JPH0517211B2 - - Google Patents
Info
- Publication number
- JPH0517211B2 JPH0517211B2 JP19005386A JP19005386A JPH0517211B2 JP H0517211 B2 JPH0517211 B2 JP H0517211B2 JP 19005386 A JP19005386 A JP 19005386A JP 19005386 A JP19005386 A JP 19005386A JP H0517211 B2 JPH0517211 B2 JP H0517211B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- present
- alkyl group
- carbon atoms
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000007613 environmental effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- -1 methyl alkyl ether Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
〔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
トラン系光学活性化合物に関する。
〔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
型化されコンピユーター端末、テレビなどのデイ
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
と強まつている。高時分割化すると一般的に環境
温度の変化によつ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、などが知られている。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、従つて十分な効
果は得られない。
〔本発明が解決しようとする問題点〕
従つて、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。
本発明が解決しようなするもう一つの問題点
は、各種の実用的ネマチツ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
度依存性を充分に小ならしめ得る新規化合物を提
供することにある。
〔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
（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。
本発明に係る式（）の化合物は次の製造方法
に従つて製造することができる。
（式中Ｒ，R′および＊
Ｃ
は、
前記の通りである。）４−ヨードフエニル−1′−
メチルアルキルエーテルをジエチルアミンの如き
溶媒中で、ビス（トリフエニルフオスフイン）パ
ラジウム（）クロライドの如き触媒を用いて、
４−（トランス−4′−アルキルシクロヘキシル）
フエニルアセチレンと反応させて式（）の化合
物を製造する。
斯くして製造される式（）の代表的な化合物
の転移温度および施光度を第１表に掲げる。
[Industrial Application Field] The present invention relates to a novel tolan-based optically active compound useful as an electro-optical display material. [Prior Art] Time-division drive type liquid crystal display cells have gradually become larger in recent years, and the demand for them as displays for computer terminals, televisions, etc. is increasing. Along with this, the demand for liquid crystal materials with excellent high time-division drivability has become even stronger. In general, when high time division is used, crosstalk phenomena are more likely to occur due to changes in environmental temperature. As a method to prevent the occurrence of crosstalk phenomena due to environmental temperature changes, (1)
A method of providing a temperature compensation circuit in a liquid crystal display device. (2) The temperature of the threshold voltage of the liquid crystal material can be adjusted by adding both a chiral substance whose molecular orientation is right-handed and a chiral substance whose molecular orientation is left-handed, to the liquid crystal material. There are known methods to reduce dependence. However, in method (1), the equipment is expensive, and in method (2), a large amount of addition is required to obtain a sufficient effect, but as the amount of addition increases, the response speed becomes slower. There is a limit to the amount of addition, so sufficient effects cannot be obtained. [Problems to be solved by the present invention] Therefore, the problems to be solved by the present invention are as follows.
The object of the present invention is to effectively prevent crosstalk phenomena caused by changes in environmental temperature in high time division driving. Another problem to be solved by the present invention is to develop a new compound that can sufficiently reduce the temperature dependence of the threshold voltage in various practical nematic liquid crystal compositions by adding a small amount thereof. It is about providing. [Means for Solving the Problems] In order to solve the above-mentioned problems, the present invention provides the following: (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.) Provided is a novel optically active compound represented by: The compound of formula () according to the present invention can be produced according to the following production method. (In the formula, R, R' and *C are as described above.) 4-Iodophenyl-1'-
The methyl alkyl ether is prepared in a solvent such as diethylamine using a catalyst such as bis(triphenylphosphine)palladium() chloride.
4-(trans-4'-alkylcyclohexyl)
A compound of formula () is produced by reacting with phenylacetylene. Table 1 lists the transition temperatures and degrees of light exposure of representative compounds of formula () thus produced.
【表】
→
117(Ch I)
←
【table】
→
117(Ch I)
←
Claims (1)
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。）で表わされる化合物。[Claims] 1. General formula (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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19005386A JPS6348240A (en) | 1986-08-13 | 1986-08-13 | Novel tolan based optically active compound |
| US07/061,242 US4814516A (en) | 1986-06-17 | 1987-06-15 | Novel optically active tolan derivatives |
| EP87108627A EP0249933B1 (en) | 1986-06-17 | 1987-06-16 | Novel optically active tolan derivatives and process for preparing same |
| DE8787108627T DE3762846D1 (en) | 1986-06-17 | 1987-06-16 | OPTICALLY ACTIVE TOLANDERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF. |
| US07/269,817 US4961874A (en) | 1986-06-17 | 1988-11-10 | Optically active tolan derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19005386A JPS6348240A (en) | 1986-08-13 | 1986-08-13 | Novel tolan based optically active compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6348240A JPS6348240A (en) | 1988-02-29 |
| JPH0517211B2 true JPH0517211B2 (en) | 1993-03-08 |
Family
ID=16251557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19005386A Granted JPS6348240A (en) | 1986-06-17 | 1986-08-13 | Novel tolan based optically active compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6348240A (en) |
-
1986
- 1986-08-13 JP JP19005386A patent/JPS6348240A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6348240A (en) | 1988-02-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |