JPH027307B2 - - Google Patents
Info
- Publication number
- JPH027307B2 JPH027307B2 JP20349282A JP20349282A JPH027307B2 JP H027307 B2 JPH027307 B2 JP H027307B2 JP 20349282 A JP20349282 A JP 20349282A JP 20349282 A JP20349282 A JP 20349282A JP H027307 B2 JPH027307 B2 JP H027307B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- cyano
- type
- benzoic 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 20
- 239000000203 mixture Substances 0.000 claims description 8
- -1 chlorophenyl ester Chemical group 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical class C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XWQDMIXVAYAZGB-UHFFFAOYSA-N 5-chloro-2-hydroxybenzonitrile Chemical compound OC1=CC=C(Cl)C=C1C#N XWQDMIXVAYAZGB-UHFFFAOYSA-N 0.000 description 2
- OEABBNGVFWXEJP-JOCQHMNTSA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C(Cl)=O)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C(Cl)=O)C=C1 OEABBNGVFWXEJP-JOCQHMNTSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FXAILOLNECSGMI-RUDMXATFSA-N 4-chloro-2-[(E)-hydroxyiminomethyl]phenol Chemical compound O\N=C\C1=C(O)C=CC(Cl)=C1 FXAILOLNECSGMI-RUDMXATFSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 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
- 239000000470 constituent Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Description
本発明は負の誘電異方性を有する新規な液晶性
化合物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が持つ光学異方性及び
誘電異物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、電気、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すものが求め
られている。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。
最近、最にカラー液晶表示方法の一方式である
ゲスト・ホスト型液晶表示素子が注目される様に
なつて来た。これは液晶と色素の混合物を使用す
るものであるがポジ型のゲスト・ホスト型表示素
子には負の誘電異方性を有する液晶が使用され
る。従つてその液晶の構成成分としていろいろな
特性をもつた相溶性のよい誘電異方性が負の液晶
化合物が求められている。
本発明の目的はこの様な用途に適した新規な液
晶化合物を提供することにある。
即ち、本発明は一般式
（上式に於てＸはＲ、
The present invention relates to a novel liquid crystal compound having negative dielectric anisotropy and a liquid crystal composition containing the same. Liquid crystal display elements utilize the optical anisotropy and dielectric foreign material properties of liquid crystal materials, and depending on the display format, there are TN type (twisted nematic type), DS type (dynamic scattering type), and guest/host type. There are various types, such as 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 need to be stable against moisture, electricity, heat, light, etc., and they are also required to exhibit a liquid crystal phase over as wide a temperature range as possible, centered around room temperature. ing. 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. Recently, guest-host type liquid crystal display devices, which are one type of color liquid crystal display method, have been attracting attention. This uses a mixture of liquid crystal and dye, but liquid crystal with negative dielectric anisotropy is used for positive guest-host type display elements. Therefore, there is a need for liquid crystal compounds having various properties, good compatibility, and negative dielectric anisotropy as constituent components of the liquid crystal. An object of the present invention is to provide a novel liquid crystal compound suitable for such uses. That is, the present invention is based on the general formula (In the above formula, X is R,
【式】【formula】
(1) ２−シアノ−４−クロロフエノールの製造
５−クロロサリチルアルデヒドオキシム20ｇ
を無水酢酸100mlに溶かし、10時間還流する。
反応後無水酢酸を減圧で留去する。残つた油状
物に水酸化カリウム20ｇを水100mlに溶かした
ものとエタノール100ml加え、５時間80℃にて
加温する。室温にしてから6NHClで完全に酸
性にすると結晶が析出する。この結晶を過
し、乾燥する。mp.164〜168℃、収量14ｇであ
つた。このままつぎの反応に使用した。
(2) エステル化
２−シアノ−４−クロロフエノール1.5ｇを
ピリジン30mlに溶かしておき、これによく振り
まぜながら４−（トランス−４−プロピルシク
ロヘキシル）安息香酸クロリド2.4ｇを加える。
反応後一晩放置してからトルエン200mlを加え、
水にあける。トルエン層を分離し、6N塩酸、
2N水酸化ナトリウム溶液ついで水で洗滌し、
最後に無水硫酸ナトリウムで乾燥する。トルエ
ンを減圧で留去すると結晶物が残るので、それ
をエタノールで再結晶する目的物である４−
（トランス−４−プロピルシクロヘキシル）安
息香酸−２−シアノ−４−クロロフエニルエス
テルが2.1ｇ得られた。収率55％。このものの
Ｃ−Ｎ点は112.6〜113.6℃、Ｎ−Ｉ点は127.3℃
であつた。
実施例 ２〜16
実施例１と同様にして４−（トランス−４−プ
ロピルシクロヘキシル）安息香酸クロリドの代り
にそれぞれに対応するカルボン酸クロリドを使用
して目的の化合物を製造した。これらの結果を実
施例１の結果と共に第１表に示す。
(1) Production of 2-cyano-4-chlorophenol 20 g of 5-chlorosalicylaldehyde oxime
Dissolve in 100 ml of acetic anhydride and reflux for 10 hours.
After the reaction, acetic anhydride is distilled off under reduced pressure. Add 20 g of potassium hydroxide dissolved in 100 ml of water and 100 ml of ethanol to the remaining oil and heat at 80°C for 5 hours. When the mixture is brought to room temperature and completely acidified with 6NHCl, crystals will precipitate. The crystals are filtered and dried. mp.164-168°C, yield 14g. This was used as it was in the next reaction. (2) Esterification 1.5 g of 2-cyano-4-chlorophenol is dissolved in 30 ml of pyridine, and 2.4 g of 4-(trans-4-propylcyclohexyl)benzoic acid chloride is added to this while stirring well.
After the reaction, leave it overnight and add 200ml of toluene.
Pour into water. Separate the toluene layer and add 6N hydrochloric acid,
Wash with 2N sodium hydroxide solution and then with water.
Finally, dry with anhydrous sodium sulfate. When toluene is distilled off under reduced pressure, a crystalline substance remains, which is recrystallized with ethanol to obtain the target product, 4-
2.1 g of (trans-4-propylcyclohexyl)benzoic acid-2-cyano-4-chlorophenyl ester was obtained. Yield 55%. The C-N point of this product is 112.6-113.6℃, and the N-I point is 127.3℃.
It was hot. Examples 2 to 16 Target compounds were produced in the same manner as in Example 1, using the corresponding carboxylic acid chlorides in place of 4-(trans-4-propylcyclohexyl)benzoic acid chloride. These results are shown in Table 1 together with the results of Example 1.
【表】
実施例 17（使用例）
エステル系のネマチツク液晶組成物リクソン
（LIXON）FN−46（チツソ(株)製）のＮ−Ｉ点は
63.4℃、△εは−0.9、20℃における粘度は18.5cp
である。この混合物に市販のメルク社製色素Ｇ−
224を１％添加したものをセルに封入してゲス
ト・ホストセルを作り、そのしきい電圧を測定し
たところ3.80Vであつた。
つぎに本発明の化合物である４−ペンチルビフ
エニリル−4′−カルボン酸−２−シアノ−４−ク
ロロフエニルエステル10部及び４−ヘプチルビフ
エニリル−4′−カルボン酸−２−シアノ−４−ク
ロロフエニルエステル10部を上記FN−45 80部
と混合した液晶組成物を調製した。そのＮ−Ｉ点
は71℃、△εは−4.0、20℃に於ける粘度は29cp
で、これに先と同じく色素Ｇ−224を１％添加し
たものでゲスト・ホスト型液晶セルを作つてその
しきい電圧を測定したところ3.30Vと大きく低下
した。[Table] Example 17 (Usage example) The N-I point of the ester-based nematic liquid crystal composition LIXON FN-46 (manufactured by Chitsuso Corporation) is
63.4℃, △ε is -0.9, viscosity at 20℃ is 18.5cp
It is. This mixture was added with commercially available dye G-
A guest-host cell was created by filling a cell with 1% 224 added, and its threshold voltage was measured to be 3.80V. Next, 10 parts of 4-pentylbiphenyl-4'-carboxylic acid-2-cyano-4-chlorophenyl ester and 4-heptylbiphenylyl-4'-carboxylic acid-2-cyano- A liquid crystal composition was prepared by mixing 10 parts of 4-chlorophenyl ester with 80 parts of the above FN-45. Its N-I point is 71℃, △ε is -4.0, and the viscosity at 20℃ is 29cp.
Then, when we created a guest-host type liquid crystal cell by adding 1% of the dye G-224 as before and measured its threshold voltage, we found that it dropped significantly to 3.30V.
Claims (1)
で表わされる４−置換安息香酸−２−シアノ−４
−クロロフエニルエステル。 ２ 一般式 （上式に於てＸはＲ、【式】 【式】のいずれかであり、又Ｒは炭素 数１〜10のアルキル基又はアルコキシ基を示す）
で表わされる４−置換安息香酸−２−シアノ−４
−クロロフエニルエステルを少なくとも一種含有
する液晶組成物。[Claims] 1. General formula (In the above formula, X is either [Formula] [Formula], and R represents an alkyl group or an alkoxy group having 1 to 10 carbon atoms)
4-substituted benzoic acid-2-cyano-4 represented by
-chlorophenyl ester. 2 General formula (In the above formula, X is either R, [Formula] [Formula], or R represents an alkyl group or an alkoxy group having 1 to 10 carbon atoms)
4-substituted benzoic acid-2-cyano-4 represented by
- A liquid crystal composition containing at least one chlorophenyl ester.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20349282A JPS5995254A (en) | 1982-11-19 | 1982-11-19 | Benzoic acid derivative having negative dielectric anisotropy |
| US06/530,786 US4603018A (en) | 1982-09-27 | 1983-09-09 | 2-cyano-4-halogenophenyl esters |
| DE8383305765T DE3363290D1 (en) | 1982-09-27 | 1983-09-27 | 2-CYANO-4-HALOGENOPHENYL ESTERS |
| EP83305765A EP0106588B1 (en) | 1982-09-27 | 1983-09-27 | 2-cyano-4-halogenophenyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20349282A JPS5995254A (en) | 1982-11-19 | 1982-11-19 | Benzoic acid derivative having negative dielectric anisotropy |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5995254A JPS5995254A (en) | 1984-06-01 |
| JPH027307B2 true JPH027307B2 (en) | 1990-02-16 |
Family
ID=16475047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20349282A Granted JPS5995254A (en) | 1982-09-27 | 1982-11-19 | Benzoic acid derivative having negative dielectric anisotropy |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5995254A (en) |
-
1982
- 1982-11-19 JP JP20349282A patent/JPS5995254A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5995254A (en) | 1984-06-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6366825B2 (en) | ||
| JPH0150694B2 (en) | ||
| JPS634817B2 (en) | ||
| JPH027307B2 (en) | ||
| JPH0239497B2 (en) | 44 * TORANSUU4 ** ARUKIRUSHIKUROHEKISHIRU * ANSOKUKOSAN2 * 44JIHAROGENOFUENIRUESUTERU | |
| JPS6321658B2 (en) | ||
| JPS59141540A (en) | Tricyclic carboxylic acid ester derivative | |
| JPH0150693B2 (en) | ||
| JPH0150691B2 (en) | ||
| JPS64386B2 (en) | ||
| JPH039895B2 (en) | ||
| JPH0326184B2 (en) | ||
| JPH0247455B2 (en) | 44ARUFUA * ARUFUA * ARUFUAATORIFURUOROMECHIRUANSOKUKOSANN44 * TORANSUU4 ** ARUKIRUSHIKUROHEKISHIRU * FUENIRUESUTERU | |
| JPS6334852B2 (en) | ||
| JPS6131A (en) | Naphthalene derivative | |
| JPS64384B2 (en) | ||
| JPS61282345A (en) | Ester compound | |
| JPH045015B2 (en) | ||
| JPH0144177B2 (en) | ||
| JPH0210817B2 (en) | ||
| JPH0141137B2 (en) | ||
| JPH037653B2 (en) | ||
| JPH0251893B2 (en) | ||
| JPS59118754A (en) | Benzoic acid derivative having negative dielectric anisotropic value | |
| JPH0142260B2 (en) |