JPS62260841A - Ferroelectric composite film - Google Patents
Ferroelectric composite filmInfo
- Publication number
- JPS62260841A JPS62260841A JP10421286A JP10421286A JPS62260841A JP S62260841 A JPS62260841 A JP S62260841A JP 10421286 A JP10421286 A JP 10421286A JP 10421286 A JP10421286 A JP 10421286A JP S62260841 A JPS62260841 A JP S62260841A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- general formula
- group
- formulas
- tables
- 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
- 239000002131 composite material Substances 0.000 title claims abstract description 26
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 63
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 229920005992 thermoplastic resin Polymers 0.000 claims abstract description 16
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 claims abstract description 5
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000012528 membrane Substances 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 9
- 238000000034 method Methods 0.000 abstract description 9
- 230000010287 polarization Effects 0.000 abstract description 6
- 238000002156 mixing Methods 0.000 abstract description 5
- 238000000465 moulding Methods 0.000 abstract 2
- 238000000807 solvent casting Methods 0.000 abstract 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 description 19
- 239000010408 film Substances 0.000 description 19
- 229920000642 polymer Polymers 0.000 description 15
- -1 polytetrafluoroethylene Polymers 0.000 description 10
- 239000010409 thin film Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 230000005684 electric field Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004990 Smectic liquid crystal Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 241000594009 Phoxinus phoxinus Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000005621 ferroelectricity Effects 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000131 polyvinylidene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IVRFYNSETZKRSJ-UHFFFAOYSA-N ClC=C.N#CC=CC=CC1=CC=CC=C1 Chemical compound ClC=C.N#CC=CC=CC1=CC=CC=C1 IVRFYNSETZKRSJ-UHFFFAOYSA-N 0.000 description 1
- 229920001393 Crofelemer Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 101100113507 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cnh-1 gene Proteins 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- ZZAGLMPBQOKGGT-UHFFFAOYSA-N [4-[4-(4-prop-2-enoyloxybutoxy)benzoyl]oxyphenyl] 4-(4-prop-2-enoyloxybutoxy)benzoate Chemical compound C1=CC(OCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1)=CC=C1OC(=O)C1=CC=C(OCCCCOC(=O)C=C)C=C1 ZZAGLMPBQOKGGT-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- OXTBKAVZYIKAPK-UHFFFAOYSA-N buta-1,3-diene hydrochloride Chemical group C=CC=C.Cl OXTBKAVZYIKAPK-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- SQNNHEYXAJPPKH-UHFFFAOYSA-N chloroethene;prop-2-enoic acid Chemical compound ClC=C.OC(=O)C=C SQNNHEYXAJPPKH-UHFFFAOYSA-N 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229920000314 poly p-methyl styrene Polymers 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920005671 poly(vinyl chloride-propylene) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920001447 polyvinyl benzene Polymers 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000003440 styrenes Polymers 0.000 description 1
- 125000003011 styrenyl group Polymers [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Abstract
Description
【発明の詳細な説明】 [産業上の利用分野1 本発明は、強誘電性複合膜に関するものである。[Detailed description of the invention] [Industrial application field 1 The present invention relates to a ferroelectric composite film.
更に詳しくは、室温付近で熱力学的に安定な強誘電相を
形成しうる液晶と熱可塑性樹脂とを含有する強誘電性複
合膜に関するものである。More specifically, the present invention relates to a ferroelectric composite film containing a liquid crystal and a thermoplastic resin that can form a thermodynamically stable ferroelectric phase near room temperature.
[従来の技術]
カイラル分子から構成されるスメクチックC液晶は、強
誘電性を示す液晶として知られている。[Prior Art] A smectic C liquid crystal composed of chiral molecules is known as a liquid crystal that exhibits ferroelectricity.
カイラルスメクチックC液晶であって代表的な強誘電性
液晶としては、p−デシルオキシベンノリデンーp°−
7ミノー2−メチルブチルシンナメー) (p−de
cyloxybenzylidene−p’−amin
o −2−5ethylbuty!cinnamate
)(以下これを[DOBAMBCJという、)がある。A typical ferroelectric liquid crystal that is a chiral smectic C liquid crystal is p-decyloxybennolidene-p°-
7 minnow 2-methylbutylcinname) (p-de
cyloxybenzylidene-p'-amin
o -2-5ethylbuty! cinnamate
) (hereinafter referred to as [DOBAMBCJ)].
強誘電性液晶の螺旋のピッチは、通常数ミクロン程度で
あるが、液晶層の厚さがこの螺旋のピッチよりも薄くな
ると、螺旋構造が解消されて液晶分子が一方向に揃うよ
うになる。このような状態の液晶に直流電圧を印加する
ことにより、電圧の正または負の極性により双極子の方
向、すなわち液晶分子の向きを切り替えることができる
。この切り替えに必要な時間は、液晶ディスプレイとし
て最も広く一般に使用されているネマチック液晶素子な
どにおけるそれに較べて、極めて短く、100万分の1
秒よりも短い応答時間が得られる。The helical pitch of a ferroelectric liquid crystal is usually on the order of several microns, but when the thickness of the liquid crystal layer becomes thinner than this helical pitch, the helical structure is dissolved and the liquid crystal molecules become aligned in one direction. By applying a DC voltage to the liquid crystal in such a state, the direction of the dipole, that is, the direction of the liquid crystal molecules can be switched depending on the positive or negative polarity of the voltage. The time required for this switching is extremely short, one millionth, compared to that of nematic liquid crystal elements, which are the most widely used liquid crystal displays.
Response times of less than seconds can be obtained.
電圧の印加をオフにしても、液晶分子の向きはそのまま
保持されるので、双安定効果やメモリー特性を実現する
ことができる。Even when the voltage is turned off, the orientation of the liquid crystal molecules is maintained, making it possible to achieve bistable effects and memory properties.
このようなカイラルスメクチックC液晶は、ネマチック
液晶やフレステリック液晶には見られない優れた利点を
もつものの、現在までのところほとんど実用化されてい
ない、それは、ネマチック液晶のように、室温付近で熱
力学的に安定した強誘電性を有するカイラルスメクチッ
ク液晶が、見つかっていないからである0例えば、前述
のDOBAMBCは、その強誘電相領域が64〜92℃
であり、室温よりかなり高温側にある。Although such chiral smectic C liquid crystals have excellent advantages not found in nematic liquid crystals or freesteric liquid crystals, they have hardly been put into practical use to date. This is because no chiral smectic liquid crystal with mechanically stable ferroelectricity has been found.
, which is considerably higher than room temperature.
一方、強誘電性液晶の一種として知られているエステル
系液晶は、上のDOBAMBCとは異なり、室温付近で
強誘電性を示すが、熱力学的に不安定であるという欠、
αがある。On the other hand, ester-based liquid crystals, which are known as a type of ferroelectric liquid crystal, exhibit ferroelectricity near room temperature, unlike DOBAMBC, but they have the disadvantage of being thermodynamically unstable.
There is α.
[発明が解決しようとした問題点」
本発明者らは、かかる状況にあって、室温付近で熱力学
的に安定した強誘電相を形成しうる複合膜を提供すべく
、鋭意検討した結果、DOBAMBCに代表されるカイ
ラルスメクチックC液晶に、特定のエステル系液晶を混
合し、この混合液晶にさらに熱可塑性樹脂を混合して薄
膜化したものは、この目的が連成されることを見出し、
本発明を完成するに到ったものである。[Problems to be Solved by the Invention] Under such circumstances, the inventors of the present invention have conducted intensive studies to provide a composite film that can form a thermodynamically stable ferroelectric phase near room temperature. We discovered that this purpose can be achieved by mixing a specific ester-based liquid crystal with a chiral smectic C liquid crystal represented by DOBAMBC, and further mixing a thermoplastic resin with this mixed liquid crystal to form a thin film.
This has led to the completion of the present invention.
[問題を解決するための手段1
しかして本発明の要旨とするところは、熱可塑性樹脂(
A)、一般式1−1または一般式1−2で表わされるア
ゾメチン系液晶群、一般式11−1または一般式11−
2で表わされるアゾキシ系液晶群、および一般式■で表
わされるエステル系液晶群の中の少なくとも2つの群か
ら選ばれた強誘電性液晶混合物(B)を含有することを
特徴とする複合膜に存する。[Means for solving the problem 1 However, the gist of the present invention is that thermoplastic resin (
A), azomethine liquid crystal group represented by general formula 1-1 or general formula 1-2, general formula 11-1 or general formula 11-
A composite film comprising a ferroelectric liquid crystal mixture (B) selected from at least two groups of the azoxy liquid crystal group represented by 2 and the ester liquid crystal group represented by the general formula 2. Exists.
一般式:
・・・・1−1
1一般式1−1において、八は水素、ノ10デン原子、
CnH−1炭素fgf−数1〜5の炭化水素基から選ば
れた原子または基を意味し、Bはハロゲン原子、炭素数
1〜5の炭化水素基から選ばれた原子または基を表わし
、nは1〜20の整数を表わす、l・・・・1−2
1一般式1−2において、nは1〜20の整数を表わし
、鴫は1〜15の整数を表わす、1
・・・・n−1
【一般式ロー1において、nは1へ、15の9敗を表わ
す、1・・・・ll−2
【一般式11−2において、nは1〜15の整数を表わ
す、1[一般式■にオイて、XはCnH2n+I O−
* CnHtn++ 8 で表わされ、かつ、nが1
〜2oの整数の基、Cm82m+1 t CmHts
−+O−テ1h%h、カッ、mが1%20の基を表わす
、]
以下、本発明の詳細な説明する。General formula: ...1-1 1 In general formula 1-1, 8 is hydrogen, 10 dene atoms,
CnH-1 carbon fgf- means an atom or group selected from a hydrocarbon group having 1 to 5 carbon atoms, B represents an atom or group selected from a halogen atom, a hydrocarbon group having 1 to 5 carbon atoms, and n represents an integer from 1 to 20, l...1-2 1 In general formula 1-2, n represents an integer from 1 to 20, and 雫 represents an integer from 1 to 15, 1... n-1 [In the general formula Row 1, n represents 1, 9 losses of 15, 1...ll-2 [In the general formula 11-2, n represents an integer from 1 to 15, 1 [ In the general formula ■, X is CnH2n+I O-
* Represented by CnHtn++ 8 and n is 1
A group of integers of ~2o, Cm82m+1 t CmHts
--+O-TE1h%h, ka, m represents a group of 1%20] Hereinafter, the present invention will be described in detail.
本発明に係る複合膜に含まれる熱可塑性樹脂(A)は、
強誘電性混合物(B)と相溶性があれば、待に制限はな
い、具体的には、ポリ塩化ビニル、ポリ臭化ビニル、ポ
リ7フ化ビニル、塩化ビニル−酢酸ビニル共重合体、塩
化ビニル−エチレン共重合体、塩化ビニル−プロピレン
共重合体、塩化ビニル−塩化ビニリデン共重合体、塩化
ビニル−ブタノエン共重合体、塩化ビニル−アクリル酸
エステル共重合体、塩化ビニル−7クリロニトリル共重
合体、塩化ビニル−スチレン−アクリロニトリル三元共
重合体、塩化ビニル−塩化ビニリデン−酢酸ビニル共重
合体、ポリ塩化ビニリデン、ポリテトラフルオロエチレ
ン、ポリテトラフルオロクロルエチレン、ポリ7フ化ビ
ニリデン等のハロゲン化ビニル重合体または、共重合体
;ポリビニルアルコール、ポリ7リルアルコール、ポリ
ビニルエーテル、ポリアリルエーテル等の不飽和アルコ
ールまだはエーテルの重合体または共電合体ニ
アクリル酸またはメタクリル酸等の不飽和カルボン酸の
重合体または共重合体;
ポリ酢酸ビニル等のポリビニルエステル、ポリ7タル酸
等のポリアリルエステル等のアルコール残基中に不飽和
結合をもつものの重合体または共重合体;
ポリアクリル酸エステル、ポリメタクリル酸エステル、
マレイン醇エステルまたは7マル酸エステルの重合体等
の酸残基または酸残基とアルコール残基中に不飽和結合
をもつものの重合体または共重合体;
アクリロニトリルまたはメタクリロニトリルの重合体ま
たは共重合体、ポリシアン化ビニリデン、マロノニトリ
ルまたは770ニトリルの重合体または共重合体等の不
飽和ニトリル重合体または共重合体;
ポリスチレン、ポリフル7Tメチルスチレン、ポリパラ
メチルスチレン、スチレン−アルファメチルスチレン共
重合体、スチレン−バラメチルスチレン共重合体、ポリ
ビニルベンゼン、ポリハロゲン化スチレン等の芳香族ビ
ニル化合物の重合体または共重合体;
ポリビニルピリジン、ポリN−ビニルピロリジン、ポリ
N−ビニルピロリドン等の複素環式化合物の重合体また
は共重合体:
ポリカーボネート等のポリエステル銘合物、ナイロン6
、ナイロン6・6等のポリアミド縮合物;無水マレイン
酸、無水7マル酸およびそのイミド化物を含む重合体ま
たは共重合体;
ポリアミドイミド、ポリエーテルイミド、ポリイミド、
ポリフェニレンオキサイド、ポリ7エ二レンサル7フイ
ド、ポリスルホン、ポリエーテルスルホン、ポリ7リレ
ート等の耐熱性有機高分子;等があげられる。これら例
示は、本発明を限定するものではない。The thermoplastic resin (A) contained in the composite membrane according to the present invention is
There are no limitations as long as it is compatible with the ferroelectric mixture (B). Specifically, polyvinyl chloride, polyvinyl bromide, polyvinyl heptafluoride, vinyl chloride-vinyl acetate copolymer, chloride Vinyl-ethylene copolymer, vinyl chloride-propylene copolymer, vinyl chloride-vinylidene chloride copolymer, vinyl chloride-butanoene copolymer, vinyl chloride-acrylic acid ester copolymer, vinyl chloride-7crylonitrile copolymer halogenation of vinyl chloride-styrene-acrylonitrile terpolymer, vinyl chloride-vinylidene chloride-vinyl acetate copolymer, polyvinylidene chloride, polytetrafluoroethylene, polytetrafluorochloroethylene, polyvinylidene heptafluoride, etc. Vinyl polymers or copolymers; polymers or copolymers of unsaturated alcohols or ethers such as polyvinyl alcohol, poly7lyl alcohol, polyvinyl ether, polyallyl ether; polymers or copolymers of unsaturated carboxylic acids such as diacrylic acid or methacrylic acid; Polymers or copolymers; Polyvinyl esters such as polyvinyl acetate, polyallyl esters such as polyheptatalic acid, and other polymers or copolymers with unsaturated bonds in their alcohol residues; Polyacrylic esters, polyesters, etc. methacrylic acid ester,
Polymers or copolymers of acid residues, such as polymers of maleic acid esters or 7-malate esters, or polymers or copolymers of acid residues and alcohol residues having unsaturated bonds; Polymers or copolymers of acrylonitrile or methacrylonitrile unsaturated nitrile polymers or copolymers, such as polyvinylidene cyanide, malononitrile or 770 nitrile polymers or copolymers; polystyrene, polyfluor 7T methylstyrene, polyparamethylstyrene, styrene-alphamethylstyrene copolymers, Polymers or copolymers of aromatic vinyl compounds such as styrene-baramethylstyrene copolymer, polyvinylbenzene, and polyhalogenated styrene; Heterocyclic compounds such as polyvinylpyridine, polyN-vinylpyrrolidine, and polyN-vinylpyrrolidone Polymers or copolymers: Polyester compounds such as polycarbonate, nylon 6
, polyamide condensates such as nylon 6 and 6; polymers or copolymers containing maleic anhydride, 7-maric anhydride, and imidized products thereof; polyamide-imide, polyetherimide, polyimide,
Examples include heat-resistant organic polymers such as polyphenylene oxide, poly7-enylene sulfide, polysulfone, polyethersulfone, and poly7-rylate. These examples are not intended to limit the invention.
本発明に係る複合膜に含まれる強誘電性液晶混合物(B
)は、一般式1−1または一般式1−2で表わされるア
ゾメチン系液晶群(以下第1群という、)、一般式H−
1または一般式1−2で表わされるアゾキシ系液晶群(
以下第■群という、)、一般式■で表わされるエステル
系液晶群(以下節■群という、)の3つの液晶群のうち
少なくとも2つの群りより選ばれた液晶を組み合せ混合
されたものである。The ferroelectric liquid crystal mixture (B
) is an azomethine liquid crystal group (hereinafter referred to as 1st group) represented by general formula 1-1 or general formula 1-2, general formula H-
1 or azoxy liquid crystal group represented by general formula 1-2 (
A mixture of liquid crystals selected from at least two of the three liquid crystal groups: (hereinafter referred to as Group ■) and the ester-based liquid crystal group represented by the general formula ■ (hereinafter referred to as Group ■). be.
これは各群の中から少なくとも1種を選んだ場合には、
前記のごとき欠点が発現され、本発明の目的は達成され
ない、各群の中から少なくとも1種を選び、少なくとも
2つの群より選ばれた液晶を組み合せ混合すると、本発
明の目的が達成される。This means that if you select at least one species from each group,
The above disadvantages occur and the object of the present invention is not achieved.If at least one liquid crystal is selected from each group and liquid crystals selected from at least two groups are combined and mixed, the object of the present invention is achieved.
本発明において7ジメチン系液晶群とは、前記一般式■
−1*たけ一般式1−2で表わされる液晶をいう、その
具体例としては、次のような化合物があげられる。In the present invention, the 7-dimethine liquid crystal group refers to the general formula
-1*Take Specific examples of the liquid crystal represented by the general formula 1-2 include the following compounds.
p−デシルオキシベンジリデン−po−7ミ/−2−7
チルプチルシンナメート(DOMAMBC)、p−へキ
シルオキシベンジリデン−po−アミノ−2−クロロ−
α−プロビルシンナノート(HOBACPC)、
p−オクチルオキシベンジリデン−po−7ミノー2−
メチルブチル−a−クロロシンナメート(OOBAMB
CC)、
0−ヒドロキシ−p−3−メチルへブトキシベンジリデ
ン−pI−7ミノオクチルベンゼン。p-decyloxybenzylidene-po-7mi/-2-7
Tilbutylcinnamate (DOMAMBC), p-hexyloxybenzylidene-po-amino-2-chloro-
α-provir cinnanote (HOBACPC), p-octyloxybenzylidene-po-7 minnow 2-
Methylbutyl-a-chlorocinnamate (OOBAMB
CC), 0-hydroxy-p-3-methylhebutoxybenzylidene-pI-7 minooctylbenzene.
本発明においてアゾキシ系液晶群とは、前記一般式H−
1または一般式ll−2で表わされる液晶をいう、その
具体例としては、次のような化合物があげられる。In the present invention, the azoxy liquid crystal group refers to the general formula H-
Specific examples of liquid crystals represented by formula 1 or 11-2 include the following compounds.
494°−7ゾキシケイ皮酸−2−メチルブチルエステ
ル、
4.4′−アゾキシフェニルペンチルエーテル。494°-7zoxycinnamic acid-2-methylbutyl ester, 4,4'-azoxyphenylpentyl ether.
本発明においてエステル系液晶群とは、前記一般式■で
表わされる液晶をいう、その具体例としては、次のよう
な化合物があげられる。In the present invention, the ester liquid crystal group refers to liquid crystals represented by the general formula (2) above, and specific examples thereof include the following compounds.
p−n−へキシルオキシベンゾイックアシド−po−(
2−メチルブトキシカルボニル)フェニルエステル、
pn−オクチルオキシベンゾイックアシド−po−(2
−メチルブトキシカルボニル)フェニルエステル、
p−n−ノナノオキシベンゾイツク7シドー、I−(2
−メチルブトキシカルボニル)7ヱニルエステル、
p−n−デカオキシベンゾイック7シドーp’−(2−
メチルブトキシカルボニル)フェニルエステル、pn−
ドデカオキシベンゾイックアシド−po−(2−メチル
ブトキシカルボニル)フェニルエステル、
p−n−テトラデカオキシベンゾイックアシド−po−
(2−メチルブトキシカルボニル)フェニルエステル、
p−n−へキサデカオキシベンゾイック7シドーp’−
(2−メチルブトキシカルボニル)フェニルエステル。p-n-hexyloxybenzoic acid-po-(
2-methylbutoxycarbonyl) phenyl ester, pn-octyloxybenzoic acid-po-(2
-methylbutoxycarbonyl) phenyl ester, p-n-nonanooxybenzoic 7side, I-(2
-methylbutoxycarbonyl) 7enyl ester, p-n-decaoxybenzoic 7side p'-(2-
methylbutoxycarbonyl) phenyl ester, pn-
Dodecaoxybenzoic acid-po-(2-methylbutoxycarbonyl)phenyl ester, p-n-tetradecaoxybenzoic acid-po-
(2-methylbutoxycarbonyl)phenyl ester, p-n-hexadecaoxybenzoic 7-side p'-
(2-Methylbutoxycarbonyl)phenyl ester.
上の各液晶群に含まれる化合物の例示は、本発明をこれ
ら例示したものに限定するものではない。The above examples of compounds included in each liquid crystal group are not intended to limit the present invention to these examples.
本発明者らの実験によれば、更に、3つの群から選ばれ
た液晶を組み合せる場合、最も少ない群の液晶成分の占
める割合が20モル%以上とすると、本発明の目的が効
果的に達成できることが分った。According to the experiments of the present inventors, when liquid crystals selected from three groups are combined, the object of the present invention can be effectively achieved if the ratio of the liquid crystal component of the smallest group is 20 mol% or more. I found out that it can be achieved.
本発明の(B)成分である液晶混合物には、液晶分子の
配向を助けるために極性界面活性剤を添加することがで
きるし、カラー表示するために2色性色素を添加するこ
ともできる6
前記熱可塑性樹脂(A)と液晶混合物(B)との配合割
合は、熱可塑性樹脂(A)の割合を20〜60重景%の
置部とするのがよい。熱可塑性樹脂が20重置部未満で
あると、本発明に係る組成物から薄膜を得るのが困難と
なり、60重量%を超えると強誘電相を形成する薄膜が
得られなくなるので、好ましくない。A polar surfactant can be added to the liquid crystal mixture which is the component (B) of the present invention in order to assist in the alignment of liquid crystal molecules, and a dichroic dye can also be added in order to display color. The blending ratio of the thermoplastic resin (A) and the liquid crystal mixture (B) is preferably such that the ratio of the thermoplastic resin (A) is 20 to 60% by weight. If the amount of thermoplastic resin is less than 20 parts, it will be difficult to obtain a thin film from the composition according to the present invention, and if it exceeds 60% by weight, it will be impossible to obtain a thin film that forms a ferroelectric phase, which is not preferable.
本発明に係る強誘電性薄膜は、平膜、スパイラル膜、中
空系膜等種々の形態で使用できる。平膜として使用する
場合には、極薄膜として使用されることが多く、その性
能を充分に発揮することができる。The ferroelectric thin film according to the present invention can be used in various forms such as a flat film, a spiral film, and a hollow film. When used as a flat film, it is often used as an extremely thin film, and its performance can be fully demonstrated.
本発明に係る強誘電性薄膜を調製するには、乾湿製膜法
、溶液流延法、溶液塗布法、水−ヒ延展法等のいずれの
方法によってもよい。性能を充分に発揮する平膜状の極
薄膜を得るには、熱可塑性樹脂(A)と液晶混合物(B
)との混合物を、熱可塑性樹脂(A)の良溶媒または良
溶媒と1を溶媒との混合液に溶解し、溶液流延法、溶液
塗布法、水上延展法等によって製膜するのが好適である
。The ferroelectric thin film according to the present invention may be prepared by any method such as a wet-dry film forming method, a solution casting method, a solution coating method, and a water-hydrogen spreading method. In order to obtain a flat, ultra-thin film that exhibits sufficient performance, a mixture of thermoplastic resin (A) and liquid crystal mixture (B) is required.
) is preferably dissolved in a good solvent for the thermoplastic resin (A) or a mixture of a good solvent and a solvent and formed into a film by a solution casting method, a solution coating method, a water spreading method, etc. It is.
本発明に係る強誘電性薄膜は、電気光学素子、大型液晶
ディスプレイ、温度センサー、液晶光シャッター、光変
調器等に応用することができる。The ferroelectric thin film according to the present invention can be applied to electro-optical elements, large liquid crystal displays, temperature sensors, liquid crystal optical shutters, optical modulators, and the like.
[発明の効果]
本発明は次のように特別に顕著な効果を奏し、その#−
,業上の利用価値は啄めて大である。[Effects of the Invention] The present invention has the following particularly remarkable effects, and #-
,The commercial value is enormous.
(1)本発明に係る複合膜は、常温付近で強誘電相を形
成し、ディスプレイの用途に使用した場合、優れた輝度
が達成される。これは第1群の液晶または第■群の液晶
から選択した液晶単独と、熱可塑性樹脂を含む複合膜で
は達成できなかった顕著な効果である。(1) The composite film according to the present invention forms a ferroelectric phase at around room temperature and achieves excellent brightness when used in display applications. This is a remarkable effect that could not be achieved with a composite film containing a thermoplastic resin and a liquid crystal selected from the first group of liquid crystals or the liquid crystal of the first group.
(2) tjSm群の液晶単独と熱可塑性ム(ITh
tとを含む複合膜は、常温付近のわずかな温度変化によ
って液晶の結晶構造が変化する傾向が強いが、本発明に
係る複合膜は、常温付近で熱力学的に安定であり、わず
かの温度変化では結晶構造が変化しにくい性質をもって
いる。また、常温での分極反転時間が短く、スイッチ等
の用途に好適である。(2) tjSm group liquid crystal alone and thermoplastic rubber (ITh
Composite films containing t have a strong tendency for the crystal structure of the liquid crystal to change due to slight temperature changes near room temperature, but the composite film according to the present invention is thermodynamically stable near room temperature and Its crystal structure does not change easily when subjected to changes. In addition, the polarization reversal time at room temperature is short, making it suitable for applications such as switches.
「実施例」
以下、本発明を実施例、比較例にもとづいて詳細に説明
するが、本発明はその要旨を遁えない限り、以下の例に
限定されるものではない。"Examples" Hereinafter, the present invention will be explained in detail based on Examples and Comparative Examples, but the present invention is not limited to the following examples unless the gist thereof is departed from.
実施例、比較例
〈強誘電性液晶混合物の調製〉
液晶として、ff11群に属するp−デシルオキシベン
ノリデン−1)’ 7ミノー2−メチルブチルシンナ
メー)(DOBAMBC)と、第m群1こ属するpn−
t’デカオキシベンゾイックアシド−p’−(2−メチ
ルブ)4ジカルボニル)フェニルエステル(以下これを
「C−1□」という。)とを、DOBAMBC/C−,
2トのモル比を50150とし、それぞれ混合した強誘
電性液晶混合物を得た。Examples and Comparative Examples <Preparation of ferroelectric liquid crystal mixture> As liquid crystals, p-decyloxybennolidene-1)'7 minnow 2-methylbutylcinname) (DOBAMBC) belonging to the ff11 group and Belongs to pn-
t'decaoxybenzoic acid-p'-(2-methylbu)4dicarbonyl)phenyl ester (hereinafter referred to as "C-1□"), DOBAMBC/C-,
A ferroelectric liquid crystal mixture was obtained by setting the molar ratio of 2 and 2 to 50,150, respectively.
〈熱可塑性0(脂との混合〉
上の液晶混合物(実施例)と、DOBAMnCのみ(比
較例)の合計2種間の液晶に、ポリ塩化ビニル(平均重
合度、1.050のもの)の粉末を、液晶/ポリ塩化ビ
ニルとを重唯比で70/30の割合で混合した。<Thermoplasticity 0 (mixing with fat)> A total of two types of liquid crystals, the above liquid crystal mixture (example) and DOBAMnC only (comparative example), were mixed with polyvinyl chloride (average degree of polymerization, 1.050). The powder was mixed with liquid crystal/polyvinyl chloride in a weight ratio of 70/30.
く薄膜の調製〉
上の2NMの清、合物を、それぞれシクロヘキサノンに
溶解し、樹脂の濃度が10重量%の溶液を調製した、
上の重合体溶液のそれぞれを、283Kに保たれた水槽
中の水面の壁際に1滴靜かに落とし、水面−ヒに薄膜を
形成させ、直ちにすくい上げ、室温で真空乾燥して約3
0旧自のV(水面展開膜)を得た。このようにして得ら
れた水面展開膜をテフロン板上に40枚積層したのち、
この膜をリング状7レームに固定してから、7レームご
とテア0ン板から剥離し、窒素雰囲気中で333にで数
分間処理して、皺や弛みのない膜を調製した。Preparation of thin film> The above 2NM polymer solution and compound were each dissolved in cyclohexanone to prepare a solution with a resin concentration of 10% by weight. Each of the above polymer solutions was placed in a water bath maintained at 283K. Drop one drop gently on the wall of the water surface to form a thin film on the water surface, scoop it up immediately, and dry it under vacuum at room temperature for about 30 minutes.
0 original V (water surface development film) was obtained. After laminating 40 sheets of the water surface deployable membrane thus obtained on a Teflon plate,
After fixing this film into 7 ring-shaped frames, each 7 frames were peeled off from the tare plate and treated at 333° C. for several minutes in a nitrogen atmosphere to prepare a film without wrinkles or loosening.
〈複合膜についてのスイッチング効果の測定〉複合膜に
ついてのスイッチング効果を、次のようにして測定した
。<Measurement of switching effect on composite membrane> The switching effect on the composite membrane was measured as follows.
2枚のスライドグラスのそれぞれの片面上に、幅約りn
+m’?’帯状にアルミニツムを真空蒸着し、これを電
極とした。電極面を対向させた間に、上で得られた複合
膜をはさみ、第1図に概略斜視図、第2図に第1[71
rl−11部分での縦断側面図として示したような試験
装置を準備した。なす(、第1図および第2図では、上
側のスライドグラスが省略されている。On one side of each of the two glass slides,
+m'? 'Aluminum was vacuum-deposited in a strip shape and used as an electrode. The composite membrane obtained above was sandwiched between the electrode surfaces facing each other, and a schematic perspective view is shown in FIG.
A test device as shown in the longitudinal side view of the rl-11 section was prepared. Eggplant (in Figures 1 and 2, the upper slide glass is omitted.
第1図および第2図において、1はスライドグラス、2
.3はアルミニウム電極、4は複合膜、5.6はリード
線をそれぞれ示す。In Figures 1 and 2, 1 is a slide glass, 2
.. 3 indicates an aluminum electrode, 4 indicates a composite membrane, and 5.6 indicates a lead wire.
上の試験装置を用い、両電極間に直流電界を印加し、直
流電界印加に伴なう試料複合膜の分極変化を、電界を印
加してからの時間に対してプロットすることにより求め
た。Using the above test device, a DC electric field was applied between both electrodes, and the polarization change of the sample composite film due to the application of the DC electric field was determined by plotting against the time after the electric field was applied.
Pt53図は、D OB A M B C/ C−,2
の50150(モル比)での液晶混合物を含む複合膜に
ついての320にの分極反転時間の電界依存性を示して
おり、Pt54図は比較のためDOBAMBCLか含ま
ない複合膜についての358におよび353にでの分極
反転時間の電界依存性を示している。Pt53 diagram is DOB A M B C/ C-,2
The Pt54 diagram shows the electric field dependence of the polarization reversal time at 320 for a composite film containing a liquid crystal mixture at a molar ratio of 50150 (molar ratio); It shows the electric field dependence of the polarization reversal time at .
第3図およびm4図は、本発明に係る複合膜は低温にお
いてもスイッチング時間が短いことを示す。Figures 3 and m4 show that the composite membrane according to the invention has a short switching time even at low temperatures.
Pt51図は、複合膜についてのスイッチング効果測定
に使用した試験装置の概略斜視図、第2図はPt51図
の■−■部分での縦断側面図である。第3図および第4
図は、分極反転時間の電界依存性を示しており、第3図
は実施例のもの、第4図は比較例のものを示す。
図において、1はスライドグラス、2.3はアルミニウ
ム電極、4は複合膜、5.6はリード線をそれぞれ示す
。Pt51 diagram is a schematic perspective view of a test device used to measure the switching effect of the composite membrane, and FIG. 2 is a longitudinal cross-sectional side view of the Pt51 diagram at the section ■-■. Figures 3 and 4
The figures show the electric field dependence of the polarization inversion time, with FIG. 3 showing the example and FIG. 4 showing the comparative example. In the figure, 1 is a slide glass, 2.3 is an aluminum electrode, 4 is a composite membrane, and 5.6 is a lead wire.
Claims (4)
式 I −2で表わされるアゾメチン系液晶群、一般式II
−1または一般式II−2で表わされるアゾキシ系液晶群
、および一般式IIIで表わされるエステル系液晶群の中
の少なくとも2つの群から選ばれた強誘電性液晶混合物
(B)を含有することを特徴とする強誘電性複合膜。 一般式: ▲数式、化学式、表等があります▼・・・・ I −1 [一般式 I −1において、Aは水素、ハロゲン原子、
C≡N−、炭素数1〜5の炭化水素基から選ばれた原子
または基を意味し、Bはハロゲン原子、炭素数1〜5の
炭化水素基から選ばれた原子または基を表わし、nは1
〜20の整数を表わす。]▲数式、化学式、表等があり
ます▼ [一般式 I −2において、nは1〜20の整数を表わ
し、mは1〜15の整数を表わす。] ▲数式、化学式、表等があります▼・・・・II−1 [一般式II−1において、nは1〜15の整数を表わす
。]▲数式、化学式、表等があります▼・・・・II−2 [一般式II−2において、nは1〜15の整数を表わす
。]▲数式、化学式、表等があります▼・・・・III [一般式IIIにおいて、XはC_nH_2_n_+_1
O−、▲数式、化学式、表等があります▼で表わされ、
かつ、nが1〜20の整数の基、▲数式、化学式、表等
があります▼から選ばれた基を表わし、Yは C_mH_2_m_+_1−、C_mH_2_m_+_
1O−で表わされ、かつ、mが1〜20の整数の基、▲
数式、化学式、表等があります▼、▲数式、化学式、表
等があります▼から選ばれた 基を表わす。](1) Thermoplastic resin (A), azomethine liquid crystal group represented by general formula I-1 or general formula I-2, general formula II
-1 or the azoxy liquid crystal group represented by general formula II-2, and the ferroelectric liquid crystal mixture (B) selected from at least two groups among the ester liquid crystal group represented by general formula III. A ferroelectric composite film characterized by: General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼... I-1 [In the general formula I-1, A is hydrogen, halogen atom,
C≡N-, means an atom or group selected from a hydrocarbon group having 1 to 5 carbon atoms, B represents an atom or group selected from a halogen atom, a hydrocarbon group having 1 to 5 carbon atoms, and n is 1
Represents an integer between ~20. ]▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In general formula I-2, n represents an integer from 1 to 20, and m represents an integer from 1 to 15. ] ▲There are mathematical formulas, chemical formulas, tables, etc.▼...II-1 [In general formula II-1, n represents an integer from 1 to 15. ]▲There are mathematical formulas, chemical formulas, tables, etc.▼...II-2 [In general formula II-2, n represents an integer from 1 to 15. ]▲There are mathematical formulas, chemical formulas, tables, etc.▼...III [In general formula III, X is C_nH_2_n_+_1
O-, ▲There are mathematical formulas, chemical formulas, tables, etc. Represented by ▼,
And, n represents an integer group of 1 to 20, a group selected from ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and Y is C_mH_2_m_+_1-, C_mH_2_m_+_
A group represented by 1O- and where m is an integer of 1 to 20, ▲
Represents a group selected from ▼, ▲ includes mathematical formulas, chemical formulas, tables, etc. ▼ includes mathematical formulas, chemical formulas, tables, etc. ]
て、最も少ない群の液晶が占める割合が20モル%以上
であることを特徴とする、特許請求の範囲第(1)項記
載の強誘電性複合膜。(2) The strength according to claim (1), characterized in that among the plurality of groups of liquid crystals contained in the liquid crystal mixture (B), the proportion of the liquid crystal of the smallest group is 20 mol% or more. Dielectric composite membrane.
る複合膜において、熱可塑性樹脂(A)の割合が20〜
60重量%であることを特徴とする、特許請求の範囲第
(1)項ないし第(2)項いずれかに記載の強誘電性複
合膜。(3) In the composite film containing the thermoplastic resin (A) and the liquid crystal mixture (B), the proportion of the thermoplastic resin (A) is 20 to
60% by weight of the ferroelectric composite film according to any one of claims (1) to (2).
溶媒と貧溶媒との混合液に溶解し、この溶液から製膜さ
れたものであることを特徴とする、特許請求の範囲第(
1)項ないし第(3)項いずれかに記載の強誘電性複合
膜。(4) Claims characterized in that the composite membrane is produced by dissolving the thermoplastic resin (A) in a good solvent or a mixture of a good solvent and a poor solvent, and forming a membrane from this solution. No. (
The ferroelectric composite film according to any one of items 1) to (3).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10421286A JPH0721085B2 (en) | 1986-05-07 | 1986-05-07 | Ferroelectric composite film |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10421286A JPH0721085B2 (en) | 1986-05-07 | 1986-05-07 | Ferroelectric composite film |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS62260841A true JPS62260841A (en) | 1987-11-13 |
JPH0721085B2 JPH0721085B2 (en) | 1995-03-08 |
Family
ID=14374655
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP10421286A Expired - Lifetime JPH0721085B2 (en) | 1986-05-07 | 1986-05-07 | Ferroelectric composite film |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0721085B2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0586014A1 (en) * | 1992-09-01 | 1994-03-09 | Koninklijke Philips Electronics N.V. | Optical modulation device |
US5389287A (en) * | 1992-07-14 | 1995-02-14 | Mitsui Petrochemical Industries, Ltd. | Antiferroelectric liquid crystal composite material, process for preparing the same, and liquid crystal element using the same |
US5589959A (en) * | 1992-09-01 | 1996-12-31 | U.S. Philips Corporation | Optical modulation device having a polymer network containing free molecules of a chiral liquid crystalline material |
-
1986
- 1986-05-07 JP JP10421286A patent/JPH0721085B2/en not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5389287A (en) * | 1992-07-14 | 1995-02-14 | Mitsui Petrochemical Industries, Ltd. | Antiferroelectric liquid crystal composite material, process for preparing the same, and liquid crystal element using the same |
EP0586014A1 (en) * | 1992-09-01 | 1994-03-09 | Koninklijke Philips Electronics N.V. | Optical modulation device |
US5589959A (en) * | 1992-09-01 | 1996-12-31 | U.S. Philips Corporation | Optical modulation device having a polymer network containing free molecules of a chiral liquid crystalline material |
Also Published As
Publication number | Publication date |
---|---|
JPH0721085B2 (en) | 1995-03-08 |
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