JPH0142260B2 - - Google Patents
Info
- Publication number
- JPH0142260B2 JPH0142260B2 JP1536984A JP1536984A JPH0142260B2 JP H0142260 B2 JPH0142260 B2 JP H0142260B2 JP 1536984 A JP1536984 A JP 1536984A JP 1536984 A JP1536984 A JP 1536984A JP H0142260 B2 JPH0142260 B2 JP H0142260B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- trans
- fluoro
- compound
- cyclohexanecarboxylic acid
- 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
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 11
- -1 cyclohexanecarboxylic acid 3-fluoro-4-cyanophenyl ester Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- REIVHYDACHXPNH-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(F)=C1 REIVHYDACHXPNH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- VHEDZXHFMYOPBT-UHFFFAOYSA-N 3-fluoro-4-(hydroxyiminomethyl)phenol Chemical compound FC1=C(C=NO)C=CC(=C1)O VHEDZXHFMYOPBT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LNEMDIUSUQPKIP-UHFFFAOYSA-N 2-phenyl-1,3-dioxane Chemical compound O1CCCOC1C1=CC=CC=C1 LNEMDIUSUQPKIP-UHFFFAOYSA-N 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- GOEQUGKNPZMAKX-UHFFFAOYSA-N C1=C(C#N)C(F)=CC(OC(=O)C2CCCCC2)=C1 Chemical compound C1=C(C#N)C(F)=CC(OC(=O)C2CCCCC2)=C1 GOEQUGKNPZMAKX-UHFFFAOYSA-N 0.000 description 1
- MTNZGYZWCQZBFV-KTSLABGISA-N C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C(Cl)=O)CC1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C(Cl)=O)CC1 MTNZGYZWCQZBFV-KTSLABGISA-N 0.000 description 1
- JXPGQFKJNKWDKP-KTSLABGISA-N C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C(O)=O)CC1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C(O)=O)CC1 JXPGQFKJNKWDKP-KTSLABGISA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- VJCWGXGMXAVKJU-UHFFFAOYSA-N cyclohexyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1CCCCC1 VJCWGXGMXAVKJU-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 230000005685 electric field effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
本発明は新規な有機化合物に関し、更に詳しく
は誘電異方性が正の液晶材料の一成分として使用
する事が出来る新規な化合物に関するものであ
る。
周知のように、液晶性化合物はその液晶相にお
ける誘電率異方性および届折率異方性を利用して
種々の表示装置に使用されている。これらのデイ
スプレイは液晶の電気光学効果を応用した液晶表
示素子や液晶の熱光学効果およびその他の光学効
果を応用したものであり、エレクトロニクスの進
歩と相俟つて、ねじれネマチツク効果、ゲスト・
ホスト効果などの電界効果を応用した液晶表示素
子に数多の液晶性化合物が使用されている。
これらの液晶材料は単独の化合物ではその諸特
性、例えば液晶温度範囲、動作電圧、応答性能等
で実用的な使用に耐えるものはなく、実用的には
数種の液晶化合物あるいは非液晶化合物を混合し
てある程度の使用に耐え得る物を得ているのが現
状である。
本発明の目的はこの様な実用的な性能の優れた
且つ安定な液晶組成物を構成する一成分として有
用な化合物を提供することにある。
本発明は一般式
（式中、Ｒは炭素数が１〜10のアルキル基を示
す。）で表わされるトランス−４−（トランス−４
−アルキルシクロヘキシル）シクロヘキサンカル
ボン酸３−フルオロ−４−シアノフエニルエステ
ルおよび該化合物を含有することを特徴とする液
晶組成物である。
本発明によつて提供される化合物は＋17程度の
大きな正の誘電異方性値をもち、液晶温度範囲が
広く、かつ透明点の高い安定性に優れた新規な液
晶性化合物である。
本発明の化合物は融点が高いためこの化合物単
独では実用的ではないが相溶性に優れ、他のＰ型
又はＮ型液晶例えばシツフ塩基系、アゾキシ系、
安息香酸フエニルエステル系、シクロヘキサンカ
ルボン酸フエニルエステル系、シクロヘキサンカ
ルボン酸シクロヘキシルエステル系、ビフエニル
系、フエニルシクロヘキサン系、フエニルメタジ
オキサン系、フエニルピリミジン系等の液晶の一
種類の系と、あるいは数種類の系の混合物と混合
させる事により得られた液晶組成物の透明点を上
昇せしめる、いわゆる高温液晶として有用であ
る。
本発明の化合物は次に示す反応によつて製造す
る事ができる。
すなわち、トランス−４−（トランス−４−ア
ルキルシクロヘキシル）シクロヘキサンカルボン
酸クロリド（）と３−フルオロ−４−シアノフ
エノール（）とをピリジンの存在下で反応させ
れば目的のエステル化合物（）が得られる。
原料の３−フルオロ−４−シアノフエノールは
２−フルオロ−４−ヒドロキシベンズアルデヒド
オキシム（）を無水酢酸により脱水すれば得ら
れる。これは次式で示される。
以下実施例および応用例により本発明の化合物
の製造方法および使用例を詳細に説明する。
実施例 １
トランス−４−（トランス−４−プロピルシク
ロヘキシル）シクロヘキサンカルボン酸３−フ
ルオロ−４−シアノフエニルエステルの製造
３−フルオロ−４−シアノフエノール1.5ｇ
（11ｍmol）を乾燥したピリジン20mlに溶解して
おき、これにトランス−４−（トランス−４−プ
ロピルシクロヘキシル）シクロヘキサンカルボン
酸クロリド3.0ｇ（11ｍmol）を乾燥トルエン20
mlに溶解した溶液を加え、60℃にて３時間加熱反
応させた。反応終了後、反応物を水100ml中に投
入し、トルエン層を分離し6N塩酸、次いで2N水
酸化ナトリウム水溶液、次いで水で洗浄し、トル
エン層を無水硫酸ナトリウム上で乾燥した。この
トルエン溶液からトルエンを溜去し、残つた油状
物を酢酸エチルエステル10mlから再結晶して、目
的のトランス−４−（トランス−４−プロピルシ
クロヘキシル）シクロヘキサンカルボン酸３−フ
ルオロ−４−シアノフエニルエステル2.7ｇが得
られた。収率は69％であつた。
この物の結晶−ネマチツク点（Ｃ−Ｎ点）は
65.1℃、ネマチツク−透明点（Ｎ−Ｉ点）は211
℃であつた。
実施例 ２〜６
実施例１に準じた方法により、表１に示したア
ルキル置換基をもつた化合物を製造した。これら
の化合物の物性値を実施例１の結果とともに表１
示す。
The present invention relates to a novel organic compound, and more particularly to a novel compound that can be used as a component of a liquid crystal material with positive dielectric anisotropy. As is well known, liquid crystal compounds are used in various display devices by utilizing the dielectric anisotropy and the refractive index anisotropy in the liquid crystal phase. These displays utilize liquid crystal display elements that apply the electro-optic effect of liquid crystals, thermo-optic effects of liquid crystals, and other optical effects. Together with advances in electronics, twisted nematic effects, guest
Many liquid crystal compounds are used in liquid crystal display devices that utilize electric field effects such as host effects. These liquid crystal materials cannot be used as a single compound in terms of their properties, such as liquid crystal temperature range, operating voltage, response performance, etc., and for practical purposes, it is necessary to mix several types of liquid crystal compounds or non-liquid crystal compounds. At present, we have obtained products that can withstand a certain level of use. An object of the present invention is to provide a compound useful as a component of such a stable liquid crystal composition with excellent practical performance. The present invention is based on the general formula (In the formula, R represents an alkyl group having 1 to 10 carbon atoms.)
-Alkylcyclohexyl) cyclohexanecarboxylic acid 3-fluoro-4-cyanophenyl ester and a liquid crystal composition containing the compound. The compound provided by the present invention is a novel liquid crystal compound that has a large positive dielectric anisotropy value of about +17, has a wide liquid crystal temperature range, and has a high clearing point and excellent stability. The compound of the present invention has a high melting point, so it is not practical to use alone, but it has excellent compatibility with other P-type or N-type liquid crystals, such as Schiff base type, azoxy type,
One type of liquid crystal system such as benzoic acid phenyl ester system, cyclohexanecarboxylic acid phenyl ester system, cyclohexanecarboxylic acid cyclohexyl ester system, biphenyl system, phenylcyclohexane system, phenylmetadioxane system, phenylpyrimidine system, etc. Alternatively, it is useful as a so-called high-temperature liquid crystal that increases the clearing point of a liquid crystal composition obtained by mixing it with a mixture of several types of systems. The compound of the present invention can be produced by the following reaction. That is, by reacting trans-4-(trans-4-alkylcyclohexyl)cyclohexanecarboxylic acid chloride () and 3-fluoro-4-cyanophenol () in the presence of pyridine, the desired ester compound () can be obtained. It will be done. The raw material 3-fluoro-4-cyanophenol can be obtained by dehydrating 2-fluoro-4-hydroxybenzaldehyde oxime (2) with acetic anhydride. This is shown by the following equation. The manufacturing method and usage examples of the compound of the present invention will be explained in detail below using Examples and Application Examples. Example 1 Production of trans-4-(trans-4-propylcyclohexyl)cyclohexanecarboxylic acid 3-fluoro-4-cyanophenyl ester 1.5 g of 3-fluoro-4-cyanophenol
(11 mmol) was dissolved in 20 ml of dry pyridine, and 3.0 g (11 mmol) of trans-4-(trans-4-propylcyclohexyl)cyclohexanecarboxylic acid chloride was dissolved in 20 ml of dry toluene.
ml of the solution was added, and the mixture was reacted by heating at 60°C for 3 hours. After the reaction was completed, the reaction product was poured into 100 ml of water, and the toluene layer was separated and washed with 6N hydrochloric acid, then with a 2N aqueous sodium hydroxide solution, and then with water, and the toluene layer was dried over anhydrous sodium sulfate. Toluene was distilled off from this toluene solution, and the remaining oil was recrystallized from 10 ml of ethyl acetate to obtain the desired trans-4-(trans-4-propylcyclohexyl)cyclohexanecarboxylic acid 3-fluoro-4-cyanophyl ester. 2.7 g of enyl ester were obtained. The yield was 69%. The crystal-nematic point (C-N point) of this product is
65.1℃, nematic clearing point (N-I point) is 211
It was warm at ℃. Examples 2 to 6 Compounds having alkyl substituents shown in Table 1 were produced by a method similar to Example 1. Table 1 shows the physical property values of these compounds along with the results of Example 1.
show.
【表】
晶相、ネマチツク相および等方性液相を表
わす。
応用例 １[Table] Shows crystalline phase, nematic phase, and isotropic liquid phase.
Application example 1
【式】30重量部[Formula] 30 parts by weight
【式】40重量部[Formula] 40 parts by weight
【式】30重量部
なる割合の液晶組成物のネマチツク液晶温度範囲
は−5゜〜52.1℃である。この液晶組成物をセル厚
10μｍのTNセルに封入したものの動作しきい電
圧は1.54V、飽和電圧は2.13Vであつた。又粘度
は20℃で23.4cpであつた。
上記の液晶組成物85重量部に本発明の化合物の
一つである実施例１に示したトランス−４−（ト
ランス−４−プロピルシクロヘキシル）シクロヘ
キサンカルボン酸３−フルオロ−４−シアノフエ
ニルエステル15重量部を加えた液晶組成物のネマ
チツク液晶温度範囲は−10゜〜70.0℃になりこれ
を前記のTNセルに封入したものの動作しきい電
圧は1.53V、飽和電圧は2.14Vであつた。又、粘
度は20℃で28.2cpであつた。
以上の事により、本発明の化合物を使用する事
によつてその液晶組成物の粘度をそれほど上昇さ
せることなくネマチツク液晶温度範囲を拡大する
事ができ、その効果は著しい事が判明した。The nematic liquid crystal temperature range of the liquid crystal composition in the proportion of 30 parts by weight is -5° to 52.1°C. This liquid crystal composition has a cell thickness of
When sealed in a 10 μm TN cell, the operating threshold voltage was 1.54V and the saturation voltage was 2.13V. The viscosity was 23.4 cp at 20°C. Trans-4-(trans-4-propylcyclohexyl)cyclohexanecarboxylic acid 3-fluoro-4-cyanophenyl ester 15 shown in Example 1, which is one of the compounds of the present invention, was added to 85 parts by weight of the above liquid crystal composition. The nematic liquid crystal temperature range of the liquid crystal composition to which the weight part was added was -10° to 70.0°C, and when this was sealed in the above-mentioned TN cell, the operating threshold voltage was 1.53V and the saturation voltage was 2.14V. Further, the viscosity was 28.2 cp at 20°C. From the above, it has been found that by using the compound of the present invention, the nematic liquid crystal temperature range can be expanded without significantly increasing the viscosity of the liquid crystal composition, and the effect is remarkable.
Claims (1)
す。） で表わされるトランス−４−（トランス−４−ア
ルキルシクロヘキシル）シクロヘキサンカルボン
酸３−フルオロ−４−シアノフエニルエステル。 ２ 一般式 （式中、Ｒは炭素数が１〜10のアルキル基を示
す。） で表わされるトランス−４−（トランス−４−ア
ルキルシクロヘキシル）シクロヘキサンカルボン
酸３−フルオロ−４−シアノフエニルエステルを
含有することを特徴とする液晶組成物。[Claims] 1. General formula (In the formula, R represents an alkyl group having 1 to 10 carbon atoms.) trans-4-(trans-4-alkylcyclohexyl)cyclohexanecarboxylic acid 3-fluoro-4-cyanophenyl ester. 2 General formula (In the formula, R represents an alkyl group having 1 to 10 carbon atoms.) Contains trans-4-(trans-4-alkylcyclohexyl)cyclohexanecarboxylic acid 3-fluoro-4-cyanophenyl ester A liquid crystal composition characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1536984A JPS60161957A (en) | 1984-01-31 | 1984-01-31 | Substituted bicyclohexanecarboxylic acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1536984A JPS60161957A (en) | 1984-01-31 | 1984-01-31 | Substituted bicyclohexanecarboxylic acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60161957A JPS60161957A (en) | 1985-08-23 |
| JPH0142260B2 true JPH0142260B2 (en) | 1989-09-11 |
Family
ID=11886868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1536984A Granted JPS60161957A (en) | 1984-01-31 | 1984-01-31 | Substituted bicyclohexanecarboxylic acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60161957A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2967129D1 (en) * | 1979-05-28 | 1984-08-30 | Merck Patent Gmbh | Liquid-crystal compositions |
-
1984
- 1984-01-31 JP JP1536984A patent/JPS60161957A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60161957A (en) | 1985-08-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |