JPS60199856A - Alpha-methyl-beta-(4-substituted phenyl)propionic acid phenyl ester derivative - Google Patents
Alpha-methyl-beta-(4-substituted phenyl)propionic acid phenyl ester derivativeInfo
- Publication number
- JPS60199856A JPS60199856A JP5692584A JP5692584A JPS60199856A JP S60199856 A JPS60199856 A JP S60199856A JP 5692584 A JP5692584 A JP 5692584A JP 5692584 A JP5692584 A JP 5692584A JP S60199856 A JPS60199856 A JP S60199856A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- methyl
- liquid crystal
- beta
- alpha
- 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
Abstract
Description
【発明の詳細な説明】
本発明はフェニルプロピオンｉ穎のフェニルエステル誘
導体による耕規化合物および該化合物を含有する液晶組
成物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a liquid crystal composition comprising a phenyl ester derivative of phenylpropion i and a liquid crystal composition containing the compound.
液晶を使用した表示素子は時ハ１．′亀早などに広く使
用されている。これらの液晶衣が素子は液晶物質の元竿
異方性および誘＆異方性を利用したもので、液晶相には
ネマチック液晶相、スメクチック液晶相、コレステリン
ク液晶相があり、そのうちネマチック液晶を利用したも
のが最も広く笑用化されている。それらにｆｌＴＮ型（
ねじれネマチック型）、ＤＳ型（動的散乱型）、ゲスト
・ボス） Ｍ ｓ Ｄ Ａ Ｐ型などがあり、それぞれ
に使用される献品化合物に要求きれる性質は異る。こ扛
ら表示素子に使用されめ叡晶化合物は自然界のなるべく
広いｏｊＬ度軛四で液晶相を示すものが望ましく、現在
のところ単一の化合物でその様な条件をみたす＠な化合
物はなく、′１ｃＶｉａｆの液晶化合物又は非液晶化合
物を混合して実用に供している。これらの化合物は水分
、光、熱、窒気寺に対して安定であることを要求され、
さらに表示素子を駆動させるのに必要なしきい′重圧、
飽和′電圧がなるべく低いことが望ましい。Display elements using liquid crystals have the following characteristics: 'It is widely used in Kamehaya etc. These liquid crystal devices utilize the basic anisotropy and dielectric anisotropy of liquid crystal materials.The liquid crystal phases include nematic liquid crystal phase, smectic liquid crystal phase, and cholesteric liquid crystal phase. The most widely used one is the one that has been made fun of. flTN type (
There are three types: twisted nematic type (twisted nematic type), DS type (dynamic scattering type), Guest Boss type), M s D A P type, etc., and the required properties of the donated compound used for each type are different. It is desirable that the crystalline compound used in these display elements be one that exhibits a liquid crystal phase over as wide an ojL degree as possible in nature, and at present there is no single compound that satisfies such conditions. '1cViaf liquid crystal compounds or non-liquid crystal compounds are mixed and put into practical use. These compounds are required to be stable against moisture, light, heat, and nitrogen.
Furthermore, the threshold pressure required to drive the display element,
It is desirable that the saturation voltage be as low as possible.
本発明の化合物＆ｊ：液晶組成物の成分に用いて山川な
もので、液晶組成物の液晶温度範囲を低温域にｖ８ける
ことができる。Compound &j of the present invention: When used as a component of a liquid crystal composition, it is possible to extend the liquid crystal temperature range of the liquid crystal composition to a low temperature range.
本発明は一般式
（式中でＲ１およびＲ３はそれぞれ炭素数１〜１５のア
ルキル基またはアルコキシ基を示し、Ｒ２はイ）−（）
（）−？たけ（）で粧を示す）で辰わせるａ−メチル−
β−（４−置換フェニル）フロピオン酸のフェニルエス
テル誘導体、および該化合物を含有する液晶組成物であ
る。The present invention is based on the general formula (in the formula, R1 and R3 each represent an alkyl group or an alkoxy group having 1 to 15 carbon atoms, and R2 is a)-()
()−? a-methyl-
A phenyl ester derivative of β-(4-substituted phenyl)furopionic acid, and a liquid crystal composition containing the compound.
本発明の化合物を示す一般式でＲ２刀・（洲のものは液
晶−透明点が０°Ｃ以庫のものも得られる。本発明の化
合物を示す一般式で１工２が＃如≠４−ｏ−Ｏ−ｉ ＊
ｎ ％ ｏ モノｕ ４０°Ｃ前後の液晶−透明点を
有する。本発明の化合物はいずれのものも水分、熱、光
等に対する安定性が良好である。In the general formula showing the compound of the present invention, R2 sword (the one with liquid crystal clearing point is above 0°C is also available.In the general formula showing the compound of the present invention, 1 and 2 are like -o-O-i *
n % o Mono u Has a liquid crystal-clearing point around 40°C. All compounds of the present invention have good stability against moisture, heat, light, etc.
次に本発明の示す化合物の製造法ケ示す。Next, a method for producing the compound of the present invention will be shown.
α−メチル−β−（４−１ｆｔ換フエニル）フロピオン
酵クロリドをピリジンの存在下で反応きせる化合物とし
てそれぞれ４−置換フェノール、４−（トランス−４−
ａ：換シクロヘキシル）フェノールまたは４−ヒドロキ
シ−” ｌｆｉ＞ビフェニルを用いることにより、α−
メチル−β−（４−ｆｔｆ換）−ｃニル）フロピオン酸
のフェニル誘導体を製造することができる。4-substituted phenol, 4-(trans-4-
α-
A phenyl derivative of methyl-β-(4-ftf-converted)-c-nyl)furopionic acid can be produced.
製造法を化学式で次に示す。The manufacturing method is shown below using the chemical formula.
Ｃ１１゜
Ｃ」（３
（式中のＲ１、Ｒ３、Ｒ２はＭｉｌ述に同じである）以
下、実施例により４・発明をさらに酎−細に説明する。C11°C'' (3 (R1, R3, R2 in the formula are the same as described by Mil) Hereinafter, the invention will be explained in more detail with reference to Examples.
各例中でガ２明相を■、融点をｍ、 ｐ、、ネマチック
相をＮと略す己する。In each example, the clear phase is abbreviated as ■, the melting point is m, p, and the nematic phase is abbreviated as N.
’１６ ＭＩＪｒ トリ １
ａ −メチル−β−（４−ペンチルオキシフェニル）プ
ロピオンｒｇ： −４’−プａビル−４−ビフェニリル
エステルの製造
４−ヒドロキシ−４′−プロピルビフェニル２．５ＩＩ
（０，０１２モル）をピリジン１０ｒｙｔに溶ツＩＪ：
Ｐシ、よく振＃）１せながらβ−（４−ペンチルオキシ
フェニル）プロピオン敵クロリド２．５ｆ（０，０１モ
ル）を加えた。この反応液を一晩放置後１００鰐ｌの氷
にあけ、トルエン１０ （ｌ ｔｎｌで油状物を抽出し
た。トルエン８４を６ ＩＩ −１１Ｃ’ｔで、ついで
２ Ｎ −Ｎａ０）１で洸ｒ＋ した候、更に中性にな
るまで水洗してから卯過し、減圧（ｌこしでトルエンを
留去した。残った結晶をエタノールでや）結晶させて目
的物であるα−メチル−β−（４−ヘ：１−ｙ−ルオキ
シフェニル）プロピオンｆソー４′−グロビル−４−ビ
フェニリルエステルを２．５ｙ（５６％）ケ得た。ｍ、
ｐ、 ８４．０〜８４．５”Ｃ，Ｎ−Ｉ点４６．０°Ｃ
であった。（外抑植）実施例２〜５
実施例１に準じた操作を行ない目的の化合物を製造した
。それらの結果を実施列１の結果と併せて第１表に示す
。表中で（）はモノトロピックを示す。'16 MIJr Tri 1 a-Methyl-β-(4-pentyloxyphenyl)propion rg: Production of -4'-pabil-4-biphenylyl ester 4-hydroxy-4'-propylbiphenyl 2.5II
(0,012 mol) dissolved in pyridine 10 ryt IJ:
2.5 f (0.01 mol) of β-(4-pentyloxyphenyl) propionic chloride was added while shaking well. This reaction solution was left overnight, poured into 100 liters of ice, and the oil was extracted with 10 liters of toluene.Toluene 84 was diluted with 6 II-11 C't and then with 2 N-Na0) 1. The target product, α-methyl-β-(4 2.5y (56%) of 4'-globyl-4-biphenylyl ester was obtained. m,
p, 84.0~84.5"C, N-I point 46.0°C
Met. (Extrinsic explantation) Examples 2 to 5 The desired compound was produced by carrying out the same procedure as in Example 1. The results are shown in Table 1 together with the results of Example Column 1. In the table, () indicates monotropic.
使用例
なる組成の液晶組成物のネマチック６′欠品温度範囲は
０°Ｃ〜４４°Ｃである。該組成物９ＭＭ部に本発明の
化合物の一つである実施例１で製造したα−メチル−β
−（４−ペンチルオキシフェニル）プロピオン［−４’
−プロピル−４−ビフェニリルエステル１重量部からな
る組成物のネマチック液晶温度範囲は一５°Ｃ〜４４°
Ｃを示しネマチック液晶温度範囲を低温域に広げること
ができた。The nematic 6' shortage temperature range of the liquid crystal composition having the composition used as an example is 0°C to 44°C. 9MM portion of the composition contains α-methyl-β prepared in Example 1, which is one of the compounds of the present invention.
-(4-pentyloxyphenyl)propion[-4'
- The nematic liquid crystal temperature range of the composition consisting of 1 part by weight of propyl-4-biphenylyl ester is -5°C to 44°C.
C, and the nematic liquid crystal temperature range could be extended to a low temperature range.
以上that's all
Claims (2)
ルキル基またはアルコキシ基を示し、Ｒ２４ｌ−Ｑ−１
−ｏ−０−ｔ＊ は−Ｑ−Ｑ−を示す）で表わせるα−
メチル−β−（４−ｆ、を換フェニル）フロピオン酸の
フェニルエステル誘導体。(1) General formula (in the formula, R1 and R3 each represent an alkyl group or an alkoxy group having 1 to 15 carbon atoms, R24l-Q-1
-o-0-t* indicates -Q-Q-)
Phenyl ester derivative of methyl-β-(4-f, substituted phenyl)furopionic acid.
ルキル基またはアルコキシ基を示し、Ｒ２は（）、（）
（）または（）（ンを示す）で表わせるａ−メチル−β
−（４−置換フェニル）フロピオン酸のフェニルニスデ
ル誘導体を宮南する液晶組成物。(2) General formula (in the formula, R' and R3 each represent an alkyl group or alkoxy group having 1 to 15 carbon atoms, and R2 is (), ()
a-Methyl-β expressed as () or () (indicating n)
A liquid crystal composition comprising a phenylnisder derivative of -(4-substituted phenyl)furopionic acid.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5692584A JPS60199856A (en) | 1984-03-24 | 1984-03-24 | Alpha-methyl-beta-(4-substituted phenyl)propionic acid phenyl ester derivative |
| US06/709,398 US4686305A (en) | 1984-03-07 | 1985-03-07 | 4'-substituted-phenyl α-methyl-β-(4-substituted-phenyl) propionates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5692584A JPS60199856A (en) | 1984-03-24 | 1984-03-24 | Alpha-methyl-beta-(4-substituted phenyl)propionic acid phenyl ester derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS60199856A true JPS60199856A (en) | 1985-10-09 |
Family
ID=13041072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5692584A Pending JPS60199856A (en) | 1984-03-07 | 1984-03-24 | Alpha-methyl-beta-(4-substituted phenyl)propionic acid phenyl ester derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60199856A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650600A (en) * | 1983-09-17 | 1987-03-17 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystal phase |
| WO1987005012A2 (en) * | 1986-02-21 | 1987-08-27 | The Secretary Of State For Defence In Her Britanni | Liquid crystal compounds, mixtures and devices |
| US4732699A (en) * | 1985-07-01 | 1988-03-22 | Ajinomoto Co., Inc. | Biphenyl carbonic acid ester compounds and liquid crystal composition containing the same |
| US4744918A (en) * | 1984-07-11 | 1988-05-17 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystal phase |
-
1984
- 1984-03-24 JP JP5692584A patent/JPS60199856A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650600A (en) * | 1983-09-17 | 1987-03-17 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystal phase |
| US4744918A (en) * | 1984-07-11 | 1988-05-17 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystal phase |
| US4732699A (en) * | 1985-07-01 | 1988-03-22 | Ajinomoto Co., Inc. | Biphenyl carbonic acid ester compounds and liquid crystal composition containing the same |
| WO1987005012A2 (en) * | 1986-02-21 | 1987-08-27 | The Secretary Of State For Defence In Her Britanni | Liquid crystal compounds, mixtures and devices |
| WO1987005012A3 (en) * | 1986-02-21 | 1988-01-28 | Ian Charles Sage | Liquid crystal compounds, mixtures and devices |
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