JPS5818326A - 2,4,5-trifluoro-(4'-(trans-4"-alkylcyclohexyl)-cyclohexen-1'- yl)benzene - Google Patents

2,4,5-trifluoro-(4'-(trans-4"-alkylcyclohexyl)-cyclohexen-1'- yl)benzene

Info

Publication number
JPS5818326A
JPS5818326A JP11731481A JP11731481A JPS5818326A JP S5818326 A JPS5818326 A JP S5818326A JP 11731481 A JP11731481 A JP 11731481A JP 11731481 A JP11731481 A JP 11731481A JP S5818326 A JPS5818326 A JP S5818326A
Authority
JP
Japan
Prior art keywords
liquid crystal
benzene
trans
compound
cyclohexen
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.)
Granted
Application number
JP11731481A
Other languages
Japanese (ja)
Other versions
JPS644497B2 (en
Inventor
Shigeru Sugimori
滋 杉森
Tetsuhiko Kojima
哲彦 小島
Masakazu Tsuji
正和 辻
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JNC Corp
Original Assignee
Chisso Corp
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 Chisso Corp filed Critical Chisso Corp
Priority to JP11731481A priority Critical patent/JPS5818326A/en
Publication of JPS5818326A publication Critical patent/JPS5818326A/en
Publication of JPS644497B2 publication Critical patent/JPS644497B2/ja
Granted legal-status Critical Current

Links

Abstract

NEW MATERIAL:The compound of formulaI(R is 1-10C alkyl). EXAMPLE:2, 4, 5-Trifluoro-[4'-( trans-4''-propylcyclohexyl )cyclohexen-1'-yl]-benzene. USE:Useful as a liquid crystal material having positive dielectric anisotropy. It has especially low viscosity, and exhibits a liquid crystal phase over a wide temperature range. PROCESS:The compound of formulaIcan be prepared by reacting 3,4,6-trifluoro- bromobenzene with metallic magnesium reacting the resultant 3,4,6-trifluorophenylmagnesium bromide with 4-(trans-4'-alkylcyclohexyl)-cyclohexanone, and dehydrating the resultant compound with potassium hydrogen sulfate.

Description

【発明の詳細な説明】 本発明は正の誘電異方性を有する新規な液晶物質に関す
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel liquid crystal materials with positive dielectric anisotropy.

液晶表示素子は液晶物質が持つ光学異方性及び誘電異方
性を利用したものであるが、その表示様式によってＴＮ
型（ねじれネマチック型）、ＤＳ型（動的散乱型）、ゲ
スト・ホスト型、訪ψ型など各種の方式に分けられ、夫
々の使用に適する液晶物質の性質は異なる。しかしいず
れの液晶物質も水分、空気、熱、光等に安定であること
が必要であることは共通しており、又、室温を中心とし
て出来るだけ広い温度範囲で液晶相を示すものが求めら
れている。しかし現在のところ単一化合物ではこの様な
条件を満たす物質はなく、数種の液晶化合物や非液晶４
１合物を混合して得られる液晶組成物を使用しているの
が現状である。Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal materials, but depending on the display format, TN
There are various types of liquid crystal materials, including twisted nematic type (twisted nematic type), DS type (dynamic scattering type), guest-host type, and ψ type, and the properties of the liquid crystal materials suitable for each use are different. However, all liquid crystal materials have in common that they need to be stable against moisture, air, heat, light, etc., and they are also required to exhibit a liquid crystal phase over as wide a temperature range as possible, centered around room temperature. ing. However, at present there is no single compound that satisfies these conditions, and there are several types of liquid crystal compounds and non-liquid crystal compounds.
At present, a liquid crystal composition obtained by mixing one compound is used.

本発明の目的はこの様な液晶組成物の一廉分として有用
な、特に低粘度で、広い温度範囲で液晶相を示す新規な
液晶化合物を提供することにある。An object of the present invention is to provide a novel liquid crystal compound useful as a component of such liquid crystal compositions, which has a particularly low viscosity and exhibits a liquid crystal phase over a wide temperature range.

即ち、本発明は一般式 （上式中、Ｒは炭素数１〜１０のアルキル基を示す） で表わされる２、４．５−トリフルオロー〔４′−（）
ランス−４“−アルキルシクロヘキシル）シクロヘキセ
ン−１′−イル〕ベンゼン及ヒ少くともそれを１種含有
する液晶組成物である。That is, the present invention provides 2,4,5-trifluoro[4'-() represented by the general formula (in the above formula, R represents an alkyl group having 1 to 10 carbon atoms)
lance-4"-alkylcyclohexyl)cyclohexen-1'-yl]benzene and a liquid crystal composition containing at least one thereof.

本発明の化合物は約５０〜９０°Ｃの間で液晶相を示し
、又粘度が低いので本発明の化合物を含有する液晶組成
物は粘度が低くなり、低温での表示特性を改善すること
ができる。又本化合物の誘電異方性は＋２程度であるに
もかかわらず、本化合物の添加によｐ液晶組成物のしき
い電圧、飽和電圧は同等もしくは低くなる傾向にある。Since the compound of the present invention exhibits a liquid crystal phase between about 50 and 90°C and has a low viscosity, a liquid crystal composition containing the compound of the present invention has a low viscosity and can improve display characteristics at low temperatures. can. Furthermore, although the dielectric anisotropy of the present compound is about +2, the addition of the present compound tends to make the threshold voltage and saturation voltage of the p-liquid crystal composition the same or lower.

つぎに本発明の化合物の製造法を示すと、ま−ｊ’８．
４．６−）ＩＪフルオロブロムベンゼンと金属マグネシ
ウムを反応させて８．４．６−）リフルオロフェニルマ
グネシウムプロミドとし、ｊれを４−（）：５ンスー４
′−アルキルンクロヘキシル）シクロヘキサノンと反応
させて２，４゜５−トリフルオロ−（４’−（）ランス
−４“−アルキルシクロヘキシル）シクロヘキサン−１
７−オール〕ベンゼンとする。次にこれを硫酸水素カリ
ウムで脱水して、２．４．５−）リフルオロ−（４’−
’（）ランス−４７−アルキルシクロヘキシル）シクロ
ヘキセン−１′−イル〕ベンゼンを得る。Next, the method for producing the compound of the present invention is shown below.
4.6-) IJ fluorobromobenzene and metallic magnesium are reacted to form 8.4.6-) lifluorophenylmagnesium bromide, and J is 4-():5-4.
2,4゜5-trifluoro-(4'-()lans-4"-alkylcyclohexyl)cyclohexane-1
7-ol] benzene. This was then dehydrated with potassium hydrogen sulfate to give 2.4.5-)refluoro-(4'-
'() lance-47-alkylcyclohexyl)cyclohexen-1'-yl]benzene is obtained.

以上を化学式で示すと、 （１） 以下、実施例によｐ本発明の化合物の製法及び使用例に
ついて更に詳細に説明する。The above is expressed by a chemical formula: (1) Hereinafter, the manufacturing method and usage examples of the compound of the present invention will be explained in more detail with reference to Examples.

