JPS6377864A - Liquid crystal compound and liquid crystal composition - Google Patents
Liquid crystal compound and liquid crystal compositionInfo
- Publication number
- JPS6377864A JPS6377864A JP21922586A JP21922586A JPS6377864A JP S6377864 A JPS6377864 A JP S6377864A JP 21922586 A JP21922586 A JP 21922586A JP 21922586 A JP21922586 A JP 21922586A JP S6377864 A JPS6377864 A JP S6377864A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- pyrazine
- formula
- optically active
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 46
- 150000001875 compounds Chemical class 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- -1 4-methylhexyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 abstract description 38
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 20
- 230000004044 response Effects 0.000 abstract description 12
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 abstract description 8
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 6
- 230000005684 electric field Effects 0.000 abstract description 5
- 150000004820 halides Chemical class 0.000 abstract description 3
- OTVZGAXESBAAQQ-UHFFFAOYSA-N pyrazine-2,3-dicarbonitrile Chemical class N#CC1=NC=CN=C1C#N OTVZGAXESBAAQQ-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
- 229910006124 SOCl2 Inorganic materials 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 239000005973 Carvone Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KJKZZQNHNUAXEW-UHFFFAOYSA-N 5-(4-decoxyphenyl)pyrazine-2-carboxylic acid Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C1=CN=C(C(O)=O)C=N1 KJKZZQNHNUAXEW-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- VRTSODYSFIAAGC-UHFFFAOYSA-N 5-(4-octoxyphenyl)pyrazine-2-carboxylic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CN=C(C(O)=O)C=N1 VRTSODYSFIAAGC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- BLHGESSSNQTRNW-UHFFFAOYSA-N 5-(4-decylphenyl)pyrazine-2-carboxylic acid Chemical compound C(CCCCCCCCC)C1=CC=C(C=C1)C=1N=CC(=NC=1)C(=O)O BLHGESSSNQTRNW-UHFFFAOYSA-N 0.000 description 2
- MJQBIAREWGLLKB-UHFFFAOYSA-N 5-(4-dodecoxyphenyl)pyrazine-2-carboxylic acid Chemical compound C1=CC(OCCCCCCCCCCCC)=CC=C1C1=CN=C(C(O)=O)C=N1 MJQBIAREWGLLKB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- LCFKURIJYIJNRU-UHFFFAOYSA-N 2-methylhexan-1-ol Chemical compound CCCCC(C)CO LCFKURIJYIJNRU-UHFFFAOYSA-N 0.000 description 1
- LNEPRUZQMSZVIU-UHFFFAOYSA-N 5,6-bis[4-(9,9-dimethylacridin-10-yl)phenyl]pyrazine-2,3-dicarbonitrile Chemical compound CC1(C2=CC=CC=C2N(C=2C=CC=CC1=2)C1=CC=C(C=C1)C=1N=C(C(=NC=1C1=CC=C(C=C1)N1C=2C=CC=CC=2C(C2=CC=CC=C12)(C)C)C#N)C#N)C LNEPRUZQMSZVIU-UHFFFAOYSA-N 0.000 description 1
- GEEYJKKISSEGHD-UHFFFAOYSA-N 5-(4-dodecylphenyl)pyrazine-2-carboxylic acid Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1C1=CN=C(C(O)=O)C=N1 GEEYJKKISSEGHD-UHFFFAOYSA-N 0.000 description 1
- TZCXTKKQRFYIBB-UHFFFAOYSA-N 5-(4-hexoxyphenyl)pyrazine-2-carboxylic acid Chemical compound C1=CC(OCCCCCC)=CC=C1C1=CN=C(C(O)=O)C=N1 TZCXTKKQRFYIBB-UHFFFAOYSA-N 0.000 description 1
- PTHWROXULXZKHE-UHFFFAOYSA-N 5-(4-nonoxyphenyl)pyrazine-2-carboxylic acid Chemical compound C(CCCCCCCC)OC1=CC=C(C=C1)C=1N=CC(=NC=1)C(=O)O PTHWROXULXZKHE-UHFFFAOYSA-N 0.000 description 1
- WTZXNFJMDXBDSZ-UHFFFAOYSA-N 5-(4-octoxyphenyl)pyrazine-2,3-dicarbonitrile Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CN=C(C#N)C(C#N)=N1 WTZXNFJMDXBDSZ-UHFFFAOYSA-N 0.000 description 1
- VIIBBFJNKGZWQC-UHFFFAOYSA-N 5-(4-octoxyphenyl)pyrazine-2,3-dicarboxylic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CN=C(C(O)=O)C(C(O)=O)=N1 VIIBBFJNKGZWQC-UHFFFAOYSA-N 0.000 description 1
- LSPOAJCPZNEMCS-UHFFFAOYSA-N 5-(4-octylphenyl)pyrazine-2-carboxylic acid Chemical compound C(CCCCCCC)C1=CC=C(C=C1)C=1N=CC(=NC=1)C(=O)O LSPOAJCPZNEMCS-UHFFFAOYSA-N 0.000 description 1
- AJYIXHOIVLVGQB-UHFFFAOYSA-N 5-(4-undecoxyphenyl)pyrazine-2-carboxylic acid Chemical compound C1=CC(OCCCCCCCCCCC)=CC=C1C1=CN=C(C(O)=O)C=N1 AJYIXHOIVLVGQB-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 208000003464 asthenopia Diseases 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- 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性化合物及び該液晶性化合物を少な
くとも１種類含有する液晶組成物に関する。 。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel liquid crystal compound and a liquid crystal composition containing at least one kind of the liquid crystal compound. .
