TWI886146B - 鈰(iv)錯合物及其在有機電子件上的用途 - Google Patents
鈰(iv)錯合物及其在有機電子件上的用途 Download PDFInfo
- Publication number
- TWI886146B TWI886146B TW109131291A TW109131291A TWI886146B TW I886146 B TWI886146 B TW I886146B TW 109131291 A TW109131291 A TW 109131291A TW 109131291 A TW109131291 A TW 109131291A TW I886146 B TWI886146 B TW I886146B
- Authority
- TW
- Taiwan
- Prior art keywords
- phenyl
- alkyl
- bis
- aryl
- trifluoromethyl
- Prior art date
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102019213844 | 2019-09-11 | ||
| DE102019213844.6 | 2019-09-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW202116784A TW202116784A (zh) | 2021-05-01 |
| TWI886146B true TWI886146B (zh) | 2025-06-11 |
Family
ID=72432888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW109131291A TWI886146B (zh) | 2019-09-11 | 2020-09-11 | 鈰(iv)錯合物及其在有機電子件上的用途 |
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)
| 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)
| 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 |
| CN1325431A (zh) * | 1998-11-02 | 2001-12-05 | 南岸大学企业有限公司 | 场致发光材料 |
| TW201302768A (zh) * | 2011-05-25 | 2013-01-16 | Sumitomo Chemical Co | 鈰錯合物及含該鈰錯合物之有機電子元件 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| TWI467045B (zh) * | 2008-05-23 | 2015-01-01 | Sigma Aldrich Co | 高介電常數電介質薄膜與使用鈰基前驅物製造高介電常數電介質薄膜之方法 |
| 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 |
| 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 |
| 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 |
| US20170117503A1 (en) * | 2015-10-22 | 2017-04-27 | 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 |
| 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 |
-
2020
- 2020-09-07 JP JP2022515623A patent/JP7667992B2/ja active Active
- 2020-09-07 US US17/641,129 patent/US12590107B2/en active Active
- 2020-09-07 EP EP20768553.8A patent/EP4029069B1/en active Active
- 2020-09-07 EP EP25161862.5A patent/EP4557929A3/en active Pending
- 2020-09-07 WO PCT/EP2020/074918 patent/WO2021048044A1/en not_active Ceased
- 2020-09-07 KR KR1020227011367A patent/KR102849214B1/ko active Active
- 2020-09-07 CN CN202080064076.4A patent/CN114364653B/zh active Active
- 2020-09-11 TW TW109131291A patent/TWI886146B/zh active
Patent Citations (3)
| 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 |
| CN1325431A (zh) * | 1998-11-02 | 2001-12-05 | 南岸大学企业有限公司 | 场致发光材料 |
| TW201302768A (zh) * | 2011-05-25 | 2013-01-16 | Sumitomo Chemical Co | 鈰錯合物及含該鈰錯合物之有機電子元件 |
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 |
| 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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