JPWO2017002792A1 - 液晶組成物及びこれを用いた液晶表示素子 - Google Patents
液晶組成物及びこれを用いた液晶表示素子 Download PDFInfo
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- JPWO2017002792A1 JPWO2017002792A1 JP2016573145A JP2016573145A JPWO2017002792A1 JP WO2017002792 A1 JPWO2017002792 A1 JP WO2017002792A1 JP 2016573145 A JP2016573145 A JP 2016573145A JP 2016573145 A JP2016573145 A JP 2016573145A JP WO2017002792 A1 JPWO2017002792 A1 JP WO2017002792A1
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- diyl
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 116
- 239000000203 mixture Substances 0.000 title claims abstract description 94
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 125000001153 fluoro group Chemical group F* 0.000 claims description 96
- -1 naphthalene-1,4-diyl group Chemical group 0.000 claims description 73
- 125000004432 carbon atom Chemical group C* 0.000 claims description 58
- 229910052731 fluorine Inorganic materials 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 27
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 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 2
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 claims description 2
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- 239000003112 inhibitor Substances 0.000 claims description 2
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- 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 3
- OKOBUGCCXMIKDM-UHFFFAOYSA-N Irganox 1098 Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NCCCCCCNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 OKOBUGCCXMIKDM-UHFFFAOYSA-N 0.000 description 3
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- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WPMYUUITDBHVQZ-UHFFFAOYSA-M 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=CC(CCC([O-])=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-M 0.000 description 2
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical group C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 2
- 150000001565 benzotriazoles Chemical class 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000005725 cyclohexenylene group Chemical group 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
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- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000005651 substituted 1,4-phenylene group Chemical group 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 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
- XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- SSMSBSWKLKKXGG-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-isopropylaminoethanol Chemical compound CC(C)NCC(O)C1=CC=CC=C1Cl SSMSBSWKLKKXGG-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- VTFXHGBOGGGYDO-UHFFFAOYSA-N 2,4-bis(dodecylsulfanylmethyl)-6-methylphenol Chemical compound CCCCCCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCCCCCC)=C1 VTFXHGBOGGGYDO-UHFFFAOYSA-N 0.000 description 1
- VOQFZENYFWLTBF-UHFFFAOYSA-N 2,4-ditert-butyl-6-(5-chloro-2H-benzotriazol-4-yl)phenol Chemical compound CC(C)(C)c1cc(c(O)c(c1)C(C)(C)C)-c1c(Cl)ccc2[nH]nnc12 VOQFZENYFWLTBF-UHFFFAOYSA-N 0.000 description 1
- YATYZLYTTAAVIF-UHFFFAOYSA-N 2-(5-chlorobenzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O YATYZLYTTAAVIF-UHFFFAOYSA-N 0.000 description 1
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 1
- UZUNCLSDTUBVCN-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C=1C(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C(O)C=1C(C)(C)C1=CC=CC=C1 UZUNCLSDTUBVCN-UHFFFAOYSA-N 0.000 description 1
- VFBJXXJYHWLXRM-UHFFFAOYSA-N 2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCSCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VFBJXXJYHWLXRM-UHFFFAOYSA-N 0.000 description 1
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 1
- GAODDBNJCKQQDY-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCC)=C1 GAODDBNJCKQQDY-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- 125000005653 3,5-difluoro-1,4-phenylene group Chemical group [H]C1=C(F)C([*:2])=C(F)C([H])=C1[*:1] 0.000 description 1
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 description 1
- QRLSTWVLSWCGBT-UHFFFAOYSA-N 4-((4,6-bis(octylthio)-1,3,5-triazin-2-yl)amino)-2,6-di-tert-butylphenol Chemical compound CCCCCCCCSC1=NC(SCCCCCCCC)=NC(NC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=N1 QRLSTWVLSWCGBT-UHFFFAOYSA-N 0.000 description 1
- BOBHIPMYQAROLL-UHFFFAOYSA-N 4-chloro-6-imidazol-1-ylpyrimidine Chemical compound C1=NC(Cl)=CC(N2C=NC=C2)=N1 BOBHIPMYQAROLL-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 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
- 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
- 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 1
- 230000032900 absorption of visible light Effects 0.000 description 1
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- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- OOCILPYOPQKPJY-UHFFFAOYSA-N calcium;(3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinic acid Chemical compound [Ca].CCOP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 OOCILPYOPQKPJY-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000011109 contamination Methods 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- LRMJAFKKJLRDLE-UHFFFAOYSA-N dotarizine Chemical compound O1CCOC1(C=1C=CC=CC=1)CCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 LRMJAFKKJLRDLE-UHFFFAOYSA-N 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
- 239000012776 electronic material Substances 0.000 description 1
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- 239000006260 foam Substances 0.000 description 1
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- 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
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- MBAUOPQYSQVYJV-UHFFFAOYSA-N octyl 3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoate Chemical compound OC1=C(C=C(C=C1C(C)C)CCC(=O)OCCCCCCCC)C(C)C MBAUOPQYSQVYJV-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
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- 229920005989 resin Polymers 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
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- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
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- 238000002834 transmittance Methods 0.000 description 1
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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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/24—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing nitrogen-to-nitrogen bonds
-
- 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
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
-
- 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
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
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Abstract
Description
Zi1、Zi2及びZi3はそれぞれ独立して単結合、−OCH2−、−CH2O−、−C2H4−、−C4H8−、−COO−、−OCO−、−CH=CH−、−CF=CF−、−CF2O−、−OCF2−、−CF2CF2−又は−C≡C−を表し、
Ai1、Ai2、Ai3、Ai4及びAi5はそれぞれ独立して1,4−シクロヘキシレン基、1,4−フェニレン基、ナフタレン−1,4−ジイル基又はナフタレン−2,6−ジイル基を表し、Ai1、Ai2、Ai3、Ai4及びAi5中の1個又は2個以上の水素原子はそれぞれ独立してハロゲン原子又はシアノ基で置換されていてもよく、Ai1、Ai2、Ai3、Ai4及びAi5中の非隣接の一個以上の−CH=は−N=で置換されていてもよく、
Xi1及びXi2はそれぞれ独立して水素原子又はフッ素原子を表し、
mi1、mi2及びmi3はそれぞれ独立して0又は1を表すが、mi1+mi2+mi3は0又は1を表す。)で表される化合物を1種又は2種以上と、
一般式(C1)から(C3)
環G、環H、環I及び環Jはそれぞれ独立的に、トランス−1,4−シクロへキシレン基、トランスデカヒドロナフタレン−トランス−2,6−ジイル基、1〜2個のフッ素原子あるいはメチル基により置換されていてもよい1,4−フェニレン基、1個以上のフッ素原子により置換されていてもよいナフタレン−2,6−ジイル基、1〜2個のフッ素原子により置換されていてもよいテトラヒドロナフタレン−2,6−ジイル基、1〜2個のフッ素原子により置換されていてもよい1,4−シクロヘキセニレン基、1,3−ジオキサン−トランス−2,5−ジイル基、ピリミジン−2,5−ジイル基又はピリジン−2,5−ジイル基を表し、
Lg、Lh及びLiはそれぞれ独立的に単結合、エチレン基(−CH2CH2−)、1,2−プロピレン基(−CH(CH3)CH2−及び)−CH2CH(CH3)−)、1,4−ブチレン基、−COO−、−OCO−、−OCF2−、−CF2O−、−CH=CH−、−CH=CF−、−CF=CH−、−CF=CF−、−C≡C−又は−CH=NN=CH−を表し、
なお一般式(C1)から(C3)で表される化合物を組み合わせて使用する場合、異なる分子中の同一の選択肢(環GやLg等)は同一の置換基を表しても、異なる置換基を表してもよい。)
で表される化合物を1種又は2種以上含有する液晶組成物、当該液晶組成物を用いた液晶表示素子、当該液晶組成物を用いた液晶レンズ及び当該液晶組成物を用いた立体画像表示用複屈折レンズを提供する。
一般式(C1)から(C3)で表される化合物は誘電率異方性が0程度である、いわゆるノンポーラー型化合物である。
La、Lb及びLcは連結基であって、それぞれ独立的に単結合、エチレン基(−CH2CH2−)、1,2−プロピレン基(−CH(CH3)CH2−及び−CH2CH(CH3)−)、1,4−ブチレン基、−COO−、−OCO−、−OCF2−、−CF2O−、−CH=CH−、−CH=CF−、−CF=CH−、−CF=CF−、−C≡C−又は−CH=NN=CH−を表すが、単結合、エチレン基、1,4−ブチレン基、−COO−、−OCF2−、−CF2O−、−CF=CF−又は−C≡C−が好ましく、単結合又はエチレン基が特に好ましい。また、(A2)においてはその少なくとも1個が、(A3)においてはその少なくとも2個が単結合を表すことが好ましい。
さらに好ましくは、下記化合物である。
さらに好ましくは、下記化合物である。
T→N :ネマチック相となる相転移温度
Δn :298Kにおける屈折率異方性
no :
Δε :298Kにおける誘電率異方性
ε⊥ :
γ1 :298Kにおける回転粘度
Vth :厚さ8.3ミクロンのTNセルに液晶を封入し、298K、クロスニコル偏光板下において透過率が10%変化する電圧。
耐熱試験後VHR:組成物サンプルを封入した電気光学特性評価用TEG(テスト・エレメント・グループ)を130℃の恒温槽中に1時間保持した後、上述のVHR測定方法と同条件で測定した。
液晶組成物を、TN用液晶セル(セルギャップ8.3μm)に真空注入し、UV硬化性樹脂(スリーボンド社製、Three Bond 3026)で封止し、液晶セルを作製した。
液晶表示素子の焼き付き評価は、表示エリア内に所定の固定パターンを任意の試験時間表示させた後に、全画面均一な表示を行ったときの固定パターンの残像が、許容できない残像レベルに達するまでの試験時間を計測した。
1)ここで言う試験時間とは固定パターンの表示時間を示し、この時間が長いほど残像の発生が抑制されており、性能が高いことを示している。
2)許容できない残像レベルとは、出荷合否判定で不合格となる残像が観察されるレベルである。
例)
サンプルA:1000時間
サンプルB:500時間
サンプルC:200時間
サンプルD:100時間
性能は、A>B>C>Dである。
液晶表示装置の滴下痕の評価は、全面黒表示した場合における白く浮かび上がる滴下痕を目視にて以下の5段階評価で行った。
4:滴下痕ごく僅かに有るも許容できるレベル(良)
3:滴下痕僅かに有り、合否判定のボーダーラインレベル(条件付で可)
2:滴下痕有り許容できないレベル(不可)
1:滴下痕有りかなり劣悪(悪)
プロセス適合性 :
プロセス適合性は、ODFプロセスにおいて、定積計量ポンプを用いて、液晶を1回に50pLずつ「0〜100回、101〜200回、201〜300回、・・・・」と100回ずつ滴下したときの各100回滴下分の液晶の質量を計測し、質量のバラつきがODFプロセスに適合できない大きさに達した滴下回数で評価した。
滴下回数が多いほど長時間にわたって安定的に滴下可能であり、プロセス適合性が高いといえる。
例)
サンプルA:95000回
サンプルB:40000回
サンプルC:100000回
サンプルD:10000回
性能は、C>A>B>Dである。
低温での保存性評価は、組成物を調製後、1mLのサンプル瓶に組成物を0.5g秤量し、これを−25℃の温度制御式試験槽の中で240時間保存して目視にて組成物からの析出物の発生を観察し、析出物が観察されたときの試験時間を計測した。析出発生までの試験時間が長いほど低温での保存性が良好であるといえる。
液晶材料の揮発性評価は、真空攪拌脱泡ミキサーの運転状態をストロボスコープを用いて観察し、液晶材料の発泡を目視により観察することによって行った。具体的には、容量2.0Lの真空攪拌脱泡ミキサーの専用容器に組成物を0.8kg入れ、4kPaの脱気下、公転速度15S−1、自転速度7.5S−1で真空攪拌脱泡ミキサーを運転し、発泡が始まるまでの時間を計測した。
発泡が始まるまでの時間が長いほど揮発しにくく、製造装置を汚染する可能性が低いので、高性能であることを示す。
例)
サンプルA:200秒
サンプルB:45秒
サンプルC:60秒
サンプルD:15秒
性能は、A>C>B>Dである。
尚、実施例において化合物の記載について以下の略号を用いる。
(環構造)
(側鎖構造及び連結構造)
本願発明の液晶組成物及び該組成物を使用した液晶表示素子を作製し、その物性値を測定した。
更に下記組成物の物性値を示す。
Claims (11)
- 一般式(i)
Zi1、Zi2及びZi3はそれぞれ独立して単結合、−OCH2−、−CH2O−、−C2H4−、−C4H8−、−COO−、−OCO−、−CH=CH−、−CF=CF−、−CF2O−、−OCF2−、−CF2CF2−又は−C≡C−を表し、
Ai1、Ai2、Ai3、Ai4及びAi5はそれぞれ独立して1,4−シクロヘキシレン基、1,4−フェニレン基、ナフタレン−1,4−ジイル基又はナフタレン−2,6−ジイル基を表し、Ai1、Ai2、Ai3、Ai4及びAi5中の1個又は2個以上の水素原子はそれぞれ独立してハロゲン原子又はシアノ基で置換されていてもよく、Ai1、Ai2、Ai3、Ai4及びAi5中の非隣接の一個以上の−CH=は−N=で置換されていてもよく、
Xi1及びXi2はそれぞれ独立して水素原子又はフッ素原子を表し、
mi1、mi2及びmi3はそれぞれ独立して0又は1を表すが、mi1+mi2+mi3は0又は1を表す。)で表される化合物を1種又は2種以上と、
一般式(C1)から(C3)
環G、環H、環I及び環Jはそれぞれ独立的に、トランス−1,4−シクロへキシレン基、トランスデカヒドロナフタレン−トランス−2,6−ジイル基、1〜2個のフッ素原子あるいはメチル基により置換されていてもよい1,4−フェニレン基、1個以上のフッ素原子により置換されていてもよいナフタレン−2,6−ジイル基、1〜2個のフッ素原子により置換されていてもよいテトラヒドロナフタレン−2,6−ジイル基、1〜2個のフッ素原子により置換されていてもよい1,4−シクロヘキセニレン基、1,3−ジオキサン−トランス−2,5−ジイル基、ピリミジン−2,5−ジイル基又はピリジン−2,5−ジイル基を表し、
Lg、Lh及びLiはそれぞれ独立的に単結合、エチレン基(−CH2CH2−)、1,2−プロピレン基(−CH(CH3)CH2−及び)−CH2CH(CH3)−)、1,4−ブチレン基、−COO−、−OCO−、−OCF2−、−CF2O−、−CH=CH−、−CH=CF−、−CF=CH−、−CF=CF−、−C≡C−又は−CH=NN=CH−を表し、
なお一般式(C1)から(C3)で表される化合物を組み合わせて使用する場合、異なる分子中の同一の選択肢(環GやLg等)は同一の置換基を表しても、異なる置換基を表してもよい。)
で表される化合物を1種又は2種以上含有する液晶組成物。 - 一般式(i)において、Ri1及びRi2がそれぞれ独立して炭素原子数1〜12のアルキル基である請求項1に記載の液晶組成物。
- 一般式(i)において、Ai1、Ai2、Ai3、Ai4及びAi5はそれぞれ独立して無置換であるか又はAi1、Ai2、Ai3、Ai4及びAi5中の1個又は2個以上の水素原子がフッ素原子により置換されていてもよい1,4−フェニレン基である請求項1又は2に記載の液晶組成物。
- 一般式(i)において、mi1、mi2及びmi3が0である請求項1から3のいずれか一項に記載の液晶組成物。
- 更に、一般式(A1)から(A3)
環A、環B及び環Cはそれぞれ独立的にトランス−1,4−シクロへキシレン基、トランスデカヒドロナフタレン−トランス−2,6−ジイル基、1個以上のフッ素原子により置換されていてもよい1,4−フェニレン基、1個以上のフッ素原子により置換されていてもよいナフタレン−2,6−ジイル基、1個以上のフッ素原子により置換されていてもよいテトラヒドロナフタレン−2,6−ジイル基、フッ素原子により置換されていてもよい1,4−シクロヘキセニレン基、1,3−ジオキサン−トランス−2,5−ジイル基、ピリミジン−2,5−ジイル基またはピリジン−2,5−ジイル基を表し、
La、Lb及びLcはそれぞれ独立的に単結合、エチレン基(−CH2CH2−)、1,2−プロピレン基(−CH(CH3)CH2−及び−CH2CH(CH3)−)、1,4−ブチレン基、−COO−、−OCO−、−OCF2−、−CF2O−、−CH=CH−、−CH=CF−、−CF=CH−、−CF=CF−、−C≡C−又は−CH=NN=CH−を表し、
環Zは一般式(La)〜(Lc)で表される置換基を表し、
Paはフッ素原子、塩素原子、トリフルオロメトキシ基、ジフルオロメトキシ基、トリフルオロメチル基又はジフルオロメチル基あるいは2個以上のフッ素原子により置換された炭素原子数2又は3のアルコキシル基、アルキル基、アルケニル基又はアルケニルオキシ基を表し、
一般式(A1)から(A3)で表される化合物を組み合わせて使用する場合、異なる分子中の同一の選択肢(環AやLa等)は同一の置換基を表しても、異なる置換基を表してもよい。)
で表される化合物を1種又は2種以上含有する請求項1から4のいずれか一項に記載の液晶組成物。 - 更に、一般式(B1)から(B3)
環D、環E及び環Fはそれぞれ独立的にトランス−1,4−シクロへキシレン基、トランスデカヒドロナフタレン−トランス−2,6−ジイル基、1個以上のフッ素原子により置換されていてもよい1,4−フェニレン基、1個以上のフッ素原子により置換されていてもよいナフタレン−2,6−ジイル基、1個以上のフッ素原子により置換されていてもよいテトラヒドロナフタレン−2,6−ジイル基、フッ素原子により置換されていてもよい1,4−シクロヘキセニレン基、1,3−ジオキサン−トランス−2,5−ジイル基、ピリミジン−2,5−ジイル基又はピリジン−2,5−ジイル基を表し、
Ld、Le及びLfはそれぞれ独立的に単結合、エチレン基(−CH2CH2−)、1,2−プロピレン基(−CH(CH3)CH2−及び)−CH2CH(CH3)−)、1,4−ブチレン基、−COO−、−OCO−、−OCF2−、−CF2O−、−CH=CH−、−CH=CF−、−CF=CH−、−CF=CF−、−C≡C−、−OCH2−、−CH2O−又は−CH=NN=CH−を表し、
環Yは芳香環であり以下の一般式(Ld)〜(Lf)で表される置換基を表し、
末端基Pbはシアノ基(−CN)、シアナト基(−OCN)又は−C≡CCNを表し、
一般式(B1)から(B3)で表される化合物を組み合わせて使用する場合、異なる分子中の同一の選択肢(環DやLd等)は同一の置換基を表しても、異なる置換基を表してもよい。)
で表される化合物を1種又は2種以上含有する請求項1から5のいずれか一項に記載の液晶組成物。 - 屈折率異方性が0.15以上である請求項1から6のいずれか1項に記載の液晶組成物。
- 酸化防止剤、紫外線防止剤、カイラル剤、帯電防止剤及び二色性色素の少なくともいずれか1つを1種又は2種以上含有する請求項1から7のいずれか1項に記載の液晶組成物。
- 請求項1から8のいずれか1項に記載の液晶組成物を用いた液晶表示素子。
- 請求項1から8のいずれか1項に記載の液晶組成物を用いた液晶レンズ。
- 請求項1から8のいずれか1項に記載の液晶組成物を用いた立体画像表示用複屈折レンズ。
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