JP4070676B2 - Asymmetric substituted anthracene compound and organic electroluminescent device containing the asymmetric substituted anthracene compound - Google Patents

Description

  The present invention relates to a novel asymmetric substituted anthracene compound and an organic electroluminescence device comprising the asymmetric substituted anthracene 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 [see, for example, 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 element having such characteristics is expected to be applied to various light emitting elements, display elements 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. [See Non-Patent Document 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).
However, it cannot be said that these light emitting elements also have sufficient light emission luminance and light emission lifetime, and at present, further higher luminance 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

An object of the present invention is to provide a novel asymmetric substituted anthracene compound. More specifically, for example, it is to provide an asymmetric substituted anthracene compound that can be suitably used as a light emitting material of an organic electroluminescence device.

  In order to solve the above-mentioned problems, the present inventors have conducted extensive studies on various asymmetrically substituted anthracene compounds, particularly asymmetrically substituted anthracene compounds that can be suitably used for a light emitting material of an organic electroluminescent device. It came to complete. That is, the present invention provides <1>: an asymmetrically substituted anthracene compound represented by the general formula (1),

〔式中、Ｘ₁〜Ｘ₂₂は、それぞれ独立に水素原子または置換基を表し、Ｘ₁〜Ｘ₂₂の隣合う基は、それぞれ隣接する基と共に、環を形成していてもよい〕
<２>：一対の電極間に、一般式（１）で表される非対称置換アントラセン化合物を少なくとも1種含有する層を少なくとも一層挟持してなる有機電界発光素子、
<３>：一般式（１）で表される非対称置換アントラセン化合物を含有する層が、発光層である<２>記載の有機電界発光素子、
<４>：一般式（１）で表される非対称置換アントラセン化合物を含有する層が、正孔注入輸送層である<２>記載の有機電界発光素子、
<５>：一対の電極間に、さらに、正孔注入輸送層を有する<２>、<３>および<４>に記載の有機電界発光素子、
<６>：一対の電極間に、さらに、電子注入輸送層を有する<２>〜<５>のいずれかに記載の有機電界発光素子、
に関するものである。

[Wherein, X _{1 to} X ₂₂ each independently represents a hydrogen atom or a substituent, and adjacent groups of X _{1 to} X ₂₂ may form a ring together with the adjacent groups, respectively]
<2>: an organic electroluminescent device comprising at least one layer containing at least one asymmetrically substituted anthracene compound represented by the general formula (1) between a pair of electrodes,
<3>: The organic electroluminescent element according to <2>, wherein the layer containing the asymmetric substituted anthracene compound represented by the general formula (1) is a light emitting layer,
<4>: The organic electroluminescent device according to <2>, wherein the layer containing the asymmetric substituted anthracene compound represented by the general formula (1) is a hole injection transport layer,
<5>: The organic electroluminescence device according to <2>, <3>, and <4>, further having a hole injection / transport layer between the pair of electrodes.
<6>: The organic electroluminescence device according to any one of <2> to <5>, 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 asymmetric substituted anthracene compound and an organic electroluminescence device having a long emission lifetime and excellent durability.

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

〔式中、Ｘ₁〜Ｘ₂₂は、それぞれ独立に水素原子または置換基を表し、Ｘ₁〜Ｘ₂₂の隣合う基は、それぞれ隣接する基と共に、環を形成していてもよい〕
一般式（１）で表される非対称置換アントラセン化合物において、Ｘ₁〜Ｘ₂₂はそれぞれ独立に水素原子または置換基を表し、好ましくは、水素原子、ハロゲン原子、シアノ基、ニトロ基、置換または未置換のアミノ基、エステル基、炭素数１〜１０の直鎖、分岐または環状のアルキルカルボニル基、炭素数１〜１０の直鎖、分岐または環状のアルキル基、炭素数１〜１０の直鎖、分岐または環状のアルコキシ基、炭素数７〜２０の置換または未置換のアラルキル基、炭素数７〜２０の置換または未置換のアラルキルオキシ基、炭素数４〜２０の置換または未置換のアリール基または炭素数４〜２０の置換または未置換のアリールオキシ基を表し、より好ましくは、水素原子、ハロゲン原子、シアノ基、ニトロ基、置換または未置換のアミノ基、炭素数１〜８の直鎖、分岐または環状のアルキルカルボニル基、炭素数１〜８の直鎖、分岐または環状のアルキル基、炭素数１〜８の直鎖、分岐または環状のアルコキシ基、炭素数７〜１６の置換または未置換のアラルキル基、炭素数７〜１６の置換または未置換のアラルキルオキシ基、炭素数４〜１６の置換または未置換のアリール基または炭素数４〜１６の置換または未置換のアリールオキシ基を表す。
また、Ｘ₁〜Ｘ₂₂の隣合う基は、それぞれ隣接する基と共に環を形成していてもよい。
Ｘ₁〜Ｘ₂₂のハロゲン原子としては、フッ素原子、塩素原子、臭素原子等を挙げることができる。
Ｘ₁〜Ｘ₂₂の置換または未置換のアミノ基としては、例えば、アミノ基、Ｎ−メチルアミノ基、Ｎ−エチルアミノ基、Ｎ−ｎ−プロピルアミノ基、Ｎ−イソプロピルアミノ基、Ｎ−ｎ−ブチルアミノ基、Ｎ−イソブチルアミノ基、Ｎ−sec-ブチルアミノ基、Ｎ−tert-ブチルアミノ基、Ｎ−ｎ−ペンチルアミノ基、Ｎ−シクロペンチルアミノ基、Ｎ−ｎ−ヘキシルアミノ基、Ｎ−シクロヘキシルアミノ基、Ｎ−ベンジルアミノ基、Ｎ−フェネチルアミノ基、Ｎ−フェニルアミノ基、Ｎ−（１−ナフチル）アミノ基、Ｎ−（２−ナフチル）アミノ基、Ｎ−（４−フェニルフェニル）アミノ基、Ｎ−（３−フェニルフェニル）アミノ基、Ｎ−（２−フェニルフェニル）アミノ基、Ｎ−（４−メチルフェニル）アミノ基、Ｎ−（２−メチルフェニル）アミノ基、Ｎ−（２−アントラニル）アミノ基、Ｎ−（９−アントラニル）アミノ基、Ｎ，Ｎ−ジメチルアミノ基、Ｎ，Ｎ−ジエチルアミノ基、Ｎ，Ｎ−ジ−ｎ−プロピルアミノ基、Ｎ，Ｎ−ジ−イソプロピルアミノ基、Ｎ，Ｎ−ジ−ｎ−ブチルアミノ基、Ｎ，Ｎ−ジ−イソブチルアミノ基、Ｎ，Ｎ−ジ−sec-ブチルアミノ基、Ｎ，Ｎ−ジ−ｎ−ペンチルアミノ基、Ｎ，Ｎ−ジシクロペンチルアミノ基、Ｎ，Ｎ−ジシクロヘキシルアミノ基、Ｎ，Ｎ−ジベンジルアミノ基、Ｎ，Ｎ−ジフェネチルアミノ基、Ｎ−メチル−Ｎ−エチルアミノ基、Ｎ−メチル−Ｎ−ｎ−プロピルアミノ基、Ｎ−メチル−Ｎ−イソプロピルアミノ基、Ｎ−メチル−Ｎ−ｎ−ブチルアミノ基、Ｎ−メチル−Ｎ−tert-ブチルアミノ基、Ｎ−メチル−Ｎ−シクロペンチルアミノ基、Ｎ−メチル−Ｎ−シクロヘキシルアミノ基、Ｎ−メチル−Ｎ−ベンジルアミノ基、Ｎ−メチル−Ｎ−フェネチルアミノ基、Ｎ−エチル−Ｎ−tert-ブチルアミノ基、Ｎ−エチル−Ｎ−シクロヘキシルアミノ基、Ｎ−エチル−Ｎ−ベンジルアミノ基、Ｎ−イソプロピル−Ｎ−シクロペンチルアミノ基、Ｎ−イソプロピル−Ｎ−シクロヘキシルアミノ基、Ｎ−イソプロピル−Ｎ−ベンジルアミノ基、Ｎ−tert-ブチルーＮ−シクロヘキシルアミノ基、Ｎ−tert-ブチル−Ｎ−ベンジルアミノ基、Ｎ−シクロペンチル−Ｎ−ベンジルアミノ基、Ｎ−シクロヘキシル−Ｎ−ベンジルアミノ基、Ｎ，Ｎ−ジフェニルアミノ基、Ｎ，Ｎ−ジ（１−ナフチル）アミノ基、Ｎ，Ｎ−ジ（２−ナフチル）アミノ基、Ｎ，Ｎ−ジ（４−フェニルフェニル）アミノ基、Ｎ，Ｎ−（４−メチルフェニル）アミノ基、Ｎ，Ｎ−ジ（３−メチルフェニル）アミノ基、Ｎ−フェニル−Ｎ−（１−ナフチル）アミノ基、Ｎ−フェニル−Ｎ−（２−ナフチル）アミノ基、Ｎ−フェニル−Ｎ−（４−フェニルフェニル）アミノ基、Ｎ−フェニル−Ｎ−（４−メチルフェニル）アミノ基、Ｎ−（１−ナフチル）−Ｎ−（４’−フェニルフェニル）アミノ基を挙げることができる。
Ｘ₁〜Ｘ₂₂のエステル基としては、例えば、メトキシカルボニル基、エトキシカルボニル基、ｎ−プロピルオキシカルボニル基、イソプロピルオキシカルボニル基、ｎ−ブチルオキシカルボニル基、イソブチルオキシカルボニル基、tert-ブチルオキシカルボニル基、ｎ−ペンチルオキシカルボニル基、シクロペンチルオキシカルボニル基、シクロヘキシルオキシカルボニル基、ベンジルオキシカルボニル基、フェニルオキシカルボニル基、１−ナフチルオキシカルボニル基、２−ナフチルオキシカルボニル基、
アセチルオキシ基、エチルカルボニルオキシ基、ｎ−プロピルカルボニルオキシ基、ｎ−ブチルカルボニルオキシ基、tert-ブチルカルボニルオキシ基、シクロヘキシルカルボニルオキシ基、ベンジルカルボニルオキシ基、フェニルカルボニルオキシ基、１−ナフチルカルボニルオキシ基、２−ナフチルカルボニルオキシ基を挙げることができる。
Ｘ₁〜Ｘ₂₂のアルキルカルボニル基としては、例えばメチルカルボニル基、エチルカルボニル基、ｎ−プロピルカルボニル基、イソプロピルカルボニル基、ｎ−ブチルカルボニル基、tert-ブチルカルボニル基、ｎ−ペンチルカルボニル基、シクロペンチルカルボニル基、ｎ−ヘキシルカルボニル基、シクロヘキシルカルボニル基、ｎ−ヘプチルカルボニル基、ｎ−オクチルカルボニル基、ｎ−ノニルカルボニル基、ｎ−デシルカルボニル基を挙げることができる。

[Wherein, X _{1 to} X ₂₂ each independently represents a hydrogen atom or a substituent, and adjacent groups of X _{1 to} X ₂₂ may form a ring together with the adjacent groups, respectively]
In the asymmetrically substituted anthracene compound represented by the general formula (1), X _{1 to} X ₂₂ each independently represents a hydrogen atom or a substituent, and preferably a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted group. A substituted amino group, an ester group, a linear, branched or cyclic alkylcarbonyl group having 1 to 10 carbon atoms, a linear or branched alkyl group having 1 to 10 carbon atoms, a linear chain having 1 to 10 carbon atoms, A branched or cyclic alkoxy group, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, 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 Represents a substituted or unsubstituted aryloxy group having 4 to 20 carbon atoms, more preferably a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino 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 substitution having 4 to 16 carbon atoms Or an unsubstituted aryloxy group is represented.
Further, the adjacent groups of X _{1 to} X ₂₂ may form a ring together with the adjacent groups.
Examples of the halogen atom represented by X _{1 to} X ₂₂ 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 ₂₂ include an amino group, N-methylamino group, N-ethylamino group, Nn-propylamino group, N-isopropylamino group, and Nn. -Butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, Nn-pentylamino group, N-cyclopentylamino group, Nn-hexylamino group, N -Cyclohexylamino group, N-benzylamino group, N-phenethylamino group, N-phenylamino group, N- (1-naphthyl) amino group, N- (2-naphthyl) amino group, N- (4-phenylphenyl) ) Amino group, N- (3-phenylphenyl) amino group, N- (2-phenylphenyl) amino group, N- (4-methylphenyl) amino group, N- (2-methylphenyl) a Group, N- (2-anthranyl) amino group, N- (9-anthranyl) amino group, N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-propylamino group, N, N-di-isopropylamino group, N, N-di-n-butylamino group, N, N-di-isobutylamino group, N, N-di-sec-butylamino group, N, N-di- n-pentylamino group, N, N-dicyclopentylamino group, N, N-dicyclohexylamino group, N, N-dibenzylamino group, N, N-diphenethylamino group, N-methyl-N-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 N-methyl-N-cyclohexylamino group, N-methyl-N-benzylamino group, N-methyl-N-phenethylamino group, N-ethyl-N-tert-butylamino group, N-ethyl-N-cyclohexyl Amino group, N-ethyl-N-benzylamino group, N-isopropyl-N-cyclopentylamino group, N-isopropyl-N-cyclohexylamino group, N-isopropyl-N-benzylamino group, N-tert-butyl-N- Cyclohexylamino group, N-tert-butyl-N-benzylamino group, N-cyclopentyl-N-benzylamino group, N-cyclohexyl-N-benzylamino group, 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) Mention may be made of amino groups.
Examples of the ester group for X _{1 to} X ₂₂ include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propyloxycarbonyl group, an isopropyloxycarbonyl group, an n-butyloxycarbonyl group, an isobutyloxycarbonyl group, and a tert-butyloxycarbonyl group. 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 2-naphthylcarbonyloxy group.
Examples of the alkylcarbonyl group represented by X _{1 to} X ₂₂ include a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an isopropylcarbonyl group, an n-butylcarbonyl group, a tert-butylcarbonyl group, an n-pentylcarbonyl group, and a cyclopentyl group. Examples thereof include a carbonyl group, an n-hexylcarbonyl group, a cyclohexylcarbonyl group, an n-heptylcarbonyl group, an n-octylcarbonyl group, an n-nonylcarbonyl group, and an n-decylcarbonyl group.

Specific examples of the linear, branched or cyclic alkyl group of X _{1 to} X ₂₂ include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a 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 -Methylcyclohexyl group, 3-methyl Cyclohexyl 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 represented by X _{1 to} X ₂₂ 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 represented by X _{1 to} X ₂₂ include, for example, benzyl group, α-methylbenzyl group, α-ethylbenzyl group, phenethyl group, α-methylphenethyl group, β-methylphenethyl group. , Α, α-dimethylbenzyl group, α, α-dimethylphenethyl group, 4-methylphenethyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl group, 4-ethylbenzyl group, 2-ethyl Benzyl group, 4-isopropylbenzyl group, 4-tert-butylbenzyl group, 2-tert-butylbenzyl group, 4-tert-pentylbenzyl group, 4-cyclohexylbenzyl group, 4-n-octylbenzyl group, 4-tert -Octylbenzyl group, 4-allylbenzyl group, 4-benzylbenzyl group, 4-phenethylbenzyl group, 4-phenylbenzyl group, - (4'-methylphenyl) benzyl group, 4-methoxybenzyl group, 2-methoxybenzyl group, 2-ethoxy benzyl group, 4-n-butoxybenzyl group, 4-n-heptyloxy benzyl group,
4-n-decyloxybenzyl 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 An aralkyl group which may have a substituent such as a group, 2-chlorobenzyl group, 3,4-dichlorobenzyl group, 2-furfuryl group, diphenylmethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group; Can be mentioned.

Specific examples of the substituted or unsubstituted aralkyloxy group represented by X _{1 to} X ₂₂ 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 ₂₂ include, for example, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-anthracenyl group, a 9-anthracenyl group, a fluorenyl group, and 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-benzothiophenyl group, 2-benzofuryl group, 2-benzoxazolyl group, 2-benzothiazolyl Group, 2-benzimidazolyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylpheny group 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 Enyl 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-benzi 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 carbonyloxy phenyl 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′-methylphenol ) 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 ₂₂ include a substituted or unsubstituted aryloxy group derived from the above aryl group.

