DE69820612T2 - Neue polymerisierbare flüssigkristalline verbindungen - Google Patents
Neue polymerisierbare flüssigkristalline verbindungen Download PDFInfo
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- DE69820612T2 DE69820612T2 DE69820612T DE69820612T DE69820612T2 DE 69820612 T2 DE69820612 T2 DE 69820612T2 DE 69820612 T DE69820612 T DE 69820612T DE 69820612 T DE69820612 T DE 69820612T DE 69820612 T2 DE69820612 T2 DE 69820612T2
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 42
- -1 pyridine-2,5-diyl Chemical group 0.000 claims description 38
- 230000003287 optical effect Effects 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 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 claims description 6
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000006850 spacer group Chemical group 0.000 claims description 3
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 claims description 2
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 15
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- LSVLMFBVUQQWOQ-UMSPYCQHSA-N C1C[C@@H](O)CC[C@@H]1C1=CC=C(O)C=C1 Chemical compound C1C[C@@H](O)CC[C@@H]1C1=CC=C(O)C=C1 LSVLMFBVUQQWOQ-UMSPYCQHSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- FLPSQLAEXYKMGQ-UHFFFAOYSA-N 4-(6-prop-2-enoyloxyhexoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 FLPSQLAEXYKMGQ-UHFFFAOYSA-N 0.000 description 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
- 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 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- VDZDJGMSXBFJKJ-UHFFFAOYSA-N 4-(3-fluoro-4-hydroxyphenyl)cyclohexan-1-one Chemical compound C1=C(F)C(O)=CC=C1C1CCC(=O)CC1 VDZDJGMSXBFJKJ-UHFFFAOYSA-N 0.000 description 4
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- VVLHJYUGDKBRJW-UHFFFAOYSA-N pentyl 2-hydroxy-5-(4-oxocyclohexyl)benzoate Chemical compound C1=C(O)C(C(=O)OCCCCC)=CC(C2CCC(=O)CC2)=C1 VVLHJYUGDKBRJW-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- FUCGFRGQQUSOFB-UHFFFAOYSA-N 2-hydroxy-5-(4-oxocyclohexyl)benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(C2CCC(=O)CC2)=C1 FUCGFRGQQUSOFB-UHFFFAOYSA-N 0.000 description 3
- QMJAKYDVJXMKDN-UHFFFAOYSA-N 4-(3-acetyl-4-hydroxyphenyl)cyclohexan-1-one Chemical compound C1=C(O)C(C(=O)C)=CC(C2CCC(=O)CC2)=C1 QMJAKYDVJXMKDN-UHFFFAOYSA-N 0.000 description 3
- JVKPTVFUEQBSSO-UHFFFAOYSA-N 4-[4-(6-prop-2-enoyloxyhexoxy)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 JVKPTVFUEQBSSO-UHFFFAOYSA-N 0.000 description 3
- AUZPKZGIOYCYNV-UHFFFAOYSA-N 6-chlorohexyl prop-2-enoate Chemical compound ClCCCCCCOC(=O)C=C AUZPKZGIOYCYNV-UHFFFAOYSA-N 0.000 description 3
- RAYIHHANFDBPCF-UHFFFAOYSA-N 8-(3-fluoro-4-phenylmethoxyphenyl)-1,4-dioxaspiro[4.5]dec-7-ene Chemical compound FC1=CC(C=2CCC3(CC=2)OCCO3)=CC=C1OCC1=CC=CC=C1 RAYIHHANFDBPCF-UHFFFAOYSA-N 0.000 description 3
- JAZQZTVJAPQHOU-UHFFFAOYSA-N 8-(3-fluoro-4-phenylmethoxyphenyl)-1,4-dioxaspiro[4.5]decan-8-ol Chemical compound C1CC(O)(C=2C=C(F)C(OCC=3C=CC=CC=3)=CC=2)CCC21OCCO2 JAZQZTVJAPQHOU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- GIRYDGKKTYGDAI-UHFFFAOYSA-N 2-fluoro-4-(4-hydroxycyclohexyl)phenol Chemical compound C1CC(O)CCC1C1=CC=C(O)C(F)=C1 GIRYDGKKTYGDAI-UHFFFAOYSA-N 0.000 description 2
- SLJYPZJZQIHNGU-UHFFFAOYSA-N 4-(4-hydroxyphenyl)cyclohexan-1-one Chemical compound C1=CC(O)=CC=C1C1CCC(=O)CC1 SLJYPZJZQIHNGU-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KRMSDYMQXPCPPL-CTYIDZIISA-N CCCCCOC(=O)c1cc(ccc1O)[C@H]1CC[C@H](O)CC1 Chemical compound CCCCCOC(=O)c1cc(ccc1O)[C@H]1CC[C@H](O)CC1 KRMSDYMQXPCPPL-CTYIDZIISA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229940008309 acetone / ethanol Drugs 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000011097 chromatography purification Methods 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
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
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- 239000011521 glass Substances 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 230000002269 spontaneous effect Effects 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
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HKQTYQDNCKMNHZ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decan-8-ol Chemical compound C1CC(O)CCC21OCCO2 HKQTYQDNCKMNHZ-UHFFFAOYSA-N 0.000 description 1
- VKRKCBWIVLSRBJ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decan-8-one Chemical compound C1CC(=O)CCC21OCCO2 VKRKCBWIVLSRBJ-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- HEBDGRTWECSNNT-UHFFFAOYSA-N 2-methylidenepentanoic acid Chemical compound CCCC(=C)C(O)=O HEBDGRTWECSNNT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ARUBXNBYMCVENE-UHFFFAOYSA-N 4-(4-bromophenyl)phenol Chemical compound C1=CC(O)=CC=C1C1=CC=C(Br)C=C1 ARUBXNBYMCVENE-UHFFFAOYSA-N 0.000 description 1
- LSVLMFBVUQQWOQ-UHFFFAOYSA-N 4-(4-hydroxycyclohexyl)phenol Chemical compound C1CC(O)CCC1C1=CC=C(O)C=C1 LSVLMFBVUQQWOQ-UHFFFAOYSA-N 0.000 description 1
- DTBNPTQBRPZVCZ-UHFFFAOYSA-N 4-(7-oxonon-8-enoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OCCCCCCC(=O)C=C)C=C1 DTBNPTQBRPZVCZ-UHFFFAOYSA-N 0.000 description 1
- HCVUDNMNSPYSHS-UHFFFAOYSA-N 4-bromo-2-fluoro-1-phenylmethoxybenzene Chemical compound FC1=CC(Br)=CC=C1OCC1=CC=CC=C1 HCVUDNMNSPYSHS-UHFFFAOYSA-N 0.000 description 1
- HLXJEKPLQLVJGK-UHFFFAOYSA-N 4-ethynylphenol Chemical compound OC1=CC=C(C#C)C=C1 HLXJEKPLQLVJGK-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
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- OJJOBIOIMYXFNU-ZVTZDLPXSA-N OCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C#Cc1ccc(cc1)[C@H]1CC[C@H](CCCO)CC1 Chemical compound OCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C#Cc1ccc(cc1)[C@H]1CC[C@H](CCCO)CC1 OJJOBIOIMYXFNU-ZVTZDLPXSA-N 0.000 description 1
- VGYAAWYHVAAJNX-UMSPYCQHSA-N O[C@H]1CC[C@@H](CC1)c1ccc(Br)cc1 Chemical compound O[C@H]1CC[C@@H](CC1)c1ccc(Br)cc1 VGYAAWYHVAAJNX-UMSPYCQHSA-N 0.000 description 1
- KKNCFIKJIJQLKQ-CZMCAQCFSA-N O[C@H]1CC[C@@H](CC1)c1ccc(O)c(Cl)c1 Chemical compound O[C@H]1CC[C@@H](CC1)c1ccc(O)c(Cl)c1 KKNCFIKJIJQLKQ-CZMCAQCFSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- ZBTCSYDLYVZCDB-UHFFFAOYSA-N [3-chloro-4-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxyphenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C=1C=C(OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)C(Cl)=CC=1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 ZBTCSYDLYVZCDB-UHFFFAOYSA-N 0.000 description 1
