JPS63126842A - Optically active compound - Google Patents
Optically active compoundInfo
- Publication number
- JPS63126842A JPS63126842A JP27358986A JP27358986A JPS63126842A JP S63126842 A JPS63126842 A JP S63126842A JP 27358986 A JP27358986 A JP 27358986A JP 27358986 A JP27358986 A JP 27358986A JP S63126842 A JPS63126842 A JP S63126842A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- optically active
- formulas
- tables
- 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 23
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 239000004990 Smectic liquid crystal Substances 0.000 claims abstract description 19
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 230000003287 optical effect Effects 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 239000000126 substance Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 14
- 239000000463 material Substances 0.000 abstract description 13
- 230000004044 response Effects 0.000 abstract description 10
- 230000010287 polarization Effects 0.000 abstract description 8
- 230000002269 spontaneous effect Effects 0.000 abstract description 8
- 150000002148 esters Chemical class 0.000 abstract description 6
- -1 4-substituted-4'-(1-hydroxyethyl) biphenyl Chemical group 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 4
- 239000000194 fatty acid Substances 0.000 abstract description 4
- 229930195729 fatty acid Natural products 0.000 abstract description 4
- 150000004665 fatty acids Chemical class 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- PEMATPNGROZZDM-UHFFFAOYSA-N 1-[4-(4-octoxyphenyl)phenyl]ethyl hexanoate Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C(C)OC(=O)CCCCC)C=C1 PEMATPNGROZZDM-UHFFFAOYSA-N 0.000 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 34
- 239000012071 phase Substances 0.000 description 17
- 235000010290 biphenyl Nutrition 0.000 description 14
- 239000004305 biphenyl Substances 0.000 description 14
- 238000005809 transesterification reaction Methods 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 210000002858 crystal cell Anatomy 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 208000003464 asthenopia Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000007704 transition Effects 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）
本発明は液晶表示素子に用いられる液晶材料、およびそ
の成分として有用な物質に関する。さらに詳しくは、強
誘電性液晶混合物の成分として有用な新規なカイラル物
質および該物質を含有する液晶混合物に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a liquid crystal material used in a liquid crystal display element and a substance useful as a component thereof. More particularly, the present invention relates to novel chiral materials useful as components of ferroelectric liquid crystal mixtures and liquid crystal mixtures containing the materials.
（従来の技術）
液晶表示素子としてはツイストネマチック（ＴＮ）型表
示素子が現在は最も広く用いられている。液晶ディスプ
レイは受光型であるので、目の疲れが少い、消費電力が
小さいといった特徴を持っている。しかし、ＴＮ型表示
素子は発光型表示素子（エレクトロルミネッセンスディ
スプレイ、プラズマディスプレイ等）と比べて応答が遅
いという欠点が未解決である。液晶ディスプレイの応答
速度の改善は種々試みられており、ＴＮ型表示：二代わ
る別の原理による液晶ディスプレイとして強誘電性液晶
を用いる表示方式がクラーク等によって提出された（Ｎ
、Ａ 。(Prior Art) Twisted nematic (TN) type display elements are currently most widely used as liquid crystal display elements. Since liquid crystal displays are light-receiving types, they have the characteristics of less eye fatigue and lower power consumption. However, the TN type display element has an unresolved drawback that its response is slower than that of a light emitting type display element (electroluminescent display, plasma display, etc.). Various attempts have been made to improve the response speed of liquid crystal displays. TN type display: A display system using ferroelectric liquid crystal as a liquid crystal display based on an alternative principle was proposed by Clark et al.
,A.
ｃ／ａｒｋ等； Ａｐｐｌ、Ｐｈｙｓ、Ｌｅｔｔ 、３
６ 、８９９ （１９８０）参照）。c/ark etc.; Appl, Phys, Lett, 3
6, 899 (1980)).
この表示方式は強誘電性液晶のカイラルスメクチックＣ
相またはカイラルスメクチックＨ相（ＳＣ”相またはＳ
Ｈ＊相とそれぞれ略記する）を利用するものであり、Ｔ
Ｎ表示方式に比べて３つの優れた特徴を有する。第一の
特徴は高速応答であり、応答時間はＴＮ表示素子に比べ
て１／ｌ ＯＯ以下である。第二の特徴はメモリー効果
であり、高速応答性と相俟って時分割駆動を容易にする
。第三の特徴は階調が容易に得られることである。ＴＮ
方式で濃淡の階調をとるには印加電圧を調節して行なう
ため、しきい値電圧の温度依存性や応答速度の電圧依存
性などの難問があるのに比べて、 ＳＣ＊相の光スイツ
チング効果を応用する表示方式では極性の反転時間を調
節することにより階調が得られるのでグラフィック表示
に非常に適している。This display method uses chiral smectic C, a ferroelectric liquid crystal.
phase or chiral smectic H phase (SC” phase or S
(abbreviated as H* phase), and T
It has three superior features compared to the N display method. The first feature is high-speed response, and the response time is 1/lOO or less compared to TN display elements. The second feature is the memory effect, which, together with high-speed response, facilitates time-division driving. The third feature is that gradations can be easily obtained. TN
In contrast, optical switching of the SC* phase is difficult to achieve because the applied voltage is adjusted to obtain the gradation of light and shade using this method. A display method that applies effects can obtain gradation by adjusting the polarity reversal time, so it is very suitable for graphic display.
このようにすぐれた特徴のある強誘電性液晶材料として
、従来はＳＣ＊相を有する液晶化合物で自発分極のＩＮ
（Ｐｇと略記する）が大きな物が求められていた。そ
の後、スメクチック液晶に、それ自体は液晶相を示さな
いが光学活性を有するカイラルな化合物を添加すること
によっても強誘電性液晶混合物が得られることが判り、
強誘電性液晶材料の探索の範囲はさらに拡まった（例え
ば、Ｍｏ／、Ｃｒｙｓｔ 、Ｌｉｑ 、Ｃｒｙｓｔ 、
８９ 、３２７（１９８２）参照）。As a ferroelectric liquid crystal material with such excellent characteristics, conventionally, a liquid crystal compound having an SC* phase and a spontaneous polarization IN
(abbreviated as Pg) was required. Later, it was discovered that a ferroelectric liquid crystal mixture could also be obtained by adding a chiral compound that does not itself exhibit a liquid crystal phase but has optical activity to a smectic liquid crystal.
The scope of exploration of ferroelectric liquid crystal materials has further expanded (e.g. Mo/, Crystal, Liq, Crystal,
89, 327 (1982)).
（発明が解決しようとする問題点）
前述したことからも判るように、本発明の第一の目的は
、既存の液晶物質と相溶性があり、スメクチック液晶に
溶解することにより強誘電性液晶混合物を得られるよう
な、新規な光学活性物質を提供することにある０本発明
の他の目的は大きな自発分極の値を有するスメクチック
液晶混合物ならびに応答速度の大きい光スイツチング素
子を提供することにある。(Problems to be Solved by the Invention) As can be seen from the above, the first object of the present invention is to create a ferroelectric liquid crystal mixture that is compatible with existing liquid crystal materials and is dissolved in a smectic liquid crystal. Another object of the present invention is to provide a smectic liquid crystal mixture having a large spontaneous polarization value and an optical switching device having a high response speed.
２（問題点を解決する手段）
本発明の第一は・
（１）一般式
（（１）式中、Ｒ１は炭素数１〜１日のアルキル基もし
くはアルキルオキン基を示し、Ｒ２は炭素ロゲン原子ま
たはンアノ基を示す。）にて表わされる光学活性化合物
、
であり、本発明の第二は、
（２）少くとも１つのスメクチック液晶物質および前項
に記載の一般式（冨）にて表わされる光学活性化合物く
とも１つを含有することを特徴とする強誘電性液晶混合
物、
であり、本発明の第三は、
（３）前記第（２）項に記載の強誘電性液晶混合物を用
いることを特徴とする光スイツチング素子・である。2 (Means for Solving Problems) The first aspect of the present invention is: (1) General formula (In formula (1), R1 represents an alkyl group or an alkylokyne group having 1 to 1 carbon atoms, and R2 represents a carbon halogen atom. The second aspect of the present invention is an optically active compound represented by (2) at least one smectic liquid crystal substance and an optically active compound represented by the general formula (among) described in the preceding section. A ferroelectric liquid crystal mixture characterized by containing at least one active compound, and the third aspect of the present invention is (3) using the ferroelectric liquid crystal mixture according to item (2) above. This is an optical switching element characterized by:
本発明により提供される物質は光学活性な４−アルキル
−４’−（１−アルカノイルオキンエチル）ビフェニル
および４−アルキルオキン−４’−（１−フルカノイル
オキンエチル）ビフェニルおよびこれらの化合物のベン
ゼン遥の側位の唯１つがハロゲンもしくはンアノ基で置
換された光学活性化合物である。例えば、
４−ペンチル−４’−（１−ヘキサノイルオキンエチル
）ビフェニル、
４−ペンチル−４’−（１−ブタノイルオキンエチル）
ビフェニル、
４−オクチルオキン−４’−（１−ヘキサノイルオキン
エチル）ビフェニル、
４−オクチルオキン−４’−（１−ブタノイルオキンエ
チル）ビフェニル
などの光学活性なビフェニル誘導体、側位の３−位もし
くは３′−位をＦ原子で置換した光学活性なビフェニル
誘導体などを挙げることができる。The substances provided by the present invention are optically active 4-alkyl-4'-(1-alkanoyl-oquinethyl)biphenyl and 4-alkyl-4'-(1-flukanoyl-oquinethyl)biphenyl and their compounds. It is an optically active compound in which only one side of benzene is substituted with a halogen or an ano group. For example, 4-pentyl-4'-(1-hexanoyl quinethyl)biphenyl, 4-pentyl-4'-(1-butanoyl quinethyl)
optically active biphenyl derivatives such as biphenyl, 4-octyloquine-4'-(1-hexanoyloquinethyl)biphenyl, and 4-octyloquine-4'-(1-butanoyloquinethyl)biphenyl; Examples include optically active biphenyl derivatives in which the F atom is substituted at the 3'-position or the 3'-position.
本発明により提供される光学活性なビフェニル誘導体は
既存の多くの液晶性物質に溶解するので液晶材料の成分
として混合できる。特に強誘電性液晶混合物の成分とし
て好ましく用いられる。後述する実施例に示されるよう
に、本発明の光学活性ビフェニル誘導体は、たとえそれ
自体が液晶相を示さない物であってもスメクチック液晶
混合物の成分として用いるとき・得られるスメクチツク
相において大きなＰ３値を実現できる。このような潜在
的自発分極は本発明の光学活性ビフェニル誘導体をスメ
クチックＣ液晶に添加することによって最も優れた効果
をもたらす。本発明の光学活性化合物を添加することに
より得られるスメクチックＣ液晶混合物に誘起される自
発分極の大きさは数ｎｃ／ｃｒ／ｌの値であり、高速応
答の光スイツチング素子の材料として充分実用にできる
大きさの値である。The optically active biphenyl derivative provided by the present invention is soluble in many existing liquid crystal materials, so it can be mixed as a component of a liquid crystal material. It is particularly preferably used as a component of a ferroelectric liquid crystal mixture. As shown in the Examples below, even if the optically active biphenyl derivative of the present invention does not exhibit a liquid crystal phase itself, when used as a component of a smectic liquid crystal mixture, the resulting smectic phase exhibits a large P3 value. can be realized. Such latent spontaneous polarization brings about the most excellent effect by adding the optically active biphenyl derivative of the present invention to the smectic C liquid crystal. The magnitude of the spontaneous polarization induced in the smectic C liquid crystal mixture obtained by adding the optically active compound of the present invention is several nc/cr/l, which is sufficient for practical use as a material for high-speed response optical switching devices. This value is as large as possible.
本発明の光学活性ビフェニル誘導体は、例えば（１）式
で表わされる、光学活性な４−置換−４′−（１−ヒド
ロキンエチル）ビフェニルと（り式で表わされる脂肪酸
とを縮合させることによって得られる。The optically active biphenyl derivative of the present invention can be obtained by condensing optically active 4-substituted-4'-(1-hydroquinethyl)biphenyl represented by the formula (1) with a fatty acid represented by the formula (1). can get.
す
（リ （璽）（り（これらの式中
、Ｒ１、Ｒ１および人はそれぞれ前記した意味をもつ）
、（１）式の光学活性アルコールは市販のラセミアル
コール、または例えば以下に示す合成ルートに従って得
られるラセミアルコールと、低級脂肪酸のトリグリセラ
イドとの間で生化学的不斉エステル交換反応を行なうこ
とにより得られる。すなわち、生化学的エステル交換を
ラセミアルコールの一対の対掌体のいずれか一方のみが
起すよう（＝・しであるので、得られるエステルの加水
分解により生成するアルコールと生化学的にエステルを
形成しなかったアルコールとは互いに対掌体ななしてい
る。(In these formulas, R1, R1 and person each have the meanings given above)
The optically active alcohol of formula (1) can be obtained by performing a biochemical asymmetric transesterification reaction between a commercially available racemic alcohol or, for example, a racemic alcohol obtained according to the synthetic route shown below and a triglyceride of a lower fatty acid. It will be done. In other words, biochemical transesterification occurs with only one of the pair of enantiomers of the racemic alcohol (=・), so it is possible to biochemically form an ester with the alcohol produced by hydrolysis of the resulting ester. They are mutually enantiomers with alcohol.
（Ｒ１がアルキルオキン基であるラセミアルコール）
（Ｂｔがアルキル基であるラセミアルコール）フェニレ
ン環の側位をへロゲン原子もしくはンアノ基で置換され
たラセミアルコールも上記の合成法に準じて調製するこ
とができる。(Racemic alcohol in which R1 is an alkyl group) (Racemic alcohol in which Bt is an alkyl group) Racemic alcohol in which the side position of the phenylene ring is substituted with a herogen atom or an ano group can also be prepared according to the above synthesis method. can.
前記した生化学的不斉エステル交換反応は実質的に水の
不存在の液相で、酵素として例えばリパーゼを用い、３
０〜４５℃で行われる。反応はおよそ１日ないし３０日
間で行われる。ラセミアルコールとトリグリセライドだ
けで均一な液相を得られない場合には１ヘプタン１ヘキ
サン、トルエンなどの炭化水素を溶媒として用いて不斉
エステル交換反応を行なうことができる。The biochemical asymmetric transesterification reaction described above is carried out in a liquid phase substantially in the absence of water, using lipase as an enzyme, and
It is carried out at 0-45°C. The reaction takes approximately 1 to 30 days. If a homogeneous liquid phase cannot be obtained using only racemic alcohol and triglyceride, an asymmetric transesterification reaction can be carried out using a hydrocarbon such as 1-heptane, 1-hexane, or toluene as a solvent.
本発明の光学活性エステルの対掌体の一方は前述の生化
学的エステル交換によっても得ることができる。他方の
対掌体エステルは生化学的にエステル形成しなかったア
ルコールを原料に（１）式に従って調製できる。One of the enantiomers of the optically active ester of the present invention can also be obtained by the biochemical transesterification described above. The other enantiomer ester can be prepared according to formula (1) using an alcohol that has not biochemically formed an ester as a raw material.
本発明により提供される強誘電性液晶混合物は既知のス
メクチック液晶物質に（１）式で表わされる光学活性化
合物を溶解することにより容易に得られる。スメクチッ
ク液晶物質としてはスメクチックＣ相（ＳＣ相と略記す
る）を示す物が好ましく用いられる。ＳＣ相を示す液晶
化合物としては以下に示す。The ferroelectric liquid crystal mixture provided by the present invention can be easily obtained by dissolving the optically active compound represented by formula (1) in a known smectic liquid crystal material. As the smectic liquid crystal substance, a substance exhibiting a smectic C phase (abbreviated as SC phase) is preferably used. Liquid crystal compounds exhibiting SC phase are shown below.
（これらの式においてＲおよびＷは独立にアルキル基を
示す。）などの一般式で表わされる化合物を挙げること
ができる。(In these formulas, R and W independently represent an alkyl group.) Compounds represented by general formulas such as the following can be mentioned.
