JP6523953B2 - ビメソゲン化合物およびメソゲン媒体 - Google Patents
ビメソゲン化合物およびメソゲン媒体 Download PDFInfo
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- JP6523953B2 JP6523953B2 JP2015518885A JP2015518885A JP6523953B2 JP 6523953 B2 JP6523953 B2 JP 6523953B2 JP 2015518885 A JP2015518885 A JP 2015518885A JP 2015518885 A JP2015518885 A JP 2015518885A JP 6523953 B2 JP6523953 B2 JP 6523953B2
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- 150000001875 compounds Chemical class 0.000 title claims description 144
- 239000004973 liquid crystal related substance Substances 0.000 claims description 67
- 229910052731 fluorine Inorganic materials 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000006850 spacer group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 98
- 239000012071 phase Substances 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- -1 Piperidine-1,4-diyl Chemical group 0.000 description 37
- 210000004027 cell Anatomy 0.000 description 28
- 239000000463 material Substances 0.000 description 28
- 239000000758 substrate Substances 0.000 description 26
- 230000003287 optical effect Effects 0.000 description 23
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- 230000005684 electric field Effects 0.000 description 17
- 239000010410 layer Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 12
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- 239000000047 product Substances 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 230000007704 transition Effects 0.000 description 9
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 230000004044 response Effects 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000004988 Nematic liquid crystal Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 239000013067 intermediate product Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 210000002421 cell wall Anatomy 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- MRQYTJXVULSNIS-UHFFFAOYSA-N 4-bromo-3-fluorophenol Chemical compound OC1=CC=C(Br)C(F)=C1 MRQYTJXVULSNIS-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 102000004856 Lectins Human genes 0.000 description 2
- 108090001090 Lectins Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 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
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- JHAYEQICABJSTP-UHFFFAOYSA-N decoquinate Chemical group N1C=C(C(=O)OCC)C(=O)C2=C1C=C(OCC)C(OCCCCCCCCCC)=C2 JHAYEQICABJSTP-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 239000010408 film Substances 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
- 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 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000002523 lectin Substances 0.000 description 2
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- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 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 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
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- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920000642 polymer 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
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
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- 238000004381 surface treatment Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- OCODJNASCDFXSR-UHFFFAOYSA-N 1-bromo-2-fluoro-4-iodobenzene Chemical compound FC1=CC(I)=CC=C1Br OCODJNASCDFXSR-UHFFFAOYSA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- NOLJPCPMOUBRJN-UHFFFAOYSA-N 2-bromoundecanoic acid Chemical compound CCCCCCCCCC(Br)C(O)=O NOLJPCPMOUBRJN-UHFFFAOYSA-N 0.000 description 1
- MLISZBPTIMZRFF-UHFFFAOYSA-N 3-hydroxy-4-phenylbenzonitrile Chemical group OC1=CC(C#N)=CC=C1C1=CC=CC=C1 MLISZBPTIMZRFF-UHFFFAOYSA-N 0.000 description 1
- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- LBUNNMJLXWQQBY-UHFFFAOYSA-N 4-fluorophenylboronic acid Chemical compound OB(O)C1=CC=C(F)C=C1 LBUNNMJLXWQQBY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QRMPKOFEUHIBNM-UHFFFAOYSA-N CC1CCC(C)CC1 Chemical compound CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- PXQRBGJTHKQWBC-UHFFFAOYSA-N CC1CNC(C)NC1 Chemical compound CC1CNC(C)NC1 PXQRBGJTHKQWBC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PHMHDRYYFAYWEG-UHFFFAOYSA-N Rhapontigenin Natural products C1=C(O)C(OC)=CC=C1C=CC1=CC(O)=CC(O)=C1 PHMHDRYYFAYWEG-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
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- 230000001680 brushing effect Effects 0.000 description 1
