JPH08259934A - Electroluminescent element - Google Patents
Electroluminescent elementInfo
- Publication number
- JPH08259934A JPH08259934A JP7060749A JP6074995A JPH08259934A JP H08259934 A JPH08259934 A JP H08259934A JP 7060749 A JP7060749 A JP 7060749A JP 6074995 A JP6074995 A JP 6074995A JP H08259934 A JPH08259934 A JP H08259934A
- Authority
- JP
- Japan
- Prior art keywords
- group
- light emitting
- electroluminescent device
- layer
- lower alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、各種の表示装置として
広範囲に利用される発光素子であって、低い駆動電圧、
高輝度、かつ安定性に優れた電界発光素子に関するもの
である。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a light emitting element widely used as various display devices, which has a low driving voltage,
The present invention relates to an electroluminescent device having high brightness and excellent stability.
【０００２】[0002]
【従来の技術】電界発光素子は、自己発光のために液晶
素子に比較して明るく、鮮明な表示が可能であるため従
来多くの研究者によって研究されてきた。2. Description of the Related Art Electroluminescent devices have been researched by many researchers because they are self-luminous and can display brighter and sharper images than liquid crystal devices.
【０００３】現在、実用レベルに達した電界発光素子と
しては無機材料のＺｎＳを用いた素子がある。At present, as an electroluminescent device which has reached a practical level, there is a device using ZnS which is an inorganic material.
【０００４】しかし、この様な無機の電界発光素子は発
光のための駆動電圧として２００Ｖ以上が必要で広く使
用されるには至っていない。However, such an inorganic electroluminescent device requires a driving voltage of 200 V or more for emitting light and has not been widely used.
【０００５】これに対して有機材料を用いた電界発光素
子である有機電界発光素子は、従来実用的なレベルから
はほど遠いものであったが、１９８７年にコダック社の
Ｃ．Ｗ．Ｔａｎｇらによって開発された積層構造素子に
よりその特性が飛躍的に進歩した。On the other hand, an organic electroluminescence device, which is an electroluminescence device using an organic material, is far from a practical level in the past, but in 1987, a C.D. W. The laminated structure element developed by Tang et al. Has dramatically improved its characteristics.
【０００６】彼らは蒸着膜の構造が安定で電子を輸送す
ることの出来る蛍光体と、正孔を輸送することの出来る
有機物を積層し、両方のキャリヤーを蛍光体中に注入し
て発光させることに成功した。[0006] They have a structure in which a vapor-deposited film is stable and stack a phosphor capable of transporting electrons and an organic material capable of transporting holes, and both carriers are injected into the phosphor to emit light. succeeded in.
【０００７】これによって有機電界発光素子の発光効率
が向上し、１０Ｖ以下の電圧で１０００ｃｄ／ｍ2 以上
の発光が得られる様になった。As a result, the luminous efficiency of the organic electroluminescent device was improved, and light emission of 1000 cd / m 2 or more was obtained at a voltage of 10 V or less.
【０００８】その後多くの研究者によってその特性向上
のための研究が行われ、現在では１００００ｃｄ／ｍ2
以上の発光特性が得られている。[0008] Since then, many researchers have conducted research to improve the characteristics, and at present, 10,000 cd / m 2
The above emission characteristics are obtained.
【０００９】この様な有機電界発光素子の基本的な発光
特性はすでに十分実用範囲にあり、現在その実用化を妨
げている最も大きな課題は、駆動時の発光特性の安定性
の不足にある。The basic light emitting characteristics of such an organic electroluminescent device are already in a practical range, and the biggest problem that hinders its practical use is the lack of stability of the light emitting characteristics during driving.
【００１０】具体的には、発光輝度が低下したり、ダー
クスポットと呼ばれる発光しない領域が発生したり、素
子の短絡により破壊が起きてしまうことである。Specifically, the light emission luminance is lowered, a dark spot, which is a non-light emitting region, is generated, or the element is short-circuited to cause destruction.
【００１１】[0011]
【発明が解決しようとする課題】本発明は、以上の様な
状況を鑑み、従来の電界発光素子の技術的課題を解決
し、駆動電圧が低く、高輝度でさらに発光安定性に優れ
た有機電界発光素子を実現出来る新規な電界発光素子を
提供することを目的とすし、特に連続発光時の発光輝度
の低下が格段に優れた電界発光素子を提供することにあ
る。SUMMARY OF THE INVENTION In view of the above situation, the present invention solves the technical problems of the conventional electroluminescent device, has a low driving voltage, high brightness, and is excellent in light emission stability. It is an object of the present invention to provide a novel electroluminescent device that can realize the electroluminescent device, and particularly to provide an electroluminescent device that is remarkably excellent in reduction in emission luminance during continuous light emission.
【００１２】[0012]
【課題を解決するための手段】上記目的を達成するため
に、本発明者らは様々な電界発光素子を試作し、発光の
安定性の評価を行った。In order to achieve the above object, the present inventors made various electroluminescent devices as prototypes and evaluated the stability of light emission.
【００１３】その結果、請求項１から８記載の電界発光
素子では発光安定性が大きく向上することを見出した。As a result, it has been found that the electroluminescence device according to claims 1 to 8 has a significantly improved light emission stability.
