KR100920912B1 - 키랄 화합물 - Google Patents
키랄 화합물 Download PDFInfo
- Publication number
- KR100920912B1 KR100920912B1 KR1020037015130A KR20037015130A KR100920912B1 KR 100920912 B1 KR100920912 B1 KR 100920912B1 KR 1020037015130 A KR1020037015130 A KR 1020037015130A KR 20037015130 A KR20037015130 A KR 20037015130A KR 100920912 B1 KR100920912 B1 KR 100920912B1
- Authority
- KR
- South Korea
- Prior art keywords
- liquid crystal
- formula
- chiral
- compound
- compounds
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 162
- 239000000203 mixture Substances 0.000 claims abstract description 117
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 95
- 230000003287 optical effect Effects 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 11
- 239000002537 cosmetic Substances 0.000 claims abstract description 6
- 238000003860 storage Methods 0.000 claims abstract description 6
- 229920000106 Liquid crystal polymer Polymers 0.000 claims abstract description 5
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims abstract description 4
- 239000000853 adhesive Substances 0.000 claims abstract description 4
- 230000001070 adhesive effect Effects 0.000 claims abstract description 4
- 229920003002 synthetic resin Polymers 0.000 claims abstract description 4
- 239000000057 synthetic resin Substances 0.000 claims abstract description 4
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 230000003098 cholesteric effect Effects 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 8
- 125000002947 alkylene 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
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 claims description 4
- -1 diagnostics Substances 0.000 abstract description 51
- 239000002019 doping agent Substances 0.000 abstract description 38
- 229920000642 polymer Polymers 0.000 abstract description 17
- 239000000049 pigment Substances 0.000 abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 5
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 description 31
- 239000000460 chlorine Substances 0.000 description 25
- 229910052801 chlorine Inorganic materials 0.000 description 23
- 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
- 239000012071 phase Substances 0.000 description 15
- 239000011295 pitch Substances 0.000 description 15
- 239000010410 layer Substances 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000008859 change Effects 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 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
- 229910052794 bromium Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 125000000524 functional group Chemical group 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 0 CC(C)(CC1)CCC1N* Chemical compound CC(C)(CC1)CCC1N* 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 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
- 239000004904 UV filter Substances 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
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004435 hydrogen atom Chemical group [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
- 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
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 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
- 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
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-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
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Chemical group 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 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
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
- 230000000694 effects Effects 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
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 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
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 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
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 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
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- SJSRFXJWBKOROD-UHFFFAOYSA-N 1,1'-bi(cyclohexyl)-1-carboxylic acid Chemical compound C1CCCCC1C1(C(=O)O)CCCCC1 SJSRFXJWBKOROD-UHFFFAOYSA-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
- JYNLTWJPPFIEFR-UHFFFAOYSA-N 1,2-dicyclohexylcyclohexene Chemical compound C1CCCCC1C1=C(C2CCCCC2)CCCC1 JYNLTWJPPFIEFR-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
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-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
- RFFCUDDJJDOFLS-UHFFFAOYSA-N 1-cyclohexylcyclohexene Chemical compound C1CCCCC1C1=CCCCC1 RFFCUDDJJDOFLS-UHFFFAOYSA-N 0.000 description 1
- BMEVZVXFJBPTKE-UHFFFAOYSA-N 1-hexylcyclohexane-1-carboxylic acid Chemical compound CCCCCCC1(C(O)=O)CCCCC1 BMEVZVXFJBPTKE-UHFFFAOYSA-N 0.000 description 1
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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
- ZKTFZNPTAJIXMK-UHFFFAOYSA-N 2-cyclohexylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1CCCCC1 ZKTFZNPTAJIXMK-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
- WLNDDIWESXCXHM-UHFFFAOYSA-N 2-phenyl-1,4-dioxane Chemical group C1OCCOC1C1=CC=CC=C1 WLNDDIWESXCXHM-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 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
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-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
- 239000005711 Benzoic acid Substances 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
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-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
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 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
- 238000012663 cationic photopolymerization Methods 0.000 description 1
- 150000001768 cations Chemical class 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
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 238000007697 cis-trans-isomerization reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 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
- 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
- 239000000032 diagnostic agent Substances 0.000 description 1
- 229940039227 diagnostic agent Drugs 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
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 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
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000706 filtrate 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
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003999 initiator Substances 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
- 239000010977 jade Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 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
- 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
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 230000000704 physical effect 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
- 230000008569 process Effects 0.000 description 1
- 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
- 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
- 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
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000010409 thin film Substances 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
- 229910052721 tungsten Inorganic materials 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
- 238000010626 work up procedure Methods 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
-
- 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
-
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01111954.2 | 2001-05-21 | ||
| EP01111954 | 2001-05-21 | ||
| PCT/EP2002/004574 WO2002094805A1 (en) | 2001-05-21 | 2002-04-25 | Chiral compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20040018374A KR20040018374A (ko) | 2004-03-03 |
| KR100920912B1 true KR100920912B1 (ko) | 2009-10-12 |
Family
ID=8177451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020037015130A Expired - Lifetime KR100920912B1 (ko) | 2001-05-21 | 2002-04-25 | 키랄 화합물 |
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) |
Families Citing this family (115)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100338054C (zh) * | 2001-05-21 | 2007-09-19 | 默克专利股份有限公司 | 手性化合物 |
| 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 |