実施例１（２，４，５−）リフルオロ−〔４′−（トラ
ンス−４７−プロピルシクロヘキシル）シクロヘキセン
−１′−イル〕ベンゼンの製造〕 削り状マグネシウム１．２ｇ（０，０４９モル）を３つ
ロフラスコに入れ、２．４．５−トリノルオロプロムベ
ンゼン９．５ｆＩ（０，０４９モル）Ｎ２気流中で反応
温度を８０〜８５°Ｃに保ちなからゆつく９滴下して行
くと反応して８時間でマグネシウムは溶けて均一にな＃
）２．４．５−）リフルオロフェニルマグネシウムプロ
ミドを生ずる。これに４−（トランス−４′−プロピル
シクロヘキシル）シクロヘキサノンの９．０ｆ（０，０
４１モル）をテトラヒドロフランに溶かして５０ｇ／と
じたものを、反応温度を５〜１０゛Ｃに保ちつつなるべ
く速かに滴下する。滴下後、室温まで昇温し１時間攪拌
し、ついで８Ｎ塩酸ＩＱＱｇ／を加える。反応液を分液
枦斗にとり１００ｇ／のトルエンで８回抽出後、合わせ
たトルエン層を飽和食塩水で洗液が中性になるまで洗浄
してからトルエンを減圧留去する。残留した油状物は２
．４．５−）リフルオロ−（４′−（トランス−４“−
プロピルシクロヘキシル）シクロヘキシル−１′−オー
ル〕ベンゼンでアリ、これに硫酸水素カリウム２．Ｏｆ
を加えＮ２気流中１５０°Ｃで１時間脱水する。冷却後
２００　ｗｌのし、トルエン層を洗液が中性になるまで
水洗する。次いでトルエンを減圧留去し、残る油状物を
エチルアルコールで再結晶して得られるのが２．４．５
−）リフルオロ−（４’−（トランス−４“−プロピル
シクロヘキシル）シクロヘキセン−１′−イル〕ベンゼ
ンである。このものの相転移点は結晶−ネマチック点（
ＣＮ点）４６．０°Ｃ１ネマチック−透明点（ＮＩ点）
８２．０°Ｃであった。収量１．５ｆ、収率１１％であ
った。Example 1 Production of (2,4,5-)lifluoro-[4'-(trans-47-propylcyclohexyl)cyclohexen-1'-yl]benzene] 1.2 g (0,049 mol) of magnesium turnings were Add 9.5 fI (0,049 mol) of 2.4.5-trinoroloprombenzene to a two-cell flask and slowly add 9 drops of 2.4.5-trinoroloprombenzene in a N2 stream while keeping the reaction temperature at 80-85°C. After 8 hours, the magnesium will dissolve and become uniform.
) 2.4.5-) yields trifluorophenylmagnesium bromide. To this, 9.0f (0,0
41 mol) dissolved in tetrahydrofuran and added dropwise as quickly as possible while maintaining the reaction temperature at 5-10°C. After the dropwise addition, the mixture was heated to room temperature and stirred for 1 hour, and then 8N hydrochloric acid (IQQg/) was added. The reaction solution was taken into a separator and extracted eight times with 100 g of toluene. The combined toluene layer was washed with saturated brine until the washings became neutral, and the toluene was distilled off under reduced pressure. The remaining oil is 2
．． 4.5-) refluoro-(4'-(trans-4"-
(propylcyclohexyl)cyclohexyl-1'-ol] benzene, and potassium hydrogen sulfate 2. Of
and dehydrated at 150°C for 1 hour in a N2 stream. After cooling, 200 liters of the toluene layer was washed with water until the washing liquid became neutral. Next, toluene is distilled off under reduced pressure, and the remaining oil is recrystallized with ethyl alcohol to obtain 2.4.5.
-)lifluoro-(4'-(trans-4"-propylcyclohexyl)cyclohexen-1'-yl)benzene. The phase transition point of this is the crystal-nematic point (
CN point) 46.0°C1 nematic-clearing point (NI point)
The temperature was 82.0°C. The yield was 1.5 f, and the yield was 11%.

実施例２ 実施例１に於ける４−（トランス−４″−プロピルシク
ロヘキシル）シクロヘキサノンの代９に４−（）ランス
−４“−ブチルシクロヘキシル）シクロヘキサノン８．
７ｇを使用する外は実施例１と同様にして２．４．５−
）リフルオロ−（４’−（）ランス−４“−ブチルシク
ロヘキシル）シクロヘキセン−１′−イル〕ベンゼンヲ
得り。Example 2 In place of 4-(trans-4″-propylcyclohexyl)cyclohexanone in Example 1, 4-()trans-4″-butylcyclohexyl)cyclohexanone 8.
2.4.5- in the same manner as in Example 1 except that 7 g was used.
) refluoro-(4'-() lance-4"-butylcyclohexyl)cyclohexen-1'-yl]benzene was obtained.

収量１．Ｏｆ、収率６．９％であった。このものの結晶
−ネマチック点は４５．１°Ｃ，ネマチック−透明点は
８８，５°Ｃであった。Yield 1. Of, the yield was 6.9%. The crystal-nematic point of this product was 45.1°C, and the nematic-clearing point was 88.5°C.

