JPH0533942B2 - - Google Patents
Info
- Publication number
- JPH0533942B2 JPH0533942B2 JP61173921A JP17392186A JPH0533942B2 JP H0533942 B2 JPH0533942 B2 JP H0533942B2 JP 61173921 A JP61173921 A JP 61173921A JP 17392186 A JP17392186 A JP 17392186A JP H0533942 B2 JPH0533942 B2 JP H0533942B2
- Authority
- JP
- Japan
- Prior art keywords
- derivatives
- liquid crystal
- formula
- alkyl group
- carbon atoms
- 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.)
- Expired - Lifetime
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000004973 liquid crystal related substance Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 238000013329 compounding Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 description 15
- 230000003287 optical effect Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000008204 material by function Substances 0.000 description 5
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000004694 iodide salts Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- SKIDNYUZJPMKFC-UHFFFAOYSA-N 1-iododecane Chemical compound CCCCCCCCCCI SKIDNYUZJPMKFC-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000003098 cholesteric effect Effects 0.000 description 3
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical group OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 150000003862 amino acid derivatives Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001841 cholesterols Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BTUGGGLMQBJCBN-UHFFFAOYSA-N 1-iodo-2-methylpropane Chemical compound CC(C)CI BTUGGGLMQBJCBN-UHFFFAOYSA-N 0.000 description 1
- BUZZUHJODKQYTF-UHFFFAOYSA-N 1-iodo-3-methylbutane Chemical compound CC(C)CCI BUZZUHJODKQYTF-UHFFFAOYSA-N 0.000 description 1
- ZQUIJUNLTMQRAA-UHFFFAOYSA-N 1-iodo-3-methylcyclohexane Chemical compound CC1CCCC(I)C1 ZQUIJUNLTMQRAA-UHFFFAOYSA-N 0.000 description 1
- SWGRLCBZNPROCQ-UHFFFAOYSA-N 1-iodoheptadecane Chemical compound CCCCCCCCCCCCCCCCCI SWGRLCBZNPROCQ-UHFFFAOYSA-N 0.000 description 1
- LMHCYRULPLGEEZ-UHFFFAOYSA-N 1-iodoheptane Chemical compound CCCCCCCI LMHCYRULPLGEEZ-UHFFFAOYSA-N 0.000 description 1
- KMWHQYDMBYABKL-UHFFFAOYSA-N 1-iodohexadecane Chemical compound CCCCCCCCCCCCCCCCI KMWHQYDMBYABKL-UHFFFAOYSA-N 0.000 description 1
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 1
- UYBWORFIJZQKEP-UHFFFAOYSA-N 1-iodoicosane Chemical compound CCCCCCCCCCCCCCCCCCCCI UYBWORFIJZQKEP-UHFFFAOYSA-N 0.000 description 1
- LXFODWIENIOBLX-UHFFFAOYSA-N 1-iodononadecane Chemical compound CCCCCCCCCCCCCCCCCCCI LXFODWIENIOBLX-UHFFFAOYSA-N 0.000 description 1
- OGSJMFCWOUHXHN-UHFFFAOYSA-N 1-iodononane Chemical compound CCCCCCCCCI OGSJMFCWOUHXHN-UHFFFAOYSA-N 0.000 description 1
- ZNJOCVLVYVOUGB-UHFFFAOYSA-N 1-iodooctadecane Chemical compound CCCCCCCCCCCCCCCCCCI ZNJOCVLVYVOUGB-UHFFFAOYSA-N 0.000 description 1
