CN101941922B - 液晶化合物 - Google Patents
液晶化合物 Download PDFInfo
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- CN101941922B CN101941922B CN2010102372335A CN201010237233A CN101941922B CN 101941922 B CN101941922 B CN 101941922B CN 2010102372335 A CN2010102372335 A CN 2010102372335A CN 201010237233 A CN201010237233 A CN 201010237233A CN 101941922 B CN101941922 B CN 101941922B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 67
- 239000004973 liquid crystal related substance Substances 0.000 title abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 239000001301 oxygen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 20
- 125000003342 alkenyl group Chemical group 0.000 abstract description 15
- 125000004122 cyclic group Chemical group 0.000 abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 abstract description 10
- 125000003302 alkenyloxy group Chemical group 0.000 abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 8
- 229910052736 halogen Inorganic materials 0.000 abstract description 6
- 150000002367 halogens Chemical class 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 abstract description 3
- 125000005842 heteroatom Chemical group 0.000 abstract description 3
- 125000006850 spacer group Chemical group 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 23
- 239000010408 film Substances 0.000 description 21
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 20
- -1 LCP compound Chemical class 0.000 description 17
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 14
- 239000003960 organic solvent Substances 0.000 description 14
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 238000000605 extraction Methods 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 10
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 238000003818 flash chromatography Methods 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229960001866 silicon dioxide Drugs 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 7
- 230000002194 synthesizing effect Effects 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 4
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229960004839 potassium iodide Drugs 0.000 description 4
- 235000007715 potassium iodide Nutrition 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YDFAJMDFCCJZSI-UHFFFAOYSA-N 8-chlorooctan-1-ol Chemical compound OCCCCCCCCCl YDFAJMDFCCJZSI-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000007766 curtain coating 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
- 125000004386 diacrylate group Chemical group 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 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 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011833 salt mixture Substances 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- CFQPVBJOKYSPKG-UHFFFAOYSA-N 1,3-dimethylimidazol-2-one Chemical compound CN1C=CN(C)C1=O CFQPVBJOKYSPKG-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N 1-Pyrroline Chemical class C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 1
- CEEOUTFAPZOUHS-UHFFFAOYSA-N 2-(6-prop-2-enoyloxyhexoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCCCCCOC(=O)C=C CEEOUTFAPZOUHS-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 1
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- CXDHJGCWMIOAQP-UHFFFAOYSA-N 2-pyridin-3-yl-1,4,5,6-tetrahydropyrimidine;hydrochloride Chemical compound Cl.C1CCNC(C=2C=NC=CC=2)=N1 CXDHJGCWMIOAQP-UHFFFAOYSA-N 0.000 description 1
- CWPKTBMRVATCBL-UHFFFAOYSA-N 3-[1-[1-[(2-methylphenyl)methyl]piperidin-4-yl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound CC1=CC=CC=C1CN1CCC(N2CCC(CC2)N2C(NC3=CC=CC=C32)=O)CC1 CWPKTBMRVATCBL-UHFFFAOYSA-N 0.000 description 1
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 description 1
- ICTHGQKQYABWMV-UHFFFAOYSA-N 4-(2,2-dimethylpropyl)phenol Chemical compound CC(C)(C)CC1=CC=C(O)C=C1 ICTHGQKQYABWMV-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
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVWFQEGFNMOVMP-UHFFFAOYSA-N C=CC(OCCCCCCOc(cc1)ccc1C(Oc(cc1Cc2ccc[o]2)ccc1OC(c(cc1)ccc1OCCCCCCOC(C=C)=O)=O)=O)=O Chemical compound C=CC(OCCCCCCOc(cc1)ccc1C(Oc(cc1Cc2ccc[o]2)ccc1OC(c(cc1)ccc1OCCCCCCOC(C=C)=O)=O)=O)=O BVWFQEGFNMOVMP-UHFFFAOYSA-N 0.000 description 1
- MBZCBFTWZWEHDN-UHFFFAOYSA-O C=CC([OH2+])OCCCCCCOc1ccc(C(O)Oc(cc2C(OCCCCCCCCCCCOC(c3ccc[o]3)=O)=O)ccc2OC(c(cc2)ccc2OCCCCCCOC(C=C)=O)=O)cc1 Chemical compound C=CC([OH2+])OCCCCCCOc1ccc(C(O)Oc(cc2C(OCCCCCCCCCCCOC(c3ccc[o]3)=O)=O)ccc2OC(c(cc2)ccc2OCCCCCCOC(C=C)=O)=O)cc1 MBZCBFTWZWEHDN-UHFFFAOYSA-O 0.000 description 1
- BMJWQWVQGHSPSF-UHFFFAOYSA-N COc(cc1)ccc1-c(cc1C(O)=O)ccc1O Chemical compound COc(cc1)ccc1-c(cc1C(O)=O)ccc1O BMJWQWVQGHSPSF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- SXWLULZBOIVXND-UHFFFAOYSA-N N#Cc(cc1)ccc1OCCCCCCCCOC(c1cc(O)ccc1O)=O Chemical compound N#Cc(cc1)ccc1OCCCCCCCCOC(c1cc(O)ccc1O)=O SXWLULZBOIVXND-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- JJDQZIJKWRZLSJ-UHFFFAOYSA-N [O].C=CCCCC Chemical compound [O].C=CCCCC JJDQZIJKWRZLSJ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- BQAQHFMZRLEURF-UHFFFAOYSA-N bromo(butyl)phosphane Chemical compound CCCCPBr BQAQHFMZRLEURF-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QOQHDJZWGSAHFL-UHFFFAOYSA-N butylphosphanium;bromide Chemical class [Br-].CCCC[PH3+] QOQHDJZWGSAHFL-UHFFFAOYSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- XBECFEJUQZXMFE-UHFFFAOYSA-N n-(4-aminobutyl)acetamide;hydrochloride Chemical compound Cl.CC(=O)NCCCCN XBECFEJUQZXMFE-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000002512 suppressor factor Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C09K19/06—Non-steroidal liquid crystal compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
- C07C255/14—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton containing cyano groups and esterified hydroxy groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
-
- 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
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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
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
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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
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- 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
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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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
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- 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9903670.9A GB9903670D0 (en) | 1999-02-17 | 1999-02-17 | Liquid crystal compounds |
| GB9903670.9 | 1999-02-17 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN00803872A Division CN1340041A (zh) | 1999-02-17 | 2000-02-01 | 液晶化合物 |
Publications (2)
| Publication Number | Publication Date |
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| CN101941922A CN101941922A (zh) | 2011-01-12 |
| CN101941922B true CN101941922B (zh) | 2012-02-29 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2010102372335A Expired - Lifetime CN101941922B (zh) | 1999-02-17 | 2000-02-01 | 液晶化合物 |
| CN00803872A Pending CN1340041A (zh) | 1999-02-17 | 2000-02-01 | 液晶化合物 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN00803872A Pending CN1340041A (zh) | 1999-02-17 | 2000-02-01 | 液晶化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6676851B1 (https=) |
| EP (1) | EP1154981B1 (https=) |
| JP (1) | JP4619541B2 (https=) |
| KR (1) | KR100619468B1 (https=) |
| CN (2) | CN101941922B (https=) |
| AT (1) | ATE271538T1 (https=) |
| AU (1) | AU2123800A (https=) |
| DE (1) | DE60012308T2 (https=) |
| GB (1) | GB9903670D0 (https=) |
| WO (1) | WO2000048985A1 (https=) |
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| GB9906168D0 (en) * | 1999-03-17 | 1999-05-12 | Rolic Ag | Liquid crystal compounds |
| GB9908934D0 (en) * | 1999-04-19 | 1999-06-16 | Rolic Ag | Liquid crystalline compounds |
| EP1295863A1 (en) * | 2001-09-24 | 2003-03-26 | Rolic AG | Liquid crystalline "laterally polymerizable" compounds |
| US6919946B2 (en) | 2002-04-16 | 2005-07-19 | 3M Innovative Properties Company | Compensators for liquid crystal displays and the use and manufacture of the compensators |
| EP1689827B1 (en) * | 2003-12-04 | 2008-07-09 | Rolic AG | Additive components for liquid crystalline materials |
| KR101436795B1 (ko) | 2006-09-13 | 2014-09-03 | 롤리크 아게 | 체적 광-정렬 지연판 |
| US7927671B2 (en) | 2006-09-21 | 2011-04-19 | Chisso Corporation | Trifunctional compound, composition and polymer thereof |
