JPH0210817B2 - - Google Patents
Info
- Publication number
- JPH0210817B2 JPH0210817B2 JP12690881A JP12690881A JPH0210817B2 JP H0210817 B2 JPH0210817 B2 JP H0210817B2 JP 12690881 A JP12690881 A JP 12690881A JP 12690881 A JP12690881 A JP 12690881A JP H0210817 B2 JPH0210817 B2 JP H0210817B2
- Authority
- JP
- Japan
- Prior art keywords
- trans
- liquid crystal
- cyclohexanecarboxylic acid
- acid
- viscosity
- 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 27
- 239000000203 mixture Substances 0.000 claims description 21
- -1 trans-4-substituted cyclohexanecarboxylic acid Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 3
- 229910001887 tin oxide Inorganic materials 0.000 description 3
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- ZGOWXOZNUNZPAV-UHFFFAOYSA-N 4-(4-heptylphenyl)benzonitrile Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 ZGOWXOZNUNZPAV-UHFFFAOYSA-N 0.000 description 2
- GPGGNNIMKOVSAG-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 GPGGNNIMKOVSAG-UHFFFAOYSA-N 0.000 description 2
- HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-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
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- PBMCTXQDYLSLTP-UHFFFAOYSA-N 4-(4-pentylphenyl)-3-phenylbenzonitrile Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1C1=CC=CC=C1 PBMCTXQDYLSLTP-UHFFFAOYSA-N 0.000 description 1
- ZKMUKBBWORLNLA-UHFFFAOYSA-N 4-chloro-2-fluorophenol Chemical compound OC1=CC=C(Cl)C=C1F ZKMUKBBWORLNLA-UHFFFAOYSA-N 0.000 description 1
- JMAUQQIVJIRNDQ-UHFFFAOYSA-N 4-heptylcyclohexane-1-carboxylic acid Chemical compound CCCCCCCC1CCC(C(O)=O)CC1 JMAUQQIVJIRNDQ-UHFFFAOYSA-N 0.000 description 1
- WRZOHCRRNHPSMR-HDRKRICHSA-N C(C)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C(=O)Cl Chemical compound C(C)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C(=O)Cl WRZOHCRRNHPSMR-HDRKRICHSA-N 0.000 description 1
- XXUSEPRYHRDKFV-CTYIDZIISA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-CTYIDZIISA-N 0.000 description 1
- FURZYCFZFBYJBT-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-JCNLHEQBSA-N 0.000 description 1
- OQIHEFMTIUJJET-HDRKRICHSA-N CC[C@H]1CC[C@@H](CC1)[C@H]1CC[C@@H](CC1)C(O)=O Chemical compound CC[C@H]1CC[C@@H](CC1)[C@H]1CC[C@@H](CC1)C(O)=O OQIHEFMTIUJJET-HDRKRICHSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
本発明は液晶相を示し、かつ低粘性の新規な化
合物に関する。
液晶表示素子は液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
式によつてTN型（ねじれネマチツク型）、DS型
（動的散乱型）、ゲスト・ホスト型、DAP型など
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。しかしいずれの液晶物質も水
分、空気、熱、光等に安定であることが必要であ
ることは共通しており、又、室温を中心として出
来るだけ広い温度範囲で液晶相を示し、更に表示
素子の種類によつて異なる最適な誘電異方性値
（Δε）を有する様にしなければならない。しかし
現在のところ単一化合物ではこの様な条件を満た
す物質はなく、数種の液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
が現状である。
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、特にΔε値を調節するに適した新規
な液晶化合物を提供することにある。
即ち、本発明は一般式
（上式中ｎは１又は２であり、Ｒは炭素数１〜10
のアルキル基、ＸはＦ又はClを示す）で表わされ
るトランス―４―置換シクロヘキサンカルボン酸
２―ハロゲノ―４―クロロフエニルエステル及び
これ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。
本発明の化合物はΔεが−0.1と小さく、又粘度
が低く、液晶組成物に加えることによりもとの液
晶組成物のしきい値電圧及び飽和電圧を下げるこ
とができる。また（）式中ｎ＝１のものは室温
近くでネマチツク液晶相を示し、ｎ＝２の化合物
は広い範囲で、高温までネマチツク液晶相を示す
ので、組成物のＮ−Ｉ点を上昇させるのに有効で
ある。
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ロリド
とし、ついでピリジン存在下２―ハロゲノ―４―
クロロフエ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
（上式中ｎ、Ｒ、Ｘは前記と同じ）
以下実施例により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。
実施例 １
〔トランス―４―（トランス―4′―エチルシク
ロヘキシル）シクロヘキサンカルボン酸２―フ