Specific examples of the asymmetrically substituted anthracene compound represented by the general formula (1) according to the present invention include the following compounds, but the present invention is not limited thereto.
1.9-Phenyl-10- (9'-phenanthryl) anthracene 2.9- (4'-methylphenyl) -10- (9 "-phenanthryl) anthracene 3.9- (3'-methylphenyl) -10- (9 "-phenanthryl) anthracene 4.9- (2'-methylphenyl) -10- (9" -phenanthryl) anthracene 5.9- (4'-ethylphenyl) -10- (9 "-phenanthryl) anthracene 6 .9- (3′-Ethylphenyl) -10- (9 ″ -phenanthryl) anthracene 7.9- (2′-ethylphenyl) -10- (9 ″ -phenanthryl) anthracene 8.9- (4′-isopropyl) Phenyl) -10- (9 ″ -phenanthryl) anthracene 9.9- (3′-isopropylphenyl) -10- (9 ″ -phenanthryl) anthracene 10.9- (4′-tert-butylphenyl) -10- (9 ″ -phenanthryl) anthracene 11.9- (3′-tert-butylphenyl) -10- (9 ″ -phenanthryl) anthracene 12 9- (4′-Methoxyphenyl) -10- (9 ″ -phenanthryl) anthracene 13.9- (3′-methoxyphenyl) -10- (9 ″ -phenanthryl) anthracene 14.9- (2′-methoxy) Phenyl) -10- (9 "-phenanthryl) anthracene 15.9- (3'-ethoxyphenyl) -10- (9" -phenanthryl) anthracene 16.9- (2'-ethoxyphenyl) -10- (9 " -Phenanthryl) anthracene 17.9- (4'-methylthiophenyl) -10- (9 "-phenanthryl) anthracene 18.9- (3'-trifluoro) Methyloxy phenyl) -10- (9 "- Fenantori Le) anthracene 19.9- (3'-trifluoromethylphenyl) -10- (9" - phenanthryl) A anthracene
20.9- (2′-Chlorophenyl) -10- (9 ″ -phennatryl) anthracene 21.9- (3′-chlorophenyl) -10- (9 ″ -phenanthryl) anthracene 22.9- (4′-chlorophenyl) -10- (9 "-phenanthryl) anthracene 23.9- (4'-fluorophenyl) -10- (9" -phenanthryl) anthracene 24.9- (3'-fluorophenyl) -10- (9 "-phenanthryl) ) Anthracene 25.9- (2′-fluorophenyl) -10- (9 ″ -phenanthryl) anthracene 26.9- (3′-acetylphenyl) -10- (9 ″ -phenanthryl) anthracene 27.9- (3 ', 5'-dimethylphenyl) -10- (9 "-phenanthryl) anthracene 28.9- (2', 4'-dimethylphenyl) -10- (9 "-phenanthryl) anthracene 29.9- (3 ', 5'-dimethoxyphenyl) -10- (9" -phenanthryl) anthracene 30.9- (2', 4'-dimethoxyphenyl) -10- (9 "-phenanthryl) anthracene 31.9- (3'-fluoro-4'-methylphenyl) -10- (9" -phenanthryl) anthracene 32.9- (4'-fluoro-3 ' -Methylphenyl) -10- (9 "-phenanthryl) anthracene 33.9- (2'-fluoro-4'-methylphenyl) -10- (9" -phenanthryl) anthracene 34.9- (4'- Vinylphenyl) -10- (9 ″ -phenanthryl) anthracene 35.9- (3 ′, 4 ′, 5′-trimethoxyphenyl) -10- (9 ″ -phenanthryl) anthracene 3 .9- (4′-N, N-dimethylaminophenyl) -10- (9 ″ -phenanthryl) anthracene 37.9- (4′-N, N-diethylaminophenyl) -10- (9 ″ -phenanthryl) ) Anthracene 38.9- (4′-N, N-diisopropylaminophenyl) -10- (9 ″ -phenanthryl) anthracene 39.9- (4′-cyclohexylphenyl) -10- (9 ″ -phenanthryl) ant Helene 40.9- (4′-Cyclopentylphenyl) -10- (9 ″ -phenanthryl) anthracene 41.9- (4′-phenylphenyl) -10- (9 ″ -phenanthryl) anthracene 42.9- (3 '-Phenylphenyl) -10- (9 "-phenanthryl) anthracene 43.9- (2'-phenylphenyl) -10- (9" -F Nantril) anthracene 44.9- (4′-phenyl-3′-fluorophenyl) -10- (9 ″ -phenanthryl) anthracene 45.9- (4′-phenoxyphenyl) -10- (9 ″ -phenanthryl) Anthracene 46.9- (3'-phenoxyphenyl) -10- (9 "-phenanthryl) anthracene 47.9- [4 '-(1" -methyl-1 "-phenylethyl) phenyl] -10-
(9 ″ ′-phenanthryl) anthracene 48.9- (1′-naphthyl) -10- (9 ″ -phenanthryl) anthracene 49.9- (2′-naphthyl) -10- (9 ″ -phenanthryl) anthracene 9- (4′-Phenyl-1′-naphthyl) -10- (9 ″ -phenanthryl) anthracene 51.9- (9′H-fluoren-2′-yl) -10- (9 ″ -phenanthryl) an Tracene 52.9- (9 ′, 9′-Dimethyl-9′H-fluoren-2′-yl) -10- (9 ″ -phenanthryl) anthracene 53.9- (9 ′, 9′-diethyl-9 ′ H-fluoren-2'-yl) -10- (9 "
-Phenanthryl) anthracene 54.9- (9 ', 9'-dicyclohexyl-9'H-fluoren-2'-yl) -10
-(9 "-phenanthryl) anthracene 55.9- (9 ', 9'-diphenyl-9'H-fluoren-2'-yl) -10-
(9 "-Fentryl) anthracene 56.9- (9 ', 9'-dicyclopentyl-9'H-fluoren-2'-yl) -10
-(9 "-phenanthryl) anthracene 57.9- (7'-tert-butyl-9 ', 9'-dimethyl-9'H-fluorene-2'-
Yl) -10- (9 "-phenanthryl) anthracene 58.9- (7'-tert-butyl-9 ', 9'-diethyl-9'H-fluorene-2'-
Yl) -10- (9 "-phenanthryl) anthracene 59.9- (7'-tert-butyl-9 ', 9'-dicyclohexyl-9'H-fluoren-2'-yl) -10- (9"- Phenanthryl) anthracene 60.9- (7'-tert-butyl-9 ', 9'-diphenyl-9'H-fluorene-
2'-yl) -10- (9 "-phentolyl) anthracene 61.9- (7'-tert-butyl-9 ', 9'-dicyclopentyl-9'H-fluoren-2'-yl) -10- (9 ″ -phenanthryl) anthracene 62.1,9-diphenyl-10- (9′-phenanthryl) anthracene 63.2,9-diphenyl-10- (9′-phenanthryl) anthracene 64.4,9-diphenyl-10 -(9'-phenanthryl) anthracene 65.2,3,9-triphenyl-10- (9'-phenanthryl) anthracene 66.2,3-diphenyl-9- (4'-phenylphenyl) -10- (9 "-Phenanthryl) anthracene 67.2,3-diphenyl-9- (4'-cyclohexylphenyl) -10- (9"-
Phenanthryl) anthracene 68.2,3-diphenyl-9- (4′-tert-butylphenyl) -10- (9 ″ -phenanthryl) anthracene 69.2-methyl-9-phenyl-10- (9′-phenanthryl) ) Anthracene 70.2-methyl-9- (4′-isopropylphenyl) -10- (9 ″ -phenanthryl) anthracene 71.2-methyl-9- (4′-N, N-dimethylaminophenyl) -10 -(9 "-
Phenanthryl) anthracene 72.2-ethyl-9- (3'-trifluoromethyloxy) -10- (9 "-phenanthryl) anthracene 73.2-n-propyl-9- (3'-chlorophenyl) -10- (9 ″ -phenanthryl) anthracene 74.2-isopropyl-9- (2′-ethoxyphenyl) -10- (9 ″ -phenanthryl) anthracene 75.2-tert-butyl-9-phenyl-10- (9 '-Phenanthryl) anthracene 76.2-tert-butyl-9- (4'-methylphenyl) -10- (9 "-phenanthryl) anthracene 77.2-tert-butyl-9- (4'-cyclohexylphenyl) -10- (9 "-phenanthryl) anthracene 78.2-tert-butyl-9- (4'-phenylphenyl) -10- (9" -phenanthate ) Anthracene 79.2-tert-butyl-9- (3'-phenylphenyl) -10- (9 "-phenanthryl) anthracene 80.2-tert-butyl-9- (9'H-fluorene-2 ' -Ill) -10- (9 "-
Phenanthryl) anthracene 81.2-tert-butyl-9- (9 ′, 9′-dimethyl-9′H-fluoren-2′-yl) -10- (9 ″ -phenanthryl) anthracene 82.3-tert- Butyl-9- (9 ′, 9′-dimethyl-9′H-fluorene-2′-yl) -10- (9 ″ -phenanthryl) anthracene 83.2-tert-butyl-9- (9 ′, 9 '-Dicyclohexyl-9'H-fluorene-
2'-yl) -10- (9 "-phenanthryl) anthracene 84.3-tert-butyl-9- (9 ', 9'-dicyclohexyl-9'H-fluorene-
2'-yl) -10- (9 "-phenanthryl) anthracene 85.3-tert-butyl-9- (9 ', 9'-diphenyl-9'H-fluorene-2'-
Yl) -10- (9 "-phenanthryl) anthracene 86.2-cyclohexyl-9- (4'-methoxyphenyl) -10- (9" -phenanthryl) anthracene 87.3-cyclohexyl-9- (4'- Phenylphenyl) -10- (9 ″ -phenanthryl) anthracene 88.2-cyclohexyl-9- (4′-cyclopentylphenyl) -10- (9 ″-
Phenanthryl) anthracene 89.3-cyclohexyl-9- (3 ′, 5′-diphenylphenyl) -10- (9 ″-
Phenanthryl) anthracene 90.2-cyclopentyl-9- (3′-phenylphenyl) -10- (9 ″ -phenanthryl) anthracene 91.2-cyclopropyl-9- (2′-phenylphenyl) -10- (9 "-Phenanthryl) anthracene 92.3-phenyl-9- (4'-phenylphenyl) -10- (9" -phenanthryl) anthracene 93.2-phenyl-9- (4'-cyclohexylphenyl) -10- (9 "-phenanthryl) anthracene 94.3- (1'-naphthyl) -9-phenyl-10- (9" -phenanthryl) anthracene 95.2- (4'-methoxyphenyl) -9-phenyl-10 -(9 "-phenanthryl) anthracene 96.2- (4'-phenylphenyl) -9- (3" -phenylphenyl)- 10-
(9 "'-phenanthryl) anthracene 97.2- (4'-cyclohexylphenyl) -9- (3", 5 "-dicyclohexylphenyl) -10- (9"'-phenanthryl) anthracene 98.9- (4 ' -Phenylphenyl) -10- (2 "-phenyl-9" -phenanthryl) anthracene 99.9-phenyl-10- (1'-phenyl-9'-phenanthryl) anthracene 100.9- (3 ', 4' , 5'-trimethylphenyl) -10- (2 "-methyl-9"
-Phenanthryl) anthracene 101.9- (4'-cyclohexylphenyl) -10- (1 "-methyl-9" -phenanthryl) anthracene 102.9- (4'-cyclopentylphenyl) -10- (2 "- Phenyl-9 "-phenanthryl) anthracene 103.2-tert-butyl-9- (3'-phenylphenyl) -10- (2" -methyl-
9 "-phenanthryl) anthracene 104.3-cyclohexyl-9- (3 ', 5'-diphenylphenyl) -10-
(2′-Cyclohexyl-9 ″ -phenanthryl) anthracene The asymmetrically substituted anthracene compound represented by the general formula (1) of the present invention can be produced, for example, by the steps shown below.
Production of asymmetrically substituted anthracene compound represented by general formula (1)