【００１４】以下順次説明する。請求項１から４記載の
発明では、以下の（化７）、（化８）、（化９）、（化
１０）で記述されるアミン化合物と発光材の混合層を発
光層に接して設けた。The steps will be sequentially described below. In the invention according to claims 1 to 4, a mixed layer of an amine compound and a light emitting material described in the following (Chemical formula 7), (Chemical formula 8), (Chemical formula 9) and (Chemical formula 10) is provided in contact with the luminous layer. It was
【００１５】[0015]
【化７】 [Chemical 7]
【００１６】[0016]
【化８】 Embedded image
【００１７】[0017]
【化９】 [Chemical 9]
【００１８】[0018]
【化１０】 ただし、（化７）におけるＲ1、Ｒ2は水素原子、低級ア
ルキル基、低級アルコキシ基、フェニル基、低級アルキ
ル基または低級アルコキシ基を置換基として有するフェ
ニル基、Ｒ3は水素原子、メチル基、メトキシ基、また
は塩素原子を表し、Ｒ1、Ｒ2の少なくとも一方は、ノル
マルブチル基、イソブチル基、セカンダリブチル基、タ
ーシャルブチル基、フェニル基、低級アルキル基または
低級アルコキシ基を有するフェニル基を表す。[Chemical 10] However, R 1 and R 2 in (Chemical Formula 7) are a hydrogen atom, a lower alkyl group, a lower alkoxy group, a phenyl group, a phenyl group having a lower alkyl group or a lower alkoxy group as a substituent, and R 3 is a hydrogen atom or a methyl group. , A methoxy group, or a chlorine atom, and at least one of R 1 and R 2 is a phenyl group having a normal butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a phenyl group, a lower alkyl group or a lower alkoxy group. Represents
【００１９】また、（化８）におけるＲ4、Ｒ5、Ｒ6は
同一でも異なっていてもよく、水素原子、低級アルキル
基、低級アルコキシ基、置換または無置換のアリール基
を表し、Ｒ7は水素原子、低級アルキル基、低級アルコ
キシ基、または塩素原子を表し、Ａ1は以下の（Ａ）か
ら（Ｍ）のいずれかの構造を有する置換基を表す。R 4 , R 5 and R 6 in the chemical formula 8 may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a substituted or unsubstituted aryl group, and R 7 Represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a chlorine atom, and A 1 represents a substituent having a structure of any of the following (A) to (M).
【００２０】[0020]
【化１１】 ここで、（Ｃ）中のＲ8は水素原子、メチル基、メトキ
シ基、または塩素原子を表す。[Chemical 11] Here, R 8 in (C) represents a hydrogen atom, a methyl group, a methoxy group, or a chlorine atom.
【００２１】また、（化９）におけるＲ9 、Ｒ10は水素
原子、低級アルキル基、低級アルコキシ基、置換または
無置換のフェニル基を表し、Ｒ11は水素原子、メチル
基、メトキシ基、塩素原子を表す。Further, R 9 and R 10 in the chemical formula 9 represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a substituted or unsubstituted phenyl group, and R 11 represents a hydrogen atom, a methyl group, a methoxy group or chlorine. Represents an atom.
【００２２】また、（化１０）における、Ｒ12、Ｒ13は
同一でも異なっていてもよく、水素原子、低級アルキル
基、低級アルコキシ基、置換または無置換のアリール基
を表し、Ｒ14は水素原子、低級アルキル基、低級アルコ
キシ基、または塩素原子を表し、Ａ2は以下の（Ａ）か
ら（Ｍ）のいずれかの構造を有する置換基を表す。R 12 and R 13 in the chemical formula 10 may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a substituted or unsubstituted aryl group, and R 14 is hydrogen. Represents an atom, a lower alkyl group, a lower alkoxy group, or a chlorine atom, and A 2 represents a substituent having a structure of any of (A) to (M) below.
【００２３】[0023]
【化１２】 ここで、（Ｃ）中のＲ8は水素原子、メチル基、メトキ
シ基、または塩素原子を表す。[Chemical 12] Here, R 8 in (C) represents a hydrogen atom, a methyl group, a methoxy group, or a chlorine atom.
【００２４】また、混合層の形成方法としては真空蒸着
法などの乾式成膜法や、スピンコート法などの湿式成膜
法などがあげられる。Examples of the method for forming the mixed layer include a dry film forming method such as a vacuum vapor deposition method and a wet film forming method such as a spin coating method.
【００２５】さらに真空蒸着法では、複数の蒸着源より
同時に異なった材料を蒸着して混合層を作製することが
好まれるが、複数の材料を混合させ単一の蒸着源を用い
て蒸着を行い混合層を作製することも可能である。な
お、混合層の膜厚は１００ｎｍ以下が適当であり、さら
には５０ｎｍ以下が特に好ましい。Further, in the vacuum vapor deposition method, it is preferable that different materials are simultaneously vapor-deposited from a plurality of vapor deposition sources to form a mixed layer. However, a plurality of materials are mixed and vapor deposition is performed using a single vapor deposition source. It is also possible to create mixed layers. The thickness of the mixed layer is preferably 100 nm or less, more preferably 50 nm or less.
【００２６】また、発光材としては各種の金属錯体化合
物、オキサジアゾール誘導体などの有機色素化合物、ポ
リパラフェニレンビニレンなどの高分子化合物など各種
の材料を用いることができるが、発光層に用いる発光材
と混合層に用いる発光材は基本的には同一の材料が好適
である。As the light emitting material, various materials such as various metal complex compounds, organic dye compounds such as oxadiazole derivatives, and polymer compounds such as polyparaphenylene vinylene can be used. Basically, the same material is suitable for the light emitting material used for the material and the mixed layer.
【００２７】また、発光層にキナクリドンやクマリンな
どのドーパントを添加することによりさらに高性能の電
界発光素子を作製することができる。Further, by adding a dopant such as quinacridone or coumarin to the light emitting layer, a higher performance electroluminescent device can be manufactured.
【００２８】また、請求項５記載の発明のようにアミン
化合物としては上記で示されるものから複数種選んで発
光材と混合してもよい。Further, as in the invention described in claim 5, as the amine compound, a plurality of kinds may be selected from the compounds shown above and mixed with the light emitting material.
【００２９】また、請求項７の発明のように陽極からの
正孔の注入を改善するためにホール輸送層を設けるとよ
い。A hole transport layer may be provided to improve the injection of holes from the anode as in the seventh aspect of the invention.
【００３０】このホール輸送層は単一の化合物でも複数
の化合物から形成されていてもよく、また単層でも積層
されていてもよく、さらには、本発明で示したアミン化
合物を用いるとなおよい。This hole transport layer may be formed of a single compound or a plurality of compounds, may be a single layer or may be laminated, and it is more preferable to use the amine compound shown in the present invention. .
【００３１】また、請求項８記載の発明のように陰極と
発光層の間に電子輸送層を設け陰極からの電子の注入を
改善するとさらによい。It is more preferable to provide an electron transport layer between the cathode and the light emitting layer to improve injection of electrons from the cathode.
【００３２】[0032]
【作用】本発明の構成中のアミン化合物は、耐熱性の向
上した優れた正孔輸送性の化合物であり、本発明は、こ
のような化合物と発光材の混合した層を発光層に接して
設けた素子構成を有する。The amine compound in the constitution of the present invention is a compound having an excellent hole transporting property with improved heat resistance. In the present invention, a layer in which such a compound and a light emitting material are mixed is brought into contact with the light emitting layer. It has the element configuration provided.
