JPH0142261B2 - - Google Patents
Info
- Publication number
- JPH0142261B2 JPH0142261B2 JP4002984A JP4002984A JPH0142261B2 JP H0142261 B2 JPH0142261 B2 JP H0142261B2 JP 4002984 A JP4002984 A JP 4002984A JP 4002984 A JP4002984 A JP 4002984A JP H0142261 B2 JPH0142261 B2 JP H0142261B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- benzoic acid
- crystal composition
- fluoro
- 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 37
- 239000000203 mixture Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- LJXCFVJGBORMRW-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) benzoate Chemical compound C1=C(C#N)C(F)=CC(OC(=O)C=2C=CC=CC=2)=C1 LJXCFVJGBORMRW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000004988 Nematic liquid crystal Substances 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- KIQUBJMVGFNXSO-WKILWMFISA-N COC[C@@H]1CC[C@H](CC1)C1=CC=C(C(=O)OC2=CC(=C(C=C2)C#N)F)C=C1 Chemical compound COC[C@@H]1CC[C@H](CC1)C1=CC=C(C(=O)OC2=CC(=C(C=C2)C#N)F)C=C1 KIQUBJMVGFNXSO-WKILWMFISA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000126 substance Substances 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
- VHEDZXHFMYOPBT-UHFFFAOYSA-N 3-fluoro-4-(hydroxyiminomethyl)phenol Chemical compound FC1=C(C=NO)C=CC(=C1)O VHEDZXHFMYOPBT-UHFFFAOYSA-N 0.000 description 1
- QHKZFBWALKFPND-WGSAOQKQSA-N C(CCC)OC[C@@H]1CC[C@H](CC1)C1=CC=C(C(=O)OC2=CC(=C(C=C2)C#N)F)C=C1 Chemical compound C(CCC)OC[C@@H]1CC[C@H](CC1)C1=CC=C(C(=O)OC2=CC(=C(C=C2)C#N)F)C=C1 QHKZFBWALKFPND-WGSAOQKQSA-N 0.000 description 1
- UCNZOZUGADTBEK-MXVIHJGJSA-N C(CCCC)OC[C@@H]1CC[C@H](CC1)C1=CC=C(C(=O)OC2=CC(=C(C=C2)C#N)F)C=C1 Chemical compound C(CCCC)OC[C@@H]1CC[C@H](CC1)C1=CC=C(C(=O)OC2=CC(=C(C=C2)C#N)F)C=C1 UCNZOZUGADTBEK-MXVIHJGJSA-N 0.000 description 1
- LTDOGFZSKALWMM-HAQNSBGRSA-N COC[C@@H]1CC[C@H](CC1)C1=CC=C(C(=O)Cl)C=C1 Chemical compound COC[C@@H]1CC[C@H](CC1)C1=CC=C(C(=O)Cl)C=C1 LTDOGFZSKALWMM-HAQNSBGRSA-N 0.000 description 1
- FHWSOPHYDCUXQE-WKILWMFISA-N COC[C@@H]1CC[C@H](CC1)C1=CC=C(C(=O)OC2=CC(=C(C=C2)C#N)Cl)C=C1 Chemical compound COC[C@@H]1CC[C@H](CC1)C1=CC=C(C(=O)OC2=CC(=C(C=C2)C#N)Cl)C=C1 FHWSOPHYDCUXQE-WKILWMFISA-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
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 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
- 239000000470 constituent Substances 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- -1 ester compound Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005693 optoelectronics 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
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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。
周知の様に液晶性化合物はその液晶相における
誘電率の異方性および届折率の異方性を利用して
種々の表示装置に使用されている。
これらのデイスプレーは液晶の電気光学効果を
応用した液晶表示素子や、液晶の熱光学効果を応
用したものであり、捩れた液晶配列を持つネマチ
ツク液晶を用いる表示素子に利用できる他、適当
な色素物質を含有する液晶性化合物ないし液晶混
合物を用いたゲスト・ホスト効果を応用した液晶
表示素子にも使用されている。
これらの液晶材料は単独の化合物ではその諸特
性即ち、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。
例えばネマチツク液晶表示素子に用いられるネ
マチツク液晶組成分は液晶表示素子を低電圧で駆
動できるものとして、誘電異方性値（Δε＝ε−
ε⊥）が大きな正の値を示すものが求められてい
る。液晶組成物は液晶表示素子の応答速度を早め
るために粘度が低いものが望ましい。
液晶組成物を対向基板の電極に挾持する液晶表
示素子は対向電極間隔の部分的な不均一により色
むらを生ずることがあり、光学的異方性値（Δn
＝n−n⊥）の大きな液晶組成物を用いて色む
らの発生を軽減できることが知られている。対向
電極間隔が小さいものは同じ印加電圧で電界強度
を大きく与えることができ、液晶組成物のΔnを
大きくする成分が求められている。
液晶表示素子に用いる液晶組成物は液晶相を呈
する温度範囲の広いものが望まれ、添加成分を混
合した場合に液晶組成物の粘度を大幅に増加させ
ることがなく液晶相−等方性液体相の転移点を上
昇させることのできるものが望まれている。
本願出願人は以上のような事情に鑑みて次の一
般式で表わされる化合物を特開昭58−121266号公
報で示した。
（上式中R′は炭素数１〜８のアルキル基を示
す。）
本発明は改良された性質を有する化合物を提供
するもので、その目的は実用的な性質が優れ安定
な液晶組成物を構成する成分として有用な化合物
を提供することである。
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
４−（トランス−４−アルキルオキシメチルシク
ロヘキシル）安息香酸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＋40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。本発明による化合物は相溶性
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
ス系、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ことにより粘度を大幅
に上昇させることなく得られた液晶組成物の透明
点を上せしめ、いわゆる高温液晶成分として有用
である。本発明の示す化合物は液晶表示素子の駆
動電圧を低下させる液晶組成物の成分として有用
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、４−（トランス−４−アルキルオキ
シメチルシクロヘキシル）安息香酸クロリド
（）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。
ここで用いた４−（トランス−４−アルキルオ
キシメチルシクロヘキシル）安息香酸クロリドは
特開昭58−131942号公報に記載の方法により合成
することができる。又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て脱水して、
次いで例えばアルカリを用いて加水分解して製造
することができる。これを反応式で示すと
以下実施例により本発明の化合物の製造方法お
よび応用例により用途を詳細に説明する。
実施例 １
４−（トランス−４−メチルオキシメチルシク
ロヘキシル）安息香酸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５mlに溶解して
おき、これに４−（トランス−４−メチルオキシ
メチルシクロヘキシル）安息香酸クロリド2.7ｇ
（11ｍmol）を乾燥トルエン10ml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、2N水酸化ナトリウム
水溶液、次いで水で洗浄し、次いでトルエン層を
無水硫酸ナトリウム上で乾燥した。トルエン層か
らトルエンを留去し、残つた固型物をエタノール
８mlから再結晶して、目的の４−（トランス−４
−メチルオキシメチルシクロヘキシル）安息香酸
３−フルオロ−４−シアノフエニルエステル2.7
ｇが得られた。収率は66％であつた。
この物の結晶−ネマチツク点は（Ｃ−Ｎ点）は
109.3℃、ネマチツク−透明点（Ｎ−Ｉ点）は
193.4℃であつた。
実施例 ２、３
実施例１に準じた方法により次に示す他のアル
キル置換基をもつた化合物を製造した。
４−（トランス−４−ブチルオキシメチルシク
ロヘキシル）安息香酸３−フルオロ−４−シアノ
フエニルエステル
Ｃ−Ｎ点 45.2℃
Ｎ−Ｉ点 126.6℃
４−（トランス−４−ペンチルオキシメチルシ
クロヘキシル）安息香酸３−フルオロ−４−シア
ノフエニルエステル
Ｃ−Ｎ点 63.1℃
Ｎ−Ｉ点 122.3℃
比較例
特開昭58−121266号公報の示す次の化合物を製
造した。
４−（トランス−４−メチルオキシメチルシク
ロヘキシル）安息香酸３−クロロ−４−シアノフ
エニルエステル
Ｃ−Ｎ点 99.4℃
Ｎ−Ｉ点 137.0℃
応用例
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 anisotropy of the dielectric constant and the anisotropy of the refractive index in the liquid crystal phase. These displays can be used for liquid crystal display elements that apply the electro-optical effect of liquid crystals, or those that apply the thermo-optical effect of liquid crystals, and can be used for display elements that use nematic liquid crystals with twisted liquid crystal alignment, as well as display elements that use suitable dyes. It is also used in liquid crystal display elements that apply the guest-host effect using liquid crystal compounds or liquid crystal mixtures containing substances. 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. I have obtained something that can withstand some use. For example, the nematic liquid crystal composition used in a nematic liquid crystal display element has a dielectric anisotropy value (Δε=ε−
ε⊥) exhibiting a large positive value is desired. The liquid crystal composition desirably has a low viscosity in order to increase the response speed of the liquid crystal display element. In a liquid crystal display element in which a liquid crystal composition is sandwiched between electrodes on a counter substrate, color unevenness may occur due to local unevenness in the spacing between the counter electrodes, and the optical anisotropy value (Δn
It is known that the occurrence of color unevenness can be reduced by using a liquid crystal composition with a large value (=n−n⊥). A liquid crystal composition with a small spacing between opposing electrodes can provide a large electric field strength with the same applied voltage, and a component that increases Δn of the liquid crystal composition is desired. It is desirable that the liquid crystal composition used in liquid crystal display elements exhibits a liquid crystal phase over a wide temperature range, and when additive components are mixed, the viscosity of the liquid crystal composition does not increase significantly and the liquid crystal phase - isotropic liquid phase is achieved. What is desired is something that can raise the transition point of . In view of the above circumstances, the applicant of the present application disclosed a compound represented by the following general formula in Japanese Patent Application Laid-Open No. 121266/1983. (In the above formula, R' represents an alkyl group having 1 to 8 carbon atoms.) The present invention provides a compound with improved properties, and its purpose is to provide a stable liquid crystal composition with excellent practical properties. The object of the present invention is to provide a compound useful as a constituent component. The present invention is based on the general formula (In the formula, R represents an alkyl group having 1 to 10 carbon atoms.) Contains 4-(trans-4-alkyloxymethylcyclohexyl)benzoic acid 3-fluoro-4-cyanophenyl ester and the compound This is a liquid crystal composition characterized by: The compound provided by the present invention is a novel liquid crystal compound that has a large positive dielectric anisotropy value of about +40, has a wide liquid crystal temperature range, and has a high clearing point and excellent stability. The compound according to the present invention has excellent compatibility with other P-type or N-type liquid crystals such as Schiff base type, azoxy type, benzoic acid phenyl ester type,
Cyclohexanecarboxylic acid phenyl ester,
By mixing with one type of liquid crystal system such as cyclohexyl esteth cyclohexanecarboxylate, biphenyl, phenylcyclohexane, phenylmetadioxane, or phenylpyrimidine, or with a mixture of several types, the viscosity can be significantly increased. It increases the clearing point of the obtained liquid crystal composition without raising it, and is useful as a so-called high-temperature liquid crystal component. The compound of the present invention is useful as a component of a liquid crystal composition that lowers the driving voltage of a liquid crystal display element. The compound of the present invention can be produced by the following reaction. That is, by reacting 4-(trans-4-alkyloxymethylcyclohexyl)benzoic acid chloride () and 3-fluoro-4-cyanophenol in the presence of pyridine, the desired ester compound () can be obtained. The 4-(trans-4-alkyloxymethylcyclohexyl)benzoic acid chloride used here can be synthesized by the method described in JP-A-58-131942. 3-Fluoro-4-cyanophenol is obtained by dehydrating 2-fluoro-4-hydroxybenzaldehyde oxime with acetic anhydride.
It can then be produced by hydrolysis using, for example, an alkali. This is shown in the reaction equation Hereinafter, the method for producing the compound of the present invention and its uses will be explained in detail with reference to Examples. Example 1 Production of 4-(trans-4-methyloxymethylcyclohexyl)benzoic acid 3-fluoro-4-cyanophenyl ester 1.5 g of 3-fluoro-4-cyanophenol
(11 mmol) was dissolved in 5 ml of dry pyridine, and 2.7 g of 4-(trans-4-methyloxymethylcyclohexyl)benzoic acid chloride was dissolved in 5 ml of dry pyridine.
A solution of (11 mmol) dissolved in 10 ml of dry toluene 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, 2N aqueous sodium hydroxide solution, and then water, and then the toluene layer was dried over anhydrous sodium sulfate. Toluene was distilled off from the toluene layer, and the remaining solid was recrystallized from 8 ml of ethanol to obtain the desired 4-(trans-4
-Methyloxymethylcyclohexyl)benzoic acid 3-fluoro-4-cyanophenyl ester 2.7
g was obtained. The yield was 66%. The crystal-nematic point of this substance (C-N point) is
109.3℃, nematic clearing point (N-I point)
It was 193.4℃. Examples 2 and 3 Compounds having other alkyl substituents shown below were produced by a method similar to Example 1. 4-(trans-4-butyloxymethylcyclohexyl)benzoic acid 3-fluoro-4-cyanophenyl ester C-N point 45.2℃ N-I point 126.6℃ 4-(trans-4-pentyloxymethylcyclohexyl)benzoic acid 3-Fluoro-4-cyanophenyl ester C-N point 63.1°C N-I point 122.3°C Comparative Example The following compound disclosed in JP-A-58-121266 was produced. 4-(trans-4-methyloxymethylcyclohexyl)benzoic acid 3-chloro-4-cyanophenyl ester C-N point 99.4℃ N-I point 137.0℃ Application example
【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
なる割合のネマチツク液晶組成物Ａを用意し本発
明の示す化合物または比較例の示す化合物を添加
しその特性を測定した。結果を第１表に示す。表
中でVthはしきい値電圧、Vsatは飽和電圧を示
し、セル厚10μｍのねじれネマチツクセルを用い
て測定した値を示す。[Formula] A nematic liquid crystal composition A in a proportion of 30 parts by weight was prepared, a compound according to the present invention or a compound according to a comparative example was added thereto, and its properties were measured. The results are shown in Table 1. In the table, Vth indicates a threshold voltage and Vsat indicates a saturation voltage, which are values measured using a twisted nematic cell with a cell thickness of 10 μm.
Claims (1)
ロヘキシル）安息香酸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 ４−（トランス−４−アルキルオキシメチルシク
ロヘキシル）安息香酸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.) 4-(trans-4-alkyloxymethylcyclohexyl)benzoic acid 3-fluoro-4-cyanophenyl ester. 2 General formula (In the formula, R represents an alkyl group having 1 to 10 carbon atoms.) Characteristic liquid crystal composition.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4002984A JPS60184060A (en) | 1984-03-02 | 1984-03-02 | 3-fluoro-4-cyanophenyl 4-(trans-4-alkyloxymethylcyclohexyl) benzoate |
| US06/706,609 US4661283A (en) | 1984-03-02 | 1985-02-28 | Benzoate derivatives having a large positive dielectric anisotropy value and liquid crystal compositions containing same |
| DE8585301457T DE3560259D1 (en) | 1984-03-02 | 1985-03-04 | Benzoate derivatives having positive dielectric anisotropy and liquid crystal compositions containing them |
| EP85301457A EP0155792B1 (en) | 1984-03-02 | 1985-03-04 | Benzoate derivatives having positive dielectric anisotropy and liquid crystal compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4002984A JPS60184060A (en) | 1984-03-02 | 1984-03-02 | 3-fluoro-4-cyanophenyl 4-(trans-4-alkyloxymethylcyclohexyl) benzoate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60184060A JPS60184060A (en) | 1985-09-19 |
| JPH0142261B2 true JPH0142261B2 (en) | 1989-09-11 |
Family
ID=12569478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4002984A Granted JPS60184060A (en) | 1984-03-02 | 1984-03-02 | 3-fluoro-4-cyanophenyl 4-(trans-4-alkyloxymethylcyclohexyl) benzoate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60184060A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4839524B2 (en) * | 2001-04-26 | 2011-12-21 | Ｄｉｃ株式会社 | Liquid crystal composition |
| CN113930792B (en) * | 2021-10-22 | 2023-04-21 | 华南理工大学 | Electrochemical preparation method of 3-cyanoindole compound |
-
1984
- 1984-03-02 JP JP4002984A patent/JPS60184060A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60184060A (en) | 1985-09-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |