JP2737458B2 - Organic thin film EL device - Google Patents
Organic thin film EL deviceInfo
- Publication number
- JP2737458B2 JP2737458B2 JP3175927A JP17592791A JP2737458B2 JP 2737458 B2 JP2737458 B2 JP 2737458B2 JP 3175927 A JP3175927 A JP 3175927A JP 17592791 A JP17592791 A JP 17592791A JP 2737458 B2 JP2737458 B2 JP 2737458B2
- Authority
- JP
- Japan
- Prior art keywords
- organic
- thin film
- film layer
- aluminum
- organic thin
- 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.)
- Expired - Lifetime
Links
- 239000010409 thin film Substances 0.000 title claims description 41
- -1 aluminum quinoline derivative Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000003248 quinolines Chemical class 0.000 claims description 3
- 238000002347 injection Methods 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- 229910052782 aluminium Inorganic materials 0.000 description 13
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 12
- 239000007983 Tris buffer Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 4
- 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
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- 239000011521 glass 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
- 239000000758 substrate Substances 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 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
- 125000003118 aryl group Chemical group 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
- 150000001875 compounds Chemical class 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
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 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 compound 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Luminescent Compositions (AREA)
- Electroluminescent Light Sources (AREA)
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 for a flat light source or a display.
【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。2. Description of the Related Art EL (Electroluminescence) using an organic substance as a raw material
Devices have attracted attention as realizing inexpensive large-area full-color display devices. For example, a DC-driven organic thin film EL device thinned by a LB (Langmuir-Blodgett) method or a vacuum evaporation method using a condensed ring aromatic system such as anthracene or perylene as a raw material is manufactured, and its light emission characteristics are studied. ing. However, the conventional organic thin-film EL device has a high driving voltage, and its emission luminance and efficiency are lower than those of the inorganic thin-film EL device. In addition, the light emission characteristics were significantly deteriorated, and a practical level was not obtained. However, in recent years, a new type of organic thin film EL device having a stacked structure in which an organic thin film has a two-layer structure has been reported, and has received a great deal of interest (Applied Physics Letters, 51
Vol., P. 913, 1987). According to reports,
As shown in FIG. 1, this organic thin-film EL element uses an organic substance that emits strong fluorescence for the organic light-emitting thin-film layer 24 and an amine-based material for the hole-injecting layer 23 of a hole-conductive organic substance. It is disclosed that bright green light emission was obtained by sandwiching these between the ITO transparent electrode 22 and the electron injection electrode 25, and a luminance of several hundred cd / m 2 when a DC voltage of 6 to 7 V was applied. Have gained. The maximum luminous efficiency is 1.5 lm / W, which is a performance close to a 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。As described above, a new organic thin film EL device having a structure in which an organic light emitting thin film and an organic hole injection layer are stacked in two layers has a maximum light emission luminance of 1 layer.
It emits bright green light of 000 cd / m 2 or more. Since this element is of a current-driven type, a current of 100 mA / cm 2 or more must be passed to obtain the above luminance. However, in the case of an unsubstituted aluminum quinolium complex conventionally used for an organic luminous body thin film layer, -1.84 V vs. 1.9.
Since the SCE and the reduction potential were large, the efficiency of electron injection from the electron injection electrode was poor, and a sufficient current could not flow stably. The present invention has been made in view of the above-described conventional circumstances, and further improves the device luminous efficiency.
Further, it is an object of the present invention to provide an organic thin-film EL device in which the rate of deterioration of light emission luminance is reduced.
【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：According to the present invention, there is provided an organic thin film EL device having at least one organic light emitting thin film layer between a pair of transparent electrodes, or an organic light emitting thin film layer and an organic charge transporting thin film layer. And organic thin film EL laminated
In the device, the main component of the organic luminescent thin film layer is represented by 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。Embedded image (Wherein, R 1 , R 2 and R 3 may be the same or different and each is a group selected from halogen atoms. R 4 to R 18 may be the same or different, An organic quinoline derivative represented by the following formula (1): an aluminum quinoline derivative represented by the following formula:
【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。As an organic thin film EL device of the present invention, FIG.
