JP5317382B2 - キラルな化合物ｉｉ - Google Patents
キラルな化合物ｉｉ Download PDFInfo
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- JP5317382B2 JP5317382B2 JP2002512102A JP2002512102A JP5317382B2 JP 5317382 B2 JP5317382 B2 JP 5317382B2 JP 2002512102 A JP2002512102 A JP 2002512102A JP 2002512102 A JP2002512102 A JP 2002512102A JP 5317382 B2 JP5317382 B2 JP 5317382B2
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- chiral
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- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 153
- 239000000203 mixture Substances 0.000 claims abstract description 103
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 95
- -1 diagnostics Substances 0.000 claims abstract description 58
- 239000002019 doping agent Substances 0.000 claims abstract description 40
- 229920000642 polymer Polymers 0.000 claims abstract description 18
- 239000002537 cosmetic Substances 0.000 claims abstract description 8
- 230000003287 optical effect Effects 0.000 claims abstract description 8
- 229920000106 Liquid crystal polymer Polymers 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 230000003098 cholesteric effect Effects 0.000 claims description 32
- 229910052731 fluorine Inorganic materials 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- 125000006850 spacer group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 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 4
- 230000008859 change Effects 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000000049 pigment Substances 0.000 abstract description 12
- 239000007788 liquid Substances 0.000 abstract description 5
- 238000003860 storage Methods 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract description 3
- 230000001070 adhesive effect Effects 0.000 abstract description 3
- 229920003002 synthetic resin Polymers 0.000 abstract description 3
- 239000000057 synthetic resin Substances 0.000 abstract description 3
- 239000000460 chlorine Substances 0.000 description 27
- 239000012071 phase Substances 0.000 description 26
- 239000000758 substrate Substances 0.000 description 17
- 229920000728 polyester Polymers 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000011295 pitch Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 229920006254 polymer film Polymers 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 125000005529 alkyleneoxy group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- 239000004904 UV filter Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- SJSRFXJWBKOROD-UHFFFAOYSA-N 1,1'-bi(cyclohexyl)-1-carboxylic acid Chemical compound C1CCCCC1C1(C(=O)O)CCCCC1 SJSRFXJWBKOROD-UHFFFAOYSA-N 0.000 description 2
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 0 C*(C1CCC(*[C@@](C)C2CC2)CC1)c(cc1)ccc1O Chemical compound C*(C1CCC(*[C@@](C)C2CC2)CC1)c(cc1)ccc1O 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 239000012952 cationic photoinitiator Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 150000002500 ions Chemical class 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
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 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 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- IWIOHRVOBOYWQE-UHFFFAOYSA-N (1-cyclohexylcyclohexyl)benzene Chemical compound C1CCCCC1C1(C=2C=CC=CC=2)CCCCC1 IWIOHRVOBOYWQE-UHFFFAOYSA-N 0.000 description 1
