KR102849214B1 - 세륨(iv) 착물 및 유기 전자공학에서의 용도 - Google Patents

세륨(iv) 착물 및 유기 전자공학에서의 용도

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Publication number
KR102849214B1
KR102849214B1 KR1020227011367A KR20227011367A KR102849214B1 KR 102849214 B1 KR102849214 B1 KR 102849214B1 KR 1020227011367 A KR1020227011367 A KR 1020227011367A KR 20227011367 A KR20227011367 A KR 20227011367A KR 102849214 B1 KR102849214 B1 KR 102849214B1
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KR
South Korea
Prior art keywords
phenyl
alkyl
bis
haloalkyl
aryl
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KR1020227011367A
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English (en)
Korean (ko)
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KR20220062026A (ko
Inventor
사샤 도록
마르커스 파프메이어
레오나드 아이만
Original Assignee
크레독시스 게엠베하
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/92—Ketonic chelates
    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • 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]
    • H10K50/17—Carrier injection 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
    • H10K85/30—Coordination compounds
    • H10K85/351—Metal complexes comprising lanthanides or actinides, e.g. comprising europium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/50—Photovoltaic [PV] devices
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electromagnetism (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Thin Film Transistor (AREA)
  • Photovoltaic Devices (AREA)
KR1020227011367A 2019-09-11 2020-09-07 세륨(iv) 착물 및 유기 전자공학에서의 용도 Active KR102849214B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102019213844 2019-09-11
DE102019213844.6 2019-09-11
PCT/EP2020/074918 WO2021048044A1 (en) 2019-09-11 2020-09-07 Cerium (iv) complexes and their use in organic electronics

Publications (2)

Publication Number Publication Date
KR20220062026A KR20220062026A (ko) 2022-05-13
KR102849214B1 true KR102849214B1 (ko) 2025-08-21

Family

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Family Applications (1)

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KR1020227011367A Active KR102849214B1 (ko) 2019-09-11 2020-09-07 세륨(iv) 착물 및 유기 전자공학에서의 용도

Country Status (7)

Country Link
US (1) US12590107B2 (https=)
EP (2) EP4029069B1 (https=)
JP (1) JP7667992B2 (https=)
KR (1) KR102849214B1 (https=)
CN (1) CN114364653B (https=)
TW (1) TWI886146B (https=)
WO (1) WO2021048044A1 (https=)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3859811B1 (en) 2020-01-28 2025-03-19 Novaled GmbH An organic electronic device comprising an anode layer, a cathode layer, at least one emission layer (eml) and at least one hole injection layer (hil)
CN111302926B (zh) * 2020-04-14 2024-04-02 湖北固润科技股份有限公司 β-二酮铈(IV)类化合物及其制备和应用
WO2022023260A1 (en) 2020-07-27 2022-02-03 Novaled Gmbh Metal complexes of 3-(2,3,5-trifluoro-6-(trifluoromethyl)pyridin-4-yl)pentane-2,4-dione and similar ligands as semiconductor materials for use in electronic devices
EP4496458A3 (en) * 2020-07-27 2025-03-26 Novaled GmbH Metal complexes of 3-(2,3,5-trifluoro-6-(trifluoromethyl)pyridin-4-yl)pentane-2,4-dione and similar ligands as semiconductor materials for use in electronic devices
US20230242562A1 (en) 2020-07-28 2023-08-03 Novaled Gmbh Compound of Formula (I), a Semiconductor Material Comprising at Least One Compound of Formula (I), a Semiconductor Layer Comprising at Least One Compound of Formula (I) and an Electronic Device Comprising at Least One Compound of Formula (I)
EP3945125A1 (en) 2020-07-28 2022-02-02 Novaled GmbH Compound of formula (i), a semiconductor material comprising at least one compound of formula (i), an semiconductor layer comprising at least one compound of formula (i) and an electronic device comprising at least one compound of formula (i)
WO2022101343A1 (de) 2020-11-16 2022-05-19 Credoxys GmbH Cer-ethylendiaminketonartige - und cer-salenartige-komplexe und deren verwendung in der organischen elektronik
US20240247004A1 (en) 2021-03-10 2024-07-25 Credoxys GmbH New cerium (iv) complexes and their use in organic electronics
EP4106031A1 (en) * 2021-06-18 2022-12-21 Novaled GmbH Sheet resistance component
EP4199131A1 (en) * 2021-12-15 2023-06-21 Novaled GmbH A ce(iv) metal complex, an organic electronic device comprising an anode layer, a cathode layer and a charge generation layer, wherein the charge generation layer comprises a p-type charge generation layer that comprises the ce(iv) metal complex and a n-type charge generation layer
KR20240067095A (ko) 2021-09-20 2024-05-16 노발레드 게엠베하 기판, 애노드층, 캐소드층, 적어도 하나의 제1 방출층, 및 금속 착화합물을 포함하는 정공 주입층을 포함하는 유기 전자 장치, 및 금속 착화합물
KR20240067934A (ko) * 2021-09-20 2024-05-17 노발레드 게엠베하 화합물, 화합물을 포함하는 반도체층 및 유기 전자 장치
EP4152426A1 (en) * 2021-09-20 2023-03-22 Novaled GmbH An organic electronic device comprising a substrate, an anode layer, a cathode layer, at least one first emission layer, and a hole injection layer that comprises a metal complex as well as a metal complex
WO2023247416A1 (en) 2022-06-21 2023-12-28 Dottikon Es Holding Ag Tetraarylbenzidine type compounds and their use in organic electronics
EP4340581A1 (en) * 2022-09-19 2024-03-20 Novaled GmbH An electroluminescent device comprising an anode layer, a cathode layer, a first emission layer, a hole injection layer and a first hole transport layer that comprises a compound containing a metal
KR20250073113A (ko) * 2022-09-19 2025-05-27 노발레드 게엠베하 전하 발생층을 포함하는 유기 전자 소자
WO2024133366A1 (en) 2022-12-23 2024-06-27 Merck Patent Gmbh Electronic device
WO2024160820A1 (en) 2023-01-31 2024-08-08 Credoxys GmbH Cerium-diketonate complexes and use thereof in organic electronics
EP4478861A1 (en) 2023-06-15 2024-12-18 Novaled GmbH Organic electroluminescent device comprising a first metal compound and a second metal compound, and a display device comprising the organic electroluminescent device
EP4478862A1 (en) 2023-06-15 2024-12-18 Novaled GmbH Organic electroluminescent device comprising a first metal compound and a second metal compound, and a display device comprising the organic electroluminescent device
WO2025195961A1 (de) 2024-03-19 2025-09-25 Merck Patent Gmbh Organische lichtemittierende vorrichtungen
EP4646076A1 (en) * 2024-04-30 2025-11-05 CREDOXYS GmbH Light harvesting component
EP4646085A1 (en) 2024-04-30 2025-11-05 CREDOXYS GmbH Indacene compounds and the use thereof
EP4683484A1 (en) 2024-07-19 2026-01-21 CREDOXYS GmbH Binuclear metal complexes and the use thereof in organic electronics
EP4716436A1 (en) 2024-09-19 2026-03-25 CREDOXYS GmbH Oled display comprising cerium-diketonate complexes and method to produce such an oled display

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011525699A (ja) * 2008-05-23 2011-09-22 シグマ−アルドリッチ・カンパニー、エルエルシー 高ｋ誘電性膜およびセリウム系前駆体を用いる製造方法
JP2017069280A (ja) 2015-09-28 2017-04-06 シャープ株式会社 発光装置および発光システム
US20190221771A1 (en) * 2015-10-22 2019-07-18 Universal Display Corporation Buffer layer for organic light emitting devices and method of making the same

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4036605A (en) 1971-09-01 1977-07-19 Gulf Research & Development Company Chelates of cerium (IV), their preparation and gasoline containing said chelates
JPS601324B2 (ja) * 1975-09-10 1985-01-14 三菱レイヨン株式会社 水溶性ビニル化合物の重合方法
US4511515A (en) * 1983-06-28 1985-04-16 Corning Glass Works Method for making a volatile cerium diketonate compound
JP2505244B2 (ja) * 1988-04-07 1996-06-05 出光興産株式会社 薄膜ｅｌ素子
JPH11302288A (ja) * 1998-04-23 1999-11-02 Nippon Steel Corp 新規なセリウム錯体
GB9823761D0 (en) * 1998-11-02 1998-12-23 South Bank Univ Entpr Ltd Novel electroluminescent materials
GB9826405D0 (en) * 1998-12-02 1999-01-27 South Bank Univ Entpr Ltd Method for forming films or layers
WO2002018394A1 (en) 2000-08-28 2002-03-07 Advanced Technology Materials, Inc. Source reagent compositions and method for forming metal films on a substrate by chemical vapor deposition
US7811676B2 (en) * 2002-12-24 2010-10-12 Merck Patent Gmbh Electroluminescent materials and devices
US20040214362A1 (en) * 2003-01-22 2004-10-28 Hill Steven E. Doped semiconductor nanocrystal layers and preparation thereof
GB2440367A (en) 2006-07-26 2008-01-30 Oled T Ltd Electroluminescent device
EP2180029B1 (en) 2008-10-23 2011-07-27 Novaled AG Radialene compounds and their use
JP5735791B2 (ja) * 2010-12-07 2015-06-17 住友化学株式会社 金属錯体を含む素子
WO2012161205A1 (ja) * 2011-05-25 2012-11-29 住友化学株式会社 セリウム錯体及び該セリウム錯体を含む有機電子素子
CN102617616A (zh) * 2012-02-23 2012-08-01 沈阳化工大学 微波固相法制备一种金属铈有机发光材料
DE102012007795B3 (de) 2012-04-20 2013-02-21 Novaled Ag Aromatische Amin-Terphenyl-Verbindungen und Verwendung derselben in organischen halbleitenden Bauelementen
CN104673292A (zh) * 2013-11-27 2015-06-03 海洋王照明科技股份有限公司 铟锆酸盐发光薄膜、电致发光器件及二者的制备方法
US10297770B2 (en) * 2015-03-27 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
JP2017141192A (ja) * 2016-02-10 2017-08-17 国立研究開発法人産業技術総合研究所 セリウムペルオキソ錯体
JP6903374B2 (ja) * 2017-03-27 2021-07-14 東ソー株式会社 セリウム錯体組成物、製造方法及びその用途
TWI774767B (zh) 2017-05-12 2022-08-21 瑞士商多蒂孔股份有限公司 茚烷衍生物及其在有機電子產品的用途
DE102020103268B8 (de) 2020-02-10 2023-04-20 Sichuan Knowledge Express Institute For Innovative Technologies Co., Ltd. Ce(III)-Komplexe, Zusammensetzung aufweisend Ce(III)-Komplexe, optoelektronische Vorrichtung, Verfahren zu deren Herstellung, Verfahren zum Dublett-Harvesting und Verfahren für Hyperfluoreszenz mit sehr kurzer Abklingzeit
CN111302926B (zh) * 2020-04-14 2024-04-02 湖北固润科技股份有限公司 β-二酮铈(IV)类化合物及其制备和应用

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011525699A (ja) * 2008-05-23 2011-09-22 シグマ−アルドリッチ・カンパニー、エルエルシー 高ｋ誘電性膜およびセリウム系前駆体を用いる製造方法
JP2017069280A (ja) 2015-09-28 2017-04-06 シャープ株式会社 発光装置および発光システム
US20190221771A1 (en) * 2015-10-22 2019-07-18 Universal Display Corporation Buffer layer for organic light emitting devices and method of making the same

Also Published As

Publication number Publication date
JP2022548551A (ja) 2022-11-21
KR20220062026A (ko) 2022-05-13
US20230092935A1 (en) 2023-03-23
WO2021048044A1 (en) 2021-03-18
TWI886146B (zh) 2025-06-11
EP4029069A1 (en) 2022-07-20
TW202116784A (zh) 2021-05-01
EP4557929A3 (en) 2025-07-30
EP4557929A2 (en) 2025-05-21
US12590107B2 (en) 2026-03-31
JP7667992B2 (ja) 2025-04-24
CN114364653B (zh) 2026-02-17
EP4029069B1 (en) 2025-04-09
CN114364653A (zh) 2022-04-15

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