JPH0256447A - Optically active compound and use thereof - Google Patents
Optically active compound and use thereofInfo
- Publication number
- JPH0256447A JPH0256447A JP20638688A JP20638688A JPH0256447A JP H0256447 A JPH0256447 A JP H0256447A JP 20638688 A JP20638688 A JP 20638688A JP 20638688 A JP20638688 A JP 20638688A JP H0256447 A JPH0256447 A JP H0256447A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- compound
- formula
- liquid crystal
- active compound
- 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 60
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 230000003287 optical effect Effects 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 11
- 230000010287 polarization Effects 0.000 abstract description 11
- 230000002269 spontaneous effect Effects 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract description 7
- 150000002148 esters Chemical class 0.000 abstract description 7
- -1 phenol compound Chemical class 0.000 abstract description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 5
- 239000012320 chlorinating reagent Substances 0.000 abstract description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 22
- 230000004044 response Effects 0.000 description 12
- 230000007704 transition Effects 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 8
- NWHKQJPPILAVDT-UHFFFAOYSA-N 4-decoxyphenol Chemical compound CCCCCCCCCCOC1=CC=C(O)C=C1 NWHKQJPPILAVDT-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- FTLHGQOBAPTEHE-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-hydroxybenzoic acid Chemical group OC(=O)C1=C(F)C(F)=C(O)C(F)=C1F FTLHGQOBAPTEHE-UHFFFAOYSA-N 0.000 description 5
- 210000002858 crystal cell Anatomy 0.000 description 5
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 5
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KLAVPNKIYBZAOK-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propanoyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)OC(F)(C(Cl)=O)C(F)(F)F KLAVPNKIYBZAOK-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 230000005621 ferroelectricity Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
- CSEBNABAWMZWIF-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-(heptafluoropropoxy)propanoic acid Chemical compound OC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F CSEBNABAWMZWIF-UHFFFAOYSA-N 0.000 description 1
- INICGXSKJYKEIV-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzonitrile Chemical compound ClC1=C(Cl)C(Cl)=C(C#N)C(Cl)=C1Cl INICGXSKJYKEIV-UHFFFAOYSA-N 0.000 description 1
- YXWJGZQOGXGSSC-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzonitrile Chemical compound FC1=C(F)C(F)=C(C#N)C(F)=C1F YXWJGZQOGXGSSC-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- YVXBUUNZSDRJNX-UHFFFAOYSA-N 3-chloro-2,5,6-trifluoro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=C(F)C(F)=C(O)C(Cl)=C1F YVXBUUNZSDRJNX-UHFFFAOYSA-N 0.000 description 1
- YNBBQLUKHHSKPW-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 YNBBQLUKHHSKPW-UHFFFAOYSA-N 0.000 description 1
- CGTLMVREWQIWEC-UHFFFAOYSA-N 4-decylphenol Chemical compound CCCCCCCCCCC1=CC=C(O)C=C1 CGTLMVREWQIWEC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101150030061 Eloc gene Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000861914 Plecoglossus altivelis Species 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical group 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- DMZTYLSOWBKORG-UHFFFAOYSA-N decyl 4-(4-hydroxyphenyl)benzoate Chemical compound C1=CC(C(=O)OCCCCCCCCCC)=CC=C1C1=CC=C(O)C=C1 DMZTYLSOWBKORG-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- SVKXWHNJGAEURC-UHFFFAOYSA-N hexyl 4-(4-hydroxyphenyl)benzoate Chemical compound C1=CC(C(=O)OCCCCCC)=CC=C1C1=CC=C(O)C=C1 SVKXWHNJGAEURC-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野コ
本発明は新規な光学活性化合物、当該化合物を含有する
液晶組成物及び当該化合物あるいは当該化合物の少なく
と４１１種を成分として含有する液晶組成物を使用して
構成されることを特徴とする光スイツチング素子に関す
る。Detailed Description of the Invention [Industrial Field of Application] The present invention relates to a novel optically active compound, a liquid crystal composition containing the compound, and a liquid crystal composition containing the compound or at least 411 types of the compound as components. The present invention relates to an optical switching element characterized in that it is constructed using.
液晶表示素子の表示方式として現在広く実市に供されて
いるものは、ねじれネマチック型（’ｒＭ）及び動的散
乱型（ＤＢ）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が、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く、最
高数ｉす秒のオーダーの応答速度しか得られないという
事実があげられる。そしてこのことがネマチック液晶セ
ルの応用範囲を制約する−因となっている。これに対し
て最近スメクチック液晶セルを用いればよ）高速な応答
が得られることが明らかになって龜た。The display systems of liquid crystal display devices that are currently widely used in the market are the twisted nematic type ('rM) and the dynamic scattering type (DB). These are displays using nematic liquid crystal cells that mainly contain nematic liquid crystals, but one of the disadvantages of conventional nematic liquid crystal cells is the fact that the response speed is slow, and the maximum response speed can only be on the order of several i seconds. can be given. This is a factor that limits the range of applications of nematic liquid crystal cells. Recently, however, it has become clear that a smectic liquid crystal cell can provide a faster response.
光学活性なスメクチック液晶の中には強誘電性を示すも
のがあることが知られておシ、その応用に関して大きな
関心が持たれている。強誘電性液晶は、１９７５年、Ｒ
，Ｂ、メイヤー（Ｒ，Ｂ。It is known that some optically active smectic liquid crystals exhibit ferroelectricity, and there is great interest in their applications. Ferroelectric liquid crystal was developed in 1975 by R.
, B., Mayer (R.B.
Ｍｅｙｅｒ ）ら〔ジュルナール・ド・フイジーク（Ｊ
、 Ｐｈｙａ、 ）、＃＆５６巻、謁Ｌ６９貞（１９７
５）］によ）最初に合成され九が、それは、４−（４−
ｎ−デシルオキシベンジリデンアミノ）−２′−メテル
ブチルシンナメー） （ＤＯＢＡＭＥＯ）を代表列とす
るシッフ塩基系の化合物であシ、これカ光学活性の状態
、向えばカイラルスメクチック０相において強誘電性を
示すことを特徴とするものである。その後、組ム、クラ
ーク（舅、ム。Meyer) et al.
, Phya, ), Volume # & 56, Audience L69 Tei (197
5)] is first synthesized by 9, which is 4-(4-
It is a Schiff base-based compound represented by n-decyloxybenzylideneamino)-2'-methylbutylcinnamee (DOBAMEO), which is ferroelectric in the optically active state, that is, in the chiral smectic 0 phase. It is characterized by showing the following. After that, Kumu, Clark (father-in-law, Mu).
Ｑｌａｒｋ ）ら〔アプライド・フイジクス・レターズ
（ＡｐｐＬ Ｐｈｙｓ、 Ｌｓｔｔ、 ）第３６巻、第
８９９頁（１９８０）］により、ＤＯＢＡＭＢＣの薄膜
セルにおいて、マイクロ秒オーダーの高速応答性が発見
され、これが契機となって強誘電性液晶はその高速応答
性やメモリ性を利用して、液晶テレビ等のデイスプレィ
用のみならず、元プリンターヘット、光フーリエ変換素
子、ライトパルプ等のオプトエレクトロニクス関係素子
の部品にも使用可能な材料として注目を集めている。強
誘電性液晶セルにおいては、誘電率が高く、自発分極が
大きい材料を用いるほどセルを高速駆動できて有利であ
るため、自発分極の大きい材料の開発が望まれている。Qlark et al. [Applied Physics Letters (AppL Phys, Lstt.) Vol. 36, p. 899 (1980)] discovered a high-speed response on the microsecond order in the thin film cell of DOBAMBC, and this became an opportunity. By taking advantage of its high-speed response and memory properties, ferroelectric liquid crystals are used not only for displays such as LCD televisions, but also for parts of optoelectronic devices such as former printer heads, optical Fourier transform elements, and light pulp. It is attracting attention as a possible material. In ferroelectric liquid crystal cells, it is advantageous to use a material with a high dielectric constant and a large spontaneous polarization because the cell can be driven at high speed, so there is a desire to develop a material with a large spontaneous polarization.
また実用上は、液晶化合物あるいは組成物自身が安定で
あ夛、更には、室温を中心とする広い温度範囲で強Ｆｉ
Ｉｊ電性を示すことが必要である。In addition, in practice, it is important that the liquid crystal compound or composition itself is stable, and that it has a strong Fi
It is necessary to show Ij conductivity.
〔発明が解決しようとする課題］
しかし、ＤＯＢＡＭＥＯなどのシック塩基型の化合物は
水や光等に対する安定性の点で難点がわり、また強誘電
性を示す温度範囲も室温より４０℃黄よ１１．、あ、ヶ
５、え、１．第５゜アユなかった。そこで、強誘電性液
晶材料として、物理的化学的に安定で、しかも大きい自
発分極を持り材料系の実況が強く期待されている。[Problems to be Solved by the Invention] However, thick base type compounds such as DOBAMEO have some drawbacks in terms of stability against water, light, etc., and the temperature range in which they exhibit ferroelectricity is from room temperature to 40 degrees Celsius. , Ah, 5, E, 1. No. 5: There was no sweetfish. Therefore, there are strong expectations for the development of materials that are physically and chemically stable and have large spontaneous polarization as ferroelectric liquid crystal materials.
本発明の目的は化学的安定性、光安定性に優れ、自発分
極が大きく、かつカイラルスメクチックＣ相の温度範囲
の広い新規光学活性化合物を得ることにある。また本発
明はこのような光学活性化合物あるいは液晶組成物を用
いて高速応答性を有する衆示素子等を提供しようとする
ものである。An object of the present invention is to obtain a novel optically active compound that has excellent chemical stability and photostability, has large spontaneous polarization, and has a wide temperature range in the chiral smectic C phase. Further, the present invention aims to provide a display device having high-speed response using such an optically active compound or liquid crystal composition.
〔課題を解決するための手段］
本発明（ｉ−概説すれば、本発明の第１の発明は光学活
性化合物に関する発明であって、下記′−般式ｌ：
〔式中、Ｗ、Ｘ、ｙ及び２はフッ素又は塩素、ｍは１又
は２の数、Ｒ嬬炭素数４以上のアルキル基、アルキルオ
キシ基又はアル中ルオΦジカルボニル基を示し、０ｓ１
１．００’ＩＣＯＩＦ、）基あるいは基Ｒのうち、少な
くとも一方は光学活性１である］で表されることを特徴
とする。[Means for Solving the Problems] The present invention (i- To summarize, the first invention of the present invention is an invention relating to an optically active compound, which has the following '- general formula l: [where W, X, y and 2 are fluorine or chlorine; m is a number of 1 or 2;
1.00'ICOIF, at least one of the ) group or the group R has an optical activity of 1.
また、本発明の第２の発明は液晶組成物に関する発明で
あって、第１の発明の光学活性化合物の少なくと４１橿
を成分として含有することを特徴とする。Further, the second invention of the present invention relates to a liquid crystal composition, and is characterized in that it contains at least 41 g of the optically active compound of the first invention as a component.
そして、本発明のａＪ５の発明は光スイツチング素子に
関する発明であって、第１の発明の光学活性化合物、あ
るいはこの化合物の少なくとも１橿を成分として含有す
る液晶組成物を使用して構成されることを特徴とする。The invention of aJ5 of the present invention relates to an optical switching element, and is constructed using the optically active compound of the first invention or a liquid crystal composition containing at least one member of this compound as a component. It is characterized by
前記一般式（りの化合物は、中心骨格が安息香酸エステ
ル構造を有してお夛、更に分子の両末端に長鎖の置換基
（炭素数４〜１８が好ましい）が存在するのでそれ自身
が液晶性を示すものである。また、この化合物く不斉炭
素にカルボニル基を直接結合させているほか、フッ素あ
るいは塩素の双極子モーメントが分子長軸に対して横方
向に作用するので高い旋光性を有している。また、複数
のフッ素の存在により表面工ネルギーの低下が起こるた
め、強誘電性液晶に不可欠な薄いセル内において、ドメ
インの回転に対する抵抗が非フツ素系化合物に比較して
減少することが予想され、これらがあいまって表示素子
として使用する場合に高速応答性が期待できる。The compound of the above general formula (RI) has a central skeleton having a benzoic acid ester structure, and also has long-chain substituents (preferably 4 to 18 carbon atoms) at both ends of the molecule, so it itself has a benzoic acid ester structure. It exhibits liquid crystallinity.In addition, in addition to the carbonyl group being directly bonded to the asymmetric carbon of this compound, the dipole moment of fluorine or chlorine acts transversely to the long axis of the molecule, resulting in high optical rotation. In addition, since the presence of multiple fluorine atoms causes a decrease in surface engineering energy, the resistance to domain rotation within the thin cell essential for ferroelectric liquid crystals is lower than that of non-fluorine compounds. It is expected that this will decrease, and when these factors are used together as a display element, high-speed response can be expected.
本発明における一般式（りの光学活性化合物は、例えば
次のような合成経路に従って製造することができる。The optically active compound of the general formula (R) in the present invention can be produced, for example, according to the following synthetic route.
（■）
！Ｚ
（ｎ） （ｉｌｌ）Ｘ２
（ｆｌ／）
上記製造過程を概説すると、光学活性パーフルオロー２
−プロピルオキシプロピオン酸クロライド（１１）と４
−ヒドロキシポリフルオロ安息香酸類（ｉｌｌ）とを塩
基性物質の存在下に反応させてカルボン酸化合物（ＩＶ
）を製造する。（ＪＶ）を塩化チオニルなどの塩素化剤
にょ）酸クロライド（Ｖ）とする。(■)! Z (n) (ill)X2
(fl/) To outline the above manufacturing process, optically active perfluoro 2
-Propyloxypropionic acid chloride (11) and 4
-Hydroxypolyfluorobenzoic acids (ill) are reacted in the presence of a basic substance to form a carboxylic acid compound (IV
) is manufactured. Let (JV) be a chlorinating agent such as thionyl chloride (V).
なお化合物（ＩＩ）は、文献１：パーテヤル（Ｊ。Compound (II) is described in Document 1: Parteyal (J.
Ｍ、Ｂｉｒｃｈａｌｌ ） ほか、ジャーナル・オプ
・ケミカル・ンサエテイ（Ｊ、Ｏｈｅｍ、Ｅｌｏｃ、
） １９７１年、第１３４５頁あるいは文献２：高
岡昭生、石川地力ほか、日本化学会誌、１９８５年、第
２１５５頁に従い、ペンタフルオロ−あるいはペンタク
ロロ−ベンゾニトリルから製造することができる。M, Birchall) et al., Journal of Chemical Engineering (J, Ohem, Eloc,
) 1971, p. 1345 or Document 2: Akio Takaoka, Jiki Ishikawa et al., Journal of the Chemical Society of Japan, 1985, p. 2155, it can be produced from pentafluoro- or pentachloro-benzonitrile.
ｃｏｓＴ１ａａ特願昭６３−１１０４１３４号明ｍ誉記
載の通シである。CosT1aa Japanese Patent Application No. 1104134/1983.
最後に酸クロライド（Ｖ） ’ｌｃ塩基性物質の存在下
、フェノール化合物（Ｍ）と反応させて一般式ｌで示さ
れる化合物を製造することができる。Finally, acid chloride (V) can be reacted with a phenol compound (M) in the presence of a basic substance to produce a compound represented by general formula 1.
またラセミ体のパーフルオロ−２−プロピルオキシプロ
ピオン酸を用いる場合には、一般式（■）の化合物の基
Ｒ中のアルキル基が光学活性である化合物を使用して一
般式（１） （Ｄ化合物を製造することができる。In addition, when racemic perfluoro-2-propyloxypropionic acid is used, a compound of the general formula (■) in which the alkyl group in the group R is optically active is used, and a compound of the general formula (1) (D compounds can be manufactured.
以下、本発明を実ＩＩ／ａ列によシ更に具体的に説明す
るが、本発明の適用範囲はこれらの実施列によって限定
される−のではない。Hereinafter, the present invention will be explained in more detail using series II/a, but the scope of application of the present invention is not limited by these series.
実施列１
（ａ） 元’ｆ−活性−バーフルオロ−２−７’ ｏ
ヒ／Ｉ／オ争シブロビオ／酸りロライド五５ｆｉトルエ
ン浴媒とし、４−ヒドロキシテトラフルオロ安息香＃１
ｔ（ｉｌｌ）の水和物２．５ｔのピリジン３０−の溶液
に徐々にｌ４下して５５〜６５Ｃにて５時間反応６せ、
−夜装置した俊水ｔ−加えてエーテル抽出し、水で洗浄
して無水−酸マグネシウムで乾課し、エーテルを留去し
てヘキサンｔ−溶媒とするシリカゲルのカラムクロマト
グラフィで種実Ｌ％４−（パーフルオロ−１−プロピル
オキシエチル）カルボニルオキシテトラフルオロ安息香
酸（ＩＶ） ｔ−得た。Example row 1 (a) Original 'f-activated-verfluoro-2-7' o
Hi/I/O Sibrobio/Acid loride 5fi toluene bath medium, 4-hydroxytetrafluorobenzoin #1
The hydrate of t(ill) was gradually added to a solution of 2.5 t of pyridine 30- and reacted at 55 to 65 C for 5 hours.
- Shunsui t prepared at night - Add ether extraction, wash with water, dry with anhydrous acid magnesium, distill off the ether and use hexane t - Column chromatography on silica gel using seed L%4- (Perfluoro-1-propyloxyethyl)carbonyloxytetrafluorobenzoic acid (IV) t-obtained.
（１）） （１！Ｌ）で得られ友化合＊ ＜ｙ＞ １．
ｓ ｔ ニ塩化チオニル１（ｌｄｔ’／Ｊ１１えて２
時間１ＪＩＪ熱後項化チオニルを減圧下留去して、これ
をトルエン溶液とし、４−デシルオキシフェノール（％
Ａ）１１７ｆのピリジン５０−の溶液に徐々に滴下して
５７〜６６℃にて５時間反応させ、−夜装置した後１ｑ
ｋ水酸化す） ＩＪウム水水溶液−で水で洗浄し、無水
硫酸マグネシウムで乾燥後溶媒を留去して、残留物乞ヘ
キサン−トルエンを溶媒とするシリカゲルのカラムクロ
マトグラフィによｌ［し、更にヘプタンを用いて低温で
再結晶して化合物■：４−（パーフルオロ−１−プロピ
ルオキシエチル）カルボニルオキシテトラフルオロ安息
香酸−４’−テシルオキシフェニルエステルｆ：ＩＪＪ
造した。(1)) Friend compound obtained by (1!L) * <y> 1.
s t thionyl dichloride 1 (ldt'/J11 et 2
After heating for 1 JIJ, the thionyl compound was distilled off under reduced pressure, and this was made into a toluene solution, and 4-decyloxyphenol (%
A) 117f was gradually added dropwise to a solution of 50-pyridine and reacted at 57-66°C for 5 hours.
The residue was washed with water using an aqueous solution of IJ and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. Recrystallized from heptane at low temperature to obtain compound (1): 4-(perfluoro-1-propyloxyethyl)carbonyloxytetrafluorobenzoic acid-4'-tesyloxyphenyl ester f: IJJ
Built.
