JPH0633047A - Organic thin film luminescent element - Google Patents

Organic thin film luminescent element

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Publication number
JPH0633047A
JPH0633047A JP4184229A JP18422992A JPH0633047A JP H0633047 A JPH0633047 A JP H0633047A JP 4184229 A JP4184229 A JP 4184229A JP 18422992 A JP18422992 A JP 18422992A JP H0633047 A JPH0633047 A JP H0633047A
Authority
JP
Japan
Prior art keywords
light emitting
layer
thin film
organic thin
injection layer
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
Application number
JP4184229A
Other languages
Japanese (ja)
Other versions
JP3099529B2 (en
Inventor
Yoshinobu Sugata
好信 菅田
Yotaro Shiraishi
洋太郎 白石
Masami Kuroda
昌美 黒田
Noboru Kosho
昇 古庄
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fuji Electric Co Ltd
Original Assignee
Fuji Electric Co Ltd
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Filing date
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  • Luminescent Compositions (AREA)

Abstract

PURPOSE:To provide the subject luminescent element generating stable green luminescence having a high brightness, excellent in the film-forming property, and useful for display devices, etc., by adding a specific compound to a luminescent layer disposed between a positive hole-injected layer and an electron- injected layer which are nipped with a pair of electrodes comprising an anode and a cathode. CONSTITUTION:The objective luminescent element is characterized by having a pair of electrodes consisting of an anode 2 and a cathode 6, a charge-injected layer and a luminescent layer 4, both the layers being nipped with the electrodes, the charge-injected layer comprising at least one of an electron-injected layer 5 and a positive hole-injected layer 3, and the luminescent layer 4 being nipped with the charge-injected layers, the injected electrons and the position holes being recombined with each other to generate light, and containing an ethylenic compound of the formula (R1-R5 are H, halogen, alkyl, alkoxy, aryl; R6, R7 are H, alkyl).

Description

【発明の詳細な説明】Detailed Description of the Invention

【0001】[0001]

【産業上の利用分野】この発明は各種表示装置の発光源
として用いる有機薄膜発光素子に係り、特に素子の発光
層に用いられる発光物質に関する。
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic thin film light emitting device used as a light emitting source of various display devices, and more particularly to a light emitting substance used for a light emitting layer of the device.

【0002】[0002]

【従来の技術】従来のブラウン管に代わるフラットディ
スプレイの需要の急増に伴い、各種表示素子の開発及び
実用化が精力的に進められている。エレクトロルミネッ
センス素子(以下EL素子とする)もこうしたニ−ズに
即するものであり、特に全固体の自発発光素子として、
他のディスプレイにはない高解像度及び高視認性により
注目を集めている。現在、実用化されているものは、発
光層にZnS/Mn系を用いた無機材料からなるEL素
子である。しかるに、この種の無機EL素子は発光に必
要な駆動電圧が100V以上と高いため駆動方法が複雑
となり製造コストが高いといった問題点がある。また、
青色発光の効率が低いため、フルカラ−化が困難であ
る。これに対して、有機材料を用いた薄膜発光素子は、
発光に必要な駆動電圧が大幅に低減でき、かつ各種発光
材料の適用によりフルカラ−化の可能性を充分に持つこ
とから、近年研究が活発化している。
2. Description of the Related Art With the rapid increase in demand for flat displays replacing conventional cathode ray tubes, various display elements have been vigorously developed and put into practical use. An electroluminescence element (hereinafter referred to as an EL element) is also adapted to such a need, and in particular, as an all solid state spontaneous light emitting element,
It attracts attention due to its high resolution and high visibility that other displays do not have. At present, what has been put into practical use is an EL element made of an inorganic material using a ZnS / Mn system in the light emitting layer. However, this type of inorganic EL element has a problem that the driving method is complicated and the manufacturing cost is high because the driving voltage required for light emission is as high as 100 V or more. Also,
Since the efficiency of blue light emission is low, full colorization is difficult. On the other hand, a thin film light emitting device using an organic material is
Since the driving voltage required for light emission can be significantly reduced and the potential for full color conversion can be sufficiently obtained by applying various light emitting materials, research has been actively conducted in recent years.