- FQCKIWWAEIOPSD-UHFFFAOYSA-N [3-methyl-4-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxyphenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C=1C=C(OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)C(C)=CC=1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 FQCKIWWAEIOPSD-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012468 concentrated sample Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 150000005690 diesters Chemical class 0.000 description 1
- 239000006185 dispersion Substances 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
- 230000005684 electric field Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 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
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 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
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—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
- C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—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
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
-
- 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
- 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
- C09K19/3833—Polymers with mesogenic groups in the side chain
- C09K19/3842—Polyvinyl derivatives
- C09K19/3852—Poly(meth)acrylate derivatives
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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
-
- 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
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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
- C09K2019/0477—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by the positioning of substituents on phenylene
- C09K2019/0481—Phenylene substituted in meta position
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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
- C09K2019/0477—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by the positioning of substituents on phenylene
- C09K2019/0485—Phenylene substituted in ortho position
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Pyridine Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97108259 | 1997-05-22 | ||
| EP97108259 | 1997-05-22 | ||
| PCT/IB1998/000789 WO1998052905A1 (en) | 1997-05-22 | 1998-05-22 | New polymerisable liquid crystalline compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69820612D1 DE69820612D1 (de) | 2004-01-29 |
| DE69820612T2 true DE69820612T2 (de) | 2004-10-14 |
Family
ID=8226813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69820612T Expired - Fee Related DE69820612T2 (de) | 1997-05-22 | 1998-05-22 | Neue polymerisierbare flüssigkristalline verbindungen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6395351B1 (https=) |
| EP (1) | EP0983225B1 (https=) |
| JP (1) | JP2001527570A (https=) |
| KR (1) | KR100566684B1 (https=) |
| CN (1) | CN1213989C (https=) |
| AU (1) | AU7227698A (https=) |
| DE (1) | DE69820612T2 (https=) |
| WO (1) | WO1998052905A1 (https=) |
Families Citing this family (91)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1051454B1 (en) * | 1998-01-27 | 2004-03-10 | Rolic AG | Liquid-crystalline photocrosslinkable mixture |
| EP1046631A1 (en) * | 1999-04-19 | 2000-10-25 | Rolic AG | Liquid crystalline compounds |
| GB9908934D0 (en) * | 1999-04-19 | 1999-06-16 | Rolic Ag | Liquid crystalline compounds |
| US6514578B1 (en) | 1999-06-30 | 2003-02-04 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Polymerizable mesogenic tolanes |
| GB2359809B (en) * | 1999-12-24 | 2004-01-14 | Sumitomo Chemical Co | Phenylacetylene compound liquid crystal composition, polymer optically anisotropic product, and liquid crystal or optical element |
| WO2001053248A1 (en) * | 2000-01-21 | 2001-07-26 | Dainippon Ink And Chemicals, Inc. | Polymerizable composition showing liquid-crystal phase and optically anisotropic object made with the same |
| DE10016524A1 (de) * | 2000-04-03 | 2001-10-04 | Basf Ag | Polymerisierbare Flüssigkristalle |
| JP4836335B2 (ja) * | 2000-04-25 | 2011-12-14 | 住友化学株式会社 | フェニルアセチレン重合物、光学異方体及び光学又は液晶用素子 |
| DE10025782A1 (de) * | 2000-05-26 | 2001-12-06 | Basf Ag | Flüssigkristalline Stoffgemenge |
| JP2002003845A (ja) * | 2000-06-26 | 2002-01-09 | Fuji Photo Film Co Ltd | 液晶性組成物、カラーフィルタおよび光学フィルム |
| KR100694936B1 (ko) * | 2000-07-20 | 2007-03-14 | 메르크 파텐트 게엠베하 | 중합성 메소제닉 톨란 |
| KR100977427B1 (ko) * | 2002-08-07 | 2010-08-24 | 후지필름 가부시키가이샤 | 위상차판 및 원편광판 |
| DE10246774A1 (de) * | 2002-10-07 | 2004-04-15 | Merck Patent Gmbh | Flüssigkristalline Medien enthaltend Polymere |
| US7364670B2 (en) * | 2003-07-17 | 2008-04-29 | Fujifilm Corporation | Liquid crystalline compound, liquid crystalline composition and retardation film |
| EP1873228B1 (en) * | 2005-04-13 | 2011-03-09 | Asahi Glass Company, Limited | Polymerizable liquid crystal composition, optical anisotropic material, optical element, and optical head device |
| JP5186116B2 (ja) * | 2006-06-12 | 2013-04-17 | 富士フイルム株式会社 | 化合物、それを含有する液晶組成物、異方性材料、偏光板保護フィルム、光学補償フィルムならびに液晶表示装置 |
| KR101436795B1 (ko) | 2006-09-13 | 2014-09-03 | 롤리크 아게 | 체적 광-정렬 지연판 |
| JP5140991B2 (ja) * | 2006-10-31 | 2013-02-13 | Ｄｉｃ株式会社 | 重合性液晶化合物 |
| EP2094815B1 (en) * | 2006-12-22 | 2012-06-27 | Rolic AG | Patternable liquid crystal polymer comprising thio-ether units |
| US8425990B2 (en) * | 2007-02-23 | 2013-04-23 | Zeon Corporation | Liquid crystalline compound, liquid crystalline composition, optical film, and optical laminate |
| JP5186120B2 (ja) * | 2007-03-05 | 2013-04-17 | 富士フイルム株式会社 | 化合物、それを含有する液晶組成物、異方性材料、偏光板保護フィルム、光学補償フィルムならびに液晶表示装置 |
| JP5168976B2 (ja) * | 2007-03-28 | 2013-03-27 | Ｄｉｃ株式会社 | ビフェニル及びテルフェニル化合物、該化合物を含有する重合性液晶組成物 |
| JP5345293B2 (ja) * | 2007-03-29 | 2013-11-20 | 株式会社Ａｄｅｋａ | 重合性化合物及び重合性組成物 |
| KR101676231B1 (ko) * | 2007-08-30 | 2016-11-14 | 메르크 파텐트 게엠베하 | 액정 디스플레이 |
| CN101903494B (zh) | 2007-12-21 | 2016-03-02 | 罗利克有限公司 | 光校准组合物 |
| KR101499238B1 (ko) * | 2008-08-07 | 2015-03-05 | 삼성디스플레이 주식회사 | 액정 표시 장치 |
| JP2010196016A (ja) * | 2009-02-27 | 2010-09-09 | Mitsubishi Electric Corp | 樹脂組成物及び樹脂硬化物 |
| JP2010196015A (ja) * | 2009-02-27 | 2010-09-09 | Mitsubishi Electric Corp | 樹脂組成物及び樹脂硬化物 |
| WO2010143682A1 (ja) | 2009-06-11 | 2010-12-16 | 富士フイルム株式会社 | 光反射膜の製造方法 |
| JP5020289B2 (ja) | 2009-06-11 | 2012-09-05 | 富士フイルム株式会社 | 赤外光反射板、及び赤外光反射性合わせガラス |
| JP5259501B2 (ja) | 2009-06-11 | 2013-08-07 | 富士フイルム株式会社 | 赤外光反射板、赤外光反射性合わせガラス、並びにコレステリック液晶層を有する積層体及び合わせガラス |
| TWI490316B (zh) | 2009-07-09 | 2015-07-01 | Rolic Ag | 用於光學或光電元件之含酯基液晶 |
| EP2272937A1 (en) | 2009-07-09 | 2011-01-12 | Rolic AG | Ester group containing compounds for optical or electro optical devices |
| KR20110021587A (ko) * | 2009-08-26 | 2011-03-04 | 삼성전자주식회사 | 액정 표시 장치 및 그 제조 방법 |
| KR101734598B1 (ko) * | 2009-09-03 | 2017-05-11 | 스미또모 가가꾸 가부시끼가이샤 | 디에폭시 화합물, 그 제조 방법 및 그 디에폭시 화합물을 함유하는 조성물 |
| US8257639B2 (en) * | 2009-09-22 | 2012-09-04 | Kent State University | Method of making stimuli responsive liquid crystal-polymer composite fibers |
| JP2011154215A (ja) | 2010-01-27 | 2011-08-11 | Fujifilm Corp | 赤外光反射板、合わせガラス用積層中間膜シート及びその製造方法、並びに合わせガラス |
| JP5671365B2 (ja) | 2011-02-18 | 2015-02-18 | 富士フイルム株式会社 | 赤外光反射板並びに合わせガラス用積層中間膜シート及び合わせガラスとそれらの製造方法 |
| JP5723641B2 (ja) | 2011-03-16 | 2015-05-27 | 富士フイルム株式会社 | 重合性化合物、重合性液晶組成物、高分子化合物およびフィルム |
| JP5718260B2 (ja) | 2011-09-08 | 2015-05-13 | 富士フイルム株式会社 | 重合性液晶化合物、重合性組成物、高分子材料、及びフィルム |
| JP5962949B2 (ja) * | 2011-11-28 | 2016-08-03 | Dic株式会社 | 重合性液晶化合物 |
| JP6051566B2 (ja) * | 2012-04-05 | 2016-12-27 | Dic株式会社 | 飽和環構造を有する重合性化合物 |
| JP5961498B2 (ja) | 2012-09-18 | 2016-08-02 | 富士フイルム株式会社 | 熱線カットフィルムおよびその製造方法、合わせガラス並びに熱線カット部材 |
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| EP2998769A4 (en) | 2013-05-16 | 2016-12-21 | Nippon Kayaku Kk | INFRARED SHIELDING FOIL, METHOD FOR THE PRODUCTION THEREOF AND APPLICATION THEREOF |
| CN105593713B (zh) | 2013-10-03 | 2018-07-31 | 富士胶片株式会社 | 投影图像显示用半反射镜及其制造方法以及投影图像显示系统 |
| JP2015072410A (ja) | 2013-10-04 | 2015-04-16 | 富士フイルム株式会社 | コレステリック液晶層を含む熱圧着貼合用フィルムおよびその応用 |
| DE102015000119A1 (de) * | 2014-01-24 | 2015-07-30 | Merck Patent Gmbh | Verfahren zur Herstellung von Bis-[4-(6-acryloyloxy-hexyl)-phenyl]cyclohexan-1,4- dicarbonsäureester |
| JP6080884B2 (ja) | 2014-03-28 | 2017-02-15 | 富士フイルム株式会社 | 重合性化合物、ポリマー、重合性組成物、フィルム、および投映像表示用ハーフミラー |
| JP6343348B2 (ja) * | 2014-09-05 | 2018-06-13 | 富士フイルム株式会社 | 重合性化合物、ポリマー、重合性組成物、およびフィルム |
| EP3199561B1 (en) * | 2014-09-25 | 2019-01-09 | FUJIFILM Corporation | Polymerizable composition comprising polymerizable compounds, film, and half mirror for projected-image display |
| JP6689755B2 (ja) | 2014-12-19 | 2020-04-28 | 日本化薬株式会社 | 光反射フィルム及びこれを有する積層体 |
| JPWO2016129645A1 (ja) | 2015-02-10 | 2017-10-26 | 富士フイルム株式会社 | 光学部材、光学素子、液晶表示装置および近接眼光学部材 |
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| JPWO2025018426A1 (https=) | 2023-07-20 | 2025-01-23 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2636684C3 (de) | 1976-08-14 | 1980-06-19 | Merck Patent Gmbh, 6100 Darmstadt | Phenylcyclohexanderivate und ihre Verwendung in flüssigkristallinen Dielektrika |
| DE2853728A1 (de) | 1978-12-13 | 1980-07-17 | Merck Patent Gmbh | Fluessigkristalline carbonsaeureester, verfahren zu ihrer herstellung, diese enthaltende dielektrika und elektrooptisches anzeigeelement |
| EP0122389B1 (de) | 1983-03-16 | 1987-08-05 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Flüssigkristallkomponenten mit einer Alkenylseitenkette |
| GB2155465B (en) * | 1984-01-23 | 1987-12-31 | Dainippon Ink & Chemicals | Tolan-type nematic liquid crystalline compounds |
| DE3667170D1 (de) | 1985-03-26 | 1990-01-04 | Hoffmann La Roche | Alkenylsubstituierte phenylisothiocyanate und benzonitrile. |
| DE3534778A1 (de) | 1985-09-30 | 1987-04-02 | Hoechst Ag | Chirale ester mesogener carbonsaeuren, ein verfahren zu deren herstellung und ihre verwendung als dotierstoff in fluessigkristall-phasen |
| DE3604462A1 (de) | 1986-02-13 | 1987-08-20 | Merck Patent Gmbh | Smektische fluessigkristalline phasen |
| US4696990A (en) | 1986-03-31 | 1987-09-29 | Eastman Kodak Company | Novel photocrosslinkable liquid crystalline polymers |
| EP0591508B2 (en) * | 1992-04-27 | 2003-01-15 | MERCK PATENT GmbH | Electrooptical liquid crystal system |
| KR100257886B1 (ko) | 1993-01-29 | 2000-06-01 | 손욱 | 고분자 액정 복합체 |
| US5518652A (en) | 1993-07-05 | 1996-05-21 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystalline copolymer |
| EP0648827B1 (en) * | 1993-10-15 | 1999-12-22 | MERCK PATENT GmbH | Reactive liquid crystal compounds |
| DE4405316A1 (de) * | 1994-02-19 | 1995-08-24 | Basf Ag | Neue polymerisierbare flüssigkristalline Verbindungen |
| DE4408171A1 (de) * | 1994-03-11 | 1995-09-14 | Basf Ag | Neue polymerisierbare flüssigkristalline Verbindungen |
| US5567349A (en) | 1994-03-30 | 1996-10-22 | Hoffmann-La Roche Inc. | Photo cross-linkable liquid crystals |
| DE59509361D1 (de) * | 1994-06-24 | 2001-08-02 | Rolic Ag Zug | Optisches Bauelement |
| US5593617A (en) | 1994-09-12 | 1997-01-14 | Hoffmann-Laroche Inc. | Photochemically polymerizable liquid crystals |
| GB2298202B (en) | 1995-02-24 | 1998-09-16 | Merck Patent Gmbh | Chiral polymerizable binaphthol derivatives |
| US5707544A (en) | 1995-06-07 | 1998-01-13 | Rolic Ag | Chromophore-containing photo cross-linkable liquid crystals |
| DE19520704A1 (de) | 1995-06-09 | 1996-12-12 | Basf Ag | Polymerisierbare chirale Verbindungen und deren Verwendung |
| DE59605841D1 (de) | 1995-07-28 | 2000-10-12 | Rolic Ag Zug | Photovernetzbare Chirale Dotierstoffe |
| US6174457B1 (en) * | 1996-09-27 | 2001-01-16 | Chisso Corporation | Compound having alkadienyl group as side chain, and liquid crystal composition using same |
-
1998
- 1998-05-22 AU AU72276/98A patent/AU7227698A/en not_active Abandoned
- 1998-05-22 DE DE69820612T patent/DE69820612T2/de not_active Expired - Fee Related
- 1998-05-22 CN CNB988053357A patent/CN1213989C/zh not_active Expired - Fee Related
- 1998-05-22 JP JP55018298A patent/JP2001527570A/ja not_active Ceased
- 1998-05-22 KR KR1019997010737A patent/KR100566684B1/ko not_active Expired - Fee Related
- 1998-05-22 WO PCT/IB1998/000789 patent/WO1998052905A1/en not_active Ceased
- 1998-05-22 EP EP98919404A patent/EP0983225B1/en not_active Expired - Lifetime
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1999
- 1999-11-19 US US09/443,214 patent/US6395351B1/en not_active Expired - Fee Related
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| JP2001527570A (ja) | 2001-12-25 |
| EP0983225A1 (en) | 2000-03-08 |
| HK1026195A1 (en) | 2000-12-08 |
| EP0983225B1 (en) | 2003-12-17 |
| WO1998052905A1 (en) | 1998-11-26 |
| KR100566684B1 (ko) | 2006-04-03 |
| CN1257473A (zh) | 2000-06-21 |
| AU7227698A (en) | 1998-12-11 |
| US6395351B1 (en) | 2002-05-28 |
| CN1213989C (zh) | 2005-08-10 |
| DE69820612D1 (de) | 2004-01-29 |
| KR20010012775A (ko) | 2001-02-26 |
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