JP4425545B2 - キラルな化合物 - Google Patents
キラルな化合物 Download PDFInfo
- Publication number
- JP4425545B2 JP4425545B2 JP2002591478A JP2002591478A JP4425545B2 JP 4425545 B2 JP4425545 B2 JP 4425545B2 JP 2002591478 A JP2002591478 A JP 2002591478A JP 2002591478 A JP2002591478 A JP 2002591478A JP 4425545 B2 JP4425545 B2 JP 4425545B2
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- JP
- Japan
- Prior art keywords
- liquid crystal
- atoms
- chiral
- independently
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 150000001875 compounds Chemical class 0.000 title claims description 152
- 239000000203 mixture Substances 0.000 claims description 103
- 239000004973 liquid crystal related substance Substances 0.000 claims description 94
- -1 1,3-dioxolane-4,5-diyl Chemical group 0.000 claims description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 229910052731 fluorine Inorganic materials 0.000 claims description 39
- 239000002019 doping agent Substances 0.000 claims description 37
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- 230000003098 cholesteric effect Effects 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 230000003287 optical effect Effects 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 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
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000002537 cosmetic Substances 0.000 claims description 7
- 239000000049 pigment Substances 0.000 claims description 7
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 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 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000003860 storage Methods 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 229920000106 Liquid crystal polymer Polymers 0.000 claims description 4
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims description 4
- 239000004904 UV filter Substances 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 239000000057 synthetic resin Substances 0.000 claims description 3
- 229920003002 synthetic resin Polymers 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 description 25
- 239000010408 film Substances 0.000 description 18
- 239000012071 phase Substances 0.000 description 17
- 239000000758 substrate Substances 0.000 description 17
- 229920000728 polyester Polymers 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000011295 pitch Substances 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920006254 polymer film Polymers 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000005529 alkyleneoxy group Chemical group 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 125000006850 spacer group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 230000001419 dependent effect Effects 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000002411 adverse Effects 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 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
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- 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 2
- SJSRFXJWBKOROD-UHFFFAOYSA-N 1,1'-bi(cyclohexyl)-1-carboxylic acid Chemical compound C1CCCCC1C1(C(=O)O)CCCCC1 SJSRFXJWBKOROD-UHFFFAOYSA-N 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-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
- 239000005711 Benzoic acid Substances 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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 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
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000012952 cationic photoinitiator Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 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
- 238000005034 decoration Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000006260 foam Substances 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000000746 purification 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
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 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
