JPH02696A - Liquid crystal composition and liquid crystal element prepared by using same - Google Patents
Liquid crystal composition and liquid crystal element prepared by using sameInfo
- Publication number
- JPH02696A JPH02696A JP988889A JP988889A JPH02696A JP H02696 A JPH02696 A JP H02696A JP 988889 A JP988889 A JP 988889A JP 988889 A JP988889 A JP 988889A JP H02696 A JPH02696 A JP H02696A
- Authority
- JP
- Japan
- Prior art keywords
- formulas
- tables
- liquid crystal
- chemical
- chemical formulas
- 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
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 170
- 239000000203 mixture Substances 0.000 title claims abstract description 100
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 53
- 125000001424 substituent group Chemical group 0.000 claims abstract description 24
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 239000007788 liquid Substances 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims 101
- 230000004044 response Effects 0.000 abstract description 67
- 230000003247 decreasing effect Effects 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 53
- 230000005684 electric field Effects 0.000 description 29
- 230000003287 optical effect Effects 0.000 description 28
- 239000012071 phase Substances 0.000 description 25
- 239000010410 layer Substances 0.000 description 24
- 230000007704 transition Effects 0.000 description 17
- 239000011521 glass Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 230000010287 polarization Effects 0.000 description 9
- 230000002269 spontaneous effect Effects 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000004990 Smectic liquid crystal Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- 230000001747 exhibiting effect Effects 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 125000006850 spacer group Chemical group 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- KBJAZDKVSZDVDM-SHTZXODSSA-N CCC[C@H]1CC[C@H](CCC(C=C2)=CC=C2S(O)(=O)=O)CC1 Chemical compound CCC[C@H]1CC[C@H](CCC(C=C2)=CC=C2S(O)(=O)=O)CC1 KBJAZDKVSZDVDM-SHTZXODSSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000011810 insulating material Substances 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000009719 polyimide resin Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000010409 thin film Substances 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- -1 Lithium aluminum hydride Chemical compound 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 229910052770 Uranium Inorganic materials 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BLBNEWYCYZMDEK-UHFFFAOYSA-N $l^{1}-indiganyloxyindium Chemical compound [In]O[In] BLBNEWYCYZMDEK-UHFFFAOYSA-N 0.000 description 1
- AGBINQHSDMZNBI-UHFFFAOYSA-N (4-propylcyclohexyl)methanol Chemical compound CCCC1CCC(CO)CC1 AGBINQHSDMZNBI-UHFFFAOYSA-N 0.000 description 1
- MTUCYAOJXPTLHZ-UHFFFAOYSA-N 1-cyclohexylbutan-1-ol Chemical compound CCCC(O)C1CCCCC1 MTUCYAOJXPTLHZ-UHFFFAOYSA-N 0.000 description 1
- AQFOPOSIKGCYAM-UHFFFAOYSA-N 4-(5-decylpyrimidin-2-yl)phenol Chemical compound N1=CC(CCCCCCCCCC)=CN=C1C1=CC=C(O)C=C1 AQFOPOSIKGCYAM-UHFFFAOYSA-N 0.000 description 1
- NMZPWKRKMBJEOZ-UHFFFAOYSA-N 4-propylcyclohexane-1-carbonyl chloride Chemical compound CCCC1CCC(C(Cl)=O)CC1 NMZPWKRKMBJEOZ-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 235000003403 Limnocharis flava Nutrition 0.000 description 1
- 244000278243 Limnocharis flava Species 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910052774 Proactinium Inorganic materials 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical class OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- HWPNVPPNLZWUID-UHFFFAOYSA-N ethyl 4-propylcyclohexane-1-carboxylate Chemical compound CCCC1CCC(C(=O)OCC)CC1 HWPNVPPNLZWUID-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical group OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 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
- 239000002052 molecular layer Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 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
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920003055 poly(ester-imide) 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
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 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
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、新規な液晶組成物およびそれを使用した液晶
素子に関し、さらに詳しくは電界に対する応答特性が改
善された新規な液晶組成物、およびそれを使用した液晶
表示素子や液晶−光シヤツター等に利用される液晶素子
に関するものである。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a novel liquid crystal composition and a liquid crystal element using the same, and more particularly to a novel liquid crystal composition with improved response characteristics to an electric field, and The present invention relates to liquid crystal elements used in liquid crystal display elements, liquid crystal light shutters, etc. using the same.
［従来の技術］
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、例えばエム シャット（Ｍ。[Prior Art] Liquid crystals have conventionally been applied as electro-optical elements in various fields. Most of the liquid crystal elements currently in practical use are, for example, M-Shut (M.
５ｃｈａｄｔ）とダブリュ ヘルフリッヒ（Ｗ、Ｉ（ｅ
ｌｆｒｉｃｈ）著“アプライド フィジックス レター
ズ（“Ａｐｐｌｉｅｄ Ｐｈｙｇｉｃｓ Ｌｅｔｔ
ｅｒｓ ″ ） Ｖｏ、１８． Ｎｏ、４（１９
７１，２，１５）Ｐ、１２７〜１２８ の “Ｖｏｌ
ｔａｇｅ ＤｅｐｅｎｄｅｎｔＯｐｔｉｃａｌ Ａ
ｃｔｉｖｉｔｙ ｏｆ ａ Ｔｗｉｓｔｅｄ
Ｎｅｍａｔｉｃ １ｉｑｕｉｄＣｒｙｓｔａｌ”に示
されたＴＮ（Ｔｗｉｓｔｅｄ Ｎｅｍａｔｉｃ）型の液
晶を用いたものである。5chadt) and W. Helfrich (W, I(e
“Applied Physics Letts” by lfrich)
ers'') Vo, 18. No, 4 (19
71, 2, 15) P, 127-128 “Vol.
stage Dependent Optical A
activity of a twisted
This uses a TN (Twisted Nematic) type liquid crystal shown in "Nematic 1quid Crystal".
これらは、液晶の誘電的配列効果に基づいておリ、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に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、多くの応用のためには遅すぎる。一方、大型平
面デイスプレィへの応用では、価格、生産性などを考え
合わせると、単純マトリクス方式による駆動か最も有力
である。単純マトリクス方式においては、走査電極群と
信号電極群をマトリクス状に構成した電極構成が採用さ
れ、その駆動のためには、走査電極群に順次周期的にア
ドレス信号を選択印加し、信号電極群には所定の情報信
号をアドレス信号と同期させて並列的に選択印加する時
分割駆動方式か採用されている。These are based on the dielectric alignment effect of liquid crystal, 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 limit of these devices is said to be milliseconds, which is too slow for many applications. On the other hand, for application to large flat displays, a simple matrix drive method is most likely, considering cost, productivity, etc. In the simple matrix method, an electrode configuration in which a scanning electrode group and a signal electrode group are arranged in a matrix is adopted, and in order to drive the electrode group, an address signal is selectively and periodically applied to the scanning electrode group, and the signal electrode group is A time division driving method is adopted in which a predetermined information signal is selectively applied in parallel in synchronization with an address signal.
しかし、この様な駆動方式の素子に前述したＴＮ型の液
晶を採用すると、走査電極が選択され、信号電極が選択
されない領域、或いは走査電極か選択されず、信号電極
が選択される領域（所謂“半選択点″）にも有限に電界
がかかってしまう。However, if the above-mentioned TN type liquid crystal is adopted as an element of such a driving method, there will be a region where the scan electrode is selected and the signal electrode is not selected, or a region where the scan electrode is not selected and the signal electrode is selected (so-called A finite electric field is also applied to the “half-selected point”.
選択点にかかる電圧と、半選択点にかかる電圧の差が充
分に大きく、液晶分子を電界に垂直に配列させるのに要
する電圧閾値がこの中間の電圧値に設定されるならば、
表示素子は正常に動作するわけであるか、走査線数（Ｎ
）を増加して行った場合、画面全体（ｌフレーム）を走
査する間に一つの選択点に有効な電界がかかつている時
間（ｄｕｔｙ比）がｌ／Ｎの割合で減少してしまう。If the difference between the voltage applied to the selected point and the voltage applied to the half-selected point is sufficiently large, and the voltage threshold required to align the liquid crystal molecules perpendicular to the electric field is set to an intermediate voltage value,
Does the display element operate normally?The number of scanning lines (N
), the time during which an effective electric field is applied to one selected point (duty ratio) while scanning the entire screen (1 frame) decreases at a rate of 1/N.
このために、くり返し走査を行なった場合の選択点と非
選択点にかかる実効値としての電圧差は、走査線数か増
えれば増える程小さくなり、結果的には画像コントラス
トの低下やクロストークか避は難い欠点となっている。For this reason, when repeated scanning is performed, the effective voltage difference between selected points and non-selected points becomes smaller as the number of scanning lines increases, resulting in reduced image contrast and crosstalk. This is a drawback that is difficult to avoid.
この様な現象は、双安定性を有さない液晶（電極面に対
し、液晶分子か水平に配向しているのが安定状態であり
、電界が有効に印加されている間のみ垂直に配向する）
を時間的蓄積効果を利用して駆動する（即ち、繰り返し
走査する）ときに生ずる本質的には避は難い問題点であ
る。This phenomenon is caused by liquid crystals that do not have bistability (the stable state is when the liquid crystal molecules are aligned horizontally with respect to the electrode surface, and they are aligned vertically only while an electric field is effectively applied). )
This is essentially an unavoidable problem that arises when driving using the temporal accumulation effect (that is, repeatedly scanning).
この点を改良するために、電圧平均化法、２周波駆動法
や、多重マトリクス法等が既に提案されているが、いず
れの方法でも不充分であり、表示製子の大画面化や高密
度化は走査線数が充分に増やせない２とによって頭打ち
になっているのが現状である。In order to improve this point, voltage averaging method, dual frequency driving method, multiple matrix method, etc. have already been proposed, but all of these methods are insufficient, and it is necessary to increase the screen size of the display screen and increase the density. Currently, the number of scanning lines has reached a plateau due to the inability to increase the number of scanning lines sufficiently.
この様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か、クラーク（（：
Ｉａｒｋ）およびラガウェル（Ｌａｇｅｒｗａｌｌ）に
より提案されている（特開昭５６−１０７２１６号公報
、米国特許第４３６７９２４号明細書等）。To improve these drawbacks of conventional liquid crystal elements, the use of bistable liquid crystal elements or Clark ((:
Irk) and Lagerwall (Japanese Unexamined Patent Publication No. 107216/1983, US Pat. No. 4,367,924, etc.).
双安定性液晶としては、一般にカイラルスメクティック
Ｃ相（Ｓａｃ”相）又はＨ相（Ｓ■Ｈ８相）を有する強
誘電性液晶が用いられる。As the bistable liquid crystal, generally used is a ferroelectric liquid crystal having a chiral smectic C phase (Sac'' phase) or H phase (S■H8 phase).
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ている。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、かつ、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。This ferroelectric liquid crystal has a bistable state consisting of a first optically stable state and a second optically stable state in response to an electric field, and therefore is different from the optical modulation element used in the above-mentioned TN type liquid crystal. Differently, for example, the liquid crystal is oriented in a first optically stable state with respect to one electric field vector, and the liquid crystal is oriented in a second optically stable state with respect to the other electric field vector. Furthermore, this type of liquid crystal 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.
以上の様な双安定性を有する特徴に加えて、強誘電性液
晶は高速応答性であるという優れた特徴を持つ。それは
強誘電性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.
この様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、この様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
質的な改善か得られる。特に、高速光学光シャッターや
高密度、大画面デイスプレィへの応用が期待される。こ
のため強誘電性を持つ液晶材料に関しては広く研究がな
されているか、現在までに開発された強誘電性液晶材料
は、低温作動特性、高速応答性等を含めて液晶素子に用
いる十分な特性を備えているとは言い難い。In this way, ferroelectric liquid crystals potentially have extremely excellent properties, and by utilizing these properties, many of the problems of conventional TN-type devices mentioned above can be solved, which is quite essential. Improvements can be obtained. In particular, it is expected to be applied to high-speed optical shutters and high-density, large-screen displays. For this reason, extensive research has been conducted on liquid crystal materials with ferroelectric properties, and the ferroelectric liquid crystal materials developed to date have sufficient characteristics for use in liquid crystal devices, including low-temperature operation characteristics and high-speed response. It is hard to say that we are prepared.
応答時間でと自発分極の大きさＰｓおよび粘度ηの間に
は、下記の式［Ａ］
η ［Ａ］
””Ｐｓ−Ｅ
（たたし、Ｅは印加電界である）
の関係か存在する。したかって応答速度を速くするには
、
（ア）自発分極の大きさＰｓを大きくする（イ）粘度η
を小さくする
（つ）印加電界Ｅを大きくする
方法がある。しかじ印加電界は、ＩＣ等で駆動するため
上限があり、出来るだけ低い方か望ましい。The relationship between the response time, the magnitude of spontaneous polarization Ps, and the viscosity η is expressed by the following formula [A] η [A] ””Ps-E (where E is the applied electric field) . Therefore, in order to increase the response speed, (a) increase the magnitude of spontaneous polarization Ps (b) increase the viscosity η
There is a method of increasing the applied electric field E. The applied electric field has an upper limit because it is driven by an IC or the like, and it is desirable that it be as low as possible.
よつて、実際には粘度ηを小さくするか、自発分極の大
きさＰｓの値を大きくする必要かある。Therefore, it is actually necessary to reduce the viscosity η or increase the value of the spontaneous polarization Ps.
−旧市に自発分極の大きい強誘電性カイラルスメクチッ
ク液晶化合物においては、自発分極のもたらすセルの内
部電界も大きく、双安定状態をとり得る素子構成への制
約が多くなる傾向にある。-For ferroelectric chiral smectic liquid crystal compounds with large spontaneous polarization, the internal electric field of the cell caused by the spontaneous polarization is also large, and there tends to be more restrictions on device configurations that can achieve a bistable state.
又、いたずらに自発分極を大きくしても、それにつれて
粘度も大きくなる傾向にあり、結果的には応答速度はあ
まり速くならないことか考えられる。Furthermore, even if the spontaneous polarization is unnecessarily increased, the viscosity tends to increase as well, and as a result, it is thought that the response speed will not become very fast.
また、実際のデイスプレィとしての使用温度範囲か、例
えば５〜４０°Ｃ程度とした場合、応答速度の変化か一
般に２０倍程もあり、駆動電圧及び周波数による調部の
限界を越えているのか現状である。In addition, when the actual operating temperature range for a display is set to, for example, 5 to 40°C, the response speed generally changes by about 20 times, and it is unclear whether the adjustment limit due to drive voltage and frequency is exceeded at present. It is.
以上述べたように、強誘電性液晶素子を実用化するため
には、粘度が低く高速応答性を有し、かつ応答速度の温
度依存性の小さな強誘電性カイラルスメクチック液晶組
成物か要求される。As mentioned above, in order to put ferroelectric liquid crystal elements into practical use, a ferroelectric chiral smectic liquid crystal composition that has low viscosity, high-speed response, and small temperature dependence of response speed is required. .
［発明が解決しようとする課題］
本発明の目的は１強誘電性液晶素子を実用できるように
するために、応答速度か速く、シかもその応答速度の温
度依存性が軽減された液晶組成物、特に強誘電性カイラ
ルスメクチック液晶組成物、および該液晶組成物を使用
する液晶素子を提供することにある。[Problems to be Solved by the Invention] An object of the present invention is to provide a liquid crystal composition that has a high response speed and reduces the temperature dependence of the response speed, in order to make a ferroelectric liquid crystal device practical. In particular, it is an object of the present invention to provide a ferroelectric chiral smectic liquid crystal composition and a liquid crystal element using the liquid crystal composition.
［課題を解決するための手段］および［作用］即ち、本
発明の第一の発明は、
下記−旧式［Ｉ］
Ｒ，−（Ｅ）−ＣＨｔＯ−Ａ−Ｒｚ ［Ｉ ］
（式中、Ｒ１は置換基を有していてもよい炭素原子ｆｉ
１〜１６のアルキル基、Ｒ２は置換基を有していてもよ
い炭素原子数ｌへ１６のアルキル基、アルコキシ基、ア
ルコキシカルボニル基、アシルオキシ基、アルコキシカ
ルボニルオキシ基のいずれかを示し、Ａは置換基を有し
ていてもよい
で表わされる液晶性化合物を少なくとも１種類含有する
ことを特徴とする液晶組成物、特に強誘電性カイラルス
メクチック液晶組成物に係わる。但し、前記−旧式［１
］において、Ｒ１は置換基を有していてもよい炭素原子
数２〜８のアルキル基がより好ましく、またＲ２は置換
基を有していてもよい炭素原子数４〜１４のアルキル基
が好ましく、より好ましくは”ｒＲＺ原子数６〜１２の
アルキル基が良い。[Means for Solving the Problems] and [Operation] That is, the first invention of the present invention is as follows:
(In the formula, R1 is a carbon atom fi which may have a substituent
1 to 16 alkyl group, R2 represents any one of 16 alkyl groups, alkoxy groups, alkoxycarbonyl groups, acyloxy groups, and alkoxycarbonyloxy groups in which the number of carbon atoms is 1, which may have a substituent, and A is The present invention relates to a liquid crystal composition, in particular a ferroelectric chiral smectic liquid crystal composition, characterized by containing at least one type of liquid crystal compound represented by optionally having a substituent. However, the above - old style [1
], R1 is more preferably an alkyl group having 2 to 8 carbon atoms which may have a substituent, and R2 is preferably an alkyl group having 4 to 14 carbon atoms which may have a substituent. , more preferably an alkyl group having 6 to 12 atoms.
さらに、第二の発明は、前記液晶組成物を使用すること
を特徴とする液晶素子、具体的には、前記液晶組成物を
一対の電極基板間に配置してなる強誘電性液晶素子に係
わる。Furthermore, a second invention relates to a liquid crystal element using the liquid crystal composition, specifically a ferroelectric liquid crystal element in which the liquid crystal composition is disposed between a pair of electrode substrates. .
本発明者等は、以上の液晶組成物およびそれを使用した
液晶素子を用いることにより、高速応答性、応答速度の
温度依存性の軽減等の諸特性の改良かなされ、良好な表
示特性か得られることを見い出したものである。The present inventors have found that by using the above liquid crystal composition and a liquid crystal element using the same, various characteristics such as high-speed response and reduced temperature dependence of response speed can be improved, and good display characteristics can be obtained. This is what we discovered.
以下１本発明の詳細な説明する。The present invention will be explained in detail below.
前記−旧式［Ｉ］で表わされる液晶性化合物の具体的な
４］造式の例を以下に示す。A specific example of the formula 4] of the liquid crystalline compound represented by the old formula [I] is shown below.
Ｃ，１１，、舎Ｃ１１□０（）（沢ＯＣ，２１１２５Ｃ
５１１□＋ＣＩ＋２叶◎（トｏｃ、、８．９（Ｉ３）
Ｃ，Ｈ，３８ｃＨ□０（）（沢０→ＣＨ□÷−〇ｓＨ＋
：＋υ
υ
Ｎ
Ｃ，Ｈ，舎Ｃ１１２０３０Ｃ＋ ＯＨ２１υ
ＣｘＩＩｔ＋ＣＨｔＯ＋ ａＨ、ｔ
ｃ ３ｕ、−／、う［Ｘ＝）−ＣＨ，０−（（＝＝シ〕
ｘ−−１ぐ■〆〉−Ｃ−２Ｈ２Ｓ次に本発明て用いる液
晶性化合物の代表的な合成例を下記に示す。C,11,,shaC11□0()(Sawa OC,21125C
511□+CI+2 Kano◎(Tooc,,8.9(I3) C,H,38cH□0()(Sawa0→CH□÷−〇sH+
:+υ υ N C,H,sha C112030C+ OH21υ CxIIt+CHtO+ aH,t c 3u,-/,U[X=)-CH,0-((==shi)
x--1g■〆〉-C-2H2S Next, a typical synthesis example of the liquid crystalline compound used in the present invention is shown below.
合成例１（前記例示化合物Ｎｏ、 ４の合成）（■）
トランス−４−ｎ−プロピルシクロヘキサンカルボン酸
クロライドｌＯｇ （５：１．６■諷ｏｉｌ）をエタノ
ール３ｈｊ＋にとかし、これに少量のトリエチルアミン
を加え室温て１０時間攪拌した。反応混合物を氷水１０
０ｍｆｌに注入し、６Ｎ塩酸水溶液を加え酸性側とした
後、イソプロピルエーテルにより抽出した。有機層を洗
液が中性となるまで水洗を繰り返した後、硫酸マグネシ
ウムにより乾燥した。溶媒留去後、シリカゲルカラムク
ロマトグラフィーにより精製し、トランス−４−ｎ−プ
ロピルシクロヘキサンカルボン酸エチルエステル９．９
ｇを得た。Synthesis Example 1 (Synthesis of Exemplified Compound No. 4) (■)
Trans-4-n-propylcyclohexanecarboxylic acid chloride 10g (5:1.6 ml) was dissolved in ethanol 3hj+, a small amount of triethylamine was added thereto, and the mixture was stirred at room temperature for 10 hours. Pour the reaction mixture into ice water for 10 minutes.
The mixture was injected into 0 mfl, made acidic by adding 6N aqueous hydrochloric acid solution, and then extracted with isopropyl ether. The organic layer was washed with water repeatedly until the washing liquid became neutral, and then dried with magnesium sulfate. After distilling off the solvent, it was purified by silica gel column chromatography to obtain trans-4-n-propylcyclohexanecarboxylic acid ethyl ester9.9
I got g.
１） 水素化アルミニウムリチウム０．７３ｇ（１９
，１ｍｍｏｊ’）を乾燥エーテル３０ｔＩ！に添加し、
１時間加熱還流した。氷水浴中で１０℃程度まで冷却し
た後、乾燥エーテル３０ｆｆ１２に溶かしたトランス−
４−ｎ−プロピルシクロヘキサンカルボン酸エチルエス
テル５ ｇ （２５，５ｍｍｏｆ’）を徐々に滴下した
。滴下終了後、室温で１時間攪拌し、さらに１時間加熱
還流させた。これを酢酸エチル、 ６Ｎ塩酸水溶液で処
理した後、氷水２００■Ｐに注入した。1) Lithium aluminum hydride 0.73g (19
, 1 mmoj') with 30 tI of dry ether! added to,
The mixture was heated under reflux for 1 hour. After cooling to about 10°C in an ice water bath, trans-
5 g (25.5 mmof') of 4-n-propylcyclohexanecarboxylic acid ethyl ester was gradually added dropwise. After the dropwise addition was completed, the mixture was stirred at room temperature for 1 hour, and further heated under reflux for 1 hour. This was treated with ethyl acetate and a 6N aqueous hydrochloric acid solution, and then poured into 200 P of ice water.
イソプロピルエーテルにより抽出した後、有機相を水、
水酸化ナトリウム水＃液、木て順次洗浄し、硫酸マグネ
シウムにより乾燥した。溶媒留去後、シリカゲルカラム
クロマトクラフィーにより精製し、トランス−４−ｎ−
プロピルシクロヘキシルメタノール３．５ｇを得た。After extraction with isopropyl ether, the organic phase was extracted with water,
It was sequentially washed with aqueous sodium hydroxide and wood, and dried with magnesium sulfate. After distilling off the solvent, it was purified by silica gel column chromatography to obtain trans-4-n-
3.5 g of propylcyclohexylmethanol was obtained.
（ｍ） トランス−４−ｎ−プロとルシクロ＼キシルメ
タノール３．４ｇ （２２，４ｍｍｏｆ’）をピリジン
２０ＩＩｊ！に溶かした。これにピリジン２０ｔＩ！に
溶かしたｐ−トルエンスルホン酸クロライド５．３ｇを
氷水浴中て５℃以下に冷却しながら滴下した。室温で１
０時間攪拌した後、氷水２００ｓｊ）に注入した。６Ｎ
塩酸水溶液により酸性側とした後、イソプロピルエーテ
ルで抽出した。有機相を洗液か中性となるまで水洗を繰
り返した後、硫酸マグネシウムにより乾燥した。これを
溶媒留去して、トランス−４−１−プロピルシクロヘキ
シルメチル−ｐ−トルエンスルホネートを得た。(m) Trans-4-n-pro and 3.4 g (22,4 mmof') of lucyclylmethanol in pyridine 20IIj! It was dissolved in Add 20tI of pyridine to this! 5.3 g of p-toluenesulfonic acid chloride dissolved in water was added dropwise while cooling to 5° C. or lower in an ice water bath. 1 at room temperature
After stirring for 0 hours, the mixture was poured into ice water (200 sj). 6N
After making the mixture acidic with an aqueous hydrochloric acid solution, the mixture was extracted with isopropyl ether. The organic phase was washed with water repeatedly until the washing solution became neutral, and then dried with magnesium sulfate. The solvent was distilled off to obtain trans-4-1-propylcyclohexylmethyl-p-toluenesulfonate.
（ＩＶ） ジメチルホルムアミド４０ｔｓｌに５−デ
シル−２−（４’−ヒドロキシフェニル）ピリミジン６
．３ｇ（２０、２ｍｍｏｊ’）を溶かした。これに８５
％水酸化カリウム１．５ｇを加え、＋００’Ｃで１時間
攪拌した。これにトランス−４−ｎ−プロピルシクロヘ
キシルメチル−ｐ−トルエンスルホネート６．９ｇを加
え、さらにＩｏｏｏＣて４時間攪拌した。反応終了後、
これを氷水２００ｍＩ！に注入し、ベンゼンて抽出した
。有機相を水洗した後、硫酸マグネシウムにより乾燥し
た。溶媒留去後、シリカゲルカラムクロマトグラフィー
により精製し、これをさらにエタノール／酢酸エチル混
合溶媒から再結晶して、前記例示化合物Ｎｏ、 ４を得
た。(IV) 5-decyl-2-(4'-hydroxyphenyl)pyrimidine 6 in 40 tsl dimethylformamide
．． 3 g (20.2 mmoj') was dissolved. 85 for this
% potassium hydroxide was added and stirred at +00'C for 1 hour. To this was added 6.9 g of trans-4-n-propylcyclohexylmethyl-p-toluenesulfonate, and the mixture was further stirred at IoooC for 4 hours. After the reaction is complete,
Add this to 200ml of ice water! and extracted with benzene. After washing the organic phase with water, it was dried with magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography, and further recrystallized from a mixed solvent of ethanol/ethyl acetate to obtain the above-mentioned Exemplified Compound No. 4.
