JPS63137984A - Ferroelectric liquid crystal device - Google Patents
Ferroelectric liquid crystal deviceInfo
- Publication number
- JPS63137984A JPS63137984A JP61283463A JP28346386A JPS63137984A JP S63137984 A JPS63137984 A JP S63137984A JP 61283463 A JP61283463 A JP 61283463A JP 28346386 A JP28346386 A JP 28346386A JP S63137984 A JPS63137984 A JP S63137984A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- ferroelectric liquid
- tables
- formulas
- group
- 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.)
- Pending
Links
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 title claims abstract description 83
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 230000005621 ferroelectricity Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 1
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- 238000006467 substitution reaction Methods 0.000 abstract 2
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- 239000010409 thin film Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
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- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JTNNVZKEKJAWNR-UHFFFAOYSA-N 1-(trifluoromethoxy)butane Chemical group CCCCOC(F)(F)F JTNNVZKEKJAWNR-UHFFFAOYSA-N 0.000 description 1
- ZNPNIRDITDQGKG-UHFFFAOYSA-N 1-(trifluoromethoxy)propane Chemical compound CCCOC(F)(F)F ZNPNIRDITDQGKG-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
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
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- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- ALRHLSYJTWAHJZ-UHFFFAOYSA-N beta-hydroxy propionic acid Natural products OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- 229910000420 cerium oxide Inorganic materials 0.000 description 1
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- RHZWSUVWRRXEJF-UHFFFAOYSA-N indium tin Chemical compound [In].[Sn] RHZWSUVWRRXEJF-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
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- 229910052745 lead Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
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- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔技術分野〕
本発明は、表示素子や、液晶−光シヤツター等に利用さ
れる液晶素子、更に詳しくは、電界に対する応答特性が
改善された新規な強誘電性液晶組成物を使用する強誘電
性液晶素子に関するものである。Detailed Description of the Invention [Technical Field] The present invention relates to liquid crystal elements used in display elements, liquid crystal light shutters, etc., and more specifically, to novel ferroelectric liquid crystal compositions with improved response characteristics to electric fields. The present invention relates to a ferroelectric liquid crystal device using a ferroelectric liquid crystal device.
従来より、液晶は電気光学素子として種々の分野で応用
されている。現在実用化されている液晶素子はほとんど
が、例えばM、5chadtとW、He1frich著
“Applied Physics Letters”
Vo、18、No、4 (1971,,2,15)、P
、127〜128の“Voltage−Dpenden
t 0ptical Activity of
aT w i s t e d N e m a t
i c L i q u i d Cr y s t
a l″に示されたTN (twisted ne
matic)型の液晶を用いたものである。Conventionally, liquid crystals have been applied as electro-optical elements in various fields. Most of the liquid crystal elements currently in practical use are, for example, M, 5chadt and W, “Applied Physics Letters” by Helfrich.
Vo, 18, No. 4 (1971, 2, 15), P
, 127-128 “Voltage-Dpenden
t 0ptical Activity of
aT w i s t e d N e m a t
i c L i q u i d C ry s t
TN (twisted ne
matic) type liquid crystal.
これらは、液晶の誘電的配列効果に基づいており、液晶
分子の誘電異方性のために平均分子軸方向が、加えられ
た電場により特定の方向を向く効果を利用している。こ
れらの素子の光学的な応答速度の限界はミリ秒であると
いわれ、多(の応用のためには遅すぎる。These are based on the dielectric alignment effect of liquid crystals, and utilize the effect that the average molecular axis direction is oriented in a specific direction due to the dielectric anisotropy of liquid crystal molecules due to an applied electric field. The optical response speed of these devices is said to have a limit of milliseconds, which is too slow for many applications.
このような従来型の液晶素子の欠点を改善するものとし
て、双安定性を有する液晶素子の使用がC1arkおよ
びLagerwallにより提案されている(特開昭5
6−107216号公報、米国特許第4367924号
明細書等)。双安定性液晶としては、一般にカイラルス
メクテイツクC相(S m C”)又はH相(SmH”
)を有する強誘電性液晶が用いられる。この強誘電性液
晶は電界に対して第1の光学的安定状態と第2の光学的
安定状態からなる双安定状態を有し、従って前述のTN
型の液晶で用いられた光学変調素子とは異なり、例えば
一方の電界ベクトルに対して第1の光学的安定状態に液
晶が配向し、他方の電界ベクトルに対しては第2の光学
的安定状態に液晶が配向される。またこの型の液晶は、
加えられる電界に応答して、上記2つの安定状態のいず
れかを取り、且つ電界の印加のないときはその状態を維
持する性質(双安定性)を有する。To improve the drawbacks of conventional liquid crystal devices, the use of bistable liquid crystal devices has been proposed by C1ark and Lagerwall (Japanese Patent Application Laid-Open No.
6-107216, US Pat. No. 4,367,924, etc.). Bistable liquid crystals are generally chiral smectic C phase (SmC") or H phase (SmH").
) is used. This ferroelectric liquid crystal has a bistable state consisting of a first optically stable state and a second optically stable state with respect to an electric field, and thus has a bistable state consisting of a first optically stable state and a second optically stable state.
Unlike the optical modulation elements used in type liquid crystals, for example, the liquid crystal is oriented in a first optically stable state for one electric field vector and in a second optically stable state for the other electric field vector. The liquid crystal is aligned. In addition, this type of liquid crystal
It has a property (bistability) of taking one of the above two stable states in response to an applied electric field and maintaining that state when no electric field is applied.
以上のような双安定性を有する特徴に加えて、強誘電液
晶は高速応答性であるという優れた特徴を持つ。それは
強誘電液晶の持つ自発分極と印加電場が直接作用して配
向状態の転移を誘起するためであり、誘電率異方性と電
場の作用による応答速度より3〜4オーダー速い。In addition to the above-mentioned feature of bistability, ferroelectric liquid crystals have the excellent feature of high-speed response. This is because the spontaneous polarization of the ferroelectric liquid crystal and the applied electric field directly act to induce a transition in the orientation state, which is 3 to 4 orders of magnitude faster than the response speed due to the effect of the dielectric anisotropy and the electric field.
このように強誘電性液晶はきわめて優れた特性を潜在的
に有しており、このような性質を利用することにより、
上述した従来のTN型素子の問題点の多くに対して、か
なり本質的な改善が得られる。In this way, ferroelectric liquid crystals potentially have extremely excellent properties, and by utilizing these properties,
Significant substantial improvements are obtained over many of the problems of conventional TN type devices mentioned above.
特に高速光学光シャッターや、高密度、大画面ディスプ
レイへの応用が期待される。In particular, it is expected to be applied to high-speed optical shutters and high-density, large-screen displays.
このため、強誘電性液晶素子に用いる強誘電性を持つ液
晶材料に関しても広(研究がなされているが、現在まで
報告されている強誘電性液晶素子で■低温作動の温度範
囲を広げ、■低温での高速応答性を増すことを満足する
ものはほとんど無い。For this reason, extensive research has been conducted on liquid crystal materials with ferroelectric properties used in ferroelectric liquid crystal devices, but the ferroelectric liquid crystal devices reported to date have been able to: ■ widen the temperature range of low-temperature operation; There is hardly anything that satisfies the need to increase high-speed response at low temperatures.
本発明の目的は前述の欠点又は不利を解消した強誘電性
液晶素子を提供することにある。SUMMARY OF THE INVENTION It is an object of the present invention to provide a ferroelectric liquid crystal element which eliminates the above-mentioned drawbacks or disadvantages.
また、本発明の別の目的は新規な強誘電性液晶組成物を
提供することにある。又、更に本発明の別の目的は双安
定なモノドメイン性を示す良好な配向状態を有する強誘
電性液晶素子を提供することにある。Another object of the present invention is to provide a novel ferroelectric liquid crystal composition. Still another object of the present invention is to provide a ferroelectric liquid crystal element that exhibits bistable monodomain properties and has a good alignment state.
強誘電性液晶素子に使用される強誘電性液晶組成物は本
発明者らの研究によれば下記一般式(I)で表される液
晶化合物を混合することにより、それを添加していない
場合に比ベスメクチツクC相を与える温度領域が特に低
温側において広がり且つ、応答速度が向上し、表示特性
が改善されることが見出されたのである。According to research by the present inventors, a ferroelectric liquid crystal composition used in a ferroelectric liquid crystal element can be prepared by mixing a liquid crystal compound represented by the following general formula (I); It has been found that the temperature range that gives a vesmectic C phase is expanded, especially on the low temperature side, and that the response speed is improved and the display characteristics are improved.
以下本発明を更に詳細に説明する。以下の記載において
量比を表す「%」および「部」はいずれも重量基準とす
る。The present invention will be explained in more detail below. In the following description, both "%" and "part" expressing quantitative ratio are based on weight.
Rl−A 、−X 、−0−A2−X2−C−R2・・
・・・・・(I)(式中、R8は置換基を有していても
良い分岐または直鎖の鎖状基を示す。Rl-A, -X, -0-A2-X2-C-R2...
...(I) (wherein R8 represents a branched or straight chain group which may have a substituent.
好ましくは、R1は置換基を有しても良い、メチル、エ
チル、プロピル、ブチル、ペンチル、ヘキシル、イソプ
ロピル等のアルキル基、メトキシ、エトキシ、プロピル
オキシ、ブトキシ、2−メチルブトキシ基等のアルコキ
シ基、アセチル、プロピオニル、ブチニル、バレリル、
バルミトイル、2−メチルプロピオニル等のアシル基、
アセチルオキシ、プロピオニルオキシ、ブチニルオキシ
、2−メチルプロピルオキシ等のアシルオキシ基、メト
キシカルボニル、エトキシカルボニル、ブトキシカルボ
ニル、2−メチルブトキシカルボニル等のアルコキシカ
ルボニル基、及びメトキシカルボニルオキシ、エトキシ
カルボニルオキシ、ブトキシカルボニルオキシ、2−メ
チルブトキシカルボニルオキシ等アルコキシカルボニル
オキシ基から選ばれ、R2は置換基を有しても良い、メ
チル、エチル、プロピル、ブチル、ペンチル、ヘキシル
、イソプロピル等のアルキル基及びメトキシ、エトキシ
、プロピルオキシ、ブトキシ、2−メチルブトキシ等の
アルコキシ基から選ばれる。Preferably, R1 is an alkyl group such as methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, etc., or an alkoxy group such as methoxy, ethoxy, propyloxy, butoxy, 2-methylbutoxy group, which may have a substituent. , acetyl, propionyl, butynyl, valeryl,
Acyl groups such as valmitoyl and 2-methylpropionyl,
Acyloxy groups such as acetyloxy, propionyloxy, butynyloxy, 2-methylpropyloxy, alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, butoxycarbonyl, 2-methylbutoxycarbonyl, and methoxycarbonyloxy, ethoxycarbonyloxy, butoxycarbonyloxy , 2-methylbutoxycarbonyloxy, etc., and R2 is an alkyl group such as methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, which may have a substituent, and methoxy, ethoxy, propyl. It is selected from alkoxy groups such as oxy, butoxy, and 2-methylbutoxy.
さらに好ましくは、R1及びR2の少なくともいずれか
一方は不斉炭素を持つ置換基を有していても良い分岐ま
たは直鎖アルキル基を有する鎖状基を示す。更にR1及
びR2の示す置換基としては、フッ素、塩素、臭素等の
ハロゲン原子、メトキシ、エトキシ、プロピルオキシ、
ブトキシ等のアルコキシ基、トリフルオロメタン又はシ
アノ基等が挙げられる。More preferably, at least one of R1 and R2 represents a chain group having a branched or straight chain alkyl group which may have a substituent having an asymmetric carbon. Further, substituents represented by R1 and R2 include halogen atoms such as fluorine, chlorine, and bromine, methoxy, ethoxy, propyloxy,
Examples include alkoxy groups such as butoxy, trifluoromethane, and cyano groups.
A1及びA2は置換基を有していても良い、六員環を有
する2価の基を示す。A、及びA2の示す六員環を有す
る基の好ましい具体例は下記一般式%式%
(式中、A3及びA4は置換基を有していても良い(つ
。A1 and A2 represent a divalent group having a six-membered ring which may have a substituent. Preferred specific examples of the group having a six-membered ring represented by A and A2 are represented by the following general formula % (wherein A3 and A4 may have a substituent).
より選択するのが好ましく、m、nは0. 1または2
であり、かつm 十n = 1または2で示される。It is preferable to select m and n from 0. 1 or 2
and is represented by m tenn = 1 or 2.
又、更にA3及びA4の示す置換基としては、フッ素、
塩素、臭素等のハロゲン原子、メチル、エチル、プロピ
ル、ブチル等のアルキル基、メトキシ、エトキシ、プロ
ポキシ等のアルコキシ基、トリフルオロメタン又はシア
ノ基等が挙げられる。)Xl及びx2は2価の鎖状基で
あり、好ましくは一0CH2C−から選ばれ、X2が−
CH=CH−、、]1
−CH2CH2−及び−CH2−から選ばれることが望
ましい。Furthermore, the substituents represented by A3 and A4 include fluorine,
Examples include halogen atoms such as chlorine and bromine, alkyl groups such as methyl, ethyl, propyl, and butyl, alkoxy groups such as methoxy, ethoxy, and propoxy, trifluoromethane, and cyano groups. ) Xl and x2 are divalent chain groups, preferably selected from 10CH2C-, and X2 is -
CH=CH-, ]1 -CH2CH2- and -CH2- are preferable.
以下に、一般式(I)で示す化合物についての代例示化
合物No。Below, typical exemplified compound No. of the compound represented by general formula (I) is shown.
CT4ワ
Oす
次に本発明で用いる化合物の代表的な合成例を下記に示
す。Next, typical synthesis examples of the compounds used in the present invention are shown below.
〔合成例1)P−プロピルベンジルオキシ−P’ −(
2−エトキシプロピルオキシカルボニルビニレン)ビフ
ェニル(化合物例(16))の合成P−ヒドロキシ−(
2−エトキシプロピルオキシカルボニルビニレン)ビフ
ェニル0.99gをテトラヒドロフラン5mlに溶解さ
せた所へ水素化ナトリウム0.08gテトラヒドロフラ
ン3mj2と共に加え撹拌した。次いで、P−プロピル
ベンジルアルコール0.45gをテトラヒドロフラン3
mlに溶解させたものを反応溶液中に加え、撹拌しなが
ら、2時間加熱還流させた後にさらに室温で6時間反応
させた。[Synthesis Example 1) P-propylbenzyloxy-P'-(
Synthesis of 2-ethoxypropyloxycarbonylvinylene)biphenyl (compound example (16)) P-hydroxy-(
To a solution of 0.99 g of 2-ethoxypropyloxycarbonylvinylene)biphenyl dissolved in 5 ml of tetrahydrofuran, 0.08 g of sodium hydride and 3 mj2 of tetrahydrofuran were added and stirred. Next, 0.45 g of P-propylbenzyl alcohol was added to 3 g of tetrahydrofuran.
ml was added to the reaction solution, heated under reflux for 2 hours while stirring, and then reacted at room temperature for 6 hours.
次に反応混合物を水に注入した後酢酸で中和し、イソプ
ロピルエーテルで抽出した。得られた有機層を硫酸ナト
リウムで乾燥後、溶媒を留去しシリカゲルカラムクロマ
トグラフィーで精製した。(移動層、5%メタノール/
クロロホルム)収量 0.83g〔合成例2’IP−オ
クトキシ安息香酸P’ −(2−エトキシプロピル)オ
キシカルボニルフェネチルエステル(化合物例(1))
の合成
3−ヒドロキシプロピオン酸2−エトキシプロピルエス
テル1.0gにピリジン3.2mI!を加え氷冷した後
、P−オクチルオキシカルボン酸塩化物1.0gを6m
jl!のトルエン溶液としたものを滴下して加え20℃
以下で3時間撹拌した後、室温で20時間撹拌した。反
応終了後、反応混合物を水に注入し、lNHClで酸性
にした後、酢酸エチルで抽出を行った。得られた有機層
はさらに水で洗浄し、硫酸ナトリウムで乾燥後溶媒を留
去し、シリカゲルカラムクロマトグラフィー(移動層、
ヘキサン;酢酸エチル=3 : 1)で精製した。収量
1.2g以上、代表的な化合物の合成法について述べた
が、一般式(I)で示される他の化合物も同様にして合
成された。The reaction mixture was then poured into water, neutralized with acetic acid, and extracted with isopropyl ether. The obtained organic layer was dried over sodium sulfate, the solvent was distilled off, and the layer was purified by silica gel column chromatography. (Mobile phase, 5% methanol/
Chloroform) Yield: 0.83 g [Synthesis Example 2'IP-octoxybenzoic acid P'-(2-ethoxypropyl)oxycarbonylphenethyl ester (Compound Example (1))
Synthesis of 3.2 mI of pyridine to 1.0 g of 3-hydroxypropionic acid 2-ethoxypropyl ester! After adding and cooling on ice, 1.0 g of P-octyloxycarboxylic acid chloride was added to 6 m
jl! Add dropwise a toluene solution of
After stirring for 3 hours below, the mixture was stirred at room temperature for 20 hours. After the reaction was completed, the reaction mixture was poured into water, acidified with 1N HCl, and extracted with ethyl acetate. The obtained organic layer was further washed with water, dried over sodium sulfate, the solvent was distilled off, and subjected to silica gel column chromatography (mobile phase,
Purification was performed using hexane: ethyl acetate = 3:1). Although the method for synthesizing a typical compound with a yield of 1.2 g or more has been described, other compounds represented by the general formula (I) were also synthesized in the same manner.
前記一般式(I)で表される化合物において、−X3ニ
ーCH−CH−2−CH2CH2−9−CH2−9−O
CH2−、単結合
P :0または1
とするとこの・化合物は以下のようにして合成される。In the compound represented by the general formula (I), -X3niCH-CH-2-CH2CH2-9-CH2-9-O
CH2-, single bond P: 0 or 1, this compound is synthesized as follows.
p=oのとき(例:合成例1)
R、−A 、−X 、−1+ HO−A2−x2−c−
R2P=1のとき(例:合成例2)
R,−A、−X、−CI!+HO−A2−X2−C−R
2ここで使用している記号は前項で定義した通りである
。When p=o (Example: Synthesis Example 1) R, -A, -X, -1+ HO-A2-x2-c-
When R2P=1 (Example: Synthesis Example 2) R, -A, -X, -CI! +HO-A2-X2-C-R
2 The symbols used here are as defined in the previous section.
本発明の液晶素子は、上記のように得られた一般式(I
)で与えられる化合物を少なくとも1種類、配合成分と
して含有する液晶組成物を用いたものである。The liquid crystal element of the present invention has the general formula (I
) is used as a liquid crystal composition containing at least one compound as a compounding component.
また、本発明による強誘電性液晶素子は前記液晶組成物
を真空中、等方性液体温度まで加熱し、素子セル中に封
入し、除々に冷却し液晶相を形成させ常圧に戻すことに
より得るのが望ましい。Further, the ferroelectric liquid crystal element according to the present invention can be produced by heating the liquid crystal composition in vacuum to an isotropic liquid temperature, sealing it in an element cell, gradually cooling it to form a liquid crystal phase, and returning it to normal pressure. It is desirable to obtain.
本発明に用いる他の強誘電性液晶化合物とじて[亘]
本発明の化合物と本発明の化合物以外の1種以上の上述
強誘電性液晶化合物(以下強誘電性液晶材料と略す)と
の配合割合は、強誘電性液晶材料100重量部当たり本
発明の化合物を1〜500重量部とすることが好ましい
。また、本発明の化合物を2種以上用いる場合も、強誘
電性液晶材料との配合割合は前述した強誘電性液晶材料
100重量部当たり本発明の化合物の2種以上の混合物
を1〜500重量部とすることが好ましい。Other ferroelectric liquid crystal compounds used in the present invention [Wataru] Combination of the compound of the present invention and one or more of the above-mentioned ferroelectric liquid crystal compounds other than the compound of the present invention (hereinafter abbreviated as ferroelectric liquid crystal material) The ratio is preferably 1 to 500 parts by weight of the compound of the present invention per 100 parts by weight of the ferroelectric liquid crystal material. Also, when using two or more compounds of the present invention, the blending ratio with the ferroelectric liquid crystal material is 1 to 500 parts by weight of the mixture of two or more compounds of the present invention per 100 parts by weight of the above-mentioned ferroelectric liquid crystal material. It is preferable to set it as part.
第1図は強誘電性液晶素子の構成の説明のために、本発
明の強誘電性液晶層を有する液晶表示素子の1例の断面
概略図である。FIG. 1 is a schematic cross-sectional view of an example of a liquid crystal display element having a ferroelectric liquid crystal layer according to the present invention, for explaining the structure of the ferroelectric liquid crystal element.
第1図において付号lは強誘電性液晶層、2はガラス基
板、3は透明電極、4は絶縁性配向制御膜、5はスペー
サー、6はリード線、7は電源、8は偏光板、9は光源
を示している。In FIG. 1, the number l is a ferroelectric liquid crystal layer, 2 is a glass substrate, 3 is a transparent electrode, 4 is an insulating alignment control film, 5 is a spacer, 6 is a lead wire, 7 is a power source, 8 is a polarizing plate, 9 indicates a light source.
2枚のガラス基板2には、それぞれIn203 、 5
n02あるいはITO(Indium−Tin 0x
ide)等の薄膜から成る透明電極が被覆されている。The two glass substrates 2 have In203 and In205, respectively.
n02 or ITO (Indium-Tin 0x
A transparent electrode made of a thin film such as IDE) is coated.
その上にポリイミドの様な高分子の薄膜をガーゼやアセ
テート植毛布等でラビングして、液晶をラビング方向に
並べる絶縁性配向制御層が形成されている。また絶縁物
質として例えばシリコン窒化物、水素を含有するシリコ
ン炭化物、シリコン酸化物、硼素窒化物、水素を含有す
る硼素窒化物、セリウム酸化物、アルミニウム酸化物、
ジルコニウム酸化物、チタン酸化物やフッ化マグネシウ
ムなどの無機物質絶縁層を形成し、その上にポリビニル
アルコール、ポリイミド、ポリアミドイミド、ポリエス
テルイミド、ポリパラキシレン、ポリエステル、ポリカ
ーボネート、ポリビニルアセクール、ポリ塩化ビニル、
ポリ酢酸ビニル、ポリアミド、ポリスチレン、セルロー
ス樹脂、メラミン樹脂、ユリャ樹脂、アクリル樹脂やフ
ォトレジスト樹脂などの有機絶縁物質を配向制御膜とし
て、2層で絶縁性配向制御層が形成されていてもよく、
また無機物質絶縁性配向制御層あるいは有機物質絶縁性
配向制御層単層であっても良い。この絶縁性配向制御層
が無機系ならば蒸着法などで形成でき、有機系ならば有
機絶縁物質を溶解させた溶液、またはその前駆体溶液(
溶剤に0.1〜20重量%、好ましくは0.2〜10重
量%)を用いて、スピンナー塗布法、浸漬塗布法、スク
リーン印刷法、スピジー塗布法、ロール塗布法等で塗布
し、所定の硬化条件下(例えば加熱)下で硬化させ形成
させることができる。On top of this, a thin film of a polymer such as polyimide is rubbed with gauze or acetate flocked cloth to form an insulating alignment control layer that aligns the liquid crystals in the rubbing direction. Examples of insulating materials include silicon nitride, hydrogen-containing silicon carbide, silicon oxide, boron nitride, hydrogen-containing boron nitride, cerium oxide, aluminum oxide,
Form an inorganic insulating layer of zirconium oxide, titanium oxide, magnesium fluoride, etc., and then apply polyvinyl alcohol, polyimide, polyamideimide, polyesterimide, polyparaxylene, polyester, polycarbonate, polyvinyl acecool, polyvinyl chloride. ,
The insulating alignment control layer may be formed of two layers using an organic insulating material such as polyvinyl acetate, polyamide, polystyrene, cellulose resin, melamine resin, Yulia resin, acrylic resin, or photoresist resin as the alignment control film,
Alternatively, it may be a single layer of an insulating orientation control layer made of an inorganic material or an insulating orientation control layer of an organic material. If this insulating orientation control layer is inorganic, it can be formed by a vapor deposition method, or if it is organic, it can be formed using a solution containing an organic insulating material or its precursor solution (
0.1 to 20% by weight, preferably 0.2 to 10% by weight) in a solvent, and applied by spinner coating method, dip coating method, screen printing method, swige coating method, roll coating method, etc. It can be cured and formed under curing conditions (eg, heating).
絶縁性配向層の層の厚みは通常50人〜1μ、好ましく
は100人〜5000人さらに好ましくは500人〜3
000人が適している。The thickness of the insulating alignment layer is usually 50 to 1μ, preferably 100 to 5,000, more preferably 500 to 3
000 people is suitable.
この2枚のガラス基板2はスペーサー5によって任意の
間か(に保たれている。例えば所定の直径を持つシリカ
ビーズ、アルミナビーズをスペーサーとしてガラス基板
2枚で挟持し、周囲をシール材、例えばエポキシ系接着
材を用いて密封する方法がある。その他スペーサーとし
て高分子フィルムやガラスファイバーを使用しても良い
。その間に強誘電性液晶が封入されている。These two glass substrates 2 are kept at an arbitrary distance by a spacer 5. For example, silica beads or alumina beads having a predetermined diameter are used as spacers to sandwich the two glass substrates, and the periphery is covered with a sealing material, for example. There is a method of sealing using an epoxy adhesive.Also, a polymer film or glass fiber may be used as a spacer.The ferroelectric liquid crystal is sealed between them.
強誘電性液晶が封入される素子セル厚は、一般に0.5
μ〜20μ、好ましくは1μ〜5μである。The device cell thickness in which the ferroelectric liquid crystal is sealed is generally 0.5
μ to 20 μ, preferably 1 μ to 5 μ.
透明電極3からはリード線によって外部電源7に接続さ
れている。またガラス基板2の外側には偏光板8が貼り
合わせである。The transparent electrode 3 is connected to an external power source 7 by a lead wire. Further, a polarizing plate 8 is bonded to the outside of the glass substrate 2.
第1図は透過型なので光源9を備えている。The device shown in FIG. 1 is of a transmission type, so it is equipped with a light source 9.
第2図は、強誘電性液晶素子の動作説明のために、セル
の例を模式的に描いたものである。21aと21bはそ
れぞれIn203,5n02あるいはITO(Indi
um−Tin 0xide)等の薄膜からなる透明電
極で被覆された基板(ガラス板)であり、その間に液晶
分子層22がガラス面に垂直になるよう配向したSmC
*相又はSmH*相の液晶が封入されている。太線で示
した線23が液晶分子を表わしており、この液晶分子2
3はその分子に直交した方向に双極子モーメント(P土
)24を有している。基板21aと21b上の電極間に
一定の閾値以上の電圧を印加すると、液晶分子23のら
せん構造がほどけ、双極子モーメント(P±)24がす
べて電界方向に向(よう、液晶分子23は配向方向を変
えることができる。液晶分子23は、細長い形状を有し
ており、その長袖方向と短軸方向で屈折率異方性を示し
、従って例えばガラス面の上下に互いにクロスニコルの
偏光子を置けば、電圧印加極性によって光学特性が変わ
る液晶光学変調素子となることは、容易に理解される。FIG. 2 schematically depicts an example of a cell for explaining the operation of a ferroelectric liquid crystal element. 21a and 21b are In203, 5n02 or ITO (Indi
A substrate (glass plate) coated with a transparent electrode made of a thin film such as um-Tin oxide), between which a liquid crystal molecular layer 22 is oriented perpendicular to the glass surface.
*phase or SmH* phase liquid crystal is enclosed. A thick line 23 represents a liquid crystal molecule, and this liquid crystal molecule 2
3 has a dipole moment (P soil) 24 in the direction perpendicular to its molecule. When a voltage higher than a certain threshold is applied between the electrodes on the substrates 21a and 21b, the helical structure of the liquid crystal molecules 23 is unraveled, and the dipole moments (P±) 24 are all directed in the direction of the electric field. The direction can be changed.The liquid crystal molecules 23 have an elongated shape and exhibit refractive index anisotropy in the long axis direction and the short axis direction. It is easily understood that if the device is placed in the same position, it becomes a liquid crystal optical modulation element whose optical characteristics change depending on the polarity of applied voltage.
本発明の光学変調素子で好ましく用いられる液晶セルは
、その厚さを充分に薄く(例えば10μ以下)すること
ができる。このように液晶層が薄くなるにしたがい、第
3図に示すように電界を印加していない状態でも液晶分
子のらせん構造がほどけ、その双極子モーメントPaま
たはPbは上向き(34a)又は下向き(34b)のど
ちらかの状態をとる。このようなセルに、第3図に示す
如く一定の閾値以上の極性の異る電界Ea又はEbを電
圧印加手段31aと31bにより付与すると、双極子モ
ーメントは電界Ea又はEbの電界ベクトルに対応して
上向き34a又は下向き34bと向きを変え、それに応
じて液晶分子は、第1の安定状態33aかあるいは第2
の安定状態33bの何れか1方に配向する。The liquid crystal cell preferably used in the optical modulation element of the present invention can have a sufficiently thin thickness (for example, 10 μm or less). As the liquid crystal layer becomes thinner, the helical structure of the liquid crystal molecules unravels even when no electric field is applied, as shown in Figure 3, and the dipole moment Pa or Pb is directed upward (34a) or downward (34b). ). When an electric field Ea or Eb of different polarity above a certain threshold value is applied to such a cell by the voltage applying means 31a and 31b as shown in FIG. 3, the dipole moment corresponds to the electric field vector of the electric field Ea or Eb. The liquid crystal molecules change direction upward 34a or downward 34b, and accordingly the liquid crystal molecules are in the first stable state 33a or in the second stable state 33a.
is oriented in one of the stable states 33b.
このような強誘電性を光学変調素子として用いることの
利点は、先にも述べたが2つある。As mentioned earlier, there are two advantages to using such ferroelectricity as an optical modulation element.
その第1は、応答速度が極めて速いことであり、第2は
液晶分子の配向が双安定性を有することである。第2の
点を例えば第2図によって更に説明すると、電界Eaを
印加すると液晶分子は第1の安定状態33aに配向する
が、この状態は電界を切っても安定である。又、逆向き
の電界Ebを印加すると、液晶分子は第2の安定状態2
3bに配向してその分子の向きを変えるが、やはり電界
を切ってもこの状態に留っている。又、与える電界Ea
あるいはEbが一定の閾値を越えない限り、それぞれ前
の配向状態にやはり維持されている。The first is that the response speed is extremely fast, and the second is that the alignment of liquid crystal molecules has bistability. To further explain the second point with reference to FIG. 2, for example, when the electric field Ea is applied, the liquid crystal molecules are oriented in a first stable state 33a, and this state remains stable even when the electric field is turned off. Moreover, when an electric field Eb in the opposite direction is applied, the liquid crystal molecules enter the second stable state 2.
3b and changes the orientation of the molecule, but it remains in this state even after the electric field is turned off. Also, the applied electric field Ea
Alternatively, each previous orientation state is still maintained as long as Eb does not exceed a certain threshold.
以下実施例により本発明の化合物について更に詳細に説
明するが、本発明はこれらの実施例に限定されるもので
はない。The compounds of the present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to these Examples.
実施例1
2枚の0.7m厚のガラス板を用意し、それぞれのガラ
ス板上にITO膜を形成し、電圧印加電極を作成した。Example 1 Two 0.7 m thick glass plates were prepared, and an ITO film was formed on each glass plate to create a voltage application electrode.
さらにこの上にSiO2を蒸着させ絶縁層とした。Furthermore, SiO2 was deposited on top of this to form an insulating layer.
ガラス板上にシランカップリン剤〔信越化学■製KBM
−602:I O,2%イソプロピルアルコール溶液を
回転数200Or、p、mのスピードで15秒間塗布し
表面処理を施した。この後120℃にて20分間加熱乾
燥処理を施した。Silane coupling agent [KBM manufactured by Shin-Etsu Chemical Co., Ltd.] on the glass plate
-602: A 2% isopropyl alcohol solution of IO was applied for 15 seconds at a rotational speed of 200 Orr, p, m for surface treatment. Thereafter, a heat drying treatment was performed at 120° C. for 20 minutes.
さらに表面処理を行ったITO膜付きのガラス板上にポ
リイミド樹脂前駆体〔東しくIteSP−510) 2
%ジメチルアセトアミド溶液を回転数2000r、p、
mのスピンナーで15秒間塗布した。成膜後、60分間
300℃加加熱台焼成処理を施した。この時の塗膜の膜
厚は約700人であった。Furthermore, a polyimide resin precursor (Toshiku IteSP-510) was placed on a glass plate with an ITO film that had been surface-treated.
% dimethylacetamide solution at rotation speed 2000 r, p,
It was applied for 15 seconds using a spinner. After the film was formed, a heating table baking treatment was performed at 300° C. for 60 minutes. The thickness of the coating film at this time was about 700.
