JP7667992B2 - セリウム（ｉｖ）複合体及びそれらの有機電子工学における使用 - Google Patents

セリウム（ｉｖ）複合体及びそれらの有機電子工学における使用 Download PDF

Info

Publication number
JP7667992B2
JP7667992B2 JP2022515623A JP2022515623A JP7667992B2 JP 7667992 B2 JP7667992 B2 JP 7667992B2 JP 2022515623 A JP2022515623 A JP 2022515623A JP 2022515623 A JP2022515623 A JP 2022515623A JP 7667992 B2 JP7667992 B2 JP 7667992B2
Authority
JP
Japan
Prior art keywords
formula
alkyl
haloalkyl
aryl
unsubstituted
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.)
Active
Application number
JP2022515623A
Other languages
English (en)
Japanese (ja)
Other versions
JP2022548551A (ja
JP2022548551A5 (https=
Inventor
ドロク、サシャ
パプマイヤー、マーカス
エイマン、レオナール
Original Assignee
クレドクシス ゲーエムベーハー
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 クレドクシス ゲーエムベーハー filed Critical クレドクシス ゲーエムベーハー
Publication of JP2022548551A publication Critical patent/JP2022548551A/ja
Publication of JP2022548551A5 publication Critical patent/JP2022548551A5/ja
Application granted granted Critical
Publication of JP7667992B2 publication Critical patent/JP7667992B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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)
JP2022515623A 2019-09-11 2020-09-07 セリウム（ｉｖ）複合体及びそれらの有機電子工学における使用 Active JP7667992B2 (ja)

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 (3)

Publication Number Publication Date
JP2022548551A JP2022548551A (ja) 2022-11-21
JP2022548551A5 JP2022548551A5 (https=) 2023-07-10
JP7667992B2 true JP7667992B2 (ja) 2025-04-24

Family

ID=72432888

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2022515623A Active JP7667992B2 (ja) 2019-09-11 2020-09-07 セリウム（ｉｖ）複合体及びそれらの有機電子工学における使用

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 (9)

* 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
JP2012124252A (ja) 2010-12-07 2012-06-28 Sumitomo Chemical Co Ltd 金属錯体を含む素子
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
US20160285016A1 (en) 2015-03-27 2016-09-29 Universal Display Corporation Organic electroluminescent materials and devices
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
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
JP2018162399A (ja) 2017-03-27 2018-10-18 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
US20190221771A1 (en) 2015-10-22 2019-07-18 Universal Display Corporation Buffer layer for organic light emitting devices and method of making the same
JP2023511056A (ja) 2020-02-10 2023-03-16 四川知本快車創新科技研究院有限公司 光電デバイスに適用可能で、デュアル捕獲機構と超短減衰時間を備えた超蛍光セリウム（ｉｉｉ）含有キレート

Family Cites Families (17)

* 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
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
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
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
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 (9)

* 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
JP2012124252A (ja) 2010-12-07 2012-06-28 Sumitomo Chemical Co Ltd 金属錯体を含む素子
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
US20160285016A1 (en) 2015-03-27 2016-09-29 Universal Display Corporation Organic electroluminescent materials and devices
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
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
JP2018162399A (ja) 2017-03-27 2018-10-18 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
JP2023511056A (ja) 2020-02-10 2023-03-16 四川知本快車創新科技研究院有限公司 光電デバイスに適用可能で、デュアル捕獲機構と超短減衰時間を備えた超蛍光セリウム（ｉｉｉ）含有キレート

Also Published As

Publication number Publication date
JP2022548551A (ja) 2022-11-21
KR20220062026A (ko) 2022-05-13
KR102849214B1 (ko) 2025-08-21
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
CN114364653B (zh) 2026-02-17
EP4029069B1 (en) 2025-04-09
CN114364653A (zh) 2022-04-15

Similar Documents

Publication Publication Date Title
JP7667992B2 (ja) セリウム（ｉｖ）複合体及びそれらの有機電子工学における使用
JP2024508788A (ja) 新規なセリウム（ｉｖ）複合体及びそれらの有機電子工学における使用
KR101768731B1 (ko) 유기 전자 장치 및 유기 반도체 매트릭스 재료를 도핑하기 위한 도판트
Koskin et al. Selectively Fluorinated Furan‐Phenylene Co‐Oligomers Pave the Way to Bright Ambipolar Light‐Emitting Electronic Devices
TWI618699B (zh) 光電轉換材料、光電轉換元件、光感測器及攝像元件
EP3442022B1 (en) Compound and organic photoelectric device, image sensor and electronic device including the same
JP2023550703A (ja) セリウム－エチレンジアミンケトン型及びセリウム－サレン型複合体及びそれらの有機電子工学における使用
EP1829132B8 (en) Material for doped and undoped hole and electron transport layer
EP4634187A1 (en) Indacene and azaindacene compounds and higher homologues and the use thereof
HK40126473A (en) Cerium (iv) complexes and their use in organic electronics
US20240292740A1 (en) Organic electronic device comprising a compound of formula (i), display device comprising the organic electronic device as well as compounds of formula (i)
EP4646076A1 (en) Light harvesting component
EP4716436A1 (en) Oled display comprising cerium-diketonate complexes and method to produce such an oled display
WO2024160820A1 (en) Cerium-diketonate complexes and use thereof in organic electronics
KR20230127248A (ko) 화합물 및 유기 전자 소자에서의 이의 용도
Holzer Pentacene-and chalcogeneophene-based conjugated compounds as functinonal organic materials
KR20070100949A (ko) 도핑 및 비도핑 정공 및 전자 수송층을 위한 재료

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20220308

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20230628

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20230628

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20240321

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20240410

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20240625

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20240904

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20241108

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20250214

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: 20250314

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20250405

R150 Certificate of patent or registration of utility model

Ref document number: 7667992

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150