JPH03239788A - Liquid crystal compound and liquid crystal composition containing it - Google Patents
Liquid crystal compound and liquid crystal composition containing itInfo
- Publication number
- JPH03239788A JPH03239788A JP3387590A JP3387590A JPH03239788A JP H03239788 A JPH03239788 A JP H03239788A JP 3387590 A JP3387590 A JP 3387590A JP 3387590 A JP3387590 A JP 3387590A JP H03239788 A JPH03239788 A JP H03239788A
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- liquid crystal
- mathematical
- chemical formulas
- Prior art date
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Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 47
- 150000001875 compounds Chemical class 0.000 title claims abstract description 38
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 19
- 230000000704 physical effect Effects 0.000 abstract description 2
- 230000002269 spontaneous effect Effects 0.000 abstract description 2
- 230000010287 polarization Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000005620 antiferroelectricity Effects 0.000 description 4
- 238000001142 circular dichroism spectrum Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 210000004027 cell Anatomy 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 230000003098 cholesteric effect Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- -1 diol compound Chemical class 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000010587 phase diagram Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (1R)-1,3-butanediol Natural products CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- PUPZLCDOIYMWBV-SCSAIBSYSA-N (R)-butane-1,3-diol Chemical compound C[C@@H](O)CCO PUPZLCDOIYMWBV-SCSAIBSYSA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-butanediol Substances OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- UTIMESSLYFMSPO-UHFFFAOYSA-N 2-methylbutyl 3-[4-[(4-decoxyphenyl)methylideneamino]phenyl]prop-2-enoate Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C=NC1=CC=C(C=CC(=O)OCC(C)CC)C=C1 UTIMESSLYFMSPO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005243 carbonyl alkyl group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は新矧な液晶化合物及び該液晶化合物を含む液晶
組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a fresh liquid crystal compound and a liquid crystal composition containing the liquid crystal compound.
液晶表示素子の表示方式として、塑在広く実用化されて
いるものは、ねじれネマチック５ｂよび動的散乱型のも
のである。これらはネマチック液晶を主成分としたネマ
チック液晶セルによる表示である。従来のネマチック液
晶セルの短所の一つに、応答速度が遅いことが挙げられ
ている。The display systems of liquid crystal display elements that have been widely put into practical use are the twisted nematic type 5b and the dynamic scattering type. These are displays using nematic liquid crystal cells containing nematic liquid crystal as a main component. One of the disadvantages of conventional nematic liquid crystal cells is slow response speed.
たかだか数ｍｇのオーターの応答速度しか得られず、動
画表示液晶デイスプレィへの応用を制限している。A response speed of only a few milligrams or less can be obtained at most, which limits its application to liquid crystal displays that display moving images.
最近に至って光学活性なスメクチック液晶の中には強誘
電性を示すものがめることが明らかＫなってきて釦υ、
４− （４−ｎ−デシルオキシベンジリデンアミノ）ケ
イ皮酸−２−メチルブチルエステル（ＤＯＢＡＭＢＣ）
を代表とする化合物がそれに６たる。これらはそのキラ
ルスメクテツクＣ相において強ｌ！電性を示すことｔ−
特徴とするものであり、薄膜セルにかいて１０′″′秒
オーダーの高速応答性が見出されている。この高速応答
性を利用して液晶テレビ等のデイスプレィ用のみならず
、光プリンターヘッド、光フーリエ変＃素子、ライトバ
ルブ等のオプトエレクトロニクス関連素子の素材として
も有用な材料として注目を集めている。Recently, it has become clear that some optically active smectic liquid crystals exhibit ferroelectricity.
4-(4-n-decyloxybenzylideneamino)cinnamic acid-2-methylbutyl ester (DOBAMBC)
There are six representative compounds. These have strong l! in their chiral smect C phase. Showing electrical conductivity t-
It has been found that a thin film cell has a high-speed response on the order of 10''' seconds.Using this high-speed response, it can be used not only for displays such as LCD televisions, but also for optical printer heads. It is also attracting attention as a useful material for optoelectronic devices such as optical Fourier variable elements and light valves.
強誘電性液晶はこのように大変注目を隼めている材料で
あるが、セルに＃！上げたときに双状態安定スイッチン
グを可能ならしむるためには２μｍ程度の極めて薄膜の
セルとしなければならないため、技術的に大変な困難が
伴うっさらに薄膜セルに封じこめた強誘電性液晶には欠
陥が生じやすいこともまたよく知られている事実である
。双状態安定スイッチングはデイスプレィにメモリー性
を付与することができるが、使用状況によってはこのメ
モリー性は電源を消しても画像が消えない、長時間同じ
ノ（ターンを出すと絶縁破壊を起こすなどの欠点につな
がる。Ferroelectric liquid crystal is a material that is attracting a lot of attention in this way, but it is #! In order to make bi-state stable switching possible when the cell is heated up, the cell must have an extremely thin film of about 2 μm, which poses great technical difficulties. It is also a well-known fact that they are prone to defects. Bi-state stable switching can add memory to the display, but depending on the usage situation, this memory can cause problems such as the image not disappearing even when the power is turned off, or dielectric breakdown occurring when the display is turned on for a long period of time. lead to shortcomings.