現在、液晶は表示材料として広く用いられているが、そ
うした表示素子のほとんどはネマチック相に属する液晶
材料を用いるところのＴＮ（Ｔｗｉｓｔｅｄ Ｎｅｍａ
ｔｉｃ）型表示方式である。このＴＮ型表示方式は受光
型のため目が疲れない、消費電力が極めて少ないなど優
れた特長を持つものであるが、応答速度が遅いこと、視
る角度によってはコントラストがとれないこと、大画面
で高精細な表示素子をつくるためにはＴ Ｐ Ｔ （Ｔ
ｈｉｎ ｆｉｌ＋＊ｔｒａｎｓｉｓｔｏｒ）等の能動素
子をつけ加える必要があることなどの欠点がある。最近
は、表示装置に対して高速応答性が要求されており、こ
うした要求に答えるべく液晶材料の改良が試みられてき
た。しかし、他の発光型ディスプレイ（ＣＲ’ｒ、ＥＬ
、プラズマディスプレイ等）と比較すると、応答速度は
十分でなく、高精細な表示もできなかった。受光型、低
消費電力といった液晶の特長を生かし、なおかつ発光型
ディスプレイに匹敵する応答速度と高精細性を確保する
ためにはネマチック相を利用するＴＮ型表示方式に代わ
る新しい液晶表示方式が必要である。新しい液晶表示方
式の中で上記の優れた特性を持つことが期待されるもの
として、強誘電性液晶の光スイツチング現象を利用した
表示方式（Ｎ、Ａ、Ｃ１ａｒｋ、Ｓ、Ｔ、Ｌａｇｅｒｗ
ａｌｌ ；Ａｐｐｌ、Ｐｈｙｓ、Ｌｅｔｔ、、 ３６
、８９９ （１９８０） ）がある０強誘電性液晶は１
９７５午にＲ，Ｂ、Ｍｅｙｅｒらによってその存在が発
表されたもので（Ｒ，Ｂ。Currently, liquid crystals are widely used as display materials, but most of these display elements are TN (Twisted Nema), which uses liquid crystal materials belonging to the nematic phase.
tic) type display method. This TN type display system has excellent features such as being light-receiving type so it does not cause eye strain and consumes very little power, but it has slow response speed, lack of contrast depending on the viewing angle, and large screen size. In order to create high-definition display elements using T P T (T
There are disadvantages such as the need to add active elements such as hin fil+*transistor). Recently, high-speed response has been required for display devices, and attempts have been made to improve liquid crystal materials in order to meet these demands. However, other emissive displays (CR'r, EL
, plasma displays, etc.), the response speed was not sufficient and high-definition display was not possible. In order to take advantage of the features of liquid crystals, such as light-receiving type and low power consumption, and still ensure response speed and high definition comparable to light-emitting displays, a new liquid crystal display method is needed to replace the TN display method that uses the nematic phase. be. Among the new liquid crystal display systems, display systems that utilize the optical switching phenomenon of ferroelectric liquid crystals (N, A, C1ark, S, T, Lagerw) are expected to have the above-mentioned excellent characteristics.
all ;Appl, Phys, Lett,, 36
, 899 (1980)), the 0 ferroelectric liquid crystal has 1
Its existence was announced in 1975 by R, B, Meyer et al. (R, B.
Ｍｅ７ｅｒ ｅｔ ａｌ、、Ｊ、Ｐｈｙｓ、（Ｐａｒｉ
ｓ） ３６ 、 Ｌ −６９（１９７５））、液晶の構
造上からカイラルスメクチックＣ相（ＳｍＣ”相）、あ
るいはカイラルスメクチックＨ相（ＳｍＨ”相）に属す
る。その後さらにカイラルスメクチックＩ相（Ｓ ｍ
ｒ ”相）、カイラルスメクチックＦ相（ＳｍＦ”相）
、カイラルスメクチックＣ相（Ｓ ｍＧ”相）、カイラ
ルスメクチックＪ相（ＳｍＪ”相）、カイラルスメクチ
ックに相（ＳｍＫ”相）が強誘電性を示す液晶相として
明らかとなった０強誘電性液晶性化合物としては後記衣
１に示したものが知−られている（Ｐｈ、Ｍａｒｔｉｎ
ｏｔ−Ｌａｇａｒｄｅ、Ｊ、Ｐｈ７ｇ、（Ｐａｒｉｓ）
止７．Ｃ５−１２９（１９７６）等）。Me7er et al., J. Phys.
s) 36, L-69 (1975)), and belongs to the chiral smectic C phase (SmC" phase) or chiral smectic H phase (SmH" phase) from the structure of the liquid crystal. Thereafter, the chiral smectic I phase (S m
r” phase), chiral smectic F phase (SmF” phase)
, chiral smectic C phase (SmG" phase), chiral smectic J phase (SmJ" phase), and chiral smectic phase (SmK" phase) have been revealed as liquid crystal phases exhibiting ferroelectric properties. As compounds, those shown in 1 below are known (Ph, Martin
ot-Lagarde, J, Ph7g, (Paris)
Stop 7. C5-129 (1976) etc.).
この強誘電性液晶は、自発分極を有するために非常に速
い応答速度を有する上にメモリー性のある双安定状態を
発現させることができ、さらに視野角特性もすぐれてい
ることから、大容量大画面のディスプレイとして適して
いる。This ferroelectric liquid crystal has a very fast response speed due to its spontaneous polarization, and can develop a bistable state with memory properties.Furthermore, it has excellent viewing angle characteristics, and has a large capacity. Suitable as a screen display.
ところが、これらの強誘電性液晶性化合物は、それぞれ
カイラルスメクチック相の温度範囲が高い、自発分極が
小さい、閾値特性が悪い等の欠点を持っており、必ずし
も満足すべきものではない。However, these ferroelectric liquid crystal compounds each have drawbacks such as a high chiral smectic phase temperature range, small spontaneous polarization, and poor threshold characteristics, and are not necessarily satisfactory.
本発明者らは、強誘電性液晶の光スイツチング現象を利
用した表示方式に利用することに適した液晶物質の開発
を主たる目的として種々の化合物を検討した結果１本発
明に到達した。The present inventors have arrived at the present invention as a result of studying various compounds with the main purpose of developing a liquid crystal material suitable for use in a display system utilizing the optical switching phenomenon of ferroelectric liquid crystal.
本発明は一般式（Ｉ）
（上記一般式中、Ｒ１は炭素原子数ｔ−ｔａのアルキル
基もしくはアルコキシ基であり、Ｒ８は光学活性な好ま
しくは炭素数が４〜１６のアルキル基を示す）で表わさ
れる液晶性化合物を提供するものである。The present invention is represented by the general formula (I) (In the above general formula, R1 is an alkyl group or an alkoxy group having t-ta carbon atoms, and R8 is an optically active alkyl group preferably having 4 to 16 carbon atoms.) The present invention provides a liquid crystalline compound represented by:
また本発明は、上記光学活性な液晶性化合物を少なくと
も１種類配合成分として含有する液晶組成物をも提供す
るものである。The present invention also provides a liquid crystal composition containing at least one of the optically active liquid crystal compounds described above as a compounding component.
上記一般式（Ｉ）の液晶性化合物は、例えば、一般式（
ＩＩ）
（式中Ｒは炭素原子数１〜１８のアルキル基もしくはア
ルコキシ基である）
で示される２、３−ジシアノピラジン誘導体を加水分解
後、脱炭酸し、一般式（ｍ）：
で示される２−カルボキシピラジン誘導体を、得、これ
をハロゲン化して酸ハロゲン化物となし、これに一般式
（■）：
ＨＯ−Ｒ” （ＩＶ）（式中Ｒ８
は光学活性なアルキル基を示す）で示される化合物を反
応せしめてエステル化することにより製造するができる
。The liquid crystal compound of the above general formula (I) may be, for example, a liquid crystal compound of the general formula (I).
II) (wherein R is an alkyl group or an alkoxy group having 1 to 18 carbon atoms) After hydrolyzing a 2,3-dicyanopyrazine derivative represented by the following formula, decarboxylation is performed to obtain a compound represented by the general formula (m): A 2-carboxypyrazine derivative was obtained, which was halogenated to give an acid halide, which was given the general formula (■): HO-R" (IV) (in the formula R8
It can be produced by reacting and esterifying a compound represented by (representing an optically active alkyl group).
なお、一般式（ＩＩ ）で示される２、３−ジシアノピ
ラジン銹導体は、それ自体公知の製造方法〔津田忠敬ら
、日本農芸化学会誌ｆＪＳ５２＠、２１３頁（１９７８
年）〕を用いることによって得られるものである。The 2,3-dicyanopyrazine rust conductor represented by the general formula (II) can be produced by a method known per se [Tadataka Tsuda et al., Journal of the Japanese Society of Agricultural Chemistry fJS52@, p. 213 (1978
year)].
このようにして得られる本発明の一般式（Ｉ）で示され
る液晶性化合物としては下記の化合物があげられる。Examples of the liquid crystalline compound represented by the general formula (I) of the present invention thus obtained include the following compounds.
５−（ｐ−ｎ−へキシルオキシフェニル）ピラジン−２
−カルボン酸−２′−メチルブチルエステル、５−（ｐ
−ｎ−オクチルオキシフェニル）ピラジン−２−カルボ
ン酸−２′−メチルブチルエステル、５−（ｐ−ｎ−へ
キシルオキシフェニル）ピラジン−２−カルボンｍ−３
’−メチルヘプチルエステル、５−（ｐ−ｎ−へプチル
オキシフェ三ル）ピラジン−２−カルボン酸−３′−メ
チルヘプチルエステル、５−（ｐ−ｎ−オクチルオキシ
フェニル）ピラジン−２−カルボン酸−３′−メチルヘ
プチルエステル、５−（ｐ−ｎ−デシルオキシフェニル
）ピラジン−２−カルボンＭ −３”−メチルヘプチル
エステル、５−（ｐ−ｎ−へキシルフェニル）ピラジン
−２−カルボン酸−３′−メチルヘプチルエステル、５
−（ｐ−ｎ−へブチルフェニル）ピラジン−２−カルボ
ン酸−３７−メチルへブチルエステル、５− （ｐ−ｎ
−ペンチルオキシフェニル）ピラジン−２−力ルポンｍ
ｔ′−メチルヘキシルエステル、５−（ｐ−ｎ−へキシ
ルオキシフェニル）ピラジン−２−カルボンｓ４′−メ
チルヘキシルエステル、５−（ｐ−ｎ−オクチルオキシ
フェニル）ピラジン−２−カルボン酸−４′−メチルヘ
キシルエステル、５−（ｐ−ｎ−デシルオキシフェニル
）ピラジン−２−カルボン酸−４′−メチルヘキシルエ
ステル、５−（ｐ−ｎ−ドデシルオ・キシフェニル）ピ
ラジン−２−カルボン酸−４′−メチルヘキシルエステ
ル、５−（ｐ−ｎ−）リゾシルオキシフェニル）ピラジ
ン−２−カルボン酸−４′−メチルヘキシルエステル、
５−（ｐ−ｎ−テトラデシルオキシフェニル）ピラジン
−２−カルボン酸−４′−メチルヘキシルエステル、５
−（ｐ−ｎ−ヘキサデシルオキシフェニル）ピラジン−
２−カルボン酸−４′−メチルヘキシルエステル
ル）ピラジン−２−カルボン酸−４′−メチルヘキシル
エステル、５−（ｐ−ｎ−オクチルフェニル）ピラジン
−２−カルボン酸−４′−メチルヘキシルエステル、５
−（ｐ−ｎ−デシルフェニル）ピラジン−２−カルボン
酸−４′−メチルヘキシルエステル、５−（ｐ−ｎ−ド
デシルフェニル）ピラジン−２−カルボン酸−４′−メ
チルヘキシルエステル、 ５ − （ｐ−ｎ−デシルオ
キシフェニル）ピラジン−２−カルボン酸−５′−メチ
ルヘプチルエステル、５−（ｐ−ｎ−ドデシルオキシフ
ェニル）ビラジン−２−カルボン−酸−５′−メチルヘ
プチルエステル、５−（ｐ−ｎ−テトラデシルオキシフ
ェニル）ピラジン−２−カルボン酸−５′−メチルヘプ
チルエステル、５−（ｐ−ｎ−へキシルオキシフェニル
）ヒラジン−２−カルボン酸−６′−メチルオクチルエ
ステル、５−（ｐ−ｎ−オクチルオキシフェニル）ピラ
ジン−２−カルボン酸−６′−メチルオクチルエステル
、５−（ｐ−ｎ−ノニルオキシフェニル）ピラジン−２
−カルボン酸−６′−メチルオクチルエステル、５−（
ｐ−ｎ−デシルオキシフェニル）ピラジン−２−カルボ
ン酸−６′−メチルオクチルエステル、５−（ｐ−ｎ−
ウンデシルオキシフェニル）ピラジン−２−カルボン酸
−６′−メチルオクチルエステル、５−（ｐ−ｎ−ドデ
シルオキシフェニル）ピラジン−２−カルボンＭ６′−
メチルオクチルエステル、５−（ｐ−ｎ−トリデシルオ
キシフェニル）ピラジン−２−カルボン酸−６′−メチ
ルオクチルエステル５−（ｐ−ｎ−テトラデシルオキシ
フェニル）ピラジンー２−カルボンｍ−６′−メチルオ
ク・チルエステル、５−（ｐ−ｎ−ヘキサデシルオキシ
フェニル）ピラジン−２−カルボン酸−６′−メチルオ
クチルエステル、５−（ｐ−ｎ−デシルフェニル）ピラ
ジン−２−カルボン酸−６′−メチルオクチルエステル
、５−（ｐ−ｎ−ドデシルフェニル）ピラジン−２−カ
ルボンｍ−６’−メチルオクチルエステル、５−（ｐ−
ｎ−デシルオキシフェニル）ピラジン−２−カルボン酸
−１′−メチルプロピルエステル、５−（ｐ−ｎ−デシ
ルオキシフェニル）ピラジン−２−カルボン酸−１′−
メチルブチルエステル、５−（ｐ−ｎ−ドデシルオキシ
フェニル）ピラジン−２−カルボン酸−１′−メチルブ
チルエステル、５−（ｐ−ｎ−デシルオキシフェニル）
ピラジン−２−カルボン酸−ｔ’−メチルヘプチルエス
テル、５− （ｐ−ｎ−ドデシルオキシフェニル）ピラ
ジン−２−カルボンＭ −ｔ ′−メチルヘプチルエス
テル、５−（ｐ−ｎ−Ｆ７”シルフェニル）ピラジン−
２−カルボン酸−１′−メチルヘプチルエステル。5-(pn-hexyloxyphenyl)pyrazine-2
-carboxylic acid-2'-methylbutyl ester, 5-(p
-n-octyloxyphenyl)pyrazine-2-carboxylic acid-2'-methylbutyl ester, 5-(pn-hexyloxyphenyl)pyrazine-2-carvone m-3
'-Methylheptyl ester, 5-(pn-heptyloxyphe3yl)pyrazine-2-carboxylic acid-3'-methylheptyl ester, 5-(pn-octyloxyphenyl)pyrazine-2-carboxylic acid Acid-3'-methylheptyl ester, 5-(pn-decyloxyphenyl)pyrazine-2-carvone M -3''-methylheptyl ester, 5-(pn-hexylphenyl)pyrazine-2-carvone Acid-3'-methylheptyl ester, 5
-(p-n-hebutylphenyl)pyrazine-2-carboxylic acid-37-methylhebutyl ester, 5-(p-n
-pentyloxyphenyl)pyrazine-2-powerupon m
t'-Methylhexyl ester, 5-(p-n-hexyloxyphenyl)pyrazine-2-carboxylic acid-4 '-Methylhexyl ester, 5-(p-n-decyloxyphenyl)pyrazine-2-carboxylic acid-4'-methylhexyl ester, 5-(p-n-dodecyloxyphenyl)pyrazine-2-carboxylic acid-4 '-Methylhexyl ester, 5-(p-n-)lysosyloxyphenyl)pyrazine-2-carboxylic acid-4'-methylhexyl ester,
5-(p-n-tetradecyloxyphenyl)pyrazine-2-carboxylic acid-4'-methylhexyl ester, 5
-(pn-hexadecyloxyphenyl)pyrazine-
2-carboxylic acid-4'-methylhexyl ester) pyrazine-2-carboxylic acid-4'-methylhexyl ester, 5-(p-n-octylphenyl)pyrazine-2-carboxylic acid-4'-methylhexyl ester , 5
-(p-n-decylphenyl)pyrazine-2-carboxylic acid-4'-methylhexyl ester, 5-(p-n-dodecylphenyl)pyrazine-2-carboxylic acid-4'-methylhexyl ester, 5-( p-n-decyloxyphenyl)pyrazine-2-carboxylic acid-5'-methylheptyl ester, 5-(p-n-dodecyloxyphenyl)virazine-2-carboxylic acid-5'-methylheptyl ester, 5- (pn-tetradecyloxyphenyl)pyrazine-2-carboxylic acid-5'-methylheptyl ester, 5-(pn-hexyloxyphenyl)hyrazine-2-carboxylic acid-6'-methyloctyl ester, 5-(p-n-octyloxyphenyl)pyrazine-2-carboxylic acid-6'-methyloctyl ester, 5-(p-n-nonyloxyphenyl)pyrazine-2
-carboxylic acid-6'-methyloctyl ester, 5-(
p-n-decyloxyphenyl) pyrazine-2-carboxylic acid-6'-methyloctyl ester, 5-(p-n-
undecyloxyphenyl)pyrazine-2-carboxylic acid-6'-methyloctyl ester, 5-(p-n-dodecyloxyphenyl)pyrazine-2-carboxylic acid M6'-
Methyloctyl ester, 5-(p-n-tridecyloxyphenyl)pyrazine-2-carboxylic acid-6'-methyloctyl ester 5-(p-n-tetradecyloxyphenyl)pyrazine-2-carboxylic acid-6'- Methyloctyl ester, 5-(p-n-hexadecyloxyphenyl)pyrazine-2-carboxylic acid-6'-methyloctyl ester, 5-(p-n-decylphenyl)pyrazine-2-carboxylic acid-6'- Methyloctyl ester, 5-(p-n-dodecylphenyl)pyrazine-2-carvone m-6'-methyloctyl ester, 5-(p-
n-decyloxyphenyl)pyrazine-2-carboxylic acid-1'-methylpropyl ester, 5-(pn-decyloxyphenyl)pyrazine-2-carboxylic acid-1'-
Methylbutyl ester, 5-(pn-dodecyloxyphenyl)pyrazine-2-carboxylic acid-1'-methylbutyl ester, 5-(pn-decyloxyphenyl)
Pyrazine-2-carboxylic acid-t'-methylheptyl ester, 5-(p-n-dodecyloxyphenyl)pyrazine-2-carvone M-t'-methylheptyl ester, 5-(p-n-F7'' sylphenyl) Pyrazine
2-carboxylic acid-1'-methylheptyl ester.
本発明において上記一般式（１）で表わさ、れる化合物
で強誘電性カイラルスメクチック相を有するものは、エ
ヌ、ニー、クラーク（Ｎ、Ａ、Ｃ１ａｒｋ ）らによっ
て示されたような表示素子として使用する場合に、電界
応答に対する閾値特性にすぐれているため、特に強誘１
Ｃ性カイラルスメクチック液晶を単純マトリックス電極
にて駆動するディスプレイに使用した場合に、クロスト
ークを防止し良好なコントラストを与えることが可能と
なる。このような特徴は、単独でカイラルスメクチック
相を持たない化合物を含む本発明における一般式（１）
で表わされる液晶性化合物を少なくとも１種含む液晶組
成物についても同様であり。In the present invention, a compound represented by the above general formula (1) having a ferroelectric chiral smectic phase is used as a display element as shown by N. A. Clark et al. In the case of ferroelectric 1, it has excellent threshold characteristics for electric field response.
When C-type chiral smectic liquid crystal is used in a display driven by a simple matrix electrode, crosstalk can be prevented and good contrast can be provided. Such characteristics are due to the general formula (1) in the present invention, which contains a compound that does not have a chiral smectic phase alone.
The same applies to a liquid crystal composition containing at least one liquid crystal compound represented by:
強誘電性カイラルスメクチック液晶を高精細大画面表示
素子として使用する場合にもすぐれている。Ferroelectric chiral smectic liquid crystals are also excellent when used as high-definition, large-screen display elements.
さらに、本発明の新規な液晶性化合物は１通常のネマチ
ック液晶に対して混合して使用することにより、ＴＮ型
液晶素子として使用する場合の閾値特性を改善すること
ができる。Furthermore, by mixing the novel liquid crystal compound of the present invention with one ordinary nematic liquid crystal, it is possible to improve the threshold characteristics when used as a TN type liquid crystal element.
上記のように、本発明の液晶性化合物は、゛それ単独で
強誘電性液晶素子材料として使用し得るが１例えば次表
１で示されるような強銹電性液晶と組合せることにより
、カイラルスメクチック相の温度範囲を拡大することが
可能となる。このような場合においては、一般式（Ｉ）
で示される本発明の液晶性化合物の少なくとも１種類を
、得られる液晶組成物の１〜９９重量％、特に５〜９５
重量％となる割合で使用することが好ましい。As mentioned above, the liquid crystal compound of the present invention can be used alone as a ferroelectric liquid crystal element material, but when combined with a ferroelectric liquid crystal as shown in Table 1 below, it can be used as a chiral compound. It becomes possible to expand the temperature range of the smectic phase. In such cases, general formula (I)
1 to 99% by weight, especially 5 to 95% by weight of the liquid crystal composition obtained, of at least one liquid crystalline compound of the present invention represented by
It is preferable to use it in a proportion of % by weight.
表１ 結晶；＝ゴ豊ＩＩ；＝ｉＳＩＩＡ；＝二等号相ＣＭ。Table 1 Crystal;=Goho II;=iSIIA;=Isometric phase CM.
■
−ＣＯＯＣＨ２ＣＨＣ２Ｈａ
４．４゛−７ゾキシシンナミ７クアシフドービス（２−
メチルブチル）エステル〔実施例〕
以下、実施例により、本発明を更に具体的に説１！ＩＩ
する。■ -COOCH2CHC2Ha 4.4゛-7zoxycinnami7quasifdobis(2-
(Methylbutyl) ester (Example) The present invention will be explained in more detail with reference to Examples 1! II
do.
実」Ｌ例」２
５−（ｐ−オクチルオキシフェニル）ピラジン−２−カ
ルボンＭ −４’−メチルへキシルエステル。Example 2 5-(p-octyloxyphenyl)pyrazine-2-carvone M -4'-methylhexyl ester.
（１）５−（ｐ−オクチルオキシフェニル）ピラジン−
２，３−ジカルボニトリルの合成。(1) 5-(p-octyloxyphenyl)pyrazine-
Synthesis of 2,3-dicarbonitrile.
二酸化セレン１１．４ｇ（０，１国０１）、ジオキサン
１００ ｍ文、水２ｍ交を混合し、７０〜７５℃で２
時間攪拌した後、ｐ−才クチルオキシアセトフェノン２
４．８ｇ （０，ｌ＋ａｏｌ ）−ジオキサン（６０Ｉ
ｌ１Ｍ）の溶液を加えた。２時間還流後冷却し、析出し
た全屈セレンを濾過した。ｐ液にＤＡＭＮＩ ０ 、８
ｇ （０、１ｍｏｌ ） 、酢酸３゜０１１文を加え、
９０〜９３°Ｃで２時間還流した。Mix 11.4 g of selenium dioxide (0.1 country 01), 100 m of dioxane, and 2 m of water, and heat at 70 to 75°C for 2 hours.
After stirring for an hour, p-cutyloxyacetophenone 2
4.8g (0,l+aol)-dioxane (60I
A solution of 1M) was added. After refluxing for 2 hours, the mixture was cooled and the precipitated total selenium was filtered. DAMNI 0, 8 in p solution
g (0.1 mol), add 3°011 acetic acid,
It was refluxed at 90-93°C for 2 hours.
反応後冷却し濾過した後、ろ液を濃縮し粗生成物を得た
。ヘキサンから再結晶後、２７．２ｇ（８２％収率）の
生成物を得た。融点７９℃。After the reaction was cooled and filtered, the filtrate was concentrated to obtain a crude product. After recrystallization from hexane, 27.2 g (82% yield) of product was obtained. Melting point: 79°C.
Ｉ Ｒ（ＦＣｌｌ−’） ： ２２４５ （Ｃ＝Ｎ）
。I R(FCll-'): 2245 (C=N)
.
