JPH06128196A - Ester derivative - Google Patents
Ester derivativeInfo
- Publication number
- JPH06128196A JPH06128196A JP4303253A JP30325392A JPH06128196A JP H06128196 A JPH06128196 A JP H06128196A JP 4303253 A JP4303253 A JP 4303253A JP 30325392 A JP30325392 A JP 30325392A JP H06128196 A JPH06128196 A JP H06128196A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- acid
- ester derivative
- crystal composition
- reduced pressure
- 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.)
- Granted
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 24
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 46
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004185 ester group Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 25
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 10
- 239000000463 material Substances 0.000 abstract description 9
- UNROFSAOTBVBBT-UHFFFAOYSA-N 4-ethylcyclohexane-1-carboxylic acid Chemical compound CCC1CCC(C(O)=O)CC1 UNROFSAOTBVBBT-UHFFFAOYSA-N 0.000 abstract description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 6
- RPEPGIOVXBBUMJ-UHFFFAOYSA-N 2,3-difluorophenol Chemical compound OC1=CC=CC(F)=C1F RPEPGIOVXBBUMJ-UHFFFAOYSA-N 0.000 abstract description 4
- -1 2,3-difluorophenyl ester Chemical class 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 238000010992 reflux Methods 0.000 abstract description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000000862 absorption spectrum Methods 0.000 description 12
- 238000010586 diagram Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000010410 layer Substances 0.000 description 3
- 239000012044 organic layer Substances 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZOSBAYFWABIRBV-UHFFFAOYSA-N 1-pentylcyclohexane-1-carboxylic acid Chemical compound CCCCCC1(C(O)=O)CCCCC1 ZOSBAYFWABIRBV-UHFFFAOYSA-N 0.000 description 1
- ZVBMXGLAFRTOJS-UHFFFAOYSA-N 1-propylcyclohexane-1-carboxylic acid Chemical compound CCCC1(C(O)=O)CCCCC1 ZVBMXGLAFRTOJS-UHFFFAOYSA-N 0.000 description 1
- KAWUBNUJMFOOOE-UHFFFAOYSA-N 3-amino-3-(3,5-dibromo-4-hydroxyphenyl)propanoic acid Chemical compound OC(=O)CC(N)C1=CC(Br)=C(O)C(Br)=C1 KAWUBNUJMFOOOE-UHFFFAOYSA-N 0.000 description 1
- CWYNKKGQJYAHQG-UHFFFAOYSA-N 4-pentylbenzoic acid Chemical compound CCCCCC1=CC=C(C(O)=O)C=C1 CWYNKKGQJYAHQG-UHFFFAOYSA-N 0.000 description 1
- RVLAXPQGTRTHEV-XYPYZODXSA-N CCCCC[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound CCCCC[C@H]1CC[C@H](C(O)=O)CC1 RVLAXPQGTRTHEV-XYPYZODXSA-N 0.000 description 1
- BALGERHMIXFENA-MGCOHNPYSA-N CCCC[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound CCCC[C@H]1CC[C@H](C(O)=O)CC1 BALGERHMIXFENA-MGCOHNPYSA-N 0.000 description 1
- QCNUKEGGHOLBES-KYZUINATSA-N CCC[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound CCC[C@H]1CC[C@H](C(O)=O)CC1 QCNUKEGGHOLBES-KYZUINATSA-N 0.000 description 1
- OUBGXJOVPXVFKX-XYPYZODXSA-N CC[C@H](CC1)CC[C@@H]1C(OC(C=CC=C1F)=C1F)=O Chemical compound CC[C@H](CC1)CC[C@@H]1C(OC(C=CC=C1F)=C1F)=O OUBGXJOVPXVFKX-XYPYZODXSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical class C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は液晶材料として有用なエ
ステル誘導体に関し、さらにこのエステル誘導体を含有
する液晶組成物に関するものである。FIELD OF THE INVENTION The present invention relates to an ester derivative useful as a liquid crystal material, and further to a liquid crystal composition containing the ester derivative.
【０００２】[0002]
【従来の技術】液晶表示装置は、時計、電卓をはじめワ
ープロ、テレビ等に広く利用されている。これらの液晶
表示装置の中で特に多く使用されているのは、液晶材料
の光学的異方性および誘電異方性を利用したＴＮ型（ね
じれネマティック型）液晶表示装置である。2. Description of the Related Art Liquid crystal display devices are widely used in word processors, televisions, etc. as well as watches and calculators. Among these liquid crystal display devices, a TN type (twisted nematic type) liquid crystal display device that utilizes the optical anisotropy and the dielectric anisotropy of the liquid crystal material is particularly often used.
【０００３】[0003]
【発明が解決しようとする課題】現在ＴＮ型などの液晶
表示装置に用いられている液晶材料に要求される特性と
しては、液晶温度範囲が広いこと、電気光学的な応答速
度が速いこと、視野角範囲が広いこと、駆動電圧が低い
こと、化学的および光学的に安定であることなどが挙げ
られる。The liquid crystal materials currently used in liquid crystal display devices such as TN type are required to have a wide liquid crystal temperature range, a high electro-optical response speed, and a visual field. It has a wide angular range, a low driving voltage, and is chemically and optically stable.
【０００４】広視野角、高コントラストを得るために
は、液晶層のリターデーション△ｎ・ｄ（△ｎは液晶材
料の複屈折、ｄは液晶層の厚み）を最適化する必要があ
る。しかし、実際に使用されている液晶表示装置では液
晶層の厚みがある範囲内に設定されてしまうため、液晶
材料のΔｎの最適化が必要となっていた。In order to obtain a wide viewing angle and high contrast, it is necessary to optimize the retardation Δn · d (Δn is the birefringence of the liquid crystal material, d is the thickness of the liquid crystal layer) of the liquid crystal layer. However, in a liquid crystal display device that is actually used, the thickness of the liquid crystal layer is set within a certain range, so it is necessary to optimize Δn of the liquid crystal material.
【０００５】また、駆動電圧はしきい値電圧Ｖthの値に
依存し、しきい値電圧Ｖthを小さくすることにより、よ
り低い電圧で液晶表示装置を駆動させることができる。
よって、しきい値電圧Ｖthを小さくする液晶材料が必要
となっていた。The driving voltage depends on the value of the threshold voltage Vth, and by lowering the threshold voltage Vth, the liquid crystal display device can be driven at a lower voltage.
Therefore, a liquid crystal material that reduces the threshold voltage Vth has been required.
【０００６】以上のような特性を全て満足する単一の液
晶化合物は未だに見い出されていない。そのためにいろ
いろな特性をもった数種の液晶化合物を混合したり、あ
るいは非液晶化合物を混合したりして実用に供している
のが現状である。A single liquid crystal compound satisfying all the above characteristics has not yet been found. Therefore, at present, several kinds of liquid crystal compounds having various characteristics are mixed or non-liquid crystal compounds are mixed for practical use.
【０００７】そこで本発明の目的は、液晶組成物に混合
することによって、Δｎおよびしきい値電圧Ｖthを小さ
くすることのできるエステル誘導体を提供することであ
る。Therefore, an object of the present invention is to provide an ester derivative which can reduce Δn and threshold voltage Vth by being mixed with a liquid crystal composition.
【０００８】[0008]
【課題を解決するための手段】本発明のエステル誘導体
は一般式（Ｉ）で表されるものである。Means for Solving the Problems The ester derivative of the present invention is represented by the general formula (I).
【０００９】[0009]
【化２】 [Chemical 2]
【００１０】（ただし、Ｒは炭素原子数が１〜１０のア
ルキル基、Ａはフェニル基またはシクロヘキシル基を示
す。）(However, R represents an alkyl group having 1 to 10 carbon atoms, and A represents a phenyl group or a cyclohexyl group.)
【００１１】また、本発明の液晶組成物は、一般式
（Ｉ）で表されるエステル誘導体を少なくとも一種含有
するものである。The liquid crystal composition of the present invention contains at least one ester derivative represented by the general formula (I).
【００１２】本発明のエステル誘導体の製造方法につい
て説明する。化３はその一例を示したものである。な
お、式中Ｒ、Ａは前記した意味を示す。まず４−アルキ
ルシクロヘキサンカルボン酸または４−アルキル安息香
酸（ａ）に塩化チオニル、五酸化リン等のハロゲン化剤
を作用させて酸塩化物（ｂ）を製造する。次に酸塩化物
（ｂ）と２，３−ジフルオロフェノール（ｃ）とをピリ
ジン等の不活性有機溶媒中で反応させた後、反応混合物
を水洗、乾燥、再結晶することにより一般式（Ｉ）で表
されるエステル誘導体を得ることができる。The method for producing the ester derivative of the present invention will be described. Chemical formula 3 shows an example thereof. In the formula, R and A have the above-mentioned meanings. First, a 4-alkylcyclohexanecarboxylic acid or 4-alkylbenzoic acid (a) is reacted with a halogenating agent such as thionyl chloride or phosphorus pentoxide to produce an acid chloride (b). Next, the acid chloride (b) and 2,3-difluorophenol (c) are reacted in an inert organic solvent such as pyridine, and then the reaction mixture is washed with water, dried, and recrystallized to give the compound of the general formula (I). An ester derivative represented by
【００１３】[0013]
【化３】 [Chemical 3]
【００１４】本発明のエステル誘導体は多くの液晶化合
物と混合し液晶組成物を製造することができる。本発明
のエステル誘導体と混合可能な液晶化合物としてはエス
テル系、シクロヘキシルフェニル系、ビフェニル系、ピ
リミジン系、ジオキサン系、トラン系などが挙げられ
る。The ester derivative of the present invention can be mixed with many liquid crystal compounds to produce a liquid crystal composition. Examples of the liquid crystal compound that can be mixed with the ester derivative of the present invention include ester compounds, cyclohexylphenyl compounds, biphenyl compounds, pyrimidine compounds, dioxane compounds, and tolan compounds.
【００１５】[0015]
【実施例】実施例を用いて本発明を具体的に説明する
が、本発明はこれら実施例に限定されるものではない。EXAMPLES The present invention will be specifically described with reference to examples, but the present invention is not limited to these examples.
【００１６】（実施例１）トランス−４−エチルシクロ
ヘキサンカルボン酸１５．６ｇに塩化チオニル２４ｇを
加え、還流下で２時間反応させ、反応終了後減圧下で塩
化チオニルを留去し、その後２０ｍｍＨｇで減圧蒸留
し、シクロヘキサンカルボン酸酸塩化物１０ｇを得た。
これをトルエン５０ｍｌに溶解し、２，３−ジフルオロ
フェノール８ｇとピリジン８ｇを加え４０℃で３時間反
応させた。反応終了後１００ｍｌの水を加えて有機層を
分離し、希塩酸次いで希アルカリ水溶液の順で洗浄し、
さらに飽和食塩水で洗浄した後、無水硫酸ナトリウムを
加えて乾燥させた。次にこの有機層を濾過し、濾液から
溶媒を減圧留去した。得られた反応生成物をエタノール
から再結晶し、１ｍｍＨｇで減圧蒸留を行い、化４で表
されるトランス−４−エチルシクロヘキサンカルボン酸
−（２，３−ジフルオロ）−フェニルエステル９ｇを得
た。この化合物は融点２６．０℃であった。また、この
化合物の赤外線吸収スペクトルを図１に示す。(Example 1) 24 g of thionyl chloride was added to 15.6 g of trans-4-ethylcyclohexanecarboxylic acid and reacted for 2 hours under reflux. After completion of the reaction, thionyl chloride was distilled off under reduced pressure, and then at 20 mmHg. Distillation under reduced pressure gave 10 g of cyclohexanecarboxylic acid chloride.
This was dissolved in 50 ml of toluene, 8 g of 2,3-difluorophenol and 8 g of pyridine were added, and the mixture was reacted at 40 ° C. for 3 hours. After completion of the reaction, 100 ml of water was added to separate the organic layer, and the organic layer was washed with diluted hydrochloric acid and then diluted alkaline aqueous solution in this order.
After further washing with saturated saline, anhydrous sodium sulfate was added and dried. Next, this organic layer was filtered, and the solvent was distilled off from the filtrate under reduced pressure. The obtained reaction product was recrystallized from ethanol and distilled under reduced pressure at 1 mmHg to obtain 9 g of trans-4-ethylcyclohexanecarboxylic acid- (2,3-difluoro) -phenyl ester represented by Chemical formula 4. This compound had a melting point of 26.0 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【００１７】[0017]
【化４】 [Chemical 4]
【００１８】（実施例２）トランス−４−エチルシクロ
ヘキサンカルボン酸１５．６ｇの代わりにトランス−４
−プロピルシクロヘキサンカルボン酸１７．０ｇを使用
する以外は実施例１と同様の方法で化５で表されるトラ
ンス−４−プロピルシクロヘキサンカルボン酸−（２，
３−ジフルオロ）−フェニルエステル１０ｇを得た。こ
の化合物は融点３８．０℃であった。また、この化合物
の赤外線吸収スペクトルを図２に示す。Example 2 Trans-4-ethylcyclohexanecarboxylic acid Instead of 15.6 g, trans-4 was used.
In the same manner as in Example 1 except that 17.0 g of propylcyclohexanecarboxylic acid was used, trans-4-propylcyclohexanecarboxylic acid- (2,
10 g of 3-difluoro) -phenyl ester was obtained. This compound had a melting point of 38.0 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【００１９】[0019]
【化５】 [Chemical 5]
【００２０】（実施例３）トランス−４−エチルシクロ
ヘキサンカルボン酸１５．６ｇの代わりにトランス−４
−ブチルシクロヘキサンカルボン酸１８．４ｇを使用す
る以外は実施例１と同様の方法で化６で表されるトラン
ス−４−ブチルシクロヘキサンカルボン酸−（２，３−
ジフルオロ）−フェニルエステル１１ｇを得た。この化
合物は融点３２．８℃であった。また、この化合物の赤
外線吸収スペクトルを図３に示す。(Example 3) trans-4-ethylcyclohexanecarboxylic acid Instead of 15.6 g, trans-4 was used.
In the same manner as in Example 1 except that 18.4 g of -butylcyclohexanecarboxylic acid was used, trans-4-butylcyclohexanecarboxylic acid- (2,3-
11 g of difluoro) -phenyl ester was obtained. This compound had a melting point of 32.8 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【００２１】[0021]
【化６】 [Chemical 6]
【００２２】（実施例４）トランス−４−エチルシクロ
ヘキサンカルボン酸１５．６ｇの代わりにトランス−４
−ペンチルシクロヘキサンカルボン酸１９．８ｇを使用
する以外は実施例１と同様の方法で化７で表されるトラ
ンス−４−ペンチルシクロヘキサンカルボン酸−（２，
３−ジフルオロ）−フェニルエステル１２ｇを得た。こ
の化合物は融点３５．５℃であった。また、この化合物
の赤外線吸収スペクトルを図４に示す。(Example 4) trans-4-ethylcyclohexanecarboxylic acid Instead of 15.6 g, trans-4 was used.
In the same manner as in Example 1 except that 19.8 g of pentylcyclohexanecarboxylic acid was used, trans-4-pentylcyclohexanecarboxylic acid- (2,
12 g of 3-difluoro) -phenyl ester was obtained. This compound had a melting point of 35.5 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【００２３】[0023]
【化７】 [Chemical 7]
【００２４】（実施例５）トランス−４−エチルシクロ
ヘキサンカルボン酸１５．６ｇの代わりに４−プロピル
安息香酸１５．０ｇを使用する以外は実施例１と同様の
方法で化８で表される４−プロピル安息香酸−（２，３
−ジフルオロ）−フェニルエステル９ｇを得た。この化
合物は融点３６．２℃であった。また、この化合物の赤
外線吸収スペクトルを図５に示す。(Example 5) 4 represented by Chemical formula 8 in the same manner as in Example 1 except that 15.0 g of 4-propylbenzoic acid was used instead of 15.6 g of trans-4-ethylcyclohexanecarboxylic acid. -Propylbenzoic acid- (2,3
9 g of -difluoro) -phenyl ester was obtained. This compound had a melting point of 36.2 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【００２５】[0025]
【化８】 [Chemical 8]
【００２６】（実施例６）トランス−４−エチルシクロ
ヘキサンカルボン酸１５．６ｇの代わりに４−ペンチル
安息香酸２９．２ｇを使用する以外は実施例１と同様の
方法で化９で表される４−ペンチル安息香酸−（２，３
−ジフルオロ）−フェニルエステル１１ｇを得た。この
化合物は融点４６．５℃であった。また、この化合物の
赤外線吸収スペクトルを図６に示す。(Example 6) 4 represented by Chemical formula 9 in the same manner as in Example 1 except that 29.2 g of 4-pentylbenzoic acid was used in place of 15.6 g of trans-4-ethylcyclohexanecarboxylic acid. -Pentylbenzoic acid- (2,3
11 g of -difluoro) -phenyl ester was obtained. This compound had a melting point of 46.5 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【００２７】[0027]
【化９】 [Chemical 9]
【００２８】（実施例７）化１０で表される化合物を混
合した液晶組成物９０重量部に、実施例１で製造した本
発明のエステル誘導体を１０重量部加え液晶組成物を作
製した。その液晶組成物の特性を表１に示す。Example 7 A liquid crystal composition was prepared by adding 10 parts by weight of the ester derivative of the present invention prepared in Example 1 to 90 parts by weight of the liquid crystal composition prepared by mixing the compound represented by Chemical formula 10. The characteristics of the liquid crystal composition are shown in Table 1.
【００２９】ここで、化１０で表される化合物のみから
なる液晶組成物の特性はＮ−Ｉ点７２℃、Δｎ０．１３
８、粘度２７．９ｃｐ、Ｖth１．６８ｖであった。The characteristics of the liquid crystal composition consisting only of the compound represented by Chemical formula 10 are as follows: NI point 72 ° C., Δn 0.13
8, the viscosity was 27.9 cp, and the Vth was 1.68v.
【００３０】[0030]
【化１０】 [Chemical 10]
【００３１】[0031]
【表１】 [Table 1]
【００３２】（実施例８〜１２）実施例７と同様に化１
０で表される化合物を混合した液晶組成物９０重量部
に、実施例２〜６で製造したエステル誘導体をそれぞれ
１０重量部ずつ加え、液晶組成物を作製した。その液晶
組成物の特性を表１に示す。(Examples 8 to 12) Chemical formula 1 as in Example 7
10 parts by weight of each of the ester derivatives produced in Examples 2 to 6 was added to 90 parts by weight of the liquid crystal composition in which the compound represented by 0 was mixed to prepare a liquid crystal composition. The characteristics of the liquid crystal composition are shown in Table 1.
【００３３】表１から明らかなように、本発明のエステ
ル誘導体は、Δｎおよびしきい値電圧Ｖthを小さくする
ものである。As is clear from Table 1, the ester derivative of the present invention reduces Δn and the threshold voltage Vth.
【００３４】[0034]
【発明の効果】本発明のエステル誘導体は、液晶組成物
に混合することによって、Δｎおよびしきい値電圧Ｖth
を小さくすることができる。また、粘度を低下させるも
のもある。そのため本発明のエステル誘導体を含有する
液晶組成物は液晶材料として優れた特性を有し、またこ
の液晶組成物を搭載した液晶表示装置は良好な表示特性
を有する。さらに、本発明のエステル誘導体は種々の化
合物との相互溶解性が大きく、液晶組成物の構成物質と
して多くの液晶材料と組み合わせて使用することがで
き、液晶組成物の特性改良に有用なものである。The ester derivative of the present invention can be mixed with a liquid crystal composition to obtain Δn and a threshold voltage Vth.
Can be made smaller. In addition, there are some that lower the viscosity. Therefore, a liquid crystal composition containing the ester derivative of the present invention has excellent properties as a liquid crystal material, and a liquid crystal display device equipped with this liquid crystal composition has good display properties. Furthermore, the ester derivative of the present invention has a high mutual solubility with various compounds, can be used in combination with many liquid crystal materials as a constituent of a liquid crystal composition, and is useful for improving the characteristics of the liquid crystal composition. is there.
【図１】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 1 is a diagram showing an infrared absorption spectrum of an ester derivative of the present invention.
【図２】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 2 is a diagram showing an infrared absorption spectrum of the ester derivative of the present invention.
【図３】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 3 is a diagram showing an infrared absorption spectrum of the ester derivative of the present invention.
【図４】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 4 is a diagram showing an infrared absorption spectrum of the ester derivative of the present invention.
【図５】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 5 is a diagram showing an infrared absorption spectrum of the ester derivative of the present invention.
【図６】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 6 is a diagram showing an infrared absorption spectrum of the ester derivative of the present invention.
Claims (2)
体。 【化１】 （ただし、Ｒは炭素原子数が１〜１０のアルキル基、Ａ
はフェニル基またはシクロヘキシル基を示す。）1. An ester derivative represented by the general formula (I). [Chemical 1] (However, R is an alkyl group having 1 to 10 carbon atoms, A
Represents a phenyl group or a cyclohexyl group. )
とも一種含有する液晶組成物。2. A liquid crystal composition containing at least one ester derivative according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30325392A JP3291331B2 (en) | 1992-10-16 | 1992-10-16 | Liquid crystal composition containing ester derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30325392A JP3291331B2 (en) | 1992-10-16 | 1992-10-16 | Liquid crystal composition containing ester derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06128196A true JPH06128196A (en) | 1994-05-10 |
| JP3291331B2 JP3291331B2 (en) | 2002-06-10 |
Family
ID=17918729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30325392A Expired - Fee Related JP3291331B2 (en) | 1992-10-16 | 1992-10-16 | Liquid crystal composition containing ester derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3291331B2 (en) |
-
1992
- 1992-10-16 JP JP30325392A patent/JP3291331B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP3291331B2 (en) | 2002-06-10 |
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