JP2002083682A - Organic electroluminescent device - Google Patents
Organic electroluminescent deviceInfo
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- JP2002083682A JP2002083682A JP2000341560A JP2000341560A JP2002083682A JP 2002083682 A JP2002083682 A JP 2002083682A JP 2000341560 A JP2000341560 A JP 2000341560A JP 2000341560 A JP2000341560 A JP 2000341560A JP 2002083682 A JP2002083682 A JP 2002083682A
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- organic electroluminescent
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】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、高効率かつ
安定性に優れた有機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 device widely used as various display devices, and to an organic electroluminescent device having high efficiency 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
素子にくらべて明るく、鮮明な表示が可能であるため、
古くから多くの研究者によって研究されてきた。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Ｚ
ｎＳを用いた素子がある。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
が必要であるため、広く使用されるには至っていない。2. Description of the Related Art An electroluminescent device is capable of displaying a brighter and clearer display than a liquid crystal device due to self-luminous light.
It has been studied by many researchers since ancient times. As the electroluminescent device that has reached the practical level at present, the inorganic material Z
There is an element using nS. However, such an inorganic electroluminescent element has not been widely used since a driving voltage of 200 V or more is required for light emission.
【０００３】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年にイーストマン
・コダック社のシー・ダブリュ・タン（Ｃ．Ｗ．Ｔａｎ
ｇ）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。彼らは蒸着膜の構造が安定で電子
を輸送することのできる蛍光体からなる層（電子輸送性
発光層）と、正孔を輸送することのできる有機物からな
る層（正孔輸送層）とを積層し、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。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。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。On the other hand, an organic electroluminescent device, which is an electroluminescent device using an organic material, was far from a practical level in the past, but in 1987 C.D. Tan (CW Tan)
g) have greatly improved its characteristics by the laminated structure element developed by them. They consist of a layer composed of a phosphor that can transport electrons with a stable structure of the deposited film (electron transporting light emitting layer) and a layer composed of an organic substance capable of transporting holes (hole transport layer). After stacking, both carriers were successfully injected into the phosphor to emit light. 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. Since then, many researchers have studied to improve the characteristics, and at present, luminescence characteristics of 10,000 cd / m 2 or more have been obtained.
【０００４】この様な有機電界発光素子においては、素
子の有機層と電極を構成する有機材料と金属材料によっ
て特性が大きく変化する。特に有機層は、電荷の注入・
輸送・再結合・発光といった重要な機能を果たしてお
り、特性の優れた素子を実現するには、それぞれの層の
機能に適した材料を選択することが重要である。また、
耐久性に優れた素子を得るためには、有機層に凝集を起
こさない安定性に優れた膜を用いることが重要である。[0004] In such an organic electroluminescent device, the characteristics greatly change depending on the organic material and the metal material constituting the organic layer and the electrode of the device. In particular, the organic layer
It performs important functions such as transport, recombination, and light emission. To realize a device having excellent characteristics, it is important to select a material suitable for the function of each layer. Also,
In order to obtain an element having excellent durability, it is important to use a film having excellent stability that does not cause aggregation in the organic layer.
【０００５】電荷注入輸送層は、正孔注入輸送層と電子
注入輸送層に大別される。それぞれ、電極からの電荷の
注入を容易にし、注入された電荷を発光領域まで輸送す
るという働きをする。電荷注入層と電荷輸送層を一つの
材料で兼ねる場合と別々の材料を用いる場合とがある。
正孔注入層のための材料としては、陽極からの正孔の注
入を容易にするため、ＨＯＭＯレベルの小さい材料が使
用される。具体的には銅フタロシアニン（ＣｕＰｃ）、
トリス｛４−[（３-メチルフェニル）フェニルアミノ]
フェニル｝アミン（ｍ−ＭＴＤＡＴＡ）などが挙げられ
る。また、正孔輸送材料としてはトリフェニルアミン誘
導体が一般的に用いられている。特許２８２６３８１号
公報によれば、正孔注入層あるいは正孔注入輸送層とし
ての有機半導体域を形成する材料として、導電性高分子
のオリゴマー、特にチオフェンオリゴマーを含むものが
好ましいとされている。一方、電子輸送材料としては、
オキサジアゾール誘導体やトリス（８−ヒドロキシキノ
リラト）アルミニウム（Ａｌｑ）などに代表されるキノ
リノール金属錯体などが検討されている。[0005] The charge injection transport layer is roughly classified into a hole injection transport layer and an electron injection transport layer. Each of them functions to facilitate injection of charge from the electrode and transport the injected charge to the light emitting region. The charge injection layer and the charge transport layer may be made of one material, or may be made of different materials.
As a material for the hole injection layer, a material having a small HOMO level is used to facilitate injection of holes from the anode. Specifically, copper phthalocyanine (CuPc),
Tris 4-[(3-methylphenyl) phenylamino]
Phenyl diamine (m-MTDATA) and the like. As a hole transporting material, a triphenylamine derivative is generally used. According to Japanese Patent No. 2826381, as a material for forming an organic semiconductor region as a hole injection layer or a hole injection transport layer, a material containing a conductive polymer oligomer, particularly a thiophene oligomer, is preferable. On the other hand, as electron transport materials,
An oxadiazole derivative and a quinolinol metal complex represented by tris (8-hydroxyquinolinolato) aluminum (Alq) and the like have been studied.
【０００６】しかしこれらの材料の中には、チオフェン
オリゴマー、オキサジアゾール誘導体などのように、電
荷の注入輸送機能には優れていても、薄膜の安定性にか
けるものも多い。However, among these materials, there are many such as a thiophene oligomer and an oxadiazole derivative, which are excellent in charge injection / transport function, but affect thin film stability.
【０００７】発光層用の材料としては数多くの化合物群
が検討されている。また、製膜性に優れた材料の中に蛍
光性の色素を少量分散させた膜を発光層として用いるこ
とにより、素子の高効率化、長寿命化および発光色の調
整をすることも検討されている。この手法は、単独では
結晶化しやすい、あるいは濃度消光を起こしやすい蛍光
色素に対して非常に有効である。しかし、発光効率・駆
動耐久性ともに、実用化するためには十分な特性を満た
すものは得られていなかった。[0007] Numerous compounds have been studied as materials for the light emitting layer. It has also been considered to use a film in which a small amount of a fluorescent dye is dispersed in a material with excellent film-forming properties as a light-emitting layer to increase the efficiency, prolong the life of the device, and adjust the emission color. ing. This method is very effective for fluorescent dyes that are liable to crystallize or cause concentration quenching by themselves. However, none of them have sufficient properties for practical use in both luminous efficiency and driving durability.
【０００８】連続駆動時の輝度低下を抑制するために
は、発光材料以外にも様々な検討がされている。たとえ
ば、発光層と電荷輸送層との間に両者の構成材料の混合
物からなる層を設ける、あるいは電荷輸送層の高耐熱化
などが行われている。しかし、これらの手法は必ずしも
有効であるとは限らない。In order to suppress a decrease in luminance during continuous driving, various studies have been made in addition to a light emitting material. For example, a layer made of a mixture of both constituent materials is provided between the light-emitting layer and the charge transport layer, or the charge transport layer is improved in heat resistance. However, these techniques are not always effective.
【０００９】[0009]
【発明が解決しようとする課題】本発明の目的は、有機
電界発光素子に用いる有機材料およびその使用法を改良
することによって、発光効率が高く駆動耐久性に優れた
有機電界発光素子を実現することにある。SUMMARY OF THE INVENTION An object of the present invention is to provide an organic electroluminescent device having high luminous efficiency and excellent driving durability by improving the organic material used for the organic electroluminescent device and the use thereof. It is in.
【００１０】[0010]
【課題を解決するための手段】本発明の有機電界発光素
子は、一対の電極とその間に挟まれた少なくとも一層以
上の有機層を有しており、その有機層の一つである発光
層が置換または無置換のチオフェンオリゴマーを含む複
数の材料で構成されていることを特徴としたものであ
る。あるいは素子を構成する発光層と電極の間に蛍光材
料が混合された領域を有し、その領域が発光層から離れ
ていることを特徴としたものである。The organic electroluminescent device of the present invention has a pair of electrodes and at least one or more organic layers sandwiched between the electrodes, and one of the organic layers is a light emitting layer. It is characterized by being composed of a plurality of materials including a substituted or unsubstituted thiophene oligomer. Alternatively, there is provided a region in which a fluorescent material is mixed between a light emitting layer and an electrode constituting an element, and the region is separated from the light emitting layer.
【００１１】[0011]
【発明の実施の形態】本発明の請求項１に記載の発明
は、一対の電極と、前記一対の電極の間に発光層を有
し、前記発光層が置換または無置換のチオフェンオリゴ
マーを含む複数の有機材料を含む有機電界発光素子であ
り、発光色を変化させ、かつ効率を向上させるという作
用を有する。BEST MODE FOR CARRYING OUT THE INVENTION The invention according to claim 1 of the present invention has a pair of electrodes and a light emitting layer between the pair of electrodes, and the light emitting layer contains a substituted or unsubstituted thiophene oligomer. An organic electroluminescent element including a plurality of organic materials, which has an effect of changing a luminescent color and improving efficiency.
【００１２】請求項２に記載の発明は、チオフェンオリ
ゴマーが４つ以上のチオフェン環を有する請求項１記載
の有機電界発光素子であり、このようなオリゴマーを用
いることにより、より効率よい安定した発光を得ること
ができる。According to a second aspect of the present invention, there is provided the organic electroluminescent device according to the first aspect, wherein the thiophene oligomer has four or more thiophene rings, and by using such an oligomer, more efficient and stable light emission. Can be obtained.
【００１３】請求項３に記載の発明は一対の電極と、前
記一対の電極の間に発光層、正孔注入層及び正孔輸送層
を有し、前記正孔注入層又は前記正孔輸送層が２種類以
上の有機材料の混合物からなっており、前記有機材料の
うちの少なくとも一つがオリゴマー材料である有機電界
発光素子であり、正孔の注入輸送を容易にすると同時
に、膜の安定性を向上させることにより、素子の効率お
よび駆動耐久性を向上させるという作用を有する。According to a third aspect of the present invention, there is provided a light emitting layer, a hole injection layer and a hole transport layer between the pair of electrodes, wherein the hole injection layer or the hole transport layer is provided. Is a mixture of two or more kinds of organic materials, wherein at least one of the organic materials is an organic electroluminescent element that is an oligomer material, which facilitates the injection and transport of holes and at the same time, improves the stability of the film. Improving the function has the effect of improving the efficiency and driving durability of the element.
【００１４】請求項４に記載の発明は、有機材料の少な
くとも一つが無置換または置換基を有するトリフェニル
アミンオリゴマーである請求項３記載の有機電界発光素
子であり、正孔輸送注入性に優れた材料を用いることに
より、より素子の高効率化および駆動耐久性の向上が可
能となるという作用を有する。According to a fourth aspect of the present invention, there is provided the organic electroluminescent device according to the third aspect, wherein at least one of the organic materials is an unsubstituted or substituted triphenylamine oligomer, and has excellent hole transport and injection properties. The use of such a material has an effect that the efficiency of the element can be further improved and the driving durability can be improved.
【００１５】請求項５に記載の発明は、有機材料の少な
くとも一つが置換または無置換のチオフェンオリゴマー
である請求項３記載の有機電界発光素子であり、正孔輸
送注入性に優れた材料を用いることにより、より素子の
高効率化および駆動耐久性の向上が可能となるという作
用を有する。According to a fifth aspect of the present invention, there is provided the organic electroluminescent device according to the third aspect, wherein at least one of the organic materials is a substituted or unsubstituted thiophene oligomer, wherein a material having excellent hole transport and injection properties is used. This has the effect that the efficiency of the element can be increased and the driving durability can be further improved.
【００１６】請求項６に示すように、正孔注入層と正孔
輸送層の代りに、正孔を注入、輸送する正孔注入輸送層
を有する有機電界発光素子であっても良い。According to a sixth aspect of the present invention, an organic electroluminescent device having a hole injection / transport layer for injecting and transporting holes may be used instead of the hole injection layer and the hole transport layer.
【００１７】請求項７に記載の発明は、一対の電極と、
前記一対の電極の間に発光層と少なくとも一層以上の有
機層を有し、前記発光層と隣接する有機層に、発光層か
ら発せられる光のピーク波長よりも短波長の吸収ピーク
波長を有する蛍光材料が混合されている有機電界発光素
子であり、駆動耐久性を向上させるという作用を有す
る。[0017] According to a seventh aspect of the present invention, a pair of electrodes,
A fluorescent layer having a light emitting layer and at least one or more organic layers between the pair of electrodes, and an organic layer adjacent to the light emitting layer having an absorption peak wavelength shorter than the peak wavelength of light emitted from the light emitting layer. An organic electroluminescent device in which materials are mixed, and has an effect of improving driving durability.
【００１８】請求項８に記載の発明は、一対の電極と、
前記一対の電極の間に発光層と少なくとも一層以上の有
機層を有し、前記発光層と隣接しない有機層に蛍光材料
が混合されている有機電界発光素子であり、駆動耐久性
を向上させるという作用を有する。[0018] According to the invention described in claim 8, a pair of electrodes,
An organic electroluminescent element having a light-emitting layer and at least one or more organic layers between the pair of electrodes, and a fluorescent material mixed with an organic layer not adjacent to the light-emitting layer to improve driving durability. Has an action.
【００１９】以下に、本発明の実施の形態について、図
面を用いて具体的に説明する。Hereinafter, embodiments of the present invention will be specifically described with reference to the drawings.
【００２０】（実施の形態１）図１に本発明第１の実施
の形態における有機電界発光素子の構成の断面図を示
す。ガラス基板１上に陽極２を形成し、その上に正孔注
入層３、正孔輸送層４、発光層５、電子輸送層６、電子
注入層７、陰極８を形成したものである。正孔注入層と
正孔輸送層、電子輸送層と電子注入層はそれぞれ一つの
層で兼ねることもできる。さらに発光層と正孔注入輸送
層、発光層と電子注入輸送層を兼ねることもできる。(Embodiment 1) FIG. 1 is a sectional view showing the structure of an organic electroluminescent device according to a first embodiment of the present invention. An anode 2 is formed on a glass substrate 1, and a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8 are formed thereon. The hole injection layer and the hole transport layer, and the electron transport layer and the electron injection layer may each serve as one layer. Further, the light emitting layer and the hole injecting and transporting layer, and the light emitting layer and the electron injecting and transporting layer can also be used.
【００２１】陽極２には透明電極としてインジウム錫酸
化物（ＩＴＯ）や半透明電極として金薄膜を用いること
ができる。The anode 2 can be made of indium tin oxide (ITO) as a transparent electrode or a gold thin film as a translucent electrode.
【００２２】正孔注入層７、正孔輸送層８としては、従
来の技術の項であげた、銅フタロシアニン（ＣｕＰｃ）
やトリス｛４−[（３-メチルフェニル）フェニルアミ
ノ]フェニル｝アミン（ｍ−ＭＴＤＡＴＡ）、トリフェ
ニルアミン誘導体などのほか、本発明によるオリゴマー
材料を含む混合物を用いることができる。さらにオリゴ
マー材料として、トリフェニルアミンオリゴマーやチオ
フェンオリゴマーなど、正孔輸送性の強い材料を用いる
ことにより、特性を向上させることができる。また、発
光層はチオフェンオリゴマーを含む複数の材料で構成さ
れているが、チオフェンオリゴマーの割合としては１０
ｍｏｌ％以下が望ましい。The hole injection layer 7 and the hole transport layer 8 are made of copper phthalocyanine (CuPc) described in the section of the prior art.
In addition to tris {4-[(3-methylphenyl) phenylamino] phenyl} amine (m-MTDATA) and triphenylamine derivatives, a mixture containing the oligomer material according to the present invention can be used. Further, the characteristics can be improved by using a material having a strong hole transporting property such as a triphenylamine oligomer or a thiophene oligomer as the oligomer material. The light-emitting layer is composed of a plurality of materials including a thiophene oligomer.
mol% or less is desirable.
【００２３】電子輸送層６、電子注入層７を構成する材
料としては従来の技術の項であげた、オキサジアゾール
誘導体やトリス（８−ヒドロキシキノリラト）アルミニ
ウム（Ａｌｑ）などに代表されるキノリノール金属錯体
を用いることができる。The materials constituting the electron transporting layer 6 and the electron injecting layer 7 are represented by oxadiazole derivatives, tris (8-hydroxyquinolylato) aluminum (Alq) and the like described in the section of the prior art. A quinolinol metal complex can be used.
【００２４】陰極８には有機膜に電子が注入でき、かつ
た耐環境安定性に優れていることが必要であり、具体的
にはアルミニウム、マグネシウム、あるいはこれらの金
属の合金を用いることができる。The cathode 8 is required to be capable of injecting electrons into an organic film and having excellent environmental stability. Specifically, aluminum, magnesium, or an alloy of these metals can be used. .
【００２５】さらに、本発明によれば、正孔輸送層４ま
たは電子輸送層６に発光層から発せられる光のピーク波
長よりも短波長に吸収ピーク波長を有する蛍光材料を混
合させて用いることにより、素子の駆動耐久性を向上さ
せることが可能となる。Furthermore, according to the present invention, the hole transporting layer 4 or the electron transporting layer 6 is mixed with a fluorescent material having an absorption peak wavelength shorter than the peak wavelength of light emitted from the light emitting layer. Thus, the driving durability of the element can be improved.
【００２６】（実施の形態２）図２に本発明第２の実施
の形態における有機電界発光素子の構成の断面図を示
す。ガラス基板１上に陽極２を形成し、その上に正孔注
入層３、正孔輸送層４、発光層５、電子輸送層６、電子
注入層７、陰極８を形成したものであり、正孔輸送層４
の一部に蛍光材料を混合した混合層９を設ける。陽極
２、正孔注入層３、正孔輸送層４、発光層５、電子輸送
層６、電子注入層７、陰極８は実施の形態１に記載した
ものと同様なものを使用することができる。混合層９は
発光層５と離して設ければ、どこでも良い。混合層に用
いる蛍光材料としては、有機電界発光素子に用いられる
有機材料を用いることができる。また、実施の形態１の
場合と同様に、正孔注入層と正孔輸送層、電子輸送層と
電子注入層はそれぞれ一つの層で兼ねることができる。(Embodiment 2) FIG. 2 is a sectional view showing the structure of an organic electroluminescent device according to a second embodiment of the present invention. An anode 2 is formed on a glass substrate 1, and a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8 are formed thereon. Hole transport layer 4
Is provided with a mixed layer 9 in which a fluorescent material is mixed. The anode 2, the hole injection layer 3, the hole transport layer 4, the light emitting layer 5, the electron transport layer 6, the electron injection layer 7, and the cathode 8 can be the same as those described in Embodiment 1. . The mixed layer 9 may be provided anywhere as long as it is provided apart from the light emitting layer 5. As a fluorescent material used for the mixed layer, an organic material used for an organic electroluminescent element can be used. In addition, as in the case of Embodiment 1, each of the hole injecting layer and the hole transporting layer, and the electron transporting layer and the electron injecting layer can serve as one layer.
【００２７】なお、ここでは正孔輸送層に混合層を設け
た場合について説明したが、電子輸送層に混合層を設け
る場合も同様に実施することができる。Although the case where the mixed layer is provided in the hole transport layer has been described here, the same can be applied to the case where the mixed layer is provided in the electron transport layer.
【００２８】[0028]
【実施例】次に、本発明の実施例を説明する。Next, an embodiment of the present invention will be described.
【００２９】（実施例１）以下、本発明第１の実施例を
説明する。基板にはガラス上に透明な陽極としてインジ
ウム錫酸化膜（ＩＴＯ）をあらかじめ形成し、電極の形
にパターニングしたもの用いた。この基板を充分に洗浄
した後、蒸着する材料と一緒に真空装置内にセットし、
１０-4Ｐａまで排気した。その後、正孔注入輸送層とし
てN,N'-ビス[4'-(N,N-ジフェニルアミノ)-4-ビフェニリ
ル]-N,N'-ジフェニルベンジジン（ＴＰＴ）を５０ｎｍ
製膜した。その後、発光層としてＡｌｑと（化１）に示
すチオフェン誘導体（１）の混合膜を２５ｎｍ製膜し
た。(Embodiment 1) Hereinafter, a first embodiment of the present invention will be described. The substrate used was one in which an indium tin oxide film (ITO) was previously formed as a transparent anode on glass and patterned in the form of an electrode. After thoroughly cleaning this substrate, set it in a vacuum device together with the material to be deposited,
Evacuation was performed to 10 -4 Pa. Then, N, N'-bis [4 '-(N, N-diphenylamino) -4-biphenylyl] -N, N'-diphenylbenzidine (TPT) was used as a hole injection / transport layer at 50 nm.
A film was formed. Thereafter, a 25 nm mixed film of Alq and the thiophene derivative (1) shown in Chemical Formula 1 was formed as a light emitting layer.
