JPH06136360A - Electroluminescent element - Google Patents
Electroluminescent elementInfo
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- JPH06136360A JPH06136360A JP4312618A JP31261892A JPH06136360A JP H06136360 A JPH06136360 A JP H06136360A JP 4312618 A JP4312618 A JP 4312618A JP 31261892 A JP31261892 A JP 31261892A JP H06136360 A JPH06136360 A JP H06136360A
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- electroluminescent device
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は電界発光素子に関する。FIELD OF THE INVENTION The present invention relates to an electroluminescent device.
【０００２】[0002]
【従来の技術】有機材料の電界発光現象は１９６３年Ｐ
ｏｐｅらによってアントラセン単結晶で観測され（Ｊ．
Ｃｈｅｍ．Ｐｈｙｓ．３８（１９６３）２０４２）、そ
れに続き１９６５年ＨｅｌｆｉｎｎｃｈとＳｃｈｎｅｉ
ｄｅｒは注入効率の良い溶液電極系を用いることにより
比較的強い注入型エレクトロルミネッセンス（ＥＬ）の
観測に成功している（Ｐｈｙｓ．Ｒｅｖ．Ｌｅｔｔ．１
４（１９６５）２２９）。それ以来、米国特許３，１７
２，８６２、米国特許３，１７３，０５０、米国特許
３，７１０，１６７、Ｊ．Ｃｈｅｍ．Ｐｈｙｓ．４４
（１９６６）２９０２、Ｊ．Ｃｈｅｍ．Ｐｈｙｓ．５０
（１９６９）１４３６４、Ｊ．Ｃｈｅｍ．Ｐｈｙｓ．５
８（１９７３）１５４２あるいはＣｈｅｍ．Ｐｈｙｓ．
Ｌｅｔｔ．３６（１９７５）３４５などに報告されてい
るように、共役の有機ホスト物質と縮合ベンゼン環を持
つ共役の有機活性化剤とで有機発光性物質を形成した研
究が行われた。ナフタレン、アンスラセン、フェナンス
レン、テトラセン、ピレン、ベンゾピレン、クリセン、
ピセン、カルバゾ−ル、フルオレン、ビフェニル、タ−
フェニル、トリフェニレンオキサイド、ジハロビフェニ
ル、トランス−スチルベンおよび１，４−ジフェニルブ
タジエンなどが有機ホスト物質の例として示され、アン
スラセン、テトラセンおよびペンタセンなどが活性化剤
の例として挙げられた。しかし、これらの有機発光性物
質はいずれも１μｍ以上を超える厚さを持つ単一層とし
て存在し、発光には高電界が必要であった。このため、
真空蒸着法による薄膜素子の研究が進められた（例えば
Ｔｈｉｎｎ Ｓｏｌｉｄ Ｆｉｌｍｓ９４（１９８２）
１７１、Ｐｏｌｙｍｅｒ２４（１９８３）７４８、Ｊｐ
ｎ．Ｊ．Ａｐｐｌ．Ｐｈｙｓ．２５（１９８６）Ｌ７７
３）。しかし薄膜化は駆動電圧の低減には有効ではあっ
たが、実用レベルの高輝度の素子を得るには至らなかっ
た。2. Description of the Related Art The electroluminescence phenomenon of organic materials is 1963 P.
observed in anthracene single crystal (J.
Chem. Phys. 38 (1963) 2042), followed by 1965 Helfinnch and Schnei.
der has succeeded in observing relatively strong injection electroluminescence (EL) by using a solution electrode system having a high injection efficiency (Phys. Rev. Lett. 1).
4 (1965) 229). Since then, US Patent 3,17
2,862, U.S. Pat. No. 3,173,050, U.S. Pat. No. 3,710,167, J. Chem. Phys. 44
(1966) 2902, J. Chem. Phys. Fifty
(1969) 14364, J. Am. Chem. Phys. 5
8 (1973) 1542 or Chem. Phys.
Lett. 36 (1975) 345, etc., studies have been conducted on forming an organic light-emitting substance from a conjugated organic host substance and a conjugated organic activator having a condensed benzene ring. Naphthalene, anthracene, phenanthrene, tetracene, pyrene, benzopyrene, chrysene,
Picene, carbazole, fluorene, biphenyl, tar
Phenyl, triphenylene oxide, dihalobiphenyl, trans-stilbene, 1,4-diphenylbutadiene, etc. were shown as examples of organic host materials, and anthracene, tetracene, pentacene, etc. were mentioned as examples of activators. However, all of these organic light-emitting substances existed as a single layer having a thickness of 1 μm or more, and a high electric field was required for light emission. For this reason,
Research on thin film devices by the vacuum deposition method has been advanced (for example, Thinn Solid Films 94 (1982).
171, Polymer 24 (1983) 748, Jp.
n. J. Appl. Phys. 25 (1986) L77
3). However, although thinning was effective in reducing the driving voltage, it was not possible to obtain a practically high brightness device.
【０００３】近年、Ｔａｎｎｇｓらにより（Ａｐｐｌ．
Ｐｈｙｓ．Ｌｅｔｔ．５１（１９８７）９１３あるいは
米国特許４，３５６，４２９）陽極と陰極との間に極め
て薄い２層（電荷輸送層と発光層）を真空蒸着で積層し
たＥＬ素子を考案し、低い駆動電圧で高輝度を実現し
た。この種の積層型有機ＥＬデバイスはその後も活発に
研究され、例えば特開昭５９−１９４３９３、米国特許
４，５３９，５０７、特開昭５９−１９４３９３、米国
特許４，７２０，４３２、特開昭６３−２６４６９２、
Ａｐｐｌ．Ｐｈｙｓ．Ｌｅｔｔ．５５（１９８６）１４
６７、特開平３−１６３１８８などに記載されている。Recently, Tanngs et al. (Appl.
Phys. Lett. 51 (1987) 913 or US Pat. No. 4,356,429) We devised an EL device in which two very thin layers (a charge transport layer and a light emitting layer) were laminated by vacuum evaporation between an anode and a cathode, and a high driving voltage was obtained at a low driving voltage. Realized brightness. This type of laminated organic EL device has been actively researched since then, and is disclosed in, for example, JP-A-59-194393, US Pat. No. 4,539,507, JP-A-59-194393, US Pat. 63-264692,
Appl. Phys. Lett. 55 (1986) 14
67, JP-A-3-163188 and the like.
【０００４】また更にＪｐｎ．Ｊ．Ａｐｐｌ．Ｐｈｙ
ｓ．２７（１９８８）Ｌ２６９，Ｌ７１３にはキャリア
輸送と発光の機能を分離した３層構造のＥＬ素子が報告
されており、発光色を決める発光層の色素の選定に際し
てもキャリア輸送性能の制約が緩和され選択の自由度が
かなり増し、更には中央の発光層にホ−ルと電子（ある
いは励起子）を有効に閉じ込めて発光の向上を図る可能
性も示唆される。Furthermore, Jpn. J. Appl. Phy
s. 27 (1988) L269, L713, an EL device having a three-layer structure in which the functions of carrier transport and light emission are separated has been reported, and restrictions on carrier transport performance are alleviated when selecting a dye for the light-emitting layer that determines the emission color. It also suggests that the degree of freedom in selection is considerably increased, and further that holes and electrons (or excitons) are effectively confined in the central light emitting layer to improve the light emission.
【０００５】積層型有機ＥＬ素子作成には、一般に真空
蒸着法が用いられているが、キャスティング法によって
もかなりの明るさの素子が得られることが報告されてい
る（例えば、第５０回応物学会学術講演会講演予稿集１
００６（１９８９）および第５１回応物学会学術講演会
講演予稿集１０４１（１９９０））。A vacuum evaporation method is generally used for producing a laminated organic EL element, but it has been reported that an element having a considerable brightness can be obtained also by a casting method (for example, the 50th Society of Applied Physics). Academic Lecture Lecture Proceedings 1
006 (1989) and Proceedings of the 51st Academic Meeting of the Society of Biological Sciences 1041 (1990)).
【０００６】更には、ホ−ル輸送化合物としてポリビニ
ルカルバゾ−ル、電子輸送化合物としてオキサジアゾ−
ル誘導体および発光体としてクマリン６を混合した溶液
から浸漬塗布法で形成した混合１層型ＥＬ素子でもかな
り高い発光効率が得られることが報告されている（例え
ば、第３８回応物関係連合講演会講演予稿集１０８６
（１９９１））。Further, polyvinylcarbazole is used as a hole transport compound, and oxadiazo is used as an electron transport compound.
It has been reported that even a mixed single-layer type EL device formed by a dip coating method from a solution in which a carboxylic acid derivative and coumarin 6 as a luminescent material are mixed can provide a considerably high luminous efficiency (for example, the 38th Joint Meeting on Vehicular Relations). Lecture Proceedings 1086
(1991)).
【０００７】上述のように有機ＥＬデバイスにおける最
近の進歩は著しく広汎な用途の可能性を示唆している。
しかし、それらの研究の歴史はまだまだ浅く、未だその
材料研究やデバイス化への研究は十分なされていない。
現状では更なる高輝度の光出力や長時間の使用による経
時変化や酸素を含む雰囲気気体や湿気などによる劣化な
どの耐久性の面に未だ問題がある。更にはフルカラ−デ
ィスプレ−などへの応用を考えた場合の青、緑、赤の発
光色相を精密に選択できるための発光波長の多様化など
の問題も未だ十分に解決されていない。As mentioned above, the recent advances in organic EL devices suggest a remarkably wide range of potential applications.
However, the history of those studies is still shallow, and the researches for materials and devices have not been sufficiently conducted.
At present, there are still problems in terms of durability such as higher brightness light output, deterioration with time due to long-term use, and deterioration due to atmospheric gas containing oxygen or moisture. Further, in consideration of application to full-color displays and the like, problems such as diversification of emission wavelengths for precisely selecting emission hues of blue, green and red have not yet been sufficiently solved.
【０００８】[0008]
【発明が解決しようとする課題】本発明の目的は第一に
極めて高輝度の光出力を有する電界発光素子を提供する
こと、第二に発光波長に多様性があり、種々の発光色相
を呈するとともに極めて耐久性のある電界発光素子を提
供すること、第三に製造が容易で、かつ、比較的安価に
提供できる電界発光素子材料を提供することである。An object of the present invention is to firstly provide an electroluminescent device having a light output of extremely high brightness, and secondly, there are various emission wavelengths and various emission hues. At the same time, it is to provide an electroluminescent device having extremely high durability, and thirdly to provide an electroluminescent device material which is easy to manufacture and can be provided at a relatively low cost.
【０００９】[0009]
【課題を解決するための手段】本発明は陽極および陰極
と、これらの間に挟持された一層または複数層の有機化
合物より構成される電界発光素子において、前記有機化
合物層のうち少なくとも一層が下記一般式（１）で示さ
れるアミン骨格を有し、かつ、同一分子内にカルボニル
基を有する化合物を含有することを特徴とする電界発光
素子から構成される。一般式（１）The present invention provides an electroluminescent device comprising an anode and a cathode and one or a plurality of layers of an organic compound sandwiched therebetween, wherein at least one of the organic compound layers is as follows. The electroluminescent device is characterized by having an amine skeleton represented by the general formula (1) and containing a compound having a carbonyl group in the same molecule. General formula (1)
【化３】 式中、Ｒは、置換基を有してもよい、アルキル基または
アラルキル基を示し、Ａｒ1 およびＡｒ2 は、置換基を
有してもよい、芳香環基を示す。[Chemical 3] In the formula, R represents an alkyl group or an aralkyl group which may have a substituent, and Ar 1 and Ar 2 represent an aromatic ring group which may have a substituent.
【００１０】また、本発明は陽極および陰極と、これら
の間に挟持された一層または複数層の有機化合物より構
成される電界発光素子において、前記有機化合物層のう
ち少なくとも一層が下記一般式（２）で示される化合物
を含有することを特徴とする電界発光素子から構成され
る。一般式（２）Further, in the present invention, in an electroluminescent device comprising an anode and a cathode and one or more layers of organic compound sandwiched therebetween, at least one of the organic compound layers has the following general formula (2): ). The electroluminescent device is characterized by containing a compound represented by the formula (1). General formula (2)
【化４】 式中、Ａｒは、置換基を有してもよい、縮合多環芳香環
基を示し、Ｒ1 、Ｒ2およびＲ3 は、水素原子、置換基
を有してもよい、アルキル基、アラルキル基または芳香
環基を示し（ただし、Ｒ1 とＲ2 が同時に水素原子であ
る場合を除く）、ｎは０または１の整数を示す。[Chemical 4] In the formula, Ar represents a condensed polycyclic aromatic ring group which may have a substituent, and R 1 , R 2 and R 3 each represent a hydrogen atom, an alkyl group which may have a substituent, or an aralkyl. A group or an aromatic ring group (provided that R 1 and R 2 are simultaneously hydrogen atoms), and n represents an integer of 0 or 1.
【００１１】上記一般式（１）における基の定義におい
て、具体的には、アルキル基としては炭素数１〜６の
基、アラルキル基としてはベンジル、フェネチル、ナフ
チルメチルなどの基、芳香環基としてはフェニル、ナフ
チルなどの基が挙げられる。In the definition of the group in the above general formula (1), specifically, the alkyl group is a group having 1 to 6 carbon atoms, the aralkyl group is a group such as benzyl, phenethyl and naphthylmethyl, and the aromatic ring group. Include groups such as phenyl and naphthyl.
【００１２】また、上記基における置換基としては炭素
数１〜４のアルキル基、メトキシ、エトキシなどのアル
コキシ基、フッ素原子、塩素原子、臭素原子などのハロ
ゲン原子、ジメチルアミノ、ジフェニルアミノなどのア
ミノ基またはフェニル、ナフチルなどの芳香環基などが
挙げられる。The substituent in the above groups is an alkyl group having 1 to 4 carbon atoms, an alkoxy group such as methoxy and ethoxy, a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom, and an amino group such as dimethylamino and diphenylamino. Group or an aromatic ring group such as phenyl or naphthyl.
【００１３】また、上記一般式（２）における基の定義
において、具体的には、縮合多環芳香環基としてはナフ
タレン、アントラセン、ピレン、アセナフチレン、フェ
ナンスレン、フルオランセン、トリフェニレン、クリセ
ン、ペリレン、テトラセン、ペンタセン、コロナンなど
の基、アルキル基としては炭素数１〜４の基、アラルキ
ル基としてはベンジル、フェネチル、ナフチルメチルな
どの基、芳香環基としてはフェニル、ナフチルなどの基
が挙げられる。In the definition of the group in the above general formula (2), specifically, the condensed polycyclic aromatic ring group is naphthalene, anthracene, pyrene, acenaphthylene, phenanthrene, fluoranthene, triphenylene, chrysene, perylene, tetracene, Examples include groups such as pentacene and coronane; examples of alkyl groups include groups having 1 to 4 carbon atoms; examples of aralkyl groups include groups such as benzyl, phenethyl, and naphthylmethyl; examples of aromatic ring groups include groups such as phenyl and naphthyl.
【００１４】また、上記基における置換基としては炭素
数１〜４のアルキル基、ベンジル、フェネチルなどのア
ラルキル基、フェニル、ナフチルなどの芳香環基、メト
キシ、エトキシ、プロポキシなどのアルコキシ基、フェ
ノキシ、ナフトキシなどのアリ−ルオキシ基、フッ素原
子、塩素原子、臭素原子などのハロゲン原子、ベンゾイ
ル、ナフトイル、アセチル、ブチリルなどのアシル基、
水酸基、ニトロ基またはシアノ基などが挙げられる。The substituents in the above groups are alkyl groups having 1 to 4 carbon atoms, aralkyl groups such as benzyl and phenethyl, aromatic ring groups such as phenyl and naphthyl, alkoxy groups such as methoxy, ethoxy and propoxy, and phenoxy. An aryloxy group such as naphthoxy, a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom, an acyl group such as benzoyl, naphthoyl, acetyl and butyryl,
Examples thereof include a hydroxyl group, a nitro group and a cyano group.
【００１５】一般式（１）で示されるアミン骨格を有
し、かつ、同一分子内にカルボニル基を有する化合物お
よび一般式（２）で示される化合物について、その代表
例を表１〜８に挙げる。但し、本発明はこれらの化合物
に限定されるものではない。Typical examples of the compounds having the amine skeleton represented by the general formula (1) and having a carbonyl group in the same molecule and the compounds represented by the general formula (2) are shown in Tables 1 to 8. . However, the present invention is not limited to these compounds.
【表１】 [Table 1]
【表２】 [Table 2]
【表３】 [Table 3]
【表４】 [Table 4]
【表５】 [Table 5]
【表６】 [Table 6]
【表７】 [Table 7]
【表８】 [Table 8]
【００１６】本発明の電界発光素子は、一般式（１）で
示されるアミン骨格を有し、かつ、同一分子内にカルボ
ニル基を有する化合物および一般式（２）で示される化
合物から選ばれる化合物を真空蒸着法や溶液塗布法など
により陽極および陰極の間に形成する。その有機層の厚
みは２μｍより薄く、好ましくは０．５μｍより小さく
薄膜化することが好ましい。The electroluminescent device of the present invention is a compound having an amine skeleton represented by the general formula (1) and having a carbonyl group in the same molecule and a compound represented by the general formula (2). Is formed between the anode and the cathode by a vacuum deposition method or a solution coating method. The thickness of the organic layer is smaller than 2 μm, preferably smaller than 0.5 μm and is preferably thin.
【００１７】本発明を更に図面に添って詳細に説明す
る。図１は基盤１上に陽極２、発光層３および陰極４を
順次設けた構成のものである。ここで使用する発光素子
はそれ自体でホ−ル輸送能、エレクトロン輸送能および
発光性の性能を単一で有している場合やそれぞれの特性
を有する化合物を混ぜて使う場合に有用である。The present invention will be described in detail with reference to the drawings. FIG. 1 shows a structure in which an anode 2, a light emitting layer 3 and a cathode 4 are sequentially provided on a substrate 1. The light emitting device used here is useful when it has a single hole transporting ability, an electron transporting ability and a light emitting ability by itself, or when compounds having respective properties are mixed and used.
【００１８】図２は基盤１上に陽極２、ホ−ル輸送層
５、エレクトロン輸送層６および陰極４を順次設けた構
成のものである。この場合は発光物質はホ−ル輸送性か
あるいはエレクトロン輸送性のいずれかあるいは両方の
機能を有している材料をそれぞれの層に用い、発光性の
ない単なるホ−ル輸送物質あるいはエレクトロン輸送物
質と組み合わせて用いる場合に有用である。FIG. 2 shows a structure in which an anode 2, a hole transport layer 5, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. In this case, the light-emitting substance is a material having a hole-transporting property, an electron-transporting property, or both, for each layer, and a mere hole-transporting substance or electron-transporting substance having no light-emitting property is used. It is useful when used in combination with.
【００１９】図３は基盤１上に陽極２、ホ−ル輸送層
５、発光層３、エレクトロン輸送層６および陰極４を順
次設けた構成のものである。これはキャリア輸送と発光
の機能を分離したものであり、ホ−ル輸送性、エレクト
ロン輸送性、発光性の各特性を有した化合物と適宜組み
合わせて用いられ極めて材料の選択の自由度が増すとと
もに、発光波長を異にする種々の化合物が使用できるた
め、発光色相の多様化が可能となる。また、更に、中央
の発光層にホ−ルとエレクトロン（あるいは励起子）を
有効に閉じ込めて発光効率の向上を図ることも可能にな
る。FIG. 3 shows a structure in which an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. This is one in which the functions of carrier transport and light emission are separated, and it is used in combination with a compound having hole transportability, electron transportability, and light emission properties as appropriate, and the degree of freedom in selecting materials is greatly increased. Since various compounds having different emission wavelengths can be used, the emission hue can be diversified. Further, it becomes possible to effectively confine holes and electrons (or excitons) in the central light emitting layer to improve the light emitting efficiency.
【００２０】前記一般式（１）で示されるアミン骨格を
有し、かつ、同一分子内にカルボニル基を有する化合物
および一般式（２）で示される化合物から選ばれる化合
物は、従来の化合物に比べていずれも極めて発光特性の
優れた化合物であり、必要に応じて図１、図２または図
３のいずれの形態でも使用することが可能である。The compound selected from the compound having the amine skeleton represented by the general formula (1) and having a carbonyl group in the same molecule and the compound represented by the general formula (2) is higher than conventional compounds. All of them are compounds having extremely excellent light emission characteristics, and can be used in any of the forms shown in FIGS. 1, 2 and 3 as required.
【００２１】また、化合物の構造によりホ−ル輸送性あ
るいはエレクトロン輸送性のいずれかあるいは両方の性
能を有し、図１、図２または図３のいずれの形態の場合
でも前記一般式（１）で示されるアミン骨格を有し、か
つ、同一分子内にカルボニル基を有する化合物および一
般式（２）で示される化合物から選ばれる化合物を必要
に応じ２種類以上使用してもかまわない。Further, depending on the structure of the compound, it has a hole transporting property, an electron transporting property, or both, and in any of the forms shown in FIG. 1, FIG. 2 or FIG. If desired, two or more compounds selected from the compound having an amine skeleton represented by and having a carbonyl group in the same molecule and the compound represented by the general formula (2) may be used.
【００２２】本発明においては、発光層構成成分として
一般式（１）で示されるアミン骨格を有し、かつ、同一
分子内にカルボニル基を有する化合物および一般式
（２）で示される化合物から選ばれる化合物を用いるも
のであるが、必要に応じて電子写真感光体分野などで研
究されているホ−ル輸送性化合物やこれまで知られてい
るホ−ル輸送性発光体化合物（例えば表９〜１０に挙げ
られる化合物など）あるいはエレクトロン輸送性化合物
やこれまで知られているエレクトロン輸送性発光体化合
物（例えば表１１に挙げられる化合物など）を一緒に使
用することもできる。In the present invention, a compound having an amine skeleton represented by the general formula (1) and having a carbonyl group in the same molecule as a constituent of the light emitting layer and a compound represented by the general formula (2) are selected. If desired, a hole-transporting compound that has been studied in the field of electrophotographic photoreceptors or a hole-transporting luminescent compound that has hitherto been known (for example, Table 9- 10) or an electron transporting compound or an electron transporting light emitting compound known so far (for example, a compound listed in Table 11) can be used together.
【００２３】ホ−ル輸送性化合物Hole-transporting compound
【表９】 [Table 9]
【表１０】 [Table 10]
【００２４】エレクトロン輸送性化合物Electron transporting compound
【表１１】 [Table 11]
【００２５】本発明の一般式（１）で示されるアミン骨
格を有し、かつ、同一分子内にカルボニル基を有する化
合物および一般式（２）で示される化合物から選ばれる
化合物を用いた電界発光素子は、一般には真空蒸着ある
いは適当な結着性樹脂と組み合わせて薄膜を形成する。Electroluminescence using a compound having an amine skeleton represented by the general formula (1) of the present invention and having a carbonyl group in the same molecule and a compound selected from the compound represented by the general formula (2). The device is generally vacuum-deposited or combined with a suitable binder resin to form a thin film.
【００２６】結着剤としては広範囲な結着性樹脂より選
択でき、例えばポリビニルカルバゾ−ル、ポリカ−ボネ
−ト、ポリエステル、ポリアリレ−ト、ブチラ−ル樹
脂、ポリスチレン、ポリビニルアセタ−ル、ジアリルフ
タレ−ト樹脂、アクリル樹脂、メタクリル樹脂、フェノ
−ル樹脂、エポキシ樹脂、シリコン樹脂、ポリスルホ
ン、尿素樹脂などが挙げられるが、これらに限定される
ものではない。これらの樹脂は単独または共重合体ポリ
マ−として１種または２種以上混合して用いることがで
きる。The binder can be selected from a wide range of binder resins, such as polyvinyl carbazole, polycarbonate, polyester, polyarylate, butyral resin, polystyrene, polyvinyl acetal, Examples thereof include, but are not limited to, diallyl phthalate resin, acrylic resin, methacrylic resin, phenol resin, epoxy resin, silicone resin, polysulfone, and urea resin. These resins may be used alone or in combination of two or more as a copolymer polymer.
