JPS6348239A - Novel optically active compound - Google Patents
Novel optically active compoundInfo
- Publication number
- JPS6348239A JPS6348239A JP19005486A JP19005486A JPS6348239A JP S6348239 A JPS6348239 A JP S6348239A JP 19005486 A JP19005486 A JP 19005486A JP 19005486 A JP19005486 A JP 19005486A JP S6348239 A JPS6348239 A JP S6348239A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- liquid crystal
- formula
- expressed
- straight
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 21
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 11
- 239000000203 mixture Substances 0.000 abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 8
- 239000000463 material Substances 0.000 abstract description 8
- 239000004988 Nematic liquid crystal Substances 0.000 abstract description 7
- 230000007613 environmental effect Effects 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000012769 display material Substances 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to novel optically active compounds useful as electro-optic display materials.
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
コンビエータ一端末、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Ｆｔ、
（１１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２ル物質と左ねじれと
なるカイ２ル物質の両物質を液晶材料に添加することに
よシ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シ、（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々るので添加量には限界があ）、
従って十分な効果は得られない。Time-division drive type liquid crystal display cells have gradually become larger in recent years, and the demand for them as displays for combiator 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. Conventionally, Ft,
(11 Method of providing temperature compensation circuit in liquid crystal display device, (2
) A method of reducing the temperature dependence of the threshold voltage of a liquid crystal material by adding to the liquid crystal material both a chi2le substance whose molecular orientation is right-handed and a chi2le substance whose molecular orientation is left-handed. , etc. are known. 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 may become slow. There is a limit to the amount added)
Therefore, sufficient effects cannot be obtained.
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。Therefore, the problem to be solved by the present invention is to effectively prevent crosstalk caused by changes 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充分に小なら
しめ得る新規化合物を提供することＫある。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. I have a lot to offer.
本発明は、上記問題点を解決するために、で表わされる
新規な光学活性化合物を提供する。In order to solve the above problems, the present invention provides a novel optically active compound represented by:
本発明に係る式（Ｉｌの化合物は次の製造方法に従って
製造することができる。The compound of formula (Il) according to the present invention can be produced according to the following production method.
（式中 Ｒ、Ｒ’、 ｎおよびＣは前記の通シである。(In the formula, R, R', n and C are as defined above.
）（Ｓ）−（ト）−１−メｆルアルキルー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、式叩の如きフェノール誘導体と
反応させて、式中の化合物を製造する。) (S)-(t)-1-Mef-alkyl-P-toluenesulfonate is reacted with a phenol derivative such as the formula in a solvent such as ethanol in the presence of a base such as potassium hydroxide to form a compound of the formula Manufacture.
斯くして製造される式（Ｉ）の代表的な化合物の転移温
度および旋光度を第１表に掲げる。Table 1 lists the transition temperatures and optical rotations of representative compounds of formula (I) thus produced.
第 １ 表
式中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 in Table 1 to many currently used nematic liquid crystal compositions, 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使用されている
混合液晶囚と、該混合液晶（８）に式（Ｉｔの化合物７
ｇ６１を０４９重量％添加して得られるカイラルネマチ
ック液晶組成物の夫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。Figure 1 shows a mixed liquid crystal compound currently used as a nematic liquid crystal material and a compound 7 of the formula (It) in the mixed liquid crystal (8).
2 shows the temperature dependence of the threshold voltage of each chiral nematic liquid crystal composition obtained by adding 0.49% by weight of g61. This chiral nematic liquid crystal composition has a pitch of 100 μm.
尚、混合液晶（イ）は、 １３重量％の ９重量％の １３重量％の １０重量％の ２重量％の ゝＦ ７重量％の ５重量％の ５重量％の ４重量％の ９重量％の ４重量％の ４重量％の ８重量％の 及び ７重量％の から成るものである。In addition, the mixed liquid crystal (a) is 13% by weight 9% by weight 13% by weight 10% by weight 2% by weight ゝF 7% by weight 5% by weight 5% by weight 4% by weight 9% by weight 4% by weight 4% by weight 8% by weight as well as 7% by weight It consists of
これらのことから、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 facts, it can be understood that adding a small amount of the compound of formula (I) to a nematic liquid crystal composition has the effect of reducing the temperature dependence of the threshold voltage of the composition.
実施例１
（１０２０モル）を水酸化カ□リウムｔ５ｓ’（［，０
２２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）−（ト）−１−メｆルーへブチル−
Ｐ−）ルエンスルホネート５．７ｆ（（１０２モル）を
滴下し、５時間加熱還流する。Example 1 (1020 mol) was added to potassium hydroxide t5s' ([,0
(22 mol) was dissolved in 90% aqueous ethanol under heating under reflux.
5.7f (102 mol) of P-)luenesulfonate was added dropwise and heated under 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
質 Ａ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４．５ｆ（α０１４モル）を得た。After the reaction was completed, the reaction mixture was extracted with ether, washed with water, dried, and the solvent was removed under reduced pressure. The residue was purified by recrystallization from ethanol to obtain the following compound 4.5f (α014 mol).
収率７０％
転移温度 液体
〔α）、−−ａ７０
〔発明の効果〕
本発明に係る光学活性化合物は、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整に有効である
。Yield 70% Transition temperature Liquid [α), --a70 [Effects of the invention] The optically active compound according to the present invention can be added to a currently widely used nematic liquid crystal composition in a small amount to improve the threshold value of the composition. This is a compound that can reduce the temperature dependence of voltage. Therefore, the compound according to the present invention is effective in adjusting a liquid crystal material that can effectively prevent the occurrence of crosstalk caused by changes in environmental temperature in 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
混合液晶囚に本発明の光学活性化合物７ｇ６１をＱ、４
９重量％添加して得られるカイラルネマチック液晶組成
物のしきい値電圧の温度依存性を示した図表である。Figure 1 shows the addition of the optically active compound 7g61 of the present invention to Q, 4 mixed liquid crystals, which are currently widely used as nematic liquid crystal materials.
It is a chart showing the temperature dependence of the threshold voltage of a chiral nematic liquid crystal composition obtained by adding 9% by weight.
Claims (1)
しわし、Ｒ′は炭素原子数１〜２０の直鎖状アルキル基
あるいは、直鎖状アルコキシ基を表わし、ｎは０又は１
を表わし、■は不斉炭素原子を表わす。） で、表わされる化合物。[Claims] ▲ Numerical formulas, chemical formulas, tables, etc. represents a linear alkyl group or a linear alkoxy group, n is 0 or 1
, and ■ 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 true JPS6348239A (en) | 1988-02-29 |
| JPH085830B2 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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5990873A (en) * | 1989-10-03 | 1999-11-23 | Fuji Xerox Co., Ltd. | Single-key input system |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61255988A (en) * | 1985-05-09 | 1986-11-13 | Asahi Glass Co Ltd | Liquid crystal composition |
-
1986
- 1986-08-13 JP JP61190054A patent/JPH085830B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61255988A (en) * | 1985-05-09 | 1986-11-13 | Asahi Glass Co Ltd | Liquid crystal composition |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5990873A (en) * | 1989-10-03 | 1999-11-23 | Fuji Xerox Co., Ltd. | Single-key input system |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH085830B2 (en) | 1996-01-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |