KR100849981B1 - 키랄 화합물 ｉ - Google Patents
키랄 화합물 ｉ Download PDFInfo
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- KR100849981B1 KR100849981B1 KR1020037000358A KR20037000358A KR100849981B1 KR 100849981 B1 KR100849981 B1 KR 100849981B1 KR 1020037000358 A KR1020037000358 A KR 1020037000358A KR 20037000358 A KR20037000358 A KR 20037000358A KR 100849981 B1 KR100849981 B1 KR 100849981B1
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- South Korea
- Prior art keywords
- formula
- liquid crystal
- chiral
- group
- groups
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 152
- 239000000203 mixture Substances 0.000 claims abstract description 108
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 100
- -1 diagnostics Substances 0.000 claims abstract description 59
- 239000002019 doping agent Substances 0.000 claims abstract description 40
- 229920000642 polymer Polymers 0.000 claims abstract description 15
- 239000000049 pigment Substances 0.000 claims abstract description 14
- 230000003287 optical effect Effects 0.000 claims abstract description 13
- 239000002537 cosmetic Substances 0.000 claims abstract description 9
- 229920000106 Liquid crystal polymer Polymers 0.000 claims abstract description 6
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims abstract description 6
- 238000003860 storage Methods 0.000 claims abstract description 5
- 239000000853 adhesive Substances 0.000 claims abstract description 4
- 230000001070 adhesive effect Effects 0.000 claims abstract description 4
- 230000000379 polymerizing 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 230000003098 cholesteric effect Effects 0.000 claims description 30
- 229910052731 fluorine Inorganic materials 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000006850 spacer group Chemical group 0.000 claims description 7
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 238000000034 method Methods 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
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
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- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
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- 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 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 150000003505 terpenes Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 5
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- 230000005855 radiation Effects 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 7
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- 230000009471 action Effects 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
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 4
- 0 C[C@]1*CCCC1 Chemical compound C[C@]1*CCCC1 0.000 description 4
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- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
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- 239000003381 stabilizer Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 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
- 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
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 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
- 238000010586 diagram Methods 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
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- 239000000178 monomer Substances 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920005597 polymer membrane Polymers 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 239000012952 cationic photoinitiator Substances 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 2
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 239000011159 matrix material Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
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- 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
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- 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
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- 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