ルオロ―４―クロロフエニルエステルの製造〕
トランス―４―（トランス―4′―エチルシクロ
ヘキシル）シクロヘキサンカルボン酸2.4ｇ
（0.01モル）と塩化チオニル10mlをフラスコに入
れ、50℃に加温する。３時間で均一となる。過剰
の塩化チオニルを減圧にて留去する。残つた油状
物がトランス―４―（トランス―4′―エチルシク
ロヘキシル）シクロヘキサンカルボン酸クロリド
である。一方２―フルオロ―４―クロロフエノー
ル1.5ｇ（0.01モル）をピリジン10mlにとかして
おいたものを先に得られた酸クロリドを加え、乾
燥トルエン100ml加え、よくふりまぜ、一晩放置
する。反応液を水にあけ、6N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後過し、ト
ルエンを減圧にて留去する。残つた油状物をエタ
ノールで再結晶すると目的のトランス―４―（ト
ランス―4′―エチルシクロヘキシル）シクロヘキ
サンカルボン酸２―フルオロ―４―クロロフエニ
ルエステルが得られた。収量1.8ｇ、収率49％。
そのＣ−Ｎ点70.1〜71.0℃、NI点176.0℃であつ
た。
実施例 ２〜12
実施例１に於けるトランス―４―（トランス―
4′―エチルシクロヘキシル）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―（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又はトランス―４
―アルキルシクロヘキサンカルボン酸を使用して
同様の操作で第１表の実施例２〜12の欄に示す
（）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。
実施例 13〜24
〔トランス―４―置換シクロヘキサンカルボン
酸2.4―ジクロロフエニルエステルの製造〕
実施例１と同様にトランス―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
ルボン酸又はトランス―４―アルキルシクロヘキ
サンカルボン酸を使用し、又２―フルオロ―４―
クロロフエノールの代りに2.4―ジクロロフエノ
ール1.7ｇ（0.01モル）を使用して同様の操作で
第２表の実施例13〜24の欄に示す（）式の化合
物を製造した。これらの収率、物性値等を第２表
に示す。
The present invention relates to novel compounds that exhibit a liquid crystal phase and have low viscosity. Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal materials, and depending on the display format, there are TN type (twisted nematic type), DS type (dynamic scattering type), and guest type. There are various types such as host type and DAP type, and the properties of the liquid crystal materials suitable for each type of use are different. However, all liquid crystal materials have in common that they must be stable against moisture, air, heat, light, etc., and they must exhibit a liquid crystal phase over as wide a temperature range as possible, centering on room temperature. It is necessary to have an optimum dielectric anisotropy value (Δε) that differs depending on the type of material. However, at present, there is no single compound that satisfies these conditions, and the current situation is to use liquid crystal compositions obtained by mixing several types of liquid crystal compounds and non-liquid crystal compounds. An object of the present invention is to provide a novel liquid crystal compound useful as a component of such a liquid crystal composition, and particularly suitable for adjusting the Δε value. That is, the present invention is based on the general formula (In the above formula, n is 1 or 2, R is a carbon number of 1 to 10
This is a liquid crystal composition characterized by containing trans-4-substituted cyclohexanecarboxylic acid 2-halogeno-4-chlorophenyl ester represented by the alkyl group (X represents F or Cl) and at least one thereof. The compound of the present invention has a small Δε of -0.1 and a low viscosity, and by adding it to a liquid crystal composition, it is possible to lower the threshold voltage and saturation voltage of the original liquid crystal composition. Furthermore, compounds with n=1 in formula () exhibit a nematic liquid crystal phase near room temperature, and compounds with n=2 exhibit a nematic liquid crystal phase over a wide range up to high temperatures. It is effective for Next, a method for producing the compound of the present invention will be described. First, trans-4-substituted cyclohexanecarboxylic acid corresponding to the target product is reacted with thionyl chloride to form trans-4-substituted cyclohexanecarboxylic acid chloride, and then 2-halogeno-4- in the presence of pyridine.
React with chlorophenol to obtain the desired compound. Showing this as a chemical formula: (In the above formula, n, R, and X are the same as above.) Hereinafter, the manufacturing method and usage examples of the compound of the present invention will be explained in more detail with reference to Examples. Example 1 [Production of trans-4-(trans-4'-ethylcyclohexyl)cyclohexanecarboxylic acid 2-fluoro-4-chlorophenyl ester] 2.4 g of trans-4-(trans-4'-ethylcyclohexyl)cyclohexanecarboxylic acid
(0.01 mol) and 10 ml of thionyl chloride are placed in a flask and heated to 50°C. It becomes uniform in 3 hours. Excess thionyl chloride is distilled off under reduced pressure. The remaining oil is trans-4-(trans-4'-ethylcyclohexyl)cyclohexanecarboxylic acid chloride. On the other hand, 1.5 g (0.01 mol) of 2-fluoro-4-chlorophenol was dissolved in 10 ml of pyridine, and then the acid chloride obtained earlier was added, followed by 100 ml of dry toluene, mixed well, and left overnight. Pour the reaction solution into water and wash with 6N hydrochloric acid, 2N sodium hydroxide, and then water until neutral. The toluene layer was dried over anhydrous sodium sulfate and filtered, and the toluene was distilled off under reduced pressure. The remaining oil was recrystallized from ethanol to obtain the desired trans-4-(trans-4'-ethylcyclohexyl)cyclohexanecarboxylic acid 2-fluoro-4-chlorophenyl ester. Yield 1.8g, yield 49%.
The C-N point was 70.1-71.0°C and the NI point was 176.0°C. Examples 2 to 12 Transformer-4- (trans-
trans-4-(trans-4'-alkylcyclohexyl)cyclohexanecarboxylic acid or trans-4-(trans-4'-alkylcyclohexyl)cyclohexanecarboxylic acid having another alkyl group in place of 4'-ethylcyclohexyl)cyclohexanecarboxylic acid
Compounds of the formula () shown in the columns of Examples 2 to 12 in Table 1 were prepared in the same manner using -alkylcyclohexanecarboxylic acid. These yields, physical properties, etc. are shown in Table 1 together with the results of Example 1. Examples 13 to 24 [Production of trans-4-substituted cyclohexanecarboxylic acid 2,4-dichlorophenyl ester] In the same manner as in Example 1, trans-4-(trans-
4′-alkylcyclohexyl)cyclohexanecarboxylic acid or trans-4-alkylcyclohexanecarboxylic acid, and 2-fluoro-4-
Compounds of the formula ( ) shown in the Examples 13 to 24 column of Table 2 were prepared in the same manner using 1.7 g (0.01 mol) of 2,4-dichlorophenol in place of chlorophenol. Their yields, physical properties, etc. are shown in Table 2.
【表】【table】
【表】
実施例 25（使用例１）
４―ペンチル―4′―シアノビフエニル 45％
４―ヘプチル―4′―シアノビフエニル 29％
４―オクチルオキシ―4′―シアノビフエニル
15％
４―ペンチル―4′―シアノターフエニル 11％
なる組成の液晶混合物のＮ−Ｉ点は63.3℃、粘度
は20℃で46cp、誘電異方性は＋12.4である。この
液晶混合物をケイ素でコーテイングし、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
組み立てた厚さ10μmのセルに封入して液晶セル
とし、25℃でその特性を測定したところ、しきい
電圧1.65V、飽和電圧は2.31Vであつた。
この液晶混合物90部に本発明の実施例11のトラ
ンス―４―ヘプチルシクロヘキサンカルボン酸２
―フルオロ―４―クロロフエニルエステル10部か
らなる組成の液晶混合物のＮ−Ｉ点は60.7℃と低
くなつたが、粘度は20℃で40cp、誘電異方性は
＋10.5と夫々低くなり、又しきい電圧は1.63V、
飽和電圧は2.22Vと低くなつた。
実施例 26（使用例２）
４―ペンチル―4′―シアノビフエニル 51％
４―ヘプチル―4′―シアノビフエニル 32％
４―オクチルオキシ―4′―シアノビフエニル
17％
なる組成の液晶混合物のＮ−Ｉ点は44.3℃、粘度
は20℃で40cp、誘電異方性は＋12.4である。この
液晶混合物をケイ素でコーテイングし、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
組み立てた厚さ10μmのセルに封入して液晶セル
とし、25℃でその特性を測定したところ、しきい
電圧1.65V、飽和電圧は2.31Vであつた。
この液晶混合物90部に本発明実施例１によるト
ランス―４―（トランス―4′―エチルシクロヘキ
シル）シクロヘキサンカルボン酸２―フルオロ―
４―クロロフエニルエステル10部を加えた液晶混
合物のＮ−Ｉ点57.4℃に上り、誘電異方性値は＋
11.0、粘度は20℃で38cpに下がつた。又しきい電
圧は1.61V、飽和電圧は2.25Vに下がつた。
実施例 27（使用例３）
トランス―４―プロピル―（4′―シアノフエニ
ル）シクロヘキサン 24％
トランス―４―ペンチル―（4′―シアノフエニ
ル）シクロヘキサン 36％
トランス―４―ヘプチル―（4′―シアノフエニ
ル）シクロヘキサン 25％
トランス―４―ペンチル―（4′―シアノフエニ
ル―４）シクロヘキサン 15％
なる組成の液晶組成物Ａのネマチツク温度範囲は
−10〜70℃であり粘度は20℃で29cp、誘電異方
性値Δεは＋11.4である。この液晶組成物を、ガ
ラス基板上の酸化スズ透明電極に酸化珪素をコー
テイングして配向性を持たせたもの２枚を組み合
わせて構成した厚さ10μmのセルに封入して、そ
のしきい電圧を測定1.8V、飽和電圧は2.5Vであ
つた。
この液晶組成物A9部に対し本発明実施例５に
よるトランス―４―ペンチルシクロヘキサンカル
ボン酸２―フルオロ―４―クロロフエニルエステ
ル１部を加えた液晶混合物のネマチツク温度範囲
は−15〜63℃であり、粘度は20℃で26.8cp、しき
い電圧は1.66V、飽和電圧は2.40Vであつた。[Table] Example 25 (Usage Example 1) 4-pentyl-4'-cyanobiphenyl 45% 4-heptyl-4'-cyanobiphenyl 29% 4-octyloxy-4'-cyanobiphenyl
A liquid crystal mixture having a composition of 15% 4-pentyl-4'-cyanoterphenyl and 11% has an N-I point of 63.3°C, a viscosity of 46 cp at 20°C, and a dielectric anisotropy of +12.4. This liquid crystal mixture was coated with silicon and sealed in a 10 μm thick cell made by assembling two substrates with rubbed tin oxide transparent electrodes, and its properties were measured at 25°C. The threshold voltage was 1.65V, and the saturation voltage was 2.31V. Trans-4-heptylcyclohexanecarboxylic acid 2 of Example 11 of the present invention was added to 90 parts of this liquid crystal mixture.
The N-I point of a liquid crystal mixture containing 10 parts of -fluoro-4-chlorophenyl ester was as low as 60.7°C, but the viscosity was 40 cp at 20°C, and the dielectric anisotropy was low as +10.5. Also, the threshold voltage is 1.63V,
The saturation voltage was as low as 2.22V. Example 26 (Use example 2) 4-pentyl-4'-cyanobiphenyl 51% 4-heptyl-4'-cyanobiphenyl 32% 4-octyloxy-4'-cyanobiphenyl
The N-I point of a liquid crystal mixture with a composition of 17% is 44.3°C, the viscosity is 40 cp at 20°C, and the dielectric anisotropy is +12.4. This liquid crystal mixture was coated with silicon and sealed in a 10 μm thick cell made by assembling two substrates with rubbed tin oxide transparent electrodes, and its properties were measured at 25°C. The threshold voltage was 1.65V and the saturation voltage was 2.31V. 90 parts of this liquid crystal mixture was added to 2-fluoro-trans-4-(trans-4'-ethylcyclohexyl)cyclohexanecarboxylic acid according to Example 1 of the present invention.
The N-I point of the liquid crystal mixture to which 10 parts of 4-chlorophenyl ester was added rose to 57.4°C, and the dielectric anisotropy value was +
11.0, and the viscosity decreased to 38 cp at 20°C. Also, the threshold voltage decreased to 1.61V and the saturation voltage decreased to 2.25V. Example 27 (Use example 3) Trans-4-propyl-(4'-cyanophenyl)cyclohexane 24% Trans-4-pentyl-(4'-cyanophenyl)cyclohexane 36% Trans-4-heptyl-(4'-cyanophenyl) Liquid crystal composition A with a composition of 25% cyclohexane and 15% trans-4-pentyl-(4'-cyanophenyl-4)cyclohexane has a nematic temperature range of -10 to 70°C, a viscosity of 29 cp at 20°C, and a dielectric anisotropy. The value Δε is +11.4. This liquid crystal composition was encapsulated in a 10 μm thick cell constructed by combining two transparent tin oxide electrodes on glass substrates coated with silicon oxide to give orientation properties, and the threshold voltage was The measurement was 1.8V, and the saturation voltage was 2.5V. The nematic temperature range of a liquid crystal mixture obtained by adding 1 part of trans-4-pentylcyclohexanecarboxylic acid 2-fluoro-4-chlorophenyl ester according to Example 5 of the present invention to 9 parts of this liquid crystal composition A was -15 to 63°C. The viscosity was 26.8 cp at 20°C, the threshold voltage was 1.66V, and the saturation voltage was 2.40V.
Claims (1)
のアルキル基、ＸはＦ又はClを示す）で表わされ
るトランス―４―置換シクロヘキサンカルボン酸
２―ハロゲノ―４―クロロフエニルエステル。 ２ 一般式 （上式中ｎは１又は２であり、Ｒは炭素数１〜10
のアルキル基、ＸはＦ又はClを示す）で表わされ
るトランス―４―置換シクロヘキサンカルボン酸
２―ハロゲノ―４―クロロフエニルエステルを少
なくとも一種含有することを特徴とする液晶組成
物。[Claims] 1. General formula (In the above formula, n is 1 or 2, R is a carbon number of 1 to 10
trans-4-substituted cyclohexanecarboxylic acid 2-halogeno-4-chlorophenyl ester represented by an alkyl group of 2 General formula (In the above formula, n is 1 or 2, R is a carbon number of 1 to 10
1. A liquid crystal composition comprising at least one trans-4-substituted cyclohexanecarboxylic acid 2-halogeno-4-chlorophenyl ester represented by the following alkyl group (X represents F or Cl).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12690881A JPS5829745A (en) | 1981-08-13 | 1981-08-13 | Trans-4-substituted cyclohexanecarboxylic acid 2-halogeno-4-chlorophenyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12690881A JPS5829745A (en) | 1981-08-13 | 1981-08-13 | Trans-4-substituted cyclohexanecarboxylic acid 2-halogeno-4-chlorophenyl ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5829745A JPS5829745A (en) | 1983-02-22 |
| JPH0210817B2 true JPH0210817B2 (en) | 1990-03-09 |
Family
ID=14946862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12690881A Granted JPS5829745A (en) | 1981-08-13 | 1981-08-13 | Trans-4-substituted cyclohexanecarboxylic acid 2-halogeno-4-chlorophenyl ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5829745A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0576403A (en) * | 1991-06-13 | 1993-03-30 | Takashi Kiyohara | Heating insole for shoe |
| JPH05115310A (en) * | 1991-07-15 | 1993-05-14 | Takashi Kiyohara | Heating mid sheet for shoes |
-
1981
- 1981-08-13 JP JP12690881A patent/JPS5829745A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0576403A (en) * | 1991-06-13 | 1993-03-30 | Takashi Kiyohara | Heating insole for shoe |
| JPH05115310A (en) * | 1991-07-15 | 1993-05-14 | Takashi Kiyohara | Heating mid sheet for shoes |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5829745A (en) | 1983-02-22 |
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