JPS6147455A - 4-cyano-4'-(hydroxyalkoxy)biphenyl - Google Patents
4-cyano-4'-(hydroxyalkoxy)biphenylInfo
- Publication number
- JPS6147455A JPS6147455A JP16894184A JP16894184A JPS6147455A JP S6147455 A JPS6147455 A JP S6147455A JP 16894184 A JP16894184 A JP 16894184A JP 16894184 A JP16894184 A JP 16894184A JP S6147455 A JPS6147455 A JP S6147455A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- cyano
- formula
- biphenyl
- 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.)
- Pending
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】
本発明は液晶組成物に添加して有用な新規毒化合物に関
する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel toxic compounds useful in addition to liquid crystal compositions.
液晶表示素子は液晶物質が有する光学異方性及び誘電異
方性を利用したものであるが、その表示方式にはＴＮ型
（ねじれネマチック型）、ＤＳ型（動的散乱型）、ゲス
ト・ホスト型、ＤＡＰ型、ホワイト・ティラー型など各
種の方式があり、それぞれの方式によシ使用される液晶
物質に要求される性質も異る。例えば表示素子の種類に
よって、液晶物質として誘電異方性Δεが正のものを必
要としたり、負のものを必要としたり、或はその中間的
な値のものが適したわする。使用される液晶物質はでき
るだけ広い温度範囲で液晶相を示し、又水分、熱、空機
、光などに対して安定である必要がある。現在のと″こ
ろ単−化谷物でこの様な条件をすべて満たすものはなく
、数種の液晶化合物や非液晶化合物を混合して使用され
ている。Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal materials, and their display methods include TN type (twisted nematic type), DS type (dynamic scattering type), and guest/host type. There are various types of liquid crystals, such as type, DAP type, white-tiller type, etc., and the properties required of the liquid crystal material used for each type are different. For example, depending on the type of display element, a liquid crystal material with a positive or negative dielectric anisotropy Δε may be required, or a liquid crystal material with an intermediate value may be suitable. The liquid crystal material used must exhibit a liquid crystal phase over as wide a temperature range as possible, and must be stable against moisture, heat, air, light, etc. At present, there is no monolithic compound that satisfies all of these conditions, and a mixture of several types of liquid crystal compounds and non-liquid crystal compounds is used.
によって得られる。従ってΔε値の大きい液晶組成物を
得るにはΔε値の出来るだけ大きい成分を使用する。そ
の場合に他の成分との相溶性が良いことを要求され、新
たに得る液晶組成物の粘度をさほど上昇させないことを
要求される。obtained by. Therefore, in order to obtain a liquid crystal composition with a large Δε value, components with as large a Δε value as possible are used. In this case, it is required to have good compatibility with other components, and it is required not to increase the viscosity of the newly obtained liquid crystal composition so much.
本発明の化合物は液晶組成物の成分に用いて有用なもの
である。The compounds of the present invention are useful as components of liquid crystal compositions.
本発明は一般式
（式中で、Ｒは炭素数１ないし１０のヒドロキシアルキ
ル基で、ヒドロキシ基はアルキル基の末端または中間に
ある。）で表わされる４−シアノ−４’−（ヒト買キシ
アルコキシ）ビフェニル（および該化合物を含有する液
晶組成物である。The present invention relates to 4-cyano-4'-(human hydroxyl) represented by the general formula (in the formula, R is a hydroxyalkyl group having 1 to 10 carbon atoms, and the hydroxy group is located at the end or in the middle of the alkyl group). alkoxy)biphenyl (and a liquid crystal composition containing the compound).
本発明の化合物は正の誘電異方性を示しネマチック−透
明点（以下、Ｎ−Ｉ点と略記する。）が例えば７９℃以
上のものが得られ液晶組成物のＮ−Ｉ点を上昇させるこ
とができ、液晶組成□物を用いた液晶セルの駆動電圧を
下げることができるものである。The compound of the present invention exhibits positive dielectric anisotropy and has a nematic clearing point (hereinafter abbreviated as N-I point) of, for example, 79°C or higher, thereby increasing the N-I point of the liquid crystal composition. Therefore, the driving voltage of a liquid crystal cell using a liquid crystal composition □ can be lowered.
つぎに本発明の化合物の製造法について述べる。Next, a method for producing the compound of the present invention will be described.
臭素化アルコール（■）（アルコールを形成するアルキ
ル基は前述ヒドロキシアルキル基のアルキル基と共通の
ものである。）および４−シアノ−４′−ヒドロキシビ
フェニル（２）をエタノール中で水酸化カリウム、水酸
化ナトリウムの存在下で反応させて本発明の４−シアノ
−４′−（ヒドロキシアルコキシ）ビフェニル（１）を
製造することができる。かかる反応をつぎに化学式で示
す。Brominated alcohol (■) (the alkyl group forming the alcohol is the same as the alkyl group of the hydroxyalkyl group mentioned above) and 4-cyano-4'-hydroxybiphenyl (2) were dissolved in ethanol with potassium hydroxide, The 4-cyano-4'-(hydroxyalkoxy)biphenyl (1) of the present invention can be produced by reacting in the presence of sodium hydroxide. This reaction is shown below using a chemical formula.
（ＩＩ） （ＩＩＩ） （
１）（式中で、Ｒは前述に同じものを示す）つぎに、本
発明を実施例により説明する。(II) (III) (
1) (In the formula, R is the same as described above.) Next, the present invention will be explained by examples.
実坤例１
４−シアノ−４’−（３−ヒドロキシプロポキシ）ビフ
ェニル
３−プロモー１＝；プ、ロバノール（ｎ）、５．６ｇ（
０，０４モル）および４−シアノ−４′−ヒドロキシビ
フェニル（２）６．０ ｇ（０，０，２モｊ！／）をエ
タノール３０ ｏｔｒｔｌに溶かし、室温下撹拌し、別
に水酸化カリウム１０ｇを水２０１ｒＬｌに溶解したも
のを用意し３０分間にわたり徐々に滴下、その後４０時
間撹拌した。ついで減圧してエタール約２００ｍａｌ留
去し、水５ｏｏ１ｎｌＱ加え固形物を析出させた。該混
合系にトルエン３００ｄを加え不溶分を濾別して除去し
、トルエン溶液を２ Ｎ −ＮａＯＨで２回、ついで水
で３回洗い、ついで無水硫酸す） ＋Ｊウムで乾燥させ
、ついでトルエンを留去した。得られた結晶をメタノー
ルを用いて再結晶し４−シアノ−４’−（３−ヒドロキ
シアルキシ）ビフェニルを得た。このものの収量は２Ｉ
（収率２８％）、結晶−ネマチック点は１０９．０〜１
１０．７℃、Ｎ−Ｉ点は１１３．６℃であった。Practical Example 1 4-Cyano-4'-(3-hydroxypropoxy)biphenyl 3-promo 1=;pro, lobanol (n), 5.6 g (
0,04 mole) and 6.0 g (0,0,2 moj!/) of 4-cyano-4'-hydroxybiphenyl (2) were dissolved in 30 otrtl of ethanol, stirred at room temperature, and separately dissolved with 10 g of potassium hydroxide. was dissolved in 201 rL of water and gradually added dropwise over 30 minutes, followed by stirring for 40 hours. Then, about 200 mal of etal was distilled off under reduced pressure, and 5001 nlQ of water was added to precipitate a solid. 300 d of toluene was added to the mixed system to remove insoluble matter by filtration, and the toluene solution was washed twice with 2 N NaOH and then three times with water, then dried with anhydrous sulfuric acid, and then the toluene was distilled off. did. The obtained crystals were recrystallized using methanol to obtain 4-cyano-4'-(3-hydroxyalxy)biphenyl. The yield of this product is 2I
(yield 28%), crystal-nematic point 109.0-1
The temperature was 10.7°C, and the N-I point was 113.6°C.
実施例２および３ 実施例１に準じた方法でつぎの化合物を得た。Examples 2 and 3 The following compound was obtained in the same manner as in Example 1.
４−シアノ−４’−（２−ヒドロキシエトキシ）ビフェ
ニル
融点１２４．０〜１２６．９℃、Ｎ−Ｉ点１２２．５℃
４−シアノ−４’ −（２−ヒドロキシプロポキシ）ビ
フェニル
融点１１１．９〜１１３．８℃、Ｎ−Ｉ点 ７９．４℃
実施例４（液晶組成物に用いた場合）
１０μｍの間隔で内部に対向透明電極を有するＴＮセル
に該組成物を入れたもののしきい電圧は１、５４ Ｖ
、飽和電圧は２．１２ Ｖである。4-cyano-4'-(2-hydroxyethoxy)biphenyl melting point 124.0-126.9°C, N-I point 122.5°C
4-cyano-4'-(2-hydroxypropoxy)biphenyl melting point 111.9-113.8°C, N-I point 79.4°C
Example 4 (When used in a liquid crystal composition) The composition was placed in a TN cell having opposing transparent electrodes at an interval of 10 μm, and the threshold voltage was 1.54 V.
, the saturation voltage is 2.12 V.
該液晶組成物９重量部および本発明の実施例１による４
−シアノ−４’＝（３−ヒドロキシブ２０℃における粘
度は３６ ｃｐで、前述のＴＮセルに入れたもののしき
い電圧は１．３４Ｖ、飽和電圧は１．８５ Ｖであった
。9 parts by weight of the liquid crystal composition and 4 parts by weight according to Example 1 of the present invention.
-Cyano-4'=(3-hydroxyb) The viscosity at 20°C was 36 cp, the threshold voltage of the TN cell described above was 1.34V, and the saturation voltage was 1.85V.
以上that's all
Claims (2)
ル基で、ヒドロキシ基はアルキル基の末端または中間に
ある。）で表わされる４−シアノ−４′−（ヒドロキシ
アルコキシ）ビフェニル。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R is a hydroxyalkyl group having 1 to 10 carbon atoms, and the hydroxy group is at the end or in the middle of the alkyl group.) 4 -cyano-4'-(hydroxyalkoxy)biphenyl.
ル基で、ヒドロキシ基はアルキル基の末端または中間に
ある。）で表わされる４−シアノ−４′−（ヒドロキシ
アルコキシ）ビフェニルを含有することを特徴とする液
晶組成物。(2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R is a hydroxyalkyl group having 1 to 10 carbon atoms, and the hydroxy group is at the end or in the middle of the alkyl group.) 4 - A liquid crystal composition containing cyano-4'-(hydroxyalkoxy)biphenyl.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16894184A JPS6147455A (en) | 1984-08-13 | 1984-08-13 | 4-cyano-4'-(hydroxyalkoxy)biphenyl |
| US06/764,781 US4654162A (en) | 1984-08-13 | 1985-08-12 | Alcohol derivatives |
| DE8585110153T DE3563437D1 (en) | 1984-08-13 | 1985-08-13 | Alcohol derivatives and liquid crystal composition containing them |
| EP85110153A EP0171794B1 (en) | 1984-08-13 | 1985-08-13 | Alcohol derivatives and liquid crystal composition containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16894184A JPS6147455A (en) | 1984-08-13 | 1984-08-13 | 4-cyano-4'-(hydroxyalkoxy)biphenyl |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6147455A true JPS6147455A (en) | 1986-03-07 |
Family
ID=15877377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16894184A Pending JPS6147455A (en) | 1984-08-13 | 1984-08-13 | 4-cyano-4'-(hydroxyalkoxy)biphenyl |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6147455A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008144638A (en) * | 2006-12-08 | 2008-06-26 | Across Corp | Piston |
-
1984
- 1984-08-13 JP JP16894184A patent/JPS6147455A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008144638A (en) * | 2006-12-08 | 2008-06-26 | Across Corp | Piston |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0194879A1 (en) | Cyclohexane derivative | |
| GB2065158A (en) | Anthraquinone Dichroic Dyes | |
| JPS632246B2 (en) | ||
| JPS6168467A (en) | Ester derivative having positive dielectric anisotropy | |
| JPS6147455A (en) | 4-cyano-4'-(hydroxyalkoxy)biphenyl | |
| EP0171794B1 (en) | Alcohol derivatives and liquid crystal composition containing them | |
| JPS5935900B2 (en) | 1-Cyclohexyl-2-(4'-halolobiphenyl)ethane derivative | |
| JPS60222458A (en) | P-substituted phenylisothiocyanate | |
| JPS5935901B2 (en) | 1-Cyclohexyl-2-(4'-halolophenyl)ethane derivative | |
| JP2829436B2 (en) | Cyclobutane derivative | |
| JPH0518814B2 (en) | ||
| JPH0460976B2 (en) | ||
| JPH0479329B2 (en) | ||
| JP2822079B2 (en) | Cyclopropane derivative | |
| JPS60130542A (en) | Ether bond-containing substituted cyclohexane derivative | |
| JPS6334852B2 (en) | ||
| JPS6023476A (en) | 4-(substituted carbonyloxy)biphenylyl-4'-carboxylic acid alkyl ester | |
| JPH0142261B2 (en) | ||
| JPS6261017B2 (en) | ||
| JPS62286943A (en) | 4'-substituted biphenyl crotyl ether derivative | |
| JPS5976029A (en) | Biphenyl derivative containing fluorine | |
| JPS60197637A (en) | Beta-(4-substituted phenyl)propionic acid phenyl ester derivative | |
| JPH0358334B2 (en) | ||
| JPS58210048A (en) | Ester derivative of trans-4-(4-halogenobenzoyloxy)-trans-4'- bicyclohexanol | |
| JPS59144748A (en) | Ester of 4-hydroxy-3-methoxybenzonitrile |