JPH03162481A - Electroluminescent element - Google Patents
Electroluminescent elementInfo
- Publication number
- JPH03162481A JPH03162481A JP1301498A JP30149889A JPH03162481A JP H03162481 A JPH03162481 A JP H03162481A JP 1301498 A JP1301498 A JP 1301498A JP 30149889 A JP30149889 A JP 30149889A JP H03162481 A JPH03162481 A JP H03162481A
- Authority
- JP
- Japan
- Prior art keywords
- group
- organic
- phosphor
- thin film
- cathode
- 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.)
- Pending
Links
- -1 heteromonocyclic compound Chemical class 0.000 claims abstract description 18
- 239000010409 thin film Substances 0.000 claims abstract description 17
- 150000001787 chalcogens Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 20
- 150000002894 organic compounds Chemical class 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 4
- 230000005684 electric field Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- DZFWNZJKBJOGFQ-UHFFFAOYSA-N julolidine Chemical compound C1CCC2=CC=CC3=C2N1CCC3 DZFWNZJKBJOGFQ-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 229910052798 chalcogen Inorganic materials 0.000 abstract 1
- 230000027756 respiratory electron transport chain Effects 0.000 abstract 1
- 230000005525 hole transport Effects 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000010408 film Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- KYGSXEYUWRFVNY-UHFFFAOYSA-N 2-pyran-2-ylidenepropanedinitrile Chemical compound N#CC(C#N)=C1OC=CC=C1 KYGSXEYUWRFVNY-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000006617 triphenylamine group Chemical group 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
Description
【発明の詳細な説明】
技術分野
本発明は電界発光素子に関し、特に有機化合物を発光体
として構成される電界発光素子に関する。DETAILED DESCRIPTION OF THE INVENTION Technical Field The present invention relates to an electroluminescent device, and particularly to an electroluminescent device constructed using an organic compound as a light emitter.
背景技術
この種の電界発光素子として、第2図に示すように、陰
極である金属電極1と陽極である透明電極2との間に有
機化合物からなり互いに積層された有機蛍光体薄膜3及
び有機正孔輸送層4が配された2層構造のものや、第3
図に示すように、金属電極1と透明電極2との間に互い
に積層された有機電子輸送層5、有機蛍光体薄膜3及び
有機正孔輸送層4が配された3層構造のものが知られて
いる。ここで、有機正孔輸送層4は陽極から正孔を注入
させ易くする機能と電子をブロックする機能とを有し、
有機電子輸送層5は陰極から電子を注入させ易くする機
能を有している。BACKGROUND ART As shown in FIG. 2, this type of electroluminescent device uses an organic phosphor thin film 3 made of an organic compound and laminated on each other between a metal electrode 1 serving as a cathode and a transparent electrode 2 serving as an anode. Those with a two-layer structure in which a hole transport layer 4 is arranged, and those with a third layer structure.
As shown in the figure, a three-layer structure is known in which an organic electron transport layer 5, an organic phosphor thin film 3, and an organic hole transport layer 4 are stacked on each other between a metal electrode 1 and a transparent electrode 2. It is being Here, the organic hole transport layer 4 has a function of facilitating injection of holes from the anode and a function of blocking electrons,
The organic electron transport layer 5 has a function of facilitating injection of electrons from the cathode.
これら電界発光素子において、透明電極2の外側にはガ
ラス基板6が配されており、金属電極1から注入された
電子と透明電極2から注入された正孔との再結合によっ
て励起子が生じ、この励起子が放射失活する過程で光を
放ち、この光が透明電極2及びガラス基阪6を介して外
部に放出されることになる。In these electroluminescent devices, a glass substrate 6 is disposed outside the transparent electrode 2, and excitons are generated by recombination of electrons injected from the metal electrode 1 and holes injected from the transparent electrode 2. The excitons emit light in the process of being radiatively deactivated, and this light is emitted to the outside via the transparent electrode 2 and the glass substrate 6.
また、上述した構或の従来の電界発光素子においては、
特定の色の蛍光帯域を有するものが開発されているが、
さらにその他種々の色を発光させるべく、より多くの種
類の有機蛍光体の電界発光素子の開発が望まれている。Furthermore, in the conventional electroluminescent device having the above-mentioned structure,
Products with fluorescent bands of specific colors have been developed, but
Furthermore, in order to emit light of various other colors, it is desired to develop electroluminescent devices using more types of organic phosphors.
発明の概要
[発明の目的]
本発明は、上述した従来の要望を満すべくなされたもの
であって、有機蛍光体を効率良く高n度にて発光させる
ことができる電界発光素子を提供することを目的とする
。Summary of the Invention [Object of the Invention] The present invention has been made to satisfy the above-mentioned conventional needs, and provides an electroluminescent device that can efficiently cause an organic phosphor to emit light at a high n degree. The purpose is to
[発明の構成]
本発明による電界発光素子においては、有機化合物から
なり互いに積層された蛍光体発光層及び正孔輻送層が隘
極及び陽極間に配された構成の電界発光素子であって、
前記蛍光体発光層は下記構造式(A)で示され、
上記構造式(A)中、Xはカルコゲン原子であり、R1
及びR2は独立に、アミノスチリル基,アルキルアミノ
スチリル基,ジアルキルアミノスチリル基,ジュロリジ
ン環.アルキル基.及びアリール基からなる群から選ば
れる官能基である4位にジシアノメチレン基を有する凌
素6員単環化合物を含む蛍光体薄膜からなることを特徴
とする。[Structure of the Invention] The electroluminescent device according to the present invention has a structure in which a phosphor emitting layer and a hole transporting layer made of an organic compound and stacked on each other are arranged between a dead electrode and an anode. ,
The phosphor emitting layer is represented by the following structural formula (A), in which X is a chalcogen atom, and R1
and R2 independently represent an aminostyryl group, an alkylaminostyryl group, a dialkylaminostyryl group, a julolidine ring. Alkyl group. It is characterized by comprising a phosphor thin film containing a six-membered monocyclic compound having a dicyanomethylene group at the 4-position, which is a functional group selected from the group consisting of and aryl groups.
以下、本発明を図に基づいて詳細に説明する。Hereinafter, the present invention will be explained in detail based on the drawings.
第1図は本発明の一実施例を示す構造図であり、図中第
2図及びM3図と同等部分には同一符号が付されている
。FIG. 1 is a structural diagram showing an embodiment of the present invention, in which the same parts as in FIGS. 2 and M3 are given the same reference numerals.
図において、陰極である金属電極lには、アルミニウム
の1500入膜厚の薄膜を用いる。また、陰極1には、
仕事関数が小さな金属、例えば厚さが約500人以上の
アルミニウム、マグネシウム、インジウム、銀又はこれ
らの合金が用い得る。In the figure, a thin film of aluminum with a thickness of 1500 mm is used for the metal electrode l which is the cathode. In addition, in the cathode 1,
Metals with low work functions can be used, such as aluminum, magnesium, indium, silver, or alloys thereof, with a thickness of about 500 mm or more.
陽極である透明電極2には、インジウムすず酸化物(1
. T. O. )の2000入膜厚の薄膜を用いる。The transparent electrode 2, which is an anode, is made of indium tin oxide (1
.. T. O. ) is used with a film thickness of 2000.
また、陽極2には、仕事関数の大きな導電性材料、例え
ば厚さが1000〜3000入程度の1. 7. O,
又は厚さが800〜1500人程度の金が用い得る。な
お、金を電極材料として用いた場合には、1G極2は半
透明の状態となる。In addition, the anode 2 is made of a conductive material with a large work function, for example, a conductive material having a thickness of about 1,000 to 3,000. 7. O,
Alternatively, gold having a thickness of about 800 to 1,500 gold can be used. Note that when gold is used as the electrode material, the 1G electrode 2 becomes translucent.
金属電極1と透明電極2との間には、図の上から順に積
層された有機蛍光体薄膜7及び有機正孔輻送層4が配さ
れている。An organic phosphor thin film 7 and an organic hole transport layer 4 are arranged between the metal electrode 1 and the transparent electrode 2, which are laminated in order from the top in the figure.
有機正孔暢送層4には、トリフエニルアミン誘導体、例
えば下記式(1)の化合物の薄膜を用いる。For the organic hole transporting layer 4, a thin film of a triphenylamine derivative, for example, a compound of the following formula (1) is used.