【００３０】[0030]
【化１】 Embedded image
【００３１】製膜は２つの材料を別々の蒸着源から蒸発
させる共蒸着法により行い、Ａｌｑに対する化合物
（１）の混合比は１ｍｏｌ％とした。さらに、電子注入
輸送層としてＡｌｑを２５ｎｍ製膜した後、陰極として
ＡｌＬｉ合金を１５０ｎｍの厚さで製膜し、素子を作成
した。これらの製膜は一度も真空を破ることなく、連続
して行った。なお、膜厚は水晶振動子によってモニター
した。素子作製後、直ちに乾燥窒素中で電極の取り出し
を行い、引き続き特性測定を行った。得られた素子に電
圧を印加したところ、均一な黄色の発光が得られた。１
００ｍＡ／ｃｍ2の電流を印加した場合の駆動電圧なら
びに発光輝度を測定したところ、駆動電圧５．５Ｖ、発
光輝度は３８５０ｃｄ／ｍ2であった。The film was formed by a co-evaporation method in which two materials were evaporated from separate evaporation sources, and the mixing ratio of the compound (1) to Alq was 1 mol%. Further, a film of Alq was formed to a thickness of 25 nm as an electron injecting / transporting layer, and then a film of an AlLi alloy was formed to a thickness of 150 nm as a cathode to produce a device. These films were continuously formed without breaking the vacuum. The film thickness was monitored with a quartz oscillator. Immediately after the device was manufactured, the electrodes were taken out in dry nitrogen, and the characteristics were measured. When voltage was applied to the obtained device, uniform yellow luminescence was obtained. 1
When the drive voltage and the light emission luminance when a current of 00 mA / cm 2 was applied were measured, the drive voltage was 5.5 V and the light emission luminance was 3850 cd / m 2 .
【００３２】この素子を乾燥窒素中において、初期輝度
１０００ｃｄ／ｍ2で連続駆動（定電流）したところ、
輝度が初期の半分である５００ｃｄ／ｍ2になるのに要
する時間（輝度半減期）は８５０ｈであった。また、５
００ｈ駆動後の電圧上昇分は０．８Ｖであった。The device was continuously driven (constant current) at an initial luminance of 1000 cd / m 2 in dry nitrogen.
The time required for the luminance to reach 500 cd / m 2 , which is half of the initial value (luminance half-life), was 850 h. Also, 5
The voltage rise after the driving for 00h was 0.8 V.
【００３３】（実施例２）以下、本発明第２の実施例を
説明する。第２の実施例では、発光層としてＡｌｑと
(化２)に示すチオフェン誘導体（２）との混合膜を用い
たこと以外は第１の実施例と同様に素子を作製した。(Embodiment 2) Hereinafter, a second embodiment of the present invention will be described. In the second embodiment, Alq is used as the light emitting layer.
A device was manufactured in the same manner as in the first example except that a mixed film with the thiophene derivative (2) shown in (Chemical Formula 2) was used.
【００３４】[0034]
【化２】 Embedded image
【００３５】Ａｌｑに対するチオフェン誘導体（２）の
混合比は１ｍｏｌ％とした。得られた素子に電圧を印加
したところ、均一な橙色の発光が得られた。１００ｍＡ
／ｃｍ2の電流を印加した場合の駆動電圧ならびに発光
輝度を測定したところ、駆動電圧５．４Ｖ、発光輝度は
４２００ｃｄ／ｍ2であった。この素子を乾燥窒素中に
おいて、初期輝度１０００ｃｄ／ｍ2で連続駆動（定電
流）したところ、輝度半減期は９００ｈであった。ま
た、５００ｈ駆動後の電圧上昇分は０．６Ｖであった。The mixing ratio of the thiophene derivative (2) to Alq was 1 mol%. When voltage was applied to the obtained element, uniform orange light emission was obtained. 100mA
When the driving voltage and the emission luminance when a current of / cm 2 were applied were measured, the driving voltage was 5.4 V and the emission luminance was 4200 cd / m 2 . When the device was continuously driven (constant current) at an initial luminance of 1000 cd / m 2 in dry nitrogen, the luminance half-life was 900 hours. Further, the voltage increase after driving for 500 hours was 0.6 V.
【００３６】（実施例３）以下、本発明第３の実施例を
説明する。第３の実施例では、基板にはガラス上に透明
な陽極としてインジウム錫酸化膜（ＩＴＯ）をあらかじ
め形成し、電極の形にパターニングしたもの用いた。こ
の基板を充分に洗浄した後、蒸着する材料と一緒に真空
装置内にセットし、１０-4Ｐａまで排気した。その後、
正孔注入層として（化１）に示すチオフェン誘導体
（１）とＴＰＴの混合膜を２５ｎｍ製膜した。 混合膜
は２つの材料を別々の蒸着源から蒸発させて作製し、混
合比はモル比で１：１とした。それから、正孔輸送層と
してＴＰＴを２５ｎｍ製膜した。その後、発光層兼電子
注入輸送層としてＡｌｑを５０ｎｍ製膜した。(Embodiment 3) Hereinafter, a third embodiment of the present invention will be described. In the third embodiment, an indium tin oxide film (ITO) was previously formed as a transparent anode on glass and patterned into an electrode shape. After sufficiently washing the substrate, the substrate was set in a vacuum device together with the material to be deposited, and the substrate was evacuated to 10 -4 Pa. afterwards,
As the hole injection layer, a mixed film of thiophene derivative (1) shown in Chemical Formula 1 and TPT was formed to a thickness of 25 nm. The mixed film was prepared by evaporating two materials from different evaporation sources, and the mixing ratio was 1: 1 in molar ratio. Then, 25 nm of TPT was formed as a hole transport layer. Thereafter, Alq was formed to a thickness of 50 nm as a light emitting layer and an electron injection / transport layer.
【００３７】さらに、陰極としてＡｌＬｉ合金を１５０
ｎｍの厚さで製膜し、素子を作成した。これらの製膜は
一度も真空を破ることなく、連続して行った。なお、膜
厚は水晶振動子によってモニターした。素子作製後、直
ちに乾燥窒素中で電極の取り出しを行い、引き続き特性
測定を行った。得られた素子に電圧を印加したところ、
均一な黄緑色の発光が得られた。１００ｍＡ／ｃｍ2の
電流を印加した場合の駆動電圧ならびに発光輝度を測定
したところ、駆動電圧５．１Ｖ、発光輝度は２３５０ｃ
ｄ／ｍ2であった。この素子を乾燥窒素中において、初
期輝度１０００ｃｄ／ｍ2で連続駆動（定電流）したと
ころ、輝度半減期は５４０ｈであった。また、５００ｈ
駆動後の電圧上昇分は０．５Ｖであった。Further, an AlLi alloy is used as a cathode for 150
A film was formed with a thickness of nm to produce a device. These films were continuously formed without breaking the vacuum. The film thickness was monitored with a quartz oscillator. Immediately after the device was manufactured, the electrodes were taken out in dry nitrogen, and the characteristics were measured. When voltage was applied to the obtained device,
Uniform yellow-green emission was obtained. When the driving voltage and the emission luminance when a current of 100 mA / cm 2 was applied were measured, the driving voltage was 5.1 V and the emission luminance was 2350 c.
d / m 2 . When this device was continuously driven (constant current) at an initial luminance of 1000 cd / m 2 in dry nitrogen, the luminance half-life was 540 h. Also, 500h
The voltage increase after driving was 0.5V.
【００３８】（実施例４）以下、本発明第４の実施例を
説明する。第４の実施例では、正孔注入層に（化１）に
示すチオフェン誘導体（１）と（化３）に示すチオフェ
ン誘導体（３）の混合膜を用いたこと以外は第３の実施
例と同様に素子を作成した。Embodiment 4 Hereinafter, a fourth embodiment of the present invention will be described. The fourth embodiment is similar to the third embodiment except that a mixed film of the thiophene derivative (1) shown in (Chemical Formula 1) and the thiophene derivative (3) shown in (Chemical Formula 3) is used for the hole injection layer. An element was prepared similarly.
