CN116731725A - Liquid crystal composition, liquid crystal element, and light adjusting element - Google Patents
Liquid crystal composition, liquid crystal element, and light adjusting element Download PDFInfo
- Publication number
- CN116731725A CN116731725A CN202310195012.3A CN202310195012A CN116731725A CN 116731725 A CN116731725 A CN 116731725A CN 202310195012 A CN202310195012 A CN 202310195012A CN 116731725 A CN116731725 A CN 116731725A
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- mass
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- general formula
- liquid crystal
- crystal composition
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 363
- 239000000203 mixture Substances 0.000 title claims abstract description 320
- 150000001875 compounds Chemical class 0.000 claims abstract description 759
- 239000000049 pigment Substances 0.000 claims abstract description 97
- 125000004432 carbon atom Chemical group C* 0.000 claims description 235
- 125000000217 alkyl group Chemical group 0.000 claims description 124
- -1 Naphthalene-2, 6-diyl Chemical group 0.000 claims description 117
- 125000003342 alkenyl group Chemical group 0.000 claims description 97
- 125000001153 fluoro group Chemical group F* 0.000 claims description 63
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
- 229910052731 fluorine Inorganic materials 0.000 claims description 43
- 238000006467 substitution reaction Methods 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- 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 claims description 12
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 230000003078 antioxidant effect Effects 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 3
- 239000004611 light stabiliser Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 58
- 241001591024 Samea Species 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 description 46
- 230000000694 effects Effects 0.000 description 43
- 230000007704 transition Effects 0.000 description 38
- 206010047571 Visual impairment Diseases 0.000 description 25
- 238000010521 absorption reaction Methods 0.000 description 24
- 230000006872 improvement Effects 0.000 description 24
- 239000012071 phase Substances 0.000 description 22
- 239000000975 dye Substances 0.000 description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 21
- 150000003254 radicals Chemical class 0.000 description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- 230000004044 response Effects 0.000 description 19
- 239000000758 substrate Substances 0.000 description 19
- 210000004027 cell Anatomy 0.000 description 18
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
- 239000010410 layer Substances 0.000 description 16
- 239000000654 additive Substances 0.000 description 15
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 13
- 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 description 13
- 230000000996 additive effect Effects 0.000 description 12
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 125000005647 linker group Chemical group 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 9
- 239000010408 film Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000006096 absorbing agent Substances 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000003302 alkenyloxy group Chemical group 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 239000000565 sealant Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 102220492401 Ribulose-phosphate 3-epimerase_L12A_mutation Human genes 0.000 description 4
- 125000005755 decalin-2,6-ylene group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C([H])([*:2])C([H])([H])C([H])([H])C2([H])C([H])([H])C1([H])[*:1] 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 125000006017 1-propenyl group Chemical group 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 210000002858 crystal cell Anatomy 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- FJDLQLIRZFKEKJ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanamide Chemical compound CC(C)(C)C1=CC(CCC(N)=O)=CC(C(C)(C)C)=C1O FJDLQLIRZFKEKJ-UHFFFAOYSA-N 0.000 description 2
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000005725 cyclohexenylene group Chemical group 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 150000001988 diarylethenes Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 239000001044 red dye Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 239000004984 smart glass Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- 125000005450 2,3-difluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C(F)=C(F)C([*:1])=C1[H] 0.000 description 1
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000032900 absorption of visible light Effects 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000005125 dioxazines Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Chemical class N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical class [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- BIGSSBUECAXJBO-UHFFFAOYSA-N terrylene Chemical group C12=C3C4=CC=C2C(C=25)=CC=CC5=CC=CC=2C1=CC=C3C1=CC=CC2=CC=CC4=C21 BIGSSBUECAXJBO-UHFFFAOYSA-N 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 150000004905 tetrazines Chemical class 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C09K19/04—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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
- C09K19/3497—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and nitrogen atoms
-
- 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
- C09K19/60—Pleochroic dyes
-
- 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
- G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
- G02F1/13725—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on guest-host interaction
-
- 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
- G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
- G02F1/13731—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on a field-induced phase transition
- G02F1/13737—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on a field-induced phase transition in liquid crystals doped with a pleochroic dye
Abstract
The application provides a liquid crystal composition containing a pigment compound, a liquid crystal element or a light-adjusting element, which has a large dichroic ratio, a high contrast, a high solubility of the pigment compound and the liquid crystal composition, an excellent light resistance and an excellent heat resistance. The present application provides a liquid crystal composition containing a pigment compound and a liquid crystal composition containing a pigment compound, wherein the pigment compound is represented by the following general formula (1), and the liquid crystal composition contains a compound represented by the general formula (II), and the liquid crystal composition using the sameA liquid crystal display element or a light adjusting element of the liquid crystal composition containing the pigment compound. The solubility of the pigment compound of the liquid crystal composition containing the pigment compound provided by the application is kept excellent with the solubility, and further, the liquid crystal composition has excellent two-color ratio and light resistance. In addition, by using the liquid crystal composition containing a pigment compound as a structural member, a liquid crystal display element or a light adjusting element having high contrast can be provided.[ chemical formula 1 ]]
Description
Technical Field
The present application relates to a liquid crystal composition containing a pigment compound, and a liquid crystal display element or a light control element using the same.
Background
The following studies were performed on a light control element that electrically controls transmission of light: for use in interior and exterior decoration of buildings such as electric vehicles and buildings which are driven by a secondary battery provided in a window. Such a window is called a smart window (smart window), and as a light control element that can be used, a liquid crystal (GH) system in which a dichroic dye is added, a liquid crystal system in which a polymer network is provided in a cell, a system in which electrochromic (electrochromic) is used, and the like are known. Among them, the GH liquid crystal system is expected as a system that allows high-speed switching of light transmission, does not transmit light, and does not require a polarizing plate, and thus a dimming element having high transmittance can be realized at low cost.
With respect to GH liquid crystal compositions, studies have been made earlier, and attempts have been made to develop liquid crystal display elements or light control elements having useful element properties (for example, large dichroic ratio, high contrast, high solubility with the liquid crystal composition, excellent light resistance, excellent heat resistance) (patent documents 1 to 4).
However, there are liquid crystal compositions unsuitable for use in liquid crystal display devices and light control devices depending on the components constituting the composition, and further improvement in performance is demanded. For example, in order to obtain a large dichroic ratio, it is necessary to contain a large amount of a dichroic dye in the liquid crystal composition, and there is a problem of solubility of the composition in which the dichroic dye or the liquid crystal compound is precipitated. In particular, in order to be used as a light control element, it is necessary to exhibit a nematic liquid crystal phase in a wide temperature range, and since the molecular weight of the dye is larger than that of the liquid crystal compound, there is a problem in terms of solubility at low temperature.
In order to solve the above-described problems, it is important to combine a liquid crystal composition as a main component with a dichroic dye. In particular, in order to achieve high contrast, it is necessary that the dichroic dye exhibits high solubility in the host liquid crystal in addition to a large dichroic ratio.
To date, a large number of dichroic dyes have been studied, and compounds exhibiting a large dichroic ratio generally have a large mesogen in large numbers, and basically lack solubility in host liquid crystals, and further improvement is demanded. For example, as a dye compound, the following compounds are reported (patent document 5), but these compounds do not have a large dichroic ratio, high solubility, and high light resistance at the same time.
[ chemical 1]
[ Prior Art literature ]
[ patent literature ]
[ patent document 1] International publication No. 2017/038616 handbook
Patent document 2 japanese patent laid-open publication No. 2019-85681
[ patent document 3] International publication No. 2018/078968 handbook
[ patent document 4] Japanese patent application laid-open No. 2017-513975
[ patent document 5] Chinese patent application publication No. 109369684
Disclosure of Invention
[ problem to be solved by the invention ]
The present invention addresses the problem of providing a liquid crystal composition containing a pigment compound which exhibits a large dichroic ratio, a high contrast, a high solubility between the pigment compound and the liquid crystal composition, excellent light resistance, and excellent heat resistance. In particular, a liquid crystal composition containing a pigment compound excellent in solubility and in a dichroic ratio and light resistance is provided, and a liquid crystal display element or a light control element using the liquid crystal composition containing a pigment compound as a structural member is provided.
[ means of solving the problems ]
The present inventors have made various studies to solve the above problems, and as a result, have provided a liquid crystal composition containing a compound represented by the general formula (1) as a coloring compound and a coloring compound containing a liquid crystal composition containing one or more compounds represented by the general formula (II), together with a liquid crystal display element or a light control element using the liquid crystal composition containing the coloring compound.
[ chemical 2]
(wherein U is any one selected from the group represented by the general formula (2) and the general formula (3),
R 1 、R 2 、R 3 、R 4 r is R 5 Independently of one another, a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, 1-CH present in these groups 2 -or not more than 2-CH 2 -can be represented by-NR 6 -、-O-、-S-、-CO-、-CS-、-COO-、-OCO-、-CO-S-、-S-CO-、-SO-、-SO 2 -, -O-CO-O-, -CO-NH-; -NH-CO- -CH=CH-, -CF=CF-, or-C≡C-substitution, the hydrogen atoms present in these radicals may be substituted by fluorine atoms, where R 6 Represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, 1-CH being present in these groups 2 -or not more than 2-CH 2 Can be selected from the group consisting of-O-, -S-, -COO- -an OCO-or-CO-substitution, the hydrogen atoms present in these groups may be substituted by fluorine atoms,
R a 、R b R is R c Independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, which are present in these groups1-CH 2 -or not more than 2-CH 2 -can be represented by-NR 7 -、-O-、-S-、-CO-、-CS-、-COO-、-OCO-、-CO-S-、-S-CO-、-SO-、-SO 2 -, -O-CO-O-, -CO-NH-; -NH-CO- -CH=CH-, -CF=CF-, or-C≡C-substitution, the hydrogen atoms present in these radicals may be substituted by fluorine atoms, where R 7 Represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, 1-CH being present in these groups 2 -or not more than 2-CH 2 Can be selected from the group consisting of-O-, -S-, -COO- -an OCO-or-CO-substitution, the hydrogen atoms present in these groups may be substituted by fluorine atoms,
X a 、X b x is X c Each independently represents-S-or-O-,
A 1 、A 2 、A 4 、A 5 、A a a is a b Each independently represents a hydrocarbon ring or a heterocyclic ring having 3 to 16 carbon atoms which may be substituted,
Z 1 、Z 2 、Z 4 、Z 5 、Z a 、Z b z is as follows c Each independently represents-CH 2 O-、-OCH 2 -、-CF 2 O-、-OCF 2 -、-COO-、-OCO-、-CH 2 CH 2 -、-CF 2 CF 2 -, -CH=CH-, -CF=CF-, -N=CH-; -CH=N-, -N=N-, -C≡C-, or a single bond,
i. j, a, b, c and d each independently represent an integer of 0 to 4,
at A 1 、A 2 、A 4 、A 5 、A a A is a b In the case of a plurality of A 1 、A 2 、A 4 、A 5 、A a A is a b May be the same or different, at Z 1 、Z 2 、Z 4 、Z 5 、Z a 、Z b Z is as follows c In the case of a plurality of Z' s 1 、Z 2 、Z 4 、Z 5 、Z a 、Z b Z is as follows c May be the same or different, in which case a plurality of R's are present 6 In the case of (1), a plurality of R 6 May or may not be the sameTogether with the other parts
[ chemical 3]
[ chemical 4]
(in the general formula (II),
R II1 represents an alkyl group having 1 to 10 carbon atoms, 1 of the alkyl groups being non-adjacent to or greater than 2-CH 2 Each independently is composed of-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution,
A II1 a is a II2 Each independently represents a radical selected from the group consisting of,
(a) 1, 4-Cyclohexylene (1-CH present in the radical) 2 -or not more than 2-CH 2 -can be substituted by-O-)
(b) 1, 4-phenylene (1-ch=or more than 2-ch=that are not adjacent to each other present in the group may be substituted with-n=)
(c) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-ch=or non-contiguous 2 or more-ch=present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted to-n=)
The groups (a), (b) and (c) may each be independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z II1 represents a single bond, -CH 2 CH 2 -、-(CH 2 ) 4 -、-OCH 2 -、-CH 2 O-、-COO-、-OCO-、-OCF 2 -、-CF 2 O-, -ch=n-n=ch-, -ch=ch-, -cf=cf-or-c≡c-,
Y II1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group or an alkyl group having 1 to 10 carbon atoms, 1 of which is not adjacent to or more than 2-CH 2 -can be independently of each other from-CH=CH-, -C.ident.C-, -O-, -CO-, -COO-or-OCO-substitution, in addition, in the case of the optical fiber, 1 or more than 2 hydrogen atoms in the alkyl group may be substituted with fluorine atoms,
m II1 represents 1, 2, 3 or 4, at m II1 In the case of 2, 3 or 4, a plurality of A II1 A plurality of Z II1 Can be the same or different respectively)
[ Effect of the invention ]
The solubility of the pigment compound of the liquid crystal composition containing the pigment compound represented by the general formula (1) and the pigment compound represented by the general formula (II) is excellent, and the solubility is excellent, and the liquid crystal composition further has excellent dichroic ratio and light resistance. In addition, by using the liquid crystal composition containing a pigment compound as a structural member, a liquid crystal display element or a light adjusting element having high contrast can be provided.
Detailed Description
< pigment Compound >)
In general formula (1) as the coloring matter compound, U is preferably a structure represented by general formula (3) in order to increase the dichroic ratio, and in the case where light resistance and solubility in a host liquid crystal are important, U is preferably a structure represented by general formula (2).
In the general formula (1), R 1 、R 2 、R 3 、R 4 R is R 5 Each independently is preferably an alkyl group having 2 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, which represents a fluorine atom, a cyano group, 1-CH present in these groups 2 -or not more than 2-CH 2 Also preferably from the group consisting of-O-, -S-, -CO-, -CS-, -COO-, and-OCO-, -CO-S-, -S-CO-, -SO 2 -substitution. In order to improve the solubility in the host liquid crystal, each independently is preferably an alkyl group or alkenyl group having 1 to 20 carbon atoms, more preferably an unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, still more preferably an unsubstituted straight-chain or branched alkyl group having 4 to 20 carbon atoms, and particularly preferably an unsubstituted branched alkyl group having 4 to 20 carbon atoms. In order to show a high dichroic ratio, R 3 Preferably straight-chain alkyl or fluorinated alkyl having 1 to 5 carbon atomsRadicals, 1-CH present in these radicals 2 -or not more than 2-CH 2 Preferably consisting of-CO-; -COO-or-OCO-substitution, methyl or trifluoromethyl is particularly preferred. In order to lengthen the absorption wavelength, R 3 Preferred are fluorine atom, cyano group, thioether group, alkylsulfonyl group, N-dialkylsulfonamide group, alkanoyl group, alkylcarbonyloxy group or alkyloxycarbonyl group.
In the general formula (1), R a 、R b R is R c Each independently is preferably an alkyl group having 2 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, which groups have 1-CH 2 -or not more than 2-CH 2 Also preferably from the group consisting of-O-, -S-, -CO-, -CS-, -COO-, and-OCO-, -CO-S-, -S-CO-, -SO 2 -substitution. In order to improve the solubility in the host liquid crystal, each independently is preferably an alkyl group or alkenyl group having 1 to 20 carbon atoms, more preferably an unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, still more preferably an unsubstituted straight-chain or branched alkyl group having 4 to 20 carbon atoms, and particularly preferably an unsubstituted branched alkyl group having 4 to 20 carbon atoms. On the other hand, hydrogen atoms are preferable from the viewpoints of high dichroic ratio and ease of production. In order to increase the absorption wavelength, alkylsulfonyl, N-dialkylsulfonamide, and alkanoyl are preferable.
In the general formula (1), X a 、X b X is X c Each independently represents-S-or-O-, from the viewpoint of solubility and lengthening the absorption wavelength, preferably-S-and-O-are preferred from the viewpoints of dichroic ratio, light resistance and ease of manufacture.
In the general formula (1), A 1 、A 2 、A 4 、A 5 、A a A is a b Each independently is preferably a hydrocarbon ring or a heterocyclic ring having 3 to 16 carbon atoms which may be substituted. Here, the hydrocarbon ring may be an aliphatic ring or an aromatic ring, or may have a substituent on the ring. The heterocyclic ring may be an aliphatic ring or an aromatic ring, or may contain at least one hetero element among elements constituting the ring structure and have a substituent on the ring. Here, A 1 、A 2 、A 4 、A 5 、A a A is a b Each independently preferably represents a group selected from the group consisting of,
(a) 1, 4-Cyclohexylene (1-CH present in the radical) 2 -or not more than 2-CH 2 -can be substituted by-O-or-S-, 1 CH or more than 2 CH not adjacent in said radical can be substituted by N)
(b) 1, 4-phenylene (1-ch=or more than 2 non-adjacent-ch=present in the radical may be substituted to-n=)
(c) 1, 4-cyclohexenylene, bicyclo [2.2.2] octane-1, 4-diyl, naphthalene-2, 6-diyl, naphthalene-1, 4-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 5,6,7, 8-tetrahydronaphthalene-1, 4-diyl, decahydronaphthalene-2, 6-diyl, anthracene-1, 4-diyl, anthracene-9, 10-diyl, phenanthrene-2, 7-diyl (the hydrogen atoms present in these groups may be substituted by fluorine atoms or chlorine atoms, in addition, naphthalene-2, 6-diyl, naphthalene-1, 4-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 5,6,7, 8-tetrahydronaphthalene-1, 4-diyl, anthracene-2, 6-diyl, anthracene-1, 4-diyl, anthracene-9, 10-diyl or phenanthrene-2, 7-diyl may be substituted by = in 1 or by ch=n-2 =
(d) Thiophene-2, 5-diyl, thiophene-2, 4-diyl, benzothiophene-2, 5-diyl, benzothiophene-2, 6-diyl, dibenzothiophene-3, 7-diyl, dibenzothiophene-2, 6-diyl, thieno [3,2-b ] thiophene-2, 5-diyl (1-ch=or non-contiguous more than 2-ch=present in said groups may be substituted to-n=)
These radicals are also preferably unsubstituted or substituted by more than one substituent L 2 And (3) substitution.