【0003】特に、電極/正孔注入層/発光層/電極か
らなる積層型において、発光剤にトリス(8−ヒドロキ
シキノリン)アルミニウムを、正孔注入剤に1,1’−
ビス(4−N,N−ジトリアミノフェニル)シクロヘキ
サンを用いることにより、10V以下の印加電圧で10
00cd/cm2 以上の輝度が得られたという報告がな
されて以来開発に拍車がかけられた(Appl.Phys.Lett.
51,913,(1987))。
In particular, in the laminated type composed of electrode / hole injection layer / light emitting layer / electrode, tris (8-hydroxyquinoline) aluminum is used as the light emitting agent and 1,1′-is used as the hole injection agent.
By using bis (4-N, N-ditriaminophenyl) cyclohexane, an applied voltage of 10 V or less
The development was spurred since it was reported that a brightness of more than 00 cd / cm 2 was obtained (Appl.Phys.Lett.
51 , 913, (1987)).

【0004】[0004]

【発明が解決しようとする課題】この様に、有機材料を
用いた薄膜発光素子は低電圧駆動やフルカラ−化の可能
性等を強く示唆しているものの、性能面で解決しなけれ
ばならない課題が多く残されている。特に約1万時間の
長時間駆動に伴う特性劣化の問題は乗り越えなければな
らない課題である。また、フルカラー化におけるRGB
三原色の発光を可能にする発光材料の開発、また有機層
の膜厚が1μm以下であるために、成膜性が良好でピン
ホール等の電気的欠陥がなく、電子,正孔の輸送能力に
優れた有機材料の開発、有機層への電荷の注入性に優れ
る電極材料の選択等がある。
As described above, although the thin film light emitting device using an organic material strongly suggests the possibility of low voltage driving and full colorization, the problem to be solved in terms of performance. There are many left. In particular, the problem of characteristic deterioration due to long-time driving of about 10,000 hours is a problem that must be overcome. In addition, RGB in full color
Development of light-emitting material that enables emission of three primary colors, and because the organic layer has a thickness of 1 μm or less, film formation is good, there are no electrical defects such as pinholes, and electron and hole transporting ability Development of excellent organic materials, selection of electrode materials with excellent charge injection properties into organic layers, etc.

【0005】さらには量産性の観点から大量製造が可能
で安価な有機材料の開発や素子形成方法の改良等も重要
な課題である。この発明は上述の点に鑑みてなされその
目的は、高輝度で安定性に優れるうえに成膜性が良好な
新規な緑色発光物質を開発することにより高輝度で安定
性に優れ、安価かつ容易に製造可能な有機薄膜発光素子
を提供することにある。
Further, from the viewpoint of mass productivity, the development of inexpensive organic materials that can be mass-produced and the improvement of the element forming method are important issues. The present invention has been made in view of the above points, and an object thereof is to develop a novel green light-emitting substance having high brightness and excellent stability as well as good film-forming property. Another object is to provide a manufacturable organic thin film light emitting device.

【0006】[0006]

【課題を解決するための手段】上述の目的はこの発明に
よれば正極と負極とからなる一対の電極と、その間に挟
まれた電荷注入層と発光層とを有し、電荷注入層は電子
注入層と正孔注入層の内の少なくとも一方からなり、発
光層は電荷注入層に挟まれてなり、注入された電子と正
孔を再結合させて発光するものであり、下記一般式
(I)のエチレン系化合物を含むものであるとすること
により達成される。
According to the present invention, the above-mentioned object has a pair of electrodes consisting of a positive electrode and a negative electrode, and a charge injection layer and a light emitting layer sandwiched therebetween, and the charge injection layer is an electron. The light emitting layer is composed of at least one of an injection layer and a hole injection layer, and the light emitting layer is sandwiched between charge injection layers, and recombines the injected electrons and holes to emit light. ) It is achieved by including the ethylene compound.

【0007】[0007]

【化2】 [Chemical 2]

【0008】〔式(I)中、R1 ,R2 ,R3 ,R4
5 ,R8 ,R9 ,R10,R11,R12はそれぞれ水素原
子,ハロゲン原子,アルキル基,アルコキシ基またはア
リール基、R6 ,R7 は水素原子,アルキル基を表
す。〕一般式(I)で示されるエチレン系化合物の具体
例が以下に示される。
[In the formula (I), R 1 , R 2 , R 3 , R 4 ,
R 5 , R 8 , R 9 , R 10 , R 11 , and R 12 represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an aryl group, and R 6 and R 7 represent a hydrogen atom and an alkyl group. Specific examples of the ethylene compound represented by formula (I) are shown below.

【0009】[0009]

【化3】 [Chemical 3]

【0010】[0010]

【化4】 [Chemical 4]

【0011】[0011]

【作用】本発明者等は前記目的を達成するために各種物
質について多くの実験を重ねた結果、詳細は不明である
が前記一般式(I)で示されるエチレン系化合物が有効
であることを見い出した。
The present inventors have conducted many experiments on various substances in order to achieve the above-mentioned object, and as a result, although the details are unknown, it is found that the ethylene compound represented by the general formula (I) is effective. I found it.

【0012】[0012]

【実施例】本発明におけるエチレン系化合物を用いた有
機薄膜発光素子の具体的実施例について、図面を参照し
ながら説明する。一般式(I)に示すエチレン系化合物
のうち対称な化合物は一般式(IV)に示す中間体を用
い、テトラヒドロフラン等の有機溶媒中で四塩化チタン
と亜鉛とによるカプリング反応により合成することがで
きる。
EXAMPLES Specific examples of the organic thin film light emitting device using the ethylene compound according to the present invention will be described with reference to the drawings. A symmetrical compound among the ethylene compounds represented by the general formula (I) can be synthesized by using the intermediate represented by the general formula (IV) by a coupling reaction between titanium tetrachloride and zinc in an organic solvent such as tetrahydrofuran. .

【0013】[0013]

【化5】 [Chemical 5]

【0014】〔式(I)中、R1 ,R2 ,R3 ,R4
5 はそれぞれ水素原子,ハロゲン原子,アルキル基,
アルコキシ基またはアリール基、R6 は水素原子,アル
キル基を表す。〕図1はこの発明の実施例に係る有機薄
膜発光素子を示す断面図である。図2はこの発明の異な
る実施例に係る有機薄膜発光素子を示す断面図である。
[In the formula (I), R 1 , R 2 , R 3 , R 4 ,
R 5 is a hydrogen atom, a halogen atom, an alkyl group,
An alkoxy group or an aryl group, R 6 represents a hydrogen atom or an alkyl group. FIG. 1 is a sectional view showing an organic thin film light emitting device according to an embodiment of the present invention. FIG. 2 is a sectional view showing an organic thin film light emitting device according to another embodiment of the present invention.

【0015】図3はこの発明のさらに異なる実施例に係
る有機薄膜発光素子を示す断面図である。1は絶縁性基
板、2は正極、3は正孔注入層、4は発光層、5は電子
注入層、6は負極である。絶縁性基板1は素子の支持体
でガラス,樹脂等を用いる。発光面となるときは透明な
材料を用いる。
FIG. 3 is a sectional view showing an organic thin film light emitting device according to another embodiment of the present invention. 1 is an insulating substrate, 2 is a positive electrode, 3 is a hole injection layer, 4 is a light emitting layer, 5 is an electron injection layer, and 6 is a negative electrode. The insulating substrate 1 is made of glass, resin or the like as a support for the element. A transparent material is used for the light emitting surface.

【0016】正極2は金,ニッケル等の半透膜やインジ
ウムスズ酸化物(ITO),酸化スズ(SnO2 )等の
透明導電膜からなり抵抗加熱蒸着、電子ビ−ム蒸着、ス
パッタ法により形成する。該正極2は、透明性を持たせ
るために、100〜3000Åの厚さにすることが望ま
しい。正孔注入層3は正孔を効率良く輸送し、且つ注入
することが必要で発光した光の発光極大領域においてで
きるだけ透明であることが望ましい。成膜方法としてス
ピンコ−ト、キャスティング、LB法、抵抗加熱蒸着、
電子ビ−ム蒸着等があるが抵抗加熱蒸着が一般的であ
る。膜厚は200ないし5000Åであり、好適には3
00ないし800Åである。正孔注入物質としてはヒド
ラゾン化合物,ピラゾリン化合物,スチルベン化合物,
アミン系化合物などが用いられる。代表的な正孔注入物
質が以下に示される。
The positive electrode 2 is made of a semi-permeable film of gold, nickel or the like or a transparent conductive film of indium tin oxide (ITO), tin oxide (SnO 2 ) or the like, and is formed by resistance heating vapor deposition, electron beam vapor deposition, or sputtering. To do. It is desirable that the positive electrode 2 has a thickness of 100 to 3000 Å in order to have transparency. The hole injection layer 3 is required to efficiently transport and inject holes, and it is desirable that the hole injection layer 3 be as transparent as possible in the emission maximum region of the emitted light. Spin coating, casting, LB method, resistance heating vapor deposition,
Although there are electron beam vapor deposition and the like, resistance heating vapor deposition is general. The film thickness is 200 to 5000Å, preferably 3
It is 00 to 800Å. As a hole injection material, a hydrazone compound, a pyrazoline compound, a stilbene compound,
An amine compound or the like is used. Representative hole injecting materials are shown below.

【0017】[0017]

【化6】 [Chemical 6]

【0018】発光層は正孔注入層または正極から注入さ
れた正孔と、負極または電子注入層より注入された電子
の再結合により効率良く発光を行う。成膜方法はスピン
コ−ト、キャスティング、LB法、抵抗加熱蒸着、電子
ビ−ム蒸着等があるが抵抗加熱蒸着が一般的である。膜
厚は200ないし5000Åであるが好適には300な
いし800Åである。
The light emitting layer efficiently emits light by recombination of holes injected from the hole injection layer or the positive electrode and electrons injected from the negative electrode or the electron injection layer. Film forming methods include spin coating, casting, LB method, resistance heating evaporation, electron beam evaporation and the like, but resistance heating evaporation is common. The film thickness is 200 to 5000Å, preferably 300 to 800Å.

【0019】電子注入層5は電子を効率良く発光層に注
入することが望ましい。成膜方法はスピンコ−ト、キャ
スティング、LB法、抵抗加熱蒸着、電子ビ−ム蒸着等
があるが抵抗加熱蒸着が一般的である。膜厚は200な
いし5000Åであるが好適には300ないし800Å
である。電子注入物質としてはオキサジアゾール誘導
体,ペリレン誘導体などが用いられる。以下に代表的な
電子注入物質が示される。
It is desirable for the electron injection layer 5 to efficiently inject electrons into the light emitting layer. Film forming methods include spin coating, casting, LB method, resistance heating evaporation, electron beam evaporation and the like, but resistance heating evaporation is common. The film thickness is 200 to 5000Å, preferably 300 to 800Å
Is. An oxadiazole derivative, a perylene derivative, etc. are used as an electron injection substance. Representative electron injecting materials are shown below.

【0020】[0020]

【化7】 [Chemical 7]

【0021】負極6は電子を効率良く有機層に注入する
ことが必要である。成膜方法としては抵抗加熱蒸着,電
子ビーム蒸着,スパッタ法が用いられる。負極6用材料
としては、仕事関数の小さいMg,Ag,In,Ca,
Al等およびこれらの合金,積層体等が用いられる。 実施例1 膜厚約1000ÅのITOを設けた50mm角のガラス
を基板とし該基板を抵抗加熱蒸着装置内にセットし、前
記図1に示すように正孔注入層、発光層と順次成膜し
た。成膜に際して、真空槽内圧は8×10-4Paとし
た。正孔注入層には前記化学式(II−1)に示される化
合物を用い600Å形成した。続けて発光層として前記
化学式(I−1)に示されるエチレン系化合物を用いボ
−ト温度約210ないし240℃にて加熱し、成膜速度
を約2Å/sとして600Å形成した。この後、基板を
真空槽から取り出し、直径5mmドットパタ−ン用ステ
ンレス製マスクを取りつけ、新たに抵抗加熱蒸着装置内
にセットし負極6として Mg/In(10:1の重量
比率)を形成した。
The negative electrode 6 needs to efficiently inject electrons into the organic layer. As a film forming method, resistance heating evaporation, electron beam evaporation, or sputtering method is used. As the material for the negative electrode 6, Mg, Ag, In, Ca, which has a small work function,
Al and the like, alloys of these and laminated bodies are used. Example 1 Using a glass of 50 mm square provided with ITO having a film thickness of about 1000 Å as a substrate, the substrate was set in a resistance heating vapor deposition apparatus, and a hole injection layer and a light emitting layer were sequentially formed as shown in FIG. . During film formation, the internal pressure of the vacuum chamber was 8 × 10 −4 Pa. The hole injection layer was formed to a thickness of 600Å using the compound represented by the chemical formula (II-1). Subsequently, the ethylene compound represented by the chemical formula (I-1) was used as the light emitting layer and heated at a boat temperature of about 210 to 240 ° C. to form a film of 600 Å at a film forming rate of about 2 Å / s. Then, the substrate was taken out from the vacuum chamber, a stainless mask for a dot pattern with a diameter of 5 mm was attached, and the substrate was newly set in a resistance heating vapor deposition device to form Mg / In (weight ratio of 10: 1) as the negative electrode 6.

【0022】上記実施例1において、該エチレン系化合
物からなる発光層は均一な蒸着膜となり、かつ該直径5
mmの有機薄膜発光素子に直流電圧を印加したところ、
緑色(発光中心波長510〜530nm)の均一な発光
が得られた。また発光輝度120cd/cm2 で100
h以上の安定性を確認した。 実施例2 膜厚約1000ÅのITOを設けた50mm角のガラス
を基板とし該基板を抵抗加熱蒸着装置内にセットし、発
光層、電子注入層と順次成膜した。成膜に際して、真空
槽内圧は8×10-4Paとした。発光層には前記化学式
(I−1)に示される化合物を用いボ−ト温度約210
ないし240℃にて加熱し、成膜速度を約2Å/sとし
て600Å形成した。続けて電子注入層として化学式
(III −4)に示される化合物を用い600Å形成し
た。この後、基板を真空槽から取り出し、直径5mmド
ットパタ−ン用ステンレス製マスクを取りつけ、新たに
抵抗加熱蒸着装置内にセットし負極6として Mg/I
n(10:1の重量比率)を形成した。
In Example 1, the light emitting layer made of the ethylene compound was a uniform vapor deposition film and had a diameter of 5 mm.
When a DC voltage was applied to the organic thin film light emitting element of mm,
Uniform green light emission (emission center wavelength 510 to 530 nm) was obtained. The emission brightness is 120 cd / cm 2 and is 100
The stability of h or more was confirmed. Example 2 A glass of 50 mm square provided with ITO having a film thickness of about 1000 Å was used as a substrate, the substrate was set in a resistance heating vapor deposition apparatus, and a light emitting layer and an electron injection layer were sequentially formed. During film formation, the internal pressure of the vacuum chamber was 8 × 10 −4 Pa. The compound represented by the chemical formula (I-1) is used for the light emitting layer, and the boat temperature is about 210.
To 240 ° C. to form 600 Å at a film forming rate of about 2 Å / s. Subsequently, the compound represented by the chemical formula (III-4) was used as an electron injection layer to form 600 Å. Then, the substrate was taken out from the vacuum chamber, a stainless mask for a dot pattern with a diameter of 5 mm was attached, and the substrate was newly set in a resistance heating vapor deposition device to form Mg / I as a negative electrode 6.
n (10: 1 weight ratio) was formed.

【0023】上記実施例2において、該エチレン系化合
物からなる発光層は均一な蒸着膜となり、かつ該直径5
mmの有機発光素子に直流電圧を印加したところ、緑色
(発光中心波長510〜530nm)の均一な発光が得
られた。また発光輝度100cd/cm2 で120h以
上の安定性を確認した。 実施例3 膜厚約1000ÅのITOを設けた50mm角のガラス
を基板とし該基板を抵抗加熱蒸着装置内に装着し、前記
図3に示す様に正孔注入層、発光層、電子注入層と順次
成膜した。真空槽内圧は8×10-4Paとした。正孔注
入層には前記化学式(II−1)に示される化合物を用い
600Å形成した。続いて発光層として前記エチレン系
化合物のうち化学式(I−1)で示される化合物を用い
ボ−ト温度約210ないし240℃にて加熱し、成膜速
度を約2Å/sとして600Å形成した。さらに続けて
電子注入層として前記化学式(III −4)で示される化
合物をを用い、600Å形成した。この後該基板を真空
槽から取り出し、直径5mmのドットパタ−ンからなる
ステンレス製マスクを取りつけ、新たに抵抗加熱蒸着装
置内に装着し負極6としてMg/In(10:1の比
率)を形成した。
In Example 2, the light emitting layer made of the ethylene compound was a uniform vapor deposition film and had a diameter of 5 mm.
When a DC voltage was applied to the organic light-emitting device having a size of mm, uniform green light emission (emission center wavelength: 510 to 530 nm) was obtained. Further, it was confirmed that the light emission luminance was 100 cd / cm 2 and the stability was 120 hours or more. Example 3 Using a glass of 50 mm square provided with ITO having a film thickness of about 1000 Å as a substrate, the substrate was mounted in a resistance heating vapor deposition apparatus, and a hole injection layer, a light emitting layer, and an electron injection layer were formed as shown in FIG. The films were sequentially formed. The internal pressure of the vacuum chamber was 8 × 10 −4 Pa. The hole injection layer was formed to a thickness of 600Å using the compound represented by the chemical formula (II-1). Then, a compound represented by the chemical formula (I-1) among the above-mentioned ethylene compounds was heated as a light emitting layer and heated at a boat temperature of about 210 to 240 ° C. to form 600 Å at a film forming rate of about 2 Å / s. Further, subsequently, 600 Å was formed as the electron injection layer by using the compound represented by the chemical formula (III-4). After that, the substrate was taken out from the vacuum chamber, a stainless mask made of a dot pattern having a diameter of 5 mm was attached, and the substrate was newly mounted in a resistance heating vapor deposition device to form Mg / In (ratio of 10: 1) as the negative electrode 6. .

【0024】前記実施例3において、該エチレン系化合
物からなる発光層は均一な蒸着膜となり、かつ該直径5
mmの有機薄膜発光素子に直流電圧を印加したところ、
緑色(発光中心波長510〜530nm)の均一な発光
が得られた。また発光輝度180cd/cm2 で150
h以上の安定性を確認した。
In Example 3, the light emitting layer made of the ethylene compound was a uniform vapor deposition film and had a diameter of 5 mm.
When a DC voltage was applied to the organic thin film light emitting element of mm,
Uniform green light emission (emission center wavelength 510 to 530 nm) was obtained. Also, the emission brightness is 180 cd / cm 2 and is 150
The stability of h or more was confirmed.

【0025】[0025]

【発明の効果】この発明によれば正極と負極とからなる
一対の電極と、その間に挟まれた電荷注入層と発光層と
を有し、電荷注入層は電子注入層と正孔注入層の内の少
なくとも一方からなり、発光層は電荷注入層に挟まれて
なり、注入された電子と正孔を再結合させて発光するも
のであり、下記一般式(I)のエチレン系化合物を含む
ものであるので高輝度かつ安定な緑色発光が実現する。
また成膜性に優れ、安価かつ容易に合成されることか
ら、大量製造が容易な有機薄膜発光素子が得られる。
According to the present invention, it has a pair of electrodes consisting of a positive electrode and a negative electrode, and a charge injection layer and a light emitting layer sandwiched therebetween, and the charge injection layer is composed of an electron injection layer and a hole injection layer. The light emitting layer is made of at least one of the above, and the light emitting layer is sandwiched between the charge injecting layers and recombines the injected electrons and holes to emit light, and contains an ethylene compound of the following general formula (I). Therefore, high brightness and stable green light emission are realized.
Further, since it has excellent film-forming properties and is inexpensively and easily synthesized, it is possible to obtain an organic thin film light emitting device that can be easily mass-produced.

【0026】[0026]

【化8】 [Chemical 8]

【0027】〔式(I)中、R1 ,R2 ,R3 ,R4
5 ,R8 ,R9 ,R10,R11,R12はそれぞれ水素原
子,ハロゲン原子,アルキル基,アルコキシ基またはア
リール基、R6 ,R7 は水素原子,アルキル基を表
す。〕
[In the formula (I), R 1 , R 2 , R 3 , R 4 ,
R 5 , R 8 , R 9 , R 10 , R 11 , and R 12 represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an aryl group, and R 6 and R 7 represent a hydrogen atom and an alkyl group. ]

【図面の簡単な説明】[Brief description of drawings]

【図1】この発明の実施例に係る有機薄膜発光素子を示
す断面図
FIG. 1 is a sectional view showing an organic thin film light emitting device according to an embodiment of the present invention.

【図2】この発明の異なる実施例に係る有機薄膜発光素
子を示す断面図
FIG. 2 is a sectional view showing an organic thin film light emitting device according to another embodiment of the present invention.

【図3】この発明のさらに異なる実施例に係る有機薄膜
発光素子を示す断面図
FIG. 3 is a sectional view showing an organic thin film light emitting device according to still another embodiment of the present invention.

【符号の説明】[Explanation of symbols]

1 絶縁性透明基板 2 正極 3 正孔注入層 4 発光層 5 電子注入層 6 負極 1 Insulating transparent substrate 2 Positive electrode 3 Hole injection layer 4 Light emitting layer 5 Electron injection layer 6 Negative electrode

───────────────────────────────────────────────────── フロントページの続き (72)発明者 古庄 昇 神奈川県川崎市川崎区田辺新田1番1号 富士電機株式会社内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Noboru Furusho 1-1, Tanabe Nitta, Kawasaki-ku, Kawasaki-shi, Kanagawa Fuji Electric Co., Ltd.

Claims (4)

【特許請求の範囲】[Claims] 【請求項1】正極と負極とからなる一対の電極と、その
間に挟まれた電荷注入層と発光層とを有し、 電荷注入層は電子注入層と正孔注入層の内の少なくとも
一方からなり、 発光層は電荷注入層に挟まれてなり、注入された電子と
正孔を再結合させて発光するものであり、下記一般式
(I)のエチレン系化合物を含むものであることを特徴
とする有機薄膜発光素子。 【化1】 〔式(I)中、R1 ,R2 ,R3 ,R4 ,R5 ,R8
9 ,R10,R11,R12はそれぞれ水素原子,ハロゲン
原子,アルキル基,アルコキシ基またはアリール基、R
6 ,R7 は水素原子,アルキル基を表す。〕
1. A pair of electrodes consisting of a positive electrode and a negative electrode, and a charge injection layer and a light emitting layer sandwiched therebetween, wherein the charge injection layer comprises at least one of an electron injection layer and a hole injection layer. The light emitting layer is sandwiched between the charge injection layers and recombines the injected electrons and holes to emit light. The light emitting layer contains an ethylene compound represented by the following general formula (I). Organic thin film light emitting device. [Chemical 1] [In the formula (I), R 1 , R 2 , R 3 , R 4 , R 5 , R 8 ,
R 9 , R 10 , R 11 and R 12 are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or an aryl group, R
6 and R 7 represent a hydrogen atom and an alkyl group. ]
【請求項2】請求項1記載の素子において、アルキル基
はメチル基であることを特徴とする有機薄膜発光素子。
2. The organic thin film light emitting device according to claim 1, wherein the alkyl group is a methyl group.
【請求項3】請求項1記載の素子において、アルコキシ
基はメトキシ基であることを特徴とする有機薄膜発光素
子。
3. The organic thin film light emitting device according to claim 1, wherein the alkoxy group is a methoxy group.
【請求項4】請求項1記載の素子において、アリール基
はフェニル基であることを特徴とする有機薄膜発光素
子。
4. The organic thin film light emitting device according to claim 1, wherein the aryl group is a phenyl group.
JP04184229A 1992-07-13 1992-07-13 Organic thin film light emitting device Expired - Lifetime JP3099529B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP04184229A JP3099529B2 (en) 1992-07-13 1992-07-13 Organic thin film light emitting device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP04184229A JP3099529B2 (en) 1992-07-13 1992-07-13 Organic thin film light emitting device

Publications (2)

Publication Number Publication Date
JPH0633047A true JPH0633047A (en) 1994-02-08
JP3099529B2 JP3099529B2 (en) 2000-10-16

Family

ID=16149638

Family Applications (1)

Application Number Title Priority Date Filing Date
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Country Status (1)

Country Link
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EP1074601A2 (en) * 1999-08-02 2001-02-07 Nec Corporation Organic electroluminescent material and electroluminescent device using the same
JP2008106054A (en) * 2006-09-29 2008-05-08 Semiconductor Energy Lab Co Ltd Stilbene derivative, light emitting element, display device, and electronic equipment
EP1744380B1 (en) * 2005-07-15 2008-12-10 Samsung SDI Co., Ltd. Organic light emitting display device
US8704215B2 (en) 2006-09-29 2014-04-22 Semiconductor Energy Laboratory Co., Ltd. Stilbene derivatives, light-emitting element, display device, and electronic device

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1074601A2 (en) * 1999-08-02 2001-02-07 Nec Corporation Organic electroluminescent material and electroluminescent device using the same
EP1074601A3 (en) * 1999-08-02 2004-12-01 Samsung SDI Co., Ltd. Organic electroluminescent material and electroluminescent device using the same
EP1744380B1 (en) * 2005-07-15 2008-12-10 Samsung SDI Co., Ltd. Organic light emitting display device
US7646011B2 (en) 2005-07-15 2010-01-12 Samsung Mobile Display Co., Ltd. Organic light emitting display device
JP2008106054A (en) * 2006-09-29 2008-05-08 Semiconductor Energy Lab Co Ltd Stilbene derivative, light emitting element, display device, and electronic equipment
US8704215B2 (en) 2006-09-29 2014-04-22 Semiconductor Energy Laboratory Co., Ltd. Stilbene derivatives, light-emitting element, display device, and electronic device
US9174927B2 (en) 2006-09-29 2015-11-03 Semiconductor Energy Laboratory Co., Ltd. Stilbene derivatives, light-emitting element, display device, and electronic device

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