JP5314709B2 - 液晶化合物 - Google Patents
液晶化合物 Download PDFInfo
- Publication number
- JP5314709B2 JP5314709B2 JP2011001377A JP2011001377A JP5314709B2 JP 5314709 B2 JP5314709 B2 JP 5314709B2 JP 2011001377 A JP2011001377 A JP 2011001377A JP 2011001377 A JP2011001377 A JP 2011001377A JP 5314709 B2 JP5314709 B2 JP 5314709B2
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- Japan
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- formula
- liquid crystal
- compounds
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- alkenyl
- Prior art date
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- Expired - Lifetime
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 83
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 20
- -1 tetrahydropyran-2,5-diyl group Chemical group 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 abstract 1
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 abstract 1
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 235000019256 formaldehyde Nutrition 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- 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 abstract 1
- 239000000203 mixture Substances 0.000 description 58
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000012071 phase Substances 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 0 *C(CC1)CCC1c1cc(F)c(-c2cc(I)c(*)c(I)c2)c(F)c1 Chemical compound *C(CC1)CCC1c1cc(F)c(-c2cc(I)c(*)c(I)c2)c(F)c1 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 229910021538 borax Inorganic materials 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- IKGLACJFEHSFNN-UHFFFAOYSA-N hydron;triethylazanium;trifluoride Chemical compound F.F.F.CCN(CC)CC IKGLACJFEHSFNN-UHFFFAOYSA-N 0.000 description 4
- 235000010339 sodium tetraborate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- WJAVYWPXOXAOBS-UHFFFAOYSA-N Cc1cc(F)c(C)cc1 Chemical compound Cc1cc(F)c(C)cc1 WJAVYWPXOXAOBS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
- MRQYTJXVULSNIS-UHFFFAOYSA-N 4-bromo-3-fluorophenol Chemical compound OC1=CC=C(Br)C(F)=C1 MRQYTJXVULSNIS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- YEJCHVFCLNKZPU-UHFFFAOYSA-N CC1COC(C)CC1 Chemical compound CC1COC(C)CC1 YEJCHVFCLNKZPU-UHFFFAOYSA-N 0.000 description 2
- HBXFIXSFKULBOG-UHFFFAOYSA-N Cc1cc(F)c(C)c(F)c1 Chemical compound Cc1cc(F)c(C)c(F)c1 HBXFIXSFKULBOG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 208000032369 Primary transmission Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- BTTUMVHWIAXYPJ-UHFFFAOYSA-N 1,3-dithian-2-yl(trimethyl)silane Chemical compound C[Si](C)(C)C1SCCCS1 BTTUMVHWIAXYPJ-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
- AUXIEQKHXAYAHG-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbonitrile Chemical class C=1C=CC=CC=1C1(C#N)CCCCC1 AUXIEQKHXAYAHG-UHFFFAOYSA-N 0.000 description 1
- 102220545768 116 kDa U5 small nuclear ribonucleoprotein component_C60S_mutation Human genes 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- ZRTWIJKGTUGZJY-UHFFFAOYSA-N 3,4,5-trifluorophenol Chemical compound OC1=CC(F)=C(F)C(F)=C1 ZRTWIJKGTUGZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 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