ｙ−＋−ＩちのＳＣ妨島にＷＬ合すスｍ才のを蛍沃袢物
署の割合は、ＳＣ液晶の種類および混合比によっても異
なるが、概ね１〜３０重量％が適当である。The proportion of y-+-I to SC and WL varies depending on the type of SC liquid crystal and the mixing ratio, but is approximately 1 to 30% by weight.
（り式のカイラル化合物の含量が１重量％未満では充分
なＰｓ値を得難く・また含量が３０重量％を越えると得
られる混合物のＳＣ＊相温度領域が狭くなるという欠点
が目立ってくる。(If the content of the chiral compound of formula (2) is less than 1% by weight, it is difficult to obtain a sufficient Ps value. If the content exceeds 30% by weight, the disadvantage that the SC* phase temperature range of the resulting mixture becomes narrow becomes noticeable.
本発明によ′つて提供される光学活性化合物は在来のス
メクチックＣ液晶に添加した場合・その粘度を大きく上
昇させることはないので強誘電性液晶混合物の成分とし
て用い易い。The optically active compound provided by the present invention does not significantly increase the viscosity when added to conventional smectic C liquid crystals, so it can be easily used as a component of ferroelectric liquid crystal mixtures.
さらに１本発明によれば、一対の対掌体が容易に得られ
、これらは互いに逆の向きの自発分極もしくは潜在的自
発分極を示すので強誘電性液晶材料としての使用に制約
が少いという利点もある。Furthermore, according to the present invention, a pair of enantiomers can be easily obtained, and since these exhibit spontaneous polarization or potential spontaneous polarization in opposite directions, there are fewer restrictions on their use as ferroelectric liquid crystal materials. There are also advantages.
また、本発明の光学活性化合物は後記される参考例に示
すように、在来のネマチック液晶にカイラル剤として微
量添加して用いることもできる。Further, the optically active compound of the present invention can also be used by adding a small amount of it to a conventional nematic liquid crystal as a chiral agent, as shown in the reference examples described later.
（実施例）
以下に実施例により本発明の詳細な説明するが本発明は
これらの実施例に限定されるものではない。(Examples) The present invention will be described in detail below with reference to Examples, but the present invention is not limited to these Examples.
実施例Ｉ
Ｈ−４−オクチルオキン−４’−（１−ヘキナノイルオ
キンエチル）ビフェニル
℃）をトリブチリンとの間で生化学的エステル交換して
得られた光学活性Ｈ−４−オクチルオキンー４’−（１
−ヒドロキンエチル）ビフェニル（８点１ｚ３，６℃１
．： α） ２４°’ −２７，０° （ＣＩ、０ 、
ＣＨＣｌ５ ） ） ？、Ｏｆ （２１ｍ−ｍｏｌ
りをシンクロへキシルカルボジイミド（ＤＤＣと略記す
る）７．５ ｆ （３６ｍ−ｍｏｌ ）およびジメチル
アミノピリジン（ＤＭＡＰと略記する） １．ｏ ｆと
ともにジクロロメタン２００−に溶解した。この溶液に
カプロン酸３．４ ｆ （２９ｍ−ｔｏｏｌ ）を加え
て室温下に６時間攪拌した。析出した結晶なｒ別し１Ｆ
液に純水２００ｆＲ１を加えて、有機層を分離した。こ
の有機層を６Ｎ塩酸、次いで２Ｎ水酸化ナトリウム水溶
液で中和した後、洗滌水が中性になる迄純水で洗滌した
。得られた溶液から溶媒および低沸分を溜去した残渣を
エタノールから再結晶して目的のＨ−４−オクチルオキ
ンー４’−（１−ヘキサノイルオキンエチル）ビフェニ
ル６．８ｆを得た。この物の融点は６０．８℃％ 比に
光度＃ｉ （ａ ）、；” −７８，４° （Ｃ０，８
Ｂ。Example I Optically active H-4-octyloquine-4' obtained by biochemical transesterification of H-4-octyloquine-4'-(1-hequinanoyloquinethyl)biphenyl °C) with tributyrin −(1
-Hydroquinethyl)biphenyl (8 points 1z3, 6℃1
．． : α) 24°' -27,0° (CI, 0,
CHCl5))? , Of (21 m-mol
7.5 f (36 m-mol) of synchhexylcarbodiimide (abbreviated as DDC) and dimethylaminopyridine (abbreviated as DMAP) 1. It was dissolved in dichloromethane 200°C along with of. 3.4 f (29 m-tool) of caproic acid was added to this solution, and the mixture was stirred at room temperature for 6 hours. Separate the precipitated crystals 1F
200 fR1 of pure water was added to the liquid and the organic layer was separated. This organic layer was neutralized with 6N hydrochloric acid and then with a 2N aqueous sodium hydroxide solution, and then washed with pure water until the washing water became neutral. The solvent and low-boiling components were distilled off from the resulting solution, and the residue was recrystallized from ethanol to obtain the desired H-4-octyloquine-4'-(1-hexanoyloquinethyl)biphenyl 6.8f. The melting point of this substance is 60.8°C%.
B.
Ｃ，Ｈ，ＯＨ）であった。C, H, OH).
実施例２
光学活性４−ペンチルー４’−（１−ヘキサ／イルオキ
ンヱチル）ビフェニル
ラセミ仕）−４−ペンチルー４’−（１−ヒドロキン・
エチル）ビフェニル（融点９０．０℃）を生化学的エス
テル交換により光学分割して得られた、Ｈ−４−ペンチ
ル−４′−（１−ヒドロキンエチル）ビフェニルＩＭ点
８３．８℃、〔α〕。Example 2 Optically active 4-pentyl-4'-(1-hexa/yloquinethyl)biphenyl racemic)-4-pentyl-4'-(1-hydroquinethyl)
H-4-pentyl-4'-(1-hydroquinethyl)biphenyl IM point 83.8°C, obtained by optical resolution of H-4-pentyl-4'-(1-hydroquinethyl)biphenyl (melting point 90.0°C) by biochemical transesterification. α〕.
−２５，０° （Ｃ１，０、Ｃ１３０Ｈ） ） ５．
Ｏｆ 、ＤＤＣ７、Ｏｆ、ＤＭＡＰＩ、Ｏｆおよびカブ
°ｃｒｙ酸３，０ｔを用いて・実施例１と同様にして光
学活性４−ヘンチル−４’−（１−ヘキチノイルオキン
エテル）ビフェニル３．２２を得た。この物の融点は１
０℃であった。-25,0° (C1,0, C130H)) 5.
Using Of, DDC7, Of, DMAPI, Of and 3.0 t of cabbic acid, optically active 4-hentyl-4'-(1-hexitynoyl oxyne ether) biphenyl 3.22 was prepared in the same manner as in Example 1. I got it. The melting point of this substance is 1
It was 0°C.
実施例３
以下の６成分
からなる液晶混合物四の相転移は
４℃ ６５℃ ７９℃ ９０℃Ｃ−
一→ ＳＣ−一→ ８人−一→ Ｎ−−一→ 工（ここ
でｃ、ｇｈ、Ｎ及びＩはそれぞれ結晶。Example 3 The phase transition of liquid crystal mixture 4 consisting of the following six components is 4℃ 65℃ 79℃ 90℃C-
1 → SC-1 → 8 people-1 → N--1 → Engineering (where c, gh, N, and I are each a crystal.
スメクチック人、ネマチックおよび等方性液体の各相を
意味する）であった。smectic, nematic and isotropic liquid phases).
この混合物（Ａ） ９０重量部に実施例１で調製した１
０］ｉ量部
を添加して液晶混合物を調製した。1 prepared in Example 1 was added to 90 parts by weight of this mixture (A).
0]i parts to prepare a liquid crystal mixture.
この混合物は２℃〜３７℃の温度範囲でＳＣ＊相を示し
、２５℃におけるＰｓ値は４，４ ｎＣ／ｃｒ１．傾き
角は１２°であった。This mixture exhibits an SC* phase in the temperature range from 2°C to 37°C, and the Ps value at 25°C is 4.4 nC/cr1. The tilt angle was 12°.
またこの混合物を配向処理剤としてポリビニルアルコー
ルを塗布した表面をラビングして平行配向処理を施した
、透明電極を備えたセル厚２μ悔のセルに封入して液晶
セルを作成した。この液晶セルを直交する２枚の偏光板
の間に置いて、波高値１０Ｖの矩形波を印加したところ
、透過光強闇の変化が観察された。透過光強度の変化か
ら求めたこの液晶セルの応答時間は２５℃でｌ ＯＯｐ
ｍｅｃ、であった。Further, this mixture was sealed in a cell having a cell thickness of 2 μm and equipped with transparent electrodes, which was subjected to a parallel alignment treatment by rubbing the surface coated with polyvinyl alcohol as an alignment treatment agent to prepare a liquid crystal cell. When this liquid crystal cell was placed between two orthogonal polarizing plates and a rectangular wave with a peak value of 10 V was applied, changes in the intensity of transmitted light were observed. The response time of this liquid crystal cell, determined from the change in transmitted light intensity, is l OOp at 25°C.
It was mec.
参考例
以下の４成分
Ｃ，Ｈ８→４Ｎ ２０重量％ｎｎ−Ｃ５Ｈ１
１Ｒ〉べφΣ−ＣＮ ３５１ｔｓｎ−Ｃ９Ｈ
１１１ヘ？〉べφΣ（Ｎ ２５重量％からなる
ネマチック液晶混合物を、配向処理剤として、ポリビニ
ルアルコールを塗布し、その表面をラビングして平行配
向処理を施した透明電極材の電極間隔１０μ鴨のセル；
；注入してＴＮ型表示セルとし、これを偏光顕微鐘下で
観察したところ・リバース・ツイストドメインを生じて
いるのが観察された。このネマチック液晶混合物に実施
例２で調製した光学活性化合物を０．１重量％添加し、
同様１：： Ｔ Ｎ型セルにて観察したところリバース
・ツイストドメインは解消され、均一なネマチック相が
観察された。Reference example: 4 components C, H8 → 4N 20% by weight nn-C5H1
1R>beφΣ-CN 351tsn-C9H
To 111? 〉BeφΣ(A nematic liquid crystal mixture consisting of 25% by weight of N, coated with polyvinyl alcohol as an alignment treatment agent, and subjected to a parallel alignment treatment by rubbing the surface of the transparent electrode material, with an electrode spacing of 10 μm);
When the cell was injected into a TN type display cell and observed under a polarizing microscope, it was observed that a reverse twist domain was formed. Adding 0.1% by weight of the optically active compound prepared in Example 2 to this nematic liquid crystal mixture,
Similar 1:: TN When observed in an N-type cell, the reverse twist domain was eliminated and a uniform nematic phase was observed.
（発明の効果）
前述したように、本発明１：より提供される光学活性化
合物はスメクチックＣ液晶に混合することにより混合物
のＳＣ＊相において大きな自発分極な誇起し、該液晶混
合物を液晶材料に用いて応答速度が非常に大きい強誘電
性液晶表示素子が得られる。(Effects of the Invention) As described above, when the optically active compound provided by the present invention 1 is mixed with a smectic C liquid crystal, it exhibits a large spontaneous polarization in the SC* phase of the mixture, and the liquid crystal mixture can be used as a liquid crystal material. A ferroelectric liquid crystal display element with extremely high response speed can be obtained.
以上
特許出願人 チ ッ ソ 株 式 会 社代理人 弁
理士 佐々井 彌太部
同 上 野中克彦Patent applicant Chisso Co., Ltd. Company agent Patent attorney Yatabe Sasai Katsuhiko Nonaka
Claims (3)
アルキルオキシ基を示し、Ｒ＾２は炭素数１〜１８のア
ルキル基を示し、Ａは▲数式、化学式、表等があります
▼、▲数式、化学式、表等があります▼または▲数式、
化学式、表等があります▼を示し、Ｘはハ ロゲン原子またはシアノ基を示す。）にて表わされる光
学活性化合物。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R^1 represents an alkyl group or alkyloxy group having 1 to 18 carbon atoms, and R^2 represents an alkyl group having 1 to 18 carbon atoms. , and A is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ Mathematical formulas,
There are chemical formulas, tables, etc. ▼ indicates, and X indicates a halogen atom or a cyano group. ) An optically active compound represented by
式 ▲数式、化学式、表等があります▼ （式中、Ｒ＾１は炭素数１〜１８のアルキル基もしくは
アルキルオキシ基を示し、Ｒ＾２は炭素数１〜１８のア
ルキル基を示し、Ａは▲数式、化学式、表等があります
▼、▲数式、化学式、表等があります▼または▲数式、
化学式、表等があります▼を示し、Ｘはハ ロゲン原子またはシアノ基を示す。）にて表わされる光
学活性化合物少くとも１つを含有することを特徴とする
強誘電性液晶混合物。(2) At least one smectic liquid crystal substance and general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R^1 represents an alkyl group or alkyloxy group having 1 to 18 carbon atoms, and R^2 is Indicates an alkyl group having 1 to 18 carbon atoms, and A is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲Mathematical formulas,
There are chemical formulas, tables, etc. ▼ indicates, and X indicates a halogen atom or a cyano group. ) A ferroelectric liquid crystal mixture containing at least one optically active compound represented by:
アルキルオキシ基を示し、Ｒ＾２は炭素数１〜１８のア
ルキル基を示し、Ａは▲数式、化学式、表等があります
▼、▲数式、化学式、表等があります▼または▲数式、
化学式、表等があります▼を示し、Ｘはハ ロゲン原子またはシアノ基を示す。）にて表わされる化
合物少くとも１つを含む強誘電性液晶混合物を用いる光
スイッチング素子。(3) At least one smectic liquid crystal substance and general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R^1 represents an alkyl group or alkyloxy group having 1 to 18 carbon atoms, and R^2 is Indicates an alkyl group having 1 to 18 carbon atoms, and A is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲Mathematical formulas,
There are chemical formulas, tables, etc. ▼ indicates, and X indicates a halogen atom or a cyano group. ) An optical switching element using a ferroelectric liquid crystal mixture containing at least one compound represented by:
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27358986A JPH0784412B2 (en) | 1986-11-17 | 1986-11-17 | Optically active compound |
| US07/113,763 US4882084A (en) | 1986-11-07 | 1987-10-28 | Optically active substituted biphenyl compounds |
| DE8787309626T DE3769289D1 (en) | 1986-11-07 | 1987-10-30 | OPTICALLY ACTIVE CONNECTIONS. |
| EP87309626A EP0270243B1 (en) | 1986-11-07 | 1987-10-30 | Optically active compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27358986A JPH0784412B2 (en) | 1986-11-17 | 1986-11-17 | Optically active compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63126842A true JPS63126842A (en) | 1988-05-30 |
| JPH0784412B2 JPH0784412B2 (en) | 1995-09-13 |
Family
ID=17529895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27358986A Expired - Fee Related JPH0784412B2 (en) | 1986-11-07 | 1986-11-17 | Optically active compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0784412B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63254421A (en) * | 1987-04-13 | 1988-10-21 | Matsushita Electric Ind Co Ltd | Liquid crystal display device |
| JPS63256688A (en) * | 1987-04-13 | 1988-10-24 | Matsushita Electric Ind Co Ltd | Liquid crystal composition |
| JPH01104025A (en) * | 1987-07-07 | 1989-04-21 | Sumitomo Chem Co Ltd | Optically active benzene derivative and its production |
| JPH01139689A (en) * | 1987-11-26 | 1989-06-01 | Chisso Corp | Ferroelectric liquid crystal composition |
-
1986
- 1986-11-17 JP JP27358986A patent/JPH0784412B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63254421A (en) * | 1987-04-13 | 1988-10-21 | Matsushita Electric Ind Co Ltd | Liquid crystal display device |
| JPS63256688A (en) * | 1987-04-13 | 1988-10-24 | Matsushita Electric Ind Co Ltd | Liquid crystal composition |
| JPH01104025A (en) * | 1987-07-07 | 1989-04-21 | Sumitomo Chem Co Ltd | Optically active benzene derivative and its production |
| JPH01139689A (en) * | 1987-11-26 | 1989-06-01 | Chisso Corp | Ferroelectric liquid crystal composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0784412B2 (en) | 1995-09-13 |
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