JPS5813544A - Trans-4-substituted cyclohexanecarboxylic acid 3-chloro-4- fluorophenyl ester - Google Patents
Trans-4-substituted cyclohexanecarboxylic acid 3-chloro-4- fluorophenyl esterInfo
- Publication number
- JPS5813544A JPS5813544A JP11046081A JP11046081A JPS5813544A JP S5813544 A JPS5813544 A JP S5813544A JP 11046081 A JP11046081 A JP 11046081A JP 11046081 A JP11046081 A JP 11046081A JP S5813544 A JPS5813544 A JP S5813544A
- Authority
- JP
- Japan
- Prior art keywords
- trans
- liquid crystal
- chloro
- cyclohexanecarboxylic acid
- fluorophenyl ester
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は正の誘電異方性値有する液晶物質及び非箪晶物
質に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to liquid crystal materials and non-crystalline materials having positive dielectric anisotropy values.
液晶表示素子拡涼晶物質が持つ光学異方性及び誘電異方
性を利用したものであるが、その表示様式によってＴＮ
ｉｌ（ねじれネマチック蓋）、Ｄ８１１（動的散ＩＬＩ
Ｉ）、ゲスト・ホスト臘、ＤＡＰＩＩなど各種の方式に
分けられ、夫々の使用に適する液晶物質の性質は異る。Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of the expansion crystal material, but depending on the display format, TN
il (twisted nematic lid), D811 (dynamic dispersion ILI)
There are various methods such as I), guest-host method, and DAPII method, and the properties of the liquid crystal material suitable for each method are different.
しかし、いずれの液晶物質も、水分、空気、熱、党勢に
安定でな妙ればならないことは共通して＃勢、又室温を
中心として出来るだけ広い温度範囲で箪晶相であら、更
Ｋｌ！！示素子の様式に適した誘電異方性値（ΔＣ）を
有していなければならない、しかし現在のところ、単一
化合物でＦｉこの橡な条件をみたす様な物質はなく、数
種の箪晶化合物や非液晶化合物を混合して得られる液晶
組成物を使用しているのがｌｌｌ状である。However, all liquid crystal materials have in common that they must be stable against moisture, air, heat, and heat, and they must be stable in a crystalline phase over a wide temperature range centered around room temperature. ! ! Fi must have a dielectric anisotropy value (ΔC) suitable for the type of display element, but at present there is no single compound that satisfies this strict condition, and several types of crystals are available. The llll type uses a liquid crystal composition obtained by mixing compounds and non-liquid crystal compounds.
本発明の目的はこの様な液晶組成物の一成分として有用
な、４１ＩＫΔｇの値を＃１４節し、更に粘度を低（す
るのに遣した新規な液晶仕合物を提供するととＫある。The object of the present invention is to provide a novel liquid crystal formulation useful as a component of such liquid crystal compositions, which has a value of 41IKΔg of #14 and further reduces viscosity.
即ち、本発明は一般式
（上式中飼社１又＃１２であり、Ｒ＃ｉ炭素数１〜１０
のアルキル基を示す）
で表わされるトランス−４−９１換シクロヘキサンカル
ボン酸３−クロロ−４−フルオーフェニルエステル及び
ζわを少なくとも一種含有することを特徴とする液晶組
成物である。That is, the present invention relates to the general formula (the above formula Nakakaisha 1 or #12, R#i carbon number 1 to 10
This is a liquid crystal composition characterized by containing at least one type of trans-4-91-substituted cyclohexanecarboxylic acid 3-chloro-4-fluorophenyl ester (indicating an alkyl group) and ζ.
本発明の化合物はΔＣが＋４１１度であり、又粘度が低
く、纏威物に加ｉ’；ｓｅとによりもとの組成物の電気
的特性、すなわちしきい値電圧及び飽和電圧を下けるこ
とができる。また（１）式中、論＝１の化合物は非晶化
合物であるが、ｎ；２の化合物は広い範囲で、高温まで
ネマデック液晶相を示すので、組成物のＮ−Ｉを上昇さ
せるのに有効である。The compound of the present invention has a ΔC of +411 degrees, has a low viscosity, and has the ability to lower the electrical properties of the original composition, that is, the threshold voltage and saturation voltage, due to the addition of ions. I can do it. In addition, in formula (1), the compound with theory = 1 is an amorphous compound, but the compound with n; 2 exhibits a nemadec liquid crystal phase over a wide range and up to high temperatures, so it can be used to increase the N-I of the composition. It is valid.
つぎに本発明の化合物の製造法を示す。まず目的物に対
応するトランス−４−置換シクロヘキサンカルボン酸を
塩化チオニルを反応させて、トランス−４−置換シクロ
ヘキサンカルボン酸クーリドとし、ついでピリジン存在
下３−クーロ−４−フルオロフェノールと反応して目的
の化合物を得る。これを化学式で示すと
、・□・′□・１、
（上式中ｎ、Ｒは前記と同じ）
以下実施例によ抄本発明の化合物の製造法及び使用例に
ついて更に詳細に説明する。Next, a method for producing the compound of the present invention will be described. First, trans-4-substituted cyclohexanecarboxylic acid corresponding to the desired product is reacted with thionyl chloride to obtain trans-4-substituted cyclohexanecarboxylic acid coulide, and then reacted with 3-curo-4-fluorophenol in the presence of pyridine to obtain the desired product. The compound is obtained. This is represented by the chemical formula: ・□・′□・1 (In the above formula, n and R are the same as above) The method for producing and using the compound of the present invention will be explained in more detail with reference to Examples below.
実施Ｍｌ（）ランス−４−（トランス−４′−エテルシ
クロヘキシル）シクロヘキサンカルボン１１１３−／Ｅ
ｌロー４−フルオ■フ□工二ルエステルの製造〕
トランス−４−（）ランス−４′−エチルシフ−ヘキシ
ル）シクロヘキサンカルボン□酸Ｌ４１（ａ０１毫ル）
と塩化チオニル１０一番フラス□コに入れ、５＠ＵＫ加
温す６．３時間’ｔ’′均一どなる。Implementation Ml() trans-4-(trans-4'-ethelcyclohexyl)cyclohexanecarvone 1113-/E
Production of 4-fluorophyl ester] trans-4-()trans-4'-ethylsif-hexyl)cyclohexanecarboxylic acid L41 (a01)
Pour thionyl chloride into a 10-Inch flask and heat at 5@UK for 6.3 hours until it sizzles uniformly.
遥刺の塩化チオニルを減圧にて１去する。′！１つ転−
状物がトランス−４−（トランス−４′−エテルシクロ
ヘキシル）シクロヘキサンカルボン酸り冒リドである。Thionyl chloride from the thorns is removed under reduced pressure. ′! One roll-
The product is trans-4-(trans-4'-ethelcyclohexyl)cyclohexanecarboxylic acid chloride.
一方３−り！１０−４−フルオロフェノール１１Ｆ（０
，０１モル）をピリジン１０−にとかしておいたものに
先に得られた酸クーリドを加え、乾燥トルエン１（１ｍ
加え、よ（ふ〜まぜ、−晩装置する。反応液を□水にあ
ゆ、・・Ｎ塩酸、２Ｎ水酸化ナトリウム、ついで中性に
なるまで水洗する。トルエン層を無水硫酸ナトリウムで
乾燥ＩＰ遇してから、トルエンを減圧にて１去し、残っ
た油状物をエタノールで再結晶すると、目的のトランス
−４−（トラ、ンスー゛４′−エチルシクμヘキシル）
シクロヘキサン力ｋｄ１７１１１３−クロロ−４−フル
オロフェニルエステルが得られた。収量１９１．収率５
２−０その融点扛８４．７〜８＆６ＣＳＮ−１点は５ａ
ｏｃであった。On the other hand, 3-ri! 10-4-fluorophenol 11F (0
, 01 mol) dissolved in pyridine 10-, the acid coulide obtained earlier was added, and 1 mol of dry toluene (1 mol) was dissolved in pyridine 10-.
Add, mix well, and set aside overnight. Add the reaction solution to □ water, wash with N hydrochloric acid, 2N sodium hydroxide, and then water until neutral. Dry the toluene layer with anhydrous sodium sulfate. Then, the toluene was removed under reduced pressure, and the remaining oil was recrystallized with ethanol to obtain the desired trans-4-(tra-4'-ethylcyclohexyl).
Cyclohexane kd171113-chloro-4-fluorophenyl ester was obtained. Yield: 191. Yield 5
2-0 Its melting point is 84.7~8&6CSN-1 point is 5a
It was oc.
実施例２〜１２
実ａｌｌｌｌＫ於けるトランス−４−（トランス−４′
−エチルシタロヘキシに）シクロヘキサンカルボン酸の
代りに他のアルキル基を有するトランス−４−（）ラン
ス−４′−アルキルシクロヘキシル）シフ諺ヘキザンカ
ルボン酸又はトランス−４−アルキルシクロへキサンカ
ルボン酸を使用して同様の操作で第１表に示す（１）式
の化合物を製造した。これらの収率、物性値等を実施例
１の結果と共に第１表に示す。Examples 2 to 12 Trans-4-(trans-4' in allllK)
-ethylcitalohexy)trans-4-()trans-4'-alkylcyclohexyl)Schiff proverbial hexanecarboxylic acid or trans-4-alkylcyclohexanecarboxylic acid with another alkyl group instead of cyclohexanecarboxylic acid Compounds of formula (1) shown in Table 1 were produced in the same manner using . These yields, physical properties, etc. are shown in Table 1 together with the results of Example 1.
実施例１３（使用例１）
４−ペンチル−４′−シアノビフェニル ４５嘩
’４−へブチル−４′−シアノビフェニル ２９
４Ｉ４−オタチルオキシー４′−シアノビフェニル
１５饅４−ヘ：／ｆシル−′−シアノターフェニル
１１１！なる組成・の液晶混合物のＮ−ＩＡ
は６３．３Ｃ。Example 13 (Use example 1) 4-pentyl-4'-cyanobiphenyl 45 4-hebutyl-4'-cyanobiphenyl 29
4I4-Otatyloxy-4'-cyanobiphenyl
15饅4-H:/fSyl-'-cyanoterphenyl 111! N-IA of a liquid crystal mixture with the composition:
is 63.3C.
粘度は！Ｏｒで４６ Ｃｐ、誘電異方性は＋１２４であ
る。この液晶混合物をケイ素でコーティングし、ラビン
グ処理した酸化スズ透明電極を倫えた２枚の基板を組み
立てた厚さ１０部票のセルに封入して液晶セルとし、２
５Ｃでその特性を一定したところ、シ赤い電圧ｔａｓｖ
、飽和電圧社１３１Ｖであった。The viscosity! Or is 46 Cp, and the dielectric anisotropy is +124. This liquid crystal mixture was coated with silicon and sealed in a cell with a thickness of 10 parts, which was made by assembling two substrates with rubbed tin oxide transparent electrodes to form a liquid crystal cell.
When the characteristics were kept constant at 5C, the red voltage tasv
The saturation voltage was 131V.
との液晶混合物９０部に本発明実施例１１のトランス−
４−へプチルシクνヘキサンカルボン＃３−クロａ−４
−フルオロフェニルエステル１０部からなる組成の液晶
混合物のＮ−１点゛は４Ｂ、ＯＣと低くかったが、粘度
１ｊ２０Ｃで３８ ｃｐ、誘電異方性は＋１１６と夫々
低くなり、又し赤い電圧は１．５０Ｖ、飽和電圧は！１
（ｌと低くなった。Inventive Example 11 trans-
4-heptylsicvhexanecarvone #3-chloroa-4
- The N-1 point of the liquid crystal mixture with a composition consisting of 10 parts of fluorophenyl ester was low at 4B and OC, but the viscosity was 38 cp at 1j20C, the dielectric anisotropy was low at +116, and the red voltage was low. 1.50V, the saturation voltage is! 1
(It became as low as l.
使用例２
４−ペンチル−４′−シアノビフェニル ５１１
！４−へブチル−４′−シアノビフェニル ３２
−４−オクチルオ中シー４′−シアノビフェニル
１７Ｉｓな一義威の液晶混合物のＮ−Ｉ点Ｆ１４表
３ｃ。Use example 2 4-pentyl-4'-cyanobiphenyl 511
! 4-Hebutyl-4'-cyanobiphenyl 32
-4-octyl-4'-cyanobiphenyl
N-I point F14 Table 3c of the liquid crystal mixture of 17Is Yiyiwei.
粘＃ｆはｗｅＣで４・ｃｐ、誘電異方性は＋ＩＬ４であ
る。ヒの液晶混合物をケイ素でコーティングし、ラビン
グ処理した酸化スズ透明電極を備えた２枚の基板を■み
立てた厚さ１０ＩＩｍのセルに封入して液晶セルとし、
２５ｃでその特性を一定したところ、し赤い電圧Ｌ６５
Ｖ、飽和電圧は１３１ｖであった。The viscosity #f is 4·cp in weC, and the dielectric anisotropy is +IL4. A liquid crystal cell is obtained by coating the above liquid crystal mixture with silicon and sealing it in a 10 IIm thick cell made of two substrates equipped with rubbed tin oxide transparent electrodes.
When the characteristics were kept constant at 25c, the red voltage L65
V, the saturation voltage was 131v.
仁の液晶混合物ｌ０ＩＩＩＫ本１ｍ＠実施例２のトラン
ス−４−（トランス−４′−プロビルシクロヘキシル）
シクーヘキナンカルボンｍ５−ｐロロー４−フルオーフ
ェニルエステル１０ｍを加えた液晶混合物のＮ−ＩＡけ
５叡３ＣＫ上り、誘電異方性値は＋１１５、粘度Ｆｉ２
０Ｃ”Ｑ、３７ｃｐに下がった。又し赤い電圧は１．Ｓ
５Ｖ、飽和電圧は！２０ＶＫ下ｚた。Liquid crystal mixture lOIIIK 1 m@trans-4-(trans-4'-propylcyclohexyl) of Example 2
N-IA of a liquid crystal mixture containing 10m of cyclohequinane carbon m5-p rolow 4-fluorophenyl ester, dielectric anisotropy value +115, viscosity Fi2
0C"Q, dropped to 37cp. Also, the red voltage is 1.S
5V, the saturation voltage is! 20VK lower.
以 上that's all
Claims (1)
ルキル基を示す） で真わ参れるトランス−４−置換シクロヘキナンカルボ
ン酸３−りａ ａ −４−フルオロフェニルエステル。 （上式中ｎ ＃１１又は２であり、Ｒは炭素数１〜１０
のアルキル基を示す） で表わされるトランス−４−置換シタロヘキすンカルポ
ン酸３−り闘ロー４−フルオロフェニルエステルを少な
くとも一種含有することを特徴とする液晶組成物。[Scope of Claims] (In the above formula, n is 1 or 2, and R represents an alkyl group having 1 to 10 carbon atoms) -4-Fluorophenyl ester. (In the above formula, n is #11 or 2, and R has 1 to 10 carbon atoms.
1. A liquid crystal composition comprising at least one trans-4-substituted citalohexanecarboxylic acid 3-fluorophenyl ester represented by the following alkyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11046081A JPS5813544A (en) | 1981-07-15 | 1981-07-15 | Trans-4-substituted cyclohexanecarboxylic acid 3-chloro-4- fluorophenyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11046081A JPS5813544A (en) | 1981-07-15 | 1981-07-15 | Trans-4-substituted cyclohexanecarboxylic acid 3-chloro-4- fluorophenyl ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5813544A true JPS5813544A (en) | 1983-01-26 |
| JPH0150694B2 JPH0150694B2 (en) | 1989-10-31 |
Family
ID=14536266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11046081A Granted JPS5813544A (en) | 1981-07-15 | 1981-07-15 | Trans-4-substituted cyclohexanecarboxylic acid 3-chloro-4- fluorophenyl ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5813544A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4502974A (en) * | 1982-03-31 | 1985-03-05 | Chisso Corporation | High temperature liquid-crystalline ester compounds |
| JPS6045549A (en) * | 1983-08-23 | 1985-03-12 | Dainippon Ink & Chem Inc | Novel nematic liquid crystal compound |
| US4550981A (en) * | 1982-09-30 | 1985-11-05 | Hoffmann-La Roche Inc. | Liquid crystalline esters and mixtures |
| US4683078A (en) * | 1985-03-12 | 1987-07-28 | Chisso Corporation | Dihalogeno-aromatic compound |
| US4696759A (en) * | 1985-05-22 | 1987-09-29 | Chisso Corporation | Ester compound |
| US4710315A (en) * | 1984-04-16 | 1987-12-01 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Anisotropic compounds and liquid crystal mixtures therewith |
| JP2011207783A (en) * | 2010-03-29 | 2011-10-20 | Dic Corp | Transparent insulating composition |
| JP2014177446A (en) * | 2013-10-21 | 2014-09-25 | Dic Corp | Transparent insulation composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52134978A (en) * | 1977-02-01 | 1977-11-11 | Fukutarou Komori | Fixing material adding antiiabrasion on friction material for braking of motorrcar |
-
1981
- 1981-07-15 JP JP11046081A patent/JPS5813544A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52134978A (en) * | 1977-02-01 | 1977-11-11 | Fukutarou Komori | Fixing material adding antiiabrasion on friction material for braking of motorrcar |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4502974A (en) * | 1982-03-31 | 1985-03-05 | Chisso Corporation | High temperature liquid-crystalline ester compounds |
| US4550981A (en) * | 1982-09-30 | 1985-11-05 | Hoffmann-La Roche Inc. | Liquid crystalline esters and mixtures |
| US4708441A (en) * | 1982-09-30 | 1987-11-24 | Hoffman-La Roche Inc. | Esters |
| JPS6045549A (en) * | 1983-08-23 | 1985-03-12 | Dainippon Ink & Chem Inc | Novel nematic liquid crystal compound |
| JPS6254783B2 (en) * | 1983-08-23 | 1987-11-17 | Dainippon Ink & Chemicals | |
| US4710315A (en) * | 1984-04-16 | 1987-12-01 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Anisotropic compounds and liquid crystal mixtures therewith |
| USRE36849E (en) * | 1984-04-16 | 2000-09-05 | Merck Patent Gmbh | Anisotropic compounds and liquid crystal mixtures therewith |
| US4683078A (en) * | 1985-03-12 | 1987-07-28 | Chisso Corporation | Dihalogeno-aromatic compound |
| US4816179A (en) * | 1985-03-12 | 1989-03-28 | Chisso Corporation | Dihalogeno-aromatic compound |
| US4696759A (en) * | 1985-05-22 | 1987-09-29 | Chisso Corporation | Ester compound |
| JP2011207783A (en) * | 2010-03-29 | 2011-10-20 | Dic Corp | Transparent insulating composition |
| JP2014177446A (en) * | 2013-10-21 | 2014-09-25 | Dic Corp | Transparent insulation composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0150694B2 (en) | 1989-10-31 |
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