CN117089359A - Polymer dispersed liquid crystal composition, liquid crystal element, and light adjusting element - Google Patents
Polymer dispersed liquid crystal composition, liquid crystal element, and light adjusting element Download PDFInfo
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- CN117089359A CN117089359A CN202310524879.9A CN202310524879A CN117089359A CN 117089359 A CN117089359 A CN 117089359A CN 202310524879 A CN202310524879 A CN 202310524879A CN 117089359 A CN117089359 A CN 117089359A
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- Prior art keywords
- liquid crystal
- phenylene
- group
- polymerizable
- crystal composition
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- 239000000203 mixture Substances 0.000 title claims abstract description 205
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 174
- 239000004983 Polymer Dispersed Liquid Crystal Substances 0.000 title claims abstract description 115
- 150000001875 compounds Chemical class 0.000 claims description 108
- -1 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, 2-methyl-1, 4-phenylene Chemical group 0.000 claims description 100
- 125000004432 carbon atom Chemical group C* 0.000 claims description 78
- 239000000758 substrate Substances 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 58
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 36
- 125000001153 fluoro group Chemical group F* 0.000 claims description 34
- 239000000049 pigment Substances 0.000 claims description 28
- 239000002245 particle Substances 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 23
- 229920000728 polyester Polymers 0.000 claims description 22
- 238000006467 substitution reaction Methods 0.000 claims description 22
- 125000002947 alkylene group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 239000003963 antioxidant agent Substances 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
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- 239000004611 light stabiliser Substances 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 230000003078 antioxidant effect Effects 0.000 claims description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 6
- 229920000106 Liquid crystal polymer Polymers 0.000 claims description 6
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 210000002858 crystal cell Anatomy 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 24
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- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 17
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- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 10
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- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 7
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 6
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- 125000004122 cyclic group Chemical group 0.000 description 5
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 5
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- 125000006850 spacer group Chemical group 0.000 description 5
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- 238000000149 argon plasma sintering Methods 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- CSFWPUWCSPOLJW-UHFFFAOYSA-N lawsone Chemical compound C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 238000005096 rolling process Methods 0.000 description 4
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- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 3
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-UHFFFAOYSA-N 0.000 description 3
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 3
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 3
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- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 3
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- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical compound C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 3
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 3
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- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 3
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 1
- 229960002479 isosorbide Drugs 0.000 description 1
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BUGISVZCMXHOHO-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2-[[1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(CO)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(CO)(CO)CO BUGISVZCMXHOHO-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- SKEQOTBKQUCUGK-UHFFFAOYSA-N o-(2-hydroxyethyl) propanethioate Chemical compound CCC(=S)OCCO SKEQOTBKQUCUGK-UHFFFAOYSA-N 0.000 description 1
- XVKLLVZBGMGICC-UHFFFAOYSA-N o-[3-propanethioyloxy-2,2-bis(propanethioyloxymethyl)propyl] propanethioate Chemical compound CCC(=S)OCC(COC(=S)CC)(COC(=S)CC)COC(=S)CC XVKLLVZBGMGICC-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 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
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/542—Macromolecular compounds
- C09K19/544—Macromolecular compounds as dispersing or encapsulating medium around the liquid crystal
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/56—Aligning agents
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1334—Constructional arrangements; Manufacturing methods based on polymer dispersed liquid crystals, e.g. microencapsulated liquid crystals
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1334—Constructional arrangements; Manufacturing methods based on polymer dispersed liquid crystals, e.g. microencapsulated liquid crystals
- G02F1/13345—Network or three-dimensional gels
Abstract
The invention provides a polymer dispersed liquid crystal composition, a liquid crystal element and a light adjusting element, which have excellent adhesion with a base material, reliability, heat resistance, transmittance after heating, transparency when voltage is switched on, high-speed response in a low-temperature area and scattering retention in a high-temperature environment. The polymer dispersed liquid crystal composition contains a polymerizable composition (MA) and a non-polymerizable liquid crystal composition (LB). The value of dielectric anisotropy of the non-polymerizable liquid crystal composition (LB) is positive sign, and the rotational viscosity [ gamma 1[ mPa.sec ] at 25 ℃ is 400 or less.
Description
Technical Field
The present invention relates to a polymer dispersed liquid crystal composition, a liquid crystal element obtained using the polymer dispersed liquid crystal composition, and a light control element using the liquid crystal element. The light modulation element comprises: dimming elements used in Smart Windows (SW), window glass of buildings such as houses or buildings, doors, partition boards (partition), private glass (private glass), and the like; dimming elements for use in glass windows, mirrors, roofs, etc. used in transportation media such as automobiles, airplanes, ships, electric trains, etc.; light control elements used for light control of digital cameras, smart phones, etc., light scattering plates for light sources for displays, light guiding plates, reflection plates for reflective displays, transparent displays, etc.
Background
A polymer dispersed liquid crystal element (PDLC) in which a liquid crystal material is dispersed in a polymer matrix or a polymer network type liquid crystal element (PNLC) in which a liquid crystal material is present in a polymer network space is different from a general liquid crystal element, and the degree of transmission/scattering of the element can be adjusted. According to the above feature, the present invention can be expected to be applied to a high-value display such as a reflective display, a transparent display, a local dimming (local dimming) light diffusion element, and a variable reflective element. On the other hand, regarding applications in window Glass for building materials or transportation, interior decoration, exterior appearance (exterior), personal Glass (Straight Glass (SG)), smart Glass for variable projector screens, digital signage, or the like, or Smart Window (SW), etc., which flexibly utilize a light-adjusting function of transmission/scattering, a light-adjusting material for realizing the applications is desired because a mobile terminal is used with the development of communication technology in recent years and control of various equipment and machines can be realized both for industrial use and for home use.
In particular, when the glass is spread on the smart glass or the Smart Window (SW), the entire surface of the polymer dispersed liquid crystal element or the entire surface of the polymer dispersed liquid crystal element is dimmed, and therefore, in general, a voltage is applied to the entire surface with a simple structure such as a transparent substrate, a transparent electrode layer, the liquid crystal element layer, a transparent electrode layer, and a transparent substrate layer. When used in a smart window or the like, high scattering is desired because the state of the facing surface is not clear, and high transparency is required even in a transparent state. Further, these states can be electrically switched, but power saving is required, and a low driving voltage of ON (ON) and OFF (OFF) switching voltages is desired. In addition, from the viewpoint of productivity, it is important that the film be directly formed on a flexible substrate such as a polyethylene terephthalate (Polyethylene Terephthalate, PET) film or a Polycarbonate (PC) film by a roll-to-roll method. In order to produce the liquid crystal element by the roll-to-roll method, the adhesion (adhesion) between the substrate and the liquid crystal element is also an important characteristic, and high adhesion to the substrate is also required. Further, smart windows and the like are sometimes used outdoors and the like, and therefore high light resistance and high heat resistance are also required.
Patent document 1 discloses an example of low-voltage driving using a specific monomer compound, but has a problem of insufficient adhesion. In patent document 2, a specific liquid crystal compound is used to improve light resistance, and a certain effect is observed in light resistance, but there is a problem that light scattering property is insufficient. Patent document 3 discloses that a specific polymerizable compound is used to improve adhesion, and that the adhesion has a certain effect, but has a problem of high driving voltage. As described above, a method for improving scattering property, driving voltage, and adhesion with good balance is demanded.
Further, in the case of an intelligent window used for a glass window or the like used for a transportation medium, a driving temperature range is required to be wide so that a dimming operation is performed without any problem from a hot in midsummer to an extremely cold air temperature in a long winter. Patent document 4 proposes a liquid crystal composite comprising a liquid crystal composition and a polymerizable compound, which can produce a liquid crystal light control element having improved weather resistance, and a certain effect is observed in terms of improving the durability to external light, but the drivability and high-speed responsiveness in a low-temperature region (for example, -10 ℃ to-30 ℃) have not been studied.
[ Prior Art literature ]
[ patent literature ]
[ patent document 1] Japanese patent laid-open No. 6-208107
Patent document 2 Japanese patent laid-open No. 2007-91850
Patent document 3 japanese patent laid-open publication No. 2011-026526
[ patent document 4] Japanese patent laid-open No. 2021-066875
Disclosure of Invention
[ problem to be solved by the invention ]
As described above, in particular, in applications such as windows of buildings where the light modulator is placed in contact with the outside air, or in applications such as transportation media where the light modulator is used in a wide temperature environment including extremely cold temperatures ranging from hot in midsummer to cold in winter, it is necessary to exhibit the characteristics required for various light modulator elements in a wide temperature range. That is, it is required to satisfy characteristics such as adhesion to a substrate, reliability, drive voltage, transparency when voltage is on, high-speed response, scattering property, and the like in a wide temperature range from high temperature to low temperature, and it is required to realize transmission scattering property, drive voltage, and adhesion in a low temperature region at an excellent level.
Accordingly, an object of the present invention is to provide a polymer dispersed liquid crystal composition capable of producing a liquid crystal light-adjusting element having high transparency in a transmission state, high scattering property in a scattering state, low driving voltage, and excellent adhesion particularly in a low temperature region, and to provide a liquid crystal element and a light-adjusting element using the polymer dispersed liquid crystal composition.
[ means of solving the problems ]
The present inventors have made an intensive study to solve the above-mentioned problems, and as a result, have found that a polymer dispersed liquid crystal composition capable of producing a liquid crystal light adjusting element having high transparency in a transmission state, high scattering property in a scattering state, low driving voltage, and excellent adhesion, particularly in a low temperature region, can be obtained by using a polymer dispersed liquid crystal composition exhibiting a specific composition and physical property values, and have completed the present invention.
That is, the present invention provides the following polymer dispersed liquid crystal composition, liquid crystal element, and light control element.
[1] A polymer-dispersed liquid crystal composition comprising a polymerizable composition (MA) and a non-polymerizable liquid crystal composition (LB), wherein the non-polymerizable liquid crystal composition (LB) has a positive value of dielectric anisotropy and a rotational viscosity [ gamma 1[ mPa-sec ] at 25 ℃ of 400 or less.
[2] The polymer dispersed liquid crystal composition according to [1], wherein the polymerizable composition (MA) contains one or more kinds of polymerizable compounds represented by the following general formula (ii).
P ii1 -Z ii1 -A ii1 (ii)
(wherein P ii1 Represents a polymerizable group and is preferably a polymerizable group,
Z ii1 represents a single bond or an alkylene group having 1 to 7 carbon atoms, one or more of which are not adjacent to each other-CH 2 -independently of each other through-O-, in such a way that the oxygen atoms are not directly adjacent-CO-, -COO-or-OCO-substitution,
A ii1 the expression of the formulas (ii-1) to (ii-20);
(wherein, more than one-CH 2 -can be independently passed through-O-, -S-, -COO-, -OCO-, -NH-, -NCH 3 -or-CO-substitution, in the case where in total more than two oxygen atoms and/or sulfur atoms are present in the general formulae (ii-1) to (ii-20), they are not bonded to each other as in-O-O-, -O-S-or-S-S-, and in addition, more than one-CH 2 -CH 2 -may be substituted with-ch=ch-group, and in addition, the hydrogen atom in the general formulae (ii-1) to (ii-20) may be substituted with an alkyl group having 1 to 8 carbon atoms, one or more of the alkyl groups being not adjacent-CH 2 -each independently substituted by-O-, -CO-, -COO-or-OCO-in such a way that the oxygen atoms are not directly adjacent; in addition, the black dots in the formula represent the direction Z ii1 Bond) of (c))
[3] The polymer-dispersed liquid crystal composition according to [1] or [2], wherein the non-polymerizable liquid crystal composition (LB) contains one or more compounds represented by the following general formula (iii).
(wherein R is iii1 Independently of one another, is an n-alkyl, n-alkoxy, alkenyl, alkenyloxy or alkoxyalkyl radical having from 1 to 7 carbon atoms,
R iii2 represents fluorine atom, chlorine atom, cyano group, CF 3 Radical, OCF 3 Radical, OCHF 2 A group, NCS group or C1-10 alkyl group, one or both of which are not adjacent to each other, -CH 2 The radical may be substituted by oxygen atoms, -COO-, -OCO-, and, in addition, more than one-CH 2 CH 2 Can be substituted by-CH=CH-or-C≡C) -,
A iii1 represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, 2-methyl-1, 4-phenylene, 3-methyl-1, 4-phenylene, 2, 3-dimethyl-1, 4-phenylene, 3, 5-dimethyl-1, 4-phenylene or 2, 6-dimethyl-1, 4-phenylene,
A iii2 a is a iii3 Each independently of the others represents 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, 2-methyl-1, 4-phenylene, 3-methyl-1, 4-phenylene, 2, 3-dimethyl-1, 4-phenylene, 3, 5-dimethyl-1, 4-phenylene or 2, 6-dimethyl-1, 4-phenylene,
Z iii1 Z is as follows iii2 One of them is-C.ident.C-, the other, when present, is-C.ident.C-, -CF 2 O-、-OCF 2 -、-CH＝CH-、-CF＝CF-、-COO-、-CH 2 -CH 2 -、-CF 2 -CF 2 -or a single bond,
n iii is 0 or 1)
[4] The polymer dispersed liquid crystal composition according to any one of [1] to [3], wherein the polymerizable composition (MA) contains one or more polymerizable compounds represented by the following general formula (v).
P v1 -R v1 (v)
(wherein P v1 Represents a polymerizable group and is preferably a polymerizable group,
R v1 represents a linear or branched alkyl group having 1 to 22 carbon atoms, one or more of which are-CH 2 -can be substituted independently of one another by-O-, -CO-, -COO-, -OCO-or-P (=o) (-OH) -in such a way that the oxygen atoms are not directly adjacent, one or more hydrogen atoms present in the alkyl radical being each independently substituted by fluorine atoms or-OH)
[5] The polymer dispersed liquid crystal composition according to any one of [1] to [4], wherein the polymerizable composition (MA) contains one or two or more polyfunctional (meth) acrylate oligomers (i) having a weight average molecular weight of 2000 or more.
[6] The polymer-dispersed liquid crystal composition according to any one of [1] to [5], wherein the polymerizable composition (MA) contains one or more selected from the group consisting of a polyfunctional polymerizable oligomer and a polyfunctional polymerizable monomer having a weight average molecular weight of less than 2000 represented by the following general formula (iv).
(wherein Y is iv1 Represents a hydrogen atom or a methyl group,
X iv1 n represents 130 or less carbon atoms iv1 A linear, branched or cyclic hydrocarbon group having a valence, and at least one of the linear, branched or cyclic hydrocarbon groups-CH 2 The radicals may each independently be interrupted by-O-, by oxygen atoms which are not directly adjacent to one another-NH-, -CO-, -COO-, -OCO-, -CH=CH-, or-C≡C-substitution, one or more hydrogen atoms present in the linear, branched or cyclic hydrocarbon group may be each independently substituted with a fluorine atom or-OH,
n iv1 an integer of 2 to 6
[7] The polymer-dispersed liquid crystal composition according to any one of [1] to [6], wherein the polymerizable composition (MA) further contains an additive represented by the following general formula (X).
(wherein Y is X1 Represents a hydrogen atom or a methyl group,
X X1 n represents 130 or less carbon atoms X1 A linear, branched or cyclic hydrocarbon group having a valence, and at least one of the linear, branched or cyclic hydrocarbon groups-CH 2 The radicals may each independently be interrupted by-O-, by oxygen atoms which are not directly adjacent to one another-NH-, -CO-, -COO-, -OCO-, -CH=CH-, or-C≡C-substitution, one or more hydrogen atoms present in the linear, branched or cyclic hydrocarbon group may be each independently substituted with a fluorine atom or-OH,
n X1 An integer of 1 to 6 is represented,
here, X is X1 At least one of-CH 2 -the radical is substituted by the following formula (X-1)
[8] The polymer dispersed liquid crystal composition according to any one of [1] to [7], further comprising a polymerization initiator.
[9] The polymer-dispersed liquid crystal composition according to any one of [5] to [8], wherein the multifunctional (meth) acrylate oligomer (i) having a weight average molecular weight of 2000 or more is one or two or more selected from the group consisting of urethane-based (meth) acrylate oligomers and polyester-based (meth) acrylate oligomers.
[10] The polymer-dispersed liquid crystal composition according to any one of [1] to [9], wherein the polymerizable composition (MA) further contains one or more selected from the group consisting of a polymerization inhibitor, an antioxidant, a light stabilizer, particles having a particle diameter of less than 1 μm, a pigment and a pigment.
[11] A liquid crystal element obtained by using the polymer dispersed liquid crystal composition according to any one of [1] to [10 ].
[12] A dimming element, comprising:
a pair of transparent electrode substrates; and
a liquid crystal polymer complex disposed between the transparent electrode substrates and comprising a polymer network and a liquid crystal compound,
In the light-adjusting element, the light-adjusting element is provided with a light-adjusting element,
the polymer network being derived from the polymerizable composition (MA) contained in the polymer dispersed liquid crystal composition according to any one of [1] to [10],
the liquid crystal compound is the non-polymerizable liquid crystal composition (LB) contained in the polymer dispersed liquid crystal composition according to any one of [1] to [10 ].
[ Effect of the invention ]
The present invention provides a polymer dispersed liquid crystal composition which can produce a liquid crystal light-adjusting element having high transparency in a transmission state, high scattering property in a scattering state, low driving voltage, and excellent adhesion particularly in a low temperature region, and a liquid crystal element and a light-adjusting element using the polymer dispersed liquid crystal composition.
Detailed Description
Embodiments of the polymer-dispersed liquid crystal composition and polymer-dispersed liquid crystal element using the same according to the present invention will be described.
The present embodiment is described as a specific example for better understanding of the gist of the present invention, and the present invention is not limited to the specific example unless specified.
Polymer dispersed liquid Crystal composition
As described above, the polymer dispersed liquid crystal composition of the present invention contains the polymerizable composition (MA) and the non-polymerizable liquid crystal composition (LB).
In the polymer dispersed liquid crystal composition of the present invention, the weight ratio (LB/MA) of the non-polymerizable liquid crystal composition (LB) to the polymerizable composition (MA) is preferably in the range of 30/70 to 70/30, more preferably 40/60 to 60/40, still more preferably 45/55 to 60/40, and particularly preferably 50/50. Hereinafter, each component constituting the polymerizable composition (MA) and each component constituting the non-polymerizable liquid crystal composition (LB) will be specifically described.
In the present invention, the value of the dielectric anisotropy of the non-polymerizable liquid crystal composition (LB) is positive sign, and the rotational viscosity γ1[ mPa.sec ] at 25℃is 400 or less.
In a liquid crystal cell, in order to improve the responsiveness of a liquid crystal material, it is important to reduce the rotational viscosity of the liquid crystal material. This applies to the polymer dispersed liquid crystal element using the polymer dispersed liquid crystal composition of the present invention. The rotational viscosity of the non-polymerizable liquid crystal composition (LB) having a positive value of dielectric anisotropy is determined by a method described in, for example, japanese patent application laid-open No. 2006-243638. That is, the value of dielectric anisotropy is determined by applying a pulse voltage to a liquid crystal test cell for sandwiching a nematic liquid crystal material having a positive sign with a substrate subjected to horizontal alignment, and measuring a transition current waveform flowing through the liquid crystal test cell.
The non-polymerizable liquid crystal compound having a positive sign in dielectric anisotropy preferably has a rotational viscosity γ1 at 25 ℃ of 600 or less, preferably 500 or less, preferably 450 or less, more preferably 400 or less, further preferably 350 or less, further preferably 300 or less, and particularly preferably 250 or less.
[ polymerizable composition (MA) ]
The polymerizable composition (MA) preferably contains the following second component, first component, fourth component and/or fifth component.
[ second component ]
The second component is a cyclic monofunctional polymerizable compound represented by the following general formula (ii).
P ii1 -Z ii1 -A ii1 (ii)
(wherein P ii1 Represents a polymerizable group and is preferably a polymerizable group,
Z ii1 represents a single bond or an alkylene group having 1 to 7 carbon atoms, one or more of which are not adjacent to each other-CH 2 -independently of each other through-O-, in such a way that the oxygen atoms are not directly adjacent-CO-, -COO-or-OCO-substitution,
A ii1 represented by the formulae (ii-1) to (ii-20),
(wherein, more than one-CH 2 -can be independently passed through-O-, -S-, -COO-, -OCO-, -NH-, -NCH 3 -or-CO-substitution, in the case where in total more than two oxygen atoms and/or sulfur atoms are present in the general formulae (ii-1) to (ii-20), they are not bonded to each other as in-O-O-, -O-S-or-S-S-, and in addition, more than one-CH 2 -CH 2 -may be substituted with-ch=ch-group, and in addition, the hydrogen atom in the general formulae (ii-1) to (ii-20) may be substituted with an alkyl group having 1 to 8 carbon atoms, one or more of the alkyl groups being not adjacent-CH 2 -each independently substituted by-O-, -CO-, -COO-or-OCO-in such a way that the oxygen atoms are not directly adjacent; in addition, the black dots in the formula represent the direction Z ii1 Bond) of (c))
The compound represented by the general formula (ii) is a material having excellent flexibility, and when the compound is used, cloudiness can be maintained even in a curved state. In addition, the compatibility of the components in the polymerizable composition can be improved while improving the adhesion. The compound represented by the general formula (ii) is a non-liquid crystalline compound.
In the compound represented by the general formula (ii), P in the formula ii1 Preferably, the polymerizable groups are each independently represented by any one of the following formulas (P-1) to (P-21). In the following formulas (P-1) to (P-21), the bond to a carbon atom or other atom is represented.
Among the polymerizable groups represented by the above formulae (P-1) to (P-21), the formula (P-1), the formula (P-2), the formula (P-7), the formula (P-12), the formula (P-13) or the formula (P-21) is preferable, the formula (P-1), the formula (P-2), the formula (P-7) and the formula (P-21) are more preferable, and the formula (P-1), the formula (P-2) and the formula (P-21) are particularly preferable from the viewpoint of improving the polymerizability and the storage stability.
In the compound represented by the general formula (ii), Z in the formula ii1 Represents a single bond or an alkylene group having 1 to 7 carbon atoms, one or more of which are-CH 2 -each independently substituted by-O-, -CO-, -COO-, or-OCO-in such a manner that the oxygen atoms are not directly adjacent, and one or more hydrogen atoms present in the alkylene group may each independently be substituted by a fluorine atom. Wherein Z is ii1 Preferably a single bond or an alkylene group having 1 to 6 carbon atoms, more preferably a single bond or an alkylene group having 1 to 3 carbon atoms, particularly preferably a single bond or-CH 2 -a radical.
In the compound represented by the general formula (ii), A is ii1 In view of further improving the adhesion, the adhesion is preferably improved by the following formula A ii1 More specifically, the heterocyclic structure containing a nitrogen atom, an oxygen atom and a sulfur atom is preferably represented by the following formulas (ii-a 1) to (ii-a 11).
(wherein, more than one-CH 2 Each independently substituted by-CO-, and in addition, the hydrogen atom in the formulae (ii-a 1) to (ii-a 11) may be substituted by an alkyl group having 1 to 8 carbon atoms, one or more of the alkyl groups being not adjacent to-CH 2 -each independently substituted by-O-, -CO-, -COO-or-OCO-in such a way that the oxygen atoms are not directly adjacent; in addition, the hydrogen atom in the general formulae (ii-a 1) to (ii-a 11) may be substituted with an alkyl group having 1 to 8 carbon atoms, the alkyl group may be a straight chain or a branched chain, and one or more of the alkyl groups may be a non-adjacent-CH group 2 Can be free of oxygen atomsDirectly adjacent to each other via-O-, respectively and independently-CO-, -COO-or-OCO-substitution; in addition, the black dots in the formula represent the direction Z ii1 Is a key of (a) bonding key(s)
In particular, when the cyclic structure has a nitrogen atom, the adhesion of the cyclic structure can be further improved by the presence of the nitrogen atom.
Specifically, the compounds represented by the general formula (II) are preferably the following compounds (II-34) to (II-51).
(wherein X 5 Represents a hydrogen atom or a methyl group)
Of the structural formulae (II-34) to (II-51), more preferable are (II-34), (II-36), (II-38), (II-39), (II-40), (II-43), (II-45) and (II-47).
In terms of improving the adhesion, the content of the compound represented by the general formula (ii) is preferably 10% by mass or more, more preferably 20% by mass or more, and particularly preferably 30% by mass or more, relative to 100% by mass of the total amount of the polymerizable composition (MA) contained in the polymer-dispersed liquid crystal composition of the present invention, in terms of improving the compatibility of the components in the polymerizable composition. In view of the reduction of the voltage, it is preferably 80 mass% or less, preferably 70 mass% or less, preferably 60 mass% or less, more preferably 50 mass% or less, and particularly preferably 40 mass% or less.
In the present application, the group-CH may be substituted with various structures such as alkyl, alkylene, etc 2 In the case of the above, the number of carbon atoms of the alkyl group and the like means the number of carbon atoms before substitution. For example, when the definition is "alkyl having 1 to 8 carbon atoms", the definition is substituted with a structure containing two carbon atoms, and the total carbon number is 9. In the substitution of-CH by various structures 2 CH 2 In the case of-also, the number of carbon atoms before substitution.
[ first component ]
The first component is a multifunctional (meth) acrylate oligomer having a weight average molecular weight of 2000 or more.
The multifunctional (meth) acrylate oligomer is a compound required for introducing a crosslinked structure into the network structure of the polymer and for obtaining good adhesion. Among the multifunctional (meth) acrylate oligomers, difunctional acrylate oligomers are preferred. Further, in order to pay attention to adhesion to a substrate, a urethane acrylate oligomer or a polyester acrylate oligomer is preferable, and a urethane acrylate oligomer is more preferable. In the urethane acrylate oligomer, the polyol skeleton structure is a polyester-based polyol skeleton structure, a polyether-based polyol skeleton structure, or the like, but a polyether-based polyol skeleton structure is preferable. The molecular weight is 2000 or more, preferably 2000 to 60000, more preferably 2500 to 40000, still more preferably 2800 to 35000, still more preferably 3000 to 30000. This is because: if the molecular weight is too small, the degree of hardening shrinkage increases due to an increase in the crosslinking density caused by an increase in the (meth) acrylic group contained in one molecule, and on the other hand, if the molecular weight is too large, the inter-crosslinking distance becomes long, and therefore the gap becomes large and liquid crystal is easily absorbed, and therefore the scattering property as a polymer dispersed liquid crystal decreases. Namely, because: if left in an environment at high temperature, the polymer absorbs liquid crystal and the characteristics change greatly. In addition, when the molecular weight is large, the degree of decrease in the transition point Tnm of the polymer dispersed liquid crystal due to the addition of the polymerizable compound becomes small, and in order to keep Tnm at room temperature or less, a material having low Tni of the liquid crystal composition itself must be used, and as a result, there is also a problem that the operating temperature range becomes narrow.
The multifunctional urethane (meth) acrylate oligomer is obtained by reacting a hydroxyl group-containing acrylate with a polyol or a polyisocyanate. As the polyol, there may be mentioned: polyether polyols, polyester polyols, polycarbonate polyols, polycaprolactone polyols, polybutadiene polyols, and the like, and as the polyether polyols, there can be mentioned: polyethylene glycol, polypropylene glycol, polytetramethylene glycol, and the like.