〔式中、Ｘ₁〜Ｘ₂₂は一般式（１）と同様の意味を表し、Ｌ₁はハロゲン原子を表す〕
すなわち、一般式（Ａ）で表されるボロン酸誘導体と一般式（Ｂ）で表されるハロゲン化アントラセン誘導体をパラジウム触媒［例えば、テトラキス（トリフェニルホスフィン）パラジウム、酢酸パラジウム／トリ-tert-ブチルホスフィン］の存在下に反応させることにより製造することができる。
尚、一般式（Ｂ）で表される化合物は、例えば、以下の工程（化５）により製造することができる。

[Wherein, X _{1 to} X ₂₂ represent the same meaning as in general formula (1), and L ₁ represents a halogen atom]
That is, a boronic acid derivative represented by the general formula (A) and a halogenated anthracene derivative represented by the general formula (B) are converted into a palladium catalyst [for example, tetrakis (triphenylphosphine) palladium, palladium acetate / tri-tert-butyl It can be produced by reacting in the presence of phosphine].
In addition, the compound represented by general formula (B) can be manufactured by the following processes (chemical formula 5), for example.

〔式中、Ｘ₁〜Ｘ₁₃は一般式（１）と同様の意味を表し、Ｌ₁はハロゲン原子を表す〕
すなわち、一般式（Ｃ）で表されるハロゲン化アントラセン誘導体と、一般式（Ｄ）で表されるフェニルボロン酸誘導体をパラジウム触媒〔例えば、テトラキス（トリフェニルホスフィン）パラジウム、トリス（ジベンジリデンアセトン）ジパラジウム〕、および塩基（例えば、炭酸カリウム、炭酸ナトリウム、トリエチルアミン、ピリジン）の存在下に反応させ、一般式（Ｅ）で表される化合物を製造した後、一般式（Ｅ）で表される化合物にハロゲン化剤（たとえば、Ｎ−ブロモスクシンイミド、Ｎ−ヨードスクシンイミド）を作用させ、一般式（Ｂ）で表されるハロゲン化アントラセン誘導体を製造することができる。
また、一般式（Ａ）で表されるボロン酸誘導体は、例えば、下記の工程（化６）に従い製造することができる。

[Wherein, X _{1 to} X ₁₃ represent the same meaning as in general formula (1), and L ₁ represents a halogen atom]
That is, a halogenated anthracene derivative represented by the general formula (C) and a phenylboronic acid derivative represented by the general formula (D) are converted into a palladium catalyst [for example, tetrakis (triphenylphosphine) palladium, tris (dibenzylideneacetone). Dipalladium] and a base (for example, potassium carbonate, sodium carbonate, triethylamine, pyridine) to produce a compound represented by the general formula (E), and then represented by the general formula (E) A halogenated agent (for example, N-bromosuccinimide, N-iodosuccinimide) is allowed to act on the compound to produce a halogenated anthracene derivative represented by the general formula (B).
Moreover, the boronic acid derivative represented by the general formula (A) can be produced, for example, according to the following step (Chemical Formula 6).

〔式中、Ｘ₁₄〜Ｘ₂₂は一般式（１）と同様の意味を表し、Ｌ₂はハロゲン原子を表し、Ｒは低級アルキル基を表す〕
すなわち、一般式（Ｆ）で表されるフェナントレン誘導体にマグネシウムまたは、ｎ−ブチルリチウムを作用させ、その後、ホウ酸トリアルキル（例えば、ホウ酸トリメチル、ホウ酸トリイソプロピル）を作用させ、さらに酸で加水分解することにより製造することができる。
次に本発明の有機電界発光素子について説明する。本発明の有機電界発光素子は、一対の電極間に、一般式（１）で表される非対称置換アントラセン化合物を少なくとも１種含有する層を少なくとも一層挟持してなるものである。有機電界発光素子は、通常一対の電極間に少なくとも１種の発光成分を含有する発光層を少なくとも一層挟持してなるものである。発光層に使用する化合物の正孔注入および正孔輸送、電子注入および電子輸送の各機能レベルを考慮し、所望に応じて、正孔注入成分を含有する正孔注入輸送層および／または電子注入輸送成分を含有する電子注入輸送層を設けることもできる。
例えば、発光層に使用する化合物の正孔注入機能、正孔輸送機能および／または電子注入機能、電子輸送機能が良好な場合には、発光層が正孔注入輸送層および／または電子注入輸送層を兼ねた型の素子構成として一層型の素子構成とすることができる。また、発光層が正孔注入機能および／または正孔輸送機能に乏しい場合には発光層の陽極側に正孔注入輸送層を設けた二層型の素子構成、発光層が電子注入機能および／または電子輸送機能に乏しい場合には発光層の陰極側に電子注入輸送層を設けた二層型の素子構成とすることができる。さらには発光層を正孔注入輸送層と電子注入輸送層で挟み込んだ構成の三層型の素子構成とすることも可能である。
また、正孔注入輸送層、電子注入輸送層および発光層のそれぞれの層は、一層構造であっても多層構造であってもよく、正孔注入輸送層および電子注入輸送層は、それぞれの層において、注入機能を有する層と輸送機能を有する層を別々に設けて構成することもできる。
本発明の有機電界発光素子において、一般式（１）で表される非対称置換アントラセン化合物は、正孔注入輸送層および／または発光層の構成成分として使用することが好ましく、発光層の構成成分として使用することがより好ましい。
本発明の有機電界発光素子において、一般式（１）で表される非対称置換アントラセン化合物は、単独で使用してもよく、また複数併用してもよい。

[Wherein X _{14 to} X ₂₂ represent the same meaning as in general formula (1), L ₂ represents a halogen atom, and R represents a lower alkyl group]
That is, magnesium or n-butyl lithium is allowed to act on the phenanthrene derivative represented by the general formula (F), and then trialkyl borate (for example, trimethyl borate, triisopropyl borate) is allowed to act on the phenanthrene derivative. It can be produced by hydrolysis.
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 asymmetrically substituted anthracene 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 injection transport layer is provided on the cathode side of the light emitting layer can be obtained. Furthermore, a three-layer device structure in which the light-emitting layer is sandwiched between a hole injecting and transporting layer and an electron injecting and transporting 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 asymmetric substituted anthracene compound represented by the general formula (1) is preferably used as a component of the hole injection transport layer and / or the light emitting layer, and as a component of the light emitting layer. More preferably it is used.
In the organic electroluminescent element of the present invention, the asymmetric substituted anthracene 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 may be an asymmetrically substituted anthracene compound represented by the general formula (1) or other compound having a hole injecting and transporting function (for example, phthalocyanine derivatives, triarylamine derivatives, triarylmethane derivatives, oxazole derivatives) , Hydrazone derivatives, stilbene derivatives, pyrazoline derivatives, polysilane derivatives, polyphenylene vinylene and derivatives thereof, polythiophene and derivatives thereof, poly-N-vinylcarbazole, etc.).
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 an asymmetrically substituted anthracene 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 asymmetrically substituted anthracene compound represented by the general formula (1) of the present invention that can be used in the organic electroluminescent 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 Cyclo Hexane, 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 (diphenyl Amino) benzene, 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 [N- (4'-diphenylamino] benzene, etc., polythiophene and its derivatives, poly-N-vinylcarbazole and its derivatives are more preferred.
When the asymmetrically substituted anthracene compound represented by the general formula (1) and another compound having a hole injection function are used in combination, the asymmetrically substituted anthracene compound represented by the general formula (1) in the hole injecting and transporting layer The content 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 uses an asymmetric substituted anthracene compound represented by the general formula (1) as a host material, and at least one compound having a light emitting function other than the asymmetric substituted anthracene compound represented by the general formula (1) as a guest material. And an asymmetrically substituted anthracene represented by the general formula (1) using at least one compound having a light emitting function other than the asymmetrically substituted anthracene compound represented by the general formula (1) as a host material. It can also be formed using compounds as guest materials.
As a compound (guest material / host material) having a light emitting function other than the asymmetrically substituted anthracene compound represented by the general formula (1), for example, an acridone derivative, a quinacridone derivative, a diketopyrrolopyrrole derivative, 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) Examples of the functional compound include the compounds described above), 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 (for example, coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 10 , 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, cinnamate derivatives, poly-N-vinylcarbazole and derivatives thereof, polythiophene and derivatives thereof, polyphenylene and derivatives thereof, polyfluorene and derivatives thereof , Polyphenylene vinylene and derivatives thereof, polybiphenylene vinylene and derivatives thereof, polyterphenylene vinylene and derivatives thereof, polynaphthylene vinyl Examples include nylene and its derivatives, polythienylene vinylene and its derivatives, and the like. Compounds having a light emitting function other than the asymmetrically substituted anthracene compound represented by the general formula (1) (guest material / host material) include acridone derivatives, quinacridone derivatives, polycyclic aromatic compounds, triarylamine derivatives, organometallic complexes And stilbene derivatives are preferred, and polycyclic aromatic compounds and organometallic complexes are more preferred.
The organic electroluminescent element of the present invention preferably contains an asymmetric substituted anthracene compound represented by the general formula (1) as a host material in the light emitting layer.
When the asymmetric substituted anthracene compound represented by the general formula (1) is used as a host material in combination with a compound having a light emitting function (guest material), the asymmetric substitution represented by the general formula (1) in the light emitting layer The content of the anthracene compound is preferably 99.9 to 80% by weight, and more preferably 99 to 90% by weight.
A host material may be used independently and may be used together.
Moreover, a guest material may be used independently and may be used together.
When a plurality of host materials are used in combination, the ratio of the asymmetrically substituted anthracene compound represented by the general formula (1) of the present invention to the entire host material is preferably 99 to 10% by weight, more preferably 90 to 20%. % 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 vacuum deposition, the conditions for vacuum deposition are as follows. Although not particularly limited, it is usually less than 10 ⁻⁵ Torr at a boat temperature (deposition source temperature) of about 50 to 500 ° C. and a substrate temperature of about −50 to 300 ° C. It is preferable to carry out at a deposition rate of about 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, a component for forming each layer or its component and a binder resin are dissolved or dispersed in a solvent to obtain a coating solution. Examples of the solvent include organic solvents (hydrocarbon solvents such as hexane, octane, decane, toluene, xylene, ethylbenzene, and 1-methylnaphthalene, ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, dichloromethane, and chloroform. , Halogenated hydrocarbon solvents such as tetrachloromethane, dichloroethane, trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene, chlorotoluene, ester solvents such as ethyl acetate, butyl acetate, amyl acetate, ethyl lactate, methanol, propanol, butanol Alcohol solvents such as pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve, ethylene glycol, dibutyl ether, tetrahydro Ether solvents such as ethylene, dioxane, dimethoxyethane, anisole, N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide And polar solvents) and water. A solvent may be used independently and may be used together. When the components of the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer are dispersed in a solvent, for example, a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer or the like is used as a dispersion method. Can be used.
Examples of binder resins that can be used for each layer such as a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer include poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethyl methacrylate, poly Methyl acrylate, polyether, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide, polyethersulfone, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polyphenylene vinylene and derivatives thereof, polyfluorene and derivatives thereof, Examples thereof include polymer compounds such as polythienylene vinylene and its derivatives. Binder resins may be used alone or in combination. 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. The binder resin is used so 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 when a single-layer element is formed).
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 includes a panel-type light source (for example, a backlight for a clock, a liquid crystal panel, etc.), various light-emitting elements (for example, an alternative to a light-emitting element such as an LED), and various display elements [for example, information display Element (PC monitor, mobile phone / mobile terminal display element)], 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 Illustrative Compound 1 [1]: Production of 10-bromo-9-phenylanthracene 25.4 g (0.10 mol) of 9-phenylanthracene was dissolved in 300 ml of tetrahydrofuran, and 19.6 g of N-bromosuccinimide was dissolved in this solution ( 0.11 mol) was added. Thereafter, the mixture was stirred at 30 ° C. for 2 hours, tetrahydrofuran was distilled off under reduced pressure, methanol was added to the residue, and the mixture was stirred with heating to obtain 29.8 g of crude crystals. Furthermore, the crude crystals were dissolved in 200 ml of toluene by heating and insoluble matters were filtered off under heating, and then the filtrate was cooled to obtain 25.7 g of 10-bromo-9-phenylanthracene.
[2]: Preparation of 9-phenanthrylboronic acid A mixture of 3.0 g of wrought magnesium, 2 drops of 1,2-dibromoethane and 10 ml of tetrahydrofuran was heated to 60-70 ° C., and 9-bromo A mixture consisting of 25.0 g of phenanthrene and 200 ml of tetrahydrofuran was added dropwise at the same temperature over 2 hours. The mixture was stirred at the same temperature for 2 hours, and then the reaction mixture was cooled to −50 to −40 ° C. A mixture consisting of 13.1 g of trimethyl borate and 100 ml of tetrahydrofuran was added dropwise over 30 minutes, and the mixture was further stirred at the same temperature for 2 hours. Thereafter, the reaction mixture was warmed to room temperature, 100 ml of 5% aqueous sulfuric acid solution was added, and the mixture was stirred for 1 hour at room temperature. Thereafter, the aqueous layer was separated, tetrahydrofuran was distilled off under reduced pressure, and the residue was sludged to obtain 12.5 g of 9-phenanthrylboronic acid as colorless crystals.
[3]: Preparation of Exemplified Compound 1 9-phenanthrylboronic acid 4.90 g (22 mmol), 10-bromo-9-phenylanthracene 7.33 g (22 mmol), sodium carbonate 4.66 g, toluene 12 g and water 24 g Under a stream of argon, 170 mg of tetrakis (triphenylphosphine) palladium was added to the resulting mixture, heated to 80 ° C., and stirred at the same temperature for 6 hours. The reaction mixture was cooled to room temperature and the resulting solid was filtered off. The solid was purified by silica gel column chromatography, and further recrystallized twice from toluene to obtain 3.1 g of the target compound of Exemplified Compound 1 as colorless crystals. Further, this compound was purified by sublimation at 410 ° C. and 2 × 10 ⁻⁴ Pa.