元素分析 Ｃ２゜Ｈ２２Ｎ、Ｏとして
計算値： Ｃ７１，８３Ｈ６，６３
Ｎ １６．７５
実ｉ１＋１１値： Ｃ７２，０２Ｈ６，７５Ｎ １
６．５５゜
（２）５−（ｐ−オクチルオキシフェニル）ピラジン−
２，３−ジカルボン酸の合成。Elemental analysis Calculated value as C2゜H22N,O: C71,83H6,63N 16.75 Actual i1+11 value: C72,02H6,75N 1
6.55゜(2)5-(p-octyloxyphenyl)pyrazine-
Synthesis of 2,3-dicarboxylic acids.
５−（ｐ−オクチルオキシフェニル）ピラジン−２，３
−ジカルボニトリル（８，７ｇ、０．０２６履ｏｆ）を
水酸化ナトリウム（１５ｇ、０，３７５履ｏｆ ）−水
（６００−文）の′溶液中に入れ、９５℃で３時間攪拌
した０反応後、濃塩酸を、加えて反応液を酸性にして、
析出物を濾過した。６０ＩＩ文の水で５回洗浄し、真空
乾燥後８．１ｇ（８４％収率）の生成物を得た。エタ／
−ルー水から再結晶後、融点１６３℃、ＩＲ（シｃ＋ｗ
−’）：３４００〜２５５０ （ＯＨ）、１７３０．１
６９５（Ｃ＝Ｏ）。5-(p-octyloxyphenyl)pyrazine-2,3
- Dicarbonitrile (8.7 g, 0.026 mm) was placed in a solution of sodium hydroxide (15 g, 0.375 mm) - water (600 mm) and stirred at 95°C for 3 hours. After the reaction, add concentrated hydrochloric acid to make the reaction solution acidic.
The precipitate was filtered. After washing 5 times with 60ml of water and drying in vacuo, 8.1 g (84% yield) of product was obtained. Eta/
-After recrystallization from roux water, melting point 163℃, IR (shi c + w
-'): 3400-2550 (OH), 1730.1
695 (C=O).
元素分析 Ｃ２゜Ｈ２４Ｎ２０．として計算値： Ｃ
６４，５０Ｈ６，５Ｏ
Ｎ ７．５２
実測値： Ｃ６４，５２Ｈ６，７Ｏ
Ｎ ７．３６゜
（３）５−（ｐ−オクチルオキシフェニル）ピラジン−
２−カルボン酸の合成。Elemental analysis C2°H24N20. Calculated value as: C
64,50H6,5O N 7.52 Actual value: C64,52H6,7O N 7.36°(3) 5-(p-octyloxyphenyl)pyrazine-
Synthesis of 2-carboxylic acid.
５−（ｐ−オクチルオキシフェニル）ピラジン−２，３
−ジカルボン酸（８，１ｇ、０．０２１８ｍｏｌ）をジ
クロルベンゼン（ｌｏｏａｌ）中に入れ油浴を１６０℃
に設定して３．５時間攪拌した。−夜放置後析出物を濾
過し、ヘキサン６０履文で２回洗浄後、４．１ｇの生成
物を得た。エタノール−水から再結晶後、融点１６５℃
、゛分解点１９０℃、ＩＲ（νｃｍ−”）：３４００〜
２５００ （ＯＨ）、１６８０ （Ｃ＝Ｏ）。5-(p-octyloxyphenyl)pyrazine-2,3
- Dicarboxylic acid (8.1 g, 0.0218 mol) was placed in dichlorobenzene (looal) and the oil bath was heated to 160°C.
The mixture was stirred for 3.5 hours. - After standing overnight, the precipitate was filtered, and after washing twice with 60 g of hexane, 4.1 g of product was obtained. After recrystallization from ethanol-water, melting point 165°C
, ゛Decomposition point 190℃, IR (νcm-''): 3400~
2500 (OH), 1680 (C=O).
元素分析 ＣＩＩＨ２４Ｎ２０ｍとして計算値： Ｃ
６９，４９Ｈ７，３７
Ｎ ８．５３
天測値Ｉ Ｃ６９，６５Ｈ７，３５
Ｎ ８．３８
（４）エステル化。Elemental analysis Calculated value as CIIH24N20m: C
69,49H7,37 N 8.53 Astronomical value I C69,65H7,35 N 8.38 (4) Esterification.
５−（ｐ−オクチルオキシフェニル）ピラジン−２−カ
ルボン酸（１、６４ｇ、 ５ｍｍａｌ）を塩化チオニ
ル２０ｍＭ中に入れ、２時間還流した０反応後、過剰の
塩化チオニルを減圧留去し、残留物をトルエン５０ｍ！
Ｌに溶解した。トルエン溶液を水７０ ｖａ党で４回洗
浄し、硫酸マグネシウムで乾保後、ｐ過した。ｐ液中に
活性２− （−）−メチル−１−ヘキサノール０．５ｇ
を入れ、０℃に冷却下、役拌しながらピリジン０．４ｇ
およびトルエン１０Ｉｌ１文の混合溶液を滴下した。そ
の後、５℃以下で３０分間纜拌した後、２５°Ｃで１時
間攪拌した０反応溶液を濾過した後、ｐ液を水１・００
膳文で２回洗浄した０次にトルエン溶液を硫酸マグネシ
ウムで乾燥し、溶媒を留去した。残留物をシリカゲル（
６０ｇ）を用いたカラムクロマトグラフィーによりトル
エンで溶出させて精製し、さらに得られた結晶をヘキサ
ンから再結晶して０゜８ｇ（収率３６％）の生成物を得
た。5-(p-octyloxyphenyl)pyrazine-2-carboxylic acid (1.64 g, 5 mmal) was placed in 20 mM of thionyl chloride and refluxed for 2 hours. After the reaction, excess thionyl chloride was distilled off under reduced pressure to remove the residue. 50m of toluene!
Dissolved in L. The toluene solution was washed four times with 70 va of water, kept dry with magnesium sulfate, and then filtered. 0.5g of active 2-(-)-methyl-1-hexanol in p-liquid
Add 0.4 g of pyridine while cooling to 0℃ and stirring constantly.
A mixed solution of 10 Il and toluene was added dropwise. After that, the reaction solution was stirred for 30 minutes at 5°C or below, and stirred for 1 hour at 25°C.
The toluene solution, which had been washed twice with soap, was then dried over magnesium sulfate, and the solvent was distilled off. Remove the residue with silica gel (
The product was purified by column chromatography using 60 g of silica gel, eluted with toluene, and the resulting crystals were recrystallized from hexane to obtain 0.8 g of product (yield: 36%).
ＩＲ（ｙｃａ−”）：１７３０ （Ｃ＝Ｏ）。IR(yca-”): 1730 (C=O).
元素分析値 Ｃｘ＊ Ｈｓｓ Ｎ ２０ ｓ トＬ、、
テ。Elemental analysis value Cx* Hss N 20 s To L...
Te.
計算値：Ｃ６２，７０Ｈ１２，５Ｏ
Ｎ ９．１４゜
実測値：Ｃ６２，５１Ｈ１２，３Ｏ
Ｎ ９．２０゜
１１且又二」」
実施例１と同様にして、下表２に示す実施例２〜ｌＯの
化合物を得た。Calculated value: C62,70H12,5O N 9.14° Actual value: C62,51H12,3O N 9.20° 11 and 2'' Example 2 to lO shown in Table 2 below in the same manner as Example 1 The compound was obtained.
それらの相転移温度を表２に併せて示す０表中Ｃｒｙｓ
Ｌは結晶状７ｉ、ＳｍＣ”はカイラルスメクチック相、
ＳｍＡはスメクチックＡ相、そしてＴｓａは等方性液体
を表わす。Their phase transition temperatures are also shown in Table 2.
L is crystalline 7i, SmC" is chiral smectic phase,
SmA stands for smectic A phase and Tsa stands for isotropic liquid.
Ｓｍ３・・−ｓ＋ｅｃ 、Ｓｌ艷以外のスメクチック相
Ｃ（ルＯ０実」１例−Ｌ」
Ｉ Ｔｏ （Ｉｎｄｉｕｍ Ｔｉｎ ０ｘｉｄｅ） ８
２を電極として設けたセル厚約２ｐＬＩｌの液晶セルに
、４′−メチルへキシル−５−（ｎ−テトラデシルオキ
シフェニル）ピラジン−２−カーボネートを封入し、均
一なモノドメインのカイラルスメクチック相を得た。５
５℃において電界応答を測定したところ、駆動電圧４５
Ｖにて１ ｒｓｓｅｃ以下の応答速度が得られた。また
３０Ｖの直流電界を、Ｓ ｔａｓｅｃ印加しても反転し
ないことからすぐれた閾値特性を持つことがわかった。Sm3...-s+ec, smectic phase C other than Sl (Indium Tin Oxide) 8
4'-Methylhexyl-5-(n-tetradecyloxyphenyl)pyrazine-2-carbonate was sealed in a liquid crystal cell with a cell thickness of approximately 2 pLIl, and a uniform monodomain chiral smectic phase was formed. Obtained. 5
When the electric field response was measured at 5°C, the driving voltage was 45°C.
A response speed of 1 rssec or less was obtained at V. Furthermore, it was found that it had excellent threshold characteristics because it did not reverse even when a 30 V DC electric field was applied in Stasec.
実」Ｌ例二しヱ
本発明の液晶性化合物の２種を混合して下表３の液晶組
成物を得た。この液晶組成物は、３９〜６２℃において
ＳｍＣ”相を示した。また、この液晶組成物をＩＴＯ膜
を設けたセル厚約２＃Ｌｍの液晶セルに封入し、カイラ
ルスメクチック相を形成したところ、均一なモノドメイ
ンが得られた。Example 2 Two liquid crystal compounds of the present invention were mixed to obtain a liquid crystal composition shown in Table 3 below. This liquid crystal composition exhibited a SmC'' phase at 39 to 62°C. When this liquid crystal composition was sealed in a liquid crystal cell with an ITO film and a cell thickness of approximately 2#Lm, a chiral smectic phase was formed. , uniform monodomains were obtained.
４５°Ｃで電界応答をしらべたところ、２５ｖで１ｍ５
ｅｃ以下の応答速度を示し、良好なコントラストが得ら
れた。When examining the electric field response at 45°C, it was found that 1m5 at 25V
The response speed was less than ec, and good contrast was obtained.
表３
〔発明の効果〕
本発明の液晶性化合物、液晶組成物は、１！界応答に対
する閾値特性に優れた強誘電性カイラルスメクチック液
晶あるいは液晶組成物として有効であり、単純マトリッ
クス電極にて駆動するディスプレイに使用した場合にク
ロストークを防止し良好なコントラストを与えることが
でき、高精細・大画面表示素子として使用する場合に殊
に優れている。Table 3 [Effects of the Invention] The liquid crystal compound and liquid crystal composition of the present invention have 1! It is effective as a ferroelectric chiral smectic liquid crystal or liquid crystal composition with excellent threshold characteristics for field response, and can prevent crosstalk and provide good contrast when used in displays driven by simple matrix electrodes. It is particularly excellent when used as a high-definition, large-screen display element.
また、本発明の液晶性化合物のうち、ＳｍＣ”相に代表
されるような強誘電性を示しうる液晶相を持たないもの
においても、通常のネマチック液晶に対して混合した液
晶組成物とすること・により、ＴＮ型液晶素子として使
用する場合の閾値特性を改善することができる。Furthermore, among the liquid crystal compounds of the present invention, even those that do not have a liquid crystal phase that can exhibit ferroelectricity, such as the SmC'' phase, may be mixed with ordinary nematic liquid crystal to form a liquid crystal composition. -Threshold characteristics can be improved when used as a TN type liquid crystal element.
Claims (1)
ル基もしくはアルコキシ基であり、Ｒ＾＊は光学活性な
アルキル基を示す）で表わされる化合物。 ２、Ｒ＾＊が光学活性な４−メチルヘキシル基である特
許請求の範囲第１項記載の化合物。 ３、Ｒ＾＊が光学活性な６−メチルオクチル基である特
許請求の範囲第１項記載の化合物。 ４、Ｒ＾＊が光学活性な１−メチルヘプチル基である特
許請求の範囲第１項記載の化合物。 ５、Ｒ＿１が炭素原子数６〜１６の直鎖状アルキル基も
しくはアルコシキ基である特許請求の範囲第１項〜第４
項のいずれかに記載の化合物。 ８、一般式（ I ） ▲数式、化学式、表等があります▼（ I ） （上記一般式中Ｒ＿１は炭素原子数１〜１８のアルキル
基もしくはアルコキシ基であり、Ｒ＾＊は光学活性なア
ルキル基を示す）で表わされる化合物を少なくとも１種
含有する液晶組成物。 ７、Ｒ＾＊が光学活性な４−メチルヘキシル基である特
許請求の範囲第６項記載の液晶組成物。 ８、Ｒ＾＊が光学活性な６−メチルオクチル基である特
許請求の範囲第６項記載の液晶組成物。 ９、Ｒ＾＊が光学活性な１−メチルヘプチル基である特
許請求の範囲第６項記載の液晶組成物。 １０、Ｒ＿１が炭素原子数６〜１６の直鎖状アルキル基
もしくはアルコキシ基である特許請求の範囲第６項〜第
９項のいずれかに記載の液晶組成物。[Claims] 1. General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (I) (In the above general formula, R_1 is an alkyl group or an alkoxy group having 1 to 18 carbon atoms, and R ^* indicates an optically active alkyl group). 2. The compound according to claim 1, wherein R^* is an optically active 4-methylhexyl group. 3. The compound according to claim 1, wherein R^* is an optically active 6-methyloctyl group. 4. The compound according to claim 1, wherein R^* is an optically active 1-methylheptyl group. 5. Claims 1 to 4, wherein R_1 is a linear alkyl group or alkoxy group having 6 to 16 carbon atoms.
A compound according to any of the paragraphs. 8. General formula (I) ▲Mathematical formula, chemical formula, table, etc.▼(I) (In the above general formula, R_1 is an alkyl group or alkoxy group having 1 to 18 carbon atoms, and R^* is an optically active alkyl group. A liquid crystal composition containing at least one compound represented by the following formula. 7. The liquid crystal composition according to claim 6, wherein R^* is an optically active 4-methylhexyl group. 8. The liquid crystal composition according to claim 6, wherein R^* is an optically active 6-methyloctyl group. 9. The liquid crystal composition according to claim 6, wherein R^* is an optically active 1-methylheptyl group. 10. The liquid crystal composition according to any one of claims 6 to 9, wherein R_1 is a linear alkyl group or an alkoxy group having 6 to 16 carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61219225A JPH0730051B2 (en) | 1986-09-19 | 1986-09-19 | Liquid crystal compound and liquid crystal composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61219225A JPH0730051B2 (en) | 1986-09-19 | 1986-09-19 | Liquid crystal compound and liquid crystal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6377864A true JPS6377864A (en) | 1988-04-08 |
| JPH0730051B2 JPH0730051B2 (en) | 1995-04-05 |
Family
ID=16732160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61219225A Expired - Fee Related JPH0730051B2 (en) | 1986-09-19 | 1986-09-19 | Liquid crystal compound and liquid crystal composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0730051B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02184670A (en) * | 1989-01-06 | 1990-07-19 | Chisso Corp | Heterocycle-containing 1-methylalkyl ester |
| EP0541509A2 (en) * | 1987-06-04 | 1993-05-12 | Canon Kabushiki Kaisha | Liquid crystal composition and liquid crystal device containing same |
| WO2017082246A1 (en) * | 2015-11-10 | 2017-05-18 | 国立大学法人九州大学 | Dicyanopyrazine compound, luminescent material, light transmitter using same, and production method for 2,5-dicyano-3,6-dihalogenopyrazine |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6289669A (en) * | 1985-10-16 | 1987-04-24 | Ube Ind Ltd | Pyrazine derivative and chiral smectic liquid crystal composition containing same |
-
1986
- 1986-09-19 JP JP61219225A patent/JPH0730051B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6289669A (en) * | 1985-10-16 | 1987-04-24 | Ube Ind Ltd | Pyrazine derivative and chiral smectic liquid crystal composition containing same |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0541509A2 (en) * | 1987-06-04 | 1993-05-12 | Canon Kabushiki Kaisha | Liquid crystal composition and liquid crystal device containing same |
| JPH02184670A (en) * | 1989-01-06 | 1990-07-19 | Chisso Corp | Heterocycle-containing 1-methylalkyl ester |
| WO2017082246A1 (en) * | 2015-11-10 | 2017-05-18 | 国立大学法人九州大学 | Dicyanopyrazine compound, luminescent material, light transmitter using same, and production method for 2,5-dicyano-3,6-dihalogenopyrazine |
| JPWO2017082246A1 (en) * | 2015-11-10 | 2018-08-30 | 国立大学法人九州大学 | Dicyanopyrazine compound, light emitting material, light emitting device using the same, and method for producing 2,5-dicyano-3,6-dihalogenopyrazine |
| US10399960B2 (en) | 2015-11-10 | 2019-09-03 | Kyushu University, National University Corporation | Dicyanopyrazine compound, luminescent material, luminescence device using the same, and method for producing 2,5-dicyano-3,6-dihalogenopyrazine |
| US10497878B2 (en) | 2015-11-10 | 2019-12-03 | Kyushu University, National University Corporation | Dicyanopyrazine compound, luminescent material, luminescence device using the same, and method for producing 2,5-dicyano-3,6-dihalogenopyrazine |
| US10522763B2 (en) | 2015-11-10 | 2019-12-31 | Kyushu University, National Universit Corporation | Dicyanopyrazine compound, luminescent material, luminescence device using the same, and method for producing 2,5-dicyano-3,6-dihalogenopyrazine |
| JP2021014458A (en) * | 2015-11-10 | 2021-02-12 | 国立大学法人九州大学 | Dicyanopyrazine compound, luminescent material, and luminescence device using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0730051B2 (en) | 1995-04-05 |
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