これらの欠点を解消する液晶として最近特定の含フツ素
低分子強誘電性液晶が注目されはじめた（ Ｊａｐａｎ
ｅｓｅＪｏｕｒｎａｌ ｏｆ Ａｐｐｌｉｅｄ Ｐｈ
ｙｓｉｃａ １９８９．２８（７）、Ｌ１２６５）。こ
れらの液晶にかいては分子内の双極子モーメントが非常
に大きいために分子間で双極子が反平行にｊツキングし
そのために反強誘電性を示すものと考えられる。電場印
加によって反強誘卵−強誘雷転移が起るために３状態安
定スイツチングが実すされ、前律の双状態安定スイッチ
ングの欠点を解消し７１）−高速液晶デイスプレィが可
能となったものである。Recently, certain fluorine-containing low-molecular-weight ferroelectric liquid crystals have begun to attract attention as liquid crystals that overcome these drawbacks (Japan
eseJournal of Applied Ph
ysica 1989.28(7), L1265). It is thought that these liquid crystals have extremely large intramolecular dipole moments, causing the dipoles to swing antiparallel between molecules, which is why they exhibit antiferroelectricity. Three-state stable switching is realized because the antiferromagnetic-ferroelectric lightning transition occurs when an electric field is applied, which eliminates the drawbacks of the two-state stable switching of the previous law, and makes high-speed liquid crystal displays possible.71) It is.
本発明者等は、前述の欠点を解決すべく鋭意検討した結
果、新規な液晶化合物を見出すと共に、該化合物が、反
強誘電性を示し、自発分杼粘性、らせんピッチ、チルト
角、液晶温ｉ節囲等の諸物性を広い範囲にわたって調節
が可能であるが故に高速デイスプレィ用途にょう適した
ものであることをもＦ出し、さらＩｃ、該新規な液晶化
合物な、スメクチック液晶化合物に混合することによシ
、該スメクチック液晶組成物に卦いて反強誘電性を惹起
せしめることを見出した。As a result of intensive studies aimed at solving the above-mentioned drawbacks, the present inventors discovered a new liquid crystal compound, and found that the compound exhibits antiferroelectricity, exhibits spontaneous separation viscosity, helical pitch, tilt angle, and liquid crystal temperature. Since various physical properties such as i-node area can be adjusted over a wide range, it is suitable for high-speed display applications. In particular, it has been found that the smectic liquid crystal composition induces antiferroelectricity.
＠１の本発明は、下記−数式（Ｉ）で表される液晶化合
物に関する。The present invention @1 relates to a liquid crystal compound represented by the following formula (I).
ＲＩＸＩＹＩＺＹ”Ｘ”Ｒ” （Ｔ）（
式中、Ｒ１、Ｒ２Ｖｉ、シアノ基、炭素数４〜２ｏｏア
ルキル基、アルコキシ基、アシルオキシ基トよびアルコ
キシカルボニル基より選げれる脂肪族基またはハロゲン
ｗ：１１！！該脂肪族基を示し、ＸＩ、 Ｘ”は、
を示し、２は主鎖の炭素数が３以上の奇数の二価の脂肪
族基を示し、かつ、Ｒ１，Ｒ１およびＺにおいて、少々
くとも一つの不斉炭素原子を含有するものである。）さ
らに、第２の本発明は、スメクチック液晶化合物に、下
記−数式（１）で表される液晶化合物を混合してなる液
晶組成物に関する。RIXIYIZY”X”R” (T)(
In the formula, R1, R2Vi, an aliphatic group selected from a cyano group, an alkyl group having 4 to 2 carbon atoms, an alkoxy group, an acyloxy group, and an alkoxycarbonyl group, or a halogen w: 11! ! 2 represents an odd-numbered divalent aliphatic group in which the number of carbon atoms in the main chain is 3 or more; Furthermore, the second invention relates to a liquid crystal composition obtained by mixing a smectic liquid crystal compound with a liquid crystal compound represented by the following formula (1).
ＲＩＸＩＹＩＺＹ”Ｘ”Ｒ” （１）（
式中、Ｒ１、Ｒ２はシアノ基、炭素数４〜２０のアルキ
ル基、アルコキシ基、アシルオキシ基およびアルコキシ
カルボニル基よシ選ばれる脂肪族基憬たはハロゲ７を擲
該脂肪族基を示し、ＸＩ％Ｘ雪は、
示し、Ｙｌ、Ｙ寞は
１
Ｃ−０−
または−〇−なる構造単位
群より選ばれる構造を基本骨格とする構造単位を示し、
０
１
Ｙｌ、 Ｙ”は−ｃ−ｏ−−ｔたは一〇−なる構造単位
を示し、２は主鎖の炭素数が３以上の奇数の二価の脂肪
族基を示し、かつ、Ｒ１、Ｈ２釦よびｚＫ釦いて、少な
くとも一つの不斉炭素原子を含有するものである。）
以下、本発明を詳這する。RIXIYIZY"X"R" (1) (
In the formula, R1 and R2 represent an aliphatic group selected from a cyano group, an alkyl group having 4 to 20 carbon atoms, an alkoxy group, an acyloxy group, and an alkoxycarbonyl group, or an aliphatic group including a halogen 7, and XI %X snow indicates, Yl, Y寞 indicates a structural unit whose basic skeleton is a structure selected from the structural unit group 1 C-0- or -〇-,
0 1 Yl, Y” represents a structural unit of -c-o--t or 10-, 2 represents an odd-numbered divalent aliphatic group having 3 or more carbon atoms in the main chain, and R1 , H2 button and zK button contain at least one asymmetric carbon atom.) The present invention will be described in detail below.
本発明の液晶化合物け、一般式（１３ ％式％（１） で示される化合物であることを特徴とする。The liquid crystal compound of the present invention has the general formula (13 % formula % (1) It is characterized by being a compound represented by
一般式（１）にかいて、Ｒ’ｔたば８重は、シアノ基管
たけ炭素数４−２０、好ましくは４〜１６のアルキル基
、アルコキシ基、アシルオキシ基、アルコキシカルボニ
ル基ヨリなる群より遣ばれる脂肪族基管たはハロゲン置
拗該脂肪族基を示すものである。脂肪族基としては、長
鎖状でも分枝状でもよい。ここでいうハロゲン置捧該脂
肪族基とは、前記脂肪族基の水素原子の一部がＣ１，Ｆ
、Ｂｒ、Ｉの少なくとも１のハロゲン原子により置換さ
れているものをいう。In the general formula (1), R't is from the group consisting of a cyano group, an alkyl group, an alkoxy group, an acyloxy group, an alkoxycarbonyl group, having 4 to 20 carbon atoms, preferably 4 to 16 carbon atoms. This indicates the aliphatic group or halogen substituted aliphatic group used. The aliphatic group may be long chain or branched. The halogen-substituted aliphatic group herein means that some of the hydrogen atoms of the aliphatic group are C1, F
, Br, I which is substituted with at least one halogen atom.
