WO2012099038A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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Publication number
WO2012099038A1
WO2012099038A1 PCT/JP2012/050682 JP2012050682W WO2012099038A1 WO 2012099038 A1 WO2012099038 A1 WO 2012099038A1 JP 2012050682 W JP2012050682 W JP 2012050682W WO 2012099038 A1 WO2012099038 A1 WO 2012099038A1
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WO
WIPO (PCT)
Prior art keywords
group
layer
ring
organic
general formula
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Application number
PCT/JP2012/050682
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English (en)
Japanese (ja)
Inventor
健 波木井
宏 石代
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コニカミノルタホールディングス株式会社
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Priority to JP2012553696A priority Critical patent/JP5888243B2/ja
Publication of WO2012099038A1 publication Critical patent/WO2012099038A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • H10K50/82—Cathodes
    • H10K50/824—Cathodes combined with auxiliary electrodes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • H10K50/82—Cathodes
    • H10K50/828—Transparent cathodes, e.g. comprising thin metal layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • Y5 represents a divalent linking group comprising an arylene group, a heteroarylene group, or a combination thereof.
  • E51 to E66 each independently represent C (R3) or N, and R3 represents a hydrogen atom or a substituent.
  • Y6 to Y9 each independently represents a group derived from an aromatic hydrocarbon ring or a group derived from an aromatic heterocycle, and at least one of Y6 or Y7 and at least one of Y8 or Y9 each represents an N atom.
  • the group derived from the aromatic heterocyclic ring containing is represented.
  • n3 and n4 represent an integer of 0 to 4, and n3 + n4 is an integer of 2 or more.
  • 6 The organic electroluminescence device as described in 5 above, wherein the transparent protective layer contains a compound represented by the following general formula (3).
  • the organic EL device of the present invention is characterized in that the cathode is transparent.
  • the anode can be either transparent or opaque depending on the application.
  • the organic EL device of the present invention preferably has a top emission type structure in which films are formed in the order of anode to cathode.
  • the transparent protective layer according to the present invention is patterned. Since the transparent conductive layer and the electron injection layer are in electrical contact by patterning the transparent protective layer, electrons transported from the transparent conductive layer are transported to the electron injection layer without passing through the transparent protective layer. Therefore, it is possible to emit light at a low voltage.
  • the arylene group and heteroarylene group represented by Y5 are the arylene group and heteroarylene group described as an example of the divalent linking group represented by Y1 in general formula (1). Are synonymous with each other.
  • the total film thickness of the light emitting layer is preferably in the range of 1 to 100 nm, and more preferably 1 nm or more and 30 nm or less because a lower driving voltage can be obtained. Note that the total film thickness of the light emitting layer is a film thickness including the intermediate layer when a non-light emitting intermediate layer exists between the light emitting layers.
  • the hole transport layer is made of a hole transport material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer.
  • the hole transport layer can be provided as a single layer or a plurality of layers.
  • an electron transport material also serving as a hole blocking material used for an electron transport layer adjacent to the cathode side with respect to the light emitting layer is injected from the cathode.
  • any material can be selected and used from among conventionally known compounds. For example, nitro-substituted fluorene derivatives, diphenylquinone derivatives Thiopyrandioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives and the like.
  • an auxiliary electrode can be provided on the transparent conductive layer for the purpose of reducing the resistance.
  • a material for forming the auxiliary electrode a metal having low resistance such as gold, platinum, silver, copper, and aluminum is preferable.
  • the method for forming the auxiliary electrode include a vapor deposition method, a sputtering method, a printing method, and a mark jet method.
  • the auxiliary electrode according to the present invention is preferably formed on an unpatterned region of the transparent protective layer.
  • the auxiliary electrode preferably has a line width of 100 ⁇ m or less and a thickness of 0.5 ⁇ m or more. More preferably, the line width is 50 ⁇ m or less and the thickness is 1 ⁇ m or more.

Abstract

La présente invention concerne un élément électroluminescent organique qui présente une efficacité lumineuse et une tension de commande améliorées. Un élément électroluminescent organique de la présente invention comprend au moins une couche conductrice transparente et une couche d'injection d'électrons sur un substrat et se caractérise en ce qu'il comprend une couche protectrice transparente à motif entre la couche conductrice transparente et la couche d'injection d'électrons, ladite couche protectrice transparente étant sensiblement transparente et ayant une résistance d'au moins 100 fois la résistance de la couche conductrice transparente.
PCT/JP2012/050682 2011-01-17 2012-01-16 Élément électroluminescent organique WO2012099038A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2012553696A JP5888243B2 (ja) 2011-01-17 2012-01-16 有機エレクトロルミネッセンス素子

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011-006839 2011-01-17
JP2011006839 2011-01-17

Publications (1)

Publication Number Publication Date
WO2012099038A1 true WO2012099038A1 (fr) 2012-07-26

Family

ID=46515664

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2012/050682 WO2012099038A1 (fr) 2011-01-17 2012-01-16 Élément électroluminescent organique

Country Status (2)

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JP (1) JP5888243B2 (fr)
WO (1) WO2012099038A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013069242A1 (fr) * 2011-11-07 2013-05-16 出光興産株式会社 Matière pour éléments électroluminescents organiques et élément électroluminescent organique l'utilisant
JP2014504602A (ja) * 2011-01-24 2014-02-24 ユニバーサル ディスプレイ コーポレイション 電子輸送化合物
WO2014081206A1 (fr) * 2012-11-21 2014-05-30 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les contenant
KR20140101699A (ko) * 2013-02-12 2014-08-20 삼성전자주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
WO2014163173A1 (fr) * 2013-04-04 2014-10-09 Jnc株式会社 Matériau de transport d'électrons et dispositif électroluminescent organique l'utilisant
WO2015105251A1 (fr) * 2014-01-09 2015-07-16 삼성에스디아이 주식회사 Composé organique, dispositif optoélectronique organique et dispositif d'affichage
US9203036B2 (en) 2012-02-03 2015-12-01 Idemitsu Kosan Co., Ltd. Carbazole compound, material for organic electroluminescence device and organic electroluminescence device
JP2016534096A (ja) * 2013-07-30 2016-11-04 メルク パテント ゲーエムベーハー 電子素子のための材料
JP2016534095A (ja) * 2013-07-30 2016-11-04 メルク パテント ゲーエムベーハー 電子素子のための材料
US9847501B2 (en) 2011-11-22 2017-12-19 Idemitsu Kosan Co., Ltd. Aromatic heterocyclic derivative, material for organic electroluminescent element, and organic electroluminescent element
CN110573506A (zh) * 2017-03-24 2019-12-13 喜星素材株式会社 杂环化合物与包含其的有机发光装置

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002367784A (ja) * 2001-06-11 2002-12-20 Tdk Corp 有機ｅｌ素子
JP2004281402A (ja) * 2003-03-13 2004-10-07 Eastman Kodak Co 上面発光型有機発光ダイオード（ｏｌｅｄ）表示装置
JP2005158693A (ja) * 2003-11-21 2005-06-16 Samsung Sdi Co Ltd 有機電界発光素子
JP2007265792A (ja) * 2006-03-28 2007-10-11 Dainippon Printing Co Ltd 有機エレクトロルミネッセンス素子
JP2008098475A (ja) * 2006-10-13 2008-04-24 Fuji Electric Holdings Co Ltd 有機発光素子の構造
JP2010251675A (ja) * 2008-05-13 2010-11-04 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002367784A (ja) * 2001-06-11 2002-12-20 Tdk Corp 有機ｅｌ素子
JP2004281402A (ja) * 2003-03-13 2004-10-07 Eastman Kodak Co 上面発光型有機発光ダイオード（ｏｌｅｄ）表示装置
JP2005158693A (ja) * 2003-11-21 2005-06-16 Samsung Sdi Co Ltd 有機電界発光素子
JP2007265792A (ja) * 2006-03-28 2007-10-11 Dainippon Printing Co Ltd 有機エレクトロルミネッセンス素子
JP2008098475A (ja) * 2006-10-13 2008-04-24 Fuji Electric Holdings Co Ltd 有機発光素子の構造
JP2010251675A (ja) * 2008-05-13 2010-11-04 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014504602A (ja) * 2011-01-24 2014-02-24 ユニバーサル ディスプレイ コーポレイション 電子輸送化合物
WO2013069242A1 (fr) * 2011-11-07 2013-05-16 出光興産株式会社 Matière pour éléments électroluminescents organiques et élément électroluminescent organique l'utilisant
US9847501B2 (en) 2011-11-22 2017-12-19 Idemitsu Kosan Co., Ltd. Aromatic heterocyclic derivative, material for organic electroluminescent element, and organic electroluminescent element
US9203036B2 (en) 2012-02-03 2015-12-01 Idemitsu Kosan Co., Ltd. Carbazole compound, material for organic electroluminescence device and organic electroluminescence device
CN104781253A (zh) * 2012-11-21 2015-07-15 罗门哈斯电子材料韩国有限公司 新颖有机电致发光化合物和含有所述化合物的有机电致发光装置
JP2016503585A (ja) * 2012-11-21 2016-02-04 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 新規有機エレクトロルミネセンス化合物およびそれを含む有機エレクトロルミネセンスデバイス
WO2014081206A1 (fr) * 2012-11-21 2014-05-30 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les contenant
KR102184171B1 (ko) * 2013-02-12 2020-11-27 삼성전자주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20140101699A (ko) * 2013-02-12 2014-08-20 삼성전자주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
JPWO2014163173A1 (ja) * 2013-04-04 2017-02-16 Jnc株式会社 電子輸送材料およびこれを用いた有機電界発光素子
WO2014163173A1 (fr) * 2013-04-04 2014-10-09 Jnc株式会社 Matériau de transport d'électrons et dispositif électroluminescent organique l'utilisant
CN105051019A (zh) * 2013-04-04 2015-11-11 捷恩智株式会社 电子传输材料及使用该电子传输材料的有机电致发光元件
JP2016534096A (ja) * 2013-07-30 2016-11-04 メルク パテント ゲーエムベーハー 電子素子のための材料
JP2016534095A (ja) * 2013-07-30 2016-11-04 メルク パテント ゲーエムベーハー 電子素子のための材料
CN109666026A (zh) * 2013-07-30 2019-04-23 默克专利有限公司 用于电子器件的材料
US11588117B2 (en) 2013-07-30 2023-02-21 Merck Patent Gmbh Materials for electronic devices
CN105899501A (zh) * 2014-01-09 2016-08-24 三星Sdi株式会社 有机化合物、有机光电子装置及显示装置
KR101788094B1 (ko) * 2014-01-09 2017-10-19 제일모직 주식회사 유기 화합물, 유기 광전자 소자 및 표시 장치
US10147891B2 (en) 2014-01-09 2018-12-04 Samsung Sdi Co., Ltd. Organic compound, organic optoelectronic device, and display device
WO2015105251A1 (fr) * 2014-01-09 2015-07-16 삼성에스디아이 주식회사 Composé organique, dispositif optoélectronique organique et dispositif d'affichage
CN110573506A (zh) * 2017-03-24 2019-12-13 喜星素材株式会社 杂环化合物与包含其的有机发光装置

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