（０）この化合物を透明′電極の間隙が約３μｍのガラ
スセルに封入し、±５Ｖ、ＩＥｇ の電界を印加しなが
ら偏光顕微鏡で観察すると、温度降下時に１２．４℃か
ら電界の反転に伴いドメインも反転するのが認められた
。その他の相転移温度は他の列と共に後記表１に示しで
ある。なおｃｒｙ ｒｔ結晶状態、ＳＣ率は強誘電性の
カイラルスメクチックＣ相で、上記の電界に対して少な
くとも一部が応答する鼻相である。８Ａはスメクチック
Ａ相、Ｏｈ はコレステリック相、工は等方性液相を示
している。ま几・はその相が存在することを示している
。なお（）はその相がモノトロピックであること、−μ
その相の存在が明確でないことを示している。(0) When this compound was sealed in a glass cell with a gap of about 3 μm between transparent electrodes and observed with a polarizing microscope while applying an electric field of ±5 V, IEg, it was found that as the temperature decreased from 12.4°C, the electric field reversed. Domains are also allowed to be reversed. Other phase transition temperatures are shown in Table 1 below along with other columns. Note that the cry rt crystal state and SC rate are a ferroelectric chiral smectic C phase, which is a nasal phase that at least partially responds to the above electric field. 8A indicates the smectic A phase, Oh indicates the cholesteric phase, and H indicates the isotropic liquid phase.ま几・shows that the phase exists. Note that () indicates that the phase is monotropic, −μ
This shows that the existence of that phase is not clear.
この化合物２ｔＩＬ極間隙１２０μｍのセルに封入し、
営巣らの報告による三角波法［Ｋ、営巣、日、アベ、■
、タケゾエ、Ａ、フクダ及びＥ、クゼ（Ｋ。This compound was sealed in a cell with a 2tIL electrode gap of 120 μm,
The triangular wave method reported by Nest et al. [K, Nest, Hi, Abe, ■
, Takezoe, A., Fukuda and E., Kuze (K.
Ｍｉ７５Ｌ８ａｔＯ，８，Ａｂｅ ％Ｈ，Ｔａｋｅｚｏ
ｅ 、 Ａ、 Ｆｕｋｕ（ｉａ ％１１ｉ、 Ｋｕｚｅ
） 、 ジャパニーズ・ジャーナル・オブ・アプラ
イド・フィツクス（Ｊｐｎ、 Ｊ、ム１）ｌ−Ｐｈｙｓ
、 ）、１９８５年、ｍ２２巻、第Ｌ６６ｉ員〕で自
発分極を測定したところ、その値は１２８ ｎ０７ｍ”
であった。Mi75L8atO,8,Abe%H,Takezo
e, A, Fuku(ia%11i, Kuze
), Japanese Journal of Applied Fixtures (Jpn, J, M1) l-Phys
), 1985, volume m22, member L66i], the value was 128 n07m"
Met.
実施列２
ＦＦ”
４−ヒドロキシテトラフルオロ安息香酸に代えて４−ヒ
ドロキシ−５−クロロトリフルオロ安息香酸を用いる以
外は実施列１と同様にして化合物■：４−（／＜−フル
オロ−１−プロピルオキシエチル）カルボニルオキシ−
３−クロロトリフルオロ安息香酸−４′−デシルオキシ
フェニルエステルｔ’製造した。この化合物の相転、移
温度は表１に示す通シである。Example 2 FF'' Compound ■: 4-(/<-fluoro-1- Propyloxyethyl)carbonyloxy-
3-chlorotrifluorobenzoic acid-4'-decyloxyphenyl ester t' was prepared. The phase transition and transition temperature of this compound are shown in Table 1.
また実施列１と同様にして測定した自発分極の値は１６
８ ｎｃ／３” であった。In addition, the value of spontaneous polarization measured in the same manner as in Example 1 was 16
8 nc/3”.
実施例５
４−ヒドロキシテトラフルオロ安息香酸に代えて４−ヒ
ドロ争シー２−クロロトリフルオロ安息香酸、４−デシ
ルオキシフェノールに代えて４−デシルフェノールを用
いる以外は実施列１と同様にして化合物■：４−（パー
フルオロ−１−プロピルオキシエチル３カルボニルオ中
シー２−クロロトリフルオロ安息香ｇ−４’−ｆシルフ
ェニルエステルｔｍ造した。この化合物Ｏ相転移温度Ｊ
ｄｆｆ１に示す通）である。Example 5 A compound was prepared in the same manner as in Example 1, except that 4-hydroxytetrafluorobenzoic acid was replaced with 4-hydroxytetrafluorobenzoic acid, and 4-decyloxyphenol was used with 4-decylphenol. ■: 4-(perfluoro-1-propyloxyethyl 3-carbonyl-2-chlorotrifluorobenzoic g-4'-f sylphenyl ester tm was prepared. This compound O phase transition temperature J
dff1).
また実施ｙ′４１と同様にして測定した自発分極の値は
１０５ ｎｏ／ｃｔｎ” であった。Further, the value of spontaneous polarization measured in the same manner as in Example y'41 was 105 no/ctn''.
実施列４
ＦＩＴ’
４−デシルオキシフェノールに代えて４−オクチルオキ
シ−４′−ヒドロ午シビフェニルヲ用い、（ｂ）におけ
るカラムクロマトグラフィの溶媒にり０ｃ１ホルム−へ
午サンを用いる以外は実施例１と同様にして化合物■：
４−（パーフルオａ−１−プロピルオキシエチル）カル
ボニルオキシテトラフルオロ安息香酸−４＃−オクチル
オキシ−４′−ビフェニルエヌテルを製造した。この化
合物の相転移温度は表１に示す通りである。Example 4 FIT' Same as Example 1 except that 4-octyloxy-4'-hydro-sibiphenyl was used instead of 4-decyloxyphenol, and 0c1 form-hexane was used as the solvent for column chromatography in (b). Similarly, compound ■:
4-(Perfluoro-a-1-propyloxyethyl)carbonyloxytetrafluorobenzoic acid-4#-octyloxy-4'-biphenyl ether was produced. The phase transition temperature of this compound is shown in Table 1.
また実施例１と同様にして測定した自発分極の値は８７
ｎａ／ｃｐｓ”であった。Furthermore, the value of spontaneous polarization measured in the same manner as in Example 1 was 87
na/cps”.
実施例５
４−デシルオキシフェノールに代えて４′−ヒドロキシ
−４−ビフェニルカルボン酸デシルエステルを用いる以
外は実施例１と同様にして化合物■：４−（パーフルオ
ロ−１−プロピル亥キシエチルンカルボニルオキシテト
ラフルオロ安息香ｄｉ −４’−デシルオキシカルボニ
ル−４′−ビフェニルエステルを製造した。この化合物
の相転移温度は我１に示す通シである。Example 5 Compound (1): 4-(perfluoro-1-propyloxyethyl) was prepared in the same manner as in Example 1 except that 4'-hydroxy-4-biphenylcarboxylic acid decyl ester was used in place of 4-decyloxyphenol. Carbonyloxytetrafluorobenzoic di-4'-decyloxycarbonyl-4'-biphenyl ester was produced.The phase transition temperature of this compound was as shown in 1.
実施例６
４−ヒドロキシテトラフルオロ安息香酸に代えて４−ヒ
ドロキシ−５−クロロトリフルオロ安息香酸、４−デシ
ルオキシフェノールに代えテ４′−ヒドロキシー４−ビ
フェニルカルボン酸ヘキシルエステルを用い、（ｂ）に
おけるカラムクロマトグラフィの溶媒にクロロホルム−
ヘキサンを用いる以外は実施列１と同様にして化合物■
：４−（パーフルオロ−１−プロピルオキシエチル）カ
ルボニルオキシ−５−クロロトリフルオロ安息香！！−
４’−へキシルオキシカルボニル−４′−ピフェニルエ
ステルヲ製造した。この化合物の相転移温度は表１に示
す通υである。Example 6 Using 4-hydroxy-5-chlorotrifluorobenzoic acid in place of 4-hydroxytetrafluorobenzoic acid, and using 4'-hydroxy-4-biphenylcarboxylic acid hexyl ester in place of 4-decyloxyphenol, (b) Chloroform is used as a solvent for column chromatography in
Compound ■ was prepared in the same manner as in Example 1 except that hexane was used.
:4-(Perfluoro-1-propyloxyethyl)carbonyloxy-5-chlorotrifluorobenzoic! ! −
4'-hexyloxycarbonyl-4'-piphenyl ester was prepared. The phase transition temperature of this compound is shown in Table 1.
また実施列１と同様にして測定した自発分極の値は１４
５ ｎｏ１５Ｉ” であった。In addition, the value of spontaneous polarization measured in the same manner as in Example 1 was 14
5 no15I”.
実施例７
ｔ Ｆ
４−ヒドロキシテトラフルオロ安息香酸に代えて４−ヒ
ドロキシ−４５−ジクロロジフルオロ安息香酸、４−デ
シルオキシフェノールに代えて４−オクチルオキシ−４
′−ヒドロキシピフェニルを用いる以外は実施Ｖ／ＩＪ
１と同様にして化合物■： ４− （バーフルオロ−
１−プロピルオキシエチル）カルボニルオキシ−４５−
ジクロロジフルオロ安息香＠ −ａｌ−オクチルオキシ
−４′−ビフェニルエステルを製造した。Example 7 tF 4-hydroxy-45-dichlorodifluorobenzoic acid in place of 4-hydroxytetrafluorobenzoic acid, 4-octyloxy-4 in place of 4-decyloxyphenol
Implementation V/IJ except using '-hydroxypiphenyl
Compound ■: 4- (barfluoro-
1-propyloxyethyl)carbonyloxy-45-
Dichlorodifluorobenzoic@-al-octyloxy-4'-biphenyl ester was prepared.
