JPH01261493A - Liquid crystal composition - Google Patents
Liquid crystal compositionInfo
- Publication number
- JPH01261493A JPH01261493A JP8819188A JP8819188A JPH01261493A JP H01261493 A JPH01261493 A JP H01261493A JP 8819188 A JP8819188 A JP 8819188A JP 8819188 A JP8819188 A JP 8819188A JP H01261493 A JPH01261493 A JP H01261493A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- crystal composition
- optically active
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims description 48
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011737 fluorine Chemical group 0.000 claims abstract description 4
- 229910052731 fluorine Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052739 hydrogen Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000002269 spontaneous effect Effects 0.000 abstract description 11
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 10
- -1 biphenylcarboxylic ester Chemical class 0.000 abstract description 9
- 239000013078 crystal Substances 0.000 abstract description 5
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
- 239000012071 phase Substances 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 230000007547 defect Effects 0.000 description 10
- 230000010287 polarization Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YNBBQLUKHHSKPW-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 YNBBQLUKHHSKPW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 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 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 210000002858 crystal cell Anatomy 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000005621 ferroelectricity Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- HPXRODIQSWVJGZ-UHFFFAOYSA-N octan-2-yl 2-fluoro-4-hydroxybenzoate Chemical compound CCCCCCC(C)OC(=O)C1=CC=C(O)C=C1F HPXRODIQSWVJGZ-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- TZXJFVPLRNOQFB-UHFFFAOYSA-N 2-benzylidene-6-[(4-decoxyphenyl)methylideneamino]-4-methylhexanoic acid Chemical group C1=CC(OCCCCCCCCCC)=CC=C1C=NCCC(C)CC(C(O)=O)=CC1=CC=CC=C1 TZXJFVPLRNOQFB-UHFFFAOYSA-N 0.000 description 1
- WIPYZRZPNMUSER-UHFFFAOYSA-N 2-chloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1Cl WIPYZRZPNMUSER-UHFFFAOYSA-N 0.000 description 1
- BDDVAWDNVWLHDQ-UHFFFAOYSA-N 2-chloro-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(Cl)=C1 BDDVAWDNVWLHDQ-UHFFFAOYSA-N 0.000 description 1
- NXWTWYULZRDBSA-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1F NXWTWYULZRDBSA-UHFFFAOYSA-N 0.000 description 1
- BUGZXWUBIUJNGN-UHFFFAOYSA-N 2-fluorohexyl 4-hydroxybenzoate Chemical compound CCCCC(F)COC(=O)C1=CC=C(O)C=C1 BUGZXWUBIUJNGN-UHFFFAOYSA-N 0.000 description 1
- 125000005274 4-hydroxybenzoic acid group Chemical group 0.000 description 1
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- ARGDYOIRHYLIMT-UHFFFAOYSA-N n,n-dichloro-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N(Cl)Cl)C=C1 ARGDYOIRHYLIMT-UHFFFAOYSA-N 0.000 description 1
- DZSGCNKPXQBWGT-UHFFFAOYSA-N octan-2-yl 2-hydroxybenzoate Chemical compound CCCCCCC(C)OC(=O)C1=CC=CC=C1O DZSGCNKPXQBWGT-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は光学活性基を有する液晶組成物に関する。[Detailed description of the invention] [Industrial application field] The present invention relates to a liquid crystal composition having an optically active group.
液晶表示素子の表示方式として現在広く実用に供されて
いるものは、ねじれネマチック型（ＴＮ）及び動的散乱
型（ＤＳ）である。これらはネマチック液晶を主成分と
したネマチック液晶セルによる表示である。従来のネマ
チック液晶セルの短所の一つに応答速度が遅く、最高数
ミリ秒のオーダーの応答速度しか得られないという事実
が挙げられる。そしてこのことがネマチック液晶セルの
応用範囲を制約する一因となっている。これに対して最
近スメクチック液晶セルを用いればより高速な応答が得
られることが明らかになってきた。Currently, the display systems of liquid crystal display elements that are widely used in practical use are twisted nematic (TN) and dynamic scattering (DS). These are displays using nematic liquid crystal cells containing nematic liquid crystal as a main component. One of the disadvantages of conventional nematic liquid crystal cells is the fact that their response speeds are slow, with response times on the order of a few milliseconds at most. This is one of the factors that limits the range of applications of nematic liquid crystal cells. In contrast, it has recently become clear that a faster response can be obtained by using a smectic liquid crystal cell.
光学活性なスメクチンク液晶の中には強誘電性を示すも
のがあることが知られており、その応用に関して大きな
関心が持たれている。強誘電性液晶は、１９７５年、Ｒ
，Ｂ、メイヤー（Ｒ，Ｂ−Ｍｅ７８ｒ ）らにより最初
に合成されたが〔ジュルナール・ド・フイジーク（、ｒ
、ｐｈｙｓ、 ） 、第３６巻、第Ｌ６９頁（１９７５
））それは、４− （４’−ｎ−デシルオキシベンジリ
デンアミノ）−２−メチルブチルシンナメート（ＤＯＢ
ＡＭＢＣ）を代表例とするシップ塩基系の化合物であり
、これが光学活性の状態、すなわちカイラルスメクチッ
クＣ相において強誘を注を示すことを特徴とするもので
ある。その後、Ｎ、Ａ、クラーク（Ｎ、人。It is known that some optically active smectinic liquid crystals exhibit ferroelectricity, and there is great interest in their applications. Ferroelectric liquid crystal was developed in 1975 by R.
, B, Mayer (R,B-Me78r) et al. [Journard de Fuisique (, r
, phys, ), Volume 36, Page L69 (1975
)) It is 4-(4'-n-decyloxybenzylideneamino)-2-methylbutylcinnamate (DOB
It is a ship base-based compound of which AMBC) is a typical example, and is characterized by exhibiting strong attraction in an optically active state, that is, a chiral smectic C phase. After that, N, A, Clark (N, person.
Ｃ１ａｒｋ ）ら〔アプライド・フィツクス・レターズ
（Ａｐｐｌ、Ｐｈｙｓ、Ｉｅｔｔ、 ）、第３６巻、第
８９９頁（１９８０））により、ＤＯＢＡＭＢＣの薄膜
セルにおいてマイクロ秒オーダーの高速応答性が発見さ
れ、これが契機となって強誘電性液晶はその高速応答性
やメモリ性を利用して、液晶テレビ等のデイスプレィ用
のみならず、光プリンターヘッド、光フーリエ変換素子
、ライトバルブ等のオプトエレクトロニクス関係素子の
部品にも使用可能な材料として注目を集めている。強誘
電性液晶セルにおいては、誘電率が高く、自発分極が大
きい材料を用いるほどセルを高速駆動できて有利である
ため、自発分極の大きい材料の開発が望まれている。C1ark) et al. (Applied Fixtures Letters (Appl, Phys, Iett, ), Vol. 36, p. 899 (1980)) discovered high-speed response on the microsecond order in the thin film cell of DOBAMBC, and this became an opportunity. Due to its high-speed response and memory properties, ferroelectric liquid crystals are used not only for displays such as LCD televisions, but also for parts of optoelectronic devices such as optical printer heads, optical Fourier transform elements, and light valves. It is attracting attention as a usable material. In ferroelectric liquid crystal cells, it is advantageous to use a material with a high dielectric constant and a large spontaneous polarization because the cell can be driven at high speed, so there is a desire to develop a material with a large spontaneous polarization.
また実用上は、液晶組成物自身が安定であり、更には、
室温を中心とする広い温度範囲で強誘電性を示すことが
必要である。In addition, in practical use, the liquid crystal composition itself is stable, and furthermore,
It is necessary to exhibit ferroelectricity over a wide temperature range centered around room temperature.
しかし、ＤＯＢＡＭＢＣなどのシック塩基型の化合物は
水や光等（対する安定性の点で難点がちり、また強誘電
性を示す温度範囲も室温よジＳＯＣ程度高温側にあるな
ど、実用に適するものではなかった。そこで、強誘電性
液晶材料として、物理的化学的に安定で、しかも大きい
自発分極を持つ材料系の実現が強く期待されている。However, thick base type compounds such as DOBAMBC have some drawbacks in terms of stability against water, light, etc., and the temperature range in which they exhibit ferroelectricity is on the high temperature side of room temperature and diSOC, so they are not suitable for practical use. Therefore, there are strong expectations for the realization of a material system that is physically and chemically stable and has large spontaneous polarization as a ferroelectric liquid crystal material.
本発明の目的は化学的安定性、九安定注に優れ、自発分
極が大きく、かつカイラルスメクチックＣ相の温度範囲
の広い新規液晶組成物を得ることにある。また本発明は
このような液晶組成物を用いて高速応答性を有する表示
素子等を提供しようとするものである。An object of the present invention is to obtain a new liquid crystal composition that has excellent chemical stability and nine stability, large spontaneous polarization, and a wide temperature range of chiral smectic C phase. Further, the present invention aims to provide a display element and the like having high-speed response using such a liquid crystal composition.
本発明を概説すれば、本発明は液晶組成物に関する発明
であって、下記一般式！：
（式中、Ｒ１は炭素数４以上のアルキル基又はアルキル
オキシ基、Ｒ２は炭素数４以上のアルキル基を示し、Ｒ
７及びＲ２のいずれか一方は光学活性基であり、Ｘは塩
素又は水素、Ｙは塩素又はフッ素を示す）で表される化
合物を必須成分とすることを特徴とする。To summarize the present invention, the present invention relates to a liquid crystal composition, which has the following general formula! : (wherein, R1 represents an alkyl group or an alkyloxy group having 4 or more carbon atoms, R2 represents an alkyl group having 4 or more carbon atoms, and R
Either one of 7 and R2 is an optically active group, X is chlorine or hydrogen, and Y is chlorine or fluorine.
一般式！の光学活性化合物は、不斉炭素にカルボニル基
を直接結合させているほか、分子の長軸の横方向にフッ
素あるいは塩素の少なくとも一方を含有しているので、
高い旋光性を有している。また、中心骨格はビフェニル
カルボン酸エステル構造を有しており、更に分子両末端
に長鎖アルキル基が存在するので、それ自身が液晶性を
示すものである。General ceremony! In addition to directly bonding a carbonyl group to an asymmetric carbon, the optically active compound contains at least one of fluorine or chlorine in the lateral direction of the long axis of the molecule.
It has high optical rotation. Furthermore, since the central skeleton has a biphenylcarboxylic acid ester structure and long-chain alkyl groups are present at both ends of the molecule, it itself exhibits liquid crystallinity.
また、上記液晶組成物は、下記一般式Ｍ：（式中、Ｒ１
け炭素数４以上のアルキル基又はアルキルオキシ基、Ｒ
２Ｈ炭素数４以上のアルキル基を示し、Ｒ１及びＲ２の
いずれか一方は光学活性基である）で表される化合物を
含有してもよい。Further, the liquid crystal composition has the following general formula M: (wherein, R1
an alkyl group or alkyloxy group having 4 or more carbon atoms, R
2H represents an alkyl group having 4 or more carbon atoms, and either R1 or R2 is an optically active group).
各式中の各アルキル基の炭素数は４〜１８が好まじり６
また式！とＩでＲ１、Ｒ２は異なっていてもよい。The number of carbon atoms in each alkyl group in each formula is preferably 4 to 18, and 6
Another ceremony! and I, R1 and R2 may be different.
式１の化合物はこの化合物の存在によジカイラルスメク
チノクＣ液晶相を示す温度範囲が室温を包含して広く、
シかも欠陥の少ない液晶組成物を得ることができる。Due to the presence of this compound, the compound of formula 1 exhibits a dichiral smectinoc C liquid crystal phase in a wide temperature range including room temperature,
Furthermore, a liquid crystal composition with fewer defects can be obtained.
その他、本発明の液晶組成物において配合可能な液晶化
合物の例には通常の光学活性又は不活性のスメクチック
液晶がある。Other examples of liquid crystal compounds that can be incorporated into the liquid crystal composition of the present invention include ordinary optically active or inactive smectic liquid crystals.
本発明の式ＩとＩの化合物は、例えば次のような方法に
従って製造することができる。The compounds of formulas I and I according to the invention can be prepared, for example, according to the following method.
光学活性−２−ハロゲノ−４−ヒドロキシ安息香酸−１
−メチルへグチルエステル類は基本的には竹原らの方法
〔竹原貞夫ほか、第１１回液晶討論会予稿集、第１７６
頁（１９８５）：）で製造できるが、塩素化合物の場合
は市販の３−クロロ−４−シアンフェノールを７５％硫
散中で加水分解して、２−クロロ−４−ヒドロキシ゛安
息香酸を得る方法によった。次にこれらの２−ハロゲノ
−４−ヒドロキシ安息香酸類を硫酸触媒、トルエン溶媒
中、例えば光学活１１２−オクタツールと加熱し、生成
する水を系外に除去しながら反応させ、光学活性−２−
フルオロー又＃′１２−クロロ−４−ヒドロキシ安息香
酸−１−メチルヘプチルエステルを製造できる。Optically active 2-halogeno-4-hydroxybenzoic acid-1
- Methyl hegthyl esters are basically obtained by the method of Takehara et al. [Sadao Takehara et al., Proceedings of the 11th Liquid Crystal Symposium, No.
(1985): ), but in the case of chlorine compounds, commercially available 3-chloro-4-cyanphenol is hydrolyzed in 75% sulfur to obtain 2-chloro-4-hydroxybenzoic acid. According to Next, these 2-halogeno-4-hydroxybenzoic acids are heated with a sulfuric acid catalyst and optically active 112-octatool in a toluene solvent, and reacted with optically active 112-octatool while removing the water produced from the system.
Fluoro-12-chloro-4-hydroxybenzoic acid-1-methylheptyl ester can be produced.
ｔ７’ｃ、ｓ’−クロロ−４′−ｎ−アルキルオキシ−
４−ビフェニルカルボン酸ｔｄ、４’ −ｎ −フルキ
ルオキシ−４−ビフェニルカルボンＲ’ｔＮ、Ｎ−ジク
ロロ−ｐ−トルエンスルホン酸アミド（ジクロラミンＴ
）および塩酸触媒を用いて塩素化することによ夕裂造す
ることができる。t7'c, s'-chloro-4'-n-alkyloxy-
4-biphenylcarboxylic acid td, 4'-n-furkyloxy-4-biphenylcarboxylic acid R'tN, N-dichloro-p-toluenesulfonic acid amide (dichloramine T
) and chlorination using a hydrochloric acid catalyst.
更Ｋ、！’−／ロロー４′−アルキルオキシ−４−ビフ
ェニルカルボン酸、又は４′−アルキルオキシ−４−ビ
フェニルカルボン酸の酸クロライドと、光学活性−２−
ハロゲノ−４−ヒドロキシ安息香酸−１−メチルヘプチ
ルエステル及び光学活性アルコールとの混合物とを反応
させる方法、又は、これらのヒドロキシ安息香酸化合物
あるいけアルコールをそれぞれ単独で上記ビフェニルカ
ルボン酸の酸クロライドと反応させた後に両方の生成物
を混合する方法のいずれかにより目的とする液晶組成物
を製造することができる。Sara K! '-/RORO 4'-alkyloxy-4-biphenylcarboxylic acid or acid chloride of 4'-alkyloxy-4-biphenylcarboxylic acid and optically active -2-
A method of reacting halogeno-4-hydroxybenzoic acid-1-methylheptyl ester and a mixture with an optically active alcohol, or a method of reacting each of these hydroxybenzoic acid compounds or alcohols alone with the acid chloride of the biphenylcarboxylic acid. The desired liquid crystal composition can be manufactured by any of the methods of mixing both products after mixing the two products.
なお、この段階の反応では光学活性アルコールは２種類
以上共存していても差支えない。また光学活性ビフェニ
ルカルボン酸を使用するときには、光学不活性のアルコ
ールを使用して同様に液晶組成物を製造できる。Note that in this stage of the reaction, two or more types of optically active alcohols may coexist. Further, when using optically active biphenylcarboxylic acid, a liquid crystal composition can be similarly produced using optically inactive alcohol.
以下、本発明を実施例により更に具体的に説明するが、
本発明の適用範囲はこれらの実施例によって限定される
ものではない。Hereinafter, the present invention will be explained in more detail with reference to Examples.
The scope of application of the present invention is not limited by these examples.
比較例１
（ａ）２−フルオロ−４−ヒドロキシ安息香酸５．２Ｉ
及び光学活性−２−オクタツール６．１９を濃硫酸５ｄ
１ トルエン１２０Ｍと共に加熱還流させ、生成する水
を系外に除去しながら７時間反応させ、水を加えてトル
エン抽出し、希水酸化ナトリウム水溶液で抽出し、この
水溶液を塩酸で散在にすると油状物が得られた。これを
エーテル抽出し、水で洗浄し、無水硫酸マグネシウムで
乾燥し、エーテルを留去してヘキサンを溶媒とするシリ
カゲルのカラムクロマトで精製し、光学活性−２−フル
オロー４−ヒドロキシ安息香酸−１−メチルヘプチルエ
ステルｔ？Ｌｊｃ。Comparative Example 1 (a) 2-fluoro-4-hydroxybenzoic acid 5.2I
and optically active-2-octatool 6.19 in concentrated sulfuric acid 5d
1 Heat to reflux with 120M toluene, react for 7 hours while removing the water produced from the system, add water and extract with toluene, extract with dilute aqueous sodium hydroxide solution, and scatter this aqueous solution with hydrochloric acid to form an oily substance. was gotten. This was extracted with ether, washed with water, dried over anhydrous magnesium sulfate, distilled off the ether, and purified with silica gel column chromatography using hexane as a solvent. -Methylheptyl ester t? Ljc.
（ｂｌ 次に３′−クロロ−４７−オクチルオキシ−
４−ビフェニルカルボン酸３．９Ｉを塩化チオニル５Ｍ
と５０〜６５Ｃで５時間加熱した後−夜装置し、塩化チ
オニルを留去してトルエン４０ｆｆｉｊに溶解し、（ａ
）の光学活性−２−フルオロ−４−ヒドロキシ安息香ｒ
ｆｊｔ−ｉ−メチルヘプチルエステル２．６１のピリジ
ン５０Ｒｔの溶液に徐々に加えて５８〜７０Ｃで３時間
かくはんし、−夜放置した復水を加えてトルエンで抽出
し、トルエン層を希炭酸ナトリウム水溶液で洗浄、更に
水洗して溶媒を留去し、残留物をシリカゲルのカラムク
ロマト（溶媒ヘキサン−トルエン）で精製して、光学活
性−３′−クロロ−ｌ−オクチルオキシ−４−ビフェニ
ルカルボンＯ−Ｓ／／−フルオロ−４’−（１−メチル
へブチルオキシカルボニル）７エ二ルエステル（一般式
Ｉにおいて、Ｘ＝Ｃ／、Ｙ＝？の化合物）を製造した。(bl then 3'-chloro-47-octyloxy-
4-biphenylcarboxylic acid 3.9I to thionyl chloride 5M
After heating at 50-65C for 5 hours, the thionyl chloride was distilled off, dissolved in 40ffij of toluene, and (a
) optically active -2-fluoro-4-hydroxybenzoyl
Gradually add fjt-i-methylheptyl ester 2.61 to a solution of pyridine 50Rt, stir at 58 to 70C for 3 hours, add the condensate left overnight, extract with toluene, and add the toluene layer to dilute aqueous sodium carbonate solution. After washing with S//-fluoro-4'-(1-methylhebutyloxycarbonyl)7enyl ester (compound of general formula I, where X=C/, Y=?) was produced.
この化合物は４５〜１０１ＣでカイラルスメクチックＣ
液晶相を示した。This compound is chiral smectic C with 45-101C
It showed a liquid crystal phase.
（Ｃ１ｆａｌと同様にして光学活性−２−クロロ−４−
ヒドロキシ安息香酸−１−メチルへブチルエステルを製
造し、３′−クロロ−１−オクチルオキシ−４−ビフェ
ニルカルボン酸を上記（１）ｌと同様に反応させて光学
活性−３′−クロロ−４７−オクチルオキシ−４−ビフ
ェニルカルボン酸−３〃−クロロ−４’−（１−メチル
へブチルオキシカルボニル）フェニルエステル（一般式
■において、ｘ ＝ ｙ ＝ ｃｔ の化合物）を製
造した。また、４′−オクチルオキシ−４−ビフェニル
カルボン酸及び光学活性−２−クロロ−４−ヒドロキシ
安息香酸−１−メチルへブチルエステルを用いて同様に
して光学活性−ａ／−オクチルオキシ−４−ビフェニル
カルボン酸−ダークロロー４’−（１−メチルへブチル
オキシカルボニル）フェニルエステル（一般式■におい
て、Ｘ＝Ｈ，Ｙ＝Ｃ／（７）化合物）を製造した。(Similarly to C1fal, optically active -2-chloro-4-
Hydroxybenzoic acid-1-methylhebutyl ester was produced, and 3'-chloro-1-octyloxy-4-biphenylcarboxylic acid was reacted in the same manner as in (1)l above to obtain optically active -3'-chloro-47. -Octyloxy-4-biphenylcarboxylic acid-3-chloro-4'-(1-methylhebutyloxycarbonyl) phenyl ester (compound of general formula (1) where x = y = ct) was produced. Similarly, optically active -a/-octyloxy-4- Biphenylcarboxylic acid-darklow 4'-(1-methylhebutyloxycarbonyl)phenyl ester (in the general formula (1), X=H, Y=C/(7) compound) was produced.
更に光学活性−２−フルオロ−４−ヒドロキシ安息香酸
−１−メチルヘプチルエステル及び４′−オクチルオキ
シ−４−ビフェニルカルボン酸を用いるほかは上記ｔｂ
）と同様にして光学活性−４′−オクチルオキシ−４−
ビフェニルカルボン酸−３“−フルオロ−４’−（１−
メチルへブチルオキシカルボニル）フェニルエステル（
一般式Ｉにおいて、Ｘ＝Ｈ，Ｙ＝Ｆの化合物）を製造し
た。The above tb except that optically active 2-fluoro-4-hydroxybenzoic acid-1-methylheptyl ester and 4'-octyloxy-4-biphenylcarboxylic acid are further used.
) in the same manner as optically active -4'-octyloxy-4-
Biphenylcarboxylic acid-3"-fluoro-4'-(1-
methylhebutyloxycarbonyl) phenyl ester (
A compound of general formula I, where X=H, Y=F) was produced.
［ｄｌ 上記（ｂ）及び（Ｃ）における生成物をポリ
イミド膜をつけてラビング処理済入のガラスよりなるセ
ルに挟み、偏光顕微鏡で観察したところ、ドメインに欠
陥が多く、倍率１００倍でいずれも約５０ないし４０個
以上の欠陥が認められた。[dl When the products in (b) and (C) above were sandwiched between cells made of rubbed glass with a polyimide film attached, and observed with a polarizing microscope, there were many defects in the domains, and both were observed at 100x magnification. Approximately 50 to 40 or more defects were observed.
実施例１
＋１１式に相当する成分
（１１式に相当する成分
Ｃｒ
比較例１（ａ）と同様に反応を行った後、トルエン溶液
を水で洗浄し、無水硫酸マグネシウムで乾燥し、トルエ
ンを留去して光学活性−２−フルオロ−４−ヒドロキシ
安息香酸−１−メチルヘプチルエステルと光学活性−２
−オクタツールとの混合物を得た。Example 1 Component corresponding to formula +11 (component Cr corresponding to formula 11) After carrying out the reaction in the same manner as in Comparative Example 1(a), the toluene solution was washed with water, dried over anhydrous magnesium sulfate, and the toluene was distilled off. to give optically active 2-fluoro-4-hydroxybenzoic acid-1-methylheptyl ester and optically active 2-fluoro-4-hydroxybenzoic acid-1-methylheptyl ester.
- A mixture with octatool was obtained.
次に１３′−クロロ−４′−オクチルオキシ−４−ビフ
ェニルカルボン酸３．８ 、！ｉ’の酸クロライドをト
ルエン溶液とし、前記の光学活性−２−フルオロー４−
ヒドロキシ安息香酸−１−メチルヘプチルエステルと光
学活性−２−オクタツールとの混合物２．７９のピリジ
ン５ａｒｎｌの溶液に徐々に加えて５５〜７０Ｃ’で３
時間かくはんし、−夜放置した復水を加えてトルエンで
抽出し、トルエン層を希塩酸で洗浄、更に水洗して溶媒
を留去し、残留物をシリカゲルのカラムクロマト（溶媒
ヘキサン−トルエン）で精製して、液晶組成物■を得た
。Next, 13'-chloro-4'-octyloxy-4-biphenylcarboxylic acid 3.8,! The acid chloride of i' was dissolved in toluene, and the optically active -2-fluoro-4-
A mixture of hydroxybenzoic acid-1-methylheptyl ester and optically active 2-octatool was gradually added to a solution of 2.79 ml of pyridine and heated at 55 to 70 C'.
Stir for hours, add condensate left overnight, extract with toluene, wash the toluene layer with diluted hydrochloric acid, further wash with water, distill off the solvent, and purify the residue with silica gel column chromatography (solvent: hexane-toluene). As a result, a liquid crystal composition (2) was obtained.
この液晶組成物を厚さ約３μｍ の透明電極付きセルに
封入し、±５Ｖ、ＩＨｚ の電界を印加しながら偏光
顕微鏡で観察すると、２１．４〜？ ６．５ Ｃの範囲
で明りように応答するのが認められた。その他の相転移
＠度は後記光１に他の例と共に示しである。ただしＣｒ
ｙは結晶、Ｓ（１はカイラルスメクチツクＣ相で、上記
の電界に対して少なくとも一部が応答することを表して
いる。ＳＡｆ″ｉスメクチンクＡ相、Ｈ＋ はカイラ
ルネマチック相、工は等方性液相を表している。This liquid crystal composition was sealed in a cell with a transparent electrode about 3 μm thick, and when observed with a polarizing microscope while applying an electric field of ±5 V and IHz, the result was 21.4~? A clear response was observed in the range of 6.5C. Other phase transitions are shown in Light 1 below along with other examples. However, Cr
y is a crystal, S(1 is a chiral smectic C phase, which indicates that at least a part of it responds to the above electric field.SAf''i is a smectic A phase, H+ is a chiral nematic phase, It represents an orthotropic liquid phase.
捷た・けその相が存在すること、−は存在しないことを
表している。It means that the aspect of Katsuta and Keso exists, and - means that it does not exist.
この液晶組成物を厚さ６５μｍ の透明電極付きセルに
封入し、三角波法で自発分極を測定したところ、その頭
け５４ ｎＣ／ ｃｍ２であった。This liquid crystal composition was sealed in a cell with a transparent electrode having a thickness of 65 μm, and its spontaneous polarization was measured using the triangular wave method, and the initial polarization was found to be 54 nC/cm2.
また、この液晶組成物は比較例１における光学活性化合
物二３′−クロロ−４′−オクチルオキシ−４−ビフェ
ニルカルボン酸−ｓ／Ｉ−フルオロ−４’−（１−メチ
ルへブチルオキシカルボニル）フェニルエステルに比較
して室温に近く、シかも広い温度範囲でＳＣ）［−示し
ていることがわかる。In addition, this liquid crystal composition contains the optically active compound 23'-chloro-4'-octyloxy-4-biphenylcarboxylic acid-s/I-fluoro-4'-(1-methylhebutyloxycarbonyl) in Comparative Example 1. It can be seen that the temperature is closer to room temperature than that of phenyl esters, and the temperature range is wider than that of phenyl esters.
更に、比較例１と同一条件で観察したとき、この液晶組
成物は視野中の欠陥の数は１０個と少なく、この組成物
の方が単一化合物よジも明らかに優れた配向性を示した
。この原因は、粘度の低い６′−クロロ−４′−オクチ
ルオキシ−４−ヒフェニルカルボン酸−１−メチルヘフ
チルエステルが存在することにより、液晶組成物の粘度
も低下し配向性が向上するためと推定される。Furthermore, when observed under the same conditions as Comparative Example 1, this liquid crystal composition had as few as 10 defects in the field of view, and this composition clearly showed better orientation than a single compound. Ta. The reason for this is that the presence of 6'-chloro-4'-octyloxy-4-hyphenylcarboxylic acid-1-methylhephthyl ester, which has a low viscosity, reduces the viscosity of the liquid crystal composition and improves the orientation. It is estimated that this is due to
実施例２
光学活性−２−フルオロー４−ヒドロキシ安息香酸−１
−メチルへグチルエステルノ代わりに光学活性−２−ク
ロロ−４−ヒドロキシ安息香酸−１−メチルヘプチルエ
ステルｔ、３’−クロロ−４′−オクチルオキシ−４−
ビフェニルカルボン酸の代わり Ｋ ３’−クロロ−４
′−デシルオキシ−４−とフェニルカルボン酸を用いる
ほかは実施例１と同様にして液晶組成物■を、光学活性
−２−クロロ−４−ヒドロキシ安息香酸−１−メチルヘ
プチルエステル及び４′−オクチルオキシ−４−ビフェ
ニルカルボン酸ヲ用いるほかは実施例１と同様にして液
晶組成物■を、まり４′−オクチルオキシ−４−ビフェ
ニルカルボン酸を用いるほかは実施例１と同様にして液
晶組成物■を製造した。これらの液晶組成物の相転移温
度は表１に示しである。Example 2 Optically active-2-fluoro-4-hydroxybenzoic acid-1
- Optically active -2-chloro-4-hydroxybenzoic acid-1-methylheptyl ester t, 3'-chloro-4'-octyloxy-4-
Substitute for biphenylcarboxylic acid K 3'-chloro-4
Liquid crystal composition (1) was prepared in the same manner as in Example 1 except that '-decyloxy-4- and phenylcarboxylic acid were used. A liquid crystal composition (2) was prepared in the same manner as in Example 1, except that oxy-4-biphenylcarboxylic acid was used, and a liquid crystal composition was prepared in the same manner as in Example 1, except that 4'-octyloxy-4-biphenylcarboxylic acid was used. ■ was manufactured. The phase transition temperatures of these liquid crystal compositions are shown in Table 1.
また、実施例１と同一条件で測定した自発分ＸＯ値け■
５７、■３９及び■４７ ｎＣ／ｃ１１Ｌ２であった。In addition, the spontaneous XO value measured under the same conditions as Example 1
57, ■39 and ■47 nC/c11L2.
更に、比較例１と同一条件で観祭したとき、これらの液
晶組成物は視野中の欠陥の数＃′１１０〜１２個前後と
少なく、これらの組成物の方が単一化合物よりも明らか
に優れた配向性を示した。Furthermore, when viewed under the same conditions as Comparative Example 1, these liquid crystal compositions had fewer defects in the field of view, around #'110 to 12, and these compositions clearly had more defects than single compounds. It showed excellent orientation.
実施例３
ｆｌ１式に相当する成分
用式に相当する成分
比較例１と同様にして光学活性−３′−クロロ−４７−
オクチルオキシ−４−ビフェニルカルボン酸−３１−フ
ルオロ−４’−（１−メチルへブチルオキ７カルボニル
）フェニルエステルヲ裂造した。この化合物の１０重量
部と、４′−オクチルオキシ−４−ビフェニルカルボン
酸及びラセミ体の２−オクタツールを用いるほかは比較
例１の（ｂｌと同様にして製造した４′〜オクチルオキ
シ−４−ビフェニルカルボン酸−１−メチルヘプチルエ
ステルの９０重量部とを混合して液晶組成物■を製造し
た。この液晶組成物の相転移温度は表ＩＫ示しである。Example 3 Component corresponding to fl1 formula Optically active -3'-chloro-47-
Octyloxy-4-biphenylcarboxylic acid-31-fluoro-4'-(1-methylhebutylox7carbonyl)phenyl ester was prepared. 4'-octyloxy-4 produced in the same manner as in Comparative Example 1 (bl) except that 10 parts by weight of this compound, 4'-octyloxy-4-biphenylcarboxylic acid and racemic 2-octatool were used. -Biphenylcarboxylic acid-1-methylheptyl ester (90 parts by weight) was mixed to prepare a liquid crystal composition (2).The phase transition temperature of this liquid crystal composition is shown in Table IK.
また、実施例１と同一条件で測定した自発分極の値Ｆｉ
５２ｒ１Ｃ／ｃＩｒＬ２であった。In addition, the spontaneous polarization value Fi measured under the same conditions as Example 1
52r1C/cIrL2.
