JPS6346741B2 - - Google Patents
Info
- Publication number
- JPS6346741B2 JPS6346741B2 JP8335880A JP8335880A JPS6346741B2 JP S6346741 B2 JPS6346741 B2 JP S6346741B2 JP 8335880 A JP8335880 A JP 8335880A JP 8335880 A JP8335880 A JP 8335880A JP S6346741 B2 JPS6346741 B2 JP S6346741B2
- Authority
- JP
- Japan
- Prior art keywords
- trans
- liquid crystal
- cyclohexanecarboxylic acid
- cyanophenyl ester
- parts
- 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 17
- 239000000203 mixture Substances 0.000 claims description 9
- -1 trans-4-(trans-4'-substituted cyclohexyl)-cyclohexanecarboxylic acid Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- JXPGQFKJNKWDKP-UHFFFAOYSA-N 4-(4-propylcyclohexyl)cyclohexane-1-carboxylic acid Chemical compound C1CC(CCC)CCC1C1CCC(C(O)=O)CC1 JXPGQFKJNKWDKP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 2
- SGHBRHKBCLLVCI-UHFFFAOYSA-N 3-hydroxybenzonitrile Chemical compound OC1=CC=CC(C#N)=C1 SGHBRHKBCLLVCI-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
- 238000004519 manufacturing process Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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 1
- 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 1
- MTNZGYZWCQZBFV-UHFFFAOYSA-N 4-(4-propylcyclohexyl)cyclohexane-1-carbonyl chloride Chemical compound C1CC(CCC)CCC1C1CCC(C(Cl)=O)CC1 MTNZGYZWCQZBFV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FLJRBFMGAYFGNF-VVPTUSLJSA-N C(CCCCCC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C(=O)O Chemical compound C(CCCCCC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C(=O)O FLJRBFMGAYFGNF-VVPTUSLJSA-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
- 239000002253 acid Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
本発明は正の誘電異方性を示す新規な液晶物質
及びそれを含有する液晶組成物に関する。
液晶表示素子は液晶物質の特性である光学異方
性及び誘電異方性を利用したものである。液晶表
示素子にはTN（ねじれネマチツク）型、DS（動
的散乱）型、ゲスト・ホスト型、DAP型など各
種の方式のものがあり、それぞれの方式により、
使用される液晶物質に要求される特性は異る。し
かしいずれの方式に於ても液晶物質は水分、熱、
空気などに安定であることが必要であり、又出来
るだけ広い温度範囲で液晶相を示す物質が望まし
い。しかし現在のところ単一の化合物ではこの様
な条件を満たすものはなく、数種の液晶化合物や
非液晶化合物を混合したものを使用しているのが
現状である。液晶化合物を混合する場合、一般に
誘電異方性値△εの正のものと負のものを混合す
れば△εはその中間の値のものが得られるが、△
εの正と負のものの絶体値の大きなもの同志は相
溶性があまりよくないので混合しにくく、配合制
限を受ける。
従つて△εの絶体値の小さいものの方が各種の
液晶組成物を調製する上で適している。
本発明の化合物は△εが＋２程度の小さい値を
有する、各種の液晶組成物を調製するために有用
な化合物である。
即ち本発明は一般式
（上式中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―（トランス―4′―置
換シクロヘキシル）―シクロヘキサンカルボン酸
3″―シアノフエニルエステル及び少くともそれを
１成分含有する液晶組成物である。
本発明の化合物は次の様な工程で得ることが出
来る。
即ちトランス―４―（トランス―4′―置換シク
ロヘキシル）―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酸塩化物とし、これにピリ
ジン中で３―シアノフエノールを反応させて目的
のトランス―４―（トランス―4′―置換シクロヘ
キシル）―シクロヘキサンカルボン酸3″―シアノ
フエニルエステルが得られる。
以下に実施例として、本発明の化合物の製造例
及応用例を示して、本発明について更に詳しく説
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″―シアノフエニルエステルの製造〕
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５ｇ
（0.02モル）に塩化チオニル10mlを加え、加温す
ると１時間位で均一になる。更に１時間位加温し
た後減圧で過剰の塩化チオニルを留去して残つた
ものがトランス―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酸
塩化物である。一方３―シアノフエノール2.2ｇ
（0.02モル）をピリジン10mlに溶かしておき、こ
の中へ先の酸塩化物を加え、よく撹拌してから１
晩放置する。それにトルエン100mlを加え、その
トルエン層を分液斗で6N塩酸で、ついで2N苛
性ソーダ溶液で、最後に水で中性になるまで洗浄
し、無水硫酸ナトリウムで乾燥後、減圧でトルエ
ンを留去する。残つた結晶を50mlのエタノールで
再結晶すると目的のトランス―４―（トランス―
4′―プロピルシクロヘキシル）―シクロヘキサン
カルボン酸3″―シアノフエニルエステルが4.5ｇ
得られた。その相転移点及び元素分析値などを第
１表に示す。
The present invention relates to a novel liquid crystal material exhibiting positive dielectric anisotropy and a liquid crystal composition containing the same. Liquid crystal display elements utilize optical anisotropy and dielectric anisotropy, which are characteristics of liquid crystal materials. There are various types of liquid crystal display elements, such as TN (twisted nematic) type, DS (dynamic scattering) type, guest-host type, and DAP type.
