JP3228348B2 - Polymer liquid crystal compound, liquid crystal composition and liquid crystal element - Google Patents
Polymer liquid crystal compound, liquid crystal composition and liquid crystal elementInfo
- Publication number
- JP3228348B2 JP3228348B2 JP19899192A JP19899192A JP3228348B2 JP 3228348 B2 JP3228348 B2 JP 3228348B2 JP 19899192 A JP19899192 A JP 19899192A JP 19899192 A JP19899192 A JP 19899192A JP 3228348 B2 JP3228348 B2 JP 3228348B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- polymer
- film
- polymer liquid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims description 95
- 239000005264 High molar mass liquid crystal Substances 0.000 title claims description 59
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 52
- 239000000203 mixture Substances 0.000 title claims description 21
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000010408 film Substances 0.000 description 50
- 229920000642 polymer Polymers 0.000 description 21
- 239000000758 substrate Substances 0.000 description 20
- 239000007788 liquid Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 15
- 239000010409 thin film Substances 0.000 description 13
- 230000003287 optical effect Effects 0.000 description 12
- -1 polypropylene Polymers 0.000 description 11
- 239000011521 glass Substances 0.000 description 7
- 239000011810 insulating material Substances 0.000 description 7
- 229920001721 polyimide Polymers 0.000 description 7
- 239000004642 Polyimide Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000004988 Nematic liquid crystal Substances 0.000 description 5
- 239000004990 Smectic liquid crystal Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000015654 memory Effects 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- VVYHWYFUTOHXRH-UHFFFAOYSA-N 4-(6-hydroxyhexoxy)benzoic acid Chemical compound OCCCCCCOC1=CC=C(C(O)=O)C=C1 VVYHWYFUTOHXRH-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 229920000106 Liquid crystal polymer Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920002620 polyvinyl fluoride Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004043 responsiveness Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- CEEOUTFAPZOUHS-UHFFFAOYSA-N 2-(6-prop-2-enoyloxyhexoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCCCCCOC(=O)C=C CEEOUTFAPZOUHS-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- MPAIWVOBMLSHQA-UHFFFAOYSA-N 3,6-dihydroxybenzene-1,2-dicarbonitrile Chemical compound OC1=CC=C(O)C(C#N)=C1C#N MPAIWVOBMLSHQA-UHFFFAOYSA-N 0.000 description 1
- GZEFZLXJPGMRSP-UHFFFAOYSA-N 37,38,39,40-tetrazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1(37),2,4,6,8,10,12(39),13,15,17,19,21,23,25,27,29,31,33,35-nonadecaene Chemical class c1ccc2c3cc4[nH]c(cc5nc(cc6[nH]c(cc(n3)c2c1)c1ccccc61)c1ccccc51)c1ccccc41 GZEFZLXJPGMRSP-UHFFFAOYSA-N 0.000 description 1
- FLPSQLAEXYKMGQ-UHFFFAOYSA-N 4-(6-prop-2-enoyloxyhexoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 FLPSQLAEXYKMGQ-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- 229920001342 Bakelite® Polymers 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000005041 Mylar™ Substances 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- YVRQEGLKRIHRCH-UHFFFAOYSA-N [1,4]benzothiazino[2,3-b]phenothiazine Chemical compound S1C2=CC=CC=C2N=C2C1=CC1=NC3=CC=CC=C3SC1=C2 YVRQEGLKRIHRCH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 239000004637 bakelite Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- QCCDYNYSHILRDG-UHFFFAOYSA-K cerium(3+);trifluoride Chemical compound [F-].[F-].[F-].[Ce+3] QCCDYNYSHILRDG-UHFFFAOYSA-K 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920006262 high density polyethylene film Polymers 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene 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
- 230000000873 masking effect Effects 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 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
- 238000000059 patterning Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920003055 poly(ester-imide) Polymers 0.000 description 1
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 238000010008 shearing Methods 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
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Liquid Crystal (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
【0001】[0001]
【産業上の利用分野】本発明は高分子液晶化合物、高分
子液晶組成物、それらを用いた液晶素子に関するもので
ある。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a polymer liquid crystal compound, a polymer liquid crystal composition, and a liquid crystal device using the same.
【0002】本発明の高分子液晶化合物、高分子液晶組
成物は、ディスプレイ、メモリ−に代表されるオプトエ
レクトロニクス材料、光学機器材料等として使用するこ
とができる。 The polymer liquid crystal compound and the polymer liquid crystal composition of the present invention can be used as optoelectronic materials and optical device materials typified by displays and memories.
【0003】[0003]
【従来の技術】従来の液晶素子としては、例えばエム・
シャット(M.Schadt)とダブリュー・ヘルフリ
ッヒ(W.Helfrich)著“アプライド・フィジ
ックス・レターズ”(“Applied Physic
s Letters”)第18巻、第4号(1971年
2月15日発行)第127頁〜128頁の“ボルテージ
・ディペンダント・オプティカル・アクティビィティー
・オブ・ア・ツイステッド・ネマチック・リキッド・ク
リスタル”(“Voltage Dependent
Optical Activity of a Twi
sted Nematic Liquid Cryst
al”)に示されたツイステッド・ネマチック(twi
sted nematic)液晶を用いたものが知られ
ている。しかしながら、このTN液晶は、画素密度を高
くしたマトリクス電極構造を用いた時分割駆動の時、ク
ロストークを発生する問題点があるため、画素数が制限
されていた。2. Description of the Related Art As a conventional liquid crystal element, for example,
“Applied Physics Letters” by M. Schadt and W. Helfrich (“Applied Physic”).
Vol. 18, No. 4, Issued Feb. 15, 1971, pp. 127-128, "Voltage Dependent Optical Activity of a Twisted Nematic Liquid Crystal" (“Voltage Dependent
Optical Activity of a Twi
sted Nematic Liquid Cryst
al "), the twisted nematic (twi
A device using a liquid crystal (stable nematic) is known. However, the TN liquid crystal has a problem in that crosstalk occurs in time-division driving using a matrix electrode structure having a high pixel density, so that the number of pixels is limited.
【0004】また、電界応答が遅く視野角特性が悪いた
めにディスプレイとしての用途は限定されていた。ま
た、各画素に薄膜トランジスタを形成する工程が極めて
煩雑な上、大面積の表示素子を作成することが難しい問
題点がある。In addition, applications as displays have been limited due to slow electric field response and poor viewing angle characteristics. Further, there is a problem that a process of forming a thin film transistor in each pixel is extremely complicated and it is difficult to form a large-area display element.
【0005】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、双安定性からなる液晶素子の使用が、ク
ラーク(Clark)およびラガウェル(Lagerw
all)により提案されている。(特開昭56−107
216号公報、米国特許第4367924号明細書等)
この双安定性からなる液晶としては、一般にカイラルス
メクティックC相(Sm* C)又はH相(Sm* H)か
らなる強誘電性液晶が用いられている。この強誘電性液
晶は、自発分極からなるために非常に速い応答速度から
なる上に、メモリー性のある双安定状態を発現させるこ
とができる。さらに、視野角特性もすぐれていることか
ら、大容量、大面積のディスプレイ用材料として適して
いると考えられる。しかし、実際に液晶セルを形成する
場合、広い面積にわたってモノドメイン化することは困
難であり、大画面の表示素子を作るには技術上の問題が
あった。As an improvement over the conventional liquid crystal device, the use of a bistable liquid crystal device has been proposed by Clark and Lagerw.
all). (JP-A-56-107
No. 216, U.S. Pat. No. 4,367,924, etc.)
As the liquid crystal having the bistability, a ferroelectric liquid crystal having a chiral smectic C phase (Sm * C) or an H phase (Sm * H) is generally used. The ferroelectric liquid crystal has a very fast response speed because of spontaneous polarization, and can exhibit a bistable state with memory properties. Further, since the viewing angle characteristics are excellent, it is considered that the material is suitable as a display material having a large capacity and a large area. However, when actually forming a liquid crystal cell, it is difficult to form a monodomain over a wide area, and there is a technical problem in producing a large-screen display element.
【0006】また、高分子液晶をメモリー媒体として用
いる例が知られている。例えば、ブィ・シバエフ(V.
Shibaev)、エス・コストロミン(S.Kost
romin)、エヌ・プラーテ(N.Pla´te)、
エス・イワノフ(S.Iva ov)、ブィ・ヴェスト
ロフ(V.Vestrov)、アイ・ヤコブレフ(I.
Yakovlev)著の“ポリマー・コミュニケーショ
ンズ”(“Polymer Communicatio
ns”)第24巻、第364頁〜365頁の“サーモト
ロピック・リキッドクリスタリン・ポリマーズ.14”
(“Thermotropic Liquid Cry
stalline Polymers.14”)に示さ
れる熱書き込みメモリーを挙げることができる。Further, there is known an example in which a polymer liquid crystal is used as a memory medium. For example, V. Shibaev (V.
Shibaev), S. Kostromin (S. Kost)
romin), N. Pla'te,
S. Ivaov, V. Vestrov, I. Yakovlev (I.
"Polymer Communications", written by Yakovlev.
ns "), Vol. 24, pp. 364-365," Thermotropic Liquid Crystalline Polymers. 14 "
("Thermotropic Liquid Cry
stalline Polymers. 14 ").
【0007】しかしながら、この方法は読みとりとして
光の散乱を利用しているのでコントラストが悪く、かつ
高分子化に伴なう応答速度の遅れという問題もあって実
用化には至っていない。However, this method has not been put to practical use due to the problems of poor contrast because of the use of light scattering for reading, and a delay in response speed due to polymerization.
【0008】また、高分子液晶を用いた大面積の液晶素
子を作成する試みもなされているが、分子量が充分に大
きくないため、大面積化の障害となる欠点があった。Attempts have also been made to produce large-area liquid crystal devices using polymer liquid crystals, but the molecular weight is not sufficiently large, which has the disadvantage of hindering an increase in area.
【0009】一方、液晶の光学的異方性と高分子のフィ
ルム性を利用して高分子液晶を光学薄膜として利用する
試みもなされている。(特開昭63−303385号公
報等)また、同様な考え方から、高分子液晶を液晶素子
の配向膜として用いる試みもなされている。(特開平2
−101431号公報)しかしながら、この様な試み
は、高分子液晶の分子量が十分に大きくなかったため、
膜性が充分でないためによれが生じたり、あるいは、液
晶と相溶したりする欠点があった。On the other hand, attempts have been made to use polymer liquid crystals as optical thin films by utilizing the optical anisotropy of liquid crystals and the film properties of polymers. (Japanese Unexamined Patent Publication No. 63-303385, etc.) From the same concept, attempts have been made to use a polymer liquid crystal as an alignment film of a liquid crystal element. (Japanese Patent Laid-Open No. 2
However, in such an attempt, since the molecular weight of the polymer liquid crystal was not sufficiently large,
There is a drawback in that the film is not sufficiently formed to be warped or to be compatible with the liquid crystal.
【0010】また、この様な欠点を補うため、架橋した
高分子液晶を用いる試みもなされている。[ポリマー
サイエンス アンド テクノロジー(プレナム)198
5年,28巻,275〜368頁)しかしながら、架橋
成分の構造が液晶と異なる構造であったため、液晶性が
阻害されるという欠点があった。[0010] In order to make up for such disadvantages, attempts have been made to use crosslinked polymer liquid crystals. [polymer
Science and Technology (Plenum) 198
However, since the structure of the cross-linking component is different from that of the liquid crystal, there is a disadvantage that the liquid crystallinity is hindered.
【0011】[0011]
【発明が解決しようとする課題】本発明は、このような
従来例の欠点を回避する新規な反応性液晶性化合物を見
出したものであり、該反応性液晶性化合物を用いて、フ
ィルム性の優れた、応答性の良好な、大面積の液晶素子
が可能であり、また光学的特性に優れた電気光学薄膜を
得ることが出来る、該化合物を使用した高分子液晶化合
物、高分子組成物を用いた液晶素子を提供することを目
的とするものである。DISCLOSURE OF THE INVENTION The present invention has found a novel reactive liquid crystalline compound which avoids such disadvantages of the prior art, and uses the reactive liquid crystalline compound to form a film. Excellent, good responsiveness, a large-area liquid crystal element is possible, and it is also possible to obtain an electro-optical thin film having excellent optical characteristics, a polymer liquid crystal compound using the compound, a polymer composition It is an object of the present invention to provide a used liquid crystal element.
【0012】[0012]
【課題を解決するための手段】即ち、本発明の第一の発
明は、下記一般式〔1〕で表される反応性液晶性化合物
を重合成分として有する高分子液晶化合物である。That is, a first invention of the present invention is a reactive liquid crystalline compound represented by the following general formula [1]:
Is a polymer liquid crystal compound having a polymer component .
【0013】[0013]
【化4】 Embedded image
【0014】(式中、R1 は水素原子、アルキル基また
はハロゲン基を表わす。U,V,W,X,Yはそれぞれ
同一もしくは異なる、単結合,−O−,−OCO−また
は−COO−を表わす。aは0または1を表わす。b,
fはそれぞれ同一もしくは異なる0から15までの整数
を表わす。c,d,eはそれぞれ同一もしくは異なる0
から2までの整数を表わす。)(In the formula, R 1 represents a hydrogen atom, an alkyl group or a halogen group. U, V, W, X and Y are the same or different and are each a single bond, -O-, -OCO- or -COO- A represents 0 or 1. b,
f represents the same or different integers from 0 to 15; c, d and e are the same or different 0
Represents an integer from 1 to 2. )
【0015】本発明の第二の発明は、第一の発明の高分
子液晶化合物を含有する高分子液晶組成物である。 The second invention of the present invention is a polymer liquid crystal composition containing the polymer liquid crystal compound of the first invention .
【0016】そして、本発明の第三の発明は、一般式
〔1〕で表される構造を有する液晶性化合物を使用して
得ることができる高分子液晶化合物を含有する高分子液
晶組成物を用いることを特徴とする液晶素子である。The third invention of the present invention relates to a polymer liquid crystal composition containing a polymer liquid crystal compound obtainable by using a liquid crystal compound having a structure represented by the general formula [1]. A liquid crystal element characterized by being used.
【0017】以下、本発明を詳細に説明する。本発明の
第一の発明で用いられる反応性液晶性化合物は、上記一
般式〔1〕で表される構造を有する化合物である。前記
一般式〔1〕において、両末端は反応性官能基であり、
中央付近はメソーゲンで有り、メソーゲンと反応性官能
基を結ぶものがフレキシブルスペーサである。この反応
性液晶化合物の具体例としては次の構造で表わされる化
合物が挙げられる。Hereinafter, the present invention will be described in detail. The reactive liquid crystalline compound used in the first invention of the present invention is a compound having a structure represented by the general formula [1]. In the general formula [1], both terminals are reactive functional groups,
The vicinity of the center is a mesogen, and what connects the mesogen and the reactive functional group is a flexible spacer. Specific examples of the reactive liquid crystal compound include a compound represented by the following structure.
【0018】[0018]
【化5】 Embedded image
【0019】[0019]
【化6】 Embedded image
【0020】[0020]
【化7】 Embedded image
【0021】[0021]
【化8】 Embedded image
【0022】本発明の反応性液晶性化合物は上記具体例
に制限されるものでないことは言うまでもない。又、本
発明の代表的な反応性液晶性化合物の合成方法を下記に
しめす。Needless to say, the reactive liquid crystalline compound of the present invention is not limited to the above specific examples. A method for synthesizing a typical reactive liquid crystalline compound of the present invention is described below.
【0023】[0023]
【化9】 DCCはジシクロカルボキシイミドを示す。Embedded image DCC stands for dicyclocarboximide.
【0024】次に、本発明の第一の発明の高分子液晶化
合物は、一般式〔1〕で表される構造を有する反応性液
晶性化合物を重合成分として有する高分子液晶化合物で
ある。該高分子液晶化合物の製造法としては、一般的に
は他の反応性液晶性化合物と一般式〔1〕で表される反
応性液晶性化合物を重合反応する方法が挙げられる。具
体的な製造方法としては以下に挙げる方法があるが、勿
論以下の方法に限定されるものではない。Next, the polymer liquid crystal compound of the first invention of the present invention is a polymer liquid crystal compound having a reactive liquid crystal compound having a structure represented by the general formula [1] as a polymerization component. As a method for producing the polymer liquid crystal compound, there is generally mentioned a method of polymerizing a reactive liquid crystal compound represented by the general formula [1] with another reactive liquid crystal compound. Specific production methods include the following methods, but, of course, are not limited to the following methods.
【0025】1)重合性官能基を持つ反応性液晶性化合
物と一般式〔1〕で表される構造を有する化合物を溶液
状態で、ラジカル重合あるいはイオン重合を行うことに
より得る方法。 2)反応部位を有する主鎖を持つ高分子化合物に、該高
分子化合物に反応する官能基を持つ反応性液晶性化合物
と、一般式〔1〕で表される構造を有する化合物をグラ
フト重合的に反応して得る方法。 3)重合性官能基を持つ反応性液晶性化合物と一般式
〔1〕で表される構造を有する化合物を液晶状態、又は
溶融状態あるいは固体状態、あるいは溶液状態でUV照
射等を行い重合反応して得る方法。1) A method in which a reactive liquid crystalline compound having a polymerizable functional group and a compound having a structure represented by the general formula [1] are obtained by performing radical polymerization or ionic polymerization in a solution state. 2) A polymer having a main chain having a reactive site is graft-polymerized with a reactive liquid crystalline compound having a functional group reactive with the polymer and a compound having a structure represented by the general formula [1]. How to get in response to. 3) A reactive liquid crystalline compound having a polymerizable functional group and a compound having a structure represented by the general formula [1] undergo a polymerization reaction by performing UV irradiation or the like in a liquid crystal state, a molten state, a solid state, or a solution state. How to get.
【0026】本発明の高分子液晶化合物において、一般
式〔1〕で表される構造を有する反応性液晶性は任意の
割合で用いられる。また、液晶性を持たない反応性化合
物を共重合して用いることもできる。反応性を有する色
素等の機能性化合物を共重合して用いることも出来る。In the polymer liquid crystal compound of the present invention, the reactive liquid crystal having the structure represented by the general formula [1] is used in an arbitrary ratio. In addition, a reactive compound having no liquid crystallinity can be copolymerized and used. Functional compounds such as reactive dyes may be copolymerized and used.
【0027】上記の重合方法の1)〜3)で用いられる
他の反応性液晶性化合物の具体例としては、以下に挙げ
る化合物が挙げられるが、勿論以下の化合物に限定され
るものではない。Specific examples of the other reactive liquid crystalline compounds used in the above polymerization methods 1) to 3) include the following compounds, but are not limited to the following compounds.
【0028】[0028]
【化10】 Embedded image
【0029】[0029]
【化11】 Embedded image
【0030】[0030]
【化12】 Embedded image
【0031】また、重合方法の2)で用いられる、反応
部位を有する主鎖を持つ高分子化合物の具体例として以
下の繰り返し単を持つ位化合物が挙げられる。Specific examples of the high molecular compound having a main chain having a reactive site used in the polymerization method 2) include a compound having a repeating unit shown below.
【0032】[0032]
【化13】 Embedded image
【0033】(E)の場合、触媒存在下、ビニル基をも
つ液晶性化合物をグラフト的に反応して製造することが
できる。(F),(G)の場合も同様にカルボン酸に、
反応性をもつ官能基を有する液晶性化合物をグラフト的
に反応して製造することができる。In the case of (E), it can be produced by graft-reacting a liquid crystal compound having a vinyl group in the presence of a catalyst. Similarly, in the case of (F) and (G),
It can be produced by reacting a liquid crystalline compound having a reactive functional group in a graft manner.
【0034】本発明の高分子液晶化合物の数平均分子量
は2,000から10,000,000、好ましくは十
分なフィルム性、安定した膜性という観点から20,0
00から10,000,000である。The number average molecular weight of the high-molecular liquid crystal compound of the present invention is from 2,000 to 10,000,000, preferably from 20,000 in view of sufficient film properties and stable film properties.
00 to 10,000,000.
【0035】次に、本発明の第二の発明は、第一の発明
の高分子液晶化合物を含有する高分子液晶組成物であ
る。該高分子液晶組成物の他の含有成分としては、低分
子化合物、低分子液晶化合物、高分子化合物、高分子液
晶化合物等があげられる。また、色素、安定剤、UV吸
収剤等を含有することができる。Next, a second invention of the present invention is a polymer liquid crystal composition containing the polymer liquid crystal compound of the first invention . Other components contained in the polymer liquid crystal composition include a low molecular compound, a low molecular liquid crystal compound, a high molecular compound, a high molecular liquid crystal compound and the like. Further, it may contain a dye, a stabilizer, a UV absorber and the like.
【0036】低分子液晶化合物の具体例としては、以下
のものが挙げられるが、勿論以下のものに限定されるわ
けではない。Specific examples of the low-molecular liquid crystal compound include the following, but are not limited to the following.
【0037】[0037]
【化14】 Embedded image
【0038】[0038]
【化15】 Embedded image
【0039】[0039]
【化16】 Embedded image
【0040】[0040]
【化17】 Embedded image
【0041】[0041]
【化18】 Embedded image
【0042】[0042]
【化19】 Embedded image
【0043】[0043]
【化20】 Embedded image
【0044】[0044]
【化21】 Embedded image
【0045】(20)メルク社 Z−1625 ネマチック温度範囲 −10〜60℃ (21)BDH社 E−7 ネマチック温度範囲 −10〜60℃ (22)ロッシュ社 R−200 ネマチック温度範囲 0〜65℃ (23)大日本インキ社 D−X01A ネマチック温度範囲 −26〜68℃ (24)メルク社 ZLI−2008 Tcl=
64℃ (25)メルク社 ZLI−1840 Tcl=
90℃ (26)DIC TN403 Tcl=
82℃(20) Merck Z-1625 nematic temperature range -10 to 60 ° C (21) BDH E-7 nematic temperature range -10 to 60 ° C (22) Roche R-200 nematic temperature range 0 to 65 ° C (23) Dainippon Ink D-X01A Nematic Temperature Range -26 to 68 ° C (24) Merck ZLI-2008 Tcl =
64 ° C. (25) Merck ZLI-1840 Tcl =
90 ° C (26) DIC TN403 Tcl =
82 ° C
【0046】高分子液晶化合物の具体例としては、、以
下のものが挙げられるが、勿論以下のものに限定される
わけではない。Specific examples of the polymer liquid crystal compound include , but are not limited to, the following.
【0047】(下記式(31)〜(43)中、15>n
≧1である。)(In the following formulas (31) to (43), 15> n
≧ 1. )
【0048】[0048]
【化22】 Embedded image
【0049】[0049]
【化23】 Embedded image
【0050】(下記式(44)〜(46)中、p=5〜
1000,p1 +p2 =5〜1000,q=1〜1
6,q1 =1〜16,q2 =1〜16である。)(In the following formulas (44) to (46), p = 5 to
1000, p 1 + p 2 = 5 to 1000, q = 1 to 1
6, q 1 = 1 to 16, and q 2 = 1 to 16. )
【0051】[0051]
【化24】 Embedded image
【0052】(式(45),(46)中、Rは炭素数1
〜12のアルキル基もしくはアルコキシ基を示す。) (下記式(47)〜(75)中、*は不斉炭素中心を示
し、n=5〜1000である。)(In the formulas (45) and (46), R represents 1 carbon atom.
And 12 to 12 alkyl groups or alkoxy groups. (In the following formulas (47) to (75), * indicates an asymmetric carbon center, and n is 5 to 1000.)
【0053】[0053]
【化25】 Embedded image
【0054】[0054]
【化26】 Embedded image
【0055】[0055]
【化27】 Embedded image
【0056】[0056]
【化28】 Embedded image
【0057】[0057]
【化29】 Embedded image
【0058】[0058]
【化30】 Embedded image
【0059】[0059]
【化31】 Embedded image
【0060】[0060]
【化32】 Embedded image
【0061】[0061]
【化33】 Embedded image
【0062】本発明の高分子液晶組成物中における高分
子液晶化合物の含有量は、通常5wt%以上、好ましく
は10wt%以上が望ましい。5wt%未満では十分な
フィルム性、安定した膜性が得られない場合がある。The content of the polymer liquid crystal compound in the polymer liquid crystal composition of the present invention is usually 5 wt% or more, preferably 10 wt% or more. If it is less than 5 wt%, sufficient film properties and stable film properties may not be obtained.
【0063】本発明の第一の発明の高分子液晶化合物、
第二の発明の高分子液晶組成物は、ネマチック液晶相を
示す場合、従来のTN型液晶と同様のスイッチングモー
ドを用いた液晶素子に用いることが出来る。また、カイ
ラルスメクチック液晶相を示す場合、双安定性を有する
強誘電性のスイッチングモードを用いた液晶素子に用い
ることが出来る。また、配向を固定して、ネマチック液
晶相あるいはスメクチック液晶相の電気光学性を持つ電
気光学薄膜として、液晶素子中にあるいは液晶素子とし
て用いることが出来る。The polymer liquid crystal compound of the first invention of the present invention,
When the polymer liquid crystal composition of the second invention exhibits a nematic liquid crystal phase, it can be used for a liquid crystal element using the same switching mode as a conventional TN liquid crystal. In the case of showing a chiral smectic liquid crystal phase, it can be used for a liquid crystal element using a ferroelectric switching mode having bistability. Further, it can be used in a liquid crystal element or as a liquid crystal element as an electro-optic thin film having the electro-optic property of a nematic liquid crystal phase or a smectic liquid crystal phase with a fixed orientation.
【0064】そして、本発明の第三の発明は、一般式
〔1〕で表される構造を有する液晶性化合物を使用して
得ることができる高分子液晶化合物を含有する高分子液
晶組成物を使用した液晶素子である。The third invention of the present invention relates to a polymer liquid crystal composition containing a polymer liquid crystal compound obtainable by using a liquid crystal compound having a structure represented by the general formula [1]. This is the liquid crystal element used.
【0065】本発明の高分子液晶素子の一例は、ガラ
ス,プラスチック又は金属等の任意の材料からなる基板
の上に、本発明の高分子液晶化合物又は高分子液晶組成
物を塗布等の方法でフィルムを形成するが、基板上にI
TO膜などの透明電極やパターン化された電極を形成す
ることができる。One example of the polymer liquid crystal device of the present invention is a method of coating the polymer liquid crystal compound or the polymer liquid crystal composition of the present invention on a substrate made of any material such as glass, plastic or metal. A film is formed, but I
A transparent electrode such as a TO film or a patterned electrode can be formed.
【0066】図1(a),(b)は本発明の高分子液晶
素子の一例を示し、図1(a)は本発明の高分子液晶素
子の平面図、図1(b)はそのAA′線断面図である。
同図1は本発明の高分子液晶化合物を表示素子に適用し
た例を示す。FIGS. 1A and 1B show an example of the polymer liquid crystal device of the present invention. FIG. 1A is a plan view of the polymer liquid crystal device of the present invention, and FIG. FIG.
FIG. 1 shows an example in which the polymer liquid crystal compound of the present invention is applied to a display device.
【0067】同図1において、本発明の高分子液晶素子
は、ガラス板又はプラスチック板などからなる一対の基
板1,1′(少なくとも一方の基板が複屈折を有する)
をスペーサ4で所定の間隔に保持し、この一対の基板
1,1′をシーリングするために接着剤6で接着したセ
ル構造を有しており、さらに基板1の上には複数の透明
電極2からなる電極群(例えば、マトリクス電極構造の
うちの走査電圧印加用電極群)が、例えば帯状パターン
などの所定パターンで形成されている。また、基板1′
の上には前述の透明電極2と交差させた複数の透明電極
2′からなる電極群(例えば、マトリクス電極構造のう
ちの信号電圧印加用電極群)が形成されている。In FIG. 1, the polymer liquid crystal device of the present invention has a pair of substrates 1 and 1 'made of a glass plate or a plastic plate (at least one of the substrates has birefringence).
Are held at predetermined intervals by spacers 4 and have a cell structure bonded with an adhesive 6 to seal the pair of substrates 1 and 1 ′. (For example, a scanning voltage application electrode group in a matrix electrode structure) is formed in a predetermined pattern such as a strip pattern. Also, the substrate 1 '
An electrode group (for example, a signal voltage application electrode group in a matrix electrode structure) formed of a plurality of transparent electrodes 2 ′ crossing the above-mentioned transparent electrode 2 is formed on the substrate.