【００３９】[0039]
【化３】 Embedded image
【００４０】得られた素子に電圧を印加したところ、均
一な黄緑色の発光が得られた。１００ｍＡ／ｃｍ2の電
流を印加した場合の駆動電圧ならびに発光輝度を測定し
たところ、駆動電圧５．８Ｖ、発光輝度は２４４０ｃｄ
／ｍ2であった。この素子を乾燥窒素中において、初期
輝度１０００ｃｄ／ｍ2で連続駆動（定電流）したとこ
ろ、輝度半減期は６２０ｈであった。また、５００ｈ駆
動後の電圧上昇分は０．７Ｖであった。When a voltage was applied to the obtained device, uniform yellow-green light emission was obtained. When the driving voltage and the emission luminance when a current of 100 mA / cm 2 was applied were measured, the driving voltage was 5.8 V and the emission luminance was 2440 cd.
/ M 2 . When this element was continuously driven (constant current) at an initial luminance of 1000 cd / m 2 in dry nitrogen, the luminance half-life was 620 h. The voltage increase after driving for 500 hours was 0.7 V.
【００４１】（実施例５）以下、本発明第５の実施例を
説明する。第５の実施例では、基板にはガラス上に透明
な陽極としてインジウム錫酸化膜（ＩＴＯ）をあらかじ
め形成し、電極の形にパターニングしたもの用いた。こ
の基板を充分に洗浄した後、蒸着する材料と一緒に真空
装置内にセットし、１０-4Ｐａまで排気した。その後、
正孔注入層としてＴＰＴを２５ｎｍ製膜した。さらに正
孔輸送層として、ＴＰＴとペリレン（吸収ピーク波長４
３８ｎｍ）の混合膜を２５ｎｍ製膜した。(Embodiment 5) Hereinafter, a fifth embodiment of the present invention will be described. In the fifth embodiment, an indium tin oxide film (ITO) was previously formed as a transparent anode on glass and patterned into an electrode shape. After sufficiently washing the substrate, the substrate was set in a vacuum device together with the material to be deposited, and the substrate was evacuated to 10 -4 Pa. afterwards,
25 nm of TPT was formed as a hole injection layer. Further, TPT and perylene (absorption peak wavelength 4
38 nm) to form a 25 nm mixed film.
【００４２】製膜は２つの材料を別々の蒸着源から蒸発
させる共蒸着法により行い、ＴＰＴに対するペリレンの
混合比は１ｍｏｌ％とした。さらに、発光層兼電子注入
輸送層としてＡｌｑ（蛍光ピーク波長５２５ｎｍ）を５
０ｎｍ製膜した後、陰極としてＡｌＬｉ合金を１５０ｎ
ｍの厚さで製膜し、素子を作成した。得られた素子に電
圧を印加したところ、均一な黄緑色の発光が得られた。
ＥＬスペクトルを測定したところ、ペリレンからの発光
は観測されなかった。１００ｍＡ／ｃｍ2の電流を印加
した場合の駆動電圧ならびに発光輝度を測定したとこ
ろ、駆動電圧５．９Ｖ、発光輝度は２３００ｃｄ／ｍ2
であった。この素子を乾燥窒素中において、初期輝度１
０００ｃｄ／ｍ2で連続駆動（定電流）したところ、輝
度半減期は６１０ｈであった。また、５００ｈ駆動後の
電圧上昇分は１．５Ｖであった。The film was formed by a co-evaporation method in which two materials were evaporated from different evaporation sources, and the mixing ratio of perylene to TPT was 1 mol%. Further, Alq (fluorescence peak wavelength: 525 nm) is used as a light emitting layer and an electron injection / transport layer.
After forming a 0 nm film, an AlLi alloy was used for 150 n as a cathode.
m was formed to form a device. When a voltage was applied to the obtained device, uniform yellow-green light emission was obtained.
When the EL spectrum was measured, no light emission from perylene was observed. When the driving voltage and the emission luminance when a current of 100 mA / cm 2 was applied were measured, the driving voltage was 5.9 V and the emission luminance was 2300 cd / m 2.
Met. The device was dried in dry nitrogen at an initial luminance of 1
As a result of continuous driving (constant current) at 000 cd / m 2 , the luminance half-life was 610 h. The voltage rise after driving for 500 hours was 1.5 V.
【００４３】（実施例６）以下、本発明第６の実施例を
説明する。第６の実施例では、ペリレンの代わりに９，
１０-ジフェニルアントラセン（吸収ピーク波長２７７
ｎｍ）を用いたこと以外は第５の実施例と同様にして素
子を作成した。(Embodiment 6) Hereinafter, a sixth embodiment of the present invention will be described. In a sixth embodiment, instead of perylene, 9,
10-diphenylanthracene (absorption peak wavelength 277
A device was prepared in the same manner as in the fifth example except that (nm) was used.
【００４４】得られた素子に電圧を印加したところ、均
一な黄緑色の発光が得られた。発光スペクトルを測定し
たところ、９，１０-ジフェニルアントラセンからの発
光は観測されなかった。１００ｍＡ／ｃｍ2の電流を印
加した場合の駆動電圧ならびに発光輝度を測定したとこ
ろ、駆動電圧６．１Ｖ、発光輝度は２２１０ｃｄ／ｍ 2
であった。この素子を乾燥窒素中において、初期輝度１
０００ｃｄ／ｍ2で連続駆動（定電流）したところ、輝
度半減期は４２０ｈであった。また、５００ｈ駆動後の
電圧上昇分は１．７Ｖであった。When a voltage was applied to the obtained device,
One yellow-green emission was obtained. Measure the emission spectrum
The emission from 9,10-diphenylanthracene
No light was observed. 100mA / cmTwoMark the current
The drive voltage and light emission brightness were measured.
Of course, the driving voltage is 6.1 V and the emission luminance is 2210 cd / m. Two
Met. The device was dried in dry nitrogen at an initial luminance of 1
000cd / mTwoWhen driven continuously (constant current) with
The degree half-life was 420 h. Also, after 500 hours of driving
The voltage rise was 1.7V.
【００４５】（実施例７）以下、本発明第７の実施例を
説明する。第７の実施例では、ペリレンの代わりにクマ
リン５１５（Ｅｘｃｉｔｏｎ社製、吸収ピーク波長４１
０ｎｍ）を用いたこと以外は第５の実施例と同様にして
素子を作成した。Embodiment 7 Hereinafter, a seventh embodiment of the present invention will be described. In the seventh embodiment, coumarin 515 (manufactured by Exciton, absorption peak wavelength 41) was used instead of perylene.
A device was prepared in the same manner as in the fifth example except that the thickness of the device was 0 nm.
【００４６】得られた素子に電圧を印加したところ、均
一な黄緑色の発光が得られた。発光スペクトルを測定し
たところ、クマリン５１５からの発光は観測されなかっ
た。１００ｍＡ／ｃｍ2の電流を印加した場合の駆動電
圧ならびに発光輝度を測定したところ、駆動電圧６．３
Ｖ、発光輝度２３８０ｃｄ／ｍ2であった。この素子を
乾燥窒素中において初期輝度１０００ｃｄ／ｍ2で連続
駆動（定電流）したところ、輝度半減期は５００ｈであ
った。また５００ｈ駆動後の電圧上昇分は１．２Ｖであ
った。When a voltage was applied to the obtained device, uniform yellow-green light emission was obtained. When the emission spectrum was measured, no emission from coumarin 515 was observed. When the driving voltage and the emission luminance when a current of 100 mA / cm 2 was applied were measured, the driving voltage was 6.3.
V, emission luminance was 2380 cd / m 2 . When this device was continuously driven (constant current) at an initial luminance of 1000 cd / m 2 in dry nitrogen, the luminance half life was 500 hours. The voltage rise after driving for 500 hours was 1.2 V.
【００４７】（実施例８）以下、本発明第８の実施例を
説明する。第８の実施例では、基板にはガラス上に透明
な陽極としてインジウム錫酸化膜（ＩＴＯ）をあらかじ
め形成し、電極の形にパターニングしたもの用いた。こ
の基板を充分に洗浄した後、蒸着する材料と一緒に真空
装置内にセットし、１０-4Ｐａまで排気した。その後、
ＴＰＴと９、１０―ジフェニルアントラセンの混合膜を
２５ｎｍ製膜した。Embodiment 8 Hereinafter, an eighth embodiment of the present invention will be described. In the eighth embodiment, a substrate was used in which an indium tin oxide film (ITO) was previously formed on a glass as a transparent anode and patterned in the form of an electrode. After sufficiently washing the substrate, the substrate was set in a vacuum device together with the material to be deposited, and the substrate was evacuated to 10 -4 Pa. afterwards,
A 25 nm mixed film of TPT and 9,10-diphenylanthracene was formed.
【００４８】製膜は２つの材料を別々の蒸着源から蒸発
させる共蒸着法により行い、ＴＰＴに対する９、１０―
ジフェニルアントラセンの混合比は１ｍｏｌ％とした。
さらに、その上にＴＰＴを２５ｎｍ製膜した。その後、
発光層兼電子注入輸送層としてＡｌｑを５０ｎｍ製膜し
た後、陰極としてＡｌＬｉ合金を１５０ｎｍの厚さで製
膜し、素子を作成した。The film is formed by a co-evaporation method in which the two materials are evaporated from separate evaporation sources, and a 9, 10-
The mixing ratio of diphenylanthracene was 1 mol%.
Further, 25 nm of TPT was formed thereon. afterwards,
After forming Alq to a thickness of 50 nm as a light emitting layer and an electron injection / transport layer, an AlLi alloy was formed to a thickness of 150 nm as a cathode to form a device.
【００４９】得られた素子に電圧を印加したところ、均
一な黄緑色の発光が得られた。ＥＬスペクトルを測定し
たところ、９、１０―ジフェニルアントラセンからの発
光は観測されなかった。１００ｍＡ／ｃｍ2の電流を印
加した場合の駆動電圧ならびに発光輝度を測定したとこ
ろ、駆動電圧６．７Ｖ、発光輝度は２５９０ｃｄ／ｍ 2
であった。この素子を乾燥窒素中において、初期輝度１
０００ｃｄ／ｍ2で連続駆動（定電流）したところ、輝
度半減期は３８０ｈであった。また、５００ｈ駆動後の
電圧上昇分は１．８Ｖであった。When a voltage was applied to the obtained device,
One yellow-green emission was obtained. Measure the EL spectrum
The emission from 9,10-diphenylanthracene
No light was observed. 100mA / cmTwoMark the current
The drive voltage and light emission brightness were measured.
The driving voltage is 6.7 V and the emission luminance is 2590 cd / m. Two
Met. The device was dried in dry nitrogen at an initial luminance of 1
000cd / mTwoWhen driven continuously (constant current) with
The degree half-life was 380 h. Also, after 500 hours of driving
The voltage rise was 1.8V.
【００５０】（実施例９）以下、本発明第９の実施例を
説明する。第９の実施例では、９、１０―ジフェニルア
ントラセンの代わりにクマリン５１５（Ｅｘｃｉｔｏｎ
社製）を用いたこと以外は第８の実施例と同様にして素
子を作成した。Embodiment 9 Hereinafter, a ninth embodiment of the present invention will be described. In the ninth embodiment, coumarin 515 (Exciton) was used instead of 9,10-diphenylanthracene.
A device was prepared in the same manner as in the eighth embodiment except that the above-described device was used.
【００５１】得られた素子に電圧を印加したところ、均
一な黄緑色の発光が得られた。発光スペクトルを測定し
たところ、クマリン５１５からの発光は観測されなかっ
た。１００ｍＡ／ｃｍ2の電流を印加した場合の駆動電
圧ならびに発光輝度を測定したところ、駆動電圧６．２
Ｖ、発光輝度２４６０ｃｄ／ｍ2であった。この素子を
乾燥窒素中において初期輝度１０００ｃｄ／ｍ2で連続
駆動（定電流）したところ、輝度半減期は５００ｈであ
った。また５００ｈ駆動後の電圧上昇分は１．０Ｖであ
った。When a voltage was applied to the obtained device, uniform yellow-green light emission was obtained. When the emission spectrum was measured, no emission from coumarin 515 was observed. When the driving voltage and emission luminance when a current of 100 mA / cm 2 was applied, the driving voltage was 6.2.
V, emission luminance was 2460 cd / m 2 . When this device was continuously driven (constant current) at an initial luminance of 1000 cd / m 2 in dry nitrogen, the luminance half life was 500 hours. The voltage rise after driving for 500 hours was 1.0 V.
【００５２】（実施例１０）以下、本発明第１０の実施
例を説明する。第１０の実施例では、９、１０―ジフェ
ニルアントラセンの代わりにＤＣＭ（Ｅｘｃｉｔｏｎ社
製）を用いたこと以外は第８の実施例と同様にして素子
を作成した。Embodiment 10 Hereinafter, a tenth embodiment of the present invention will be described. In the tenth embodiment, a device was fabricated in the same manner as the eighth embodiment except that DCM (manufactured by Exciton) was used instead of 9,10-diphenylanthracene.
【００５３】得られた素子に電圧を印加したところ、均
一な黄緑色の発光が得られた。発光スペクトルを測定し
たところ、ＤＣＭからの発光は観測されなかった。１０
０ｍＡ／ｃｍ2の電流を印加した場合の駆動電圧ならび
に発光輝度を測定したところ、駆動電圧６．５Ｖ、発光
輝度２４８０ｃｄ／ｍ2であった。この素子を乾燥窒素
中において初期輝度１０００ｃｄ／ｍ2で連続駆動（定
電流）したところ、輝度半減期は３００ｈであった。ま
た５００ｈ駆動後の電圧上昇分は１．５Ｖであった。When a voltage was applied to the obtained device, uniform yellow-green light emission was obtained. When the emission spectrum was measured, no emission from DCM was observed. 10
When the drive voltage and the emission luminance when a current of 0 mA / cm 2 was applied were measured, the drive voltage was 6.5 V and the emission luminance was 2480 cd / m 2 . When this device was continuously driven (constant current) at an initial luminance of 1000 cd / m 2 in dry nitrogen, the luminance half life was 300 h. The voltage rise after driving for 500 hours was 1.5V.
【００５４】（実施例１１）以下、本発明第１１の実施
例を説明する。第１１の実施例では、基板にはガラス上
に透明な陽極としてインジウム錫酸化膜（ＩＴＯ）をあ
らかじめ形成し、電極の形にパターニングしたもの用い
た。この基板を充分に洗浄した後、蒸着する材料と一緒
に真空装置内にセットし、１０-4Ｐａまで排気した。Ｔ
ＰＴを１０ｎｍ製膜した後、ＴＰＴと９、１０―ジフェ
ニルアントラセンの混合膜を２５ｎｍ製膜した。Embodiment 11 Hereinafter, an eleventh embodiment of the present invention will be described. In the eleventh embodiment, an indium tin oxide film (ITO) was previously formed as a transparent anode on glass and patterned into an electrode shape. After sufficiently washing the substrate, the substrate was set in a vacuum device together with the material to be deposited, and the substrate was evacuated to 10 -4 Pa. T
After forming 10 nm of PT, 25 nm of a mixed film of TPT and 9,10-diphenylanthracene was formed.
【００５５】製膜は２つの材料を別々の蒸着源から蒸発
させる共蒸着法により行い、ＴＰＴに対する９、１０―
ジフェニルアントラセンの混合比は１ｍｏｌ％とした。
さらに、その上にＴＰＴを１５ｎｍ製膜した。その後、
発光層兼電子注入輸送層としてＡｌｑを５０ｎｍ製膜し
た後、陰極としてＡｌＬｉ合金を１５０ｎｍの厚さで製
膜し、素子を作成した。The film formation is performed by a co-evaporation method in which two materials are evaporated from separate evaporation sources, and a 9, 10-
The mixing ratio of diphenylanthracene was 1 mol%.
Further, a 15-nm thick TPT was formed thereon. afterwards,
After forming Alq to a thickness of 50 nm as a light emitting layer and an electron injection / transport layer, an AlLi alloy was formed to a thickness of 150 nm as a cathode to form a device.
【００５６】得られた素子に電圧を印加したところ、均
一な黄緑色の発光が得られた。ＥＬスペクトルを測定し
たところ、９、１０―ジフェニルアントラセンからの発
光は観測されなかった。１００ｍＡ／ｃｍ2の電流を印
加した場合の駆動電圧ならびに発光輝度を測定したとこ
ろ、駆動電圧６．５Ｖ、発光輝度は２５３０ｃｄ／ｍ 2
であった。この素子を乾燥窒素中において、初期輝度１
０００ｃｄ／ｍ2で連続駆動（定電流）したところ、輝
度半減期は３７０ｈであった。また、５００ｈ駆動後の
電圧上昇分は１．６Ｖであった。When a voltage was applied to the obtained device,
One yellow-green emission was obtained. Measure the EL spectrum
The emission from 9,10-diphenylanthracene
No light was observed. 100mA / cmTwoMark the current
The drive voltage and light emission brightness were measured.
The driving voltage is 6.5 V and the emission luminance is 2530 cd / m. Two
Met. The device was dried in dry nitrogen at an initial luminance of 1
000cd / mTwoWhen driven continuously (constant current) with
The degree half-life was 370 h. Also, after 500 hours of driving
The voltage rise was 1.6V.
【００５７】（実施例１２）以下、本発明第１２の実施
例を説明する。第１２の実施例では、９、１０―ジフェ
ニルアントラセンの代わりにクマリン５１５（Ｅｘｃｉ
ｔｏｎ社製）を用いたこと以外は第１１の実施例と同様
にして素子を作成した。Embodiment 12 Hereinafter, a twelfth embodiment of the present invention will be described. In the twelfth embodiment, coumarin 515 (Exci) is used instead of 9,10-diphenylanthracene.
An element was prepared in the same manner as in the eleventh example except that the device was manufactured by Ton Inc.
【００５８】得られた素子に電圧を印加したところ、均
一な黄緑色の発光が得られた。発光スペクトルを測定し
たところ、ＤＣＭからの発光は観測されなかった。１０
０ｍＡ／ｃｍ2の電流を印加した場合の駆動電圧ならび
に発光輝度を測定したところ、駆動電圧６．８Ｖ、発光
輝度２５７０ｃｄ／ｍ2であった。この素子を乾燥窒素
中において初期輝度１０００ｃｄ／ｍ2で連続駆動（定
電流）したところ、輝度半減期は４２０ｈであった。ま
た５００ｈ駆動後の電圧上昇分は１．３Ｖであった。When a voltage was applied to the obtained device, uniform yellow-green light emission was obtained. When the emission spectrum was measured, no emission from DCM was observed. 10
When the driving voltage and the emission luminance when a current of 0 mA / cm 2 was applied were measured, the driving voltage was 6.8 V and the emission luminance was 2570 cd / m 2 . When this device was continuously driven (constant current) at an initial luminance of 1000 cd / m 2 in dry nitrogen, the luminance half life was 420 h. The voltage rise after driving for 500 hours was 1.3 V.
【００５９】（比較例１）比較例１として、発光層と電
荷注入輸送層の代りに発光層兼電子注入輸送層としてＡ
ｌｑを用いたこと以外は第１の実施例と同様に素子を作
製した。この素子に電圧を印加したところ、均一な黄緑
色の発光が得られた。１００ｍＡ／ｃｍ2印加時の駆動
電圧は６．２Ｖ、発光輝度は２３１０ｃｄ／ｍ2であっ
た。また、初期輝度１０００ｃｄ／ｍ2で連続駆動（定
電流）したときの輝度半減期は３００ｈ、５００ｈ駆動
後の電圧上昇分は２．０Ｖであった。(Comparative Example 1) As Comparative Example 1, instead of the light emitting layer and the charge injection / transport layer, A was used as the light emitting layer and the electron injection / transport layer.
A device was manufactured in the same manner as in the first example except that lq was used. When a voltage was applied to this element, uniform yellow-green light emission was obtained. The driving voltage at the time of application of 100 mA / cm 2 was 6.2 V, and the emission luminance was 2310 cd / m 2 . The luminance half-life during continuous driving (constant current) at an initial luminance of 1000 cd / m 2 was 300 h, and the voltage increase after driving for 500 h was 2.0 V.
【００６０】（比較例２）比較例２として、正孔注入層
に（化１）に示すチオフェン誘導体（１）を用いたこと
以外は第３の実施例と同様に素子を作製した。この素子
に電圧を印加したところ、均一な黄緑色の発光が得られ
た。１００ｍＡ／ｃｍ2印加時の駆動電圧は５．７Ｖ、
発光輝度は２０８０ｃｄ／ｍ2であった。また、初期輝
度１０００ｃｄ／ｍ2で連続駆動（定電流）したとこ
ろ、輝度が半減する前に電極間が短絡し、素子として機
能しなくなった。Comparative Example 2 As Comparative Example 2, a device was produced in the same manner as in the third example except that the thiophene derivative (1) shown in Chemical Formula 1 was used for the hole injection layer. When a voltage was applied to this element, uniform yellow-green light emission was obtained. The driving voltage when applying 100 mA / cm 2 is 5.7 V,
The light emission luminance was 2080 cd / m 2 . Further, when the electrode was continuously driven (constant current) at an initial luminance of 1000 cd / m 2 , the electrodes were short-circuited before the luminance was reduced by half, and the element did not function as an element.
【００６１】実施例１から１２および比較例１、２に示
した結果より、本実施例で得られた素子は比較例で得ら
れた素子よりも発光効率や駆動耐久性に優れていること
が明らかになった。From the results shown in Examples 1 to 12 and Comparative Examples 1 and 2, it can be seen that the device obtained in this example is more excellent in luminous efficiency and driving durability than the device obtained in the comparative example. It was revealed.
【００６２】[0062]
【発明の効果】以上のように本発明によれば、発光効率
が高く、駆動耐久性に優れた有機電界発光素子が得られ
るという有利な効果が得られる。As described above, according to the present invention, there is obtained an advantageous effect that an organic electroluminescent device having high luminous efficiency and excellent driving durability can be obtained.
【図１】本発明第１の実施の形態における有機電界発光
素子の構成の断面図FIG. 1 is a cross-sectional view of a configuration of an organic electroluminescent device according to a first embodiment of the present invention.
【図２】本発明第２の実施の形態における有機電界発光
素子の構成の断面図FIG. 2 is a cross-sectional view of a configuration of an organic electroluminescent device according to a second embodiment of the present invention.
１ ガラス基板 ２ 陽極 ３ 正孔注入層 ４ 正孔輸送層 ５ 発光層 ６ 電子輸送層 ７ 電子注入層 ８ 陰極 ９ 混合層 REFERENCE SIGNS LIST 1 glass substrate 2 anode 3 hole injection layer 4 hole transport layer 5 light emitting layer 6 electron transport layer 7 electron injection layer 8 cathode 9 mixed layer
───────────────────────────────────────────────────── フロントページの続き (72)発明者 堀 義和 大阪府門真市大字門真1006番地 松下電器 産業株式会社内 Ｆターム(参考） 3K007 AB03 AB04 AB11 CA01 CB01 DA01 DB03 EB00 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Yoshikazu Hori 1006 Kadoma Kadoma, Osaka Prefecture Matsushita Electric Industrial Co., Ltd. F term (reference) 3K007 AB03 AB04 AB11 CA01 CB01 DA01 DB03 EB00
Claims (8)
光層を有し、前記発光層が置換または無置換のチオフェ
ンオリゴマーを含む複数の有機材料を含む有機電界発光
素子。1. An organic electroluminescent device having a pair of electrodes and a light emitting layer between the pair of electrodes, wherein the light emitting layer includes a plurality of organic materials including a substituted or unsubstituted thiophene oligomer.
フェン環を有する請求項１記載の有機電界発光素子。2. The organic electroluminescent device according to claim 1, wherein the thiophene oligomer has four or more thiophene rings.
光層、正孔注入層及び正孔輸送層を有し、前記正孔注入
層又は前記正孔輸送層が２種類以上の有機材料の混合物
からなっており、前記有機材料のうちの少なくとも一つ
がオリゴマー材料である有機電界発光素子。3. A light-emitting layer, a hole-injection layer, and a hole-transport layer between the pair of electrodes and the pair of electrodes. An organic electroluminescent device comprising a mixture of materials, wherein at least one of the organic materials is an oligomer material.
は置換基を有するトリフェニルアミンオリゴマーである
請求項３記載の有機電界発光素子。4. The organic electroluminescent device according to claim 3, wherein at least one of the organic materials is an unsubstituted or substituted triphenylamine oligomer.
無置換のチオフェンオリゴマーである請求項３記載の有
機電界発光素子。5. The organic electroluminescent device according to claim 3, wherein at least one of the organic materials is a substituted or unsubstituted thiophene oligomer.
を注入、輸送する正孔注入輸送層を有する請求項３、４
又は５記載の有機電界発光素子。6. A hole injecting and transporting layer for injecting and transporting holes, instead of the hole injecting layer and the hole transporting layer.
Or the organic electroluminescent element of 5.
発光層と少なくとも一層以上の有機層を有し、前記発光
層と隣接する有機層に、発光層から発せられる光のピー
ク波長よりも短波長の吸収ピーク波長を有する蛍光材料
が混合されている有機電界発光素子。7. A light-emitting layer and at least one or more organic layers between the pair of electrodes and the pair of electrodes, wherein an organic layer adjacent to the light-emitting layer has a peak wavelength of light emitted from the light-emitting layer. An organic electroluminescent device in which a fluorescent material having a short absorption peak wavelength is mixed.
光層と少なくとも一層以上の有機層を有し、前記発光層
と隣接しない有機層に蛍光材料が混合されている有機電
界発光素子。8. An organic electroluminescent device having a pair of electrodes, a light emitting layer and at least one or more organic layers between the pair of electrodes, and a fluorescent material mixed in an organic layer not adjacent to the light emitting layer. .
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000341560A JP3664069B2 (en) | 1999-12-24 | 2000-11-09 | Organic electroluminescence device |
| US09/740,858 US6730929B2 (en) | 1999-12-24 | 2000-12-21 | Organic electroluminescent device |
| EP00128364A EP1111695A3 (en) | 1999-12-24 | 2000-12-22 | Organic electroluminescent device |
| KR10-2000-0080567A KR100409146B1 (en) | 1999-12-24 | 2000-12-22 | Organic electroluminescent device |
| US10/694,025 US20040061108A1 (en) | 1999-12-24 | 2003-10-28 | Organic electroluminescent device |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP36720099 | 1999-12-24 | ||
| JP11-367200 | 1999-12-24 | ||
| JP2000-196111 | 2000-06-29 | ||
| JP2000196111 | 2000-06-29 | ||
| JP2000341560A JP3664069B2 (en) | 1999-12-24 | 2000-11-09 | Organic electroluminescence device |
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| JP2005007363A Division JP2005101017A (en) | 1999-12-24 | 2005-01-14 | Organic electroluminescent element |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005116247A (en) * | 2003-10-06 | 2005-04-28 | Mitsui Chemicals Inc | Organic electroluminescent element and amine compound |
| WO2006061954A1 (en) * | 2004-12-08 | 2006-06-15 | Fuji Electric Holdings Co., Ltd. | Organic el element |
| WO2007058172A1 (en) * | 2005-11-17 | 2007-05-24 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| JP2012134457A (en) * | 2010-12-21 | 2012-07-12 | Shanghai Casail Display Technology Ltd | Solid solution induction layer for weak epitaxy growth of nonplanar phthalocyanine |
| JP2013515016A (en) * | 2009-12-22 | 2013-05-02 | 上海 カサイル ディスプレイ テクノロジー エルティーディ | Induction layer material for weak epitaxial films of non-planar metal phthalocyanine |
-
2000
- 2000-11-09 JP JP2000341560A patent/JP3664069B2/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005116247A (en) * | 2003-10-06 | 2005-04-28 | Mitsui Chemicals Inc | Organic electroluminescent element and amine compound |
| JP4563015B2 (en) * | 2003-10-06 | 2010-10-13 | 三井化学株式会社 | Organic electroluminescence device |
| WO2006061954A1 (en) * | 2004-12-08 | 2006-06-15 | Fuji Electric Holdings Co., Ltd. | Organic el element |
| GB2436226A (en) * | 2004-12-08 | 2007-09-19 | Fuji Electric Holdings Co | Organic EL element |
| WO2007058172A1 (en) * | 2005-11-17 | 2007-05-24 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| JP2013515016A (en) * | 2009-12-22 | 2013-05-02 | 上海 カサイル ディスプレイ テクノロジー エルティーディ | Induction layer material for weak epitaxial films of non-planar metal phthalocyanine |
| JP2012134457A (en) * | 2010-12-21 | 2012-07-12 | Shanghai Casail Display Technology Ltd | Solid solution induction layer for weak epitaxy growth of nonplanar phthalocyanine |
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