Ｉｎ （ａｍ伺）
２９２０．２８／１０，１６０８，１５８４，１４２８
，１２５８゜１１５４、 ８００
相転移温度（”Ｃ）
（Ｓｍ２はＳ＋ｓＡ、 Ｓａｃ以外のスメクチック相、
未同定）合成例２（前記例示化合物Ｎｏ、 １２の合成
）（Ａが−Ｃの−ｉ 山かアルコキシカルボニル基の
場合）
（１） 合成例１（Ｉ）、（ＩＩ）と同様に合成した
トランス−４−ｎ−プロピルシクロヘキシルメタノール
４．０ｇ （２６，３ｍｍｏｊｌ’）をピリジン２５１
２に溶かした。これにピリジン２５＋ｓｉ’に溶かした
ｐ−ｔ−ルエンスルホン酸クロライド６．０ｇを氷水浴
中で５℃以下に冷却しながら滴下した。室温で１２時間
攪拌した後、氷水２００■Ｐに注入した。６Ｎ塩酸水溶
液により酸性側とした後、イソプロピルエーテルて抽出
した。有機相を洗液が中性となるまて水洗を繰り返した
後、硫酸マグネシウムにより乾燥した。これを溶媒留去
してトランス−４−ｎ−プロピルシクロヘキシルメチル
−ｐ−トルエンスルホネートな得た。In (am visit) 2920.28/10, 1608, 1584, 1428
,1258°1154, 800 Phase transition temperature ("C) (Sm2 is S+sA, smectic phase other than Sac,
(Unidentified) Synthesis Example 2 (Synthesis of Exemplified Compound No. 12) (When A is the -i mountain of -C or an alkoxycarbonyl group) (1) Synthesized in the same manner as Synthesis Example 1 (I) and (II) Trans-4-n-propylcyclohexylmethanol 4.0g (26.3mmojl') was added to pyridine 251
Dissolved in 2. 6.0 g of pt-toluenesulfonic acid chloride dissolved in pyridine 25+si' was added dropwise to this while cooling to 5° C. or lower in an ice water bath. After stirring at room temperature for 12 hours, the mixture was poured into 200 μP of ice water. The mixture was made acidic with a 6N aqueous hydrochloric acid solution, and then extracted with isopropyl ether. The organic phase was washed with water repeatedly until the washing solution became neutral, and then dried with magnesium sulfate. The solvent was distilled off to obtain trans-4-n-propylcyclohexylmethyl-p-toluenesulfonate.
＜ ＩＩ ） ジメチルホルムアミド７０＋＊βに４
−デシルオキシカルボニル−４′−ヒドロキシビフェニ
ル９．３ｇ（２６，：ｌｎｍｏｊりを溶かした。これに
８５％水酸化カリウム２．１ｇを加え、１００°Ｃで１
時間３０分攪拌した。これにトランス−４−ｎ−プロピ
ルシクロヘキシルメチル−ｐ−トルエンスルホネート７
．４ｇを加え、さらに１００°Ｃて５時間攪拌した。こ
れを氷水２００ｍｆに注入し、ベンゼンで抽出した。有
機相を水洗した後、硫酸マグネシウムにより乾燥した。<II) Dimethylformamide 70+*β to 4
9.3 g of -decyloxycarbonyl-4'-hydroxybiphenyl (26,:lnmoj) was dissolved. To this was added 2.1 g of 85% potassium hydroxide, and the mixture was heated at 100°C for 1
The mixture was stirred for 30 minutes. To this, trans-4-n-propylcyclohexylmethyl-p-toluenesulfonate 7
．． 4 g was added and further stirred at 100°C for 5 hours. This was poured into 200 mf of ice water and extracted with benzene. After washing the organic phase with water, it was dried with magnesium sulfate.
溶媒留去後、シリカゲルカラムクロマトグラフィーによ
り精製し、さらにエタノール／酢酸エチル混合溶媒から
再結晶して前記例示化合物Ｎｏ、 １２を得た。After distilling off the solvent, the residue was purified by silica gel column chromatography, and further recrystallized from a mixed solvent of ethanol/ethyl acetate to obtain the above-mentioned Exemplary Compound No. 12.
Ｉｎ （ａｍ−’）
２９２０．２８４０，１７１０． ＋６０４． １２
８８，１１９８゜１１１０．８３０． ７７２
相転移温度（°Ｃ）
１１ Ｕ 、 Ｕ
１４１１ 、 ′Ｊ
（Ｓｍ２はＳｍＡ、 Ｓａｃ以外のスメクチック相、未
同定）以上代表的な液晶性化合物の合成法について述べ
たが、一般式［ＩＩで示される他の液晶性化合物も、一
般にパラ置換シクロヘキシルメタノールなトシル化もし
くはハロゲン化した後、アルカリ存在下で、それぞれ対
応するフェノール類と反応させることにより容易に合成
することか出来る。In (am-') 2920.2840,1710. +604. 12
88,1198°1110.830. 772 Phase transition temperature (°C) 11 U, U 1411, 'J (Sm2 is a smectic phase other than SmA and Sac, unidentified) The synthesis method of typical liquid crystalline compounds has been described above. The other liquid crystalline compounds shown can also be easily synthesized by tosylating or halogenating para-substituted cyclohexylmethanol and then reacting the compound with the corresponding phenol in the presence of an alkali.
次に、その主な合成経路を下記に示す。Next, the main synthetic routes are shown below.
Ｒ、−（Ｅ）−ＣＨ□ＯＨ＋ Ｒ、−（Ｅ）−ＣＩｔ
。Ｘ（ｘ； −３Ｏ：ｌへΦトＣＩ＋３ 、 ハ０ゲ
ン）Ｒ，−（Ｅ）−ＣＩ１２Ｘ ＋ ＋＋ｏ＄Ｒ２
（ただし、−ＧＤ−〇〇−はＡを示し、Ａ、 Ｒ，、Ｒ
２はいずれも前記定義の通りである。）
本発明の液晶組成物は前記一般式［ＩＩで示される液晶
性化合物１種以上と他の強誘電性液晶化合物１挿具１−
１あるいは他の強誘電性液晶組成物とを適ちな１１．１
合て混合することにより得ることがてきる。また、本発
明による液晶組成物は、強誘電性液晶Ｍｌ成物、特に強
誘電性カイラルスメクチック液晶組成物か好ましい。R, -(E)-CH□OH+ R, -(E)-CIt
. X(x; -3O:l to Φ CI+3, ha0gen)R, -(E)-CI12X +++o$R2
(However, -GD-〇〇- indicates A, A, R,, R
2 are as defined above. ) The liquid crystal composition of the present invention comprises one or more liquid crystal compounds represented by the general formula [II and other ferroelectric liquid crystal compounds 1-
1 or other ferroelectric liquid crystal compositions as appropriate 11.1
It can be obtained by mixing together. Further, the liquid crystal composition according to the present invention is preferably a ferroelectric liquid crystal composition, particularly a ferroelectric chiral smectic liquid crystal composition.
ＪＬ体的には、前記−旧式［■］て示される液晶性化合
物１種以上と、下記−旧式［ｒｌ］て示される液晶性化
合物１種以上とを有する液晶組成物は、応答速度の温度
依存性か小さい液晶組成物をＩＩ多るのに有効に１動く
。In terms of JL system, a liquid crystal composition having one or more liquid crystal compounds represented by the above-old formula [■] and one or more liquid crystal compounds represented by the following -old formula [rl] has a temperature of response speed. The liquid crystal composition has a small dependence, but it works effectively.
（式中、Ｒ３は直鎖状の）Ｒ素原子数１〜１６のアルキ
ル基、１７４は直鎖状の炭素原子数１〜１２のアルキル
但し、−旧式［ＩＴ］において、Ｒ３は直鎖状の炭素原
子数４〜Ｉ２のアルキル基がより好ましく、Ｒ４は直鎖
状の炭素原子数２−８のアルキル基かより好ましい。(In the formula, R3 is a straight-chain R alkyl group having 1 to 16 atoms, 174 is a straight-chain alkyl group having 1 to 12 carbon atoms. However, - In the old formula [IT], R3 is a straight-chain alkyl group having 1 to 16 carbon atoms. is more preferably an alkyl group having 4 to I2 carbon atoms, and more preferably R4 is a linear alkyl group having 2 to 8 carbon atoms.
また、前記−旧式［ＩＩで表わされる液晶性化合物の少
なくとも１種と、前記−旧式［１１］で示される液晶性
化合物の１種以上と、以下の一般式［ｍ］、［ｌＶ］お
よび［Ｖ］のうちの少なくともいずれか１種以上の液晶
性化合物とを有する液晶組ｒ＆物は、応答速度の温度依
存性を軽減させたまま、さらに低温作動特性を改善させ
ることがてきる。Furthermore, at least one liquid crystal compound represented by the old formula [II], one or more liquid crystal compounds represented by the old formula [11], and the following general formulas [m], [lV] and [ A liquid crystal composite containing at least one kind of liquid crystalline compound among [V] can further improve the low-temperature operating characteristics while reducing the temperature dependence of the response speed.
かから選ばれたものを示す。）
（式中、Ｒ５及びＲ６は直鎖状の炭素原子数ｌ〜１４の
アルキル基を示す。）
イ（］］シ一般式式Ｉ［ＩＩ、［１７１において、Ｒ５
及びＲ６は直鎖状の炭素原子数４〜１２のアルキル基か
より好ましい。Show the selected one. ) (In the formula, R5 and R6 represent a linear alkyl group having 1 to 14 carbon atoms.) In the general formula I [II, [171], R5
and R6 is more preferably a linear alkyl group having 4 to 12 carbon atoms.
一般°式［ＩＩ ］て示される例示化合物（式中、Ｒ７
は直鎖状の炭素原子数１〜１４のアルキル基、Ｒ８は直
鎖状の炭素原子数ｌ〜１４のアルキル基を示す。）
但し、−旧式［Ｖ］において、Ｒ７は直鎖状の炭素原子
数６〜１０のアルキル基かより好ましく、１１８は直鎖
状の炭素原子数２〜８のアルキル基かより好ましい。Exemplary compounds represented by the general formula [II] (wherein R7
represents a linear alkyl group having 1 to 14 carbon atoms, and R8 represents a linear alkyl group having 1 to 14 carbon atoms. ) However, in -old formula [V], R7 is more preferably a linear alkyl group having 6 to 10 carbon atoms, and 118 is more preferably a linear alkyl group having 2 to 8 carbon atoms.
本発明に用いる前記−旧式［１１］ 、ｔｍｌ 、［ｒ
ｖ］及び［Ｖ］て示される液晶性化合物として下記に示
す化合物か使用できる。The above-old type [11], tml, [r
The following compounds can be used as the liquid crystalline compounds represented by [v] and [V].
（２−：ｌ） υ （２−１ｔ） υ υ υ υ 前記−旧式 ［ＴＩ ］ で示される液晶性化合物は、 特開昭６３−２２［］４２ 号公報。(2-:l) υ (2-1t) υ υ υ υ Said - old style [TI] The liquid crystalline compound represented by JP-A-63-22[]42 Publication No.
特開昭６３−１２２６５１号公
報または特開昭６２−２７７３０６号公報等に記載され
ている方法により合成することかてきる。It can be synthesized by the method described in JP-A-63-122651 or JP-A-62-277306.
一般式［Ｉ１１］
て示される例示化合物
（：ｌ−１）
（：１−６）
（］−７）
一般式［ＩＶ］
て示される例示化合物
υ
υ
υ
・服代［Ｖ］
て示される例示化合物
（５−１：１）
υ
（Ｓ−ｔＳ）
前記−服代［Ｖ］
で示される液晶性化合物は、
特開昭６２−１：１８４５４号公報に記載されている方
法により得ることかできる。General formula [I11] Exemplary compound represented by (:l-1) (:1-6) (]-7) General formula [IV] Exemplary compound represented by υ υ υ ・Clothing fee [V] Example shown by The liquid crystalline compound represented by the compound (5-1:1) υ (S-tS) above can be obtained by the method described in JP-A-62-1:18454. .
さらに、本発明者等の実験によれば、前記−服代［Ｉ］
で示される液晶性化合物の少なくとも１種と、
現れる。Furthermore, according to the experiments of the present inventors, the above-mentioned - Clothes cost [I]
Appears with at least one liquid crystalline compound represented by:
ところで、本発明の液晶組成物には、前述の液晶組成物
に、さらに他の液晶性化合物を添加してもよく、例えば
下記の化合物を挙げることかてきる。By the way, in the liquid crystal composition of the present invention, other liquid crystal compounds may be added to the above-mentioned liquid crystal composition, for example, the following compounds may be mentioned.
υ
のうち少なくとも１種の液晶性化合物とを有する液晶組
成物は、低温作動特性の改善に有効であることかわかっ
た。It has been found that a liquid crystal composition containing at least one liquid crystal compound among υ is effective in improving low-temperature operating characteristics.