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- AAFJXZWCNVJTMK-KVTDHHQDSA-N (1S,2S)-1,2-bis[(2R)-oxiran-2-yl]ethane-1,2-diol Chemical compound C([C@@H]1[C@@H](O)[C@H](O)[C@@H]2OC2)O1 AAFJXZWCNVJTMK-KVTDHHQDSA-N 0.000 description 1
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 description 1
- ZKJNETINGMOHJG-GGWOSOGESA-N (e)-1-[(e)-prop-1-enoxy]prop-1-ene Chemical group C\C=C\O\C=C\C ZKJNETINGMOHJG-GGWOSOGESA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- QQFSIGWYINAJOB-UHFFFAOYSA-N 1,4-dicyclohexylbenzene Chemical compound C1CCCCC1C1=CC=C(C2CCCCC2)C=C1 QQFSIGWYINAJOB-UHFFFAOYSA-N 0.000 description 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
- GRZJZRHVJAXMRR-UHFFFAOYSA-N 1-cyclohexyl-2-phenylbenzene Chemical group C1CCCCC1C1=CC=CC=C1C1=CC=CC=C1 GRZJZRHVJAXMRR-UHFFFAOYSA-N 0.000 description 1
- OLUVNSGCKHZQJQ-UHFFFAOYSA-N 1-cyclohexyl-4-(4-cyclohexylphenyl)benzene Chemical group C1CCCCC1C1=CC=C(C=2C=CC(=CC=2)C2CCCCC2)C=C1 OLUVNSGCKHZQJQ-UHFFFAOYSA-N 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
- GDOBGDUGIFUCJV-UHFFFAOYSA-N 2,2-dimethylbutane;2-methylprop-2-enoic acid Chemical compound CCC(C)(C)C.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O GDOBGDUGIFUCJV-UHFFFAOYSA-N 0.000 description 1
- YQSAPDQJFZPHOJ-UHFFFAOYSA-N 2-cyclohexyl-1,3-dithiane Chemical compound C1CCCCC1C1SCCCS1 YQSAPDQJFZPHOJ-UHFFFAOYSA-N 0.000 description 1
- SMHSPYVJAUGNOI-UHFFFAOYSA-N 2-cyclohexyl-1,4-dioxane Chemical compound C1CCCCC1C1OCCOC1 SMHSPYVJAUGNOI-UHFFFAOYSA-N 0.000 description 1
- HYYFAYFMSHAWFA-UHFFFAOYSA-N 2-cyclohexylethylbenzene Chemical compound C1CCCCC1CCC1=CC=CC=C1 HYYFAYFMSHAWFA-UHFFFAOYSA-N 0.000 description 1
- IBLVSWYGUFGDMF-UHFFFAOYSA-N 2-cyclohexylethylcyclohexane Chemical compound C1CCCCC1CCC1CCCCC1 IBLVSWYGUFGDMF-UHFFFAOYSA-N 0.000 description 1
- HUTHUTALXJNNRS-UHFFFAOYSA-N 2-cyclohexylpyridine Chemical compound C1CCCCC1C1=CC=CC=N1 HUTHUTALXJNNRS-UHFFFAOYSA-N 0.000 description 1
- YJDDXMSIMBMMGY-UHFFFAOYSA-N 2-cyclohexylpyrimidine Chemical compound C1CCCCC1C1=NC=CC=N1 YJDDXMSIMBMMGY-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- PLKROHNMZPCGLD-UHFFFAOYSA-N 3-cyclohexylpyridazine Chemical compound C1CCCCC1C1=CC=CN=N1 PLKROHNMZPCGLD-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
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- YFWMKHJNNZCGHF-UHFFFAOYSA-N 4-[1,1,2,2-tetrafluoro-2-(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1C(F)(F)C(F)(F)C1=CC=C(O)C=C1 YFWMKHJNNZCGHF-UHFFFAOYSA-N 0.000 description 1
- RIQIOKOQHGSKLN-UHFFFAOYSA-N 5,5-dibromo-1,3-dimethylimidazolidine-2,4-dione Chemical compound CN1C(=O)N(C)C(Br)(Br)C1=O RIQIOKOQHGSKLN-UHFFFAOYSA-N 0.000 description 1
- QNGKGXNZGWIDGS-UHFFFAOYSA-N 6-cyclohexyl-5-ethyl-5-phenylcyclohexa-1,3-diene Chemical compound C=1C=CC=CC=1C1(CC)C=CC=CC1C1CCCCC1 QNGKGXNZGWIDGS-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- ADIAPCNCEHFEPJ-UHFFFAOYSA-N [4-(2-cyclohexylethyl)cyclohexyl]benzene Chemical compound C1CCCCC1CCC(CC1)CCC1C1=CC=CC=C1 ADIAPCNCEHFEPJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
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- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
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- 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 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