【0068】この様な透明電極2,2′を設けた基板
1,1′には、例えば、一酸化珪素,二酸化珪素,酸化
アルミニウム,ジルコニア,フッ化マグネシウム,酸化
セリウム,フッ化セリウム,シリコン窒化物,シリコン
炭化物,ホウ素窒化物などの無機絶縁物質やポリビニル
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,ポリパラキシレリン,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,ポリアミド,ポリスチレン,セルロース樹脂,メラ
ミン樹脂,ユリア樹脂やアクリル樹脂などの有機絶縁物
質を用いて被膜形成した配向制御膜5,5′を設けるこ
とができる。The substrates 1, 1 'on which such transparent electrodes 2, 2' are provided include, for example, silicon monoxide, silicon dioxide, aluminum oxide, zirconia, magnesium fluoride, cerium oxide, cerium fluoride, silicon nitride. Material, silicon carbide, boron nitride and other inorganic insulating materials, polyvinyl alcohol, polyimide, polyamide imide, polyester imide, polyparaxylerin, polyester, polycarbonate, polyvinyl acetal, polyvinyl chloride, polyamide, polystyrene, cellulose resin, melamine resin Orientation control films 5, 5 'formed by using an organic insulating material such as urea resin or acrylic resin can be provided.
【0069】この配向制御膜5,5′は、前述の如き無
機絶縁物質又は有機絶縁物質を被膜形成した後に、その
表面をビロード、布や紙で一方向に摺擦(ラビング)す
ることによって得られる。本発明の別の好ましい具体例
では、SiOやSiO2 などの無機絶縁物質を基板1,
1′の上に斜め蒸着法によって被膜形成することによっ
て配向制御膜5,5′を得ることができる。The orientation control films 5 and 5 'are obtained by forming a film of the above-mentioned inorganic insulating material or organic insulating material and then rubbing the surface thereof in one direction with velvet, cloth or paper. Can be In another preferred embodiment of the present invention, the substrate 1 of an inorganic insulating material such as SiO or SiO 2,
The orientation control films 5, 5 'can be obtained by forming a film on 1' by oblique evaporation.
【0070】また、別の具体例ではガラス又はプラスチ
ックからなる基板1,1′の表面あるいは基板1,1′
の上に前述した無機絶縁物質や有機絶縁物質を被膜形成
した後に、該被膜の表面を斜方エッチング法によりエッ
チングすることにより、その表面に配向制御効果を付与
することができる。In another embodiment, the surface of the substrate 1, 1 'made of glass or plastic or the substrate 1, 1'
After a film of the above-mentioned inorganic insulating material or organic insulating material is formed thereon, the surface of the film is etched by an oblique etching method, whereby an orientation control effect can be imparted to the surface.
【0071】前述の配向制御膜5,5′は、同時に絶縁
膜としても機能させることが好ましく、このためにこの
配向制御膜の膜厚は一般に100Å〜1μm、好ましく
は500Å〜5000Åの範囲に設定することができ
る。この絶縁層は高分子液晶層3に微量に含有される不
純物等のために生ずる電流の発生を防止できる利点をも
有しており、従って動作を繰り返し行っても液晶化合物
を劣化させることがない。It is preferable that the alignment control films 5 and 5 'also function as an insulating film at the same time. Therefore, the thickness of the alignment control film is generally set in the range of 100 to 1 μm, preferably 500 to 5000 °. can do. This insulating layer also has the advantage of preventing the generation of current generated due to impurities and the like contained in the polymer liquid crystal layer 3 in a very small amount. Therefore, the liquid crystal compound does not deteriorate even if the operation is repeated. .
【0072】また、本発明の高分子液晶素子では、基板
1もしくは基板1′の高分子液晶化合物を含有する高分
子液晶層に接する面の片側だけに配向制御膜を設けても
よい。In the polymer liquid crystal device of the present invention, an alignment control film may be provided only on one side of the substrate 1 or the substrate 1 'in contact with the polymer liquid crystal layer containing the polymer liquid crystal compound.
【0073】前記、高分子液晶化合物及びその組成物は
配向膜を用いた配向法のみでなく、下記のような配向法
によっても良好な配向が得られる。分子配列を確実に行
うものとしては、一軸延伸、二軸延伸、インフレーショ
ン延伸等の延伸法やシエアリングによる再配列が好まし
い。単独ではフィルム性がなく延伸が困難なものはフィ
ルムにサンドイッチすることで共延伸し、望ましい配向
を得ることができる。The polymer liquid crystal compound and the composition thereof can obtain good alignment not only by the alignment method using an alignment film but also by the following alignment method. As a method for ensuring the molecular arrangement, a stretching method such as uniaxial stretching, biaxial stretching, or inflation stretching, or rearrangement by shearing is preferable. Those which do not have film properties by themselves and are difficult to stretch can be co-stretched by sandwiching them with a film to obtain a desired orientation.
【0074】次に、基板1,1′として用いることがで
きるポリマーフィルムには、下記に示すようなものが挙
げられるが、これらに限定されるものではない。すなわ
ち、低密度ポリエチレンフィルム、高密度ポリエチレン
フィルム(三井東圧化学 ハイブロン等)、ポリプロピ
レンフィルム(東レ トレファン等)、ポリエステルフ
ィルム(デュポン マイラー等)、ポリビニルアルコー
ルフィルム(日本合成化学工業 ハイセロン等)、ポリ
アミドフィルム(東洋合成フィルム レイファン等)、
ポリカーボネートフィルム(帝人 テイジンパンライト
等)、ポリイミドフィルム(デュポン KAPTON
等)、ポリ塩化ビニルフィルム(三菱樹脂 ヒシレック
ス等)、ポリ四ふっ化エチレンフィルム(三井フロロケ
ミカル テフロン等)、ポリアクリルフィルム(住友ベ
ークライト スミライト)、ポリスチレンフィルム(旭
ダウ スタイロシート)、ポリ塩化ビニリデンフィルム
(旭ダウ サランフィルム)、セルロースフィルム、ポ
リフッ化ビニルフィルム(デュポン テドラー)等が挙
げられる。Next, examples of polymer films that can be used as the substrates 1 and 1 'include, but are not limited to, the following. That is, low-density polyethylene film, high-density polyethylene film (Mitsui Toatsu Chemical Hiblon, etc.), polypropylene film (Toray Trefane, etc.), polyester film (DuPont Mylar, etc.), polyvinyl alcohol film (Nippon Synthetic Chemical Industry, Hiselon, etc.), polyamide Film (Toyo Gosei Film Reifan, etc.),
Polycarbonate film (Teijin Teijin Panlite etc.), Polyimide film (Dupont KAPTON)
Etc.), polyvinyl chloride film (Mitsubishi Hishilex, etc.), polytetrafluoroethylene film (Mitsui Fluorochemical Teflon, etc.), polyacryl film (Sumitomo Bakelite Sumilite), polystyrene film (Asahi Dow Stylosheet), polyvinylidene chloride Film (Asahi Dow Saran Film), cellulose film, polyvinyl fluoride film (Dupont Tedlar) and the like.
【0075】本発明において、偏光子7,7′としては
偏光フィルム,偏光ビームスプリッター等を用いること
ができる。In the present invention, a polarizing film, a polarizing beam splitter or the like can be used as the polarizers 7 and 7 '.
【0076】本発明の高分子液晶表示素子において、加
熱による効果を用いて表示を行なう場合は、サーマルヘ
ッドやレーザー光を用いることが出来る。In the polymer liquid crystal display device of the present invention, when performing display using the effect of heating, a thermal head or a laser beam can be used.
【0077】レーザー光としては、He−Neガスレー
ザー,Ar2+ガスレーザー,N2 ガスレーザー等のガス
レーザーや、ルビーレーザー,ガラスレーザー,YAG
レーザー等の固体レーザーや、半導体レーザー等を用い
ることが望ましい。また、600nm〜1600nmの
波長範囲の半導体レーザーが好ましく用いられる。特に
好ましくは600〜900nmの波長範囲の半導体レー
ザーが用いられる。また、これらのレーザー光の第2高
調波、第3高調波を用いれば短波長化が可能となる。As the laser light, gas lasers such as He—Ne gas laser, Ar 2+ gas laser, N 2 gas laser, ruby laser, glass laser, YAG
It is desirable to use a solid laser such as a laser, a semiconductor laser, or the like. Further, a semiconductor laser having a wavelength range of 600 nm to 1600 nm is preferably used. Particularly preferably, a semiconductor laser having a wavelength range of 600 to 900 nm is used. The use of the second and third harmonics of these laser beams makes it possible to shorten the wavelength.
【0078】レーザー光を用いる場合は、光吸収層を別
途設けるか、もしくは表示層中に分散・溶解して用いら
れる。表示面に光吸収層もしくは光吸収剤の影響が出る
場合は、可視光域に吸収のないものが望ましい。When a laser beam is used, a light absorbing layer is separately provided, or the light absorbing layer is dispersed and dissolved in a display layer. When the display surface is affected by the light absorbing layer or the light absorbing agent, it is desirable that the light absorbing layer or the light absorbing agent does not absorb light in the visible light region.
【0079】高分子液晶層へ添加するレーザー光吸収化
合物の例としては、アゾ系化合物、ビスアゾ系化合物、
トリスアゾ系化合物、アンスラキノン系化合物、ナフト
キノン系化合物、フタロシアニン系化合物、ナフタロシ
アニン系化合物、テトラベンゾポルフィリン系化合物、
アミニウム塩系化合物、ジイモニウム塩系化合物、金属
キレート系化合物等がある。Examples of the laser light absorbing compound to be added to the polymer liquid crystal layer include an azo compound, a bisazo compound,
Trisazo compounds, anthraquinone compounds, naphthoquinone compounds, phthalocyanine compounds, naphthalocyanine compounds, tetrabenzoporphyrin compounds,
There are aminium salt compounds, diimonium salt compounds, metal chelate compounds and the like.
【0080】前記のレーザー光吸収化合物のうち半導体
レーザー用化合物は近赤外域に吸収をもち、安定な光吸
収色素として有用であり、かつ高分子液晶化合物に対し
て相溶性もしくは分散性がよい。また、中には二色性を
有するものもあり、これら二色性を有する化合物を高分
子液晶中に混合すれば、熱的に安定なホスト−ゲスト型
のメモリー及び表示媒体を得ることもできる。また高分
子液晶化合物中には上記の化合物が二種類以上含有され
ていてもよい。Of the above-mentioned laser light absorbing compounds, compounds for semiconductor lasers have absorption in the near infrared region, are useful as stable light absorbing dyes, and have good compatibility or dispersibility with high molecular liquid crystal compounds. In addition, some have dichroism, and if these dichroic compounds are mixed in a polymer liquid crystal, a thermally stable host-guest type memory and display medium can be obtained. . Further, the polymer liquid crystal compound may contain two or more of the above compounds.
【0081】また、上記化合物と他の近赤外吸収色素や
2色性色素を組み合せてもよい。好適に組み合せられる
近赤外吸収色素の代表的な例としては、シアニン、メロ
シアニン、フタロシアニン、テトラヒドロコリン、ジオ
キサジン、アントラキノン、トリフェノジチアジン、キ
サンテン、トリフェニルメタン、ピリリウム、クロコニ
ウム、アズレンおよびトリフェニルアミン等の色素が挙
げられる。Further, the above compound may be combined with other near infrared absorbing dyes or dichroic dyes. Representative examples of near infrared absorbing dyes that are suitably combined include cyanine, merocyanine, phthalocyanine, tetrahydrocholine, dioxazine, anthraquinone, triphenodithiazine, xanthene, triphenylmethane, pyrylium, croconium, azulene and triphenylamine. And the like.
【0082】なお、高分子液晶化合物に対する上記化合
物の添加量は重量%で、0.1〜20%程度、好ましく
は、0.5〜10%がよい。The amount of the compound to be added to the polymer liquid crystal compound is about 0.1 to 20% by weight, preferably 0.5 to 10%.
【0083】上記高分子液晶素子は、ネマチック液晶相
を示す場合、従来のTN型液晶と同様のスイッチングモ
ードを用いることが出来、カイラルスメクチック液晶相
を示す場合、双安定性を有する強誘電性のスイッチング
モードを用いることが出来る。カイラルスメクチック液
晶相を示して、強誘電性のスイッチングモードを用いる
場合、素子に双安定性を実現するために、らせんの解消
を行なう必要があり、そのためには、膜厚が十分薄くす
る必要がある。具体的には10μm以下にすればよい。The above polymer liquid crystal device can use the same switching mode as a conventional TN type liquid crystal when exhibiting a nematic liquid crystal phase, and can exhibit bistable ferroelectricity when exhibiting a chiral smectic liquid crystal phase. A switching mode can be used. When a chiral smectic liquid crystal phase is used and a ferroelectric switching mode is used, it is necessary to eliminate the helix in order to realize bistability in the device, and for that purpose, the film thickness must be made sufficiently thin. is there. Specifically, the thickness may be set to 10 μm or less.
【0084】本発明の第四の発明の液晶素子のもう一つ
の代表的な例は、配向を固定して、その電気的、光学的
異方性を利用した薄膜としての、あるいは薄膜を利用し
た素子である。Another typical example of the liquid crystal device according to the fourth aspect of the present invention is a thin film utilizing the electrical and optical anisotropy of a fixed orientation and utilizing the thin film. Element.
【0085】このような薄膜は、例えば、本発明の第一
の発明の一般式〔1〕で表される構造を有する化合物
と、先に示したa)からw)のような反応性液晶性化合
物を含む液晶組成物をポリイミドラビング膜やSiO2
斜方蒸着膜等の配向制御膜を有する基板に塗布し、液晶
状態で配向させた後、紫外線等を照射し、重合硬化する
ことにより得ることができる。一般式〔1〕で表される
構造を有する化合物とその他の反応性液晶性化合物を含
む液晶組成物中には、感光開始剤、色素、酸化防止剤等
の添加物を添加することができる。Such a thin film is formed, for example, by reacting the compound having the structure represented by the general formula [1] of the first invention of the present invention with a reactive liquid crystalline compound such as a) to w) shown above. A liquid crystal composition containing a compound is rubbed with a polyimide rubbing film or SiO 2
It can be obtained by applying the composition on a substrate having an orientation control film such as an oblique deposition film, orienting it in a liquid crystal state, and then irradiating ultraviolet rays or the like and polymerizing and curing. Additives such as a photoinitiator, a dye and an antioxidant can be added to the liquid crystal composition containing the compound having the structure represented by the general formula [1] and other reactive liquid crystal compounds.
【0086】このような薄膜は、液晶の持つ光学的特性
に起因して大きな複屈折性を有しているため、偏光板、
1/4波長板、光記録媒体等に利用することができる。
露光時にマスキングすることにより、パターニングする
ことが可能であり、光導波路として使用することもでき
る。通常用いられている光学薄膜に比べ膜厚を非常に薄
くすることができるので透過率が格段に大きいという利
点を持ち、応用範囲は非常に広い。Since such a thin film has a large birefringence due to the optical characteristics of the liquid crystal, a polarizing plate,
It can be used for a quarter-wave plate, an optical recording medium, and the like.
