KR101538534B1 - 중수소화된 방향족 화합물의 제조 방법 - Google Patents

중수소화된 방향족 화합물의 제조 방법 Download PDF

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KR101538534B1
KR101538534B1 KR1020127013666A KR20127013666A KR101538534B1 KR 101538534 B1 KR101538534 B1 KR 101538534B1 KR 1020127013666 A KR1020127013666 A KR 1020127013666A KR 20127013666 A KR20127013666 A KR 20127013666A KR 101538534 B1 KR101538534 B1 KR 101538534B1
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acid
deuterated
deuterium
aromatic
hydrogenated
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KR1020127013666A
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KR20120101029A (ko
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에릭 마우리스 스미쓰
칼린디 도그라
크리스티나 엠. 올더
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이 아이 듀폰 디 네모아 앤드 캄파니
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/001Acyclic or carbocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20Polycyclic condensed hydrocarbons
    • C07C15/24Polycyclic condensed hydrocarbons containing two rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20Polycyclic condensed hydrocarbons
    • C07C15/27Polycyclic condensed hydrocarbons containing three rings
    • C07C15/30Phenanthrenes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05Isotopically modified compounds, e.g. labelled
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/025Sulfonic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/02Ortho- or ortho- and peri-condensed systems
    • C07C2603/04Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24Anthracenes; Hydrogenated anthracenes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/02Ortho- or ortho- and peri-condensed systems
    • C07C2603/40Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/02Ortho- or ortho- and peri-condensed systems
    • C07C2603/40Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/48Chrysenes; Hydrogenated chrysenes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/02Ortho- or ortho- and peri-condensed systems
    • C07C2603/40Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/50Pyrenes; Hydrogenated pyrenes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/02Ortho- or ortho- and peri-condensed systems
    • C07C2603/52Ortho- or ortho- and peri-condensed systems containing five condensed rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
KR1020127013666A 2009-10-26 2009-12-21 중수소화된 방향족 화합물의 제조 방법 KR101538534B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US25484309P 2009-10-26 2009-10-26
US61/254,843 2009-10-26

Publications (2)

Publication Number Publication Date
KR20120101029A KR20120101029A (ko) 2012-09-12
KR101538534B1 true KR101538534B1 (ko) 2015-07-21

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Country Status (6)

Country Link
EP (1) EP2493835A4 (zh)
JP (1) JP5662461B2 (zh)
KR (1) KR101538534B1 (zh)
CN (1) CN102574753B (zh)
TW (1) TW201114735A (zh)
WO (1) WO2011053334A1 (zh)

Cited By (14)

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KR20210081291A (ko) * 2019-12-23 2021-07-01 주식회사 엘지화학 방향족 화합물의 제조방법
WO2021210898A1 (ko) * 2020-04-16 2021-10-21 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20210152727A (ko) 2020-06-09 2021-12-16 주식회사 엘지화학 안트라센계 화합물, 이를 포함하는 코팅조성물 및 유기 발광 소자
KR20220006313A (ko) 2020-07-08 2022-01-17 주식회사 엘지화학 안트라센계 화합물, 이를 포함하는 코팅조성물 및 유기 발광 소자
KR20220065453A (ko) 2020-11-13 2022-05-20 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20220065449A (ko) 2020-11-13 2022-05-20 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20220065451A (ko) 2020-11-13 2022-05-20 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20220065950A (ko) 2020-11-13 2022-05-23 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20220100362A (ko) 2021-01-08 2022-07-15 주식회사 엘지화학 안트라센계 화합물, 및 이를 포함하는 유기 발광 소자
KR20220100361A (ko) 2021-01-08 2022-07-15 주식회사 엘지화학 안트라센계 화합물, 및 이를 포함하는 유기 발광 소자
WO2023282676A1 (ko) 2021-07-07 2023-01-12 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20230018162A (ko) 2021-07-29 2023-02-07 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20230018160A (ko) 2021-07-29 2023-02-07 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20230018159A (ko) 2021-07-29 2023-02-07 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