この焼成後の被膜にはアセテート植毛布によるラビング
処理がなされ、その後イソプロピルアルコール液で洗浄
し、平均粒径2μmのアルミナビーズを一方のガラス板
上に散布した後、それぞれのラビング処理軸が互いに平
行となる様にし、接着シール剤〔リクソンボンド(チッ
ソ■)〕を用いてガラス板をはり合わせ、60分間10
0℃にて加熱乾燥しセルを作成した。このセルのセル厚
をベレツク位相板によって測定したところ、約2μmで
あった。This fired coating is rubbed with acetate flocked cloth, then washed with isopropyl alcohol, and alumina beads with an average particle size of 2 μm are sprinkled on one glass plate, so that the rubbing axes are parallel to each other. Then, glue the glass plates together using an adhesive sealant [Rixon Bond (Chisso)], and leave them together for 60 minutes.
A cell was prepared by heating and drying at 0°C. The cell thickness of this cell was measured using a Bereck phase plate and was found to be approximately 2 μm.
次に前記例示化合物Nα1と下記構造式で示される強誘
電性液晶化合物を下記の重量部で混合し、重量部
例示化合物No、 1
5(以下 *印は不斉炭素を示す)
等吉相下、均一混合液体状態で前述の方法で作製したセ
ル内に真空注入した。等吉相から0.5°C/hで30
℃まで徐冷することにより、強誘電性液晶素子を作成し
た。Next, the exemplified compound Nα1 and the ferroelectric liquid crystal compound represented by the following structural formula were mixed in the following parts by weight, and the exemplified compound Nos. 1 and 1 were mixed in the following parts by weight.
5 (hereinafter, the mark * indicates an asymmetric carbon) Under the Tokichi phase, a uniformly mixed liquid state was vacuum injected into the cell prepared by the method described above. 30 at 0.5°C/h from Tokichi phase
A ferroelectric liquid crystal device was created by slowly cooling it to ℃.
この強誘電性液晶素子を使ってピーク・トウ・ピーク電
圧20Vの電圧印加により直交ニコル下での光学的な応
答を電圧印加時から透過光量変化が90%変化するまで
の間を検知して応答速度(以後光学応答速度という)を
測定した。その結果を次に示す。Using this ferroelectric liquid crystal element, by applying a peak-to-peak voltage of 20V, the optical response under crossed Nicols is detected and responded from the time the voltage is applied until the amount of transmitted light changes by 90%. The speed (hereinafter referred to as optical response speed) was measured. The results are shown below.
20°C30°C’ 40°C370μ5ec
340μ5eC295μSeC比較例1
実施例1で使用した例示化合物N001を強誘電性液晶
層に含有させなかった以外は全〈実施例1と同様の方法
で強誘電性液晶素子を作成し、光学応答速度を測定した
。その結果を次に示す。20°C30°C' 40°C370μ5ec
340μ5eC295μSeC Comparative Example 1 A ferroelectric liquid crystal element was created in the same manner as in Example 1, except that the exemplified compound N001 used in Example 1 was not included in the ferroelectric liquid crystal layer, and the optical response speed was measured. did. The results are shown below.
208C30°0 40℃
420μ5eC380μ5eC325μSeC実施例2
実施例1で使用した強誘電性液晶化合物lに代えて、下
記構造式で示す強誘電性液晶化合物を各重量部で用いた
ほかは、実施例1と同様の方法で強誘電性液晶素子を作
成し、実施例1と同様の方法で光重置部
25°0 35°0 50℃600μ
SeC450μSeC200μSeC比較例2
実施例2で使用した例示化合物No、1を強誘電性液晶
層に含有させなかった他は実施例2と同様の方法で強誘
電性液晶素子を作成し、実施例1と同様の方法で光学応
答速度を測定した。その結果を夕暮こ示す。208C30°0 40°C 420μ5eC380μ5eC325μSeC Example 2 Same as Example 1 except that in place of the ferroelectric liquid crystal compound l used in Example 1, a ferroelectric liquid crystal compound represented by the following structural formula was used in each part by weight. A ferroelectric liquid crystal element was prepared by the method described in the following, and the light superimposition portion was heated at 25°0 35°0 50°C600μ in the same manner as in Example 1.
SeC450μSeC200μSeC Comparative Example 2 A ferroelectric liquid crystal element was prepared in the same manner as in Example 2, except that the exemplified compound No. 1 used in Example 2 was not included in the ferroelectric liquid crystal layer, and the same method as in Example 1 was made. The optical response speed was measured using the method described above. I'll show you the results at dusk.
20°025°G 3580 50℃ 60
’C80”C1100μsec 730 μsec
510μsec 230μsec 170 p
sec 100μsec実施例3
実施例1で使用した強誘電性液晶化合物に代えて、下記
構造式で示す、強誘電性液晶化合物を各重量部で用いた
ほかは、実施例1と同様の方法で強誘電性液晶素子を作
成し、実施例1と同様の方法で光学応答速度を測定した
。その結果を次に示す。20°025°G 3580 50℃ 60
'C80''C1100μsec 730μsec
510μsec 230μsec 170p
sec 100 μsec Example 3 In place of the ferroelectric liquid crystal compound used in Example 1, a ferroelectric liquid crystal compound represented by the following structural formula was used in each part by weight. A dielectric liquid crystal element was prepared, and the optical response speed was measured in the same manner as in Example 1. The results are shown below.
25°C; 3200μsec 35°C; 260
0μsec 45°C; 1600 μsec比較例
3
実施例3で使用した例示化合物No、1を強誘電性液晶
層に含有させなかった他は実施例3と同様の方法で強誘
電性液晶素子を作成し、実施例1と同様の方法で光学応
答速度を測定した。その結果を次に示す。25°C; 3200μsec 35°C; 260
0 μsec 45°C; 1600 μsec Comparative Example 3 A ferroelectric liquid crystal element was produced in the same manner as in Example 3, except that the ferroelectric liquid crystal layer did not contain Exemplary Compound No. 1 used in Example 3. The optical response speed was measured in the same manner as in Example 1. The results are shown below.
20°C25°C35°C45°C
5400μsec 3600 μsec 29
00 p sec 1800 μsec実施例4
実施例1で使用した強誘電性液晶化合物に代えて、下記
構造式で示す強誘電性液晶化合物を各重量部で用いたほ
かは、実施例1と同様の方法で強誘電性液晶素子を作成
し、実施例1と同様の方法で光学応答速度を測定した。20°C25°C35°C45°C 5400μsec 3600μsec 29
00 p sec 1800 μsec Example 4 The same method as in Example 1 except that the ferroelectric liquid crystal compound shown by the following structural formula was used in each part by weight instead of the ferroelectric liquid crystal compound used in Example 1. A ferroelectric liquid crystal device was prepared in this manner, and the optical response speed was measured in the same manner as in Example 1.
その結果を次に示す。The results are shown below.
55°C; 1007zsec 65°C;9
0μ5eC70°C;測定不能比較例4
実施例4で使用した例示化合物N001を強誘電性液晶
層に含有させなかった他は実施例4と同様の方法で強誘
電性液晶素子を作成し、実施例1と同様の方法で光学応
答速度を測定した。その結果を次に示す。55°C; 1007zsec 65°C; 9
0μ5eC70°C; Unmeasurable Comparative Example 4 A ferroelectric liquid crystal element was prepared in the same manner as in Example 4, except that the exemplified compound N001 used in Example 4 was not contained in the ferroelectric liquid crystal layer. The optical response speed was measured in the same manner as in Example 1. The results are shown below.
75℃ ; Zoo μsec
実施例5
実施例1で使用した強誘電性液晶化合物に代えて、下記
構造式で示す強誘電性液晶化合物を各重量部で用いたほ
かは、実施例1と同様の方法で強誘電性液晶素子を作成
し、実施例1と同様の方法で光学応答速度を測定した。75°C; Zoo μsec Example 5 The same method as Example 1 was used, except that each part by weight of a ferroelectric liquid crystal compound represented by the following structural formula was used instead of the ferroelectric liquid crystal compound used in Example 1. A ferroelectric liquid crystal device was prepared in this manner, and the optical response speed was measured in the same manner as in Example 1.
その結果を次に示す。The results are shown below.
25°C; 15007zsec 35°C; 13
00μsec 45°C;870μSeC比較例5
実施例5で使用した例示化合物No、1を強誘電性液晶
層に含有させなかった他は実施例5と同様の方法で強誘
電性液晶素子を作成し、実施例1と同様の方法で光学応
答速度を測定した。その結果を次に示す。25°C; 15007zsec 35°C; 13
00 μsec 45°C; 870 μSeC Comparative Example 5 A ferroelectric liquid crystal element was prepared in the same manner as in Example 5 except that the exemplified compound No. 1 used in Example 5 was not included in the ferroelectric liquid crystal layer. The optical response speed was measured in the same manner as in Example 1. The results are shown below.
35°C45°C50°C
1500μsec 1000 μsec
800 μsec実施例6
実施例1で使用した強誘電性液晶化合物に代えて、下記
構造式で示す強誘電性液晶化合物を各重量部で用いたほ
かは、実施例1と同様の方法で強誘電性液晶素子を作成
し、実施例1と同様の方法で光学応答速度を測定した。35°C45°C50°C 1500μsec 1000μsec
800 μsec Example 6 The ferroelectric liquid crystal compound used in Example 1 was replaced with a ferroelectric liquid crystal compound represented by the following structural formula in each part by weight. A liquid crystal device was prepared, and the optical response speed was measured in the same manner as in Example 1.
その結果を次に示す。The results are shown below.
5°C; 750μsec 206C; 500μ
sec 35°C; 430μsec比較例6
実施例6で使用した例示化合物No、lを強誘電性液晶
層に含有させなかった他は実施例6と同様の方法で強誘
電性液晶素子を作成し、実施例1と同様の方法で光学応
答速度を測定した。その結果を次に示す。5°C; 750μsec 206C; 500μ
sec 35°C; 430 μsec Comparative Example 6 A ferroelectric liquid crystal element was prepared in the same manner as in Example 6, except that the exemplified compounds No. and 1 used in Example 6 were not contained in the ferroelectric liquid crystal layer. The optical response speed was measured in the same manner as in Example 1. The results are shown below.
5°C20°C35°C
900μsec 560μsec 480μs
ec実施例8
実施例1で使用したポリイミド樹脂前駆体2%ジメチル
アセトアミド溶液に代えて、ポリビニルアルコール樹脂
〔クラレ■製PVA−11732%水溶液を用いた他は
全く同様の方法で強誘電性液晶素子を作成し、光学応答
速度を測定した。5°C20°C35°C 900μsec 560μsec 480μs
ec Example 8 A ferroelectric liquid crystal element was produced in exactly the same manner except that a 2% dimethylacetamide solution of polyimide resin precursor used in Example 1 was replaced with a 32% aqueous solution of polyvinyl alcohol resin (PVA-11 manufactured by Kuraray ■). was created and the optical response speed was measured.
20°C30℃ 40°C
380μsec 350μsec 290μs
ec実施例9
実施例1で使用した5iO7を用いずに、ポリイミド樹
脂だけで絶縁性配向制御層を作成した以外は、全〈実施
例1と同様の方法で強誘電性液晶素子を作成し、光学応
答速度を測定した。20°C30°C 40°C 380μsec 350μsec 290μs
ec Example 9 A ferroelectric liquid crystal element was created in the same manner as in Example 1, except that the insulating alignment control layer was created only with polyimide resin without using 5iO7 used in Example 1. The optical response speed was measured.
20°C30°C40°C
370μsec 350 p sec 3
10 μsec実施例10〜18
実施例2で用いた例示化合物N011に代えて、例示化
合物2.4.6.9. 12. 14.■5. 16を
表1に示す重量部で使用した以外は、実施例例2と全く
同様の方法で強誘電性液晶素子を作成し、光学応答速度
を測定した。その結果を表1に示す。20°C30°C40°C 370 μsec 350 p sec 3
10 μsec Examples 10 to 18 In place of exemplified compound N011 used in Example 2, exemplified compound 2.4.6.9. 12. 14. ■5. A ferroelectric liquid crystal device was prepared in exactly the same manner as in Example 2, except that No. 16 was used in the weight parts shown in Table 1, and the optical response speed was measured. The results are shown in Table 1.
表 1
〔発明め効果〕
本発明の化合物は強誘電性液晶素子の低温作動特性、高
速応答性等を改善し向上させる化合物であり、強誘電性
液晶素子に該化合物を含有させることによって、■低温
作動の温度範囲が広がり、■低温での高速応答性が増し
、■液晶層を良好な配向状態とした改善された強誘電性
液晶素子を得ることができた。Table 1 [Effects of the invention] The compound of the present invention is a compound that improves and improves the low-temperature operating characteristics, high-speed response, etc. of a ferroelectric liquid crystal element, and by incorporating the compound into a ferroelectric liquid crystal element, We were able to obtain an improved ferroelectric liquid crystal device with a wider temperature range for low-temperature operation, (1) increased high-speed response at low temperatures, and (2) a liquid crystal layer in a good alignment state.
第1図は本発明の強誘電性液晶を用いた、液晶表示素子
の1例の断面概略図、
第2図および第3図は強誘電液晶素子の動作説明のため
に、素子セルの一例を模式的に表わす斜視図。
第1図において、
1・・・強誘電液晶層 2・・・ガラス基板3・
・・透明電極 4・・・絶縁性配向制御膜5
・・・スペーサー 6・・・リード線7・・・
電源 8・・・偏光板9・・・光源
■。・・・入射光■・・・透過光
第2図において、
21a・・・基板 21b・・・基板22
・・・強誘電液晶層 23・・・液晶分子24・
・・双極子モーメント(P土)
第3図において、Fig. 1 is a schematic cross-sectional view of an example of a liquid crystal display element using the ferroelectric liquid crystal of the present invention, and Figs. 2 and 3 show an example of an element cell to explain the operation of the ferroelectric liquid crystal element. FIG. 2 is a schematic perspective view. In FIG. 1, 1... Ferroelectric liquid crystal layer 2... Glass substrate 3.
...Transparent electrode 4...Insulating alignment control film 5
...Spacer 6...Lead wire 7...
Power supply 8...Polarizing plate 9...Light source
■. ...Incoming light ■...Transmitted light In Fig. 2, 21a...Substrate 21b...Substrate 22
...Ferroelectric liquid crystal layer 23...Liquid crystal molecules 24.
...Dipole moment (P soil) In Figure 3,
Claims (9)
晶層を包含する強誘電性液晶素子において該強誘電性液
晶層が下記一般式( I ) ▲数式、化学式、表等があります▼・・・・・・・(
I ) で表される化合物を少なくとも1種以上包含するもので
あることを特徴とする強誘電性液晶素子。 (但し、式中R_1及びR_2は置換基を有していても
良い分岐または直鎖の鎖状基を示し、R_1とR_2は
同一であっても異なっいても良い。A_1及びA_2は
置換基を有していても良い、六員環を有する2価の基を
示し、A_1及びA_2は同一であっても異なっていて
も良く、X_1及びX_2は2価の鎖状基である。)(1) In a ferroelectric liquid crystal element that includes a substrate, a voltage application means, an alignment control layer, and a ferroelectric liquid crystal layer, the ferroelectric liquid crystal layer has the following general formula (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼・・・・・・・・・(
A ferroelectric liquid crystal device comprising at least one compound represented by I). (However, in the formula, R_1 and R_2 represent a branched or straight chain group that may have a substituent, and R_1 and R_2 may be the same or different. A_1 and A_2 have a substituent. (A_1 and A_2 may be the same or different, and X_1 and X_2 are divalent chain groups.)
していても良い分岐または直鎖のアルキル基、アシル基
、アシルオキシ基、アルコキシ基、アルコキシカルボニ
ル基及びアルコキシカルボニルオキシ基から選ばれ、R
_2が置換基を有していても良い直鎖または分岐のアル
キル基及びアルコキシ基からそれぞれ選ばれることを特
徴とする特許請求の範囲第1項記載の強誘電性液晶素子
。(2) In the general formula (I), R_1 is selected from a branched or straight-chain alkyl group, an acyl group, an acyloxy group, an alkoxy group, an alkoxycarbonyl group, and an alkoxycarbonyloxy group, which may have a substituent, R
2. The ferroelectric liquid crystal device according to claim 1, wherein _2 is each selected from a linear or branched alkyl group and an alkoxy group which may have a substituent.
少なくともいずれか一方は不斉炭素を持つことを特徴と
する特許請求の範囲第1項記載の強誘電性液晶素子。(3) The ferroelectric liquid crystal device according to claim 1, wherein in the general formula (I), at least one of R_1 and R_2 has an asymmetric carbon.
下記一般式(II)で示されることを特徴とする特許請求
の範囲第1項記載の強誘電性液晶素子。 −(A_3)−_m−(A_4)−_n(II)(ただし
、式中A_3及びA_4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▼又は▲数式、化学式、表
等があります▼で表される置換基を有していても良い六
員環を有する基であり、m、nは0、1又は2であり、
かつm+n=1または2で示される。)(4) The ferroelectric liquid crystal device according to claim 1, wherein in the general formula (I), A_1 and A_2 are represented by the following general formula (II). -(A_3)-_m-(A_4)-_n(II) (However, A_3 and A_4 in the formula are ▲Mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas,
There are chemical formulas, 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. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. A six-membered ring that may have a substituent represented by ▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ is a group having m and n are 0, 1 or 2,
and m+n=1 or 2. )
学式、表等があります▼、▲数式、化学式、表等があり
ます▼、−CH_2CH_2−、▲数式、化学式、表等
があります▼、 −CH_2−、▲数式、化学式、表等があります▼及び
▲数式、化学式、表等があります▼から選ばれ、X_2
が−CH=CH−、−CH_2CH_2−、及び−CH
_2−から選ばれることを特徴とする特許請求の範囲第
1項記載の強誘電性液晶素子。(5) In the above general formula (I), X_1 is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2CH_2-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, - CH_2−, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ and ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and X_2
are -CH=CH-, -CH_2CH_2-, and -CH
The ferroelectric liquid crystal element according to claim 1, characterized in that the ferroelectric liquid crystal element is selected from _2-.
置換基がハロゲン原子、アルコキシ基、トリフルオロメ
チル基及びシアノ基から選ばれることを特徴とする特許
請求の範囲第1項記載の強誘電性液晶素子。(6) Ferroelectricity according to claim 1, characterized in that in the general formula (I), the substituents for R_1 and R_2 are selected from a halogen atom, an alkoxy group, a trifluoromethyl group, and a cyano group. liquid crystal element.
置換基がハロゲン原子、アルキル基、アルコキシ基、ト
リフルオロメチル基及びシアノ基から選ばれることを特
徴とする特許請求の範囲第1項記載の強誘電性液晶素子
。(7) The substituent of A_1 and A_2 in the general formula (I) is selected from a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, and a cyano group. Ferroelectric liquid crystal element.
液晶光変調素子である特許請求の範囲第1項記載の強誘
電性液晶素子。(8) The ferroelectric liquid crystal device according to claim 1, wherein the ferroelectric liquid crystal device according to claim 1 is a liquid crystal light modulation device.
、液晶表示素子である特許請求の範囲第1項記載の強誘
電性液晶素子。(9) The ferroelectric liquid crystal device according to claim 1, wherein the ferroelectric liquid crystal device according to claim 1 is a liquid crystal display device.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61283463A JPS63137984A (en) | 1986-11-28 | 1986-11-28 | Ferroelectric liquid crystal device |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61283463A JPS63137984A (en) | 1986-11-28 | 1986-11-28 | Ferroelectric liquid crystal device |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS63137984A true JPS63137984A (en) | 1988-06-09 |
Family
ID=17665869
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61283463A Pending JPS63137984A (en) | 1986-11-28 | 1986-11-28 | Ferroelectric liquid crystal device |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS63137984A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4892393A (en) * | 1987-11-06 | 1990-01-09 | Chisso Corporation | Ferroelectric liquid crystal composition |
-
1986
- 1986-11-28 JP JP61283463A patent/JPS63137984A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4892393A (en) * | 1987-11-06 | 1990-01-09 | Chisso Corporation | Ferroelectric liquid crystal composition |
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