WO2011033023A1 - Organic electronic device and dopant for doping an organic semiconducting matrix material - Google Patents

Organic electronic device and dopant for doping an organic semiconducting matrix material Download PDF

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Publication number
WO2011033023A1
WO2011033023A1 PCT/EP2010/063619 EP2010063619W WO2011033023A1 WO 2011033023 A1 WO2011033023 A1 WO 2011033023A1 EP 2010063619 W EP2010063619 W EP 2010063619W WO 2011033023 A1 WO2011033023 A1 WO 2011033023A1
Authority
WO
WIPO (PCT)
Prior art keywords
copper
electronic device
organic
matrix material
organic electronic
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.)
Ceased
Application number
PCT/EP2010/063619
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English (en)
French (fr)
Inventor
Günter Schmid
Jan Hauke Wemken
Marina A. Petrukhina
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.)
Ams Osram International GmbH
Original Assignee
Osram Opto Semiconductors GmbH
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 Osram Opto Semiconductors GmbH filed Critical Osram Opto Semiconductors GmbH
Priority to JP2012529272A priority Critical patent/JP5836275B2/ja
Priority to KR1020127009765A priority patent/KR101768731B1/ko
Priority to EP10754509.7A priority patent/EP2478576B9/en
Priority to CN201080041456.2A priority patent/CN102576802B/zh
Publication of WO2011033023A1 publication Critical patent/WO2011033023A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • H10K85/30—Coordination compounds
    • H10K85/371—Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver
    • 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
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
    • 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
    • H10K50/15—Hole transporting 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
    • H10K50/15—Hole transporting layers
    • H10K50/155—Hole transporting layers comprising dopants
    • 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]
    • H10K50/18—Carrier blocking layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the ligand L coordinating to the copper atom contains a group R
  • perfluorinated, homo- and heteroaromatic compounds can be used as moieties R and R' ', respectively.
  • examples are the anions of fluorinated benzoic acids:
  • Ei and E2 are defined as above, wherein Yi, Y2, Y 3 , Y 4 and Y5 represent the same or different groups or atoms and wherein Yi, Y2, Y 3 , Y 4 and Y5 are independently selected from the following atoms and/or groups: C-F, C-Cl, C-Br, C-NO2, C- CN, N, C-N 3 , C-OCN, C-NCO, C-CNO, C-SCN, C-NCS, and C-SeCN, particulary independently selected from the following atoms and/or groups C-F, C-NO2, C-CN, and N.
  • ligands L may for example be selected from the following ligands:
  • a dopant for doping an organic semiconducting matrix material comprising at least two copper atoms, and at least one ligand L bridging the two copper atoms, wherein the ligand L is represented by the following formula:
  • the copper complex comprises four, particularly in a "four-membered” ring, or six copper atoms, particularly in a "six-membered” ring, or polymeric species comprising a plurality of copper atoms in a chain-like structure .

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Photovoltaic Devices (AREA)
PCT/EP2010/063619 2009-09-18 2010-09-16 Organic electronic device and dopant for doping an organic semiconducting matrix material Ceased WO2011033023A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2012529272A JP5836275B2 (ja) 2009-09-18 2010-09-16 有機電子デバイス、並びに有機半導体マトリックス材料をドープするためのドーパント
KR1020127009765A KR101768731B1 (ko) 2009-09-18 2010-09-16 유기 전자 장치 및 유기 반도체 매트릭스 재료를 도핑하기 위한 도판트
EP10754509.7A EP2478576B9 (en) 2009-09-18 2010-09-16 Organic electronic device and dopant for doping an organic semiconducting matrix material
CN201080041456.2A CN102576802B (zh) 2009-09-18 2010-09-16 有机电子器件和用于掺杂有机半导体基质材料的掺杂剂

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US24392709P 2009-09-18 2009-09-18
US61/243,927 2009-09-18

Publications (1)

Publication Number Publication Date
WO2011033023A1 true WO2011033023A1 (en) 2011-03-24

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2010/063619 Ceased WO2011033023A1 (en) 2009-09-18 2010-09-16 Organic electronic device and dopant for doping an organic semiconducting matrix material

Country Status (6)

Country Link
US (2) US8624229B2 (https=)
EP (1) EP2478576B9 (https=)
JP (1) JP5836275B2 (https=)
KR (1) KR101768731B1 (https=)
CN (1) CN102576802B (https=)
WO (1) WO2011033023A1 (https=)

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DE102010062954A1 (de) * 2010-12-13 2012-06-14 Osram Opto Semiconductors Gmbh Optoelektronisches Bauelement und Verwendung eines Kupferkomplexes in einer Ladungserzeugungsschichtfolge
DE102010062877A1 (de) * 2010-12-13 2012-06-21 Osram Opto Semiconductors Gmbh Organisches Lichtemittierendes Bauelement und Verwendung eines Kupferkomplexes in einer Ladungstransportschicht
WO2012136422A1 (de) * 2011-04-08 2012-10-11 Osram Opto Semiconductors Gmbh Optoelektronisches bauelement und verwendung eines kupferkomplexes als dotierstoff zum dotieren einer schicht
WO2013182383A1 (de) * 2012-06-06 2013-12-12 Siemens Aktiengesellschaft Metallkomplexe als p-dotanden für organische elektronische matrixmaterialien
WO2014005766A1 (de) 2012-07-06 2014-01-09 Osram Opto Semiconductors Gmbh Organisches licht emittierendes bauelement
WO2013182389A3 (de) * 2012-06-06 2014-01-30 Siemens Aktiengesellschaft Hauptgruppenmetallkomplexe als p-dotanden für organische elektronische matrixmaterialien
WO2014044344A1 (de) 2012-09-18 2014-03-27 Merck Patent Gmbh Materialien für elektronische vorrichtungen
DE102013106949A1 (de) 2013-07-02 2015-01-08 Osram Opto Semiconductors Gmbh Optoelektronisches Bauelement, organische funktionelle Schicht und Verfahren zur Herstellung eines optoelektronischen Bauelements
DE202014106226U1 (de) 2014-09-30 2015-10-28 Osram Oled Gmbh Organisches elektronisches Bauteil
EP2960315A1 (de) 2014-06-27 2015-12-30 cynora GmbH Organische Elektrolumineszenzvorrichtung
WO2016012274A1 (en) 2014-07-21 2016-01-28 Basf Se Organic-inorganic tandem solar cell
WO2016042070A1 (de) 2014-09-17 2016-03-24 Cynora Gmbh Organische moleküle zur verwendung als emitter
DE102014114224A1 (de) 2014-09-30 2016-03-31 Osram Oled Gmbh Organisches elektronisches Bauteil, Verwendung eines Zinkkomplexes als p-Dotierungsmittel für organische elektronische Matrixmaterialien
DE102015119778A1 (de) 2015-11-16 2017-05-18 Osram Oled Gmbh Organisches elektronisches Bauelement, Verwendung eines p-Dotierstoffs für ein Matrixmaterial
DE102016101710A1 (de) 2016-02-01 2017-08-03 Osram Oled Gmbh OLED und Verfahren zur Herstellung einer OLED
WO2018234346A1 (en) 2017-06-23 2018-12-27 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2019175149A1 (en) 2018-03-16 2019-09-19 Merck Patent Gmbh Materials for organic electroluminescent devices

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KR102037819B1 (ko) * 2012-12-24 2019-10-29 엘지디스플레이 주식회사 유기전계발광표시장치 및 그 제조방법
KR102253438B1 (ko) * 2014-03-26 2021-05-20 삼성디스플레이 주식회사 아민계 화합물 및 이를 포함한 유기 발광 소자
DE102015102866B4 (de) 2015-02-27 2023-02-02 Tdk Electronics Ag Keramisches Bauelement, Bauelementanordnung und Verfahren zur Herstellung eines keramischen Bauelements
DE102015121844A1 (de) * 2015-12-15 2017-06-22 Osram Oled Gmbh Organisches elektronisches Bauelement und Verwendung eines fluorierten Sulfonimid-Metallsalzes
KR102534789B1 (ko) * 2016-05-02 2023-05-19 한양대학교 산학협력단 과불소화산 처리된 전도성 고분자 박막의 제조방법 및 이의 용도
KR102675576B1 (ko) * 2016-07-04 2024-06-18 삼성디스플레이 주식회사 유기 발광 표시 장치
KR102078435B1 (ko) * 2016-07-14 2020-02-17 주식회사 엘지화학 유기 전계 발광 소자 및 이의 제조 방법
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EP3503234B1 (en) * 2017-12-20 2020-11-04 Novaled GmbH Organic electronic device comprising an inverse coordination complex and a method for preparing the same
CN114639788A (zh) * 2020-12-15 2022-06-17 云谷（固安）科技有限公司 发光器件、材料筛选方法及显示面板
CN113337276B (zh) * 2021-05-10 2022-07-15 武汉大学 发光材料、喷墨打印薄膜光学器件的方法及其应用
KR20250128345A (ko) 2022-12-23 2025-08-27 메르크 파텐트 게엠베하 전자 디바이스

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KR20130025897A (ko) * 2010-03-31 2013-03-12 오스람 옵토 세미컨덕터스 게엠베하 유기 반도체 부품용 정공 도체 층을 위한 도펀트, 그리고 이와 같은 도펀트의 용도
CN102947414B (zh) * 2010-03-31 2016-04-27 欧司朗光电半导体有限公司 用于有机半导体器件的空穴导电层的掺杂材料及其应用
US9276223B2 (en) 2010-03-31 2016-03-01 Osram Oled Gmbh Dopant for a hole conductor layer for organic semiconductor components, and use thereof
US9006716B2 (en) 2010-03-31 2015-04-14 Osram Opto Semiconductors Gmbh Dopant for a hole conductor layer for organic semiconductor components, and use thereof
WO2011120709A1 (de) * 2010-03-31 2011-10-06 Osram Opto Semiconductors Gmbh Dotierstoff für eine lochleiterschicht für organische halbleiterbauelemente und verwendung dazu
CN102947414A (zh) * 2010-03-31 2013-02-27 欧司朗光电半导体有限公司 用于有机半导体器件的空穴导电层的掺杂材料及其应用
KR101705136B1 (ko) 2010-03-31 2017-02-09 오스람 오엘이디 게엠베하 유기 반도체 부품용 정공 도체 층을 위한 도펀트, 그리고 이와 같은 도펀트의 용도
KR101757888B1 (ko) 2010-03-31 2017-07-14 오스람 오엘이디 게엠베하 유기 반도체 부품용 정공 도체 층을 위한 도펀트, 그리고 이와 같은 도펀트의 용도
EP2652809B1 (de) * 2010-12-13 2015-07-01 OSRAM Opto Semiconductors GmbH Organisches lichtemittierendes bauelement und verwendung eines kupferkomplexes in einer ladungstransportschicht
US9520575B2 (en) 2010-12-13 2016-12-13 Osram Oled Gmbh Organic light-emitting component and use of a copper complex in a charge transport layer
US9490438B2 (en) 2010-12-13 2016-11-08 Osram Oled Gmbh Optoelectronic component and use of a copper complex in a charge generation layer sequence
DE102010062954A1 (de) * 2010-12-13 2012-06-14 Osram Opto Semiconductors Gmbh Optoelektronisches Bauelement und Verwendung eines Kupferkomplexes in einer Ladungserzeugungsschichtfolge
EP2652811B1 (de) * 2010-12-13 2015-07-08 OSRAM Opto Semiconductors GmbH Optoelektronisches bauelement und verwendung eines kupferkomplexes in einer ladungserzeugungsschichtfolge
DE102010062877A1 (de) * 2010-12-13 2012-06-21 Osram Opto Semiconductors Gmbh Organisches Lichtemittierendes Bauelement und Verwendung eines Kupferkomplexes in einer Ladungstransportschicht
DE102011007052A1 (de) * 2011-04-08 2012-10-11 Osram Opto Semiconductors Gmbh Optoelektronisches Bauelement und Verwendung eines Kupferkomplexes als Dotierstoff zum Dotieren einer Schicht
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CN103493236A (zh) * 2011-04-08 2014-01-01 欧司朗光电半导体有限公司 光电子器件和铜络合物作为掺杂材料以用于对层进行掺杂的应用
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US9929362B2 (en) 2012-06-06 2018-03-27 Siemens Aktiengesellschaft Metal complexes as P-type dopants for organic electronic matrix materials
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JP2015526881A (ja) * 2012-06-06 2015-09-10 シーメンス アクチエンゲゼルシヤフトＳｉｅｍｅｎｓ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ 有機電子マトリクス材料のためのｐ−型ドーパントとしての金属錯体
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KR101736560B1 (ko) * 2012-06-06 2017-05-16 지멘스 악티엔게젤샤프트 유기 전자 매트릭스 물질을 위한 p-도펀트로서의 주족 금속 착물
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US8624229B2 (en) 2014-01-07
US20110089408A1 (en) 2011-04-21
US20140107364A1 (en) 2014-04-17
EP2478576B1 (en) 2017-05-31
JP5836275B2 (ja) 2015-12-24
KR20120080609A (ko) 2012-07-17
EP2478576B9 (en) 2017-09-06
EP2478576A1 (en) 2012-07-25
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US9166178B2 (en) 2015-10-20
KR101768731B1 (ko) 2017-08-16

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