- UWLHSHAHTBJTBA-UHFFFAOYSA-N 1-iodooctane Chemical compound CCCCCCCCI UWLHSHAHTBJTBA-UHFFFAOYSA-N 0.000 description 1
- HHXJMIXXUWDKIA-UHFFFAOYSA-N 1-iodopentadecane Chemical compound CCCCCCCCCCCCCCCI HHXJMIXXUWDKIA-UHFFFAOYSA-N 0.000 description 1
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 1
- FHQCFGPKNSSISL-UHFFFAOYSA-N 1-iodotetradecane Chemical compound CCCCCCCCCCCCCCI FHQCFGPKNSSISL-UHFFFAOYSA-N 0.000 description 1
- FKUQOQPBCHJHAP-UHFFFAOYSA-N 1-iodoundecane Chemical compound CCCCCCCCCCCI FKUQOQPBCHJHAP-UHFFFAOYSA-N 0.000 description 1
- ICEBAZPURYIURB-UHFFFAOYSA-N 2-(2-methylbutyl)benzoic acid Chemical compound CCC(C)CC1=CC=CC=C1C(O)=O ICEBAZPURYIURB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical group CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- IQRUSQUYPCHEKN-UHFFFAOYSA-N 2-iodobutane Chemical compound CCC(C)I IQRUSQUYPCHEKN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical class C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical class C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical class C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 150000001788 chalcone derivatives Chemical class 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical class C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000006480 iodobenzyl group Chemical group 0.000 description 1
- ZQCXCNPOYCQOEW-UHFFFAOYSA-N iodocycloheptane Chemical compound IC1CCCCCC1 ZQCXCNPOYCQOEW-UHFFFAOYSA-N 0.000 description 1
- FUCOMWZKWIEKRK-UHFFFAOYSA-N iodocyclohexane Chemical compound IC1CCCCC1 FUCOMWZKWIEKRK-UHFFFAOYSA-N 0.000 description 1
- LDKYPRVLJQWKBI-UHFFFAOYSA-N iodocyclooctane Chemical compound IC1CCCCCCC1 LDKYPRVLJQWKBI-UHFFFAOYSA-N 0.000 description 1
- PCEBAZIVZVIQEO-UHFFFAOYSA-N iodocyclopentane Chemical compound IC1CCCC1 PCEBAZIVZVIQEO-UHFFFAOYSA-N 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- -1 polycyclic hydrocarbon Chemical class 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Description
［産業上の利用分野］
本発明は分子構造の変更が容易でかつ光学活性
を有する乳酸誘導体、それを含有する組成物に関
するものである。
本発明の化合物は、光学活性を有することを特
徴とする種々の光学素子を形成する場合に必要な
機能性材料を合成するための光学活性中間体とし
て特に有用である。光学活性を有することを特徴
とする光学素子としては、具体的には、
(1) 液晶状態においてコレステリツク・ネマテイ
ツク相転移効果を利用するもの〔J.Jウイソキ、
A.アダムス及びW.ハース；フイジカル・レビ
ユー・レターズ、20、1024（1968）（J.J.
Wysoki、A.Adams and W.Haas；Phys.Rev.
Lett.、20、1024（1968））〕
(2) 液晶状態においてホワイト・テイラー形ゲス
ト・ホスト効果を利用するもの〔D.L.ホワイト
及びG.N.テイラー；ツアイトシユリフト・フ
エア・フイジカリツシエ・ヘミー．、45、4718
（1974）（D.L.White and G.N.Taylor；Z.
Appl.Phys.、45、4718（1974））〕、
(3) 液晶状態においてカイラル・スメクチツクソ
相、Ｈ相、Ｆ相、Ｉ相、Ｇ相の強誘電性効果を
利用するもの〔N.A.クラーク及びS.T.ラガー
ウオール；アプライド・フイジツクス・レター
ズ．、36、899（1980）（N.A.Clark and S.T.
Lagerwall；Appl.Phys.Lett.、36，899
（1980））〕、
(4) 液晶状態においてコレステリツク相を持つも
のをマトリツクス中へ固定することにより、そ
の選択散乱特性を利用し、ノツチフイルターや
ドンドパスフイルターとして利用するもの〔F.
J.カーン、アプライド・フイジツクス、レター
ズ、18、231（1971）（F.J.Kahn、Appl.Phys.
Lett.、18、231（1971））〕、円偏光特性を利用し
た円偏光ビームスプリツターとして利用するも
の〔S.D.ヤコブス、エス・ピー・アイ・イー、
37、98（1981）（S.D.Jacobs、SPIE、37、98
（1981））〕
等が知られている。個々の方式についての詳細な
説明は省略するが、表示素子・変調素子として重
要である。
また、ツイステツド・ネマチツク（TN）型表
示素子用のネマチツク液晶組成物にごく少量添加
することにより表示面のしま模様（リバースドメ
イン）の発生を防止し、その表示の均一性を増大
させることにも利用することが出来る。
従来、光学活性を有することを特徴とする光学
素子に必要な機能性材料を合成するための光学活
性中間体としては、２−メチルブタノール、２級
オクチルアルコール、２級ブチルアルコール、塩
化ｐ−（２−メチルブチル）安息香酸、２級フエ
ネチルアルコール、アミノ酸誘導体、シヨウノウ
誘導体、コレステロール誘導体等が知られてい
る。
しかし、これらは次のような欠点を有してい
る。光学活性な鎖状炭化水素誘導体は構造の変更
が困難で、しかも一部のものを除き非常に高価な
ものである。アミノ酸誘導体は比較的安価な上に
構造の変更も容易であるがアミンの水素基が化学
的に活性が強く、水素結合や化学反応を生じやす
いために機能性材料の特性を制限してしまいやす
い。シヨウノウ誘導体・コレステロール誘導体は
構造の変更が困難なうえに立体的な障害によつて
機能性材料の特性に悪影響を与えやすい。
上記のような欠点は、種々の材料を開発する上
で大きな制約となつていた。
［発明が解決しようとする問題点］
本発明は、上記の点に鑑みなされたものであ
る。すなわち、本発明は、適度な分子間力と形状
をもつた機能性材料中間体と光学活性を損うこと
なく結合させることができ、分子設計を自由に行
うことができる化合物を提供することを目的とす
る。
本発明はアルキル基の長さを変更することが容
易で、このことにより〔H.アーノルド、ジヤー
ナル・オブ・フイジカル・ケミストリー（H.
Arnold、J.Phys.Chem.、226、146（1964））〕に示
されるように液状状態において発現する液晶相の
種類や温度範囲を制御することが可能な液晶性化
合物及びそれを少なくとも１種類配合成分として
含有する液晶組成物を提供することを目的とす
る。またLB膜法により単分子累積膜を作製する
場合には容易に疎水基を制御することが出来、安
定に成膜することが可能な化合物の提供を目的と
する。
［問題点を解決するための手段及び作用］
本発明は、一般式（）：
（上記一般式中Ｒは炭素数１〜18の直鎖状アルキ
ル基を示す。又、＊は不斉炭素数原子を示す。Ａ
は化学的に活性な置換基を示す。）
で表わされる光学活性な乳酸誘導体から誘導され
る、
一般式（）
（上記一般式中Ｒは炭素数１〜18の直鎖状アルキ
ル基を示す。R′は炭素数４〜18のアルキル基も
しくはアルコキシ基を示す。Ｂは
[Industrial Field of Application] The present invention relates to a lactic acid derivative whose molecular structure can be easily changed and which has optical activity, and a composition containing the same. The compound of the present invention is particularly useful as an optically active intermediate for synthesizing functional materials necessary for forming various optical elements characterized by having optical activity. Specifically, optical elements characterized by having optical activity include: (1) those that utilize cholesteric-nematic phase transition effects in a liquid crystal state [JJ Wysocki,
A. Adams and W. Haas; Physical Review Letters, 20, 1024 (1968) (JJ
Wysoki, A.Adams and W.Haas; Phys.Rev.
Lett., 20, 1024 (1968))] (2) One that utilizes the White-Taylor type guest-host effect in the liquid crystal state [DL White and GN Taylor; , 45 , 4718
(1974) (DL White and GNTaylor; Z.
Appl.Phys., 45 , 4718 (1974)], (3) Those that utilize the ferroelectric effects of the chiral-smectic phase, H phase, F phase, I phase, and G phase in the liquid crystal state [NA Clark and ST Lagerwall; Applied Physics Letters. , 36 , 899 (1980) (NAClark and ST.
Lagerwall; Appl.Phys.Lett., 36, 899
[F.
J. Kahn, Applied Physics, Letters, 18 , 231 (1971) (FJKahn, Appl.Phys.
Lett., 18, 231 (1971)], used as a circularly polarized beam splitter using circular polarization characteristics [SD Jacobs, SPI,
37, 98 (1981) (SD Jacobs, SPIE, 37 , 98
(1981))] etc. are known. Although detailed explanations of individual methods will be omitted, they are important as display elements and modulation elements. In addition, by adding a very small amount to a nematic liquid crystal composition for twisted nematic (TN) type display elements, it can prevent the formation of striped patterns (reverse domains) on the display surface and increase the uniformity of the display. It can be used. Conventionally, optically active intermediates for synthesizing functional materials required for optical elements characterized by having optical activity include 2-methylbutanol, secondary octyl alcohol, secondary butyl alcohol, and p-(chloride). Known examples include 2-methylbutylbenzoic acid, secondary phenethyl alcohol, amino acid derivatives, synthetic derivatives, and cholesterol derivatives. However, these have the following drawbacks. It is difficult to change the structure of optically active chain hydrocarbon derivatives and, with the exception of some, they are very expensive. Amino acid derivatives are relatively inexpensive and their structures can be easily changed, but the hydrogen groups of amines are chemically active and easily cause hydrogen bonds and chemical reactions, which tends to limit the properties of functional materials. . It is difficult to change the structure of chemical derivatives and cholesterol derivatives, and they tend to adversely affect the properties of functional materials due to steric hindrance. The above-mentioned drawbacks have been a major constraint on the development of various materials. [Problems to be Solved by the Invention] The present invention has been made in view of the above points. That is, the present invention aims to provide a compound that can be bonded to a functional material intermediate having appropriate intermolecular force and shape without impairing optical activity, and allows for free molecular design. purpose. In the present invention, it is easy to change the length of the alkyl group, and this makes it possible to change the length of the alkyl group [H. Arnold, Journal of Physical Chemistry (H.
Arnold, J.Phys.Chem., 226, 146 (1964)], a liquid crystal compound capable of controlling the type and temperature range of the liquid crystal phase developed in a liquid state, and at least one type thereof. It is an object of the present invention to provide a liquid crystal composition containing the present invention as a compounding component. Furthermore, when producing a monomolecular cumulative film by the LB film method, the present invention aims to provide a compound whose hydrophobic groups can be easily controlled and which can be stably formed into a film. [Means and effects for solving the problems] The present invention is based on the general formula (): (In the above general formula, R represents a linear alkyl group having 1 to 18 carbon atoms. Also, * represents an asymmetric carbon atom.A
indicates a chemically active substituent. ) Derived from an optically active lactic acid derivative represented by the general formula () (In the above general formula, R represents a linear alkyl group having 1 to 18 carbon atoms. R' represents an alkyl group or alkoxy group having 4 to 18 carbon atoms. B is
【式】【formula】
【式】を表わす。）
で表わされる光学活性な液晶性の乳酸誘導体及び
それを少なくとも１種類配向成分として含有する
液晶組成物を提供する。
上記一般式中、Ｒは炭素数原子数１〜18の直鎖
状アルキル基であり、19以上では最終的な機能材
料としたときの粘度やモル体積が増加するため好
ましくない。また好ましいＲの炭素原子数は４〜
16である。又、＊は不斉炭素原子を示す。
ＡはOH基、ハロゲン原子、アルコキシ基、フ
エノキシ基トルエンスルホン酸基、チオール基等
の着脱可能な化学的に活性な置換基を示す。すな
わち、Ｒは、適当な反応条件下で、反応試薬と反
応して他の基によつて容易に置き換えることがで
きる。この場合反応試薬を種々変化させることに
より、液晶性化合物その他の機能性化合物を得る
ことができる。
光学素子・変調素子等の用途に適した機能性材
料を合成するためには、本発明により提供される
光学活性な乳酸誘導体と分子制御を行うことので
きる適度な分子間力と形状をもつた機能性材料中
間体とを光学活性を損うことなく結合することが
有効である。本発明の乳酸誘導体と組み合わせる
ことの有効な機能性材料中間体としては、アゾ
−、アゾキシ誘導体、環集合炭化水素誘導体、縮
合多環式炭化水素誘導体、複素環誘導体、縮合複
素環誘導体、環集合複素環誘導体等で具体的に
は、アゾベンゼン誘導体、アゾキシベンゼン誘導
体、ビフエニル誘導体、ターフエニル誘導体、フ
エニルシクロヘキサン誘導体、安息香酸誘導体、
ピリミジン誘導体、ピラジン誘導体、ピリジン誘
導体、スチルベン誘導体、トラン誘導体、カルコ
ン誘導体、ビシクロヘキサン誘導体、ケイ皮酸誘
導体等である。
次に、一般式（）で示される光学活性な乳酸
誘導体のうち、Ａが着脱可能な化学的に活性な置
換基である化合物の合成方法の例を示す。
上記反応式におけるRIは炭素数の広い範囲に
わたつて選択することが可能であり、具体的には
ヨードブタン、ヨードペンタン、ヨードヘキサ
ン、ヨードヘプタン、ヨードオクタン、ヨードノ
ナン、ヨードデカン、ヨードウンデカン、ヨード
デカン、ヨードトリデカン、ヨードテトラデカ
ン、ヨードペンタデカン、ヨードヘキサデカン、
ヨードヘプタデカン、ヨードオクタデカン、ヨー
ドノナデカン、ヨードエイコサン等の直鎖状飽和
炭化水素ヨウ化物；２−ヨードブタン、１−ヨー
ド−２−メチルプロパン、１−ヨード−３−メチ
ルブタン等の分岐状飽和炭化水素ヨウ化物；ヨー
ドベンジル、ヨードフエナシル、３−ヨード−１
−シクロヘキセン等の環状不飽和炭化水素ヨウ化
物；ヨードシクロペンタン、ヨードシクロヘキサ
ン、１−ヨード−３−メチルシクロヘキサン、ヨ
ードシクロヘプタン、ヨードシクロオクタン等の
環状飽和炭化水素ヨウ化物がある。
以上のようなヨウ化物から自由に選択すること
により光学活性な乳酸誘導体を得ることができ
る。
表１にこのようにして得られた光学活性な乳酸
誘導体の旋光度を示す。Represents [formula]. ) An optically active liquid crystal lactic acid derivative represented by the following formula and a liquid crystal composition containing at least one kind thereof as an alignment component are provided. In the above general formula, R is a linear alkyl group having 1 to 18 carbon atoms, and if it is 19 or more, it is not preferable because the viscosity and molar volume of the final functional material increase. The number of carbon atoms in R is preferably 4 to 4.
It is 16. Further, * indicates an asymmetric carbon atom. A represents a removable chemically active substituent such as an OH group, a halogen atom, an alkoxy group, a phenoxy group, a toluenesulfonic acid group, or a thiol group. That is, R can be easily replaced by another group by reacting with a reaction reagent under appropriate reaction conditions. In this case, liquid crystalline compounds and other functional compounds can be obtained by variously changing the reaction reagents. In order to synthesize functional materials suitable for applications such as optical elements and modulation elements, it is necessary to combine the optically active lactic acid derivative provided by the present invention with an appropriate intermolecular force and shape that allows for molecular control. It is effective to bond the functional material intermediate without impairing optical activity. Functional material intermediates that are effective in combination with the lactic acid derivatives of the present invention include azo, azoxy derivatives, ring assembled hydrocarbon derivatives, fused polycyclic hydrocarbon derivatives, heterocyclic derivatives, fused heterocyclic derivatives, ring assembled Specific examples of heterocyclic derivatives include azobenzene derivatives, azoxybenzene derivatives, biphenyl derivatives, terphenyl derivatives, phenylcyclohexane derivatives, benzoic acid derivatives,
These include pyrimidine derivatives, pyrazine derivatives, pyridine derivatives, stilbene derivatives, tolan derivatives, chalcone derivatives, bicyclohexane derivatives, and cinnamic acid derivatives. Next, an example of a method for synthesizing a compound in which A is a removable chemically active substituent among optically active lactic acid derivatives represented by the general formula () will be shown. RI in the above reaction formula can be selected from a wide range of carbon numbers, and specifically includes iodobutane, iodopentane, iodohexane, iodoheptane, iodooctane, iodononane, iododecane, iodoundecane, iododecane, and iododecane. tridecane, iodotetradecane, iodopentadecane, iodohexadecane,
Linear saturated hydrocarbon iodides such as iodoheptadecane, iodooctadecane, iodononadecane, iodoeicosane; branched saturated hydrocarbons such as 2-iodobutane, 1-iodo-2-methylpropane, 1-iodo-3-methylbutane, etc. Iodide; iodobenzyl, iodophenocil, 3-iodo-1
- Cyclic unsaturated hydrocarbon iodides such as cyclohexene; cyclic saturated hydrocarbon iodides such as iodocyclopentane, iodocyclohexane, 1-iodo-3-methylcyclohexane, iodocycloheptane, and iodocyclooctane. Optically active lactic acid derivatives can be obtained by freely selecting from the above iodides. Table 1 shows the optical rotation of the optically active lactic acid derivative thus obtained.
【表】【table】
【表】
このような方法により得られた種々の乳酸誘導
体より次に示す合成経路によつて下記一般式
（）〜（）に示される本発明の液晶性の乳酸
誘導体を得た。
［但し、上記一般式（）において、Ｒは炭素原
子数１〜18の直鎖状アルキル基を示し、R′は炭
素原子数４〜18のアルキル基またはアルコキシ基
を示す。］
表２に、このようにして得られた液晶性化合物
の相転移温度を示す。[Table] From the various lactic acid derivatives obtained by such methods, liquid crystalline lactic acid derivatives of the present invention represented by the following general formulas () to () were obtained by the following synthetic route. [However, in the above general formula (), R represents a linear alkyl group having 1 to 18 carbon atoms, and R' represents an alkyl group or an alkoxy group having 4 to 18 carbon atoms. ] Table 2 shows the phase transition temperature of the liquid crystalline compound thus obtained.
【表】
表中、相転移温度の欄における記号は、それぞ
れ以下の相を示す。
Cryst.：結晶相、SmA：スメクチツクＡ相、
SmC*：カイラルスメクチツクＣ相、Ｎ：ネマチ
ツク相、Ch：コレステリツク相、Iso：等方相、
Sm1、Sm2：SmA、SmC*以外のスメクチツク相
（未同定）。
［但し、上記一般式（）において、Ｒは炭素原
子数１〜18の直鎖状アルキル基を示し、R′は炭
素原子数４〜18のアルキル基またはアルコキシ基
を示す。］
本発明の液晶組成物は、
一般式（）
（上記一般式中Ｒは炭素数１〜18の直鎖状アルキ
ル基を示す。R′は炭素数４〜18のアルキル基も
しくはアルコキシル基を示す。Ｂは
[Table] In the table, the symbols in the phase transition temperature column indicate the following phases. Cryst.: Crystal phase, SmA: Smectic A phase,
SmC * : chiral smectic C phase, N: nematic phase, Ch: cholesteric phase, Iso: isotropic phase,
Sm1, Sm2: Smektic phases other than SmA and SmC * (unidentified). [However, in the above general formula (), R represents a linear alkyl group having 1 to 18 carbon atoms, and R' represents an alkyl group or an alkoxy group having 4 to 18 carbon atoms. ] The liquid crystal composition of the present invention has the general formula () (In the above general formula, R represents a linear alkyl group having 1 to 18 carbon atoms. R' represents an alkyl group or alkoxyl group having 4 to 18 carbon atoms. B is
【式】【formula】
【式】を表わす。）
で表わされる光学活性な液晶性の乳酸誘導体を少
なくとも１種類配合成分として含有するものであ
る。
本発明の乳酸誘導体を少なくとも１種類配合成
分として含有するネマチツク液晶はツイステツド
ネマチツク（TN）型セルにして使用する場合に
リバースドメインの発生を防止することができ好
ましい。
また本発明の乳酸誘導体の少なくとも１種類と
強誘電性液晶化合物とを含有する組成物は、強誘
電性液晶の性質の改良という観点から本発明にお
ける殊に好ましい態様をなすものである。この液
晶組成物において使用される強誘電性液晶化合物
の具体例を表２に掲げる。
また本発明の光学活性基を持つ液晶性化合物を
少なくとも１種類配合成分として含有する液晶組
成物に対して表３に示すようなコレステリツク液
晶化合物もしくは光学活性基を含む液晶性化合物
を添加することにより組成物のスメクチツク相も
しくはコレステリツク相におけるらせんピツチを
最適値に制御することは実用上好ましい。
一般式（）の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においては、一般
式（）の化合物を0.1〜99重量％含有するのが
好ましい。Represents [formula]. ) Contains at least one optically active liquid crystalline lactic acid derivative represented by the following formula as a compounding component. A nematic liquid crystal containing at least one lactic acid derivative of the present invention as a compounding ingredient is preferred because it can prevent the generation of reverse domains when used in a twisted nematic (TN) type cell. Further, a composition containing at least one lactic acid derivative of the present invention and a ferroelectric liquid crystal compound constitutes a particularly preferred embodiment of the present invention from the viewpoint of improving the properties of the ferroelectric liquid crystal. Table 2 lists specific examples of ferroelectric liquid crystal compounds used in this liquid crystal composition. Furthermore, by adding a cholesteric liquid crystal compound or a liquid crystal compound containing an optically active group as shown in Table 3 to a liquid crystal composition containing at least one liquid crystal compound having an optically active group according to the present invention as a compounding component. It is practically preferable to control the helical pitch in the smectic phase or cholesteric phase of the composition to an optimum value. In a liquid crystal composition containing at least one compound of general formula () as a compounding component, the content of the compound of general formula () is preferably from 0.1 to 99% by weight.
【表】【table】
【表】【table】
【表】
結晶 コレステリツク相 等方相
74.3℃ 81.0℃
SmC＊←[Table] Crystal Cholesteric phase Isotropic phase
74.3℃ 81.0℃
SmC ＊ ←
Claims (1)
ル基を示す。R′は炭素数４〜18のアルキル基も
しくはアルコキシ基を示す。Ｂは
【式】 【式】を表わす。） で表わされる光学活性な液晶性の乳酸誘導体。 ２ 一般式（） （上記一般式中Ｒは炭素数１〜18の直鎖状アルキ
ル基を示す。R′は炭素数４〜18のアルキル基も
しくはアルコキシル基を示す。Ｂは
【式】 【式】を表わす。） で表わされる光学活性な液晶性の乳酸誘導体を少
なくとも１種類配合成分として含有することを特
徴とする液晶組成物。[Claims] 1 General formula () (In the above general formula, R represents a linear alkyl group having 1 to 18 carbon atoms. R' represents an alkyl group or alkoxy group having 4 to 18 carbon atoms. B represents [formula] [formula].) An optically active liquid crystalline lactic acid derivative represented by 2 General formula () (In the above general formula, R represents a linear alkyl group having 1 to 18 carbon atoms. R' represents an alkyl group or alkoxyl group having 4 to 18 carbon atoms. B represents [formula] [formula].) A liquid crystal composition comprising at least one optically active liquid crystal lactic acid derivative represented by the following formula as a compounding component.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8619693A GB2181429B (en) | 1985-08-13 | 1986-08-13 | Lactic acid derivative and liquid crystal composition containing same |
| DE19863627443 DE3627443A1 (en) | 1985-08-13 | 1986-08-13 | AROMATIC CARBONIC ACID ESTERS AND AROMATIC AETHER DERIVATIVES, THIS CONTAINING LIQUID CRYSTAL MIXTURE AND LIQUID CRYSTAL DEVICE |
| US07/291,325 US4882085A (en) | 1985-08-13 | 1988-12-28 | Lactic acid derivative and liquid crystal composition containing same |
| US07/406,541 US5114613A (en) | 1985-08-13 | 1989-09-13 | Lactic acid derivative and liquid crystal composition containing same |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60-176938 | 1985-08-13 | ||
| JP17693885 | 1985-08-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62123141A JPS62123141A (en) | 1987-06-04 |
| JPH0533942B2 true JPH0533942B2 (en) | 1993-05-20 |
Family
ID=16022362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17392186A Granted JPS62123141A (en) | 1985-08-13 | 1986-07-25 | Lactic acid derivative and liquid crystal composition containing same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62123141A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62228036A (en) * | 1985-12-24 | 1987-10-06 | Ajinomoto Co Inc | Optical active compound |
| JP2562606B2 (en) * | 1986-09-08 | 1996-12-11 | ダイセル化学工業株式会社 | Optically active compound |
| JPH07107011B2 (en) * | 1987-02-05 | 1995-11-15 | チッソ株式会社 | Optically active-2-substituted propyl ethers and liquid crystal composition |
| WO1992020641A1 (en) * | 1991-05-20 | 1992-11-26 | Chisso Corporation | Optically active trifluorolactic acid derivative and liquid crystal composition |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50148523A (en) * | 1974-04-26 | 1975-11-28 | ||
| JPS5536496A (en) * | 1978-08-28 | 1980-03-14 | Ciba Geigy Ag | 11phenoxyy22alkynyloxyethane*its manufacture and noxious organism expellent containing it |
| JPS61112038A (en) * | 1984-11-07 | 1986-05-30 | Canon Inc | Lactic acid derivative and liquid crystal composition containing same |
| JPS61176544A (en) * | 1985-01-30 | 1986-08-08 | Fuji Photo Film Co Ltd | Aromatic ether |
-
1986
- 1986-07-25 JP JP17392186A patent/JPS62123141A/en active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50148523A (en) * | 1974-04-26 | 1975-11-28 | ||
| JPS5536496A (en) * | 1978-08-28 | 1980-03-14 | Ciba Geigy Ag | 11phenoxyy22alkynyloxyethane*its manufacture and noxious organism expellent containing it |
| JPS61112038A (en) * | 1984-11-07 | 1986-05-30 | Canon Inc | Lactic acid derivative and liquid crystal composition containing same |
| JPS61176544A (en) * | 1985-01-30 | 1986-08-08 | Fuji Photo Film Co Ltd | Aromatic ether |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62123141A (en) | 1987-06-04 |
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