- SGJOQFDORNSERE-UHFFFAOYSA-N CC(CC1)COC1c(cc1)ccc1O Chemical compound CC(CC1)COC1c(cc1)ccc1O SGJOQFDORNSERE-UHFFFAOYSA-N 0.000 description 1
- CROKKJCBPVRHHF-UHFFFAOYSA-N CC1CC(F)=C(C)CC1 Chemical compound CC1CC(F)=C(C)CC1 CROKKJCBPVRHHF-UHFFFAOYSA-N 0.000 description 1
- KMGDYKOGDOVDCW-UHFFFAOYSA-N CC1CC=C(C)CC1 Chemical compound CC1CC=C(C)CC1 KMGDYKOGDOVDCW-UHFFFAOYSA-N 0.000 description 1
- QRMPKOFEUHIBNM-UHFFFAOYSA-N CC1CCC(C)CC1 Chemical compound CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- RPMUDXVQHUECRE-UHFFFAOYSA-N CC1COC(C)OC1 Chemical compound CC1COC(C)OC1 RPMUDXVQHUECRE-UHFFFAOYSA-N 0.000 description 1
- NRYJYCZRGKAYMG-UHFFFAOYSA-N CC1OCC(C)=CC1 Chemical compound CC1OCC(C)=CC1 NRYJYCZRGKAYMG-UHFFFAOYSA-N 0.000 description 1
- DYSJQUQJVBYIOT-UHFFFAOYSA-N Cc1ccc(C)c(F)c1F Chemical compound Cc1ccc(C)c(F)c1F DYSJQUQJVBYIOT-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Cc1ccc(C)cc1 Chemical compound Cc1ccc(C)cc1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- IAXMOTRFVPINOJ-UHFFFAOYSA-N Oc(cc1)ccc1-c(cc1F)cc(F)c1F Chemical compound Oc(cc1)ccc1-c(cc1F)cc(F)c1F IAXMOTRFVPINOJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 241000620457 Telestes souffia Species 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000002051 biphasic effect 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 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 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- YDGSUPBDGKOGQT-UHFFFAOYSA-N lithium;dimethylazanide Chemical compound [Li+].C[N-]C YDGSUPBDGKOGQT-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—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
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
-
- 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
-
- 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
-
- 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
-
- 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
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
-
- 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
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
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Description
TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H.,
Proc. Eurodisplay 84, Sept. 1984: A 210-288 Matrix LCD Controlled by Double Stage Diode Rings,
p. 141 ff, Paris;および STROMER, M., Proc. Eurodisplay 84, Sept. 1984: Design of
Thin Film Transistors for Matrix Addressing of Television Liquid Crystal
Displays, p.145 ff, Paris)。抵抗が低下するほど、MLCディスプレイのコントラストが劣化し、また、残像消去の問題も生じうる。液晶混合物の比抵抗は、ディスプレイの内部表面との相互作用のために、一般に、MLCディスプレイの寿命の全体に渡って低下するので、許容される耐用年数を得るためには、高い(初期)抵抗を有することが非常に重要である。特に、低電圧用混合物の場合には、高い抵抗値を達成することは従来不可能であった。さらに、比抵抗の増加が、温度の上昇に伴い、および加熱および/またはUV照射後に可能な限り小さいことも重要である。さらに、従来技術の混合物の低温特性もまた特に不利である。低温であっても、結晶および/またはスメクチック相が生じないことが要求され、さらに、粘性の温度依存性もできるだけ低いことが要求される。先行技術で公知のMLCディスプレイは今日の必要条件を満たさない。
−極度に低い温度でのスイッチ能力(アウトドア用途、自動車、航空電子工学)
−紫外線照射に対する増大された抵抗(より長い寿命)
先行技術から入手可能な媒体では、これらの利点を、同時に他のパラメーターを保持しながら達成することはできない。
R1およびR2は、互いに独立してそれぞれ、H、ハロゲン、ハロゲン化もしくは無置換の炭素数1〜15のアルキル基もしくはアルコキシ基であり、但し、この基において1または2以上のCH2基は、O原子同士が直接結合しないことを条件として、−C≡C−、−CH=CH−、−O−、−CO−O−または−O−CO−で置換されていても良く、ここで、基R1およびR2の1つは、CN、OCN、SCN、NCSまたはSF5を表してもよく、
A1、A2、A3およびA4は、互いに独立してそれぞれ、
Z1、Z2およびZ3は、互いに独立してそれぞれ、−CO−O−、−O−CO−、−CF2O−、−OCF2−、−CH2O−、−OCH2−、−CH2CH2−、−(CH2)4−、−C2F4−、−CH2CF2−、−CF2CH2−、−CF=CF−、−CH=CH−、−C≡C−または単結合を表し、
a、bおよびcは、互いに独立してそれぞれ、0、1、2または3を表し、ここでa+b+c≦3である。
Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag,
Stuttgart等)。正確にはこのような合成に知られており適した条件が選ばれる。また、ここにはより詳しくは述べないが、それ自身公知の異なる方法によることもできる。
(1989); K. Niwa et al., Proc. SID Conference, San Francisco, June 1984, p. 304
(1984); G. Weber et al., Liquid Crystals 5, 1381 (1989)]により、式Iの化合物を含有する本発明の混合物は、式:
X0は、F、Cl、それぞれ炭素数7までのハロゲン化アルキル、ハロゲン化アルケニル、ハロゲン化アルケニルオキシまたはハロゲン化アルコキシを表し、
Z0は、−CH=CH−、−C2H4−、−(CH2)4−、−C2F4−、−CH2O−、−OCH2−、−CF=CF−、−CF2O−、−OCF2−または−COO−を表し、
Y1、Y2、Y3およびY4は、互いに独立して、それぞれHまたはFを表し、
rは、0または1である。
の化合物の1または2以上を含有する。
dは、0、1または2を表し、
Y1は、HまたはFを表し、
alkylまたはalkyl*はそれぞれ、互いに独立して、1〜9個の炭素原子を有する直鎖または分岐アルキルを表し、
alkenylまたはalkenyl*はそれぞれ、互いに独立して、9個までの炭素原子を有する直鎖または分岐アルケニルを表す。
表Cは、本発明の混合物に一般に0.1から10重量%の量で添加される使用可能なドーパントを示す。
例えば本発明の混合物に添加することができる安定剤を下に示す。
n−BuLi:ヘキサン中n−ブチルリチウム 1.6モル溶液
DMAP:4−(ジメチルアミノ)ピリジン
THF:テトラヒドロフラン
DCC:N,N’−ジシクロヘキシルカルボジイミド
LDA:リチウムジメチルアミド
RT:室温
例1
ステップ 2.1
下記式のエナンチオマーの分離:
3.74 g enantio-HPLC: 98.25 % - 旋光度: −28.0°
Claims (10)
- 式Iで示される1種類以上の化合物と、式RI〜RIXで示される化合物から成る群より選択される1種類以上の化合物とを含む液晶媒体。
R1およびR2は、互いに独立してそれぞれ、H、ハロゲン、ハロゲン化もしくは無置換の炭素数1〜15のアルキル基もしくはアルコキシ基であり、但し、この基において1または2以上のCH2基は、O原子同士が直接結合しないことを条件として、−C≡C−、−CH=CH−、−O−、−CO−O−または−O−CO−で置換されていても良く、ここで、基R1およびR2の1つは、CN、OCN、SCN、NCSまたはSF5を表してもよく、
A1、A2、A3およびA4は、互いに独立してそれぞれ、
Z1、Z2およびZ3は、互いに独立してそれぞれ、−CO−O−、−O−CO−、−CF2O−、−OCF2−、−CH2O−、−OCH2−、−CH2CH2−、−(CH2)4−、−C2F4−、−CH2CF2−、−CF2CH2−、−CF=CF−、−CH=CH−、−C≡C−または単結合を表し、
a、bおよびcは、互いに独立してそれぞれ、0、1、2または3を表し、ここでa+b+c≦3である。)
R 0 は、それぞれ、9個までの炭素原子を有するn−アルキル、オキサアルキル、フルオロアルキル、アルケニルオキシまたはアルケニルを表し、
dは、0、1または2を表し、
Y 1 は、HまたはFを表し、
alkylまたはalkyl * は、それぞれ互いに独立して、1〜9個の炭素原子を有する直鎖または分岐アルキルを表し、
alkenylまたはalkenyl * は、それぞれ互いに独立して、9個までの炭素原子を有する直鎖または分岐アルケニルを表す。) - a=1およびb=0、またはa=0およびb=1であることを特徴とする請求項1または2に記載の液晶媒体。
- L1がフッ素を示し、L2がフッ素または水素を示すことを特徴とする請求項2に記載の液晶媒体。
- L1およびL2がフッ素を示すことを特徴とする請求項2に記載の液晶媒体。
- 一般式II〜IXからなる群より選ばれる1種または2種以上の化合物を含有することを特徴とする請求項1記載の液晶媒体。
R0は、それぞれ炭素数9までのn−アルキル、オキサアルキル、フルオロアルキル、アルケニルオキシまたはアルケニルを表し、
X0は、F、Cl、それぞれ炭素数7までのハロゲン化アルキル、ハロゲン化アルケニル、ハロゲン化アルケニルオキシまたはハロゲン化アルコキシを表し、
Z0は、−CH=CH−、−C2H4−、−(CH2)4−、−C2F4−、−CH2O−、−OCH2−、−CF=CF−、−CF2O−、−OCF2−または−COO−を表し、
Y1、Y2、Y3およびY4は、互いに独立して、それぞれHまたはFを表し、
rは、0または1である。) - 請求項1〜8のいずれか1項に記載の液晶媒体の電気光学目的のための使用。
- 請求項1〜8のいずれか1項に記載の液晶媒体を含有する電気光学液晶ディスプレイ。
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JP2006508150A (ja) | 2006-03-09 |
CN101294079A (zh) | 2008-10-29 |
JP2011136998A (ja) | 2011-07-14 |
KR101070102B1 (ko) | 2011-10-05 |
US20060061699A1 (en) | 2006-03-23 |
ATE374232T1 (de) | 2007-10-15 |
EP1565540A1 (de) | 2005-08-24 |
KR20050086861A (ko) | 2005-08-30 |
CN101294079B (zh) | 2013-06-19 |
AU2003302394A1 (en) | 2004-06-18 |
DE50308290D1 (de) | 2007-11-08 |
TWI320054B (en) | 2010-02-01 |
EP1565540B1 (de) | 2007-09-26 |
WO2004048501A1 (de) | 2004-06-10 |
JP4711392B2 (ja) | 2011-06-29 |
DE10353658A1 (de) | 2004-06-09 |
TW200418961A (en) | 2004-10-01 |
CN1717468A (zh) | 2006-01-04 |
US7291367B2 (en) | 2007-11-06 |
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