DE102015200699A1 - Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik - Google Patents

Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik Download PDF

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Publication number
DE102015200699A1
DE102015200699A1 DE102015200699.9A DE102015200699A DE102015200699A1 DE 102015200699 A1 DE102015200699 A1 DE 102015200699A1 DE 102015200699 A DE102015200699 A DE 102015200699A DE 102015200699 A1 DE102015200699 A1 DE 102015200699A1
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Prior art keywords
dopant
phenyl
bis
substituents
group
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Withdrawn
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DE102015200699.9A
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German (de)
English (en)
Inventor
Florian Kessler
Stefan Regensburger
Günter Schmid
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Siemens AG
Siemens Corp
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Siemens AG
Siemens Corp
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Priority to DE102015200699.9A priority Critical patent/DE102015200699A1/de
Priority to EP15816100.0A priority patent/EP3230295B1/de
Priority to JP2017537399A priority patent/JP6526211B2/ja
Priority to US15/544,490 priority patent/US10230050B2/en
Priority to CN201580073924.7A priority patent/CN107210364B/zh
Priority to PCT/EP2015/078749 priority patent/WO2016116202A1/de
Priority to KR1020177023143A priority patent/KR102073261B1/ko
Publication of DE102015200699A1 publication Critical patent/DE102015200699A1/de
Withdrawn legal-status Critical Current

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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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
    • C07F9/6584—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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/24—Electrically-conducting paints
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/30—Doping active layers, e.g. electron transporting 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • 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)
DE102015200699.9A 2015-01-19 2015-01-19 Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik Withdrawn DE102015200699A1 (de)

Priority Applications (7)

Application Number Priority Date Filing Date Title
DE102015200699.9A DE102015200699A1 (de) 2015-01-19 2015-01-19 Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik
EP15816100.0A EP3230295B1 (de) 2015-01-19 2015-12-07 Aminophosphazen-basen als n-dotierstoffe in der organischen elektronik
JP2017537399A JP6526211B2 (ja) 2015-01-19 2015-12-07 有機エレクトロニクスにおけるｎ−ドーパントとしてのアミノフォスファゼン塩基
US15/544,490 US10230050B2 (en) 2015-01-19 2015-12-07 Amino phosphazene bases as n-dopants in organic electronics
CN201580073924.7A CN107210364B (zh) 2015-01-19 2015-12-07 氨基磷腈碱作为有机电子产品中的n型掺杂剂
PCT/EP2015/078749 WO2016116202A1 (de) 2015-01-19 2015-12-07 Aminophosphazen-basen als n-dotierstoffe in der organischen elektronik
KR1020177023143A KR102073261B1 (ko) 2015-01-19 2015-12-07 유기 전자기기에서 ｎ-도펀트로서의 아미노 포스파젠 염기

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102015200699.9A DE102015200699A1 (de) 2015-01-19 2015-01-19 Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik

Publications (1)

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DE102015200699A1 true DE102015200699A1 (de) 2016-07-21

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DE102015200699.9A Withdrawn DE102015200699A1 (de) 2015-01-19 2015-01-19 Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik

Country Status (7)

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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

Citations (5)

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Publication number Priority date Publication date Assignee Title
WO2009153276A1 (de) 2008-06-20 2009-12-23 Basf Se Cyclische phosphazenverbindungen und deren verwendung in organischen leuchtdioden
JP2010062334A (ja) * 2008-09-03 2010-03-18 Japan Vam & Poval Co Ltd リン拡散用塗布液
WO2012175535A1 (de) * 2011-06-22 2012-12-27 Novaled Ag Organisches elektronisches bauelement
WO2012175219A1 (en) 2011-06-22 2012-12-27 Novaled Ag Electronic device and compound
DE102012217587A1 (de) * 2012-09-27 2014-03-27 Siemens Aktiengesellschaft Salze des Cyclopentadiens als n-Dotierstoffe für die organische Elektronik

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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
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Publication number Priority date Publication date Assignee Title
WO2009153276A1 (de) 2008-06-20 2009-12-23 Basf Se Cyclische phosphazenverbindungen und deren verwendung in organischen leuchtdioden
JP2010062334A (ja) * 2008-09-03 2010-03-18 Japan Vam & Poval Co Ltd リン拡散用塗布液
WO2012175535A1 (de) * 2011-06-22 2012-12-27 Novaled Ag Organisches elektronisches bauelement
WO2012175219A1 (en) 2011-06-22 2012-12-27 Novaled Ag Electronic device and compound
DE102012217587A1 (de) * 2012-09-27 2014-03-27 Siemens Aktiengesellschaft Salze des Cyclopentadiens als n-Dotierstoffe für die organische Elektronik

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"Superbases for Organic Synthesis – Guanidines, Amidines, Phosphazenes and Related Organocatalysts" von Tsutomo Ishikawa (WILEY, 2009, ISBN: 978-0-470-51800-7)
ALLCOCK, Harry R., LEVIN, Michael L., AUSTIN, Paul E.: Quaternized Cyclic and High Polymeric Phosphazenes and their Interactions with Tetracyanoquinodimethane. In: Inorganic Chemistry, 1986, Bd. 25, S. 2281 - 2288. *
JP 2010 062334 A (Maschinenübersetzung) AIPN [online] JPO, [abgerufen am 06.08.2015]

Also Published As

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
KR102073261B1 (ko) 2020-02-04
KR20170102024A (ko) 2017-09-06
US20180019396A1 (en) 2018-01-18
EP3230295A1 (de) 2017-10-18
WO2016116202A1 (de) 2016-07-28
EP3230295B1 (de) 2019-07-31

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