| JP2010510168A (ja) * | 2006-11-22 | 2010-04-02 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 官能化窒化ホウ素ナノチューブ |
| EP2094815B1 (en) | 2006-12-22 | 2012-06-27 | Rolic AG | Patternable liquid crystal polymer comprising thio-ether units |
| EP2222740B1 (en) | 2007-12-21 | 2017-10-11 | Rolic AG | Functionalized photoreactive compounds |
| CN101903494B (zh) * | 2007-12-21 | 2016-03-02 | 罗利克有限公司 | 光校准组合物 |
| EP2272937A1 (en) | 2009-07-09 | 2011-01-12 | Rolic AG | Ester group containing compounds for optical or electro optical devices |
| 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 |
| US8257639B2 (en) * | 2009-09-22 | 2012-09-04 | Kent State University | Method of making stimuli responsive liquid crystal-polymer composite fibers |
| EP2502973A4 (en) * | 2009-11-18 | 2014-07-23 | Adeka Corp | LIQUID CRYSTAL COMPOSITION COMPRISING A POLYMERIZABLE COMPOUND AND A LIQUID CRYSTAL DISPLAY ELEMENT COMPRISING THIS LIQUID CRYSTAL COMPOSITION |
| US9927625B2 (en) * | 2010-12-27 | 2018-03-27 | Dic Corporation | Birefringent lens material for stereoscopic image display device and method for producing birefringent lens for stereoscopic image display device |
| JP5905419B2 (ja) * | 2013-03-13 | 2016-04-20 | 富士フイルム株式会社 | 重合性液晶化合物、液晶組成物、高分子材料とその製造方法、フィルム、偏光板および液晶表示装置 |
| JP5839147B2 (ja) * | 2013-11-29 | 2016-01-06 | Dic株式会社 | 化合物、重合体、液晶配向膜、液晶表示素子、及び光学異方体 |
| KR102074956B1 (ko) | 2014-01-10 | 2020-02-10 | 삼성디스플레이 주식회사 | 액정 표시 장치 |
| JP2017518413A (ja) | 2014-05-21 | 2017-07-06 | ロリク アーゲーＲｏｌｉｃ Ａｇ | 重合性二色性染料 |
| DE102016120096A1 (de) * | 2015-10-21 | 2017-04-27 | Ks Kolbenschmidt Gmbh | Verbundwerkstoff für einen Kolben |
| CN109477930A (zh) | 2016-07-29 | 2019-03-15 | 罗利克技术有限公司 | 在液晶聚合物材料上产生取向的方法 |
| EP3953434B1 (en) * | 2019-04-08 | 2024-09-04 | Rolic Technologies AG | Liquid crystal compounds |
| CN118259397A (zh) | 2019-07-24 | 2024-06-28 | 罗利克技术有限公司 | 可光致配向的正c板延迟器 |
| JP7078089B2 (ja) * | 2020-10-06 | 2022-05-31 | Dic株式会社 | 重合性化合物及び光学異方体 |
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| US5164111A (en) * | 1986-06-27 | 1992-11-17 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Polymerizable liquid-crystal material and polymers exhibiting liquid-crystal phases |
| US5567349A (en) * | 1994-03-30 | 1996-10-22 | Hoffmann-La Roche Inc. | Photo cross-linkable liquid crystals |
| US5593617A (en) * | 1994-09-12 | 1997-01-14 | Hoffmann-Laroche Inc. | Photochemically polymerizable liquid crystals |
| EP1051454B1 (en) | 1998-01-27 | 2004-03-10 | Rolic AG | Liquid-crystalline photocrosslinkable mixture |
| GB9812636D0 (en) * | 1998-06-11 | 1998-08-12 | Rolic Ag | Optical component orientation layer and layerable polymerisable mixture |
| GB9815269D0 (en) * | 1998-07-14 | 1998-09-09 | Rolic Ag | Compositions |
| TW394852B (en) * | 1998-08-26 | 2000-06-21 | Merck Patent Gmbh | Reflective film |
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1999
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2000
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- 2000-02-01 AU AU21238/00A patent/AU2123800A/en not_active Abandoned
- 2000-02-01 CN CN2010102372335A patent/CN101941922B/zh not_active Expired - Lifetime
- 2000-02-01 WO PCT/IB2000/000098 patent/WO2000048985A1/en not_active Ceased
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- 2000-02-01 EP EP00901280A patent/EP1154981B1/en not_active Expired - Lifetime
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- 2000-02-01 DE DE60012308T patent/DE60012308T2/de not_active Expired - Lifetime
- 2000-02-01 CN CN00803872A patent/CN1340041A/zh active Pending
Also Published As
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|---|---|
| HK1038734A1 (en) | 2002-03-28 |
| CN1340041A (zh) | 2002-03-13 |
| KR100619468B1 (ko) | 2006-09-05 |
| KR20010102136A (ko) | 2001-11-15 |
| AU2123800A (en) | 2000-09-04 |
| DE60012308T2 (de) | 2005-03-24 |
| ATE271538T1 (de) | 2004-08-15 |
| JP4619541B2 (ja) | 2011-01-26 |
| DE60012308D1 (de) | 2004-08-26 |
| EP1154981B1 (en) | 2004-07-21 |
| WO2000048985A1 (en) | 2000-08-24 |
| CN101941922A (zh) | 2011-01-12 |
| GB9903670D0 (en) | 1999-04-14 |
| JP2002537280A (ja) | 2002-11-05 |
| US6676851B1 (en) | 2004-01-13 |
| EP1154981A1 (en) | 2001-11-21 |
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