また、Ｒ１とＲ２は互いにｎ−でも異なってもよい。Further, R1 and R2 may be n- or different from each other.
Ｒ１，Ｒ２のよシ具体的な例としては例えば、−ＣｎＨ
２ｎ＋１、−〇〇ｎＨ２ｎ＋１、−〇−Ｃ−ＣｍＨ２ｍ
＋１、１
ＣＨ８−（−Ｃｌ宜＋Ｖ＋Ｃ）ＴヤＣＨｚ ＋、、不斉
炭素原子を示す）などが例示できる。Specific examples of R1 and R2 include -CnH
2n+1, -〇〇nH2n+1, -〇-C-CmH2m
+1, 1CH8-(-Cl+V+C)TyaCHz+, indicating an asymmetric carbon atom), etc. can be exemplified.
一般式（Ｔ）にかいて、ＸＩ、Ｘ”は、（ここで４≦ｎ
≦２０．３重ｍ≦１９、ｐ＞０゜１≦ｑ≦３、ｒ ）
Ｏ１３≦ｐ ＋ ｑ ＋ ｒ≦１９、ＸはハＩｆｆゲ７
またはアルキル基を示す。ただ１７、Ｘがアルキル基の
場合は、Ｈ１オたはＲ２に訃ける全炭素数は２ｏを越え
ないものとする）などの一般式で示されるものが挙げら
れ、好１しくけ、−ＣｎＨ，ｎ＋、（ｎは４がら１２の
弊数）、−〇ＣｎＨ２ｎ＋、（ｎは４から１２の整ｅ、
） ％ −ｏｃｃｎｕ、ｎ＋。In the general formula (T), XI, X'' are (where 4≦n
≦20.3 m≦19, p>0゜1≦q≦3, r)
O13≦p + q + r≦19,
Or represents an alkyl group. However, when X is an alkyl group, the total number of carbon atoms in H1 or R2 shall not exceed 2 o). , n+, (n is an integral number from 4 to 12), -〇CnH2n+, (n is an integer e from 4 to 12,
) % −occnu, n+.
１
からなる群より選ばれる構造を基本骨格とする構造単位
を示すものである。ここでかかる構造を基本骨格とする
構造単位とは、該構造そのもの１工び該構造単位の芳香
環の水素原子の一部がその機能に悪影響を与えない置換
基、例えば炭素数４以下のアルキル基あるいけノ・ロゲ
ン原子によシｆｖｔｐされたものを意味する。該置檜さ
れたものとしては、例えば、
ＣＨ。1 indicates a structural unit whose basic skeleton is a structure selected from the group consisting of: Here, a structural unit having such a structure as its basic skeleton means that the structure itself is a part of the structure, and some of the hydrogen atoms of the aromatic ring of the structural unit are substituents that do not adversely affect the function, such as alkyl having 4 or less carbon atoms. It means a substance formed by fvtp by a group or an iogen atom. For example, CH.
などが挙げられる。ＸｌおよびＸｌとじては、とくにＣ
Ｉ（。Examples include. For Xl and Xl, especially C
I(.
ｔ
１
ｙｌ、 Ｙｌは、−Ｃ−０−または−〇−なる構造単位
を示し、ＹｌとｙＱ＝を互いにＨ−でも異なってもよい
。t 1 yl, Yl represents a structural unit of -C-0- or -0-, and Yl and yQ= may be H- or different from each other.
２は、主鎖の炭素数が３以上の奇数、好！シ〈は３〜１
３の奇数である２価の脂肪族基を示すものであり、例え
ば＋ｃｕｔ＋１ （３≦ｎ≦１３かつ、ｎは奇数）、
（ここで ｐ≧Ｏ％ｑ≧０．２≦ｐ＋Ｑ≦１２、Ｐ＋（
ｌは偶数、ｐ＼ｑ、Ｘはハロゲン原子筐たは炭素数１〜
５、好１しくは１〜３のアルキル基を示す）
なる−数式で表される２価の脂肪族基などが挙げられ、
好１しくは、
＋ ＣＨｚ ＋、、、＋ ＣＨｚ ％ 、千ＣＨｔ ＋
７ 、キｃｕｔへ、などが例示される。2 is an odd number with 3 or more carbon atoms in the main chain, good! 〈is 3-1
It indicates a divalent aliphatic group that is an odd number of 3, for example +cut+1 (3≦n≦13 and n is an odd number),
(Here p≧O%q≧0.2≦p+Q≦12, P+(
l is an even number, p\q, X is a halogen atom box or a carbon number of 1 to
5, preferably 1 to 3 alkyl groups) - Divalent aliphatic groups represented by the formula:
Preferably, + CHz +,,, + CHz %, 1,000 CHt +
7, to cut, etc. are exemplified.
筐た、−ｐ式（１）においては、Ｈｌ、 Ｂ ！ １工
び２のうち少なくとも一種以上の基またけ構造単位に一
つ以上の不斉炭素原子を必須に含有するものである。In equation (1), Hl, B ! One or more asymmetric carbon atoms are essentially contained in at least one group-spanning structural unit in one or more of the two groups.
本発明の一般式（Ｉ）で表される液晶化合物の製造方法
は、特に限定されるものではないが、例えばｘｔ−ｔた
はＸｌをメソケ゛ンとし、かつＲ１またばＲ３を含むカ
ルボン酸（−数式ＲＸＣＯＯＨ１ただし、ＲはＲ１−１
たばＲ２、ＸはＸｌまたは）（Ｘｌ示す）またはその誘
導体と、２を構造単位として含むジオール化合物（−数
式）（ＯＺ ＯＨ）との反応、あるいは、Ｘ１！たはＸ
ｌをメソゲンとし、かつＲ１−１たはＲ宜を含むフェノ
ール性化合物（−数式ＲＸＯＨ１ただし、ＲＶｉＲ”筐
たばＲ１、ＸけＸｌまたけＸ２を示す）と２をフレキシ
ブル鎖とするジカルボン酸（−数式ＨＯＯＣＺＣＯＯＨ
） との反応などで反応生成物を合成し、該生成物を
公知の方法により配向させることにより容易に製造する
ことができる。なお、これらの原料のＲＩ、Ｒ”、Ｘ’
、Ｘ”ｂＬびｚＦｉ−数式（１）におけるそれと同一の
ものを意味するものである。The method for producing the liquid crystal compound represented by the general formula (I) of the present invention is not particularly limited, but for example, xt-t or Xl is used as a mesochain, and a carboxylic acid (- Formula RXCOOH1 However, R is R1-1
Reaction of R2, X is Xl or ) (Xl is shown) or a derivative thereof with a diol compound (-formula) (OZ OH) containing 2 as a structural unit, or X1! or X
A phenolic compound in which l is a mesogen and contains R1-1 or R (-formula RXOH1, however, RViR" shows R1, -Formula HOOCZCOOH
) can be easily produced by synthesizing a reaction product, such as by reacting with In addition, RI, R", X' of these raw materials
, X''bL and zFi - means the same as that in formula (1).
これらの反応方法の具体例としては、例えば、カルボン
酵クロリドと水に藁、カルボン酸とアセチル化された水
酸井、カルボン階アルキルエステルと水階基のような組
合せを用いる公知の反応方法が採用され、−例としてｔ
−ｔｘ−ｔメソーゲンとして含むカルボン酸と塩化チオ
ニルとの反応で得られるカルボン酸クロライドを、酸受
容体としてのピリジンなどの填基存存下に、２単付を含
むジオール化合物と加勢下に反応さぜる方法などが好１
しく採用される。Specific examples of these reaction methods include known reaction methods that use combinations such as carboxylic acid chloride and water with straw, carboxylic acid and acetylated hydroxyl, and carbonyl alkyl ester and aqueous group. adopted, - as an example t
-tx-t A carboxylic acid chloride obtained by the reaction of a carboxylic acid contained as a mesogen with thionyl chloride is reacted with a diol compound containing a divalent group in the presence of a filler such as pyridine as an acid acceptor. I like the method of stirring etc.
be hired properly.
これらの反応はピリジン、テトラクロロエチレン、テト
ラクロロエタン、０−ジクロロベンゼン、トルエン、キ
シレンなどの有機溶媒中で行うことができ、反応温度と
してけ０℃から２００℃、好管しくＦｉ５０℃から１５
０℃が採用され、溶＃を加熱還流しながら行う方法など
が好適に用いられる。反応はＸを含む化合物２モルに対
して２を含む化合物１モルの仕込み組成で行うが、反応
を完結させるためにどちらかの成分を過刹にして行うこ
ともできる。反応雰囲気は空党下、窒素雰囲気、窒素気
流下などで行われるが、かとえげ酔クロライドの水によ
る分解などの副反応を防ぐためには、窒素を用いた雰囲
気下で行うことが好ましい。生成物の単離は蒸留、再結
晶、カラムクロマトグラフィーによる分離などの、通常
の有機合成で用いられる手法を採用することができる。These reactions can be carried out in organic solvents such as pyridine, tetrachloroethylene, tetrachloroethane, 0-dichlorobenzene, toluene, xylene, etc., and the reaction temperature ranges from 0°C to 200°C, preferably from 50°C to 15°C.
A temperature of 0° C. is employed, and a method of heating the solution while refluxing is preferably used. The reaction is carried out using a charging composition of 2 moles of the compound containing X and 1 mole of the compound containing 2, but it is also possible to carry out the reaction with an excess of either component in order to complete the reaction. The reaction is carried out under an empty atmosphere, a nitrogen atmosphere, a nitrogen stream, etc., but in order to prevent side reactions such as decomposition of chloride by water, it is preferable to carry out the reaction under a nitrogen atmosphere. For isolation of the product, methods commonly used in organic synthesis, such as distillation, recrystallization, and separation by column chromatography, can be employed.
本発明の一般式（１）で表される液晶化合物は、それ自
体が反強誘電性を示す特長を有するっまた、本発明の液
晶化合物をスメクチック液晶化合物と混合することによ
り、スメクチック液晶組成物に反強誘雷、性を惹起させ
ることもまた可能である。The liquid crystal compound represented by the general formula (1) of the present invention has the feature of exhibiting antiferroelectricity by itself.Also, by mixing the liquid crystal compound of the present invention with a smectic liquid crystal compound, a smectic liquid crystal composition can be obtained. It is also possible to induce antiferrotonic lightning.
スメクチック液晶化合物としては、スメクチックＡタイ
プ、スメクチックＣタイプのいずれかの液晶化合物が挙
げら力、具体的には、
などのスメクチックＡ液晶化合物や
などのスメクチックＣ液晶化合物が好適な例として挙げ
ら力る。一般式（Ｔ）で弄される液晶化合物とスメクチ
ック液晶化合物の混合割合は特に限定されないが、通常
、一般式（１）で表される液晶化合物／スメクチック液
晶化合物が０１〜５０／９９．９〜５０、好ｔ Ｌ、＜
ｕｌ〜２０／９９〜８０（重骨比）である。Smectic liquid crystal compounds include either smectic A type or smectic C type liquid crystal compounds, and specifically, smectic A liquid crystal compounds such as smectic A liquid crystal compounds and smectic C liquid crystal compounds such as smectic C liquid crystal compounds are suitable examples. Ru. The mixing ratio of the liquid crystal compound represented by the general formula (T) and the smectic liquid crystal compound is not particularly limited, but usually the liquid crystal compound/smectic liquid crystal compound represented by the general formula (1) is 01-50/99.9- 50, good L, <
ul~20/99~80 (heavy bone ratio).
なか、両者の混合は公知の方法により容易になされる。Among them, mixing of the two can be easily done by a known method.
川下に実加例ケのべるが、これらは本発明を実施するた
めの押開用のものであって、本発明はとからに制阻され
るものではない。Practical examples are shown below, but these are for pushing open to carry out the present invention, and the present invention is not necessarily inhibited.
〈実施例１〉
（１）エチル（４，４’−ヒドロキシアゾベンゾエート
）フェノール１０Ｆ、水酸化ナトリウム５，８２を水２
５〇−に溶解した。別にｐ−アシノ安息香酸エステル１
７．５９１＠ｔ！Ｊ３０−と水３０ｍ／の溶液に加え、
加熱しながらさらに水を加えて宗全に溶解させた。溶解
後枠氷上に注ぎ冷却し、たのち、堺硝酸ナトリウム８．
１２訃よび水５８−から成る水溶液を、ヨウ化カリでん
粉紙が変色する量だけ加えた。この溶ｇを先に調製した
フェノール水溶液に加え、その後析出物をろ別、水洗、
乾燥後、エタノール／水中で再結晶して合成した。<Example 1> (1) Ethyl (4,4'-hydroxyazobenzoate) phenol 10F, sodium hydroxide 5,82 and water 2
It was dissolved in 50-. Separately, p-acinobenzoic acid ester 1
7.591@t! In addition to a solution of J30- and water 30m/
While heating, more water was added to dissolve the sozen. After melting, pour on ice and cool, then add Sakai sodium nitrate8.
An aqueous solution consisting of 12 ml and water was added in an amount sufficient to discolor the potassium iodide starch paper. This molten g was added to the previously prepared aqueous phenol solution, and then the precipitate was filtered off, washed with water,
After drying, the product was synthesized by recrystallization in ethanol/water.
（２）４．４’−ｎ−ブチルオキシアゾベンゼンカルボ
ン単エチル（４，４’−ヒドロキシアゾベンゾニー））
２（ｌを、水酸化す） ＩＪウムのエタノール溶液中で
４５分間還流させ、加水分解して得た４、４′−ヒドロ
キシアゾベン七ンカルボン酸１２．７Ｆを、水酸化カリ
ウムのエタノール溶液に加え、加熱しながら溶解するだ
けり水を加えた。次に臭化ブチル４４−を滴下、２０時
間還流させた。冷却後エタノールを留去し水を加えて、
さらに塩酸酸性とした。析出物をｐ過、水洗、乾燥後ジ
メチルスルホキシド／エタノール中で再結晶して合成し
たつ
（３）ＢｕＡｚ −３＊
４．４”ｎ−ブチルオキシアゾベンゼンカルボン酸１３
．６ｍｍｏｌおよびジメチルホルムアミド数滴を塩化チ
オニル３〇−中に力０え２時間還流、放冷後塩化チオニ
ルを減圧留去し六。残留物にピリジン３０−を滴下後、
猜拌しながら（Ｒ） −（−） −１，３−ブタンジオ
ール７ ｍｍｏ ｌのピリジン溶液を滴下した。１５時
間還流後塩醇酸性にして生成物を沈殿させ、Ｆ’Ｊ、洗
浄、乾燥後、さらに展開溶媒にクロロホルムを用いてカ
ラムクロマトグラフィーにより分離し、再結晶してＢｕ
Ａｚ −３を得た。ＩＨ−ＮＭＲスペクトルを図１に
示した。(2) 4.4'-n-butyloxyazobenzenecarboxylic monoethyl (4,4'-hydroxyazobenzony))
2 (Hydroxylate l) 4,4'-Hydroxyazoben7anecarboxylic acid 12.7F, obtained by refluxing and hydrolyzing IJium in an ethanol solution for 45 minutes, was added to an ethanol solution of potassium hydroxide. Add enough water to dissolve the mixture while heating. Next, 44-butyl bromide was added dropwise and the mixture was refluxed for 20 hours. After cooling, ethanol was distilled off and water was added.
It was further made acidic with hydrochloric acid. The precipitate was filtered, washed with water, dried, and then recrystallized in dimethyl sulfoxide/ethanol to synthesize (3) BuAz-3*4.4''n-butyloxyazobenzenecarboxylic acid 13
．． 6 mmol and a few drops of dimethylformamide were poured into 30% thionyl chloride and refluxed for 2 hours. After cooling, thionyl chloride was distilled off under reduced pressure. After dropping pyridine 30- into the residue,
A solution of 7 mmol of (R)-(-)-1,3-butanediol in pyridine was added dropwise while stirring. After refluxing for 15 hours, the product was precipitated with salt solution, washed, dried, and further separated by column chromatography using chloroform as a developing solvent, and recrystallized to obtain Bu.
Az-3 was obtained. The IH-NMR spectrum is shown in FIG.