| WO2004053022A1 (de) * | 2002-12-07 | 2004-06-24 | Merck Patent Gmbh | Flüssigkristallines medium und flüssigkristallanzeige mit hoher verdrillung |
| DE102004062962B4 (de) * | 2004-01-19 | 2014-06-18 | Merck Patent Gmbh | Flüssigkristallines Medium und ihre Verwendung in einerFlüssigkristallanzeige mit hoher Verdrillung |
| JP4846724B2 (ja) * | 2004-09-06 | 2011-12-28 | 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 | 重合性液晶材料 |
| KR101355300B1 (ko) * | 2004-11-26 | 2014-01-23 | 샤프 가부시키가이샤 | 액정 매질 |
| ATE444346T1 (de) | 2004-12-17 | 2009-10-15 | Merck Patent Gmbh | Flüssigkristallines system undflüssigkristalline anzeige |
| US7771800B2 (en) * | 2005-09-30 | 2010-08-10 | Merck Patent Gmbh | Chiral compounds |
| CN101277943B (zh) * | 2005-09-30 | 2012-05-23 | 默克专利股份有限公司 | 手性化合物 |
| 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 |
| WO2008077261A1 (en) | 2006-12-22 | 2008-07-03 | 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 |
| EP2065361B1 (de) | 2007-11-30 | 2014-12-17 | 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 |
| WO2010022891A1 (en) * | 2008-08-29 | 2010-03-04 | Merck Patent Gmbh | Liquid crystalline medium and liquid crystal display |
| KR101648601B1 (ko) | 2008-12-22 | 2016-08-16 | 메르크 파텐트 게엠베하 | 액정 디스플레이 |
| 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 |
| 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 |
| CN104893743A (zh) | 2011-03-29 | 2015-09-09 | 默克专利股份有限公司 | 液晶介质 |
| US8691111B2 (en) * | 2011-04-27 | 2014-04-08 | Kent Displays Inc. | Tetraoxybiphenyl ester chiral dopants for cholesteric liquid crystal displays |
| KR101997297B1 (ko) | 2011-05-27 | 2019-07-05 | 메르크 파텐트 게엠베하 | 중합성 화합물 및 이의 액정 매질 및 액정 디스플레이에서의 용도 |
| 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 |
| EP2864444B1 (en) | 2012-06-26 | 2018-08-01 | Merck Patent GmbH | Method of preparing a birefringent polymer film |
| 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 |
| CN105659121B (zh) | 2013-10-21 | 2019-04-30 | 默克专利股份有限公司 | 制备双折射聚合物膜的方法 |
| US9796926B2 (en) | 2014-02-13 | 2017-10-24 | Merck Patent Gmbh | Reactive mesogen based polymer particles |
| CN106661451A (zh) | 2014-07-18 | 2017-05-10 | 默克专利股份有限公司 | 液晶介质和包含其的高频组件 |
| EP2990460B1 (de) | 2014-08-22 | 2019-04-03 | 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 |
| 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 |
| EP3359625B1 (en) * | 2015-10-06 | 2019-10-23 | Merck Patent GmbH | Chiral compounds |
| KR102810583B1 (ko) | 2016-02-08 | 2025-05-22 | 메르크 파텐트 게엠베하 | 액정 매질 및 이를 포함하는 고-주파수 부품 |
| KR20180130569A (ko) | 2016-04-13 | 2018-12-07 | 메르크 파텐트 게엠베하 | 나노캡슐화를 위한 조성물 및 액정 매질을 포함하는 나노캡슐 |
| JP2019521372A (ja) * | 2016-05-17 | 2019-07-25 | 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 | 光変調素子 |
| 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 |
| KR20190075994A (ko) | 2016-10-24 | 2019-07-01 | 메르크 파텐트 게엠베하 | 액정 매질 |
| KR20190077034A (ko) | 2016-10-31 | 2019-07-02 | 메르크 파텐트 게엠베하 | 액정 매질을 포함하는 나노캡슐 |
| US20210115337A1 (en) | 2017-03-16 | 2021-04-22 | Merck Patent Gmbh | Liquid-crystalline medium |
| WO2018189068A1 (en) | 2017-04-10 | 2018-10-18 | Merck Patent Gmbh | Composition for nanoencapsulation and nanocapsules comprising a liquid-crystalline medium |
| US11124705B2 (en) | 2017-04-20 | 2021-09-21 | 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 |
| 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 |
| US11788009B2 (en) | 2017-12-06 | 2023-10-17 | Merck Patent Gmbh | Liquid-crystalline medium for use in a switching element |
| EP3720925B1 (en) | 2017-12-06 | 2023-02-15 | Merck Patent GmbH | Window element |
| 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 |
| EP3543314B1 (en) | 2018-03-23 | 2020-09-09 | Merck Patent GmbH | Liquid-crystalline medium |
| EP3543313B1 (en) | 2018-03-23 | 2020-10-07 | Merck Patent GmbH | Liquid-crystalline medium |
| CN111936315A (zh) | 2018-04-25 | 2020-11-13 | 巴斯夫欧洲公司 | 在柔性基材上制备强粘附性液晶膜的方法 |
| 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 |
| JP2022513827A (ja) | 2018-12-12 | 2022-02-09 | 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 | 重合性液晶インク配合物 |
| DE102019008592A1 (de) | 2018-12-12 | 2020-06-18 | Merck Patent Gmbh | Komponenten für die Hochfrequenztechnik und Flüssigkristallmedium |
| EP3894415A1 (en) | 2018-12-13 | 2021-10-20 | Merck Patent GmbH | Liquid-crystal medium |
| CN113195683B (zh) | 2018-12-19 | 2025-01-10 | 默克专利股份有限公司 | 用于切换元件的切换层 |
| KR102803509B1 (ko) | 2019-01-25 | 2025-05-09 | 메르크 파텐트 게엠베하 | 액정 매질 |
| IL274057B2 (en) | 2019-04-30 | 2024-03-01 | Merck Patent Gmbh | Isothiocyantotoluenes |
| EP3969540A1 (en) | 2019-05-15 | 2022-03-23 | 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 |
| EP3983501B1 (en) | 2019-06-17 | 2025-02-26 | Merck Patent GmbH | Liquid crystal-based light valve |
| EP4017938A1 (en) | 2019-08-19 | 2022-06-29 | Basf Se | A process for the production of fingerprint texture free liquid crystal films |
| TWI868205B (zh) | 2019-08-28 | 2025-01-01 | 德商馬克專利公司 | 芳香性異硫氰酸酯 |
| WO2021069535A1 (en) | 2019-10-10 | 2021-04-15 | Merck Patent Gmbh | Fluorinated aromatic compounds |
| WO2021116080A1 (en) | 2019-12-10 | 2021-06-17 | Merck Patent Gmbh | Aromatic isothiocyanates |
| EP3839008B1 (en) | 2019-12-17 | 2023-07-26 | Merck Patent GmbH | Liquid crystal medium |
| CN115667461B (zh) | 2020-05-18 | 2025-02-25 | 默克专利股份有限公司 | 液晶介质 |
| KR20230033724A (ko) | 2020-07-03 | 2023-03-08 | 메르크 파텐트 게엠베하 | 액정 매질 |
| WO2022003001A1 (en) | 2020-07-03 | 2022-01-06 | Merck Patent Gmbh | Liquid crystal medium |
| EP3933009B1 (en) | 2020-07-03 | 2023-08-16 | Merck Patent GmbH | Liquid crystal medium |
| US12258509B2 (en) | 2020-07-08 | 2025-03-25 | 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 |
| 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 |
| EP4237508B1 (en) | 2020-10-28 | 2025-04-30 | 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 |
| US12203023B2 (en) | 2021-03-31 | 2025-01-21 | Merck Patent Gmbh | Aromatic isothiocyanates |
| CN117203307A (zh) | 2021-04-29 | 2023-12-08 | 默克专利股份有限公司 | 液晶介质 |
| JP2024521031A (ja) | 2021-05-07 | 2024-05-28 | 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 | 反応性メソゲン |
| 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 |
| EP4399258A1 (en) | 2021-09-08 | 2024-07-17 | Merck Patent GmbH | Liquid-crystal medium |
| EP4306615A1 (en) | 2022-07-11 | 2024-01-17 | Merck Patent GmbH | Liquid-crystal medium |
| WO2024096003A1 (ja) * | 2022-11-04 | 2024-05-10 | 株式会社村田製作所 | 芳香族アミン化合物、液晶組成物、液晶素子、表示装置および調光装置 |
| CN120787252A (zh) | 2023-02-24 | 2025-10-14 | 默克专利股份有限公司 | 二氢萘衍生物 |
| WO2024200626A1 (en) | 2023-03-31 | 2024-10-03 | Merck Patent Gmbh | Reactive mesogens with high birefringence |
| KR20250169252A (ko) | 2023-03-31 | 2025-12-02 | 메르크 파텐트 게엠베하 | 키랄 반응성 메소겐 혼합물 |
| WO2024235946A1 (en) | 2023-05-17 | 2024-11-21 | Merck Patent Gmbh | Optical element comprising a chiral lc polymer film |
| WO2024260902A1 (en) | 2023-06-20 | 2024-12-26 | Merck Patent Gmbh | Liquid crystal medium |
| WO2024260930A1 (en) | 2023-06-20 | 2024-12-26 | Merck Patent Gmbh | Half-wave plate |
| 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 |
|---|---|---|---|---|
| CN100338054C (zh) * | 2001-05-21 | 2007-09-19 | 默克专利股份有限公司 | 手性化合物 |
| KR20040010703A (ko) * | 2001-06-13 | 2004-01-31 | 메르크 파텐트 게엠베하 | 유체 결정성 매질 및 고비틀림 액정 표시 소자 |
| AU2002366720A1 (en) * | 2001-12-12 | 2003-07-09 | 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 CN CNB028101901A patent/CN100338054C/zh not_active Expired - Lifetime
- 2002-04-25 US US10/477,896 patent/US7223450B2/en not_active Expired - Lifetime
- 2002-04-25 KR KR1020037015130A patent/KR100920912B1/ko not_active Expired - Lifetime
- 2002-04-25 EP EP02740515A patent/EP1389199B1/en not_active Expired - Lifetime
- 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
-
2007
- 2007-05-24 US US11/753,400 patent/US7425356B2/en not_active Expired - Lifetime
Non-Patent Citations (4)
| Title |
|---|
| Chirality 12: 278-286 (2000) |
| J. Am. Chem. Soc. 105: 7318-7321 (1983) |
| J. Am. Chem. Soc. 116: 4852-4857 (1994) |
| J. Am. Chem. Soc. 120: 9810-9817 (1998) |
Also Published As
| Publication number | Publication date |
|---|---|
| US7223450B2 (en) | 2007-05-29 |
| EP1389199A1 (en) | 2004-02-18 |
| JP2005501003A (ja) | 2005-01-13 |
| US7425356B2 (en) | 2008-09-16 |
| US20040135119A1 (en) | 2004-07-15 |
| WO2002094805A1 (en) | 2002-11-28 |
| JP4425545B2 (ja) | 2010-03-03 |
| CN1509280A (zh) | 2004-06-30 |
| CN100338054C (zh) | 2007-09-19 |
| HK1065310A1 (zh) | 2005-02-18 |
| KR20040018374A (ko) | 2004-03-03 |
| US20070229732A1 (en) | 2007-10-04 |
| EP1389199B1 (en) | 2013-02-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100920912B1 (ko) | 키랄 화합물 | |
| JP4549611B2 (ja) | キラル化合物 | |
| JP5317382B2 (ja) | キラルな化合物ｉｉ | |
| JP5265838B2 (ja) | キラルな化合物ｉ | |
| EP1326854B1 (en) | Chiral binaphthol derivatives | |
| JP5111715B2 (ja) | キラルな化合物ｉｉｉ | |
| JP5355838B2 (ja) | キラルな光異性化可能な化合物 | |
| JP6913084B2 (ja) | キラル化合物 | |
| EP1273585B1 (en) | Chiral compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20031120 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| AMND | Amendment | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20070425 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20080623 Patent event code: PE09021S01D |
|
| AMND | Amendment | ||
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20090408 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20080623 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |
|
| J201 | Request for trial against refusal decision | ||
| PJ0201 | Trial against decision of rejection |
Patent event date: 20090507 Comment text: Request for Trial against Decision on Refusal Patent event code: PJ02012R01D Patent event date: 20090408 Comment text: Decision to Refuse Application Patent event code: PJ02011S01I Appeal kind category: Appeal against decision to decline refusal Decision date: 20090701 Appeal identifier: 2009101004198 Request date: 20090507 |
|
| AMND | Amendment | ||
| PB0901 | Examination by re-examination before a trial |
Comment text: Amendment to Specification, etc. Patent event date: 20090528 Patent event code: PB09011R02I Comment text: Request for Trial against Decision on Refusal Patent event date: 20090507 Patent event code: PB09011R01I Comment text: Amendment to Specification, etc. Patent event date: 20081222 Patent event code: PB09011R02I Comment text: Amendment to Specification, etc. Patent event date: 20070425 Patent event code: PB09011R02I |
|
| B701 | Decision to grant | ||
| PB0701 | Decision of registration after re-examination before a trial |
Patent event date: 20090701 Comment text: Decision to Grant Registration Patent event code: PB07012S01D Patent event date: 20090609 Comment text: Transfer of Trial File for Re-examination before a Trial Patent event code: PB07011S01I |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20091001 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20091005 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| FPAY | Annual fee payment |
Payment date: 20120919 Year of fee payment: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20120919 Start annual number: 4 End annual number: 4 |
|
| FPAY | Annual fee payment |
Payment date: 20130924 Year of fee payment: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20130924 Start annual number: 5 End annual number: 5 |
|
| FPAY | Annual fee payment |
Payment date: 20140923 Year of fee payment: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20140923 Start annual number: 6 End annual number: 6 |
|
| FPAY | Annual fee payment |
Payment date: 20150917 Year of fee payment: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 20150917 Start annual number: 7 End annual number: 7 |
|
| FPAY | Annual fee payment |
Payment date: 20160921 Year of fee payment: 8 |
|
| PR1001 | Payment of annual fee |
Payment date: 20160921 Start annual number: 8 End annual number: 8 |
|
| FPAY | Annual fee payment |
Payment date: 20170920 Year of fee payment: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 20170920 Start annual number: 9 End annual number: 9 |
|
| FPAY | Annual fee payment |
Payment date: 20180920 Year of fee payment: 10 |
|
| PR1001 | Payment of annual fee |
Payment date: 20180920 Start annual number: 10 End annual number: 10 |
|
| FPAY | Annual fee payment |
Payment date: 20190919 Year of fee payment: 11 |
|
| PR1001 | Payment of annual fee |
Payment date: 20190919 Start annual number: 11 End annual number: 11 |
|
| PR1001 | Payment of annual fee |
Payment date: 20210916 Start annual number: 13 End annual number: 13 |
|
| PC1801 | Expiration of term |
Termination date: 20221025 Termination category: Expiration of duration |