As the polyisocyanate, there may be mentioned: 2, 4-toluene diisocyanate (Tolylene Diisocyanate, TDI), O-toluidine diisocyanate (O-Toluidine Diisocyanate, TODI), naphthylene diisocyanate (Naphthylene Diisocyanate, NDI), xylylene diisocyanate (Xylylene Diisocyanate, XDI), 4 '-diphenylmethane diisocyanate (4, 4' -Diphenyl Methane Diisocyanate, MDI), methylenebis (4-cyclohexyl isocyanate), hydrogenated xylylene diisocyanate, hexamethylene diisocyanate, trans-cyclohexane 1, 4-diisocyanate, 1,6, 11-undecane triisocyanate, 1, 8-diisocyanate-4-isocyanate methyl octane, 1,3, 6-hexamethylene triisocyanate, bicycloheptane triisocyanate, trimethylhexamethylene diisocyanate, dicyclopentadiene diisocyanate, norbornene diisocyanate, isophorone diisocyanate, carbodiimide-modified MDI, polymethylene polyphenyl polyisocyanate (polymethylene polyphenyl polyisocyanate), and the like.
Examples of the hydroxyl group-containing (meth) acrylate include: 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, polypropylene glycol mono (meth) acrylate, 1, 4-cyclohexanedimethanol monoacrylate, epsilon-caprolactone modified mono (meth) acrylate, and the like.
Specifically, aliphatic urethane (meth) acrylate, aromatic urethane (meth) acrylate, and polyurethane diacrylate oligomer are preferable, polyether polyol, polyester polyol, and polycaprolactone polyol are preferable as the polyol to be used, polyether polyol and polyester polyol are particularly preferable, and polyisocyanate having a cyclic structure is preferable as the polyisocyanate to be used, and polyisocyanate having an alicyclic structure is particularly preferable. More specifically, o-toluidine diisocyanate (TODI), methylenebis (4-cyclohexyl isocyanate), xylylene diisocyanate, hydrogenated xylylene diisocyanate, trans-cyclohexane 1, 4-diisocyanate, 1,6, 11-undecane triisocyanate, bicycloheptane triisocyanate, dicyclopentadiene diisocyanate, norbornene diisocyanate, isophorone diisocyanate, carbodiimide-modified MDI, and particularly, methylenebis (4-cyclohexyl isocyanate), xylylene diisocyanate, hydrogenated xylylene diisocyanate, trans-cyclohexane 1, 4-diisocyanate, 1,6, 11-undecane triisocyanate, bicycloheptane triisocyanate, dicyclopentadiene diisocyanate, norbornene diisocyanate, isophorone diisocyanate are preferable.
The hydroxyl group-containing (meth) acrylate used is preferably 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 1, 4-cyclohexanedimethanol monoacrylate, and mono (meth) acrylate modified with epsilon-caprolactone, and particularly preferably 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
In addition, the compounds of the following general formula (i-1) are also preferable.
(wherein X is i1 Each independently represents a hydrogen atom or a methyl group, B 1 Each independently represents an alkyl group having 1 to 4 carbon atoms, and at least one of the alkyl groups is-CH 2 -can be substituted by oxygen atoms, -CO-, -COO-, -OCO-, b represents 1-20, B 2 Is a structure obtained by repeating a combination of groups selected from the following groups (i-2) to (i-6) or a single group selected from them,
B 3 is a group selected from the group consisting of groups of the following general formula (i-7), general formula (i-8) and general formula (i-9), and groups selected from them, wherein the groups are repeatedly linked, or a plurality of groupsStructure obtained by combination connection
(wherein X is i2 Represents a hydrogen atom or a methyl group, X i3 An alkylene group having 1 to 9 carbon atoms,
Y 5 an alkylene group having 1 to 15 carbon atoms, a divalent aromatic group, a divalent alicyclic hydrocarbon group,
Y 3 y and Y 4 Represents a hydrogen atom or a methyl group,
at X i1 、X i2 、X i3 、B 1 、B 2 、B 3 、Y 3 、Y 4 Or Y 5 Where a plurality of them are present, they may be the same or different, t1 and t2 each independently represent an integer of from 0 to 300, and t+t1+t2 represents an integer of from 20 to 300)
Here, in the present application, examples of the divalent aromatic group include 1, 4-phenylene group, pyridine-2, 5-diyl group, pyrimidine-2, 5-diyl group, pyrazine-2, 5-diyl group, thiophene-2, 5-diyl group, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl group, naphthylene-1, 4-diyl group, naphthylene-1, 5-diyl group, naphthylene-1, 6-diyl group, naphthylene-2, 6-diyl group, phenanthrene-2, 7-diyl group, 9, 10-dihydrophenanthrene-2, 7-diyl group, benzothiazolyl group, 1,2,3, 4a,9,10 a-octahydrophenanthrene-2, 7-diyl group, benzo [1,2-b:4,5-b ]']Dithiophene-2, 6-diyl, benzo [1,2-b:4,5-b ]']Diselenophen-2, 6-diyl, [1 ]]Benzothieno [3,2-b ]]Thiophene-2, 7-diyl, [1]Benziselenopheno [3,2-b ]]Selenophene-2, 7-diyl or fluorene-2, 7-diyl are preferred. These radicals may be unsubstituted or substituted by more than one L 1 And (3) substitution.
Examples of the divalent alicyclic hydrocarbon group include 1, 2-cyclopropylene, 1, 3-cyclobutylene, 2, 5-cyclopentylene, octahydro-4, 7-methano-1H-indene-1, 5-diyl, octahydro-4, 7-methano-1H-indene-1, 6-diyl, octahydro-4, 7-methano-1H-indene-2, 5-diyl, and tricyclo [3.3.1.1 ] 3,7 ]-1, 3-diyl, 1, 4-cyclohexylene, 1, 4-cyclohexenylene, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, tetrahydrothiopyran-2, 5-diyl, 1, 4-bicyclo (2, 2) octyleneDecahydronaphthalene-2, 6-diyl is a preferred example. These radicals may be unsubstituted or substituted by more than one L 1 And (3) substitution.
Further, aliphatic urethane acrylate and polyurethane diacrylate oligomers are particularly preferable.
From the viewpoint of improving the adhesion, the content of the polymerizable compound selected from the polyfunctional (meth) acrylate oligomer having a weight average molecular weight of 2000 or more is preferably 5% by mass or more, more preferably 15% by mass or more, still more preferably 20% by mass or more, and particularly preferably 25% by mass or more, relative to 100% by mass of the total amount of the polymerizable composition (MA) contained in the polymer dispersed liquid crystal composition of the present invention. In view of the reduction of the voltage, the amount is preferably 80% by mass or less, more preferably 60% by mass or less, still more preferably 50% by mass or less, and particularly preferably 40% by mass or less.
[ fourth component ]
The fourth component is a compound selected from the group consisting of a polyfunctional polymerizable oligomer and a polyfunctional polymerizable monomer having a weight average molecular weight of less than 2000 represented by the following general formula (iv). The molecular weight of the polyfunctional polymerizable oligomer and/or the polyfunctional polymerizable monomer is preferably 2000 or less, more preferably 1000 or less.
(wherein Y is iv1 Represents a hydrogen atom or a methyl group,
X iv1 n represents 130 or less carbon atoms iv1 A linear, branched or cyclic hydrocarbon group having a valence, and at least one of the linear, branched or cyclic hydrocarbon groups-CH 2 The radicals may each independently be interrupted by-O-, by oxygen atoms which are not directly adjacent to one another-NH-, -CO-, -COO-, -OCO-, -CH=CH-, or-C≡C-substitution, one or more hydrogen atoms present in the linear, branched or cyclic hydrocarbon group may be each independently substituted with a fluorine atom or-OH,
n iv1 an integer of 2 to 6
The polyfunctional polymerizable oligomer or the polyfunctional polymerizable monomer having a weight molecular weight of less than 2000 represented by the general formula (iv) is preferably a polymerizable compound represented by the general formula (iv-1).
(wherein Y is iv2 Y and Y iv3 Represents a hydrogen atom or a methyl group,
X iv2 represents a straight-chain or branched alkylene group having 2 to 80 carbon atoms, any carbon atom of the alkylene group may be substituted by-O-, -CO-, -COO-, -OCO-, -ch=ch-, -c≡c-or OH substitution)
Here, in the general formula (iv-1), X iv2 The linear or branched alkylene group of (a) is preferably in the range of 2 to 70 carbon atoms, preferably in the range of 4 to 70 carbon atoms, more preferably in the range of 5 to 60 carbon atoms, and particularly preferably in the range of 5 to 50 carbon atoms from the viewpoint of reduction in driving voltage.
Examples of the polymerizable compound represented by the general formula (iv-1) include compounds having the following structures (iv-1-1) to (iv-1-10).
(wherein n and m represent n+m is 1 to 10, n 2 Represents 1 to 18, n 3 M 2 Represents n 3 +m 2 Has a value of 1 to 18, n 4 Represents 1 to 23, n 5 Represents 1 to 23, n 6 Represents 4 to 30, n 7 Represents 2 to 10, n 8 N is as follows 9 Representation 2-10)
The content of the polymerizable compound represented by the general formula (iv) is preferably 2 mass% or more, more preferably 5 mass% or more, still more preferably 10 mass% or more, and particularly preferably 50 mass% or less, 40 mass% or less, 30 mass% or less, and 25 mass% or less, with respect to 100 mass% of the total amount of the polymerizable composition (MA) contained in the polymer-dispersed liquid crystal composition of the present invention, from the viewpoint of improving heat resistance.
[ fifth component ]
The fifth component is a cyclic monofunctional polymerizable compound represented by the following general formula (v).
P v1 -R v1 (v)
(wherein P v1 Represents a polymerizable group and is preferably a polymerizable group,
R v1 represents a linear or branched alkyl group having 1 to 22 carbon atoms, one or more of which are-CH 2 -can be substituted independently of one another by-O-, -CO-, -COO-, -OCO-or-P (=o) (-OH) -in such a way that the oxygen atoms are not directly adjacent, one or more hydrogen atoms present in the alkyl radical being each independently substituted by fluorine atoms or-OH)
In the compound represented by the general formula (v), P in the formula v1 Represents a polymerizable group, preferably P in the general formula (ii) ii1 The polymerizable groups represented are the same.
In the compound represented by the general formula (v), R in the formula v1 More preferably a straight-chain or branched alkyl group having 3 to 20 carbon atoms, particularly preferably a straight-chain or branched alkyl group having 6 to 18 carbon atoms, still more preferably a branched alkyl group having 9 to 24 carbon atoms, in order to suppress crystallinity.
At R v1 In the case of a linear alkyl group, the compound represented by the general formula (v) is preferably a mono (methyl) having a linear alkyl chain such as ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, hexadecyl (meth) acrylate, stearyl (meth) acrylate, and behenyl (meth) acrylate An acrylic acid ester, or a mono (meth) acrylic acid ester having a linear alkyl chain represented by the following structure.
The compound represented by the general formula (v) is preferably R in the general formula (v) v1 An acrylic acid ester having a linear ether chain structure. The acrylic acid ester having the ether chain structure is preferably a compound represented by the following structures of the formulae (v-a 1) to (v-a 3).
(wherein q represents an integer of 1 to 12, preferably an integer of 1 to 5, more preferably an integer of 1 to 3)
In the general formula (v), it is preferable to use a mono (meth) acrylate having a linear alkyl chain, in particular, from the viewpoint of maintaining the transparency at the time of no voltage application well and making the effect of reducing the driving voltage remarkable.
At R v1 In the case of a branched alkyl group, the compound represented by the general formula (v) is preferably a mono (meth) acrylate having a branched alkyl chain represented by the following structure. The compound represented by the general formula (v) is preferably isobutyl (meth) acrylate, isononyl (meth) acrylate, isodecyl (meth) acrylate, isomyristyl (meth) acrylate, or isostearyl (meth) acrylate.
The compound represented by the general formula (v) is preferably R in the general formula (v) v1 An acrylic acid ester having a linear ether chain structure. The acrylic acid ester having the ether chain structure is preferably a compound represented by the following structure.
(wherein q represents an integer of 1 to 10, preferably an integer of 1 to 5, more preferably an integer of 1 to 3)
Among these compounds, in particular, mono (meth) acrylate having branched alkyl chains is preferably used in order to maintain transparency when no voltage is applied and to make the effect of reducing the driving voltage remarkable.
In view of low-voltage driving, the content of the chain monofunctional polymerizable compound represented by the general formula (v) is preferably 5% by mass or more, more preferably 10% by mass or more, and particularly preferably 15% by mass or more, relative to 100% by mass of the total amount of the polymerizable composition (MA) contained in the polymer-dispersed liquid crystal composition of the present invention, from the viewpoint of improving the compatibility of the components in the polymerizable composition. In view of adhesion, it is preferably 60 mass% or less, more preferably 50 mass% or less, and particularly preferably 40 mass% or less.
[ other polymerizable Compound ]
The polymerizable composition (MA) may or may not contain a polymerizable compound having a mesogenic skeleton as another polymerizable compound. Examples of such polymerizable compounds include compounds represented by the following general formulae (2) to (8).
In the general formulae (2) to (8), P 11 ～P 74 Preferably, the polymerizable groups are each independently represented by any one of the following formulas (P-1) to (P-20). In the following formulas (P-1) to (P-20), the bond to a carbon atom or other atom is represented.
Among the polymerizable groups represented by the formulae (P-1) to (P-20), the formulae (P-1) and (P-2) are preferable from the viewpoint of improving the polymerizability and the storage stability.
X 11 ～X 72 Each independently represents-O-, -S-, -OCH 2 -、-CH 2 O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH 2 -、-CH 2 S-、-CF 2 O-、-OCF 2 -、-CF 2 S-、-SCF 2 -、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-COO-CH 2 CH 2 -、-OCO-CH 2 CH 2 -、-CH 2 CH 2 -COO-、-CH 2 CH 2 -OCO-、-COO-CH 2 -、-OCO-CH 2 -、-CH 2 -COO-、-CH 2 -OCO-, -ch=ch-, -n=n-, -ch=n-n=ch-, -cf=cf-, -c≡c-, or a single bond, in X 11 ～X 72 Where there are plural, they may each be the same or different (wherein each P- (S-X) -bond does not contain-O-), particularly preferred are groups selected from the group consisting of single bonds, -O-, -S-, -CO-, -COO-, -OCO-.
M 11 、M 21 、M 31 、M 51 、M 71 Each independently represents a mesogenic group represented by the following general formula (9-a).
(in the general formula (9-a), A 91 、A 92 、A 93 Each independently is a divalent radical having at least one or more ring structures, said divalent radical representing a member selected from the group consisting of 1, 2-cyclopropylene, 1, 3-cyclobutylene, 2, 5-cyclopentylene, octahydro-4, 7-methano-1H-indene-1, 5-diyl, octahydro-4, 7-methano-1H-indene-1, 6-diyl, octahydro-4, 7-methano-1H-indene-2, 5-diyl, tricyclo [3.3.1.1 ] 3,7 ]-1, 3-diyl, 1, 4-phenylene, 1, 4-cyclohexylene, 1, 4-cyclohexenylene, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, tetrahydrothiopyran-2, 5-diyl, 1, 4-bicyclo (2, 2) octylene, decalin-2, 6-diyl, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, pyrazine-2, 5-diyl, thiophene-2, 5-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, naphthylene-1, 4-diyl, naphthylene-1, 5-diyl Group, naphthylene-1, 6-diyl, naphthylene-2, 6-diyl, phenanthrene-2, 7-diyl, 9, 10-dihydrophenanthrene-2, 7-diyl, benzothiazolyl, 1,2,3, 4a,9,10 a-octahydrophenanthrene-2, 7-diyl, benzo [1,2-b ] 4,5-b ]']Dithiophene-2, 6-diyl, benzo [1,2-b:4,5-b ]']Diselenophen-2, 6-diyl, [1 ]]Benzothieno [3,2-b ]]Thiophene-2, 7-diyl, [1]Benziselenopheno [3,2-b ]]Selenophene-2, 7-diyl or fluoren-2, 7-diyl, which can be unsubstituted or substituted by more than one L 1 Substituted, but in which a plurality of A's are present 91 And/or A 92 Each of which may be the same or different,
Z 91 z is as follows 92 Each independently represents-O-, -S-, -OCH 2 -、-CH 2 O-、-CH 2 CH 2 -、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH 2 -、-CH 2 S-、-CF 2 O-、-OCF 2 -、-CF 2 S-、-SCF 2 -、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-COO-CH 2 CH 2 -、-OCO-CH 2 CH 2 -、-CH 2 CH 2 -COO-、-CH 2 CH 2 -OCO-、-COO-CH 2 -、-OCO-CH 2 -、-CH 2 -COO-、-CH 2 -OCO-, -ch=ch-, -n=n-, -ch=n-, -n=ch-, -ch=n-n=ch-, -cf=cf-, -c≡c-, or a single bond, but in the presence of a plurality of Z' s 91 And/or Z 92 Each of which may be the same or different,
j 91 j 92 Each independently represents 0 to 4,j 91 +j 92 Represents an integer of 1 to 4, L 1 Represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfonyl group, a nitro group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a-CH group 2 -or not more than two adjacent-CH 2 Each independently through-O-, -S-, -CO-, -COO-; -OCO-, -CO-S-, -S-CO-, -O-CO-O-, and-CO-NH-, -NH-CO-, -ch=ch-COO-, -ch=ch-OCO-, -COO-ch=ch-, -OCO-ch=ch-,CF＝CF-、-N＝N-、-CR 1 ＝N-N＝CR 1 -or-C≡C-substituted straight-chain alkyl or branched alkyl having 1 to 20 carbon atoms, wherein any hydrogen atom in the alkyl group may be substituted with a fluorine atom (further, R 1 An alkyl group having 1 to 20 carbon atoms, which may be linear or branched, wherein any hydrogen atom in the alkyl group may be substituted with a fluorine atom, and wherein one of the alkyl groups is-CH 2 -or not more than two adjacent-CH 2 Each independently through-O-, -S-, and-CO-, -COO-, -OCO-, -CO-S-, and-S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-or-C≡C-substitution))
In addition, M 41 Is provided with as the A 91 、A 92 、A 93 Exemplary trivalent organic groups of the ring structure, M 61 Is provided with as the A 91 、A 92 、A 93 Tetravalent organic radicals of the exemplified ring structures.
In the general formulae (2) to (8), R 11 、R 31 Each represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, or an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group may be linear or branched, any hydrogen atom in the alkyl group may be substituted with a fluorine atom, and one of the alkyl groups may be-CH 2 -or not more than two adjacent-CH 2 Each independently through-O-, -S-, and-CO-, -COO-, -OCO-, -CO-S-, and-S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, or-C≡C-substitution.
m1 to m7, n2 to n7, l4 to l6, and k6 each independently represent an integer of 0 to 5. In the general formulae (2) to (8), S 11 ～S 72 Each independently represents a spacer or represents a single bond, the S 11 ～S 72 The spacer represented represents an alkylene group having 1 to 18 carbon atoms (the alkylene group may be substituted with one or more halogen atoms, CN groups, alkyl groups having 1 to 8 carbon atoms, or alkyl groups having 1 to 8 carbon atoms having a polymerizable group, one CH being present in the group) 2 Based on or not adjacent two or more CH' s 2 The radicals can each independently of one another be bound directly to one another by-O-, in the form of oxygen atoms-S-, -NH-, -N (CH) 3 ) Of these spacers, linear alkylene groups having 2 to 8 carbon atoms, alkylene groups having 2 to 6 carbon atoms substituted with fluorine atoms, and alkylene groups having 5 to 14 carbon atoms partially substituted with-O-are preferable in terms of orientation. In addition, at S 11 ～S 72 Where there are plural, they may be the same or different from each other.
In the general formulae (2) to (8), m1 to m7, n2 to n7, l4 to l6, and k6 each independently represent an integer of 0 to 5, and m1 to m7, n2 to n7, l4 to l6, and k6 each independently preferably are 0 or 1.
The total content of the polymerizable compounds other than the first component, the second component, the fourth component and the fifth component is preferably 2% by mass or more, more preferably 5% by mass or more, and particularly preferably 10% by mass or more, relative to 100% by mass of the total amount of the polymerizable composition (MA) contained in the polymer-dispersed liquid crystal composition of the present invention, from the viewpoints of alignment and transparency. In view of scattering property and low-voltage driving, it is preferably 80 mass% or less, more preferably 70 mass% or less, and particularly preferably 60 mass% or less.
[ additives ]
In order to achieve a composition in which adhesion is more important, the polymerizable composition (MA) of the present invention preferably contains an additive represented by the following general formula (X) in addition to the first component, the second component, the fourth component, the fifth component, and the other polymerizable compound.
(wherein Y is X1 Represents a hydrogen atom or a methyl group,
X X1 n represents 130 or less carbon atoms X1 A linear, branched or cyclic hydrocarbon group having a valence of one of the linear, branched or cyclic hydrocarbon groupson-CH 2 The radicals may each independently be interrupted by-O-, by oxygen atoms which are not directly adjacent to one another-NH-, -CO-, -COO-, -OCO-, -CH=CH-, or-C≡C-substitution, one or more hydrogen atoms present in the linear, branched or cyclic hydrocarbon group may be each independently substituted with a fluorine atom or-OH,
n X1 an integer of 1 to 6 is represented,
here, X is X1 At least one of-CH 2 -the radical is substituted by the following formula (X-1)
Specifically, the following compounds are preferably added.
(wherein X 6 、X 7 X is X 8 Each independently represents a hydrogen atom or a methyl group, q, r and s represent 1 to 4)
The amount of the compound having the group represented by the general formula (X-1) added is preferably 0.005 mass% or more and 2 mass% or less, more preferably 0.01 mass% or more and 0.5 mass% or less, and still more preferably 0.01 mass% or more and 0.2 mass% or less, based on the total amount of the polymer-dispersed liquid crystal composition.
[ non-polymerizable liquid Crystal composition (LB) ]
[ third component ]
The non-polymerizable liquid crystal composition (LB) may contain one or two or more of tolane (tolane) compounds represented by the following general formula (iii) as a third component.
(wherein R is iii1 Independently of one another, n-alkyl, n-alkoxy having 1 to 7 carbon atoms, havingAlkenyl having 2 to 7 carbon atoms, alkenyloxy or alkoxyalkyl,
R iii2 represents fluorine atom, chlorine atom, cyano group, CF 3 Radical, OCF 3 Radical, OCHF 2 A group, NCS group or C1-10 alkyl group, one or both of which are not adjacent to each other, -CH 2 The radical may be substituted by oxygen atoms, -COO-, -OCO-, and, in addition, more than one-CH 2 CH 2 -alkyl which may be substituted by-ch=ch-or-c≡c-, preferably having 1 to 5 carbon atoms, cyano or fluorine (one or two of said alkyl groups being non-contiguous-CH 2 The radical may be substituted by oxygen atoms, in addition, more than one-CH 2 CH 2 Can be substituted by-CH=CH-or-CH≡CH-,
A iii1 represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, 2-methyl-1, 4-phenylene, 3-methyl-1, 4-phenylene, 2, 3-dimethyl-1, 4-phenylene, 3, 5-dimethyl-1, 4-phenylene or 2, 6-dimethyl-1, 4-phenylene,
A iii2 a is a iii3 Each independently of the others represents 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, 2-methyl-1, 4-phenylene, 3-methyl-1, 4-phenylene, 2, 3-dimethyl-1, 4-phenylene, 3, 5-dimethyl-1, 4-phenylene or 2, 6-dimethyl-1, 4-phenylene,
Z iii1 Z is as follows iii2 One of them is-C.ident.C-, the other, when present, is-C.ident.C-, -CF 2 O-、-OCF 2 -、-CH＝CH-、-CF＝CF-、-COO-、-CH 2 -CH 2 -、-CF 2 -CF 2 -or a single bond,
n iii is 0 or 1)
The non-polymerizable liquid crystal composition (LB) contains one or two or more of the diphenylacetylene compounds represented by the general formula (iii), and thus, in a liquid crystal element using a polymer dispersed liquid crystal composition comprising the non-polymerizable liquid crystal composition (LB), the adhesion and light scattering properties are excellent, and low-voltage driving at room temperature and at low temperature can be realized.
In the compound represented by the general formula (iii), A iii1 Preferred are trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene and 3-fluoro-1, 4-phenylene. From the viewpoint of improving scattering properties, A iii1 Preferably 1, 4-phenylene.
In addition, A iii2 A is a iii3 Preference is given to 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, 2-methyl-1, 4-phenylene, 3-methyl-1, 4-phenylene. From the viewpoint of high-speed response, it is preferable to contain A iii2 A is a iii3 Is that
Is a compound of (a).
The compound represented by the formula (iii) is preferably a compound represented by the following formulae (iii-1) to (iii-8).
(wherein R is iii1 R is R iii2 Has the meaning shown in the formula (iii), Y iii1 Y and Y iii2 Are independently of each other H or F, Y iii3 Is a hydrogen atom, a fluorine atom or a methyl group)
Of these, the compounds represented by the general formula (iii) are more preferably compounds represented by the subordinate general formulae (iii-6) to (iii-8).
The compound represented by the general formula (iii) as the third component is preferably 10 mass% or more and 80 mass% or less, more preferably 25 mass% or more and 70 mass% or less, and still more preferably 35 mass% or more and 60 mass% or less, relative to 100 mass% of the total amount of the non-polymerizable liquid crystal composition (LB).
[ sixth ingredient ]
The non-polymerizable liquid crystal composition (LB) may further contain one or more compounds represented by the following general formula (vi-0) as a sixth component (wherein the third component is excluded).
(wherein R is 11 Represents an alkyl group having 1 to 10 carbon atoms, one or two of which are not adjacent to each other, -CH 2 The radical may be substituted by oxygen atoms, -COO-, -OCO-, and, in addition, more than one-CH 2 CH 2 Can be substituted by-CH≡CH-, R 12 Represents fluorine atom, chlorine atom, cyano group, CF 3 Radical, OCF 3 Radical, OCHF 2 A group, NCS group, cyano group or C1-10 alkyl group, one or both of which are not adjacent to each other, -CH 2 The radical may be substituted by oxygen atoms, -COO-, -OCO-, and, in addition, more than one-CH 2 CH 2 Alkyl which may be substituted by-C.ident.C-, preferably by fluorine, cyano or C1-5 alkyl (non-contiguous one or two CH in said alkyl 2 The groups may be substituted with oxygen atoms),
Z 11 z is as follows 12 Each independently represents a single bond, -COO-, -OCO-, -CH 2 -CH 2 -、-CH＝CH-、-CF 2 O-、-OCF 2 -or-C≡C-, at Z 12 Where there are plural, they may be the same or different,
A 11 、A 12 a is a 13 Independently of one another, 1, 4-phenylene, 1, 4-cyclohexylene, 1, 4-cyclohexenylene, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, decalin-2, 6-diyl, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, pyrazine-2, 5-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 2, 6-naphthylene, which 1, 4-phenylene, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 2, 6-naphthylene may be unsubstituted or provided withHaving one or more fluorine atoms, chlorine atoms, CF 3 Radical, OCF 3 Radicals or CH 3 The radicals being substituents, in A 13 Where there are plural, they may be the same or different,
n 11 0, 1 or 2)
As the compound of the formula (vi-0), R in the formula (vi-0) 11 Preferably an alkyl group having 1 to 5 carbon atoms (one or two of the non-adjacent CH's in the alkyl group) 2 The radicals may be substituted by oxygen atoms), R 12 Preferably a fluorine atom, a cyano group or an alkyl group having 1 to 5 carbon atoms (one or two of the alkyl groups being not adjacent to each other CH 2 Groups may be substituted by oxygen atoms), Z 11 Z is as follows 12 Preferably each independently is a single bond, -COO-, -OCO-, -CH 2 -CH 2 -、-CF 2 O-or-OCF 2 - (at Z) 11 Where plural are present, they may be the same or different), more preferably a single bond, -COO-or-CF 2 O-，A 11 、A 12 A is a 13 Preferably each independently is 1, 4-phenylene, 1, 4-cyclohexylene, 1, 3-dioxane-2, 5-diyl, pyrimidine-2, 5-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or 2, 6-naphthylene (the 1, 4-phenylene, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 2, 6-naphthylene may be unsubstituted or have one or more fluorine atoms or CH 3 The radicals being substituents, in A 13 And may be the same or different when present in plural), more preferably 1, 4-phenylene, 1, 4-cyclohexylene, pyrimidine-2, 5-diyl, or 2, 6-naphthylene (the 1, 4-phenylene, 2, 6-naphthylene may be unsubstituted or have one or more fluorine atoms or CH 3 The radicals being substituents, in A 13 The same or different when a plurality of n are present), n 11 Preferably 0 or 1.
The compound represented by the general formula (vi-0) is more preferably one or two or more of the liquid crystalline compounds represented by the following general formula (vi) (except the third component).
(wherein R is 3 Represents an alkyl group having 1 to 10 carbon atoms, one or more non-adjacent-CH groups in the alkyl group 2 The radical may be substituted by an oxygen atom, -CH=CH-, -COO-, -OCO-,
A 6 represents 1, 4-phenylene, 1, 4-cyclohexylene, 1, 3-dioxane-2, 5-diyl, pyridine-2, 5-diyl or pyrimidine-2, 5-diyl, the 1, 4-phenylene radical being unsubstituted or having one or more fluorine atoms, chlorine atoms, CF 3 、OCF 3 Or a methyl group as a substituent,
A 7 represents 1, 4-phenylene or 1, 4-cyclohexylene, the 1, 4-phenylene radicals being unsubstituted or having one or more fluorine atoms, chlorine atoms, CF 3 、OCF 3 Or a methyl group as a substituent,
A 8 represents 1, 4-phenylene, which 1, 4-phenylene may be unsubstituted or have one or more fluorine atoms, chlorine atoms, CF 3 、OCF 3 Or a methyl group as a substituent,
Z 6 z is as follows 7 Each independently represents a single bond, -COO-, -OCO-, -CH 2 -CH 2 -、-CH＝CH-、-CF 2 O-、-OCF 2 -or-c≡c-,
n 12 represents 0 or 1; wherein the third component is excluded
In the general formula (vi), R 3 More preferably an alkyl group having 1 to 10 carbon atoms or an alkoxy group. A is that 6 A is a 7 More preferred are 1, 4-phenylene and 1, 4-cyclohexylene (the 1, 4-phenylene may be unsubstituted or have one or more fluorine atoms as substituents). Z is Z 6 Z is as follows 7 More preferably, each independently is a single bond, -COO-, -OCO-, -CH 2 -CH 2 -, more preferably a single bond or-COO-.
In the general formula (vi), R 3 Represents an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 2 to 7 carbon atoms, more preferably an alkyl group having 2 to 5 carbon atoms,
A 7 is 1, 4-phenylene or 1, 4-cyclohexylene, the 1, 4-phenylene radical being unsubstituted or having a fluorine atom as a constituentThe substituent, in order to reduce the viscosity of the liquid crystal and improve the low-temperature drivability, most preferably contains at least n 12 A compound representing 0.
When a compound represented by the general formula (vi) wherein A is 7 A is a 8 Represents a 1, 4-phenylene group, any one of the 1, 4-phenylene groups having at least one or more fluorine atoms as a substituent, Z 6 、Z 7 Z is as follows 8 Represents a single bond or-COO-, A 6 Represents 1, 4-phenylene or 1, 4-cyclohexylene, n 12 Representing 0 or 1.
Specifically, the following compounds (vi-1) to (vi-11) are exemplified.
(wherein R is 51 Represents an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, Y 11 ～Y 66 Each independently represents a hydrogen atom or a fluorine atom; y is Y 11 ～Y 66 Can be all hydrogen atoms or one or more of them can be fluorine atoms
Specifically, the following compounds (vi-A) to (vi-G) are exemplified.
(wherein R is 511 An alkyl group having 2 to 7 carbon atoms or an alkoxy group having 2 to 7 carbon atoms, preferably an alkyl group having 2 to 5 carbon atoms or an alkoxy group having 2 to 5 carbon atoms
The compound represented by the general formula (vi-0) is preferably 20 mass% or more and 90 mass% or less, more preferably 30 mass% or more and 75 mass% or less, and still more preferably 40 mass% or more and 65 mass% or less, relative to 100 mass% of the total amount of the non-polymerizable liquid crystal composition (LB).
The total content of the liquid crystal compounds represented by the general formula (vi) is preferably 2 mass% or more and 70 mass% or less, more preferably 5 mass% or more and 50 mass% or less, and still more preferably 10 mass% or more and 30 mass% or less, with respect to 100 mass% of the total amount of the non-polymerizable liquid crystal composition (LB).
Further, the total content of the liquid crystalline compounds represented by the general formulae (vi-1) to (vi-11) is preferably 2% by mass or more and 70% by mass or less, more preferably 5% by mass or more and 50% by mass or less, and still more preferably 10% by mass or more and 30% by mass or less, based on 100% by mass of the total amount of the non-polymerizable liquid crystal composition (LB).
Further, the total content of the liquid crystalline compounds represented by the general formulae (vi-a) to (vi-G) is preferably 2% by mass or more and 70% by mass or less, more preferably 5% by mass or more and 50% by mass or less, and still more preferably 10% by mass or more and 30% by mass or less, based on 100% by mass of the total amount of the non-polymerizable liquid crystal composition (LB).
In particular, the total content of the liquid crystalline compounds represented by the general formulae (vi-A), (vi-B), (vi-C) and (vi-G) is preferably 2 to 70 mass%, more preferably 5 to 50 mass%, still more preferably 10 to 30 mass%, based on 100 mass% of the total amount of the non-polymerizable liquid crystal composition (LB).
The refractive index anisotropy (Δn) of the non-polymerizable liquid crystal composition used in the polymer dispersed liquid crystal element is generally preferably high, and Δn is preferably 0.16 or more, more preferably 0.18 or more, still more preferably 0.20 or more, and most preferably 0.22 or more. The ordinary refractive index (no) of the non-polymerizable liquid crystal composition having the Δn is usually about 1.50 to 1.54. When a voltage is applied to the polymer dispersed liquid crystal element to make it transparent, high transparency can be obtained if no of the non-polymerizable liquid crystal composition is substantially equal to the refractive index (np) of the polymer forming the network structure. However, when the monomers and oligomers are polymerized by Ultraviolet (UV) irradiation or the like, the actual polymer has a higher refractive index than that of a pure polymer because the monomers and oligomers are cured as a non-polymerizable liquid crystal composition surrounding a part. Therefore, the refractive index of the monomer and oligomer is preferably less than 1.5, more preferably 1.48 or less, and still more preferably 1.47 or less.
[ polymerization initiator ]
The polymer dispersed liquid crystal composition of the present invention may contain a polymerization initiator. The polymerization initiator used in the present invention is used for polymerizing the polymerizable composition (MA) of the present invention. The photopolymerization initiator used for polymerization by irradiation with light is not particularly limited, and a conventionally known photopolymerization initiator may be used to such an extent that the alignment state of the non-polymerizable liquid crystal composition (LB) is not hindered.
Examples include: 1-hydroxycyclohexyl phenyl ketone "Ornidad (Omnirad) 184", 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one "Ornidad (Omnirad) 1173", 2-methyl-1- [ (methylthio) phenyl ] -2-morpholinopropane-1 "Ornidad (Omnirad) 907", 2-dimethoxy-1, 2-diphenylethane-1-one "Ornidad (Omnirad) BDK", 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone "Ornidad (Omnirad) 369", 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholinophenyl) butan-1-one "Ornidad (Omnii) 379", 2-dimethoxy-2-phenyl "Ornidad (Omnirad) 651", 2-dimethoxy-1, 2-diphenylethane-1, 2-dion (Omnirad) BDK ", 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone (Omnirad) 369", triphenyl-O-m-4-morpholinophenone (Omnirad) 3, 1- [4- (phenylthio) -,2- (o-benzoyl oxime), ethanone "yanjia solid (Irgacure) OXE 01"), 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -,1- (O-acetyl oxime) "Bright (Irgacure) OXE02", "Bright (Irgacure) OXE04" (manufactured by Basf Co., ltd.), "Adjacobian (Adeka cruise) NCI-831", "Adjacobian (Adeka cruise) NCI-930", "Adjacobian (Adeka cruise) N-1919" (manufactured by Ai Dike (ADEKA)) and a mixture of 2, 4-diethylthioxanthone (manufactured by Japanese chemical Co. "Kayacure (Kayacure) DETX") and ethyl p-dimethylaminobenzoate (manufactured by Japanese chemical Co. "Kayacure EPA"): mixtures of isopropylthioxanthone (Wo Debu Ron Jin Suopu (Ward Blenkinsop) manufactured by Kuntze (Quantacure) ITX ") with ethyl p-dimethylaminobenzoate," easy sun cure (Esacum) ONE "," easy sun cure (Esacum) KIP150"," easy sun cure (Esacum) KIP160"," easy sun cure (Esacum) 1001M "," easy sun cure (Esacum) A198"," easy sun cure (Esacum) KIP IT "," easy sun cure (Esacum) KTO46" "easy solid (Esacure) TZT" (Ning Baidi (manufactured by lamberti) inc., "solid of si (SpeedCure) BMS", "solid of si (SpeedCure) PBZ", "benzophenone" (manufactured by LAMBSON) and the like. Further, as the photo cation initiator, a photoacid generator can be used. As the photoacid generator, there may be mentioned: diazodisulfone compounds, triphenylsulfonium compounds, phenylsulfone compounds, sulfonylpyridine compounds, triazine compounds, diphenyliodine compounds, and the like.
The content of the photopolymerization initiator is preferably 0.1 mass% or more and 10 mass% or less, more preferably 0.2 mass% or more and 6 mass% or less, relative to 100 mass% of the total amount of the polymerizable composition (MA) used in the polymer-dispersed liquid crystal composition of the present invention. They may be used alone or in combination of two or more.
As the thermal polymerization initiator used in the thermal polymerization, a known conventional thermal polymerization initiator can be used, and for example, it is possible to use: methyl acetoacetate peroxide, cumene hydroperoxide, benzoyl peroxide, bis (4-t-butylcyclohexyl) peroxydicarbonate, t-butyl peroxybenzoate, methyl ethyl ketone peroxide, 1-bis (t-hexyl peroxy) 3, 5-trimethylcyclohexane, para-pentahydroperoxide, t-butyl hydroperoxide, dicumyl peroxide, isobutyl peroxide, bis (3-methyl-3-methoxybutyl) peroxydicarbonate organic peroxides such as 1, 1-bis (t-butylperoxy) cyclohexane, azonitrile compounds such as 2,2' -azobisisobutyronitrile and 2,2' -azobis (2, 4-dimethylvaleronitrile), azoamidine compounds such as 2,2' -azobis (2-methyl-N-phenylpropionamidine) dihydrochloride, azoamide compounds such as 2,2' -azobis { 2-methyl-N- [1, 1-bis (hydroxymethyl) -2-hydroxyethyl ] propionamide }, and alkylazo compounds such as 2,2' -azobis (2, 4-trimethylpentane). The content of the thermal polymerization initiator is preferably 0.1 mass% or more and 10 mass% or less, more preferably 1 mass% or more and 6 mass% or less, relative to 100 mass% of the total amount of the polymerizable composition (MA) used in the polymerizable composition of the polymer-dispersed liquid crystal composition of the present invention. They may be used alone or in combination of two or more.
The polymer-dispersed liquid crystal composition of the present invention may contain a polymerization inhibitor, an antioxidant, a light stabilizer, a chain transfer agent, a pigment, particles having a particle diameter of less than 1 μm, a chiral compound or an alignment material in such a range that practical electro-optical properties and adhesion properties at the time of producing a polymer-dispersed liquid crystal element are not impaired. Among them, the polymer dispersed liquid crystal composition preferably contains one or more selected from the group consisting of polymerization inhibitors, antioxidants, light stabilizers, particles having a particle diameter of less than 1 μm, pigments, and pigments.
[ polymerization inhibitor ]
The polymerization inhibitor used in the present invention can be used for adjusting the electro-optical properties by controlling the polymerization reaction of the polymer dispersed liquid crystal composition of the present invention. As such a compound, a known conventional compound can be used.
Preferred examples thereof include phenol compounds such as p-methoxyphenol, cresol, t-butylcatechol, 3, 5-di-t-butyl-4-hydroxytoluene, 2' -methylenebis (4-methyl-6-t-butylphenol), 2' -methylenebis (4-ethyl-6-t-butylphenol), 4' -thiobis (3-methyl-6-t-butylphenol), 4-methoxy-1-naphthol, 4' -dialkoxy-2, 2' -bi-1-naphthol, and quinone compounds such as hydroquinone, methylhydroquinone, t-butylhydroquinone, p-benzoquinone, methyl-p-benzoquinone, t-butyl-p-benzoquinone, 2, 5-diphenylbenzoquinone, 2-hydroxy-1, 4-naphthoquinone, 2, 3-dichloro-1, 4-naphthoquinone, anthraquinone, and diphenoquinone, and particularly preferred examples thereof are p-methoxyphenol, 4-methoxy-1-naphthol, t-butylhydroquinone, 2-hydroxy-1, 4-naphthoquinone.
When the polymerization inhibitor is contained, the content of the polymerization inhibitor is preferably 0.001 mass% or more and 2.0 mass% or less, more preferably 0.01 mass% or more and 0.5 mass% or less, relative to 100 mass% of the total amount of the polymerizable composition (MA) used in the polymerizable composition of the polymer-dispersed liquid crystal composition of the present invention.
[ antioxidant ]
The antioxidant used in the present invention can be used to impart practical durability to the polymer dispersed liquid crystal element of the present invention. As such a compound, hydroquinone derivatives, nitrosamine polymerization inhibitors, hindered phenol antioxidants, and the like can be used.
In particular, the method comprises the steps of, preferred are t-butylhydroquinone, and "Q-1300", "Q-1301", pentaerythritol tetrakis [3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ] "Yi Lunuo s (IRGANOX) 1010", thiodiethylene bis [3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ] "Yi Lunuo s (IRGANOX) 1035", octadecyl-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate "IRGANOX 1076", "Yi Lunuo s (IRGANOX) 1135", "Yi Lunuo s (IRGANOX) 1330", 4, 6-bis (octylthiomethyl) -o-cresol "Yi Lunuo s (IRGANOX) 1520L", from Wako pure chemical industries, inc.; "Yi Lunuo S (IRGANOX) 1726", "Yi Lunuo S (IRGANOX) 245", "Yi Lunuo S (IRGANOX) 259", "Yi Lunuo S (IRGANOX) 3114", "Yi Lunuo S (IRGANOX) 3790", "Yi Lunuo S (IRGANOX) 5057", "Yi Lunuo S (IRGANOX) 565" (manufactured above by Basf Co., ltd.), ai Dike (ADEKA) manufactured by Addisosta waves (Adekstab) AO-20, AO-30, AO-40, AO-50, AO-60, AO-80, sumizer's Su Milai (Sumizer) BHT of Sumitomo chemical Co., ltd.), su Milai (Sumizer) BBM-S and Su Milai (Sumizer) GA-80, and compounds having structures represented by the following general formulae (H-1) to (H-4).
In the general formulae (H-1) to (H-3), R H1 Representation ofAlkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkenyl having 2 to 10 carbon atoms or alkenyloxy having 2 to 10 carbon atoms, one-CH present in the group 2 -or not more than two adjacent-CH 2 Each independently substituted with-O-or-S-, and further, one or more hydrogen atoms present in the group may each independently be substituted with a fluorine atom or a chlorine atom. More specifically, it is preferably an alkyl group having 2 to 7 carbon atoms, an alkoxy group having 2 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms or an alkenyloxy group having 2 to 7 carbon atoms, and further preferably an alkyl group having 3 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms. In addition, in the general formula (H-4), sp H1 Represents an alkylene group having 1 to 10 carbon atoms, but one-CH present in the group 2 -or not more than two adjacent-CH 2 Each of which may be independently substituted with-O-or-S-, and one or more hydrogen atoms present in the radical may be independently substituted with a fluorine atom or a chlorine atom.
Among them, pentaerythritol tetrakis [3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ], octadecyl-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate and the compounds represented by the above general formulae (H-2) to (H-3) are particularly preferable.
When the antioxidant is contained, the content of the antioxidant is preferably 0.001 mass% or more and 2.0 mass% or less, more preferably 0.01 mass% or more and 0.5 mass% or less, relative to 100 mass% of the total amount of the polymerizable composition (MA) used in the polymer-dispersed liquid crystal composition of the present invention.
[ light stabilizer ]
The light stabilizer used in the present invention can be used to impart practical durability to the polymer dispersed liquid crystal element of the present invention. Examples of such a compound include: "Di-Nun (TINUVIN) 111FDL", "Di-Nun (TINUVIN) 123", "Di-Nun (TINUVIN) 144", "Di-Nun Binn (TINUVIN) 152", "Di-Nun Binn (TINUVIN) 292", "Di-Nun Binn (TINUVIN) 622", "Di-Nun Binn (TINUVIN) 770", "Di-Nun Binn (TINUVIN) 780", "Di-Nun Binn (TINUVIN) 905", "Di-Nun Binn (TINUVIN) 5100", "Di-Nun Binn (TINUVIN) 5050", "Di-Nun (TINUVIN) 5060", "Di-Nun Binn (TINUVIN) 5151", "Di-Nun (CHIMASORB) 119FL", "Di-Nun (CHIMASSB) FL", "Di-Ke-Ten (CHIMASSB) Usb) (CHIMASSB) upper limit (LALA) 62", "Di-Katsumab", "AdNei-Katsumab (AdNei-Katsumab) 62", "Di-Katsumada (Adtsumada) 62, etc.
When the light stabilizer is contained, the amount of the light stabilizer to be added is preferably 0.001 mass% or more and 2.0 mass% or less, more preferably 0.01 mass% or more and 1.0 mass% or less, relative to the total amount of the polymerizable composition (MA) used in the polymer-dispersed liquid crystal composition of the present invention.
[ chain transfer agent ]
The chain transfer agent used in the present invention can be used to further improve the adhesion between the polymer dispersed liquid crystal composition and the substrate. Examples of the chain transfer agent include: thiol compounds such as octylthiol, N-butylthiol, N-pentylmercaptan, N-hexadecylthiol, N-tetradecylthiol, N-dodecylthiol, t-tetradecylthiol, t-dodecylthiol, etc., thiol compounds such as hexanedithiol, decanedithiol, 1, 4-butanediol dithiopropionate, 1, 4-butanediol dithioglycolate, ethylene glycol dithiopropionate, trimethylolpropane trithioglycolate, trimethylolpropane trithiopropionate, trimethylolpropane tris (3-mercaptobutyrate), pentaerythritol tetrathioglycolate, pentaerythritol tetrathiopropionate, trimercapto-propionic acid tris (2-hydroxyethyl) isocyanurate, 1, 4-dimethylmercaptobenzene, 2,4, 6-trimercapto-s-triazine, thiol compounds such as 2- (N, N-dibutylamino) -4, 6-dimercapto-s-triazine, etc., pentacene, alpha-methylstyrene dimer, acrolein, allyl, terpinolene, alpha-terpene, gamma-terpene, dipentene, etc., preferably represented by the general formula (9-alpha-methyl) and the following general formula (9-alpha-methyl) and the like, preferably represented by the general formula (9-alpha-methyl) and the following (alpha-methyl) styrene compounds.
Wherein R is 95 An alkyl group having 1 to 18 carbon atoms, wherein the alkyl group may be a straight chain or a branched chain, and wherein at least one methylene group in the alkyl group may be substituted with an oxygen atom, a sulfur atom, -CO-, -OCO-, -COO-or-CH=CH-in such a manner that the oxygen atom and the sulfur atom are not directly bonded to each other, and R 96 And represents an alkylene group having 2 to 18 carbon atoms, wherein at least one methylene group in the alkylene group may be substituted with an oxygen atom, a sulfur atom, -CO-, -OCO-, -COO-or-ch=ch-in such a manner that the oxygen atom and the sulfur atom are not directly bonded to each other.
When the chain transfer agent is contained, the content of the chain transfer agent is preferably 0.001 mass% or more and 10 mass% or less, more preferably 0.01 mass% or more and 5.0 mass% or less, relative to 100 mass% of the total amount of the polymerizable composition (MA) of the polymer-dispersed liquid crystal composition of the present invention.
[ pigment ]
The pigment used in the present invention can be used to impart color to the polymer dispersed liquid crystal element of the present invention or to control color. The pigment is not particularly limited, and a known conventional pigment can be used in a range of being soluble in liquid crystal or dispersed in a polymer network. Examples of the dye include a dichromatic dye and a fluorescent dye. Examples of such pigments include: the azo dye, anthraquinone dye, quinacridone dye, dioxazine dye, quinophthalone dye, cyanine dye, phthalocyanine dye, perylene dye, viol dye, squaraine dye, and the like are preferably those showing liquid crystallinity from the viewpoint of addition. Examples include: japanese patent application laid-open No. 51-2885, japanese patent application laid-open No. 61-21163, japanese patent application laid-open No. 62-555, japanese patent application laid-open No. 63-301850, japanese patent application laid-open No. 7-48520, japanese patent application laid-open No. 7-179858, japanese patent application laid-open No. 10-279945, japanese patent application laid-open No. 11-172252, japanese patent application laid-open No. 2000-239664, japanese patent application laid-open No. 2012-82400, and the like an anthraquinone dye shown in Japanese patent application laid-open No. 59-20355, japanese patent application laid-open No. 59-172549, japanese patent application laid-open No. 61-148291, japanese patent application laid-open No. 1-161086, japanese patent application laid-open No. 8-67822, a quinophthalone dye shown in Japanese patent application laid-open No. 59-51947, japanese patent application laid-open No. 61-148292, japanese patent application laid-open No. 2000-44825, japanese patent application laid-open No. 2001-49135, and the like.
When the pigment is contained, the content of the pigment is preferably 0.01 mass% or more and 8 mass% or less, more preferably 0.1 mass% or more and 4 mass% or less, relative to 100 mass% of the total amount of the non-polymerizable liquid crystal composition (LB) used in the polymer-dispersed liquid crystal composition of the present invention.
[ pigment ]
The pigment used in the present invention can be used to impart color or control color to the polymerizable liquid crystal element of the present invention. The pigment is not particularly limited, and any known conventional pigment can be used in a range of being dispersed in a liquid crystal or a network polymer. Examples of such pigments include: azo pigments, diketopyrrolopyrrole pigments, quinacridone pigments, dioxazine pigments, perylene pigments, phthalocyanine pigments, carbon black pigments, and the like are preferable to be excellent in dispersibility in the network polymer from the viewpoint of effectively imparting colorability.
When the pigment is contained, the content of the pigment is preferably 0.01 mass% or more and 8 mass% or less, more preferably 0.1 mass% or more and 4 mass% or less, relative to 100 mass% of the total amount of the non-polymerizable liquid crystal composition (LB) used in the polymer-dispersed liquid crystal composition of the present invention.
[ particles having a particle diameter of less than 1 μm ]
The particles having a particle diameter of less than 1 μm used in the present invention can be used to impart various functions to the polymer dispersed liquid crystal element of the present invention. The particles are not particularly limited, and may be used in a range that does not impair the electro-optical properties or adhesion of the liquid crystal element. Examples of such particles include: inorganic fillers such as alumina, titanium white, titanium black, aluminum hydroxide, talc, clay, mica, barium titanate, zinc oxide, and glass fiber, metal powders such as silver powder and copper powder, and thermally conductive fillers such as aluminum nitride, boron nitride, silicon nitride, gallium nitride, silicon carbide, magnesia (magnesium oxide), silica, crystalline silica (silicon oxide), fused silica (silicon oxide), graphite, and carbon fiber containing carbon nanofibers, silver nanoparticles, quantum Dots (QD) emitter particles, and perovskite type emitter particles.
The particles are preferably particles having good dispersibility in the network polymer. When the particles are contained, the content of the particles is preferably 0.001 mass% or more and 5 mass% or less, more preferably 0.01 mass% or more and 3 mass% or less, relative to 100 mass% of the total amount of the non-polymerizable liquid crystal composition (LB) used in the polymer-dispersed liquid crystal composition of the present invention.
[ chiral Compounds ]
The chiral compound used in the present invention can be used to impart various functions to the polymer dispersed liquid crystal element of the present invention. The chiral compound is not particularly limited, and may be used in a range that does not impair the electro-optical properties or adhesion of the liquid crystal element. Specifically, examples thereof include: cholesterol nonanoate having a cholesterol group as a chiral group, cholesterol stearate, BDH company having a 2-methylbutyl group as a chiral group, "CB-15", "C-15", merck (Merck) company, "S-1082", chisso (Chisso) company, "CM-19", "CM-20", "CM", 1-methylheptyl group as a chiral group, "S-811" by Merck (Merck) company, "CM-21", "CM-22" by Chisso (Chisso) company, basoff (BASF) company "LC756" having an isosorbide (isosorbide) skeleton as a chiral group, japanese patent application laid-open No. 2009-515818, japanese patent application laid-open No. 2010-90108, japanese patent application laid-open No. 2013-87109, and the like.
When the chiral compound is contained, the amount of the value (d/P) obtained by dividing the thickness (d) of the polymer obtained by addition by the helical pitch (P) in the polymer is preferably in the range of 0.1 to 100, more preferably in the range of 0.1 to 20, depending on the use of the polymer dispersed liquid crystal composition of the present invention.
In order to exert the characteristics of the liquid crystal composition, the chiral compound is preferably contained in an amount as small as possible to obtain a desired helical pitch. When the chiral compound is contained, the content of the chiral compound is preferably 0.01 mass% or more and 8 mass% or less, more preferably 0.1 mass% or more and 4 mass% or less, relative to 100 mass% of the total amount of the non-polymerizable liquid crystal composition (LB) used in the polymer-dispersed liquid crystal composition of the present invention.
[ oriented Material ]
The polymer dispersed liquid crystal composition of the present invention may contain an alignment material in order to control the alignment of the liquid crystal element. The alignment material used in the present invention is a known conventional alignment material insofar as it is insoluble in the liquid crystal composition. Examples of such an orientation material include: a polymerizable compound having a polar group at one end of a mesogenic skeleton and a long-chain alkyl group at the other end, a polymerizable liquid crystal compound having a polar group at a lateral position (lateral position) of a mesogenic skeleton, a polymerizable compound having a plurality of mesogenic skeletons and a polar group at a side chain of a long-chain alkyl group bonding one of the mesogenic skeletons to the mesogenic skeleton, or the like.
< liquid Crystal element >)
The liquid crystal element using the polymer dispersed liquid crystal composition of the present invention includes at least a layer (phase separation liquid crystal layer) in which liquid crystal phase separates from a network polymer, an electrode, and a substrate. Or comprises a phase separation liquid crystal layer, an orientation film phase, an electrode and a substrate for supporting the phase separation liquid crystal layer, the orientation film layer and the electrode.
The phase separated liquid crystal phase is obtained by: the polymer network derived from each polymerizable component contained in the polymerizable composition (MA) is formed by polymerizing the polymerizable composition (MA) contained in the polymer dispersed liquid crystal composition.
The liquid crystal element of the present invention can be brought into a light scattering state by a network structure based on a polymer and liquid crystal molecules existing in voids thereof, for example, when no voltage is applied. On the other hand, when a voltage is applied, the liquid crystal molecules are aligned perpendicularly to the substrate, and thus the liquid crystal display device can be in a transparent state. As described above, the liquid crystal element of the present invention changes the light transmission state according to the presence or absence of an applied voltage, and is therefore useful as a liquid crystal light control element used for a device requiring a light control function or a liquid crystal display element used for a display for image display.
The liquid crystal element of the present invention may be configured to control the alignment of liquid crystal molecules by applying a voltage, but is preferably configured as a vertical electric field type liquid crystal element. A vertical electric field type liquid crystal element is a liquid crystal element in which electrodes are arranged so as to generate an electric field perpendicular to an alignment film. In a vertical electric field type liquid crystal element, electrodes are generally provided on both of two transparent substrates sandwiching a phase separation liquid crystal layer.
The structure of the vertical electric field type liquid crystal element of the present invention comprises: each of the liquid crystal display device includes a first substrate and a second substrate each including a transparent electrode (layer) made of a transparent conductive material, and a phase separation liquid crystal layer sandwiched between the first substrate and the second substrate. The phase separation liquid crystal layer includes a polymer dispersed liquid crystal material containing liquid crystal molecules and a polymer component contained in the liquid crystal composition.
[ substrate ]
The substrate used in the liquid crystal device of the present invention is a substrate commonly used in a liquid crystal display device, an organic light emitting display device, other display devices, optical parts, a light adjusting device, a colorant, a mark, a printed matter, or an optical film, and is not particularly limited as long as it is a material having practical transparency and is suitable for applications in which tolerable heat resistance or transmittance is important in a temperature range of heating and use in the manufacturing process of the liquid crystal device.
Examples of such a substrate include: organic materials such as glass substrates, metal substrates, ceramic substrates, plastic substrates, and papers. In particular, when the base material is an organic material, there can be mentioned: cellulose derivatives, polyolefins, polyesters, polycarbonates, polyacrylates, polyarylates, polyethersulfones, polyimides, polyphenylene sulfides, polyphenylene oxides, nylons or polystyrenes, and the like. Among them, a plastic substrate such as polyester, polystyrene, polyolefin, cellulose derivative, polyarylate, polycarbonate, polyimide, or the like is preferably used.
In the case of having two substrates, one of the substrates may have transparency which is practical as a liquid crystal element, and the other substrate may not have transparency.
The shape of the substrate is a flat plate, but may be other shapes such as a curved shape. The substrate may have an electrode layer, an antireflection function, and a reflection function as needed.
In order to improve the adhesion of the liquid crystal element of the present invention, the surface treatment of these substrates may be performed. As the surface treatment, there may be mentioned: ozone treatment, plasma treatment, corona discharge treatment, silane coupling treatment, and the like. In order to adjust the transmittance or reflectance of light, an organic thin film, an inorganic oxide thin film, a metal thin film, or the like may be provided on the surface of the substrate by a method such as vapor deposition, or the substrate may be a pickup lens, a rod lens, an optical disk, a retardation film, a light diffusion film, a microlens sheet, a color filter, or the like in order to impart an optical added value.
[ electrode: transparent electrode layer
The electrode used in the liquid crystal element of the present invention is provided so as to generate an electric field in the liquid crystal element that can control the alignment of liquid crystal molecules in the phase separation liquid crystal layer. The electric field strength is controlled according to the degree to which a voltage is applied to the electrodes.
The shape of the electrode is not particularly limited, and the conductive portion may be stripe-shaped, mesh-shaped, or random mesh-shaped.
The electrode material is preferably a metal material, specifically Al, cu, au, ag, cr, ta, ti, mo, W, ni or an alloy containing at least one of them, and preferably Al or an alloy containing Al.
In order to improve the transparency of the liquid crystal element, the electrode is preferably constituted by a transparent electrode layer. Such a transparent electrode layer may include, for example, a known transparent conductive material such as Indium Tin Oxide (ITO), indium zinc Oxide (Indium Zinc Oxide, IZO), indium zinc Tin Oxide (Indium Zinc Tin Oxide, IZTO). In the case where one of the substrates contains a material that does not have transparency, the electrode provided on the substrate that does not have transparency is not required to have transparency, and can be appropriately selected from known metal materials.
[ alignment film layer ]
The substrate may be subjected to an alignment treatment so that the liquid crystal molecules in the polymer dispersed liquid crystal element of the present invention are aligned horizontally or vertically, or an alignment film may be provided. As the orientation treatment, there may be mentioned: extension treatment, rubbing treatment, polarized ultraviolet visible light irradiation treatment, ion beam treatment, siO 2 Oblique vapor deposition treatment on a substrate, and the like. As such an orientation film, there may be mentioned: polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene oxide, polyarylate, polyethylene terephthalate, polyethersulfone, epoxy resin, epoxyacrylate resin, acrylic resin, azo compound, coumarin compound, chalcone compound, cinnamate compound, fulgide (fulgide) compound, anthraquinone compound, arylvinyl compound, or the like, or a polymer or copolymer of the compounds. In order to impart an inclination angle to the liquid crystal molecules, in the case of performing a rubbing treatment, the compound to be subjected to an alignment treatment by rubbing is preferably a compound to promote crystallization of a material by adding a heating step after the alignment treatment or the alignment treatment. Among the compounds subjected to the alignment treatment other than rubbing, a photo-alignment material is preferably used.
In general, when a liquid crystal composition is brought into contact with a substrate having an alignment function, liquid crystal molecules are aligned in the vicinity of the substrate in a direction in which the substrate is subjected to an alignment treatment. The alignment treatment method for the substrate has a great influence on whether the liquid crystal molecules are aligned horizontally or obliquely or vertically with respect to the substrate.
[ example of method for manufacturing liquid Crystal element ]
In view of productivity, the liquid crystal element of the present invention is preferably produced by laminating a counter substrate with a polymer dispersed liquid crystal composition by, for example, a roll-to-roll method, and dropping or applying the polymer dispersed liquid crystal composition onto a substrate by, for example, a Drop Fill (ODF) method.
In the step of manufacturing the liquid crystal element by the roll-to-roll method, the polymer dispersed liquid crystal composition is applied to the first electrode, or the glass substrate having the alignment film and the first electrode, or the plastic substrate, and the second electrode, or the glass substrate having the alignment film and the second electrode, or the electrode side of the plastic substrate, or the alignment film side is bonded to the liquid crystal composition, and the thickness is made uniform, whereby the liquid crystal element can be manufactured. Examples of the method for applying the polymer-dispersed liquid crystal composition used in the present invention include known and customary methods such as an applicator method, a bar coating method, a roll coating method, a direct gravure coating method, a reverse gravure coating method, an ink jet method, a die coating method, and a cover coating method (cap coating method). In the step of manufacturing the liquid crystal element according to the ODF method, a sealing agent for a liquid crystal display, such as a curable sealing agent, which is formed by photo-heating an epoxy resin on one of a back plate and a front plate of a hollow element, is drawn in a closed-loop bank shape by using a dispenser, and a predetermined amount of the liquid crystal composition is dropped under deaeration, and then the front plate is bonded to the back plate, whereby the liquid crystal element can be manufactured.
The liquid crystal element of the present invention can be manufactured from a liquid crystal element by interposing a spacer for holding a space between two substrates, as in the case of the known liquid crystal element. The thickness between the substrates, that is, the thickness of the phase separation layer is preferably 2 μm to 50 μm, more preferably 10 μm to 30 μm. The spacers may be dispersed on the substrate in advance, or may be mixed in the polymer dispersed liquid crystal composition in advance and applied on the substrate simultaneously with the polymer dispersed liquid crystal composition.
The method of sandwiching the polymer dispersed liquid crystal composition between two substrates may be a usual vacuum injection method, but is preferably carried out by dropping or coating by ODF method or the like. The polymer dispersed liquid crystal composition is preferably in a uniform isotropic (isotropic) state during the period from the dropping or coating to the polymerizable composition for polymerization.
In the case of dropping or coating, a method of sandwiching the polymer dispersed liquid crystal composition between two substrates may be performed by a method of sandwiching the two substrates with a laminator or the like.
The polymer dispersed liquid crystal composition of the present invention can be used as a composition in which particles for determining the thickness of a liquid crystal element are mixed, and the composition can be held between hollow elements. As such particles, known and conventional glass particles or polymer particles used in a general liquid crystal display element or liquid crystal display can be used.
In this case, the following method is preferable: a method in which the polymer-dispersed liquid crystal composition and a composition containing particles for determining the thickness of the liquid crystal element are coated on a plastic substrate containing a first electrode, and then the plastic substrate containing a second electrode is bonded so that the first electrode and the second electrode face each other, and then ultraviolet light is immediately irradiated; a method of irradiating ultraviolet rays in a state where pressure is applied to the first plastic base material and the second plastic base material; or a method in which a liquid crystal composition for a liquid crystal element and a composition containing particles for determining the thickness of the liquid crystal element are applied onto a first plastic substrate containing a first electrode, the first plastic substrate and the applied liquid crystal composition are brought into a vacuum state, and a second plastic substrate containing a second electrode is bonded to face the first electrode and the second electrode in a vacuum state, and ultraviolet rays are irradiated.
[ polymerization Process ]
As a method for polymerizing the polymer dispersed liquid crystal composition of the present invention, ultraviolet irradiation is suitable. As the lamp that generates ultraviolet light, a metal halide lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, or the like can be used. The wavelength of the ultraviolet light to be irradiated is preferably ultraviolet light in a wavelength region which is an absorption wavelength region of a photopolymerization initiator contained in the polymer dispersed liquid crystal composition and is not an absorption wavelength region of the contained liquid crystal composition, and specifically, ultraviolet light having a wavelength of 330nm or less is preferably used by using a metal halide lamp, a high pressure mercury lamp, or an extra-high pressure mercury lamp. In addition, it is also preferable to use an Ultraviolet (UV) -light emitting diode (Light Emitting Diode, LED) lamp that can radiate a single wavelength.
The intensity of the irradiated ultraviolet rays can be suitably adjusted to obtain a target light adjusting layer, preferably 1mW/cm 2 ～200mW/cm 2 More preferably 5mW/cm 2 ～50mW/cm 2 . The time for irradiation of ultraviolet rays is appropriately selected depending on the intensity of the ultraviolet rays to be irradiated, but is preferably 10 seconds to 300 seconds.
The temperature at the time of ultraviolet irradiation is an important factor for determining the characteristics of the light control layer, but is preferably a temperature higher than the isotropic-nematic transition point (Tnm) of the polymer dispersed liquid crystal composition.
The liquid crystal element of the present invention may be used as it is or may be applied to other substrates. In addition, an adhesive or an adhesive layer, a protective film, a polarizing film, or the like may be laminated.
[ other electric fields ]
The liquid crystal element of the present invention may employ a transverse electric field type or other electric field type in addition to the vertical electric field type. Fringe fields used for fringe field switching (Fringe Field Switching, FFS) drive modes can also be used. In that case, a horizontally oriented layer may also be provided. The horizontally oriented layer may comprise known materials.
The liquid crystal element of the present invention is preferably used for a light control unit in a building material, a light control glass, a smart window for a vehicle, an organic light emitting diode (Organic Light Emitting Diode, OLED) display, or the like, for example. The liquid crystal display element of the present invention can be used for the same applications as the conventional polymer dispersed liquid crystal display element, and in particular, can be preferably used for a transmissive display, a flexible display, and the like. More specifically, the present invention is applicable to articles such as architectural light control elements for windows, skylights, roofs, walls, partition walls, door leaves, transportation light control elements for doors, windows, doors, helmets, sliding roofs, decorative light control elements for sunglasses, eyeglasses, sun visors, watches, mirrors, reflection plates, flexible liquid crystal display elements, reflective liquid crystal display elements, transparent liquid crystal display elements, and display members such as variable diffusion films.
< light modulation element >)
The light modulation element of the invention has a pair of transparent electrode substrates; and a composite layer disposed between the pair of transparent electrode substrates and comprising a polymer network and a liquid crystal compound. The polymer network is derived from a polymerizable composition (MA) contained in the polymer-dispersed liquid crystal composition, and the liquid crystal compound is a non-polymerizable liquid crystal composition (LB) contained in the polymer-dispersed liquid crystal composition.
The light control element may be an element that uses the liquid crystal element using the polymer dispersed liquid crystal composition and electrically controls the transmittance of light of the liquid crystal element. The light control element may be formed by attaching only the voltage applying device to the liquid crystal element, but may be formed by laminating a glass sheet with an intermediate film such as polyvinyl butyral (Polyvinyl Butyral, PVB), ethylene vinyl acetate copolymer resin (Ethyl Vinyl Acetate, EVA), thermoplastic urethane (Thermoplastic Urethanes, TPU) (polyurethane system), or an ionic intermediate film (SGP) interposed therebetween, and sandwiching the liquid crystal element between two glass sheets. Further, a functional film such as ultraviolet ray blocking and heat ray blocking may be added.
Examples (example)
The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. In the following examples and comparative examples, "parts" in the compositions means "parts by weight".
The non-polymerizable liquid crystal compositions (LB) used in examples and comparative examples described below are shown in tables 1 and 2, respectively. Table 3 shows descriptions of the components of the polymerizable composition (MA) used in examples and comparative examples, which will be described later.
TABLE 1
TABLE 2
The following shows the meanings of symbols showing the structures of the respective liquid crystal compounds in tables 1 and 2. In table 1, "1", "2", "3", "4" and "5" at the end of each component refer to the number of carbon atoms in the side chain.
For example, the structure of the liquid crystal compound corresponds to the expression as follows.
TABLE 3
Synthesis example 1
To a flask equipped with stirring vanes, 44.4 parts (0.2 mol) of isophorone diisocyanate (Isophorone Diisocyanate, IPDI) was added, and stirring was performed, while taking care of heat generation, 810 parts (0.1 mol) of polypropylene glycol (average molecular weight Mw: 8100) was added, and then the temperature was raised to 70 ℃. The reaction was carried out at the above temperature for 7 hours to obtain a urethane polymer having an isocyanate group at the terminal. Then, 23.2 parts (0.2 mol) of 2-hydroxyethyl acrylate (molecular weight 116) was added, and the reaction was further carried out at the above temperature for 7 hours. After confirming the disappearance of NCO absorption by infrared absorption spectrum, the resultant was taken out to obtain urethane acrylate UA-1 (average molecular weight Mw: 29800).
In the present invention, the number average molecular weight (Mn) and the weight average molecular weight (Mw) are values obtained by measuring by gel permeation chromatography (Gel Permeation Chromatography, GPC) and converting them into polystyrene. The measurement conditions of GPC are as follows.
[ measurement conditions of GPC ]
Measurement device: HLC-8320GPC manufactured by Tosoh Co., ltd "
And (3) pipe column: protective column "Su Bo (Super) HZ-L" manufactured by Tosoh Co., ltd., "Su Bo (Super) HZ2000" x 3 "manufactured by Tosoh Co., ltd.," T Su Bo (TSuper) HZM-M "manufactured by Tosoh Co., ltd.,"
A detector: built-in Refractive Index (RI) detector
And (3) data processing: "Aikesk (EcoSEC) -WorkStation (workbench) Ver2.01" manufactured by Tosoh Co., ltd "
Measurement conditions: column temperature 40 ℃, developing solvent tetrahydrofuran, flow rate 1.0 ml/min
Standard: according to the apparatus measurement manual, monodisperse polystyrene of known molecular weight is used.
Example 1
The polymerizable composition (MA) of the present invention was obtained by mixing 30 parts by weight of UA-1 produced in Synthesis example 1 as the first component, 2 to 1 part by weight of 2 to 2 parts by weight of the second component, 4 to 15 parts by weight of the fourth component and 5 to 1 part by weight of the fifth component, and further adding 0.1 part by weight of additive X-A and 184.3 parts by weight of Ornidad (Omnirad) as the polymerization initiator, and dissolving the mixture while stirring at 50 ℃. In addition, a liquid crystal composition LC1 shown in table 1 was prepared as a non-polymerizable liquid crystal composition (LB).
To the obtained polymerizable compound MA-1, the liquid crystal composition LC1 was added so that the weight ratio of the polymerizable composition (MA)/the non-polymerizable liquid crystal composition (LB) (MA/LB weight ratio) became 49/51, and the mixture was dissolved while stirring at 50 ℃.
After the obtained polymer dispersed liquid crystal composition PL1 was poured into a glass tank (structure of glass substrate/transparent electrode layer/air layer/transparent electrode layer/glass substrate) having a thickness of 15 μm at room temperature, ultraviolet rays were irradiated at room temperature, thereby obtaining a liquid crystal element having a liquid crystal polymer composite. The ultraviolet light is provided by a UV-LED lamp with a wavelength of 365nm and an intensity of 15mW/cm 2 The time was 60 seconds. The irradiation intensity of ultraviolet rays was measured using an ultraviolet luminance meter UIT-201 manufactured by a bovine tail motor (USHIO) and a sensor UVD-365 PD.
(evaluation of transmittance)
A rectangular wave 60Hz, 0V to 100V voltage was applied to a liquid crystal device having the obtained liquid crystal polymer composite using LCD-5200 (manufactured by tsukamureluct electronics Co., ltd.). The transmittance at 0V is defined as T 0 The transmittance when an alternating current (Alternating Current, AC) of 100V is applied is defined as T 100 And evaluated. The respective transmittance at 25℃was 0.13% and 87.5%.
(evaluation of drive Voltage)
Using a liquid crystal element having the obtained liquid crystal polymer composite, the transmittance (T) at 0V was measured at 25 ℃ 0 ) When the transmittance was set to 0%, the value of the transmittance (T) 100 ) When the transmittance is set to 100%, the voltage at which the transmittance reaches 90% is defined as the driving voltage (V 90 ) And the measurement was performed. The driving voltage was 37V.
(evaluation of Low temperature drivability)
For a liquid crystal element having the obtained liquid crystal polymer composite, a voltage dependence of transmittance was measured using LCD-5200 (manufactured by tsukamurelectronic corporation) while lowering the temperature from 25 ℃ to-30 ℃ in units of 5 ℃. At this time, the change width (T 100 -T 0 ) The change width (T) at 25 ℃ or more below the measurement temperature 100 -T 0 ) The lowest measured temperature of 90% of the range is set to the lowest driving temperature [ DEGC ]]. The minimum driving temperature was-20 ℃.
(evaluation of adhesion)
The adhesion was evaluated by the following method. First, glass beads having a particle size of 15 μm were spread on one of the transparent electrode faces of two PET films with transparent electrodes, and the liquid crystal composition was dropped thereon and applied with an applicator. Then, another PET film was bonded to the coated surface so that the transparent electrode surface and the coated surface were in contact with each other, to thereby prepare a film laminate. The liquid crystal composition is made to have a substantially uniform thickness by sandwiching the film laminate between two glass plates and uniformly applying pressure to the entire surface of the film laminate. The film laminate sandwiched between the glass plates was irradiated with a UV-LED lamp having a light source of 365nm wavelength at room temperature for 60 seconds at an intensity of 15mW/cm 2 After ultraviolet rays of (2), the glass plate was removed, whereby a polymer dispersed liquid crystal element was obtained. Further, the ultraviolet intensity was measured using an ultraviolet photometer UIT-201 manufactured by a bovine tail motor (USHIO) and a sensor UVD-365PD.
The polymer-dispersed liquid crystal element was cut into a long strip shape so that the width became 25mm, and 180 ° peel test was performed. The average peel strength of the two transparent electrode-equipped PET film ends at one end of the strip were peeled from each other in the 180℃direction at a tensile speed of 50 mm/min using a force tester (force tester) MCT2150 manufactured by A & D company. The intensity was 0.5N.
(examples 2 to 5, comparative examples 1 to 2)
Polymer dispersed liquid crystal compositions PL2 to PL5 and polymer dispersed liquid crystal compositions PL11 to PL12 were prepared in the same manner as PL1 except that the respective components were used in the formulation ratios shown in Table 4.
Using these polymer-dispersed liquid crystal compositions PL2 to PL5 and PL11 to PL12, polymer-dispersed liquid crystal elements of examples 2 to 5 and comparative examples 1 to 2 were obtained in the same manner as in example 1.
Using the obtained polymer dispersed liquid crystal element, each evaluation was performed in the same manner as in example 1. The blending ratio and evaluation results of the respective components are shown in table 4.
TABLE 4
From the above results, the polymer dispersed liquid crystal elements of examples 1 to 5 can realize both low transmittance in the scattering state and high transmittance in the transmitting state, and can be driven at a sufficiently low driving voltage. In addition, a sufficiently low driving voltage can be maintained even under low temperature conditions, and a minimum driving temperature can be achieved as low as-20 ℃. Further, the adhesive property test showed excellent values.
In contrast, in comparative examples 1 to 2, the driving voltage increased under low temperature conditions, and in particular, the driving voltage increased significantly at-20 ℃. In addition, the minimum driving temperature was also-5℃but insufficient.
Claims (12)
1. A polymer-dispersed liquid crystal composition comprising a polymerizable composition (MA) and a non-polymerizable liquid crystal composition (LB), wherein the non-polymerizable liquid crystal composition (LB) has a positive value of dielectric anisotropy and a rotational viscosity [ gamma ] 1 at 25 ℃ of 400 mPa-sec or less.
2. The polymer-dispersed liquid crystal composition according to claim 1, wherein the polymerizable composition (MA) contains one or more polymerizable compounds represented by the following general formula (ii);
P ii1 -Z ii1 -A ii1 (ii)
Wherein P is ii1 Represents a polymerizable group and is preferably a polymerizable group,
Z ii1 represents a single bond or an alkylene group having 1 to 7 carbon atoms, one or more of which are not adjacent to each other-CH 2 -independently of each other through-O-, in such a way that the oxygen atoms are not directly adjacent-CO-, -COO-or-OCO-substitution,
A ii1 the expression of the formulas (ii-1) to (ii-20);
wherein more than one-CH 2 -can be independently passed through-O-, -S-, -COO-, -OCO-, -NH-, -NCH 3 -or-CO-substitution, in the case where in total more than two oxygen atoms and/or sulfur atoms are present in the general formulae (ii-1) to (ii-20), they are not bonded to each other as in-O-O-, -O-S-or-S-S-, and in addition, more than one-CH 2 -CH 2 -may be substituted with-ch=ch-group, and in addition, the hydrogen atom in the general formulae (ii-1) to (ii-20) may be substituted with an alkyl group having 1 to 8 carbon atoms, one or more of the alkyl groups being not adjacent-CH 2 -each independently substituted by-O-, -CO-, -COO-or-OCO-in such a way that the oxygen atoms are not directly adjacent; in addition, the black dots in the formula represent the direction Z ii1 Is a bond of (a).
3. The polymer-dispersed liquid crystal composition according to claim 1 or 2, wherein the non-polymerizable liquid crystal composition (LB) contains one or two or more compounds represented by the following general formula (iii);
Wherein R is iii1 Independently of one another, is an n-alkyl, n-alkoxy, alkenyl, alkenyloxy or alkoxyalkyl radical having from 1 to 7 carbon atoms,
R iii2 represents fluorine, chlorine or cyano groups、CF 3 Radical, OCF 3 Radical, OCHF 2 A group, NCS group or C1-10 alkyl group, one or both of which are not adjacent to each other, -CH 2 The radical may be substituted by oxygen atoms, -COO-, -OCO-, and, in addition, more than one-CH 2 CH 2 Can be substituted by-CH=CH-or-C≡C-,
A iii1 represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, 2-methyl-1, 4-phenylene, 3-methyl-1, 4-phenylene, 2, 3-dimethyl-1, 4-phenylene, 3, 5-dimethyl-1, 4-phenylene or 2, 6-dimethyl-1, 4-phenylene,
A iii2 a is a iii3 Each independently of the others represents 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, 2-methyl-1, 4-phenylene, 3-methyl-1, 4-phenylene, 2, 3-dimethyl-1, 4-phenylene, 3, 5-dimethyl-1, 4-phenylene or 2, 6-dimethyl-1, 4-phenylene,
Z iii1 Z is as follows iii2 One of them is-C.ident.C-, the other, when present, is-C.ident.C-, -CF 2 O-、-OCF 2 -、-CH＝CH-、-CF＝CF-、-COO-、-CH 2 -CH 2 -、-CF 2 -CF 2 -or a single bond,
n iii 0 or 1.
4. The polymer-dispersed liquid crystal composition according to claim 1 or 2, wherein the polymerizable composition (MA) contains one or two or more polymerizable compounds represented by the following general formula (v);
P v1 -R v1 (v)
wherein P is v1 Represents a polymerizable group and is preferably a polymerizable group,
R v1 represents a linear or branched alkyl group having 1 to 22 carbon atoms, one or more of which are-CH 2 -independently of each other through-O-, in such a way that the oxygen atoms are not directly adjacent-CO-, -COO-, -OCO-or-P (=O) (-A-OH) -substitution, one or more hydrogen atoms present in the alkyl group may each independently be substituted with a fluorine atom or-OH.
5. The polymer dispersed liquid crystal composition according to claim 1 or 2, wherein the polymerizable composition (MA) contains one or two or more polyfunctional (meth) acrylate oligomers (i) having a weight average molecular weight of 2000 or more.
6. The polymer dispersed liquid crystal composition according to claim 1 or 2, wherein the polymerizable composition (MA) contains one or two or more selected from the group consisting of a polyfunctional polymerizable oligomer having a weight average molecular weight of less than 2000 represented by the following general formula (iv) and a polyfunctional polymerizable monomer;
Wherein Y is iv1 Represents a hydrogen atom or a methyl group,
X iv1 n represents 130 or less carbon atoms iv1 A linear, branched or cyclic hydrocarbon group having a valence, and at least one of the linear, branched or cyclic hydrocarbon groups-CH 2 The radicals may each independently be interrupted by-O-, by oxygen atoms which are not directly adjacent to one another-NH-, -CO-, -COO-, -OCO-, -CH=CH-, or-C≡C-substitution, one or more hydrogen atoms present in the linear, branched or cyclic hydrocarbon group may be each independently substituted with a fluorine atom or-OH,
n iv1 an integer of 2 to 6.
7. The polymer-dispersed liquid crystal composition according to claim 1 or 2, wherein the polymerizable composition (MA) further contains an additive represented by the following general formula (X);
wherein Y is X1 Represents a hydrogen atom or a methyl group,
X X1 n represents 130 or less carbon atoms X1 A linear, branched or cyclic hydrocarbon group having a valence, and at least one of the linear, branched or cyclic hydrocarbon groups-CH 2 The radicals may each independently be interrupted by-O-, by oxygen atoms which are not directly adjacent to one another-NH-, -CO-, -COO-, -OCO-, -CH=CH-, or-C≡C-substitution, one or more hydrogen atoms present in the linear, branched or cyclic hydrocarbon group may be each independently substituted with a fluorine atom or-OH,
n X1 An integer of 1 to 6 is represented,
here, X is X1 At least one of-CH 2 The radicals are substituted by the following formula (X-1),
8. the polymer dispersed liquid crystal composition according to claim 1 or 2, further comprising a polymerization initiator.
9. The polymer dispersed liquid crystal composition according to claim 5, wherein the multifunctional (meth) acrylate oligomer (i) having a weight average molecular weight of 2000 or more is one or two or more selected from the group consisting of urethane-based (meth) acrylate oligomers and polyester-based (meth) acrylate oligomers.
10. The polymer dispersed liquid crystal composition according to claim 1 or 2, wherein the polymerizable composition (MA) further comprises one or more selected from the group consisting of a polymerization inhibitor, an antioxidant, a light stabilizer, particles having a particle diameter of less than 1 μm, a pigment, and a pigment.
11. A liquid crystal cell obtained by using the polymer dispersed liquid crystal composition according to claim 1 or 2.
12. A dimming element, comprising:
a pair of transparent electrode substrates; and
a liquid crystal polymer complex disposed between the transparent electrode substrates and comprising a polymer network and a liquid crystal compound,
In the light-adjusting element, the light-adjusting element is provided with a light-adjusting element,
the polymer network being derived from the polymerizable composition (MA) contained in the polymer dispersed liquid crystal composition according to claim 1 or 2,
the liquid crystal compound is the non-polymerizable liquid crystal composition (LB) contained in the polymer dispersed liquid crystal composition according to claim 1 or 2.
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