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- RFFCUDDJJDOFLS-UHFFFAOYSA-N 1-cyclohexylcyclohexene Chemical compound C1CCCCC1C1=CCCCC1 RFFCUDDJJDOFLS-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
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- 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
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
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- DQZKGSRJOUYVPL-UHFFFAOYSA-N cyclohexyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCCCC1 DQZKGSRJOUYVPL-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- 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
- 230000000694 effects Effects 0.000 description 1
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- IKGLACJFEHSFNN-UHFFFAOYSA-N hydron;triethylazanium;trifluoride Chemical compound F.F.F.CCN(CC)CC IKGLACJFEHSFNN-UHFFFAOYSA-N 0.000 description 1
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- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 1
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- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 1
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- 125000006410 propenylene group Chemical group 0.000 description 1
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- 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
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- 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 | ||
| EP00115250.3 | 2000-07-13 | ||
| PCT/EP2001/007217 WO2002006196A1 (en) | 2000-07-13 | 2001-06-25 | Chiral compounds i |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20030022269A KR20030022269A (ko) | 2003-03-15 |
| KR100849981B1 true KR100849981B1 (ko) | 2008-08-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020037000358A Expired - Lifetime KR100849981B1 (ko) | 2000-07-13 | 2001-06-25 | 키랄 화합물 ｉ |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7060331B2 (https=) |
| EP (1) | EP1299334B1 (https=) |
| JP (1) | JP5265838B2 (https=) |
| KR (1) | KR100849981B1 (https=) |
| AT (1) | ATE384036T1 (https=) |
| AU (1) | AU2001266092A1 (https=) |
| DE (1) | DE60132456T2 (https=) |
| TW (1) | TW538118B (https=) |
| WO (1) | WO2002006196A1 (https=) |
Families Citing this family (116)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003161835A (ja) | 2001-07-02 | 2003-06-06 | Merck Patent Gmbh | 光学可変マーキング |
| 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 |
| WO2004050594A1 (de) * | 2002-12-03 | 2004-06-17 | Merck Patent Gmbh | Verfahren zur herstellung von naphthalinderivaten |
| CA2554696C (en) | 2004-02-13 | 2009-06-30 | Warner-Lambert Company Llc | Androgen receptor modulators |
| JP2007530470A (ja) | 2004-03-25 | 2007-11-01 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | 液晶化合物、液晶媒体および液晶ディスプレイ |
| WO2005100305A1 (en) | 2004-04-13 | 2005-10-27 | Warner-Lambert Company Llc | Androgen modulators |
| JP2007533726A (ja) * | 2004-04-22 | 2007-11-22 | 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 | アンドロゲンモジュレーター |
| DE602005003131T2 (de) * | 2004-07-07 | 2008-08-14 | Merck Patent Gmbh | Biaxialfilm mit periodisch variierender lokaler doppelbrechung |
| EP1789514B1 (en) * | 2004-07-07 | 2007-11-14 | MERCK PATENT GmbH | Biaxial film ii |
| MXPA06015169A (es) | 2004-07-08 | 2007-08-21 | Warner Lambert Co | Moduladores de androgenos. |
| EP1781599A1 (en) * | 2004-08-18 | 2007-05-09 | Warner-Lambert Company LLC | Androgen modulators |
| US7794621B2 (en) | 2004-12-17 | 2010-09-14 | 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 |
| WO2008061606A1 (en) | 2006-11-24 | 2008-05-29 | Merck Patent Gmbh | Cyclohexylene reactive mesogens and their applications |
| WO2008077261A1 (en) | 2006-12-22 | 2008-07-03 | 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 |
| ATE528377T1 (de) | 2008-03-05 | 2011-10-15 | Merck Patent Gmbh | Flüssigkristallines medium und flüssigkristallanzeige mit verdrehtem garn |
| US8545720B2 (en) | 2008-12-22 | 2013-10-01 | Merck Patent Gmbh | Liquid-crystal display |
| 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 |
| CN102753171A (zh) | 2009-04-02 | 2012-10-24 | 科鲁西德制药公司 | 2,4,6-三氟-n-[6-(1-甲基-哌啶-4-羰基)-吡啶-2-基]-苯甲酰胺的组合物 |
| 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 |
| US8697876B2 (en) | 2010-04-02 | 2014-04-15 | Colucid Pharmaceuticals, Inc. | Compositions and methods of synthesis of pyridinolypiperidine 5-HT1F agonists |
| DE102011015546A1 (de) | 2010-04-26 | 2012-01-26 | Merck Patent Gmbh | Polymerisierbare Verbindungen und ihre Verwendung in Flüssigkristallmedien und Flüssigkristallanzeigen |
| US8940716B2 (en) | 2010-05-06 | 2015-01-27 | Bristol-Myers Squibb Company | Bicyclic heteroaryl compounds as GPR119 modulators |
| 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 |
| CN103459554B (zh) | 2011-03-29 | 2018-07-10 | 默克专利股份有限公司 | 液晶介质 |
| US9315729B2 (en) | 2011-05-27 | 2016-04-19 | Merck Patent Gmbh | Polymerizable compounds and their use in liquid crystal media and liquid crystal displays |
| 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 |
| WO2013017197A1 (en) | 2011-08-01 | 2013-02-07 | Merck Patent Gmbh | Liquid crystal medium and liquid crystal display |
| EP2568032B1 (en) | 2011-09-06 | 2014-11-26 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| KR101983867B1 (ko) | 2011-09-06 | 2019-05-29 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 디스플레이 |
| 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 |
| KR20150002847A (ko) | 2012-04-20 | 2015-01-07 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 디스플레이 |
| DK2858986T3 (da) * | 2012-06-12 | 2019-11-25 | Chong Kun Dang Pharmaceutical Corp | Piperidinderivater som gpr119-agonister |
| EP2708587B1 (en) | 2012-09-18 | 2015-07-15 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| KR102162137B1 (ko) | 2012-10-02 | 2020-10-06 | 메르크 파텐트 게엠베하 | 액정 매질 및 액정 디스플레이 |
| 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 |
| CN104797686B (zh) | 2012-11-27 | 2017-06-09 | 默克专利股份有限公司 | 透镜元件 |
| KR20150144787A (ko) | 2013-04-19 | 2015-12-28 | 메르크 파텐트 게엠베하 | 메소젠성 화합물, 액정 매질 및 액정 디스플레이 |
| CN110028494A (zh) | 2013-11-26 | 2019-07-19 | 株式会社钟根堂 | 酰胺衍生物、其立体异构体或其药学上可接受的盐及包含其的药物组合物 |
| 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 |
| JP6576350B2 (ja) | 2013-12-30 | 2019-09-18 | 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 |
| EP3105302B1 (en) | 2014-02-13 | 2020-08-05 | Merck Patent GmbH | Reactive mesogen based polymer particles |
| JP2017524046A (ja) | 2014-07-18 | 2017-08-24 | 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コンポーネント |
| 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 |
| KR102534329B1 (ko) | 2014-12-29 | 2023-05-22 | 메르크 파텐트 게엠베하 | 액정 매질 및 이를 포함하는 고주파 부품 |
| CN107109234A (zh) | 2014-12-30 | 2017-08-29 | 默克专利股份有限公司 | 液晶介质和包含其的高频组件 |
| EP3124573B1 (en) | 2015-07-31 | 2018-03-28 | Merck Patent GmbH | Liquid crystal medium and liquid crystal display |
| EP3414300B1 (en) | 2016-02-08 | 2019-10-30 | Merck Patent GmbH | Liquid-crystalline medium and high-frequency components comprising same |
| US20190127642A1 (en) | 2016-04-13 | 2019-05-02 | Merck Patent Gmbh | Composition for nanoencapsulation and nanocapsules comprising a liquid-crystalline medium |
| US20190177618A1 (en) | 2016-08-24 | 2019-06-13 | Merck Patent Gmbh | Liquid crystalline medium and liquid crystal display |
| 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 |
| JP2019535498A (ja) | 2016-10-31 | 2019-12-12 | 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Ｍｅｒｃｋ Ｐａｔｅｎｔ ＧｍｂＨ | 液晶媒体を含むナノカプセル |
| CN110392726B (zh) | 2017-03-16 | 2023-11-03 | 默克专利股份有限公司 | 液晶介质 |
| WO2018189068A1 (en) | 2017-04-10 | 2018-10-18 | Merck Patent Gmbh | Composition for nanoencapsulation and nanocapsules comprising a liquid-crystalline medium |
| EP3612615B1 (en) | 2017-04-20 | 2024-10-16 | 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 |
| JP7420717B2 (ja) | 2017-12-06 | 2024-01-23 | 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 | スイッチング要素に使用するための液晶媒体 |
| 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 |
| EP3543313B1 (en) | 2018-03-23 | 2020-10-07 | Merck Patent GmbH | Liquid-crystalline medium |
| EP3543314B1 (en) | 2018-03-23 | 2020-09-09 | Merck Patent GmbH | Liquid-crystalline medium |
| 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 |
| DE102019008592A1 (de) | 2018-12-12 | 2020-06-18 | Merck Patent Gmbh | Komponenten für die Hochfrequenztechnik und Flüssigkristallmedium |
| US12460134B2 (en) | 2018-12-12 | 2025-11-04 | Merck Patent Gmbh | Polymerizable liquid crystal ink formulations |
| WO2020120586A1 (en) | 2018-12-13 | 2020-06-18 | 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 |
| 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 |
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| 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 |
| TWI829107B (zh) | 2019-07-09 | 2024-01-11 | 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 |
| EP4022007B1 (en) | 2019-08-28 | 2024-04-03 | Merck Patent GmbH | Aromatic isothiocyanates |
| JP7701914B2 (ja) | 2019-10-10 | 2025-07-02 | 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 | フッ素化芳香族化合物 |
| EP4073205B1 (en) | 2019-12-10 | 2024-06-12 | 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 |
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| EP4176021B1 (en) | 2020-07-03 | 2025-01-01 | Merck Patent GmbH | Liquid crystal medium |
| EP3933009B1 (en) | 2020-07-03 | 2023-08-16 | Merck Patent GmbH | Liquid crystal medium |
| WO2022008474A1 (en) | 2020-07-08 | 2022-01-13 | Merck Patent Gmbh | Optical component |
| EP3940040B1 (en) | 2020-07-16 | 2024-10-16 | Merck Patent GmbH | Liquid-crystalline medium |
| IL299921A (en) | 2020-08-28 | 2023-03-01 | 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 |
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| US12359128B2 (en) | 2020-12-17 | 2025-07-15 | Merck Patent Gmbh | Heteroaromatic isothiocyanates |
| 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 |
| KR20240004668A (ko) | 2021-04-29 | 2024-01-11 | 메르크 파텐트 게엠베하 | 액정 매질 |
| 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 |
| JP2024009784A (ja) | 2022-07-11 | 2024-01-23 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 液晶媒体 |
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| WO2025061649A1 (en) | 2023-09-20 | 2025-03-27 | Merck Patent Gmbh | Liquid crystal medium |
| US12528988B2 (en) | 2023-11-08 | 2026-01-20 | Merck Patent Gmbh | Liquid crystal medium |
| WO2025196107A1 (en) | 2024-03-22 | 2025-09-25 | Merck Patent Gmbh | Indene derivatives |
| WO2025261973A1 (en) | 2024-06-19 | 2025-12-26 | Merck Patent Gmbh | Thiophene derivatives |
| WO2026052594A1 (en) | 2024-09-05 | 2026-03-12 | Merck Patent Gmbh | Liquid crystal-based light valve |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0640578A1 (en) * | 1993-08-30 | 1995-03-01 | Chisso Corporation | Novel liquid crystalline compound having a 1,1,2,3,3,3,-hexafluoropropyl group and liquid crystal composition |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04506815A (ja) * | 1990-04-21 | 1992-11-26 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | フェニルシクロヘキサン化合物、および液晶相 |
| 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 |
| 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 DE DE60132456T patent/DE60132456T2/de not_active Expired - Lifetime
- 2001-06-25 EP EP01943543A patent/EP1299334B1/en not_active Expired - Lifetime
- 2001-06-25 JP JP2002512103A patent/JP5265838B2/ja not_active Expired - Fee Related
- 2001-06-25 WO PCT/EP2001/007217 patent/WO2002006196A1/en not_active Ceased
- 2001-06-25 KR KR1020037000358A patent/KR100849981B1/ko not_active Expired - Lifetime
- 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 US US10/332,470 patent/US7060331B2/en not_active Expired - Lifetime
- 2001-06-27 TW TW090115635A patent/TW538118B/zh not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0640578A1 (en) * | 1993-08-30 | 1995-03-01 | Chisso Corporation | Novel liquid crystalline compound having a 1,1,2,3,3,3,-hexafluoropropyl group and liquid crystal composition |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60132456D1 (de) | 2008-03-06 |
| JP2004504286A (ja) | 2004-02-12 |
| EP1299334A1 (en) | 2003-04-09 |
| TW538118B (en) | 2003-06-21 |
| US20030175445A1 (en) | 2003-09-18 |
| KR20030022269A (ko) | 2003-03-15 |
| ATE384036T1 (de) | 2008-02-15 |
| AU2001266092A1 (en) | 2002-01-30 |
| US7060331B2 (en) | 2006-06-13 |
| WO2002006196A1 (en) | 2002-01-24 |
| JP5265838B2 (ja) | 2013-08-14 |
| DE60132456T2 (de) | 2009-01-08 |
| EP1299334B1 (en) | 2008-01-16 |
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