As shown in FIG. 1, in addition to those having only the organic light emitting thin film layer 14 between the transparent electrode 12 and the electron injection electrode 15, those having the organic light emitting thin film layer 24 and the organic hole injection layer 23 as shown in FIG. Further, as shown in FIG. 3, there are three types including those having an organic luminous body thin film layer 34, an organic hole injecting layer 33, and an organic electron injecting layer 36. By using, an element having extremely excellent luminous efficiency can be obtained. In particular, as shown in FIG. 1, an aromatic tertiary amine compound or a phthalocyanine-based compound exhibiting p-type semiconductor characteristics is used as a material of a hole injection layer 23 on an ITO transparent electrode 22 which is a transparent and hole injection electrode. It is more effective to increase the hole injection efficiency from the ITO electrode 22 and the transport efficiency in 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 one. For example, other than ITO,
SnO 2 : Sb, ZnO: Al, Au and the like. In, Mg, Ag, Mg: Ag, Mg:
In or the like is used. Specific examples of the aluminum quinoline derivative 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 and the like, but not limited thereto. As described above, an important point in the present invention is an organic thin-film EL element characterized in that the material used for the light-emitting layer is an aluminum quinoline derivative having a halogen atom. 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２１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２４
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Ｍｇ
Ｉｎ（Ｉｎ：１０％）を電子ビーム蒸着法で１５００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 ｌ
ｍ／Ｗである。また、輝度半減時間は、５００時間以上
であった。Next, embodiments of the present invention will be described in detail. As an organic luminescent material, tris (5-chloro-8-
(Quinolinolato) aluminum was synthesized and used as follows. 5-Chloro-8-quinolinol (Tokyo Chemical Co., Ltd.)
Was dissolved in an aqueous acetic acid solution, and added dropwise to a dilute hydrochloric acid solution of 19 g (0.12 mol) of AlK (SO 4 ) 2 heated to 70 ° C. The mixture is stirred while an aqueous solution of ammonium acetate is added to completely precipitate the complex. The reaction was allowed to react for 1 hour, cooled, and the precipitate was washed well with water several times and dried under reduced pressure. The identification was performed by mass spectrum. The reduction potential was -1.72V vs. SCE. Next, as shown in FIG. 1, an ITO transparent electrode 22 is formed on a glass substrate 21 and then a hole injection layer 23 is formed.
A 1,1-bis (4-N, N-ditolylaminophenol) cyclohexane thin film of 500 Å, and an organic luminescent thin film layer 24 of tris (5-chloro-8-quinolinolato) aluminum according to the present invention.
Was formed by vapor deposition in a vacuum of 700 Å, 10 −7 Torr. Finally, Mg is used as the electron injection electrode 25.
In (In: 10%) was formed by electron beam evaporation at 1500 Å to produce an organic thin film EL device.
When the light emission characteristics of this device were measured in dry nitrogen, a bright green light emission of 200 cd / m 2 was obtained by applying a DC voltage of about 8 V, and the luminous efficiency was 1.
It was 7 lm / W. In a conventional EL device, 1.5 l
m / W. Further, the luminance half 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 described above, according to the present invention, there is provided an organic thin film EL device having significantly improved light emission characteristics and reliability. Thus, the organic thin film E according to the present invention is
The L element is extremely effective as a low-voltage driven thin-film illuminant, 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 sectional view of one embodiment of an organic thin film EL device 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 sectional view of one embodiment of the organic thin film EL device 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 sectional view of one embodiment of the organic thin film EL device 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 １５，２５，３５ 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 luminescent thin film layer 15, 25, 35 Electron injection electrode 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。An organic thin film EL having at least one organic light emitting thin film layer between a pair of transparent electrodes.
In the device, the main component of the organic luminescent thin film layer has a general formula: (Wherein, R 1 , R 2 and R 3 may be the same or different and each is a group selected from halogen atoms. R 4 to R 18 may be the same or different, An organic quinoline derivative represented by the formula (1): an aluminum quinoline derivative represented by the following formula:
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 is a general formula. : (Wherein, R 1 , R 2 and R 3 may be the same or different and each is a group selected from halogen atoms. R 4 to R 18 may be the same or different, An organic quinoline derivative represented by the formula (1): an aluminum quinoline derivative represented by the following formula:
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 JPH04372688A (en) | 1992-12-25 |
| JP2737458B2 true 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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100446301C (en) * | 2006-02-24 | 2008-12-24 | 太原理工大学 | A yellow light-emitting organic electroluminescent diode and its preparation method |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3269345B2 (en) * | 1995-08-24 | 2002-03-25 | 松下電器産業株式会社 | Organic light emitting device |
| DE10351556A1 (en) * | 2003-11-03 | 2005-06-02 | Covion Organic Semiconductors Gmbh | Halogenated coordination compounds, their representation and use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2869446B2 (en) * | 1989-01-13 | 1999-03-10 | 株式会社リコー | EL device |
| JP2902745B2 (en) * | 1990-07-27 | 1999-06-07 | 株式会社東芝 | Organic electroluminescence device |
-
1991
- 1991-06-21 JP JP3175927A patent/JP2737458B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100446301C (en) * | 2006-02-24 | 2008-12-24 | 太原理工大学 | A yellow light-emitting organic electroluminescent diode and its preparation method |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04372688A (en) | 1992-12-25 |
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