-
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/323—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a binaphthyl
-
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/325—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a tetrahydronaphthalene, e.g. -2,6-diyl (tetralin)
-
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/326—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a decahydronaphthalene, e.g. -2,6-diyl (decalin)
-
- 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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
-
- 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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/03—Viewing layer characterised by chemical composition
- C09K2323/031—Polarizer or dye
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00115251 | 2000-07-13 | ||
| EP00115251.1 | 2000-07-13 | ||
| PCT/EP2001/007215 WO2002006195A1 (en) | 2000-07-13 | 2001-06-25 | Chiral compounds ii |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004504285A JP2004504285A (ja) | 2004-02-12 |
| JP2004504285A5 JP2004504285A5 (enExample) | 2008-08-14 |
| JP5317382B2 true JP5317382B2 (ja) | 2013-10-16 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002512102A Expired - Fee Related JP5317382B2 (ja) | 2000-07-13 | 2001-06-25 | キラルな化合物ｉｉ |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7318950B2 (enExample) |
| EP (1) | EP1299335B1 (enExample) |
| JP (1) | JP5317382B2 (enExample) |
| CN (1) | CN1206197C (enExample) |
| AT (1) | ATE372314T1 (enExample) |
| AU (1) | AU2001281884A1 (enExample) |
| DE (1) | DE60130338T2 (enExample) |
| WO (1) | WO2002006195A1 (enExample) |
Families Citing this family (116)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7081282B2 (en) | 2001-07-02 | 2006-07-25 | Merck Patent Gmbh | Optically variable marking |
| DE10257711B4 (de) | 2001-12-27 | 2019-09-26 | Merck Patent Gmbh | Polymerisierbare monocyclische Verbindungen enthaltende Flüssigkristallmischungen |
| US6699532B2 (en) | 2002-06-25 | 2004-03-02 | Mitsubishi Gas Chemical Company, Inc. | Optically active compound and liquid crystal composition containing the compound |
| DE10253606A1 (de) * | 2002-11-15 | 2004-05-27 | Merck Patent Gmbh | Elektrooptisches Lichtsteuerelement, elektrooptische Anzeige und Steuermedium |
| TW585898B (en) | 2002-12-26 | 2004-05-01 | Ind Tech Res Inst | Liquid crystal compounds with optical activities having high helical twisting power, method for preparing the same, and liquid crystal composition containing the compounds |
| ATE353319T1 (de) | 2003-08-20 | 2007-02-15 | Axys Pharm Inc | Acetylenderivate als inhibitoren von histondeacetylase |
| DE112005000732T5 (de) | 2004-03-25 | 2008-09-04 | Merck Patent Gmbh | Flüssigkristallverbindungen, Flüssigkristallmedium und Flüssigkristallanzeige |
| US7776307B2 (en) * | 2004-09-16 | 2010-08-17 | Etamota Corporation | Concentric gate nanotube transistor devices |
| US7462890B1 (en) | 2004-09-16 | 2008-12-09 | Atomate Corporation | Nanotube transistor integrated circuit layout |
| US7345296B2 (en) * | 2004-09-16 | 2008-03-18 | Atomate Corporation | Nanotube transistor and rectifying devices |
| US7943418B2 (en) * | 2004-09-16 | 2011-05-17 | Etamota Corporation | Removing undesirable nanotubes during nanotube device fabrication |
| WO2006063662A1 (en) | 2004-12-17 | 2006-06-22 | Merck Patent Gmbh | Liquid crystal system and liquid crystal display |
| JP2006273978A (ja) * | 2005-03-29 | 2006-10-12 | 21 Aomori Sangyo Sogo Shien Center | ビナフチル基をもつ化合物を含む液晶組成物 |
| CA2644917A1 (en) * | 2006-03-15 | 2007-09-20 | Trustees Of Tufts College | Fluorinated carbohydrates and their use in tumor visualization, tissue engineering, and cancer chemotherapy |
| EP1911828B1 (de) | 2006-10-12 | 2010-09-01 | Merck Patent GmbH | Flüssigkristallanzeige |
| EP2094815B1 (en) | 2006-12-22 | 2012-06-27 | Rolic AG | Patternable liquid crystal polymer comprising thio-ether units |
| US20080272361A1 (en) * | 2007-05-02 | 2008-11-06 | Atomate Corporation | High Density Nanotube Devices |
| DE102008056221A1 (de) | 2007-11-30 | 2009-06-04 | Merck Patent Gmbh | Polymerisierbare Verbindungen |
| KR20100110853A (ko) * | 2007-12-31 | 2010-10-13 | 아토메이트 코포레이션 | 에지-접촉된 수직형 탄소 나노튜브 트랜지스터 |
| EP2098584B1 (en) | 2008-03-05 | 2011-10-12 | Merck Patent GmbH | Liquid-crystalline medium and liquid-crystal display having high twist |
| WO2009153168A1 (de) * | 2008-06-17 | 2009-12-23 | Basf Se | Polymerisierbare chirale verbindungen, enthaltend 2,6-naphthyl- und isomannit-einheiten, und deren verwendung als chirale dotierstoffe |
| US8426626B2 (en) | 2008-10-28 | 2013-04-23 | Fujifilm Corporation | Compound having asymmetric carbon atom, oxidation-reduction reaction causing portion, and liquid crystal substituent |
| DE102009055829A1 (de) | 2008-12-22 | 2010-06-24 | Merck Patent Gmbh | Flüssigkristallanzeige |
| DE102010006691A1 (de) | 2009-02-06 | 2010-10-28 | Merck Patent Gmbh | Flüssigkristallines Medium und Flüssigkristallanzeige |
| EP2218764B1 (en) | 2009-02-13 | 2012-01-18 | Merck Patent GmbH | Chiral reactive mesogen mixture |
| US8176924B2 (en) * | 2009-03-11 | 2012-05-15 | Kent Displays Incorporated | Color changing artificial fingernails |
| DE102010012900A1 (de) | 2009-04-23 | 2010-11-25 | Merck Patent Gmbh | Flüssigkristallanzeige |
| US8168084B2 (en) | 2009-12-18 | 2012-05-01 | Vanderbilt University | Polar nematic compounds |
| DE102011011836A1 (de) | 2010-03-09 | 2011-09-15 | Merck Patent Gmbh | Polymerisierbare Verbindungen und ihre Verwendung in Flüssigkristallmedien und Flüssigkristallanzeigen |
| JP2011225520A (ja) | 2010-04-02 | 2011-11-10 | Jnc Corp | 重合性基を有する光学活性化合物ならびにその重合体 |
| DE102011015546A1 (de) | 2010-04-26 | 2012-01-26 | Merck Patent Gmbh | Polymerisierbare Verbindungen und ihre Verwendung in Flüssigkristallmedien und Flüssigkristallanzeigen |
| EP2399972B1 (en) | 2010-06-25 | 2015-11-25 | Merck Patent GmbH | Liquid-crystalline medium and liquid-crystal display having high twist |
| WO2012084200A1 (en) | 2010-12-21 | 2012-06-28 | Stichting Dutch Polymer Institute | Process for coating a curved article |
| TWI443180B (zh) | 2010-12-23 | 2014-07-01 | Ind Tech Res Inst | 對掌性雙萘基化合物 |
| DE102012003796A1 (de) | 2011-03-18 | 2012-09-20 | Merck Patent Gmbh | Flüssigkristallines Medium |
| KR102088166B1 (ko) | 2011-03-29 | 2020-03-12 | 메르크 파텐트 게엠베하 | 액정 매질 |
| DE102012009631A1 (de) | 2011-05-27 | 2012-11-29 | Merck Patent Gmbh | Polymerisierbare Verbindungen und ihre Verwendung in Flüssigkristallmedien und Flüssigkristallanzeigen |
| KR101986858B1 (ko) | 2011-06-01 | 2019-06-07 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 디스플레이 |
| CN103717707B (zh) | 2011-08-01 | 2016-06-22 | 默克专利股份有限公司 | 液晶介质和液晶显示器 |
| JP6386378B2 (ja) | 2011-09-06 | 2018-09-05 | 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 | 液晶媒体および液晶ディスプレイ |
| EP2568032B1 (en) | 2011-09-06 | 2014-11-26 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| DE102012024126A1 (de) | 2011-12-20 | 2013-06-20 | Merck Patent Gmbh | Flüssigkristallines Medium |
| EP2623927A1 (en) | 2012-02-02 | 2013-08-07 | Stichting Dutch Polymer Institute | Optical strain sensor |
| US9862887B2 (en) | 2012-04-20 | 2018-01-09 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal display |
| EP2708587B1 (en) | 2012-09-18 | 2015-07-15 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| EP2904068B1 (en) | 2012-10-02 | 2016-10-12 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| KR20150090161A (ko) | 2012-11-27 | 2015-08-05 | 메르크 파텐트 게엠베하 | 렌즈 소자 |
| AU2014226533A1 (en) * | 2013-03-05 | 2015-08-13 | Archer Daniels Midland Company | Isohexide monotriflates and process for synthesis thereof |
| EP2778212B1 (en) * | 2013-03-15 | 2016-01-20 | OpSec Security Group, Inc. | Security device using liquid crystals |
| US9809749B2 (en) | 2013-04-19 | 2017-11-07 | Merck Patent Gmbh | Mesogenic compound, liquid-crystal medium and liquid crystal display |
| WO2015101405A1 (en) | 2013-12-30 | 2015-07-09 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal display |
| EP3105302B1 (en) | 2014-02-13 | 2020-08-05 | Merck Patent GmbH | Reactive mesogen based polymer particles |
| JP6441899B2 (ja) * | 2014-03-20 | 2018-12-19 | 富士フイルム株式会社 | 組成物、光反射膜、輝度向上フィルム、バックライトユニット及び液晶表示装置 |
| KR20170032408A (ko) | 2014-07-18 | 2017-03-22 | 메르크 파텐트 게엠베하 | 액정 매질 및 이를 포함하는 고주파 부품 |
| DE102015009924A1 (de) | 2014-08-22 | 2016-02-25 | Merck Patent Gmbh | Flüssigkristallines Medium |
| DE102015015108A1 (de) | 2014-12-17 | 2016-06-23 | Merck Patent Gmbh | Flüssigkristallines Medium |
| US11208594B2 (en) | 2014-12-29 | 2021-12-28 | Merck Patent Gmbh | Liquid-crystalline medium and high-frequency components comprising same |
| JP6752795B2 (ja) | 2014-12-30 | 2020-09-09 | 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 | 液晶媒体およびそれを含む高周波数素子 |
| EP3124573B1 (en) | 2015-07-31 | 2018-03-28 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| CN108603121B (zh) | 2016-02-08 | 2023-02-10 | 默克专利股份有限公司 | 液晶介质及含有其的高频组件 |
| US20190127642A1 (en) | 2016-04-13 | 2019-05-02 | Merck Patent Gmbh | Composition for nanoencapsulation and nanocapsules comprising a liquid-crystalline medium |
| CN109642160A (zh) | 2016-08-24 | 2019-04-16 | 默克专利股份有限公司 | 液晶介质和液晶显示器 |
| EP3312257B1 (en) | 2016-10-18 | 2019-11-20 | Merck Patent GmbH | Liquid-crystalline medium and high-frequency components comprising same |
| JP7097878B2 (ja) | 2016-10-24 | 2022-07-08 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 液晶媒体 |
| WO2018078078A1 (en) | 2016-10-31 | 2018-05-03 | Merck Patent Gmbh | Nanocapsules comprising a liquid-crystalline medium |
| JP6866625B2 (ja) * | 2016-12-08 | 2021-04-28 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| KR101827801B1 (ko) | 2017-02-23 | 2018-02-09 | 한국화학연구원 | 아이소헥사이드 다이안하이드라이드 단량체, 이로부터 제조된 폴리이미드 및 이들의 제조방법 |
| CN110392726B (zh) | 2017-03-16 | 2023-11-03 | 默克专利股份有限公司 | 液晶介质 |
| TW201900854A (zh) | 2017-04-10 | 2019-01-01 | 德商馬克專利公司 | 用於奈米封裝之組合物及包含液晶介質之奈米囊 |
| WO2018192896A1 (en) | 2017-04-20 | 2018-10-25 | Merck Patent Gmbh | Light modulation element |
| KR20190039639A (ko) | 2017-10-05 | 2019-04-15 | 메르크 파텐트 게엠베하 | 작용화된 폴리비닐 알콜을 포함하는 조성물 및 액정 매질을 함유하는 나노캡슐 |
| WO2019110458A1 (en) | 2017-12-06 | 2019-06-13 | Merck Patent Gmbh | Liquid-crystalline medium for use in a switching element |
| EP3720924A1 (en) | 2017-12-06 | 2020-10-14 | Merck Patent GmbH | Liquid-crystalline medium for use in a switching element |
| EP3502210B1 (en) | 2017-12-20 | 2020-09-09 | Merck Patent GmbH | Liquid-crystal medium |
| EP3543313B1 (en) | 2018-03-23 | 2020-10-07 | Merck Patent GmbH | Liquid-crystalline medium |
| EP3543314B1 (en) | 2018-03-23 | 2020-09-09 | Merck Patent GmbH | Liquid-crystalline medium |
| CN110483472A (zh) * | 2018-05-15 | 2019-11-22 | 石家庄诚志永华显示材料有限公司 | 手性化合物、包含该手性化合物的液晶组合物、光学各向异性体及液晶显示器件 |
| EP3739020B1 (en) | 2018-05-16 | 2023-08-23 | Merck Patent GmbH | Liquid-crystalline medium |
| WO2020120353A1 (en) | 2018-12-12 | 2020-06-18 | Merck Patent Gmbh | Polymerizable liquid crystal ink formulations |
| DE102019008592A1 (de) | 2018-12-12 | 2020-06-18 | Merck Patent Gmbh | Komponenten für die Hochfrequenztechnik und Flüssigkristallmedium |
| US20220073822A1 (en) | 2018-12-13 | 2022-03-10 | Merck Patent Gmbh | Liquid-crystal medium |
| JP7612584B2 (ja) | 2018-12-19 | 2025-01-14 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | スイッチング素子に使用されるスイッチング層 |
| TWI845599B (zh) | 2019-01-25 | 2024-06-21 | 德商馬克專利公司 | 液晶介質 |
| IL274057B2 (en) | 2019-04-30 | 2024-03-01 | Merck Patent Gmbh | Isothiocyantotoluenes |
| JP7562566B2 (ja) | 2019-05-15 | 2024-10-07 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 液晶に基づくスイッチング素子の製造方法 |
| GB2589659B (en) | 2019-05-28 | 2023-04-05 | Merck Patent Gmbh | Compositions comprising polymerizable oligoethyleneglycol derivatives and nanocapsules containing a liquid-crystalline medium |
| EP3983501B1 (en) | 2019-06-17 | 2025-02-26 | Merck Patent GmbH | Liquid crystal-based light valve |
| CN114302872A (zh) | 2019-08-28 | 2022-04-08 | 默克专利股份有限公司 | 芳香族异硫氰酸酯 |
| CN110669529A (zh) * | 2019-09-10 | 2020-01-10 | 苏州大学 | 彩色液晶材料及其应用 |
| TWI877236B (zh) | 2019-10-10 | 2025-03-21 | 德商馬克專利公司 | 氟化芳族化合物 |
| US11834599B2 (en) | 2019-12-10 | 2023-12-05 | Merck Patent Gmbh | Aromatic isothiocyanates |
| KR20210077615A (ko) | 2019-12-17 | 2021-06-25 | 메르크 파텐트 게엠베하 | 액정 매질 |
| EP4153700B1 (en) | 2020-05-18 | 2025-02-26 | Merck Patent GmbH | Liquid-crystalline medium |
| CN115867629A (zh) | 2020-07-03 | 2023-03-28 | 默克专利股份有限公司 | 液晶介质 |
| KR20230035354A (ko) | 2020-07-03 | 2023-03-13 | 메르크 파텐트 게엠베하 | 액정 매질 |
| EP3933009B1 (en) | 2020-07-03 | 2023-08-16 | Merck Patent GmbH | Liquid crystal medium |
| WO2022008474A1 (en) | 2020-07-08 | 2022-01-13 | Merck Patent Gmbh | Optical component |
| EP3940040B1 (en) | 2020-07-16 | 2024-10-16 | Merck Patent GmbH | Liquid-crystalline medium |
| EP4204515A1 (en) | 2020-08-28 | 2023-07-05 | Merck Patent GmbH | Aromatic isothiocyanates |
| CN114525139B (zh) | 2020-10-07 | 2025-07-25 | 默克专利股份有限公司 | 液晶介质 |
| US20230392076A1 (en) | 2020-10-28 | 2023-12-07 | Merck Patent Gmbh | Aromatic isothiocyanates |
| EP4263750B1 (en) | 2020-12-16 | 2025-06-04 | Merck Patent GmbH | Heteroaromatic isothiocyanates |
| JP2023553699A (ja) | 2020-12-17 | 2023-12-25 | 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 | ヘテロ芳香族イソチオシアネート類 |
| US11802243B2 (en) | 2021-02-26 | 2023-10-31 | Merck Patent Gmbh | Liquid-crystal medium |
| WO2022207584A2 (en) | 2021-03-31 | 2022-10-06 | Merck Patent Gmbh | Aromatic isothiocyanates |
| EP4330343A1 (en) | 2021-04-29 | 2024-03-06 | Merck Patent GmbH | Liquid crystal medium |
| TW202317855A (zh) | 2021-08-06 | 2023-05-01 | 德商馬克專利公司 | 用於窗元件之切換層 |
| KR20240055826A (ko) | 2021-09-08 | 2024-04-29 | 메르크 파텐트 게엠베하 | 액정 매질 |
| JP7390676B1 (ja) * | 2022-05-17 | 2023-12-04 | パナソニックＩｐマネジメント株式会社 | 非線形光吸収材料、記録媒体、情報の記録方法及び情報の読出方法 |
| WO2023248719A1 (ja) | 2022-06-21 | 2023-12-28 | 富士フイルム株式会社 | 画像記録物及び画像記録物の製造方法、並びに、加飾成形体 |
| EP4306615A1 (en) | 2022-07-11 | 2024-01-17 | Merck Patent GmbH | Liquid-crystal medium |
| WO2024175615A1 (en) | 2023-02-24 | 2024-08-29 | Merck Patent Gmbh | Dihydronapthalene derivatives |
| WO2024260902A1 (en) | 2023-06-20 | 2024-12-26 | Merck Patent Gmbh | Liquid crystal medium |
| WO2025061649A1 (en) | 2023-09-20 | 2025-03-27 | Merck Patent Gmbh | Liquid crystal medium |
| US20250154412A1 (en) | 2023-11-08 | 2025-05-15 | Merck Patent Gmbh | Liquid crystal medium |
| WO2025196107A1 (en) | 2024-03-22 | 2025-09-25 | Merck Patent Gmbh | Indene derivatives |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3675136D1 (de) * | 1985-09-30 | 1990-11-29 | Hoechst Ag | Chirale phenolester mesogener carbonsaeuren und ihre verwendung als dotierstoff in fluessigkristal-phasen. |
| DE3534780A1 (de) * | 1985-09-30 | 1987-04-02 | Hoechst Ag | Chirale phenolester mesogener carbonsaeuren, ein verfahren zu deren herstellung und ihre verwendung als dotierstoff in fluessigkristall-phasen |
| US5585036A (en) * | 1988-03-04 | 1996-12-17 | Displaytech, Inc. | Liquid crystal compounds containing chiral 2-halo-2-methyl ether and ester tails |
| DE59004491D1 (de) * | 1989-09-01 | 1994-03-17 | Hoffmann La Roche | Chirale Dotierstoffe für Flüssigkristalle. |
| JP3187611B2 (ja) * | 1993-05-17 | 2001-07-11 | キヤノン株式会社 | 液晶性化合物、これを含む液晶組成物、それを有する液晶素子、それらを用いた表示方法および表示装置 |
| GB2298202B (en) | 1995-02-24 | 1998-09-16 | Merck Patent Gmbh | Chiral polymerizable binaphthol derivatives |
| US5702637A (en) * | 1995-04-19 | 1997-12-30 | Minnesota Mining And Manufacturing Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| CN1108325C (zh) | 2000-03-12 | 2003-05-14 | 吉林大学 | 手性环状预聚物的合成 |
-
2001
- 2001-06-25 WO PCT/EP2001/007215 patent/WO2002006195A1/en not_active Ceased
- 2001-06-25 AU AU2001281884A patent/AU2001281884A1/en not_active Abandoned
- 2001-06-25 EP EP01960376A patent/EP1299335B1/en not_active Expired - Lifetime
- 2001-06-25 CN CNB018127266A patent/CN1206197C/zh not_active Expired - Lifetime
- 2001-06-25 US US10/332,806 patent/US7318950B2/en not_active Expired - Fee Related
- 2001-06-25 JP JP2002512102A patent/JP5317382B2/ja not_active Expired - Fee Related
- 2001-06-25 DE DE60130338T patent/DE60130338T2/de not_active Expired - Lifetime
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| EP1299335A1 (en) | 2003-04-09 |
| AU2001281884A1 (en) | 2002-01-30 |
| US7318950B2 (en) | 2008-01-15 |
| JP2004504285A (ja) | 2004-02-12 |
| ATE372314T1 (de) | 2007-09-15 |
| US20030178601A1 (en) | 2003-09-25 |
| CN1206197C (zh) | 2005-06-15 |
| DE60130338D1 (de) | 2007-10-18 |
| EP1299335B1 (en) | 2007-09-05 |
| DE60130338T2 (de) | 2008-05-29 |
| CN1441765A (zh) | 2003-09-10 |
| WO2002006195A1 (en) | 2002-01-24 |
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