KR102073261B1 - 유기 전자기기에서 ｎ-도펀트로서의 아미노 포스파젠 염기 - Google Patents

유기 전자기기에서 ｎ-도펀트로서의 아미노 포스파젠 염기 Download PDF

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KR102073261B1
KR102073261B1 KR1020177023143A KR20177023143A KR102073261B1 KR 102073261 B1 KR102073261 B1 KR 102073261B1 KR 1020177023143 A KR1020177023143 A KR 1020177023143A KR 20177023143 A KR20177023143 A KR 20177023143A KR 102073261 B1 KR102073261 B1 KR 102073261B1
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dopant
organic
bis
layer
diphenyl
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KR20170102024A (ko
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플로리안 케슬러
스테판 레겐스부르거
귄터 슈미트
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지멘스 악티엔게젤샤프트
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    • H01L51/005—
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/062—Organo-phosphoranes without P-C bonds
    • C07F9/065—Phosphoranes containing the structure P=N-
    • C—CHEMISTRY; METALLURGY
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • C—CHEMISTRY; METALLURGY
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503—Five-membered rings
    • C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
    • C—CHEMISTRY; METALLURGY
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6524—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having four or more nitrogen atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
    • C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
    • C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
    • C—CHEMISTRY; METALLURGY
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    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
    • C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
    • C07F9/65848—Cyclic amide derivatives of acids of phosphorus, in which two nitrogen atoms belong to the ring
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    • H10K50/14—Carrier transporting layers
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • 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
    • 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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Manufacturing & Machinery (AREA)
  • Wood Science & Technology (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Thin Film Transistor (AREA)
  • Photovoltaic Devices (AREA)
KR1020177023143A 2015-01-19 2015-12-07 유기 전자기기에서 ｎ-도펀트로서의 아미노 포스파젠 염기 Expired - Fee Related KR102073261B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102015200699.9 2015-01-19
DE102015200699.9A DE102015200699A1 (de) 2015-01-19 2015-01-19 Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik
PCT/EP2015/078749 WO2016116202A1 (de) 2015-01-19 2015-12-07 Aminophosphazen-basen als n-dotierstoffe in der organischen elektronik

Publications (2)

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KR20170102024A KR20170102024A (ko) 2017-09-06
KR102073261B1 true KR102073261B1 (ko) 2020-02-04

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US (1) US10230050B2 (https=)
EP (1) EP3230295B1 (https=)
JP (1) JP6526211B2 (https=)
KR (1) KR102073261B1 (https=)
CN (1) CN107210364B (https=)
DE (1) DE102015200699A1 (https=)
WO (1) WO2016116202A1 (https=)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102015200699A1 (de) 2015-01-19 2016-07-21 Siemens Aktiengesellschaft Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik
WO2018121005A1 (zh) * 2016-12-26 2018-07-05 青岛科技大学 寡聚磷腈化合物及其制备方法和用途
CN108239117B (zh) * 2016-12-26 2020-08-14 青岛博远高分子材料研究院有限公司 环状寡聚磷腈化合物及其制备方法和用途
JP7232016B2 (ja) * 2018-11-15 2023-03-02 日本放送協会 有機薄膜および有機薄膜の製造方法、有機エレクトロルミネッセンス素子、表示装置、照明装置、有機薄膜太陽電池、薄膜トランジスタ、塗料組成物
CN110172275A (zh) * 2019-05-22 2019-08-27 深圳市华星光电半导体显示技术有限公司 电子传输层墨水及其制备方法、电致发光器件
US20240166824A1 (en) * 2021-03-02 2024-05-23 Nippon Shokubai Co., Ltd. Phosphazene bond-containing polymer

Family Cites Families (18)

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Publication number Priority date Publication date Assignee Title
JPH0512990A (ja) * 1991-06-27 1993-01-22 Canon Inc Ｍｉｍ型電子放出素子の製造方法
CN1853288B (zh) * 2003-09-19 2010-12-15 默克专利有限公司 有机电致发光元件
JP2006278549A (ja) * 2005-03-28 2006-10-12 Fuji Photo Film Co Ltd 有機ｅｌ素子及び有機ｅｌディスプレイ
US7683536B2 (en) 2005-03-31 2010-03-23 The Trustees Of Princeton University OLEDs utilizing direct injection to the triplet state
KR101361710B1 (ko) * 2006-03-21 2014-02-10 노발레드 아게 도핑된 유기 반도체 물질을 제조하는 방법 및 이러한 방법에 사용되는 포뮬레이션
EP1837927A1 (de) 2006-03-22 2007-09-26 Novaled AG Verwendung von heterocyclischen Radikalen zur Dotierung von organischen Halbleitern
EP1837926B1 (de) * 2006-03-21 2008-05-07 Novaled AG Heterocyclisches Radikal oder Diradikal, deren Dimere, Oligomere, Polymere, Dispiroverbindungen und Polycyclen, deren Verwendung, organisches halbleitendes Material sowie elektronisches Bauelement
JP5393945B2 (ja) * 2006-07-31 2014-01-22 ポリプラスチックス株式会社 安定化ポリアセタール樹脂の製造方法、安定化ポリアセタール樹脂、組成物及び成形体
CN102099942B (zh) 2008-06-20 2013-05-15 巴斯夫欧洲公司 环状磷腈化合物及其在有机发光二极管中的用途
JP2010062334A (ja) * 2008-09-03 2010-03-18 Japan Vam & Poval Co Ltd リン拡散用塗布液
US20110266525A1 (en) * 2009-10-29 2011-11-03 E. I. Du Pont De Nemours And Company Organic light-emitting diode luminaires
CN103180993B (zh) 2010-11-09 2016-01-27 皇家飞利浦电子股份有限公司 有机电致发光器件
US9502660B2 (en) * 2011-06-22 2016-11-22 Novaled Gmbh Electronic device and compound
US20140203254A1 (en) 2011-06-22 2014-07-24 Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V. Organic Electronic Component
DE102012217587A1 (de) * 2012-09-27 2014-03-27 Siemens Aktiengesellschaft Salze des Cyclopentadiens als n-Dotierstoffe für die organische Elektronik
WO2014136758A1 (ja) 2013-03-05 2014-09-12 国立大学法人九州大学 電荷輸送材料、ホスト材料、薄膜および有機発光素子
DE102014100993A1 (de) * 2013-12-05 2015-06-11 Osram Opto Semiconductors Gmbh Organisches lichtemittierendes Bauelement und Verfahren zur Herstellung des organischen lichtemittierenden Bauelements
DE102015200699A1 (de) 2015-01-19 2016-07-21 Siemens Aktiengesellschaft Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik

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Publication number Publication date
JP2018505162A (ja) 2018-02-22
JP6526211B2 (ja) 2019-06-05
CN107210364B (zh) 2021-05-04
CN107210364A (zh) 2017-09-26
US10230050B2 (en) 2019-03-12
KR20170102024A (ko) 2017-09-06
DE102015200699A1 (de) 2016-07-21
US20180019396A1 (en) 2018-01-18
EP3230295A1 (de) 2017-10-18
WO2016116202A1 (de) 2016-07-28
EP3230295B1 (de) 2019-07-31

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