JP6526211B2 - 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 - Google Patents

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 Download PDF

Info

Publication number
JP6526211B2
JP6526211B2 JP2017537399A JP2017537399A JP6526211B2 JP 6526211 B2 JP6526211 B2 JP 6526211B2 JP 2017537399 A JP2017537399 A JP 2017537399A JP 2017537399 A JP2017537399 A JP 2017537399A JP 6526211 B2 JP6526211 B2 JP 6526211B2
Authority
JP
Japan
Prior art keywords
dopant
layer
organic
aminophosphazene
electron transport
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.)
Expired - Fee Related
Application number
JP2017537399A
Other languages
English (en)
Japanese (ja)
Other versions
JP2018505162A (ja
JP2018505162A5 (enExample
Inventor
ケスラー、フローリアン
レーゲンスブルガー、シュテファン
シュミット、ギュンター
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Siemens AG
Original Assignee
Siemens AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Siemens AG filed Critical Siemens AG
Publication of JP2018505162A publication Critical patent/JP2018505162A/ja
Publication of JP2018505162A5 publication Critical patent/JP2018505162A5/ja
Application granted granted Critical
Publication of JP6526211B2 publication Critical patent/JP6526211B2/ja
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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

Landscapes

  • 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)
JP2017537399A 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 Expired - Fee Related JP6526211B2 (ja)

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 (3)

Publication Number Publication Date
JP2018505162A JP2018505162A (ja) 2018-02-22
JP2018505162A5 JP2018505162A5 (enExample) 2018-04-12
JP6526211B2 true JP6526211B2 (ja) 2019-06-05

Family

ID=55022423

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2017537399A Expired - Fee Related 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

Country Status (7)

Country Link
US (1) US10230050B2 (enExample)
EP (1) EP3230295B1 (enExample)
JP (1) JP6526211B2 (enExample)
KR (1) KR102073261B1 (enExample)
CN (1) CN107210364B (enExample)
DE (1) DE102015200699A1 (enExample)
WO (1) WO2016116202A1 (enExample)

Families Citing this family (5)

* 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
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
JP7092381B2 (ja) 2016-12-26 2022-06-28 青島科技大学 オリゴホスファゼン化合物及びその調製方法と使用
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

Family Cites Families (18)

* Cited by examiner, † Cited by third party
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
WO2005034260A1 (de) * 2003-09-19 2005-04-14 Covion Organic Semiconductors Gmbh Organisches elektrolumineszenzelement
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
ATE394800T1 (de) * 2006-03-21 2008-05-15 Novaled Ag Heterocyclisches radikal oder diradikal, deren dimere, oligomere, polymere, dispiroverbindungen und polycyclen, deren verwendung, organisches halbleitendes material sowie elektronisches bauelement
EP1837927A1 (de) 2006-03-22 2007-09-26 Novaled AG Verwendung von heterocyclischen Radikalen zur Dotierung von organischen Halbleitern
TWI353677B (en) 2006-03-21 2011-12-01 Novaled Ag Method for preparing doped organic semiconductor m
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
KR102174125B1 (ko) 2008-06-20 2020-11-06 오엘이디워크스 게엠베하 환형 포스파젠 화합물 및 유기 발광 다이오드에서 이의 용도
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
JP6059662B2 (ja) 2010-11-09 2017-01-11 コーニンクレッカ フィリップス エヌ ヴェＫｏｎｉｎｋｌｉｊｋｅ Ｐｈｉｌｉｐｓ Ｎ．Ｖ． 有機エレクトロルミネッセンス装置
CN103765621B (zh) * 2011-06-22 2017-02-22 诺瓦尔德股份有限公司 电子器件和化合物
WO2012175535A1 (de) * 2011-06-22 2012-12-27 Novaled Ag Organisches elektronisches bauelement
DE102012217587A1 (de) 2012-09-27 2014-03-27 Siemens Aktiengesellschaft Salze des Cyclopentadiens als n-Dotierstoffe für die organische Elektronik
CN105027314B (zh) * 2013-03-05 2017-09-29 九州有机光材股份有限公司 电荷传输材料、主体材料、薄膜及有机发光元件
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

Also Published As

Publication number Publication date
EP3230295A1 (de) 2017-10-18
EP3230295B1 (de) 2019-07-31
KR20170102024A (ko) 2017-09-06
WO2016116202A1 (de) 2016-07-28
US10230050B2 (en) 2019-03-12
US20180019396A1 (en) 2018-01-18
CN107210364B (zh) 2021-05-04
JP2018505162A (ja) 2018-02-22
KR102073261B1 (ko) 2020-02-04
CN107210364A (zh) 2017-09-26
DE102015200699A1 (de) 2016-07-21

Similar Documents

Publication Publication Date Title
EP2463927B1 (en) Material for organic electronic device and organic electronic device
KR101768731B1 (ko) 유기 전자 장치 및 유기 반도체 매트릭스 재료를 도핑하기 위한 도판트
CN104067400B (zh) 有机电子器件
KR102530868B1 (ko) 반도체의 유기층을 형성하기 위한 잉크 조성물
WO2020018476A1 (en) Fluorinated porphyrin derivatives for optoelectronic applications
EP2887412B1 (en) Semiconducting material
JP6526211B2 (ja) 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
KR20120052891A (ko) 유기 전자 장치를 위한 화합물 및 유기 전자 장치
CN104302618A (zh) 芳族胺-三联苯化合物及其在有机半导体组件中的用途
KR20180082536A (ko) 금속 함유 층을 제조하는 공정
US10361376B2 (en) Proazaphosphatranes as n-dopants in organic electronics
US10941168B2 (en) Phosphepine matrix compound for a semiconducting material
KR102697369B1 (ko) 두 개의 금속 도펀트를 포함한 n-도핑된 반도전성 물질

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20180228

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20180228

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20180927

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20181016

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20190116

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20190315

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20190315

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20190326

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20190409

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20190507

R150 Certificate of patent or registration of utility model

Ref document number: 6526211

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

LAPS Cancellation because of no payment of annual fees