JPH085830B2 - New optically active compound - Google Patents
New optically active compoundInfo
- Publication number
- JPH085830B2 JPH085830B2 JP61190054A JP19005486A JPH085830B2 JP H085830 B2 JPH085830 B2 JP H085830B2 JP 61190054 A JP61190054 A JP 61190054A JP 19005486 A JP19005486 A JP 19005486A JP H085830 B2 JPH085830 B2 JP H085830B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- optically active
- active compound
- general formula
- 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.)
- Expired - Fee Related
Links
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は電気光学的表示材料として有用な新規光学活
性化合物に関する。TECHNICAL FIELD The present invention relates to a novel optically active compound useful as an electro-optical display material.
［従来の技術］ 時分割駆動方式の液晶表示セルは近年次第に大型化さ
れ、コンピューター端末、テレビなどのディスプレーと
して需要を拡大しつつある。これに伴い高時分割駆動性
の優れた液晶材料の要求が一段と強まっている。高時分
割化すると一般的に環境温度の変化によってクロストー
ク現象が発生し易くなる。環境温度変化によるクロスト
ーク現象の発生を防止するための方法として、従来よ
り、（１）液晶表示装置に温度補償回路を設ける方法、
（２）分子配向が右ねじれとなるカイラル物質と左ねじ
れとなるカイラル物質の両物質を液晶材料に添加するこ
とにより液晶材料のしきい値電圧の温度依存性を小なら
しめる方法等が知られている。しかし、（１）の方法で
は装置が高価格になり、（２）の方法では、十分な効果
を得るためには多量の添加が必要となるが、添加量が増
えると応答速度が遅くなるので添加量には限界があり、
従って十分な効果は得られない。[Prior Art] A time-division drive type liquid crystal display cell has been gradually increased in size in recent years, and its demand is expanding as a display for computer terminals, televisions and the like. Along with this, the demand for liquid crystal materials having excellent high time-division driveability has further increased. If the time division is increased, generally, the crosstalk phenomenon is likely to occur due to the change in the environmental temperature. As a method for preventing the occurrence of a crosstalk phenomenon due to a change in environmental temperature, (1) a method of providing a temperature compensation circuit in a liquid crystal display device has been conventionally used,
(2) A method is known in which the temperature dependence of the threshold voltage of a liquid crystal material is reduced by adding both a chiral substance having a right-handed twist and a chiral substance having a left-handed twist to the liquid crystal material. ing. However, the method (1) makes the apparatus expensive, and the method (2) requires a large amount of addition to obtain a sufficient effect, but the response speed becomes slower as the amount added increases. There is a limit to the amount of addition,
Therefore, a sufficient effect cannot be obtained.
［本発明が解決しようとする問題点］ 従って、本発明が解決しようとする問題点は、高時分
割駆動において環境温度の変化によるクロストーク現象
を有効に防止することにある。[Problems to be Solved by the Present Invention] Therefore, a problem to be solved by the present invention is to effectively prevent a crosstalk phenomenon due to a change in environmental temperature in high time division driving.
本発明が解決しようとするもう一つの問題点は、各種
の実用的ネマチック液晶組成物に少量添加するだけで該
組成物におけるしきい値電圧の温度依存性を十分に小な
らしめ得る新規化合物を提供することにある。Another problem to be solved by the present invention is to provide a novel compound capable of sufficiently reducing the temperature dependence of the threshold voltage in various practical nematic liquid crystal compositions by adding it in a small amount. To provide.
［問題点を解決するための手段］ 本発明は上記問題点を解決するために、一般式（Ｉ） （式中、Ｒは炭素原子数２〜８の直鎖状アルキル基を表
わし、Ｒ′は炭素原子数１〜20の直鎖状アルキル基を表
わし、C*は不斉炭素原子を表わす。）で表わされる新規
な光学活性化合物を提供する。[Means for Solving the Problems] In order to solve the above problems, the present invention provides a compound represented by the general formula (I): (In the formula, R represents a linear alkyl group having 2 to 8 carbon atoms, R'represents a linear alkyl group having 1 to 20 carbon atoms, and C * represents an asymmetric carbon atom.) A novel optically active compound represented by
本発明に係る一般式（Ｉ）の化合物は例えば、次の製
造方法に従って製造することができる。The compound of general formula (I) according to the present invention can be produced, for example, according to the following production method.
（式中、Ｒ、Ｒ′及びC*は一般式（Ｉ）におけると同じ
意味を表わす。） （Ｓ）−（＋）−１−メチルアルキル−ｐ−トルエン
スルホネートをエタノールの如き溶媒中で、水酸化カリ
ウムの如き塩基存在下、一般式（II）の如きフェノール
誘導体と反応させて、一般式（Ｉ）の化合物を製造す
る。 (In the formulae, R, R ′ and C * have the same meanings as in the general formula (I).) (S)-(+)-1-methylalkyl-p-toluenesulfonate in a solvent such as ethanol, A compound of general formula (I) is prepared by reacting with a phenol derivative of general formula (II) in the presence of a base such as potassium hydroxide.
斯くして製造される一般式（Ｉ）の代表的な化合物の
転移温度及び施光度を第１表に掲げる。Table 1 shows the transition temperature and the degree of optical rotation of the representative compound of the general formula (I) thus produced.
本発明の一般式（Ｉ）の化合物は現在汎用されている
多くのネマチック液晶組成物に少量添加することによっ
て該組成物のしきい値電圧の温度依存性を充分に小さく
することができる。 By adding a small amount of the compound of the general formula (I) of the present invention to many nematic liquid crystal compositions which are widely used at present, the temperature dependence of the threshold voltage of the composition can be sufficiently reduced.
第１図はネマチック液晶材料として現在汎用されてい
る混合液晶（Ａ）と、該混合液晶（Ａ）に式（Ｉ）の化
合物No.1を0.49重量％添加して得られるカイラルネマチ
ック液晶組成物の各々のしきい値電圧の温度依存性を示
したものである。このカイラルネマチック液晶組成物は
100μｍのピッチを有する。FIG. 1 shows a mixed liquid crystal (A) which is currently widely used as a nematic liquid crystal material, and a chiral nematic liquid crystal composition obtained by adding 0.49% by weight of the compound No. 1 of the formula (I) to the mixed liquid crystal (A). 3 shows the temperature dependence of each threshold voltage. This chiral nematic liquid crystal composition
It has a pitch of 100 μm.
尚、混合液晶（Ａ）は、 及び から成るものである。The mixed liquid crystal (A) is as well as It consists of
これらのことから、一般式（Ｉ）の化合物はネマチッ
ク液晶組成物に少量添加することによって該組成物のし
きい値電圧の温度依存性を小さくする効果があることが
理解できる。From these, it can be understood that the compound of the general formula (I) has the effect of reducing the temperature dependence of the threshold voltage of the composition by adding it in a small amount to the nematic liquid crystal composition.
［実施例］ （実施例１） 式 の化合物4.4g（0.020モル）を水酸化カリウム1.5％（0.
022モル）を溶解した90％含水エタノールに溶解した。
加熱還流下で（Ｓ）−（＋）−１−メチル−ヘプチル−
ｐ−トルエンスルホネート5.7g（0.02モル）を滴下し、
５時間加熱還流する。[Example] (Example 1) Formula Compound of 4.4 g (0.020 mol) was added to potassium hydroxide 1.5% (0.
022 mol) was dissolved in 90% hydrous ethanol.
(S)-(+)-1-methyl-heptyl-under heating under reflux.
5.7 g (0.02 mol) of p-toluenesulfonate was added dropwise,
Heat to reflux for 5 hours.
反応終了後、エーテル抽出、水洗、乾燥し、溶媒を減
圧留去した後、残渣をエタノールから再結晶精製して、
下記化合物4.5g（0.014モル）を得た。After completion of the reaction, extraction with ether, washing with water and drying, the solvent was distilled off under reduced pressure, and the residue was purified by recrystallization from ethanol.
4.5 g (0.014 mol) of the following compound was obtained.
収 率 70％ 転移温度 液体 ［α］D 25＝−8.70 ［発明の効果］ 本発明の一般式（Ｉ）の化合物は、現在汎用されてい
るネマチック液晶組成物に少量添加することによって該
組成物のしきい値電圧の温度依存性を小さくすることの
できる化合物である。従って、本発明に係る化合物は高
時分割駆動において環境温度の変化によるクロストーク
現象の発生を有効に防止し得る液晶材料の調製に有効で
ある。 Yield 70% Transition temperature liquid [α] D 25 = −8.70 [Effect of the invention] The compound of the general formula (I) of the present invention is added to a currently widely used nematic liquid crystal composition in a small amount. It is a compound that can reduce the temperature dependence of the threshold voltage of. Therefore, the compound according to the present invention is effective for preparing a liquid crystal material capable of effectively preventing the occurrence of the crosstalk phenomenon due to the change of the ambient temperature in the high time-division driving.
第１図は、ネマチック液晶材料として現在汎用されてい
る混合液晶（Ａ）に本発明の光学活性化合物No.1を0.49
％添加して得られるカイラルネマチック液晶組成物のし
きい値電圧の温度依存性を示した図表である。FIG. 1 shows that 0.49 of the optically active compound No. 1 of the present invention was added to the mixed liquid crystal (A) which is currently widely used as a nematic liquid crystal material.
3 is a chart showing the temperature dependence of the threshold voltage of the chiral nematic liquid crystal composition obtained by adding the above composition.
Claims (1)
わし、Ｒ′は炭素原子数１〜20の直鎖状アルキル基を表
わし、C*は不斉炭素原子を表わす。） で表わされる化合物。1. A general formula (I) (In the formula, R represents a linear alkyl group having 2 to 8 carbon atoms, R'represents a linear alkyl group having 1 to 20 carbon atoms, and C * represents an asymmetric carbon atom.) A compound represented by.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61190054A JPH085830B2 (en) | 1986-08-13 | 1986-08-13 | New optically active compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61190054A JPH085830B2 (en) | 1986-08-13 | 1986-08-13 | New optically active compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6348239A JPS6348239A (en) | 1988-02-29 |
| JPH085830B2 true JPH085830B2 (en) | 1996-01-24 |
Family
ID=16251575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61190054A Expired - Fee Related JPH085830B2 (en) | 1986-08-13 | 1986-08-13 | New optically active compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH085830B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0666048B2 (en) * | 1989-10-06 | 1994-08-24 | 富士ゼロックス株式会社 | Operation procedure batch registration device |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0717905B2 (en) * | 1985-05-09 | 1995-03-01 | 旭硝子株式会社 | Liquid crystal composition |
-
1986
- 1986-08-13 JP JP61190054A patent/JPH085830B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6348239A (en) | 1988-02-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |