JPS6168449A - Biphenyl-type diester compound and liquid crystal containing said compound - Google Patents
Biphenyl-type diester compound and liquid crystal containing said compoundInfo
- Publication number
- JPS6168449A JPS6168449A JP59189232A JP18923284A JPS6168449A JP S6168449 A JPS6168449 A JP S6168449A JP 59189232 A JP59189232 A JP 59189232A JP 18923284 A JP18923284 A JP 18923284A JP S6168449 A JPS6168449 A JP S6168449A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- alkyl group
- compound
- halogenated
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 37
- -1 diester compound Chemical class 0.000 title claims abstract description 17
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 18
- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 5
- 230000001747 exhibiting effect Effects 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 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 abstract description 2
- 239000002253 acid Substances 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 description 16
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 7
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 7
- 230000005621 ferroelectricity Effects 0.000 description 7
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-methylpentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 4
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 3
- 210000002858 crystal cell Anatomy 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- 239000001618 (3R)-3-methylpentan-1-ol Substances 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- BAVONGHXFVOKBV-UHFFFAOYSA-N Carveol Chemical compound CC(=C)C1CC=C(C)C(O)C1 BAVONGHXFVOKBV-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical group 0.000 description 2
- QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical compound CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 description 2
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- 230000007423 decrease Effects 0.000 description 2
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- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 2
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- 238000002156 mixing Methods 0.000 description 2
- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- BAVONGHXFVOKBV-ZJUUUORDSA-N (-)-trans-carveol Natural products CC(=C)[C@@H]1CC=C(C)[C@@H](O)C1 BAVONGHXFVOKBV-ZJUUUORDSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- BTANRVKWQNVYAZ-SCSAIBSYSA-N (2R)-butan-2-ol Chemical compound CC[C@@H](C)O BTANRVKWQNVYAZ-SCSAIBSYSA-N 0.000 description 1
- OJRHUICOVVSGSY-RXMQYKEDSA-N (2s)-2-chloro-3-methylbutan-1-ol Chemical compound CC(C)[C@H](Cl)CO OJRHUICOVVSGSY-RXMQYKEDSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 1
- BITYXLXUCSKTJS-UHFFFAOYSA-N 2-isopropylmalic acid Chemical compound CC(C)C(O)(C(O)=O)CC(O)=O BITYXLXUCSKTJS-UHFFFAOYSA-N 0.000 description 1
- YNPVNLWKVZZBTM-UHFFFAOYSA-N 4-methylhexan-1-ol Chemical compound CCC(C)CCCO YNPVNLWKVZZBTM-UHFFFAOYSA-N 0.000 description 1
- PCWGTDULNUVNBN-UHFFFAOYSA-N 4-methylpentan-1-ol Chemical compound CC(C)CCCO PCWGTDULNUVNBN-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- LCWXJXMHJVIJFK-UHFFFAOYSA-N Hydroxylysine Natural products NCC(O)CC(N)CC(O)=O LCWXJXMHJVIJFK-UHFFFAOYSA-N 0.000 description 1
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- NOOLISFMXDJSKH-LPEHRKFASA-N Isomenthol Natural products CC(C)[C@@H]1CC[C@H](C)C[C@H]1O NOOLISFMXDJSKH-LPEHRKFASA-N 0.000 description 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- AGPKZVBTJJNPAG-UHNVWZDZSA-N L-allo-Isoleucine Chemical compound CC[C@@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-UHNVWZDZSA-N 0.000 description 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
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- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 238000000862 absorption spectrum Methods 0.000 description 1
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- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
（い）産業上の利用分野
本発明は新規な液晶物及び該液晶物質を含む液晶組成物
に間し、特に、スメクチック液晶組成物に間する。DETAILED DESCRIPTION OF THE INVENTION (1) Industrial Application Field The present invention relates to a novel liquid crystal substance and a liquid crystal composition containing the liquid crystal substance, and particularly to a smectic liquid crystal composition.
又本明５ｓ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 the present specification, the term "liquid crystalline substance" means 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.
（ろ）従来の技術
液晶表示素子の表示方式として、現在広く実用化されて
いるものは、ねしれネマチック型（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（α晶セルによる表示である。(B) Prior Art The display systems of liquid crystal display devices that are currently in widespread use are the twisted nematic type (TN type) and the dynamic scattering type (DS type). These are nematic liquid crystals,
It is displayed using nematic (α crystal cells) as the main component.
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、たかたか数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。そして、こ
のことがネマチック液晶セルの応用範囲をせばめる°−
因となっている。しかし、最近に至ってスメクチックγ
α品セルを用いれば、より高速な応答が得られるという
ことかわかってきた。One of the disadvantages of conventional nematic liquid crystal cells is the fact that the response speed is slow, and the response speed is only on the order of a few msec. This narrows the range of applications for nematic liquid crystal cells.
This is the cause. However, recently, smectic γ
It has become clear that faster response can be obtained by using α-product cells.
光学活性なスメクチックγα品の中には、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
用に関して、大きな期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、下記構造式で示される
４−（４−ｎ−ダン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、ＤＯＢＡＭＢ
Ｃ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、Ｓｍ Ｃ零相と略
記する。）において、強誘電性を示すことを特徴とする
ものである（、Ｊ、Ｐｈｙｓｉｑｕｅ、３ｊ３−、Ｌ−
６９（１９７５））。It has become clear that some optically active smectic γα products exhibit ferroelectricity, and there are great expectations for their use. Liquid crystals exhibiting ferroelectric properties, that is, ferroelectric liquid crystals, were developed in 1975 by R.B.
4-(4-n-danyloxybenzylideneamino)cinnamic acid-2-methylbutyl ester (hereinafter referred to as DOBAMB) synthesized by Meyer et al.
Abbreviated as C. ) is a typical example, and the
It is characterized by exhibiting ferroelectricity in the chiral smectic C phase (hereinafter abbreviated as Sm C zero phase) (J, Physique, 3j3-, L-
69 (1975)).
ＤＯＢＡＭＢＣ
近年、Ｎ、Ａ、Ｃ１ａｒｋら（Ａｐｐｌ、Ｐｈｙｓ、Ｌ
ｅ ｔ ｔ、３６．８９ （１９８０））によって、Ｄ
ＯＢＡＭＢＣの薄膜セルにおいて、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γ材用にも使用可能な材料として注目を集めている
。DOBAMBC In recent years, N, A, C1ark et al. (Appl, Phys, L
et t t, 36.89 (1980)), D
With the discovery of high-speed response on the μsec order in OBAMBC's thin film cells, ferroelectric liquid crystals have been used not only for displays such as LCD televisions, but also for optical printer heads, by utilizing their high-speed response. It is attracting attention as a material that can be used as a gamma material for optoelectronic related elements such as optical Fourier transform elements and light valves.
（は）発明が解決しようとしＣいる問題点しかし、ＤＯ
ＢＡＭＢＣは強誘電性を示す温度範囲が比較的狭く、ま
たシッフ塩基であるため、その物理的化学的安定性に難
がある。そこで、強誘電性液晶材料として、物理的化学
的に安定で、強訴電性を示す温度範囲が広く、低電圧駆
動が可能な誘電率が大きい化合物の出現が強く望まれて
いる。(is) the problem that the invention seeks to solve; however, DO
BAMBC has a relatively narrow temperature range in which it exhibits ferroelectricity, and since it is a Schiff base, its physical and chemical stability is poor. Therefore, as a ferroelectric liquid crystal material, there is a strong desire for a compound that is physically and chemically stable, exhibits ferroelectricity over a wide temperature range, and has a high dielectric constant that can be driven at a low voltage.
（に）問題点を解決するための手段
本発明者らは、上述のような欠点を改善するために種々
の液晶物質を探索し本発明に到達した。(2) Means for Solving the Problems The present inventors searched for various liquid crystal materials to improve the above-mentioned drawbacks and arrived at the present invention.
即ち、本発明は一般式（１）
て表わされる化合物及びそれを含有する液晶組成物であ
る。That is, the present invention is a compound represented by the general formula (1) and a liquid crystal composition containing the same.
（１）式の化合物は次のように合成される。The compound of formula (1) is synthesized as follows.
４−（４’−ヒドロキシ）−ビフェニルカルボン酸とア
ルキルカルボン酸クロライドを反応させ４−（４°−ア
ルキルカルボニルオキシ）ビフェニルカルボン酸を得る
。つずいて塩化チオニルを作用させ４− （４’−フル
キルカルボニルオキシ）ビフェニルカルボン酸クロライ
ドとする。４−（４“−アルキルカルボニルオキシ）ビ
フェニルカルボン酸クロライドとアルコールを反応させ
目的物である４−（４’ −フルキルカルボニルオキシ
）ビフェニルカルボン酸エステルを得る。4-(4'-hydroxy)-biphenylcarboxylic acid and alkylcarboxylic acid chloride are reacted to obtain 4-(4°-alkylcarbonyloxy)biphenylcarboxylic acid. Subsequently, thionyl chloride is reacted to give 4-(4'-furkylcarbonyloxy)biphenylcarboxylic acid chloride. 4-(4"-alkylcarbonyloxy)biphenylcarboxylic acid chloride and alcohol are reacted to obtain the target product, 4-(4'-furkylcarbonyloxy)biphenylcarboxylic acid ester.
上記一般式（１）中、Ｒ２０によって表わされる不斉縣
は例えば次のような光学活性アルコ、ルから誘導される
。In the above general formula (1), the asymmetric group represented by R20 is derived from, for example, the following optically active alcohol.
２−ハロー１−プロパツール、２．３−ジハロ−１−プ
ロパツール、２，３，３．３−テトラハロー１−プロパ
ツール、２−メチル−１−ブタノール、３−メチル−１
−ペンタノール、４−メチル−１−ヘキサノール、２−
ブタノール、２−ペンタノール、２−ヘキサノール、２
−ヘプタツール、３−ヘキサノール、２−オクタツール
、１−フェニルエタノール、リナロール、ネロリトール
、ソプレロール、カルボメントール、メントール、イソ
メントール、ボルネオール、イソボルネオール、カルベ
オール、コレステロール、２−へロー２−フェニルエタ
ノール、２−フェニル−３−ハローｌ−プロパツール、
３−フェニル−２−ハロー１−プロパツール、１−フェ
ニル−２−へローｌ−プロパツール、３−ハロー２−メ
チル−１−プロパツール、１，１．１−）リムロー２−
プロパツール、２−ハロー１−ブタノール、３−ハロー
１−ブタノール、２．３−ジハロ−１−ブタノール、
２゜４−ジハロ−
１−ブタノール、３．４−ジハロ−１−ブタノール、１
．１．１−トリハロー２−ブタノール、４，４．４−）
リムロー３−ｔ１ｃｌ−１−ブタノール、２，３．４−
）リムローｌ−ブタノール、３，３，４，４．４−ペン
タハロー２−ブタノール、２−ハロー３−メチル−１−
ブタノール、２−ハロー３．３−ジメチル−１−ブタノ
ール、２−へ〇−ｌ−ペンタノール、３−ハローｌ−ペ
ンタノール、４−へローｌ−ペンタノール、２．４−シ
バａ−１−ペンタノール、２，６−ジハロ−ｌ−ペンタ
ノール、１，１．１−）リムロー２−ペンタノール、１
，１，１．２．２−ペン９ Ａ Ｏ−３−ペンタノール
、２−ハロー３−メチル−１−ペンタノール、２−へロ
ー４−メチルー１−ペンタノール、２−ハロー３−モノ
ハロメチルー４−メチルー１−ペンタノール、２−ハロ
ー１−ヘキサノール、３−ハロー１−ヘキサノール、４
−ハロー１−ヘキサノール、５−ハロー１−ヘキサノー
ル、２，５−ジハロ−１−ヘキサノール、２．６−シハ
ロー１−ヘキサノール、１，１．１−トリハロー２−’
＼キサノール、２．５．６−ト１．１ ハＣ１−１−ヘ
キサノール、２−へローｌ−ヘプタツール、！、１．Ｉ
−）ダハロー２−ヘプタツール、２−ハロー１−オクタ
ツール、ｌ、１．１−トリハロー２−オクタツール等。2-halo-1-propatol, 2,3-dihalo-1-propatol, 2,3,3.3-tetrahalo-1-propatol, 2-methyl-1-butanol, 3-methyl-1
-pentanol, 4-methyl-1-hexanol, 2-
Butanol, 2-pentanol, 2-hexanol, 2
- heptatool, 3-hexanol, 2-octatool, 1-phenylethanol, linalool, nerolitol, soprelol, carbomenthol, menthol, isomenthol, borneol, isoborneol, carveol, cholesterol, 2-hero 2-phenylethanol, 2-phenyl-3-halo l-propertool,
3-phenyl-2-halo 1-propatol, 1-phenyl-2-halo 1-propatol, 3-halo 2-methyl-1-propatol, 1,1.1-)rimuro 2-
propatool, 2-halo-1-butanol, 3-halo-1-butanol, 2,3-dihalo-1-butanol,
2゜4-dihalo-
1-butanol, 3.4-dihalo-1-butanol, 1
．． 1.1-trihalo-2-butanol, 4,4.4-)
Rimulow 3-t1cl-1-butanol, 2,3.4-
) Limulo l-butanol, 3,3,4,4.4-pentahalo 2-butanol, 2-halo 3-methyl-1-
Butanol, 2-halo 3.3-dimethyl-1-butanol, 2-halo-l-pentanol, 3-halo l-pentanol, 4-halo l-pentanol, 2.4-shiba a-1 -pentanol, 2,6-dihalo-l-pentanol, 1,1.1-) rimlow 2-pentanol, 1
,1,1.2.2-pen9 A O-3-pentanol, 2-halo 3-methyl-1-pentanol, 2-halo 4-methyl-1-pentanol, 2-halo 3-monohalomethyl-4 -Methyl-1-pentanol, 2-halo 1-hexanol, 3-halo 1-hexanol, 4
-Halo 1-hexanol, 5-halo 1-hexanol, 2,5-dihalo-1-hexanol, 2.6-cyhalo 1-hexanol, 1,1.1-trihalo 2-'
\xanol, 2.5.6-to1.1 haC1-1-hexanol, 2-herol l-heptatool,! , 1. I
-) Dahalo 2-heptatool, 2-halo 1-octatool, l, 1.1-trihalo 2-octatool, etc.
（但し上記化学式中ハロとは、フッ素、塩素、又は臭素
を表わす。）
上記の光学活性アルコールのうちあるものは、対応する
ケトンの不斉金属触媒、微生物又は酵素による不斉還元
により、容易に得られる。またあるものは、天然に存在
するか、又は分割により得られる次のような光学活性ア
ミノ酸及び光学活性オキシ酸から誘導できる。バリン、
ロイシン、イソロイシン、フェニルアラニン、スレオニ
ン、アロスレオニン、ホモセリン、アロイソロイシン、
ｔｅｒｔ−ロイシン、２−アミノ酪酸、ノルバリン、ノ
ルロイシン、オルニチン、リジン、ヒドロキシリジン、
フェニルグリシン、アスパラギン酸、グルタミン酸、マ
ンデル酸、トロバ酸、３−ヒドロキシ酪酸、リンゴ酸、
酒石酸、イソプロピルリンゴ酸等。(However, halo in the above chemical formula represents fluorine, chlorine, or bromine.) Some of the above optically active alcohols can be easily reduced by asymmetric reduction of the corresponding ketone with an asymmetric metal catalyst, microorganism, or enzyme. can get. Others can be derived from optically active amino acids and optically active oxyacids, such as those naturally occurring or obtained by resolution. Balin,
Leucine, isoleucine, phenylalanine, threonine, allothreonine, homoserine, alloisoleucine,
tert-leucine, 2-aminobutyric acid, norvaline, norleucine, ornithine, lysine, hydroxylysine,
Phenylglycine, aspartic acid, glutamic acid, mandelic acid, trobic acid, 3-hydroxybutyric acid, malic acid,
Tartaric acid, isopropylmalic acid, etc.
（は）作用
本発明の化合物は強訴電性をしめす。また、単独では強
誘電性液晶とはならない物質も、上記の強誘電性液晶物
質と混合することにより、その強誘電性を損なうことな
く強誘電性液晶温度範囲を低下させることができる。(a) Action The compound of the present invention exhibits strong electrostatic properties. Further, by mixing a substance that does not form a ferroelectric liquid crystal by itself with the above-mentioned ferroelectric liquid crystal substance, the temperature range of the ferroelectric liquid crystal can be lowered without impairing its ferroelectricity.
本発明の化合物は１種又は２種以上混合して用いられる
。混合することにより、その強誘電性を損なうことなく
強誘電性液晶温度範囲を低下させることができる。本発
明の化合物のなかで光学活性な化合物は、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
止用等の目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。The compounds of the present invention may be used alone or in combination of two or more. By mixing, the temperature range of the ferroelectric liquid crystal can be lowered without impairing its ferroelectric properties. Among the compounds of the present invention, optically active compounds may be added to nematic liquid crystals for purposes such as white tiller type color display, cholesteric nematic phase transition type display, and prevention of reverse domain generation in TN type cells. 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.
（と）発明の効果
本発明の化合物は化学的に安定であり、なおかつ室温域
で強誘電性を示す。本発明の化合物は例えば、ＤＯＢＡ
ＭＢＣと異なりシッフ塩基を持たないためＤＯＢＡＭＢ
Ｃに比べて逼かに安定である。また、強誘電性を示す温
度範囲も降温時においテＤ ＯＢＡＭＢ Ｃ＋７）９２
℃−６３℃に比へ（ｓ）−３−メチル−２−クロルブチ
ル−４−（４’ −° ヘプチルカルボニルオキシ）−
ビフェニルカルボン酸エステルでは３２℃−一１１”Ｃ
と逼かに低下する。(and) Effects of the Invention The compound of the present invention is chemically stable and exhibits ferroelectricity at room temperature. Compounds of the invention include, for example, DOBA
Unlike MBC, DOBAMB does not have a Schiff base.
It is much more stable than C. In addition, the temperature range in which ferroelectricity is exhibited also changes when the temperature decreases.
(s)-3-Methyl-2-chlorobutyl-4-(4'-°heptylcarbonyloxy)-
For biphenylcarboxylic acid ester, 32℃-11”C
and decreases sharply.
（ち）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。(H) Examples The compounds of the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.
実施例１
（Ｓ ）、−３−メチル−２−クロルブチル−４−（４
’−オクチルカルボニルオキシ）−ビフェニルカルボン
酸エステル（Ａ）の製造及び物性４−（１−ヒドロキシ
）−ビフェニルカルボン酸４．５ｇを四塩化炭素３００
ｍ１、ビリシン５０ｍ１に、分散し加熱する。還流下、
ノナン酸クロライド３．７ｇｔｉ：ｎかし、次いで３時
間加熱する。溶媒を留去したのちに、少量の水を加え未
反応のノナン酸クロライドを分解し、残さをメタノール
で洗浄し４− （４’−オクチルカルボニルオキシ）−
ビフェニルカルボンｍ （Ｂ）６．５ｇを得る。（Ｂ）
を四塩化炭素２００ ｍ ｌに分散し、塩化チオニル１
０ｍ１を加え、還流下、３時間反応させる。溶媒を留去
し４−（４’−オクチルカルボニルオキシ）−ビフェニ
ルカルボン酸クロライド （Ｃ）６．０ｇを得る。Example 1 (S), -3-methyl-2-chlorobutyl-4-(4
Production and physical properties of '-octylcarbonyloxy)-biphenylcarboxylic acid ester (A) 4.5 g of 4-(1-hydroxy)-biphenylcarboxylic acid was added to 300 g of carbon tetrachloride.
Disperse and heat in 50ml of bilicin. Under reflux,
Add 3.7 gti:n of nonanoyl chloride and then heat for 3 hours. After distilling off the solvent, a small amount of water was added to decompose unreacted nonanoyl chloride, and the residue was washed with methanol to give 4-(4'-octylcarbonyloxy)-
6.5 g of biphenylcarbon m (B) is obtained. (B)
was dispersed in 200 ml of carbon tetrachloride, and 1 thionyl chloride was added.
Add 0ml and react under reflux for 3 hours. The solvent was distilled off to obtain 6.0 g of 4-(4'-octylcarbonyloxy)-biphenylcarboxylic acid chloride (C).
（Ｃ）１．５ｇを、四塩化炭素８０ｍ１とピリジン１０
ｍ１に溶解し、冷却する。冷却下、（Ｓ）−３−メチル
−２−クロルブタノールを０．４ｇ加えしばらく攪はん
する。−晩、放置し、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、ヘキサン
で再結晶し目的物（Ａ）を得る。収量０．８ｇ。(C) 1.5g, 80ml of carbon tetrachloride and 10ml of pyridine
Dissolve in m1 and cool. While cooling, add 0.4 g of (S)-3-methyl-2-chlorobutanol and stir for a while. - Leave to stand overnight, filter out the precipitated crystals, distill off the solvent, purify with a silica gel column, and recrystallize from hexane to obtain the desired product (A). Yield 0.8g.
この化合物は、ＳＣ本相反びＳＡ相を示すスメクチック
液晶化合物であり、その相転移温度は表１に示されてい
る。This compound is a smectic liquid crystal compound exhibiting an SC main phase and an SA phase, and its phase transition temperature is shown in Table 1.
該化合物の【Ｒスペクトルを図１に示す。The [R spectrum of the compound is shown in FIG. 1.
厚さ２５μｍのポリエチレンテレフタレートフィルムを
スペーサーとし、ネサガラスで構成したセルに（Ｓ）−
３−メチル−２−クロルブチル−４−（４’−オクチル
カルボニルオキシ）−ビフェニルカルボン酸エステルを
封入し、１００Ｈｚの交流をかけ、ブリッジ法で誘電率
を測定した。Using a 25 μm thick polyethylene terephthalate film as a spacer, (S)-
3-Methyl-2-chlorobutyl-4-(4'-octylcarbonyloxy)-biphenylcarboxylic acid ester was sealed, an alternating current of 100 Hz was applied, and the dielectric constant was measured by the bridge method.
その結果を図２に示した。尚、比較例としてＤＯＢＡＭ
ＢＣの誘電率について測定した結果を併せて図２に示し
た。同図から明らかなように、（Ｓ）−３−メチル−２
−クロルブチル−４−（４’ −オクチルカルボニルオ
キシ）−ビフェニルカルボン酸エステル（図中、実線）
はＤＯＢＡＭＢＣ（図中、点線）に比へ誘電率の値も非
常に大きい。The results are shown in FIG. As a comparative example, DOBAM
The results of measuring the dielectric constant of BC are also shown in FIG. 2. As is clear from the figure, (S)-3-methyl-2
-Chlorbutyl-4-(4'-octylcarbonyloxy)-biphenylcarboxylic acid ester (solid line in the figure)
The value of the dielectric constant is also very large compared to DOBAMBC (dotted line in the figure).
ポリエチレンテレフタレートフィルムをスペーサーとし
、ネサガラスで構成したセルに（Ｓ）−３−メチル−２
−クロルブチル−４−（４’−オクチルカルボニルオキ
シ）−ビフェニルカルボン酸エステルを封入し、矩形波
を印加して顕微鏡下で電気光学効果を観察した。非常に
はっきりしたコントラストに加えて、すばやい応答が視
認され、（Ｓ）−３−メチル−２−クロルブチル−４−
（４’−オうチルカルボニルオキシ）−ビフェニルカル
ボン酸エステルが液晶ディスプレイに応用できることが
証明された。(S)-3-methyl-2 was placed in a cell made of Nesa glass using a polyethylene terephthalate film as a spacer.
-Chlorbutyl-4-(4'-octylcarbonyloxy)-biphenylcarboxylic acid ester was encapsulated, a square wave was applied, and the electro-optic effect was observed under a microscope. In addition to the very sharp contrast, a quick response was visible and (S)-3-methyl-2-chlorobutyl-4-
It has been demonstrated that (4'-otylcarbonyloxy)-biphenylcarboxylic acid ester can be applied to liquid crystal displays.
実施例 ２
実施例Ｉと同様にして合成した本発明の代表的化合物の
相転移点を一括して表１に示す。Example 2 The phase transition points of representative compounds of the present invention synthesized in the same manner as in Example I are summarized in Table 1.
図１は実施例１で得た（Ｓ）−３−メチル−２−クロル
ブチル−４−（４’ −オクチルカルボニルオキシ）−
ビフェニルカルボン酸エステルの赤外線吸収スペクトル
を示す。
図２は（Ｓ）−３−メチル−２−クロルブチル−４−（
４’−オクチルカルボニルオキシ）−ビフェニルカルボ
ン酸エステル及び既知物質４−（４−ｎ−デシルオキシ
へンジリダンアミノ）ケイ皮酸−２−メチルブチルエス
テルについて測定した誘電率と温度との関係を示す図面
である。Figure 1 shows the (S)-3-methyl-2-chlorobutyl-4-(4'-octylcarbonyloxy)- obtained in Example 1.
The infrared absorption spectrum of biphenylcarboxylic acid ester is shown. Figure 2 shows (S)-3-methyl-2-chlorobutyl-4-(
4 is a diagram showing the relationship between the dielectric constant and temperature measured for 4'-octylcarbonyloxy)-biphenylcarboxylic acid ester and the known substance 4-(4-n-decyloxyhenzilidanamino)cinnamic acid-2-methylbutyl ester. .
Claims (21)
、又は、ハロゲン化アラルキル基を示し、Ｒ２Ｏはアル
コキシ基、ハロゲン化アルコキシ基、または、ハロゲン
化アラルキルオキシ基を示す。）で表わされる化合物。(1) General formula (1) ▲Mathematical formulas, chemical formulas, tables, etc.▼(1) (However, in the formula, R1 represents an alkyl group, a halogenated alkyl group, or a halogenated aralkyl group, and R2O represents an alkoxy group, A compound represented by a halogenated alkoxy group or a halogenated aralkyloxy group.
