JPS5962547A - Optical active compound - Google Patents
Optical active compoundInfo
- Publication number
- JPS5962547A JPS5962547A JP17438682A JP17438682A JPS5962547A JP S5962547 A JPS5962547 A JP S5962547A JP 17438682 A JP17438682 A JP 17438682A JP 17438682 A JP17438682 A JP 17438682A JP S5962547 A JPS5962547 A JP S5962547A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- compound
- methylvaleric acid
- optical active
- 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
Abstract
Description
【発明の詳細な説明】
本発明は光学活性液晶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 an optically active liquid crystal compound 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、各種の方式のものがあるが
、その代表的なものにＴｅｌ型（ねじれネマチック型）
の表示セルがある。Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy that are the characteristics of liquid crystal materials, and there are various types, but the representative one is the Tel type (twisted nematic type).
There are display cells.
この方式のものに用いられる液晶物質としては正の誘電
異方性を有する液晶組成物が用いらぺこれらは他の場合
と同様、光、熱、水分、空気等に対し安定で、かつ室温
を含む出来るだけ広い温度範囲で液晶相を示すことが必
要である。The liquid crystal material used in this method is a liquid crystal composition with positive dielectric anisotropy.As in other cases, these materials are stable against light, heat, moisture, air, etc., and are stable at room temperature. It is necessary to exhibit a liquid crystal phase over as wide a temperature range as possible.
ＴＮ型表示素子ではその他その品質が次の点で問題にな
る場合が多い。即ち表示面にいわゆるリバースドメイン
（しま模様）が発生する場合があり、この様な現象を防
ぐためには光学活性物質を添加すればよいことが知られ
ている。In addition, the quality of TN type display elements often poses problems in the following points. That is, a so-called reverse domain (striped pattern) may occur on the display surface, and it is known that in order to prevent such a phenomenon, it is sufficient to add an optically active substance.
本発明の化合物はこの様な目的に使用して有効な光学活
性を有する新規な化合物である。The compound of the present invention is a novel compound that has effective optical activity and can be used for such purposes.
即ち、本発明は一般式
（上式中−（七トはイ］−又は−０−を示し、ｎは１又
は２であり、Ｒは炭素数１〜１ｏのアルキル基を示す。That is, the present invention is directed to the general formula (in the above formula, -(7 is i)- or -0-, n is 1 or 2, and R is an alkyl group having 1 to 1 o carbon atoms).
又＊は不整炭素原子を示す）て表わされる（＋） （Ｓ
） −３−メチル吉草酸のエステル誘導体及びこれを少
なくとも一種含有する液晶組成物である。(* indicates an asymmetric carbon atom) (+) (S
) -An ester derivative of 3-methylvaleric acid and a liquid crystal composition containing at least one thereof.
本発明の化合物はあるものは非液晶化合物であり、又あ
るものはコレステリック相又はスメ＊
クチツク相（Ｓｍ）を示すが、いずれもそのコレステリ
ックのら旋ピッチは２０〜３０ ｐｍ程度で、ＴＮ型表
示素子用の液晶組成物に本化合物を０．５〜５チ位添加
することによりリバースドメインの発生を防ぐことが可
能となる。又近年＊
注目されているＳｍＯを応用した表示素子にも応用でき
る可能性がある。Some of the compounds of the present invention are non-liquid crystal compounds, and some exhibit a cholesteric phase or a sme*ctic phase (Sm), but in all cases, the cholesteric helical pitch is about 20 to 30 pm, and they are TN type. By adding this compound to a liquid crystal composition for display devices at 0.5 to 5 degrees, it is possible to prevent the occurrence of reverse domains. It may also be applicable to display elements using SmO, which has been attracting attention in recent years.
つぎに本発明の化合物の製造方法を示すと。Next, a method for producing the compound of the present invention will be described.
（ト）（Ｓ）−３−メチル吉草酸クロリドと対応するフ
ェノール又はアルコール誘導体と反応して目的の化合物
を製造した。これを化学式で示すと（上式中８．ｎ、Ｒ
は前記に同じ）
以下実施例により本化合物について東に詳細に説明する
。(g)(S)-3-Methylvaleric acid chloride was reacted with the corresponding phenol or alcohol derivative to produce the desired compound. This is shown as a chemical formula (in the above formula, 8.n, R
(same as above) The present compound will be explained in detail below with reference to Examples.
実施例１ （（＋）（Ｓ） −３−メチル吉草酸−４−
（トランス−４−ヘゲチルシクロヘキシル）フェニルエ
ステルの製造〕
４−（）ランス−４−ヘゲチルシクロヘキシル）フェノ
ール２．８２をピリジン２Ｑｍｌに溶かしたものに（＋
） （Ｓ） −３−メチル吉草酸クロリド１．４ｆを加
えよく振りまぜ、−晩放置後１００ｆｎｔの水にあける
。析出する結晶をトルエン３００−で抽出し、６Ｎ塩酸
、ついで２ＮＮ水辺化ナトリウムで洗った後、水で中性
になるまで洗浄する。無水硫酸ナトリウムで乾燥後トル
エンを威圧にて留去し、残る結晶をエタノールで４ＩＩ
結晶して目的物である（＋バ５）−３−メチル吉草＋Ｗ
−４−（）ランス−４−へグチルシクロヘキシル）フェ
ニルエステルを得ル。収量＊
１．２ｆ、収率３２％。そのＣ−ｓｍ点は３０’Ｃ以＊
ＦｌＳｍ−１点は４３．７℃であった。Example 1 ((+)(S)-3-methylvaleric acid-4-
Production of (trans-4-hegetylcyclohexyl)phenyl ester] In a solution of 2.82 4-()trans-4-hegetylcyclohexyl)phenol in 2Qml of pyridine, (+
) (S) Add 1.4f of -3-methylvaleric acid chloride, shake well, and leave to stand overnight, then pour into 100fnt of water. The precipitated crystals are extracted with 300 g of toluene, washed with 6N hydrochloric acid, then with 2N sodium hydrate, and then with water until neutral. After drying over anhydrous sodium sulfate, the toluene was distilled off under pressure, and the remaining crystals were diluted with ethanol.
(+B5)-3-methylvalerin + W which is the target product after crystallization
-4-() lance-4-hegtylcyclohexyl)phenyl ester was obtained. Yield* 1.2f, yield 32%. Its C-sm point was 30'C or higher* and its FlSm-1 point was 43.7°C.
実施例２〜５
実施例１と同様にして実施例１における４−（トランス
−４−へグチルシクロヘキシル）フェノールの代りにそ
れぞれに対応するフェノール又はアルコールを用いて第
１表に示す（＋） （８） −３−メチル吉草酸のエス
テル誘導体を製造した。Examples 2 to 5 In the same manner as in Example 1, the corresponding phenols or alcohols were used in place of 4-(trans-4-hegtylcyclohexyl)phenol in Example 1, and the (+) ( 8) An ester derivative of -3-methylvaleric acid was produced.
それらの相転移点を第１表に示す。Their phase transition points are shown in Table 1.
第１表
実施例６（使用例）
市販のＴＮ用液晶組成物リクノンＧＲ−５３（チッソ■
製ビフェニル系液晶）９９部に本発明の実施例１の化合
物の１っである（」→（Ｓ） −３−メチル吉操、酸−
４−（トランス−４−ヘゲチルシクロヘキシル）フェニ
／Ｌ−丁スＪル１ 部ｔ ／ＪＩＩえた液晶組成物を使
用したＴＮセルｅゴ、この化合物を晧；ノロしないで製
造したＴＮセルに比較してリバースドメインが大巾に減
少していることが肉眼により観察された。Table 1 Example 6 (Usage example) Commercially available liquid crystal composition for TN Likunon GR-53 (Chisso ■
One of the compounds of Example 1 of the present invention (''→(S) -3-methylkisao, acid-
4-(trans-4-hegetylcyclohexyl)phenylene/L-dichloromethane 1 part t/JII prepared TN cell using a liquid crystal composition, this compound was added to a TN cell manufactured without slag. In comparison, it was observed with the naked eye that the reverse domain was significantly reduced.
Claims (1)
を示す。又＊は不整炭素原子を示す） で表わされる（→−バ５）−３−メチル吉草酸のエステ
ル誘導体。 （上式申分は−０−又は−０−を示し、ｎｔま１又は２
であり、Ｒは炭素数１〜１ｏのアルキル尤を示す。又＊
は不整炭素原子を示す） で表わされる（＋）（Ｓ） −３−メチル吉草酸のエス
テル誘導体を少なくとも一種含有する液晶組成物。[Claims] (]) General formula n is l or 2, and R is alkyl 4 having 1 to 10 carbon atoms.
shows. (* indicates an asymmetric carbon atom) An ester derivative of (→-5)-3-methylvaleric acid represented by: (The above formula indicates -0- or -0-, and nt is 1 or 2.
and R represents an alkyl group having 1 to 1 carbon atoms. or*
represents an asymmetric carbon atom) A liquid crystal composition containing at least one ester derivative of (+)(S)-3-methylvaleric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17438682A JPS5962547A (en) | 1982-10-04 | 1982-10-04 | Optical active compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17438682A JPS5962547A (en) | 1982-10-04 | 1982-10-04 | Optical active compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5962547A true JPS5962547A (en) | 1984-04-10 |
| JPH0525869B2 JPH0525869B2 (en) | 1993-04-14 |
Family
ID=15977700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17438682A Granted JPS5962547A (en) | 1982-10-04 | 1982-10-04 | Optical active compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5962547A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4620938A (en) * | 1982-03-30 | 1986-11-04 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Hydroterphenyls |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5323957A (en) * | 1976-08-14 | 1978-03-06 | Merck Patent Gmbh | Cyclohexane derivatives |
| JPS5738877A (en) * | 1980-06-26 | 1982-03-03 | Merck Patent Gmbh | Liquid crystal dielectric |
| JPS58154532A (en) * | 1982-02-20 | 1983-09-14 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Bicyclohexyl derivative |
| JPS58189124A (en) * | 1982-03-30 | 1983-11-04 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Hydroterphenyl compound |
-
1982
- 1982-10-04 JP JP17438682A patent/JPS5962547A/en active Granted
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5323957A (en) * | 1976-08-14 | 1978-03-06 | Merck Patent Gmbh | Cyclohexane derivatives |
| JPS5495985A (en) * | 1976-08-14 | 1979-07-28 | Merck Patent Gmbh | Liquid crystal dielectric substance |
| JPS5738877A (en) * | 1980-06-26 | 1982-03-03 | Merck Patent Gmbh | Liquid crystal dielectric |
| JPS58154532A (en) * | 1982-02-20 | 1983-09-14 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Bicyclohexyl derivative |
| JPS58189124A (en) * | 1982-03-30 | 1983-11-04 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Hydroterphenyl compound |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4620938A (en) * | 1982-03-30 | 1986-11-04 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Hydroterphenyls |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0525869B2 (en) | 1993-04-14 |
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