L 2 Each independently is preferably a hydrogen atom, a fluorine atom, a chlorine atom, a pentafluorothioyl group, a nitro group, a cyano 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 1-CH 2 -or more than 2-CH 2 Each independently of the others is composed of-O-, -S-, -CO-, -CS-, -COO-, -OCO-, and CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO--ch=ch-COO-, -ch=ch-OCO-, -COO-ch=ch-, -OCO-ch=ch-, -cf=cf-, or-c≡c-substituted linear alkyl of 1 to 20 carbon atoms or branched or cyclic alkyl of 3 to 20 carbon atoms, each independently further preferably being a hydrogen atom, a fluorine atom, a chlorine atom, a pentafluorothio group, a nitro group, a cyano group, an isocyano group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a thioisocyano group, a methyl group, an ethyl group, a propyl group, a methoxy group, an ethoxy group or an acetyl group.
In addition, as A 1 、A 2 、A 4 、A 5 、A a A is a b Preferably represents a group selected from the following groups.
[ chemical 5]
Here, R is e Each independently preferably represents a methyl group, an ethyl group, a propyl group, a 2-propyl group, a butyl group, a 2-butyl group, a methoxy group, an ethoxy group, a methylthio group, an ethylthio group, a dimethylamino group, a diethylamino group, a cyano group, a nitro group, a fluorine atom or a chlorine atom. Specifically, in order to improve the solubility in the host liquid crystal, trans-1, 4-cyclohexylene, unsubstituted 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3-fluoro-1, 4-phenylene, 2-alkyl-1, 4-phenylene, 3-alkyl-1, 4-phenylene, unsubstituted thiophene-2, 5-diyl, unsubstituted thiophene-2, 4-diyl, 4-alkyl-thiophene-2, 5-diyl or 5-alkyl-thiophene-2, 4-diyl is preferable. At this time, at A 1 A is a 2 When there are plural, plural A 1 A is a 2 Preferably, each of the structures is different. In order to increase the dichroic ratio, unsubstituted 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3-fluoro-1, 4-phenylene, unsubstituted thiophene-2, 5-diyl, unsubstituted thiophene-2, 4-diyl, unsubstituted naphthalene-2, 6-diyl, unsubstituted naphthalene-1, 4-diyl or unsubstituted thieno [3,2-b ] are preferred]Thiophene-2, 5-diyl. In order to increase the absorption wavelength, an electron donating ring is preferable, and thiophene-2, 5-diyl is particularly preferable, Thiophene-2, 4-diyl, thieno [3,2-b]Thiophene-2, 5-diyl or piperidine-1, 4-diyl. In addition, in order to improve solubility in host liquid crystal, R e Preferably represents a methyl group, an ethyl group, a propyl group, a fluorine atom or a chlorine atom, and more preferably a methyl group, an ethyl group or a fluorine atom. In order to lengthen the absorption wavelength, R e The electron donating substituent is preferable, and methoxy, ethoxy, dimethylamino, diethylamino are more preferable, and methoxy, ethoxy, or dimethylamino are particularly preferable.
In the general formula (1), Z 1 、Z 2 、Z 4 、Z 5 、Z a 、Z b Z is as follows c Each independently preferably represents-CH 2 CH 2 -, -CH=CH-, -CF=CF-, -N=N-, -C≡C-, or a single bond. In addition, in order to improve the solubility in the host liquid crystal, it is preferably-CH 2 O-、-OCH 2 -、-CH 2 CH 2 -or a single bond, and preferably-CH 2 CH 2 -or a single bond. In order to increase the ratio of the two colors, preferably-CH=CH-, -CF=CF-, -N=CH-, -CH=N-, -N=N-, -C≡C-, or a single bond, further preferably-CH=CH-, -N=N-, -c≡c-or a single bond. In order to exhibit high light resistance, a single bond is preferable.
In the general formula (1), i, j, a, b, c and d are each independently preferably an integer of 0 to 3, and more preferably an integer of 1 to 2 from the viewpoint of solubility. In view of a high dichroic ratio and a long wavelength of the absorption wavelength, i, j, c, and d are each independently preferably an integer of 1 to 3. In order to increase the dichroic ratio, a and b are each independently preferably 0 or 1, and particularly preferably 0.
In general formula (1), it is preferable that oxygen atoms and/or oxygen atoms and sulfur atoms are not directly bonded to each other in view of stability of the compound.
The compound represented by the general formula (1) has a skeleton represented by U in its structure and R in its structure 1 、R 2 、R 3 、R 4 R is R 5 The alkyl group and the like are shown to have high solubility in the liquid crystal composition. Especially inHaving A in the structure 1 、A 2 、A 4 、A 5 、A a A is a b In the case of the ring structure shown, since the compound is entirely close to a rod-like structure, the solubility in the liquid crystal composition is improved, and dichroism when used as a pigment can be improved. In particular, when these rings are aromatic rings, the pi-electron conjugated system is extended in the whole molecule, and thus is effective for increasing the wavelength of light absorption.
The compound represented by the general formula (1) is preferably represented by the following formulas (1-A) to (1-D).
[ chemical 6]
(wherein R is 1 、R 2 、R 3 、R 4 、R 5 、R a 、R b 、R c 、A 1 、A 2 、A 4 、A 5 、A a 、A b 、Z 1 、Z 2 、Z 4 、Z 5 、Z a 、Z b 、Z c I, j, a, b, c and d each represent R in the general formula (1) 1 、R 2 、R 3 、R 4 、R 5 、R a 、R b 、R c 、A 1 、A 2 、A 4 、A 5 、A a 、A b 、Z 1 、Z 2 、Z 4 、Z 5 、Z a 、Z b 、Z c I, j, a, b, c and d have the same meaning)
Further, among the compounds represented by the general formulae (1-A) to (1-D), the structure represented by the general formula (1-E) is preferable.
[ chemical 7]
(wherein R is 1 、R 2 、R 3 R is R a R in the general formula (1) 1 、R 2 、R 3 R is R a The same meaning, A 11 、A 12 A is a 13 And each may be the same or different and represents A as in formula (1) 1 The same meaning or a single bond, A 21 、A 22 A is a 23 And each may be the same or different and represents A as in formula (1) 2 The same meaning or single bond)
Of the general formulae (1), the compounds represented by the following general formulae (1-1) to (1-28) and general formulae (1-51) to (1-80) are particularly preferable.
[ chemical 8]
(wherein R is 1 、R 2 R is R 3 R in the general formula (1) 1 、R 2 R is R 3 The same meaning)
[ chemical 9]
(wherein R is 1 、R 2 R is R 3 R in the general formula (1) 1 、R 2 R is R 3 The same meaning)
[ chemical 10]
(wherein R is 1 、R 2 R is R 3 R in the general formula (1) 1 、R 2 R is R 3 The same meaning)
[ chemical 11]
(wherein R is 1 、R 2 R is R 3 R in the general formula (1) 1 、R 2 R is R 3 The same meaning)
[ chemical 12]
(wherein R is 1 、R 2 R is R 3 R in the general formula (1) 1 、R 2 R is R 3 The same meaning)
[ chemical 13]
(wherein R is 1 、R 2 R is R 3 R in the general formula (1) 1 、R 2 R is R 3 The same meaning)
[ chemical 14]
(wherein R is 1 、R 2 、R 3 R is R a R in the general formula (1) 1 、R 2 、R 3 R is R a The same meaning)
[ 15]
(wherein R is 1 、R 2 、R 3 R is R a R in the general formula (1) 1 、R 2 、R 3 R is R a The same meaning)
[ 16]
(wherein R is 1 、R 2 、R 3 R is R a R in the general formula (1) 1 、R 2 、R 3 R is R a The same meaning)
The compound represented by the general formula (1) preferably has a maximum absorption wavelength of 350nm to 750 nm. In particular, in the case where the compound represented by the general formula (1) is a red dye, it is preferable that the compound has a maximum absorption of 500nm to 600nm, in the case of a yellow dye, it is preferable that the compound has a maximum absorption of 400nm to 500nm, and in the case of a blue dye, it is preferable that the compound has a maximum absorption of 600nm to 750 nm. By using these compounds showing the maximum absorption wavelength in combination, a liquid crystal composition containing a pigment compound showing a desired color tone can be prepared, and particularly in the case where black is to be obtained, it is preferable to use pigments showing red, yellow, and blue, respectively, in combination. Further, a dichroic dye is also preferable in which the compound represented by the general formula (1) is used in combination with other structures.
The lower limit value of the total content of the compounds represented by the general formula (1) is preferably 0.1 mass% or more, preferably 0.2 mass% or more, preferably 0.3 mass% or more, preferably 0.4 mass% or more, preferably 0.5 mass% or more, preferably 0.7 mass% or more, preferably 1 mass% or more, relative to 100 mass% of the liquid crystal composition containing no pigment compound and additive.
The upper limit value of the compound represented by the general formula (1) is preferably 20 mass% or less, more preferably 15 mass% or less, more preferably 12 mass% or less, more preferably 10 mass% or less, more preferably 8 mass% or less, more preferably 5 mass% or less, relative to 100 mass% of the liquid crystal composition containing no pigment compound or additive.
The total content of the compounds represented by the general formula (1) is preferably 0.1 to 20% by mass, more preferably 0.2 to 15% by mass, still more preferably 0.3 to 15% by mass, still more preferably 0.5 to 12% by mass, still more preferably 0.8 to 10% by mass, still more preferably 1 to 8% by mass, still more preferably 1 to 6% by mass, based on 100% by mass of the liquid crystal composition excluding the coloring compounds and the additives.
< liquid Crystal composition >
The liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (II).
[ chemical 17]
(in the general formula (II), R II1 Represents an alkyl group having 1 to 10 carbon atoms, 1 of the alkyl groups being non-adjacent to or greater than 2-CH 2 Each independently is composed of-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution,
A II1 a is a II2 Each independently represents a radical selected from the group consisting of,
(a) 1, 4-Cyclohexylene (1-CH present in the radical) 2 -or not more than 2-CH 2 -can be substituted by-O-)
(b) 1, 4-phenylene (1-ch=or more than 2-ch=that are not adjacent to each other present in the group may be substituted with-n=)
(c) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-ch=or non-contiguous 2 or more-ch=present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted to-n=)
The groups (a), (b) and (c) may each be independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z II1 represents a single bond, -CH 2 CH 2 -、-(CH 2 ) 4 -、-OCH 2 -、-CH 2 O-、-COO-、-OCO-、-OCF 2 -、-CF 2 O-, -ch=n-n=ch-, -ch=ch-, -cf=cf-or-c≡c-,
Y II1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group or an alkyl group having 1 to 10 carbon atoms, 1 or 2 or more of which are not adjacent to each other -CH 2 Each independently is composed of-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution, in addition, 1 or more than 2 hydrogen atoms in the alkyl group may be substituted with fluorine atoms,
m II1 represents 1, 2, 3 or 4, at m II1 In the case of 2, 3 or 4, a plurality of A II1 A plurality of Z II1 Can be the same or different respectively)
The liquid crystal composition of the present invention can adjust the magnitude of dielectric anisotropy by combining one or two or more compounds represented by the general formula (II). The liquid crystal composition of the present invention may be a negative liquid crystal composition having a negative dielectric anisotropy (Δε) and an absolute value (|Δε|) of 2 or more, or a positive liquid crystal composition having a positive dielectric anisotropy (Δε) and an absolute value (|Δε|) of 1.5 or more. The specific value of dielectric anisotropy will be described below.
The compound represented by the general formula (II) may be a liquid crystal compound having negative dielectric anisotropy (Δε) according to dielectric anisotropy (first mode), a liquid crystal compound having positive dielectric anisotropy (Δε) (second mode), or a nonpolar (non-npolar) liquid crystal compound having dielectric anisotropy (Δε) in the vicinity of 0 (third mode). The dielectric anisotropy of the compound represented by the general formula (II) was set to a value at 25 ℃. Hereinafter, the compounds represented by the general formula (II) will be described in each mode.
[1] A first mode of the compound represented by the general formula (II)
The first mode of the compound represented by the general formula (II) (hereinafter, the compound of the first mode may be referred to as a compound of the first mode) is a liquid crystal compound having negative dielectric anisotropy (Δ∈). The compound of the first aspect preferably has a negative sign of Δε and an absolute value of Δε of greater than 2, and more preferably has an absolute value of Δε of greater than 3.
As the compound of the first embodiment, compounds selected from the group of compounds represented by the following general formulae (N-1) to (N-3) are exemplified.
[ chemical 18]
(wherein R is N11 、R N12 、R N21 、R N22 、R N31 R is R N32 Independently represent an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent to or greater than 2-CH 2 Each independently is composed of-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution,
A N11 、A N12 、A N21 、A N22 、A N31 a is a N32 Each independently represents a radical selected from the group consisting of,
(a) 1, 4-Cyclohexylene (1-CH present in the radical) 2 -or not more than 2-CH 2 Can be substituted by-O-)
(b) 1, 4-phenylene (1-ch=or more than 2-ch=that are not adjacent to each other present in the group may be substituted with-n=)
(c) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-ch=or non-contiguous 2 or more-ch=present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted to-n=)
The groups (a), (b) and (c) may each be independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z N11 、Z N12 、Z N21 、Z N22 、Z N31 z is as follows N32 Respectively and independently represent a single bond, -CH 2 CH 2 -、-(CH 2 ) 4 -、-OCH 2 -、-CH 2 O-、-COO-、-OCO-、-OCF 2 -、-CF 2 O-, -ch=n-n=ch-, -ch=ch-, -cf=cf-or-c≡c-,
X N21 represents a hydrogen atom or a fluorine atom,
T N31 represents-CH 2 -or an oxygen atom,
n N11 、n N12 、n N21 、n N22 、n N31 n is as follows N32 Each independently represents an integer of 0 to 3, n N11 +n N12 、n N21 +n N22 N is as follows N31 +n N32 Each independently is 1, 2 or 3,
at A N11 To A N32 、Z N11 To Z N32 Where there are plural, they may be the same or different; wherein the compound represented by the general formula (N-2) and the general formula (N-3) is other than the compound represented by the general formula (N-1), and the compound represented by the general formula (N-3) is other than the compound represented by the general formula (N-2)
In the case where the dielectric anisotropy (. DELTA.. Epsilon.) of the liquid crystal composition of the present invention at 25℃has a negative value, the liquid crystal composition of the present invention preferably contains one or more compounds selected from the group of compounds represented by the general formulae (N-1), (N-2) and (N-3).
In the general formula (N-1), the general formula (N-2) and the general formula (N-3), R N11 、R N12 、R N21 、R N22 、R N31 R is R N32 Each independently is preferably an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, still more preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, particularly preferably an alkenyl (propenyl) having 3 carbon atoms.
In addition, at R N11 、R N12 、R N21 、R N22 、R N31 R is R N32 In the case where the ring structures to which each is bonded are phenyl (aromatic), R N11 、R N12 、R N21 、R N22 、R N31 R is R N32 Each independently is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or an alkenyl group having 4 to 5 carbon atoms. On the other hand, at R N11 、R N12 、R N21 、R N22 、R N31 R is R N32 R in the case where the ring structures bonded to each are saturated ring structures such as cyclohexane, pyran and dioxane N11 、R N12 、R N21 、R N22 、R N31 R is R N32 Each independently is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a linear alkenyl group having 2 to 5 carbon atoms.
To stabilize the nematic phase, R N11 、R N12 、R N21 、R N22 、R N31 R is R N32 The total amount of carbon atoms and oxygen atoms is preferably 5 or less, and the carbon atoms and oxygen atoms are preferably linear.
The alkenyl group is preferably selected from groups represented by any one of the formulae (R1) to (R5). The black dots in the formulae (R1) to (R5) represent carbon atoms in the ring structure to which the alkenyl group is bonded.
[ chemical 19]
In case of requiring an increase in Δn, A N11 、A N12 、A N21 、A N22 、A N31 A is a N32 Each independently is preferably aromatic. On the other hand, in order to improve the response speed, A N11 、A N12 、A N21 、A N22 、A N31 A is a N32 Each independently is preferably aliphatic, preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [ 2.2.2.2 ]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decalin-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl.
Wherein A is N11 、A N12 、A N21 、A N22 、A N31 A is a N32 Each of the structures is preferably independently any one of the structures described below.
[ chemical 20]
Further, A N11 、A N12 、A N21 、A N22 、A N31 A is a N32 Each independently preferably represents trans-1, 4-cyclohexylene or 1, 4-phenylene.
Z N11 、Z N12 、Z N21 、Z N22 、Z N31 Z is as follows N32 Each independently preferably represents-CH 2 O-、-CF 2 O-、-CH 2 CH 2 -、-CF 2 CF 2 -or a single bond, and preferably-CH 2 O-、-CH 2 CH 2 -or a single bond, particularly preferably-CH 2 O-or a single bond.
X N21 Fluorine atoms are preferred.
T N31 Preferably an oxygen atom.
n N11 +n N12 、n N21 +n N22 N is as follows N31 +n N32 Preferably 1 or 2, preferably n N11 Is 1 and n N12 A combination of 0, n N11 Is 2 and n N12 A combination of 0, n N11 Is 1 and n N12 A combination of 1, n N11 Is 2 and n N12 A combination of 1, n N21 Is 1 and n N22 A combination of 0, n N21 Is 2 and n N22 A combination of 0, n N31 Is 1 and n N32 A combination of 0, n N31 Is 2 and n N32 A combination of 0.
The liquid crystal composition of the present invention preferably contains one or more kinds of Z selected from the group consisting of the general formula (N-1) N11 Z is as follows N12 At least one of (C) represents-CH 2 O-compounds, Z in the general formula (N-2) N21 Z is as follows N22 At least one of (C) represents-CH 2 O-compounds and Z in the general formula (N-3) N31 Z is as follows N32 At least one of (C) represents-CH 2 O-compounds, and a group of compounds. The reason is that these compounds have-CH within their molecular structure 2 The linking group represented by O-may be used in combination with the above-mentioned compound having-CH 2 O-represented by the formula (H)Effect of the light stabilizer.
The lower limit of the content of the compound represented by the formula (N-1) is preferably 0 mass%, 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content of the compound represented by the formula (N-1) is preferably 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The upper and lower limits of the content of the compound represented by the formula (N-2) and the upper and lower limits of the content of the compound represented by the formula (N-3) may be set to be the same as the upper and lower limits of the content of the compound represented by the formula (N-1), respectively.
When it is necessary to keep the viscosity of the liquid crystal composition of the present invention low and to provide a composition having a high response speed, it is preferable that the lower limit value and the upper limit value be low. Further, when it is necessary to maintain Tni of the liquid crystal composition of the present invention high and a composition having good temperature stability is required, it is preferable that the lower limit value and the upper limit value are low. In order to increase the dielectric anisotropy in order to keep the driving voltage low, the lower limit value and the upper limit value are preferably high.
Among them, the liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (N-1). As the compound represented by the general formula (N-1), there may be mentioned a group of compounds represented by the following general formulae (N-1 a) to (N-1 g). Due to having-CH therein 2 The linking group represented by O-is therefore preferably a compound represented by one or more of the general formula (N-1 d) or the general formula (N-1 f), more preferably a compound represented by one or more of the general formula (N-1 d).
[ chemical 21]
(wherein R is N11 R is R N12 R in the general formula (N-1) N11 R is R N12 Identical meaning, n Na11 Represents 0 or 1, n Nb11 Represents 1 or 2, n Nc11 Represents 0 or 1, n Nd11 Represents 1 or 2, n Ne11 Represents 1 or 2, n Nf12 Represents 1 or 2, n Ng11 Represents 1 or 2, A Ne11 Represents trans-1, 4-cyclohexylene or 1, 4-phenylene, A Ng11 Represents trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene or 1, 4-phenylene, at least one of which represents 1, 4-cyclohexenylene, Z Ne11 Represents a single bond or ethylene, at least one of which represents ethylene and a plurality of A are present in the molecule Ne11 、Z Ne11 And/or A Ng11 Can be the same or different
More specifically, the compound represented by the general formula (N-1) is preferably a compound selected from the group of compounds represented by the general formulae (N-1-1) to (N-1-21).
The compound represented by the general formula (N-1-1) is the following compound.
[ chemical 22]
(wherein R is N111 R is R N112 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N111 Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propyl group, a pentyl group or a vinyl group. R is R N112 Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group or a butoxy group.
The compounds represented by the general formula (N-1-1) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content to be high, in the case where solubility at low temperature is important, if the content is set to be high, the effect is high, and in the case where T is important NI If the content is set to be low, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the formula (N-1-1) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 50 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-1) is preferably a compound selected from the group of compounds represented by the formulas (N-1-1.1) to (N-1-1.22), preferably a compound represented by the formulas (N-1-1.1) to (N-1-1.4), preferably a compound represented by the formulas (N-1-1.1) and (N-1-1.3).
[ chemical 23]
The compounds represented by the formulae (N-1-1.1) to (N-1-1.22) can also be used alone or in combination. The lower limit value of the content of the compounds represented by the formulae (N-1-1.1) to (N-1-1.22) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 50 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-2) is the following compound.
[ chemical 24]
(wherein R is N121 R is R N122 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N121 Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, propyl group, butyl group or pentyl group. R is R N122 Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably a methyl group, a propyl group, a methoxy group, an ethoxy group or a propoxy group.
The compounds represented by the general formula (N-1-2) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content high, in the case where solubility at low temperature is important, the effect is high, and in the case where T is important, it is preferable to set the content low NI If the content is set to be high, the effect is high. Further, at In the case of improving the drop trace or afterimage characteristics, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the formula (N-1-2) is preferably 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass%, 37 mass%, 40 mass%, 42 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 50 mass%, 48 mass%, 45 mass%, 43 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-2) is preferably a compound selected from the group of compounds represented by the formulas (N-1-2.1) to (N-1-2.22), preferably a compound represented by the formulas (N-1-2.3) to (N-1-2.7), the formulas (N-1-2.10), the formulas (N-1-2.11), the formulas (N-1-2.13) and the formulas (N-1-2.20), and in the case of paying attention to improvement of Δε, a compound represented by the formulas (N-1-2.3) to (N-1-2.7) is preferable, and in the case of paying attention to T NI In the case of improvement of (C), the compounds represented by the formulas (N-1-2.10), (N-1-2.11) and (N-1-2.13) are preferable, and in the case of paying attention to improvement of the response speed, the compounds represented by the formulas (N-1-2.20) are preferable.
[ chemical 25]
The compounds represented by the formulae (N-1-2.1) to (N-1-2.22) can also be used alone or in combination. The lower limit of the content of these compounds is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 50 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-3) is the following compound.
[ chemical 26]
(wherein R is N131 R is R N132 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N131 Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, propyl group or butyl group. R is R N132 Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably a 1-propenyl group, an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-3) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content to be high, in the case where solubility at low temperature is important, if the content is set to be high, the effect is high, and in the case where T is important NI If the content is set to be high, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the general formula (N-1-3) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-3) is preferably a compound selected from the group of compounds represented by the formulas (N-1-3.1) to (N-1-3.21), preferably a compound selected from the group of compounds represented by the formulas (N-1-3.1) to (N-1-3.7) and (N-1-3.21), preferably a compound selected from the group of compounds represented by the formulas (N-1-3.1), (N-1-3.2), formula (N-1-3.3), formula (N-1-3.4) and (N-1-3.6).
[ chemical 27]
The compounds represented by the formulae (N-1-3.1) to (N-1-3.4), the formulae (N-1-3.6) and (N-1-3.21) can also be used alone, and can also be used in combination, preferably a combination of the formulae (N-1-3.1) and (N-1-3.2), a combination of two or three selected from the formulae (N-1-3.3), the formulae (N-1-3.4) and (N-1-3.6). The lower limit of the content of these compounds is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-4) is the following compound.
[ chemical 28]
(wherein R is N141 R is R N142 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N141 R is R N142 Each independently is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably a methyl group, a propyl group, an ethoxy group or a butoxy group.
The compounds represented by the general formula (N-1-4) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content to be high, in the case where solubility at low temperature is important, if the content is set to be high, the effect is high, and in the case where T is important NI If the content is set to be low, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the general formula (N-1-4) is preferably 3 mass%, 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 11 mass%, 10 mass%, 8 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-4) is preferably a compound selected from the group of compounds represented by the formulas (N-1-4.1) to (N-1-4.14), preferably a compound represented by the formulas (N-1-4.1) to (N-1-4.4), preferably a compound represented by the formulas (N-1-4.1), (N-1-4.2) and (N-1-4.4).
[ chemical 29]
The compounds represented by the formulae (N-1-4.1) to (N-1-4.14) can be used alone or in combination. The lower limit of the content of these compounds is preferably 3 mass%, 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 11 mass%, 10 mass%, 8 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-5) is the following compound.
[ chemical 30]
(wherein R is N151 R is R N152 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N151 R is R N152 Each independently is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
The compounds represented by the general formula (N-1-5) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
At the weight ofIn the case of improving Δε, it is preferable to set the content high, and in the case of focusing on solubility at low temperature, it is preferable to set the content low, so that the effect is high, and in the case of focusing on T NI If the content is set to be high, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the general formula (N-1-5) is preferably 5 mass%, 8 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-5) is preferably a compound selected from the group of compounds represented by the formulas (N-1-5.1) to (N-1-5.6), and preferably a compound represented by the formulas (N-1-5.1), (N-1-5.2) and (N-1-5.4).
[ 31]
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The compounds represented by the formula (N-1-5.1), the formula (N-1-5.2) and the formula (N-1-5.4) can be used alone or in combination. The lower limit of the content of these compounds is preferably 5 mass%, 8 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-10) is the following compound.
[ chemical 32]
(wherein R is N1101 R is R N1102 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N1101 Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, propyl group, butyl group, vinyl group or 1-propenyl group.
R N1102 The alkyl group having 1 to 5 carbon atoms, the alkenyl group having 4 to 5 carbon atoms, or the alkoxy group having 1 to 4 carbon atoms is preferable, and the alkoxy group having 1 to 4 carbon atoms is preferable. At R N1102 In the case of an alkoxy group, the 2, 3-difluoro-1, 4-phenylene groups in the general formula (N-1-10) each adopt a linking group (-CH) 2 Oxygen atom of O-) and R N1102 The structure of the oxygen atom bond of the alkoxy group. The compound having such a structure may exhibit negative dielectric anisotropy (Δε) and a large absolute value of dielectric anisotropy. Thus, in particular, a liquid crystal composition having negative dielectric anisotropy can increase Δε by comprising the compound. In the alkoxy group having 1 to 4 carbon atoms, R N1102 More preferably ethoxy, propoxy or butoxy.
The compounds represented by the general formula (N-1-10) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content to be high, in the case where solubility at low temperature is important, if the content is set to be high, the effect is high, and in the case where T is important NI If the content is set to be low, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the general formula (N-1-10) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-10) is preferably a compound selected from the group of compounds represented by the formulas (N-1-10.1) to (N-1-10.14), preferably a compound represented by the formulas (N-1-10.1) to (N-1-10.5), preferably a compound represented by the formulas (N-1-10.1) and (N-1-10.2).
[ 33]
The compounds represented by the formula (N-1-10.1) and the formula (N-1-10.2) can be used alone or in combination. The lower limit of the content of these compounds is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-11) is the following compound.
[ chemical 34]
(wherein R is N1111 R is R N1112 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N1111 Preferably isAlkyl having 1 to 5 carbon atoms or alkenyl having 2 to 5 carbon atoms is preferably ethyl, propyl, butyl, vinyl or 1-propenyl.
R N1112 The alkyl group having 1 to 5 carbon atoms, the alkenyl group having 4 to 5 carbon atoms, or the alkoxy group having 1 to 4 carbon atoms is preferable, and the alkoxy group having 1 to 4 carbon atoms is preferable. For the reason thereof, R in the general formula (N-1-10) N1102 The same reason for representing alkoxy groups is preferable. In the alkoxy group having 1 to 4 carbon atoms, R N1112 More preferably ethoxy, propoxy or butoxy.
The compounds represented by the general formula (N-1-11) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content high, in the case where solubility at low temperature is important, the effect is high, and in the case where T is important, it is preferable to set the content low NI If the content is set to be high, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the general formula (N-1-11) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-11) is preferably a compound selected from the group of compounds represented by the formulas (N-1-11.1) to (N-1-11.14), preferably a compound represented by the formulas (N-1-11.2) and (N-1-11.4).
[ 35]
The compounds represented by the formula (N-1-11.2) and the formula (N-1-11.4) can be used alone or in combination. The lower limit of the content of these compounds is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-12) is the following compound.
[ 36]
(wherein R is N1121 R is R N1122 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N1121 Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, propyl group or butyl group. R is R N1122 Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-12) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content to be high, in the case where solubility at low temperature is important, if the content is set to be high, the effect is high, and in the case where T is important NI If the content is set to be low, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the general formula (N-1-12) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-13) is the following compound.
[ 37]
(wherein R is N1131 R is R N1132 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N1131 Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, propyl group or butyl group. R is R N1132 Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
Attach importance toIn the case of improvement of Δε, it is preferable to set the content high, and in the case of focusing on solubility at low temperature, if the content is set high, the effect is high, and in the case of focusing on T NI If the content is set to be high, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the general formula (N-1-13) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-14) is the following compound.
[ 38]
(wherein R is N1141 R is R N1142 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N1141 Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, propyl group or butyl group. R is R N1142 Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-14) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content to be high, in the case where solubility at low temperature is important, if the content is set to be high, the effect is high, and in the case where T is important NI If the content is set to be low, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the general formula (N-1-14) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-15) is the following compound.
[ 39]
(wherein R is N1151 R is R N1152 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N1151 Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, propyl group or butyl group. R is R N1152 Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-15) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content to be high, in the case where solubility at low temperature is important, if the content is set to be high, the effect is high, and in the case where T is important NI If the content is set to be high, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the formula (N-1-15) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-16) is the following compound.
[ 40]
(wherein R is N1161 R is R N1162 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N1161 Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, propyl group or butyl group. R is R N1162 Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-16) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content to be high, in the case where solubility at low temperature is important, if the content is set to be high, the effect is high, and in the case where T is important NI If the content is set to be high, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the formula (N-1-16) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-17) is the following compound.
[ chemical 41]
(wherein R is N1171 R is R N1172 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N1171 Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, propyl group or butyl group. R is R N1172 Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-17) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content to be high, in the case where solubility at low temperature is important, if the content is set to be high, the effect is high, and in the case where T is important NI If the content is set to be high, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the formula (N-1-17) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-18) is the following compound.
[ chemical 42]
(wherein R is N1181 R is R N1182 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N1181 Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a methyl group, an ethyl group, a propyl group or a butyl group. R is R N1182 Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-18) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content to be high, in the case where solubility at low temperature is important, if the content is set to be high, the effect is high, and in the case where T is important NI If the content is set to be high, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the formula (N-1-18) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-18) is preferably a compound selected from the group of compounds represented by the formulas (N-1-18.1) to (N-1-18.5), preferably a compound represented by the formulas (N-1-18.1) to (N-1-18.3), preferably a compound represented by the formulas (N-1-18.2) and (N-1-18.3).
[ chemical 43]
/>
The compound represented by the general formula (N-1-20) is the following compound.
[ 44]
(wherein R is N1201 R is R N1202 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N1201 R is R N1202 Each independently is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
The compounds represented by the general formula (N-1-20) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content to be high, in the case where solubility at low temperature is important, if the content is set to be high, the effect is high, and in the case where T is important NI If the content is set to be high, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the formula (N-1-20) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-21) is the following compound.
[ 45]
(wherein R is N1211 R is R N1212 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N1211 R is R N1212 Are each independently preferably an alkyl group having 1 to 5 carbon atoms or a carbon atomAlkenyl of 2 to 5 is preferably ethyl, propyl or butyl.
The compounds represented by the general formula (N-1-21) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content to be high, in the case where solubility at low temperature is important, if the content is set to be high, the effect is high, and in the case where T is important NI If the content is set to be high, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the formula (N-1-21) is preferably 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-22) is the following compound.
[ chemical 46]
(wherein R is N1221 R is R N1222 R in the general formula (N-1) is represented independently of each other N11 R is R N12 The same meaning)
R N1221 R is R N1222 Each independently is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group.
The compounds represented by the general formula (N-1-22) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the case where improvement of Δε is important, it is preferable to set the content to be high, in the case where solubility at low temperature is important, if the content is set to be high, the effect is high, and in the case where T is important NI If the content is set to be high, the effect is high. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the formula (N-1-22) is preferably 1 mass%, 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 5 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (N-1-22) is preferably a compound selected from the group of compounds represented by the formulas (N-1-22.1) to (N-1-22.12), preferably a compound represented by the formulas (N-1-22.1) to (N-1-22.5), preferably a compound represented by the formulas (N-1-22.1) to (N-1-22.4).
[ 47]
[2] A second mode of the compound represented by the general formula (II)
The second mode of the compound represented by the general formula (II) (hereinafter, the compound of the second mode may be referred to as a compound of the second mode) is a liquid crystal compound having positive dielectric anisotropy (Δ∈). The compound of the second mode preferably has a Δ∈ of greater than 2.
As the compound of the second embodiment, a compound selected from the group of compounds represented by the following general formula (M) and general formula (K) is exemplified.
[ 48]
(wherein R is M1 R is R K1 Independently represent an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent to or greater than 2-CH 2 Each independently is composed of-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution,
n M1 n is as follows K1 Each independently represents 0, 1, 2, 3 or 4,
A M1 a is a M2 A is a K1 A is a K2 Each independently represents a radical selected from the group consisting of,
(a) 1, 4-Cyclohexylene (1-CH present in the radical) 2 -or not more than 2-CH 2 -can be substituted by-O-or-S-)
(b) 1, 4-phenylene (1-ch=or more than 2 non-adjacent-ch=present in the radical may be substituted to-n=)
The hydrogen atoms on the radicals (a) and (b) may each independently be substituted by cyano groups, fluorine atoms or chlorine atoms,
Z M1 Z is as follows M2 Z is as follows K1 Z is as follows K2 Respectively and independently represent a single bond, -CH 2 CH 2 -、-(CH 2 ) 4 -、-OCH 2 -、-CH 2 O-、-OCF 2 -、-CF 2 O-, -COO-, -OCO-or-C.ident.C-,
in the general formula (M), at n M1 Is 2, 3 or 4 and A M2 Z is as follows M1 In the case where there are plural, plural A M2 Z is as follows M1 Which may be the same or different from each other,
in the general formula (K), at n K1 Is 2, 3 or 4 and A K2 Z is as follows K1 In the case where there are plural, plural A K2 Z is as follows K1 Which may be the same or different from each other,
X M1 x is X M3 X is as follows K1 X is X K3 Each independently represents a hydrogen atom, a chlorine atom or a fluorine atom,
X M2 x is X K2 Independently of one another, represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a 2, 2-trifluoroethyl group
In the case where the dielectric anisotropy (. DELTA.. Epsilon.) of the liquid crystal composition of the present invention at 25℃has a positive value, the liquid crystal composition of the present invention preferably contains one or more compounds selected from the group of compounds represented by the general formulae (M) and (K).
The liquid crystal composition of the present invention preferably contains one or more kinds of Z selected from the group consisting of the general formula (M) M1 Z is as follows M2 At least one of (C) represents-CH 2 O-compound, Z in the general formula (K) K1 Z is as follows K2 At least one of (C) represents-CH 2 O-compounds, and a group of compounds. The reason is that these compounds have-CH within their molecular structure 2 The linking group represented by O-may be used in combination with the above-mentioned compound having-CH 2 The effect of the compound having a linking group represented by O-and the photostabilizer represented by the general formula (H).
In the liquid crystal composition of the present invention, the total content of the compounds selected from the group of compounds represented by the general formula (M) and the general formula (K) can be suitably adjusted according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, drop trace, afterimage, dielectric anisotropy, and the like.
The lower limit of the total content of the compounds selected from the group of compounds represented by the general formula (M) and the general formula (K) is preferably 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass% with respect to the total amount of the liquid crystal composition of the present invention, and on the other hand, the upper limit of the total content is preferably 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass% with respect to the total amount of the liquid crystal composition of the present invention.
When it is necessary to keep the viscosity of the liquid crystal composition of the present invention low and to provide a composition having a high response speed, the total content of the compounds selected from the group of compounds represented by the general formulae (M) and (K) is preferably low in the lower limit and low in the upper limit. When it is necessary to maintain Tni of the liquid crystal composition of the present invention high and a composition having good temperature stability is required, the total content of the compounds selected from the group of compounds represented by the general formula (M) and the general formula (K) is preferably set to be low in the lower limit value and low in the upper limit value. In order to increase the dielectric anisotropy in order to keep the driving voltage low, the total content of the compounds selected from the group of compounds represented by the general formulae (M) and (K) is preferably set to be high at the lower limit and high at the upper limit.
The compounds represented by the general formulae (M) and (K) will be described below.
< Compound represented by the general formula (M) >)
In the general formula (M), R M1 Preferably an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, still more preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, particularly preferably an alkenyl group (propenyl group) having 3 carbon atoms.
In addition, regarding R M1 In the case where reliability is important, alkyl is preferable, and in the case where viscosity reduction is important, alkenyl is preferable.
In addition, at R M1 Bonded A M1 In the case where the ring structure of (a) is phenyl (aromatic), R M1 Preferably a linear alkyl group having 1 to 5 carbon atoms, a linear chainAn alkoxy group having 1 to 4 carbon atoms and an alkenyl group having 4 to 5 carbon atoms. On the other hand, at R M1 Bonded A M1 In the case where the ring structure is a saturated ring structure such as cyclohexane, pyran or dioxane, R M1 Preferred are a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms.
To stabilize the nematic phase, R M1 The total amount of carbon atoms and oxygen atoms is preferably 5 or less, and is preferably linear.
The alkenyl group is preferably selected from the group represented by any one of the formulae (R1) to (R5) described in the first mode "one of the compounds represented by the general formula (II) described in the above" [1 ].
In case of requiring an increase in Δn, A M1 A is a M2 Each independently is preferably aromatic. In addition, in order to improve the response speed, A M1 A is a M2 Each independently is preferably aliphatic, preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [ 2.2.2.2]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decalin-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl.
Wherein A is M1 A is a M2 More preferably, each of the structures independently represents any of the following structures.
[ 49]
Further, A M1 A is a M2 Each of the structures is preferably independently any one of the structures described below.
[ 50]
Z M1 Z is as follows M2 Are respectively independent of The site is preferably represented by-CH 2 O-、-CF 2 O-、-CH 2 CH 2 -、-CF 2 CF 2 -or a single bond, and preferably-CF 2 O-、-CH 2 CH 2 -or a single bond, particularly preferably-CF 2 O-or a single bond.
n M1 Preferably 0, 1, 2 or 3, preferably 0, 1 or 2. With emphasis on improvement of Δε, n M1 Preferably 0 or 1, and n is n when Tni is emphasized M1 Preferably 1 or 2.
The types of the combinable compounds are not particularly limited, and may be used in combination according to desired properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, one, two, and three as one embodiment of the present invention. In another embodiment of the present invention, the number of the elements is four, five, six, seven or more.
In the liquid crystal composition of the present invention, the content of the compound represented by the general formula (M) needs to be appropriately adjusted in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, drop trace, afterimage, dielectric anisotropy, and the like.
The lower limit of the content of the compound represented by the general formula (M) is preferably 0 mass%, 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content of the compound represented by the general formula (M) is preferably 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass% with respect to the total amount of the liquid crystal composition of the present invention.
In the case where a composition having a low viscosity and a high response speed is required for the liquid crystal composition of the present invention, the content of the compound represented by the general formula (M) is preferably set to a low lower limit value and an upper limit value. When it is necessary to maintain Tni of the liquid crystal composition of the present invention high and a composition having good temperature stability is required, the content of the compound represented by the general formula (M) is preferably set to be low in the lower limit value and low in the upper limit value. In order to increase the dielectric anisotropy in order to keep the driving voltage low, the content of the compound represented by the general formula (M) is preferably set to be high at a lower limit value and high at an upper limit value.
The liquid crystal compound represented by the general formula (M) is preferably selected from the group of compounds represented by the following general formulae (M-1) and (M-2).
[ 51]
(wherein R is 31 Represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms,
X 31 x is X 32 Each independently represents a hydrogen atom or a fluorine atom,
Y 31 represents a fluorine atom or OCF 3 ，
M 31 To M 33 Each independently represents trans-1, 4-cyclohexylene or 1, 4-phenylene, one or both of the trans-1, 4-cyclohexylene groups being-CH 2 -O-substituted in such a way that the oxygen atoms are not directly adjacent, one or two hydrogen atoms in the phenylene group being substituted by fluorine atoms,
n 31 N is as follows 32 Each independently represents 0, 1 or 2,
n 31 +n 32 representing 1, 2 or 3)
Among them, the liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (M-2). The reason is that the compound represented by the general formula (M-2) has a structure in its molecular structure, namely via-CH 2 The structure in which two adjacent ring structures are linked by a linking group represented by O-can be exhibited by the combination of the above-mentioned groups having-CH 2 The effect of the compound having a linking group represented by O-and the photostabilizer represented by the general formula (H).
Specifically, the liquid crystal compounds represented by the general formula (M-1) are preferably compounds represented by the following general formulae (M-1-a) to (M-1-f).
[ 52]
(wherein R is 31 、X 31 、X 32 Y and Y 31 R in the general formula (M) 31 、X 31 、X 32 Y and Y 31 Identical meaning, X 34 To X 39 Independently represent a hydrogen atom or a fluorine atom)
Specifically, the liquid crystal compounds represented by the general formula (M-2) are preferably compounds represented by the following general formulae (M-2-a) to (M-2-n).
[ 53]
[ 54]
(wherein R is 31 、X 31 、X 32 Y and Y 31 R in the general formula (M) 31 、X 31 、X 32 Y and Y 31 Identical meaning, X 34 To X 39 Independently represent a hydrogen atom or a fluorine atom)
Specifically, the liquid crystal compound represented by the general formula (M) is preferably a compound represented by the following general formulae (M-3) to (M-26).
[ 55]
[ 56]
(wherein R is 31 、X 31 、X 32 Y and Y 31 R in the general formula (M) 31 、X 31 、X 32 Y and Y 31 Identical meaning, X 34 To X 39 Independently represent a hydrogen atom or a fluorine atom)
< 2 > Compounds represented by the general formula (K)
In the general formula (K), R K1 Preferably an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, still more preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, particularly preferably an alkenyl group (propenyl group) having 3 carbon atoms.
With respect to R K1 In the case where reliability is important, alkyl is preferable, and in the case where viscosity reduction is important, alkenyl is preferable.
At R K1 Bonded A K1 In the case where the ring structure of (a) is phenyl (aromatic), R K1 Preferred are a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and an alkenyl group having 4 to 5 carbon atoms. On the other hand, at R K1 Bonded A K1 In the case where the ring structure is a saturated ring structure such as cyclohexane, pyran or dioxane, R K1 Preferred are a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms.
To stabilize the nematic phase, R K1 Preferably, the total amount of carbon atoms and oxygen atoms is 5 or less, in which case R K1 Preferably straight.
At R K1 In the case of an alkenyl group, the alkenyl group is preferablyIs selected from the group consisting of the "[1 ]]The first mode of the compound represented by the general formula (II)' in the group represented by any one of the formulae (R1) to (R5) described in one item.
In case of requiring an increase in Δn, A K1 A is a K2 Each independently is preferably aromatic. In addition, in order to improve the response speed, A K1 A is a K2 Each independently is preferably aliphatic, preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [ 2.2.2.2]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decalin-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl.
Wherein A is K1 A is a K2 Each of the structures is preferably independently any one of the structures described below.
[ 57]
Further, A K1 A is a K2 Each of the structures is preferably independently any one of the structures described below.
[ 58]
Z K1 Z is as follows K2 Each independently preferably represents-CH 2 O-、-CF 2 O-、-CH 2 CH 2 -、-CF 2 CF 2 -or a single bond, and preferably-CF 2 O-、-CH 2 CH 2 -or a single bond, particularly preferably-CF 2 O-or a single bond.
n K1 Preferably 0, 1, 2 or 3, preferably 0, 1 or 2. With emphasis on improvement of Δε, n K1 Preferably 0 or 1, and n is n when Tni is emphasized K1 Preferably 1 or 2.
The types of the combinable compounds are not particularly limited, and may be used in combination according to desired properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, one, two, three, four, five, six, seven or more.
In the liquid crystal composition of the present invention, the content of the compound represented by the general formula (K) needs to be appropriately adjusted in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, drop trace, afterimage, dielectric anisotropy, and the like.
The lower limit of the content of the compound represented by the general formula (K) is preferably 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit value of the content of the compound represented by the general formula (K) is preferably 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass% with respect to the total amount of the liquid crystal composition of the present invention.
In the case where a composition having a low viscosity and a high response speed is required for the liquid crystal composition of the present invention, the content of the compound represented by the general formula (K) is preferably set to a low lower limit value and an upper limit value. When it is necessary to maintain Tni of the liquid crystal composition of the present invention high and a composition having good temperature stability is required, the content of the compound represented by the general formula (K) is preferably set to be low in the lower limit value and low in the upper limit value. In order to increase the dielectric anisotropy in order to keep the driving voltage low, the content of the compound represented by the general formula (K) is preferably set to be high at a lower limit value and high at an upper limit value.
The liquid crystal compound represented by the general formula (K) is preferably selected from the group of compounds represented by the following general formulae (K-1) and (K-2).
[ 59]
(wherein R is 41 Represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms,
X 41 x is X 42 Each independently represents a hydrogen atom or a fluorine atom,
Y 41 represents a fluorine atom or OCF 3 ，
M 41 To M 43 Each independently represents trans-1, 4-cyclohexylene or 1, 4-phenylene, one or both of the trans-1, 4-cyclohexylene groups being-CH 2 -O-substituted in such a way that the oxygen atoms are not directly adjacent, one or two hydrogen atoms in the phenylene group being substituted by fluorine atoms,
n 41 N is as follows 42 Each independently represents 0, 1 or 2, n 41 +n 42 Representing 1, 2 or 3)
Among them, the liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (K-2). The reason is that the compound represented by the general formula (K-2) has a structure in its molecular structure, namely via-CH 2 The structure in which two adjacent ring structures are linked by a linking group represented by O-can be exhibited by the combination of the above-mentioned groups having-CH 2 The effect of the compound having a linking group represented by O-and the photostabilizer represented by the general formula (H).
Specifically, the liquid crystal compounds represented by the general formula (K-1) are preferably compounds represented by the following general formulae (K-1-a) to (K-1-d).
[ chemical 60]
(wherein R is 41 、X 41 、X 42 Y and Y 41 R in the general formula (K) 41 、X 41 、X 42 Y and Y 41 Identical meaning, X 44 ～X 49 Independently represent a hydrogen atom or a fluorine atom)
Specifically, the liquid crystal compounds represented by the general formula (K-2) are preferably compounds represented by the following general formulae (K-2-a) to (K-2-g).
[ chemical 61]
(wherein R is 41 、X 41 、X 42 Y and Y 41 R in the general formula (K) 41 、X 41 、X 42 Y and Y 41 Identical meaning, X 44 ～X 49 Independently represent a hydrogen atom or a fluorine atom)
Specifically, the liquid crystal compound represented by the general formula (K) is preferably a compound represented by the following general formulae (K-3) to (K-5).
[ 62]
(wherein R is 41 、X 41 、X 42 Y and Y 41 R in the general formula (K) 41 、X 41 、X 42 Y and Y 41 Identical meaning, X 44 ～X 49 Independently represent a hydrogen atom or a fluorine atom)
[3] Third mode of the Compound represented by the general formula (II)
The third mode of the compound represented by the general formula (II) (hereinafter, referred to as a third mode) is a compound having a dielectric anisotropy of about 0, a so-called nonpolar liquid crystal compound. The compound of the third embodiment preferably has a dielectric anisotropy (. DELTA.. Epsilon.) at 25℃of not less than-2 and not more than 2.
The compound of the third embodiment may be a compound represented by the following general formula (L). That is, the liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (L).
[ 63]
(wherein R is L1 R is R L2 Independently represent an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent to or greater than 2-CH 2 Each independently is composed of-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution,
n L1 represents 0, 1, 2 or 3,
A L1 、A L2 a is a L3 Each independently represents a radical selected from the group consisting of,
(a) 1, 4-Cyclohexylene (1-CH present in the radical) 2 -or not more than 2-CH 2 Can be substituted by-O-)
(b) 1, 4-phenylene (1-ch=or more than 2 non-adjacent-ch=present in the radical may be substituted to-n=)
(c) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-ch=or non-contiguous 2 or more-ch=present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted to-n=)
The groups (a), (b) and (c) may each be independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z L1 z is as follows L2 Respectively and independently represent a single bond, -CH 2 CH 2 -、-(CH 2 ) 4 -、-OCH 2 -、-CH 2 O-、-COO-、-OCO-、-OCF 2 -、-CF 2 O-, -ch=n-n=ch-, -ch=ch-, -cf=cf-or-c≡c-,
at n L1 Is 2 or 3 and A L2 Where there are plural, they may be the same or different, and where n L1 Is 2 or 3 and Z L2 Where there are plural, they may be the same or different;
wherein the compounds represented by the general formula (M) and the general formula (K) and the compounds represented by the general formula (N-1), the general formula (N-2) and the general formula (N-3) are excluded
The compound represented by the general formula (L) corresponds to a compound having substantially neutral dielectric properties (the value of Δε at 25 ℃ C. Is-2 or more and 2 or less). Accordingly, the compound represented by the general formula (L) preferably has 2 or less, preferably 1 or less, preferably no polar groups such as halogens in the molecule.
The compounds represented by the general formula (L) may be used alone, but may also be used in combination. The types of the combinable compounds are not particularly limited, and may be suitably used in combination in accordance with desired properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of the compounds used are, for example, one, two, three, four, five, six, seven, eight, nine, ten or more.
The content of the compound represented by the general formula (L) needs to be appropriately adjusted in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, drop trace, residual image, dielectric anisotropy, and the like. The lower limit of the content of the compound represented by the general formula (L) is preferably 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content of the compound represented by the general formula (L) is preferably 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass% with respect to the total amount of the liquid crystal composition of the present invention.
In the case where a liquid crystal composition having a low viscosity and a high response speed is required, the content of the compound represented by the general formula (L) is preferably high at a lower limit value and high at an upper limit value. In the case where a liquid crystal composition having high Tni and good temperature stability is required, the content of the compound represented by the general formula (L) is preferably high at the lower limit and high at the upper limit. In order to increase the dielectric anisotropy in order to keep the driving voltage low, the content of the compound represented by the general formula (L) is preferably low in the lower limit value and low in the upper limit value.
With respect to R L1 R is R L2 In the case where reliability is important, alkyl groups are preferable, in the case where volatility of the compound is important to be reduced, alkoxy groups are preferable, and in the case where viscosity is important to be reduced, at least one of them is preferably alkenyl groups.
R L1 R is R L2 At A to which they are bonded L1 A is a L3 When the ring structure of (a) is phenyl (aromatic), each independently is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or an alkenyl group having 4 to 5 carbon atoms. In addition, R L1 R is R L2 At A to which they are bonded L1 A is a L3 When the ring structure is a saturated ring structure such as cyclohexane, pyran or dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a linear alkenyl group having 2 to 5 carbon atoms. In addition, R is for stabilizing the nematic phase L1 R is R L2 The total amount of carbon atoms and oxygen atoms is preferably 5 or less, and in this case, the carbon atoms and oxygen atoms are preferably linear.
The alkenyl group is preferably selected from the group represented by any one of the formulae (R1) to (R5) described in the first mode "one of the compounds represented by the general formula (II) described in the above" [1 ].
Regarding n L1 When the response speed is important, it is preferably 0, and in order to improve the upper limit temperature of the nematic phase, it is preferably 2 or 3, and in order to achieve the balance, it is preferably 1. In order to satisfy the characteristics required as a liquid crystal composition, n is preferably selected from the group consisting of L1 The compounds represented by the general formula (L) are combined to have different values.
With respect to A L1 、A L2 A is a L3 In the case where an increase in Δn is required, aromatic is preferable, aliphatic is preferable for improving the response speed, and each independently represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [ 2.2.2.2 ]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decalin-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl.
Wherein A is L1 、A L2 A is a L3 More preferably, each independently represents the following structure, and still more preferably represents trans-1, 4-cyclohexylene or 1, 4-phenylene.
[ 64]
In the case of paying attention to the response speed, Z L1 Z is as follows L2 Preferably a single bond.
Among the compounds represented by the general formula (L), 0, 1,2 or 3, preferably 0 or 1 halogen atoms are preferably present in the molecule, and 1 is preferable in consideration of compatibility with other liquid crystal molecules.
The liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (L-1A) as the compound represented by the general formula (L).
[ 65]
(in the general formula (L-1A), R i1A R is R i2A Independently represent an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent to or greater than 2-CH 2 Each independently is composed of-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution, but R is i1A R is R i2A In at least one of the alkyl groups, 1 or non-contiguous 2 or more-CH 2 Each independently substituted with-ch=ch-)
In the compound represented by the general formula (L-1A), R i1A R is R i2A At least one of (2) represents 1 or non-contiguous more than 2-CH in the alkyl group 2 -each independently substituted with-ch=ch-. Namely, R in the compound represented by the general formula (L-1A) i1A R is R i2A At least one of (2) and (8) represents an alkenyl group having 2 to 8 carbon atoms.
Wherein R is i1A R is R i2A Is preferably represented by any one of the formulae (R1) to (R5). In addition, regarding R i1A R is R i2A Can be alkenyl, or R i1A R is R i2A Both are alkenyl groups. At R i1A R is R i2A In the case of alkenyl groups, R i1A R is R i2A May be the same or different.
Wherein R is i1A R is R i2A Preferably, at least one of them is an alkenyl group having 2 to 5 carbon atoms.
The liquid crystal composition of the present invention preferably contains at least one compound represented by the general formula (L-1A). Two or more kinds may be contained in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more.
The lower limit of the content of the compound represented by the general formula (L-1A) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 15 mass%, 20 mass%, 25 mass%, 30 mass%, 35 mass%, 40 mass%, 45 mass%, 50 mass%, 55 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-1A) is preferably a compound selected from the group of compounds represented by the general formula (L-1A-1).
[ chemical 66]
/>
(wherein R is L12A Represents the same meaning as in the general formula (L-1A)
The compound represented by the general formula (L-1A-1) is preferably a compound selected from the group of compounds represented by the formulas (L-1A-1.1) to (L-1A-1.3), preferably a compound represented by the formula (L-1A-1.2) or (L-1A-1.3), and particularly preferably a compound represented by the formula (L-1A-1.3).
[ 67]
The lower limit value of the preferable content of the compound represented by the formula (L-1A-1) is 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass% with respect to the total amount of the liquid crystal composition of the present invention. The compound represented by the formula (L-1A-3) is preferably contained within the ranges of the lower limit and the upper limit.
The compound represented by the general formula (L-1A) is preferably a compound selected from the group of compounds represented by the general formula (L-1A-2).
[ chemical 68]
(wherein R is L12A Represents the same meaning as in the general formula (L-1A)
The lower limit of the content of the compound represented by the formula (L-1A-2) is preferably 1 mass%, 5 mass%, 10 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 35 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 60 mass%, 55 mass%, 50 mass%, 45 mass%, 42 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-1A-2) is preferably a compound selected from the group of compounds represented by the formulas (L-1A-2.1) to (L-1A-2.4), and preferably a compound represented by the formulas (L-1A-2.2) to (L-1A-2.4). In particular, the compound represented by the formula (L-1A-2.2) is preferable because the response speed of the liquid crystal composition of the present invention is particularly improved. In the case where Tni is more required than the response speed, the compound represented by the formula (L-1A-2.3) or the formula (L-1A-2.4) is preferably used. In order to improve the solubility at low temperatures, the content of the compounds represented by the formulas (L-1A-2.3) and (L-1A-2.4) is not preferred to be 30% by mass or more.
[ 69]
When the liquid crystal composition of the present invention contains the compound represented by the formula (L-1A-2.2), the lower limit value of the content of the compound represented by the formula (L-1A-2.2) is preferably 10 mass%, 15 mass%, 18 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass%, 38 mass%, 40 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 60 mass%, 55 mass%, 50 mass%, 45 mass%, 43 mass%, 40 mass%, 38 mass%, 35 mass%, 32 mass%, 30 mass%, 27 mass%, 25 mass%, 22 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The liquid crystal composition of the present invention preferably contains both the compound represented by the formula (L-1A-1.3) and the compound represented by the formula (L-1A-2.2). The lower limit of the content of the compound represented by the formula (L-1A-1.3) and the compound represented by the formula (L-1A-2.2) is preferably 10 mass%, 15 mass%, 20 mass%, 25 mass%, 27 mass%, 30 mass%, 35 mass%, 40 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 60 mass%, 55 mass%, 50 mass%, 45 mass%, 43 mass%, 40 mass%, 38 mass%, 35 mass%, 32 mass%, 30 mass%, 27 mass%, 25 mass%, 22 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-1A) is preferably a compound selected from the group of compounds represented by the general formula (L-1A-4) and the general formula (L-1A-5).
[ 70]
(wherein R is L12A Represents the same meaning as in the general formula (L-1A)
In the general formula (L-1A-4) and the general formula (L-1A-5), R L12A The alkyl group having 1 to 8 carbon atoms, the alkoxy group having 1 to 8 carbon atoms, or the alkenyl group having 2 to 8 carbon atoms is preferable, and the alkyl group having 1 to 5 carbon atoms, the alkoxy group having 1 to 4 carbon atoms, and the alkenyl group having 2 to 5 carbon atoms are preferable.
The lower limit of the content of the compound represented by the formula (L-1A-4) is preferably 1 mass%, 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 25 mass%, 23 mass%, 20 mass%, 17 mass%, 15 mass%, 13 mass%, 10 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The lower limit of the content of the compound represented by the formula (L-1A-5) is preferably 1 mass%, 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 25 mass%, 23 mass%, 20 mass%, 17 mass%, 15 mass%, 13 mass%, 10 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-1A-4) and the general formula (L-1A-5) is preferably a compound selected from the group of compounds represented by the general formulae (L-1A-4.1) to (L-1A-5.3), and preferably a compound represented by the general formulae (L-1A-4.2) or (L-1A-5.2).
[ chemical 71]
When the liquid crystal composition of the present invention contains the compound represented by the formula (L-1A-4.2), the lower limit value of the content of the compound represented by the formula (L-1A-4.2) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 18 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 17 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-1A) is preferably a compound selected from the group of compounds represented by the general formula (L-1A-6).
[ chemical 72]
(wherein R is L17 R is R L18 Each independently represents a methyl group or a hydrogen atom)
The lower limit of the content of the compound represented by the formula (L-1A-6) is preferably 1 mass%, 5 mass%, 10 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 35 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 60 mass%, 55 mass%, 50 mass%, 45 mass%, 42 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-1A-6) is preferably a compound selected from the group of compounds represented by the formulas (L-1A-6.1) to (L-1A-6.3).
[ 73]
The liquid crystal composition of the present invention preferably contains, as the compound represented by the general formula (L), one or more compounds selected from the group consisting of the compounds represented by the general formulae (L-1B) and (L-2) to (L-7), in addition to the compound represented by the general formula (L-1A).
The compound represented by the general formula (L-1B) is the following compound.
[ chemical 74]
(wherein R is L11B R is R L12B Independently represent an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent to or greater than 2-CH 2 Each independently of the others is composed of-C.ident.C-, -O-, -CO-, -COO-or-OCO-substitution)
R is as follows L11B R is R L12B In the sense that one or both of them do not represent an alkenyl group, the compound represented by the general formula (L-1B) is different from the compound represented by the general formula (L-1A).
R L11B R is R L12B Preferably a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms.
The liquid crystal composition of the present invention may contain one compound represented by the general formula (L-1B), or may contain two or more compounds in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more.
The lower limit of the content of the compound represented by the formula (L-1B) is preferably 1 mass%, 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 30 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 37 mass%, 35 mass%, 33 mass%, 30 mass%, 27 mass%, 25 mass%, 23 mass%, 20 mass%, 17 mass%, 15 mass%, 13 mass%, 10 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-1B) is preferably a compound selected from the group of compounds represented by the formulas (L-1B-1) to (L-1B-13), and preferably a compound selected from the group of compounds represented by the formulas (L-1B-1), (L-1B-3) and (L-1B-4). In particular, the compound represented by the formula (L-1B-1) is preferable because the response speed of the liquid crystal composition of the present invention is particularly improved. In the case where Tni is more required than the response speed, it is preferable to use a compound selected from the group of compounds represented by the formula (L-1B-3), the formula (L-1B-4), the formula (L-1B-11) and the formula (L-1B-12). In order to improve the solubility at low temperatures, it is not preferable that the total content of the compounds represented by the formulas (L-1B-3), (L-1B-4), (L-1B-11) and (L-1B-13) is 20% by mass or more.
[ 75]
When the liquid crystal composition of the present invention contains the compound represented by the formula (L-1B-1), the lower limit value of the content of the compound represented by the formula (L-1B-1) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 18 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 17 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The liquid crystal composition of the present invention preferably contains two or more compounds selected from the group of compounds represented by the formula (L-1A-1.3), the formula (L-1A-2.2), the formula (L-1B-1), the formula (L-1B-3), the formula (L-1B-4), the formula (L-1B-11) and the formula (L-1B-12) in combination. The liquid crystal composition of the present invention preferably contains two or more compounds selected from the group consisting of the compounds represented by the formulae (L-1A-1.3), (L-1A-2.2), (L-1B-1), (L-1B-3), (L-1B-4) and (L-1A-4.2). The lower limit of the total content of these compounds is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 18 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 80 mass%, 70 mass%, 60 mass%, 50 mass%, 45 mass%, 40 mass%, 37 mass%, 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention.
In the case where importance is attached to the reliability of the liquid crystal composition, it is preferable to combine two or more compounds selected from the group consisting of the compounds represented by the formula (L-1B-1), the formula (L-1B-3) and the formula (L-1B-4). In addition, in the case where importance is attached to the response speed of the liquid crystal composition, it is preferable to combine two or more compounds selected from the compounds represented by the formulae (L-1A-1.3) and (L-1A-2.2).
The liquid crystal composition of the present invention preferably contains one or more compounds represented by the general formula (L-1A) and one or more compounds represented by the general formula (L-1B). The lower limit of the total amount of the compound represented by the general formula (L-1A) and the compound represented by the general formula (L-1B) is preferably 1% by mass, 2% by mass, 3% by mass, 5% by mass, 7% by mass, 10% by mass, 15% by mass, 20% by mass, 25% by mass, 30% by mass, 35% by mass, 40% by mass, 45% by mass, 50% by mass, and 55% by mass relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 95 mass%, 90 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass% with respect to the total amount of the liquid crystal composition of the present invention.
When it is necessary to maintain the viscosity of the liquid crystal composition of the present invention low and a composition having a high response speed is required, it is preferable that the total amount of the compound represented by the general formula (L-1A) and the compound represented by the general formula (L-1B) is high in the lower limit and high in the upper limit. When it is desired to maintain Tni of the liquid crystal composition of the present invention high and a composition having good temperature stability is desired, it is preferable that the total amount of the compound represented by the general formula (L-1A) and the compound represented by the general formula (L-1B) is of a lower limit and of an upper limit. In order to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the total amount of the compound represented by the general formula (L-1A) and the compound represented by the general formula (L-1B) is low in the lower limit and low in the upper limit.
The compound represented by the general formula (L-2) is the following compound.
[ chemical 76]
(wherein R is L21 R is R L22 R in the general formula (L) is respectively and independently represented L1 R is R L2 The same meaning)
R L21 Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms. In addition, R L22 Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and the unsaturated bond of the alkenyl group is preferably not directly bonded to benzene.
The compounds represented by the general formula (L-2) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
When importance is attached to the solubility at low temperature, the effect is high if the content is set to be high, whereas when importance is attached to the response speed, the effect is high if the content is set to be low. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The lower limit of the content of the compound represented by the formula (L-2) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-2) is preferably a compound selected from the group of compounds represented by the formulas (L-2.1) to (L-2.6), and preferably a compound represented by the formulas (L-2.1), (L-2.3), (L-2.4) and (L-2.6).
[ chemical 77]
The compound represented by the general formula (L-3) is the following compound.
[ 78]
(wherein R is L31 R is R L32 R in the general formula (L) is respectively and independently represented L1 R is R L2 The same meaning)
R L31 R is R L32 Each independently is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. The unsaturated bond of the alkenyl group is preferably not directly bonded to benzene.
The compound represented by the general formula (L-3) may be used alone, but two or more compounds may be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
The lower limit of the content of the compound represented by the formula (L-3) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass% with respect to the total amount of the liquid crystal composition of the present invention.
When a high birefringence is obtained, the effect is high if the content is set to be high, whereas when a high Tni is emphasized, the effect is high if the content is set to be low. Further, in the case of improving the drop trace or the afterimage property, the content range is preferably set to the middle.
The compound represented by the general formula (L-3) is preferably a compound selected from the group of compounds represented by the formulas (L-3.1) to (L-3.7), and preferably a compound represented by the formulas (L-3.2) to (L-3.5).
[ chemical 79]
The compound represented by the general formula (L-4) is the following compound.
[ 80]
(wherein R is L41 R is R L42 R in the general formula (L) is respectively and independently represented L1 R is R L2 The same meaning)
R L41 Preferably carbon atomsAlkyl group having 1 to 5 carbon atoms or alkenyl group having 2 to 5 carbon atoms, R L42 Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. The unsaturated bond of the alkenyl group is preferably not directly bonded to benzene.
The compound represented by the general formula (L-4) may be used alone, but two or more compounds may be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the liquid crystal composition of the present invention, the content of the compound represented by the general formula (L-4) is required to be appropriately adjusted in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, drop trace, afterimage, dielectric anisotropy, etc.
The lower limit of the content of the compound represented by the formula (L-4) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 14 mass%, 16 mass%, 20 mass%, 23 mass%, 26 mass%, 30 mass%, 35 mass%, 40 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 50 mass%, 40 mass%, 35 mass%, 30 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compounds represented by the general formula (L-4) are preferably, for example, compounds represented by the formulae (L-4.1) to (L-4.3).
[ 81]
The compound represented by the formula (L-4.1) may be contained, the compound represented by the formula (L-4.2) may be contained, both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) may be contained, and all of the compounds represented by the formulas (L-4.1) to (L-4.3) may be contained, depending on the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence. The lower limit of the content of the compound represented by the formula (L-4.1) or the formula (L-4.2) is preferably 3 mass%, 5 mass%, 7 mass%, 9 mass%, 11 mass%, 12 mass%, 13 mass%, 18 mass%, 21 mass%, and the upper limit is preferably 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass% with respect to the total amount of the liquid crystal composition of the present invention.
When both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) are contained, the lower limit of the total content of both compounds is preferably 15 mass%, 19 mass%, 24 mass%, 30 mass% relative to the total amount of the liquid crystal composition of the present invention, and the upper limit of the total content is preferably 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% relative to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-4) is preferably a compound represented by the formulae (L-4.4) to (L-4.6), for example, and is preferably a compound represented by the formula (L-4.4).
[ chemical 82]
The compound represented by the formula (L-4.4) may be contained, or the compound represented by the formula (L-4.5) may be contained, or both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) may be contained, depending on the required properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
The lower limit of the content of the compound represented by the formula (L-4.4) or the formula (L-4.5) is preferably 3 mass%, 5 mass%, 7 mass%, 9 mass%, 11 mass%, 12 mass%, 13 mass%, 18 mass%, 21 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass% with respect to the total amount of the liquid crystal composition of the present invention.
When both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) are contained, the lower limit value of the total content of both compounds is preferably 15 mass%, 19 mass%, 24 mass%, 30 mass% relative to the total amount of the liquid crystal composition of the present invention, and the upper limit value of the total content is preferably 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass% relative to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-4) is preferably a compound represented by the formulae (L-4.7) to (L-4.10), and particularly preferably a compound represented by the formula (L-4.9).
[ 83]
The compound represented by the general formula (L-5) is the following compound.
[ chemical 84]
(wherein R is L51 R is R L52 R in the general formula (L) is respectively and independently represented L1 R is R L2 The same meaning)
R L51 Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, R L52 Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. The unsaturated bond of the alkenyl group is preferably not directly bonded to benzene.
The compounds represented by the general formula (L-5) may be used alone, but two or more compounds may also be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
In the liquid crystal composition of the present invention, the content of the compound represented by the general formula (L-5) is required to be appropriately adjusted in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, drop trace, afterimage, dielectric anisotropy, etc.
The lower limit of the content of the compound represented by the formula (L-5) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 14 mass%, 16 mass%, 20 mass%, 23 mass%, 26 mass%, 30 mass%, 35 mass%, 40 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 50 mass%, 40 mass%, 35 mass%, 30 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.1) or the formula (L-5.2), and particularly preferably a compound represented by the formula (L-5.1).
[ chemical 85]
The lower limit of the content of the compound represented by the formula (L-5.1) or the formula (L-5.2) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, or 7 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 9 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.3) or the formula (L-5.4).
[ 86]
The lower limit of the content of the compound represented by the formula (L-5.3) or the formula (L-5.4) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, or 7 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 9 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-5) is preferably a compound selected from the group of compounds represented by the formulas (L-5.5) to (L-5.7), and particularly preferably a compound represented by the formula (L-5.7).
[ 87]
The lower limit of the content of these compounds is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 9 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-6) is the following compound.
[ 88]
(wherein R is L61 R is R L62 R in the general formula (L) is respectively and independently represented L1 R is R L2 Identical meaning, X L61 X is X L62 Respectively are provided withIndependently represents a hydrogen atom or a fluorine atom; wherein the compound represented by the general formula (N-1) is excluded
R L61 R is R L62 Each independently is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms. The unsaturated bond of the alkenyl group is preferably not directly bonded to benzene.
X L61 X is X L62 Preferably, one of them is a fluorine atom and the other is a hydrogen atom.
The compound represented by the general formula (L-6) may be used alone, but two or more compounds may be used in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. The types of the compounds used are, for example, one, two, three, four, five or more types as one embodiment of the present invention.
The lower limit of the content of the compound represented by the formula (L-6) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 14 mass%, 16 mass%, 20 mass%, 23 mass%, 26 mass%, 30 mass%, 35 mass%, 40 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content is preferably 50 mass%, 40 mass%, 35 mass%, 30 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass% with respect to the total amount of the liquid crystal composition of the present invention. In the case of focusing on increasing Δn, the content is preferably increased, and in the case of focusing on precipitation at a low temperature, the content is preferably decreased.
The compounds represented by the general formula (L-6) are preferably compounds represented by the formulae (L-6.1) to (L-6.9).
[ chemical 89]
The types of the combinable compounds are not particularly limited, and one to three of these compounds are preferably contained, and one to four are more preferably contained. Further, since the molecular weight distribution of the selected compound is also effective for solubility, for example, it is preferable to select one compound from the compounds represented by the formula (L-6.1) or the formula (L-6.2), one compound from the compounds represented by the formula (L-6.4) or the formula (L-6.5), one compound from the compounds represented by the formula (L-6.6) or the formula (L-6.7), one compound from the compounds represented by the formula (L-6.8) or the formula (L-6.9), and appropriately combine them. Among them, preferred are compounds represented by the formulae (L-6.1), (L-6.3), (L-6.4), (L-6.6) and (L-6.9).
The compound represented by the general formula (L-6) is, for example, preferably a compound represented by the formulae (L-6.10) to (L-6.17), and among these, a compound represented by the formula (L-6.11) is preferable.
[ chemical 90]
The lower limit of the content of these compounds is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass% relative to the total amount of the liquid crystal composition of the present invention. The upper limit of the content of these compounds is preferably 20 mass%, 15 mass%, 13 mass%, 10 mass%, 9 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The compound represented by the general formula (L-7) is the following compound.
[ 91]
(wherein R is L71 R is R L72 R in the general formula (L) is respectively and independently represented L1 R is R L2 The same meaning, A L71 A is a L72 Each independently represents A in the general formula (L) L2 A is a L3 The same meaning, A L71 A is a L72 The hydrogen atoms of the radicals may be substituted independently of one another by fluorine atoms, Z L71 Z in the general formula (L) L2 Identical meaning, X L71 X is X L72 Each independently represents a fluorine atom or a hydrogen atom; wherein the compounds represented by the general formulae (N-1) to (N-3) are excluded
Wherein R is L71 R is R L72 Each independently is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. The unsaturated bond of the alkenyl group is preferably not directly bonded to benzene.
A L71 A is a L72 Each independently is preferably 1, 4-cyclohexylene or 1, 4-phenylene, A L71 A is a L72 The hydrogen atoms may be each independently substituted with a fluorine atom.
Z L71 Preferably a single bond or COO-, preferably a single bond.
X L71 X is X L72 Preferably all are hydrogen atoms.
The types of the compounds to be combined are not particularly limited, and they are combined according to the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, one, two, three, and four as one embodiment of the present invention.
In the liquid crystal composition of the present invention, the content of the compound represented by the general formula (L-7) is required to be appropriately adjusted in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, drop trace, afterimage, dielectric anisotropy, etc.
The lower limit of the content of the compound represented by the formula (L-7) is preferably 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 14 mass%, 16 mass%, 20 mass% with respect to the total amount of the liquid crystal composition of the present invention. The upper limit of the content of the compound is preferably 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 10 mass%, 5 mass% with respect to the total amount of the liquid crystal composition of the present invention.
The liquid crystal composition of the present invention is preferably used in an embodiment in which a high Tni is desired, and the content of the compound represented by the formula (L-7) is preferably used in an embodiment in which a low viscosity is desired.
The compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.1) to (L-7.4), and more preferably a compound represented by the formula (L-7.2).
[ chemical 92]
The compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.11) to (L-7.13), and more preferably a compound represented by the formula (L-7.11).
[ 93]
/>
The compounds represented by the general formula (L-7) are compounds represented by the formulae (L-7.21) to (L-7.23). The compound represented by the formula (L-7.21) is preferable.
[ 94]
The compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.31) to (L-7.34), and more preferably a compound represented by the formulae (L-7.31) or/and (L-7.32).
[ 95]
The compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.41) to (L-7.44), and more preferably a compound represented by the formulae (L-7.41) or/and (L-7.42).
[ chemical 96]
/>
The compounds represented by the general formula (L-7) are preferably compounds represented by the formulae (L-7.51) to (L-7.53).
[ 97]
[4] Others
In the liquid crystal composition of the present invention, the total content of the compounds represented by the general formula (II) is preferably 80% by mass or more, 85% by mass or more, 88% by mass or more, 90% by mass or more, 92% by mass or more, 93% by mass or more, 94% by mass or more, 95% by mass or more, 96% by mass or more, 97% by mass or more, 98% by mass or more, and 99% by mass or more, relative to the total amount of the liquid crystal composition of the present invention. The total content is preferably not more than 99.99 mass%, not more than 99.95 mass%, not more than 99.5 mass%, not more than 99.0 mass%, not more than 98 mass%, not more than 95 mass% based on the total amount of the liquid crystal composition of the present invention.
When the dielectric anisotropy (Δε) of the liquid crystal composition of the present invention at 25 ℃ has a positive value, the total content of the compound selected from the group of compounds represented by general formula (M) and general formula (K) and the compound represented by general formula (L) is preferably 80 mass% or more, 85 mass% or more, 88 mass% or more, 90 mass% or more, 92 mass% or more, 93 mass% or more, 94 mass% or more, 95 mass% or more, 96 mass% or more, 97 mass% or more, 98 mass% or more, or 99 mass% or more, based on the total amount of the liquid crystal composition of the present invention. The total content is preferably not more than 99.99 mass%, not more than 99.95 mass%, not more than 99.5 mass%, not more than 99.0 mass%, not more than 98 mass%, not more than 95 mass% based on the total amount of the liquid crystal composition of the present invention.
When the dielectric anisotropy (Δε) of the liquid crystal composition of the invention at 25℃has a negative value, the total content of the compound selected from the group of compounds represented by general formulae (N-1) to (N-3) and the compound represented by general formula (L) is preferably 80 mass% or more, 85 mass% or more, 88 mass% or more, 90 mass% or more, 92 mass% or more, 93 mass% or more, 94 mass% or more, 95 mass% or more, 96 mass% or more, 97 mass% or more, 98 mass% or more, or 99 mass% or more, based on the total amount of the liquid crystal composition of the invention. The total content is preferably not more than 99.99 mass%, not more than 99.95 mass%, not more than 99.5 mass%, not more than 99.0 mass%, not more than 98 mass%, not more than 95 mass% based on the total amount of the liquid crystal composition of the present invention.
In the case of using the compound represented by the general formula (II), the total content of the compound represented by the general formula (L) and the compounds represented by the general formulae (M) and (K) is preferably 95 to 100 mass%, and more preferably 97 to 100 mass%, of the liquid crystal composition containing the coloring compound, in terms of achieving both high light resistance and high solubility of the liquid crystal composition. The total content of the compound represented by the general formula (L) and the compounds represented by the general formulae (N-1) to (N-3) is preferably 95 to 100% by mass, and more preferably 97 to 100% by mass, based on 100% by mass of the liquid crystal composition containing the pigment compound.
The compound represented by the general formula (L) is preferably a compound selected from the group consisting of the general formula (L-1A), the general formula (L-1B), the general formula (L-2), the general formula (L-3), the general formula (L-4), the general formula (L-5), the general formula (L-6) and the general formula (L-7). The total content of the compounds represented by the general formula (L) is preferably 90% or more, more preferably 95% or more, of the total content of the compounds selected from the group consisting of the general formula (L-1A), the general formula (L-1B), the general formula (L-2), the general formula (L-3), the general formula (L-4), the general formula (L-5), the general formula (L-6) and the general formula (L-7).
The compound represented by the general formula (L) preferably contains one or more compounds selected from the group consisting of the general formula (L-1A), the general formula (L-1B), the general formula (L-2) and the general formula (L-3), and contains one or more compounds selected from the group consisting of the general formula (L-4), the general formula (L-5), the general formula (L-6) and the general formula (L-7).
The relationship of the content may be applied to any lower concepts of the compounds represented by the general formula (II), the compounds represented by the general formula (M) and the general formula (K), and/or the compounds represented by the general formulae (N-1) to (N-3), and may be applied to any combinations of the compounds represented by the general formula (II), the compounds represented by the general formulae (M) and the general formula (K), and/or the compounds represented by the general formulae (N-1) to (N-3) including the lower concepts.
The liquid crystal composition of the present invention preferably contains a large amount of compounds having all 6-membered ring structures in the molecule. The content of the compound having all 6-membered rings in the molecule is preferably 80% by mass or more, more preferably 90% by mass or more, still more preferably 95% by mass or more, based on the total amount of the liquid crystal composition of the present invention, and the liquid crystal composition of the present invention is most preferably constituted by substantially only the compound having all 6-membered rings in the molecule.
In order to suppress deterioration caused by oxidation of the liquid crystal composition, the liquid crystal composition of the present invention preferably has a small content of a compound having a cyclohexenylene group as a ring structure. The content of the compound having a cyclohexenylene group is preferably 10 mass% or less, more preferably 8 mass% or less, still more preferably 5 mass% or less, still more preferably 3 mass% or less, and still more preferably substantially no content relative to the total amount of the liquid crystal composition of the present invention.
In the present specification, the term "substantially free" means that the material is not contained except for an unexpectedly contained material (unavoidable impurities).
In the case where the liquid crystal composition of the present invention has positive dielectric anisotropy (Δε), the dielectric anisotropy (Δε) at 25 ℃ of the liquid crystal composition of the present invention is preferably in the range of 1.5 to 20.0, more preferably in the range of 1.5 to 18.0, still more preferably in the range of 1.5 to 15.0, yet more preferably in the range of 1.5 to 11, and particularly preferably in the range of 1.5 to 8.
In addition, in the case where the liquid crystal composition of the present invention has negative dielectric anisotropy (Δε), the dielectric anisotropy (Δε) at 25℃of the liquid crystal composition of the present invention is preferably-2 or less, more specifically, in the range of-2.0 to-8.0, preferably-2.0 to-6.0, still more preferably-2.0 to-5.0, and particularly preferably-2.5 to-4.0.
The refractive index anisotropy (Δn) of the liquid crystal composition of the present invention at 25 ℃ is preferably in the range of 0.08 to 0.14, more preferably in the range of 0.09 to 0.13, and particularly preferably in the range of 0.09 to 0.12. In further detail, the range of 0.10 to 0.13 is preferable in the case of a thin cell gap, and the range of 0.08 to 0.10 is preferable in the case of a thick cell gap.
The viscosity (. Eta.) of the liquid crystal composition of the present invention at 25℃is from 10 mPas to 50 mPas, more preferably from 10 mPas to 40 mPas, particularly preferably from 10 mPas to 35 mPas.
The liquid crystal composition of the present invention has a rotational viscosity (. Gamma.) at 25 ℃ 1 ) Preferably in the range from 40 mPas to 130 mPas, more preferably in the range from 50 mPas to 110 mPas, and particularly preferably in the range from 60 mPas to 100 mPas.
The nematic phase-isotropic liquid phase transition temperature (Tni) of the liquid crystal composition of the invention is preferably in the range of 60 ℃ to 120 ℃, more preferably in the range of 70 ℃ to 100 ℃, particularly preferably in the range of 70 ℃ to 85 ℃.
< pigment Compound >)
The liquid crystal composition containing a pigment compound of the present invention preferably contains one or more pigment compounds in addition to the pigment compound represented by the general formula (1), and preferably contains a total of three or more pigment compounds represented by the general formula (1) and other pigment compounds. When a plurality of dye compounds are used, the plurality of dye compounds preferably have different absorption wavelengths from each other, and thus can be produced in a desired color such as black.
The pigment compound preferably has a maximum absorption wavelength between 350nm and 750 nm. In particular, in the case where the compound represented by the general formula (1) is a red dye, it is preferable that the compound has a maximum absorption of 500nm to 600nm, in the case of a yellow dye, it is preferable that the compound has a maximum absorption of 400nm to 500nm, and in the case of a blue dye, it is preferable that the compound has a maximum absorption of 600nm to 750 nm.
The method for measuring the maximum absorption wavelength is as follows.
First, 1.0 part by mass of a pigment compound was added to 100 parts by mass of any liquid crystal composition in which the pigment compound was soluble, and the mixture was dissolved to prepare a sample.
Next, a cell including an inlet was fabricated using two glass substrates having an Indium Tin Oxide (ITO) electrode and including an alignment film for horizontal alignment on the ITO electrode, the cell including an ITO electrode layer as the inner side of the cell, and the cell thickness was adjusted to 10 μm by plastic particles.
The cell was filled with a sample, and the injection port was plugged with a sealing material, thereby producing an element.
Then, the absorption spectrum between 350nm and 750nm was measured using a spectrometer (manufactured by tsukamurelba electronics corporation, "LCD-5200") at 25 ℃ without applying a voltage, and the maximum absorption wavelength of the pigment compound was obtained.
The dye compound is preferably a dichroic dye.
The dye compound is preferably selected from the group consisting of azo compounds, anthraquinone compounds, methine compounds, azomethine compounds, merocyanine compounds, quinone compounds, naphthoquinone compounds, tetrazine compounds, perylene compounds, trinaphthalene (terrylene) compounds, quartilene (quaterylene) compounds, homonaphthacene (higher rylene) compounds, indigo compounds, dioxazine compounds, pyrrole methylene compounds, spiropyran compounds and diarylethene (diarylethene) compounds.
Examples of the azo compound include a disazo compound and a trisazo compound.
The type of the pigment compound used in the liquid crystal composition is one or two or more, preferably one to five, preferably one to four, preferably one to three.
The lower limit value of the total content of the pigment compounds including the compound represented by the general formula (1) is preferably 0.1 mass% or more, preferably 0.2 mass% or more, preferably 0.3 mass% or more, preferably 0.4 mass% or more, preferably 0.5 mass% or more, preferably 0.7 mass% or more, and preferably 1 mass% or more, relative to 100 mass% of the liquid crystal composition including no pigment compound and no additive.
The upper limit value of the pigment compound including the compound represented by the general formula (1) is preferably 20 mass% or less, more preferably 15 mass% or less, still more preferably 12 mass% or less, yet more preferably 10 mass% or less, yet more preferably 8 mass% or less, yet more preferably 5 mass% or less, relative to 100 mass% of the liquid crystal composition including no pigment compound and no additive.
The total content of the pigment compounds including the compound represented by the general formula (1) is preferably 0.1 to 20% by mass, more preferably 0.2 to 15% by mass, still more preferably 0.3 to 15% by mass, still more preferably 0.5 to 12% by mass, still more preferably 0.8 to 10% by mass, still more preferably 1 to 8% by mass, and still more preferably 1 to 6% by mass, relative to 100% by mass of the liquid crystal composition containing no pigment compounds and additives.
< additive >)
The liquid crystal composition containing the pigment compound of the present invention can be produced by mixing the above-mentioned other compounds and additives as required. Examples of the additive include: stabilizers, chiral agents, antistatic agents, nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, polymerizable compounds, and the like.
As the stabilizer, there may be mentioned: antioxidants, ultraviolet (UV) absorbers, light stabilizers, infrared absorbers, and the like.
As the antioxidant, there may be mentioned: hydroquinone derivatives, nitrosamine polymerization inhibitors, hindered phenol antioxidants, and the like.
More specifically, it is possible to list: tert-butylhydroquinone, methylhydroquinone, and "Q-1300", "Q-1301", manufactured by the photo-pure chemical industries, inc., BASF ", yi Lunuo s (IRGANOX) 1010", "Yi Lunuo s (IRGANOX) 1035", "Yi Lunuo s (IRGANOX) 1076", "Yi Lunuo s (IRGANOX) 1098", "Yi Lunuo s (IRGANOX) 1135", "Yi Lunuo s (IRGANOX) 1330", "Yi Lunuo s (IRGANOX) 1425", "Yi Lunuo s (IRGANOX) 1520", "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", and the like.
As the Ultraviolet (UV) absorber, an Ultraviolet (UV) absorber having a wavelength of 400nm or more and having little absorption of visible light is preferable in terms of excellent absorption of ultraviolet rays having a wavelength of 370nm or less and good liquid crystal display property.
More specifically, for example, there may be mentioned: hindered phenol compounds, benzotriazole compounds, hydroxybenzophenone compounds, salicylate compounds, benzophenone compounds, cyanoacrylate compounds, nickel complex compounds, triazine compounds, and the like.
Examples of the hindered phenol compound include: 2, 6-di-tert-butyl-p-cresol, pentaerythritol-tetrakis [ 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], N' -hexamethylenebis (3, 5-di-tert-butyl-4-hydroxy-hydrocinnamamide), 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) benzene, tris- (3, 5-di-tert-butyl-4-hydroxybenzyl) -isocyanurate.
Examples of the benzotriazole-based compound include: 2- (2 '-hydroxy-5' -methylphenyl) benzotriazole, 2-methylenebis (4- (1, 3-tetramethylbutyl) -6- (2H-benzotriazol-2-yl) phenol), 2, 4-bis- (N-octylthio) -6- (4-hydroxy-3, 5-di-tert-butylphenyl) -1,3, 5-triazine, triethylene glycol-bis [ 3- (3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate ], N '-hexamethylenebis (3, 5-di-tert-butyl-4-hydroxy-hydrocinnamamide), 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) benzene, 2- (2' -hydroxy-3 ',5' -di-tert-butylphenyl) -5-chlorobenzotriazole, 2- (2 '-hydroxy-3', 5-di-tert-pentylphenyl) -5-chlorobenzo-2, 6-di-tert-butyl-p-triazole, pentaerythritol-3- (3, 5-di-tert-butylphenyl) propionate.
More specifically, it is possible to list: "Di-Nelumbo (TINUVIN) 109", "Di-Nelumbo (TINUVIN) 171", "Di-Nelumbo (TINUVIN) 326", "Di-Nelumbo (TINUVIN) 327", "Di-Nelumbo (TINUVIN) 328", "Di-Nelumbo (TINUVIN) 770", "Di-Nelumbo (TINUVIN) 900", "Di-Nelumbo (TINUVIN) 928", kai Mi Buluo "KemisORB) 71", "KemisORB) 73", "KemisORB) 74", etc. manufactured by Chemipro Kasei (strand).
The type of stabilizer used in the liquid crystal composition containing the pigment compound is one or two or more, preferably one to five, preferably one to four, preferably one to three, preferably one to two.
When the stabilizer is used, the lower limit of the total content of the stabilizers is preferably 0.01 mass% or more, preferably 0.05 mass% or more, and preferably 0.1 mass% or more, based on 100 mass% of the liquid crystal composition containing no pigment compound or additive.
When the stabilizer is used, the upper limit of the total content of the stabilizers is preferably 2.0 mass% or less, more preferably 1.5 mass% or less, and still more preferably 1.0 mass% or less, based on 100 mass% of the liquid crystal composition containing no pigment compound or additive.
When a stabilizer is used, the total content of the stabilizers is preferably 0.01 to 2.0 mass%, more preferably 0.05 to 1.5 mass%, and even more preferably 0.1 to 1.0 mass%, based on 100 mass% of the liquid crystal composition excluding the pigment compound and the additive.
In addition, by using a chiral agent in a liquid crystal composition containing a pigment compound, twist can be induced in the liquid crystal. The chiral agent may be either dextrorotatory or levorotatory, as long as it is appropriately used separately according to the structure of the element. Further, as the chiral agent, a chiral agent used in a Twisted Nematic (TN) mode or a super twisted nematic (super twisted nematic, STN) mode can be used.
For example, examples of Chiral agents include "Chiral (Chiral) S-811 (a compound represented by the following structural formula (CA-1)", and the like.
[ 98]
In the structural formula (CA-1), the "×" indicates an uneven center.
The chiral agent used in the liquid crystal composition containing the pigment compound is one or more, preferably one to five, preferably one to four, preferably one to three, preferably one to two, preferably one.
When the chiral agent is used, the lower limit of the total content of the chiral agent is preferably 0.05 mass% or more, preferably 0.1 mass% or more, preferably 0.3 mass% or more, and preferably 0.5 mass% or more, based on 100 mass% of the liquid crystal composition containing no pigment compound or additive.
When the chiral agent is used, the upper limit of the total content of the chiral agent is preferably 5 mass% or less, more preferably 3.0 mass% or less, still more preferably 2.0 mass% or less, and still more preferably 1.5 mass% or less, based on 100 mass% of the liquid crystal composition containing no pigment compound or additive.
When the chiral agent is used, the total content of the chiral agent is preferably 0.05 to 5% by mass, more preferably 0.1 to 3.0% by mass, still more preferably 0.3 to 2.0% by mass, and still more preferably 0.5 to 1.5% by mass, based on 100% by mass of the liquid crystal composition containing no pigment compound and additive.
Upper limit temperature of liquid crystal phase (T) NI ) A temperature at which the liquid crystal composition used in the liquid crystal composition containing the pigment compound changes phase from a nematic phase to an isotropic phase. T is right NI The higher the temperature, the more dimension can be realizedFrom the standpoint that the driving temperature range can be widely obtained by maintaining the nematic phase, the upper limit temperature (T) of the liquid crystal phase of the liquid crystal composition used in the liquid crystal composition containing a pigment compound of the present invention NI ) Preferably 95℃or higher, preferably 100℃to 150℃and preferably 100℃to 130 ℃.
Lower limit temperature of liquid crystal phase (T) →N ) The temperature at which the liquid crystal composition used in the liquid crystal composition containing the pigment compound changes phase from other phases (glass, smectic phase, crystalline phase) to nematic phase. T is right →N The lower the temperature, the nematic phase can be maintained at a lower temperature, and therefore the lower limit temperature (T →N ) Preferably below-15 ℃, preferably between-78 ℃ and-20 ℃, preferably between-65 ℃ and-25 ℃.
The refractive index anisotropy (. DELTA.n) at 25℃and 589nm of the liquid crystal composition used in the liquid crystal composition containing a pigment compound of the present invention is preferably 0.05 or more, preferably 0.06 to 0.20, preferably 0.07 to 0.15, preferably 0.08 to 0.13.
The refractive index (n) of the liquid crystal composition used in the liquid crystal composition containing the pigment compound of the present invention in the long axis direction of the liquid crystal molecules at 25℃and 589nm e ) Preferably 1.4 or more, preferably 1.45 to 1.65, preferably 1.50 to 1.63.
The refractive index (n) in the short axis direction of liquid crystal molecules at 25℃and 589nm of the liquid crystal composition used in the liquid crystal composition containing a pigment compound of the present invention o ) Preferably 1.3 or more, preferably 1.35 to 1.55, preferably 1.40 to 1.53.
In addition, an Abbe refractometer may be used to determine n of a liquid crystal composition used in a liquid crystal composition containing a pigment compound e 、n o And Δn is calculated.
The liquid crystal composition used in the liquid crystal composition containing a pigment compound of the present invention has a rotational viscosity (. Gamma.) at 25 ℃ 1 ) Preferably from 100 mPas to 180 mPas, preferably from 105 mPas to 175 mPas, preferably from 110 mPas to 170 mPas, preferably from 115 mPas to 165 mPas.
The liquid crystal composition used in the liquid crystal composition containing a pigment compound of the present invention has an elastic constant K at 25 DEG C 11 Preferably 1.0pN to 30.0pN, preferably 5.0pN to 25.0pN, preferably 10.0pN to 20.0pN.
The liquid crystal composition used in the liquid crystal composition containing a pigment compound of the present invention has an elastic constant K at 25 DEG C 22 Preferably 1.0pN to 25.0pN, preferably 3.0pN to 20.0pN, preferably 5.0pN to 15.0pN.
The liquid crystal composition used in the liquid crystal composition containing a pigment compound of the present invention has an elastic constant K at 25 DEG C 33 Preferably 1.0pN to 35.0pN, preferably 5.0pN to 30.0pN, preferably 10.0pN to 25.0pN.
< element >
Next, an element using the liquid crystal composition containing a pigment compound will be described.
As the use of the element, a light adjusting element is preferable. The structure of the element is preferably as follows: the substrate having the first transparent electrode layer and the substrate having the second transparent electrode layer are disposed opposite to each other so that the transparent electrode layers are positioned inward, and the liquid crystal composition is sandwiched between the substrates.
The transparent electrode layer is preferably an ITO electrode. The substrate having the first transparent electrode layer and/or the second transparent electrode layer may include an alignment film on the transparent electrode layer. As the alignment film, an alignment film for horizontal alignment is preferable.
In addition, by adding a chiral agent to the liquid crystal composition containing a pigment compound, the liquid crystal can be twisted and aligned. In terms of improving absorbance, the twist of liquid crystal molecules in the liquid crystal composition containing the dye compound when the chiral agent is added is preferably 180 ° or more, more preferably 180 ° to 720 °, still more preferably 270 ° to 540 °, still more preferably 270 ° to 450 °.
The twist of the liquid crystal molecules can also be adjusted by: the angle of the orientation axis is adjusted by disposing a substrate having a first transparent electrode layer and a substrate having a second transparent electrode layer.
The twist pitch (p) in the liquid crystal composition containing the pigment compound when the chiral agent is added is preferably 2 μm to 30 μm, and more preferably 5 μm to 20 μm.
Regarding the twist pitch (p), a liquid crystal composition containing a predetermined amount of chiral agent is injected into an antiparallel rubbed wedge-shaped liquid crystal cell having two substrates with a cell thickness gradually varying, and the gap L between disclination lines (disclination line) of the wedge-shaped liquid crystal cell obtained by measuring the inclination angle θ (inclination of the substrate on the upper surface) of the wedge-shaped liquid crystal cell with a length measuring device or the like is calculated to be p=2×l×tan θ.
The d/p value as a relation between the twist pitch (p) and the cell thickness (d) is preferably 0.1 to 2.2, and more preferably 0.5 to 1.5. Specifically, it is preferable to adjust the relationship d/p between the twist pitch (p) and the cell thickness (d) so that the relationship d/p becomes optimal according to the twist angle. The optimal d/p value is a region where no alignment defect such as a reverse twist region or a fringe region occurs. The domains are preferably observed visually or microscopically or the like and adjusted so as not to generate alignment defects.
The pretilt angle of the liquid crystal composition containing the pigment compound in the element is preferably 0.1 ° to 10 °, and preferably 0.5 ° to 5 °. Pretilt angle can be measured using opathicon (OPTIPRO) manufactured by shitec (Shintech).
The spacing (cell thickness) of the substrates is preferably 1 μm to 100. Mu.m, preferably 1.5 μm to 30. Mu.m, preferably 5 μm to 20. Mu.m. The spacing of the substrates may also be adjusted using spacers. Examples of the spacer include: glass particles, plastic particles, alumina particles, photoresist materials, and the like.
In addition, the element of the present invention may also include an ultraviolet cut film in terms of preventing deterioration caused by ultraviolet rays. For example, an Ultraviolet (UV) cut-off film that cuts off light having a wavelength of 400nm or less may be laminated on the element, or an Ultraviolet (UV) cut-off film that cuts off light having a wavelength of 400nm or less may be attached to the element.
The element of the present invention may be used in the form of a single layer, or a plurality of elements may be stacked in two or more layers. When a plurality of elements are stacked for use, it is preferable that the antiparallel alignment-treated elements are stacked so that the alignment-treated directions are 90 ° orthogonal in terms of improvement of contrast.
The element may be fabricated as follows.
For example, a sealant such as an epoxy thermosetting composition is drawn on a substrate having a first transparent electrode layer in a form in which an injection port is provided, and the substrate having a second transparent electrode layer and the substrate are bonded to each other, and thereafter, the sealant is heated to thermally harden the sealant, whereby an empty cell can be produced. Then, a liquid crystal composition containing a pigment compound is sandwiched between two substrates in the cell by a normal vacuum injection method or the like, whereby a liquid crystal element can be produced.
Further, a sealant such as an epoxy thermosetting composition is drawn on a substrate having a first transparent electrode layer, a liquid crystal composition containing a pigment compound is dropped by a Drop Fill (ODF) method or an inkjet method under vacuum, and then the substrate having a second transparent electrode layer and the substrate are bonded to each other, and thereafter, the sealant is heated to thermally harden the sealant, whereby a liquid crystal element can be manufactured.
In addition, when the contrast is to be further improved, an optical film such as a polarizing axis may be further disposed at a predetermined angle in the element.
Examples (example)
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to the examples.
The compositions of the following examples and comparative examples contain the respective compounds in the proportions shown in the table, and the contents are described as "mass%. The following abbreviations are used as shown in tables 1 and 2. Unless otherwise specified, compounds of the cis-form and the trans-form may be used to represent the trans-form.
Structure of ring
[ chemical 99]
< terminal structure >)
TABLE 1
| Short for short | Chemical structure |
| -n | -C n H 2n+1 |
| n- | C n H 2n+1 - |
| -On | -OC n H 2n+1 |
| nO- | C n H 2n+1 O- |
| -F | -F |
| -CN | -CN |
| -V | -CH＝CH 2 |
| V- | CH 2 ＝CH- |
| -2V | -CH 2 -CH 2 -CH＝CH 2 |
| V2- | CH 2 ＝CH-CH 2 -CH 2 - |
| -V1 | -CH＝CH-CH 3 |
| 1V- | CH 3 -CH＝CH- |
(wherein n in the table is a natural number)
Connection structure
TABLE 2
| Short for short | Chemical structure |
| - | Single key |
| -n- | -C n H 2n - |
| -E1- | -C(＝O)-O- |
| -E2- | -O-C(＝O)- |
< pigment Compound >)
[ 100]
[ 101]
/>
[ chemical 102]
TABLE 3
The following dye is a commercially available azo dye having a structure different from that of the general formula (1).
AZO-1: blue dichroic dye compound (azo system) having maximum absorption wavelength of 633nm
AZO-2: dichroic dye compound (azo system) exhibiting red color, and maximum absorption wavelength of 517nm
AZO-3: dichroic dye compound (azo system) exhibiting yellow color, and having maximum absorption wavelength of 405nm
< antioxidant >
Yi Lunuo si (IRGANOX) 1076: hindered phenol antioxidant
Ultraviolet (UV) absorber
Kem Mi Suobu (KEMISORB) 71: benzotriazole-based compound
Physical Properties of liquid Crystal composition used in liquid Crystal composition containing pigment Compound
Physical properties were measured for a liquid crystal composition used in a liquid crystal composition containing a pigment compound. The meaning of each item is as follows.
T NI (. Degree.C.): liquid crystal compositionTemperature at which nematic phase changes to isotropic phase (upper limit temperature)
T →N (. Degree.C.): temperature at which the liquid crystal composition changes from other nematic phase (lower limit temperature)
An: refractive index anisotropy of liquid Crystal composition at 25 ℃ and 589nm
Δε: dielectric anisotropy at 25 ℃ of liquid crystal composition
γ 1 (mPas): rotational tack at 25℃
(example 1 to example 19 and comparative example 1 to comparative example 4)
Preparation of liquid Crystal composition used in liquid Crystal composition containing pigment Compound
Liquid crystal compositions LC-1 to LC-9 used in the liquid crystal compositions containing the pigment compounds were prepared by mixing the respective liquid crystal compounds in respective proportions, and physical properties were measured. The results are shown in tables 4 to 7.
TABLE 4
| Liquid crystal compound | LC1 | LC2 | LC3 | LC4 | LC5 |
| V-Cy-Cy-Ph3-F | 20 | ||||
| V-Cy-Cy-Ph-1 | 15 | 15 | |||
| V2-Cy-Cy-Ph-1 | 15 | 15 | 15 | 15 | 20 |
| 3-Cy-Cy-Ph3-F | 14 | 14 | 15 | ||
| V-Cy-Cy-Ph3-F | 15 | ||||
| 3-Cy-Ph-Ph35-F | 15 | 15 | 15 | ||
| 2-Ph-Ph3-Ph35-F | 8 | 5 | |||
| 3-Cy-Ph-O1 | 15 | 16 | |||
| 3-Cy-Ph-O2 | 16 | 12 | 12 | 12 | 16 |
| 3-Cy-Ph35-CN | 10 | 12 | |||
| 5-Cy-E1-Ph3-F | 8 | 8 | |||
| 3-Cy-Cy-E1-Ph3-F | 3 | 5 | 5 | ||
| 3-Cy-2-Cy-E1-Ph3-F | 2 | ||||
| 4-Cy-2-Cy-E1-Ph3-F | 2 | ||||
| 2-Cy-Cy-Ph-Ph3-F | 4 | 4 | 4 | 4 | |
| 3-Cy-Cy-Ph-Ph3-F | 4 | 4 | 4 | 4 | |
| 3-Cy-Cy-V | 15 | ||||
| 5-Ph-Ph-CN | 10 | ||||
| 3-Cy-Ph-Ph-1 | 5 | ||||
| 3-Cy-Cy-E1-Ph-Cy-2 | 2 | 4 | 4 | 4 | |
| 3-Cy-Cy-E1-Ph-Cy-3 | 3 | 3 | |||
| 3-Cy-Cy-E1-Ph-Cy-4 | 3 | 3 | 4 | 4 | 4 |
| Total (mass%) | 100 | 100 | 100 | 100 | 100 |
TABLE 5
| Liquid crystal compound | LC6 | LC7 | LC8 | LC9 |
| 3-Cy-Cy-2 | 14 | |||
| 3-Cy-Cy-4 | 5 | |||
| 3-Cy-Ph-O2 | 14 | 10 | 10 | 8 |
| 3-Cy-Cy-V | 21 | 19 | 21 | |
| 3-Cy-Ph-Ph-2 | 6 | 6 | 6 | 6 |
| 5-Cy-Ph-Ph-2 | 6 | 6 | 6 | 6 |
| V-Cy-Cy-Ph-1 | 4 | |||
| V2-Cy-Cy-Ph-1 | 7 | 13 | 15 | 15 |
| 3-Cy-1O-Ph5-O2 | 4 | 10 | 10 | 10 |
| 3-Cy-Cy-E1-Ph5-O2 | 6 | |||
| 3-Cy-Cy-Ph5-O2 | 5 | |||
| 2-Cy-Cy-1O-Ph5-O2 | 12 | 14 | 12 | 14 |
| 3-Cy-Cy-1O-Ph5-O2 | 12 | 20 | 17 | 20 |
| V-Cy-Cy-1O-Ph5-O2 | 5 | |||
| V-Cy-Cy-1O-Ph5-O3 | 5 | |||
| Total (mass%) | 100 | 100 | 100 | 100 |
TABLE 6
| Physical property values | LC1 | LC2 | LC3 | LC4 | LC5 |
| T NI (℃) | 108.2 | 116.8 | 118.2 | 106.4 | 103.0 |
| T →N (℃) | G-53 | G-45 | G-50 | G-55 | G-54 |
| Δn | 0.116 | 0.100 | 0.110 | 0.102 | 0.111 |
| Δε | 6.8 | 6.0 | 5.0 | 3.8 | 3.4 |
| γ 1 | 149 | 153 | 139 | 145 | 133 |
TABLE 7
| Physical property values | LC6 | LC7 | LC8 | LC9 |
| T NI (℃) | 104.5 | 99.4 | 103.1 | 102.2 |
| T →N (℃) | G-53 | G-52 | G-52 | G-52 |
| Δn | 0.095 | 0.094 | 0.097 | 0.095 |
| Δε | -3.2 | -2.9 | -3.2 | -3.0 |
| γ 1 | 141 | 118 | 130 | 122 |
Manufacture of element, dichroism test and solubility test
The liquid crystal composition containing the pigment compound was prepared by mixing and dissolving the pigment compound, the antioxidant, and the UV absorber in LC1 to LC 9. Next, two glass substrates having ITO electrodes and including an alignment film (AL 1051) for horizontal alignment on the ITO electrodes were used to fabricate a cell including an inlet, which was formed by using an ITO electrode layer as the inner side of the cell and adjusting the cell thickness to 10 μm by plastic particles. The liquid crystal composition containing the pigment compound was injected into the cell, and the injection port was closed with a sealing material, thereby manufacturing an element. Then, a dichroism test and a solubility test were performed using the fabricated element. The results are shown in tables 5 to 7.
In tables 5 to 7, the amounts (parts by mass) of the pigment compound, the antioxidant, and the chiral agent added are shown as amounts per 100 parts by mass of the liquid crystal composition.
(dichroism test)
The dichroic ratio (R) was determined as follows. When the transmittance at the maximum absorption wavelength at which the orientation direction of the test panel is parallel to the linear polarization is A0 and the transmittance at the maximum absorption wavelength at which the orientation direction is orthogonal to the linear polarization by rotating the test panel is a90, the dichroic ratio (R) is calculated from the equation r=a0/a 90, using linear polarization as the light source of the transmittance meter.
(solubility test)
The liquid crystal composition containing the pigment compound was stored at room temperature, and the presence or absence of precipitation was visually observed every 48 hours within 500 hours.
The evaluation criteria are as follows.
A: no precipitation was confirmed until 500 hours later.
B: precipitation was confirmed in a period of 48 hours to less than 500 hours.
C: precipitation was confirmed in a period of less than 48 hours.
TABLE 8
TABLE 9
From examples 1 to 15 and comparative examples 1 to 3, it was confirmed that the liquid crystal compositions containing the pigment compound comprising the pigment compound represented by the general formula (1) and the liquid crystal composition containing the compound represented by the general formula (II) can achieve both high dichroism and good solubility, compared with the case of using the pigment compound of comparative examples 1 to 3.
TABLE 10
From examples 16 to 19 and comparative example 4, it was confirmed that the liquid crystal composition containing the pigment compound comprising the pigment compound represented by the general formula (1) and the liquid crystal composition containing the compound represented by the general formula (II) can achieve both high dichroism and good solubility, compared with the case of using the pigment compound of comparative example 4.
Further, the black liquid crystal composition obtained by adjusting the dichroic dye containing three or more dye compounds represented by the general formula (1) is excellent in both the dichroic ratio and the solubility. Accordingly, it was confirmed that the liquid crystal composition containing the pigment compound of the present application can adjust the color tone while simultaneously achieving both the dichroic ratio and the solubility.
[ Industrial applicability ]
The liquid crystal composition containing the pigment compound can be used for a light-adjusting element.
Claims (10)
1. A liquid crystal composition containing a pigment compound, comprising one or more compounds represented by the general formula (1) and a liquid crystal composition containing one or more compounds represented by the general formula (II),
wherein U is any one selected from the group represented by the general formula (2) and the general formula (3),
R 1 、R 2 、R 3 、R 4 r is R 5 Independently of one another, a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, 1-CH present in these groups 2 -or not more than 2-CH 2 -can be represented by-NR 6 -、-O-、-S-、-CO-、-CS-、-COO-、-OCO-、-CO-S-、-S-CO-、-SO-、-SO 2 -, -O-CO-O-, -CO-NH-; -NH-CO- -CH=CH-, -CF=CF-, or-C≡C-substitution, the hydrogen atoms present in these radicals may be substituted by fluorine atoms, where R 6 Represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, 1-CH being present in these groups 2 -or not more than 2-CH 2 Can be selected from the group consisting of-O-, -S-, -COO- -an OCO-or-CO-substitution, the hydrogen atoms present in these groups may be substituted by fluorine atoms,
R a 、R b r is R c Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, 1-CH being present in these groups 2 -or not more than 2-CH 2 -can be represented by-NR 7 -、-O-、-S-、-CO-、-CS-、-COO-、-OCO-、-CO-S-、-S-CO-、-SO-、-SO 2 -, -O-CO-O-, -CO-NH-; -NH-CO- -CH=CH-, -CF=CF-, or-C≡C-substitution, the hydrogen atoms present in these radicals may be substituted by fluorine atoms, where R 7 Represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, 1-CH being present in these groups 2 -or not more than 2-CH 2 Can be selected from the group consisting of-O-, -S-, -COO- -an OCO-or-CO-substitution, the hydrogen atoms present in these groups may be substituted by fluorine atoms,
X a 、X b x is X c Each independently represents-S-or-O-,
A 1 、A 2 、A 4 、A 5 、A a A is a b Each independently represents a hydrocarbon ring or a heterocyclic ring having 3 to 16 carbon atoms which may be substituted,
Z 1 、Z 2 、Z 4 、Z 5 、Z a 、Z b z is as follows c Each independently represents-CH 2 O-、-OCH 2 -、-CF 2 O-、-OCF 2 -、-COO-、-OCO-、-CH 2 CH 2 -、-CF 2 CF 2 -, -CH=CH-, -CF=CF-, -N=CH-; -CH=N-, -N=N-, -C≡C-, or a single bond,
i. j, a, b, c and d each independently represent an integer of 0 to 4,
at A 1 、A 2 、A 4 、A 5 、A a A is a b In the case of a plurality of A 1 、A 2 、A 4 、A 5 、A a A is a b May be the same or different, at Z 1 、Z 2 、Z 4 、Z 5 、Z a 、Z b Z is as follows c In the case of a plurality of Z' s 1 、Z 2 、Z 4 、Z 5 、Z a 、Z b Z is as follows c May be the same or different, in which case a plurality of R's are present 6 In the case of (1), a plurality of R 6 May be the same as or different from each other,
in the general formula (II),
R II1 represents an alkyl group having 1 to 10 carbon atoms, 1 of the alkyl groups being non-adjacent to or greater than 2-CH 2 Each independently is composed of-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution,
A II1 a is a II2 Each independently represents a radical selected from the group consisting of,
(a) 1, 4-cyclohexylene, 1-CH present in the radical 2 -or not more than 2-CH 2 Can be substituted by-O-,
(b) 1, 4-phenylene, 1-ch=or more than 2-ch=that are not contiguous present in the radical can be substituted to-n=and
(c) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl, wherein 1-ch=or more than 2-ch=that are not adjacent to 1-ch=present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted to-n=,
The groups (a), (b) and (c) may each be independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z II1 represents a single bond, -CH 2 CH 2 -、-(CH 2 ) 4 -、-OCH 2 -、-CH 2 O-、-COO-、-OCO-、-OCF 2 -、-CF 2 O-, -ch=n-n=ch-, -ch=ch-, -cf=cf-or-c≡c-,
Y II1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group or an alkyl group having 1 to 10 carbon atoms, 1 of which is not adjacent to or more than 2-CH 2 Each independently is composed of-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution, in addition, 1 or more than 2 hydrogen atoms in the alkyl group may be substituted with fluorine atoms,
m II1 represents 1, 2, 3 or 4, at m II1 In the case of 2, 3 or 4, a plurality of A II1 A plurality of Z II1 May be the same or different.
2. According to claim 1The liquid crystal composition containing a pigment compound, wherein in the general formula (1), A 1 、A 2 、A 4 、A 5 、A a A is a b Each independently represents a radical selected from the group consisting of,
(a) 1, 4-cyclohexylene, 1-CH present in the radical 2 -or not more than 2-CH 2 Can be substituted by-O-or-S-, 1 CH or more than 2 CH not adjacent in said radical can be substituted by N,
(b) 1, 4-phenylene, 1-ch=or more than 2-ch=that are not contiguous present in the radical can be substituted to-n=,
(c) 1, 4-cyclohexenylene, bicyclo [2.2.2] octane-1, 4-diyl, naphthalene-2, 6-diyl, naphthalene-1, 4-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 5,6,7, 8-tetrahydronaphthalene-1, 4-diyl, decahydronaphthalene-2, 6-diyl, anthracene-1, 4-diyl, anthracene-9, 10-diyl, phenanthrene-2, 7-diyl, the hydrogen atoms present in these groups may be substituted by fluorine atoms or chlorine atoms, and additionally naphthalene-2, 6-diyl, naphthalene-1, 4-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 5,6,7, 8-tetrahydronaphthalene-1, 4-diyl, anthracene-2, 6-diyl, anthracene-1, 4-diyl, anthracene-9, 10-diyl or phenanthrene-2, 7-diyl may be substituted by = in 1,2, 7-CH = N-2 =, or the presence of = -CH-2 =.
(d) Thiophene-2, 5-diyl, thiophene-2, 4-diyl, benzothiophene-2, 5-diyl, benzothiophene-2, 6-diyl, dibenzothiophene-3, 7-diyl, dibenzothiophene-2, 6-diyl, thieno [3,2-b ] thiophene-2, 5-diyl, 1-ch=or more than 2-ch=that are not contiguous present in said groups may be substituted to-n=,
these radicals may be unsubstituted or substituted by more than one substituent L 2 Instead of the above-mentioned,
L 2 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorothioyl group, a nitro group, a cyano 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 1-CH 2 -or more than 2-CH 2 Each independently of the others is composed of-O-, -S-,-CO-, -CS-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -ch=ch-COO-, -ch=ch-OCO-, -COO-ch=ch-, -cf=cf-, or-c≡c-substituted linear alkyl of 1 to 20 carbon atoms or branched alkyl of 3 to 20 carbon atoms or cyclic alkyl of which oxygen atoms are not directly bonded to each other, any hydrogen atom in the alkyl group being substituted with a fluorine atom.
3. The liquid crystal composition containing a pigment compound according to claim 1 or 2, which contains a compound selected from the group of compounds represented by the general formula (L) as the compound represented by the general formula (II),
wherein R is L1 R is R L2 Independently represent an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent to or greater than 2-CH 2 Each independently is composed of-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution,
n L1 represents 0, 1, 2 or 3,
A L1 、A L2 a is a L3 Each independently represents a radical selected from the group consisting of,
(a) 1, 4-cyclohexylene, 1-CH present in the radical 2 -or not more than 2-CH 2 -can be substituted by-O-
(b) 1, 4-phenylene, 1-ch=or more than 2-ch=that are not contiguous present in the radical can be substituted to-n=,
(c) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl, wherein 1-ch=or more than 2-ch=that are not adjacent to 1-ch=present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted to-n=,
the groups (a), (b) and (c) may each be independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z L1 z is as follows L2 Respectively and independently represent a single bond, -CH 2 CH 2 -、-(CH 2 ) 4 -、-OCH 2 -、-CH 2 O-、-COO-、-OCO-、-OCF 2 -、-CF 2 O-, -ch=n-n=ch-, -ch=ch-, -cf=cf-or-c≡c-,
at n L1 Is 2 or 3 and A L2 Where there are plural, they may be the same or different, and where n L1 Is 2 or 3 and Z L2 Where there are plural, they may be the same or different;
wherein the compounds represented by the general formulae (M) and (K) and the compounds represented by the general formulae (N-1), (N-2) and (N-3) are excluded.
4. A liquid crystal composition containing a pigment compound according to any one of claims 1 to 3, which contains a compound selected from the group of compounds represented by the general formulae (M) and (K) as a compound represented by the general formula (II),
wherein R is M1 R is R K1 Independently represent an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent to or greater than 2-CH 2 Each independently is composed of-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution,
n M1 N is as follows K1 Each independently represents 0, 1, 2, 3 or 4,
A M1 a is a M2 A is a K1 A is a K2 Each independently represents a radical selected from the group consisting of,
(a) 1, 4-cyclohexylene, 1-CH present in the radical 2 -or not more than 2-CH 2 -can be substituted by-O-or-S-
(b) 1, 4-phenylene, 1-ch=or more than 2-ch=that are not contiguous present in the radical can be substituted to-n=,
the hydrogen atoms on the radicals (a) and (b) may each independently be substituted by cyano groups, fluorine atoms or chlorine atoms,
Z M1 z is as follows M2 Z is as follows K1 Z is as follows K2 Respectively and independently represent a single bond, -CH 2 CH 2 -、-(CH 2 ) 4 -、-OCH 2 -、-CH 2 O-、-OCF 2 -、-CF 2 O-, -COO-, -OCO-or-C.ident.C-,
in the general formula (M), at n M1 Is 2, 3 or 4 and A M2 Z is as follows M1 In the case where there are plural, plural A M2 Z is as follows M1 Which may be the same or different from each other,
in the general formula (K), at n K1 Is 2, 3 or 4 and A K2 Z is as follows K1 In the case where there are plural, plural A K2 Z is as follows K1 Which may be the same or different from each other,
X M1 x is X M3 X is as follows K1 X is X K3 Each independently represents a hydrogen atom, a chlorine atom or a fluorine atom,
X M2 x is X K2 Each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a 2, 2-trifluoroethyl group.
5. A liquid crystal composition containing a pigment compound according to any one of claims 1 to 3, which contains a compound selected from the group of compounds represented by the general formulae (N-1) to (N-3) as a compound represented by the general formula (II),
Wherein R is N11 、R N12 、R N21 、R N22 、R N31 R is R N32 Independently represent an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent to or greater than 2-CH 2 Each independently is composed of-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution,
A N11 、A N12 、A N21 、A N22 、A N31 a is a N32 Each independently represents a radical selected from the group consisting of,
(a) 1, 4-cyclohexylene, 1-CH present in the radical 2 -or not more than 2-CH 2 Can be substituted by-O-,
(b) 1, 4-phenylene, 1-ch=or more than 2 non-adjacent-ch=present in the radical can be substituted to-n=, and
(c) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl, wherein 1-ch=or more than 2-ch=that are not adjacent to 1-ch=present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted to-n=,
the groups (a), (b) and (c) may each be independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z N11 、Z N12 、Z N21 、Z N22 、Z N31 z is as follows N32 Respectively and independently represent a single bond, -CH 2 CH 2 -、-(CH 2 ) 4 -、-OCH 2 -、-CH 2 O-、-COO-、-OCO-、-OCF 2 -、-CF 2 O-, -ch=n-n=ch-, -ch=ch-, -cf=cf-or-c≡c-,
X N21 represents a hydrogen atom or a fluorine atom,
T N31 represents-CH 2 -or an oxygen atom,
n N11 、n N12 、n N21 、n N22 、n N31 n is as follows N32 Each independently represents an integer of 0 to 3, n N11 +n N12 、n N21 +n N22 N is as follows N31 +n N32 Each independently is 1,2 or 3,
At A N11 To A N32 、Z N11 To Z N32 Where there are plural, they may be the same or different; wherein the compounds represented by the general formula (N-2) and the general formula (N-3) are excluded from the compounds represented by the general formula (N-1), and the compounds represented by the general formula (N-2) are excluded from the compounds represented by the general formula (N-3).
6. The liquid crystal composition containing a pigment compound according to any one of claims 3 to 5, which contains a compound selected from the group consisting of a compound represented by the general formula (L-1A), a compound represented by the general formula (L-1B), a compound represented by the general formula (L-2), a compound represented by the general formula (L-3), a compound represented by the general formula (L-4), a compound represented by the general formula (L-5), a compound represented by the general formula (L-6) and a compound represented by the general formula (L-7),
in the general formula (L-1A), R i1A R is R i2A Independently represent an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent to or greater than 2-CH 2 Each independently is composed of-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution, R is R i1A R is R i2A In at least one of the alkyl groups, 1 or non-contiguous 2 or more-CH 2 -each independently substituted with-ch=ch-,
wherein R is L11B R is R L12B Independently represent an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups being non-adjacent to or greater than 2-CH 2 Each independently of the others is composed of-C.ident.C-, -O-, -CO-, -COO-or-OCO-substitution,
Wherein R is L21 R is R L22 R in the general formula (L) is respectively and independently represented L1 R is R L2 The meaning of the same is that,
wherein R is L31 R is R L32 R in the general formula (L) is respectively and independently represented L1 R is R L2 The meaning of the same is that,
wherein R is L41 R is R L42 R in the general formula (L) is respectively and independently represented L1 R is R L2 The meaning of the same is that,
wherein R is L51 R is R L52 R in the general formula (L) is respectively and independently represented L1 R is R L2 The meaning of the same is that,
wherein R is L61 R is R L62 R in the general formula (L) is respectively and independently represented L1 R is R L2 Identical meaning, X L61 X is X L62 Each independently represents a hydrogen atom or a fluorine atom; wherein, except for the compound represented by the general formula (N-1),
wherein R is L71 R is R L72 R in the general formula (L) is respectively and independently represented L1 R is R L2 The same meaning, A L71 A is a L72 Each independently represents A in the general formula (L) L2 A is a L3 The same meaning, A L71 A is a L72 The hydrogen atoms of the radicals may be substituted independently of one another by fluorine atoms, Z L71 Z in the general formula (L) L2 Identical meaning, X L71 X is X L72 Each independently represents a fluorine atom or a hydrogen atom; wherein the compounds represented by the general formulae (N-1) to (N-3) are excluded.
7. The liquid crystal composition containing a pigment compound according to any one of claims 1 to 6, wherein the total amount of the content of the general formula (1) is 0.01 mass% or more and 10 mass% or less with respect to the total amount of the liquid crystal composition.
8. The liquid crystal composition containing a pigment compound according to any one of claims 1 to 7, which contains one or two or more compounds selected from the group consisting of a light stabilizer, an antioxidant and an ultraviolet absorber.
9. The liquid crystal composition containing a pigment compound according to any one of claims 1 to 8, which contains one or two or more polymerizable compounds.
10. A liquid crystal display element or a light adjusting element using the liquid crystal composition containing the pigment compound according to any one of claims 1 to 9.
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| JP2022037023A JP2023131973A (en) | 2022-03-10 | 2022-03-10 | Liquid crystal composition and liquid crystal element |
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| JP (1) | JP2023131973A (en) |
| CN (1) | CN116731725A (en) |
| TW (1) | TW202340431A (en) |
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| TW202340431A (en) | 2023-10-16 |
| JP2023131973A (en) | 2023-09-22 |
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