この化合物の相転移温度は表１に示す通シであシ、ｓｅ
ｅ相は示さなかったが、実施列９に示すように、ノンカ
イラル液晶化合物との混合によシ、ＳＣ＊相の発現が観
察され九。The phase transition temperature of this compound is shown in Table 1.
Although no e-phase was observed, as shown in Example 9, the development of SC* phase was observed upon mixing with a non-chiral liquid crystal compound.
実施例８
ヒトΩキシ−２−クロロトリフルオロ安息香酸、４−デ
シルオキシフェノールに代えて光学活性−４−（１−メ
チルへブチルオキシ）−４′−ヒドロキシビフェニルを
用いる以外は実施ガ１と同様にして化合物■：４−（パ
ーフルオロ−１−プロピルオキシエチル）カルボニルオ
キシ−２−りＯｔ２トリフルオロ安息香酸−４′〜（１
−メチルへブチルオキシ） −４’−ビフェニルエステ
ルｌｒ：製造した。この化合物の相転移温度は表１に示
す通りである。Example 8 Same as Example 1 except that optically active -4-(1-methylhebutyloxy)-4'-hydroxybiphenyl was used in place of human Ω-x-2-chlorotrifluorobenzoic acid and 4-decyloxyphenol. Compound ■: 4-(perfluoro-1-propyloxyethyl)carbonyloxy-2-trifluorobenzoic acid-4'-(1
-Methylhebutyloxy) -4'-biphenyl ester lr: Manufactured. The phase transition temperature of this compound is shown in Table 1.
実施ｆ！１ＩＵ１と同様にして測定した自発分極の値は
５５ ｎ０７ｍ”であった。Implementation f! The spontaneous polarization value measured in the same manner as 1IU1 was 55 n07m''.
光学活性−バーフルオロー２−プロビルオキシグロビオ
ン酸に代えてそのラセミ体、４−ヒドロキシテトラフル
オロ安息香酸に代えて４−実施Ｎ９
く液晶組成物〉
実施列７で製造した化合物の０２０直量部に対して、ノ
ンカイラルのスメクチック液晶である下記構造式の４’
−（２−メチルブチル）−４−ビフェニルカルボン酸（
４−オクチルオキシフェニル）エステル２５重量部、及
び４′−オクチルオキシ−４−ビフェニルカルボン酸（
４−ノニルオ午ジフェニル）エステル５５ｔｉｌ［Ｂｉ
混合して液晶組成物を調製した。Optically active liquid crystal composition> 020 parts of the compound prepared in Example 7, in place of the racemate thereof in place of the optically active barfluoro-2-probyloxyglobionic acid, and in place of 4-hydroxytetrafluorobenzoic acid On the other hand, 4' of the following structural formula is a non-chiral smectic liquid crystal.
-(2-methylbutyl)-4-biphenylcarboxylic acid (
25 parts by weight of 4-octyloxyphenyl) ester, and 4'-octyloxy-4-biphenylcarboxylic acid (
4-nonylodiphenyl) ester 55til[Bi
A liquid crystal composition was prepared by mixing.
この液晶組成物は１０〜６２℃の範囲でＢＣ＊相を示し
、その温度範囲が単独の化合物に比較して著しく拡大さ
れた。This liquid crystal composition exhibited a BC* phase in the range of 10 to 62°C, and its temperature range was significantly expanded compared to that of a single compound.
実施例１０
（液晶組成物〉
実ｍ列１．２及び５において製造した化合物■、■及び
■のそれぞれ１０．１２、及び１５重量部に対して、実
施列９におけるノンカイラルのスメクチック液晶をそれ
ぞれ４０及び２５重量部混合して液晶組成物？：調製し
た。この液晶組成物は６〜５９℃の範囲でＳＣ本相を示
し、その温度範囲が単独の化合物に比較して著しく拡大
された。Example 10 (Liquid crystal composition) 40 parts of the nonchiral smectic liquid crystal in Example Example 9 was added to 10.12 and 15 parts by weight of the compounds ■, ■, and ■ produced in Actual m rows 1.2 and 5, respectively. and 25 parts by weight were mixed to prepare a liquid crystal composition.This liquid crystal composition showed an SC main phase in the range of 6 to 59°C, and its temperature range was significantly expanded compared to that of a single compound.
以上２つの実施列で示し九ように、構造の異なる液晶化
合物を混合することによシ、単独で用いるよりも広い温
度範囲、しかも室温の上下でカイラルスメクチック０液
晶となる液晶組成物ｔ−４ることができる。As shown in the above two examples, by mixing liquid crystal compounds with different structures, liquid crystal composition t-4 becomes a chiral smectic 0 liquid crystal over a wider temperature range than when used alone, and moreover above and below room temperature. can be done.
実施列１１
く光スイツチング素子〉
ポリイミド膜にラビング配向処理を施した、透明電極の
間隙約３μｍのガラスセルに、実施列５で得られる化合
物■を加熱して等方性液体として充てんした。このセル
を徐冷して２４℃に保持し、上２０’７．ＩＤ１１ｍ
の方形波を印加したときの透過光強度の変化を光電子増
倍管で測定した結果、光強度００〜９０僑変化による応
答時間ｔＩ′１２１０μθθＣであシ、高速な応答性を
示した。Example 11 Optical Switching Element> Compound (1) obtained in Example 5 was heated and filled as an isotropic liquid into a glass cell in which a polyimide film had been subjected to rubbing alignment treatment and the gap between transparent electrodes was about 3 μm. This cell was slowly cooled and kept at 24°C, and the upper 20'7. ID11m
As a result of measuring the change in the transmitted light intensity with a photomultiplier tube when a square wave of 200 nm was applied, it was found that the response time tI' was 1210 μθθC when the light intensity changed from 00 to 90, indicating a high-speed response.
実施例１２
く光スイツチング素子〉
実施列？及び１０で調製した液晶組成物を用いて、実施
列１１と同様にしてセルを作製した。Example 12 Light switching element〉 Implementation row? A cell was produced in the same manner as in Example 11 using the liquid crystal compositions prepared in 1 and 10.
測定温度ｆ：３５℃とする以外は実施列１１と同一条件
で求めた応答時間はそれぞれ１４０及び５０μｓｅａで
あυ、高速な応答性を示した。The response times determined under the same conditions as Example 11 except that the measurement temperature f was 35° C. were 140 and 50 μsea, respectively, indicating high-speed response.
以上説明し九ように本発明によれば、一般式Ｉで表され
る光学活性化合物、あるいはこの光学活性化合物の少な
くとも１種を成分として含有する液晶組成物を用いるこ
とによシ、自発分極が大きいために表示素子として用い
る場合に高速応答が可能であるのみならず、広い温度範
囲でカイラルスメクチック相を示す材料系及び光スイツ
チング素子を提供することができる。As explained above, according to the present invention, spontaneous polarization can be achieved by using an optically active compound represented by the general formula I or a liquid crystal composition containing at least one of the optically active compounds as a component. Due to its large size, it not only enables high-speed response when used as a display element, but also provides a material system and optical switching element that exhibits a chiral smectic phase over a wide temperature range.
Claims (1)
は２０数、Ｒは炭素数４以上のアルキル基、アルキルオ
キシ基又はアルキルオキシカルボニル基を示し、Ｃ＿３
Ｆ＿７ＯＣＦ（ＣＦ＿３）基あるいは基Ｒのうち、少な
くとも一方は光学活性基である〕で表されることを特徴
とする光学活性化合物。 ２、請求項１記載の光学活性化合物の少なくとも１種を
成分として含有することを特徴とする液晶組成物。 ３、請求項１記載の光学活性化合物、あるいはこの化合
物の少なくとも１種を成分として含有する液晶組成物を
使用して構成されることを特徴とする光スイッチング素
子。[Claims] 1. The following general formula I: ▲There are mathematical formulas, chemical formulas, tables, etc.▼...[I] [In the formula, W, X, Y, and Z are fluorine or chlorine, and m is 1 or 20 number, R represents an alkyl group, alkyloxy group, or alkyloxycarbonyl group having 4 or more carbon atoms, and C_3
An optically active compound characterized in that at least one of the F_7OCF (CF_3) group and the group R is an optically active group. 2. A liquid crystal composition containing at least one optically active compound according to claim 1 as a component. 3. An optical switching element constructed using the optically active compound according to claim 1 or a liquid crystal composition containing at least one of the compounds as a component.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63206386A JPH0830034B2 (en) | 1988-08-22 | 1988-08-22 | Optically active compound and its use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63206386A JPH0830034B2 (en) | 1988-08-22 | 1988-08-22 | Optically active compound and its use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0256447A true JPH0256447A (en) | 1990-02-26 |
| JPH0830034B2 JPH0830034B2 (en) | 1996-03-27 |
Family
ID=16522487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63206386A Expired - Fee Related JPH0830034B2 (en) | 1988-08-22 | 1988-08-22 | Optically active compound and its use |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0830034B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5051527A (en) * | 1988-02-29 | 1991-09-24 | Showa Shell Sekiyu K.K. | Liquid crystal compounds having fluoroalkyl radical |
| US5087777A (en) * | 1990-12-04 | 1992-02-11 | Allied-Signal Inc. | Partially fluorinated alkenes having a tertiary structure |
-
1988
- 1988-08-22 JP JP63206386A patent/JPH0830034B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5051527A (en) * | 1988-02-29 | 1991-09-24 | Showa Shell Sekiyu K.K. | Liquid crystal compounds having fluoroalkyl radical |
| US5087777A (en) * | 1990-12-04 | 1992-02-11 | Allied-Signal Inc. | Partially fluorinated alkenes having a tertiary structure |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0830034B2 (en) | 1996-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |