JP2564841B2 - Optically active liquid crystal compound - Google Patents
Optically active liquid crystal compoundInfo
- Publication number
- JP2564841B2 JP2564841B2 JP62206094A JP20609487A JP2564841B2 JP 2564841 B2 JP2564841 B2 JP 2564841B2 JP 62206094 A JP62206094 A JP 62206094A JP 20609487 A JP20609487 A JP 20609487A JP 2564841 B2 JP2564841 B2 JP 2564841B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- optically active
- acid
- ester
- independently
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 16
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 16
- 239000000203 mixture Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- -1 2-substituted propionic acid Chemical class 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VSDNNWKISVRDNT-UHFFFAOYSA-N 2-octoxybenzoic acid Chemical compound CCCCCCCCOC1=CC=CC=C1C(O)=O VSDNNWKISVRDNT-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- ZHMMPVANGNPCBW-UHFFFAOYSA-N 4-Hydroxyhydratropate Chemical compound OC(=O)C(C)C1=CC=C(O)C=C1 ZHMMPVANGNPCBW-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- XIIIHRLCKLSYNH-UHFFFAOYSA-N 4-Hexyloxyphenol Chemical compound CCCCCCOC1=CC=C(O)C=C1 XIIIHRLCKLSYNH-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000007788 liquid Substances 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
【発明の詳細な説明】 本発明は、新規な液晶性化合物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel liquid crystal compound.
更に詳しくは、本発明は一般式〔Ｉ〕 〔式中、R1、R2はそれぞれ独立してC2乃至C16の直鎖ア
ルキル基、Ｘ、Ｙはそれぞれ独立して−CO2−又は−OCO
−結合、＊は不斉炭素原子を示す。〕 で表される光学活性化合物又はそのラセミ体及び該化合
物を含有する液晶組成物に関する。More specifically, the present invention has the general formula [I] [In the formula, R 1 and R 2 are each independently a C 2 to C 16 straight-chain alkyl group, and X and Y are each independently —CO 2 — or —OCO.
-Bond, * indicates an asymmetric carbon atom. ] It is related with the optically active compound represented by these, or its racemic body, and the liquid crystal composition containing this compound.
従来、液晶化合物は、種々の電子光学的表示装置に液
晶材料として用いられている。最適な液晶物質の性質は
それぞれの表示方式により異なるが、水分、熱、空気、
光及び電場等に対して、物理的、化学的且つ電気的に安
定であることが要求される。加えて、液晶の温度範囲が
広いこと、駆動電圧の低いこと、応答速度の速いこと、
時分割特性の良好なこと及び視野角の広いこと等も要求
される。Conventionally, liquid crystal compounds have been used as liquid crystal materials in various electro-optical display devices. The optimum liquid crystal substance properties vary depending on the display method used, but there are
It is required to be physically, chemically and electrically stable against light and electric field. In addition, the temperature range of the liquid crystal is wide, the driving voltage is low, the response speed is fast,
Good time division characteristics and wide viewing angle are also required.
しかし、単一化合物でこれらの諸条件を満足するもの
は今のところ得られておらず、実用的には個々に優れた
性質をもつ数種類の液晶化合物又は非液晶化合物を混合
して液晶組成物としてある程度の使用に耐え得る材料を
得ているのが現状である。However, no single compound satisfying these conditions has been obtained so far, and practically, several kinds of liquid crystal compounds or non-liquid crystal compounds each having excellent properties are mixed to prepare a liquid crystal composition. The current situation is to obtain a material that can withstand some use.
本発明の目的は、実用的性能に優れた液晶組成物の素
材として有利な化合物を提供することにある。An object of the present invention is to provide a compound which is advantageous as a material for a liquid crystal composition having excellent practical performance.
本発明者らはこの目的で化合物中に２−置換プロピオ
ン酸エステル骨格を有するものを多数合成し、本発明化
合物を見出すに至った。For this purpose, the present inventors have synthesized a large number of compounds having a 2-substituted propionic acid ester skeleton, and have found the compound of the present invention.
本発明の化合物は、純粋な状態では無色乃至淡黄色で
あり、化学的に安定であって、広い液晶温度範囲を有す
る。The compound of the present invention is colorless to pale yellow in a pure state, chemically stable, and has a wide liquid crystal temperature range.
更に、他の液晶物質、例えば、既存のビフェニル系、
フェニルシクロヘキサン系、安息香酸フェニルエステル
系、シクロヘキサンカルボン酸フェニルエステル系、シ
ッフ塩基系、アゾキシ系、フェニルピリミジン系及びフ
ェニルメタジオキサン系等との相溶性に優れており、こ
れらの液晶物質との混合によって液晶温度範囲を広く、
応答特性の優れた液晶組成物を構成する有用な成分であ
ることも見出した。In addition, other liquid crystal materials, such as existing biphenyl-based materials,
It has excellent compatibility with phenyl cyclohexane, benzoic acid phenyl ester, cyclohexane carboxylic acid phenyl ester, Schiff base, azoxy, phenyl pyrimidine, phenyl metadioxane, etc., and when mixed with these liquid crystal substances Wide LCD temperature range,
It was also found that it is a useful component constituting a liquid crystal composition having excellent response characteristics.
本発明の化合物は種々の方法で製造できるが、例えば
以下の方法によって製造される。The compound of the present invention can be produced by various methods, for example, the following method.
（１）４−ｎ−アルキルオキシ安息香酸の酸ハライドと
４−ヒドロキシ安息香酸４−〔１−（ｎ−アルキルオキ
シカルボニル）エチル〕フェニルエステルとの反応によ
るエステル化 （２）４−（４−ｎ−アルキルオキシフェニルカルボニ
ルオキシ）安息香酸の酸ハライドと２−（４−ヒドロキ
シフェニル）プロピオン酸ｎ−アルキルエステルとの反
応によるエステル化 （３）２−｛４−〔４−（４−アルキルオキシフェニル
カルボニルオキシ）フェニルカルボニルオキシ｝フェニ
ル〕プロピオン酸の酸ハライドとｎ−アルキルアルコー
ルとの反応によるエステル化 （４）テレフタル酸のジ酸ハライドと４−ｎ−アルキル
オキシフェノール及び２−（４−ヒドロキシフェニル）
プロピオン酸ｎ−アルキルエステルとの反応によるエス
テル化 （５）テレフタル酸モノ４−アルキルフェニルエステル
の酸ハライドと２−（４−ヒドロキシフェニル）プロピ
オン酸ｎ−アルキルエステルとの反応によるエステル化 （６）４−｛４−〔１−（ｎ−アルキルオキシカルボニ
ル）エチル〕フェノキシカルボニル｝安息香酸の酸ハラ
イドと４−アルキルオキシフェノールとの反応によるエ
ステル化 等が挙げられる。(1) Esterification by reaction of acid halide of 4-n-alkyloxybenzoic acid and 4- [1- (n-alkyloxycarbonyl) ethyl] phenyl ester of 4-hydroxybenzoic acid (2) 4- (4- (3) 2- {4- [4- (4-alkyloxy) esterification by reaction of acid halide of n-alkyloxyphenylcarbonyloxy) benzoic acid with 2- (4-hydroxyphenyl) propionic acid n-alkyl ester (Phenylcarbonyloxy) phenylcarbonyloxy} phenyl] propionic acid esterification by reaction with acid halide and n-alkyl alcohol (4) Diacid halide of terephthalic acid and 4-n-alkyloxyphenol and 2- (4-hydroxy) Phenyl)
Esterification by reaction with propionic acid n-alkyl ester (5) Esterification by reaction of acid halide of terephthalic acid mono 4-alkylphenyl ester with 2- (4-hydroxyphenyl) propionic acid n-alkyl ester (6) 4- {4- [1- (n-alkyloxycarbonyl) ethyl] phenoxycarbonyl} benzoic acid is reacted with an acid halide and 4-alkyloxyphenol to form an ester.
以下、実施例を挙げて更に詳細に説明するが、本発明
はこれらによって限定されるものではない。Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.
実施例１ 光学活性なｎ−オクチルオキシ安息香酸４−｛４−
〔１−（ｎ−ヘキシルオキシカルボニル）エチル〕フェ
ノキシカルボニル｝フェニルエステルの製造。Example 1 Optically active n-octyloxybenzoic acid 4- {4-
Production of [1- (n-hexyloxycarbonyl) ethyl] phenoxycarbonyl} phenyl ester.
ｎ−オクチルオキシ安息香酸0.25gに塩化チオニル3.0
mlを加え1.5時間加熱還流した。n-octyloxybenzoic acid 0.25g to thionyl chloride 3.0
ml was added and the mixture was heated under reflux for 1.5 hours.
過剰の塩化チオニルを減圧留去後、光学活性な２−
〔４−（４−ヒドロキシフェニルカルボニルオキシ）フ
ェニル〕プロピオン酸ｎ−ヘキシルエステル0.37g、ピ
リジン0.24ml及びクロロホルム10mlを加え、室温で18時
間撹拌した。After the excess thionyl chloride was distilled off under reduced pressure, the optically active 2-
[4- (4-Hydroxyphenylcarbonyloxy) phenyl] propionic acid n-hexyl ester (0.37 g), pyridine (0.24 ml) and chloroform (10 ml) were added, and the mixture was stirred at room temperature for 18 hours.
反応液に塩酸水を加えて分液し、有機層を飽和食塩水
で洗浄、濃縮して得られた粗製物をシリカゲルカラムク
ロマトグラフィーで分離精製し、光学活性なｎ−オクチ
ルオキシ安息香酸４−｛４−〔１−（ｎ−ヘキシルオキ
シカルボニル）エチル〕フェノキシカルボニル｝フェニ
ルエステル0.34g（収率56％）を得た。Hydrochloric acid was added to the reaction solution for partitioning, the organic layer was washed with saturated brine and concentrated, and the resulting crude product was separated and purified by silica gel column chromatography to give optically active n-octyloxybenzoic acid 4-. 0.34 g (yield 56%) of {4- [1- (n-hexyloxycarbonyl) ethyl] phenoxycarbonyl} phenyl ester was obtained.
〔α〕▲25 D▼−9.7°（ｃ＝0.94、クロロホルム） IR（KBr）:2900,1725,1600,1510,1270,1160cm-1 NMR（CDCl3）： δ6.8〜8.3（m,12H）,3.6〜4.2（m,5H）,1.50（d,J＝7.
0Hz,3H）,0.7〜2.0（m,26H）， MS（m/e）:602（M+,1）,353（12）,233（100） 実施例２ 光学活性なテレフタル酸４−ｎ−ヘキシルオキシフェ
ニル｛４−〔１−（ｎ−ヘキシルオキシカルボニル）エ
チル〕フェニル｝エステルの製造。[Α] ▲ 25 D ▼ −9.7 ° (c = 0.94, chloroform) IR (KBr): 2900,1725,1600,1510,1270,1160 cm −1 NMR (CDCl 3 ): δ6.8 to 8.3 (m, 12H ), 3.6 to 4.2 (m, 5H), 1.50 (d, J = 7.
0Hz, 3H), 0.7 to 2.0 (m, 26H), MS (m / e): 602 (M + , 1), 353 (12), 233 (100) Example 2 Production of optically active terephthalic acid 4-n-hexyloxyphenyl {4- [1- (n-hexyloxycarbonyl) ethyl] phenyl} ester.
テレフタル酸ジクロリド0.33gに４−ｎ−ヘキシルオ
キシフェノール0.39g、光学活性な２−（４−ヒドロキ
シフェニル）プロピオン酸ｎ−ヘキシルエステル0.48g
及びピリジン0.28gを加え、四塩化炭素中、70℃で３時
間撹拌した。0.33 g of terephthalic acid dichloride, 0.39 g of 4-n-hexyloxyphenol, 0.48 g of optically active 2- (4-hydroxyphenyl) propionic acid n-hexyl ester
And pyridine (0.28 g) were added, and the mixture was stirred in carbon tetrachloride at 70 ° C for 3 hours.
反応液をセライト濾過後、塩酸水及びクロロホルムを
加えて分液し、有機層を飽和食塩水で洗浄、濃縮して得
られた粗製物をシリカゲルカラムクロマトグラフィーで
分離精製し、光学活性なテレフタル酸４−ｎ−ヘキシル
オキシフェニル｛４−〔１−（ｎ−ヘキシルオキシカル
ボニル）エチル〕フェニル｝エステル0.23g（収率19
％）を得た。The reaction mixture was filtered through Celite, hydrochloric acid and chloroform were added for liquid separation, and the organic layer was washed with saturated brine and concentrated. The crude product obtained was separated and purified by silica gel column chromatography to give optically active terephthalic acid. 0.23 g of 4-n-hexyloxyphenyl {4- [1- (n-hexyloxycarbonyl) ethyl] phenyl} ester (yield 19
%) Was obtained.
〔α〕▲25 D▼−11.7°（ｃ＝0.36、クロロホルム） IR:2900,1730,1505,1240,1070,710cm-1 NMR（CDCl3）： δ6.7〜8.1（m,12H）,3.6〜4.2（m,5H）,1.58（d,J＝7.
0Hz,3H）,0.7〜1.8（m,22H） MS（m/e）:574（M+,41）,381（100） [Α] ▲ 25 D ▼ -11.7 ° (c = 0.36, chloroform) IR: 2900,1730,1505,1240,1070,710 cm -1 NMR (CDCl 3 ): δ6.7-8.1 (m, 12H), 3.6 ~ 4.2 (m, 5H), 1.58 (d, J = 7.
0Hz, 3H), 0.7 to 1.8 (m, 22H) MS (m / e): 574 (M + , 41), 381 (100)
Claims (2)
ルキル基、Ｘ、Ｙはそれぞれ独立して−CO2−又は−OCO
−結合、＊は不斉炭素原子を示す。〕 で表される光学活性化合物又はそのラセミ体。1. A general formula [I]: [In the formula, R 1 and R 2 are each independently a C 2 to C 16 straight-chain alkyl group, and X and Y are each independently —CO 2 — or —OCO.
-Bond, * indicates an asymmetric carbon atom. ] The optically active compound represented by these, or its racemic body.
ルキル基、Ｘ、Ｙはそれぞれ独立して−CO2−又は−OCO
−結合、＊は不斉炭素原子を示す。〕 で表される光学活性化合物の１種又は２種以上を含有す
ることを特徴とする液晶組成物。2. A compound of the general formula [I]: [In the formula, R 1 and R 2 are each independently a C 2 to C 16 straight-chain alkyl group, and X and Y are each independently —CO 2 — or —OCO.
-Bond, * indicates an asymmetric carbon atom. ] The liquid crystal composition characterized by containing 1 type (s) or 2 or more types of the optically active compound represented by these.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62206094A JP2564841B2 (en) | 1987-08-19 | 1987-08-19 | Optically active liquid crystal compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62206094A JP2564841B2 (en) | 1987-08-19 | 1987-08-19 | Optically active liquid crystal compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6447739A JPS6447739A (en) | 1989-02-22 |
| JP2564841B2 true JP2564841B2 (en) | 1996-12-18 |
Family
ID=16517705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62206094A Expired - Lifetime JP2564841B2 (en) | 1987-08-19 | 1987-08-19 | Optically active liquid crystal compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2564841B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090087646A1 (en) | 2007-10-01 | 2009-04-02 | Cf Supplies International Ltd. | Coated substrate, composition for treating a substrate and process of treatment |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4755329A (en) * | 1985-06-10 | 1988-07-05 | Wisconsin Alumni Research Foundation | Process and intermediates for preparing 1α-hydroxyvitamin D compounds |
| JPS6383229A (en) * | 1986-09-27 | 1988-04-13 | Kawasaki Steel Corp | Heat treatment of rolling roll |
| DE3711362A1 (en) * | 1987-04-07 | 1988-10-27 | Hoechst Ag | USE OF CHIRAL (ALPHA) -CHLORCARBONIC ACID ESTERS, PROLINDERIVATIVES, OXIRANES, THIIRANES AND (ALPHA) -OXYPROPIONIC ACID ESTERS AS COMPONENTS IN LIQUID CRYSTAL MIXTURES FOR THE UTILIZATION OF THE ELECTRODE |
-
1987
- 1987-08-19 JP JP62206094A patent/JP2564841B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6447739A (en) | 1989-02-22 |
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