenyl and the compound of Exemplary Compound 53 are deposited on the hole injecting and transporting layer at a deposition rate of 0.2 nm / sec, respectively. A light-emitting layer was formed by vapor deposition at a thickness of 40 nm at 0.02 nm / sec. Further, tris (8-quinolinolato) aluminum was vapor-deposited on the light-emitting layer to a thickness of 50 nm at a vapor deposition rate of 0.2 nm / sec. An electron injecting and transporting layer was formed. Further, magnesium and silver were co-deposited as a cathode at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form an organic electroluminescent device. 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 electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere. Initially, green light emission of 5.2 V and luminance of 960 cd / m ² was confirmed. The luminance half-life was 2400 hours.

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, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. First, 4,4 ′, 4 ″ -tris [N- (3 ″ -methylphenyl) -N-phenylamino] triphenylamine is deposited on an ITO transparent electrode at a deposition rate of 0.1 nm / sec and a thickness of 50 nm. To form a first hole injection transport layer. Subsequently, 4,4′-bis [N-phenyl-N- (1-naphthyl) amino] was deposited to a thickness of 20 nm at a deposition rate of 0.2 nm / sec to form a second hole injecting and transporting layer. Further, a compound represented by the exemplified compound 25 was deposited thereon to a thickness of 40 nm at 0.1 nm / sec to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was vapor-deposited thereon to a thickness of 50 nm at a vapor deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited as a cathode at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form an organic electroluminescent device. 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. Initially, blue light emission of 5.4 V and luminance of 940 cd / m ² was confirmed. The luminance half-life was 2200 hours.

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, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. First, poly (thiophene-2,5-diyl) was deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / sec to a thickness of 20 nm to form a first hole injection transport layer. After returning the vapor deposition tank to atmospheric pressure, the vapor deposition tank was again decompressed to 3 × 10 ⁻⁶ Torr. Next, the compound of Exemplified Compound 54 and rubrene were co-deposited from different vapor deposition sources to a thickness of 55 nm at a vapor deposition rate of 0.2 nm / sec (weight ratio 10: 1), and the second hole injection / transport layer was also provided. A light emitting layer was formed. Next, while maintaining the reduced pressure state, tris (8-quinolinolato) aluminum was deposited thereon to a thickness of 50 nm at a deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. While maintaining the reduced pressure state, magnesium and silver were further co-deposited as a cathode to a thickness of 200 nm at a deposition rate of 0.2 nm / sec (weight ratio 10: 1) to form a cathode, and an organic electroluminescent device Was made. A DC voltage was applied to the produced organic electroluminescent element, and the organic electroluminescent element was continuously driven at a constant current density of 10 mA / cm ^{2 in} a dry atmosphere. Initially, yellow light emission of 5.3 V and luminance of 960 cd / m ² was confirmed. The half life of luminance was 2500 hours.

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, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. First, Exemplified Compound 2 was deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / sec to a thickness of 20 nm to form a first hole injection transport layer. After returning the vapor deposition tank to atmospheric pressure, the vapor deposition tank was again decompressed to 3 × 10 ⁻⁶ Torr. Next, the compound of Exemplified Compound 51 and rubrene were co-deposited from different vapor deposition sources to a thickness of 55 nm at a vapor deposition rate of 0.2 nm / sec (weight ratio 10: 1), and the second hole injection transport layer was also provided. A light emitting layer was formed. Next, tris (8-quinolinolato) aluminum was deposited thereon to a thickness of 50 nm at a deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited as a cathode at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form an organic electroluminescent device. 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 electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 10 mA / cm ^{2 in} a dry atmosphere. Initially, yellow light emission of 5.1 V and luminance of 940 cd / m ² was confirmed. The luminance half-life was 2400 hours.

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 and further UV / ozone cleaned. Next, a 40 nm hole is formed on the ITO transparent electrode by a spin coating method using a 3 wt% dichloroethane solution containing a polycarbonate (weight average molecular weight 39000) and the compound of Exemplified Compound 25 in a weight ratio of 100: 50. An injection transport layer was formed. Next, the glass substrate having this hole injecting and transporting layer was fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition layer was decompressed to 3 × 10 ⁻⁶ Torr. Next, tris (8-quinolinolato) aluminum was vapor-deposited thereon to a thickness of 50 nm at a vapor deposition rate of 0.2 nm / sec to form a light-emitting layer also serving as an electron injecting and transporting layer. Further, magnesium and silver were co-deposited as a cathode at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form an organic electroluminescent device. When a DC voltage of 10 V was applied to the produced organic electroluminescent element in a dry atmosphere, a current of 89 mA / cm ² flowed. Green light emission with a luminance of 840 cd / m ² was confirmed. The luminance half-life was 500 hours.

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 and further UV / ozone cleaned. Next, on the ITO transparent electrode, polymethyl methacrylate (weight average molecular weight 25000), the compound of Exemplified Compound 53, and tris (8-quinolinolato) aluminum are respectively contained in a weight ratio of 100: 50: 0.5 3 A light emitting layer having a thickness of 100 nm was formed by spin coating using a weight% dichloroethane solution. 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 3 × 10 ⁻⁶ Torr. On the light emitting layer, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm as a cathode (weight ratio 10: 1) to form a cathode, and an organic electroluminescent device was produced. 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 820 cd / m ² was confirmed. The half life of luminance was 450 hours.

According to the present invention, it is possible to provide a novel benzofluoranthene compound and an organic electroluminescence device using the benzofluoranthene compound, which has a long emission lifetime and excellent durability.

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 (9)

A benzofluoranthene compound represented by the general formula (1), which is a compound having one benzofluoranthene skeleton in one molecule .

[In General Formula (1), X _{1 to} X ₁₀ each independently represent a hydrogen atom or a substituent, and Y ₁ and Y ₂ each independently represent a substituted or unsubstituted aryl group . However, in the general formula (1), at least one of Y ₁ and Y ₂ is a substituted or unsubstituted aryl group represented by the general formula (2).

[In General Formula (2) , one of X _{11 to} X ₁₈ represents a bond, the rest independently represents a hydrogen atom or a substituent, and R ₁ and R ₂ each independently represent a hydrogen atom or a substituent. Represents a group] ] A benzofluoranthene compound represented by the general formula (1), which is a compound having one benzofluoranthene skeleton in one molecule.

[In general formula (1), X ₁ ~ X ₁₀ Each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, an ester group, a linear, branched or cyclic alkylcarbonyl group having 1 to 10 carbon atoms, or a carbon atom having 1 to 10 carbon atoms. A linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted group having 7 to 20 carbon atoms An aralkyloxy group, a substituted or unsubstituted aryl group having 4 to 20 carbon atoms, or a substituted or unsubstituted aryloxy group having 4 to 20 carbon atoms, Y ₁ And Y ₂ Each independently represents a substituted or unsubstituted aryl group having 4 to 20 carbon atoms. However, Y ₁ And Y ₂ At least one of them represents a substituted or unsubstituted aryl group represented by the general formula (2).

[In general formula (2), X ₁₁ ~ X ₁₈ Among them, one represents a bond, and the rest each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, an ester group, a straight chain having 1 to 10 carbon atoms, branched or A cyclic alkylcarbonyl group, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms A group, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a substituted or unsubstituted aryl group having 4 to 20 carbon atoms, or a substituted or unsubstituted aryloxy group having 4 to 20 carbon atoms, R ₁ And R ₂ Are each independently a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, or a substituted or unsubstituted group having 4 to 20 carbon atoms. Represents an aryl group]] At least one layer containing at least one benzofluoranthene compound represented by the general formula (1) according to claim 1 or the general formula (1) according to claim 2 is sandwiched between the pair of electrodes. Organic electroluminescent device. The organic electroluminescent element according to claim 3, wherein the layer containing the benzofluoranthene compound represented by the general formula (1) is a light emitting layer. The organic electric field according to claim 4, wherein the light-emitting layer comprises a compound having two or more kinds of light-emitting functions, and a benzofluoranthene compound represented by the general formula (1) is used as a guest material of the light-emitting layer. Light emitting element. The organic electric field according to claim 4, wherein the light-emitting layer comprises a compound having two or more kinds of light-emitting functions, and a benzofluoranthene compound represented by the general formula (1) is used as a host material of the light-emitting layer. Light emitting element. The organic electroluminescence device according to claim 3, wherein the layer containing the benzofluoranthene compound represented by the general formula (1) is a hole injection transport layer. The organic electroluminescent element according to claim 3, further comprising a hole injecting and transporting layer between the pair of electrodes. The organic electroluminescent element according to claim 3, further comprising an electron injecting and transporting layer between the pair of electrodes.

Images