JPH02180890A - Liquid crystal compound of disiloxanes - Google Patents
Liquid crystal compound of disiloxanesInfo
- Publication number
- JPH02180890A JPH02180890A JP64000414A JP41489A JPH02180890A JP H02180890 A JPH02180890 A JP H02180890A JP 64000414 A JP64000414 A JP 64000414A JP 41489 A JP41489 A JP 41489A JP H02180890 A JPH02180890 A JP H02180890A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- compound
- present
- expressed
- 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
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 55
- 150000001875 compounds Chemical class 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 claims description 24
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 2
- 150000002989 phenols Chemical class 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
- 239000004988 Nematic liquid crystal Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- -1 phenyl ester Chemical class 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002262 Schiff base Substances 0.000 description 4
- 150000004753 Schiff bases Chemical class 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 150000004074 biphenyls Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- PRDZROBDMPYWMJ-UHFFFAOYSA-N (4-cyanophenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=C(C#N)C=C1 PRDZROBDMPYWMJ-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YVFMGBISSJHIRW-UHFFFAOYSA-N methyl 4-prop-2-enoxybenzoate Chemical compound COC(=O)C1=CC=C(OCC=C)C=C1 YVFMGBISSJHIRW-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明はジシロキサン類のエステル誘導体である液晶化
合物、および該化合物を有効成分として含有する液晶組
成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a liquid crystal compound that is an ester derivative of disiloxanes, and a liquid crystal composition containing the compound as an active ingredient.
液晶を利用した表示素子は、時計、電卓等に広く使用さ
れている。Display elements using liquid crystals are widely used in watches, calculators, and the like.
これらの液晶表示素子は液晶物質の光学異方性および誘
電異方性を利用したものである。液晶相にはネマチック
液晶相、スメクチック液晶相、コレステリック液晶相が
あり、そのうちネマチック液晶相を利用したものが最も
広く実用化されている。These liquid crystal display elements utilize optical anisotropy and dielectric anisotropy of liquid crystal materials. Liquid crystal phases include a nematic liquid crystal phase, a smectic liquid crystal phase, and a cholesteric liquid crystal phase, and among these, those utilizing the nematic liquid crystal phase are most widely put into practical use.
それらには、液晶表示に応用されている電気光学効果に
対応して、ＴＮ（ねじれネマチック）型、ＤＳ（動的散
乱）型、ゲスト・ホスト型、ＤＡＰ型等の表示素子があ
る。These display elements include TN (twisted nematic) type, DS (dynamic scattering) type, guest-host type, DAP type, etc. corresponding to the electro-optic effect applied to liquid crystal displays.
それぞれに使用される液晶物質は臼然界のなるべく広い
温度範囲で液晶相を示すものが望ましい。It is desirable that the liquid crystal materials used in each case exhibit a liquid crystal phase over as wide a natural temperature range as possible.
現在のところ、単一の液晶物質で、そのような条件をみ
たす物質はなく、数種の液晶物質、またはさらに非液晶
物質を混合して実用に徴している。At present, there is no single liquid crystal material that satisfies these conditions, and a mixture of several types of liquid crystal materials or even non-liquid crystal materials has been put into practical use.
これらの物質は、また水分、光、熱、空気等に対して安
定であることを要求されている。These materials are also required to be stable against moisture, light, heat, air, and the like.
前記のような液晶混合物、すなわち液晶組成物は低温か
ら高温まで、ネマチック液晶温度範囲を有することが望
まれる。It is desired that the liquid crystal mixture, ie, the liquid crystal composition, has a nematic liquid crystal temperature range from low to high temperatures.
本発明の目的は、広い温度範囲で液晶相を示し、また他
の液晶混合物あるいは液晶混合物と非液晶物質との混合
物に少量混合して、もとの液晶混合物の粘度をそれ程高
めることなく、液晶温度範囲を拡大する新規の液晶化合
物および該化合物を含有する液晶組成物を提供すること
である。It is an object of the present invention to produce liquid crystals that exhibit a liquid crystal phase over a wide temperature range, and that can be mixed in a small amount into other liquid crystal mixtures or mixtures of liquid crystal mixtures and non-liquid crystal substances without significantly increasing the viscosity of the original liquid crystal mixture. An object of the present invention is to provide a novel liquid crystal compound that expands the temperature range and a liquid crystal composition containing the compound.
本発明者は前記課題を解決するため鋭意研究を行った。 The present inventor conducted extensive research in order to solve the above problems.
その結果、ジシロキサン類のエステル誘導体が約２００
℃から３００℃以上まで液晶相を示し、また他の液晶組
成物に少量加えることにより、液晶組成物のＮ−Ｉ点を
上昇させることができることを見い出し、本発明を完成
した。As a result, about 200 ester derivatives of disiloxanes
It has been found that it exhibits a liquid crystal phase from .degree. C. to over 300.degree. C., and that by adding a small amount to other liquid crystal compositions, the N-I point of the liquid crystal composition can be raised, and the present invention has been completed.
すなわち本発明は、下記一般式（１）で表わされるジシ
ロキサン類液晶化合物である。That is, the present invention is a disiloxane liquid crystal compound represented by the following general formula (1).
・・・（Ｉ）
（但しく１）式において、Ｘ−Ｆ、ＣｊｌＳｎ−１゜２
、ｍは３〜１０を示す。）
また本発明は、該化合物を有効成分として含有する液晶
組成物である。...(I) (However, in formula 1), X-F, CjlSn-1゜2
, m represents 3-10. ) The present invention also provides a liquid crystal composition containing the compound as an active ingredient.
本発明の化合物の製造方法としては、例えば下記反応式
によって示される反応によって製造し得る。The compound of the present invention can be produced, for example, by a reaction represented by the following reaction formula.
Ｕ ＣＭ３ＣＨ３０
ｐｔ触媒
ピリジン
２ＣＨ２−ＣＩＭＣＨ２ザＯＯ旨（叶Ｘすなわち、２倍
モルの４− （ω−アルケニルオキシ）安息香酸メチル
エステルに、１，１，３゜３−テトラメチルシロキサン
を白金触媒で反応させて、１．３−ビス（４−メトキシ
カルボニルフェニルオキシアルキル）−１，１，３，３
−テトラメチルシロキサンとし、これにアルカリを作用
させて、加水分解反応させて安息香酸を製造した。U CM3CH30 pt Catalyst Pyridine 2CH2-CIMCH2 1,3-bis(4-methoxycarbonylphenyloxyalkyl)-1,1,3,3
-Tetramethylsiloxane was treated with an alkali to cause a hydrolysis reaction to produce benzoic acid.
この安息香酸誘導体に塩化チオニルを作用させ、酸クロ
リドとし、これと反応するフェノールを反応させて目的
とする化合物（１）を製造した。This benzoic acid derivative was reacted with thionyl chloride to form an acid chloride, and the desired compound (1) was produced by reacting the acid chloride with the reacting phenol.
また、〔Ｉ〕は４−ω−アルケニルオキシ安息香酸−４
−置換フェニルエステルと１．１，３゜３、−テトラメ
チルシロキサンと白金触媒の作用によっても製造できる
。In addition, [I] is 4-ω-alkenyloxybenzoic acid-4
It can also be produced by the action of a -substituted phenyl ester, 1,1,3°3, -tetramethylsiloxane, and a platinum catalyst.
また、本発明の液晶組成物は、前記の式に示す本発明の
化合物を少なくとも一成分含有することを特徴とする。Further, the liquid crystal composition of the present invention is characterized in that it contains at least one component of the compound of the present invention represented by the above formula.
本発明の液晶組成物の成分にできる本発明の化合物以外
の他の成分としては、例えばエステル系、シッフ塩基系
、ビフェニル系、フェニルシクロヘキサン系、複素環系
等の化合物をあげることができる。Other components other than the compound of the present invention that can be used as components of the liquid crystal composition of the present invention include, for example, ester-based, Schiff base-based, biphenyl-based, phenylcyclohexane-based, and heterocyclic-based compounds.
これらの化合物の具体例としては、エステル系の液晶化
合物としては
トランス−４−アルキルシクロへキサンカルボン酸−４
−アルキルフェニルエステル、トランス−４−アルキル
シクロへキサンカルボン酸−４−アルコキシフェニルエ
ステル、４−アルコキシ安息香酸−４−アルキルフェニ
ルエステル、
４−アルキル安息香酸−４−シアノフェニルエステル、
４− （トランス−４−アルキルシクロヘキシル）安息
香酸−４−シアノフェニルエステル等、シッフ塩基系液
晶化合物としては、
４−アルコキシベンジリデン−４−アルカノイルオキシ
アニリン、
４−アルコキシベンジリデン−４−アルアルキルアニリ
ン、
４−アルコキシベンジリデン−４−シアノアニリン等、
ビフェニル系液晶化合物としては、
４′ −アルキル−４−シアノビフェニル、４′ −ア
ルコキシ−４〜シアノビフエニル、４′ −アルコキシ
−４−アルキルビフェニル等、フェニルシクロヘキサン
系化合物としては、トランス−４−アルキル−（４−シ
アノフェニル）シクロヘキサン、
トランス−４−アルキル−（４−アルコキシフェニル）
シクロヘキサン等、
複素環系液晶化合物としては、
５−アルキル−２−（４−シアノフェニル）１．３−ジ
オキサン、
５−アルキル−２−（４−シアノフェニル）ピリミジン
５−シアノ−２−（４−アルキルフェニル）ピリミジン
等をあげることができる。Specific examples of these compounds include trans-4-alkylcyclohexanecarboxylic acid-4 as an ester-based liquid crystal compound.
-alkyl phenyl ester, trans-4-alkylcyclohexanecarboxylic acid-4-alkoxyphenyl ester, 4-alkoxybenzoic acid-4-alkyl phenyl ester, 4-alkylbenzoic acid-4-cyanophenyl ester, 4-(trans Schiff base liquid crystal compounds such as -4-alkylcyclohexyl)benzoic acid-4-cyanophenyl ester include 4-alkoxybenzylidene-4-alkanoyloxyaniline, 4-alkoxybenzylidene-4-aralkylaniline, 4-alkoxybenzylidene Biphenyl liquid crystal compounds such as -4-cyanoaniline, 4'-alkyl-4-cyanobiphenyl, 4'-alkoxy-4-cyanobiphenyl, 4'-alkoxy-4-alkylbiphenyl, etc., and phenylcyclohexane compounds include , trans-4-alkyl-(4-cyanophenyl)cyclohexane, trans-4-alkyl-(4-alkoxyphenyl)
Examples of heterocyclic liquid crystal compounds such as cyclohexane include 5-alkyl-2-(4-cyanophenyl)1,3-dioxane, 5-alkyl-2-(4-cyanophenyl)pyrimidine 5-cyano-2-(4 -alkylphenyl)pyrimidine, etc.
本発明の化合物は広い温度範囲でネマチック液晶相を示
し、かつ液晶から液体になる温度（Ｎ−１点）が高い。The compound of the present invention exhibits a nematic liquid crystal phase over a wide temperature range, and has a high temperature (N-1 point) at which it changes from liquid crystal to liquid.
また液晶組成物に少量添加することにより、液晶組成物
の液晶−液体点（Ｎ−１点）を上昇させることができ、
又粘度をそれ程高くしない。In addition, by adding a small amount to the liquid crystal composition, the liquid crystal-liquid point (N-1 point) of the liquid crystal composition can be increased.
Also, do not make the viscosity that high.
本発明の化合物は、多くの液晶化合物、すなわち、エス
テル系、シッフ塩基系、ビフェニル系、フェニルシクロ
ヘキサン系、複素環系等との相溶性がよく、本発明の化
合物を液晶化合物に少量添加することによってΔｎ （
＝ｎｌ−ｎｌ、即ち液晶軸方向に平行な屈折率と直角な
屈折率との差）を小さくすることができる。The compound of the present invention has good compatibility with many liquid crystal compounds, such as esters, Schiff bases, biphenyls, phenylcyclohexane, heterocyclics, etc., and the compound of the present invention can be added in small amounts to liquid crystal compounds. by Δn (
=nl-nl, that is, the difference between the refractive index parallel to the liquid crystal axis direction and the refractive index perpendicular to the liquid crystal axis direction) can be reduced.
以下実施例によって、本発明を更に具体的に説明するが
、本発明はこの実施例によって同等限定されるものでは
ない。The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to the same extent by these Examples.
（実施例１）
１．３−ビス（４−（４−フルオロフェニルオキシカル
ボニル）フェニルオキシプロピル〕 −１゜１．３．３
−テトラメチルシロキサンの製造（〔１３式においてＸ
ｍＦＳｎｍｌ、ｍ−３）窒素雰囲気下に、１，１，３．
３−テトラメチルシロキサン７．５ｇをトルエン５０
ｍｌに溶解し、よく攪拌する。これにアリルオキシ安息
香酸メチルエステル２３Ｋをトルエン３００ｍ１．スパ
イヤー触媒を５μｇ加えたものを４０℃にて２時間で滴
下した。更にこの温度で５０時間反応を続けた。(Example 1) 1.3-bis(4-(4-fluorophenyloxycarbonyl)phenyloxypropyl) -1°1.3.3
-Production of tetramethylsiloxane ([X in formula 13
mFSnml, m-3) under nitrogen atmosphere, 1,1,3.
7.5 g of 3-tetramethylsiloxane in 50 g of toluene
ml and stir well. To this, add 23K of allyloxybenzoic acid methyl ester to 300ml of toluene. 5 μg of Speyer's catalyst was added dropwise at 40° C. over 2 hours. The reaction was further continued at this temperature for 50 hours.
反応終了後、トルエンを留去後、残った油状物をすぐに
つぎの反応に用いた。After the reaction was completed, the toluene was distilled off, and the remaining oil was immediately used in the next reaction.
エタノール５００ｍ１を水酸化カリウム５０ｇを水１０
０ ｍｌに溶解したものに加え、これに先に得られた油
状物を加えた。500ml of ethanol, 50g of potassium hydroxide, 10ml of water
In addition to the solution in 0 ml, the oil obtained earlier was added to this.
マントルヒーター上で５時間還流した後、３Ｎ塩酸１．
５１に注ぎ込んだ。After refluxing for 5 hours on a heating mantle, 3N hydrochloric acid 1.
I poured it into 51.
析出した沈澱を濾過し、よく水洗した後、よく乾燥した
。The deposited precipitate was filtered, thoroughly washed with water, and then thoroughly dried.
これが、１．３−ビス（４−ヒドロキシカルボニルフェ
ニルオキシプロビル）−１，１，３，３−テトラメチル
シロキサンである。This is 1,3-bis(4-hydroxycarbonylphenyloxyprobyl)-1,1,3,3-tetramethylsiloxane.
このカルボン酸４．９ｇに過剰の塩化チオニルを加え、
５時間還流した。Add excess thionyl chloride to 4.9 g of this carboxylic acid,
It was refluxed for 5 hours.
減圧にて、塩化チオニルを留去すると固形物が残る。こ
れをトルエン５０ ｍｌに溶解し、別に４−フルオロフ
ェノール１．５ｇをピリジン１０ｍ１とトルエン１００
ｍ１に溶かしたものに加え、よく攪拌した。Thionyl chloride is distilled off under reduced pressure, leaving a solid. Dissolve this in 50 ml of toluene, and separately add 1.5 g of 4-fluorophenol to 10 ml of pyridine and 100 ml of toluene.
ml and stirred well.
一晩放置してから、水５００ｍ１中にあけ、トルエン１
００ｍ１を加えて抽出した。トルエン層を２Ｎ苛性ソー
ダ水溶液で洗浄した後、中性になるまで水洗した。After leaving it overnight, pour it into 500ml of water and add 11ml of toluene.
00ml was added and extracted. The toluene layer was washed with a 2N aqueous sodium hydroxide solution and then washed with water until it became neutral.
ついで無水硫酸ナトリウムで乾燥後、トルエンを減圧で
留去し、残った油状物を活性アルミナのカラムを用いて
、トルエン溶媒でクロマト処理を行った。溶出したトル
エン溶液を減圧にしてトルエンを留去し、残った固形物
をエタノールで再結晶を行って、目的とする１、３−ビ
ス（４−（４−フルオロフェニルオキシカルボニル）フ
ェニルオキシプロピル）−１，１，３，３，−テトラメ
チルシロキサンを製造した。収量は１．５ｇ（収率２２
％ンであった。After drying over anhydrous sodium sulfate, toluene was distilled off under reduced pressure, and the remaining oil was chromatographed using an activated alumina column with a toluene solvent. The eluted toluene solution is reduced in pressure to remove toluene, and the remaining solid is recrystallized with ethanol to obtain the desired 1,3-bis(4-(4-fluorophenyloxycarbonyl)phenyloxypropyl). -1,1,3,3-tetramethylsiloxane was produced. The yield was 1.5g (yield 22
It was %.
結晶−スメクチック液晶転移点（Ｃ−９ａ）
１４９．２℃スメクチック液晶−ネマチック液晶転
移点（Ｓ−Ｎ〜１８５．７℃ネマチック液晶−透明点（
Ｎ−１［有］ ２１７．３℃であった。Crystal-smectic liquid crystal transition point (C-9a)
149.2℃ smectic liquid crystal - nematic liquid crystal transition point (S-N ~ 185.7℃ nematic liquid crystal - clearing point (
N-1 [Yes] The temperature was 217.3°C.
（実施例２．３）
実施ｆｌｌにおいて、４−アリルオキシ安息香酸メチル
エステルの代りに４−ω−アルケニルオキシ安息香酸メ
チルエステルを用い、又４−フルオロフェノールの代り
に他のフェノール誘導体を用いることにより、種々のエ
ステル化合物を製造した。これらの結果を実施例１の結
果と共に表１に示した。(Example 2.3) By using 4-ω-alkenyloxybenzoic acid methyl ester instead of 4-allyloxybenzoic acid methyl ester and using other phenol derivatives instead of 4-fluorophenol in the experiment , produced various ester compounds. These results are shown in Table 1 together with the results of Example 1.
表 １
（実施例４）・・・応用例１
なる組成の液晶組成物（Ａ）のＮ−Ｉ点は５２．３℃、
Δε（＝と謡−ε上液晶軸方向に平行な誘電率と直角な
誘電率との差）は＋１０．７．２０℃におけるΔｎは０
．１１９、粘度は２１．７ｃ、ｐ、である。Table 1 (Example 4) Application example 1 The N-I point of liquid crystal composition (A) having the following composition is 52.3°C,
Δε (= and the difference between the dielectric constant parallel to the liquid crystal axis direction and the dielectric constant perpendicular to the liquid crystal axis direction) is +10.7.Δn at 20℃ is 0
．． 119, the viscosity is 21.7c,p.
液晶セルとして、酸化ケイ素をコーティングし、ラビン
グ処理した酸化スズ透明電極を有する基板を対向させて
組立てた。電極間距離が９μｍのものを用意し、前記の
液晶混合物（Ａ）を封入して、２０℃で、その特性を測
定したところ、しきい値電圧ｖｔｈは１．６０Ｖであっ
た。A liquid crystal cell was assembled by facing substrates having tin oxide transparent electrodes coated with silicon oxide and subjected to rubbing treatment. A device with an inter-electrode distance of 9 μm was prepared, the liquid crystal mixture (A) described above was sealed, and its characteristics were measured at 20° C., and the threshold voltage vth was 1.60V.
この液晶組成物（Ａ）９５ｆｆｉ量％に本発明の実施例
１で製造した１、３−ビス（４−（４−フルオロフェニ
ルオキシカルボニル）フェニルオキシプロピル）−１，
１，３，３−テトラメチルシロキサン５重量％溶解した
組成物のＮ−１点は５６．５℃、誘電率異方性（ｇ＋＋
−ε□）、Δεは＋９．５、屈折率異方性（ｎｉ ｎ
□）、Δｎは０．１１５、粘度は２１．５ｃ、ｐ、であ
った。またしきい値電圧ｖｔｈは１．６５Ｖであった。1,3-bis(4-(4-fluorophenyloxycarbonyl)phenyloxypropyl)-1, prepared in Example 1 of the present invention, was added to 95ffi% of this liquid crystal composition (A).
The N-1 point of the composition in which 5% by weight of 1,3,3-tetramethylsiloxane was dissolved was 56.5°C, and the dielectric anisotropy (g++
-ε□), Δε is +9.5, refractive index anisotropy (ni n
□), Δn was 0.115, and viscosity was 21.5c,p. Further, the threshold voltage vth was 1.65V.
このようにＮ−１点は上昇したにもかかわらず、粘度も
あまり変化せずΔｎも少し小さくなった。Although the N-1 point increased in this way, the viscosity did not change much and Δn became slightly smaller.
〔発明の効果〕
本発明の化合物は、広い温度範囲でネマチック液晶相を
示し、且つ高いＮ−１点を示し、液晶組成物に少量添加
することにより、粘度を高めることなく、液晶組成物の
Ｎ−１点を上昇させΔｎも小さくすることができる。[Effects of the Invention] The compound of the present invention exhibits a nematic liquid crystal phase over a wide temperature range and a high N-1 point, and can be added to a liquid crystal composition in a small amount without increasing the viscosity. By increasing the N-1 point, Δn can also be reduced.