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- 239000003610 charcoal Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
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- 238000000576 coating method Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920001577 copolymer Chemical group 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
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- 229940043279 diisopropylamine Drugs 0.000 description 1
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- 230000009477 glass transition Effects 0.000 description 1
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- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- LZULAZTXJLWELL-UHFFFAOYSA-N methyl hex-5-ynoate Chemical compound COC(=O)CCCC#C LZULAZTXJLWELL-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
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- 238000010899 nucleation Methods 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000000527 sonication 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
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
- C09K19/0258—Flexoelectric
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/55—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and esterified hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/30—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
- C09K19/2007—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 the chain containing -COO- or -OCO- groups
- C09K19/2014—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 the chain containing -COO- or -OCO- groups containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n-
-
- 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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP12005048 | 2012-07-06 | ||
| EP12005048.9 | 2012-07-06 | ||
| PCT/EP2013/001773 WO2014005672A1 (en) | 2012-07-06 | 2013-06-14 | Bimesogenic compounds and mesogenic media |
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| JP2018201810A Division JP2019048832A (ja) | 2012-07-06 | 2018-10-26 | ビメソゲン化合物およびメソゲン媒体 |
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| JP2015527304A JP2015527304A (ja) | 2015-09-17 |
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| EP (1) | EP2870217B1 (enExample) |
| JP (2) | JP6523953B2 (enExample) |
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| CN (1) | CN104411798B (enExample) |
| TW (1) | TWI589678B (enExample) |
| WO (1) | WO2014005672A1 (enExample) |
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| JP6523951B2 (ja) | 2012-07-06 | 2019-06-05 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ビメソゲン化合物およびメソゲン媒体 |
| KR20150036407A (ko) * | 2012-07-06 | 2015-04-07 | 메르크 파텐트 게엠베하 | 바이메소제닉 화합물 및 메소제닉 매질 |
| KR20150052136A (ko) * | 2012-08-29 | 2015-05-13 | 메르크 파텐트 게엠베하 | 바이메소제닉 화합물 및 메소제닉 매질 |
| KR20160089446A (ko) * | 2013-11-22 | 2016-07-27 | 메르크 파텐트 게엠베하 | 바이메소젠성 화합물 및 메소젠성 매질 |
| WO2016008561A1 (en) * | 2014-07-17 | 2016-01-21 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
| WO2016074762A1 (en) | 2014-11-11 | 2016-05-19 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
| CN107001935A (zh) * | 2014-12-17 | 2017-08-01 | 默克专利股份有限公司 | 双介晶化合物和介晶介质 |
| KR20170097115A (ko) * | 2014-12-19 | 2017-08-25 | 메르크 파텐트 게엠베하 | 바이메소젠성 화합물 및 메소젠성 매질 |
| CN107109222B (zh) * | 2014-12-19 | 2021-05-07 | 默克专利股份有限公司 | 双介晶化合物和介晶介质 |
| JP2018502113A (ja) * | 2014-12-30 | 2018-01-25 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ビメソゲン化合物およびメソゲン性媒体 |
| KR20180073618A (ko) * | 2015-10-23 | 2018-07-02 | 메르크 파텐트 게엠베하 | 광 변조 소자 |
| EP3383970B1 (en) * | 2015-12-02 | 2021-03-31 | Merck Patent GmbH | Liquid crystal medium and liquid crystal device |
| US20190177617A1 (en) * | 2016-05-12 | 2019-06-13 | Merck Patent Gmbh | Bimesogenic compounds and mesogenic media |
| WO2018050573A1 (en) | 2016-09-14 | 2018-03-22 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal device |
| DE112017006197T5 (de) | 2016-12-08 | 2019-08-29 | Merck Patent Gmbh | Flüssigkristallmedium und flüssigkristallvorrichtung |
| WO2019030153A1 (en) | 2017-08-08 | 2019-02-14 | Merck Patent Gmbh | LIQUID CRYSTAL MEDIUM AND LIQUID CRYSTAL DEVICE |
| DE112018004045T5 (de) | 2017-08-08 | 2020-05-14 | Merck Patent Gmbh | Flüssigkristallmedium und flüssigkristallvorrichtung |
| DE112018005688T5 (de) | 2017-10-25 | 2020-07-09 | Merck Patent Gmbh | Flüssigkristallmedium und flüssigkristallvorrichtung |
| CN111263800A (zh) | 2017-10-25 | 2020-06-09 | 默克专利股份有限公司 | 液晶介质及液晶装置 |
| WO2019121438A1 (en) | 2017-12-18 | 2019-06-27 | Merck Patent Gmbh | Liquid crystal compound and liquid crystal medium |
| WO2019179962A1 (en) | 2018-03-22 | 2019-09-26 | Merck Patent Gmbh | Liquid-crystalline medium |
| CN110467926B (zh) * | 2018-05-10 | 2023-10-31 | 江苏集萃智能液晶科技有限公司 | 液晶组合物及其液晶显示器 |
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| JP2696557B2 (ja) * | 1989-03-07 | 1998-01-14 | チッソ株式会社 | トリフルオロベンゼン誘導体 |
| DE4000451B4 (de) | 1990-01-09 | 2004-12-09 | Merck Patent Gmbh | Elektrooptisches Flüssigkristallschaltelement |
| JPH0517403A (ja) * | 1991-05-07 | 1993-01-26 | Fuji Photo Film Co Ltd | 液晶性化合物および強誘電性液晶組成物 |
| EP0916992B1 (en) | 1992-09-18 | 2003-11-26 | Hitachi, Ltd. | A liquid crystal display device |
| JP3015998B2 (ja) * | 1993-08-31 | 2000-03-06 | キヤノン株式会社 | 液晶性化合物、それを含む液晶組成物、該液晶組成物を用いた液晶素子、液晶装置、並びに表示方法 |
| WO1998000428A1 (en) | 1996-07-01 | 1998-01-08 | Merck Patent Gmbh | Chiral dopants |
| JP4102446B2 (ja) * | 1996-12-16 | 2008-06-18 | チッソ株式会社 | ジフルオロフェニル誘導体、液晶性化合物および液晶組成物 |
| DE19834162A1 (de) | 1997-08-13 | 1999-02-18 | Merck Patent Gmbh | Chirale Verbindungen |
| EP0971016B1 (en) | 1998-07-08 | 2003-05-21 | MERCK PATENT GmbH | Mesogenic estradiols |
| GB2356629B (en) * | 1999-10-04 | 2004-09-22 | Merck Patent Gmbh | Bimesogenic Compounds and Flexoelectric Devices |
| GB0225662D0 (en) * | 2001-11-16 | 2002-12-11 | Merck Patent Gmbh | Liquid crystalline medium and liquid crystal display |
| EP1408098B1 (en) * | 2002-10-08 | 2005-12-28 | MERCK PATENT GmbH | Liquid crystalline medium and liquid crystal display |
| JP4442179B2 (ja) * | 2002-10-10 | 2010-03-31 | チッソ株式会社 | アリルエーテル化合物、この化合物を含有する液晶組成物およびこの液晶組成物を含有する液晶表示素子 |
| EP1477547B1 (en) * | 2003-05-09 | 2006-06-14 | MERCK PATENT GmbH | Liquid crystalline medium and liquid crystal display |
| JP4514508B2 (ja) * | 2003-10-29 | 2010-07-28 | 株式会社Adeka | 液晶組成物及びｓｔｎ型液晶素子 |
| GB0402006D0 (en) * | 2004-01-30 | 2004-03-03 | Dow Corning Ltd | Liquid crystal materials |
| US7544400B2 (en) * | 2004-12-23 | 2009-06-09 | Merck Patent Gmbh | Bimesogenic compounds and flexoelectric devices |
| JP2007002132A (ja) * | 2005-06-24 | 2007-01-11 | Chisso Corp | 液晶組成物および液晶表示素子 |
| JP5496660B2 (ja) * | 2006-06-09 | 2014-05-21 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 液晶媒体および液晶ディスプレイ |
| EP2351741B1 (en) * | 2008-10-21 | 2016-11-30 | JNC Corporation | Pentacyclic liquid crystal compound having nitrogen-containing heterocyclic ring, liquid crystal composition, and liquid crystal display device |
| JP5672043B2 (ja) * | 2010-04-05 | 2015-02-18 | Jnc株式会社 | ５環化合物、液晶組成物および液晶表示素子 |
| WO2011137986A1 (en) * | 2010-05-06 | 2011-11-10 | Merck Patent Gmbh | Liquid crystalline medium and liquid crystal display |
| WO2012043386A1 (ja) * | 2010-09-28 | 2012-04-05 | Dic株式会社 | 新規液晶表示装置及び有用な液晶組成物 |
| KR102014557B1 (ko) * | 2011-07-05 | 2019-08-26 | 메르크 파텐트 게엠베하 | 바이메소제닉 화합물 |
| EP2855627B1 (en) * | 2012-05-25 | 2017-09-20 | Merck Patent GmbH | Bimesogenic compounds and mesogenic media |
| JP6240171B2 (ja) * | 2012-05-25 | 2017-11-29 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | メソゲン媒体および液晶ディスプレイ |
| KR20150036407A (ko) * | 2012-07-06 | 2015-04-07 | 메르크 파텐트 게엠베하 | 바이메소제닉 화합물 및 메소제닉 매질 |
| JP6523951B2 (ja) * | 2012-07-06 | 2019-06-05 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ビメソゲン化合物およびメソゲン媒体 |
| KR20150052136A (ko) * | 2012-08-29 | 2015-05-13 | 메르크 파텐트 게엠베하 | 바이메소제닉 화합물 및 메소제닉 매질 |
| CN104822800B (zh) * | 2012-12-10 | 2018-03-30 | 默克专利股份有限公司 | 双介晶化合物和介晶介质 |
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2013
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- 2013-06-14 EP EP13729268.6A patent/EP2870217B1/en not_active Not-in-force
- 2013-06-14 CN CN201380035215.0A patent/CN104411798B/zh active Active
- 2013-06-14 KR KR1020157003132A patent/KR20150036406A/ko not_active Abandoned
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2018
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- 2018-10-26 JP JP2018201810A patent/JP2019048832A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP2870217B1 (en) | 2016-07-20 |
| EP2870217A1 (en) | 2015-05-13 |
| JP2015527304A (ja) | 2015-09-17 |
| WO2014005672A1 (en) | 2014-01-09 |
| TWI589678B (zh) | 2017-07-01 |
| US20150175883A1 (en) | 2015-06-25 |
| CN104411798B (zh) | 2017-05-24 |
| JP2019048832A (ja) | 2019-03-28 |
| KR20150036406A (ko) | 2015-04-07 |
| TW201406933A (zh) | 2014-02-16 |
| CN104411798A (zh) | 2015-03-11 |
| US20190010400A1 (en) | 2019-01-10 |
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