反強誘電相の同定
（１）Ｘ線回折とＣＤスペクトル
合成したＢｕＡｚ−３＊の１００℃で調製した配向試料
を冷却して観測したＸ線回折ノ４ターンは、配向軸が上
下方向にあう、それに対して層の反射が子午線上から左
右にスプリットして現われた。さらに層の乱れた充てん
を示す反射が赤道線上にみられ、これエリＢｕＡｚ−３
は層構造を有し、かつ層に対してメソーゲンがキルトし
たスメクチックＣタイプの構造を有していることが分っ
た。ｆ＊ｃＤスペクトルの測定よりキラリティーが確か
められ、ＢｕＡｚ−３”はキシルスメクチックＣタイプ
の液晶相を有することが確認さ力た。Identification of the antiferroelectric phase (1) X-ray diffraction and CD spectra The four turns of X-ray diffraction observed after cooling the oriented sample of BuAz-3* prepared at 100°C show that the orientation axes align in the vertical direction. , on the other hand, the reflection of the layer appeared to be split left and right from the meridian. Furthermore, reflections indicating disordered filling of the layer are seen on the equator line, and this
It was found that it has a layered structure and a smectic C type structure in which mesogen is quilted between the layers. Chirality was confirmed by measuring the f*cD spectrum, and it was confirmed that BuAz-3'' had a xylsmectic C type liquid crystal phase.
（２）反射スはクトル
この液晶相の対称性を調べるために、２枚のガラス板に
はさんで１２０℃ですりを与えて垂直配向させたのち室
温１で冷却した試料について、分光計を用いて光の垂直
入射および斜め入射のときの反射スペクトルを測定した
ところ、垂直入射：１？よび斜め入射の場合ともに選択
反射ピークは１本しか現われなかった。キシルスメクチ
ックＣ相の場合は斜め入射の場合、ハーフピッチバンド
とフルピッチバンドの２本のピークが現われるはずで、
本ポリマーは強誘電性液晶であるキシルスメクチックＣ
相と異なり、コレステリック相と同じ対称性をもつこと
がわかった。すなわち本ボリエステルは反強誘電性液晶
である。(2) Reflection is a qutol In order to investigate the symmetry of this liquid crystal phase, a spectrometer was used on a sample that was sandwiched between two glass plates and abraded at 120°C to align it vertically, then cooled to room temperature. When we measured the reflection spectra when light was incident vertically and obliquely, we found that vertical incidence: 1? Only one selective reflection peak appeared in both the case of light and oblique incidence. In the case of xyl smectic C phase, two peaks, a half-pitch band and a full-pitch band, should appear in the case of oblique incidence.
This polymer is a ferroelectric liquid crystal, Xylsmectic C.
It was found that, unlike the cholesteric phase, it has the same symmetry as the cholesteric phase. In other words, this polyester is an antiferroelectric liquid crystal.
〈実施例２〉
実施例１の（２）で合成した４、４’−ｎ−ブチルオキ
シアゾベンゼンカルボン酸と１，５−ベンタンジオール
を用いて、実施例１の（３）と同様の手法でα、ω−ビ
ス（４，４’−ｎ−ブチルオキシアゾベンゼンカルボニ
ルオキシ）ペンタン（ＢｕＡｚ−５と略す）を合成した
。実施例１の（３）で合成したＢｕＡｚ−３＊１５ｗｔ
％とＢｕＡｚ−５８５ｗｔ％の混合物のＣＤスはクトル
（図２）を測定したところ６１０ ｎｍにピークがやれ
、この混合物が同様にキラリティーを有し、６１０ｎｍ
に反射スペクトルを有する層構造をもつことが確認され
か。さらにＤＳＣ測定と偏光顕微鏡観察から相図（図３
）を求めたところ、この混合物は広い温［９囲トよび広
い組成節回にわたって反強誘電液晶相（Ｓｃｌ 相）
を示し、ＢｕＡｚ−３＊の混合が反強誘電液晶相を誘起
していることがわかった。<Example 2> Using 4,4'-n-butyloxyazobenzenecarboxylic acid synthesized in Example 1 (2) and 1,5-bentanediol, the same procedure as in Example 1 (3) was carried out. α,ω-Bis(4,4′-n-butyloxyazobenzenecarbonyloxy)pentane (abbreviated as BuAz-5) was synthesized. BuAz-3*15wt synthesized in (3) of Example 1
When the CD spectrum of a mixture of % and BuAz-585wt% was measured at 610 nm (Figure 2), this mixture similarly had chirality and a peak at 610 nm.
It was confirmed that it has a layered structure with a reflection spectrum. Furthermore, the phase diagram (Fig. 3
), it was found that this mixture exhibits an antiferroelectric liquid crystal phase (Scl phase) over a wide temperature range and wide composition range.
It was found that the mixture of BuAz-3* induces an antiferroelectric liquid crystal phase.
〈実施例３〉
α、ω−ビス（４，４’−シアノビフェニルカルボニル
オキシ）アルカン
メソーゲン単位として４，４′−シアノビフェニルカル
ボン酸を、またα、ω−ジオールとして（ｓ）−２−メ
チル−１，５−ペンタンジオールを用いた以外は実施例
１の（３）と同様にしてＣＢ−５＊を合成した。得られ
たＣＢ−５＊を用いて、実施例１と同様にしてＸ＃ｉ１
回折、ＣＤスペクトルの測定、反射スぼクトルの測定を
行ったところ、ＣＢ−５＊が反強誘電性液晶相を有する
ことがわかった。<Example 3>4,4'-cyanobiphenylcarboxylic acid as the α,ω-bis(4,4'-cyanobiphenylcarbonyloxy)alkane mesogen unit and (s)-2 as the α,ω-diol CB-5* was synthesized in the same manner as in Example 1 (3) except that -methyl-1,5-pentanediol was used. Using the obtained CB-5*, X#i1 was prepared in the same manner as in Example 1.
Diffraction, CD spectrum measurements, and reflection spectral measurements revealed that CB-5* has an antiferroelectric liquid crystal phase.
〈実施例４〜８〉
以下同様にして、表１に示した液晶化合物の合成と液晶
相の一定を行い、いずれも反強誘電性液晶相を示す化合
物であることを明らかにした。<Examples 4 to 8> Similarly, the liquid crystal compounds shown in Table 1 were synthesized and the liquid crystal phase was determined, and it was revealed that all of them were compounds exhibiting an antiferroelectric liquid crystal phase.
〈比較例１〉
メソーゲン単位として４．４’−ｎ−ブチルオキシアゾ
ベンゼンカルボン酸を、またジオールとして光学的に不
活性でかつ主弁を構成する炭素数が４で偶数である１、
４−ブタンジオールを用いて実施例１の（３）と同様に
して、表１に示した化合物を合成した。この化合物の液
晶相を同定した結果、強誘電、相も反強誘電相も示さず
通常のスメクチック人相が観察された。<Comparative Example 1>4.4'-n-butyloxyazobenzenecarboxylic acid as the mesogen unit, optically inactive as the diol, and 1, which has an even number of carbon atoms of 4, which constitutes the main valve.
The compounds shown in Table 1 were synthesized in the same manner as in Example 1 (3) using 4-butanediol. As a result of identifying the liquid crystal phase of this compound, a normal smectic human phase was observed, showing neither a ferroelectric phase nor an antiferroelectric phase.
〈比較例２〉
メソーゲン単位として４．４′−シアノビフェニルカル
ボン酸を、またジオールとして光学活性でかつ主鎖を構
成する炭素数が４と偶数である（Ｓ）−１，４ブタンジ
オールを用いて、実施例１の（３）と同様にして、表１
に示した化合物を合成しか。この化合物の液晶相を同定
した結果、強誘電相を示したが１反仰誘買液晶相Ｖｉｔ
ったく１察されながった。<Comparative Example 2>4.4'-cyanobiphenylcarboxylic acid was used as the mesogen unit, and (S)-1,4-butanediol, which is optically active and has an even number of carbon atoms in the main chain of 4, was used as the diol. Then, in the same manner as in Example 1 (3), Table 1
The compound shown in can be synthesized. As a result of identifying the liquid crystal phase of this compound, it was found that it was a ferroelectric phase, but the liquid crystal phase Vit
I was completely ignored.
本発明の新規な液晶性化合物は安定した反強誘電液晶性
を示すために３状態スイツチングを利用した高速液晶デ
イスプレィに好適であるばかうでなく、スメクチックＡ
あるいけＣ液晶に混合することによって反強誘電液晶性
を誘起することができ、極めて応用範囲が広い。The novel liquid crystal compound of the present invention exhibits stable antiferroelectric liquid crystallinity, and is therefore suitable for high-speed liquid crystal displays that utilize three-state switching.
By mixing it with Arike C liquid crystal, antiferroelectric liquid crystal properties can be induced, and the range of applications is extremely wide.
第１図ＦｉＢｕＡｚ−３＊のＩＨ−ＮＭＲスはクトルを
示す。
第２図はＢｕＡｚ−３＊１５ｗｔ％とＢｕＡｚ−５８５
ｗｔ蝿の混合物の９０℃と１２０℃にかけるＣＤスペク
トルを示す。
第３図はＢｕＡｚ −３／ Ｂｕ Ａｚ −５混合系の
相図を示す。
第２図FIG. 1 IH-NMR spectra of FiBuAz-3* show chromatography. Figure 2 shows BuAz-3*15wt% and BuAz-585.
The CD spectra of a mixture of wt flies at 90°C and 120°C are shown. FIG. 3 shows the phase diagram of the BuAz-3/BuAz-5 mixed system. Figure 2
Claims (1)
＾１Ｙ＾１ＺＹ＾２Ｘ＾２Ｒ＾２（ I ）（式中、Ｒ＾
１、Ｒ＾２はシアノ基、炭素数４〜２０のアルキル基、
アルコキシ基、アシルオキシ基およびアルコキシカルボ
ニル基より選ばれる脂肪族基またはハロゲン置換該脂肪
族基を示し、Ｘ＾１、Ｘ＾２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▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼ および▲数式、化学式、表等があります▼ からなる群より選ばれる構造を基本骨格とする構造単位
を示し、 Ｙ＾１、Ｙ＾２は▲数式、化学式、表等があります▼ま
たは−Ｏ−なる構造単位を示し、Ｚは主鎖の炭素数が３
以上の奇数の二価の脂肪族基を示し、かつ、Ｒ＾１、Ｒ
＾２およびＺにおいて、少なくとも一つの不斉炭素原子
を含有するものである。）２、スメクチック液晶化合物
に下記一般式（ I ）で表される液晶化合物を混合して
なる液晶組成物 Ｒ＾１Ｘ＾１Ｙ＾１ＺＹ＾２Ｘ＾２Ｒ＾２（ I ）（式
中、Ｒ＾１、Ｒ＾２はシアノ基、炭素数４〜２０のアル
キル基、アルコキシ基、アシルオキシ基およびアルコキ
シカルボニル基より選ばれる脂肪族基またはハロゲン置
換該脂肪族基を示し、Ｘ＾１、Ｘ＾２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▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼ および▲数式、化学式、表等があります▼ からなる群より選ばれる構造を基本骨格とする構造単位
を示し、Ｙ＾１、Ｙ＾２は▲数式、化学式、表等があり
ます▼または−Ｏ−なる構造単位を示し、Ｚは主鎖の炭
素数が３以上の奇数の二価の脂肪族基を示し、かつ、Ｒ
＾１、Ｒ＾２およびＺにおいて、少なくとも一つの不斉
炭素原子を含有するものである。）[Claims] 1. Liquid crystal compound R^1X represented by the following general formula (I)
^1Y^1ZY^2X^2R^2 (I) (in the formula, R^
1, R^2 is a cyano group, an alkyl group having 4 to 20 carbon atoms,
Indicates an aliphatic group or a halogen-substituted aliphatic group selected from alkoxy groups, acyloxy groups, and alkoxycarbonyl groups, and X^1 and X^2 are ▲Mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼ and ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Indicates a structural unit whose basic skeleton is a structure selected from the group consisting of, Y^1, Y^2 are ▲ Mathematical formulas, chemical formulas, tables, etc. ▼ or -O- indicates a structural unit, Z indicates that the number of carbon atoms in the main chain is 3
Indicates the above odd-numbered divalent aliphatic group, and R^1, R
^2 and Z contain at least one asymmetric carbon atom. ) 2. Liquid crystal composition R^1X^1Y^1ZY^2X^2R^2(I) (where R^1 , R^2 represents an aliphatic group or a halogen-substituted aliphatic group selected from a cyano group, an alkyl group having 4 to 20 carbon atoms, an alkoxy group, an acyloxy group, and an alkoxycarbonyl group, and X^1 and X^2 are , ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼ and ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Indicates a structural unit whose basic skeleton is a structure selected from the group consisting of ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or -O- represents a structural unit, Z represents an odd-numbered divalent aliphatic group having 3 or more carbon atoms in the main chain, and R
^1, R^2 and Z contain at least one asymmetric carbon atom. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3387590A JPH03239788A (en) | 1990-02-16 | 1990-02-16 | Liquid crystal compound and liquid crystal composition containing it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3387590A JPH03239788A (en) | 1990-02-16 | 1990-02-16 | Liquid crystal compound and liquid crystal composition containing it |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03239788A true JPH03239788A (en) | 1991-10-25 |
Family
ID=12398692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3387590A Pending JPH03239788A (en) | 1990-02-16 | 1990-02-16 | Liquid crystal compound and liquid crystal composition containing it |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03239788A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0429219A (en) * | 1990-05-25 | 1992-01-31 | Idemitsu Kosan Co Ltd | High-polymer liquid crystal composition, liquid crystal optical element formed by using this composition and method for driving liquid crystal optical element |
| EP0582468A1 (en) * | 1992-08-05 | 1994-02-09 | Mitsubishi Gas Chemical Company, Inc. | Anti-ferroelectric liquid crystal composition and liquid crystal display device |
| GB2356629A (en) * | 1999-10-04 | 2001-05-30 | Merck Patent Gmbh | Bimesogenic compounds and their use in flexoelectric liquid crystal devices |
| JP2007070454A (en) * | 2005-09-06 | 2007-03-22 | Tokyo Institute Of Technology | Liquid crystal and method for producing the same |
| WO2007099669A1 (en) * | 2006-02-28 | 2007-09-07 | Nippon Oil Corporation | Dioxetane compound, cationically polymerizable composition, optical film and liquid crystal display unit |
| US7763182B2 (en) | 2006-04-10 | 2010-07-27 | Nippon Oil Corporation | Liquid crystalline composition with improved adhesivity, liquid crystal film comprising the composition, and liquid crystal display device equipped with the film |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62234048A (en) * | 1986-02-17 | 1987-10-14 | ヘキスト アクチェンゲゼルシャフト | Enantiomorphic reaction product consisting of mesogenic molecular element and difunctional reactive alkane diol and its use as dopant in liquid crystal phase |
| JPH01258635A (en) * | 1988-04-06 | 1989-10-16 | Adeka Argus Chem Co Ltd | Optically active bisaryl compound |
-
1990
- 1990-02-16 JP JP3387590A patent/JPH03239788A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62234048A (en) * | 1986-02-17 | 1987-10-14 | ヘキスト アクチェンゲゼルシャフト | Enantiomorphic reaction product consisting of mesogenic molecular element and difunctional reactive alkane diol and its use as dopant in liquid crystal phase |
| JPH01258635A (en) * | 1988-04-06 | 1989-10-16 | Adeka Argus Chem Co Ltd | Optically active bisaryl compound |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0429219A (en) * | 1990-05-25 | 1992-01-31 | Idemitsu Kosan Co Ltd | High-polymer liquid crystal composition, liquid crystal optical element formed by using this composition and method for driving liquid crystal optical element |
| EP0582468A1 (en) * | 1992-08-05 | 1994-02-09 | Mitsubishi Gas Chemical Company, Inc. | Anti-ferroelectric liquid crystal composition and liquid crystal display device |
| US5534190A (en) * | 1992-08-05 | 1996-07-09 | Mitsubishi Gas Chemical Company, Inc. | Anti-ferroelectric liquid crystal composition and liquid crystal display |
| GB2356629A (en) * | 1999-10-04 | 2001-05-30 | Merck Patent Gmbh | Bimesogenic compounds and their use in flexoelectric liquid crystal devices |
| GB2356629B (en) * | 1999-10-04 | 2004-09-22 | Merck Patent Gmbh | Bimesogenic Compounds and Flexoelectric Devices |
| JP2007070454A (en) * | 2005-09-06 | 2007-03-22 | Tokyo Institute Of Technology | Liquid crystal and method for producing the same |
| WO2007099669A1 (en) * | 2006-02-28 | 2007-09-07 | Nippon Oil Corporation | Dioxetane compound, cationically polymerizable composition, optical film and liquid crystal display unit |
| US7998543B2 (en) | 2006-02-28 | 2011-08-16 | Nippon Oil Corporation | Dioxetane compound, cationically polymerizable composition, optical film, and liquid crystal display device |
| KR101291392B1 (en) * | 2006-02-28 | 2013-07-30 | 제이엑스 닛코닛세키에너지주식회사 | Dioxetane compound, cationically polymerizable composition, optical film and liquid crystal display unit |
| US7763182B2 (en) | 2006-04-10 | 2010-07-27 | Nippon Oil Corporation | Liquid crystalline composition with improved adhesivity, liquid crystal film comprising the composition, and liquid crystal display device equipped with the film |
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