JP5621952B1 - 液晶組成物および液晶表示素子 - Google Patents
液晶組成物および液晶表示素子 Download PDFInfo
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- JP5621952B1 JP5621952B1 JP2014530993A JP2014530993A JP5621952B1 JP 5621952 B1 JP5621952 B1 JP 5621952B1 JP 2014530993 A JP2014530993 A JP 2014530993A JP 2014530993 A JP2014530993 A JP 2014530993A JP 5621952 B1 JP5621952 B1 JP 5621952B1
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- 239000000203 mixture Substances 0.000 title claims abstract description 163
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 113
- 150000001875 compounds Chemical class 0.000 claims abstract description 225
- 230000003287 optical effect Effects 0.000 claims abstract description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 392
- -1 1 , 4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl Chemical group 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 239000011737 fluorine Substances 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000003342 alkenyl group Chemical group 0.000 claims description 33
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical group 0.000 claims description 18
- 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 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000005701 difluoromethyleneoxy group Chemical group FC(F)([*:1])O[*:2] 0.000 claims description 8
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 7
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005453 2,5-difluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C(F)=C([H])C([*:2])=C1F 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 230000004044 response Effects 0.000 abstract description 9
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- 238000005259 measurement Methods 0.000 description 18
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- QUJIDNSQCMTYNG-UHFFFAOYSA-N 5-[4-(4-butylphenyl)-2-fluorophenyl]-2-[difluoro-(3,4,5-trifluorophenoxy)methyl]-1,3-difluorobenzene Chemical compound C1=CC(CCCC)=CC=C1C1=CC=C(C=2C=C(F)C(=C(F)C=2)C(F)(F)OC=2C=C(F)C(F)=C(F)C=2)C(F)=C1 QUJIDNSQCMTYNG-UHFFFAOYSA-N 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 239000000758 substrate Substances 0.000 description 8
- 238000002834 transmittance Methods 0.000 description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 8
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- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical group C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
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- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000006017 1-propenyl group Chemical group 0.000 description 3
- KOFASFPAZGQDKP-UHFFFAOYSA-N 2-[difluoro-(3,4,5-trifluorophenoxy)methyl]-1,3-difluoro-5-[2-fluoro-4-(4-pentylphenyl)phenyl]benzene Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C=2C=C(F)C(=C(F)C=2)C(F)(F)OC=2C=C(F)C(F)=C(F)C=2)C(F)=C1 KOFASFPAZGQDKP-UHFFFAOYSA-N 0.000 description 3
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000006039 1-hexenyl group Chemical group 0.000 description 2
- 125000006023 1-pentenyl group Chemical group 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000006040 2-hexenyl group Chemical group 0.000 description 2
- 125000006024 2-pentenyl group Chemical group 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- 125000006041 3-hexenyl group Chemical group 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 0 CCC(C)(*)C(CC1)CCC1N Chemical compound CCC(C)(*)C(CC1)CCC1N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000013213 extrapolation Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- ZKJNETINGMOHJG-GGWOSOGESA-N (e)-1-[(e)-prop-1-enoxy]prop-1-ene Chemical compound C\C=C\O\C=C\C ZKJNETINGMOHJG-GGWOSOGESA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
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- 239000000853 adhesive Substances 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
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- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011903 deuterated solvents Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
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- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
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- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
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- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- NTJBWZHVSJNKAD-UHFFFAOYSA-N triethylazanium;fluoride Chemical compound [F-].CC[NH+](CC)CC NTJBWZHVSJNKAD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 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
- C09K19/06—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
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
-
- 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
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
-
- 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
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
- C09K19/0208—Twisted Nematic (T.N.); Super Twisted Nematic (S.T.N.); Optical Mode Interference (O.M.I.)
-
- 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
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
- C09K19/0216—Super Birefringence Effect (S.B.E.); Electrically Controlled Birefringence (E.C.B.)
-
- 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
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Abstract
Description
式(1)および式(2)において、R1およびR2は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、または炭素数2から12のアルケニルであり;R3は、炭素数2から12のアルケニル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Aおよび環Bは独立して、1,4−シクロへキシレン、1,4−フェニレン、2−フルオロ−1,4−フェニレン、2,3−ジフルオロ−1,4−フェニレン、2,6−ジフルオロ−1,4−フェニレン、ピリミジン−2,5−ジイル、1,3−ジオキサン−2,5−ジイル、またはテトラヒドロピラン−2,5−ジイルであり;Z1およびZ2は独立して、単結合、エチレン、ビニレン、メチレンオキシ、カルボニルオキシ、またはジフルオロメチレンオキシであり;L1およびL2は独立して、フッ素または塩素であり;X1およびX2は独立して、水素またはフッ素であり;Y1は、フッ素、塩素、少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルコキシであり;mおよびjは独立して、0、1、2、または3であり、そしてmとjの和は3以下である。
式(1)および式(2)において、R1およびR2は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、または炭素数2から12のアルケニルであり;R3は、炭素数2から12のアルケニル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Aおよび環Bは独立して、1,4−シクロへキシレン、1,4−フェニレン、2−フルオロ−1,4−フェニレン、2,3−ジフルオロ−1,4−フェニレン、2,6−ジフルオロ−1,4−フェニレン、ピリミジン−2,5−ジイル、1,3−ジオキサン−2,5−ジイル、またはテトラヒドロピラン−2,5−ジイルであり;Z1およびZ2は独立して、単結合、エチレン、ビニレン、メチレンオキシ、カルボニルオキシ、またはジフルオロメチレンオキシであり;L1およびL2は独立して、フッ素または塩素であり;X1およびX2は独立して、水素またはフッ素であり;Y1は、フッ素、塩素、少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルコキシであり;mおよびjは独立して、0、1、2、または3であり、そしてmとjの和は3以下である。
式(1−1)から式(1−14)において、R1は、炭素数1から12のアルキル、炭素数1から12のアルコキシ、または炭素数2から12のアルケニルであり;L1およびL2は独立して、フッ素または塩素であり;X1、X2、X3、X4、X5、X6、X7、およびX8は独立して、水素またはフッ素であり;Y1は、フッ素、塩素、少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルコキシである。
式(3)において、R4およびR5は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Cおよび環Dは独立して、1,4−シクロへキシレン、1,4−フェニレン、2−フルオロ−1,4−フェニレン、または2,5−ジフルオロ−1,4−フェニレンであり;Z3は、単結合、エチレンまたはカルボニルオキシであり;nは、1、2、または3であり;ただしnが1のとき、環Cは1,4−フェニレンである。
式(3−1)から式(3−12)において、R4およびR5は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルである。
式(4)において、R6は炭素数1から12のアルキル、炭素数1から12のアルコキシ、または炭素数2から12のアルケニルであり;環Eは、1,4−シクロへキシレン、1,4−フェニレン、2−フルオロ−1,4−フェニレン、2,6−ジフルオロ−1,4−フェニレン、ピリミジン−2,5−ジイル、1,3−ジオキサン−2,5−ジイル、またはテトラヒドロピラン−2,5−ジイルであり;Z4は、単結合、エチレン、カルボニルオキシ、またはジフルオロメチレンオキシであり;X9およびX10は独立して、水素またはフッ素であり;Y2は、フッ素、塩素、少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルコキシであり;pは、1、2、3、または4である。
式(4−1)から式(4−27)において、R6は、炭素数1から12のアルキル、炭素数1から12のアルコキシ、または炭素数2から12のアルケニルである。
液晶のらせん構造を誘起してねじれ角を与える目的で光学活性化合物が組成物に添加される。このような化合物の例は、化合物(5−1)から化合物(5−5)である。光学活性化合物の好ましい割合は約5重量%以下である。さらに好ましい割合は約0.01重量%から約2重量%の範囲である。
窒素雰囲気下、化合物(T−1)(9.25g)、トルエン(20.0ml)、および2,2,4−トリメチルペンタン(20.0ml)を反応器に入れて、60℃に加熱した。そこへプロパンジチオール(4.31ml)を加え1時間撹拌したのち、トリフルオロメタンスルホン酸(7.63ml)をゆっくりと加え1時間撹拌した。続いて留出してくる水を除去しつつ、さらに2時間加熱還流を行った。反応混合物を室温まで冷却したのち、減圧下で濃縮し、残渣をt−ブチルメチルエーテルからの再結晶により精製して、化合物(T−2)(13.9g;78%)を得た。
窒素雰囲気下、化合物(T−3)(5.38g)、トリエチルアミン(5.48ml)、およびジクロロメタン(50.0ml)を反応器に入れて、−70℃に冷却した。そこへ化合物(T−2)(13.9g)のジクロロメタン(200ml)溶液をゆっくりと加え1時間撹拌した。次にフッ化水素トリエチルアミン錯体(14.8ml)をゆっくりと加え30分間撹拌した。続いて臭素(7.80ml)をゆっくりと加えさらに1時間撹拌した。反応混合物を氷水に注ぎ込み、炭酸水素ナトリウムを用いて中和したのち、水層をジクロロメタンで抽出した。一緒にした有機層を水で洗浄し、無水硫酸マグネシウムで乾燥した。この溶液を減圧下で濃縮し、残渣をシリカゲルクロマトグラフィー(ヘプタン)で精製して、化合物(T−4)(11.0g;93%)を得た。
窒素雰囲気下、化合物(T−4)(4.00g)、化合物(T−5)(1.86g)、テトラキス(トリフェニルホスフィン)パラジウム(0.119g)、炭酸カリウム(2.84g)、テトラブチルアンモニウムブロミド(TBAB)(0.663g)、トルエン(40.0ml)、ソルミックス(日本アルコール販売株式会社;登録商標)A−11(40.0ml)、および水(40.0ml)を反応器に入れて、5時間加熱還流を行った。反応混合物を水に注ぎ込み、水層をトルエンで抽出した。一緒にした有機層を水で洗浄し、無水硫酸マグネシウムで乾燥した。この溶液を減圧下で濃縮し、残渣をシリカゲルクロマトグラフィー(ヘプタン)で精製した。さらにソルミックス(日本アルコール販売株式会社;登録商標)A−11からの再結晶により精製して、化合物(No.1−4−1)(3.73g;85%)を得た。
国際公開第1996/11897号パンフレットに開示された組成物の中から実施例39を選んだ。根拠は、この組成物が化合物(4)を含有し、そしてηが最も小さいからである。この組成物の成分および特性は下記のとおりであった。
3−HBXB(F,F)−F (4) 3%
5−HBXB(F,F)−F (4) 8%
3−HBXB−OCF3 (4) 5%
2−HBB(F)−F (4) 8%
3−HBB(F)−F (4) 8%
5−HBB(F)−F (4) 16%
5−HB−F (4) 6%
7−HB−F (4) 6%
5−HHB−OCF3 (4) 8%
3−H2HB−OCF3 (4) 8%
5−H2HB−OCF3 (4) 8%
3−HH2B−OCF3 (4) 8%
5−HH2B−OCF3 (4) 8%
NI=84.9℃;Δn=0.101;Δε=5.5;Vth=2.12V;η=16.6mPa・s.
特開2001−139511号公報に開示された組成物の中から使用例18を選んだ。根拠は、この組成物が化合物(3−1)、化合物(3−4)、および化合物(4)を含有し、そしてηが最も小さいからである。この組成物の成分および特性は下記のとおりであった。
3−HBxB(2F,3F)−O2 (−) 5%
5−HBxB(2F,3F)−O2 (−) 5%
7−HB(F)−F (4) 5%
5−H2B(F)−F (4) 5%
3−HB−O2 (3−1) 10%
3−HH−4 (−) 5%
2−HHB(F)−F (4) 10%
3−HHB(F)−F (4) 10%
3−H2HB(F)−F (4) 5%
2−HBB(F)−F (4) 3%
3−HBB(F)−F (4) 3%
5−HBB(F)−F (4) 6%
2−H2BB(F)−F (4) 5%
3−H2BB(F)−F (4) 6%
3−HHB−1 (3−4) 8%
3−HHB−O1 (3−4) 5%
3−HHB−3 (3−4) 4%
NI=89.2℃;Δn=0.099;Δε=2.2;Vth=3.05V;η=20.2mPa・s.
3−BB(2F,3F)XB(F,F)−F (1−4) 19%
3−HH−V (2) 32%
3−HH−V1 (2) 5%
V−HHB−1 (3−4) 13%
1−BB(F)B−2V (3−6) 2%
2−HHBB(F,F)−F (4−17) 3%
3−HHBB(F,F)−F (4−17) 3%
3−HBBXB(F,F)−F (4−20) 8%
3−BB(F)B(F,F)XB(F,F)−F(4−25) 2%
4−BB(F)B(F,F)XB(F,F)−F(4−25) 7%
5−BB(F)B(F,F)XB(F,F)−F(4−25) 6%
NI=86.3℃;Tc<−20℃;Δn=0.116;Δε=7.6;Vth=1.56V;η=10.0mPa・s;γ1=80.1mPa・s;ε⊥/Δε=0.47.
5−HB(2F,3F)B(2F,3F)XB(F,F)−F
(1) 6%
3−GB(2F,3F)XB(F,F)−F (1−3) 7%
3−BB(2F,3F)XB(F,F)−F (1−4) 8%
4−HH−V (2) 20%
4−HH−V1 (2) 12%
7−HB−1 (3−1) 3%
3−HHEH−3 (3−3) 3%
3−HHEH−5 (3−3) 4%
3−HBB−2 (3−5) 3%
5−B(F)BB−2 (3−7) 5%
5−B(F)BB−3 (3−7) 3%
3−HHXB(F,F)−CF3 (4) 6%
3−HB−CL (4−1) 3%
3−HBB(F,F)−F (4−8) 3%
3−GB(F,F)XB(F,F)−F (4−12) 5%
3−HBB(F,F)XB(F,F)−F (4−21) 3%
3−BB(F,F)XB(F)B(F,F)−F(4−26) 3%
5−BB(F)B(F,F)XB(F)B(F,F)−F
(4−27) 3%
NI=71.4℃;Tc<−20℃;Δn=0.105;Δε=7.0;Vth=1.65V;η=13.9mPa・s;γ1=83.7mPa・s;ε⊥/Δε=0.51.
3−BB(2F,3F)XB(F)−F (1−4) 5%
3−HBB(2F,3F)XB(F,F)−F (1−7) 5%
3−dhBB(2F,3F)XB(F,F)−F(1−8) 5%
3−HH−V (2) 10%
3−HH−V1 (2) 5%
3−HH−VFF (2) 22%
V2−BB−1 (3−2) 5%
3−HB(F)HH−2 (3−8) 4%
5−HBB(F)B−2 (3−12) 4%
5−HXB(F,F)−F (4−2) 4%
3−HHXB(F,F)−F (4−5) 6%
3−BBXB(F,F)−F (4−15) 3%
3−BB(F,F)XB(F,F)−F (4−16) 3%
3−dhBB(F,F)XB(F,F)−F (4−22) 5%
3−GB(F)B(F,F)XB(F,F)−F(4−23) 5%
5−GB(F)B(F,F)XB(F,F)−F(4−23) 4%
1O1−HBBH−5 (−) 5%
NI=86.2℃;Tc<−20℃;Δn=0.112;Δε=7.8;Vth=1.53V;η=11.1mPa・s;γ1=81.1mPa・s;ε⊥/Δε=0.46.
3−BB(2F,3F)XB(F,F)−F (1−4) 10%
3−GBB(2F,3F)XB(F,F)−F (1−9) 6%
3−GBB(2F,3F)XB(F)−F (1−9) 5%
1V2−HH−1 (2) 10%
1V2−HH−3 (2) 12%
3−HH−V (2) 19%
3−BB(2F,5F)B−3 (3) 3%
3−HHEBH−3 (3−9) 5%
3−HHEBH−5 (3−9) 5%
3−HHB(F,F)−F (4−3) 6%
3−HGB(F,F)−F (4−6) 3%
V−HB(F)B(F,F)−F (4−9) 5%
3−BB(F)B(F,F)−F (4−13) 3%
3−BB(F)B(F,F)XB(F)−F (4−24) 3%
4−BB(F)B(F,F)XB(F)−F (4−24) 5%
NI=93.9℃;Tc<−20℃;Δn=0.110;Δε=5.7;Vth=1.81V;η=13.4mPa・s;γ1=83.0mPa・s;ε⊥/Δε=0.49.
3−GB(2F,3F)XB(F,F)−F (1−3) 6%
3−BB(2F,3F)XB(F)−F (1−4) 8%
3−BB(2F,3F)XB(F,F)−F (1−4) 7%
3−HH−V (2) 25%
3−HH−V1 (2) 6%
1V2−BB−1 (3−2) 4%
5−HBBH−3 (3−10) 6%
5−HEB(F,F)−F (4) 3%
3−HHB−CL (4) 5%
5−HHB−CL (4) 4%
3−HHEB(F,F)−F (4−4) 4%
5−HHEB(F,F)−F (4−4) 4%
3−HBEB(F,F)−F (4−10) 3%
5−HBEB(F,F)−F (4−10) 3%
4−HHB(F)B(F,F)−F (4−18) 7%
4−BB(F)B(F,F)XB(F、F)−F(4−25) 5%
NI=83.9℃;Tc<−20℃;Δn=0.105;Δε=6.4;Vth=1.69V;η=12.2mPa・s;γ1=82.2mPa・s;ε⊥/Δε=0.50.
3−BB(2F,3F)XB(F,F)−F (1−4) 10%
3−HBB(2F,3F)XB(F,F)−F (1−7) 5%
3−dhBB(2F,3F)XB(F,F)−F(1−8) 5%
4−HH−V (2) 12%
3−HH−V (2) 20%
3−HHB−1 (3−4) 6%
3−HHB−3 (3−4) 7%
5−HB(F)BH−3 (3−11) 2%
3−H2GB(F,F)−F (4) 4%
3−GHB(F,F)−F (4−7) 3%
5−GB(F)B(F,F)−F (4−11) 3%
3−BB(F,F)XB(F,F)−F (4−16) 6%
3−GBB(F)B(F,F)−F (4−19) 3%
3−BB(F)B(F,F)XB(F)−F (4−24) 5%
1O1−HBBH−3 (−) 3%
1O1−HBBH−4 (−) 3%
1O1−HBBH−5 (−) 3%
NI=94.9℃;Tc<−20℃;Δn=0.110;Δε=6.1;Vth=1.74V;η=14.6mPa・s;γ1=84.0mPa・s;ε⊥/Δε=0.48.
5−HB(2F,3F)B(2F,3F)XB(F,F)−F
(1) 4%
3−BB(2F,3F)XB(F,F)−F (1−4) 9%
3−GBB(2F,3F)XB(F,F)−F (1−9) 5%
3−GBB(2F,3F)XB(F)−F (1−9) 5%
3−HH−V (2) 20%
3−HH−V1 (2) 4%
3−HH−VFF (2) 3%
3−HHEH−3 (3−3) 4%
3−HHEH−5 (3−3) 3%
4−HHEH−3 (3−3) 4%
V2−BB(F)B−1 (3−6) 2%
3−HHB−F (4) 4%
5−HB−CL (4−1) 5%
1−HHXB(F,F)−F (4−5) 5%
3−HHXB(F,F)−F (4−5) 5%
3−GB(F,F)XB(F,F)−F (4−12) 8%
3−HHB(F)B(F,F)−F (4−18) 4%
3−HH−5 (−) 6%
NI=79.9℃;Tc<−20℃;Δn=0.092;Δε=6.3;Vth=1.70V;η=12.1mPa・s;γ1=82.0mPa・s;ε⊥/Δε=0.51.
3−GB(2F,3F)XB(F,F)−F (1−3) 10%
3−HBB(2F,3F)XB(F,F)−F (1−7) 5%
3−dhBB(2F,3F)XB(F,F)−F(1−8) 6%
5−HH−V (2) 6%
3−HH−V (2) 31%
3−HH−V1 (2) 8%
5−B(F)BB−2 (3−7) 3%
5−B(F)BB−3 (3−7) 2%
3−BB(F)B(F,F)−CF3 (4−14) 4%
5−HBBXB(F,F)−F (4−20) 8%
3−GB(F)B(F,F)XB(F,F)−F(4−23) 2%
4−GB(F)B(F,F)XB(F,F)−F(4−23) 5%
5−GB(F)B(F,F)XB(F,F)−F(4−23) 7%
3−HH−O1 (−) 3%
NI=78.7℃;Tc<−20℃;Δn=0.105;Δε=9.1;Vth=1.35V;η=13.0mPa・s;γ1=82.7mPa・s;ε⊥/Δε=0.47.
5−HB(2F,3F)B(2F,3F)XB(F,F)−F
(1) 4%
3−GB(2F,3F)XB(F,F)−F (1−3) 8%
3−GBB(2F,3F)XB(F,F)−F (1−9) 5%
3−GBB(2F,3F)XB(F)−F (1−9) 5%
3−HH−V (2) 18%
4−HH−V (2) 10%
5−HH−V (2) 10%
5−HB−O2 (3−1) 4%
V−HHB−1 (3−4) 8%
3−HH2BB(F,F)−F (4) 3%
4−HH2BB(F,F)−F (4) 3%
3−HHB(F,F)−F (4−3) 4%
5−HHB(F,F)−F (4−3) 3%
3−HBB(F,F)−F (4−8) 5%
3−BB(F)B(F,F)XB(F,F)−F(4−25) 2%
5−BB(F)B(F,F)XB(F,F)−F(4−25) 6%
5−BB(F)B(F,F)XB(F)B(F,F)−F
(4−27) 2%
NI=85.6℃;Tc<−20℃;Δn=0.103;Δε=6.7;Vth=1.66V;η=14.2mPa・s;γ1=83.9mPa・s;ε⊥/Δε=0.51.
3−BB(2F,3F)XB(F)−F (1−4) 6%
3−BB(2F,3F)XB(F,F)−F (1−4) 6%
3−HBB(2F,3F)XB(F,F)−F (1−7) 5%
3−dhBB(2F,3F)XB(F,F)−F(1−8) 5%
3−HH−V (2) 26%
3−HH−V1 (2) 5%
3−HH−VFF (2) 4%
1V−HBB−2 (3−5) 5%
3−HHEBH−4 (3−9) 3%
3−HHEBH−5 (3−9) 4%
5−HB(F)BH−3 (3−11) 5%
5−HXB(F,F)−F (4−2) 6%
3−BB(F)B(F,F)−F (4−13) 3%
3−HBB(F,F)XB(F,F)−F (4−21) 3%
2−BB(F)B(F,F)XB(F)−F (4−24) 3%
3−BB(F)B(F,F)XB(F)−F (4−24) 3%
4−BB(F)B(F,F)XB(F)−F (4−24) 4%
3−HH−4 (−) 4%
NI=93.2℃;Tc<−20℃;Δn=0.112;Δε=5.4;Vth=1.85V;η=9.4mPa・s;γ1=78.4mPa・s;ε⊥/Δε=0.51.
3−BB(2F,3F)XB(F,F)−CF3(1−4) 19%
3−HH−V (2) 32%
3−HH−V1 (2) 5%
V−HHB−1 (3−4) 13%
1−BB(F)B−2V (3−6) 2%
2−HHBB(F,F)−F (4−17) 3%
3−HHBB(F,F)−F (4−17) 3%
3−HBBXB(F,F)−F (4−20) 8%
3−BB(F)B(F,F)XB(F,F)−F(4−25) 2%
4−BB(F)B(F,F)XB(F,F)−F(4−25) 7%
5−BB(F)B(F,F)XB(F,F)−F(4−25) 6%
NI=85.9℃;Tc<−20℃;Δn=0.117;Δε=9.4;Vth=1.49V;η=11.6mPa・s;γ1=81.9mPa・s;ε⊥/Δε=0.48.
3−HH1OB(2F,3F)XB(F,F)−F
(1) 6%
3−BB(2F,3F)XB(F,F)−F (1−4) 8%
4−BBB(2F,3F)XB(F,F)−F (1−10) 7%
4−HH−V (2) 20%
4−HH−V1 (2) 12%
7−HB−1 (3−1) 3%
3−HHEH−3 (3−3) 3%
3−HHEH−5 (3−3) 4%
3−HBB−2 (3−5) 3%
5−B(F)BB−2 (3−7) 5%
5−B(F)BB−3 (3−7) 3%
3−HHXB(F,F)−CF3 (4) 6%
3−HB−CL (4−1) 3%
3−HBB(F,F)−F (4−8) 3%
3−GB(F,F)XB(F,F)−F (4−12) 5%
3−HBB(F,F)XB(F,F)−F (4−21) 3%
3−BB(F,F)XB(F)B(F,F)−F(4−26) 3%
5−BB(F)B(F,F)XB(F)B(F,F)−F
(4−27) 3%
NI=80.7℃;Tc<−20℃;Δn=0.112;Δε=5.9;Vth=1.70V;η=14.5mPa・s;γ1=84.0mPa・s;ε⊥/Δε=0.50.
5−HBB(2F,3F)XB(F)B(F,F)−F
(1) 5%
3−HBB(2F,3F)XB(F)−OCF3(1−7) 5%
3−BB(2F,3F)XB(F)B(F,F)−F
(1−13) 5%
3−HH−V (2) 10%
3−HH−V1 (2) 5%
3−HH−VFF (2) 22%
V2−BB−1 (3−2) 5%
3−HB(F)HH−2 (3−8) 4%
5−HBB(F)B−2 (3−12) 4%
5−HXB(F,F)−F (4−2) 4%
3−HHXB(F,F)−F (4−5) 6%
3−BBXB(F,F)−F (4−15) 3%
3−BB(F,F)XB(F,F)−F (4−16) 3%
3−dhBB(F,F)XB(F,F)−F (4−22) 5%
3−GB(F)B(F,F)XB(F,F)−F(4−23) 5%
5−GB(F)B(F,F)XB(F,F)−F(4−23) 4%
1O1−HBBH−5 (−) 5%
NI=92.7℃;Tc<−20℃;Δn=0.116;Δε=8.1;Vth=1.50V;η=13.0mPa・s;γ1=76.5mPa・s;ε⊥/Δε=0.47.
3−B(2F,3F)XB(F,F)−F (1−1) 5%
3−BB(2F,3F)XB(F,F)−F (1−4) 10%
2O−BB(2F,3F)XB(F,F)−F (1−4) 6%
1V2−HH−1 (2) 10%
1V2−HH−3 (2) 12%
3−HH−V (2) 19%
3−BB(2F,5F)B−3 (3) 3%
3−HHEBH−3 (3−9) 5%
3−HHEBH−5 (3−9) 5%
3−HHB(F,F)−F (4−3) 6%
3−HGB(F,F)−F (4−6) 3%
V−HB(F)B(F,F)−F (4−9) 5%
3−BB(F)B(F,F)−F (4−13) 3%
3−BB(F)B(F,F)XB(F)−F (4−24) 3%
4−BB(F)B(F,F)XB(F)−F (4−24) 5%
NI=75.6℃;Tc<−20℃;Δn=0.099;Δε=5.5;Vth=1.83V;η=9.2mPa・s;γ1=73.5mPa・s;ε⊥/Δε=0.50.
3−BB(2F,3F)XB(F,F)−F (1−4) 7%
2O−BB(2F,3F)XB(F,F)−CF3
(1−4) 6%
2O−BB(2F,3F)XB(F)−OCF3(1−4) 8%
3−HH−V (2) 25%
3−HH−V1 (2) 6%
1V2−BB−1 (3−2) 4%
5−HBBH−3 (3−10) 6%
5−HEB(F,F)−F (4) 3%
3−HHB−CL (4) 5%
5−HHB−CL (4) 4%
3−HHEB(F,F)−F (4−4) 4%
5−HHEB(F,F)−F (4−4) 4%
3−HBEB(F,F)−F (4−10) 3%
5−HBEB(F,F)−F (4−10) 3%
4−HHB(F)B(F,F)−F (4−18) 7%
4−BB(F)B(F,F)XB(F、F)−F(4−25) 5%
NI=89.3℃;Tc<−20℃;Δn=0.112;Δε=7.3;Vth=1.62V;η=13.1mPa・s;γ1=84.1mPa・s;ε⊥/Δε=0.49.
3−BB(2F,3F)XB(F,F)−F (1−4) 10%
1V2−BB(2F,3F)XB(F,F)−F(1−4) 5%
1V2−BB(2F,3F)XB(F,F)−CF3
(1−4) 5%
4−HH−V (2) 12%
3−HH−V (2) 20%
3−HHB−1 (3−4) 6%
3−HHB−3 (3−4) 7%
5−HB(F)BH−3 (3−11) 2%
3−H2GB(F,F)−F (4) 4%
3−GHB(F,F)−F (4−7) 3%
5−GB(F)B(F,F)−F (4−11) 3%
3−BB(F,F)XB(F,F)−F (4−16) 6%
3−GBB(F)B(F,F)−F (4−19) 3%
3−BB(F)B(F,F)XB(F)−F (4−24) 5%
1O1−HBBH−3 (−) 3%
1O1−HBBH−4 (−) 3%
1O1−HBBH−5 (−) 3%
NI=86.3℃;Tc<−20℃;Δn=0.109;Δε=6.9;Vth=1.70V;η=12.2mPa・s;γ1=80.2mPa・s;ε⊥/Δε=0.48.
3−BB(2F,3F)XB(F,F)−F (1−4) 9%
2O−BB(2F,3F)XB(F,F)−F (1−4) 5%
3−BB(2F,3F)XB(F)B(F,F)−F
(1−13) 4%
3−GBB(2F,3F)XB(F)−F (1−9) 5%
3−HH−V (2) 20%
3−HH−V1 (2) 4%
3−HH−VFF (2) 3%
3−HHEH−3 (3−3) 4%
3−HHEH−5 (3−3) 3%
4−HHEH−3 (3−3) 4%
V2−BB(F)B−1 (3−6) 2%
3−HHB−F (4) 4%
5−HB−CL (4−1) 5%
1−HHXB(F,F)−F (4−5) 5%
3−HHXB(F,F)−F (4−5) 5%
3−GB(F,F)XB(F,F)−F (4−12) 8%
3−HHB(F)B(F,F)−F (4−18) 4%
3−HH−5 (−) 6%
NI=75.2℃;Tc<−20℃;Δn=0.092;Δε=6.5;Vth=1.68V;η=9.5mPa・s;γ1=72.6mPa・s;ε⊥/Δε=0.50.
3−BB(2F,3F)XB(F,F)−CF3(1−4) 10%
3−HBB(2F,3F)XB(F,F)−F (1−7) 5%
4−BBB(2F,3F)XB(F,F)−F (1−10) 6%
5−HH−V (2) 6%
3−HH−V (2) 31%
3−HH−V1 (2) 8%
5−B(F)BB−2 (3−7) 3%
5−B(F)BB−3 (3−7) 2%
3−BB(F)B(F,F)−CF3 (4−14) 4%
5−HBBXB(F,F)−F (4−20) 8%
3−GB(F)B(F,F)XB(F,F)−F(4−23) 2%
4−GB(F)B(F,F)XB(F,F)−F(4−23) 5%
5−GB(F)B(F,F)XB(F,F)−F(4−23) 7%
3−HH−O1 (−) 3%
NI=78.2℃;Tc<−20℃;Δn=0.113;Δε=9.2;Vth=1.34V;η=12.1mPa・s;γ1=77.3mPa・s;ε⊥/Δε=0.48.
Claims (13)
- 第一成分として式(1)で表される化合物の群から選択された少なくとも1つの化合物、および第二成分として式(2)で表される化合物の群から選択された少なくとも1つの化合物を含有し、そしてネマチック相を有する液晶組成物。
式(1)および式(2)において、R1およびR2は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、または炭素数2から12のアルケニルであり;R3は、炭素数2から12のアルケニル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Aおよび環Bは独立して、1,4−シクロへキシレン、1,4−フェニレン、2−フルオロ−1,4−フェニレン、2,3−ジフルオロ−1,4−フェニレン、2,6−ジフルオロ−1,4−フェニレン、ピリミジン−2,5−ジイル、1,3−ジオキサン−2,5−ジイル、またはテトラヒドロピラン−2,5−ジイルであり;Z1およびZ2は独立して、単結合、エチレン、ビニレン、メチレンオキシ、カルボニルオキシ、またはジフルオロメチレンオキシであり;L1およびL2は独立して、フッ素または塩素であり;X1およびX2は独立して、水素またはフッ素であり;Y1は、フッ素、塩素、少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルコキシであり;mおよびjは独立して、0、1、2、または3であり、そしてmとjの和は3以下である。 - 第一成分として式(1−1)から式(1−14)で表される化合物の群から選択された少なくとも1つの化合物を含有する、請求項1に記載の液晶組成物。
式(1−1)から式(1−14)において、R1は、炭素数1から12のアルキル、炭素数1から12のアルコキシ、または炭素数2から12のアルケニルであり;L1およびL2は独立して、フッ素または塩素であり;X1、X2、X3、X4、X5、X6、X7、およびX8は独立して、水素またはフッ素であり;Y1は、フッ素、塩素、少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルコキシである。 - 液晶組成物の重量に基づいて、第一成分の割合が5重量%から40重量%の範囲であり、第二成分の割合が15重量%から60重量%の範囲である、請求項1または2に記載の液晶組成物。
- 第三成分として式(3)で表される化合物の群から選択された少なくとも1つの化合物をさらに含有する、請求項1から3のいずれか1項に記載の液晶組成物。
式(3)において、R4およびR5は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Cおよび環Dは独立して、1,4−シクロへキシレン、1,4−フェニレン、2−フルオロ−1,4−フェニレン、または2,5−ジフルオロ−1,4−フェニレンであり;Z3は、単結合、エチレンまたはカルボニルオキシであり;nは、1、2、または3であり;ただしnが1のとき、環Cは1,4−フェニレンである。 - 液晶組成物の重量に基づいて、第三成分の割合が5重量%から35重量%の範囲である、請求項4または5に記載の液晶組成物。
- 第四成分として式(4)で表される化合物の群から選択された少なくとも1つの化合物をさらに含有する、請求項1から6のいずれか1項に記載の液晶組成物。
式(4)において、R6は炭素数1から12のアルキル、炭素数1から12のアルコキシ、または炭素数2から12のアルケニルであり;環Eは、1,4−シクロへキシレン、1,4−フェニレン、2−フルオロ−1,4−フェニレン、2,6−ジフルオロ−1,4−フェニレン、ピリミジン−2,5−ジイル、1,3−ジオキサン−2,5−ジイル、またはテトラヒドロピラン−2,5−ジイルであり;Z4は、単結合、エチレン、カルボニルオキシ、またはジフルオロメチレンオキシであり;X9およびX10は独立して、水素またはフッ素であり;Y2は、フッ素、塩素、少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルコキシであり;pは、1、2、3、または4である。 - 液晶組成物の重量に基づいて、第四成分の割合が10重量%から60重量%の範囲である、請求項7または8に記載の液晶組成物。
- ネマチック相の上限温度が70℃以上であり、波長589nmにおける光学異方性(25℃で測定)が0.07以上であり、そして周波数1kHzにおける誘電率異方性(25℃で測定)が2以上である、請求項1から9のいずれか1項に記載の液晶組成物。
- 請求項1から10のいずれか1項に記載の液晶組成物を含有する液晶表示素子。
- 液晶表示素子の動作モードが、TNモード、ECBモード、OCBモード、IPSモード、FFSモード、またはFPAモードであり、液晶表示素子の駆動方式がアクティブマトリックス方式である、請求項11に記載の液晶表示素子。
- 請求項1から10のいずれか1項に記載の液晶組成物の液晶表示素子における使用。
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EP3006541B1 (en) | 2017-10-18 |
WO2014192390A1 (ja) | 2014-12-04 |
US20160090532A1 (en) | 2016-03-31 |
CN105189701B (zh) | 2019-01-18 |
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