The properties required for the liquid crystal materials used are different. However, in either method, the liquid crystal material is exposed to moisture, heat,
It is necessary to be stable in air and the like, and it is desirable to use a substance that exhibits a liquid crystal phase over as wide a temperature range as possible. However, at present, there is no single compound that satisfies these conditions, and the current situation is to use a mixture of several types of liquid crystal compounds and non-liquid crystal compounds. When mixing liquid crystal compounds, in general, if you mix positive and negative dielectric anisotropy values △ε, you can obtain △ε with an intermediate value, but △
Materials with large absolute values of positive and negative ε have poor compatibility and are difficult to mix, subject to mixing restrictions. Therefore, those having a smaller absolute value of Δε are more suitable for preparing various liquid crystal compositions. The compound of the present invention is a compound useful for preparing various liquid crystal compositions having a small value of Δε of about +2. That is, the present invention is based on the general formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms) trans-4-(trans-4'-substituted cyclohexyl)-cyclohexanecarboxylic acid
3''-cyanophenyl ester and a liquid crystal composition containing at least one component thereof. The compound of the present invention can be obtained by the following steps. That is, trans-4-(trans-4'-substituted cyclohexyl)-cyclohexanecarboxylic acid is reacted with thionyl chloride to form an acid chloride, and this is reacted with 3-cyanophenol in pyridine to form the desired trans-4-( Trans-4'-substituted cyclohexyl)-cyclohexanecarboxylic acid 3''-cyanophenyl ester is obtained. The present invention will be explained in more detail by showing production examples and application examples of the compounds of the present invention as examples below. Example 1 [Production of trans-4-(trans-4'-propylcyclohexyl)-cyclohexanecarboxylic acid 3''-cyanophenyl ester] 5 g of trans-4-(trans-4'-propylcyclohexyl)-cyclohexanecarboxylic acid
Add 10 ml of thionyl chloride to (0.02 mol) and heat to homogenize in about 1 hour. After further heating for about 1 hour, excess thionyl chloride was distilled off under reduced pressure, and what remained was trans-4-(trans-4'-propylcyclohexyl)-cyclohexanecarboxylic acid chloride. On the other hand, 2.2g of 3-cyanophenol
(0.02 mol) dissolved in 10 ml of pyridine, add the acid chloride mentioned above, stir well, and
Leave it overnight. Add 100 ml of toluene to it, wash the toluene layer with 6N hydrochloric acid in a separator, then with 2N caustic soda solution, and finally with water until neutral, dry over anhydrous sodium sulfate, and then distill off the toluene under reduced pressure. . Recrystallize the remaining crystals with 50ml of ethanol to obtain the desired trans-4-(trans-
4.5g of 4′-propylcyclohexyl)-cyclohexanecarboxylic acid 3″-cyanophenyl ester
Obtained. Table 1 shows the phase transition point, elemental analysis values, etc.
【表】【table】
【表】
実施例 ２〜３
実施例１に於けるトランス―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５ｇの代りにトランス―４―（トラン
ス―4′―ペンチルシクロヘキサンカルボン酸5.5
ｇ（実施例２）、又はトランス―４―（トランス
―4′―ヘプチルシクロヘキサンカルボン酸6.1ｇ
（実施例３）を使用する以外は実施例１と全く同
様にして第１表に示す様な結果を得た。
実施例４ （応用例）
４―ペンチル―4′―シアノビフエニル 46部
４―ヘプチル―4′―シアノビフエニル 28部
４―オクチルオキシ―4′―シアノビフエニル
15部
４―ペンチル―４―シアノフエニルエステル
11部
からなる液晶組成物は−５〜63℃のネマチツク温
度範囲を有し、20℃に於ける粘度は48cp、又こ
れをセル厚10μmのTNセルに封入した時の動作
しきい電圧は1.60V、飽和電圧は2.20Vである。
この液晶混合物86部に、更に本発明のトランス
―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″―シアノフエ
ニルエステル７部及びトランス―４―（トランス
―4′―ヘプチルシクロヘキシル）―シクロヘキサ
ンカルボン酸3″―シアノフエニルエステル７部を
加えた液晶組成物は−15〜67℃のより広いネマチ
ツク温度範囲を有し、20℃での粘度は47cp、そ
れを用いて10μmのセル厚を有するTNセルにし
たときの動作しきい電圧は1.66V、飽和電圧は
2.25Vであつた。[Table] Examples 2 to 3 Transformer-4- (trans-
Trans-4-(trans-4'-pentylcyclohexanecarboxylic acid 5.5g instead of 5g of 4'-propylcyclohexyl)-cyclohexanecarboxylic acid
g (Example 2), or 6.1 g of trans-4-(trans-4'-heptylcyclohexanecarboxylic acid)
The results shown in Table 1 were obtained in exactly the same manner as in Example 1 except that (Example 3) was used. Example 4 (Application example) 4-pentyl-4'-cyanobiphenyl 46 parts 4-heptyl-4'-cyanobiphenyl 28 parts 4-octyloxy-4'-cyanobiphenyl
15 parts 4-pentyl-4-cyanophenyl ester
The liquid crystal composition consisting of 11 parts has a nematic temperature range of -5 to 63°C, a viscosity of 48 cp at 20°C, and an operating threshold voltage of 1.60 when it is sealed in a TN cell with a cell thickness of 10 μm. V, the saturation voltage is 2.20V. To 86 parts of this liquid crystal mixture, 7 parts of trans-4-(trans-4'-propylcyclohexyl)-cyclohexanecarboxylic acid 3''-cyanophenyl ester of the present invention and trans-4-(trans-4'-heptylcyclohexyl )-cyclohexanecarboxylic acid 3''-cyanophenyl ester (7 parts) has a wider nematic temperature range of -15 to 67°C, has a viscosity of 47 cp at 20°C, and can be used to When using a TN cell with a cell thickness, the operating threshold voltage is 1.66V, and the saturation voltage is
It was 2.25V.
Claims (1)
す） で表わされるトランス―４―（トランス―4′―置
換シクロヘキシル）―シクロヘキサンカルボン酸
3″―シアノフエニルエステル。 ２ 一般式 （上式中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―（トランス―4′―置
換シクロヘキシル）―シクロヘキサンカルボン酸
3″―シアノフエニルエステルを少くとも１成分含
むことを特徴とする液晶組成物。[Claims] 1. General formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms) trans-4-(trans-4'-substituted cyclohexyl)-cyclohexanecarboxylic acid
3″-cyanophenyl ester. 2 General formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms) trans-4-(trans-4'-substituted cyclohexyl)-cyclohexanecarboxylic acid
A liquid crystal composition comprising at least one component of 3″-cyanophenyl ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8335880A JPS579752A (en) | 1980-06-19 | 1980-06-19 | Trans-4-(trans-4'-substituted cyclohexyl)- cyclohexanecarboxylic acid 3"-cyanophenyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8335880A JPS579752A (en) | 1980-06-19 | 1980-06-19 | Trans-4-(trans-4'-substituted cyclohexyl)- cyclohexanecarboxylic acid 3"-cyanophenyl ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS579752A JPS579752A (en) | 1982-01-19 |
| JPS6346741B2 true JPS6346741B2 (en) | 1988-09-19 |
Family
ID=13800201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8335880A Granted JPS579752A (en) | 1980-06-19 | 1980-06-19 | Trans-4-(trans-4'-substituted cyclohexyl)- cyclohexanecarboxylic acid 3"-cyanophenyl ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS579752A (en) |
-
1980
- 1980-06-19 JP JP8335880A patent/JPS579752A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS579752A (en) | 1982-01-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6144862B2 (en) | ||
| JPS6366825B2 (en) | ||
| JPH0144186B2 (en) | ||
| JPH0150694B2 (en) | ||
| JPS6346741B2 (en) | ||
| JPH0131499B2 (en) | ||
| JPH0150693B2 (en) | ||
| JPH0150691B2 (en) | ||
| JP2829436B2 (en) | Cyclobutane derivative | |
| JPH0320378B2 (en) | ||
| JPH0247455B2 (en) | 44ARUFUA * ARUFUA * ARUFUAATORIFURUOROMECHIRUANSOKUKOSANN44 * TORANSUU4 ** ARUKIRUSHIKUROHEKISHIRU * FUENIRUESUTERU | |
| JPH0518814B2 (en) | ||
| US4576733A (en) | 4-Halogenobenzoic acid esters | |
| JPS5920248A (en) | Trans-4-substituted-cyclohexanecarboxylic acid 2,4-difluorophenyl ester | |
| JPS6131A (en) | Naphthalene derivative | |
| JPH0142261B2 (en) | ||
| JPH0142941B2 (en) | ||
| JPH0210820B2 (en) | ||
| JPS5916841A (en) | 3-fluoro-4-substituted-(4'-(trans-4"-alkylcyclohexyl) cyclohexen-1'-yl)benzene | |
| JPS6312053B2 (en) | ||
| JPH0247979B2 (en) | FURUOROBIFUENIRUNOESUTERUJUDOTAI | |
| JPS6118540B2 (en) | ||
| JPH0528217B2 (en) | ||
| JPS60197651A (en) | Trans-4-(4-substituted phenyl)cyclohexanecarboxylic acid 3-fluoro-4-cyanophenyl ester | |
| JPH0210817B2 (en) |