DE60132456T2 - Chirale verbindungen i - Google Patents
Chirale verbindungen i Download PDFInfo
- Publication number
- DE60132456T2 DE60132456T2 DE60132456T DE60132456T DE60132456T2 DE 60132456 T2 DE60132456 T2 DE 60132456T2 DE 60132456 T DE60132456 T DE 60132456T DE 60132456 T DE60132456 T DE 60132456T DE 60132456 T2 DE60132456 T2 DE 60132456T2
- Authority
- DE
- Germany
- Prior art keywords
- chiral
- group
- compounds
- formula
- sup
- 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 154
- 239000000203 mixture Substances 0.000 claims abstract description 100
- -1 diagnostics Substances 0.000 claims abstract description 54
- 239000007788 liquid Substances 0.000 claims abstract description 48
- 239000002019 doping agent Substances 0.000 claims abstract description 40
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 32
- 239000000049 pigment Substances 0.000 claims abstract description 13
- 229920000642 polymer Polymers 0.000 claims abstract description 13
- 230000003287 optical effect Effects 0.000 claims abstract description 9
- 239000002537 cosmetic Substances 0.000 claims abstract description 8
- 229920000106 Liquid crystal polymer Polymers 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 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 38
- 230000003098 cholesteric effect Effects 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 125000006850 spacer group Chemical group 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 7
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 4
- 239000004904 UV filter Substances 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000008859 change Effects 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000013500 data storage Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000003860 storage Methods 0.000 abstract description 2
- 239000012071 phase Substances 0.000 description 28
- 239000000460 chlorine Substances 0.000 description 23
- 229920000728 polyester Polymers 0.000 description 21
- 239000000758 substrate Substances 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 12
- 229920006254 polymer film Polymers 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000004990 Smectic liquid crystal Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000005855 radiation Effects 0.000 description 7
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 7
- 125000005529 alkyleneoxy group Chemical group 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 0 CC(C)(*)c(cc1)ccc1O Chemical compound CC(C)(*)c(cc1)ccc1O 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
- 230000008901 benefit Effects 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SJSRFXJWBKOROD-UHFFFAOYSA-N 1,1'-bi(cyclohexyl)-1-carboxylic acid Chemical compound C1CCCCC1C1(C(=O)O)CCCCC1 SJSRFXJWBKOROD-UHFFFAOYSA-N 0.000 description 2
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid 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
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 239000002253 acid 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 2
- 239000012952 cationic photoinitiator Substances 0.000 description 2
- 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 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000000047 product Substances 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
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- IWIOHRVOBOYWQE-UHFFFAOYSA-N (1-cyclohexylcyclohexyl)benzene Chemical class 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 compound 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
- JYNLTWJPPFIEFR-UHFFFAOYSA-N 1,2-dicyclohexylcyclohexene Chemical class C1CCCCC1C1=C(C2CCCCC2)CCCC1 JYNLTWJPPFIEFR-UHFFFAOYSA-N 0.000 description 1
- 150000005481 1,2-diphenylethanes Chemical class 0.000 description 1
- QQFSIGWYINAJOB-UHFFFAOYSA-N 1,4-dicyclohexylbenzene Chemical class C1CCCCC1C1=CC=C(C2CCCCC2)C=C1 QQFSIGWYINAJOB-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RFFCUDDJJDOFLS-UHFFFAOYSA-N 1-cyclohexylcyclohexene Chemical class C1CCCCC1C1=CCCCC1 RFFCUDDJJDOFLS-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 class 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 class C1CCCCC1CCC1=CC=CC=C1 HYYFAYFMSHAWFA-UHFFFAOYSA-N 0.000 description 1
- IBLVSWYGUFGDMF-UHFFFAOYSA-N 2-cyclohexylethylcyclohexane Chemical class C1CCCCC1CCC1CCCCC1 IBLVSWYGUFGDMF-UHFFFAOYSA-N 0.000 description 1
- HUTHUTALXJNNRS-UHFFFAOYSA-N 2-cyclohexylpyridine Chemical class C1CCCCC1C1=CC=CC=N1 HUTHUTALXJNNRS-UHFFFAOYSA-N 0.000 description 1
- YJDDXMSIMBMMGY-UHFFFAOYSA-N 2-cyclohexylpyrimidine Chemical class 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 class 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
- RIQIOKOQHGSKLN-UHFFFAOYSA-N 5,5-dibromo-1,3-dimethylimidazolidine-2,4-dione Chemical compound CN1C(=O)N(C)C(Br)(Br)C1=O RIQIOKOQHGSKLN-UHFFFAOYSA-N 0.000 description 1
- QNGKGXNZGWIDGS-UHFFFAOYSA-N 6-cyclohexyl-5-ethyl-5-phenylcyclohexa-1,3-diene Chemical class C=1C=CC=CC=1C1(CC)C=CC=CC1C1CCCCC1 QNGKGXNZGWIDGS-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- QALHEJNNAUAFPR-UHFFFAOYSA-N CCC(C(CCC1C)C(C)C)C1=O Chemical compound CCC(C(CCC1C)C(C)C)C1=O QALHEJNNAUAFPR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 241000269913 Pseudopleuronectes americanus Species 0.000 description 1
- ADIAPCNCEHFEPJ-UHFFFAOYSA-N [4-(2-cyclohexylethyl)cyclohexyl]benzene Chemical class C1CCCCC1CCC(CC1)CCC1C1=CC=CC=C1 ADIAPCNCEHFEPJ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000004423 acyloxy 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
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001482 benzyl phenyl ethers Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 125000005569 butenylene group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 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
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000012043 crude product 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 class C=1C=CC=CC=1C(=O)OC1CCCCC1 DQZKGSRJOUYVPL-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical class C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-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
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 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
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- IKGLACJFEHSFNN-UHFFFAOYSA-N hydron;triethylazanium;trifluoride Chemical compound F.F.F.CCN(CC)CC IKGLACJFEHSFNN-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002729 menthone derivatives Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002950 monocyclic group Chemical group 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 class C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
- 239000012074 organic phase 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
- 238000000819 phase cycle Methods 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
- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 150000003214 pyranose derivatives Chemical class 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 150000001608 tolans Chemical class 0.000 description 1
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 description 1
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
-
- 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
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or 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
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- 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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Cosmetics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00115250 | 2000-07-13 | ||
| EP00115250 | 2000-07-13 | ||
| PCT/EP2001/007217 WO2002006196A1 (en) | 2000-07-13 | 2001-06-25 | Chiral compounds i |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60132456D1 DE60132456D1 (de) | 2008-03-06 |
| DE60132456T2 true DE60132456T2 (de) | 2009-01-08 |
Family
ID=8169248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60132456T Expired - Lifetime DE60132456T2 (de) | 2000-07-13 | 2001-06-25 | Chirale verbindungen i |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7060331B2 (enExample) |
| EP (1) | EP1299334B1 (enExample) |
| JP (1) | JP5265838B2 (enExample) |
| KR (1) | KR100849981B1 (enExample) |
| AT (1) | ATE384036T1 (enExample) |
| AU (1) | AU2001266092A1 (enExample) |
| DE (1) | DE60132456T2 (enExample) |
| TW (1) | TW538118B (enExample) |
| WO (1) | WO2002006196A1 (enExample) |
Families Citing this family (114)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7081282B2 (en) | 2001-07-02 | 2006-07-25 | Merck Patent Gmbh | Optically variable marking |
| DE10257711B4 (de) | 2001-12-27 | 2019-09-26 | Merck Patent Gmbh | Polymerisierbare monocyclische Verbindungen enthaltende Flüssigkristallmischungen |
| TWI263497B (en) | 2002-03-29 | 2006-10-11 | Lilly Co Eli | Pyridinoylpiperidines as 5-HT1F agonists |
| DE10253606A1 (de) * | 2002-11-15 | 2004-05-27 | Merck Patent Gmbh | Elektrooptisches Lichtsteuerelement, elektrooptische Anzeige und Steuermedium |
| CN1732142A (zh) * | 2002-12-03 | 2006-02-08 | 默克专利股份有限公司 | 萘衍生物的制备方法 |
| AP2006003700A0 (en) | 2004-02-13 | 2006-08-31 | Warner Lambert Co | Androgen receptor modulators |
| DE112005000732T5 (de) | 2004-03-25 | 2008-09-04 | Merck Patent Gmbh | Flüssigkristallverbindungen, Flüssigkristallmedium und Flüssigkristallanzeige |
| WO2005100305A1 (en) | 2004-04-13 | 2005-10-27 | Warner-Lambert Company Llc | Androgen modulators |
| CA2562672C (en) | 2004-04-22 | 2009-09-29 | Warner-Lambert Company Llc | 4-cyano-phenoxy derivatives as androgen modulators |
| EP1763689B1 (en) * | 2004-07-07 | 2007-10-31 | Merck Patent GmbH | Biaxial film having local birefringence that varies periodically |
| KR101230811B1 (ko) * | 2004-07-07 | 2013-02-06 | 메르크 파텐트 게엠베하 | 이축 필름 ⅱ |
| JP4874965B2 (ja) * | 2004-07-08 | 2012-02-15 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | アンドロゲン調節剤 |
| MX2007001248A (es) * | 2004-08-18 | 2007-03-23 | Warner Lambert Co | Moduladores de androgenos. |
| WO2006063662A1 (en) | 2004-12-17 | 2006-06-22 | Merck Patent Gmbh | Liquid crystal system and liquid crystal display |
| TW200724139A (en) * | 2005-05-05 | 2007-07-01 | Warner Lambert Co | Androgen modulators |
| US20090170886A1 (en) * | 2005-08-08 | 2009-07-02 | Pfizer Inc | Androgen modulators |
| EP2087067B1 (en) * | 2006-11-24 | 2012-06-27 | Merck Patent GmbH | Cyclohexylene reactive mesogens and their applications |
| EP2094815B1 (en) | 2006-12-22 | 2012-06-27 | Rolic AG | Patternable liquid crystal polymer comprising thio-ether units |
| CA2685266C (en) | 2007-04-27 | 2014-01-28 | Purdue Pharma L.P. | Trpv1 antagonists and uses thereof for the treatment of prevention of pain, ui and ulcer, ibd, or ibs in an animal |
| 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 |
| DE102009055829A1 (de) | 2008-12-22 | 2010-06-24 | Merck Patent Gmbh | Flüssigkristallanzeige |
| DE102010006691A1 (de) | 2009-02-06 | 2010-10-28 | Merck Patent Gmbh | Flüssigkristallines Medium und Flüssigkristallanzeige |
| EP2218764B1 (en) | 2009-02-13 | 2012-01-18 | Merck Patent GmbH | Chiral reactive mesogen mixture |
| ES2655881T5 (es) * | 2009-04-02 | 2021-11-25 | Colucid Pharmaceuticals Inc | 2,4,6-Trifluoro-N-[6-(1-metil-piperidin-4-carbonil)-piridin-2-il]-benzamida para el tratamiento de la migraña a través de la vía oral o intravenosa |
| DE102010012900A1 (de) | 2009-04-23 | 2010-11-25 | Merck Patent Gmbh | Flüssigkristallanzeige |
| DE102011011836A1 (de) | 2010-03-09 | 2011-09-15 | Merck Patent Gmbh | Polymerisierbare Verbindungen und ihre Verwendung in Flüssigkristallmedien und Flüssigkristallanzeigen |
| CA2795062A1 (en) | 2010-04-02 | 2011-10-06 | Colucid Pharmaceuticals, Inc. | Compositions and methods of synthesis of pyridinoylpiperidine 5-ht1f agonists |
| DE102011015546A1 (de) | 2010-04-26 | 2012-01-26 | Merck Patent Gmbh | Polymerisierbare Verbindungen und ihre Verwendung in Flüssigkristallmedien und Flüssigkristallanzeigen |
| EA201270778A1 (ru) | 2010-05-06 | 2013-04-30 | Бристол-Майерс Сквибб Компани | Бициклические гетероарильные аналоги в качестве модуляторов рецептора gpr119 |
| 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 |
| KR102088166B1 (ko) | 2011-03-29 | 2020-03-12 | 메르크 파텐트 게엠베하 | 액정 매질 |
| DE102012009631A1 (de) | 2011-05-27 | 2012-11-29 | Merck Patent Gmbh | Polymerisierbare Verbindungen und ihre Verwendung in Flüssigkristallmedien und Flüssigkristallanzeigen |
| KR101986858B1 (ko) | 2011-06-01 | 2019-06-07 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 디스플레이 |
| PE20141531A1 (es) | 2011-06-22 | 2014-10-23 | Purdue Pharma Lp | Antagonistas de trpv1 que incluyen sustituyentes dihidroxi y sus usos |
| CN103717707B (zh) | 2011-08-01 | 2016-06-22 | 默克专利股份有限公司 | 液晶介质和液晶显示器 |
| JP6386378B2 (ja) | 2011-09-06 | 2018-09-05 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | 液晶媒体および液晶ディスプレイ |
| EP2568032B1 (en) | 2011-09-06 | 2014-11-26 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| DE102012024126A1 (de) | 2011-12-20 | 2013-06-20 | Merck Patent Gmbh | Flüssigkristallines Medium |
| EP2623927A1 (en) | 2012-02-02 | 2013-08-07 | Stichting Dutch Polymer Institute | Optical strain sensor |
| US9862887B2 (en) | 2012-04-20 | 2018-01-09 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal display |
| CA2867114C (en) | 2012-06-12 | 2016-02-23 | Chong Kun Dang Pharmaceutical Corp. | Piperidine derivatives for gpr119 agonist |
| EP2708587B1 (en) | 2012-09-18 | 2015-07-15 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| EP2904068B1 (en) | 2012-10-02 | 2016-10-12 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| JP5850023B2 (ja) * | 2012-11-27 | 2016-02-03 | Jnc株式会社 | 末端にｃｆ２ｏｃｆ３を有する液晶化合物、液晶組成物および液晶表示素子 |
| KR20150090161A (ko) | 2012-11-27 | 2015-08-05 | 메르크 파텐트 게엠베하 | 렌즈 소자 |
| US9809749B2 (en) | 2013-04-19 | 2017-11-07 | Merck Patent Gmbh | Mesogenic compound, liquid-crystal medium and liquid crystal display |
| RU2642429C2 (ru) | 2013-11-26 | 2018-01-25 | Чон Кун Тан Фармасьютикал Корп. | Амидные производные в качестве агонистов grp119 |
| JP6358034B2 (ja) * | 2013-12-12 | 2018-07-18 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| WO2015101405A1 (en) | 2013-12-30 | 2015-07-09 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal display |
| EP3105302B1 (en) | 2014-02-13 | 2020-08-05 | Merck Patent GmbH | Reactive mesogen based polymer particles |
| KR20170032408A (ko) | 2014-07-18 | 2017-03-22 | 메르크 파텐트 게엠베하 | 액정 매질 및 이를 포함하는 고주파 부품 |
| DE102015009924A1 (de) | 2014-08-22 | 2016-02-25 | Merck Patent Gmbh | Flüssigkristallines Medium |
| DE102015015108A1 (de) | 2014-12-17 | 2016-06-23 | Merck Patent Gmbh | Flüssigkristallines Medium |
| US11208594B2 (en) | 2014-12-29 | 2021-12-28 | Merck Patent Gmbh | Liquid-crystalline medium and high-frequency components comprising same |
| JP6752795B2 (ja) | 2014-12-30 | 2020-09-09 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | 液晶媒体およびそれを含む高周波数素子 |
| EP3124573B1 (en) | 2015-07-31 | 2018-03-28 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| CN108603121B (zh) | 2016-02-08 | 2023-02-10 | 默克专利股份有限公司 | 液晶介质及含有其的高频组件 |
| US20190127642A1 (en) | 2016-04-13 | 2019-05-02 | Merck Patent Gmbh | Composition for nanoencapsulation and nanocapsules comprising a liquid-crystalline medium |
| CN109642160A (zh) | 2016-08-24 | 2019-04-16 | 默克专利股份有限公司 | 液晶介质和液晶显示器 |
| CN107955629B (zh) * | 2016-10-14 | 2021-03-05 | 石家庄诚志永华显示材料有限公司 | 一种正介电性液晶组合物 |
| EP3312257B1 (en) | 2016-10-18 | 2019-11-20 | Merck Patent GmbH | Liquid-crystalline medium and high-frequency components comprising same |
| JP7097878B2 (ja) | 2016-10-24 | 2022-07-08 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 液晶媒体 |
| WO2018078078A1 (en) | 2016-10-31 | 2018-05-03 | Merck Patent Gmbh | Nanocapsules comprising a liquid-crystalline medium |
| CN110392726B (zh) | 2017-03-16 | 2023-11-03 | 默克专利股份有限公司 | 液晶介质 |
| TW201900854A (zh) | 2017-04-10 | 2019-01-01 | 德商馬克專利公司 | 用於奈米封裝之組合物及包含液晶介質之奈米囊 |
| WO2018192896A1 (en) | 2017-04-20 | 2018-10-25 | Merck Patent Gmbh | Light modulation element |
| KR20190039639A (ko) | 2017-10-05 | 2019-04-15 | 메르크 파텐트 게엠베하 | 작용화된 폴리비닐 알콜을 포함하는 조성물 및 액정 매질을 함유하는 나노캡슐 |
| WO2019110458A1 (en) | 2017-12-06 | 2019-06-13 | Merck Patent Gmbh | Liquid-crystalline medium for use in a switching element |
| EP3720924A1 (en) | 2017-12-06 | 2020-10-14 | Merck Patent GmbH | Liquid-crystalline medium for use in a switching element |
| EP3502210B1 (en) | 2017-12-20 | 2020-09-09 | Merck Patent GmbH | Liquid-crystal medium |
| 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 |
| EP3739020B1 (en) | 2018-05-16 | 2023-08-23 | Merck Patent GmbH | Liquid-crystalline medium |
| CN108929704B (zh) * | 2018-07-02 | 2020-08-11 | 西安彩晶光电科技股份有限公司 | 一种液晶组合物及光电元件 |
| TWI826514B (zh) | 2018-09-04 | 2023-12-21 | 美商美國禮來大藥廠 | 用於預防偏頭痛之拉米迪坦(lasmiditan)長期夜間投藥 |
| WO2020120353A1 (en) | 2018-12-12 | 2020-06-18 | Merck Patent Gmbh | Polymerizable liquid crystal ink formulations |
| DE102019008592A1 (de) | 2018-12-12 | 2020-06-18 | Merck Patent Gmbh | Komponenten für die Hochfrequenztechnik und Flüssigkristallmedium |
| US20220073822A1 (en) | 2018-12-13 | 2022-03-10 | Merck Patent Gmbh | Liquid-crystal medium |
| JP7612584B2 (ja) | 2018-12-19 | 2025-01-14 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | スイッチング素子に使用されるスイッチング層 |
| TWI845599B (zh) | 2019-01-25 | 2024-06-21 | 德商馬克專利公司 | 液晶介質 |
| IL274057B2 (en) | 2019-04-30 | 2024-03-01 | Merck Patent Gmbh | Isothiocyantotoluenes |
| JP7562566B2 (ja) | 2019-05-15 | 2024-10-07 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 液晶に基づくスイッチング素子の製造方法 |
| GB2589659B (en) | 2019-05-28 | 2023-04-05 | Merck Patent Gmbh | Compositions comprising polymerizable oligoethyleneglycol derivatives and nanocapsules containing a liquid-crystalline medium |
| EP3983501B1 (en) | 2019-06-17 | 2025-02-26 | Merck Patent GmbH | Liquid crystal-based light valve |
| TWI776175B (zh) | 2019-07-09 | 2022-09-01 | 美商美國禮來大藥廠 | 大規模製備2,4,6-三氟-n-[6-(1-甲基-哌啶-4-羰基)-吡啶-2-基]-苯甲醯胺半琥珀酸鹽的方法及中間體，以及2,4,6-三氟-n-[6-(1-甲基-哌啶-4-羰基)-吡啶-2-基]-苯甲醯胺醋酸鹽之製備 |
| CN114302872A (zh) | 2019-08-28 | 2022-04-08 | 默克专利股份有限公司 | 芳香族异硫氰酸酯 |
| TWI877236B (zh) | 2019-10-10 | 2025-03-21 | 德商馬克專利公司 | 氟化芳族化合物 |
| US11834599B2 (en) | 2019-12-10 | 2023-12-05 | Merck Patent Gmbh | Aromatic isothiocyanates |
| KR20210077615A (ko) | 2019-12-17 | 2021-06-25 | 메르크 파텐트 게엠베하 | 액정 매질 |
| EP4153700B1 (en) | 2020-05-18 | 2025-02-26 | Merck Patent GmbH | Liquid-crystalline medium |
| CN115867629A (zh) | 2020-07-03 | 2023-03-28 | 默克专利股份有限公司 | 液晶介质 |
| EP3933009B1 (en) | 2020-07-03 | 2023-08-16 | Merck Patent GmbH | Liquid crystal medium |
| KR20230035354A (ko) | 2020-07-03 | 2023-03-13 | 메르크 파텐트 게엠베하 | 액정 매질 |
| WO2022008474A1 (en) | 2020-07-08 | 2022-01-13 | Merck Patent Gmbh | Optical component |
| EP3940040B1 (en) | 2020-07-16 | 2024-10-16 | Merck Patent GmbH | Liquid-crystalline medium |
| EP4204515A1 (en) | 2020-08-28 | 2023-07-05 | Merck Patent GmbH | Aromatic isothiocyanates |
| CN114525139B (zh) | 2020-10-07 | 2025-07-25 | 默克专利股份有限公司 | 液晶介质 |
| US20230392076A1 (en) | 2020-10-28 | 2023-12-07 | Merck Patent Gmbh | Aromatic isothiocyanates |
| EP4263750B1 (en) | 2020-12-16 | 2025-06-04 | Merck Patent GmbH | Heteroaromatic isothiocyanates |
| JP2023553699A (ja) | 2020-12-17 | 2023-12-25 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | ヘテロ芳香族イソチオシアネート類 |
| US11802243B2 (en) | 2021-02-26 | 2023-10-31 | Merck Patent Gmbh | Liquid-crystal medium |
| WO2022207584A2 (en) | 2021-03-31 | 2022-10-06 | Merck Patent Gmbh | Aromatic isothiocyanates |
| EP4330343A1 (en) | 2021-04-29 | 2024-03-06 | Merck Patent GmbH | Liquid crystal medium |
| TW202317855A (zh) | 2021-08-06 | 2023-05-01 | 德商馬克專利公司 | 用於窗元件之切換層 |
| KR20240055826A (ko) | 2021-09-08 | 2024-04-29 | 메르크 파텐트 게엠베하 | 액정 매질 |
| EP4306615A1 (en) | 2022-07-11 | 2024-01-17 | Merck Patent GmbH | Liquid-crystal medium |
| WO2024175615A1 (en) | 2023-02-24 | 2024-08-29 | Merck Patent Gmbh | Dihydronapthalene derivatives |
| WO2024260902A1 (en) | 2023-06-20 | 2024-12-26 | Merck Patent Gmbh | Liquid crystal medium |
| WO2025061649A1 (en) | 2023-09-20 | 2025-03-27 | Merck Patent Gmbh | Liquid crystal medium |
| US20250154412A1 (en) | 2023-11-08 | 2025-05-15 | Merck Patent Gmbh | Liquid crystal medium |
| WO2025196107A1 (en) | 2024-03-22 | 2025-09-25 | Merck Patent Gmbh | Indene derivatives |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991016291A1 (de) * | 1990-04-21 | 1991-10-31 | MERCK Patent Gesellschaft mit beschränkter Haftung | Phenylcyclohexane und flüssigkristallines medium |
| JPH0558937A (ja) * | 1991-08-26 | 1993-03-09 | Dainippon Ink & Chem Inc | フツ素置換光学活性化合物とそれを含む液晶組成物及び液晶表示素子 |
| JPH05255195A (ja) * | 1992-03-13 | 1993-10-05 | Idemitsu Petrochem Co Ltd | 新規化合物及びその製造方法、液晶材料用組成物、液晶組成物並びに液晶素子 |
| JPH06158048A (ja) * | 1992-04-28 | 1994-06-07 | Idemitsu Petrochem Co Ltd | 液晶組成物 |
| JPH06264058A (ja) * | 1993-03-12 | 1994-09-20 | Idemitsu Petrochem Co Ltd | 新規化合物並びにそれを用いた液晶組成物及び液晶素子 |
| JPH07118184A (ja) * | 1993-08-30 | 1995-05-09 | Chisso Corp | １，１，２，３，３，３−ヘキサフルオロプロピル部位を持つ新規液晶性化合物および液晶組成物 |
| DE19513007A1 (de) | 1994-04-14 | 1995-10-19 | Merck Patent Gmbh | Hexafluorpropylether und flüssigkristallines Medium |
| GB9413324D0 (en) | 1994-07-01 | 1994-08-24 | Secr Defence | Liquid crystal compounds, mixtures and devices |
| DE19531165B4 (de) * | 1994-09-06 | 2013-04-11 | Merck Patent Gmbh | Benzolderivate und flüssigkristallines Medium |
| JPH101450A (ja) * | 1996-06-14 | 1998-01-06 | Chisso Corp | フッ素置換アルキルエーテル化合物、液晶組成物および液晶表示素子 |
| JPH10109953A (ja) * | 1996-10-04 | 1998-04-28 | Seimi Chem Co Ltd | 光学活性トランス−ジフルオロエチレン化合物およびそれを含有する液晶組成物 |
| JP3287288B2 (ja) * | 1996-11-22 | 2002-06-04 | チッソ株式会社 | ポリハロアルキルエーテル誘導体とそれらを含む液晶組成物及び液晶表示素子 |
| JPH11255679A (ja) * | 1998-03-12 | 1999-09-21 | Seimi Chem Co Ltd | トランス−ジフルオロエチレン化合物、それを含有する液晶組成物および液晶表示素子 |
| JP4395945B2 (ja) * | 1999-12-10 | 2010-01-13 | チッソ株式会社 | ジフルオロメチレン結合を有する反強誘電性液晶化合物およびそれを含む液晶組成物 |
| DE10061790A1 (de) * | 2000-12-12 | 2002-06-13 | Merck Patent Gmbh | Flüssigkristalline Verbindungen |
-
2001
- 2001-06-25 EP EP01943543A patent/EP1299334B1/en not_active Expired - Lifetime
- 2001-06-25 KR KR1020037000358A patent/KR100849981B1/ko not_active Expired - Lifetime
- 2001-06-25 WO PCT/EP2001/007217 patent/WO2002006196A1/en not_active Ceased
- 2001-06-25 AT AT01943543T patent/ATE384036T1/de not_active IP Right Cessation
- 2001-06-25 AU AU2001266092A patent/AU2001266092A1/en not_active Abandoned
- 2001-06-25 DE DE60132456T patent/DE60132456T2/de not_active Expired - Lifetime
- 2001-06-25 JP JP2002512103A patent/JP5265838B2/ja not_active Expired - Fee Related
- 2001-06-25 US US10/332,470 patent/US7060331B2/en not_active Expired - Lifetime
- 2001-06-27 TW TW090115635A patent/TW538118B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20030022269A (ko) | 2003-03-15 |
| JP5265838B2 (ja) | 2013-08-14 |
| KR100849981B1 (ko) | 2008-08-01 |
| DE60132456D1 (de) | 2008-03-06 |
| AU2001266092A1 (en) | 2002-01-30 |
| TW538118B (en) | 2003-06-21 |
| EP1299334A1 (en) | 2003-04-09 |
| WO2002006196A1 (en) | 2002-01-24 |
| JP2004504286A (ja) | 2004-02-12 |
| ATE384036T1 (de) | 2008-02-15 |
| EP1299334B1 (en) | 2008-01-16 |
| US20030175445A1 (en) | 2003-09-18 |
| US7060331B2 (en) | 2006-06-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60132456T2 (de) | Chirale verbindungen i | |
| DE60105032T2 (de) | Chirale verbindungen iii | |
| DE60130338T2 (de) | Chirale verbindungen ii | |
| DE60104014T2 (de) | Chirale binaphtol-verbindungen | |
| DE60202980T2 (de) | Chirale Verbindungen | |
| DE19834162A1 (de) | Chirale Verbindungen | |
| EP1389199B1 (en) | Binaphthol derivatives as chiral dopants | |
| EP1339812B1 (en) | Chiral photoisomerizable compounds | |
| DE602004001650T2 (de) | Polymerisierbare Zimtsäurederivate mit einer seitlichen Substitution | |
| DE10257711B4 (de) | Polymerisierbare monocyclische Verbindungen enthaltende Flüssigkristallmischungen | |
| DE602005005749T2 (de) | Polymerisierbare mesogene Cyclohexylphenylderivate | |
| DE69907579T2 (de) | Polymerisierbare mesogene Fluorphenylene | |
| DE60220961T2 (de) | Cycloalkanon-Derivate | |
| DE10332220B4 (de) | Flüssigkristallines Medium und seine Verwendung in einer Flüssigkristallanzeige mit hoher Verdrillung | |
| DE69908030T2 (de) | Mesogene Estradiolen | |
| DE10033912A1 (de) | Chirale polymerisierbare Verbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |