JPH04372688A - Organic thin-film el element - Google Patents
Organic thin-film el elementInfo
- Publication number
- JPH04372688A JPH04372688A JP3175927A JP17592791A JPH04372688A JP H04372688 A JPH04372688 A JP H04372688A JP 3175927 A JP3175927 A JP 3175927A JP 17592791 A JP17592791 A JP 17592791A JP H04372688 A JPH04372688 A JP H04372688A
- Authority
- JP
- Japan
- Prior art keywords
- thin film
- organic
- aluminum
- luminescent material
- 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
Links
- 239000010409 thin film Substances 0.000 title claims abstract description 48
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims description 9
- -1 aluminum quinoline derivative Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 22
- 239000007924 injection Substances 0.000 abstract description 22
- 229910052782 aluminium Inorganic materials 0.000 abstract description 15
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 14
- 239000007983 Tris buffer Substances 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 8
- 229910017911 MgIn Inorganic materials 0.000 abstract description 2
- 239000011521 glass Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 238000000313 electron-beam-induced deposition Methods 0.000 abstract 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- CTQMJYWDVABFRZ-UHFFFAOYSA-N cloxiquine Chemical compound C1=CN=C2C(O)=CC=C(Cl)C2=C1 CTQMJYWDVABFRZ-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、平面光源やディスプレ
イに利用される有機薄膜ＥＬ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 an organic thin film EL device used in flat light sources and displays.
【０００２】0002
【従来の技術】有機物質を原料としたＥＬ（電界発光）
素子は、安価な大面積フルカラー表示素子を実現するも
のとして注目を集めている。例えば、アントラセンやペ
リレン等の縮合環芳香族系を原料としてＬＢ（ラングミ
ュアー・ブロジェット）法や真空蒸着法等で薄膜化した
直流駆動の有機薄膜ＥＬ素子が製造され、その発光特性
が研究されている。しかし、従来の有機薄膜ＥＬ素子は
、駆動電圧が高く、かつその発光輝度・効率が無機薄膜
ＥＬ素子のそれと比べて低かった。また、発光特性の劣
化も著しく、実用レベルのものはできなかった。ところ
が、近年、有機薄膜を２層構造にした積層型の新しいタ
イプの有機薄膜ＥＬ素子が報告され、強い関心を持たれ
ている（アプライド・フィジックス・レターズ、５１巻
、９１３ページ、１９８７年参照）。報告によれば、こ
の有機薄膜ＥＬ素子は、図１に示すように、強い蛍光を
発する有機物質を有機発光体薄膜層２４に使用し、アミ
ン系材料を正孔伝導性有機物質の正孔注入層２３に使用
して２層構造とし、これらをＩＴＯ透明電極２２及び電
子注入電極２５で挟むことにより、明るい緑色発光を得
たことが開示されており、６〜７Ｖの直流電圧印加で数
１００ｃｄ／ｍ２ の輝度を得ている。また、最大発光
効率は１．５ ｌｍ／Ｗと、実用レベルに近い性能を持
っている。[Prior art] EL (electroluminescence) using organic materials as raw materials
The device is attracting attention as an inexpensive, large-area, full-color display device. For example, DC-driven organic thin-film EL devices have been manufactured using condensed ring aromatic systems such as anthracene and perylene as raw materials by the LB (Langmuir-Blodgett) method or vacuum evaporation method, and their light-emitting properties have been studied. ing. However, conventional organic thin film EL devices require a high driving voltage and have lower luminance and efficiency than inorganic thin film EL devices. In addition, the luminescence properties deteriorated significantly, making it impossible to achieve a practical level. However, in recent years, a new type of laminated organic thin film EL device with a two-layer structure of organic thin films has been reported and has attracted strong interest (see Applied Physics Letters, Vol. 51, p. 913, 1987). . According to reports, this organic thin film EL device uses an organic material that emits strong fluorescence for the organic light emitting thin film layer 24, as shown in FIG. It is disclosed that bright green light emission was obtained by using the layer 23 to form a two-layer structure and sandwiching these between an ITO transparent electrode 22 and an electron injection electrode 25, and several hundred cd when a DC voltage of 6 to 7 V was applied. /m2 brightness is obtained. Furthermore, the maximum luminous efficiency is 1.5 lm/W, which is close to the practical level.
【０００３】0003
【発明が解決しようとする課題】前述したように、有機
発光性薄膜と有機物の正孔注入層とが２層積層した構造
を有する新しい有機薄膜ＥＬ素子は、最大発光輝度が１
０００ｃｄ／ｍ２ 以上の明るい緑色発光を示す。この
素子は、電流駆動型であるために、上記の輝度を得るた
めには１００ｍＡ／ｃｍ２ 以上の電流を流さなければ
ならない。しかし従来有機発光体薄膜層に使用していた
無置換のアルミキノリウム錯体では、−１．８４Ｖ
ｖｓ．ＳＣＥと還元電位が大きいために、電子注入電極
からの電子注入効率が悪く、安定して充分電流を流すこ
とができなかった。本発明は、以上述べたような従来の
事情に鑑みてなされたもので、素子発光効率がさらに向
上し、かつ発光輝度の劣化速度が低下した有機薄膜ＥＬ
素子を提供することを目的とする。[Problems to be Solved by the Invention] As mentioned above, a new organic thin film EL device having a two-layer structure of an organic luminescent thin film and an organic hole injection layer has a maximum luminance of 1.
It emits bright green light of 000 cd/m2 or more. Since this element is of a current drive type, a current of 100 mA/cm2 or more must be passed in order to obtain the above luminance. However, with the unsubstituted aluminum quinolium complex conventionally used in the organic light emitting thin film layer, -1.84V
vs. Since the SCE and reduction potential were large, the efficiency of electron injection from the electron injection electrode was poor, and a sufficient current could not be passed stably. The present invention has been made in view of the conventional circumstances as described above, and provides an organic thin film EL device that further improves device luminous efficiency and reduces the rate of deterioration of luminance.
The purpose is to provide an element.
【０００４】0004
【課題を解決するための手段】本発明は、少なくとも一
方が透明な一対の電極間に、有機発光体薄膜層を少なく
とも有する有機薄膜ＥＬ素子、あるいは有機発光体薄膜
層と有機電荷輸送性薄膜層とが積層された有機薄膜ＥＬ
素子において、有機発光体薄膜層の主成分が一般式１：
[Means for Solving the Problems] The present invention provides an organic thin film EL element having at least an organic light emitting thin film layer between a pair of electrodes, at least one of which is transparent, or an organic light emitting thin film layer and an organic charge transporting thin film layer. Organic thin film EL layered with
In the device, the main component of the organic light emitting thin film layer has the general formula 1:
【化３】
（式中、Ｒ１、Ｒ２およびＲ３はそれぞれ同一でも異な
っていてもよく、ハロゲン原子の中から選ばれる基であ
る。また、Ｒ４〜Ｒ１８はそれぞれ同一でも異なってい
てもよく、アルキル基、アリール基、ハロゲン原子、水
素原子の中から選ばれる基である。）で示されるアルミ
キノリン誘導体であることを特徴とする有機薄膜ＥＬ素
子である。[Image Omitted] (In the formula, R1, R2 and R3 may be the same or different, and are groups selected from halogen atoms. R4 to R18 may be the same or different, and are alkyl The present invention is an organic thin film EL device characterized by being an aluminum quinoline derivative represented by a group selected from group, aryl group, halogen atom, and hydrogen atom.
【０００５】本発明の有機薄膜ＥＬ素子としては、図２
に示すように、透明電極１２と電子注入電極１５の間に
有機発光体薄膜層１４のみを有するものの他、図１のよ
うに有機発光体薄膜層２４と有機正孔注入層２３を有す
るもの、さらに図３のように有機発光体薄膜層３４、有
機正孔注入層３３及び有機電子注入層３６を有するもの
の３種類が含まれ、そのいずれも有機発光体薄膜層とし
てハロゲン原子をもつアルミキノリン誘導体を用いるこ
とにより、極めて優れた発光効率を有する素子が得られ
る。特に図１に示すように、透明でかつ正孔注入電極で
あるＩＴＯ透明電極２２の上に正孔注入層２３の材料と
してｐ型半導体特性を示す芳香族第３アミン化合物やフ
タロシアニン系化合物などを用い、ＩＴＯ電極２２から
の正孔注入効率及び正孔注入層内の輸送効率を高めるこ
とはさらに有効である。The organic thin film EL device of the present invention is shown in FIG.
As shown in FIG. 1, there is only an organic light emitting thin film layer 14 between the transparent electrode 12 and the electron injection electrode 15, as well as one having an organic light emitting thin film layer 24 and an organic hole injection layer 23 as shown in FIG. Furthermore, as shown in FIG. 3, there are three types having an organic light emitting thin film layer 34, an organic hole injection layer 33, and an organic electron injection layer 36, all of which are made of aluminum quinoline derivatives having halogen atoms as the organic light emitting thin film layer. By using this, an element having extremely excellent luminous efficiency can be obtained. In particular, as shown in FIG. 1, aromatic tertiary amine compounds, phthalocyanine compounds, etc., which exhibit p-type semiconductor characteristics, are used as materials for the hole injection layer 23 on the ITO transparent electrode 22, which is transparent and serves as a hole injection electrode. It is further effective to increase the hole injection efficiency from the ITO electrode 22 and the transport efficiency within the hole injection layer.
【０００６】なお、透明電極としては、通常用いられる
ものであればいずれでもよく、例えばＩＴＯ以外では、
ＳｎＯ２：Ｓｂ，ＺｎＯ：Ａｌ，Ａｕ等が挙げられる。
電子注入電極にはＩｎ，Ｍｇ，Ａｇ，Ｍｇ：Ａｇ，Ｍｇ
：Ｉｎ等が使われる。また、本発明に用いられるハロゲ
ン原子をもつアルミキノリン誘導体の具体的な例として
は、トリス（５−クロロ−８−キノリノラト）アルミニ
ウム、トリス（５−ブロモ−８−キノリノラト）アルミ
ニウム、トリス（５−ヨード−８−キノリノラト）アル
ミニウム、トリス（５−フルオロ−８−キノリノラト）
アルミニウム、トリス（５−ヨード−７−クロロ−８−
キノリノラト）アルミニウム、トリス（５，６，７−ト
リクロロ−８−キノリノラト）アルミニウム、トリス（
５，７−ジクロロ−８−キノリノラト）アルミニウム、
トリス（５−クロロ−７−ヨード−８−キノリノラト）
アルミニウム、トリス（２−メチル−５−クロロ−８−
キノリノラト）アルミニウム等があるがこの限りではな
い。このように、本発明で重要な点は、発光層に用いる
材料がハロゲン原子をもつアルミキノリン誘導体である
ことを特徴とする有機薄膜ＥＬ素子であり、発光層以外
の素子を形成する材料については限定されない。[0006] The transparent electrode may be any commonly used material; for example, other than ITO,
Examples include SnO2:Sb, ZnO:Al, and Au. In, Mg, Ag, Mg:Ag, Mg for the electron injection electrode
:In etc. are used. Further, specific examples of aluminum quinoline derivatives having a halogen atom used in the present invention include tris(5-chloro-8-quinolinolato)aluminum, tris(5-bromo-8-quinolinolato)aluminum, tris(5- iodo-8-quinolinolato) aluminum, tris(5-fluoro-8-quinolinolato)
aluminum, tris(5-iodo-7-chloro-8-
quinolinolato)aluminum, tris(5,6,7-trichloro-8-quinolinolato)aluminum, tris(
5,7-dichloro-8-quinolinolato)aluminum,
Tris (5-chloro-7-iodo-8-quinolinolato)
Aluminum, tris(2-methyl-5-chloro-8-
quinolinolato) aluminum, but is not limited to this. As described above, the important point of the present invention is an organic thin film EL device characterized in that the material used for the light emitting layer is an aluminum quinoline derivative having a halogen atom, and the materials forming the device other than the light emitting layer are as follows. Not limited.
【０００７】[0007]
【実施例】次に、本発明の実施例について詳細に説明す
る。有機発光体材料として、トリス（５−クロロ−８−
キノリノラト）アルミニウムを以下のように合成して用
いた。５−クロロ−８−キノリノール（東京化成（株）
製）０．１ｍｏｌを酢酸水溶液に溶かし、７０℃に加熱
したＡｌＫ（ＳＯ４ ）２１９ｇ（０．１２ｍｏｌ）の
希塩酸溶液に滴下する。これに、酢酸アンモニウム水溶
液を加えながら撹拌し、錯体を完全に沈殿させる。その
まま１時間反応させてから冷却し、沈澱物を数回よく水
洗した後、減圧乾燥した。同定は、マススペクトルによ
り行った。還元電位は、−１．７２Ｖ ｖｓ．ＳＣＥで
あった。 次いで、図１に示すように、ガラス基板２
１上にＩＴＯ透明電極２２を形成してから、正孔注入層
２３として１，１−ビス（４−Ｎ，Ｎ−ジトリルアミノ
フェノール）シクロヘキサン薄膜を５００オングストロ
ーム、更に、本発明によるトリス（５−クロロ−８−キ
ノリノラト）アルミニウムからなる有機発光体薄膜層２
４を７００オングストローム、１０−７Ｔｏｒｒの真空
中で蒸着して形成した。最後に電子注入電極２５として
ＭｇＩｎ（Ｉｎ：１０％）を電子ビーム蒸着法で１５０
０オングストローム形成して有機薄膜ＥＬ素子を作製し
た。
この素子の発光特性を乾燥窒素中で測定したところ、約
８Ｖの直流電圧の印加で２００ｃｄ／ｍ２ の明るい緑
色発光が得られ、発光効率は、２０Ｖの印加電圧で、１
．７ ｌｍ／Ｗであった。従来のＥＬ素子では、１．５
ｌｍ／Ｗである。また、輝度半減時間は、５００時間
以上であった。EXAMPLES Next, examples of the present invention will be described in detail. Tris(5-chloro-8-
Quinolinolato) aluminum was synthesized and used as follows. 5-chloro-8-quinolinol (Tokyo Kasei Co., Ltd.)
0.1 mol of AlK(SO4) was dissolved in an acetic acid aqueous solution and added dropwise to a dilute hydrochloric acid solution of 219 g (0.12 mol) of AlK(SO4) heated to 70°C. To this, an aqueous ammonium acetate solution is added and stirred to completely precipitate the complex. The reaction was continued for 1 hour, then cooled, and the precipitate was thoroughly washed with water several times and then dried under reduced pressure. Identification was performed by mass spectrometry. The reduction potential is -1.72V vs. It was SCE. Next, as shown in FIG.
After forming an ITO transparent electrode 22 on the hole injection layer 23, a 500 angstrom thin film of 1,1-bis(4-N,N-ditollylaminophenol)cyclohexane was added as a hole injection layer 23, and a thin film of 500 angstroms of 1,1-bis(4-N,N-ditolylaminophenol) cyclohexane was added as a hole injection layer 23. -Chloro-8-quinolinolato) organic light emitting thin film layer 2 consisting of aluminum
4 was deposited to a thickness of 700 angstroms in a vacuum of 10 -7 Torr. Finally, as the electron injection electrode 25, MgIn (In: 10%) was deposited at 150% by electron beam evaporation.
An organic thin film EL device was fabricated by forming a thin film with a thickness of 0 angstroms. When the luminescent properties of this device were measured in dry nitrogen, bright green luminescence of 200 cd/m2 was obtained when a DC voltage of about 8 V was applied, and the luminous efficiency was 1.
．． It was 7 lm/W. In conventional EL elements, 1.5
lm/W. Further, the luminance half-life time was 500 hours or more.
【０００８】[0008]
【発明の効果】以上説明したように、本発明によれば発
光特性および信頼性が大幅に改善された有機薄膜ＥＬ素
子が提供される。このように、本発明による有機薄膜Ｅ
Ｌ素子は低電圧駆動の薄膜発光体としてきわめて有効で
あり、その工業的価値は高い。As explained above, according to the present invention, an organic thin film EL device with significantly improved light emitting characteristics and reliability is provided. In this way, the organic thin film E according to the present invention
The L element is extremely effective as a thin film light emitter driven by low voltage, and its industrial value is high.
【図１】本発明の有機薄膜ＥＬ素子の一実施例の概略断
面図である。FIG. 1 is a schematic cross-sectional view of an embodiment of an organic thin film EL element of the present invention.
【図２】本発明の有機薄膜ＥＬ素子の一実施例の概略断
面図である。FIG. 2 is a schematic cross-sectional view of one embodiment of the organic thin film EL element of the present invention.
【図３】本発明の有機薄膜ＥＬ素子の一実施例の概略断
面図である。FIG. 3 is a schematic cross-sectional view of one embodiment of the organic thin film EL element of the present invention.
１１，２１，３１ ガラス基板
１２，２２，３２ ＩＴＯ透明電極
１４，２４，３４ 有機発光体薄膜層１５，２５，３
５ 電子注入電極
２３，３３ 有機正孔注入層
３６ 有機電子注入層11, 21, 31 Glass substrate 12, 22, 32 ITO transparent electrode 14, 24, 34 Organic light emitter thin film layer 15, 25, 3
5 Electron injection electrodes 23, 33 Organic hole injection layer 36 Organic electron injection layer
Claims (2)
に、有機発光体薄膜層を少なくとも有する有機薄膜ＥＬ
素子において、有機発光体薄膜層の主成分が一般式：【
化１】 （式中、Ｒ１、Ｒ２およびＲ３はそれぞれ同一でも異な
っていてもよく、ハロゲン原子の中から選ばれる基であ
る。また、Ｒ４〜Ｒ１８はそれぞれ同一でも異なってい
てもよく、アルキル基、アリール基、ハロゲン原子、水
素原子の中から選ばれる基である。）で示されるアルミ
キノリン誘導体であることを特徴とする有機薄膜ＥＬ素
子。Claim 1: An organic thin film EL having at least an organic light emitting thin film layer between a pair of electrodes, at least one of which is transparent.
In the device, the main component of the organic light emitter thin film layer has the general formula:
Chemical formula 1] (In the formula, R1, R2 and R3 may be the same or different, and are groups selected from halogen atoms. R4 to R18 may be the same or different, and are alkyl groups. , an aryl group, a halogen atom, and a hydrogen atom).
に、有機発光体薄膜層と有機電荷輸送性薄膜層とが積層
された有機薄膜ＥＬ素子において、有機発光体薄膜層の
主成分が一般式： 【化２】 （式中、Ｒ１、Ｒ２およびＲ３はそれぞれ同一でも異な
っていてもよく、ハロゲン原子の中から選ばれる基であ
る。また、Ｒ４〜Ｒ１８はそれぞれ同一でも異なってい
てもよく、アルキル基、アリール基、ハロゲン原子、水
素原子の中から選ばれる基である。）で示されるアルミ
キノリン誘導体であることを特徴とする有機薄膜ＥＬ素
子。2. An organic thin film EL device in which an organic light emitting thin film layer and an organic charge transporting thin film layer are laminated between a pair of electrodes, at least one of which is transparent, wherein the main component of the organic light emitting thin film layer has a general formula: : [Formula 2] (wherein, R1, R2 and R3 may be the same or different, and are groups selected from halogen atoms. Also, R4 to R18 may be the same or different, An organic thin film EL device characterized in that it is an aluminum quinoline derivative represented by an alkyl group, an aryl group, a halogen atom, and a hydrogen atom.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3175927A JP2737458B2 (en) | 1991-06-21 | 1991-06-21 | Organic thin film EL device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3175927A JP2737458B2 (en) | 1991-06-21 | 1991-06-21 | Organic thin film EL device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04372688A true JPH04372688A (en) | 1992-12-25 |
| JP2737458B2 JP2737458B2 (en) | 1998-04-08 |
Family
ID=16004686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3175927A Expired - Lifetime JP2737458B2 (en) | 1991-06-21 | 1991-06-21 | Organic thin film EL device |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2737458B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0963768A (en) * | 1995-08-24 | 1997-03-07 | Matsushita Electric Ind Co Ltd | Organic luminescent element |
| WO2005042545A3 (en) * | 2003-11-03 | 2006-01-05 | Covion Organic Semiconductors | Halogenated coordination compounds preparation and use thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100446301C (en) * | 2006-02-24 | 2008-12-24 | 太原理工大学 | Organic electroluminescence LED of emitting yellow light and preparing method |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02291696A (en) * | 1989-01-13 | 1990-12-03 | Ricoh Co Ltd | Electric field luminescence element |
| JPH0485388A (en) * | 1990-07-27 | 1992-03-18 | Toshiba Corp | Organic electroluminescent element |
-
1991
- 1991-06-21 JP JP3175927A patent/JP2737458B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02291696A (en) * | 1989-01-13 | 1990-12-03 | Ricoh Co Ltd | Electric field luminescence element |
| JPH0485388A (en) * | 1990-07-27 | 1992-03-18 | Toshiba Corp | Organic electroluminescent element |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0963768A (en) * | 1995-08-24 | 1997-03-07 | Matsushita Electric Ind Co Ltd | Organic luminescent element |
| WO2005042545A3 (en) * | 2003-11-03 | 2006-01-05 | Covion Organic Semiconductors | Halogenated coordination compounds preparation and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2737458B2 (en) | 1998-04-08 |
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