また、前記−服代［Ｌ］て示される液晶性化合物の少な
くとも１種と、前記−服代［Ｖ］て示される液晶性化合
物とを有する液晶組成物も低温作動特性の４片に有効で
あることかわかった。中でも、−服代［Ｖ］て示される
液晶性化合物群より）；シ素原子数の異なる少なくとも
３種以上の化合物を一般式［Ｉ］て示される液晶性化合
物とともに含有させると、より低温作動特性の改善か顕
著に（ｌＯ）
（Ｉ４）
（Ｉ８）
（２Ｇ）
（＋００）
（＋０７）
（＋０８）
（ＩＩ＋）
（＋１９）
（＋２０）
（＋２２）
Ｃρ
Ｃρ
（１１：ｌ）
（＋１４）
（＋２９）
（＋：１０）
（１：１１）
（１：１２）
（＋３３）
（１：１４）
（＋４１）
（＋４２）
（＋４５）
Ｆ
（＋３６）
（＋４７）
（＋５５）
（＋５７）
（＋５８）
（＋６６）
（＋６７）
（＋６８）
（＋６９）
（＋７０）
（１６：１）
本発明における一般式［ＩＩて示される液晶性化合物と
上述の一般式［Ｉ］以外て示される他の強誘電性液晶性
化合物あるいは強誘電性液晶組成物（以下、強誘電性液
晶材料と略す）との配合割合は、他の強誘電性液晶材料
１００重量部当り、服代［ＩＩで示される液晶性化合物
を１〜５０１１重ｊｔ部、好ましくは１〜２００重量部
とすることか望ましい。Furthermore, a liquid crystal composition containing at least one liquid crystal compound represented by the above-mentioned -Fukujiro [L] and the liquid crystal compound represented by -Fukujiro [V] is also effective for the four types of low-temperature operating characteristics. I realized something. Among them, if at least three or more compounds having different numbers of silicon atoms are included together with the liquid crystalline compound represented by the general formula [I], lower temperature operation can be achieved. Significant improvement in characteristics (lO) (I4) (I8) (2G) (+00) (+07) (+08) (II+) (+19) (+20) (+22) Cρ Cρ (11:l) (+14) ( +29) (+:10) (1:11) (1:12) (+33) (1:14) (+41) (+42) (+45) F (+36) (+47) (+55) (+57) (+58) (+66) (+67) (+68) (+69) (+70) (16:1) Liquid crystalline compounds represented by the general formula [II] in the present invention and other ferroelectric compounds represented by other than the above-mentioned general formula [I] The compounding ratio of the liquid crystal compound or ferroelectric liquid crystal composition (hereinafter referred to as ferroelectric liquid crystal material) is as follows: per 100 parts by weight of other ferroelectric liquid crystal material, It is desirable that the amount is 1 to 5011 parts by weight, preferably 1 to 200 parts by weight.
また、■一般式［ＩＩ及び−服代［ＩＩ ］て示される
液晶性化合物を有する液晶組成物、或いは■一般式［Ｉ
Ｉ及び
のうち少なくとも１種を有する液晶組成物と、■又はく
め以外の別の強誘電性液晶材料との配合割合は、別の強
誘電性液晶材料１００重量部当り、■又は■を５〜５０
０重量部、好ましくは５〜３００重量部とすることか望
ましい。In addition, ■a liquid crystal composition having a liquid crystal compound represented by the general formula [II and -Fukudai [II], or ■a liquid crystal composition having the general formula [I
The compounding ratio of the liquid crystal composition having at least one of I and 2 or another ferroelectric liquid crystal material other than Kume is 5 to 5 parts of 1 or 2 per 100 parts by weight of the other ferroelectric liquid crystal material. 50
It is desirable that the amount is 0 parts by weight, preferably 5 to 300 parts by weight.
さらに、■と一般式［１１１］〜［Ｖ］のうちいずれか
を有する液晶組成物（■）、或いは■−一般式Ｉ］で示
される液晶性化合物及び−旧式［Ｖ］で示される液晶性
化合物のうち３種以上を有する液晶組成物と、■又は■
以外のその他の強誘電性液晶材料との配合割合は、その
他の強誘電性液晶材料１００重量部当り、■又は■を５
〜８００重量部、好ましくは１０〜４００重量部とする
ことか望ましい。Furthermore, ■ and a liquid crystal composition (■) having any one of general formulas [111] to [V], or ■ - a liquid crystal compound represented by general formula I] and - a liquid crystal compound represented by old formula [V] A liquid crystal composition containing three or more types of compounds, and ■ or ■
The blending ratio with other ferroelectric liquid crystal materials is 5 parts of ■ or ■ per 100 parts by weight of other ferroelectric liquid crystal materials.
It is desirable that the amount is 800 parts by weight, preferably 10 to 400 parts by weight.
さらに、本発明による強誘電性液晶素子における強誘電
性液晶層は、先に示したようにして作製した強誘電性液
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、徐々に冷却して液晶層を形成させ常圧に
もどすことが好ましい。Furthermore, the ferroelectric liquid crystal layer in the ferroelectric liquid crystal element according to the present invention can be obtained by heating the ferroelectric liquid crystal composition prepared as described above to an isotropic liquid temperature in vacuum, and placing it in the element cell. It is preferable to encapsulate it and gradually cool it to form a liquid crystal layer and return it to normal pressure.
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素子の一例を示す断面
概略図である。FIG. 1 is a schematic cross-sectional view showing an example of a liquid crystal element having a ferroelectric liquid crystal layer of the present invention, for explaining the structure of the ferroelectric liquid crystal element.
第１図において、符号１は強誘電性液晶層、２はガラス
基板、３は透明電極、４は絶縁性配向制御層、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, 1 is a ferroelectric liquid crystal layer, 2 is a glass substrate, 3 is a transparent electrode, 4 is an insulating alignment control layer, 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Ｉｎ２Ｏ，。The two glass substrates 2 are each made of In2O.
５１１０２あるいはＩＴＯ（インジウム チン オキサ
イド； Ｉｎｄｉｕｍ Ｔｉｎ ０ｘｉｄｅ）等の薄膜
から成る透明電極３か被覆されている。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
てラビンクして、液晶をラビング方向に並べる絶縁性配
向制御層４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、アルミニウム醜化物、ジルコニ
ウム醜化物、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、ポリビニルアセタール、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層として、２層
て絶縁性配向制御層４か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か無機
系ならば黒着法なとて形成でき、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、スプレー塗布法、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
ことかてきる。A transparent electrode 3 made of a thin film of 51102 or ITO (Indium Tin Oxide) is coated thereon. On top of this, a thin film of a polymer such as polyimide is rubbed with gauze, acetate flocked cloth, etc. to form an insulating alignment control layer 4 in which the liquid crystals are aligned in the rubbing direction. Also, as an insulating material,
For example, silicon nitride, hydrogen-containing silicon carbide, silicon oxide, boron nitride, hydrogen-containing boron nitride, cerium oxide, aluminum oxide, zirconium oxide, titanium oxide, magnesium fluoride, and other inorganic materials. Form an insulating layer of material, on which polyvinyl alcohol, polyimide, polyamideimide, polyesterimide, polyparaxylene, polyester, polycarbonate, polyvinyl acetal, polyvinyl chloride, polyvinyl acetate, polyamide, polystyrene, cellulose resin,
The two-layer insulating alignment control layer 4 may be formed by using an organic insulating material such as melamine resin, Yuria resin, acrylic resin, or photoresist resin as the alignment control layer, or an insulating alignment control layer 4 made of an inorganic material or an organic insulating material may be used as the alignment control layer. It may be a single layer of material insulating orientation control layer. If this insulating orientation control layer is inorganic, it can be formed by a black coating method, or if it is organic, it can be formed by a solution in which an organic insulating material is dissolved or its precursor solution (0.1 to 20% by weight in a solvent, preferably (0.2-10% by weight)
It can be applied by a spinner coating method, dip coating method, screen printing method, spray coating method, roll coating method, etc., and then cured and formed under predetermined curing conditions (for example, under heating).
絶縁性配向制御層４の層厚は通常５０人〜１７ｔｕ＋、
好ましくは１００人〜３０００人、さらに好ましくは１
００人〜１０００人か適している。The layer thickness of the insulating orientation control layer 4 is usually 50 to 17 tu+,
Preferably 100 to 3000 people, more preferably 1
Suitable for 00 to 1000 people.
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
間隔に保たれている。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１例えばエポキシ系接着
材を用いて密封する方法かある。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。These two glass substrates 2 are kept at an arbitrary distance by a spacer 5. For example, there is a method in which silica beads or alumina beads having a predetermined diameter are used as spacers and sandwiched between two glass substrates, and the periphery is sealed using a sealing material 1, such as an epoxy adhesive. In addition, a polymer film or glass fiber may be used as a spacer.
この２枚のガラス基板の間に強誘電性液晶が封入されて
いる。A ferroelectric liquid crystal is sealed between these two glass substrates.
強誘電性液晶か封入された強誘電性液晶層１は、一般に
は０．５〜２０ル■、好ましくは１〜５ルｌである。The ferroelectric liquid crystal layer 1 in which the ferroelectric liquid crystal is encapsulated generally has a thickness of 0.5 to 20 l, preferably 1 to 5 l.
透明電極３からはリード線によって外部の電源７に接続
されている。The transparent electrode 3 is connected to an external power source 7 by a lead wire.
またガラス基板２の外側には偏光板８か貼り合わせであ
る。Further, a polarizing plate 8 is bonded to the outside of the glass substrate 2.
第１図は透過型なのて光源９を備えている。The device shown in FIG. 1 is of a transmission type and is equipped with a light source 9.
第２図は１強話電性液晶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。２］ａと２１ｂは、そ
れぞれｌ ｎ ２０ ） 、 Ｓ ｎ ０２あるいはＩ
ＴＯ（Ｉｎｄｉｕｍ−Ｔｉｎ ０ｘｉｄｅ）ｉの薄膜か
らなる透明電極て被覆された基板（ガラス板）てあり、
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Ｓａｃ”相又はＳ＋ｓｌｌ”相の液晶か封入され
ている。太線て示した線２３か液晶分子を表わしており
、この液晶分子２３はその分子に直交した方向に双極子
モーメント（ｐｔ ） ２４を有している。基板２１ａ
と２１ｂ上の電極ｆｉｌｌに一一定の閾値以上の電圧を
印加すると、液晶分子２３のらせん構造かほどけ、双極
子モーメント（Ｐ工）２４がすべて電界方向に向くよう
、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 single strong-talk liquid crystal element. 2] a and 21b are l n 20 ), S n 02 or I
There is a substrate (glass plate) covered with a transparent electrode made of a thin film of TO (Indium-Tin Oxide),
In between, liquid crystal of Sac" phase or S+sll" phase, which is oriented so that the liquid crystal molecular layer 22 is perpendicular to the glass surface, is sealed. A thick line 23 represents a liquid crystal molecule, and this liquid crystal molecule 23 has a dipole moment (pt) 24 in a direction perpendicular to the molecule. Substrate 21a
When a voltage higher than a certain threshold is applied to the electrode fill on the electrodes 21b and 21b, the helical structure of the liquid crystal molecules 23 is unraveled, and the liquid crystal molecules 23 are aligned in the direction such that the dipole moment (P) 24 is all directed in the direction of the electric field. 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. Therefore, for example, if crossed Nicol polarizers are placed above and below the glass surface, the polarity of the applied voltage changes. It is easily understood that this results in a liquid crystal optical modulation element whose optical properties change.
本発明における光学変調素子て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１０Ｐ以下）す
ることかてきる。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かほどけ、その双極子モーメント
Ｐａまたはｐｂは上向き（：］４ａ）又は下向き（：１
４ｂ）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なる電界Ｅａ
又はＥ ｂ？ニア１！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の何れか一方
に配向する。The liquid crystal cell preferably used as the optical modulation element in the present invention can be made sufficiently thin (for example, 10P 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 (:]4a) or downward. (:1
Either state 4b) is taken. In such a cell, an electric field Ea of different polarity above a certain threshold value is applied as shown in FIG.
Or E b? Near 1! When applied by the pressure applying means 31a and 31b, the dipole moment is directed upward 34a or downward 34b depending on the electric field vector of the electric field Ea or Eb.
Accordingly, the liquid crystal molecules are oriented to either the first stable state 33a or the second stable state 33b.
このような強誘電性液晶素子を光学変調素子として用い
ることの利点は、先にも述べたか２つある。There are two advantages of using such a ferroelectric liquid crystal element as an optical modulation element as mentioned above.
その第１は、応答速度か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３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７ｑ：１３ａに配
向するか、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３３ｂに配向して、その分子の向きを変えるか、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か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, for example with reference to FIG. 3, the electric field Ea
When the voltage is applied, the liquid crystal molecules are oriented in the first stable state 7q:13a, or this state is stable even when the electric field is turned off. or,
When an electric field Eb in the opposite direction is applied, the liquid crystal molecules are oriented in a second stable state 33b and remain in this state even if the orientation of the molecules is changed or the electric field is turned off. Further, unless the applied electric field Ea or Eb exceeds a certain threshold value, the previous orientation state is maintained.
［実施例］
以下、実施例により本発明について更に詳細に説明する
か、本発明はこれらの実施例に限定されるものてはない
。[Examples] Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.
実施例１
前記例示強誘電性液晶性化合物を下記の重量部で混合し
て液晶組成物Ａを得た。Example 1 Liquid crystal composition A was obtained by mixing the exemplified ferroelectric liquid crystalline compounds in the following parts by weight.
例示化合物Ｎｏ、 重量部
（：１−１） ５６
（４−１） ＋４
（２−４） ７．５（２−５）
ｚｚ、ｓ以下に液晶組成物Ａの相転移温
度（’Ｃ）を示す。Exemplary compound No., parts by weight (:1-1) 56 (4-1) +4 (2-4) 7.5 (2-5)
The phase transition temperature ('C) of liquid crystal composition A is shown below.
相転移温度（℃）
次に、この液晶組Ｊ＆、物Ａに対して合成例１，２てと
りあげた例示化合物４．１２を
ｆｆｉ贋部
液晶組成物Ａ ９０
例示化合物Ｎｏ、 ４ ６．７例示化合物Ｎ
ｏ、１２ ３．３の割合て混合し、液晶組成
物Ｂを得た。この液晶組成物Ｂの相転移温度（°Ｃ）は
以下の通ってあった。Phase transition temperature (℃) Next, for this liquid crystal composition J&, compound A, exemplified compound 4.12 taken up in Synthesis Examples 1 and 2 was added to ffi fake liquid crystal composition A 90 exemplified compound No. 4 6.7 Compound N
A liquid crystal composition B was obtained by mixing at a ratio of 3.3 to 12 o. The phase transition temperature (°C) of this liquid crystal composition B was as follows.
相転移温度（°Ｃ）
次に、２枚の（］、７＋ａｍ厚のガラス板を用意し、そ
れぞれのガラス板りにＩＴＯ膜を形成し、電圧印加゛１
［極を作成し、さらにこの上に５ｉｎ２を蒸着させ絶縁
層とした。ガラス板−ヒにシランカップリング剤〔信越
化学■製、ＫＢＭ−６０２） ０．２％イソプロピルア
ルコール溶液を回転数２０００ｒ、ｐ、ａ＋、のスピー
ドて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。Phase transition temperature (°C) Next, two glass plates with a thickness of 7+am were prepared, an ITO film was formed on each glass plate, and a voltage was applied to the plate.
[A pole was created, and 5in2 was further deposited on top of the pole to form an insulating layer. A 0.2% isopropyl alcohol solution of a silane coupling agent (manufactured by Shin-Etsu Chemical Co., Ltd., KBM-602) was applied to the glass plate for 15 seconds at a rotational speed of 2000 r, p, a+, to perform surface treatment. After this 120
A heat drying process was performed at ℃ for 20 minutes.
さらに、表面処理を行なったＩＴＯ膜付きのガラス板上
にポリイミド樹脂前駆体（東し■製、 ５ｐ−５１０）
１．５％ジメチルアセトアミド溶液を回転数２０００
ｒ、ｐ、１１．のスピンナーで１５秒間塗布した。成：
り後、６０分間、３００°Ｃで加熱縮合焼成処理を施１
ノだ。この時の塗膜の膜厚は、約２５０人てあった。Furthermore, a polyimide resin precursor (manufactured by Toshi ■, 5p-510) was placed on a glass plate with a surface-treated ITO film.
1.5% dimethylacetamide solution at 2000 rotations.
r, p, 11. It was applied for 15 seconds using a spinner. Form:
After heating, heat condensation baking treatment was performed at 300°C for 60 minutes.
No. The thickness of the coating film at this time was about 250.
この焼成後の被膜には、アセテート植毛布によるラビン
グ処理かなされ、その後イソプロピルアルコール液て洗
浄し、平均粒径２ｇｍのアルミナビーズな一方のガラス
板りに散布した後、それぞ１１のラビング処理軸か互い
に平行となる様にし、接着シール剤（チッソ■製、リク
ソンボンド）を用いてガラス板をはり合わせ、６０分間
１００°Ｃにて加熱乾燥しセルを作成した。このセルの
セル厚をベレック（＆粗板によって測定したところ、約
２座ｍてあった。After firing, the coating was rubbed with acetate flocked cloth, then washed with isopropyl alcohol solution, and alumina beads with an average particle size of 2 gm were sprinkled on one glass plate. The glass plates were glued together using an adhesive sealant (manufactured by Chisso ■, Rixon Bond) so that they were parallel to each other, and dried by heating at 100° C. for 60 minutes to create a cell. The cell thickness of this cell was measured using a Berek plate and was found to be about 2 m thick.
このセルに前記液晶組成物Ｂを等方性液体状態て注入し
、等吉相から５６Ｃ／ｈで２５℃まて徐冷することによ
り強誘電性液晶素子を作成した。A ferroelectric liquid crystal element was prepared by injecting the liquid crystal composition B in an isotropic liquid state into this cell and slowly cooling it from the tokichi phase to 25° C. at 56 C/h.
この強誘電性液晶素子を使って自発分極の大きさＰｓと
ピーク・トウ・ピーク電圧Ｖ ｌ、ｐ＝ ２０Ｖの電圧
印加により直交ニコル下ての光学的な応答（透過光１１
Ｙ変化Ｏ〜９０％）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, the optical response under crossed Nicols (transmitted light 11
The response speed (hereinafter referred to as optical response speed) was measured by detecting the Y change (O~90%). The results are shown below.
２５ °Ｃ３５℃
応答速度（μ５ｅｃ） ２８０ １１０Ｐｓ
（ｎＣ／ｃｍ２） ２４．２ １５
．１また、２５°Ｃにおけるこの駆動時のコントラスト
は１２て明瞭なスイッチング動作か観察された。25 °C35 °C Response speed (μ5ec) 280 110Ps
(nC/cm2) 24.2 15
．． 1 Also, the contrast during this drive at 25°C was 12 and a clear switching operation was observed.
比れ例１
実施例１て混合した液晶組成物Ａをセル内に注入する以
外は、全〈実施例１と同様の方法て強誘電性液晶素子を
作成し、自発分極の大きさＰｓと光学応答速度を測定し
た。その結果を次に示す。Comparison Example 1 A ferroelectric liquid crystal device was prepared in the same manner as in Example 1 except that the liquid crystal composition A mixed in Example 1 was injected into the cell, and the spontaneous polarization magnitude Ps and optical The response speed was measured. The results are shown below.
２５℃ ３５℃
応答速度し５ｅｅ） ４３０ ｔＳＯＰｓ
（ｎＣ／ｃ１２） ３６．５ ２６．２実施例１
と比較例１より明らかな様に１本発明による液晶性化合
物を含有する強誘電性液晶素子の方か粘性か低下してお
り（前述の式［Ａ］より、２５°Ｃにおける粘度か約１
７２になっている）、自発分極の大きさのＩＩｎとは逆
に、低温における作動特性、高速応答性が改善され、か
つ応答速度の温度依存性が著しく軽減されている。25℃ 35℃ Response speed 5ee) 430 tSOPs
(nC/c12) 36.5 26.2 Example 1
As is clear from Comparative Example 1, the viscosity of the ferroelectric liquid crystal element containing the liquid crystal compound according to the present invention is lower (from the above formula [A], the viscosity at 25°C is approximately 1
72), and contrary to the spontaneous polarization of IIn, the low-temperature operating characteristics and high-speed response are improved, and the temperature dependence of the response speed is significantly reduced.
実施例２
実施例１て用いた例示化合物Ｎｏ、 ４．１２に代えて
下記の相転移を示す例示化合物Ｎｏ、５．１５を重量部
２．５．７．５の割合て混合して液晶組成物Ｃを得た。Example 2 In place of Exemplified Compound No. 4.12 used in Example 1, Exemplified Compound No. 5.15 exhibiting the following phase transition was mixed in a proportion of 2.5.7.5 parts by weight to prepare a liquid crystal composition. I got item C.
相転移温度（°Ｃ）
例示化合物Ｎｏ、 ５
例示化合物Ｎｏ、 １５
この液晶組成物Ｃを用いたほかは実施例１と同様の方法
て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、スイッチング状態等を観察した
。この液晶素子内の均一配向性は良好であり、モノドメ
イン状態が得られた。Phase transition temperature (°C) Exemplified Compound No. 5 Exemplified Compound No. 15 A ferroelectric liquid crystal element was prepared in the same manner as in Example 1 except that this liquid crystal composition C was used. The optical response speed was measured using the method and the switching state etc. were observed. The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.
測定結果を次に示す。The measurement results are shown below.
２５℃ ３５’Ｃ
応答速度（ｇｓｅｃ） ２９０ １２５Ｐｓ
（ｎｃ／ｃｍ２） ２１５ １３．８また、２
５°Ｃにおけるこの駆動時のコントラストは１１て、明
瞭なスイッチング動作がｆｉｌｌ察され、電圧印加を止
めた際の双安定性も良好であった。25℃ 35'C Response speed (gsec) 290 125Ps
(nc/cm2) 215 13.8 Also, 2
The contrast during this drive at 5° C. was 11, clear switching action was observed, and bistability was also good when voltage application was stopped.
実施例３
実施例１て用いた例示化合物Ｎｏ、 ４．１２に代えて
下記の相転移を示す例示化合物Ｎｏ、 １４．３０を重
１部ｌ０９５の割合で混合して液晶組成物りを得た。Example 3 In place of Exemplified Compound No. 4.12 used in Example 1, Exemplified Compound No. 14.30 exhibiting the following phase transition was mixed at a ratio of 1 part by weight 1095 to obtain a liquid crystal composition. .
相転移温度（℃）
例示化合物Ｎｏ、 １４
例示化合物Ｎｏ、 ３０
この液晶組成物りを用いたほかは、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、スイッチング状態等を観察し
た。この液晶素子内の均一配向性は良好であり、モノド
メイン状態か得られた。Phase transition temperature (°C) Exemplified compound No. 14 Exemplified compound No. 30 A ferroelectric liquid crystal element was prepared in the same manner as in Example 1 except that this liquid crystal composition was used. The optical response speed was measured using the method and the switching state etc. were observed. The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.
Δ１１１定結果を次に示す。The Δ111 constant results are shown below.
２５°Ｃ３５℃
応答速度（ｐｓｅｃ） ２７０ ９５Ｐｓ
（ｎＣ／ｃｍ２） ２４．８ １６．９また、
２５℃におけるこの駆動時のコントラストは１４て、明
瞭なスイッチン）り動作か観察され、電圧印加を止めた
際の双安定性も良好てあった、実施例４
実施例１て用いた例示化合物Ｎｏ、見に代えて下記の相
転移を示す例示化合物Ｎｏ、 ２７を３．３重量部混合
して液晶組ｒＲ，物Ｅを得た。25°C35°C Response speed (psec) 270 95Ps
(nC/cm2) 24.8 16.9 Also,
The contrast during this drive at 25° C. was 14, clear switching behavior was observed, and the bistability was also good when the voltage application was stopped.Example 4 Exemplary compound used in Example 1 In place of No. 2, 3.3 parts by weight of Exemplary Compound No. 27 exhibiting the following phase transition was mixed to obtain liquid crystal composition rR, product E.
相転移温度（°Ｃ）
例示化合物Ｎｏ、 ２７
この液晶組成物Ｅを用いたほかは実施例１と同様の方法
て強誘電性液晶素子を作成し、実施例１と同様の方法で
光学応答速度を側足し、スイッチング状態等を観察した
。この液晶素子内の均一配向性は良好であり、モノドメ
イン状態か得られた。Phase transition temperature (°C) Exemplary compound No. 27 A ferroelectric liquid crystal element was prepared in the same manner as in Example 1 except that this liquid crystal composition E was used, and the optical response speed was determined in the same manner as in Example 1. I put it on the side and observed the switching state, etc. The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.
測定結果を次に示す。The measurement results are shown below.
２５’Ｃ３５℃
応答速度（ｐｓｅｃ） ２６５ １００Ｐｓ
（ｎＣ／ｃｍ”） ２３．６ １４．２また、
２５℃におけるこの駆動時のコントラストは１１で、明
瞭なスイッチング動作か観察され、電圧印加を止めた際
の双安定性も良好であった。25'C35℃ Response speed (psec) 265 100Ps
(nC/cm”) 23.6 14.2 Also,
The contrast during this drive at 25° C. was 11, a clear switching operation was observed, and the bistability was also good when the voltage application was stopped.
実施例５
実施例１て用いた例示化合物Ｎｏ、 ４．１２に代えて
例示化合物Ｎｏ、 １４をＩＯ０重量部混して液晶組成
物Ｆを得た。Example 5 In place of exemplified compound No. 4.12 used in Example 1, IO0 parts by weight of exemplified compound No. 14 was mixed to obtain liquid crystal composition F.
この液晶組成物Ｆを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、スイッチング状態等を観察した
。この液晶素子内の均一配向性は良好であり、モノドメ
イン状態か得られた。A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that this liquid crystal composition F was used, and the optical response speed was measured in the same manner as in Example 1, and the switching state and the like were observed. The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.
測定結果を次に示す。The measurement results are shown below.
２５ ０Ｃ３５℃
応答速度（終５ｅｃ） ３００ １１５Ｐｓ
（ｎＣ／ｃｎ＋２） ２５．：Ｉ １５
．１また、２５℃におけるこの駆動時のコントラストは
１３て、明瞭なスイッチング動作かｉＪ２察され、電圧
印加を止めた際の双安定性も良好であった。25 0C35℃ Response speed (final 5ec) 300 115Ps
(nC/cn+2) 25. :I 15
．． 1 Furthermore, the contrast during this drive at 25° C. was 13, indicating a clear switching operation, and the bistability when voltage application was stopped was also good.
実施例６
実施例１て用いた例示化合＠Ｎｏ、 ４ 、１２に代え
て下記の相転移を示す例示化合物Ｎｏ、 １９．２１を
重７４部３．３．６．７の割合で混合して液晶組成物Ｇ
を得た。Example 6 In place of the exemplified compounds @No. 4 and 12 used in Example 1, exemplified compound No. 19.21 exhibiting the following phase transition was mixed in a proportion of 74 parts by weight and 3.3.6.7 parts by weight. Liquid crystal composition G
I got it.
相転移温度（°Ｃ）
例示化合物Ｎｏ、す
例示化合物Ｎｏ、吋
この液晶組成物Ｇを用いたほかは実施例１と同様の方法
て強誘電性液晶素子を作成し、実施ｈ１と同様の方法で
光学応答速度を測定し、スイッチング状態等を１１Ｊｌ
察した。この液晶素子内の均一配向性は良好であり、モ
ノドメイン状Ｉ凪か得られた。Phase transition temperature (°C) A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that Exemplified Compound No., Exemplified Compound No., and Exemplary Compound No. Measure the optical response speed and check the switching state etc. at 11Jl.
I guessed it. The uniform alignment within this liquid crystal element was good, and a monodomain I-mode was obtained.
測定結果を次に示す。The measurement results are shown below.
２５ ℃ ３５ °Ｃ
応答速度（ｇｓｅｃ） ２８０ １００Ｐｓ
（ｎ（：／ｃ１１２） ２：１．３
１：１．５また、２５℃におけるこの駆動時のコント
ラストはｌ！て、明瞭なスイッチング動作か観察され、
電圧印加を止めた際の双安定性も良好てあった。25 °C 35 °C Response speed (gsec) 280 100Ps
(n(:/c112) 2:1.3
1:1.5 Also, the contrast during this drive at 25°C is l! Clear switching behavior was observed,
The bistability was also good when the voltage application was stopped.
実施例７
実施例１て用いた例示化合物Ｎｏ、 ４ 、１２に代え
て下記の相転移を示す例示化合物Ｎｏ、 ３７を５重量
部混合して液晶組成物Ｈを得た。Example 7 In place of exemplified compounds No. 4 and 12 used in Example 1, 5 parts by weight of exemplified compound No. 37 exhibiting the following phase transition was mixed to obtain a liquid crystal composition H.
相転移温度（”Ｃ）
例示化合物Ｎｏ、 ３７
この液晶組成物Ｈを用いたほかは実施例１と同様の方法
て強誘電性液晶素子を作成し、実施例１と同様の方法て
光学応答速度を測定し、スイッチンク状ｙＥ等を！１１
！察した。この液晶素子内の均一配向性は良好てあり、
モノドメイン状態か得られた。Phase transition temperature ("C) Exemplary compound No. 37 A ferroelectric liquid crystal device was prepared in the same manner as in Example 1 except that this liquid crystal composition H was used, and the optical response speed was determined in the same manner as in Example 1. Measure the switch shape yE, etc.!11
! I guessed it. The uniform alignment within this liquid crystal element is excellent;
A monodomain state was obtained.
測定結果を次に示す。The measurement results are shown below.
２５ °０ ３５ ℃
応答速度（ＩＬｓｅｃ） ：１２０ １：１５
Ｐｓ （ｎｃ八：ｍ”） ２４．９
１４．１また、２５°Ｃにおけるこの駆動時のコントラ
ストは１２て、明瞭なスイッチング動作か観察され、電
圧印加を止めた際の双安定性も良好てあった。25 °0 35 °C Response speed (ILsec): 120 1:15
Ps (nc8:m”) 24.9
14.1 Furthermore, the contrast during this drive at 25° C. was 12, clear switching behavior was observed, and good bistability was observed when voltage application was stopped.
実施例８
実施例１て使用した液晶組成物Ａに代えて、前記例示強
誘電性液晶性化合物を下記の重量部で混合した液晶組成
物Ｉを用い、液晶組成物Ｊを作成Ｖ／だ。これを用いた
他は実施例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。Example 8 In place of the liquid crystal composition A used in Example 1, a liquid crystal composition J was prepared by using a liquid crystal composition I prepared by mixing the exemplified ferroelectric liquid crystal compound in the following parts by weight. A ferroelectric liquid crystal element was produced in the same manner as in Example 1 except that this was used, and the optical response speed was measured in the same manner as in Example 1.
液晶組成物Ｉ 例示化合物Ｎｏ、 重量部 （５−：ｌ） ５０ 結果を次に示す。Liquid crystal composition I Exemplary compound No., parts by weight (5-:l) 50 The results are shown below.
２５℃ ３５℃ ｓｏ−’ｃ
応答速度（ル５ｅｃ） ６２０ ：１９０
２００比較例２
実施例８で混合した液晶組成物■をセル内に柱入する以
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、実施例１と同様の方法で光学応答速度を測定した
。25℃ 35℃ so-'c response speed (le 5ec) 620:190
200 Comparative Example 2 A ferroelectric liquid crystal element was prepared in the same manner as in Example 1 except that the liquid crystal composition (■) mixed in Example 8 was injected into the cell. The optical response speed was measured.
結果を次に示す。The results are shown below.
２５℃ ３５°Ｃ５０℃
応答速度（ｇｓｅｃ） ７：１０ ５１０
２３０実施例９
実施例２て使用した実施例１の液晶組成物Ａに代えて、
実施例８て示した液晶組成物■を用い、液晶組成物Ｋを
作成した。これを用いた他は実施例１と同様の方法で強
誘電性液晶素子を作成し。25℃ 35℃50℃ Response speed (gsec) 7:10 510
230 Example 9 Instead of liquid crystal composition A of Example 1 used in Example 2,
A liquid crystal composition K was prepared using the liquid crystal composition (1) shown in Example 8. A ferroelectric liquid crystal element was produced in the same manner as in Example 1 except that this was used.
実施例１と同様の方法で光学応答速度を測定した。The optical response speed was measured in the same manner as in Example 1.
結果を次に示す。The results are shown below.
２５ ℃ ３５ ℃ ５０ ℃応答速度し
５ｅｃ） ６４０ ４０５ ２１０実施例
１〜９と比較例１．２の結果より明らかな様に、本発明
に係わる骨格中にシクロヘキサン環を有する非光学活性
液晶性化合物を含有する液晶組成物Ｂ〜Ｈ及びＪ、には
、それらを含有しない液晶組成物Ａ、Ｉと比べ低温作動
特性が非常に改善され、応答速度の温度依存性が小さく
なっていることか認られる。25°C 35°C 50°C Response speed (5 ec) 640 405 210 As is clear from the results of Examples 1 to 9 and Comparative Example 1.2, the non-optically active liquid crystal compound having a cyclohexane ring in the skeleton according to the present invention It has been observed that liquid crystal compositions B to H and J containing the above have greatly improved low-temperature operating characteristics and have reduced temperature dependence of response speed compared to liquid crystal compositions A and I that do not contain them. It will be done.
実施例１０
前記例示強誘電性液晶性化合物を下記の重量部で混合し
、液晶組成物りを作成した。Example 10 The above-mentioned exemplary ferroelectric liquid crystal compounds were mixed in the following parts by weight to prepare a liquid crystal composition.
例示化合物Ｎｏ、 重量部 これに、′例示化合物Ｎｏ、耳、ぜを 重量部 液晶組成物Ｌ ８５ 例示化合物Ｎｏ、 ３０ ｔ。Exemplary compound No., parts by weight To this, 'Exemplary compound No. Weight part Liquid crystal composition L 85 Exemplary compound No. 30 t.
例示化合物Ｎｏ、旦 ５ の割合で混合し液晶組成物Ｍを作成した。Exemplary compound No. 5 A liquid crystal composition M was prepared by mixing in the following proportions.
この液晶組成物を用いた他は実施例１と同様の方法で光
学応答速度を測定し、スイッチング状態等を観察した。The optical response speed was measured in the same manner as in Example 1 except that this liquid crystal composition was used, and the switching state and the like were observed.
この液晶素子内の均一配向性は良好であり、モノドメイ
ン状態か得られた。The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.
測定結果を次に示す。The measurement results are shown below.
２５°Ｃ３５°Ｃ４５℃
応答速度（ｍｓｅｃ） ３．８０ ２．０５
１．：１５また、明瞭なスイッチング動作が観察さ
れ、電圧印加を止めた際の双安定性も良好であった。25°C35°C45°C Response speed (msec) 3.80 2.05
1. :15 Also, a clear switching action was observed, and the bistability was also good when the voltage application was stopped.
比較例３
実施例１０て混合した液晶組成物りをセル内に注入する
以外は全〈実施例１と同様の方法て強誘電性液晶素子を
作成し、実施例１と同様の方法て光学応答速度を測定し
た。Comparative Example 3 A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that the liquid crystal composition mixed in Example 10 was injected into the cell, and an optical response was obtained in the same manner as in Example 1. The speed was measured.
Ｊｌｌｌｌｌｌ全結果示す。Show all results.
２５℃ ３５℃ ４５℃
応答速度（ｍｓｅｃ） ５．＋０ ２．７５
１．７０実施例１１
実施例１Ｏで用いた例示化合物Ｎｏ、耳、 ４２にかえ
て、例示化合物Ｎｏ、４０．５６を下記の重量部て混合
し、液晶組成物Ｎを作成した。25℃ 35℃ 45℃ Response speed (msec) 5. +0 2.75
1.70 Example 11 In place of Exemplified Compound No. 42 used in Example 1O, Exemplified Compound No. 40.56 was mixed in the following parts by weight to prepare Liquid Crystal Composition N.
重量部
液晶組成物１． ９０
０例示化物Ｎｏ、 ４０ ７
例示化合物Ｎｏ、 ５６ ３
この液晶組成物を用いた他は実施例１と同様の方法で光
学応答速度をＸ１１定し、スイ・ンチング状態等を観察
した。この液晶素子内の均一配向性は良好であり、モノ
ドメイン状態か得られた。Parts by weight Liquid crystal composition 1. 900 Exemplified Compound No. 40 7 Exemplified Compound No. 56 3 The optical response speed was determined at X11 in the same manner as in Example 1 except that this liquid crystal composition was used, and the switching state and the like were observed. The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.
測定結果を次に示す。The measurement results are shown below.
２５℃ ３５℃ ４５℃
応答速度（ｍｓｅｃ） ３．９５ ２．１０
１．４０また、明瞭なスイッチング動作か観察され
、電圧印加を止めた際の双安定性も良好てあった。25℃ 35℃ 45℃ Response speed (msec) 3.95 2.10
1.40 Also, clear switching behavior was observed, and good bistability was observed when voltage application was stopped.
実施例１０．１１と比較例３からも明らかな様に、本発
明による液晶性化合物を含有する液晶組成物Ｍ、Ｎは、
それらを含有しない液晶組成物りと比べ、特に低温での
作動特性が改善されている。As is clear from Example 10.11 and Comparative Example 3, the liquid crystal compositions M and N containing the liquid crystal compound according to the present invention were
Compared to liquid crystal compositions that do not contain them, the operating characteristics, especially at low temperatures, are improved.
また、温度依存性も若干ながら小さくなっている。Furthermore, the temperature dependence is also slightly reduced.
実施例１２
前記例示強誘電性液晶性化合物を下記の重量部で混合し
、液晶組成物Ｏを作成した。Example 12 The above-mentioned exemplary ferroelectric liquid crystal compounds were mixed in the following parts by weight to prepare a liquid crystal composition O.
例示化合物Ｎｏ、 重量部
＋、５ ２０
２−８ ＋ ５これ
に、例示化合物Ｎｏ、４２．４６を重量部
液晶組成物０８８
例示化合物Ｎｏ、 ４２ ８
例示化合物Ｎｏ、 ４６ ４
の割合て混合し液晶組ｒ＆物Ｐを作成した。Exemplified Compound No. 42.46 is mixed with Exemplified Compound No. 42.46 in a ratio of 088 Exemplified Compound No. 42 8 Exemplified Compound No. 46 4 to the Exemplified Compound No. 42.46 to form a liquid crystal composition. I created a set r&mono P.
この液晶組成物を用いた他は実施例１と同様の方法て光
学応答速度を測定し、スイッチング状態等を観察した。The optical response speed was measured in the same manner as in Example 1 except that this liquid crystal composition was used, and the switching state and the like were observed.
この液晶素子内の均一配向性は良好であり、モノドメイ
ン状態か得られた。The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.
？１１１定結果を次に示す。? 111 results are shown below.
２５℃ ３５６Ｃ４５℃
応答速度（ｐｓｅｃ） ２６０ １９５
１４０また、明瞭なスイッチング動作かｆｉｌｌ察され
、電圧印加を一ヒめた際の双安定性も良好てあった。25℃ 356C45℃ Response speed (psec) 260 195
140 Furthermore, a clear switching action was observed, and the bistability was also good when the voltage application was stopped.
比較例４
実施例１２で混合した液晶組成物０をセル内に注入する
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、実施例１と同様の方法で光学応答速度を測定し
た。Comparative Example 4 A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that the liquid crystal composition 0 mixed in Example 12 was injected into the cell, and the optical response was determined in the same manner as in Example 1. The speed was measured.
測定結果を次に示す。The measurement results are shown below.
２５６Ｃ３５℃ ４５°Ｃ
応答速度（ｐｓｅｃ） ３０５ ２２０
１４５実施例１３
実施例１２で用いた例示化合物Ｎｏ、４２．４６にかえ
て、例示化合物Ｎ０１１６．３０を下記の重量部て混合
１ノ、液晶組成物Ｑを作成した。256C35℃ 45℃ Response speed (psec) 305 220
145 Example 13 In place of Exemplified Compound No. 42.46 used in Example 12, Exemplified Compound No. 116.30 was mixed with the following parts by weight to prepare Liquid Crystal Composition Q.
重量部
液晶組成物０ ９０
例示化合物Ｎｏ、 １６ ４
例示化合物Ｎｏ、 ３０ に
の液晶組成物を用いた他は実施例１と同様の方法て光学
応答速度を測定し、スイッチング状態環τ観察した。こ
の液晶素子内の均一配向性は良好であり、モノドメイン
状態か得られた。Part by Weight Liquid Crystal Composition 0 90 Exemplary Compound No. 16 4 Exemplary Compound No. 30 The optical response speed was measured in the same manner as in Example 1, except that the liquid crystal compositions of Exemplary Compound No. 30 were used, and the switching state ring τ was observed. The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.
測定結果を次に示す。The measurement results are shown below.
２５９Ｃ３５°Ｃ４５℃
応答速度（ｐｓｅｃ） ２３０ １７５
１３０また。明瞭なスイッチング動作が観察され、電圧
印加を止めた際の双安定性も良好であった。259C35°C45°C Response speed (psec) 230 175
130 again. A clear switching behavior was observed, and good bistability was observed when the voltage application was stopped.
実施例１２． ｌ：ｌと比較例４からも明らかな様に、
本発明による液晶性化合物を含有する液晶組成物Ｐ、Ｑ
は、それらな含有しない液晶組成物０と比べ、特に低温
作動特性が改善され、応答速度の温度依存性か小さくな
っていることがわかる。Example 12. As is clear from l:l and Comparative Example 4,
Liquid crystal compositions P and Q containing liquid crystal compounds according to the present invention
It can be seen that the low-temperature operating characteristics are particularly improved and the temperature dependence of the response speed is reduced compared to the liquid crystal composition 0 which does not contain these components.
実施例１４
一実施例１て使用したポリイミド樹脂前駆体１．５％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−１１７） ２％水溶液を
用いた他は、実施例１と全く同様の方法で強誘電性液晶
素子を作成し、実施例１と同様の方法て光学応答速度を
測定した。その結果を次に示す。Example 14 The procedure of Example 1 was repeated, except that a 2% aqueous solution of polyvinyl alcohol resin (manufactured by Kuraray ■, PVA-117) was used in place of the 1.5% dimethylacetamide solution of the polyimide resin precursor used in Example 1. A ferroelectric liquid crystal device was prepared in exactly the same manner as in Example 1, and its optical response speed was measured in the same manner as in Example 1. The results are shown below.
２５ ℃ ３５ ℃
応答速度（終５ｅｅ） ２９５ １２０また、
２５°Ｃにおけるこの駆動時におけるコントラ・ストは
１４てあった。25 ℃ 35 ℃ Response speed (final 5ee) 295 120
The contrast during this drive at 25°C was 14.
実施例１５
実施例１で使用したＳｉＯ□を用いずに、ポリイミド樹
脂たけで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、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。Example 15 A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that the alignment control layer was made only of polyimide resin without using SiO□ used in Example 1. The optical response speed was measured in the same manner as in Example 1. The results are shown below.
２５℃ ３５℃
応答速度（μ５ｅｃ） ２５５ ９０実施例
１４．１５より明らかな様に、素子構成を変えた場合て
も本発明に係わる強調′電性液晶組成物を含有する素子
は、実施例１と同様に、低温作動特性が非常に改善され
、かつ、応答速度の温度依存性の軽減されたものとなっ
ている。25°C 35°C Response speed (μ5ec) 255 90 As is clear from Example 14.15, even if the element configuration is changed, the element containing the enhanced' conductive liquid crystal composition according to the present invention remains the same as in Example 1. Similarly, the low-temperature operating characteristics are greatly improved, and the temperature dependence of the response speed is reduced.
［発明の効果］
以上説明した様に、本発明の液晶性化合物を含有する強
誘電性液晶組成物を使用した素子は、スイッチング動作
か良好で、低温作動特性の改善されだ液晶素子、及び応
答速゛度の温度依存性の軽減された液晶素子とすること
ができる。[Effects of the Invention] As explained above, the device using the ferroelectric liquid crystal composition containing the liquid crystal compound of the present invention has good switching operation and improved low temperature operating characteristics. A liquid crystal element with reduced temperature dependence of speed can be obtained.
第１図は本発明の強誘電性液晶層を用いた液晶表示素子
の一例を示す断面概略図、第２図および第３図は強誘電
性液晶素子の動作説明のために、素子セルの一例を模式
的に表わす斜視図である。
■・・・強誘電性液晶層 ２・・・ガラス基板３・・・
透明電極 ４・・・絶縁性配向制御層５・・・ス
ペーサー ６・・・リード線７・・・電源
８・・・偏光板９・・・光源 Ｉ。・・
・入射光Ｉ・・・透過光
２１ａ・・・基板 ２１ｂ・・・基板２２・・
・液晶分子層 ２３・・・液晶分子２４・・・双極
子モーメント（Ｐｌ）
：ｌＩａ、３１ｂ・・・電圧印加手段
３３ａ・・・第１の安定状態
３３ｂ・・・第２の安定状態
３４ａ・・・北向き双極子モーメント
３４ｂ
・・・下向き双極子モーメント
Ｅａ・・・上向きの電界
Ｅｂ・・・下向きの電界FIG. 1 is a schematic cross-sectional view showing an example of a liquid crystal display element using a ferroelectric liquid crystal layer of the present invention, and FIGS. 2 and 3 are examples of an element cell for explaining the operation of a ferroelectric liquid crystal element. FIG. ■...Ferroelectric liquid crystal layer 2...Glass substrate 3...
Transparent electrode 4... Insulating alignment control layer 5... Spacer 6... Lead wire 7... Power supply
8...Polarizing plate 9...Light source I.・・・
- Incident light I...Transmitted light 21a...Substrate 21b...Substrate 22...
-Liquid crystal molecule layer 23...Liquid crystal molecules 24...Dipole moment (Pl): lIa, 31b...Voltage application means 33a...First stable state 33b...Second stable state 34a. ...Northward dipole moment 34b ...Downward dipole moment Ea ...Upward electric field Eb ...Downward electric field
Claims (8)
１〜１６のアルキル基、Ｒ＿２は置換基を有していても
よい炭素原子数１〜１６のアルキル基、アルコキシ基、
アルコキシカルボニル基、アシルオキシ基、アルコキシ
カルボニルオキシ基のいずれかを示し、Ａは置換基を有
していてもよい ▲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▼のいずれかを示す。 ） で表わされる液晶性化合物の少なくとも１種と、下記一
般式［II］ ▲数式、化学式、表等があります▼［II］ （式中、Ｒ＿３は直鎖状の炭素原子数１〜１６のアルキ
ル基、Ｒ＿４は直鎖状の炭素原子数１〜１２のアルキル
基、Ｘ＿１は単結合、−Ｏ−、▲数式、化学式、表等が
あります▼、▲数式、化学式、表等があります▼のいず
れかから選ばれ、Ｘ＿２は−ＯＣＨ＿２−、▲数式、化
学式、表等があります▼、▲数式、化学式、表等があり
ます▼、−ＣＨ＿２−のいずれかから選ばれ、Ｚ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▼のいずれかから選ばれたものを示す。） で示される液晶性化合物の１種以上とを有することを特
徴とする液晶組成物。(1) The following general formula [ I ] ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ [ I ] (In the formula, R_1 is an alkyl group having 1 to 16 carbon atoms that may have a substituent, and R_2 is a substituted an alkyl group having 1 to 16 carbon atoms, an alkoxy group, which may have a group;
Indicates either an alkoxycarbonyl group, an acyloxy group, or an alkoxycarbonyloxy group, and A may have a substituent ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼, ▲ Numerical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Indicate either of the following. ) and the following general formula [II] ▲ Numerical formula, chemical formula, table, etc. ▼ [II] (In the formula, R_3 is a linear alkyl having 1 to 16 carbon atoms. group, R_4 is a linear alkyl group having 1 to 12 carbon atoms, X_1 is a single bond, -O-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ X_2 is selected from -OCH_2-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2-, and Z is chosen from ▲Mathematical formulas, chemical formulas, A liquid crystal composition characterized by having one or more of the liquid crystal compounds shown in Table 1.
１〜１６のアルキル基、Ｒ＿２は置換基を有していても
よい炭素原子数１〜１６のアルキル基、アルコキシ基、
アルコキシカルボニル基、アシルオキシ基、アルコキシ
カルボニルオキシ基のいずれかを示し、Ａは置換基を有
していてもよい ▲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▼のいずれかを示す。 ） で表わされる液晶性化合物の少なくとも１種と、下記一
般式［II］ ▲数式、化学式、表等があります▼［II］ （式中、Ｒ＿３は直鎖状の炭素原子数１〜１６のアルキ
ル基、Ｒ＿４は直鎖状の炭素原子数１〜１２のアルキル
基、Ｘ＿１は単結合、−Ｏ−、▲数式、化学式、表等が
あります▼、▲数式、化学式、表等があります▼のいず
れかから選ばれ、Ｘ＿２は−ＯＣＨ＿２−、▲数式、化
学式、表等があります▼、▲数式、化学式、表等があり
ます▼、−ＣＨ＿２−のいずれかから選ばれ、Ｚ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▼のいずれかから選ばれたものを示す。） で示される液晶性化合物の１種以上と、下記一般式［I
II］、［IV］および［Ｖ］のうちの少なくともいずれか
１種以上の液晶性化合物 ▲数式、化学式、表等があります▼［III］ ▲数式、化学式、表等があります▼［IV］ （式中、Ｒ＿５及びＲ＿６は直鎖状の炭素原子数１〜１
４のアルキル基を示す。） ▲数式、化学式、表等があります▼［Ｖ］ （式中、Ｒ＿７は直鎖状の炭素原子数１〜１４のアルキ
ル基、Ｒ＿８は直鎖状の炭素原子数１〜１４のアルキル
基を示す。） とを有することを特徴とする液晶組成物。(2) The following general formula [ I ] ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ [ I ] (In the formula, R_1 is an alkyl group having 1 to 16 carbon atoms that may have a substituent, and R_2 is a substituted an alkyl group having 1 to 16 carbon atoms, an alkoxy group, which may have a group;
Indicates either an alkoxycarbonyl group, an acyloxy group, or an alkoxycarbonyloxy group, and A may have a substituent ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼, ▲ Numerical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Indicate either of the following. ) and the following general formula [II] ▲ Numerical formula, chemical formula, table, etc. ▼ [II] (In the formula, R_3 is a linear alkyl having 1 to 16 carbon atoms. group, R_4 is a linear alkyl group having 1 to 12 carbon atoms, X_1 is a single bond, -O-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ X_2 is selected from -OCH_2-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2-, and Z is selected from ▲Mathematical formulas, chemical formulas, Indicates one or more liquid crystalline compounds represented by the formula [I
II], [IV] and [V] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [III] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [IV] ( In the formula, R_5 and R_6 are linear carbon atoms of 1 to 1
4 shows the alkyl group. ) ▲There are mathematical formulas, chemical formulas, tables, etc.▼[V] (In the formula, R_7 is a linear alkyl group having 1 to 14 carbon atoms, and R_8 is a linear alkyl group having 1 to 14 carbon atoms.) A liquid crystal composition comprising:
１〜１６のアルキル基、Ｒ＿２は置換基を有していても
よい炭素原子数１〜１６のアルキル基、アルコキシ基、
アルコキシカルボニル基、アシルオキシ基、アルコキシ
カルボニルオキシ基のいずれかを示し、Ａは置換基を有
していてもよい ▲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▼のいずれかを示す。 ） で表わされる液晶性化合物の少なくとも１種と、▲数式
、化学式、表等があります▼ および ▲数式、化学式、表等があります▼ のうち少なくとも１種の液晶性化合物とを有することを
特徴とする液晶組成物。(3) The following general formula [ I ] ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ [ I ] (In the formula, R_1 is an alkyl group having 1 to 16 carbon atoms that may have a substituent, and R_2 is a substituted an alkyl group having 1 to 16 carbon atoms, an alkoxy group, which may have a group;
Indicates either an alkoxycarbonyl group, an acyloxy group, or an alkoxycarbonyloxy group, and A may have a substituent ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼, ▲ Numerical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Indicate either of the following. ) and at least one type of liquid crystal compound of ▲There are mathematical formulas, chemical formulas, tables, etc.▼ and ▲There are mathematical formulas, chemical formulas, tables, etc.▼ liquid crystal composition.
１〜１６のアルキル基、Ｒ＿２は置換基を有していても
よい炭素原子数１〜１６のアルキル基、アルコキシ基、
アルコキシカルボニル基、アシルオキシ基、アルコキシ
カルボニルオキシ基のいずれかを示し、Ａは置換基を有
していてもよい ▲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▼のいずれかを示す。 ） で表わされる液晶性化合物の少なくとも１種と、下記一
般式［Ｖ］ ▲数式、化学式、表等があります▼［Ｖ］ （式中、Ｒ＿７は直鎖状の炭素原子数１〜１４のアルキ
ル基、Ｒ＿８は直鎖状の炭素原子数１〜１４のアルキル
基を示す。） で表わされる液晶性化合物の少なくとも３種とを有する
ことを特徴とする液晶組成物。(4) The following general formula [ I ] ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ [ I ] (In the formula, R_1 is an alkyl group having 1 to 16 carbon atoms that may have a substituent, and R_2 is a substituted an alkyl group having 1 to 16 carbon atoms, an alkoxy group, which may have a group;
Indicates either an alkoxycarbonyl group, an acyloxy group, or an alkoxycarbonyloxy group, and A may have a substituent ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼, ▲ Numerical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Indicate either of the following. ) and the following general formula [V] ▲ Numerical formula, chemical formula, table, etc. ▼ [V] (In the formula, R_7 is a linear alkyl having 1 to 14 carbon atoms. R_8 represents a linear alkyl group having 1 to 14 carbon atoms.
１〜１６のアルキル基、Ｒ＿２は置換基を有していても
よい炭素原子数１〜１６のアルキル基、アルコキシ基、
アルコキシカルボニル基、アシルオキシ基、アルコキシ
カルボニルオキシ基のいずれかを示し、Ａは置換基を有
していてもよい ▲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▼のいずれかを示す。 ） で表わされる液晶性化合物の少なくとも１種と、下記一
般式［II］ ▲数式、化学式、表等があります▼［II］ （式中、Ｒ＿３は直鎖状の炭素原子数１〜１６のアルキ
ル基、Ｒ＿４は直鎖状の炭素原子数１〜１２のアルキル
基、Ｘ＿１は単結合、−Ｏ−、▲数式、化学式、表等が
あります▼、▲数式、化学式、表等があります▼のいず
れかから選ばれ、Ｘ＿２は−ＯＣＨ＿２−、▲数式、化
学式、表等があります▼、▲数式、化学式、表等があり
ます▼、−ＣＨ＿２−のいずれかから選ばれ、Ｚ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▼のいずれかから選ばれたものを示す。） で示される液晶性化合物の１種以上とを有する液晶組成
物を使用することを特徴とする液晶素子。(5) The following general formula [ I ] ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ [ I ] (In the formula, R_1 is an alkyl group having 1 to 16 carbon atoms that may have a substituent, and R_2 is a substituted an alkyl group having 1 to 16 carbon atoms, an alkoxy group, which may have a group;
Indicates either an alkoxycarbonyl group, an acyloxy group, or an alkoxycarbonyloxy group, and A may have a substituent ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼, ▲ Numerical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Indicate either of the following. ) and the following general formula [II] ▲ Numerical formula, chemical formula, table, etc. ▼ [II] (In the formula, R_3 is a linear alkyl having 1 to 16 carbon atoms. group, R_4 is a linear alkyl group having 1 to 12 carbon atoms, X_1 is a single bond, -O-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ X_2 is selected from -OCH_2-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2-, and Z is selected from ▲Mathematical formulas, chemical formulas, The liquid crystal composition is characterized by using a liquid crystal composition having one or more of the following liquid crystal compounds: A liquid crystal element.
１〜１６のアルキル基、Ｒ＿２は置換基を有していても
よい炭素原子数１〜１６のアルキル基、アルコキシ基、
アルコキシカルボニル基、アシルオキシ基、アルコキシ
カルボニルオキシ基のいずれかを示し、Ａは置換基を有
していてもよい ▲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▼のいずれかを示す。 ） で表わされる液晶性化合物の少なくとも１種と、下記一
般式［II］ ▲数式、化学式、表等があります▼［II］ （式中、Ｒ＿３は直鎖状の炭素原子数１〜１６のアルキ
ル基、Ｒ＿４は直鎖状の炭素原子数１〜１２のアルキル
基、Ｘ＿１は単結合、−Ｏ−、▲数式、化学式、表等が
あります▼、▲数式、化学式、表等があります▼のいず
れかから選ばれ、Ｘ＿２は−ＯＣＨ＿２−、▲数式、化
学式、表等があります▼、▲数式、化学式、表等があり
ます▼、−ＣＨ＿２−のいずれかから選ばれ、Ｚ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▼のいずれかから選ばれたものを示す。） で示される液晶性化合物の１種以上と、下記一般式［I
II］、［IV］および［Ｖ］のうちの少なくともいずれか
１種以上の液晶性化合物 ▲数式、化学式、表等があります▼［III］ ▲数式、化学式、表等があります▼［IV］ （式中、Ｒ＿５及びＲ＿６は直鎖状の炭素原子数１〜１
４のアルキル基を示す。） ▲数式、化学式、表等があります▼［Ｖ］ （式中、Ｒ＿７は直鎖状の炭素原子数１〜１４のアルキ
ル基、Ｒ＿８は直鎖状の炭素原子数１〜１４のアルキル
基を示す。） とを有する液晶組成物を使用することを特徴とする液晶
素子。(6) The following general formula [I] ▲ Numerical formulas, chemical formulas, tables, etc. are available▼ [I] (In the formula, R_1 is an alkyl group having 1 to 16 carbon atoms that may have a substituent, and R_2 is a substituted an alkyl group having 1 to 16 carbon atoms which may have a group, an alkoxy group,
Indicates either an alkoxycarbonyl group, an acyloxy group, or an alkoxycarbonyloxy group, and A may have a substituent ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼, ▲ Numerical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Indicates either. ) and the following general formula [II] ▲ Numerical formula, chemical formula, table, etc. ▼ [II] (In the formula, R_3 is a linear alkyl having 1 to 16 carbon atoms. group, R_4 is a linear alkyl group having 1 to 12 carbon atoms, X_1 is a single bond, -O-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ X_2 is selected from -OCH_2-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2-, and Z is chosen from ▲Mathematical formulas, chemical formulas, Indicates one or more of the liquid crystalline compounds represented by ▼, ▲Mathematical formulas, chemical formulas, tables, etc.
II], [IV] and [V] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [III] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [IV] ( In the formula, R_5 and R_6 are linear carbon atoms of 1 to 1
4 shows the alkyl group. ) ▲There are mathematical formulas, chemical formulas, tables, etc.▼[V] (In the formula, R_7 is a linear alkyl group having 1 to 14 carbon atoms, and R_8 is a linear alkyl group having 1 to 14 carbon atoms.) A liquid crystal element characterized by using a liquid crystal composition having the following.
１〜１６のアルキル基、Ｒ＿２は置換基を有していても
よい炭素原子数１〜１６のアルキル基、アルコキシ基、
アルコキシカルボニル基、アシルオキシ基、アルコキシ
カルボニルオキシ基のいずれかを示し、Ａは置換基を有
していてもよい ▲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▼のいずれかを示す。 ） で表わされる液晶性化合物の少なくとも１種と、▲数式
、化学式、表等があります▼ および ▲数式、化学式、表等があります▼ のうち少なくとも１種の液晶性化合物とを有する液晶組
成物を使用することを特徴とする液晶素子。(7) The following general formula [I] ▲ Numerical formulas, chemical formulas, tables, etc. are available▼ [I] (In the formula, R_1 is an alkyl group having 1 to 16 carbon atoms that may have a substituent, and R_2 is a substituted an alkyl group having 1 to 16 carbon atoms, an alkoxy group, which may have a group;
Indicates either an alkoxycarbonyl group, an acyloxy group, or an alkoxycarbonyloxy group, and A may have a substituent ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼, ▲ Numerical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Indicate either of the following. ) and at least one liquid crystal compound of ▲There are mathematical formulas, chemical formulas, tables, etc.▼ and ▲There are mathematical formulas, chemical formulas, tables, etc.▼ A liquid crystal element characterized by its use.
１〜１６のアルキル基、Ｒ＿２は置換基を有していても
よい炭素原子数１〜１６のアルキル基、アルコキシ基、
アルコキシカルボニル基、アシルオキシ基、アルコキシ
カルボニルオキシ基のいずれかを示し、Ａは置換基を有
していてもよい ▲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▼のいずれかを示す。 ） で表わされる液晶性化合物の少なくとも１種と、下記一
般式［Ｖ］ ▲数式、化学式、表等があります▼［Ｖ］ （式中、Ｒ＿７は直鎖状の炭素原子数１〜１４のアルキ
ル基、Ｒ＿８は直鎖状の炭素原子数１〜１４のアルキル
基を示す。） で表わされる液晶性化合物の少なくとも３種とを有する
液晶組成物を使用することを特徴とする液晶素子。(8) The following general formula [ I ] ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ [ I ] (In the formula, R_1 is an alkyl group having 1 to 16 carbon atoms that may have a substituent, and R_2 is a substituted an alkyl group having 1 to 16 carbon atoms, an alkoxy group, which may have a group;
Indicates either an alkoxycarbonyl group, an acyloxy group, or an alkoxycarbonyloxy group, and A may have a substituent ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼, ▲ Numerical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Indicate either of the following. ) and the following general formula [V] ▲ Numerical formula, chemical formula, table, etc. ▼ [V] (In the formula, R_7 is a linear alkyl having 1 to 14 carbon atoms. R_8 represents a linear alkyl group having 1 to 14 carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP988889A JPH02696A (en) | 1988-01-25 | 1989-01-20 | Liquid crystal composition and liquid crystal element prepared by using same |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63-12574 | 1988-01-25 | ||
| JP1257488 | 1988-01-25 | ||
| JP988889A JPH02696A (en) | 1988-01-25 | 1989-01-20 | Liquid crystal composition and liquid crystal element prepared by using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02696A true JPH02696A (en) | 1990-01-05 |
Family
ID=26344701
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP988889A Pending JPH02696A (en) | 1988-01-25 | 1989-01-20 | Liquid crystal composition and liquid crystal element prepared by using same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02696A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0331392A (en) * | 1989-06-29 | 1991-02-12 | Mitsui Toatsu Chem Inc | Ferroelectric liquid crystal composition and ferroelectric liquid crystal element |
| CN1083744C (en) * | 1997-08-22 | 2002-05-01 | 株式会社神户制钢所 | Coat core-wire for gas-protection arc welding |
-
1989
- 1989-01-20 JP JP988889A patent/JPH02696A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0331392A (en) * | 1989-06-29 | 1991-02-12 | Mitsui Toatsu Chem Inc | Ferroelectric liquid crystal composition and ferroelectric liquid crystal element |
| CN1083744C (en) * | 1997-08-22 | 2002-05-01 | 株式会社神户制钢所 | Coat core-wire for gas-protection arc welding |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0343488A (en) | Liquid crystal compound, liquid crystal composition containing the same compound and liquid crystal element using the composition | |
| JPH0269440A (en) | Optically active liquid-crystallizable compound, liquid crystal composition containing the same compound and liquid crystal element | |
| JP2952053B2 (en) | Optically active compound, liquid crystal composition containing the same, method of using the same, liquid crystal element using the same, and display device | |
| JP2691946B2 (en) | Liquid crystal compound, liquid crystal composition containing the same, and liquid crystal device using the same | |
| JPH0429993A (en) | Liquid crystalline compound, liquid crystal composition containing the same and liquid crystal element using the same | |
| JPH04217973A (en) | Liquid crystal compound, liquid crystal composition containing the compound and liquid crystal element and display device produced by using the same | |
| JPS63137986A (en) | Ferroelectric liquid crystal device | |
| JPH0629424B2 (en) | Ferroelectric chiral smectic liquid crystal composition and liquid crystal device containing the same | |
| JPH02696A (en) | Liquid crystal composition and liquid crystal element prepared by using same | |
| JP2749822B2 (en) | Liquid crystal composition and liquid crystal device containing the same | |
| JPH04300871A (en) | Optically active compound, liquid crystal composition containing the compound, liquid crystal element containing the composition and display and display device using the element or the like | |
| JPH0269467A (en) | Liquid crystal compound, liquid crystal composition and element containing the same compound | |
| JPH0426679A (en) | Liquid crystalline compound, liquid crystal composition containing the same and liquid crystal element using the same | |
| JPH04272989A (en) | Liquid crystal composition, liquid crystal element containing same, and display method and display device using same | |
| JPH04264052A (en) | Optically active compound, liquid crystal composition containing the same, liquid crystal element having the same and method for display and display device using the same | |
| JP2759459B2 (en) | Liquid crystal composition and liquid crystal device containing the same | |
| JPH0782256A (en) | Liquid crystal compound, liquid crystal composition containing the same, liquid crystal device containing the same and display and display device using the same | |
| JPS63291980A (en) | Ferroelectric liquid crystal element | |
| JPH0269427A (en) | Optically active liquid crystal compound, liquid crystal composition and liquid crystal element containing the same compound | |
| JP2739373B2 (en) | Liquid crystal compound, liquid crystal composition containing the same, and liquid crystal device using the same | |
| JP2510681B2 (en) | Liquid crystal composition and liquid crystal device containing the same | |
| JP2770953B2 (en) | Liquid crystal composition and liquid crystal device containing the same | |
| JPH01207280A (en) | Liquid crystal-formable compound, liquid crystal composition containing said compound and liquid crystal element using said compound | |
| JP2976109B2 (en) | Liquid crystal composition and liquid crystal device containing the same | |
| JPH02279651A (en) | Ferroelectric chiral smectic liquid crystal composition and liquid crystal elements using the same |