JPS62111950A - Liquid crystal - Google Patents
Liquid crystalInfo
- Publication number
- JPS62111950A JPS62111950A JP60250335A JP25033585A JPS62111950A JP S62111950 A JPS62111950 A JP S62111950A JP 60250335 A JP60250335 A JP 60250335A JP 25033585 A JP25033585 A JP 25033585A JP S62111950 A JPS62111950 A JP S62111950A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- coo
- general formula
- group
- liquid crystal
- 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
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 12
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 15
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 10
- -1 phenyl-4-octyloxybenzoic acid ester Chemical class 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 239000000654 additive Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 230000010287 polarization Effects 0.000 description 18
- 230000002269 spontaneous effect Effects 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000004990 Smectic liquid crystal Substances 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000004988 Nematic liquid crystal Substances 0.000 description 5
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 230000005621 ferroelectricity Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 210000002858 crystal cell Anatomy 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 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
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 2
- YXBOJGHBKKAPOG-UHFFFAOYSA-N 4-octoxybenzoyl chloride Chemical compound CCCCCCCCOC1=CC=C(C(Cl)=O)C=C1 YXBOJGHBKKAPOG-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- UTIMESSLYFMSPO-UHFFFAOYSA-N 2-methylbutyl 3-[4-[(4-decoxyphenyl)methylideneamino]phenyl]prop-2-enoate Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C=NC1=CC=C(C=CC(=O)OCC(C)CC)C=C1 UTIMESSLYFMSPO-UHFFFAOYSA-N 0.000 description 1
- MPAIWVOBMLSHQA-UHFFFAOYSA-N 3,6-dihydroxybenzene-1,2-dicarbonitrile Chemical compound OC1=CC=C(O)C(C#N)=C1C#N MPAIWVOBMLSHQA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- NXWRVVHAEIPIBZ-UHFFFAOYSA-N hexan-2-yl 2-hydroxybenzoate Chemical compound CCCCC(C)OC(=O)C1=CC=CC=C1O NXWRVVHAEIPIBZ-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000010409 thin film Substances 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)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は新規な液晶物質及び該液晶物質を含む液晶組成
物に間する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to novel liquid crystal materials and liquid crystal compositions containing the liquid crystal materials.
又本明細書に於いて液晶性物質とは、それ自体で液晶相
を呈することが検知されなくとも液晶組成物の構成成分
としてとして有用な物質を意味する。Furthermore, in this specification, the term "liquid crystalline substance" refers to a substance that is useful as a component of a liquid crystal composition even if it is not detected to exhibit a liquid crystal phase by itself.
従来の技術
液晶表示素子の表示方式としで、現在広く実用化されて
いるものは、ねじれネマチック型（ＴＮ型）および動的
散乱型（ＤＳ型）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°の短所のひとつに、応答速度
が遅く、たかだか数ｍ Ｓ ｅ Ｃのオーダーの応答速
度しか得られないという事実があげられる。そしで、こ
のことがネマチック液晶セルの応用範囲なせばめる一因
となっている。しかしら最近に至ってスメクチック液晶
セルを用いれば、より高速な応答が得られるということ
がわかってきた。BACKGROUND OF THE INVENTION The display systems of liquid crystal display elements that are currently in widespread use are twisted nematic type (TN type) and dynamic scattering type (DS type). These are nematic liquid crystals,
This is a display using a nematic liquid crystal cell as the main component. One of the disadvantages of conventional nematic liquid crystal cells is the fact that the response speed is slow, and only a response speed on the order of a few mSeC can be obtained at most. This is one of the reasons why the range of applications of nematic liquid crystal cells is becoming narrower. However, it has recently been found that faster response can be obtained by using a smectic liquid crystal cell.
光学活性なスメクチック液晶の中には、強誘電性を示す
ものがあることが、明らかになってきており、その利用
に関しで、大ぎな１１１］待が寄せられつつある。強誘
電性を示す液晶すなわち強誘電性液晶は、１９７５年Ｒ
，Ｂ、Ｍｅｙｅｒらにより合成され、４−（４−ｎ−デ
シルオキシベンジリデンアミノ）ケイ皮酸−２−メチル
ブチルエステル（以下、ＤＯＢＡＭＢＣと略記する。）
を代表例とする化合物であり、その、カイラルスメクチ
ックＣ相（以下、５ｒｎＣ＊相と略記する。）においで
、強誘電性を示すことを特徴とする特許ある（Ｊ、Ｐｈ
ｙｓｉｑｕｅ、１１．Ｌ−６９（１９７５）） 。It has become clear that some optically active smectic liquid crystals exhibit ferroelectricity, and there is a great deal of anticipation regarding their use. Liquid crystals exhibiting ferroelectric properties, ferroelectric liquid crystals, were developed in 1975 by R
, B, Meyer et al., 4-(4-n-decyloxybenzylideneamino)cinnamic acid-2-methylbutyl ester (hereinafter abbreviated as DOBAMBC).
There is a patent (J, Ph.
ysique, 11. L-69 (1975)).
近年、Ｎ、Ａ、Ｃｌａｒｋら（Ａｐｐｌ−ＰｈＶｓ、Ｌ
ｅｔｔ、３６．８９ （１９８０））によっで、ＤＯＢ
ＡＭＢＣの薄膜セルにおいで、μｓｅｃオーダーの高速
応答性が、見出されたことを契機に、強誘電性液晶はそ
の高速応答性を利用して液晶テレビ等のディスプレイ用
のみならず、光プリンターヘット゛、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連素子
の素材用にも使用可能な材料として注目を集めている。Recently, N.A. Clark et al. (Appl-PhVs, L
ett, 36.89 (1980)), DOB
With the discovery of high-speed response on the μsec order in AMBC thin-film cells, ferroelectric liquid crystals have been used not only for displays such as LCD televisions, but also for optical printer heads. It is attracting attention as a material that can be used for optoelectronic related elements such as optical Fourier transform elements and light valves.
