JPS5995255A - Optically active substance having negative dielectric anisotropy - Google Patents
Optically active substance having negative dielectric anisotropyInfo
- Publication number
- JPS5995255A JPS5995255A JP20588982A JP20588982A JPS5995255A JP S5995255 A JPS5995255 A JP S5995255A JP 20588982 A JP20588982 A JP 20588982A JP 20588982 A JP20588982 A JP 20588982A JP S5995255 A JPS5995255 A JP S5995255A
- Authority
- JP
- Japan
- Prior art keywords
- cyano
- formula
- liquid crystal
- optically active
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は負の誘電異方性を有し、光学活性な、らせん分
子構造を持った成品性化合物及びそれを含有する液晶組
成物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a commercially available compound having negative dielectric anisotropy, optically active, and a helical molecular structure, and a liquid crystal composition containing the same.
液晶表示素子は液晶物質の特性である光学異方性及び誘
電異方性を利用したもので各種の表示方式のものがある
が、そのうち現在最も実用化されているのはねじれネマ
チック型（ＴＮ型）電動的散乱型（ＤＳ型）などである
。しかし最近は他の方式の液晶表示方法の詫発も盛んに
行々われ、中でもコレステリック・ネマチック相転移型
表示及びホワイト・テーラ−型カラー表示などがその代
表的なものである。これらの表示素子に用いられる液晶
組成物はいずれもネマチック液晶に光学活性物質などを
添加して、それぞれに適したコレステリックのらせんピ
ッチをもつ様に調節される。添加する光学活性物質の分
子はねじれたらせん構造をもち、そのらせんピッｙ−は
短かく、かつ熱、光、空気、水に安定なものが望まれて
いる。本発明の化合物は以上の様な用途に使用して有用
な、光学活性を有し、ねじれた分子構造をもつ新規な化
合物である。Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy that are the characteristics of liquid crystal materials, and there are various display methods, but the currently most practically used type is the twisted nematic type (TN type). ) electric scattering type (DS type), etc. However, recently, other types of liquid crystal display methods have been frequently criticized, with cholesteric-nematic phase transition display and White-Taylor color display being representative examples. The liquid crystal compositions used in these display elements are each adjusted to have an appropriate cholesteric helical pitch by adding an optically active substance to a nematic liquid crystal. It is desired that the molecules of the optically active substance to be added have a twisted helical structure, that the helical pitch is short, and that it is stable against heat, light, air, and water. The compound of the present invention is a novel compound having optical activity and a twisted molecular structure, which is useful for the above-mentioned applications.
即ち、本発明は一般式
（」一式中ｍは○又はｌｓｎは１又は２であり、＊は不
斉炭素原予察示す）
で表わされるＳ −（＋ｌ−４−（２−メチルブチル）
基を有するカルボン酸の２−シアノ−４−クロロフェニ
ルエステル及びそれを含有する液晶組成物である。That is, the present invention provides S -(+l-4-(2-methylbutyl)
2-cyano-4-chlorophenyl ester of carboxylic acid having a group and a liquid crystal composition containing the same.
本発明の化合物けらせん分子構造を持ち、あるものはコ
レステリック相を示し、又負の誘電異方性を有している
。これらの化合物をネマチック液晶に少量添加してコレ
ステリック・ネマチック相転移型表示素子用又はホワイ
ト・テーラ−型表示素子用の液晶組成物を得ることが出
来る。この化合物をネマチック液晶に１０係添加して測
定して得られるらせんピッチの値から得られるこの化合
物自体のらせんピッ′ｆ′は０．２μｍ〜３μｍである
。又、この化合物をＴＮ型表示素子用のネマチック液晶
組成物に添加すると表示面のしま模様（いわゆるリバー
スドメイン）の発生を少くして、その性能を改善するこ
とが出来る。The compounds of the present invention have a helical molecular structure, some exhibit a cholesteric phase, and also have negative dielectric anisotropy. By adding a small amount of these compounds to a nematic liquid crystal, a liquid crystal composition for a cholesteric-nematic phase transition type display element or a White-Taylor type display element can be obtained. The helical pitch 'f' of this compound itself, obtained from the helical pitch value obtained by adding 10 parts of this compound to a nematic liquid crystal and measuring it, is 0.2 μm to 3 μm. Furthermore, when this compound is added to a nematic liquid crystal composition for a TN type display element, it is possible to reduce the occurrence of striped patterns (so-called reverse domains) on the display surface and improve its performance.
次に本発明による化合物の製造法について述べると既知
の化合物であるＳ −（＋ｌ−４−（２−メチルブチル
）安息香酸クロリド、Ｓ−１＋１−４−（２〜メチルブ
チル）ビフェニリル−４′−カルボン酸クロリド、５−
（−Ｈ−（２−メチルブチルオキシ）安息香酸クロリド
、又は４−８−１＋ｌ−４−（２−メチルブチルオキシ
）ビフェニリル−４′−カルボン酸クロリドなどのカル
ボン酸クロリドと２−シアノ−４−クロロフェノールピ
リジンの存在下で反応して目的の化合物を得ることがで
きる。以上を化学式で示すと次の通りになる。Next, the method for producing the compound according to the present invention will be described. The known compounds S-(+l-4-(2-methylbutyl)benzoic acid chloride, S-1+1-4-(2-methylbutyl)biphenylyl-4'-carvone) acid chloride, 5-
Carboxylic acid chloride such as (-H-(2-methylbutyloxy)benzoic acid chloride, or 4-8-1+l-4-(2-methylbutyloxy)biphenylyl-4'-carboxylic acid chloride and 2-cyano-4 -The target compound can be obtained by reacting in the presence of chlorophenol pyridine.The chemical formula shown above is as follows.
Ｎ
（上式中ｍ、ｎは前記と同じ）
以下、実施例によυ本化合物の製造及び物性を更に詳細
に説明する。N (in the above formula, m and n are the same as above) Hereinafter, the production and physical properties of the present compound will be explained in more detail with reference to Examples.
実施例１
（Ｓ −（＋１−４− （２−メチルブチルオキシ）安
息Ｓ［ｘ−２−シアノ−４−クロロフェニルエステルの
製造〕
５−（−＋−）−４−（２−メチルブチルオキシ）安息
香酸クロリド２．３ｔと２−シアノ−４−クロＵフエノ
ール１．５２をピリジンユＯづＶＣ７容かしたものとを
混合して反応させる。この反応液に更に無水トルエン１
００−加え、室温で一晩放置する。それを水中にあけト
ルエンを追加して抽出し、トルエン層を６Ｎ塩酸、つい
で２Ｎ苛性ソーダ水浴液で洗浄した後中性になるまで水
洗する。それを無水硫酸す１１ウムで乾繰後トルエンを
減圧で留去し、残った固型物をエタノールで再結晶する
と目的の８−１＋）−４−（２−メチルブチルオキシ）
安息香１渡−２−シアノ−４−クロロフェニルエステル
が１．５ｇ（収率４４％）得られた。このものの融点は
７８．５〜８０．５℃であった。又ネマチック液晶組成
物にこのものを１０％加えて測定したらせんピッチの値
から計嘗ニして得られるこの化合物自身のらせんピッチ
は３．４μｍであった。Example 1 (Production of S-(+1-4-(2-methylbutyloxy)benS[x-2-cyano-4-chlorophenyl ester)] 5-(-+-)-4-(2-methylbutyloxy ) 2.3 t of benzoic acid chloride and 1.52 ton of 2-cyano-4-chlorophenol in 7 liters of pyridine are mixed and reacted.Additionally, 1 t of anhydrous toluene is added to this reaction solution.
00-Add and leave overnight at room temperature. It is poured into water and extracted by adding toluene, and the toluene layer is washed with 6N hydrochloric acid, then with a 2N caustic soda water bath, and then washed with water until it becomes neutral. After drying with 11 um of anhydrous sulfuric acid, the toluene was distilled off under reduced pressure, and the remaining solid was recrystallized with ethanol to obtain the desired 8-1+)-4-(2-methylbutyloxy).
1.5 g (yield 44%) of benzoin 1-2-cyano-4-chlorophenyl ester was obtained. The melting point of this product was 78.5-80.5°C. Further, the helical pitch of this compound itself was 3.4 μm, which was calculated from the helical pitch value measured by adding 10% of this compound to a nematic liquid crystal composition.
実施例２〜４
実施例１と同様にしてＳ−（＋］ −４−（２−メチル
ブチルオキシ）安息香酸クロリドの代りにそれぞれに対
応する光学活性カルボン１′役クロリドを用いて・次表
に示す＋１）式の化合物を製造した。とれらの結果を第
１表に示す。Examples 2 to 4 In the same manner as in Example 1, the corresponding optically active carbon 1' chloride was used in place of S-(+]-4-(2-methylbutyloxy)benzoic acid chloride, and the following table was prepared. A compound of formula +1) shown below was produced. The results are shown in Table 1.
（ｃ−ｃｈはコレステリンク点、ｃｈ−Ｉは透明点を示
す）
第１表
実施例５（使用例〕
市販のＴＮ用液晶組成物リクソンＧＲ−６３（チッソ（
（（１）製ビフェニル系液晶）９９部に本発明の１つで
ある（＋） −８−４−（２−メチルブチルオキシ）
安息香Ｈ２−シアノ−４−クロロフェニルエステル１部
を加えた液晶組成物を使用したＴＮセルは、この化合物
を添加しないで製造したＴＮセルに比較してリバースド
メインが犬１４］に減少していることが肉眼により、観
察された。っ
以上
３６３−(c-ch indicates cholesteric link point, ch-I indicates clearing point) Table 1 Example 5 (Usage example) Commercially available liquid crystal composition for TN Rixon GR-63 (Chisso (
(Biphenyl liquid crystal manufactured by (1)) 99 parts of (+) -8-4-(2-methylbutyloxy) which is one of the products of the present invention
A TN cell using a liquid crystal composition to which 1 part of benzoin H2-cyano-4-chlorophenyl ester was added had a reverse domain reduced to 14% compared to a TN cell manufactured without adding this compound. was observed with the naked eye. That's all 363-
Claims (1)
炭素原子を示す） で表わされるＳ−田）−４−（２−メチルブチル）基を
有するカルボン酸の２−シアノ−４−クロロフェニルエ
ステル。 （２）一般式 （上式中ｍはＯ又は１、ｎはｌ又は２であり、＊は不斉
炭素原子を示す） で表わされるＳ−（＋） −４−（２−メチルブチル）
基を有するカルボン酸の２−シアノ−４−クロロフエニ
ルエステルヲ少す＜ 、ａ’モーＩＭ含有する液晶組成
物。[Scope of Claims] S-4-(2-methylbutyl) group represented by the general formula fll (in the above formula, m is 0, lsn is 1 or 2, and * represents an asymmetric carbon atom) 2-cyano-4-chlorophenyl ester of carboxylic acid having (2) S-(+)-4-(2-methylbutyl) represented by the general formula (in the above formula, m is O or 1, n is l or 2, and * indicates an asymmetric carbon atom)
A liquid crystal composition containing a 2-cyano-4-chlorophenyl ester of a carboxylic acid having a IM group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20588982A JPH0233697B2 (en) | 1982-11-24 | 1982-11-24 | MAKENOJUDENIHOSEIOMOTSUKOGAKUKATSUSEIBUTSUSHITSU |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20588982A JPH0233697B2 (en) | 1982-11-24 | 1982-11-24 | MAKENOJUDENIHOSEIOMOTSUKOGAKUKATSUSEIBUTSUSHITSU |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5995255A true JPS5995255A (en) | 1984-06-01 |
| JPH0233697B2 JPH0233697B2 (en) | 1990-07-30 |
Family
ID=16514404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20588982A Expired - Lifetime JPH0233697B2 (en) | 1982-11-24 | 1982-11-24 | MAKENOJUDENIHOSEIOMOTSUKOGAKUKATSUSEIBUTSUSHITSU |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0233697B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4689176A (en) * | 1984-12-26 | 1987-08-25 | Chisso Corporation | Novel optically active compound and liquid crystal composition containing same |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0591496U (en) * | 1992-05-07 | 1993-12-14 | えみ子 野波 | Western style toilet seat band |
-
1982
- 1982-11-24 JP JP20588982A patent/JPH0233697B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4689176A (en) * | 1984-12-26 | 1987-08-25 | Chisso Corporation | Novel optically active compound and liquid crystal composition containing same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0233697B2 (en) | 1990-07-30 |
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