実施例３（使用例） ４−ペンテルー４′−シアノビフェニル５０％ ４−へブチル−４′−シアノビフェニル８８％ ４−オクチルオキシ−４′−シアノビフェニル１７％ からなる液晶組成物のネマチック液晶温度範囲は−２〜
４４．Ｂ°Ｃ５粘度は２０°Ｃで４０ｃｐでそれを封入
して得られる液晶セルのしきい値電圧は１．４０Ｖ、飽
和電圧１．９０Ｖである。Example 3 (Usage Example) Nematic liquid crystal temperature of a liquid crystal composition consisting of 50% of 4-pentel-4'-cyanobiphenyl, 88% of 4-hebutyl-4'-cyanobiphenyl, and 17% of 4-octyloxy-4'-cyanobiphenyl. The range is -2~
44. The B°C5 viscosity is 40 cp at 20°C, and the liquid crystal cell obtained by enclosing it has a threshold voltage of 1.40V and a saturation voltage of 1.90V.

この混合物８０部に実施例１で得られた２゜４．５−）
リフルオロ−（４’−（）ランス−４“−プロピルシク
ロヘキシル）シクロヘキセン−１′−イル〕ベンゼンｌ
Ｏ部と実施例２で得られた２、４．５−）リフルオロ−
（４’−（）ランス−４“−ブチルシクロヘキシル）シ
クロヘキセン−１１−イル〕ベンゼンｌＯ部を加えた液
晶組成物のネマチック液晶温度範囲は−６〜５２．５°
Ｃ１粘度は２０°Ｃで８５　ｃｐ、しきい値電圧は１．
８５Ｖ、飽和電圧は１．８０Ｖであった。2°4.5-) obtained in Example 1 was added to 80 parts of this mixture.
Lifluoro-(4'-()lans-4"-propylcyclohexyl)cyclohexen-1'-yl]benzene
Part O and 2,4.5-)refluoro- obtained in Example 2
The nematic liquid crystal temperature range of the liquid crystal composition containing 10 parts of (4'-() lance-4"-butylcyclohexyl)cyclohexen-11-yl]benzene is -6 to 52.5°
C1 viscosity is 85 cp at 20°C, threshold voltage is 1.
85V, and the saturation voltage was 1.80V.

Claims (2)

【特許請求の範囲】[Claims] （１）一般式 （上式中、Ｒは炭素数１〜１０のアルキル基を示す） で表わされる２、４．５−）リフルオロ−〔４′−（ト
ランス−４“−アルキルシクロヘキシル）シクロヘキセ
ン−１’−１ル〕ベンゼン。(1) 2,4.5-)lifluoro-[4'-(trans-4"-alkylcyclohexyl)cyclohexene- 1'-1]benzene. （２）一般式 （上式中、Ｒは炭素数１〜１０のアルキル基を示す） で表わされる２、４．５−トリフルオロ−（４’−（）
ランス−４“−アルキルシクロヘキシル）シクロヘキセ
ン−１′−イル〕ベンゼンを少なくとも一種類含有する
ことを特徴とする液晶組成物。(2) 2,4,5-trifluoro-(4'-() represented by the general formula (in the above formula, R represents an alkyl group having 1 to 10 carbon atoms)
A liquid crystal composition containing at least one type of lance-4"-alkylcyclohexyl)cyclohexen-1'-yl]benzene.
JP11731481A 1981-07-27 1981-07-27 2,4,5-trifluoro-(4'-(trans-4"-alkylcyclohexyl)-cyclohexen-1'- yl)benzene Granted JPS5818326A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP11731481A JPS5818326A (en) 1981-07-27 1981-07-27 2,4,5-trifluoro-(4'-(trans-4"-alkylcyclohexyl)-cyclohexen-1'- yl)benzene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP11731481A JPS5818326A (en) 1981-07-27 1981-07-27 2,4,5-trifluoro-(4'-(trans-4"-alkylcyclohexyl)-cyclohexen-1'- yl)benzene

Publications (2)

Publication Number Publication Date
JPS5818326A true JPS5818326A (en) 1983-02-02
JPS644497B2 JPS644497B2 (en) 1989-01-25

Family

ID=14708678

Family Applications (1)

Application Number Title Priority Date Filing Date
JP11731481A Granted JPS5818326A (en) 1981-07-27 1981-07-27 2,4,5-trifluoro-(4'-(trans-4"-alkylcyclohexyl)-cyclohexen-1'- yl)benzene

Country Status (1)

Country Link
JP (1) JPS5818326A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4551264A (en) * 1982-03-13 1985-11-05 Merck Patent Gesellschaft Mit Beschrankter Haftung Polyhalogenoaromatic compounds for liquid crystal compositions
US5032313A (en) * 1989-03-07 1991-07-16 Chisso Corporation Trifluorobenzene derivative and liquid crystal composition containing the same
US5213710A (en) * 1990-09-26 1993-05-25 Merck Patent Gesellschaft Mit Beschrankter Haftung Benzene derivatives and a liquid-crystalline medium
US5308542A (en) * 1990-03-13 1994-05-03 Merck Patent Gesellschaft Mit Beschrankter Haftung 4,4'-disubstituted 2',3-difluorobisphenyls and a liquid-crystalline medium
US5324449A (en) * 1987-09-25 1994-06-28 Merck Patent Gesellschaft Mit Beschrankter Haftung Substituted phenyl trifluoromethyl ethers
US5389292A (en) * 1988-07-27 1995-02-14 Merck Patent Gesellschaft Mit Beschrankter Haftung Difluoromethyl compounds
US5487845A (en) * 1989-09-06 1996-01-30 Merck Patent Gesellschaft Mit Beschrankter Haftung Fluorobenzene derivatives and liquid-crystalline medium
US5536442A (en) * 1987-09-25 1996-07-16 Merck Patent Gesellschaft Mit Beschrankter Haftung Fluorinated liquid crystal compounds and liquid crystal medium containing same
DE4035509C2 (en) * 1990-11-08 1999-10-21 Merck Patent Gmbh Cyclohexylcyclohexenes and liquid crystalline medium
CN107573212A (en) * 2017-10-13 2018-01-12 河北美星化工有限公司 The synthetic method of trans 4 alkyl-cyclohexyl benzene structure liquid crystal intermediates and monomer

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4551264A (en) * 1982-03-13 1985-11-05 Merck Patent Gesellschaft Mit Beschrankter Haftung Polyhalogenoaromatic compounds for liquid crystal compositions
US5324449A (en) * 1987-09-25 1994-06-28 Merck Patent Gesellschaft Mit Beschrankter Haftung Substituted phenyl trifluoromethyl ethers
US5536442A (en) * 1987-09-25 1996-07-16 Merck Patent Gesellschaft Mit Beschrankter Haftung Fluorinated liquid crystal compounds and liquid crystal medium containing same
US5389292A (en) * 1988-07-27 1995-02-14 Merck Patent Gesellschaft Mit Beschrankter Haftung Difluoromethyl compounds
US5032313A (en) * 1989-03-07 1991-07-16 Chisso Corporation Trifluorobenzene derivative and liquid crystal composition containing the same
US5487845A (en) * 1989-09-06 1996-01-30 Merck Patent Gesellschaft Mit Beschrankter Haftung Fluorobenzene derivatives and liquid-crystalline medium
US5308542A (en) * 1990-03-13 1994-05-03 Merck Patent Gesellschaft Mit Beschrankter Haftung 4,4'-disubstituted 2',3-difluorobisphenyls and a liquid-crystalline medium
US5213710A (en) * 1990-09-26 1993-05-25 Merck Patent Gesellschaft Mit Beschrankter Haftung Benzene derivatives and a liquid-crystalline medium
DE4035509C2 (en) * 1990-11-08 1999-10-21 Merck Patent Gmbh Cyclohexylcyclohexenes and liquid crystalline medium
CN107573212A (en) * 2017-10-13 2018-01-12 河北美星化工有限公司 The synthetic method of trans 4 alkyl-cyclohexyl benzene structure liquid crystal intermediates and monomer
CN107573212B (en) * 2017-10-13 2020-08-04 宁夏中星显示材料有限公司 Synthesis method of trans-4-alkyl cyclohexyl benzene structure liquid crystal intermediate and monomer

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