Ｏはアルコキシ基、ハロゲン化アルコキシ基、または、
ハロゲン化アラルキルオキシ基を示す。）で表わされる
化合物。(2) General formula (2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(2) (However, in the formula, R3 is an alkyl group having 1 to 18 carbon atoms, R4
O is an alkoxy group, a halogenated alkoxy group, or
Indicates a halogenated aralkyloxy group. ).
Ｏはアルコキシ基、ハロゲン化アルコキシ基、または、
ハロゲン化アラルキルオキシ基を示す。）で表わされる
化合物を少なくとも１種含有することを特徴とする液晶
。(3) General formula (2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(2) (However, in the formula, R3 is an alkyl group having 1 to 18 carbon atoms, R4
O is an alkoxy group, a halogenated alkoxy group, or
Indicates a halogenated aralkyloxy group. ) A liquid crystal characterized by containing at least one compound represented by:
トキシ基である特許請求の範囲（２）項記載の化合物。(4) The compound according to claim (2), wherein R3 is an alkyl group having 1 to 18 carbon atoms, and R4O is a butoxy group.
２Ｓ，３Ｓ）−３−メチル−２−クロルペントキシ基で
ある特許請求の範囲（２）項記載の化合物。(5) R3 is an alkyl group having 1-18 carbon atoms, and R4O is (
The compound according to claim (2), which is a 2S,3S)-3-methyl-2-chloropentoxy group.
２Ｓ，３Ｓ）−３−メチル−２−ブロモペントキシ基で
ある特許請求の範囲（２）項記載の化合物。(6) R3 is an alkyl group having 1-18 carbon atoms, and R4O is (
The compound according to claim (2), which is a 2S,3S)-3-methyl-2-bromopentoxy group.
Ｓ）−４−メチル−２−クロルペントキシ基である特許
請求の範囲（２）項記載の化合物。(7) R3 is an alkyl group having 1-18 carbon atoms, and R4O is (
The compound according to claim (2), which is S)-4-methyl-2-chloropentoxy group.
Ｓ）−３−メチル−２−クロルブトキシ基である特許請
求の範囲（２）項記載の化合物。(8) R3 is an alkyl group having 1-18 carbon atoms, and R4O is (
The compound according to claim (2), which is S)-3-methyl-2-chlorobutoxy group.
Ｓ）−３−フェニル−２−クロルプロポキシ基である特
許請求の範囲（２）項記載の化合物。(9) R3 is an alkyl group having 1-18 carbon atoms, and R4O is (
The compound according to claim (2), which is S)-3-phenyl-2-chloropropoxy group.
（Ｓ）−３−メチル−２−ブロモブトキシ基である特許
請求の範囲（２）項記載の化合物。(10) The compound according to claim (2), wherein R3 is an alkyl group having 1 to 18 carbon atoms, and R4O is a (S)-3-methyl-2-bromobutoxy group.
（Ｓ）−２−クロルペントキシ基である特許請求の範囲
（２）項記載の化合物。(11) The compound according to claim (2), wherein R3 is an alkyl group having 1 to 16 carbon atoms, and R4O is a (S)-2-chloropentoxy group.
（Ｓ）−２−メチルブトキシ基である特許請求の範囲（
２）項記載の化合物。(12) Claims in which R3 is an alkyl group having 1 to 18 carbon atoms and R4O is a (S)-2-methylbutoxy group (
Compound described in section 2).
（Ｓ）−３−メチルペントキシ基である特許請求の範囲
（２）項記載の化合物。(13) The compound according to claim (2), wherein R3 is an alkyl group having 1 to 18 carbon atoms, and R4O is a (S)-3-methylpentoxy group.
（Ｓ）−２−クロルブトキシ基である特許請求の範囲（
２）項記載の化合物。(14) Claims in which R3 is an alkyl group having 1 to 18 carbon atoms and R4O is a (S)-2-chlorobutoxy group (
Compound described in section 2).
（２Ｒ，３Ｓ）−３−メチル−２−クロルペントキシ基
である特許請求の範囲（２）項記載の化合物。(15) The compound according to claim (2), wherein R3 is an alkyl group having 1 to 18 carbon atoms, and R4O is a (2R,3S)-3-methyl-2-chloropentoxy group.
（Ｓ）−２−クロルプロポキシ基である特許請求の範囲
（２）項記載の化合物。(16) The compound according to claim (2), wherein R3 is an alkyl group having 1 to 18 carbon atoms, and R4O is a (S)-2-chloropropoxy group.
３−メチルブトキシ基である特許請求の範囲（２）項記
載の化合物。(17) The compound according to claim (2), wherein R3 is an alkyl group having 1 to 18 carbon atoms, and R4O is a 3-methylbutoxy group.
（Ｓ）−１−メチルプロポキシ基である特許請求の範囲
（２）項記載の化合物。(18) The compound according to claim (2), wherein R3 is an alkyl group having 1 to 18 carbon atoms, and R4O is a (S)-1-methylpropoxy group.
少なくとも１種含有することを特徴とする液晶。(19) A liquid crystal containing at least one compound of claims (4) to (18).
Ｏはアルコキシ基、ハロゲン化アルコキシ基、または、
ハロゲン化アラルキルオキシ基を示す。）で表わされる
化合物の製造法。(20) General formula (2) ▲Mathematical formulas, chemical formulas, tables, etc.▼(2) (However, in the formula, R3 is an alkyl group having 1 to 18 carbon atoms, R4
O is an alkoxy group, a halogenated alkoxy group, or
Indicates a halogenated aralkyloxy group. ) A method for producing a compound represented by
製造法。(21) A method for producing the compounds of claims (4) to (18).
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59189232A JPS6168449A (en) | 1984-09-10 | 1984-09-10 | Biphenyl-type diester compound and liquid crystal containing said compound |
| DE8585306347T DE3577843D1 (en) | 1984-09-10 | 1985-09-06 | BIPHENYL DIESTER COMPOUNDS AND LIQUID CRYSTAL COMPOSITIONS CONTAINING THEM. |
| EP85306347A EP0174816B1 (en) | 1984-09-10 | 1985-09-06 | Biphenyl-based diester compounds and liquid crystal compositions containing same |
| US06/774,484 US4695651A (en) | 1984-09-10 | 1985-09-10 | Biphenyl-based diester compounds and liquid crystal compositions containing same |
| US07/041,428 US4831182A (en) | 1984-09-10 | 1987-04-23 | Biphenyl-based diester compounds and liquid crystal compositions containing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59189232A JPS6168449A (en) | 1984-09-10 | 1984-09-10 | Biphenyl-type diester compound and liquid crystal containing said compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6168449A true JPS6168449A (en) | 1986-04-08 |
| JPH0550493B2 JPH0550493B2 (en) | 1993-07-29 |
Family
ID=16237806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59189232A Granted JPS6168449A (en) | 1984-09-10 | 1984-09-10 | Biphenyl-type diester compound and liquid crystal containing said compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6168449A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4732699A (en) * | 1985-07-01 | 1988-03-22 | Ajinomoto Co., Inc. | Biphenyl carbonic acid ester compounds and liquid crystal composition containing the same |
| US4753752A (en) * | 1985-08-19 | 1988-06-28 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Secondary alcohol derivatives for use in liquid crystal materials and devices |
| JPS63165345A (en) * | 1986-12-26 | 1988-07-08 | Chisso Corp | Optically active-2-methyl-alkanoates and utilized substance thereof |
| US4778621A (en) * | 1985-10-14 | 1988-10-18 | Chisso Corporation | Ester compound |
| US5167863A (en) * | 1987-12-24 | 1992-12-01 | Hitachi, Ltd. | Optically active compound, liquid crystal composition containing said compound, and liquid crystal optical modulator using said composition |
| 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 |
-
1984
- 1984-09-10 JP JP59189232A patent/JPS6168449A/en active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4732699A (en) * | 1985-07-01 | 1988-03-22 | Ajinomoto Co., Inc. | Biphenyl carbonic acid ester compounds and liquid crystal composition containing the same |
| US4753752A (en) * | 1985-08-19 | 1988-06-28 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Secondary alcohol derivatives for use in liquid crystal materials and devices |
| US4778621A (en) * | 1985-10-14 | 1988-10-18 | Chisso Corporation | Ester compound |
| JPS63165345A (en) * | 1986-12-26 | 1988-07-08 | Chisso Corp | Optically active-2-methyl-alkanoates and utilized substance thereof |
| US5167863A (en) * | 1987-12-24 | 1992-12-01 | Hitachi, Ltd. | Optically active compound, liquid crystal composition containing said compound, and liquid crystal optical modulator using said composition |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0550493B2 (en) | 1993-07-29 |
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