【００２７】陽極材料としては仕事関数がなるべく大き
なものがよく、例えばニッケル、金、白金、パラジウ
ム、セレン、レニウム、イリジウムやこれらの合金、あ
るいは酸化錫、酸化錫インジウム（ＩＴＯ）、ヨウ化銅
が好ましい。また、ポリ（３−メチルチオフェン）、ポ
リフェニレンスルフィドあるいはポリピロ−ルなどの導
電性ポリマ−も用いることができる。As the anode material, a material having a work function as large as possible is preferable, and examples thereof include nickel, gold, platinum, palladium, selenium, rhenium, iridium and alloys thereof, tin oxide, indium tin oxide (ITO), and copper iodide. preferable. Further, a conductive polymer such as poly (3-methylthiophene), polyphenylene sulfide or polypyrrole can also be used.
【００２８】陰極材料としては仕事関数が小さな銀、
鉛、錫、マグネシウム、アルミニウム、カルシウム、マ
ンガン、インジウム、クロムあるいはこれらの合金が用
いられる。As the cathode material, silver having a small work function,
Lead, tin, magnesium, aluminum, calcium, manganese, indium, chromium or alloys thereof are used.
【００２９】また、陽極および陰極として用いる材料の
うち少なくとも一方は、素子の発光波長領域において５
０％より多くの光を透過することが好ましい。At least one of the materials used for the anode and the cathode is 5 in the emission wavelength region of the device.
It is preferable to transmit more than 0% of the light.
【００３０】本発明で用いる透明性基盤としてはガラ
ス、プラスチックフィルムなどが用いられる。As the transparent substrate used in the present invention, glass, plastic film or the like is used.
【００３１】本発明の電界発光素子は、従来の白熱灯、
蛍光灯あるいは発光ダイオ−ドなどと異なり大面積、高
分解能、薄型、軽量、高速動作、完全な固体デバイスで
あり、高度な要求を満たす可能性のあるエレクトロルミ
ネッセンス（ＥＬ）パネルに使用する。The electroluminescent element of the present invention is a conventional incandescent lamp,
Unlike fluorescent lamps or light-emitting diodes, it is a large-area, high-resolution, thin, lightweight, high-speed operation, complete solid-state device, and is used for electroluminescence (EL) panels that may meet high requirements.
【００３２】[0032]
実施例１ 酸化錫インジウム（ＩＴＯ）被膜（５０ｎｍ）ガラスの
透明陽極上に、化合物例４からなる発光層９０ｎｍ、そ
してＭｇ／Ａｇ（１０／１）合金からなる陰極２２０ｎ
ｍを各々順次真空蒸着により形成し、図１に示す構成の
電界発光素子を作成した。Example 1 On a transparent anode of indium tin oxide (ITO) -coated (50 nm) glass, a light emitting layer of Compound Example 4 having a thickness of 90 nm, and a cathode of Mg / Ag (10/1) alloy 220 n.
m were sequentially formed by vacuum vapor deposition to prepare an electroluminescent device having the structure shown in FIG.
【００３３】作成した電界発光素子の陽極と陰極をリ−
ド線で結び直流電源を接続し１０Ｖの電圧を印加したと
ころ、電流密度７．０ｍＡ／ｃｍ2 の電流が素子に流
れ、０．１０ｍＷ／ｃｍ2 の光出力が確認された。The anode and cathode of the prepared electroluminescent device were read.
When a direct current power supply was connected and a voltage of 10 V was applied by connecting with a power line, a current having a current density of 7.0 mA / cm 2 flowed through the device, and an optical output of 0.10 mW / cm 2 was confirmed.
【００３４】そして、そのままの電流密度（７．０ｍＡ
／ｃｍ2 ）を２４時間保ったところ、２４時間後でも最
終出力０．０９ｍＷ／ｃｍ2 の光出力が１０．８Ｖの印
加電圧で得られた。Then, the current density as it is (7.0 mA
/ Cm 2 ) for 24 hours, an optical output with a final output of 0.09 mW / cm 2 was obtained with an applied voltage of 10.8 V even after 24 hours.
【００３５】実施例２〜５ 実施例１で用いた化合物例４に代えて、それぞれ化合物
例６、化合物例９、化合物例１２、化合物例２０を用い
た他は、実施例１と同様にして、実施例２、実施例３、
実施例４、実施例５の電界発光素子を作成した。Examples 2 to 5 In the same manner as in Example 1 except that Compound Example 6, Compound Example 9, Compound Example 12 and Compound Example 20 were used instead of Compound Example 4 used in Example 1, respectively. Example 2, Example 3,
Electroluminescent devices of Examples 4 and 5 were produced.
【００３６】作成したそれぞれの電界発光素子に、電流
密度７．０ｍＡ／ｃｍ2 の電流を２４時間流した。結果
を表１２に示す。A current having a current density of 7.0 mA / cm 2 was applied to each of the prepared electroluminescent devices for 24 hours. The results are shown in Table 12.
【表１２】 [Table 12]
【００３７】比較例１〜５ 実施例１で用いた化合物例４に代えて、下記構造式の化
合物（ａ）、化合物（ｂ）、化合物（ｃ）、化合物
（ｄ）、化合物（ｅ）を用いた他は、実施例１と同様に
して、比較例１、比較例２、比較例３、比較例４、比較
例５の電界発光素子を作成した。化合物（ａ）Comparative Examples 1 to 5 Instead of the compound example 4 used in Example 1, a compound (a), a compound (b), a compound (c), a compound (d) and a compound (e) having the following structural formulas were used. The electroluminescent elements of Comparative Example 1, Comparative Example 2, Comparative Example 3, Comparative Example 4, and Comparative Example 5 were prepared in the same manner as in Example 1 except that the elements were used. Compound (a)
【化５】 化合物（ｂ）[Chemical 5] Compound (b)
【化６】 化合物（ｃ）[Chemical 6] Compound (c)
【化７】 化合物（ｄ）[Chemical 7] Compound (d)
【化８】 化合物（ｅ）[Chemical 8] Compound (e)
【化９】 [Chemical 9]
【００３８】作成した各電界発光素子の陽極と陰極をリ
−ド線で結び直流電源を接続し、実施例１と同様に電流
密度７．０ｍＡ／ｃｍ2 の電流を２４時間流した。結果
を表１３に示す。The anode and cathode of each of the prepared electroluminescent devices were connected by a lead wire and connected to a DC power source, and a current having a current density of 7.0 mA / cm 2 was supplied for 24 hours as in Example 1. The results are shown in Table 13.
【表１３】 [Table 13]
【００３９】表１２および表１３から明らかなように、
本発明の電界発光素子は比較例の電界発光素子に比べて
光出力および耐久性においては極めて優れていることが
知られる。As is clear from Tables 12 and 13,
It is known that the electroluminescent device of the present invention is extremely superior in light output and durability as compared with the electroluminescent device of the comparative example.
【００４０】実施例６ 酸化錫インジウム（ＩＴＯ）被膜（５０ｎｍ）ガラスの
透明陽極上に、化合物例３５からなる発光層１００ｎ
ｍ、そしてＭｇ／Ａｇ（１０／１）合金からなる陰極２
５０ｎｍを各々順次真空蒸着により形成し、図１に示す
構成の電界発光素子を作成した。Example 6 Indium tin oxide (ITO) coated (50 nm) glass on a transparent anode, a light emitting layer 100n made of Compound Example 35
m, and a cathode 2 made of Mg / Ag (10/1) alloy 2
50 nm was sequentially formed by vacuum vapor deposition to prepare an electroluminescent device having the structure shown in FIG.
【００４１】作成した電界発光素子の陽極と陰極をリ−
ド線で結び直流電源を接続し１０Ｖの電圧を印加したと
ころ、電流密度５．５ｍＡ／ｃｍ2 の電流が素子に流
れ、０．０９ｍＷ／ｃｍ2 の光出力が確認された。The anode and the cathode of the prepared electroluminescent device were read.
When a voltage of 10 V was applied by connecting with a DC line and connecting with a DC line, a current having a current density of 5.5 mA / cm 2 was passed through the element, and an optical output of 0.09 mW / cm 2 was confirmed.
【００４２】そして、そのままの電流密度（５．５ｍＡ
／ｃｍ2 ）を３６時間保ったところ、３６時間後でも最
終出力０．０７ｍＷ／ｃｍ2 の光出力が１２．５Ｖの印
加電圧で得られた。Then, the current density as it is (5.5 mA
/ Cm 2 ) for 36 hours, an optical output with a final output of 0.07 mW / cm 2 was obtained with an applied voltage of 12.5 V even after 36 hours.
【００４３】実施例７〜１１ 実施例１で用いた化合物例３５に代えて、それぞれ化合
物例３６、化合物例３９、化合物例４８、化合物例５
０、化合物例５８を用いた他は、実施例６と同様にし
て、実施例７、実施例８、実施例９、実施例１０、実施
例１１の電界発光素子を作成した。Examples 7 to 11 Instead of the compound example 35 used in the example 1, the compound example 36, the compound example 39, the compound example 48 and the compound example 5 respectively.
0, Compound Example 58 was used, and in the same manner as in Example 6, electroluminescent devices of Example 7, Example 8, Example 9, Example 10, and Example 11 were produced.
【００４４】作成したそれぞれの電界発光素子に、電流
密度５．５ｍＡ／ｃｍ2 の電流を３６時間流した。結果
を表１４に示す。A current having a current density of 5.5 mA / cm 2 was applied to each of the prepared electroluminescent devices for 36 hours. The results are shown in Table 14.
【表１４】 [Table 14]
【００４５】比較例６〜１０ 実施例６で用いた化合物例３５に代えて、下記構造式の
化合物（ｆ）、化合物（ｇ）、化合物（ｈ）、化合物
（ｉ）、前記化合物（ｅ）を用いた他は、実施例６と同
様にして、比較例６、比較例７、比較例８、比較例９、
比較例１０の電界発光素子を作成した。 化合物（ｆ）Comparative Examples 6 to 10 Instead of the compound example 35 used in Example 6, a compound (f), a compound (g), a compound (h), a compound (i) and the compound (e) having the following structural formulas are used. Comparative Example 6, Comparative Example 7, Comparative Example 8, Comparative Example 9, in the same manner as in Example 6 except that
An electroluminescent device of Comparative Example 10 was prepared. Compound (f)
【化１０】 化合物（ｇ）[Chemical 10] Compound (g)
【化１１】 化合物（ｈ）[Chemical 11] Compound (h)
【化１２】 化合物（ｉ）[Chemical 12] Compound (i)
【化１３】 [Chemical 13]
【００４６】作成した各電界発光素子の陽極と陰極をリ
−ド線で結び直流電源を接続し、実施例６と同様に電流
密度５．５ｍＡ／ｃｍ2 の電流を３６時間流した。結果
を表１５に示す。The anode and cathode of each of the prepared electroluminescent devices were connected by a lead wire and connected to a DC power source, and a current having a current density of 5.5 mA / cm 2 was supplied for 36 hours as in Example 6. The results are shown in Table 15.
【表１５】 [Table 15]
【００４７】表１４および表１５から明らかなように、
本発明の電界発光素子は比較例の電界発光素子に比べて
光出力および耐久性においては極めて優れていることが
知られる。As is clear from Tables 14 and 15,
It is known that the electroluminescent device of the present invention is extremely superior in light output and durability as compared with the electroluminescent device of the comparative example.
【００４８】実施例１２ 酸化錫インジウム（ＩＴＯ）被膜（６０ｎｍ）ガラスの
透明陽極上に、化合物例１８からなる発光層６５ｎｍ、
下記構造式の化合物Ａからなる電子輸送層５０ｎｍ、そ
してＭｇ／Ａｇ（１０／１）合金からなる陰極１８０ｎ
ｍを各々順次真空蒸着により形成し、図２に示す構成の
電界発光素子を作成した。化合物ＡExample 12 On a transparent anode of indium tin oxide (ITO) coated (60 nm) glass, a light emitting layer of Compound Example 18 having a thickness of 65 nm,
Electron transport layer 50 nm composed of compound A having the following structural formula, and cathode 180n composed of Mg / Ag (10/1) alloy
m were sequentially formed by vacuum vapor deposition to produce an electroluminescent device having the structure shown in FIG. Compound A
【化１４】 [Chemical 14]
【００４９】作成した電界発光素子の陽極と陰極をリ−
ド線で結び直流電源を接続し８．５Ｖの電圧を印加した
ところ、電流密度６．５ｍＡ／ｃｍ2 の電流が素子に流
れ、０．１８ｍＷ／ｃｍ2 の光出力が確認された。The anode and cathode of the prepared electroluminescent device were read.
When voltage was applied for connecting the tie DC power supply 8.5V with lead wire, current density 6.5 mA / cm 2 flows in the device, the light output of 0.18mW / cm 2 was confirmed.
【００５０】そして、そのままの電流密度（６．５ｍＡ
／ｃｍ2 ）を２４時間保ったところ、２４時間後でも最
終出力０．１７ｍＷ／ｃｍ2 の光出力が８．８Ｖの印加
電圧で得られた。Then, the current density as it is (6.5 mA)
/ Cm 2 ) for 24 hours, a light output with a final output of 0.17 mW / cm 2 was obtained with an applied voltage of 8.8 V even after 24 hours.
【００５１】実施例１３〜１５ 実施例１２で用いた化合物例１８に代えて、それぞれ化
合物例１９、化合物例２７、化合物例３０を用いた他
は、実施例１２と同様にして、実施例１３、実施例１
４、実施例１５の電界発光素子を作成した。Examples 13 to 15 Example 13 was repeated in the same manner as Example 12 except that Compound Example 19, Compound Example 27 and Compound Example 30 were used instead of Compound Example 18 used in Example 12. Example 1
4, the electroluminescent device of Example 15 was prepared.
【００５２】作成したそれぞれの電界発光素子に、電流
密度６．５ｍＡ／ｃｍ2 の電流を流した。結果を表１６
に示す。A current having a current density of 6.5 mA / cm 2 was passed through each of the prepared electroluminescent devices. The results are shown in Table 16
Shown in.
【表１６】 [Table 16]
【００５３】比較例１１〜１３ 実施例１２で用いた化合物例１８に代えて、下記構造式
の化合物（ｊ）、化合物（ｋ）、化合物（ｍ）を用いた
他は、実施例１２と同様にして、比較例１１、比較例１
２、比較例１３の電界発光素子を作成した。化合物
（ｊ）Comparative Examples 11 to 13 Similar to Example 12 except that the compound (j), the compound (k) and the compound (m) having the following structural formulas were used in place of the compound example 18 used in the example 12. Then, Comparative Example 11 and Comparative Example 1
2. An electroluminescent device of Comparative Example 13 was prepared. Compound (j)
【化１５】 化合物（ｋ）[Chemical 15] Compound (k)
【化１６】 化合物（ｍ）[Chemical 16] Compound (m)
【化１７】 [Chemical 17]
【００５４】作成した各電界発光素子の陽極と陰極をリ
−ド線で結び直流電源を接続し、実施例１２と同様に電
流密度６．５ｍＡ／ｃｍ2 の電流を流した。結果を表１
７に示す。The anode and cathode of each of the prepared electroluminescent devices were connected by a lead wire and connected to a direct current power source, and a current having a current density of 6.5 mA / cm 2 was supplied in the same manner as in Example 12. The results are shown in Table 1.
7 shows.
【表１７】 [Table 17]
【００５５】表１６および表１７から明らかなように、
本発明の電界発光素子は比較例の電界発光素子に比べて
光出力においては極めて優れていることが知られる。As is clear from Table 16 and Table 17,
It is known that the electroluminescent device of the present invention is extremely superior in light output as compared with the electroluminescent device of the comparative example.
【００５６】実施例１６ 酸化錫インジウム（ＩＴＯ）被膜（６０ｎｍ）ガラスの
透明陽極上に、化合物例６３からなる発光層５０ｎｍ、
化合物Ａからなる電子輸送層６０ｎｍ、そしてＭｇ／Ａ
ｇ（１０／１）合金からなる陰極２００ｎｍを各々順次
真空蒸着により形成し、図２に示す構成の電界発光素子
を作成した。Example 16 On a transparent anode of indium tin oxide (ITO) coated (60 nm) glass, a light emitting layer of Compound Example 63, 50 nm,
60 nm electron transport layer composed of compound A, and Mg / A
A 200 nm cathode made of a g (10/1) alloy was sequentially formed by vacuum vapor deposition to prepare an electroluminescent device having the structure shown in FIG.
【００５７】作成した電界発光素子の陽極と陰極をリ−
ド線で結び直流電源を接続し８．０Ｖの電圧を印加した
ところ、電流密度７．５ｍＡ／ｃｍ2 の電流が素子に流
れ、０．３５ｍＷ／ｃｍ2 の光出力が確認された。The anode and the cathode of the prepared electroluminescent device were read.
When a direct current power supply was connected and a voltage of 8.0 V was applied by connecting with a power line, a current having a current density of 7.5 mA / cm 2 flowed through the device, and an optical output of 0.35 mW / cm 2 was confirmed.
【００５８】そして、そのままの電流密度（７．５ｍＡ
／ｃｍ2 ）を４８時間保ったところ、４８時間後でも最
終出力０．３２ｍＷ／ｃｍ2 の光出力が８．５Ｖの印加
電圧で得られた。Then, the current density as it is (7.5 mA
/ Cm 2 ) for 48 hours, a light output with a final output of 0.32 mW / cm 2 was obtained with an applied voltage of 8.5 V even after 48 hours.
【００５９】実施例１７〜２０ 実施例１６で用いた化合物例６３に代えて、それぞれ化
合物例３３、化合物例４０、化合物例４９、化合物例６
０を用いた他は、実施例１６と同様にして、実施例１
７、実施例１８、実施例１９、実施例２０の電界発光素
子を作成した。Examples 17 to 20 Instead of the compound example 63 used in the example 16, the compound example 33, the compound example 40, the compound example 49 and the compound example 6 respectively.
Example 1 was repeated in the same manner as in Example 16 except that 0 was used.
Electroluminescent devices of Example 7, Example 18, Example 19, and Example 20 were prepared.
【００６０】作成したそれぞれの電界発光素子に、電流
密度７．５ｍＡ／ｃｍ2 の電流を流した。結果を表１８
に示す。A current having a current density of 7.5 mA / cm 2 was passed through each of the prepared electroluminescent devices. The results are shown in Table 18.
Shown in.
【表１８】 [Table 18]
【００６１】比較例１４〜１６ 実施例１６で用いた化合物例６３に代えて、下記構造式
の化合物（ｎ）、化合物（ｐ）、化合物（ｑ）を用いた
他は、実施例１６と同様にして、比較例１４、比較例１
５、比較例１６の電界発光素子を作成した。化合物
（ｎ）Comparative Examples 14 to 16 The same as Example 16 except that the compound (n), the compound (p) and the compound (q) having the following structural formulas were used in place of the compound example 63 used in the example 16. Comparative Example 14 and Comparative Example 1
5, an electroluminescent device of Comparative Example 16 was prepared. Compound (n)
【化１８】 化合物（ｐ）[Chemical 18] Compound (p)
【化１９】 化合物（ｑ）[Chemical 19] Compound (q)
【化２０】 [Chemical 20]
【００６２】作成した各電界発光素子の陽極と陰極をリ
−ド線で結び直流電源を接続し、実施例１２と同様に電
流密度７．５ｍＡ／ｃｍ2 の電流を流した。結果を表１
９に示す。The anode and cathode of each of the prepared electroluminescent devices were connected by a lead wire and connected to a DC power source, and a current having a current density of 7.5 mA / cm 2 was supplied as in Example 12. The results are shown in Table 1.
9 shows.
【表１９】 [Table 19]
【００６３】表１８および表１９から明らかなように、
本発明の電界発光素子は比較例の電界発光素子に比べて
光出力においては極めて優れていることが知られる。As is clear from Tables 18 and 19,
It is known that the electroluminescent device of the present invention is extremely superior in light output as compared with the electroluminescent device of the comparative example.
【００６４】実施例２１ ガラス基盤上に金からなる陽極５０ｎｍ、下記構造式の
化合物Ｂからなるホ−ル輸送層６０ｎｍ、化合物例２５
からなる発光層６０ｎｍ、そしてアルミニウムからなる
陰極２００ｎｍを各々順次真空蒸着により形成し、図２
に示す構成の電界発光素子を作成した。化合物（Ｂ）Example 21 Anode 50 nm made of gold on a glass substrate, hole transport layer 60 nm made of compound B of the following structural formula, compound example 25
A 60-nm light-emitting layer and a 200-nm cathode made of aluminum are sequentially formed by vacuum evaporation.
An electroluminescent device having the structure shown in was prepared. Compound (B)
【化２１】 [Chemical 21]
【００６５】作成した電界発光素子の陽極と陰極をリ−
ド線で結び直流電源を接続し９Ｖの電圧を印加したとこ
ろ、電流密度７．３ｍＡ／ｃｍ2 の電流が素子に流れ、
０．１１ｍＷ／ｃｍ2 の光出力が確認された。The anode and cathode of the prepared electroluminescent device were read out.
When connecting a DC power supply and applying a voltage of 9 V, a current with a current density of 7.3 mA / cm 2 flows through the element,
A light output of 0.11 mW / cm 2 was confirmed.
【００６６】実施例２２ 酸化錫インジウム（ＩＴＯ）被膜（５０ｎｍ）ガラスの
透明陽極上に、下記構造式の化合物Ｃからなるホ−ル輸
送層５０ｎｍ、化合物例３からなる発光層５０ｎｍ、下
記構造式の化合物Ｄからなる電子輸送層５０ｎｍ、そし
てＭｇ／Ａｇ（１０／１）合金からなる陰極２００ｎｍ
を各々順次真空蒸着により形成し、図３に示す構成の電
界発光素子を作成した。化合物ＣExample 22 On a transparent anode of indium tin oxide (ITO) film (50 nm) glass, a hole transport layer of compound C having the following structural formula, 50 nm, a light emitting layer of compound example 3, 50 nm, and the following structural formula Of electron transport layer consisting of compound D of 50 nm and cathode of Mg / Ag (10/1) alloy 200 nm
Were sequentially formed by vacuum vapor deposition to produce an electroluminescent device having the structure shown in FIG. Compound C
【化２２】 化合物Ｄ[Chemical formula 22] Compound D
【化２３】 [Chemical formula 23]
【００６７】作成した電界発光素子の陽極と陰極をリ−
ド線で結び直流電源を接続し８．０Ｖの電圧を印加した
ところ、電流密度８．０ｍＡ／ｃｍ2 の電流が素子に流
れ、０．１６ｍＷ／ｃｍ2 の光出力が確認された。The anode and the cathode of the prepared electroluminescent device were removed.
When a voltage of 8.0 V was applied by connecting with a DC line and connecting a direct current power supply, a current having a current density of 8.0 mA / cm 2 was passed through the element, and an optical output of 0.16 mW / cm 2 was confirmed.
【００６８】実施例２３〜２７ 実施例２２で用いた化合物例３に代えて、それぞれ化合
物例５、化合物例６、化合物例１４、化合物例２４、化
合物例２６を用いた他は、実施例２２と同様にして、実
施例２３、実施例２４、実施例２５、実施例２６、実施
例２７の電界発光素子を作成した。Examples 23 to 27 Example 22 was repeated except that Compound Example 5, Compound Example 6, Compound Example 14, Compound Example 24 and Compound Example 26 were used instead of Compound Example 3 used in Example 22, respectively. In the same manner as in Example 23, electroluminescent devices of Example 23, Example 24, Example 25, Example 26, and Example 27 were produced.
【００６９】作成したそれぞれの電界発光素子に、電流
密度８．０ｍＡ／ｃｍ2 の電流を流した。結果を表１９
に示す。A current having a current density of 8.0 mA / cm 2 was passed through each of the prepared electroluminescent devices. The results are shown in Table 19
Shown in.
【表２０】 [Table 20]
【００７０】比較例１７〜２０ 実施例２２で用いた化合物例３に代えて、下記構造式の
化合物（ｒ）、前記化合物（ｄ）、下記構造式の化合物
（ｓ）、化合物（ｔ）を用いた他は、実施例２２と同様
にして、比較例１７、比較例１８、比較例１９、比較例
２０の電界発光素子を作成した。化合物（ｒ）Comparative Examples 17 to 20 Instead of the compound example 3 used in Example 22, a compound (r) having the following structural formula, the compound (d), a compound (s) having the following structural formula, and a compound (t) were used. The electroluminescent elements of Comparative Example 17, Comparative Example 18, Comparative Example 19 and Comparative Example 20 were prepared in the same manner as in Example 22 except that the elements were used. Compound (r)
【化２４】 化合物（ｓ）[Chemical formula 24] Compound (s)
【化２５】 化合物（ｔ）[Chemical 25] Compound (t)
【化２６】 [Chemical formula 26]
【００７１】作成した各電界発光素子に実施例２２と同
様に電流密度８．０ｍＡ／ｃｍ2 の電流を流した。結果
を表２１に示す。A current having a current density of 8.0 mA / cm 2 was applied to each of the prepared electroluminescent devices in the same manner as in Example 22. The results are shown in Table 21.
【表２１】 [Table 21]
【００７２】表２０および表２１から明らかなように、
本発明の電界発光素子は比較例の電界発光素子に比べて
光出力においては極めて優れていることが知られる。As is clear from Tables 20 and 21,
It is known that the electroluminescent device of the present invention is extremely superior in light output as compared with the electroluminescent device of the comparative example.
【００７３】実施例２８ ガラス基盤上に金からなる陽極８０ｎｍ、下記構造式の
化合物Ｅからなるホ−ル輸送層８０ｎｍ、化合物例６２
からなる発光層５０ｎｍ、そしてアルミニウムからなる
陰極２００ｎｍを各々順次真空蒸着により形成し、図２
に示す構成の電界発光素子を作成した。化合物（Ｅ）Example 28 Anode 80 nm made of gold on a glass substrate, hole transport layer 80 nm made of compound E of the following structural formula, compound example 62
2 and a cathode 200 nm each made of aluminum are sequentially formed by vacuum vapor deposition.
An electroluminescent device having the structure shown in was prepared. Compound (E)
【化２７】 [Chemical 27]
【００７４】作成した電界発光素子の陽極と陰極をリ−
ド線で結び直流電源を接続し８．０Ｖの電圧を印加した
ところ、電流密度６．５ｍＡ／ｃｍ2 の電流が素子に流
れ、０．２４ｍＷ／ｃｍ2 の光出力が確認された。The anode and the cathode of the prepared electroluminescent device were read.
When voltage was applied for connecting the tie DC power supply 8.0V with lead wire, current density 6.5 mA / cm 2 flows in the device, the light output of 0.24 mW / cm 2 was confirmed.
【００７５】実施例２９ 酸化錫インジウム（ＩＴＯ）被膜（５５ｎｍ）ガラスの
透明陽極上に、前記化合物Ｃからなるホ−ル輸送層６０
ｎｍ、化合物例５２からなる発光層８０ｎｍ、下記構造
式の化合物Ｆからなる電子輸送層６０ｎｍ、そしてＭｇ
／Ａｇ（１０／１）合金からなる陰極１８０ｎｍを各々
順次真空蒸着により形成し、図３に示す構成の電界発光
素子を作成した。化合物ＦExample 29 A hole transport layer 60 made of the above compound C on a transparent anode of indium tin oxide (ITO) coated (55 nm) glass.
nm, a light emitting layer 80 nm comprising Compound Example 52, an electron transporting layer 60 nm comprising Compound F of the following structural formula, and Mg
180 nm of cathodes made of / Ag (10/1) alloy were sequentially formed by vacuum vapor deposition to prepare electroluminescent devices having the structure shown in FIG. Compound F
【化２８】 [Chemical 28]
【００７６】作成した電界発光素子の陽極と陰極をリ−
ド線で結び直流電源を接続し６．５Ｖの電圧を印加した
ところ、電流密度６．０ｍＡ／ｃｍ2 の電流が素子に流
れ、０．２１ｍＷ／ｃｍ2 の光出力が確認された。The anode and cathode of the prepared electroluminescent device were read.
When a direct current power supply was connected and a voltage of 6.5 V was applied by connecting with a lead wire, a current with a current density of 6.0 mA / cm 2 flowed through the device, and an optical output of 0.21 mW / cm 2 was confirmed.
【００７７】実施例３０〜３４ 実施例２９で用いた化合物例５２に代えて、それぞれ化
合物例４１、化合物例４６、化合物例５４、化合物例６
２並びに化合物例６５を用いた他は、実施例２９と同様
にして、実施例３０、実施例３１、実施例３２、実施例
３３並びに実施例３４の電界発光素子を作成した。Examples 30 to 34 Instead of the compound example 52 used in the example 29, the compound example 41, the compound example 46, the compound example 54 and the compound example 6 respectively.
Electroluminescent devices of Example 30, Example 31, Example 32, Example 33, and Example 34 were made in the same manner as Example 29, except that 2 and Compound Example 65 were used.
【００７８】作成したそれぞれの電界発光素子に、電流
密度６．０ｍＡ／ｃｍ2 の電流を流した。結果を表２２
に示す。A current having a current density of 6.0 mA / cm 2 was passed through each of the prepared electroluminescent devices. The results are shown in Table 22.
Shown in.
【表２２】 [Table 22]
【００７９】比較例２１〜２３ 実施例２９で用いた化合物例５２に代えて、下記構造式
の化合物（ｕ）、化合物（ｖ）、化合物（ｗ）を用いた
他は、実施例２９と同様にして、比較例２１、比較例２
２、比較例２３の電界発光素子を作成した。化合物
（ｕ）Comparative Examples 21 to 23 Similar to Example 29 except that compound (u), compound (v) and compound (w) having the following structural formulas were used in place of compound example 52 used in example 29. Comparative Example 21 and Comparative Example 2
2. An electroluminescent device of Comparative Example 23 was prepared. Compound (u)
【化２９】 化合物（ｖ）[Chemical 29] Compound (v)
【化３０】 化合物（ｗ）[Chemical 30] Compound (w)
【化３１】 [Chemical 31]
【００８０】作成した各電界発光素子に実施例２９と同
様に電流密度６．０ｍＡ／ｃｍ2 の電流を流した。結果
を表２３に示す。A current having a current density of 6.0 mA / cm 2 was applied to each of the prepared electroluminescent devices in the same manner as in Example 29. The results are shown in Table 23.
【表２３】 [Table 23]
【００８１】表２２および表２３から明らかなように、
本発明の電界発光素子は比較例の電界発光素子に比べて
光出力においては極めて優れていることが知られる。As is clear from Tables 22 and 23,
It is known that the electroluminescent device of the present invention is extremely superior in light output as compared with the electroluminescent device of the comparative example.
【００８２】実施例３５ 化合物例２８の化合物を２ｇ、下記構造式のホ−ル輸送
化合物Ｇを２ｇ、下記構造式のエレクトロン輸送化合物
Ｈを２ｇおよびポリカ−ボネ−ト（重量平均分子量３
５，０００）７ｇをテトラヒドロフラン３００ミリリッ
トルに溶解し、塗工液を調製した。この塗工液を酸化錫
インジウム（ＩＴＯ）被膜（５０ｎｍ）ガラスの透明陽
極上にマイヤ−バ−で塗布し、３２０ｎｍの層を形成し
た。そして、その上にアルミニウムを真空蒸着し２００
ｎｍの陰極を形成し、電界発光素子を作成した。化合物
ＧExample 35 2 g of the compound of Compound Example 28, 2 g of a hole transporting compound G of the following structural formula, 2 g of an electron transporting compound H of the following structural formula and polycarbonate (weight average molecular weight 3
7 g of 5,000) was dissolved in 300 ml of tetrahydrofuran to prepare a coating solution. This coating liquid was applied on a transparent anode of indium tin oxide (ITO) coated (50 nm) glass with a Mayer bar to form a 320 nm layer. Then, aluminum is vacuum-deposited on it and 200
A cathode having a thickness of 10 nm was formed to prepare an electroluminescence device. Compound G
【化３２】 化合物Ｈ[Chemical 32] Compound H
【化３３】 [Chemical 33]
【００８３】作成した電界発光素子の陽極と陰極をリ−
ド線で結び直流電源を接続し１５Ｖの電圧を印加したと
ころ、電流密度４．１ｍＡ／ｃｍ２ の電流が素子に流
れ、０．０３ｍＷ／ｃｍ２ の光出力が確認された。The anode and the cathode of the prepared electroluminescent device were removed.
When a direct current power supply was connected and a voltage of 15 V was applied by connecting with a power line, a current with a current density of 4.1 mA / cm 2 was passed through the element, and an optical output of 0.03 mW / cm 2 was confirmed.
【００８４】実施例３６ 化合物例４８の化合物を２ｇ、下記構造式のホ−ル輸送
化合物Ｊを２ｇ、下記構造式のエレクトロン輸送化合物
Ｋを３ｇおよびポリカ−ボネ−ト（重量平均分子量３
５，０００）１０ｇをテトラヒドロフラン３２０ミリリ
ットルに溶解し、塗工液を調製した。この塗工液を酸化
錫インジウム（ＩＴＯ）被膜（５０ｎｍ）ガラスの透明
陽極上にマイヤ−バ−で塗布し、４００ｎｍの層を形成
した。そして、その上にアルミニウムを真空蒸着し２０
０ｎｍの陰極を形成し、電界発光素子を作成した。化合
物ＪExample 36 2 g of the compound of Compound Example 48, 2 g of a hole transport compound J of the following structural formula, 3 g of an electron transport compound K of the following structural formula and polycarbonate (weight average molecular weight 3
5,000) 10 g was dissolved in 320 ml of tetrahydrofuran to prepare a coating liquid. This coating liquid was applied on a transparent anode of indium tin oxide (ITO) coated (50 nm) glass with a Mayer bar to form a 400 nm layer. And vacuum-deposit aluminum on it and
A 0 nm cathode was formed to prepare an electroluminescence device. Compound J
【化３４】 化合物Ｋ[Chemical 34] Compound K
【化３５】 [Chemical 35]
【００８５】作成した電界発光素子の陽極と陰極をリ−
ド線で結び直流電源を接続し１６Ｖの電圧を印加したと
ころ、電流密度３．８ｍＡ／ｃｍ2 の電流が素子に流
れ、０．０９ｍＷ／ｃｍ2 の光出力が確認された。The anode and the cathode of the prepared electroluminescent device were re-read.
When connecting the tie DC power supply lead wire voltage was applied 16V, current density 3.8 mA / cm 2 flows in the device, the light output of 0.09mW / cm 2 was confirmed.
【００８６】[0086]
【発明の効果】本発明の電界発光素子は、低い印加電圧
で極めて輝度の高い発光を得ることができ、かつ、耐久
性にも極めて優れている。また、電界発光素子の作成も
真空蒸着あるいはキャスティング法などで作成でき、比
較的安価で大面積の素子を容易に作成することが可能で
あるという顕著な効果を奏する。EFFECT OF THE INVENTION The electroluminescent element of the present invention is capable of obtaining light emission with extremely high brightness at a low applied voltage and is also extremely excellent in durability. Further, the electroluminescent element can be produced by vacuum vapor deposition or casting method, and the remarkable effect that an element having a relatively large area and a large area can be easily produced.
【図１】本発明の電界発光素子の一例の断面図である。FIG. 1 is a cross-sectional view of an example of an electroluminescent device of the present invention.
【図２】本発明の電界発光素子の一例の断面図である。FIG. 2 is a cross-sectional view of an example of the electroluminescent device of the present invention.
【図３】本発明の電界発光素子の一例の断面図である。FIG. 3 is a cross-sectional view of an example of the electroluminescent device of the present invention.
１ 基盤 ２ 陽極 ３ 発光層 ４ 陰極 ５ ホ−ル輸送層 ６ エレクトロン輸送層 1 Substrate 2 Anode 3 Light-emitting layer 4 Cathode 5 Hole transport layer 6 Electron transport layer
Claims (3)
れた一層または複数層の有機化合物より構成される電界
発光素子において、前記有機化合物層のうち少なくとも
一層が下記一般式（１）で示されるアミン骨格を有し、
かつ、同一分子内にカルボニル基を有する化合物を含有
することを特徴とする電界発光素子。一般式（１） 【化１】 式中、Ｒは、置換基を有してもよい、アルキル基または
アラルキル基を示し、Ａｒ1 およびＡｒ2 は、置換基を
有してもよい、芳香環基を示す。1. An electroluminescent device comprising an anode and a cathode and one or more layers of an organic compound sandwiched therebetween, wherein at least one of the organic compound layers is represented by the following general formula (1). Has an amine skeleton
Moreover, an electroluminescent device comprising a compound having a carbonyl group in the same molecule. General formula (1) In the formula, R represents an alkyl group or an aralkyl group which may have a substituent, and Ar 1 and Ar 2 represent an aromatic ring group which may have a substituent.
れた一層または複数層の有機化合物より構成される電界
発光素子において、前記有機化合物層のうち少なくとも
一層が下記一般式（２）で示される化合物を含有するこ
とを特徴とする電界発光素子。一般式（２） 【化２】 式中、Ａｒは、置換基を有してもよい、縮合多環芳香環
基を示し、Ｒ1 、Ｒ2およびＲ3 は、水素原子、置換基
を有してもよい、アルキル基、アラルキル基または芳香
環基を示し（ただし、Ｒ1 とＲ2 が同時に水素原子であ
る場合を除く）、ｎは０または１の整数を示す。2. An electroluminescent device comprising an anode, a cathode, and one or more layers of organic compound sandwiched therebetween, wherein at least one of the organic compound layers is represented by the following general formula (2). An electroluminescent device comprising a compound containing: General formula (2) In the formula, Ar represents a condensed polycyclic aromatic ring group which may have a substituent, and R 1 , R 2 and R 3 each represent a hydrogen atom, an alkyl group which may have a substituent, or an aralkyl. A group or an aromatic ring group (provided that R 1 and R 2 are simultaneously hydrogen atoms), and n represents an integer of 0 or 1.
いて、Ａｒが、置換基を有してもよい、ベンゼン環を４
個以上有する縮合多環芳香環基である請求項２記載の電
界発光素子。3. In the compound represented by the general formula (2), Ar is a benzene ring which may have a substituent.
The electroluminescent element according to claim 2, wherein the electroluminescent element is a condensed polycyclic aromatic ring group having two or more thereof.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4312618A JP3044142B2 (en) | 1992-10-29 | 1992-10-29 | EL device |
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|---|---|---|---|
| JP4312618A JP3044142B2 (en) | 1992-10-29 | 1992-10-29 | EL device |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11351379A Division JP3141023B2 (en) | 1999-12-10 | 1999-12-10 | EL device |
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|---|---|
| JPH06136360A true JPH06136360A (en) | 1994-05-17 |
| JP3044142B2 JP3044142B2 (en) | 2000-05-22 |
Family
ID=18031373
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4312618A Expired - Fee Related JP3044142B2 (en) | 1992-10-29 | 1992-10-29 | EL device |
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| JP (1) | JP3044142B2 (en) |
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