Preparation of Exemplified Compound 8 In [3] of Example 1, instead of using 7.33 g (22 mmol) of 10-bromo-9-phenylanthracene, 10-bromo-9- (4′-isopropylphenyl) anthracene. Except for using 25 g (22 mmol), 3.2 g of the compound of Exemplary Compound 8 was obtained as colorless crystals according to the procedure described in [3] of Example 1. Further, this compound was purified by sublimation at 400 ° C. and 2 × 10 ⁻⁴ Pa.

Preparation of Exemplary Compound 12 In [1] of Example 1, instead of using 7.33 g (22 mmol) of 10-bromo-9-phenylanthracene, 10-bromo-9- (4′-methoxyphenyl) anthracene Except for using 99 g (22 mmol), 3.6 g of Compound of Illustrative Compound 12 was obtained as colorless crystals according to the procedure described in [3] of Example 1. Further, this compound was purified by sublimation at 400 ° C. and 3 × 10 ⁻⁴ Pa.

Preparation of Exemplified Compound 27 In [3] of Example 1, instead of using 7.33 g (22 mmol) of 10-bromo-9-phenylanthracene, 10-bromo-9- (3 ′, 5′-dimethylphenyl) Except for using 7.94 g (22 mmol) of anthracene, 3.8 g of Compound of Exemplified Compound 27 was obtained as colorless crystals according to the procedure described in [3] of Example 1. Further, this compound was purified by sublimation at 410 ° C. and 2 × 10 ⁻⁴ Pa.

Preparation of Exemplified Compound 39 In [3] of Example 1, instead of using 7.33 g (22 mmol) of 10-bromo-9-phenylanthracene, 10-bromo-9- (4′-cyclohexylphenyl) anthracene. Except for using 13 g (22 mmol), 3.8 g of the compound of Exemplary Compound 39 was obtained as colorless crystals according to the procedure described in [3] of Example 1. Further, this compound was purified by sublimation at 440 ° C. and 2 × 10 ⁻⁴ Pa.

Preparation of Exemplary Compound 42 In [3] of Example 1, instead of using 7.33 g (22 mmol) of 10-bromo-9-phenylanthracene, 10-bromo-9- (3′-phenylphenyl) anthracene. Except that 00 g (22 mmol) was used, 4.1 g of the compound of Exemplified Compound 42 was obtained as colorless crystals according to the procedure described in [3] of Example 1. Further, this compound was purified by sublimation at 420 ° C. and 3 × 10 ⁻⁴ Pa.

Production of Illustrative Compound 52 [1]: Production of 10-bromo-9- (9 ′, 9′-dimethyl-9′H-fluoren-2′-yl) anthracene:
In a mixture of 75 g of 9,9-dimethyl-9H-fluoren-2-ylboronic acid, 68 g of 2-bromoanthracene, 30 g of sodium carbonate, 240 g of toluene and 120 g of water, 2.6 g of tetrakis (triphenylphosphine) palladium was added under an argon stream. The mixture was added, heated to 80 ° C., and reacted at the same temperature for 8 hours. Thereafter, the toluene layer was separated and washed with water, and then toluene was distilled off under reduced pressure. The residue was heat sludged with hexane, and 9- (9 ′, 9′-dimethyl-9′H-fluorene-2′- Il) 92 g of anthracene was obtained.
Next, 22.7 g of N-bromosuccinimide was added to a mixture of 40 g of 9- (9 ′, 9′-dimethyl-9′H-fluoren-2′-yl) anthracene and 450 g of tetrahydrofuran, and heated at 30 ° C. for 6 hours. Stir. The reaction mixture was cooled to room temperature, 130 ml of methanol was added, the temperature was raised to 80 ° C., and the resulting solid was cooled to room temperature and filtered off. The obtained solid was recrystallized from toluene to obtain 38.7 g of the intended 10-bromo-9- (9 ′, 9′-dimethyl-9′H-fluoren-2′-yl) anthracene.
[2]: Production of Exemplary Compound 52 In [3] of Example 1, instead of using 7.33 g (22 mmol) of 10-bromo-9-phenylanthracene, 10-bromo-9- (9 ′, 9 ′ Except that 9.88 g (22 mmol) of -dimethyl-9′H-fluoren-2′-yl) anthracene was used, the compound of Exemplified Compound 52 was converted to colorless crystals according to the procedure described in [3] of Example 1. 4.6 g was obtained. Further, this compound was purified by sublimation at 440 ° C. and 2 × 10 ⁻⁴ Pa.

Preparation of Exemplary Compound 54 In [3] of Example 1, instead of using 7.33 g (22 mmol) of 10-bromo-9-phenylanthracene, 10-bromo-9- (9 ′, 9′-dicyclohexyl-9 Except for using 12.87 g of 'H-fluoren-2'-yl) anthracene, 5.1 g of the compound of Exemplified Compound 54 was obtained as colorless crystals according to the procedure described in [3] of Example 1. Further, this compound was purified by sublimation at 450 ° C. and 3 × 10 ⁻⁴ Pa.

Preparation of Exemplary Compound 75 In [3] of Example 1, instead of using 7.33 g (22 mmol) of 10-bromo-9-phenylanthracene, 9-bromo-10-phenyl-2-tert-butylanthracene was used. Except that 56 g (22 mmol) was used, 3.8 g of the compound of exemplary compound 75 was obtained as colorless crystals according to the procedure described in [3] of Example 1. Further, this compound was purified by sublimation at 410 ° C. and 3 × 10 ⁻⁴ Pa.

Preparation of Exemplified Compounds 81 and 82 In [3] of Example 1, instead of using 7.33 g (22 mmol) of 10-bromo-9-phenylanthracene, 2-tert-butyl-9-bromo-10- (9 ', 9'-Dimethyl-9'H-fluoren-2'-yl) anthracene and 3-tert-butyl-9-bromo-10- (9', 9'-dimethyl-9'H-fluorene-2'- I) Except that 11.11 g (22 mmol) of the mixture of anthracene was used, the mixture of the compound of Exemplified Compound 81 and the compound of Exemplified Compound 82 as colorless crystals was obtained according to the procedure described in [3] of Example 1. 4 g was obtained. Further, this compound was purified by sublimation at 450 ° C. and 3 × 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. This 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, 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 as a light-emitting layer, and the compound of Exemplified Compound 1 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. This was applied and continuously driven at a constant current density of 10 mA / cm ^{2 in} a dry atmosphere at room temperature, and initially, a voltage value of 5.5 V and blue light emission with a luminance of 980 cd / m ² were confirmed. The half life of luminance was 2300 hours.

In Example 11, when the light emitting layer was formed, an organic electroluminescence device was prepared according to the procedure described in Example 11 except that the compound of Illustrative Example Compound 8 was used instead of the compound of Illustrative Compound 1. . Further, in the same manner as in Example 11, a DC 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 11, an organic electroluminescent device was prepared according to the procedure described in Example 11 except that the compound of Illustrative Compound 1 was used instead of the compound of Illustrative Compound 1 in forming the light emitting layer. Further, in the same manner as in Example 11, a DC 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 11, when the light emitting layer was formed, an organic electroluminescence device was prepared according to the procedure described in Example 11 except that the compound of exemplary compound 27 was used instead of the compound of exemplary compound 1. Further, in the same manner as in Example 11, a DC 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 11, an organic electroluminescent device was prepared according to the procedure described in Example 11 except that the compound of Illustrative Compound 1 was used instead of the compound of Illustrative Compound 1 in forming the light emitting layer. Further, in the same manner as in Example 11, a DC 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 11, when the light emitting layer was formed, an organic electroluminescent device was produced according to the procedure described in Example 11 except that the compound of Exemplified Compound 1 was used instead of the compound of Illustrated Compound 1. Further, in the same manner as in Example 11, a DC 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 11, an organic electroluminescent device was prepared according to the procedure described in Example 11 except that the compound of Exemplified Compound 52 was used instead of the compound of Illustrated Compound 1 in forming the light emitting layer. Further, in the same manner as in Example 11, a DC 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 11, when the light emitting layer was formed, an organic electroluminescent device was produced according to the procedure described in Example 11 except that the compound of exemplary compound 54 was used instead of the compound of exemplary compound 1. Further, in the same manner as in Example 11, a DC 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 11, when the light emitting layer was formed, instead of using the compound of Exemplified Compound 1, the same procedure as in Example 10 except that the mixture of the compound of Exemplified Compound 81 and the compound of Illustrated Compound 82 was used was used. An organic electroluminescent device was prepared according to the procedure described in Example 11. Further, a DC voltage was applied to the device in the same manner as in Example 11, the characteristics of the device were measured, and the results are shown in Table 1 (Table 1).
Comparative Example 1:
In Example 11, when the light emitting layer was formed, instead of using the compound of Exemplary Compound 1, 4,4′-bis (2 ″, 2 ″ -diphenylvinyl) biphenyl was used instead of using the compound of Example Compound 1. According to the operation, an organic electroluminescent device was produced. Blue light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
Comparative Example 2:
In Example 11, when the light emitting layer was formed, an organic electroluminescent device was produced according to the procedure described in Example 11 except that 9,10-diphenylanthracene was used instead of using the compound of Exemplary Compound 1. Blue light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
Comparative Example 3:
In Example 11, when the light emitting layer was formed, instead of using the compound of Exemplified Compound 1, 9,10-bis (3 ′, 5′-diphenylphenyl) anthracene was used, except that the compound described in Example 11 was used. According to the operation, an organic electroluminescent element was prepared. Blue-green light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

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. This 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 Example Compound 12 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 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 5.4 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. This 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, 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. Next, 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, the compound of the exemplified compound 54 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 5.7 V and a luminance of 930 cd / m ² was confirmed. The half life of luminance was 2100 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. This 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. After returning the vapor deposition tank to atmospheric pressure, the vapor deposition tank was again decompressed to 3 × 10 ⁻⁶ Torr. Subsequently, the compound of Exemplified Compound 42 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 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 5.9 V and luminance of 990 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. This 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, Exemplified Compound 75 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 39 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 5.8 V and luminance of 920 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 spin coating using a 3 wt% dichloroethane solution containing polycarbonate (weight average molecular weight 39000) and the compound of Exemplified Compound 1 in a weight ratio of 100: 50. An injection transport layer was formed. Next, the glass substrate having the 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 98 mA / cm ² flowed. Green light emission with a luminance of 860 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), a mixture of the compound of Exemplified Compound 81 prepared in Example 10 and the compound of Illustrated Compound 82, and tris (8-quinolinolato) aluminum are respectively weight ratios. A 100 nm light-emitting layer was formed by spin coating using a 3 wt% dichloroethane solution contained at a ratio of 100: 50: 0.5. 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 depressurized 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 85 mA / cm ² flowed. Green light emission with a luminance of 960 cd / m ² was confirmed. The half life of luminance was 650 hours.

According to the present invention, it is possible to provide a novel asymmetric substituted anthracene compound and an organic electroluminescence device using the asymmetric substituted anthracene compound, having a long light 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 (6)

An asymmetric substituted anthracene compound having different substituents at the 9-position and the 10-position of anthracene represented by the general formula (1).

[Wherein, X _{1 to} X ₂₂ 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 group having 1 to 10 carbon atoms. An 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 substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a substituted or unsubstituted aryl group having 4 to 20 carbon atoms, or an aryloxy group having 4 to 20 carbon atoms , which is adjacent to X ₁ to X ₅ fit groups, with each adjacent groups, when they form a ring, the partial structure of the following (Formula 2) is 1-naphthyl, 2-naphthyl, 4-phenyl-1-naphthyl, 9H-fluoren-2-yl, 9 , 9-Dimethyl-9H-fluoren-2-yl, 9,9-diethyl-9H-fluorene, 9,9-dicyclohexyl-9H-fluoren-2-yl, 9,9-diphenyl-9H-fluoren-2-yl 9,9-dicyclopentyl-9H-fluoren-2-yl, 7-tert-butyl-9,9-dimethyl-9H-fluoren-2-yl, 7-tert-butyl-9,9-diethyl-9H- Fluoren-2-yl, 7-tert-butyl-9,9-dicyclohexyl-9H-fluoren-2-yl, 7-tert-butyl-9,9-diphenyl-9H-fluoren-2-yl, and 7- It represents a group selected from tert-butyl-9,9-dicyclopentyl-9H-fluoren-2-yl. _However, X 6 _{to X 13} represents a hydrogen atom, _and when X 1 to X ₅ is a heteroaryl group are excluded. ]

An organic electroluminescence device comprising at least one layer containing at least one asymmetric anthracene compound represented by the general formula (1) according to claim 1 between a pair of electrodes. The organic electroluminescent element according to claim 2, wherein the layer containing the asymmetrically substituted anthracene compound represented by the general formula (1) is a light emitting layer. The organic electroluminescent device according to claim 2, wherein the layer containing the asymmetrically substituted anthracene compound represented by the general formula (1) is a hole injection transport layer. The organic electroluminescent element according to claim 2, further comprising a hole injecting and transporting layer between the pair of electrodes. The organic electroluminescent element according to claim 2, further comprising an electron injecting and transporting layer between the pair of electrodes.

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