多くの液晶化合物、すなわちエステル系、シッフ塩基系
、ビフェニル系、フェニルシクロヘキサン系、複素環系
等との相溶性が良好であり、本発明の化合物を液晶組成
物に少量添加することによって、粘度をそれ程上昇させ
ずに、Δｎを小さくすることができる。これらの化合物
はＳＴＮ （スーパートウイステッドネマチック）型標
示素子に有利に応用できる。It has good compatibility with many liquid crystal compounds, such as esters, Schiff bases, biphenyls, phenylcyclohexanes, and heterocyclics, and by adding a small amount of the compound of the present invention to a liquid crystal composition, the viscosity can be reduced. It is possible to reduce Δn without increasing it much. These compounds can be advantageously applied to STN (super twisted nematic) type indicating elements.
実用上の効果の大きい発明である。This invention has great practical effects.
Claims (1)
合物。 ▲数式、化学式、表等があります▼・・・〔 I 〕 （但し、〔 I 〕式において、Ｘ＝Ｆ、Ｃｌ、ｎ＝１、
２、ｍは３〜１０を示す。） ２、請求項１記載のジシロキサン類液晶化合物を少なく
とも一種類含有する液晶組成物。[Claims] 1. A disiloxane liquid crystal compound represented by the general formula [I]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼...[I] (However, in the [I] formula, X=F, Cl, n=1,
2, m indicates 3-10. 2. A liquid crystal composition containing at least one disiloxane liquid crystal compound according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP64000414A JP2718970B2 (en) | 1989-01-06 | 1989-01-06 | Disiloxane compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP64000414A JP2718970B2 (en) | 1989-01-06 | 1989-01-06 | Disiloxane compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02180890A true JPH02180890A (en) | 1990-07-13 |
| JP2718970B2 JP2718970B2 (en) | 1998-02-25 |
Family
ID=11473139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP64000414A Expired - Lifetime JP2718970B2 (en) | 1989-01-06 | 1989-01-06 | Disiloxane compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2718970B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2274652A (en) * | 1993-01-30 | 1994-08-03 | Dow Corning | Liquid crystal device containing a siloxane |
| GB2274649A (en) * | 1993-01-30 | 1994-08-03 | Dow Corning Ltd | Liquid crystal siloxanes |
| US5498368A (en) * | 1993-09-10 | 1996-03-12 | Dow Corning Limited | Liquid crystal devices |
| WO2003040812A1 (en) * | 2001-11-08 | 2003-05-15 | Qinetiq Limited | Liquid crystal compounds, liquid crystal mixtures containing them and liquid crystal devices |
-
1989
- 1989-01-06 JP JP64000414A patent/JP2718970B2/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| MOL CRYST LIQ CRYST=1988 * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2274652A (en) * | 1993-01-30 | 1994-08-03 | Dow Corning | Liquid crystal device containing a siloxane |
| GB2274649A (en) * | 1993-01-30 | 1994-08-03 | Dow Corning Ltd | Liquid crystal siloxanes |
| US5455697A (en) * | 1993-01-30 | 1995-10-03 | Dow Corning Limited | Liquid crystal device |
| US5547604A (en) * | 1993-01-30 | 1996-08-20 | Dow Corning Limited | Liquid crystal siloxanes |
| GB2274649B (en) * | 1993-01-30 | 1996-11-27 | Dow Corning | Liquid crystal siloxanes |
| GB2274652B (en) * | 1993-01-30 | 1997-07-23 | Dow Corning | Liquid crystal device |
| JP2007186695A (en) * | 1993-01-30 | 2007-07-26 | Dow Corning Ltd | Liquid crystal device |
| JP4620037B2 (en) * | 1993-01-30 | 2011-01-26 | ダウ・コーニング・リミテッド | LCD device |
| US5498368A (en) * | 1993-09-10 | 1996-03-12 | Dow Corning Limited | Liquid crystal devices |
| WO2003040812A1 (en) * | 2001-11-08 | 2003-05-15 | Qinetiq Limited | Liquid crystal compounds, liquid crystal mixtures containing them and liquid crystal devices |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2718970B2 (en) | 1998-02-25 |
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