By masking at the time of exposure, patterning is possible, and it can be used as an optical waveguide. Since the film thickness can be made extremely thin as compared with an optical thin film usually used, there is an advantage that the transmittance is remarkably large, and the application range is very wide.
【0087】[0087]
【作用】本発明の一般式〔1〕で表される構造を有する
反応性液晶性化合物は、2官能性で、液晶性の高い化学
構造を持つ架橋性の化合物であり、しかも分子長軸と垂
直な方向に、2つのシアノ基という大きな極性基を有す
る。このため、該反応性液晶性化合物を用いると高分子
液晶化合物の架橋高分子化を液晶性を損なわずに達成す
ることが出来る。また、容易に優れた特性を有する電気
光学薄膜を生成することが出来る。The reactive liquid crystalline compound having a structure represented by the general formula [1] of the present invention is a bifunctional, cross-linkable compound having a chemical structure with high liquid crystallinity, and has a molecular long axis. It has a large polar group of two cyano groups in the vertical direction. For this reason, the use of the reactive liquid crystal compound makes it possible to make the polymer liquid crystal compound crosslinked and polymerized without impairing the liquid crystallinity. Further, an electro-optical thin film having excellent characteristics can be easily produced.
【0088】[0088]
【実施例】以下、実施例を示し、本発明をさらに詳細に
説明するが、本発明は以下の実施例に限定されるもので
はない。EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to the following Examples.
【0089】合成例1 Synthesis Example 1
【0090】[0090]
【化34】 の合成Embedded image Synthesis of
【0091】 6−クロロ−ヘキサノール13.6g
とp−ヒドロキシ安息香酸11.0gをエタノール水溶
液中、KOHとともに加熱還流を10時間行なった。希
塩酸を加え、析出物をろ取した。エタノールで再結晶し
て、p−(6−ヒドロキシヘキシルオキシ)安息香酸
(a)9.5gを得た。13.6 g of 6-chloro-hexanol
And 11.0 g of p-hydroxybenzoic acid were heated and refluxed together with KOH in an aqueous ethanol solution for 10 hours. Dilute hydrochloric acid was added, and the precipitate was collected by filtration. Recrystallization from ethanol yielded 9.5 g of p- (6-hydroxyhexyloxy) benzoic acid (a).
【0092】 p−(6−ヒドロキシヘキシルオキ
シ)安息香酸(a)9.5gとアクリル酸10.0gを
ハイドロキノンの存在下、トルエン中で硫酸を加え50
時間加熱還流した。溶媒を留去し、再結晶して、p−
(6−アクリロイロキシヘキシルオキシ)安息香酸
(b)8.1gを得た。9.5 g of p- (6-hydroxyhexyloxy) benzoic acid (a) and 10.0 g of acrylic acid were added with sulfuric acid in toluene in the presence of hydroquinone to give 50 g.
Heated to reflux for an hour. The solvent was distilled off, recrystallized, and p-
8.1 g of (6-acryloyloxyhexyloxy) benzoic acid (b) was obtained.
【0093】 p−(6−アクリロイロキシヘキシル
オキシ)安息香酸(b)3.5gを2,6−ジ−t−ブ
チルフェノールの存在下、チオニルクロライド5mlと
トルエン20ml中2時間加熱還流した。これに、無水
THF10mlと無水ピリジン1mlを加え、0〜5℃
で2,3−ジシアノ−p−ハイドロキノン1.0gの無
水THF溶液を加えた。5℃で1時間、室温で1時間、
50℃で15時間撹拌した。希塩酸を加え、酢酸エチル
で連続抽出した。溶媒を留去し、カラムクロマトグラフ
ィーで精製して目的とする化合物(I)を2.1g得
た。化合物(I)のIRスペクトルを図2に示す。3.5 g of p- (6-acryloyloxyhexyloxy) benzoic acid (b) was heated to reflux in 5 ml of thionyl chloride and 20 ml of toluene for 2 hours in the presence of 2,6-di-t-butylphenol. To this, 10 ml of anhydrous THF and 1 ml of anhydrous pyridine were added, and 0 to 5 ° C was added.
Then, a solution of 1.0 g of 2,3-dicyano-p-hydroquinone in anhydrous THF was added. 1 hour at 5 ° C, 1 hour at room temperature,
Stirred at 50 ° C. for 15 hours. Dilute hydrochloric acid was added, followed by continuous extraction with ethyl acetate. The solvent was distilled off, and the residue was purified by column chromatography to obtain 2.1 g of the desired compound (I). FIG. 2 shows the IR spectrum of the compound (I).
【0094】実施例1 合成例1 で得られた化合物(I)0.046gと下記の
構造で表される化合物(II)1.00gとをDMF
中、55℃で40hr,AIBNを重合開始剤として重
合し(II)た。 Example 1 0.046 g of the compound (I) obtained in Synthesis Example 1 and 1.00 g of the compound (II) represented by the following structure were mixed with DMF.
The polymerization was carried out at 55 ° C. for 40 hours using AIBN as a polymerization initiator (II).
【0095】[0095]
【化35】 Embedded image
【0096】メタノールへ再沈殿をくり返し、ポリマー
(2a)0.72gを得た。The reprecipitation was repeated in methanol to obtain 0.72 g of a polymer (2a).
【0097】Mn= 26,300 Mw=102,200 (GPCにより測定) 相転移温度Mn = 26,300 Mw = 102,200 (measured by GPC) Phase transition temperature
【0098】[0098]
【数1】 (Equation 1)
【0099】ポリマー(2a)の 1H−NMRを図3に
示した。The 1 H-NMR of the polymer (2a) is shown in FIG.
【0100】実施例2 化合物(I)0.057gと化合物(II)1.00g
を実施例1と同様に重合反応を行なった。同様に精製し
ポリマー(3a)0.68g得た。 Example 2 0.057 g of compound (I) and 1.00 g of compound (II)
Was subjected to a polymerization reaction in the same manner as in Example 1 . Purification was performed in the same manner to obtain 0.68 g of a polymer (3a).
【0101】Mn= 31,600 Mw=129,500 相転移温度Mn = 31,600 Mw = 129,500 Phase transition temperature
【0102】[0102]
【数2】 ポリマー(3a)の 1H−NMRを図4に示した。(Equation 2) 1 H-NMR of the polymer (3a) is shown in FIG.
【0103】比較例1 化合物(II)1.00gを実施例1と同様に重合、精
製して、ポリマーAを得た。Comparative Example 1 1.00 g of the compound (II) was polymerized and purified in the same manner as in Example 1 to obtain a polymer A.
【0104】Mn= 12,400 Mw= 21,000 相転移温度Mn = 12,400 Mw = 21,000 Phase transition temperature
【0105】[0105]
【数3】 (Equation 3)
【0106】実施例3 ポリマー(2a)及び(3a)の7wt%DMF溶液を
ポリイミドラビング膜付ガラス基板に塗布した。100
℃で40時間、乾燥、アニーリングしたところ、ポリマ
ー(2a),(3a)は均一に配向した凹凸のない薄膜
が得られた。 Example 3 A 7 wt% DMF solution of the polymers (2a) and (3a) was applied to a glass substrate provided with a polyimide rubbing film. 100
After drying and annealing at 40 ° C. for 40 hours, polymers (2a) and (3a) were obtained as uniformly oriented thin films without irregularities.
【0107】比較例2 ポリマーAについて、実施例3と同様に7wt%DMF
溶液をポリイミドラビング膜付ガラス基板に塗布した。
100℃で40時間、乾燥、アニーリングしたところ、
ポリマー(2a),(3a)とは異なり、数カ所にしわ
が観測された。Comparative Example 2 For polymer A, as in Example 3 , 7 wt% DMF
The solution was applied to a glass substrate with a polyimide rubbing film.
After drying and annealing at 100 ° C for 40 hours,
Unlike the polymers (2a) and (3a), wrinkles were observed at several places.
【0108】実施例4 下記の各成分 Example 4 The following components
【0109】[0109]
【化36】 Embedded image
【0110】を混合溶融し、ポリイミドラビング膜付き
ガラス基板に塗布した。ネマチック液晶状態でホールド
して、一軸配向した。30cmの距離から150Wの紫
外線ランプを照射し重合硬化したところ、均一な一軸配
向を保持した薄膜となった。Was melted and applied to a glass substrate provided with a polyimide rubbing film. The film was held in a nematic liquid crystal state and was uniaxially oriented. When irradiated with a 150 W ultraviolet lamp from a distance of 30 cm and polymerized and cured, a thin film having uniform uniaxial orientation was obtained.
【0111】実施例5 実施例1 で得られたポリマー(2a)と化合物(II)
を用いて、以下の表1に示す2つの組成物を調整した。 Example 5 The polymer (2a) obtained in Example 1 and the compound (II)
Was used to prepare the two compositions shown in Table 1 below.
【0112】[0112]
【表1】 [Table 1]
【0113】ポリマー(2a),X,Yの3種の化合
物、組成物をそれぞれポリイミドラビング配向膜を形成
してあるITO透明電極基板に塗布し、上面からITO
透明電極基板を密着させ、セルを形成した。ネマチック
相で20V/μmの交流電界のオンオフを行なったとこ
ろ、偏光顕微鏡下、電界に追随した分子の応答が観測さ
れた。The polymer (2a), the three compounds of X and Y, and the composition were respectively applied to an ITO transparent electrode substrate on which a polyimide rubbing alignment film was formed, and ITO was applied from the upper surface.
The transparent electrode substrate was brought into close contact to form a cell. When an AC electric field of 20 V / μm was turned on and off in the nematic phase, a response of molecules following the electric field was observed under a polarizing microscope.
【0114】[0114]
【発明の効果】以上説明した様に、本発明によれば、反
応性液晶性化合物を使用した高分子液晶化合物、高分子
組成物を用いることにより、フィルム性の優れた、応答
性の良好な、大面積の液晶素子の実現が可能であり、ま
た光学的特性に優れた電気光学薄膜を得ることが出来る
効果がある。As has been described above, according to the present invention, according to the present invention, the anti
By using a polymer liquid crystal compound and a polymer composition using a responsive liquid crystal compound, it is possible to realize a large-area liquid crystal device with excellent film properties, good responsiveness, and improved optical characteristics. There is an effect that an excellent electro-optical thin film can be obtained.
【図1】本発明の高分子液晶素子の一例を示し、図1
(a)は本発明の高分子液晶素子の平面図、図1(b)
はそのAA′線断面図である。FIG. 1 shows an example of a polymer liquid crystal device of the present invention.
(A) is a plan view of the polymer liquid crystal device of the present invention, and FIG.
Is a sectional view taken along the line AA '.
【図2】合成例1の化合物(I)のIRスペクトル図で
ある。FIG. 2 is an IR spectrum of Compound (I) of Synthesis Example 1 .
【図3】実施例1のポリマー(2a)の1H−NMR
(CDCl3)を示す図である。FIG. 3 1 H-NMR of polymer (2a) of Example 1
Is a diagram showing a (CDCl 3).
【図4】実施例2のポリマー(3a)の1H−NMR
(CDCl3)を示す図である。FIG. 4 shows 1 H-NMR of polymer (3a) of Example 2 .
Is a diagram showing a (CDCl 3).
1,1′ 基板 2,2′ 透明電極 3 高分子液晶層 4 スペーサ 5,5′ 配向制御膜 6 接着剤 7,7′ 偏光子 DESCRIPTION OF SYMBOLS 1, 1 'Substrate 2, 2' Transparent electrode 3 Polymer liquid crystal layer 4 Spacer 5, 5 'Orientation control film 6 Adhesive 7, 7' Polarizer
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 FI // C07C 255/55 C07C 255/55 (72)発明者 江口 岳夫 東京都大田区下丸子3丁目30番2号 キ ヤノン株式会社内 (56)参考文献 特表 平2−502099(JP,A) J.CHEM.SOC.PERKIN TRANS.1(1990)No.8, p.1169−1177 (58)調査した分野(Int.Cl.7,DB名) CA(STN) CAOLD(STN) REGISTRY(STN)──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification symbol FI // C07C 255/55 C07C 255/55 (72) Inventor Takeo Eguchi 3-30-2 Shimomaruko, Ota-ku, Tokyo Canon Inc. (56) References Table 2-502099 (JP, A) CHEM. SOC. PERKIN TRANS. 1 (1990) No. 8, p. 116-1177 (58) Fields investigated (Int. Cl. 7 , DB name) CA (STN) CAOLD (STN) REGISTRY (STN)
Claims (4)
性化合物を重合成分として有する高分子液晶化合物。 【化2】 (式中、R1は水素原子、アルキル基またはハロゲン基
を表わす。U,V,W,X,Yはそれぞれ同一もしくは
異なる、単結合,−O−,−OCO−または−COO−
を表わす。aは0または1を表わす。b,fはそれぞれ
同一もしくは異なる0から15までの整数を表わす。
c,d,eはそれぞれ同一もしくは異なる0から2まで
の整数を表わす。)1. A polymer liquid crystal compound having a reactive liquid crystal compound represented by the following general formula [1] as a polymerization component. Embedded image (Wherein, R 1 represents a hydrogen atom, an alkyl group, or a halogen group. U, V, W, X, and Y are the same or different and are each a single bond, —O—, —OCO—, or —COO—
Represents a represents 0 or 1. b and f represent the same or different integers from 0 to 15.
c, d, and e each represent the same or different integers from 0 to 2. )
性化合物を重合成分として有するネマチック高分子液晶
化合物。 【化3】 (式中、R1は水素原子、アルキル基またはハロゲン基
を表わす。U,V,W,X,Yはそれぞれ同一もしくは
異なる、単結合,−O−,−OCO−または−COO−
を表わす。aは0または1を表わす。b,fはそれぞれ
同一もしくは異なる0から15までの整数を表わす。
c,d,eはそれぞれ同一もしくは異なる0から2まで
の整数を表わす。)2. A nematic polymer liquid crystal compound having a reactive liquid crystal compound represented by the following general formula [1] as a polymerization component. Embedded image (Wherein, R 1 represents a hydrogen atom, an alkyl group, or a halogen group. U, V, W, X, and Y are the same or different, a single bond, —O—, —OCO—, or —COO—
Represents a represents 0 or 1. b and f represent the same or different integers from 0 to 15.
c, d, and e each represent the same or different integers from 0 to 2. )
晶化合物を含有する高分子液晶組成物。3. A polymer liquid crystal composition comprising the polymer liquid crystal compound according to claim 1.
ることを特徴とする液晶素子。 4. A liquid crystal device comprising the polymer liquid crystal composition according to claim 3.
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JP19899192A JP3228348B2 (en) | 1992-07-03 | 1992-07-03 | Polymer liquid crystal compound, liquid crystal composition and liquid crystal element |
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