【００３３】このため、連続して発光させた際の発光層
界面の劣化が大幅に抑制され、発光安定性がきわめて改
善される。Therefore, the deterioration of the interface of the light emitting layer when light is emitted continuously is greatly suppressed, and the light emission stability is significantly improved.
【００３４】[0034]
【実施例】以下に、本発明につき実施例を用いてより具
体的に説明する。EXAMPLES Hereinafter, the present invention will be described more specifically by way of examples.
【００３５】本発明はこれらによって何等の限定を受け
るものではない。なお以下の実施例では、発光材とし
て、トリス（８−キノリノール）アルミニウム（Ａｌ
ｑ）を用い、陽極、正孔輸送層、混合層、発光層、陰極
を有する素子の実施例を示すが、本発明の技術的思想
は、これらの実施例の具体的構成により何等の限定を受
けるものではないことはいうまでもない。The present invention is not limited to these. In the following examples, tris (8-quinolinol) aluminum (Al
Examples of an element having an anode, a hole transport layer, a mixed layer, a light emitting layer, and a cathode are shown by using q), but the technical idea of the present invention is not limited by the specific configuration of these examples. It goes without saying that you do not receive it.
【００３６】（実施例１）以下、本発明の実施例１につ
いて説明をする。Example 1 Hereinafter, Example 1 of the present invention will be described.
【００３７】図１は、本実施例の電界発光素子の斜視図
を示す。図１において、１はガラス電極、２は透明電
極、３は正孔（ホール）輸送層、４は混合層、５は発光
層、６は電極である。FIG. 1 shows a perspective view of the electroluminescent device of this embodiment. In FIG. 1, 1 is a glass electrode, 2 is a transparent electrode, 3 is a hole transport layer, 4 is a mixed layer, 5 is a light emitting layer, and 6 is an electrode.
【００３８】この電界発光素子は、ガラス基板１上に透
明電極２としてＩＴＯ電極をあらかじめ形成したものの
上に、正孔輸送層３、アミン化合物と発光材の混合層
４、発光層５、アルミニウム／リチウム（Ａｌ／Ｌｉ）
電極６の順に蒸着して積層構造として作製したものであ
るが、その製造過程について、より詳細に説明をする。In this electroluminescent device, an ITO electrode is formed in advance as a transparent electrode 2 on a glass substrate 1, a hole transport layer 3, a mixed layer 4 of an amine compound and a light emitting material, a light emitting layer 5, and an aluminum / Lithium (Al / Li)
The electrode 6 is vapor-deposited in this order to form a laminated structure, and the manufacturing process thereof will be described in more detail.
【００３９】まず、十分に洗浄したガラス基板１（ＩＴ
Ｏ電極２は成膜済み）に対して、前記（化７）のＲ1＝
ｐ-ｔ-Ｃ4Ｈ9、Ｒ2＝Ｈ、Ｒ3＝Ｈであるアミン化合物
（１）、電子輸送性発光材として精製したＡｌｑを蒸着
装置にセットした。First, the glass substrate 1 (IT
For the O electrode 2 already formed, R 1 = (Formula 7)
The amine compound (1) having p-t-C 4 H 9 , R 2 = H, and R 3 = H, and Alq purified as an electron-transporting light-emitting material were set in a vapor deposition apparatus.
【００４０】次に、１０-6ｔｏｒｒまで排気した後、
０．１ｎｍ／秒の速度でアミン化合物（１）を蒸着し、
正孔輸送層３を５０ｎｍ形成した。Next, after exhausting to 10 -6 torr,
The amine compound (1) is vapor-deposited at a rate of 0.1 nm / sec,
The hole transport layer 3 was formed to a thickness of 50 nm.
【００４１】次に、アミン化合物（１）とＡｌｑを異な
る蒸着源より、それぞれ０．１ｎｍ／秒の速度で蒸着
し、アミン化合物（１）と発光材の混合層４を３０ｎｍ
形成した。Next, the amine compound (1) and Alq are vapor-deposited at different rates from each other at a rate of 0.1 nm / sec to form the mixed layer 4 of the amine compound (1) and the luminescent material at 30 nm.
Formed.
【００４２】次に、発光層５の蒸着はＡｌｑを０．１ｎ
ｍ／秒の速度で行い、その膜厚を５０ｎｍとし、発光層
５を積層した。Next, the light emitting layer 5 is vapor-deposited with Alq of
The light emitting layer 5 was laminated at a speed of m / sec to a thickness of 50 nm.
【００４３】最後に、Ａｌ／Ｌｉ電極６の蒸着は１ｎｍ
／秒の速度で行い、その厚さを１５０ｎｍとし、電極６
を積層し、電界発光素子を作製した。Finally, the vapor deposition of the Al / Li electrode 6 is 1 nm.
Electrode / 6
Were laminated to produce an electroluminescent device.
【００４４】なお、これらの蒸着はいずれも真空を破ら
ずに連続して行い、膜厚は水晶振動子によってモニター
した。All of these vapor depositions were continuously performed without breaking the vacuum, and the film thickness was monitored by a crystal oscillator.
【００４５】そして、素子作製後、直ちに乾燥窒素中で
電極の取り出しを行い、引続き特性測定を行った。Immediately after the device was manufactured, the electrode was taken out in dry nitrogen, and the characteristics were continuously measured.
【００４６】ここで、得られた素子の発光特性は１００
ｍＡ／ｃｍ2の電流を印加した場合の発光輝度で定義し
た。Here, the emission characteristics of the obtained device is 100.
It was defined as the emission luminance when a current of mA / cm 2 was applied.
【００４７】そして、発光の安定性は５００ｃｄ／ｍ2
の発光が得られる電流を連続で印加し、その時の発光輝
度の変化を測定した。The emission stability is 500 cd / m 2
The current for obtaining the luminescence was continuously applied, and the change in the luminescence brightness at that time was measured.
【００４８】また、発光の寿命を、輝度が半分の２５０
ｃｄ／ｍ2になるまでの時間と定義した。In addition, the life of light emission is reduced to 250, which is half the brightness.
It was defined as the time to reach cd / m 2 .
【００４９】その結果、発光特性は２５００ｃｄ／ｍ2
であり、発光の寿命は２１００ｈであった。As a result, the emission characteristic was 2500 cd / m 2.
And the life of light emission was 2100 h.
【００５０】ついで、比較のためにアミン化合物（１）
とＡｌｑとの混合層を形成しない以外は、上記と同様に
して電界発光素子を作製し特性を調べた。Then, for comparison, the amine compound (1)
And an Alq mixed layer were not formed, and an electroluminescent device was produced in the same manner as described above, and the characteristics were examined.
【００５１】その結果、発光特性、発光の寿命特性はそ
れぞれ、２５００ｃｄ／ｍ2、６２０ｈであった。As a result, the emission characteristics and the emission lifetime characteristics were 2500 cd / m 2 and 620 h, respectively.
【００５２】さらに、アミン化合物（１）の代わりに、
以下の（化１３）に示す代表的な正孔輸送性材料（略称
ＴＰＤ）を用いた以外は上記と同様に電界発光素子を作
製して特性を調べた。Further, instead of the amine compound (1),
An electroluminescent device was produced in the same manner as above except that a typical hole transporting material (abbreviation TPD) shown in the following (Chemical Formula 13) was used, and the characteristics were examined.
【００５３】[0053]
【化１３】 その結果、この比較例における発光特性、発光の寿命特
性はそれぞれ、２３００ｃｄ／ｍ2、１５０ｈであっ
た。[Chemical 13] As a result, the emission characteristics and emission lifetime characteristics of this comparative example were 2300 cd / m 2 and 150 h, respectively.
【００５４】以上より、本実施例においては、本発明に
なるアミン化合物（１）と発光材の混合層を設けた電界
発光素子は、発光特性に優れ、さらに発光寿命が格段に
向上することが確認された。As described above, in this example, the electroluminescent device provided with the mixed layer of the amine compound (1) and the light emitting material according to the present invention has excellent light emitting characteristics and the light emitting life is remarkably improved. confirmed.
【００５５】（実施例２）以下、本発明の実施例２につ
いて説明をする。(Second Embodiment) A second embodiment of the present invention will be described below.
【００５６】本実施例では、アミン化合物（１）の代わ
りに、それぞれ、アミン化合物（２）（Ｒ1＝ｐ-ｉｓｏ
-Ｃ4Ｈ9、Ｒ2＝Ｈ、Ｒ3＝Ｈ）、（３）（Ｒ1＝ｐ-ｔ-Ｃ
4Ｈ9、Ｒ2＝ｐ-ｔ-Ｃ4Ｈ9、Ｒ3＝Ｈ）、（４）（Ｒ1＝
ｐ-Ｃ6Ｈ5、Ｒ2＝ｐ-Ｃ6Ｈ5、Ｒ3＝Ｈ）、（５）（Ｒ1
＝ｐ-ＣＨ3-Ｃ6Ｈ4、Ｒ2＝ｐ-ＣＨ3-Ｃ6Ｈ4、Ｒ3＝Ｈ）
を用いた以外は実施例１と同様な方法で電界発光素子を
作製し、その特性を評価した。In this example, instead of the amine compound (1), the amine compound (2) (R 1 = p-iso) was used.
-C 4 H 9 , R 2 = H, R 3 = H), (3) (R 1 = p-t-C
4 H 9 , R 2 = p-t-C 4 H 9 , R 3 = H), (4) (R 1 =
p-C 6 H 5, R 2 = p-C 6 H 5, R 3 = H), (5) (R 1
= P-CH 3 -C 6 H 4, R 2 = p-CH 3 -C 6 H 4, R 3 = H)
An electroluminescent device was produced in the same manner as in Example 1 except that was used, and its characteristics were evaluated.
【００５７】さらに、比較のために各アミン化合物と発
光材の混合層を設けていない素子を作製し特性を評価し
た。Further, for comparison, an element having no mixed layer of each amine compound and the light emitting material was prepared and its characteristics were evaluated.
【００５８】それらの結果を以下の（表１）に示す。The results are shown in (Table 1) below.
【００５９】[0059]
【表１】 以上より、本実施例については、本発明になるアミン化
合物（２）〜（５）と発光材の混合層を用いた電界発光
素子は、発光特性に優れ、さらに発光寿命が格段に向上
することが確認された。[Table 1] As described above, in this example, the electroluminescent device using the mixed layer of the amine compounds (2) to (5) and the light emitting material according to the present invention has excellent light emitting characteristics and further has a significantly improved light emitting life. Was confirmed.
【００６０】（実施例３）以下、本発明の実施例３につ
いて説明をする。(Third Embodiment) A third embodiment of the present invention will be described below.
【００６１】本実施例では、アミン化合物（１）の代わ
りに、それぞれ、前記（化８）のアミン化合物（６）
（Ｒ4＝Ｈ、Ｒ5＝Ｈ、Ｒ6＝Ｈ、Ｒ7＝Ｈ、Ａ1＝
（Ａ））、（７）（Ｒ4＝Ｈ、Ｒ5＝Ｈ、Ｒ6＝Ｈ、Ｒ7＝
Ｈ、Ｒ8＝Ｈ、Ａ1＝（Ｃ））、（８）（Ｒ4＝ｐ-ｔ-Ｃ4
Ｈ9、Ｒ5＝ｐ-ｔ-Ｃ4Ｈ9、Ｒ6＝Ｈ、Ｒ7＝Ｈ、Ｒ8＝
Ｈ、Ａ1＝（Ｃ））、（９）（Ｒ4＝Ｈ、Ｒ5＝Ｈ、Ｒ6＝
Ｈ、Ｒ7＝Ｈ、Ａ1＝（Ｆ））、（１０）（Ｒ4＝Ｈ、Ｒ5
＝Ｈ、Ｒ6＝Ｈ、Ｒ7＝Ｈ、Ａ1＝（Ｈ））を用いた以外
は実施例１と同様な方法で電界発光素子を作製し、その
特性を評価した。In this example, instead of the amine compound (1), the amine compound (6) of the above (Chemical Formula 8) was used.
(R 4 = H, R 5 = H, R 6 = H, R 7 = H, A 1 =
(A)), (7) (R 4 = H, R 5 = H, R 6 = H, R 7 =
H, R 8 = H, A 1 = (C)), (8) (R 4 = p-t-C 4
H 9 , R 5 = p-t-C 4 H 9 , R 6 = H, R 7 = H, R 8 =
H, A 1 = (C)), (9) (R 4 = H, R 5 = H, R 6 =
H, R 7 = H, A 1 = (F), (10) (R 4 = H, R 5
= H, R 6 = H, R 7 = H, A 1 = (H)), an electroluminescent device was prepared in the same manner as in Example 1 and its characteristics were evaluated.
【００６２】さらに、比較のために各アミン化合物と発
光材の混合層を設けていない素子を作製し特性を評価し
た。Further, for comparison, an element having no mixed layer of each amine compound and the light emitting material was prepared and the characteristics were evaluated.
【００６３】それらの結果を、以下の（表２）に示す。The results are shown in (Table 2) below.
【００６４】[0064]
【表２】 以上より、本実施例については、本発明になるアミン化
合物（６）〜（１０）と発光材の混合層を用いた電界発
光素子は、発光特性に優れ、さらに発光寿命が格段に向
上することが確認された。[Table 2] As described above, in this example, the electroluminescent device using the mixed layer of the amine compounds (6) to (10) and the light emitting material according to the present invention has excellent light emitting characteristics and further has a significantly improved light emitting life. Was confirmed.
【００６５】（実施例４）以下、本発明の実施例４につ
いて説明をする。(Fourth Embodiment) The fourth embodiment of the present invention will be described below.
【００６６】本実施例では、アミン化合物（１）の代わ
りに、それぞれ、前記（化９）のアミン化合物（１１）
（Ｒ9＝Ｈ、Ｒ10＝Ｈ、Ｒ11＝Ｈ）、（１２）（Ｒ9＝ｐ
-ＣＨ3、Ｒ10＝ｐ-ＣＨ3、Ｒ11＝ＣＨ3）（１３）（Ｒ9
＝ｐ-ｔ-Ｃ4Ｈ9、Ｒ10＝ｐ-ｔ-Ｃ4Ｈ9、Ｒ11＝Ｈ）、
（１４）（Ｒ9＝ｐ-ｉｓｏ-Ｃ4Ｈ9、Ｒ10＝ｐ-ｉｓｏ-
Ｃ4Ｈ9、Ｒ11＝Ｈ）、（１５）（Ｒ9＝ｐ-Ｃ6Ｈ5、Ｒ10
＝ｐ-Ｃ6Ｈ5、Ｒ11＝Ｈ）を用いた以外は、実施例１と
同様な方法で電界発光素子を作製し、その特性を評価し
た。In the present example, instead of the amine compound (1), the amine compound (11) of the above (Chemical Formula 9) was used.
(R 9 = H, R 10 = H, R 11 = H), (12) (R 9 = p
-CH 3 , R 10 = p-CH 3 , R 11 = CH 3 ) (13) (R 9
= P-t-C 4 H 9, R 10 = p-t-C 4 H 9, R 11 = H),
(14) (R 9 = p-iso-C4H9, R10 = p-iso-
C 4 H 9 , R 11 = H), (15) (R 9 = p-C 6 H 5 , R 10
= P-C 6 H 5, R 11 = H) except for using is to produce electroluminescence device in the same manner as in Example 1, and the characteristics were evaluated.
【００６７】さらに、比較のために各アミン化合物と発
光材の混合層を設けていない素子を作製し特性を評価し
た。Further, for comparison, an element having no mixed layer of each amine compound and the light emitting material was prepared and its characteristics were evaluated.
【００６８】それらの結果を以下の（表３）に示す。The results are shown in (Table 3) below.
【００６９】[0069]
【表３】 以上より、本実施例については、本発明になるアミン化
合物（１１）〜（１５）と発光材の混合層を用いた電界
発光素子は、発光特性に優れ、さらに発光寿命が格段に
向上することが確認された。[Table 3] As described above, in this example, the electroluminescent device using the mixed layer of the amine compounds (11) to (15) and the light emitting material according to the present invention has excellent light emitting characteristics and further has a significantly improved light emitting life. Was confirmed.
【００７０】（実施例５）以下、本発明の実施例５につ
いて説明をする。(Fifth Embodiment) A fifth embodiment of the present invention will be described below.
【００７１】本実施例では、アミン化合物（１）の代わ
りに、それぞれ、前記（化１０）のアミン化合物（１
６）（Ｒ12＝ｐ-ＣＨ3、Ｒ13＝ｐ-ＣＨ3、Ｒ14＝Ｈ、Ａ
2＝（Ａ））、（１７）（Ｒ12＝Ｈ、Ｒ13＝Ｈ、Ｒ14＝
Ｈ、Ｒ8＝Ｈ、Ａ2＝（Ｃ））、（１８）（Ｒ12＝ｐ-ｔ-
Ｃ4Ｈ9、Ｒ13＝ｐ-ｔ-Ｃ4Ｈ9、Ｒ14＝Ｈ、Ｒ8＝Ｈ、Ａ2
＝（Ｃ））、（１９）（Ｒ12＝Ｈ、Ｒ13＝Ｈ、Ｒ14＝
Ｈ、Ａ2＝（Ｆ））、（２０）（Ｒ12＝Ｈ、Ｒ13＝Ｈ、
Ｒ14＝Ｈ、Ａ2＝（Ｈ））を用いた以外は実施例１と同
様な方法で電界発光素子を作製し、その特性を評価し
た。In this example, instead of the amine compound (1), the amine compound (1
6) (R 12 = p-CH 3 , R 13 = p-CH 3 , R 14 = H, A
2 = (A)), (17) (R 12 = H, R 13 = H, R 14 =
H, R 8 = H, A 2 = (C)), (18) (R 12 = p-t-
C 4 H 9 , R 13 = p-t-C 4 H 9 , R 14 = H, R 8 = H, A 2
= (C)), (19) (R 12 = H, R 13 = H, R 14 =
H, A 2 = (F)), (20) (R 12 = H, R 13 = H,
An electroluminescent device was prepared in the same manner as in Example 1 except that R 14 = H and A 2 = (H)) were used, and the characteristics thereof were evaluated.
【００７２】さらに、比較のために各アミン化合物と発
光材の混合層を設けていない素子を作製し特性を評価し
た。Further, for comparison, an element having no mixed layer of each amine compound and the light emitting material was prepared and the characteristics were evaluated.
【００７３】それらの結果を以下の（表４）に示す。The results are shown in Table 4 below.
【００７４】[0074]
【表４】 以上より、本実施例については、本発明になるアミン化
合物（１６）〜（２０）と発光材の混合層を用いた電界
発光素子は、発光特性に優れ、さらに発光寿命が格段に
向上することが確認された。[Table 4] As described above, in this example, the electroluminescent device using the mixed layer of the amine compounds (16) to (20) and the light emitting material according to the present invention is excellent in light emitting characteristics and further has a significantly improved light emitting life. Was confirmed.
【００７５】（実施例６）以下、本発明の実施例６につ
いて説明をする。(Sixth Embodiment) The sixth embodiment of the present invention will be described below.
【００７６】アミン化合物（１）の代わりに、アミン化
合物（１）と（７）を用いて、発光材であるＡｌｑとの
混合層を形成した以外は、実施例１と同様な方法で電界
発光素子を作製し、その特性を評価した。Electroluminescence was performed in the same manner as in Example 1 except that the amine compound (1) and the amine compound (7) were used in place of the amine compound (1) to form a mixed layer with Alq as a light emitting material. A device was prepared and its characteristics were evaluated.
【００７７】その結果、発光特性は２４００ｃｄ／ｍ2
であり、発光の寿命は２５００ｈであった。As a result, the emission characteristics were 2400 cd / m 2.
And the life of light emission was 2500 h.
【００７８】比較のためにアミン化合物（１）、（７）
とＡｌｑとの混合層を形成しない以外は、上記と同様に
して、電界発光素子を作製し特性を調べた。For comparison, amine compounds (1) and (7)
And an Alq mixed layer were not formed, and an electroluminescent device was produced in the same manner as above, and the characteristics were examined.
【００７９】その結果、発光特性、発光の寿命特性はそ
れぞれ、２５００ｃｄ／ｍ2、６２０ｈであった。As a result, the emission characteristics and the emission lifetime characteristics were 2500 cd / m 2 and 620 h, respectively.
【００８０】以上より、本実施例については、本発明に
なるアミン化合物（１）、（７）と発光材の混合層を設
けた電界発光素子は、発光特性に優れ、さらに発光寿命
が格段に向上することが確認された。As described above, in this example, the electroluminescent device provided with the mixed layer of the amine compounds (1) and (7) and the light emitting material according to the present invention has excellent light emitting characteristics and has a significantly long light emitting life. It was confirmed to improve.
【００８１】[0081]
【発明の効果】以上のように、本発明は、最適化された
アミン化合物と発光材の混合層を設けた電界発光素子で
あり、本発明の材料及び構成を用いることにより、従来
の電界発光素子の最も大きな技術的課題であった発光安
定性を格段に改良した電界発光素子を実現することがで
きる。INDUSTRIAL APPLICABILITY As described above, the present invention is an electroluminescent device provided with an optimized mixed layer of an amine compound and a light emitting material, and by using the material and constitution of the present invention, conventional electroluminescence is achieved. It is possible to realize an electroluminescent device in which the light emission stability, which has been the greatest technical issue of the device, is significantly improved.
【図１】本発明の一実施例における電界発光素子の構成
を示す部分断面拡大斜視図FIG. 1 is a partially enlarged cross-sectional perspective view showing a configuration of an electroluminescent device according to an embodiment of the present invention.
１ ガラス基板 ２ 透明電極 ３ 正孔輸送層 ４ アミン化合物と発光材の混合層 ５ 電子輸送層兼発光層 ６ Ａｌ／Ｌｉ電極 1 Glass Substrate 2 Transparent Electrode 3 Hole Transport Layer 4 Mixed Layer of Amine Compound and Light Emitting Material 5 Electron Transport Layer and Light Emitting Layer 6 Al / Li Electrode
Claims (9)
発光材の混合層を発光層に接して設けた電界発光素子。 【化１】 ただし、Ｒ1、Ｒ2は水素原子、低級アルキル基、低級ア
ルコキシ基、フェニル基、低級アルキル基または低級ア
ルコキシ基を置換基として有するフェニル基、Ｒ 3は水
素原子、メチル基、メトキシ基、または塩素原子を表
し、Ｒ1、Ｒ2の少なくとも一方は、イソブチル基、セカ
ンダリブチル基、ターシャルブチル基、フェニル基、低
級アルキル基または低級アルコキシ基を有するフェニル
基を表す。1. An amine compound represented by the following general formula:
An electroluminescent device in which a mixed layer of light emitting materials is provided in contact with the light emitting layer. [Chemical 1]However, R1, R2Is a hydrogen atom, a lower alkyl group, a lower alkyl
Lucoxy group, phenyl group, lower alkyl group or lower alkyl group
Phenyl group having Rucoxy group as a substituent, R 3Is water
Represents an elementary atom, a methyl group, a methoxy group, or a chlorine atom.
Then R1, R2At least one of the
Polybutyl group, tertiary butyl group, phenyl group, low
Phenyl having a primary alkyl group or a lower alkoxy group
Represents a group.
発光材の混合層を発光層に接して設けた電界発光素子。 【化２】 ただし、Ｒ4、Ｒ5、Ｒ6は同一でも異なっていてもよ
く、水素原子、低級アルキル基、低級アルコキシ基、置
換または無置換のアリール基を表し、Ｒ7は水素原子、
低級アルキル基、低級アルコキシ基、または塩素原子を
表わし、Ａ1は以下のいずれかの構造を有する置換基を
表すが、（Ｃ）中のＲ8は水素原子、メチル基、メトキ
シ基、または塩素原子を表す。 【化３】 2. An electroluminescent device comprising a mixed layer of an amine compound represented by the following general formula and a light emitting material provided in contact with the light emitting layer. Embedded image However, R 4 , R 5 , and R 6, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a substituted or unsubstituted aryl group, and R 7 is a hydrogen atom,
A lower alkyl group, a lower alkoxy group, or a chlorine atom, A 1 represents a substituent having any of the following structures, and R 8 in (C) is a hydrogen atom, a methyl group, a methoxy group, or chlorine. Represents an atom. Embedded image
発光材の混合層を発光層に接して設けた電界発光素子。 【化４】 ただし、Ｒ9 、Ｒ10は水素原子、低級アルキル基、低級
アルコキシ基、置換または無置換のフェニル基を表し、
Ｒ11は水素原子、メチル基、メトキシ基、塩素原子を表
す。3. An electroluminescent device comprising a mixed layer of an amine compound represented by the following general formula and a light emitting material provided in contact with the light emitting layer. [Chemical 4] However, R 9 and R 10 represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a substituted or unsubstituted phenyl group,
R 11 represents a hydrogen atom, a methyl group, a methoxy group or a chlorine atom.
発光材の混合層を発光層に接して設けた電界発光素子。 【化５】 ただし、Ｒ12、Ｒ13は同一でも異なっていてもよく、水
素原子、低級アルキル基、低級アルコキシ基、置換また
は無置換のアリール基を表し、Ｒ14は水素原子、低級ア
ルキル基、低級アルコキシ基、または塩素原子を表わ
し、Ａ2は以下のいずれかの構造を有する置換基を表す
が、（Ｃ）中のＲ8は水素原子、メチル基、メトキシ
基、塩素原子を表す。 【化６】 4. An electroluminescent device comprising a mixed layer of an amine compound represented by the following general formula and a light emitting material provided in contact with the light emitting layer. Embedded image However, R 12 and R 13 may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a substituted or unsubstituted aryl group, and R 14 is a hydrogen atom, a lower alkyl group or a lower alkoxy group. Or a chlorine atom, A 2 represents a substituent having any of the following structures, and R 8 in (C) represents a hydrogen atom, a methyl group, a methoxy group, or a chlorine atom. [Chemical 6]
選ばれる少なくとも２種類を含む材料と発光材の混合層
を発光層に接して設けたことを特徴とする電界発光素
子。5. An electroluminescent device, characterized in that a mixed layer of a material containing at least two kinds selected from the amine compounds according to claims 1 to 4 and a light emitting material is provided in contact with the light emitting layer.
発光層及び陰極からなる請求項１から５のいずれか記載
の電界発光素子。6. An anode, a mixed layer of an amine compound and a light emitting material,
The electroluminescent device according to claim 1, comprising an emitting layer and a cathode.
光材の混合層、発光層及び陰極からなる請求項１から５
のいずれか記載の電界発光素子。7. An anode, a hole transport layer, a mixed layer of an amine compound and a light emitting material, a light emitting layer and a cathode.
The electroluminescent element according to any one of 1.
請求項６または７記載の電界発光素子。8. The electroluminescent device according to claim 6, further comprising an electron transport layer provided between the light emitting layer and the cathode.
一である請求項１から８のいずれか記載の電界発光素
子。9. The electroluminescent device according to claim 1, wherein the light emitting material of the mixed layer and the light emitting material of the light emitting layer are the same.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP06074995A JP3449020B2 (en) | 1995-03-20 | 1995-03-20 | EL device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP06074995A JP3449020B2 (en) | 1995-03-20 | 1995-03-20 | EL device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08259934A true JPH08259934A (en) | 1996-10-08 |
| JP3449020B2 JP3449020B2 (en) | 2003-09-22 |
Family
ID=13151240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP06074995A Expired - Lifetime JP3449020B2 (en) | 1995-03-20 | 1995-03-20 | EL device |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3449020B2 (en) |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1088119A (en) * | 1996-09-11 | 1998-04-07 | Sharp Corp | Organic electroluminescent element |
| US5885498A (en) * | 1996-12-11 | 1999-03-23 | Matsushita Electric Industrial Co., Ltd. | Organic light emitting device and method for producing the same |
| WO2000014174A1 (en) * | 1998-09-09 | 2000-03-16 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and phenylenediamine derivative |
| JP2002249765A (en) * | 2000-09-25 | 2002-09-06 | Konica Corp | Organic electroluminescence element, material for organic electroluminescence element and display device |
| KR100367719B1 (en) * | 2000-07-25 | 2003-01-10 | 학교법인 포항공과대학교 | Blue light-emitting compounds, preparing method thereof and display device employing the same |
| JP2003109768A (en) * | 2001-07-25 | 2003-04-11 | Toray Ind Inc | Light emitting element |
| WO2004020548A1 (en) * | 2002-08-28 | 2004-03-11 | Canon Kabushiki Kaisha | Organic light-emitting device |
| JP2005276541A (en) * | 2004-03-24 | 2005-10-06 | Nippon Seiki Co Ltd | Organic el element |
| EP1748681A1 (en) * | 2004-03-25 | 2007-01-31 | Hodogaya Chemical Co., Ltd. | Arylamine compound and organic electroluminescent device |
| WO2007058044A1 (en) * | 2005-11-15 | 2007-05-24 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescent element employing the same |
| JP2007182432A (en) * | 2005-12-08 | 2007-07-19 | Mitsubishi Chemicals Corp | Organic compound, electric charge-transporting material, electric charge-transporting material composition and organic electric field light-emitting element |
| JP2008047935A (en) * | 2007-09-25 | 2008-02-28 | Konica Minolta Holdings Inc | Organic electroluminescent device using new amino compound |
| JP2009081447A (en) * | 1996-08-19 | 2009-04-16 | Tdk Corp | Organic el element |
| JP2009522273A (en) * | 2005-12-29 | 2009-06-11 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Compositions containing novel compounds and electronic devices made using such compositions |
| JP2010186758A (en) * | 2000-12-28 | 2010-08-26 | Semiconductor Energy Lab Co Ltd | Method for manufacturing light emitting apparatus |
| WO2015137384A1 (en) * | 2014-03-14 | 2015-09-17 | 日産化学工業株式会社 | Aniline derivative and use thereof |
| WO2015137395A1 (en) * | 2014-03-14 | 2015-09-17 | 日産化学工業株式会社 | Aniline derivative and use thereof |
-
1995
- 1995-03-20 JP JP06074995A patent/JP3449020B2/en not_active Expired - Lifetime
Cited By (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009081447A (en) * | 1996-08-19 | 2009-04-16 | Tdk Corp | Organic el element |
| JPH1088119A (en) * | 1996-09-11 | 1998-04-07 | Sharp Corp | Organic electroluminescent element |
| US5885498A (en) * | 1996-12-11 | 1999-03-23 | Matsushita Electric Industrial Co., Ltd. | Organic light emitting device and method for producing the same |
| US7399537B2 (en) | 1998-09-09 | 2008-07-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and phenylenediamine derivative |
| WO2000014174A1 (en) * | 1998-09-09 | 2000-03-16 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and phenylenediamine derivative |
| US6541129B1 (en) * | 1998-09-09 | 2003-04-01 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and phenylenediamine derivative |
| KR100367719B1 (en) * | 2000-07-25 | 2003-01-10 | 학교법인 포항공과대학교 | Blue light-emitting compounds, preparing method thereof and display device employing the same |
| JP2002249765A (en) * | 2000-09-25 | 2002-09-06 | Konica Corp | Organic electroluminescence element, material for organic electroluminescence element and display device |
| US9362518B2 (en) | 2000-12-28 | 2016-06-07 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting device and method of manufacturing the same |
| US8878431B2 (en) | 2000-12-28 | 2014-11-04 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting device and method of manufacturing the same |
| US8432094B2 (en) | 2000-12-28 | 2013-04-30 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting device and method of manufacturing the same |
| JP2010186758A (en) * | 2000-12-28 | 2010-08-26 | Semiconductor Energy Lab Co Ltd | Method for manufacturing light emitting apparatus |
| US9209418B2 (en) | 2000-12-28 | 2015-12-08 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting device and method of manufacturing the same |
| JP2003109768A (en) * | 2001-07-25 | 2003-04-11 | Toray Ind Inc | Light emitting element |
| US7632577B2 (en) | 2002-08-28 | 2009-12-15 | Canon Kabushiki Kaisha | Organic light-emitting device |
| WO2004020548A1 (en) * | 2002-08-28 | 2004-03-11 | Canon Kabushiki Kaisha | Organic light-emitting device |
| JP2005276541A (en) * | 2004-03-24 | 2005-10-06 | Nippon Seiki Co Ltd | Organic el element |
| EP1748681A4 (en) * | 2004-03-25 | 2009-05-06 | Hodogaya Chemical Co Ltd | Arylamine compound and organic electroluminescent device |
| US7862905B2 (en) | 2004-03-25 | 2011-01-04 | Hodogaya Chemical Co., Ltd. | Arylamine compound and organic electroluminescent device |
| KR101153587B1 (en) * | 2004-03-25 | 2012-06-11 | 호도가야 가가쿠 고교 가부시키가이샤 | Arylamine compound and organic electroluminescent device |
| EP1748681A1 (en) * | 2004-03-25 | 2007-01-31 | Hodogaya Chemical Co., Ltd. | Arylamine compound and organic electroluminescent device |
| WO2007058044A1 (en) * | 2005-11-15 | 2007-05-24 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescent element employing the same |
| JP2007182432A (en) * | 2005-12-08 | 2007-07-19 | Mitsubishi Chemicals Corp | Organic compound, electric charge-transporting material, electric charge-transporting material composition and organic electric field light-emitting element |
| JP2009522273A (en) * | 2005-12-29 | 2009-06-11 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Compositions containing novel compounds and electronic devices made using such compositions |
| JP2008047935A (en) * | 2007-09-25 | 2008-02-28 | Konica Minolta Holdings Inc | Organic electroluminescent device using new amino compound |
| WO2015137395A1 (en) * | 2014-03-14 | 2015-09-17 | 日産化学工業株式会社 | Aniline derivative and use thereof |
| WO2015137384A1 (en) * | 2014-03-14 | 2015-09-17 | 日産化学工業株式会社 | Aniline derivative and use thereof |
| CN106103411A (en) * | 2014-03-14 | 2016-11-09 | 日产化学工业株式会社 | Anil and utilization thereof |
| KR20160132440A (en) * | 2014-03-14 | 2016-11-18 | 닛산 가가쿠 고교 가부시키 가이샤 | Aniline derivative and use thereof |
| JPWO2015137395A1 (en) * | 2014-03-14 | 2017-04-06 | 日産化学工業株式会社 | Aniline derivatives and uses thereof |
| JPWO2015137384A1 (en) * | 2014-03-14 | 2017-04-06 | 日産化学工業株式会社 | Aniline derivatives and uses thereof |
| TWI660944B (en) * | 2014-03-14 | 2019-06-01 | 日商日產化學工業股份有限公司 | Aniline derivatives and their uses |
| CN106103411B (en) * | 2014-03-14 | 2020-10-30 | 日产化学工业株式会社 | Aniline derivative and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3449020B2 (en) | 2003-09-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4068279B2 (en) | Organic electroluminescence device | |
| JP4011325B2 (en) | Organic electroluminescence device | |
| JP3449020B2 (en) | EL device | |
| JP4129745B2 (en) | Phenylpyridine-iridium metal complex compound for organic electroluminescence device, production method thereof, and organic electroluminescence device using the same | |
| JP2015046612A (en) | Organic electroluminescent device | |
| JP2006117661A (en) | Iridium-based luminescent compound having phenylpyridine moiety with organosilicon group, and organic electroluminescent element using the compound as color-emitting material | |
| JP2006135295A (en) | Organic electroluminescence element | |
| KR100469240B1 (en) | Organic electroluminescent device | |
| JP4251553B2 (en) | Organic electroluminescence device | |
| JP3951425B2 (en) | Organic electroluminescence device | |
| JPH03162481A (en) | Electroluminescent element | |
| KR20000032065A (en) | Luminescence compound and luminescence device using the same as coupler | |
| JP2003229279A (en) | Organic electroluminescent element | |
| JP3490879B2 (en) | Organic electroluminescence device | |
| JP2000030869A (en) | Organic electroluminescence element | |
| JP3239057B2 (en) | Organic electroluminescence device | |
| JP3547945B2 (en) | Organic electroluminescence device | |
| JP3738870B2 (en) | Organic electroluminescence device | |
| JP2004031211A (en) | Organic electroluminescent element | |
| JP4733285B2 (en) | Organic electroluminescence device | |
| JPH09194831A (en) | Organic thin-film el element | |
| JP2003036980A (en) | Organic electric field light-emitting element | |
| JP3841203B2 (en) | Organic electroluminescence device | |
| JP3841202B2 (en) | Organic electroluminescence device | |
| JPH11260553A (en) | Organic electroluminescent element |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20070711 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080711 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090711 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090711 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100711 Year of fee payment: 7 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110711 Year of fee payment: 8 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110711 Year of fee payment: 8 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120711 Year of fee payment: 9 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120711 Year of fee payment: 9 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130711 Year of fee payment: 10 |
|
| S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| EXPY | Cancellation because of completion of term | ||
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |