JPH05163488A - Electroluminescent element of organic thin film - Google Patents

Electroluminescent element of organic thin film

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JPH05163488A
JPH05163488A JP33351791A JP33351791A JPH05163488A JP H05163488 A JPH05163488 A JP H05163488A JP 33351791 A JP33351791 A JP 33351791A JP 33351791 A JP33351791 A JP 33351791A JP H05163488 A JPH05163488 A JP H05163488A
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Koji Nishizaki
Shigeki Takeuchi
Kiyoshi Tamaki
喜代志 玉城
茂樹 竹内
浩二 西嵜
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Konica Corp
コニカ株式会社
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Abstract

PURPOSE: To obtain an electroluminescence element having strong emission intensity, high durability and practical level.
CONSTITUTION: In an electroluminescent element composed of a pair of counter electrodes and one or plural layers of an organic compound layer sandwiched in between the electrodes, at least one layer containing a specific polycyclic quinone compound and at least one layer containing a styryl compound are laid in the element to give an electroluminescent element of organic thin film.
COPYRIGHT: (C)1993,JPO&Japio

Description

【発明の詳細な説明】 DETAILED DESCRIPTION OF THE INVENTION

【0001】 [0001]

【産業上の利用分野】本発明は薄膜エレクトロルミネッセンス素子に関し、特に平面光源及びフラットディスプレイなどに用いられる薄膜エレクトロルミネッセンス素子に関する。 The present invention relates to an film electroluminescent device, particularly relates to a thin film electroluminescent device used such as a flat light source and a flat display.

【0002】 [0002]

【従来の技術】エレクトロルミネッセンス素子は、有機発光層および該層をはさんだ一対の対向電極から構成されており、その発光は一方の電極から注入された電子と、もう一方の電極から注入された正孔により、発光層内で再結合がおこり発光体がより高いエネルギー準位に励起され、励起された発光体が元の基底状態にもどる際にエネルギーを光として放出することにより発生する。 BACKGROUND ART electroluminescent device, organic light-emitting layer and is composed of a pair of opposing electrodes sandwiching the layer, and electrons that emission injected from one electrode, which is injected from the other electrode hole, the light emitting element recombine in the light emitting layer is excited to a higher energy level, the excited luminescent material is produced by emitting energy as light when returning to the original ground state.
このようなキャリア注入型エレクトロルミネッセンス素子は、発光層として薄膜状有機化合物を用いるようになってから発光強度の強いものが得られるようになってきた。 Such carrier injection type electroluminescent device, stronger from so a thin film-like organic compound as a light-emitting layer emission intensity has come to be obtained. 例えば、米国特許3,530,325号には発光体として単結晶アントラセン等を用いたもの、特開昭59-194393号には正孔注入層と有機発光体層を組合せたもの、特開昭 For example, those in U.S. Patent No. 3,530,325 which uses a single crystal anthracene as the luminescent material, as in JP 59-194393 a combination of a hole injection layer and the organic light emitting layer, JP
63-295695号には正孔注入輸送層と有機電子注入輸送層を組合せたもの及びJpn.Journal of Applied Physics,v The No. 63-295695 those combining hole injecting and transporting layer and the organic electron injecting and transporting layer and Jpn.Journal of Applied Physics, v
ol27,No2,P269〜271には正孔移動層と発光層と電子移動層を組合せたものなどが開示されており、これらによりこれまで発光強度は改良されてきた。 ol27, No2, P269~271 is disclosed including a combination of a hole transport layer light emitting layer and the electron transport layer, the luminous intensity by these until this has been improved.

【0003】しかしながら上述した構成の従来のエレクトロルミネッセンス素子においては、発光強度は改良されてきてはいるが、耐久性に問題があり、まだ実用レベルの発光強度及び耐久性に達していなかった。 [0003] However, in the conventional electroluminescent device with the above-emission intensity has the been improved, there is a problem in durability, it has not yet reached the emission strength and durability for practical use. 従って、 Therefore,
より発光の強度が強くかつ高耐久性のエレクトロルミネッセンス素子の開発が望まれていた。 Development of more intensity of the emission is strong and highly durable electroluminescent device has been desired.

【0004】 [0004]

【発明の目的】本発明は上記の実情を鑑みてなされたもので、その目的とするところは、より発光強度が強くかつ高耐久性の実用レベルのエレクトロルミネッセンス素子を提供することにある。 SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and an object is to provide an electroluminescent device with more luminous intensity is strong and durable for practical use.

【0005】 [0005]

【問題点を解決する手段】本発明者らは上記の目的を達成するため鋭意努力の研究を重ねた結果、一対の対向電極とこれらによって挟持された複数の有機化合物層から構成されているエレクトロルミネッセンス素子において、下記一般式〔I〕で表される有機化合物を含有する層と、下記一般式〔II〕で表されるスチリル化合物を含有する層を、それぞれ少なくとも一層以上ずつ設けたことを特徴とする有機薄膜エレクトロルミネッセンス素子により、達成されることを見出した。 The present inventors have means for solving the problems] As a result of extensive research of intensive efforts to achieve the above object, electro that is composed of a plurality of organic compound layers sandwiched with the pair of opposed electrodes characterized in luminescence element, a layer containing an organic compound represented by the following general formula (I), that a layer containing a styryl compound represented by the following general formula [II], provided by at least one layer respectively the organic thin film electroluminescent element according to found to be achieved.

【0006】 [0006]

【化3】 [Formula 3]

【0007】前記一般式〔I〕の残基Zの(Z1)〜 [0007] (Z1) of the residue Z in the general formula [I] -
(Z4)中、R 1 〜R 11はそれぞれ独立に、水素原子、 (Z4) in, in R 1 to R 11 are each independently a hydrogen atom,
ハロゲン原子、置換若しくは無置換の続記5つの基;アルキル基、不飽和鎖式炭化水素から誘導された1価の基、複素環式基、アリール基、窒素2原子以上を含む基又はスチリル基、アニシル基、アミノ基、アルキルアミノ基、ジアルキルアミノ基、アルコキシ基、アルコキシカルボニル基、アミノカルボニル基、アリールオキシカルボニル基、カルボキシル基、アシル基、アリールオキシル基、アラルキル基、アシルアミノ基、アシルオキシル基、水酸基、シアノ基、ニトロ基、スルホ基、スルホニウム基を表し、R 1とR 2 、R 2とR 3 、R 3とR 4 、R 6 Halogen atom, a substituted or unsubstituted continued serial 5 groups: alkyl groups, unsaturated chain monovalent group derived from a hydrocarbon, a heterocyclic group, an aryl group, group, or styryl group containing at least nitrogen diatomic , anisyl group, an amino group, an alkylamino group, a dialkylamino group, an alkoxy group, an alkoxycarbonyl group, an amino group, an aryloxycarbonyl group, a carboxyl group, an acyl group, an aryloxy group, an aralkyl group, an acylamino group, acyloxy group , a hydroxyl group, a cyano group, a nitro group, a sulfo group, a sulfonium group, R 1 and R 2, R 2 and R 3, R 3 and R 4, R 6
とR 7 、R 7とR 8 、R 8とR 9 、R 9とR 10 、R 10とR 11は互いに結合して置換若しくは無置換の飽和または不飽和の環構造を形成していてもよい。 Even with R 7, R 7 and R 8, R 8 and R 9, R 9 and R 10, R 10 and R 11 are to form a ring structure of a substituted or unsubstituted, saturated or unsaturated bond with each other good.

【0008】また前記一般式〔I〕の残基Zの(Z5) [0008] the radical Z of the general formula [I] (Z5)
中Xは、置換若しくは無置換の複素環を表す。 Medium X represents a substituted or unsubstituted heterocyclic.

【0009】また上記一般式〔II〕中式中、R 12及びR [0009] Medium wherein the general formula [II], R 12 and R
13は、それぞれ独立に、水素原子、置換若しくは無置換の続記4つの基;アルキル基、複素環基、アリール基、 13, each independently, a hydrogen atom, a substituted or unsubstituted continued serial 4 groups: alkyl group, a heterocyclic group, an aryl group,
不飽和鎖式炭化水素から誘導された1価の基を表し、R It represents a monovalent group derived from an unsaturated chain hydrocarbon, R
12とR 13は互いに結合して置換若しくは無置換の飽和または不飽和の環構造を形成していてもよい。 12 and R 13 may form a saturated or unsaturated ring structure substituted or unsubstituted bound to each other.

【0010】R 14は、置換若しくは無置換の続記3つの基;アルキル基、アリール基、アルコキシ基、又は− [0010] R 14 represents a substituted or unsubstituted continued serial 3 groups: alkyl group, an aryl group, an alkoxy group, or -
{p(C 6 H 4 )}−CH=C{(−R 12 )(−R 13 )}を表し、R 12及びR 13は前記と同義である。 {P (C 6 H 4) } - CH = C {(- R 12) (- R 13)} represents, R 12 and R 13 are as defined above.

【0011】R 15は水素原子、置換若しくは無置換の続記3つの基;アルキル基、アリール基、アルコキシ基を表す。 [0011] R 15 is a hydrogen atom, a substituted or unsubstituted continued serial three groups; represents an alkyl group, an aryl group, an alkoxy group.

【0012】 [0012]

【発明の具体的構成】一般式〔I〕の残基(Z−1)〜 DETAILED OF THE INVENTION The residues of the general formula [I] (Z-1) ~
(Z−5)、および一般式〔II〕の表すハロゲン原子としては塩素原子、臭素原子、弗素原子、沃素原子;置換若しくは無置換のアルキル基としてはメチル基,エチル基,プロピル基,ブチル基,シクロヘキシル基などのアルキル基;置換若しくは無置換の不飽和鎖式炭化水素から誘導された1価の基としてはビニル基,1-プロペニル基、プロピル基,アリル基,イソプロペニル基,1-ブテニル基,2-ブテニル基,2-ペンテニル基,エチニル基などの不飽和鎖式炭化水素から誘導された1価の基;置換若しくは無置換の複素環式基としてはピペリジル基,ピペリジノ基,ピローリル基,フリル基,チェニル基,イミダゾリル基,ピラゾリル基,トリアゾリル基,ピリジル基,チアゾリル基,ピリダジニル基,ピリドンよりなる1価の基,モルホリ (Z-5), and examples of the halogen atom represented by the general formula [II] a chlorine atom, a bromine atom, a fluorine atom, an iodine atom; a substituted or unsubstituted Examples of the alkyl group a methyl group, an ethyl group, a propyl group, a butyl group , alkyl groups such as a cyclohexyl group; a substituted or unsubstituted unsaturated chain vinyl group as a monovalent group derived from a hydrocarbon, a 1-propenyl group, a propyl group, an allyl group, isopropenyl group, 1-butenyl group, 2-butenyl, 2-pentenyl group, a monovalent group derived from an unsaturated chain hydrocarbon such as ethynyl group; a substituted or unsubstituted piperidyl group as the heterocyclic group, a piperidino group, a pyrrolyl group , furyl group, thienyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a pyridyl group, a thiazolyl group, a pyridazinyl group, a monovalent group formed from pyridone, Moruhori ニル基,モルホニリノ基,オキサゾリル基,イソオキサゾリル基,イソチアゾリル基,ピリミジニル基,ピラジニル基,ピラニル基,ベンゾイミダゾリル基,ベンゾチアゾリル基,ベンゾオキサゾリル基,キノリル基などの複素環式基;置換若しくは無置換のアリール基としてはフェニル基,ナフチル基,アントニル基,キシリル基,ビフェニル基,フェナントリル基などのアリール基;置換若しくは無置換の窒素2原子以上を含む基としてはアゾ基,フェニラゾ基,ナフチラゾ基,ヒドラニゾ基,ヒドラゾ基,アゾキシ基,アジド基,ジアゾアミノ基,アミディノ基,ウレイレン基,グアニディノ基などの窒素2原子以上を含む基;アルコキシル基としてはメトキシル基,エトキシル基,プロポキシル基,ブトキシル基,ペンチルオキシル Group, Moruhonirino group, oxazolyl group, isoxazolyl group, isothiazolyl group, pyrimidinyl group, pyrazinyl group, pyranyl group, benzimidazolyl group, benzothiazolyl group, benzoxazolyl group, a quinolyl group heterocyclic group; a substituted or unsubstituted phenyl group as the aryl group, a naphthyl group, Antoniru group, a xylyl group, a biphenyl group, an aryl group and phenanthryl group; Examples of the group containing more than substituted or unsubstituted nitrogen 2 atoms of the azo group, Fenirazo group, Nafuchirazo group, Hidoranizo group, hydrazo group, azoxy group, azido group, diazoamino group, Amidino group, ureylene group, a nitrogen radical containing two or more atoms, such as Guanidino groups; the alkoxyl group methoxyl group, ethoxyl group, propoxyl group, butoxyl group, pentyl oxyl ,ヘキシルオキシル基などのアルコキシル基;アルコキシカルボニル基としてはメトキシカルボニル基,エトキシカルボニル基,ブトキシカルボニル基などのアルコキシカルボニル基;アミノカルボニル基としてはアニリノカルボニル基,ジメチルアミノカルボニル基,ラルバモイル基,アラニル基などのアミノカルボニル基;アリールオキシカルボニル基としてはナフチルオキシカルボニル基,キシリルオキシカルボニル基,フェノキシカルボニル基などのアリールオキシカルボニル基;アシル基としてはホルミル基,アセチル基,プロピオニル基,ブチリル基,パレリル基,オアルミトイル基,ステアロイル基,オレオイル基,ベンゾイル基,トリオイル基,サリチロイル基,シンナモイル基,ナフトイル基,フタロイル基,オキサリ An alkoxyl group such as hexyl oxyl group; alkoxycarbonyl as the group methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl alkoxycarbonyl groups such as groups; anilinocarbonyl group as an amino group, a dimethylaminocarbonyl group, Rarubamoiru group, alanyl naphthyloxycarbonyl group as aryloxycarbonyl group, xylyl group, phenoxycarbonyl aryloxycarbonyl group such group; aminocarbonyl group such groups as acyl groups formyl group, an acetyl group, a propionyl group, a butyryl group, Pareriru group, Oarumitoiru group, stearoyl group, oleoyl group, a benzoyl group, Torioiru group, salicyloyl group, cinnamoyl group, naphthoyl group, phthaloyl group, oxalyl 基,マロニル基,スクシニル基,フロイル基などのアシル基;アリールオキシル基としてはフェノキシ基,トリルオキシ基などのアリールオキシル基;アラルキル基としてはベンジル基,フェネチル基などのアラルキル基;アシルアミノ基としてはアセチルアミノ基,プロピオニルアミノ基,ブチリルアミノ基などのアシルアミノ基;アシルオキシル基としてはアセチルオキシ基, Acetyl as acylamino group; Aryloxy as Le phenoxy group, aryloxy group such as tolyloxy; benzyl group as the aralkyl group, an aralkyl group such as a phenethyl group group, malonyl group, succinyl group, an acyl group such as furoyl acyloxyl the group acetyloxy group; an amino group, propionylamino group, an acylamino group such as butyrylamino group
プロピオニルオキシ基,ブチリルオキシ基などのアシルオキシル基である。 Propionyloxy group, an acyloxy group such as butyryloxy group.

【0013】前記の置換基とは、水素原子、ハロゲン原子、メチル基,エチル基,プロピル基,ブチル基,シクロヘキシル基などのアルキル基、ビニル基,1-プロペニル基,アリル基,イソプロペニル基,1-ブテニル基,2- [0013] The the substituent, a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, an alkyl group such as a cyclohexyl group, a vinyl group, 1-propenyl group, allyl group, isopropenyl group, 1-butenyl group, 2-
ブテニル基,2-ペンテニル基,エチニル基などの不飽和鎖式炭化水素から誘導された1価の基、ピペリジル基, Butenyl, 2-pentenyl group, a monovalent group derived from an unsaturated chain hydrocarbon such as ethynyl group, piperidyl group,
ピペリジノ基,ピローリル基,フリル基,チェニル基, Piperidino group, a pyrrolyl group, a furyl group, a thienyl group,
イミダゾリル基,ピラゾリル基,トリアゾリル基,ピリジル基,チアゾリル基,ピリダジニル基,ピリドンよりなる1価の基,モルホリニル基,モルホリニノ基,オキサゾリル基,イソオキサゾリル基,イソチアゾリル基, Imidazolyl group, a pyrazolyl group, a triazolyl group, a pyridyl group, a thiazolyl group, a pyridazinyl group, a monovalent group formed from pyridone, morpholinyl group, Moruhorinino group, oxazolyl group, isoxazolyl group, isothiazolyl group,
ピリミジニル基,ピラジニル基,ピラニル基,ベンゾイミダゾリル基,ベンゾチアゾリル基,ベンゾオキサゾリル基,キノリル基などの複素環式基、フェニル基,ナフチル基,アントニル基,キシリル基,ビフェニル基,フェナントリル基などのアリール基、アゾ基、フェニラゾ基,ナフチラゾ基,ヒドラニゾ基,ヒドラゾ基,アゾキシ基,アジド基,ジアゾアミノ基,アミディノ基,ウレイレン基,グアニディノ基などの窒素2原子以上を含む基、スチリル基、アニシル基、アミノ基、アルキルアミノ基、ジアルキルアミノ基、メトキシル基,エトキシル基,プロポキシル基,ブトキシル基,ペンチルオキシル基,ヘキシルオキシル基などのアルコキシ基、メトキシカルボニル基,エトキシカルボニル基,ブトキシカルボニル基などのアル Pyrimidinyl group, pyrazinyl group, pyranyl group, benzimidazolyl group, benzothiazolyl group, benzoxazolyl group, a heterocyclic group such as quinolyl group, a phenyl group, a naphthyl group, Antoniru group, a xylyl group, a biphenyl group, an aryl such as phenanthryl group group, an azo group, Fenirazo group, Nafuchirazo group, Hidoranizo group, hydrazo group, azoxy group, azido group, diazoamino group, Amidino group, ureylene group, group containing at least nitrogen 2 atoms such as Guanidino group, a styryl group, an anisyl group, amino group, an alkylamino group, a dialkylamino group, methoxyl group, ethoxyl group, propoxyl group, butoxyl group, Penchiruokishiru group, an alkoxy group such as hexyloxy group, a methoxycarbonyl group, an ethoxycarbonyl group, Al, such as butoxycarbonyl group キシカルボニル基、アニリノカルボニル基,ジメチルアミノカルボニル基,ラルバモイル基,アラニル基などのアミノカルボニル基、ナフチルオキシカルボニル基,キシリルオキシカルボニル基,フェノキシカルボニル基などのアリールオキシカルボニル基、カルボキシル基、ホルミル基,アセチル基,プロピオニル基,ブチリル基,パレリル基,オアルミトイル基,ステアロイル基,オレオイル基,ベンゾイル基,トリオイル基,サリチロイル基,シンナモイル基,ナフトイル基,フタロイル基,オキサリル基,マロニル基,スクシニル基,フロイル基などのアシル基、フェノキシ基,トリルオキシ基などのアリールオキシ基、ベンジル基,フェネチル基などのアラルキル基、アセチルアミノ基,プロピオニルアミノ基,ブチリルアミノ Alkoxycarbonyl group, anilino group, dimethylamino group, Rarubamoiru group, aminocarbonyl group, such as alanyl group, naphthyloxycarbonyl group, xylyl group, an aryloxycarbonyl group such as phenoxycarbonyl group, a carboxyl group, a formyl group, an acetyl group, a propionyl group, a butyryl group, Pareriru group, Oarumitoiru group, stearoyl group, oleoyl group, a benzoyl group, Torioiru group, salicyloyl group, cinnamoyl group, naphthoyl group, phthaloyl group, oxalyl group, malonyl group, succinyl group an acyl group such as a furoyl group, a phenoxy group, an aryloxy group such as tolyloxy group, a benzyl group, an aralkyl group such as a phenethyl group, acetylamino group, propionylamino group, butyrylamino などのアシルアミノ基、アセチルオキシ基,プロピオニルオキシ基,ブチリルオキシ基などのアシルオキシル基、水酸基、シアノ基、ニトロ基、スルホ基またはスルホニウム基を表す。 An acylamino group, an acetyloxy group, such as, propionyloxy group, acyloxy group such as butyryloxy group, a hydroxyl group, a cyano group, a nitro group, a sulfo group or a sulfonium group.

【0014】このような一般式〔I〕で表される有機化合物の具体例としては、次に示すものを挙げることができる。 [0014] Specific examples of the organic compound represented by the general formula [I] include those listed below.

【0015】 [0015]

【化4】 [Of 4]

【0016】 [0016]

【化5】 [Of 5]

【0017】 [0017]

【化6】 [Omitted]

【0018】 [0018]

【化7】 [Omitted]

【0019】 [0019]

【化8】 [Of 8]

【0020】 [0020]

【化9】 [Omitted]

【0021】 [0021]

【化10】 [Of 10]

【0022】 [0022]

【化11】 [Of 11]

【0023】 [0023]

【化12】 [Of 12]

【0024】 [0024]

【化13】 [Of 13]

【0025】 [0025]

【化14】 [Of 14]

【0026】 [0026]

【化15】 [Of 15]

【0027】 [0027]

【化16】 [Of 16]

【0028】 [0028]

【化17】 [Of 17]

【0029】 [0029]

【化18】 [Of 18]

【0030】 [0030]

【化19】 [Of 19]

【0031】 [0031]

【化20】 [Of 20]

【0032】 [0032]

【化21】 [Of 21]

【0033】 [0033]

【化22】 [Of 22]

【0034】 [0034]

【化23】 [Of 23]

【0035】 [0035]

【化24】 [Of 24]

【0036】 [0036]

【化25】 [Of 25]

【0037】次に一般式〔II〕で表されるスチリル化合物の具体例を示す。 The following specific examples of the styryl compound represented by the general formula [II].

【0038】 [0038]

【化26】 [Of 26]

【0039】 [0039]

【化27】 [Of 27]

【0040】 [0040]

【化28】 [Of 28]

【0041】 [0041]

【化29】 [Of 29]

【0042】 [0042]

【化30】 [Of 30]

【0043】 [0043]

【化31】 [Of 31]

【0044】 [0044]

【化32】 [Of 32]

【0045】 [0045]

【化33】 [Of 33]

【0046】 [0046]

【化34】 [Of 34]

【0047】 [0047]

【化35】 [Of 35]

【0048】 [0048]

【化36】 [Of 36]

【0049】 [0049]

【化37】 [Of 37]

【0050】 [0050]

【化38】 [Of 38]

【0051】 [0051]

【化39】 [Of 39]

【0052】これらはあくまでも、説明のために示した具体例であり本発明の請求の範囲を限定するものでは無い。 [0052] These last, be a specific example for illustrative purposes are not intended to limit the scope of the invention.

【0053】本発明一般式〔I〕で表せられる有機化合物は公知の方法(J.Chem.Soc,1957,4616等に記載されている。)で容易に合成することができる。 [0053] The organic compound to be represented in the present invention the general formula [I] can be easily synthesized by a known method (J.Chem.Soc, are described in 1957,4616, and the like.).

【0054】合成例1 掻混ぜ器と還流冷却器および滴下漏斗を取り付けた三つ口フラスコに、クロラニル(21g;mp287℃),無水マレイン酸(150g;mp55.5℃)およびペリレン(10g;mp280 [0054] three-necked flask fitted with a synthesis example 1 take-mix unit and a reflux condenser and a dropping funnel, chloranil (21g; mp287 ℃), maleic anhydride (150g; mp55.5 ℃) and perylene (10 g; MP280
℃)十分粉砕混合した物を入れ、加熱しながら弗点で10 ° C.) placed things were thoroughly pulverized and mixed, 10 dollars point while heating
分間掻混ぜた。 Minutes mixed the take. その後、滴下漏斗から温めたキシレン(200ml)を加え掻混ぜ1時間沸騰し、熱濾過した。 Then, boiling warm xylene (200ml) was added 掻混 ze 1 hour from the dropping funnel and filtered hot. 熱濾過で分離した赤茶色針状結晶をキシレンで洗い、さらにエーテルで十分に洗浄することにより赤茶色針状結晶を得た。 The reddish-brown needle crystals separated by hot filtration washed with xylene to give a red-brown needles by thoroughly washed with ether. 得られた赤茶色針状結晶を減圧昇華装置を使って300℃,10 -4 mmHgで4時間半昇華し、昇華残留物をさらに減圧昇華装置を使って400℃,10 -4 mmHgで6時間処理することにより、光沢のある赤茶色針状結晶(I−2 The resulting reddish-brown needle crystals with a vacuum sublimation apparatus 300 ° C., 10 at -4 mmHg sublimated 4.5 hours, 400 ° C. further using vacuum sublimation apparatus sublimation residue, 6 hours at 10 -4 mmHg by treating, shiny reddish-brown needle crystals (I-2
8)が得られた。 8) was obtained.

【0055】合成例2 合成例1により合成した(I−28)にo-フェニレンジアミンを非反応性溶媒,好ましくはN-メチルピロリドン、 [0055] Synthesis Example 2 was synthesized by Synthesis Example 1 (I-28) in o- phenylenediamine unreactive solvent, preferably N- methylpyrrolidone,
N,N-ジメチルホルムアミド等の非プロトン性溶媒;キノリン等の塩基性溶媒;o-ジクロルベンゼン等の塩素系溶剤の単独又は混合溶媒中、室温以上好ましくは150〜250 N, N-aprotic solvent such as dimethylformamide; basic solvent such as quinoline; alone or a mixed solvent of chlorinated solvents such as o- dichlorobenzene, above room temperature is preferably 150 to 250
℃の温度条件下で縮合反応させることにより(I−1) By condensation reaction at a temperature of ℃ (I-1)
合成することができる。 It can be synthesized.

【0056】 合成例3合成例1により合成した(I−28)に2,3-ジアミノナフタレンを非反応性溶媒,好ましくはN-メチルピロリドン、N,N-ジメチルホルムアミド等の非プロトン性溶媒;キノリン等の塩基性溶媒;o-ジクロルベンゼン等の塩素系溶剤の単独又は混合溶媒中、室温以上好ましくは150〜250℃の温度条件下で縮合反応させることにより(I−2)を合成することができる。 [0056] non-reactive solvent 2,3-diaminonaphthalene in the synthesis (I-28) by Synthesis Example 3 Synthesis Example 1, preferably N- methylpyrrolidone, N, aprotic solvent such as N- dimethylformamide; basic solvent such as quinoline; o-alone or a mixed solvent of chlorinated solvents dichlorobenzene or the like, above room temperature, preferably to synthesize (I-2) by condensation reaction at a temperature of 150 to 250 ° C. be able to.

【0057】合成例4 合成例1により合成した(I−28)にアニリンを非反応性溶媒,好ましくはN-メチルピロリドン、N,N-ジメチルホルムアミド等の非プロトン性溶媒;キノリン等の塩基性溶媒;o-ジクロルベンゼン等の塩素系溶剤の単独又は混合溶媒中、室温以上好ましくは150〜250℃の温度条件下で縮合反応させることにより(I−37)を合成することができる。 [0057] Non-reactive solvents aniline was synthesized by Synthesis Example 4 Synthesis Example 1 (I-28), preferably N- methylpyrrolidone, N, aprotic solvent such as N- dimethylformamide; basic like quinoline the solvent; o-alone or a mixed solvent of chlorinated solvents dichlorobenzene or the like, above room temperature, preferably capable of synthesizing (I-37) by condensation reaction at a temperature of 150 to 250 ° C..

【0058】合成例5 合成例1により合成した(I−28)に1,8-ジアミノナフタレンを非反応性溶媒,好ましくはN-メチルピロリドン、N,N-ジメチルホルムアミド等の非プロトン性溶媒; [0058] non-reactive solvent 1,8-diaminonaphthalene in the synthesis (I-28) by Synthesis Example 5 Synthesis Example 1, preferably N- methylpyrrolidone, N, aprotic solvent such as N- dimethylformamide;
キノリン等の塩基性溶媒;o-ジクロルベンゼン等の塩素系溶剤の単独又は混合溶媒中、室温以上好ましくは150 Basic solvent such as quinoline; alone or a mixed solvent of chlorinated solvents such as o- dichlorobenzene, above room temperature, preferably 150
〜250℃の温度条件下で縮合反応させることにより(I− By condensation reaction at a temperature of to 250 DEG ° C. (I-
95)を合成することができる。 It can be synthesized 95).

【0059】また本発明一般式〔II〕で表せられるスチリル化合物も公知の方法で容易に製造することができる。 [0059] also be easily manufactured at the present invention the general formula styryl compounds to be represented by [II] is also a known method.

【0060】一般式〔II〕で表せられるスチリル化合物は例えば下記一般式〔III〕で表される燐化合物と一般式〔IV〕で表されるジホルミル化合物とを反応させることにより得ることができる。 [0060] styryl compounds to be represented by the general formula [II] can be obtained by reacting the diformyl compound represented by, for example, phosphorus compounds of the general formula represented by the following general formula [III] [IV].

【0061】 [0061]

【化40】 [Of 40]

【0062】一般式〔III〕中、R 12 ,R 13は〔II〕と同意義、Xは−P + −(R 16 ) 3 Y−で表されるトリフェニルホスホニウム基、あるいはトリアルキルホスホニウム塩、または、−PO(OR 17 ) 2で表されるジアルキル亜燐酸塩基を示す。 [0062] In the general formula [III], R 12, R 13 are as defined as in [II], X is -P + - triphenylphosphonium group represented by (R 16) 3 Y- or trialkyl phosphonium salt, or show a dialkyl phosphorous acid base represented by -PO (oR 17) 2. 16はアルキル基、アリール基を表し、Y R 16 represents an alkyl group, an aryl group, Y
はハロゲンイオンを表し、R 17はアルキル基を表す。 It represents a halogen ion, R 17 represents an alkyl group.

【0063】一般式〔IV〕中、R 14 ,R 15は〔II〕と同意義である。 [0063] In the general formula [IV], R 14, R 15 are as defined as in [II].

【0064】一般式〔III〕で表される燐化合物は対応するハロメチル化合物とトリアリールホスフィンあるいはトリアルキルスルフィン、または亜燐酸トリアルキルとを直接あるいはトルエン、キシレン等の溶媒中で加熱することにより容易に製造することができる。 [0064] The phosphorus compound represented by the general formula [III] readily by heating the corresponding halomethyl compound and triarylphosphine or trialkyl sulfinic, or a phosphorous acid trialkyl directly or toluene, in a solvent such as xylene it can be produced in.

【0065】上記スチリル化合物の合成方法における反応溶媒としては不活性溶剤、例えば炭化水素類、アルコール類、エーテル類が良好で、メタノール、エタノール、イソプロパノール、ブタノール、2-メトキシエタノール、1,2-ジメトキシエタン、ビス(2-メトキシエチル)エーテル、ジオキサン、テトラヒドロフラン、トルエン、キシレン、ジメチルスルホキシド、N,N-ジメチルホルムアミド、N-メチルピロリドン、1,3-ジメチル-2- [0065] The inert solvent as a reaction solvent in the synthesis of styryl compounds, such as hydrocarbons, alcohols, ethers good, methanol, ethanol, isopropanol, butanol, 2-methoxyethanol, 1,2-dimethoxyethane ethane, bis (2-methoxyethyl) ether, dioxane, tetrahydrofuran, toluene, xylene, dimethyl sulfoxide, N, N- dimethylformamide, N- methylpyrrolidone, 1,3-dimethyl-2
イミダゾリジノンなどが挙げられる。 Such imidazolidinone. 中でも極性溶媒、 Among these polar solvents,
例えばN,N-ジメチルホルムアミド及びジメチルスルホキシドが好適である。 For example N, the N- dimethylformamide and dimethyl sulfoxide are preferred.

【0066】縮合剤として苛性ソーダ、苛性カリ、ナトリウムアミド水素化ナトリウム及びナトリウムメチラート、カリウム-t-ブトキシド等のアルコラートが用いられる。 [0066] sodium hydroxide as the condensing agent, potassium hydroxide, sodium amide sodium hydride and sodium methylate, alcoholates such as potassium -t- butoxide used. 反応温度は、使用する溶媒の縮合剤に対する安定性、縮合成分の反応性、縮合剤の反応性によって、約0 The reaction temperature is stable against condensing agent of the solvent used, condensation component reactive by reaction of the condensing agent, from about 0
℃〜約100℃まで広範囲に選択することができ、好ましくは10〜80℃である。 ° C. can be selected in a wide range up to about 100 ° C., preferably from 10 to 80 ° C..

【0067】合成例6 ベンジルホスホン酸ジエチル2.28g、トリフェニルアミン-4,4-ジカルボアルデヒド1.50gを1,2-ジメトキシエタン20mlに加え、これに50%水素化ナトリウム0.50gを加え、室温で3時間撹拌し反応させた。 [0067] Synthesis Example 6 Benzyl diethyl 2.28 g, was added triphenyl amine-4,4-carbaldehyde 1.50g of 1,2-dimethoxyethane 20 ml, this 50% sodium hydride 0.50g was added at room temperature in was stirred for 3 hours to react. この後約30分間加熱還流させた。 Thereafter was about 30 minutes heated to reflux. 室温まで冷却した後、反応混合物を水20 After cooling to room temperature, the reaction mixture was diluted with water 20
0mlに注ぎ、生成した沈殿物を濾取し、水洗、乾燥させ It poured into 0 ml, filtered off the precipitate formed, washing with water, dried
1.46g(収率65%)の粉末を得た。 To obtain a powder of 1.46 g (65% yield). 更にこの粉末を酢酸エチルとメタノールから再結晶し淡泊黄色の例示化合物(II−16)を得た。 Further, this powder was obtained of exemplified compound of recrystallized bland yellow ethyl acetate and methanol (II-16).

【0068】得られたスチリル化合物の融点は134〜137 [0068] The melting point of the resulting styryl compounds 134-137
℃であった。 It was ℃.

【0069】本発明の有機薄膜エレクトロルミネッセンス素子の構成には各種態様があるが、基本的には複数の有機化合物層および該層を挟んだ一対の対向電極から構成されており、具体的には、基板/陽極/正孔注入層/発光層/陰極(図1(1))、基板/陽極/発光層/電子注入層/陰極(図1(2))、基板/陽極/正孔注入層/発光層/電子注入層/陰極(図1(3))などが挙げられるが、本発明は必ずしもこの構成に限定されるものではなく、それぞれにおいて発光層,正孔注入層,電子注入層を複数層設けたり、またそれぞれにおいて正孔注入層/発光層,発光層/電子注入層,正孔注入層/発光層/電子注入層を繰返し積層した構成にしたり、発光層と電子注入層との間に電子注入材と発光材との混合層、正孔注入層と発 [0069] While the structure of the organic thin film electroluminescent device of the present invention there is various aspects, basically consists of a plurality of organic compound layers and a pair of opposing electrodes sandwiching the layer, specifically substrate / anode / hole injection layer / light emitting layer / cathode (FIG. 1 (1)), the substrate / anode / light emitting layer / electron injection layer / cathode (FIG. 1 (2)), the substrate / anode / hole injection layer / light emitting layer / electron injection layer / cathode (FIG. 1 (3)) and the like, the present invention is not necessarily limited to this configuration, the light emitting layer in each of a hole injection layer, an electron injection layer or a plurality layers, also a hole injection layer / light emitting layer in each light-emitting layer / electron injection layer, or the hole injection layer / light emitting layer / electron injection layer was repeatedly laminated structure, a light-emitting layer and an electron injection layer mixed layer of an electron injecting material and a light emitting material between a hole injection layer and the emitting 層との間に正孔注入材と発光材との混合層を設けたりまたそれぞれにおいて他の層を設けてもさしつかえない。 No problem be provided other layers in the mixed layer is provided or also each of the hole injecting material and a light emitting material between the layers.

【0070】発光層は蒸着法,スピンコート法,キャスト法などにより形成しその膜厚は10〜1000nmが好ましく、より好ましくは20〜150nmである。 [0070] The light emitting layer deposition, spin coating, its thickness was formed by a casting method is preferably 10 to 1000 nm, more preferably 20 to 150 nm. 正孔注入層は蒸着法,スピンコート法,キャスト法などにより形成しその膜厚は10〜1000nmが好ましく、より好ましくは40〜20 Hole injection layer deposition, spin coating, its thickness was formed by a casting method is preferably 10 to 1000 nm, more preferably 40 to 20
0nmである。 It is 0nm. 電子注入層は蒸着法,スピンコート法,キャスト法などにより形成しその膜厚は10〜1000nmが好ましく、より好ましくは30〜200nmである。 The electron injection layer deposition, spin coating, its thickness was formed by a casting method is preferably 10 to 1000 nm, more preferably 30 to 200 nm.

【0071】基板1は、ソーダガラス,無蛍光ガラス, [0071] The substrate 1, soda glass, non-fluorescent glass,
燐酸系ガラス,硼酸系ガラスなどのガラス板、石英、アクリル系樹脂,スチレン系樹脂,ポリカーボネート系樹脂,エポキシ系樹脂,ポリエチレン,ポリエステル,シリコーン系樹脂などのプラスチック板およびプラスチックフィルム、アルミナなどの金属板および金属ホイルなどが用いられる。 Phosphoric acid-based glass, glass plates, such as boric acid-based glass, quartz, acrylic resin, styrene resin, polycarbonate resin, epoxy resin, polyethylene, polyester, plastic plate and a plastic film such as a silicone resin, a metal plate such as alumina and a metal foil is used.

【0072】陽極2は4eVより大きい仕事関数を持つものが好ましく、炭素、アルミニウム、バナジウム、 [0072] The anode 2 is preferably one having a 4eV larger work function, carbon, aluminum, vanadium,
鉄、コバルト、ニッケル、クロム、銅、亜鉛、タングステン、銀、錫、白金、金などの金属およびこれらの合金、酸化亜鉛、酸化インジウム、ITO,NESA等の酸化錫もしくは酸化錫インジウム系等の複合化合物、沃化銅などの化合物、ZnO:Al、SnO 2 :Sbなどの酸化物と金属の混合物、更にはポリ(3-メチルチオフェン) 、ポリピロール、ポリアニリンなどの導電性ポリマーなどが用いられる。 Iron, cobalt, nickel, chromium, copper, zinc, tungsten, silver, tin, platinum, and alloys such as gold, zinc oxide, indium oxide, ITO, composite of tin oxide or tin oxide indium-based such as NESA compounds, compounds such as copper iodide, ZnO: Al, SnO 2: oxides and mixtures of metal such as Sb, more poly (3-methylthiophene), polypyrrole, a conductive polymer such as polyaniline is used. 膜厚は10〜1000nmが好ましく、 The film thickness is preferably 10~1000nm,
より好ましくは10〜200nmである。 More preferably 10~200nm.

【0073】陰極3は4eVより小さい仕事関数を持つものが好ましく、マグネシウム、カルシウム、ナトリウム、カリウム、チタニウム、インジウム、イットリウム、リチウム、ガドリニウム、イッテルビウム、ルテニウム、マンガン、アルミニウム、銀、錫、鉛などの金属及びこれらの合金、アルミニウム/酸化アルミニウム複合体などが用いられる。 [0073] cathode 3 is preferably one having a 4eV smaller work function, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, ytterbium, ruthenium, manganese, aluminum, silver, tin, such as lead metals and alloys, such as aluminum / aluminum oxide composite is used. 膜厚は10〜1000nmが好ましく、 The film thickness is preferably 10~1000nm,
より好ましくは10〜900nmである。 More preferably 10~900nm.

【0074】電極より光を取り出す場合は、陽極2、陰極3のうち少なくともどちらか一方は、透過率10%以上の透明又は半透明であり、陽極2のみが透過率10%以上の透明又は半透明である場合は基板1も透明又は半透明であることが好ましい。 [0074] When taking out the light from the electrode, the anode 2, the at least one of the cathode 3, a transmittance of 10% or more transparent or translucent, only the anode 2 is greater than or transmittance of 10% transparent or translucent it is preferred if the transparent substrate 1 is also transparent or translucent.

【0075】発光層4に用いられる発光物質の具体例としては、前記一般式により表せられる有機化合物以外にオキシノイド化合物(特開昭63-295695号,特開平2-155 [0075] Specific examples of the luminescent material used in the light-emitting layer 4, the general oxinoid compounds other than the organic compound to be represented by the formula (JP 63-295695, JP-A 2-155
95号,同2-66873号などに記載のもの)、ペリレン化合物(「Soluble Perylene Fluorescent Dyes with Photo 95 No., those described in such as Nos. 2-66873), perylene compounds ( "Soluble Perylene Fluorescent Dyes with Photo
stability,vol.115,P2927(1982)」,「Jpn.Journal ofA stability, vol.115, P2927 (1982) "," Jpn.Journal ofA
pplied Physics,vol.27,No2,L269(1988)」,「Bull.Che pplied Physics, vol.27, No2, L269 (1988) "," Bull.Che
m.Soc.Jpn.vol.25,L411(1952)」,欧州特許553,353A1 m.Soc.Jpn.vol.25, L411 (1952) ", the European patent 553,353A1
号,特開昭55-36849号,同57-51781号,特開平2-66873 JP, JP-A-55-36849, 57-51781 same issue, JP-A-2-66873
号,同2-196885号,同2-288188号,同3-791号などに記載のもの)、クマリン化合物(特開昭57-51781号,特開平2-66873号,同3-792などに記載のもの)、アザクマリン化合物(特開平3-792号などに記載のもの)、オキサゾール化合物(米国特許3,257,203号,特開平3-193763 No., the 2-196885 JP, said 2-288188 Patent, those described in such as JP same 3-791), coumarin compounds (JP-A-57-51781, JP-A-2-66873, etc. the 3-792 those described), Azakumarin compound (as described, for example, JP-a-3-792), oxazole compounds (U.S. Pat. No. 3,257,203, JP-a 3-193763
号,同3-162482号,同2-220396号などに記載のもの)、 JP, the 3-162482 issue, those described in, for example, Nos. 2-220396),
オキサジアゾール化合物(米国特許3,189,447号,特開平2-216791号などに記載のもの)、ペリノン化合物(特開平2-88689号,同2-289676号などに記載のもの)、ピロロピロール化合物(特開平2-296891号などに記載のもの)、ナフタレン化合物(特開昭57-51781号,特開平2-2 Oxadiazole compounds (U.S. Pat. No. 3,189,447, those described in such as JP-A-2-216791), perinone compound (JP-A-2-88689, those described in such as JP same 2-289676), pyrrolopyrrole compounds (JP No. including those described in JP 2-296891), naphthalene compounds (JP 57-51781, JP-2-2
55789号,同3-162485号などに記載のもの)、アントラセン化合物(特開昭56-46234号,同57-51781号,特開平 No. 55789, as described in such Nos. 3-162485), anthracene compounds (JP 56-46234, the 57-51781 JP, Hei
2-66873号,同3-162485号などに記載のもの)、フルオレン化合物(特開昭54-110837号,特開平3-162485号などに記載のもの)、フルオランテン化合物(特開平3-16 No. 2-66873, those described in such as JP same 3-162485) fluorene compound (JP 54-110837, etc. to those described JP-A-3-162485), fluoranthene compound (JP-3-16
2485号などに記載のもの)、テトラセン化合物(特開平 Such as described in No. 2485 ones), tetracene compound (JP
3-162485号などに記載のもの)、ピレン化合物(特開昭 Such as those described in JP 3-162485), pyrene compounds (JP
57-51781号,特開平3-162485号,同3-502333号などに記載のもの)、コロネン化合物(特開平3-162485号などに記載のもの)、キノロン化合物及びアザキノロン化合物(特開平3-162483号などに記載のもの)、ピラゾリン誘導体及びピラゾロン誘導体(米国特許3,180,729号,同 No. 57-51781, JP-A-3-162485, those described in such as JP same 3-502333), coronene compounds (those described in such as JP-A-3-162485), quinolone compounds and azaquinolone compound (JP-3- such as those described in JP 162 483), pyrazoline derivatives and pyrazolone derivatives (U.S. Pat. No. 3,180,729, the
4,278,746号,特開昭55-88064号,同55-88065号,同49- No. 4,278,746, JP-A-55-88064, 55-88065 same issue, the same 49-
105537号,同55-51086号,同56-80051号,同56-88141 No. 105,537, the same 55-51086 JP, same 56-80051 JP, same 56-88141
号,同57-45545号,同54-112637号,同55-74546号,特開平2-220394号,同3-162486号などに記載のもの)、ローダミン化合物(特開平2-66873号,同3-188189号などに記載のもの)、クリセン化合物(特開昭57-51781号, No., the 57-45545 JP, same 54-112637 JP, said 55-74546 Patent, JP-A-2-220394, those described in such as JP same 3-162486), rhodamine compounds (JP-A-2-66873, the such as those described in JP 3-188189), chrysene compound (JP-a-57-51781,
特開平3-502333号などに記載のもの)、フェナントレン化合物(特開昭57-51781号などに記載のもの)、シクロペンタジエン化合物(特開平2-289675号などに記載のもの)、スチルベン化合物(米国特許4,356,429号,特開昭57-51781号,同61-210363号,同61-228451号,同61-1 Those described in such as JP-A-3-502333), phenanthrene compounds (those described in such as JP-57-51781), cyclopentadiene compound (as described, for example, JP-A-2-289675), a stilbene compound ( US Pat. No. 4,356,429, JP-A-57-51781, 61-210363 same issue, same 61-228451 JP, the 61-1
4642号,同61-72255号,同62-47646号,同62-36674号, No. 4642, the same 61-72255 JP, same 62-47646 JP, same 62-36674 JP,
同62-10652号,同62-30255号,同60-934454号,同60-94 Same 62-10652 JP, same 62-30255 JP, same 60-934454 JP, the same 60-94
462号,同60-174749号,同60-175052号,同63-149652 462 No., same 60-174749 JP, same 60-175052 JP, same 63-149652
号,特開平1-173034号,同1-200262号,同1-245087号などに記載のもの)、ジフェニルキノン化合物(「Polyme No., JP-A-1-173034, the 1-200262 Patent, those described in such as JP same 1-245087), diphenyl quinone compounds ( "Polyme
r Preprints,Japan,vol.37,p681(1988)」,特開平3-152 r Preprints, Japan, vol.37, p681 (1988) ", JP-A-3-152
184号などに記載のもの)、スチリル化合物(特開平1-2 Ones) such as described in 184 No., styryl compounds (JP 1-2
45087号,同2-209988号,同2-222484号,同2-247278号などに記載のもの)、ブタジエン化合物(米国特許4,35 No. 45087, the 2-209988 Patent, the 2-222484 Patent, those described in such as Nos. 2-247278), butadiene compounds (U.S. Patent 4,35
6,429号,特開昭57-51781号などに記載のもの)、ジシアノメチレンピラン化合物(特開平2-66873号,同3-162 No. 6,429, such as those described in JP-A-57-51781), dicyanomethylenepyran compounds (JP-A-2-66873, the 3-162
481号などに記載のもの)、ジシアノメチレンチオピラン化合物(特開平2-66873号,同3-162481号などに記載のもの)、フルオレセイン化合物(特開平2-66873号などに記載のもの)、ピリリウム化合物(特開平2-66873 481 No. like to those described), dicyanomethylenethiopyran compound (JP-A-2-66873, those described in such as JP same 3-162481), fluorescein compound (such as those described JP-A-2-66873), pyrylium compounds (JP-2-66873
号などに記載のもの)、チアピリリウム化合物(特開平 No. those described in, etc.), thiapyrilium compounds (JP
2-66873号などに記載のもの)、セレナピリリウム化合物(特開平2-66873号などに記載のもの)、テルロピリリウム化合物(特開平2-66873号などに記載のもの)、 Such as those described in JP 2-66873), Serena pyrylium compounds (those described in such as JP-A-2-66873), telluropyrylium compound (such as those described JP-A-2-66873),
芳香族アルダジエン化合物(特開平2-220393号などに記載のもの)、オリゴフェニレン化合物(特開平3-162484 Aromatic Arudajien compounds (such as those described JP-A-2-220393), oligophenylene compound (JP 3-162484
号などに記載のもの)、チオキサンテン化合物(特開平 No. those described in, etc.), thioxanthene compounds (JP-A
3-177486号などに記載のもの)、アンスラセン化合物(特開平3-178942号などに記載のもの)、シアニン化合物(特開平2-66873号などに記載のもの)、アクリジン化合物(特開昭57-51781号などに記載のもの)、8-ヒドロキシキノリン化合物の金属鎖体(特開平2-8287号,同 Those described in such as JP 3-177486), anthracene compounds (those described in such as JP-A-3-178942), cyanine compounds (those described in such as JP-A-2-66873), acridine compounds (JP 57 such as those described in JP -51,781), 8 metal Kusaritai hydroxy quinoline compound (JP-a-2-8287, the
2-8290号などに記載のもの)、2,2′-ビピリジン化合物の金属鎖体(特開平2-8288号,同2-8289号などに記載のもの)、シッフ塩とIII族金属との鎖体(特開平1-29749 Those described in such as JP 2-8290), 2,2'-bipyridine compound metal Kusaritai (JP 2-8288, those described in such as JP same 2-8289), Schiff salt and group III metal and the Kusaritai (JP-A-1-29749
0号などに記載のもの)、オキシン金属鎖体(特開平3-1 No. 0 like those described), oxine metal Kusaritai (JP-3-1
76993号などに記載のもの)、希土類鎖体(特開平1-256 Such as those described in JP 76 993), rare earth Kusaritai (JP 1-256
584号,同1-282291号などに記載のもの)などの蛍光物質を使用することができる。 584 No., it is possible to use a fluorescent material, such as) such as those described in Nos. 1-282291.

【0076】これらの化合物の好ましい代表例として次に示す物が挙げられる。 [0076] The following ones as preferred representatives of these compounds.

【0077】 [0077]

【化41】 [Of 41]

【0078】 [0078]

【化42】 [Of 42]

【0079】 [0079]

【化43】 [Of 43]

【0080】 [0080]

【化44】 [Of 44]

【0081】 [0081]

【化45】 [Of 45]

【0082】 [0082]

【化46】 [Of 46]

【0083】 [0083]

【化47】 [Of 47]

【0084】 [0084]

【化48】 [Of 48]

【0085】 [0085]

【化49】 [Of 49]

【0086】 [0086]

【化50】 [Of 50]

【0087】 [0087]

【化51】 [Of 51]

【0088】 [0088]

【化52】 [Of 52]

【0089】 [0089]

【化53】 [Of 53]

【0090】 [0090]

【化54】 [Of 54]

【0091】上記代表例中、Rはそれぞれ独立に、水素原子、ハロゲン原子、置換若しくは無置換の続記5つの基;アルキル基、複素環式基、アリール基、不飽和鎖式炭化水素から誘導された1価の基、窒素2原子以上を含む基、又はスチリル基、アニシル基、アミノ基、アルキルアミノ基、ジアルキルアミノ基、アルコキシ基、アルコキシカルボニル基、アミノカルボニル基、アリールオキシカルボニル基、カルボキシル基、アシル基、アリールオキシル基、アラルキル基、アシルアミノ基、アシルオキシル基、水酸基、シアノ基、ニトロ基、スルホ基及びスルホニウム基を表し、X -はアニオンを、Yはカルコゲン原子を表す。 [0091] In the representative examples, R is each independently a hydrogen atom, a halogen atom, continued serial substituted or unsubstituted 5 groups: induction alkyl group, a heterocyclic group, an aryl group, an unsaturated chain hydrocarbon It has been a monovalent group, the nitrogen radical containing two or more atoms, or a styryl group, an anisyl group, an amino group, an alkylamino group, a dialkylamino group, an alkoxy group, an alkoxycarbonyl group, an amino group, an aryloxycarbonyl group, a carboxyl represents group, an acyl group, an aryloxy group, an aralkyl group, an acylamino group, acyloxy group, a hydroxyl group, a cyano group, a nitro group, a sulfo group and sulfonium group, X - is an anion, Y represents a chalcogen atom.

【0092】これらはあくまでも、説明のために示した具体例及び代表例であり本発明の請求の範囲を限定するものでは無い。 [0092] These last, be a specific example and representative examples for illustrative purposes are not intended to limit the scope of the invention.

【0093】正孔注入層5に用いられる正孔輸送能を有する正孔注入化合物の具体例としては、前記一般式により表せられる有機化合物以外にトリアゾール誘導体(米国特許3,112,197号などに記載のもの)、オキサジアゾール誘導体(米国特許3,189,447号などに記載のもの)、イミダゾール誘導体(特公昭37-16096号などに記載のもの)、ポリアリールアルカン誘導体(米国特許3, [0093] The hole Specific examples of injection layers hole injection compound having a hole transport property used for 5, (as described in U.S. Pat. No. 3,112,197) Formula triazole derivatives in addition to the organic compound to be represented by , oxadiazole derivatives (those described in U.S. Pat. No. 3,189,447), (such as those described JP-B-37-16096) imidazole derivative, a polyaryl alkane derivative (U.S. Patent 3,
615,402号,同3,820,989号,同3,542,544号,特公昭45- No. 615,402, the 3,820,989 Patent, the 3,542,544 Patent, JP-B-45-
555号,同51-10983号,特開昭51-93224号,同55-17105 555 No., same 51-10983, JP Nos. 51-93224, 55-17105 same
号,同56-4148号,同55-108667号,同56-36656号,同55 JP, the 56-4148 issue, same 55-108667 JP, same 56-36656 JP, the same 55
-156953号などに記載のもの)、ピラゾリン誘導体及びピラゾロン誘導体(米国特許3,180,729号,同4,278,746 Such as those described in JP -156953), pyrazoline derivatives and pyrazolone derivatives (U.S. Pat. No. 3,180,729, the 4,278,746
号,特開昭55-88064号,同55-88065号,同49-105537 JP, JP-A-55-88064, 55-88065 same issue, same 49-105537
号,同55-51086号,同56-80051号,同56-88141号,同57 Nos., The same 55-51086 JP, same 56-80051 JP, same 56-88141 JP, 57
-45545号,同54-112637号,同55-74546号などに記載のもの)、フェニレンジアミン誘導体(米国特許3,615,40 No. -45545, the 54-112637 JP, those described in such as Nos. 55-74546), phenylenediamine derivatives (U.S. Patent 3,615,40
4号,特公昭51-10105号,同46-3712号,同47-25336号, No. 4, JP-B-51-10105, 46-3712 same issue, same 47-25336 JP,
特開昭54-53435号,同54-110536号,同54-119925号などに記載のもの)、アリールアミン誘導体(米国特許3,56 JP 54-53435, the 54-110536 JP, those described in such as JP same 54-119925), arylamine derivatives (U.S. Patent 3,56
7,450号,同3,180,703号,同3,240,597号,同3,658,520 No. 7,450, the 3,180,703 Patent, the 3,240,597 Patent, the 3,658,520
号,同4,232,103号,同4,175,961号,同4,012,376号, No., 4,232,103 the same issue, the 4,175,961 Patent, the 4,012,376 Patent,
特公昭49-35702号,同39-27577号,特開昭55-144250 Japanese Patent Publication No. 49-35702, the same 39-27577, JP 55-144250
号,同56-223437号,西ドイツ特許1,110,518号などに記載のもの)、アミノ置換カルコン誘導体(米国特許3,52 No., the 56-223437 JP, those such as described in West German Patent No. 1,110,518), amino-substituted chalcone derivatives (U.S. Patent 3,52
6,501号などに記載のもの)、オキサゾール誘導体(米国特許3,257,203号などに記載のもの)、スチリルアントラセン誘導体(特開昭56-46234号などに記載のもの)、フルオレノン誘導体(特開昭54-110837号などに記載のもの)、ヒドラゾン誘導体(米国特許3,717,462 Those described in such as JP 6,501), such as those described in oxazole derivatives (U.S. Pat. No. 3,257,203), such as those described styryl anthracene derivatives (JP-56-46234), a fluorenone derivative (JP 54-110837 ones) such as described in JP, hydrazone derivatives (U.S. Patent 3,717,462
号,特開昭54-59143号,同55-52063号,同55-52064号, JP, JP-A-54-59143, 55-52063 same issue, same 55-52064 JP,
同55-46760号,同55-85495号,同57-148749号,特開平3 Same 55-46760 JP, same 55-85495 JP, same 57-148749 JP, JP-A-3
-136059号,同3-138654号などに記載のもの)、スチルベン誘導体(特開昭61-210363号,同61-228451号,同61 No. -136059, those described in such as JP same 3-138654), a stilbene derivative (JP 61-210363, the same 61-228451 JP, the 61
-14642号,同61-72255号,同62-47646号,同62-36674 No. -14642, same 61-72255 JP, same 62-47646 JP, same 62-36674
号,同62-10652号,同62-30255号,同60-934454号,同6 Nos., The same 62-10652 JP, same 62-30255 JP, same 60-934454 JP, the same 6
0-94462号,同60-174749号,同60-175052号,同63-1496 No. 0-94462, the same 60-174749 JP, same 60-175052 JP, same 63-1496
52,特開平1-173034号,同1-200262号などに記載のもの)、ポリフィリン化合物(米国特許3,935,031号,同 52, JP-A-1-173034, those described in such as JP same 1-200262), porphyrin compounds (U.S. Pat. No. 3,935,031, the
4,356,429号,特開昭63-295695号,特開平2-12795号などに記載のもの)、芳香族第三級アミン化合物及びスチリルアミン化合物(米国特許4,127,412号,特開昭53-27 No. 4,356,429, JP-63-295695, those described in such as JP-A-2-12795), aromatic tertiary amine compounds and styrylamine compounds (U.S. Pat. No. 4,127,412, JP-53-27
033号,同54-58445号,同54-149634号,同54-64299号, 033, the same 54-58445 JP, same 54-149634 JP, same 54-64299 JP,
同55-79450号,同55-144250号,同56-119132号,同61-2 Same 55-79450 JP, same 55-144250 JP, same 56-119132 JP, the 61-2
95558号,同61-98353号,同63-295695号,特開平1-2433 No. 95558, the same 61-98353 JP, same 63-295695 JP, JP-A-1-2433
93号,同3-111485号などに記載のもの)、ブタジエン化合物(特開平3-111484号などに記載のもの)、ポリスチレン誘導体(特開平3-95291号などに記載のもの)、ヒドラゾン誘導体(特開平3-137187号などに記載のもの)、トリフェニルメタン誘導体、テトラフェニルベンジン誘導体(特開平3-54289号などに記載の化合物)などを使用することができるが、特に好ましくは、ポリフィリン化合物、芳香族第三級アミン化合物及びスチリルアミン化合物である。 93 No., those described in such as JP same 3-111485), butadiene compounds (as described, for example, JP-A-3-111484), those described in such as JP polystyrene derivatives (JP-A-3-95291), hydrazone derivatives ( those described in such as JP-a-3-137187), a triphenylmethane derivative, compounds described, for example, tetraphenyl benzene derivatives (JP-a-3-54289) may be used, such as, particularly preferably, porphyrin compounds , aromatic tertiary amine compounds and styrylamine compounds. これらの化合物の代表例として、 Representative examples of these compounds,
次に示すものが挙げられる。 Those shown below can be mentioned.

【0094】 [0094]

【化55】 [Of 55]

【0095】 [0095]

【化56】 [Of 56]

【0096】 [0096]

【化57】 [Of 57]

【0097】 [0097]

【化58】 [Of 58]

【0098】 [0098]

【化59】 [Of 59]

【0099】 [0099]

【化60】 [Of 60]

【0100】 [0100]

【化61】 [Of 61]

【0101】 [0101]

【化62】 [Of 62]

【0102】 [0102]

【化63】 [Of 63]

【0103】上記代表例中、Rはそれぞれ独立に、水素原子、ハロゲン原子、置換若しくは無置換の続記5つの基;アルキル基、複素環式基、アリール基、不飽和鎖式炭化水素から誘導された1価の基、窒素2原子以上を含む基、又はスチリル基、アニシル基、アミノ基、アルキルアミノ基、ジアルキルアミノ基、アルコキシ基、アルコキシカルボニル基、アミノカルボニル基、アリールオキシカルボニル基、カルボキシル基、アシル基、アリールオキシル基、アラルキル基、アシルアミノ基、アシルオキシル基、水酸基、シアノ基、ニトロ基、スルホ基及びスルホニウム基を表し、nは1以上の整数を表し、またMは金属原子を表す。 [0103] In the representative examples, R is each independently a hydrogen atom, a halogen atom, continued serial substituted or unsubstituted 5 groups: induction alkyl group, a heterocyclic group, an aryl group, an unsaturated chain hydrocarbon It has been a monovalent group, the nitrogen radical containing two or more atoms, or a styryl group, an anisyl group, an amino group, an alkylamino group, a dialkylamino group, an alkoxy group, an alkoxycarbonyl group, an amino group, an aryloxycarbonyl group, a carboxyl group, an acyl group, an aryloxy group, an aralkyl group, an acylamino group, acyloxy group, a hydroxyl group, a cyano group, a nitro group, a sulfo group and sulfonium group, n represents an integer of 1 or more, and M a metal atom represent.

【0104】これらはあくまでも、説明のために示した具体例及び代表例であり本発明の請求の範囲を限定するものでは無い。 [0104] These last, be a specific example and representative examples for illustrative purposes are not intended to limit the scope of the invention.

【0105】電子注入層6に用いられる電子輸送能を有する電子注入化合物の具体例としては、前記一般式により表せられる有機化合物以外にニトロ置換フルオレノン誘導体チオピランジオキサイド誘導体、ジフェキノン誘導体(「Polymer Preprints、Japan,vol.37,No3,P681, [0105] Specific examples of the electron injecting compound having an electron transport property used for the electron injection layer 6, the general formula nitro-substituted fluorenone derivatives thiopyran dioxide derivative in addition to an organic compound which is represented by, Jifekinon derivative ( "Polymer Preprints , Japan, vol.37, No3, P681,
(1988)」,特開平3-152184号などに記載のもの)、ペリレンテトラカルボキシル誘導体(「Jpn.Journal of App (1988) ", etc. to those described JP-A-3-152184), perylene tetracarboxylic derivatives (" Jpn.Journal of App
lied Physics,vol.27,No2,L269(1988)」「Bull.Chem.So lied Physics, vol.27, No2, L269 (1988), "" Bull.Chem.So
c.Jpn.,vol.25,L411(1952)」などに記載のもの)アントラキノジメタン誘導体(特開昭57-149259号,同58-5545 c.Jpn., vol.25, L411 (1952) "as described in, etc.) anthraquinodimethane derivatives (JP-57-149259, the 58-5545
0号,同61-225151号,同61-133750号,同63-104061号などに記載のもの)、フレオレニリデンメタン誘導体(特開昭60-69657号,同61-143764号,同61-148159号などに記載のもの)、アントロン誘導体(特開昭61-225151 No. 0, the 61-225151 JP, same 61-133750 JP, those described in such as JP same 63-104061), deflection distyrylpyrazine derivatives (JP-60-69657, the 61-143764 JP, the 61- such as those described in JP 148 159), anthrone derivatives (JP 61-225151
号,同61-233750号などに記載のもの)、オキサジアゾール誘導体(特開平3-79692号などに記載のもの)、ペリノン誘導体(特開平2-289676号などに記載のもの)、 No., those described in such as JP same 61-233750), those described in such as oxadiazole derivatives (JP-A-3-79692), those described in such as JP perinone derivatives (JP-A-2-289676),
キノリン錯体誘導体などの化合物を使用することができる。 It may be used compounds such as quinoline complex derivatives. これらの化合物の代表例として次に示すものが挙げられる。 Those shown below as a representative example of these compounds.

【0106】 [0106]

【化64】 [Of 64]

【0107】 [0107]

【化65】 [Of 65]

【0108】 [0108]

【化66】 [Of 66]

【0109】 [0109]

【化67】 [Of 67]

【0110】上記代表例中、Rはそれぞれ独立に、水素原子、ハロゲン原子、置換基を有する若しくは有しないアルキル基、置換基を有する若しくは有しない複素環式基、置換基を有する若しくは有しないアリール基、置換基を有する若しくは有しない不飽和鎖式炭化水素から誘導された1価の基、置換基を有する若しくは有しない窒素2原子以上を含む基、スチリル基、アニシル基、アミノ基、アルキルアミノ基、ジアルキルアミノ基、アルコキシ基、アルコキシカルボニル基、アミノカルボニル基、アリールオキシカルボニル基、カルボキシル基、アシル基、アリールオキシル基、アラルキル基、アシルアミノ基、アシルオキシル基、水酸基、シアノ基、ニトロ基、スルホ基及びスルホニウム基を表し、またMは金属原子を表す。 [0110] In the representative examples, R is each independently a hydrogen atom, a halogen atom, or without an alkyl group having a substituent, or without heterocyclic group having a substituent, or without aryl having a substituent group, a monovalent group derived from or without unsaturated chain hydrocarbon having a substituent, a group containing a more or without nitrogen 2 atom having a substituent group, a styryl group, an anisyl group, an amino group, an alkylamino group, a dialkylamino group, an alkoxy group, an alkoxycarbonyl group, an amino group, an aryloxycarbonyl group, a carboxyl group, an acyl group, an aryloxy group, an aralkyl group, an acylamino group, acyloxy group, a hydroxyl group, a cyano group, a nitro group, It represents a sulfo group and sulfonium group, and M represents a metal atom.

【0111】これらはあくまでも、説明のために示した具体例及び代表例であり本発明の請求の範囲を限定するものでは無い。 [0111] These last, be a specific example and representative examples for illustrative purposes are not intended to limit the scope of the invention.

【0112】 [0112]

【実施例】次に実施例によって本発明を具体的に説明する。 EXAMPLES Next will be specifically described by way of examples the invention.

【0113】実施例1 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0113] After the substrate (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) was 150nm deposited ITO on glass as Example 1 anode was patterned into a desired shape, the grinding with water in an alumina abrasive went. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0114】つぎにこの例示化合物(II−72)スチリル化合物をタングステンボード(日本バックスメタル株式会社製SF208)に入れ、8.0×10 -7 Torrの真空条件下で [0114] Next, this exemplary compound (II-72) styryl compound was placed in a tungsten board (Japan Bucks made of metal, Ltd. SF208), under a vacuum condition of 8.0 × 10 -7 Torr
0.2nm/secの成膜速度で真空蒸着し81nmの正孔注入層を形成した。 To form a hole injection layer by vacuum deposition 81nm at a deposition rate of 0.2 nm / sec.

【0115】次いで、真空条件を破ることなく化合物(I−1)をモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で63nmの発光層を積層蒸着した。 [0115] Next, the compound without breaking the vacuum conditions (I-1) put in a molybdenum boat (Japan Bucks made of metal, Ltd. SS-1-9), 0.2nm under vacuum conditions of 8.0 × 10 -7 Torr / It was laminated deposited light emitting layer of 63nm in sec deposition rate.

【0116】さらにこの上に真空条件を破ることなくM [0116] Furthermore, without breaking the vacuum conditions on the M
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰極を形成した。 g: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition to form a cathode.

【0117】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し17V直流電圧の印加によって、最大輝度63.9cd/m 2の発行が得られた。 [0117] By the application of connecting an external power supply 17V DC to the way the organic thin film EL element obtained in the issuance of the maximum luminance 63.9cd / m 2 was obtained. また温度23℃乾燥窒素ガス雰囲気下で17V直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は1589時間であった。 Also was subjected to a continuous lighting by 17V DC voltage in an atmosphere temperature of 23 ° C. dry nitrogen gas, the time for half of the luminance was 1589 hours.

【0118】実施例2 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0118] After patterning the substrate (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) was 150nm deposited ITO on glass as Example 2 anode into the desired shape, the grinding with water in an alumina abrasive went. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0119】つぎにこの基板に例示化合物(II−19)スチリル化合物をタングステンボート(日本バックスメタル株式会社製SF208)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で真空蒸着し79nmの正孔注入層を形成した。 [0119] then placed in the exemplary compound to the substrate (II-19) tungsten boat styryl compound (Japan Bucks made of metal, Ltd. SF208), the formation of 8.0 × 10 -7 Torr 0.2nm / sec under vacuum conditions of was vacuum deposited at a rate to form a hole injection layer of 79 nm.

【0120】次いで、真空条件を破ることなく化合物(I−1)をモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で64nmの発光層を積層蒸着した。 [0120] Next, the compound without breaking the vacuum conditions (I-1) put in a molybdenum boat (Japan Bucks made of metal, Ltd. SS-1-9), 0.2nm under vacuum conditions of 8.0 × 10 -7 Torr / It was laminated deposited light emitting layer of 64nm in sec deposition rate.

【0121】さらにこの上に真空条件下を破ることなくMg:Ag(10:1原子比合金)を500nm真空蒸着し、 [0121] Further without breaking the vacuum conditions on the Mg: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition,
陰極を形成した。 To form a cathode.

【0122】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し18V直流電圧の印加によって、最大輝度58.0cd/m 2の発光が得られた。 [0122] By the application of connecting an external power supply 18V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 58.0cd / m 2 was obtained.

【0123】また温度23℃乾燥窒素ガス雰囲気下で18V [0123] In addition 18V in an atmosphere temperature of 23 ℃ dry nitrogen gas
直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は1432時間であった。 Was subjected to a continuous lighting by the DC voltage application, the time to half brightness was 1432 hours.

【0124】実施例3 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0124] After the substrate (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) was 150nm deposited ITO on glass as Example 3 anode was patterned into a desired shape, the grinding with water in an alumina abrasive went. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0125】つぎにこの基板に化合物(II−48)スチリル化合物をタングステンボート(日本バックスメタル株式会社製SF208)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で真空蒸着し80nmの正孔注入層を形成した。 [0125] Next, the film formation rate of the substrate to the compound (II-48) styryl compound was placed in a tungsten boat (Japan Bucks made of metal, Ltd. SF208), under a vacuum condition of 8.0 × 10 -7 Torr 0.2nm / sec in to form a hole injection layer of 80nm by vacuum deposition.

【0126】次いで、真空条件を破ることなく化合物(I−1)をモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で62nmの発光層を積層蒸着した。 [0126] Next, the compound without breaking the vacuum conditions (I-1) put in a molybdenum boat (Japan Bucks made of metal, Ltd. SS-1-9), 0.2nm under vacuum conditions of 8.0 × 10 -7 Torr / It was laminated deposited light emitting layer of 62nm in sec deposition rate.

【0127】さらにこの上に真空条件を破ることなくM [0127] Furthermore, without breaking the vacuum conditions on the M
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰極を形成した。 g: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition to form a cathode.

【0128】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し19V直流電圧の印加によって、最大輝度57.7cd/m 2の発光が得られた。 [0128] By the application of connecting an external power supply 19V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 57.7cd / m 2 was obtained.

【0129】また温度23℃乾燥窒素ガス雰囲気下で19V [0129] In addition 19V in an atmosphere temperature of 23 ℃ dry nitrogen gas
直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は1413時間であった。 Was subjected to a continuous lighting by the DC voltage application, the time to half brightness was 1413 hours.

【0130】実施例4 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0130] After the substrate (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) was 150nm deposited ITO on glass as Example 4 anode was patterned into a desired shape, the grinding with water in an alumina abrasive went. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0131】つぎにこの基板に化合物(II−91)スチリル化合物をタングステンボート(日本バックスメタル株式会社製SF208)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で真空蒸着し80nmの正孔注入層を形成した。 [0131] Next, the film formation rate of the substrate to the compound (II-91) styryl compound was placed in a tungsten boat (Japan Bucks made of metal, Ltd. SF208), under a vacuum condition of 8.0 × 10 -7 Torr 0.2nm / sec in to form a hole injection layer of 80nm by vacuum deposition.

【0132】次いで、真空条件を破ることなく化合物(I−1)をモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Toorの真空条件下で0.2nm/secの成膜速度で62nmの発光層を積層蒸着した。 [0132] Next, the compound without breaking the vacuum conditions (I-1) put in a molybdenum boat (Japan Bucks made of metal, Ltd. SS-1-9), 8.0 × 10 -7 0.2nm under vacuum conditions of Toor / It was laminated deposited light emitting layer of 62nm in sec deposition rate.

【0133】さらにこの上に真空条件を破ることなくM [0133] Furthermore, without breaking the vacuum conditions on the M
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰極を形成した。 g: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition to form a cathode.

【0134】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し19V直流電圧の印加によって、最大輝度57.6cd/m 2の発光が得られた。 [0134] By the application of connecting an external power supply 19V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 57.6cd / m 2 was obtained.

【0135】また温度23℃乾燥窒素ガス雰囲気下で19V [0135] In addition 19V in an atmosphere temperature of 23 ℃ dry nitrogen gas
直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は1487時間であった。 Was subjected to a continuous lighting by the DC voltage application, the time to half brightness was 1487 hours.

【0136】実施例5 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0136] After the substrate (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) was 150nm deposited ITO on glass as Example 5 anode was patterned into a desired shape, the grinding with water in an alumina abrasive went. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0137】つぎにこの基板に例示化合物(II−14)スチリル化合物をタングステンボート(日本バックスメタル株式会社製SF208)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で真空蒸着し80nmの正孔注入層を形成した。 [0137] then placed in the exemplary compound to the substrate (II-14) tungsten boat styryl compound (Japan Bucks made of metal, Ltd. SF208), the formation of 8.0 × 10 -7 Torr 0.2nm / sec under vacuum conditions of to form a hole injection layer of 80nm by vacuum deposition at a rate.

【0138】次いで、真空条件を破ることなく化合物(I−1)をモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で63nmの発光層を積層蒸着した。 [0138] Next, the compound without breaking the vacuum conditions (I-1) put in a molybdenum boat (Japan Bucks made of metal, Ltd. SS-1-9), 0.2nm under vacuum conditions of 8.0 × 10 -7 Torr / It was laminated deposited light emitting layer of 63nm in sec deposition rate.

【0139】さらにこの上に真空条件を破ることなくM [0139] Furthermore, without breaking the vacuum conditions on the M
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰極を形成した。 g: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition to form a cathode.

【0140】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し19V直流電圧の印加によって、最大輝度54.7cd/m 2の発光が得られた。 [0140] By the application of connecting an external power supply 19V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 54.7cd / m 2 was obtained.

【0141】また温度23℃乾燥窒素ガス雰囲気下で19V [0141] In addition 19V in an atmosphere temperature of 23 ℃ dry nitrogen gas
直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は1404時間であった。 Was subjected to a continuous lighting by the DC voltage application, the time to half brightness was 1404 hours.

【0142】実施例6 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0142] After the substrate (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) was 150nm deposited ITO on glass as Example 6 anode was patterned into a desired shape, the grinding with water in an alumina abrasive went. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0143】つぎにこの基板に例示化合物(II−84)スチリル化合物をタングステンボート(日本バックスメタル株式会社製SF208)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で真空蒸着し81nmの正孔注入層を形成した。 [0143] then placed in the exemplary compound to the substrate (II-84) tungsten boat styryl compound (Japan Bucks made of metal, Ltd. SF208), the formation of 8.0 × 10 -7 Torr 0.2nm / sec under vacuum conditions of was vacuum deposited at a rate to form a hole injection layer of 81 nm.

【0144】次いで、真空条件を破ることなく化合物(I−1)をモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で63nmの発光層を積層蒸着した。 [0144] Next, the compound without breaking the vacuum conditions (I-1) put in a molybdenum boat (Japan Bucks made of metal, Ltd. SS-1-9), 0.2nm under vacuum conditions of 8.0 × 10 -7 Torr / It was laminated deposited light emitting layer of 63nm in sec deposition rate.

【0145】さらにこの上に真空条件を破ることなくM [0145] Furthermore, without breaking the vacuum conditions on the M
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰極を形成した。 g: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition to form a cathode.

【0146】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し18V直流電圧の印加によって、最大輝度60.7cd/m 2の発光が得られた。 [0146] By the application of connecting an external power supply 18V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 60.7cd / m 2 was obtained.

【0147】また温度23℃乾燥窒素ガス雰囲気下で17V [0147] Also under temperature 23 ℃ a dry nitrogen gas atmosphere 17V
直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は1532時間であった。 Was subjected to a continuous lighting by the DC voltage application, the time to half brightness was 1532 hours.

【0148】実施例7 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0148] After the substrate (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) was 150nm deposited ITO on glass as Example 7 anode was patterned into a desired shape, the grinding with water in an alumina abrasive went. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0149】つぎにこの基板に例示化合物(II−72)スチリル化合物をタングステンボート(日本バックスメタル株式会社製SF208)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で真空蒸着し82nmの正孔注入層を形成した。 [0149] Then put the exemplified compounds on the substrate (II-72) a tungsten boat styryl compound (Japan Backs manufactured metal Ltd. SF208), deposition of 8.0 × 10 -7 Torr 0.2nm / sec under vacuum conditions of was vacuum deposited at a rate to form a hole injection layer of 82 nm.

【0150】次いで、真空条件を破ることなく化合物(I−1)をモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で62nmの発光層を積層蒸着した。 [0150] Next, the compound without breaking the vacuum conditions (I-1) put in a molybdenum boat (Japan Bucks made of metal, Ltd. SS-1-9), 0.2nm under vacuum conditions of 8.0 × 10 -7 Torr / It was laminated deposited light emitting layer of 62nm in sec deposition rate.

【0151】さらにこの上に真空条件を破ることなくM [0151] Furthermore, without breaking the vacuum conditions on the M
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰極を形成した。 g: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition to form a cathode.

【0152】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し18V直流電圧の印加によって、最大輝度55.1cd/m 2の発光が得られた。 [0152] By the application of connecting an external power supply 18V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 55.1cd / m 2 was obtained.

【0153】また温度23℃乾燥窒素ガス雰囲気下で18V [0153] In addition 18V in an atmosphere temperature of 23 ℃ dry nitrogen gas
直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は1529時間であった。 Was subjected to a continuous lighting by the DC voltage application, the time to half brightness was 1529 hours.

【0154】実施例8 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0154] After the substrate (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) was 150nm deposited ITO on glass as Example 8 anode was patterned into a desired shape, the grinding with water in an alumina abrasive went. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0155】つぎにこの基板に例示化合物(II−27)スチリル化合物をタングステンボート(日本バックスメタル株式会社製SF208)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で真空蒸着し81nmの正孔注入層を形成した。 [0155] then placed in the exemplary compound to the substrate (II-27) tungsten boat styryl compound (Japan Bucks made of metal, Ltd. SF208), the formation of 8.0 × 10 -7 Torr 0.2nm / sec under vacuum conditions of was vacuum deposited at a rate to form a hole injection layer of 81 nm.

【0156】次いで、真空条件を破ることなく化合物(I−28)をモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で63nmの発光層を積層蒸着した。 [0156] Next, the compound without breaking the vacuum conditions (I-28) put in a molybdenum boat (Japan Bucks made of metal, Ltd. SS-1-9), 0.2nm under vacuum conditions of 8.0 × 10 -7 Torr / It was laminated deposited light emitting layer of 63nm in sec deposition rate.

【0157】さらにこの上に真空条件を破ることなくM [0157] Furthermore, without breaking the vacuum conditions on the M
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰極を形成した。 g: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition to form a cathode.

【0158】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し22V直流電圧の印加によって、最大輝度48.3cd/m 2の発光が得られた。 [0158] By the application of connecting an external power supply 22V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 48.3cd / m 2 was obtained.

【0159】また温度23℃乾燥窒素ガス雰囲気下で22V [0159] Also under temperature 23 ℃ a dry nitrogen gas atmosphere 22V
直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は1652時間であった。 Was subjected to a continuous lighting by the DC voltage application, the time to half brightness was 1652 hours.

【0160】実施例9 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0160] After the substrate (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) was 150nm deposited ITO on glass as Example 9 an anode was patterned into a desired shape, the grinding with water in an alumina abrasive went. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0161】つぎにこの基板に例示化合物(II−72)スチリル化合物をタングステンボート(日本バックスメタル株式会社製SF208)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で真空蒸着し80nmの正孔注入層を形成した。 [0161] Then put the exemplified compounds on the substrate (II-72) a tungsten boat styryl compound (Japan Backs manufactured metal Ltd. SF208), deposition of 8.0 × 10 -7 Torr 0.2nm / sec under vacuum conditions of to form a hole injection layer of 80nm by vacuum deposition at a rate.

【0162】次いで、真空条件を破ることなく化合物(I−95)をモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で63nmの発光層を積層蒸着した。 [0162] Next, the compound without breaking the vacuum conditions (I-95) put in a molybdenum boat (Japan Bucks made of metal, Ltd. SS-1-9), 0.2nm under vacuum conditions of 8.0 × 10 -7 Torr / It was laminated deposited light emitting layer of 63nm in sec deposition rate.

【0163】さらにこの上に真空条件を破ることなくM [0163] Furthermore, without breaking the vacuum conditions on the M
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰極を形成した。 g: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition to form a cathode.

【0164】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し15V直流電圧の印加によって、最大輝度52.4cd/m 2の発光が得られた。 [0164] By the application of connecting an external power supply 15V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 52.4cd / m 2 was obtained.

【0165】また温度23℃乾燥窒素ガス雰囲気下で15V [0165] In addition 15V in an atmosphere temperature of 23 ℃ dry nitrogen gas
直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は1552時間であった。 Was subjected to a continuous lighting by the DC voltage application, the time to half brightness was 1552 hours.

【0166】実施例10 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0166] After the substrate (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) was 150nm deposited ITO on glass as Example 10 anode was patterned into a desired shape, the grinding with water in an alumina abrasive went. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0167】つぎにこの基板に例示化合物(II−72)をタングステンボート(日本バックスメタル株式会社製S [0167] Then exemplified compounds on the substrate (II-72) tungsten boat (S manufactured by Nippon Bucks Metal Co.
F208)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/se Put in F208), in a vacuum under the conditions of 8.0 × 10 -7 Torr 0.2nm / se
cの成膜速度で真空蒸着し80nmの正孔注入層を形成した。 To form a hole injection layer of 80nm by vacuum deposition at a c deposition rate.

【0168】次いで、真空条件を破ることなく化合物(I−96)をモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で62nmの発光層を積層蒸着した。 [0168] Next, the compound without breaking the vacuum conditions (I-96) put in a molybdenum boat (Japan Bucks made of metal, Ltd. SS-1-9), 0.2nm under vacuum conditions of 8.0 × 10 -7 Torr / It was laminated deposited light emitting layer of 62nm in sec deposition rate.

【0169】さらにこの上に真空条件を破ることなくM [0169] Furthermore, without breaking the vacuum conditions on the M
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰極を形成した。 g: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition to form a cathode.

【0170】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し19V直流電圧の印加によって、最大輝度50.8cd/m 2の発光が得られた。 [0170] By the application of connecting an external power supply 19V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 50.8cd / m 2 was obtained.

【0171】また温度23℃乾燥窒素ガス雰囲気下で19V [0171] In addition 19V in an atmosphere temperature of 23 ℃ dry nitrogen gas
直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は1529時間であった。 Was subjected to a continuous lighting by the DC voltage application, the time to half brightness was 1529 hours.

【0172】実施例11 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0172] After the substrate (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) was 150nm deposited ITO on glass as Example 11 anode was patterned into a desired shape, the grinding with water in an alumina abrasive went. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0173】つぎにこの基板に例示化合物(II−72)をタングステンボート(日本バックスメタル株式会社製S [0173] Then exemplified compounds on the substrate (II-72) tungsten boat (S manufactured by Nippon Bucks Metal Co.
F208)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/se Put in F208), in a vacuum under the conditions of 8.0 × 10 -7 Torr 0.2nm / se
cの成膜速度で真空蒸着し81nmの正孔注入層を形成した。 To form a hole injection layer by vacuum deposition 81nm in c deposition rate.

【0174】次いで、真空条件を破ることなく化合物(I−42)をモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で63nmの発光層を積層蒸着した。 [0174] Next, the compound without breaking the vacuum conditions (I-42) put in a molybdenum boat (Japan Bucks made of metal, Ltd. SS-1-9), 8.0 × 10 -7 Torr of 0.2nm under vacuum conditions / It was laminated deposited light emitting layer of 63nm in sec deposition rate.

【0175】さらにこの上に真空条件を破ることなくM [0175] Furthermore, without breaking the vacuum conditions on the M
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰極を形成した。 g: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition to form a cathode.

【0176】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し20V直流電圧の印加によって、最大輝度50.1cd/m 2の発光が得られた。 [0176] By the application of connecting an external power supply 20V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 50.1cd / m 2 was obtained.

【0177】また温度23℃乾燥窒素ガス雰囲気下で20V [0177] In addition 20V in an atmosphere temperature of 23 ℃ dry nitrogen gas
直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は1501時間であった。 Was subjected to a continuous lighting by the DC voltage application, the time to half brightness was 1501 hours.

【0178】比較例(1) 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0178] After the patterning comparative example (1) a substrate which the ITO was 150nm deposited on glass as an anode (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) into the desired shape, along with water in an alumina abrasive the polishing was carried out. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0179】つぎにこの基板に例示化合物(p−1); [0179] Then exemplified compounds on the substrate (p-1);
1,1-ビス(4-ジ-p-トリルアミノフェニル)シクロヘキサンをタングステンボート(日本バックスメタル株式会社製SF208)に入れ、8.0×10 -7 Torrの真空条件下で0. 1,1-bis (4-di -p- tolyl-aminophenyl) cyclohexane was placed in a tungsten boat (Japan Backs manufactured metal Ltd. SF208), 0 under a vacuum condition of 8.0 × 10 -7 Torr.
2nm/secの成膜速度で真空蒸着し80nmの正孔注入層を形成した。 To form a hole injection layer of 80nm by vacuum deposition at a deposition rate of 2 nm / sec.

【0180】次いで、真空条件を破ることなく下記化合物(L−1−1)トリス(8-ヒドロキシキノリン)アルミニウムをモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で64nmの発光層を積層蒸着した。 [0180] Next, put into the following compound without breaking the vacuum condition (L-1-1) tris (8-hydroxyquinoline) aluminum molybdenum boat (Japan Backs manufactured metal Ltd. SS-1-9), 8.0 × 10 It was laminated deposited light emitting layer of 64nm at a deposition rate of 0.2 nm / sec under vacuum conditions of -7 Torr.

【0181】 [0181]

【化68】 [Of 68]

【0182】さらにこの上に真空条件を破ることなくM [0182] Furthermore, without breaking the vacuum conditions on the M
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰極を形成した。 g: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition to form a cathode.

【0183】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し24V直流電圧の印加によって、最大輝度28.3cd/m 2の発光が得られた。 [0183] By the application of connecting an external power supply 24V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 28.3cd / m 2 was obtained.

【0184】また温度23℃乾燥窒素ガス雰囲気下で24V [0184] Further, the temperature 23 ℃ a dry nitrogen gas atmosphere 24V under
直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は630時間であった。 Was subjected to a continuous lighting by the DC voltage application, the time to half brightness was 630 hours.

【0185】比較例(2) 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0185] After the patterning comparative example (2) substrates which an ITO was 150nm deposited on glass as an anode (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) into the desired shape, along with water in an alumina abrasive the polishing was carried out. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0186】つぎにこの基板に例示化合物(II−72)スチリル化合物をタングステンボート(日本バックスメタル株式会社製SF208)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で真空蒸着し81nmの正孔注入層を形成した。 [0186] Then put the exemplified compounds on the substrate (II-72) a tungsten boat styryl compound (Japan Backs manufactured metal Ltd. SF208), deposition of 8.0 × 10 -7 Torr 0.2nm / sec under vacuum conditions of was vacuum deposited at a rate to form a hole injection layer of 81 nm.

【0187】次いで、真空条件を破ることなく化合物(L−1−1)トリス(8-ヒドロキシキノリン)アルミニウムをモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で64nmの発光層を積層蒸着した。 [0187] Then, compound without breaking the vacuum condition (L-1-1) tris (8-hydroxyquinoline) put aluminum to molybdenum boat (Japan Backs manufactured metal Ltd. SS-1-9), 8.0 × 10 - It was laminated deposited light emitting layer of 64nm at a deposition rate of 0.2 nm / sec under vacuum of 7 Torr.

【0188】さらにこの上に真空条件を破ることなくM [0188] Furthermore, without breaking the vacuum conditions on the M
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰極を形成した。 g: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition to form a cathode.

【0189】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し23V直流電圧の印加によって、最大輝度43.2cd/m 2の発光が得られた。 [0189] By the application of connecting an external power supply 23V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 43.2cd / m 2 was obtained.

【0190】また温度23℃乾燥窒素ガス雰囲気下で23V [0190] Also under temperature 23 ℃ a dry nitrogen gas atmosphere 23V
直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は932時間であった。 Was subjected to a continuous lighting by the DC voltage application, the time to half brightness was 932 hours.

【0191】比較例(3) 陽極としてガラス上にITOを150nm成膜した基板(日本板硝子株式会社製P110E-H-PS)を所望の形にパターニングを行った後、アルミナ研磨剤にて水とともに研磨を行った。 [0191] After the patterning comparative example (3) substrate and ITO was 150nm deposited on glass as an anode (manufactured by Nippon Sheet Glass Co., Ltd. P110E-H-PS) into the desired shape, along with water in an alumina abrasive the polishing was carried out. 水洗後、水超音波洗浄10分間2回、アセトン超音波洗浄10分間2回、イソプロピルアルコール超音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行った。 After washing with water, the water ultrasonic cleaning for 10 minutes twice, acetone ultrasonic cleaning for 10 minutes twice, performed twice isopropyl alcohol ultrasonic cleaning for 10 minutes, was dried with hot air at further 90 ° C..

【0192】つぎにこの基板に例示化合物(p−2)スチルベン誘導体をタングステンボート(日本バックスメタル株式会社製SF208)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で真空蒸着し79nmの正孔注入層を形成した。 [0192] Then put the exemplified compounds on the substrate (p-2) stilbene derivatives tungsten boat (Japan Backs manufactured metal Ltd. SF208), deposition of 8.0 × 10 -7 Torr 0.2nm / sec under vacuum conditions of was vacuum deposited at a rate to form a hole injection layer of 79 nm.

【0193】次いで、真空条件を破ることなく化合物(I−1)をモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で62nmの発光層を積層蒸着した。 [0193] Next, the compound without breaking the vacuum conditions (I-1) put in a molybdenum boat (Japan Bucks made of metal, Ltd. SS-1-9), 0.2nm under vacuum conditions of 8.0 × 10 -7 Torr / It was laminated deposited light emitting layer of 62nm in sec deposition rate.

【0194】さらにこの上に真空条件を破ることなくM [0194] Furthermore, without breaking the vacuum conditions on the M
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰極を形成した。 g: Ag (10: 1 atomic ratio alloy) was 500nm vacuum deposition to form a cathode.

【0195】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し20V直流電圧の印加によって、最大輝度44.1cd/m 2の発光が得られた。 [0195] By the application of connecting an external power supply 20V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 44.1cd / m 2 was obtained.

【0196】また温度23℃乾燥窒素ガス雰囲気下で20V [0196] In addition 20V in an atmosphere temperature of 23 ℃ dry nitrogen gas
直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は1240時間であった。 Was subjected to a continuous lighting by the DC voltage application, the time to half brightness was 1240 hours.

【0197】 [0197]

【発明の効果】本発明に係る特定の有機化合物を用いることにより、発光強度、耐久性において充分に実用に耐える有機薄膜エレクトロルミネッセンス素子が得られる。 By using a specific organic compound according to the present invention, the light emission intensity, an organic thin film electroluminescence device withstand sufficiently practical in durability is obtained.

【図面の簡単な説明】 BRIEF DESCRIPTION OF THE DRAWINGS

【図1】(1)〜(3)は本発明の態様例の有機薄膜エレクトロルミネッセンス素子の断面図である。 [1] (1) to (3) is a sectional view of an organic thin film electroluminescence device embodiment of the present invention.

【符号の説明】 DESCRIPTION OF SYMBOLS

1 基板 2 陽極 3 陰極 4 発光層 5 正孔注入層 6 電子注入層 1 substrate 2 anode 3 cathode 4 luminescent layer 5 hole injection layer 6 an electron injection layer

───────────────────────────────────────────────────── ────────────────────────────────────────────────── ───

【手続補正書】 [Procedure amendment]

【提出日】平成4年2月12日 [Filing date] 1992 February 12,

【手続補正1】 [Amendment 1]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0012 [Correction target item name] 0012

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0012】 [0012]

【発明の具体的構成】一般式〔I〕の残基( Z1 )〜 DETAILED OF THE INVENTION The residues of the general formula [I] (Z1) ~
Z5 )、および一般式〔II〕の表すハロゲン原子としては塩素原子、臭素原子、弗素原子、沃素原子などのハ (Z5), and examples of the halogen atom represented by the general formula [II] a chlorine atom, a bromine atom, a fluorine atom, c such iodine atoms
ロゲン原子 ;置換若しくは無置換のアルキル基としてはメチル基,エチル基,プロピル基,ブチル基,シクロヘキシル基などのアルキル基;置換若しくは無置換の不飽和鎖式炭化水素から誘導された1価の基としてはビニル基,1-プロペニル基,アリル基,イソプロペニル基,1- Androgenic atoms; substituted or The unsubstituted alkyl groups include methyl group, ethyl group, propyl group, butyl group, an alkyl group such as a cyclohexyl group; a substituted or unsubstituted monovalent radical derived from an unsaturated chain hydrocarbon vinyl group as, 1-propenyl, a Lil group, isopropenyl group, 1-
ブテニル基,2-ブテニル基,2-ペンテニル基,エチニル基などの不飽和鎖式炭化水素から誘導された1価の基; Butenyl, 2-butenyl, 2-pentenyl group, a monovalent group derived from an unsaturated chain hydrocarbon such as ethynyl group;
置換若しくは無置換の複素環式基としてはピペリジル基,ピペリジノ基,ピローリル基,フリル基,チェニル基,イミダゾリル基,ピラゾリル基,トリアゾリル基, A substituted or unsubstituted piperidyl group as the heterocyclic group, a piperidino group, a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group,
ピリジル基,チアゾリル基,ピリダジニル基,ピリドンよりなる1価の基,モルホリニル基,モルホリノ基,オキサゾリル基,イソオキサゾリル基,イソチアゾリル基,ピリミジニル基,ピラジニル基,ピラニル基,ベンゾイミダゾリル基,ベンゾチアゾリル基,ベンゾオキサゾリル基,キノリル基などの複素環式基;置換若しくは無置換のアリール基としてはフェニル基,ナフチル基, Pyridyl group, a thiazolyl group, a pyridazinyl group, a monovalent group formed from pyridone, morpholinyl group, morpholino group, oxazolyl group, isoxazolyl group, isothiazolyl group, pyrimidinyl group, pyrazinyl group, pyranyl group, benzimidazolyl group, benzothiazolyl group, oxazolyl group, a heterocyclic group such as quinolyl group; a substituted or unsubstituted Examples of the aryl group include a phenyl group, a naphthyl group,
アントニル基,キシリル基,ビフェニル基,フェナントリル基などのアリール基;置換若しくは無置換の窒素2 Antoniru group, a xylyl group, a biphenyl group, an aryl group and phenanthryl group; a substituted or unsubstituted nitrogen 2
原子以上を含む基としてはアゾ基,フェニラゾ基,ナフチラゾ基,ヒドラニゾ基,ヒドラゾ基,アゾキシ基,アジド基,ジアゾアミノ基,アミディノ基,ウレイレン基,グアニディノ基などの窒素2原子以上を含む基;アルコキシル基としてはメトキシル基,エトキシル基,プロポキシル基,ブトキシル基,ペンチルオキシル基,ヘキシルオキシル基などのアルコキシル基;アルコキシカルボニル基としてはメトキシカルボニル基,エトキシカルボニル基,ブトキシカルボニル基などのアルコキシカルボニル基;アミノカルボニル基としてはアニリノカルボニル基,ジメチルアミノカルボニル基,ラルバモイル基,アラニル基などのアミノカルボニル基;アリールオキシカルボニル基としてはナフチルオキシカルボニル基,キシリルオキシカ Azo group as the group including the above atoms, Fenirazo group, Nafuchirazo group, Hidoranizo group, hydrazo group, azoxy group, azido group, diazoamino group, Amidino group, ureylene group, group containing at least nitrogen 2 atoms such as Guanidino groups; alkoxylated methoxyl groups as group, ethoxyl group, propoxyl group, butoxyl group, Penchiruokishiru group, an alkoxyl group such as hexyl oxyl group; alkoxycarbonyl groups such as alkoxycarbonyl Examples of the carbonyl group-methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl group; the aminocarbonyl group anilinocarbonyl group, dimethylaminocarbonyl group, Rarubamoiru group, aminocarbonyl group, such as alanyl group; naphthyloxycarbonyl group as aryloxycarbonyl group, Kishiriruokishika ボニル基,フェノキシカルボニル基などのアリールオキシカルボニル基;アシル基としてはホルミル基,アセチル基,プロピオニル基,ブチリル基,パレリル基,オアルミトイル基,ステアロイル基,オレオイル基,ベンゾイル基,トリオイル基,サリチロイル基,シンナモイル基,ナフトイル基,フタロイル基,オキサリル基,マロニル基,スクシニル基,フロイル基などのアシル基;アリールオキシル基としてはフェノキシ基,トリルオキシ基などのアリールオキシル基;アラルキル基としてはベンジル基,フェネチル基などのアラルキル基;アシルアミノ基としてはアセチルアミノ基,プロピオニルアミノ基,ブチリルアミノ基などのアシルアミノ基;アシルオキシル基としてはアセチルオキシ基,プロピオニルオキシ基,ブチリル Boniru group, an aryloxycarbonyl group such as phenoxycarbonyl group; examples of the acyl group a formyl group, an acetyl group, a propionyl group, a butyryl group, Pareriru group, Oarumitoiru group, stearoyl group, oleoyl group, a benzoyl group, Torioiru group, salicyloyl group , cinnamoyl group, naphthoyl group, phthaloyl group, oxalyl group, malonyl group, succinyl group, an acyl group such as furoyl group; a phenoxy group as the aryloxy group, aryloxy groups such as tolyloxy group; Exemplary aralkyl groups include benzyl and phenethyl the acylamino group acetylamino group, propionylamino group, an acylamino group such as butyrylamino group; aralkyl group such as a group acetyloxy group as acyloxy group, propionyloxy group, butyryl キシ基などのアシルオキシル基である。 An acyloxyl group such as alkoxy group.

【手続補正2】 [Amendment 2]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0013 [Correction target item name] 0013

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0013】前記の置換基とは、水素原子、ハロゲン原子、メチル基,エチル基,プロピル基,ブチル基,シクロヘキシル基などのアルキル基、ビニル基,1-プロペニル基,アリル基,イソプロペニル基,1-ブテニル基,2- [0013] The the substituent, a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, an alkyl group such as a cyclohexyl group, a vinyl group, 1-propenyl group, allyl group, isopropenyl group, 1-butenyl group, 2-
ブテニル基,2-ペンテニル基,エチニル基などの不飽和鎖式炭化水素から誘導された1価の基、ピペリジル基, Butenyl, 2-pentenyl group, a monovalent group derived from an unsaturated chain hydrocarbon such as ethynyl group, piperidyl group,
ピペリジノ基,ピローリル基,フリル基,チェニル基, Piperidino group, a pyrrolyl group, a furyl group, a thienyl group,
イミダゾリル基,ピラゾリル基,トリアゾリル基,ピリジル基,チアゾリル基,ピリダジニル基,ピリドンよりなる1価の基,モルホリニル基,モルホリノ基,オキサゾリル基,イソオキサゾリル基,イソチアゾリル基,ピリミジニル基,ピラジニル基,ピラニル基,ベンゾイミダゾリル基,ベンゾチアゾリル基,ベンゾオキサゾリル基,キノリル基などの複素環式基、フェニル基,ナフチル基,アントニル基,キシリル基,ビフェニル基,フェナントリル基などのアリール基、アゾ基、フェニラゾ基,ナフチラゾ基,ヒドラニゾ基,ヒドラゾ基,アゾキシ基,アジド基,ジアゾアミノ基,アミディノ基,ウレイレン基,グアニディノ基などの窒素2原子以上を含む基、スチリル基、アニシル基、アミノ基、アルキルアミノ基、ジアルキルア Imidazolyl group, a pyrazolyl group, a triazolyl group, a pyridyl group, a thiazolyl group, a pyridazinyl group, a monovalent group formed from pyridone, morpholinyl group, Moruho Reno group, oxazolyl group, isoxazolyl group, isothiazolyl group, pyrimidinyl group, pyrazinyl group, pyranyl group , benzimidazolyl group, benzothiazolyl group, benzoxazolyl group, a heterocyclic group such as quinolyl group, a phenyl group, a naphthyl group, Antoniru group, a xylyl group, a biphenyl group, an aryl group such as a phenanthryl group, an azo group, Fenirazo group, Nafuchirazo group, Hidoranizo group, hydrazo group, azoxy group, azido group, diazoamino group, Amidino group, ureylene group, group containing at least nitrogen 2 atoms such as Guanidino group, a styryl group, an anisyl group, an amino group, an alkylamino group, Jiarukirua ノ基、メトキシル基,エトキシル基,プロポキシル基,ブトキシル基,ペンチルオキシル基,ヘキシルオキシル基などのアルコキシ基、メトキシカルボニル基,エトキシカルボニル基,ブトキシカルボニル基などのアルコキシカルボニル基、アニリノカルボニル基,ジメチルアミノカルボニル基,ラルバモイル基,アラニル基などのアミノカルボニル基、ナフチルオキシカルボニル基,キシリルオキシカルボニル基,フェノキシカルボニル基などのアリールオキシカルボニル基、カルボキシル基、ホルミル基,アセチル基,プロピオニル基,ブチリル基,パレリル基,オアルミトイル基,ステアロイル基,オレオイル基,ベンゾイル基,トリオイル基,サリチロイル基,シンナモイル基,ナフトイル基,フタロイル基,オキサリル基,マロ Amino group, methoxyl group, ethoxyl group, propoxyl group, butoxyl group, Penchiruokishiru group, an alkoxy group such as hexyloxy group, a methoxycarbonyl group, an alkoxycarbonyl group such as ethoxycarbonyl group, butoxycarbonyl group, anilino group, dimethylaminocarbonyl group, Rarubamoiru group, aminocarbonyl group, such as alanyl group, naphthyloxycarbonyl group, xylyl group, an aryloxycarbonyl group such as phenoxycarbonyl group, a carboxyl group, a formyl group, an acetyl group, a propionyl group, a butyryl group, Pareriru group, Oarumitoiru group, stearoyl group, oleoyl group, a benzoyl group, Torioiru group, salicyloyl group, cinnamoyl group, naphthoyl group, phthaloyl group, oxalyl group, Malo ル基,スクシニル基,フロイル基などのアシル基、フェノキシ基,トリルオキシ基などのアリールオキシ基、ベンジル基,フェネチル基などのアラルキル基、アセチルアミノ基,プロピオニルアミノ基,ブチリルアミノ基などのアシルアミノ基、アセチルオキシ基,プロピオニルオキシ基,ブチリルオキシ基などのアシルオキシル基、水酸基、シアノ基、ニトロ基、スルホ基またはスルホニウム基を表す。 Group, succinyl group, an acyl group such as furoyl group, a phenoxy group, an aryloxy group such as tolyloxy group, a benzyl group, an aralkyl group such as a phenethyl group, acetylamino group, propionylamino group, an acylamino group such as butyrylamino group, acetyl oxy group, propionyloxy group, acyloxy group such as butyryloxy group, a hydroxyl group, a cyano group, a nitro group, a sulfo group or a sulfonium group.

【手続補正3】 [Amendment 3]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0038 [Correction target item name] 0038

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0038】 [0038]

【化26】 [Of 26]

【手続補正4】 [Amendment 4]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0039 [Correction target item name] 0039

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0039】 [0039]

【化27】 [Of 27]

【手続補正5】 [Amendment 5]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0040 [Correction target item name] 0040

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0040】 [0040]

【化28】 [Of 28]

【手続補正6】 [Amendment 6]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0049 [Correction target item name] 0049

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0049】 [0049]

【化37】 [Of 37]

【手続補正7】 [Amendment 7]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0051 [Correction target item name] 0051

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0051】 [0051]

【化39】 [Of 39]

【手続補正8】 [Amendment 8]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0054 [Correction target item name] 0054

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0054】合成例1 掻混ぜ器と還流冷却器および滴下漏斗を取り付けた三つ口フラスコに、クロラニル(21g;mp287℃),無水マレイン酸(150g;mp55.5℃)およびペリレン(10g;mp280 [0054] three-necked flask fitted with a synthesis example 1 take-mix unit and a reflux condenser and a dropping funnel, chloranil (21g; mp287 ℃), maleic anhydride (150g; mp55.5 ℃) and perylene (10 g; MP280
℃) 十分粉砕混合した物を入れ、加熱しながら弗点で ° C.) placed things were thoroughly ground and mixed, in dollars point while heating
10分間掻混ぜた。 Mixed the take 10 minutes. その後、滴下漏斗から温めたキシレン(200ml)を加え掻混ぜ1時間沸騰し、熱濾過した。 Then, boiling warm xylene (200ml) was added 掻混 ze 1 hour from the dropping funnel and filtered hot. 熱濾過で分離した赤茶色針状結晶をキシレンで洗い、さらにエーテルで十分に洗浄することにより赤茶色針状結晶を得た。 The reddish-brown needle crystals separated by hot filtration washed with xylene to give a red-brown needles by thoroughly washed with ether. 得られた赤茶色針状結晶を減圧昇華装置を使って300℃,10 -4 mmHgで4時間半昇華し、昇華残留物をさらに減圧昇華装置を使って400℃,10 -4 mmHgで6時間処理することにより、光沢のある赤茶色針状結晶(I−2 The resulting reddish-brown needle crystals with a vacuum sublimation apparatus 300 ° C., 10 at -4 mmHg sublimated 4.5 hours, 400 ° C. further using vacuum sublimation apparatus sublimation residue, 6 hours at 10 -4 mmHg by treating, shiny reddish-brown needle crystals (I-2
8)が得られた。 8) was obtained.

【手続補正9】 [Amendment 9]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0064 [Correction target item name] 0064

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0064】一般式〔III〕で表される燐化合物は対応するハロメチル化合物とトリアリールホスフィンあるいはトリアルキルホスフィン 、または亜燐酸トリアルキルとを直接あるいはトルエン、キシレン等の溶媒中で加熱することにより容易に製造することができる。 [0064] The phosphorus compound represented by the general formula [III] readily by heating the corresponding halomethyl compound and triarylphosphine or trialkylphosphine or a trialkylphosphite, directly or toluene, in a solvent such as xylene it can be produced in.

【手続補正10】 [Amendment 10]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0085 [Correction target item name] 0085

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0085】 [0085]

【化49】 [Of 49]

【手続補正11】 [Amendment 11]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0086 [Correction target item name] 0086

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0086】 [0086]

【化50】 [Of 50]

【手続補正12】 [Amendment 12]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0106 [Correction target item name] 0106

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0106】 [0106]

【化64】 [Of 64]

【手続補正13】 [Amendment 13]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0117 [Correction target item name] 0117

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0117】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し17V直流電圧の印加によって、最大輝度63.9cd/m 2発光が得られた。 [0117] By the application of connecting an external power supply 17V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 63.9cd / m 2 was obtained. また温度23℃乾燥窒素ガス雰囲気下で17V直流電圧印加による連続点灯を行ったところ、輝度の半減する時間は1589時間であった。 Also was subjected to a continuous lighting by 17V DC voltage in an atmosphere temperature of 23 ° C. dry nitrogen gas, the time for half of the luminance was 1589 hours.

【手続補正14】 [Amendment 14]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0146 [Correction target item name] 0146

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0146】このようにして得られた有機薄膜エレクトロルミネッセンス素子に外部電源を接続し17V直流電圧の印加によって、最大輝度60.7cd/m 2の発光が得られた。 [0146] By the application of connecting an external power supply 17V DC voltage to the organic thin film electroluminescent element thus obtained, the light emission of the maximum luminance 60.7cd / m 2 was obtained.

【手続補正15】 [Amendment 15]

【補正対象書類名】明細書 [Correction target document name] specification

【補正対象項目名】0150 [Correction target item name] 0150

【補正方法】変更 [Correction method] change

【補正内容】 [Correction contents]

【0150】次いで、真空条件を破ることなく化合物(I− )をモリブテンボート(日本バックスメタル株式会社製SS-1-9)に入れ、8.0×10 -7 Torrの真空条件下で0.2nm/secの成膜速度で62nmの発光層を積層蒸着した。 [0150] Next, the compound without breaking the vacuum conditions (I- 2) put in a molybdenum boat (Japan Bucks made of metal, Ltd. SS-1-9), 8.0 × 10 -7 Torr of 0.2nm under vacuum conditions / It was laminated deposited light emitting layer of 62nm in sec deposition rate.

Claims (2)

    【特許請求の範囲】 [The claims]
  1. 【請求項1】 一対の対向電極とこれらによって挟持された複数の有機化合物層から構成されているエレクトロルミネッセンス素子において、下記一般式〔I〕で表わされる有機化合物を含有する層と、下記一般式〔II〕で表されるスチリル化合物を含有する層を、それぞれ少なくとも一層以上ずつ設けたことを特徴とする有機薄膜エレクトロルミネッセンス素子。 1. A pair of opposed electrodes and the electroluminescent device is composed of a plurality of organic compound layers sandwiched by these, a layer containing an organic compound represented by the following general formula [I], the following formula a layer containing a styryl compound represented by [II], respectively organic thin film electroluminescence device characterized by comprising by at least one or more layers. 【化1】 [Formula 1] 〔一般式〔I〕の残基Zの(Z1)〜(Z4)中、R 1 In [Formula residue Z of [I] (Z1) ~ (Z4), R 1 ~
    11はそれぞれ独立に、水素原子、ハロゲン原子、置換若しくは無置換の続記5つの基;アルキル基、不飽和鎖式炭化水素から誘導された1価の基、複素環式基、アリール基、窒素2原子以上を含む基、又はスチリル基、アニシル基、アミノ基、アルキルアミノ基、ジアルキルアミノ基、アルコキシ基、アルコキシカルボニル基、アミノカルボニル基、アリールオキシカルボニル基、カルボキシル基、アシル基、アリールオキシル基、アラルキル基、アシルアミノ基、アシルオキシル基、水酸基、シアノ基、ニトロ基、スルホ基、スルホニウム基を表し、R R 11 are each independently a hydrogen atom, a halogen atom, continued serial substituted or unsubstituted 5 groups: an alkyl group, a monovalent group derived from an unsaturated chain hydrocarbon, a heterocyclic group, an aryl group, nitrogen radical containing two or more atoms, or a styryl group, an anisyl group, an amino group, an alkylamino group, a dialkylamino group, an alkoxy group, an alkoxycarbonyl group, an amino group, an aryloxycarbonyl group, a carboxyl group, an acyl group, aryloxy It represents group, an aralkyl group, an acylamino group, acyloxy group, a hydroxyl group, a cyano group, a nitro group, a sulfo group, a sulfonium radical, R
    1とR 2 、R 2とR 3 、R 3とR 4 、R 6とR 7 、R 7とR 8 、R 1 and R 2, R 2 and R 3, R 3 and R 4, R 6 and R 7, R 7 and R 8, R
    8とR 9 、R 9とR 10 、R 10とR 11は互いに結合して置換若しくは無置換の飽和または不飽和の環構造を形成していてもよい。 8 and R 9, R 9 and R 10, R 10 and R 11 may form a saturated or unsaturated ring structure substituted or unsubstituted bound to each other. また上記式(Z5)中Xは、置換若しくは無置換の複素環を表す。 The above formula (Z5) Medium X represents a substituted or unsubstituted heterocyclic. 〕 【化2】 ] [Formula 2] 〔上記一般式〔II〕中、R 12及びR 13は、それぞれ独立に、水素原子、置換若しくは無置換の続記4つの基;アルキル基、複素環基、アリール基、不飽和鎖式炭化水素から誘導された1価の基を表し、R 12とR 13は互いに結合して置換若しくは無置換の飽和または不飽和の環構造を形成していてもよい。 [In the above general formula [II], R 12 and R 13 each independently represent a hydrogen atom, a substituted or unsubstituted continued serial 4 groups: alkyl group, a heterocyclic group, an aryl group, an unsaturated chain hydrocarbon represents a monovalent group derived from, R 12 and R 13 may form a saturated or unsaturated ring structure substituted or unsubstituted bound to each other. 14は、置換若しくは無置換の続記3つの基;アルキル基、アリール基、アルコキシ基又は−{p(C 6 H 4 )}−CH=C{(−R 12 )(−R 13 )}を表し、 R 14 represents a substituted or unsubstituted continued serial 3 groups: alkyl group, an aryl group, an alkoxy group or an - {p (C 6 H 4 )} - CH = C {(- R 12) (- R 13)} the stands,
    12及びR 13は前記と同義である。 R 12 and R 13 are as defined above. 15は、水素原子、 R 15 is a hydrogen atom,
    置換若しくは無置換の続記3つの基;アルキル基、アリール基、アルコキシ基を表す。 A substituted or unsubstituted continued serial 3 groups: alkyl group, an aryl group, an alkoxy group. ]
  2. 【請求項2】 前記一般式〔I〕で表される有機化合物を発光物質とし、前記一般式〔II〕で表されるスチリル化合物を正孔輸送物質としたことを特徴とする請求項1 2. A method according to claim 1, wherein the general formula and an organic compound emitting material represented by (I), and the styryl compound represented by the general formula (II) and a hole transport material
    に記載の有機薄膜エレクトロルミネッセンス素子。 The organic thin film electroluminescence device according to.
JP33351791A 1991-12-17 1991-12-17 Electroluminescent element of organic thin film Pending JPH05163488A (en)

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US07967997 US5443922A (en) 1991-11-07 1992-10-28 Organic thin film electroluminescence element

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