KR940006976A - 아세틸렌 유도체 - Google Patents

아세틸렌 유도체 Download PDF

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KR940006976A
KR940006976A KR1019930019610A KR930019610A KR940006976A KR 940006976 A KR940006976 A KR 940006976A KR 1019930019610 A KR1019930019610 A KR 1019930019610A KR 930019610 A KR930019610 A KR 930019610A KR 940006976 A KR940006976 A KR 940006976A
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carbon atoms
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샤트 마르틴
빌리거 알로이스
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프리돌린 클라우스너,롤란드 보러
에프. 호프만-라 롯슈 아크티엔게젤샤프트
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Abstract

본 발명은 하기 일반식(Ⅰ)의 화합물을 제공한다.
(Ⅰ)
상기식에서, R은 탄소원자수 1내지 12의 알킬 그룹이거나 또는 일반식의 그룹[여기서, 고리 A2는 트랜스-1,4-시클로헥실렌 또는 트랜스-1,3-디옥산-2,5디일이고, R1은 탄소원자수 1내지 12의 알킬 또는 탄소원자수 2내지 12의 알케닐 또는 알콕시알킬 그룹이다]이고, A1은 불소로 치환되거나 치환되지 않은 1,4-페닐렌 또는 피리딘-2,5-디일 또는 피리미딘-2,5-디일이고, X1은 불소, 염소, 브롬, 트리플루오로메틸, 트리플루오로 메톡시 또는 디플루오로메톡시이고, X2및 X3은 각각 수소 또는 불소이다.
또한 본 발명은 이들 화합물을 포함하는 액정혼합물 및 전기-광학적 목적을 위한 이들 화합물 및 혼합물의 용도에 관한 것이다.

Description

아세틸렌 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (9)

  1. 하기 일반식(Ⅰ)의 화합물.
    (Ⅰ)
    상기식에서, R은 탄소원자수 1내지 12의 알킬 그룹이거나 또는 일반식의 그룹[여기서, 고리 A2는 트랜스-1,4-시클로헥실렌 또는 트랜스-1,3-디옥산-2,5-디일이고, R1은 탄소원자수 1내지 12의 알킬 또는 탄소원자수 2내지 12의 알케닐 또는 알콕시알킬 그룹이다]이고, 고리 A1은 불소로 치환되거나 치환되지 않은 1,4-페닐렌 또는 피리딘-2,5-디일 또는 피리미딘-2,5-디일이고, X1은 불소, 염소, 브롬, 트리플루오로메틸, 트리플루오로 메톡시 또는 디플루오로메톡시이고, X2및 X3은 각각 수소 또는 불소이다.
  2. 제1항에 있어서, 하기 일반식(1a) 내지 (1c)의 화합물.
    (1a)
    (1b)
    (1c)
    상기식에서 R은 탄소원자수 1내지 12의 알킬 그룹이고, X1은 수소 또는 불소이다. X1및X3는 제1항에서 정의한 바와 같다.
  3. 제1항에 있어서, 하기 일반식(1d) 내지 (1i)의 화합물.
    (1d)
    (1e)
    (1f)
    (1g)
    (1h)
    (1i)
    상기식에서 R1,X1및X2는 제1항에 정의한 바와 같고, X4는 수소 또는 불소이다.
  4. 제1항 내지 제3항중 어느 한 항에 있어서, R은 탄소원자수 1내지 7의 알킬이고, R1은 탄소원자수 1내지 7의 알킬 또는 탄소원자수 2내지 7의 알콕시알킬 또는 알케닐인 화합물.
  5. 제1항, 제2항 및 제4항중 어느 한 항에 있어서, R이 탄소원자수 2내지 5의 알킬그룹인 화합물.
  6. 제1항, 제3항 및 제4항중 어느 한 항에 있어서, R1이 탄소원자수 2내지 5의 알킬또는 알케닐이고, A2가 트랜스-1,4-시클로헥실렌인 화합물.
  7. 적어도 한 성분이 제1항에서 정의된 일반식(Ⅰ)의 화합물인 액정 혼합물.
  8. 광학 또는 전기-광학적 목적을 위한 제1항에서 정의된 일반식(Ⅰ) 화합물의 용도.
  9. 광학 또는 전기-광학적 목적을 위한 제7항에 따른 액정 혼합물의 용도.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930019610A 1992-09-25 1993-09-24 아세틸렌 유도체 KR100268740B1 (ko)

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DE59010895D1 (de) * 1989-09-06 2000-02-24 Merck Patent Gmbh Fluorbenzolderivate und flüssigkristallines Medium
DE4417441A1 (de) * 1994-05-19 1995-11-23 Merck Patent Gmbh Fluormethylethinyl- und Difluormethylethinylbenzole und ihre Verwendung in Flüssigkristallmischungen
TW347412B (en) * 1994-10-05 1998-12-11 Sumitomo Kagaku Kk Liquid crystal compositions and a liquid crystal element containing the same
US5833879A (en) * 1995-02-15 1998-11-10 Chisso Corporation Liquid crystalline alkynyltolan compound, liquid crystal composition and liquid crystal display element
JP3797438B2 (ja) * 1995-06-26 2006-07-19 大日本インキ化学工業株式会社 4−フルオロ−3−トリフルオロメトキシベンゼン誘導体
JPH09151377A (ja) * 1995-11-30 1997-06-10 Chisso Corp 液晶組成物および液晶表示素子
US5858276A (en) * 1996-09-09 1999-01-12 Pioneer Electronic Corporation DAP mode liquid crystal display device
US6217793B1 (en) * 1998-06-05 2001-04-17 Mitsui Chemicals, Inc. Acetylene compound, liquid crystal composition and liquid crystal element
US6287647B1 (en) * 1999-12-03 2001-09-11 Minolta Co., Ltd. Liquid crystal composition and liquid crystal display using the same
JP4748339B2 (ja) * 2001-01-26 2011-08-17 Dic株式会社 メチレンシクロヘキサン誘導体
KR20180026378A (ko) * 2015-07-02 2018-03-12 디아이씨 가부시끼가이샤 액정 조성물 및 이것을 사용한 액정 표시 소자
US10752838B2 (en) 2015-07-02 2020-08-25 Dic Corporation Liquid crystal composition and liquid crystal display device using the same

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB155465A (en) * 1920-01-15 1920-12-23 Glenn Roy Granzow Improvements in and relating to armored tire
GB2155465B (en) * 1984-01-23 1987-12-31 Dainippon Ink & Chemicals Tolan-type nematic liquid crystalline compounds
DE3710069A1 (de) * 1987-03-27 1988-10-06 Merck Patent Gmbh Ethinderivate
DE3835803A1 (de) * 1988-03-10 1990-04-26 Merck Patent Gmbh Supertwist-fluessigkristallanzeigeelement und fluessigkristallmischung
EP0409634A3 (en) * 1989-07-20 1991-11-27 Sanyo Chemical Industries Ltd. Liquid crystal compounds and optically active compounds
GB2240544B (en) * 1990-01-29 1993-08-18 Merck Patent Gmbh Liquid crystalline fluorinated chloro tolans
JP2701083B2 (ja) * 1990-04-19 1998-01-21 旭電化工業株式会社 含フッ素トラン化合物
JP2884732B2 (ja) * 1990-07-26 1999-04-19 大日本インキ化学工業株式会社 フルオロトラン系化合物
JP3226045B2 (ja) * 1991-09-10 2001-11-05 大日本インキ化学工業株式会社 フルオロトラン系アルケニル化合物

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KR100268740B1 (ko) 2000-10-16
DE59306095D1 (de) 1997-05-15
US5447657A (en) 1995-09-05
JPH06199713A (ja) 1994-07-19
EP0589331A1 (de) 1994-03-30

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