また、有機正孔暢送層4には、更に下記式(II)〜
(Xn) のC TM (Carrier 丁r
ansmjtlng Materials )として
知られる化合物を用い得る。In addition, the organic hole transport layer 4 further includes the following formulas (II) to
(Xn) C TM (Carrier
Compounds known as ansmjtlng Materials) can be used.
有機蛍光体薄膜7としては、下記(A)式の4位にジシ
アノメチレン基を有し環に1個のカルコゲン原子を有す
る複素6員単環化合物を含む蛍光体薄膜が用いられる。As the organic phosphor thin film 7, a phosphor thin film containing a six-membered monocyclic heterocyclic compound having a dicyanomethylene group at the 4-position and one chalcogen atom in the ring of the following formula (A) is used.
かかる有機蛍光体薄膜7の膜厚は1μm以下に設定され
る。The thickness of the organic phosphor thin film 7 is set to 1 μm or less.
ここで、上記{8造式(A)中、Xはカルコゲン原子、
すなわち周期律表■に属するO, S, Se,T
eまたはPoであり、R1及びR2は独立に、アミノス
チリル基,アルキルアミノスチリル基.ジアルキルアミ
ノスチリル基,ジュロリジン環,アルキル基,及びアリ
ール基からなる群から選ばれる官能基(但し、アルキル
成分は好ましくは、炭素原子数が1〜5個であるが、6
個以上でもよく、アリール或分は好ましくは、炭素原子
数が6〜14gUであるが、18個以上でもよい)であ
る。Here, in the above {8 formula (A), X is a chalcogen atom,
In other words, O, S, Se, T belonging to the periodic table ■
e or Po, and R1 and R2 independently represent an aminostyryl group, an alkylaminostyryl group. A functional group selected from the group consisting of a dialkylaminostyryl group, a julolidine ring, an alkyl group, and an aryl group (however, the alkyl component preferably has 1 to 5 carbon atoms, but 6
The aryl group preferably has 6 to 14 gU of carbon atoms, but may have 18 or more carbon atoms.
この蛍光体薄膜を形成する復素6員単環化合物は、第1
表の官能基のNo.l−No.5の組み合わせを有する
ものが好ましい。The six-membered monocyclic compound forming this phosphor thin film is the first
No. of functional groups in the table. l-No. Those having a combination of 5 are preferred.
また、上記電界発光素子においては陰極1及び陽極2間
に有機蛍光体薄膜7及び有機正孔輸送層4を配した2層
構造としたが、従来の陰極1及び蛍光体薄膜7層間に例
えば下記(XX)式のべリレンテトラ力ルボキシル誘導
体からなる有機電子輻送層5を配した3層構造としても
同様の効果を奏する。In addition, the electroluminescent device described above has a two-layer structure in which the organic phosphor thin film 7 and the organic hole transport layer 4 are arranged between the cathode 1 and the anode 2. A three-layer structure including an organic electron transporting layer 5 made of a berylenetetracarboxyl derivative of the formula (XX) can also produce similar effects.
発明の効果
以上説明したように、本発明による電界発光素子におい
ては、有機化合物からなり互いに積層された蛍光体発光
層及び正孔暢送層が陰極及び陽極間に配された構或の電
界発光素子であって、蛍光体発光層はジシアノメチレン
ピラン染料等の上記(A)式の4位にジシアノメチレン
基を有し環に1個のカルコゲン原子を有する複素6員単
環化合物を含む蛍光体薄膜からなるので、低電圧にて効
率良く高輝度で発光させることができる。Effects of the Invention As explained above, the electroluminescent device according to the present invention has a structure in which a phosphor emitting layer and a hole transporting layer made of an organic compound and stacked on each other are arranged between a cathode and an anode. In the device, the phosphor emitting layer is a phosphor containing a 6-membered monocyclic heterocyclic compound having a dicyanomethylene group at the 4-position of the above formula (A) and one chalcogen atom in the ring, such as dicyanomethylene pyran dye. Since it is made of a thin film, it can efficiently emit light with high brightness at low voltage.
実施例
以下、本発明の実施例の電界発光素子を作或しそれを発
光さけた。EXAMPLES In the following, electroluminescent devices according to examples of the present invention were fabricated and emitted from them.
まず、ガラス基板上に陽極である透明電極のlT,
0,を2000人膜厚で或膜したものを用意した。陰極
である金属電極1には、アルミニウムを用いた。First, a transparent electrode, which is an anode, is placed on a glass substrate.