発明が解決しようとしている問題点
現在知られている強誘電性液晶には単独で実用に十分な
自発分極を室温域を含む広い温度範囲で示すものはない
。そこで数種類の物質が混合されている物が、使用され
ようとしているが、未だに実用化されていない。Problems to be Solved by the Invention None of the currently known ferroelectric liquid crystals exhibits spontaneous polarization sufficient for practical use over a wide temperature range including room temperature. Therefore, a mixture of several types of substances is being used, but it has not yet been put to practical use.
そこで、強い自発分極を広い温度範囲で示すような化合
物、温度範囲を広げることができるような化合物もしく
は、温度範囲を損なうことなく自発分極を大きくするこ
とができるような化合物が望まれている。Therefore, there is a need for compounds that exhibit strong spontaneous polarization over a wide temperature range, compounds that can extend the temperature range, or compounds that can increase spontaneous polarization without impairing the temperature range.
問題点を解決するための手段
本発明者らは、上述のような問題点を解決するために種
々の液晶物質を探索し本発明に到達した。Means for Solving the Problems In order to solve the above-mentioned problems, the present inventors searched for various liquid crystal materials and arrived at the present invention.
即ち、本発明は一般式（Ｔ）
Ｒ１−Ａ−（Ｐｈ）ａ−８−（Ｐｈ）ｂ−Ｃ−（１’ｈ
）ｃ−Ｄ−Ｒ２（Ｉ）（但し、上式に於いで、ＲＩ Ｉ
ｔ：直鎖または分岐の炭素数１〜１８のアルキル基、光
学活性ハロケン化アルキル基、光学活性ハロゲン化アラ
ルキル基、Ｒ２は、光学活性ハロゲン化アルキル基、光
学活性ハロゲン化アラルキル基を示し、ａ、１′１、Ｃ
は１．２または３で、Ａは、単結合、−ｏ−、−ＣＯＯ
−１−ｏ−ＣＯＯ−、または −ＯＣＯ−を示し、Ｂ、
Ｃは、−ＣＯＯ−、−ＯＣＯ−１−Ｎ＝Ｃｌｌ、−、−
ＣＨ＝Ｎ−１または−Ｃｌ１＝ ＣＩ＋−を示し、Ｄは
、−ＣＯＯ−１−ＣＯＯ−ＣＩ２−５または一ＯＣＯ−
を示し、Ｐｈは、１，４−フェニレン基、またはベンゼ
ン環に、ハロゲン、シアノ基、ニトロ基を、１個または
それ以上置換した１、４−フェニレン基を示す。）で表
わされる液晶物質及びそれを含有する液晶組成物に関す
る。That is, the present invention provides general formula (T) R1-A-(Ph)a-8-(Ph)b-C-(1'h
)c-D-R2(I) (However, in the above formula, RI I
t: linear or branched alkyl group having 1 to 18 carbon atoms, optically active halogenated alkyl group, optically active halogenated aralkyl group, R2 represents an optically active halogenated alkyl group, optically active halogenated aralkyl group, a ,1'1,C
is 1.2 or 3, A is a single bond, -o-, -COO
-1-o-COO- or -OCO-, B,
C is -COO-, -OCO-1-N=Cll, -, -
CH=N-1 or -Cl1=CI+-, D is -COO-1-COO-CI2-5 or 1OCO-
Ph represents a 1,4-phenylene group or a 1,4-phenylene group in which one or more halogen, cyano group, or nitro group is substituted on the benzene ring. ) and a liquid crystal composition containing the same.
一般に液晶化合物はベンゼン環などから成る核部分とア
ルキル鎖などから成る棒状構造をしている。その中でも
アルキル鎖の炭素数がある程度以上のものはスメクチッ
ク相を取りやすいことが良く知られている。そして一般
に、アルキル鎖の炭素数が若干具なっても同じ骨格を有
する化合物は同じような相系列を示すことも良く知られ
ている◇上記一般式（１）中、Ｒ１が炭素数６〜１４の
アルキル基である化合物はカイラルスメクチックＣ相を
取りやすく強誘電性液晶材料として特に有用である。ま
た、それ以外の化合物も、以下の実施例に示されている
ように強誘電性液晶用配合材料や、あるいは、一般に液
晶材料などとして使用することができる。Generally, liquid crystal compounds have a rod-like structure consisting of a core made of a benzene ring, etc., and an alkyl chain. Among them, it is well known that those whose alkyl chain has more than a certain number of carbon atoms tend to form a smectic phase. In general, it is well known that compounds having the same skeleton exhibit similar phase series even if the number of carbon atoms in the alkyl chain is slightly different.◇In the above general formula (1), R1 has 6 to 14 carbon atoms. Compounds having an alkyl group tend to form a chiral smectic C phase and are particularly useful as ferroelectric liquid crystal materials. In addition, other compounds can also be used as compounding materials for ferroelectric liquid crystals, as shown in the following examples, or as liquid crystal materials in general.
（１）式で表わされる化合物は次のように合成される。The compound represented by formula (1) is synthesized as follows.
一般式（Ｉ）で表わされる化合物のあるものは、テレフ
タル酸ジクロライドもしくはベンゼン環に各種置換基を
導入したテレフタル酸ジクロライドの誘導体もしくは、
次の一般式（あ）で表わされる安息香酸誘導体の酸クロ
ライドと、次の一一般式（い）で表わせられる各種フェ
ノール誘導体と、ピリジンのような塩基性溶媒中で反応
させれば良−い。Some of the compounds represented by the general formula (I) are terephthalic acid dichloride or derivatives of terephthalic acid dichloride with various substituents introduced into the benzene ring, or
The acid chloride of a benzoic acid derivative represented by the following general formula (A) may be reacted with various phenol derivatives represented by the following general formula (B) in a basic solvent such as pyridine. .
Ｒ１−Ａ−Ｐｈ−Ｂ−Ｐｈ−ＣＯＣＩ （あ）ＨＯ
−Ｐｈ−Ｄ−ＣＨ（Ｘ）−Ｒ３（い）＊
また、ある化合物は、ヒｉＳロキノン誘導体、もしくは
一般式（う）で表わされる各種フェノールを、一般式（
え）で表オつされる各種安息香酸クロライド誘導体と、
ピリジンのような塩基性溶媒中で反応させれば良い。R1-A-Ph-B-Ph-COCI (A) HO
-Ph-D-CH(X)-R3(I)
E) various benzoic acid chloride derivatives listed in
The reaction may be carried out in a basic solvent such as pyridine.
Ｒ１−Ａ−Ｐｈ−Ｂ−Ｐｈ−０１１（う）Ｃｌ０Ｃ−Ｐ
ｈ−Ｄ−ＣＨ（Ｘ）−Ｒ３（え）ネ
（但し、上式（あ）〜（え）に於いで、Ｒ１は直鎖また
は分岐の炭素数１〜１８のアルキル基、光学活性ハロゲ
ン化アルキル基、光学活性ハロゲン化アラルキル基、Ｒ
２は、光学活性ハロゲン化アルキル基、光学活性ハロゲ
ン化アラルキル基を示し、Ａは、単結合、−ｏ−、−Ｃ
ＯＯ−、−ｏ−ＣＯＯ−、または −〇ＣＯ−を示し、
Ｂは、−ＣＯＯ−、−ＯＣＯ−、−Ｎ＝ＣＨ−５−ＣＩ
＝Ｎ−１または−ＣＩＩ ＝ ＣＨ−を示し、Ｄは、−
Ｃ００−３−ＣＯＯ−Ｃｌ＋２−１または −ＯＣＯ−
を示し、Ｐｈは、１，４−フェニレン基、またはベンセ
ン環に、ハロゲン、シアノ基、ニトロ基を置換した１、
４−フェニレン基を示す。）
一般式（あ）〜（え）の化合物は以下の実施例に示すよ
うな方法で簡単に得られる。R1-A-Ph-B-Ph-011(u)Cl0C-P
h-D-CH(X)-R3(e)ne (However, in the above formulas (a) to (e), R1 is a linear or branched alkyl group having 1 to 18 carbon atoms, an optically active halogenated Alkyl group, optically active halogenated aralkyl group, R
2 represents an optically active halogenated alkyl group or an optically active halogenated aralkyl group, and A is a single bond, -o-, -C
Indicates OO-, -o-COO-, or -〇CO-,
B is -COO-, -OCO-, -N=CH-5-CI
=N-1 or -CII = CH-, D is -
C00-3-COO-Cl+2-1 or -OCO-
, Ph is 1,4-phenylene group, or 1 in which a benzene ring is substituted with a halogen, a cyano group, or a nitro group,
Indicates a 4-phenylene group. ) Compounds of general formulas (a) to (e) can be easily obtained by the methods shown in the following examples.
発明の作用
本発明の化合物は強誘電性液晶性をしめす。また、本発
明の化合物のうぢ＋１１独では強誘電性液晶とはならな
い物質も、強誘電性）＾品物質と混合することにより、
その強誘電性をＪｉ９強するために役立てることができ
る。Effect of the Invention The compound of the present invention exhibits ferroelectric liquid crystallinity. In addition, even substances that do not form ferroelectric liquid crystals by themselves as compounds of the present invention can be mixed with ferroelectric substances.
It can be used to increase its ferroelectricity to a level greater than Ji9.
本発明の化合物は、光学活性か化合物なので、ホワイト
ティラー型カラー表示用、コレステリックネマチック相
転移型表示用、ＴＮ型セルにおけるリバースドメイン発
生防止用等の月的でネマチック液晶に添加して用いるこ
とも可能である。Since the compound of the present invention is an optically active compound, it can also be used by adding it to nematic liquid crystals for white tiller type color display, cholesteric nematic phase change type display, prevention of reverse domain generation in TN type cell, etc. It is possible.
また本発明の化合物はスメクチック液晶となるので、熱
書込レーザー書込等の記憶型表示素子用に用いることも
可能である。Further, since the compound of the present invention becomes a smectic liquid crystal, it can also be used for memory type display elements such as thermal writing laser writing.
発明の効果
本発明の化合物のあるものは強誘電性液晶となる。そし
で、その自発分極軸以下の実施例に示されているように
、非常に大きい。例えは、実施例１に示されている化合
物は１００ ｎＣ／ｃｉもの自発分極を示す。Effects of the Invention Some of the compounds of the present invention become ferroelectric liquid crystals. Therefore, as shown in the examples below, the spontaneous polarization axis is very large. For example, the compound shown in Example 1 exhibits a spontaneous polarization of as much as 100 nC/ci.
また、本発明の化合物のあるものを、それ自身が極く弱
い自発分極しか持たない化合物に添加することにより大
きな自発分極を持つ強誘電性液晶を調製することができ
る。実施例７に示されているように実施例５の本発明の
化合物を少量添加するだけで、元の化合物の数十倍の自
発分極を持つ、強誘電性液晶組成物が得られるというよ
うな驚くべき効果が得られる。Furthermore, a ferroelectric liquid crystal having a large spontaneous polarization can be prepared by adding some of the compounds of the present invention to a compound that itself has only a very weak spontaneous polarization. As shown in Example 7, by simply adding a small amount of the compound of the present invention of Example 5, a ferroelectric liquid crystal composition having a spontaneous polarization several tens of times higher than that of the original compound can be obtained. You can get amazing results.
また、本発明の化合物は例えばＤＯＢＡＭＢＣと異なり
シッフ塩基を持たないため化学的に安定である。Further, the compound of the present invention is chemically stable because it does not have a Schiff base unlike, for example, DOBAMBC.