- KIHQZLPHVZKELA-UHFFFAOYSA-N 1,3-dibromopropan-2-ol Chemical compound BrCC(O)CBr KIHQZLPHVZKELA-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
- UTXIFKBYNJRJPH-UHFFFAOYSA-N 1-(2-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-5,6,7,8-tetrahydronaphthalen-2-ol Chemical compound C1CCCC2=C1C=CC(O)=C2C1=C2CCCCC2=CC=C1O UTXIFKBYNJRJPH-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
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-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
- 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
- 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
- 229920002799 BoPET Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000005569 butenylene group Chemical group 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
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical class OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 238000007697 cis-trans-isomerization reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- DQZKGSRJOUYVPL-UHFFFAOYSA-N cyclohexyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCCCC1 DQZKGSRJOUYVPL-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 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 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005291 magnetic effect Effects 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 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 1
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 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 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 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 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- 125000004351 phenylcyclohexyl group Chemical group C1(=CC=CC=C1)C1(CCCCC1)* 0.000 description 1
- 238000007699 photoisomerization reaction Methods 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 125000006410 propenylene group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
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- 230000007704 transition Effects 0.000 description 1
- 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 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- C07D321/12—Eight-membered rings
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
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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
- C09K19/52—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
- C09K19/588—Heterocyclic compounds
-
- 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
- C09K2019/0448—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 end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
-
- 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
- C09K2019/343—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a seven-membered ring
- C09K2019/3433—Seven-membered ring with oxygen(s) in fused, bridged or spiro ring systems
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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
- 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
- C09K2019/3438—Crown ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dermatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Toxicology (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01111954 | 2001-05-21 | ||
| PCT/EP2002/004574 WO2002094805A1 (en) | 2001-05-21 | 2002-04-25 | Chiral compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005501003A JP2005501003A (ja) | 2005-01-13 |
| JP2005501003A5 JP2005501003A5 (enExample) | 2005-12-22 |
| JP4425545B2 true JP4425545B2 (ja) | 2010-03-03 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002591478A Expired - Lifetime JP4425545B2 (ja) | 2001-05-21 | 2002-04-25 | キラルな化合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7223450B2 (enExample) |
| EP (1) | EP1389199B1 (enExample) |
| JP (1) | JP4425545B2 (enExample) |
| KR (1) | KR100920912B1 (enExample) |
| CN (1) | CN100338054C (enExample) |
| WO (1) | WO2002094805A1 (enExample) |
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| JP4425545B2 (ja) * | 2001-05-21 | 2010-03-03 | 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 | キラルな化合物 |
| US20030100803A1 (en) * | 2001-11-26 | 2003-05-29 | Lu Helen S.M. | 3-Alkylated-5,5',6,6',7,7,'8,8'-octahydro-2,2'-binaphthols and 3,3'-dialkylated-5,5',6,6',7,7',8,8'-octahydro-2,2'-binaphthols and processes for making them |
| GB2393966B (en) * | 2002-08-14 | 2006-02-22 | Merck Patent Gmbh | High-twist liquid-crystalline medium and liquid-crystal display |
| GB2394475B (en) * | 2002-09-14 | 2006-02-22 | Merck Patent Gmbh | High-twist liquid-crystalline medium and liquid-crystal display |
| AU2003288049A1 (en) * | 2002-12-07 | 2004-06-30 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal display with a highly twisted structure |
| DE102004062962B4 (de) * | 2004-01-19 | 2014-06-18 | Merck Patent Gmbh | Flüssigkristallines Medium und ihre Verwendung in einerFlüssigkristallanzeige mit hoher Verdrillung |
| DE602005007917D1 (de) * | 2004-09-06 | 2008-08-14 | Merck Patent Gmbh | Polymerisierbares flüssigkristallmaterial |
| KR101355300B1 (ko) * | 2004-11-26 | 2014-01-23 | 샤프 가부시키가이샤 | 액정 매질 |
| JP2008524347A (ja) | 2004-12-17 | 2008-07-10 | 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 ハフトング | 液晶システムおよび液晶ディスプレイ |
| EP1928980B1 (en) * | 2005-09-30 | 2011-03-09 | Merck Patent GmbH | Chiral compounds |
| EP1928854B1 (en) * | 2005-09-30 | 2009-12-16 | Merck Patent GmbH | Chiral compounds |
| EP1816180B1 (en) * | 2006-02-07 | 2008-10-29 | Merck Patent GmbH | Mesogenic compounds, liquid crystal medium, and liquid crystal display |
| DE502007004908D1 (de) * | 2006-10-12 | 2010-10-14 | Merck Patent Gmbh | Flüssigkristallanzeige |
| US8574454B2 (en) | 2006-12-22 | 2013-11-05 | Rolic Ag | Patternable liquid crystal polymer comprising thio-ether units |
| US20080259268A1 (en) | 2007-04-12 | 2008-10-23 | Fujifilm Corporation | Process of producing substrate for liquid crystal display device |
| DE102008024867A1 (de) | 2007-06-15 | 2008-12-24 | Merck Patent Gmbh | Verfahren zur Synthese von cyclischen BINOL-Derivaten |
| KR20090009652A (ko) * | 2007-07-20 | 2009-01-23 | 삼성전자주식회사 | 탄소함유 상변화 물질과 이를 포함하는 메모리 소자 및 그동작 방법 |
| DE102008056221A1 (de) | 2007-11-30 | 2009-06-04 | Merck Patent Gmbh | Polymerisierbare Verbindungen |
| EP2098584B1 (en) | 2008-03-05 | 2011-10-12 | Merck Patent GmbH | Liquid-crystalline medium and liquid-crystal display having high twist |
| KR20160118375A (ko) * | 2008-08-29 | 2016-10-11 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 디스플레이 |
| CN102264866B (zh) | 2008-12-22 | 2014-06-18 | 默克专利股份有限公司 | 液晶显示器 |
| DE102010006691A1 (de) | 2009-02-06 | 2010-10-28 | Merck Patent Gmbh | Flüssigkristallines Medium und Flüssigkristallanzeige |
| ATE541913T1 (de) * | 2009-02-13 | 2012-02-15 | Merck Patent Gmbh | Chirale reaktionsfähige mesogenmischung |
| DE102010012900A1 (de) | 2009-04-23 | 2010-11-25 | Merck Patent Gmbh | Flüssigkristallanzeige |
| TW201038527A (en) * | 2009-04-24 | 2010-11-01 | Agi Corp | 1,1'-bi-2-naphthol derivatives having (meth) acrylates group |
| TWI410424B (zh) * | 2009-11-12 | 2013-10-01 | Ind Tech Res Inst | 旋光性化合物及含有此化合物之液晶組成物 |
| 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 |
| 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 |
| DE102012003796A1 (de) | 2011-03-18 | 2012-09-20 | Merck Patent Gmbh | Flüssigkristallines Medium |
| WO2012130380A1 (de) | 2011-03-29 | 2012-10-04 | Merck Patent Gmbh | Flüssigkristallines medium |
| CN103339224B (zh) * | 2011-04-27 | 2015-07-22 | 肯特显示器公司 | 胆甾醇型液晶显示器用四氧联苯酯手性掺杂剂 |
| DE102012009631A1 (de) | 2011-05-27 | 2012-11-29 | Merck Patent Gmbh | Polymerisierbare Verbindungen und ihre Verwendung in Flüssigkristallmedien und Flüssigkristallanzeigen |
| DE102012201962A1 (de) | 2011-10-13 | 2013-04-18 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Substituierte Aminoalkohole als chirale Dotanden |
| 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 |
| CN104411800B (zh) | 2012-06-26 | 2016-11-23 | 默克专利股份有限公司 | 制备双折射聚合物膜的方法 |
