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WO2012005360A1 - Elément électroluminescent organique - Google Patents

Elément électroluminescent organique Download PDF

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Publication number
WO2012005360A1
WO2012005360A1 PCT/JP2011/065715 JP2011065715W WO2012005360A1 WO 2012005360 A1 WO2012005360 A1 WO 2012005360A1 JP 2011065715 W JP2011065715 W JP 2011065715W WO 2012005360 A1 WO2012005360 A1 WO 2012005360A1
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Prior art keywords
group
substituted
general formula
unsubstituted
layer
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PCT/JP2011/065715
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English (en)
Japanese (ja)
Inventor
健介 益居
正兒 木下
伊勢　俊大
Original Assignee
富士フイルム株式会社
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Application filed by 富士フイルム株式会社 filed Critical 富士フイルム株式会社
Priority to KR1020137003188A priority Critical patent/KR101862426B1/ko
Publication of WO2012005360A1 publication Critical patent/WO2012005360A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
    • 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
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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

Definitions

  • the present invention can be achieved by the following means.
  • a pair of electrodes consisting of an anode and a cathode, a light emitting layer between the electrodes, and at least one organic layer between the light emitting layer and the anode, between the light emitting layer and the cathode
  • An organic electroluminescent device having at least one organic layer, Containing at least one compound represented by the following general formula (1) in at least one organic layer between the light emitting layer and the cathode;
  • An organic electroluminescence device comprising at least one compound represented by the following general formula (H-1) in at least one organic layer between the light emitting layer and the anode.
  • an aryloxycarbonylamino group preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino).
  • an aryloxycarbonylamino group preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino).
  • the compounds exemplified as the compound represented by the above general formula (1) are the method described in International Publication No. 03/080760, the method described in International Publication No. 03/078541, pamphlet, International Publication No. 05/085387. It can be synthesized by various methods such as the method described in the issue pamphlet.
  • the above exemplified compound (a-3) uses m-bromobenzaldehyde as a starting material, and pamphlet [0074]-[0075] of WO 05/085387 (page 45, line 11 to page 46, 18 Line).
  • the above exemplified compound (a-17) is synthesized by the method described in International Publication No.
  • Group or terphenyl group is preferred.
  • One or more hydrogen atoms in the aryl group are a halogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a lower alkylamino group, a hydroxy group, a nitro group, a cyano group, and an amino group.
  • An amidino group, a hydrazine, a hydrazone, a carboxylic acid group, a sulfonic acid group, a phosphoric acid group and the like may be substituted.
  • R H1 , R H1 ′, R H2 , R H2 ′, R H3 , and R H3 ′ represent a substituted or unsubstituted aryloxy group
  • the aryloxy group preferably has 6 to 30 carbon atoms
  • An aryloxy group having 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms is preferable.
  • the aryloxy group include a phenyloxy group, a naphthyloxy group, and a biphenyloxy group, and a phenyloxy group and a naphthyloxy group are preferable.
  • examples of the substituent include a substituent selected from the substituent group A, preferably an alkyl group (preferably an alkyl group having 1 to 8 carbon atoms, more Preferred is an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isobutyl group, a t-butyl group, an n-butyl group, and a cyclopropyl group.
  • an alkyl group preferably an alkyl group having 1 to 8 carbon atoms, more Preferred is an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isobutyl group, a t-butyl group, an n-butyl group, and a cyclopropyl group.
  • the substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like.
  • L 61 represents a single bond or a divalent linking group.
  • a 61 independently represents a carbon atom or a nitrogen atom.
  • Z 61 and Z 62 each independently represent a nitrogen-containing aromatic heterocyclic ring.
  • Z 63 independently represents a benzene ring or an aromatic heterocycle, and Y is an anionic acyclic ligand bonded to Pt.
  • R T3 ′, R T3 , R T4 , R T5 , R T6 , E and Q are the same as R T3 ′, R T3 , R in the general formula (T-1).
  • T4 , R T5 , R T6 , E and Q represents the coordination position to iridium.
  • the electron donating dopant in the electron injection layer is preferably contained in an amount of 0.1% by mass to 50% by mass, and preferably 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the electron injection layer. More preferably, the content is 0.5 to 30% by mass.
  • the entire organic EL element may be protected by a protective layer.
  • a material contained in the protective layer any material may be used as long as it has a function of preventing materials that promote device deterioration such as moisture and oxygen from entering the device.
  • the protective layer the matters described in JP-A-2008-270736, paragraphs [0169] to [0170] can be applied to the present invention.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention a trait à un élément électroluminescent organique dont la diminution du rendement au cours d'une commande de luminosité élevée est faible, et dont la chute initiale de la durabilité de commande est faible. L'élément électroluminescent organique est équipé, sur un substrat : d'une paire d'électrodes qui comprend une électrode positive et une électrode négative ; d'une couche électroluminescente située entre lesdites électrodes ; d'au moins une couche organique située entre ladite couche électroluminescente et ladite électrode positive ; et d'au moins une couche organique située entre ladite couche électroluminescente et ladite électrode négative. Au moins un composé, par exemple le composé représenté par la formule a-3 mentionnée ci-dessous, est contenu dans la ou les couches organiques situées entre ladite couche électroluminescente et ladite électrode négative, et au moins un composé, par exemple le composé représenté par la formule h-1, est contenu dans la ou les couches organiques situées entre ladite couche électroluminescente et ladite électrode positive.
PCT/JP2011/065715 2010-07-09 2011-07-08 Elément électroluminescent organique WO2012005360A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020137003188A KR101862426B1 (ko) 2010-07-09 2011-07-08 유기 전계 발광 소자

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010157352A JP4741028B1 (ja) 2010-07-09 2010-07-09 有機電界発光素子
JP2010-157352 2010-07-09

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WO2012005360A1 true WO2012005360A1 (fr) 2012-01-12

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JP (1) JP4741028B1 (fr)
KR (1) KR101862426B1 (fr)
WO (1) WO2012005360A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120302762A1 (en) * 2011-05-27 2012-11-29 Semiconductor Energy Laboratory Co., Ltd. Carbazole Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device
WO2016117429A1 (fr) * 2015-01-20 2016-07-28 保土谷化学工業株式会社 Dérivé de pyrimidine et élément électroluminescent organique
US9406891B2 (en) 2012-12-12 2016-08-02 Samsung Electronics Co., Ltd. Compound for organic optoelectronic device, organic light emitting diode including the same, and display including the organic light emitting diode
CN106062127A (zh) * 2014-03-07 2016-10-26 九州有机光材股份有限公司 发光材料、有机发光元件及化合物
US9761812B2 (en) 2012-11-26 2017-09-12 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device
US9847501B2 (en) 2011-11-22 2017-12-19 Idemitsu Kosan Co., Ltd. Aromatic heterocyclic derivative, material for organic electroluminescent element, and organic electroluminescent element
CN111032649A (zh) * 2018-01-22 2020-04-17 株式会社Lg化学 多环化合物及包含其的有机发光器件
CN112745339A (zh) * 2019-10-30 2021-05-04 北京绿人科技有限责任公司 一种含咔唑啉结构的有机化合物及其应用和一种有机电致发光器件
US11795185B2 (en) 2017-12-13 2023-10-24 Lg Display Co., Ltd. Compound for electron-transport material and organic light emitting diode including the same

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140101661A (ko) 2011-11-22 2014-08-20 이데미쓰 고산 가부시키가이샤 방향족 복소고리 유도체, 유기 일렉트로루미네선스 소자용 재료 및 유기 일렉트로루미네선스 소자
JP6208424B2 (ja) 2012-12-05 2017-10-04 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． フッ素置換されたアリール基を有するアミン誘導体、それを含む有機ｅｌ材料及びそれを用いた有機ｅｌ素子
US9209411B2 (en) 2012-12-07 2015-12-08 Universal Display Corporation Organic electroluminescent materials and devices
KR101627748B1 (ko) * 2013-05-27 2016-06-07 제일모직 주식회사 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR102086556B1 (ko) * 2013-08-02 2020-03-10 삼성디스플레이 주식회사 유기 발광 소자
WO2015072520A1 (fr) 2013-11-13 2015-05-21 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
US10784446B2 (en) 2014-11-28 2020-09-22 Idemitsu Kosan Co., Ltd. Compound, organic electroluminescence element material, organic electroluminescence element and electronic device
US11339143B2 (en) 2018-06-26 2022-05-24 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
WO2020050217A1 (fr) * 2018-09-07 2020-03-12 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
KR102797542B1 (ko) 2019-02-13 2025-04-21 삼성디스플레이 주식회사 유기 발광 소자

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007318101A (ja) * 2006-05-29 2007-12-06 Samsung Sdi Co Ltd 有機発光素子および有機発光素子を備える平板表示装置
WO2007142083A1 (fr) * 2006-06-02 2007-12-13 Idemitsu Kosan Co., Ltd. Matériau pour élément organique électroluminescent et élément organique électroluminescent utilisant le matériau

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KR100787425B1 (ko) * 2004-11-29 2007-12-26 삼성에스디아이 주식회사 페닐카바졸계 화합물 및 이를 이용한 유기 전계 발광 소자
JP4864476B2 (ja) * 2006-02-14 2012-02-01 出光興産株式会社 有機エレクトロルミネッセンス素子

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007318101A (ja) * 2006-05-29 2007-12-06 Samsung Sdi Co Ltd 有機発光素子および有機発光素子を備える平板表示装置
WO2007142083A1 (fr) * 2006-06-02 2007-12-13 Idemitsu Kosan Co., Ltd. Matériau pour élément organique électroluminescent et élément organique électroluminescent utilisant le matériau

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013010749A (ja) * 2011-05-27 2013-01-17 Semiconductor Energy Lab Co Ltd カルバゾール化合物、発光素子、発光装置、電子機器、および照明装置
US9079855B2 (en) * 2011-05-27 2015-07-14 Semiconductor Energy Laboratory Co., Ltd. Carbazole compound, light-emitting element, light-emitting device, electronic device, and lighting device
US20120302762A1 (en) * 2011-05-27 2012-11-29 Semiconductor Energy Laboratory Co., Ltd. Carbazole Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device
US9847501B2 (en) 2011-11-22 2017-12-19 Idemitsu Kosan Co., Ltd. Aromatic heterocyclic derivative, material for organic electroluminescent element, and organic electroluminescent element
US10629823B2 (en) 2012-11-26 2020-04-21 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device
US9761812B2 (en) 2012-11-26 2017-09-12 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device
US9406891B2 (en) 2012-12-12 2016-08-02 Samsung Electronics Co., Ltd. Compound for organic optoelectronic device, organic light emitting diode including the same, and display including the organic light emitting diode
CN106062127A (zh) * 2014-03-07 2016-10-26 九州有机光材股份有限公司 发光材料、有机发光元件及化合物
US9773982B2 (en) 2014-03-07 2017-09-26 Kyulux, Inc. Light-emitting material, organic light-emitting device, and compound
US10043981B2 (en) 2014-03-07 2018-08-07 Kyulux, Inc. Light-emitting material, organic light-emitting device, and compound
JPWO2016117429A1 (ja) * 2015-01-20 2017-11-09 保土谷化学工業株式会社 ピリミジン誘導体および有機エレクトロルミネッセンス素子
CN107406415A (zh) * 2015-01-20 2017-11-28 保土谷化学工业株式会社 嘧啶衍生物和有机电致发光器件
US10566543B2 (en) 2015-01-20 2020-02-18 Hodogaya Chemical Co., Ltd. Pyrimidine derivative and organic electroluminescent devices
WO2016117429A1 (fr) * 2015-01-20 2016-07-28 保土谷化学工業株式会社 Dérivé de pyrimidine et élément électroluminescent organique
CN107406415B (zh) * 2015-01-20 2021-02-19 保土谷化学工业株式会社 嘧啶衍生物和有机电致发光器件
US11795185B2 (en) 2017-12-13 2023-10-24 Lg Display Co., Ltd. Compound for electron-transport material and organic light emitting diode including the same
CN111032649A (zh) * 2018-01-22 2020-04-17 株式会社Lg化学 多环化合物及包含其的有机发光器件
CN111032649B (zh) * 2018-01-22 2022-12-02 株式会社Lg化学 多环化合物及包含其的有机发光器件
CN112745339A (zh) * 2019-10-30 2021-05-04 北京绿人科技有限责任公司 一种含咔唑啉结构的有机化合物及其应用和一种有机电致发光器件

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KR20130043665A (ko) 2013-04-30
JP4741028B1 (ja) 2011-08-03
KR101862426B1 (ko) 2018-05-29
JP2012019172A (ja) 2012-01-26

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