また、本発明の化合物のあるものは、負の誘電率異方性
を持つので、交流を駆けることにより、光スイツチング
素子にメモリー性を持たせることができる。Further, since some of the compounds of the present invention have negative dielectric anisotropy, an optical switching element can be provided with memory properties by running an alternating current.
実施例
以下実施例により、本発明の化合物につき更に詳細に説
明するが、本発明は、これらの実施例により、限定され
るものではない。EXAMPLES The compounds of the present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to these Examples.
以下、Ｃ，５ＸＳＳＣ＊、ｓＡ、ｓｈ＊、Ｎ＊、Ｎ、Ｉ
相はそれぞれ、結晶、はっきりと同定できないスメクチ
ック相、カイラルスメクチックＣ相、スメクチックＡ相
、カイラルスメクチックＩ相、カイラルネマチック相、
ネマチック相、等方相を示す。Below, C, 5XSSC*, sA, sh*, N*, N, I
The phases are respectively crystalline, unidentifiable smectic phase, chiral smectic C phase, smectic A phase, chiral smectic I phase, chiral nematic phase,
Shows nematic phase and isotropic phase.
実施例１
（１”’ Ｓ、２” ’ ５）−４’ −（４”−（１
”２−クロロ−２”２−メチルブチルカルボニルオキシ
）ベンゾイルオキシ）フェニル−４−オクチルオキシ安
息香酸エステル（Ａ）の合成と評価＊ ｔ
Ｃ８Ｈ１７−０−Ｐｈ−ＣＯＯ−Ｐｈ−ＯＣＯ−Ｐｈ−
ＯＣＯ−Ｃｌｌ−Ｃｌｌ−Ｃ２Ｈ５ＣＩ Ｃｌｌ３
ｐ、ｐ’−ヒドロキノン８．５ｇをピリジン５０ｍ１に
溶解し、そこに４−オクチルオキシ安息香酸クロライド
１０ｇを四塩化炭素２０ｍ１に溶解したものを加えしば
らく攪はんする。塩酸により中和しクロロホルムにより
抽出する。クロロホルムを留去して得られた粗生成物を
シリカゲルカラムにより精製し、４′−ヒト゛ロキシフ
ェニルー４−オクヂルオキシ安息香酸エステル（Ｂ）を
得る。Example 1 (1"'S, 2"'5)-4'-(4"-(1
Synthesis and evaluation of “2-chloro-2”2-methylbutylcarbonyloxy)benzoyloxy)phenyl-4-octyloxybenzoic acid ester (A) * t C8H17-0-Ph-COO-Ph-OCO-Ph-
OCO-Cll-Cll-C2H5CI Cll3 Dissolve 8.5 g of p,p'-hydroquinone in 50 ml of pyridine, add 10 g of 4-octyloxybenzoic acid chloride dissolved in 20 ml of carbon tetrachloride, and stir for a while. . Neutralize with hydrochloric acid and extract with chloroform. The crude product obtained by distilling off chloroform is purified using a silica gel column to obtain 4'-hydroxyphenyl-4-ocdyloxybenzoate (B).
（Ｂ）２ｇをピリジン１０ｍ１に溶解し、そこに（１’
Ｓ、２’ ５）−４−（１’−クロロ−２′−メチル
ブチルカルボニルオキシ）安息香酸クロライド２ｇを四
塩化炭素４０ｍ！に溶解したものを加えしばらく攪はん
する。析出した結晶をろ別し溶媒を留去して得られた粗
生成物をシリカゲルカラムにより精製し、（Ａ）を得る
。Dissolve 2g of (B) in 10ml of pyridine and add (1'
S, 2' 5) -4-(1'-chloro-2'-methylbutylcarbonyloxy)benzoic acid chloride 2g and carbon tetrachloride 40m! Add the dissolved ingredients and stir for a while. The precipitated crystals are filtered and the solvent is distilled off, and the resulting crude product is purified using a silica gel column to obtain (A).
この化合物の自発分極をソーヤ−タワー法により測定し
たところ１００ ｎＣ／ｃｒＺであった。該化合物のＴ
Ｒスペクトルを図１に示す。The spontaneous polarization of this compound was measured by the Sawyer Tower method and was found to be 100 nC/crZ. T of the compound
The R spectrum is shown in FIG.
相転移温度は表１に示されている。The phase transition temperatures are shown in Table 1.
実施例２
（１”ｌ ｓ 、 Ｑ”Ｉｓ） ｔ）°、３′−ジシ
アノー４．’−（４”−（１”２−クロロ−２°゛９−
メチルブチルカルボニルオキシ）ベンゾイルオキシ）フ
ェニル−４−オクチルオキシ安息香酸エステルの合成と
評価
ｐｌｐ′−ヒドロキノンの代わりに、２，３−ジシアノ
ヒドロキノンをもちい実施例１と同様の方法で合成した
。Example 2 (1"Is, Q"Is) t)°, 3'-dicyano4. '-(4"-(1"2-chloro-2°゛9-
Synthesis and evaluation of methylbutylcarbonyloxy)benzoyloxy)phenyl-4-octyloxybenzoic acid ester Synthesis was performed in the same manner as in Example 1 using 2,3-dicyanohydroquinone instead of plp'-hydroquinone.
実施例３
（２”’ Ｓ、３” ’ Ｓ）−／ｌ’ −（４”−（
２”５−クロロ−３”９−メチルペンチルオキシカルボ
ニル）フェニルオキシカルボニル）フェニル−４−オク
チルオキシ安息香酸エステル（Ｃ）の合成と評価
：ｉ 才
Ｃ３ＨＩ ７−０− Ｐｈ−ＣＯＯ−Ｐｈ−ＣＯＯ−Ｐ
ｈ−Ｃ０Ｏ−、−ＣＨ２−Ｃｌｌ−ＣＨ−Ｃ２Ｈ５Ｉ
ＣＨ３
４−ヒドロキシ安息香ｉ！ａ６．５ｇをピリジン５０ｍ
１に溶解し、そこに４−オクチルオキシ安息香酸クロラ
イド１０ｇを四塩化炭素２０ｍ１に溶解したものを加え
しばらく攪はんする。塩酸によ−１し−
り中和し析出した結晶をろ別し４− （（４’−オクチ
ルオキシ）ベンツイルオキシ）安息香酸（Ｄ）を得る。Example 3 (2'''S, 3'''S)-/l'-(4''-(
Synthesis and evaluation of 2"5-chloro-3"9-methylpentyloxycarbonyl)phenyloxycarbonyl)phenyl-4-octyloxybenzoic acid ester (C): i C3HI 7-0- Ph-COO-Ph-COO -P
h-C0O-, -CH2-Cll-CH-C2H5I
CH3 4-Hydroxybenzoic! 6.5g of a and 50m of pyridine
1, and a solution of 10 g of 4-octyloxybenzoic acid chloride dissolved in 20 ml of carbon tetrachloride was added thereto and stirred for a while. Neutralize with hydrochloric acid and filter the precipitated crystals to obtain 4-((4'-octyloxy)benzyloxy)benzoic acid (D).
以下特にこれを精製せずに使う。、（Ｄ）を塩化チオニ
ルにより酸クロライド゛とし、実施例１と同様の方法で
（２’ Ｓ、３’ ５）−４−（２′−クロロ−３′−
メチルペンチルオキシカルボニル）フェノールと反応さ
せ（Ｃ）を得る。This will be used below without further purification. , (D) was converted into acid chloride with thionyl chloride, and (2'S,3'5)-4-(2'-chloro-3'-
(C) is obtained by reacting with (methylpentyloxycarbonyl)phenol.
相転移温度は表１に示されている。The phase transition temperatures are shown in Table 1.
実施例４
ビス−（、（２’ Ｓ、３’ Ｓ）−（４−（２’ −
クロロ−３′−メチルペンチルオキシカルボニル）フェ
ニル））テレフタル酸エステル（Ｅ）の合成と評１価
＊ ＊
Ｃ２Ｈ３−（ｊｌ（ＣＨ３）−ＣＨ（ＣＩ ）−ＣＨ２
−ＯＣＯ−Ｐｈ−ＯＣＯ−Ｐｈ−ＣＯＯ−Ｐｈ−ＣＯＯ
−ＣＨ２−ＣＨ（ＣＩ ）−、−ＣＨ（Ｃ）１３）−Ｃ
２Ｈ５１よ
テレフタル酸ジクロライド１．５ｇを四塩化炭素８０
ｒｒｔ ｌとピリジン１０ｍ１の？ｄ合物に溶解し冷却
する。水冷下、（２’ Ｓ、３’ ５）−４−（２′−
クロロ−３′−メチルペンチルオキシカルボニル）フェ
ノールを１．７ｇ加えしばらく攪はんする。−晩装置し
、析出した結晶をろ別し、溶媒を留去したのちにシリカ
ゲルカラムにより精製し、酢酸エチルで再結晶し目的物
（Ｅ）を得る。Example 4 Bis-(, (2'S, 3'S)-(4-(2'-
Synthesis and evaluation of chloro-3'-methylpentyloxycarbonyl)phenyl))terephthalic acid ester (E)* *C2H3-(jl(CH3)-CH(CI)-CH2
-OCO-Ph-OCO-Ph-COO-Ph-COO
-CH2-CH(CI)-, -CH(C)13)-C
2H51, 1.5 g of terephthalic acid dichloride, 80 g of carbon tetrachloride
rrt l and 10ml of pyridine? d Dissolve in the compound and cool. Under water cooling, (2'S, 3'5)-4-(2'-
Add 1.7 g of chloro-3'-methylpentyloxycarbonyl) phenol and stir for a while. - overnight, the precipitated crystals are filtered off, the solvent is distilled off, and the mixture is purified using a silica gel column and recrystallized from ethyl acetate to obtain the desired product (E).
相転移温度は表１に示されている。The phase transition temperatures are shown in Table 1.
実施例５
１．４−ビス−（（１”Ｓ、２” ５）−４’ −（ｌ
”−クロロ−２”−メチルブチルカルボニルオキシ）ベ
ンゾイルオキシ）ベンゼン（Ｆ）の合成と評価
＊ ４、
Ｃ２Ｈ５−ＣＨ（Ｃ）１３）−ＣＨ（ＣＩ ）−ＣＯＯ
−Ｐｈ−ＣＯＯ−Ｐｈ −ＯＣＯ−Ｐ ｈ−ＯＣＯ−Ｃ
ｌ１（ＣＩ）−Ｃｌｌ（ＣＨ３）−Ｃ２Ｈ５イ′
ネ
ヒドロキノン０．５ｇをピリジン１０ ｍ ｌに溶解し
、（１’ Ｓ、２’ ５）−４−（１’−クロロ−２′
−メチルブチルカルボニルオキシ）安息香酸クロライド
２ｇを４０ｒｒｉ＋の四塩化炭素の溶解したものをを攪
はんしながら加える。−晩装置し、析出した結晶をろ別
し、溶媒を留去したのちにシリカゲルカラムにより精製
し、酢酸エチルで再結晶し目的物（Ｆ）を得る。Example 5 1.4-bis-((1″S, 2″ 5)-4′-(l
Synthesis and evaluation of “-chloro-2”-methylbutylcarbonyloxy)benzoyloxy)benzene (F) *4, C2H5-CH(C)13)-CH(CI)-COO
-Ph-COO-Ph -OCO-P h-OCO-C
l1(CI)-Cll(CH3)-C2H5i'
Dissolve 0.5 g of nehydroquinone in 10 ml of pyridine and prepare (1'S,2'5)-4-(1'-chloro-2'
-Methylbutylcarbonyloxy)benzoic acid chloride (2 g) is added to a solution of 40 rri+ carbon tetrachloride with stirring. - overnight, the precipitated crystals are filtered off, the solvent is distilled off, and the mixture is purified using a silica gel column and recrystallized from ethyl acetate to obtain the desired product (F).
相転移温度は表１に示されている。The phase transition temperatures are shown in Table 1.
実施例６
実施例１〜５で得られた化合物および実施例１〜５と同
様の方法で得られる本発明の化合物の相転移温度を一括
して表１に示す。Example 6 The phase transition temperatures of the compounds obtained in Examples 1 to 5 and the compounds of the present invention obtained by the same method as Examples 1 to 5 are collectively shown in Table 1.
実施例７
（Ｓ）−２”′−メチルブチルー４− （４’−ウンデ
シルカルボニルオキシフェニル）安息香酸エステル（Ｇ
）
ＣＩＩＨ２３−Ｃ００−Ｐｈ−Ｐｈ−Ｃ００−Ｃｌ１２
−、−ＣＨ（、−ＣＨ３）−Ｃ２Ｈ５（Ｇ ）と１．４
−Ｌ’ス−（（１” Ｓ、２″″５）−４’ −（１”
−クロロ−２″−メチルブチルカルボニルオキシ）ベン
ゾイルオキシ）ベンゼン（Ｆ）を８１：１９で混合した
。Example 7 (S)-2”'-methylbutyl-4-(4'-undecylcarbonyloxyphenyl)benzoic acid ester (G
) CIIH23-C00-Ph-Ph-C00-Cl12
-, -CH(, -CH3)-C2H5(G) and 1.4
-L'S-((1"S, 2""5)-4'-(1"
-Chloro-2''-methylbutylcarbonyloxy)benzoyloxy)benzene (F) were mixed in a ratio of 81:19.
化合物（Ｇ）は、昇温時に４０〜５０ＴにおいてＳＣ＊
相を示し、１ ｎＣ／ｃηｆ程度の自発分極をもつ。Compound (G) was subjected to SC* at 40 to 50 T during heating.
phase, and has a spontaneous polarization of about 1 nC/cηf.
この混合物は、昇温時に４０〜５０’ＣにおいてＳＣ＊
相を示した。この混合物の自発分極をソーヤ−タワー法
により測定したところ５５ ｎＣ／ｃｔｆであった。こ
のように本発明の化合物を添加することにより強誘電性
を示す温度範囲を損なうことなしに自発分極を増大する
ことができることが証明された。This mixture was heated to SC* at 40-50'C.
It showed the phase. The spontaneous polarization of this mixture was measured by the Sawyer Tower method and was found to be 55 nC/ctf. It was thus demonstrated that by adding the compound of the present invention, spontaneous polarization can be increased without impairing the temperature range in which ferroelectricity is exhibited.
実施例８
（Ｓ）−４”−（２”２−メチルブチルオキシ）フェニ
ル−４−（４’−オクチルオキシフェニル）安息香酸エ
ステル（Ｈ）
Ｃ８Ｈ１７−０−Ｐｈ−Ｐｈ−ＣＯＯ−Ｐｈ−０−ＣＨ
２−ＣＨ（ＣＨ３）−Ｃ２Ｈ５（Ｈ）イ；
と化合物（Ｆ）を８０：２０で混合した。Example 8 (S)-4"-(2"2-methylbutyloxy)phenyl-4-(4'-octyloxyphenyl)benzoic acid ester (H) C8H17-0-Ph-Ph-COO-Ph-0 -CH
2-CH(CH3)-C2H5(H)i; and compound (F) were mixed at a ratio of 80:20.
化合物（Ｈ）は昇温時に９８〜１５２℃においてＳＣ＊
相を示し、１ ｎＣ／ｅｒｒ程度の自発分極をもつ。Compound (H) was subjected to SC* at 98-152°C during heating.
phase, and has a spontaneous polarization of about 1 nC/err.
この混合物は、昇温時に９８〜１５０℃においてＳＣ＊
相を示した。この混合物の自発分極をソーヤ−タワー法
により測定したところ３５ ｎＣ／ｃ！であった。この
ように本発明の化合物を添加することにより強誘電性を
示す温度範囲を損なうことなしに自発分極を増大するこ
とができることが証明された。This mixture was heated to SC* at 98-150°C.
It showed the phase. The spontaneous polarization of this mixture was measured by the Sawyer Tower method and was 35 nC/c! Met. It was thus demonstrated that by adding the compound of the present invention, spontaneous polarization can be increased without impairing the temperature range in which ferroelectricity is exhibited.
実施例９
（Ｓ）−４’ −（４”−（２”ゝ−メチルブチルオキ
シカルボニル）フェニル）フェニル−４−オクチルカル
ボニルオキシ安息香酸エステル（１）Ｃ８Ｈ１７−ＣＯ
ｏ−Ｐｈ−ＣＯＯ−１’ｈ−Ｐｈ−’Ｃ０Ｏ−ＣＨ２−
Ｃ）ｌ（ＣＨ３）−Ｃ２Ｈ５ｔ （１）
と１，４−ビス−（（１”Ｓ＋２”５）−４’ −（１
”−クロロ−２”−メチルブチルカルボニルオキシ）ベ
ンゾイルオキシ）ベンゼン（Ｊ）を９０＝１０で混合し
た。Example 9 (S)-4'-(4''-(2''-methylbutyloxycarbonyl)phenyl)phenyl-4-octylcarbonyloxybenzoic acid ester (1) C8H17-CO
o-Ph-COO-1'h-Ph-'C0O-CH2-
C) l(CH3)-C2H5t (1) and 1,4-bis-((1"S+2"5)-4' -(1
"-Chloro-2"-methylbutylcarbonyloxy)benzoyloxy)benzene (J) was mixed in a ratio of 90=10.
化合物（１）は、昇温時に６９〜１２４℃においてＳＣ
＊相を示し、１ ｎＣ／ｃ＆程度の自発分極をもつ。Compound (1) has an SC temperature of 69 to 124°C during heating
*It exhibits a phase and has a spontaneous polarization of about 1 nC/c&.
この混合物は、昇温時に７０〜１２９℃においてＳＣ＊
相を示した。この混合物の自発分極をソーヤ−タワー法
により測定したところ２３ ｎＣ／ｃｔ／であった。こ
のように本発明の化合物を添加することにより強誘電性
を示す温度範囲を損なうことなしに自発分極を増大する
ことができることが証明された。This mixture was heated to SC* at 70-129°C.
It showed the phase. The spontaneous polarization of this mixture was measured by the Sawyer Tower method and was found to be 23 nC/ct/. It was thus demonstrated that by adding the compound of the present invention, spontaneous polarization can be increased without impairing the temperature range in which ferroelectricity is exhibited.
Claims (8)
ｃ−Ｄ−Ｒ２（ I ）（但し、上式に於いて、Ｒ１は直
鎖または分岐の炭素数１〜１８のアルキル基、光学活性
ハロゲン化アルキル基、光学活性ハロゲン化アラルキル
基、Ｒ２は、光学活性ハロゲン化アルキル基、光学活性
ハロゲン化アラルキル基を示し、ａ、ｂ、ｃは１、２ま
たは３で、Ａは、単結合、−Ｏ−、−ＣＯＯ−、−Ｏ−
ＣＯＯ−、または−ＯＣＯ−を示し、Ｂ、Ｃは、−ＣＯ
Ｏ−、−ＯＣＯ−、−Ｎ＝ＣＨ−、−ＣＨ＝Ｎ−、また
は−ＣＨ＝ＣＨ−を示し、Ｄは、−ＣＯＯ−、−ＣＯＯ
−ＣＨ２−、または−ＯＣＯ−を示し、Ｐｈは、１，４
−フェニレン基、またはベンゼン環に、ハロゲン、シア
ノ基、ニトロ基を、１個またはそれ以上置換した１，４
−フェニレン基を示す。）で表わされる化合物。(1) General formula (I) R1-A-(Ph)a-B-(Ph)b-C-(Ph)
c-D-R2 (I) (However, in the above formula, R1 is a linear or branched alkyl group having 1 to 18 carbon atoms, an optically active halogenated alkyl group, an optically active halogenated aralkyl group, and R2 is Indicates an optically active halogenated alkyl group or an optically active halogenated aralkyl group, where a, b, and c are 1, 2, or 3, and A is a single bond, -O-, -COO-, -O-
COO- or -OCO-, B and C are -CO
O-, -OCO-, -N=CH-, -CH=N-, or -CH=CH-, and D is -COO-, -COO
-CH2- or -OCO-, Ph is 1,4
- phenylene group or benzene ring substituted with one or more halogen, cyano group, or nitro group
- indicates a phenylene group. ).
Ｈ（Ｘ）−Ｒ３（II） （Ｒ３はアルキル基、アラルキル基を、Ｘは、Ｆ、Ｃｌ
またはＢｒを、＊は光学活性な炭素原子を示す。）で表
わされる特許請求の範囲（１）項記載の化合物。(2) In general formula (I), R2 is the following general formula (II) -■
H(X)-R3(II) (R3 is an alkyl group, an aralkyl group, X is F, Cl
or Br, * represents an optically active carbon atom. ) The compound according to claim (1).
ｎＨ２ｎ＋１（III） （ｎは１〜１０の自然数を示す。）で表わされる特許請
求の範囲（１）項記載の化合物。(3) In general formula (II), R3 is the following general formula (III)-C
The compound according to claim (1), which is represented by nH2n+1(III) (n is a natural number from 1 to 10).
（ＣＨ３）２（IV） で表わされる特許請求の範囲（１）項記載の化合物。(4) In general formula (II), R3 is the following general formula (IV) -CH
A compound according to claim (1), which is represented by (CH3)2(IV).
２−ＣＨ（ＣＨ３）２（Ｖ） で表わされる特許請求の範囲（１）項記載の化合物。(5) In general formula (II), R3 is the following general formula (V) -CH
A compound according to claim (1), which is represented by 2-CH(CH3)2(V).
（ＣＨ３）−Ｃ２Ｈ５（VI） （＊は光学活性な炭素原子を示す。）で表わされる特許
請求の範囲（１）項記載の化合物。(6) In general formula (II), R3 is the following general formula (VI) -■H
A compound according to claim (1), which is represented by (CH3)-C2H5(VI) (* indicates an optically active carbon atom).
ｈ（VII） （Ｐｈはフェニル基を示す。）で表わされる特許請求の
範囲（１）項記載の化合物。(7) In general formula (II), R3 is the following general formula (VII)-P
The compound according to claim (1), which is represented by h(VII) (Ph represents a phenyl group).
ｃ−Ｄ−Ｒ２（ I ）（但し、上式に於いて、Ｒ１は直
鎖または分岐の炭素数１〜１８のアルキル基、光学活性
ハロゲン化アルキル基、光学活性ハロゲン化アラルキル
基、Ｒ２は、光学活性ハロゲン化アルキル基、光学活性
ハロゲン化アラルキル基を示し、ａ、ｂ、ｃは１、２ま
たは３で、Ａは、単結合、−Ｏ−、−ＣＯＯ−、−Ｏ−
ＣＯＯ−、または−ＯＣＯ−を示し、Ｂ、Ｃは、−ＣＯ
Ｏ−、−ＯＣＯ−、−Ｎ＝ＣＨ−、−ＣＨ＝Ｎ−、また
は−ＣＨ＝ＣＨ−を示し、Ｄは、−ＣＯＯ−、−ＣＯＯ
−ＣＨ２−、または−ＯＣＯ−を示し、Ｐｈは、１、４
−フェニレン基、またはベンゼン環に、ハロゲン、シア
ノ基、ニトロ基を、１個またはそれ以上置換した１，４
−フェニレン基を示す。）で表わされる化合物を少なく
とも一種含有することを特徴とする液晶。(8) General formula (I) R1-A-(Ph)a-B-(Ph)b-C-(Ph)
c-D-R2 (I) (However, in the above formula, R1 is a linear or branched alkyl group having 1 to 18 carbon atoms, an optically active halogenated alkyl group, an optically active halogenated aralkyl group, and R2 is Indicates an optically active halogenated alkyl group or an optically active halogenated aralkyl group, where a, b, and c are 1, 2, or 3, and A is a single bond, -O-, -COO-, -O-
COO- or -OCO-, B and C are -CO
O-, -OCO-, -N=CH-, -CH=N-, or -CH=CH-, and D is -COO-, -COO
-CH2- or -OCO-, Ph is 1, 4
- phenylene group or benzene ring substituted with one or more halogen, cyano group, or nitro group
- indicates a phenylene group. ) A liquid crystal characterized by containing at least one compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60250335A JPS62111950A (en) | 1985-11-08 | 1985-11-08 | Liquid crystal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60250335A JPS62111950A (en) | 1985-11-08 | 1985-11-08 | Liquid crystal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62111950A true JPS62111950A (en) | 1987-05-22 |
Family
ID=17206385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60250335A Pending JPS62111950A (en) | 1985-11-08 | 1985-11-08 | Liquid crystal |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62111950A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62181237A (en) * | 1986-02-05 | 1987-08-08 | Dainippon Ink & Chem Inc | Liquid crystal compound |
| JPS62294646A (en) * | 1986-05-30 | 1987-12-22 | ヘキスト・アクチエンゲゼルシヤフト | Antipodic ester comprising alpha-substituted carboxylic acidand mesogenic-hydroxy compound and use as dopant in liquid crystal phase |
| JPS632953A (en) * | 1986-06-14 | 1988-01-07 | ヘキスト アクチェンゲゼルシャフト | Antipodic ester comprising alpha-substituted phenylalkanoic acid and mesogenic-hydroxyl compound and use as dopant in liquid crystal phase |
| JPS6344550A (en) * | 1986-08-12 | 1988-02-25 | Dainippon Ink & Chem Inc | triester liquid crystal compound |
| US4828754A (en) * | 1985-01-09 | 1989-05-09 | Dainippon Ink & Chemicals, Inc. | Novel liquid crystalline compounds having substituents |
| US4961876A (en) * | 1985-08-26 | 1990-10-09 | Veb Werk Fuer Fernsehelektronik Im Veb Kombinat Mikroelektronik | Liquid crystalline ferroelectric derivatives of branched acyclic alpha-chlorocarboxylic acids |
| US5269965A (en) * | 1988-12-28 | 1993-12-14 | Takeda Chemical Industries | Optically active compounds, liquid crystal compositions comprising said compounds and liquid crystal optical modulators using said compositions |
| CN104531164A (en) * | 2014-12-05 | 2015-04-22 | 深圳市万明精工科技有限公司 | High molecular reinforced negative cholesteric phase mixed liquid crystal material and application method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6251644A (en) * | 1985-08-26 | 1987-03-06 | サムスング・エレクトロン・デイバイセス・カンパニー・リミテツド | Feproelectric derivative of liquid crystal of branched non-cyclic alpha chlorocarboxylic acid, manufacture and use |
-
1985
- 1985-11-08 JP JP60250335A patent/JPS62111950A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6251644A (en) * | 1985-08-26 | 1987-03-06 | サムスング・エレクトロン・デイバイセス・カンパニー・リミテツド | Feproelectric derivative of liquid crystal of branched non-cyclic alpha chlorocarboxylic acid, manufacture and use |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4828754A (en) * | 1985-01-09 | 1989-05-09 | Dainippon Ink & Chemicals, Inc. | Novel liquid crystalline compounds having substituents |
| US4961876A (en) * | 1985-08-26 | 1990-10-09 | Veb Werk Fuer Fernsehelektronik Im Veb Kombinat Mikroelektronik | Liquid crystalline ferroelectric derivatives of branched acyclic alpha-chlorocarboxylic acids |
| JPS62181237A (en) * | 1986-02-05 | 1987-08-08 | Dainippon Ink & Chem Inc | Liquid crystal compound |
| JPS62294646A (en) * | 1986-05-30 | 1987-12-22 | ヘキスト・アクチエンゲゼルシヤフト | Antipodic ester comprising alpha-substituted carboxylic acidand mesogenic-hydroxy compound and use as dopant in liquid crystal phase |
| JPS632953A (en) * | 1986-06-14 | 1988-01-07 | ヘキスト アクチェンゲゼルシャフト | Antipodic ester comprising alpha-substituted phenylalkanoic acid and mesogenic-hydroxyl compound and use as dopant in liquid crystal phase |
| JPS6344550A (en) * | 1986-08-12 | 1988-02-25 | Dainippon Ink & Chem Inc | triester liquid crystal compound |
| JPH0791227B2 (en) * | 1986-08-12 | 1995-10-04 | 大日本インキ化学工業株式会社 | Triester liquid crystal compound |
| US5269965A (en) * | 1988-12-28 | 1993-12-14 | Takeda Chemical Industries | Optically active compounds, liquid crystal compositions comprising said compounds and liquid crystal optical modulators using said compositions |
| CN104531164A (en) * | 2014-12-05 | 2015-04-22 | 深圳市万明精工科技有限公司 | High molecular reinforced negative cholesteric phase mixed liquid crystal material and application method thereof |
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