| CN104854217B (zh) * | 2012-12-17 | 2017-06-23 | 捷恩智株式会社 | 液晶组合物、混合物、复合材料、液晶元件及手性化合物 |
| KR102243116B1 (ko) | 2013-10-21 | 2021-04-22 | 메르크 파텐트 게엠베하 | 복굴절성 중합체 필름의 제조 방법 |
| EP3105302B1 (en) | 2014-02-13 | 2020-08-05 | Merck Patent GmbH | Reactive mesogen based polymer particles |
| WO2016008568A1 (en) | 2014-07-18 | 2016-01-21 | Merck Patent Gmbh | Liquid-crystalline medium and high-frequency components comprising same |
| 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 |
| WO2016107670A1 (en) | 2014-12-29 | 2016-07-07 | Merck Patent Gmbh | Liquid-crystalline medium and high-frequency components comprising same |
| WO2016107671A1 (en) | 2014-12-30 | 2016-07-07 | Merck Patent Gmbh | Liquid-crystalline medium and high-frequency components comprising same |
| JP6913084B2 (ja) * | 2015-10-06 | 2021-08-04 | 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 | キラル化合物 |
| US11180698B2 (en) | 2016-02-08 | 2021-11-23 | Merck Patent Gmbh | Liquid-crystalline medium and high-frequency components comprising same |
| CN109072081A (zh) | 2016-04-13 | 2018-12-21 | 默克专利股份有限公司 | 包含液晶介质的用于纳米包封的组合物及纳米胶囊 |
| KR20190009317A (ko) * | 2016-05-17 | 2019-01-28 | 메르크 파텐트 게엠베하 | 광 변조 소자 |
| CN107759560B (zh) * | 2016-08-16 | 2020-06-26 | 北京八亿时空液晶科技股份有限公司 | 一种联萘二酚类手性化合物及其制备方法与应用 |
| EP3504292B1 (en) | 2016-08-24 | 2020-05-27 | Merck Patent GmbH | Liquid crystalline medium and liquid crystal display |
| EP3312257B1 (en) | 2016-10-18 | 2019-11-20 | Merck Patent GmbH | Liquid-crystalline medium and high-frequency components comprising same |
| CN109863225B (zh) | 2016-10-24 | 2024-02-02 | 默克专利股份有限公司 | 液晶介质 |
| WO2018078078A1 (en) | 2016-10-31 | 2018-05-03 | Merck Patent Gmbh | Nanocapsules comprising a liquid-crystalline medium |
| CN110392726B (zh) | 2017-03-16 | 2023-11-03 | 默克专利股份有限公司 | 液晶介质 |
| WO2018189068A1 (en) | 2017-04-10 | 2018-10-18 | Merck Patent Gmbh | Composition for nanoencapsulation and nanocapsules comprising a liquid-crystalline medium |
| CN110536949B (zh) | 2017-04-20 | 2023-08-25 | 默克专利股份有限公司 | 光调制元件 |
| KR20190039639A (ko) | 2017-10-05 | 2019-04-15 | 메르크 파텐트 게엠베하 | 작용화된 폴리비닐 알콜을 포함하는 조성물 및 액정 매질을 함유하는 나노캡슐 |
| CN107903916B (zh) * | 2017-11-29 | 2020-12-11 | 北京化工大学 | 胆甾相液晶组合物在紫外光检测中的应用和紫外光检测器 |
| WO2019110458A1 (en) | 2017-12-06 | 2019-06-13 | Merck Patent Gmbh | Liquid-crystalline medium for use in a switching element |
| CN119823768A (zh) | 2017-12-06 | 2025-04-15 | 默克专利股份有限公司 | 用于切换元件的液晶介质 |
| EP3502210B1 (en) | 2017-12-20 | 2020-09-09 | Merck Patent GmbH | Liquid-crystal medium |
| JP7183541B2 (ja) * | 2018-01-18 | 2022-12-06 | Dic株式会社 | 液晶組成物及び液晶表示素子 |
| 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 |
| EP3784497A1 (en) | 2018-04-25 | 2021-03-03 | Basf Se | Process for the production of strongly adherent liquid crystal films on flexible substrates |
| 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 |
| DE102019008592A1 (de) | 2018-12-12 | 2020-06-18 | Merck Patent Gmbh | Komponenten für die Hochfrequenztechnik und Flüssigkristallmedium |
| US12460134B2 (en) | 2018-12-12 | 2025-11-04 | Merck Patent Gmbh | Polymerizable liquid crystal ink formulations |
| EP3894415A1 (en) | 2018-12-13 | 2021-10-20 | 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 |
| US12365838B2 (en) | 2019-05-15 | 2025-07-22 | Merck Patent Gmbh | Method for preparing a liquid crystal-based switching element |
| GB2589659B (en) | 2019-05-28 | 2023-04-05 | Merck Patent Gmbh | Compositions comprising polymerizable oligoethyleneglycol derivatives and nanocapsules containing a liquid-crystalline medium |
| JP7662542B2 (ja) | 2019-06-17 | 2025-04-15 | 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 | 液晶系光バルブ |
| EP4017938A1 (en) | 2019-08-19 | 2022-06-29 | Basf Se | A process for the production of fingerprint texture free liquid crystal films |
| WO2021037962A1 (en) | 2019-08-28 | 2021-03-04 | Merck Patent Gmbh | Aromatic isothiocyanates |
| TWI877236B (zh) | 2019-10-10 | 2025-03-21 | 德商馬克專利公司 | 氟化芳族化合物 |
| EP4073205B1 (en) | 2019-12-10 | 2024-06-12 | Merck Patent GmbH | Aromatic isothiocyanates |
| KR20210077615A (ko) | 2019-12-17 | 2021-06-25 | 메르크 파텐트 게엠베하 | 액정 매질 |
| CN115667461B (zh) | 2020-05-18 | 2025-02-25 | 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 |
| US12116521B2 (en) | 2020-07-03 | 2024-10-15 | Merck Patent Gmbh | Liquid crystal medium |
| EP3933009B1 (en) | 2020-07-03 | 2023-08-16 | Merck Patent GmbH | Liquid crystal medium |
| KR20230037041A (ko) | 2020-07-08 | 2023-03-15 | 메르크 파텐트 게엠베하 | 광학 컴포넌트 |
| EP3940040B1 (en) | 2020-07-16 | 2024-10-16 | Merck Patent GmbH | Liquid-crystalline medium |
| WO2022043376A1 (en) | 2020-08-28 | 2022-03-03 | Merck Patent Gmbh | Aromatic isothiocyanates |
| KR102858318B1 (ko) * | 2020-09-17 | 2025-09-10 | 후지필름 가부시키가이샤 | 콜레스테릭 액정층의 제조 방법 및 도포 장치 |
| CN114525139B (zh) | 2020-10-07 | 2025-07-25 | 默克专利股份有限公司 | 液晶介质 |
| JP2023547643A (ja) | 2020-10-28 | 2023-11-13 | 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 | 芳香族イソチオシアネート類 |
| US12077703B2 (en) | 2020-12-16 | 2024-09-03 | 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 |
| JP2024512675A (ja) | 2021-03-31 | 2024-03-19 | 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 | 芳香族イソチオシアネート類 |
| CN117203307A (zh) | 2021-04-29 | 2023-12-08 | 默克专利股份有限公司 | 液晶介质 |
| WO2022233908A1 (en) | 2021-05-07 | 2022-11-10 | Merck Patent Gmbh | Reactive mesogens |
| 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 |
| CN118369399A (zh) | 2021-09-08 | 2024-07-19 | 默克专利股份有限公司 | 液晶介质 |
| JP2024009784A (ja) | 2022-07-11 | 2024-01-23 | 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 |
| JPWO2024096003A1 (enExample) * | 2022-11-04 | 2024-05-10 | ||
| CN120787252A (zh) | 2023-02-24 | 2025-10-14 | 默克专利股份有限公司 | 二氢萘衍生物 |
| WO2024200529A1 (en) | 2023-03-31 | 2024-10-03 | Merck Patent Gmbh | Chiral reactive mesogen mixture |
| CN121039252A (zh) | 2023-03-31 | 2025-11-28 | 默克专利股份有限公司 | 具有高双折射率的反应性介晶 |
| WO2024235946A1 (en) | 2023-05-17 | 2024-11-21 | Merck Patent Gmbh | Optical element comprising a chiral lc polymer film |
| WO2024260930A1 (en) | 2023-06-20 | 2024-12-26 | Merck Patent Gmbh | Half-wave plate |
| 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 |
| WO2025214945A1 (en) | 2024-04-11 | 2025-10-16 | Merck Patent Gmbh | Polymerizable liquid crystal formulations |
| WO2025252654A1 (en) | 2024-06-04 | 2025-12-11 | Merck Patent Gmbh | Polymerizable liquid crystal composition |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP4425545B2 (ja) * | 2001-05-21 | 2010-03-03 | 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 | キラルな化合物 |
| US20040173775A1 (en) * | 2001-06-13 | 2004-09-09 | Juliane Suermann | Fluid crystalline medium and high-torsion liquid crystalline display device |
| EP1453933B1 (en) * | 2001-12-12 | 2005-08-31 | MERCK PATENT GmbH | Biaxial film |
| DE10332220B4 (de) * | 2002-08-03 | 2013-05-29 | Merck Patent Gmbh | Flüssigkristallines Medium und seine Verwendung in einer Flüssigkristallanzeige mit hoher Verdrillung |
| EP1422283B1 (en) * | 2002-11-02 | 2014-03-05 | Merck Patent GmbH | Printable liquid crystal material |
-
2002
- 2002-04-25 JP JP2002591478A patent/JP4425545B2/ja not_active Expired - Lifetime
- 2002-04-25 WO PCT/EP2002/004574 patent/WO2002094805A1/en not_active Ceased
- 2002-04-25 EP EP02740515A patent/EP1389199B1/en not_active Expired - Lifetime
- 2002-04-25 KR KR1020037015130A patent/KR100920912B1/ko not_active Expired - Lifetime
- 2002-04-25 CN CNB028101901A patent/CN100338054C/zh not_active Expired - Lifetime
- 2002-04-25 US US10/477,896 patent/US7223450B2/en not_active Expired - Lifetime
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| US20040135119A1 (en) | 2004-07-15 |
| EP1389199A1 (en) | 2004-02-18 |
| KR100920912B1 (ko) | 2009-10-12 |
| CN100338054C (zh) | 2007-09-19 |
| HK1065310A1 (zh) | 2005-02-18 |
| WO2002094805A1 (en) | 2002-11-28 |
| US20070229732A1 (en) | 2007-10-04 |
| EP1389199B1 (en) | 2013-02-27 |
| US7425356B2 (en) | 2008-09-16 |
| JP2005501003A (ja) | 2005-01-13 |
| CN1509280A (zh) | 2004-06-30 |
| US7223450B2 (en) | 2007-05-29 |
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