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US8759818B2 (en) 2009-02-27 2014-06-24 E I Du Pont De Nemours And Company Deuterated compounds for electronic applications
JP5567656B2 (ja) 2009-04-03 2014-08-06 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 電気活性材料
KR20120091144A (ko) 2009-09-29 2012-08-17 이 아이 듀폰 디 네모아 앤드 캄파니 발광 응용을 위한 중수소화된 화합물
EP2493887A4 (en) 2009-10-29 2013-06-19 Du Pont DETERERATED COMPOUNDS FOR ELECTRONIC APPLICATIONS
US8617720B2 (en) 2009-12-21 2013-12-31 E I Du Pont De Nemours And Company Electroactive composition and electronic device made with the composition
TW201229204A (en) 2010-12-17 2012-07-16 Du Pont Anthracene derivative compounds for electronic applications
WO2012083301A1 (en) 2010-12-17 2012-06-21 E. I. Du Pont De Nemours And Company Anthracene derivative compounds for electronic applications
US9293716B2 (en) 2010-12-20 2016-03-22 Ei Du Pont De Nemours And Company Compositions for electronic applications
KR20140015298A (ko) 2010-12-20 2014-02-06 이 아이 듀폰 디 네모아 앤드 캄파니 전자적 응용을 위한 전기활성 조성물
JP2014507401A (ja) 2010-12-20 2014-03-27 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 電子技術応用のためのトリアジン誘導体
JP5926286B2 (ja) 2010-12-21 2016-05-25 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company ピリミジン化合物を含む電子デバイス
WO2014130597A1 (en) 2013-02-25 2014-08-28 E. I. Du Pont De Nemours And Company Electronic device including a diazachrysene derivative
US10134988B2 (en) 2013-12-13 2018-11-20 E I Du Pont De Nemours And Company System for forming an electroactive layer
CN104198631B (zh) * 2014-08-11 2017-01-18 贾明宏 一种提高蛋白质在氘代试剂中氢氘原子交换效率的方法
US9944846B2 (en) 2014-08-28 2018-04-17 E I Du Pont De Nemours And Company Compositions for electronic applications
CN107074763B (zh) 2014-10-20 2021-01-05 株式会社Lg化学 蓝色发光化合物
US10804473B2 (en) 2015-05-21 2020-10-13 Lg Chem, Ltd. Electron transport materials for electronic applications
JP6789594B2 (ja) 2016-07-20 2020-11-25 エルジー・ケム・リミテッド 電気活性材料
KR102627027B1 (ko) * 2019-11-29 2024-01-18 주식회사 엘지화학 중수소화 안트라센계 화합물의 제조 방법 및 이로부터 제조된 중수소화 안트라센계 화합물을 포함하는 유기 발광 소자
CN115362148A (zh) * 2020-04-10 2022-11-18 德山新勒克斯有限公司 用于有机电气元件的化合物、使用所述化合物的有机电气元件及其电子装置
KR20210126822A (ko) * 2020-04-10 2021-10-21 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN113555519A (zh) 2020-04-24 2021-10-26 罗门哈斯电子材料韩国有限公司 有机电致发光装置
CN113896734A (zh) 2020-07-06 2022-01-07 罗门哈斯电子材料韩国有限公司 有机电致发光化合物、多种主体材料和包含其的有机电致发光装置
DE102022112831A1 (de) * 2021-05-26 2022-12-01 Rohm And Haas Electronic Materials Korea Ltd. Verfahren zur herstellung von deuterierten organischen verbindungen
US20230255102A1 (en) 2022-01-20 2023-08-10 Rohm And Haas Electronic Materials Korea Ltd. Plurality of host materials and organic electroluminescent device comprising the same
EP4231804A3 (en) 2022-02-16 2023-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US20240107880A1 (en) 2022-08-17 2024-03-28 Universal Display Corporation Organic electroluminescent materials and devices

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3389705A (en) * 1966-04-29 1968-06-25 Levavi David Cigarette smoke filter device
JP2004010550A (ja) * 2002-06-07 2004-01-15 Japan Science & Technology Corp 重水素化芳香族化合物の製造方法
WO2004011400A1 (ja) * 2002-07-26 2004-02-05 Wako Pure Chemical Industries, Ltd. 芳香環の重水素化方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3989705A (en) * 1974-04-01 1976-11-02 Canadian Patents And Development Limited Processes for the deuteration and/or tritiation of organic substrates by hydrogen substitution
JPS6153228A (ja) * 1984-08-22 1986-03-17 Nippon Sheet Glass Co Ltd 芳香族化合物に高選択的に水素同位体を導入する方法
JPH0653693B2 (ja) * 1986-07-24 1994-07-20 ユニチカ株式会社 重水素化フエノ−ル類の製造方法
JPH06228014A (ja) * 1993-01-28 1994-08-16 Tosoh Corp 重水素化芳香族化合物の製造法
JP2789084B2 (ja) * 1995-11-24 1998-08-20 勝 中原 重水素化化合物の製造方法
TW200413273A (en) * 2002-11-15 2004-08-01 Wako Pure Chem Ind Ltd Heavy hydrogenation method of heterocyclic rings
TW200413274A (en) * 2002-12-27 2004-08-01 Wako Pure Chem Ind Ltd Deuteration or tritiation method
WO2005070853A1 (ja) * 2004-01-23 2005-08-04 Wako Pure Chemical Industries, Ltd. 混合触媒を用いた重水素化方法
JP5464395B2 (ja) * 2008-02-01 2014-04-09 大陽日酸株式会社 重水素化された芳香環又は複素環を有する化合物の製造方法
EP2493887A4 (en) * 2009-10-29 2013-06-19 Du Pont DETERERATED COMPOUNDS FOR ELECTRONIC APPLICATIONS

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3389705A (en) * 1966-04-29 1968-06-25 Levavi David Cigarette smoke filter device
JP2004010550A (ja) * 2002-06-07 2004-01-15 Japan Science & Technology Corp 重水素化芳香族化合物の製造方法
WO2004011400A1 (ja) * 2002-07-26 2004-02-05 Wako Pure Chemical Industries, Ltd. 芳香環の重水素化方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Tetrahedron Letters, 2002, 43(13), pp.2389-2392 *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20210081291A (ko) * 2019-12-23 2021-07-01 주식회사 엘지화학 방향족 화합물의 제조방법
KR102594845B1 (ko) * 2019-12-23 2023-10-27 주식회사 엘지화학 방향족 화합물의 제조방법
WO2021210898A1 (ko) * 2020-04-16 2021-10-21 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20210152727A (ko) 2020-06-09 2021-12-16 주식회사 엘지화학 안트라센계 화합물, 이를 포함하는 코팅조성물 및 유기 발광 소자
KR20220006313A (ko) 2020-07-08 2022-01-17 주식회사 엘지화학 안트라센계 화합물, 이를 포함하는 코팅조성물 및 유기 발광 소자
KR20220065451A (ko) 2020-11-13 2022-05-20 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20220065449A (ko) 2020-11-13 2022-05-20 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20220065950A (ko) 2020-11-13 2022-05-23 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20220065453A (ko) 2020-11-13 2022-05-20 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20220100362A (ko) 2021-01-08 2022-07-15 주식회사 엘지화학 안트라센계 화합물, 및 이를 포함하는 유기 발광 소자
KR20220100361A (ko) 2021-01-08 2022-07-15 주식회사 엘지화학 안트라센계 화합물, 및 이를 포함하는 유기 발광 소자
WO2023282676A1 (ko) 2021-07-07 2023-01-12 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20230018162A (ko) 2021-07-29 2023-02-07 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20230018160A (ko) 2021-07-29 2023-02-07 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20230018159A (ko) 2021-07-29 2023-02-07 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

Also Published As

Publication number Publication date
CN102574753B (zh) 2015-07-08
JP5662461B2 (ja) 2015-01-28
KR20120101029A (ko) 2012-09-12
WO2011053334A1 (en) 2011-05-05
JP2013508360A (ja) 2013-03-07
CN102574753A (zh) 2012-07-11
EP2493835A1 (en) 2012-09-05
EP2493835A4 (en) 2015-07-15
TW201114735A (en) 2011-05-01

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