A film with a thickness of 2,000 layers was prepared. Aluminum was used for the metal electrode 1 serving as the cathode.
有機正孔輻送層4には、上記(1)式のトリフ工二ルア
ミン誘導体を用いた。For the organic hole transport layer 4, a triphenylamine derivative of the above formula (1) was used.
有機蛍光体薄H7としては、上記表のNo.Iの下記(
A−1)式のジシアノメチレンピラン染料を用いた。As organic phosphor thin H7, No. 1 in the above table is used. I below (
A-1) dicyanomethylenepyran dye was used.
正孔暢送層、蛍光体薄膜及び陰極を戊膜する際の真空度
、蒸着速度及び膜厚等の或膜条件は第2表の如くであり
、この表において得られた電界発光素子に電圧を印加す
ることにより得た発光特性を併記する。The film conditions such as degree of vacuum, evaporation rate, and film thickness when depositing the hole transport layer, phosphor thin film, and cathode are as shown in Table 2. The luminescence characteristics obtained by applying .
第1図は本発明の実施例を示す構造図、及び第3図は従
来例を示す構造図である。
主要部分の符号の説明
1・・・・・・金属電極(陰極)
2・・・・・・透明電極(陽極)
4・・・・・・有機正孔輻送層
6・・・・・・ガラス基板
7・・・・・・有機蛍光体薄膜
第2図FIG. 1 is a structural diagram showing an embodiment of the present invention, and FIG. 3 is a structural diagram showing a conventional example. Explanation of symbols of main parts 1...Metal electrode (cathode) 2...Transparent electrode (anode) 4...Organic hole transport layer 6... Glass substrate 7...Organic phosphor thin film Fig. 2
Claims (2)
光層及び正孔輸送層が陰極及び陽極間に配された構成の
電界発光素子であつて、前記蛍光体発光層は下記構造式
(A)で示され、 ▲数式、化学式、表等があります▼ 上記構造式(A)中、 Xはカルコゲン原子であり、 R^1及びR^2は独立に、アミノスチリル基、アルキ
ルアミノスチリル基、ジアルキルアミノスチリル基、ジ
ユロリジン環、アルキル基、及びアリール基からなる群
から選ばれる官能基である4位にジシアノメチレン基を
有する複素6員単環化合物を含む蛍光体薄膜からなるこ
とを特徴とする電界発光素子。(1) An electroluminescent device having a structure in which a phosphor-emitting layer and a hole-transporting layer made of an organic compound and stacked on each other are arranged between a cathode and an anode, wherein the phosphor-emitting layer has the following structural formula (A). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the above structural formula (A), X is a chalcogen atom, and R^1 and R^2 are independently aminostyryl group, alkylaminostyryl group, dialkyl group An electric field comprising a phosphor thin film containing a 6-membered hetero monocyclic compound having a dicyanomethylene group at the 4-position, which is a functional group selected from the group consisting of an aminostyryl group, a diurolidine ring, an alkyl group, and an aryl group. Light emitting element.
が配されたことを特徴とする請求項1記載の電界発光素
子。(2) The electroluminescent device according to claim 1, further comprising an organic electron transport layer disposed between the cathode and the phosphor layer.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1301498A JPH03162481A (en) | 1989-11-20 | 1989-11-20 | Electroluminescent element |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1301498A JPH03162481A (en) | 1989-11-20 | 1989-11-20 | Electroluminescent element |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH03162481A true JPH03162481A (en) | 1991-07-12 |
Family
ID=17897641
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1301498A Pending JPH03162481A (en) | 1989-11-20 | 1989-11-20 | Electroluminescent element |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH03162481A (en) |
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WO2007105448A1 (en) | 2006-02-28 | 2007-09-20 | Idemitsu Kosan Co., Ltd. | Naphthacene derivative and organic electroluminescent device using same |
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-
1989
- 1989-11-20 JP JP1301498A patent/JPH03162481A/en active Pending
Cited By (17)
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EP2262025A2 (en) | 2000-04-21 | 2010-12-15 | TDK Corporation | Organic electroluminescent device |
WO2007052759A1 (en) | 2005-11-07 | 2007-05-10 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element |
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