更に、比較例１と同一条件で観祭したとき、この液晶組
成物■は視野中の欠陥の数は１１個と少なく、この組成
物の方が明らかに優れた配向性を示した。Furthermore, when viewed under the same conditions as Comparative Example 1, this liquid crystal composition (1) had as few as 11 defects in the visual field, and this composition clearly showed superior alignment.
実施例４
（１）式に相当する成分
（１１式に相当する成分
比較例１と同様にして光学活性−３７−クロロ−４′−
オクチルオキシ−４−ビフェニルカルボン酸＋ ｓｒ−
フルオロ−４’−（１−メチルへフチルオキシ力ルボニ
ル）フェニルエステルヲ製造した。この化合物の１０重
量部と、４′−オクチルオキシ−４−ビフェニルカルボ
ン酸及びラセミ体の４−ヒドロキシ安息香酸−１−メチ
ルへ−ｊｆｋエステルを用いる他は比較例１のｆｂｌと
同様にして製造した４′−オクチルオキシ−４−ビフェ
ニルカルボン酸−４′−（１−メチルへフチルオキシ力
ルボニル）フェニルエステルの９０重量部とを混合して
液晶組成物を製造した。この液晶組成物は６１〜１１５
Ｃで８Ｃ１）相を示した。Example 4 Component corresponding to formula (1) (component corresponding to formula 11) Optically active -37-chloro-4'-
Octyloxy-4-biphenylcarboxylic acid + sr-
Fluoro-4'-(1-methylhephthyloxycarbonyl)phenyl ester was prepared. Produced in the same manner as fbl of Comparative Example 1, except that 10 parts by weight of this compound, 4'-octyloxy-4-biphenylcarboxylic acid, and racemic 4-hydroxybenzoic acid-1-methyl to-jfk ester were used. A liquid crystal composition was prepared by mixing with 90 parts by weight of 4'-octyloxy-4-biphenylcarboxylic acid-4'-(1-methylhephthyloxycarbonyl)phenyl ester. This liquid crystal composition has 61 to 115
C showed 8C1) phase.
実施例５
１０式に相当する成分
ｔｌｊ弐に相当する成分
４′−オクチルオキシ−４−ビフェニルカルボン酸２．
４１１からの酸クロライドと実施例１における光学活性
−２−フルオロ−４−ヒドロキ７安息香酸−１−メチル
ヘプチルエステルと光学活性−２−オクタツールとの混
合物２．８，９．及び光学活性２−メチルブタノール０
．４ｇを用いるほかは実施例１と同様にして液晶組成物
■を製造した。この液晶組成物の相転移＠度は表１に示
しである。Example 5 Component corresponding to formula 10 Component corresponding to tlj2 4'-octyloxy-4-biphenylcarboxylic acid 2.
Mixture of the acid chloride from 411 and optically active 2-fluoro-4-hydroxy7benzoic acid-1-methylheptyl ester and optically active 2-octatool in Example 1 2.8,9. and optically active 2-methylbutanol 0
．． Liquid crystal composition (2) was produced in the same manner as in Example 1 except that 4 g was used. The phase transition degree of this liquid crystal composition is shown in Table 1.
また、実施例１と同−条件で測定した自発分極の値は４
８ｎＣ／ｃｒｒＬ２であった。In addition, the value of spontaneous polarization measured under the same conditions as Example 1 was 4.
It was 8nC/crrL2.
更に、比較例１と同一条件で観察したとき、この液晶組
成物■は視野中の欠陥の数は９ ｉＩｌと少なく、この
組成物の方が明らかに優れた配向性を示した。Furthermore, when observed under the same conditions as Comparative Example 1, the number of defects in the visual field of this liquid crystal composition (1) was as small as 9 iIl, and this composition clearly showed superior alignment.
実施例６
（１１式に相当する成分
？
（１）式に相当する成分
２−フルオロ−４−ヒドロキシ安息香酸及び１−ヘキサ
ノールを用いる他は比較例１（ａ）と同様にして２−フ
ルオロ−４−ヒドロキシ安息香酸ヘキシルを製造した。Example 6 (Component corresponding to formula 11? Component corresponding to formula (1) 2-fluoro- Hexyl 4-hydroxybenzoate was produced.
次に光学活性４’−（１−メチルヘフチル）−４−ビフ
ェニルカルボン酸３．ローからの酸クロライドと、２−
フルオロ−４−ヒドロキシ安息香酸ヘキシル２．０ｇ及
び１−オクタツール０．２１を用いるほかは比較例１（
ｂ）と同様にして液晶組成物■を製造した。この液晶組
成物の相転移温度は表１に示しである。Next, optically active 4'-(1-methylhephthyl)-4-biphenylcarboxylic acid 3. acid chloride from rho and 2-
Comparative Example 1 except that 2.0 g of hexyl fluoro-4-hydroxybenzoate and 0.21 g of 1-octatool were used (
Liquid crystal composition (2) was produced in the same manner as in (b). The phase transition temperature of this liquid crystal composition is shown in Table 1.
また、実施例１と同一条件で測定した自発分極の値は６
３ｎＣ／ ｃａ２であった。In addition, the value of spontaneous polarization measured under the same conditions as Example 1 was 6
It was 3nC/ca2.
更に、比較例１と同一条件で観察したとき、この液晶組
成物■は視野中の欠陥の数は１２個と少なく、この組成
′吻の方が明らかに優れた配向性を示した。Furthermore, when observed under the same conditions as in Comparative Example 1, the number of defects in the field of view of this liquid crystal composition (1) was as small as 12, and this composition '2' clearly showed superior orientation.
以上説明したように、本発明によれば、一般弐■で表さ
れる化合物を含有する液晶組成物、特に一般式１の化合
物を含有する液晶組成物を用いることにより、自発分極
が大きく、カイラルスメクチックＣ液晶相の温度範囲が
室温を包含して広く、しかも欠陥の少ない液晶組成物を
得ることができる。As explained above, according to the present invention, by using a liquid crystal composition containing a compound represented by general formula 2, especially a liquid crystal composition containing a compound of general formula 1, the spontaneous polarization is large and the chiral A liquid crystal composition in which the temperature range of the smectic C liquid crystal phase is wide, including room temperature, and has fewer defects can be obtained.
特許出願人 日本電信電話株式会社Patent applicant: Nippon Telegraph and Telephone Corporation
Claims (1)
ルオキシ基、Ｒ＿２は炭素数４以上のアルキル基を示し
、Ｒ＿１及びＲ＿２のいずれか一方は光学活性基であり
、Ｘは塩素又は水素、Ｙは塩素又はフッ素を示す）で表
される化合物を必須成分とすることを特徴とする液晶組
成物。 ２、該液晶組成物が、下記一般式II： ▲数式、化学式、表等があります▼・・・〔II〕 （式中、Ｒ＿１は炭素数４以上のアルキル基又はアルキ
ルオキシ基、Ｒ＿２は炭素数４以上のアルキル基を示し
、Ｒ＿１及びＲ＿２のいずれか一方は光学活性基である
）で表される化合物を少なくとも１種類含有する請求項
１記載の液晶組成物。[Claims] 1 The following general formula I: ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] (In the formula, R_1 is an alkyl group or alkyloxy group having 4 or more carbon atoms, and R_2 is a carbon number 4 or more alkyl groups, one of R_1 and R_2 is an optically active group, X is chlorine or hydrogen, and Y is chlorine or fluorine) as an essential component. liquid crystal composition. 2. The liquid crystal composition has the following general formula II: ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [II] (In the formula, R_1 is an alkyl group or alkyloxy group having 4 or more carbon atoms, and R_2 is a carbon 2. The liquid crystal composition according to claim 1, which contains at least one compound represented by the following formula: 4 or more alkyl groups, and one of R_1 and R_2 is an optically active group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8819188A JPH01261493A (en) | 1988-04-12 | 1988-04-12 | Liquid crystal composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8819188A JPH01261493A (en) | 1988-04-12 | 1988-04-12 | Liquid crystal composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01261493A true JPH01261493A (en) | 1989-10-18 |
Family
ID=13936014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8819188A Pending JPH01261493A (en) | 1988-04-12 | 1988-04-12 | Liquid crystal composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01261493A (en) |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60248790A (en) * | 1984-05-23 | 1985-12-09 | Hitachi Ltd | Ferroelectric liquid crystal composition and optical device therefrom |
| JPS6187777A (en) * | 1984-10-05 | 1986-05-06 | Ajinomoto Co Inc | Liquid crystal composition |
| JPS61161244A (en) * | 1985-01-09 | 1986-07-21 | Dainippon Ink & Chem Inc | Novel compound, preparation thereof, and liquid crystal composition |
| JPS61210056A (en) * | 1985-03-14 | 1986-09-18 | Chisso Corp | Halogen-containing optically active liquid crystal compound and liquid crystal composition |
| JPS6279288A (en) * | 1985-10-02 | 1987-04-11 | Alps Electric Co Ltd | Liquid crystal composition |
| JPS62238244A (en) * | 1986-04-04 | 1987-10-19 | Takasago Corp | Liquid crystal compound |
| JPS6327590A (en) * | 1986-07-18 | 1988-02-05 | Dainippon Ink & Chem Inc | Ferroelectric liquid crystal composition |
| JPS63216849A (en) * | 1987-03-06 | 1988-09-09 | Takasago Corp | Fluorine-containing liquid crystal compound |
| JPH01213390A (en) * | 1988-02-22 | 1989-08-28 | Chisso Corp | Ferroelectric liquid crystal composition and liquid crystal display element |
-
1988
- 1988-04-12 JP JP8819188A patent/JPH01261493A/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60248790A (en) * | 1984-05-23 | 1985-12-09 | Hitachi Ltd | Ferroelectric liquid crystal composition and optical device therefrom |
| JPS6187777A (en) * | 1984-10-05 | 1986-05-06 | Ajinomoto Co Inc | Liquid crystal composition |
| JPS61161244A (en) * | 1985-01-09 | 1986-07-21 | Dainippon Ink & Chem Inc | Novel compound, preparation thereof, and liquid crystal composition |
| JPS61210056A (en) * | 1985-03-14 | 1986-09-18 | Chisso Corp | Halogen-containing optically active liquid crystal compound and liquid crystal composition |
| JPS6279288A (en) * | 1985-10-02 | 1987-04-11 | Alps Electric Co Ltd | Liquid crystal composition |
| JPS62238244A (en) * | 1986-04-04 | 1987-10-19 | Takasago Corp | Liquid crystal compound |
| JPS6327590A (en) * | 1986-07-18 | 1988-02-05 | Dainippon Ink & Chem Inc | Ferroelectric liquid crystal composition |
| JPS63216849A (en) * | 1987-03-06 | 1988-09-09 | Takasago Corp | Fluorine-containing liquid crystal compound |
| JPH01213390A (en) * | 1988-02-22 | 1989-08-28 | Chisso Corp | Ferroelectric liquid crystal composition and liquid crystal display element |
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