JP5220969B2 - 液晶化合物 - Google Patents
液晶化合物 Download PDFInfo
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- JP5220969B2 JP5220969B2 JP2000612251A JP2000612251A JP5220969B2 JP 5220969 B2 JP5220969 B2 JP 5220969B2 JP 2000612251 A JP2000612251 A JP 2000612251A JP 2000612251 A JP2000612251 A JP 2000612251A JP 5220969 B2 JP5220969 B2 JP 5220969B2
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 77
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 38
- 239000000203 mixture Substances 0.000 claims abstract description 59
- 230000003287 optical effect Effects 0.000 claims abstract description 21
- 239000000463 material Substances 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims 3
- 239000007788 liquid Substances 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 229920000106 Liquid crystal polymer Polymers 0.000 description 37
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 37
- 239000010408 film Substances 0.000 description 30
- -1 methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy , Dodecyloxy Chemical group 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 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 16
- 125000000217 alkyl group Chemical group 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 7
- 239000002178 crystalline material Substances 0.000 description 7
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 7
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 230000003098 cholesteric effect Effects 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 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 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 5
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- NCAHXPUYMMFXNN-UHFFFAOYSA-N 6-(6-bromonaphthalen-2-yl)oxyhexan-1-ol Chemical compound C1=C(Br)C=CC2=CC(OCCCCCCO)=CC=C21 NCAHXPUYMMFXNN-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 3
- VEQQKYFPDCRCCO-UHFFFAOYSA-N 2-[6-(4-bromophenoxy)hexoxy]oxane Chemical compound C1=CC(Br)=CC=C1OCCCCCCOC1OCCCC1 VEQQKYFPDCRCCO-UHFFFAOYSA-N 0.000 description 3
- HUPZYWPGEXWAEI-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl 2,5-dihydroxybenzoate Chemical compound OC1=CC=C(O)C(C(=O)OCCCCCCOC(=O)C=C)=C1 HUPZYWPGEXWAEI-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 3
- 0 CCCCC*C(c1cc(OC(c(cc2)ccc2OCCCCCCOC(C=C)=O)=O)ccc1CC*CCCCOc1ccc(Cc(cc2)cc(cc3)c2cc3OCCCCCCOC(C=C)=O)cc1)=O Chemical compound CCCCC*C(c1cc(OC(c(cc2)ccc2OCCCCCCOC(C=C)=O)=O)ccc1CC*CCCCOc1ccc(Cc(cc2)cc(cc3)c2cc3OCCCCCCOC(C=C)=O)cc1)=O 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 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 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- KNEOGDXGNAJBMM-UHFFFAOYSA-N 2-[6-(4-ethynylphenoxy)hexoxy]oxane Chemical group C1=CC(C#C)=CC=C1OCCCCCCOC1OCCCC1 KNEOGDXGNAJBMM-UHFFFAOYSA-N 0.000 description 2
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 2
- TYRGWPHXUHACSW-UHFFFAOYSA-N 6-[6-[2-[4-[6-(oxan-2-yloxy)hexoxy]phenyl]ethynyl]naphthalen-2-yl]oxyhexan-1-ol Chemical compound C1=CC2=CC(OCCCCCCO)=CC=C2C=C1C#CC(C=C1)=CC=C1OCCCCCCOC1CCCCO1 TYRGWPHXUHACSW-UHFFFAOYSA-N 0.000 description 2
- JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 2
- KBCJJQNRGNBWSI-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl 2-[6-[4-(4-cyanophenyl)phenoxy]hexoxy]-5-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxybenzoate Chemical compound C=1C=C(OCCCCCCOC=2C=CC(=CC=2)C=2C=CC(=CC=2)C#N)C(C(=O)OCCCCCCOC(=O)C=C)=CC=1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 KBCJJQNRGNBWSI-UHFFFAOYSA-N 0.000 description 2
- PYTLSGPGGXBUEU-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl 2-hydroxy-5-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxybenzoate Chemical compound C1=C(C(=O)OCCCCCCOC(=O)C=C)C(O)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 PYTLSGPGGXBUEU-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000004419 alkynylene group Chemical group 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- KRUQDZRWZXUUAD-UHFFFAOYSA-N bis(trimethylsilyl) sulfate Chemical compound C[Si](C)(C)OS(=O)(=O)O[Si](C)(C)C KRUQDZRWZXUUAD-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 2
- 125000005754 decalinylene group Chemical group 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000005562 phenanthrylene group Chemical group 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 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
- 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 1
- SYMNZQQLKBEWPM-UHFFFAOYSA-N 4-[4-(6-hydroxyhexoxy)phenyl]benzonitrile Chemical compound C1=CC(OCCCCCCO)=CC=C1C1=CC=C(C#N)C=C1 SYMNZQQLKBEWPM-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 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
- XUXWTJPSSLYNGJ-UHFFFAOYSA-N 6-[6-[2-[4-(6-hydroxyhexoxy)phenyl]ethynyl]naphthalen-2-yl]oxyhexyl prop-2-enoate Chemical compound C1=CC(OCCCCCCO)=CC=C1C#CC1=CC=C(C=C(OCCCCCCOC(=O)C=C)C=C2)C2=C1 XUXWTJPSSLYNGJ-UHFFFAOYSA-N 0.000 description 1
- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 1
- ZUHDLLNJTVWXFN-UHFFFAOYSA-N 6-iodohexyl prop-2-enoate Chemical compound ICCCCCCOC(=O)C=C ZUHDLLNJTVWXFN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 1
- WHNXLUAFPCUMAS-UHFFFAOYSA-N C=CC(OCCCCCCOc(cc1)cc(cc2)c1cc2C#Cc(cc1)ccc1OCCCCCCOC1OCCCC1)=O Chemical compound C=CC(OCCCCCCOc(cc1)cc(cc2)c1cc2C#Cc(cc1)ccc1OCCCCCCOC1OCCCC1)=O WHNXLUAFPCUMAS-UHFFFAOYSA-N 0.000 description 1
- BCLKKHCPVSMVEZ-WKILWMFISA-N CCCCC[C@H]1CC[C@H](CCCOc2ccc(O)c(F)c2F)CC1 Chemical compound CCCCC[C@H]1CC[C@H](CCCOc2ccc(O)c(F)c2F)CC1 BCLKKHCPVSMVEZ-WKILWMFISA-N 0.000 description 1
- IOWDTJPZNTZHHJ-QAQDUYKDSA-N CCCCC[C@H]1CC[C@H](CCc2ccc(O)cc2)CC1 Chemical compound CCCCC[C@H]1CC[C@H](CCc2ccc(O)cc2)CC1 IOWDTJPZNTZHHJ-QAQDUYKDSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- 101150003085 Pdcl gene Proteins 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-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
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000003074 decanoyl 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(*)=O 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
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- NCBFTYFOPLPRBX-UHFFFAOYSA-N dimethyl azodicarboxylate Substances COC(=O)N=NC(=O)OC NCBFTYFOPLPRBX-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000003104 hexanoyl group Chemical group O=C([*])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
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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
- 125000005647 linker group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- UXMYWKMKSWQGBZ-LGUFXXKBSA-N methyl (e)-3-[3-methoxy-4-[6-[4-[2-[6-(6-prop-2-enoyloxyhexoxy)naphthalen-2-yl]ethynyl]phenoxy]hexoxy]phenyl]prop-2-enoate Chemical compound COC1=CC(/C=C/C(=O)OC)=CC=C1OCCCCCCOC1=CC=C(C#CC=2C=C3C=CC(OCCCCCCOC(=O)C=C)=CC3=CC=2)C=C1 UXMYWKMKSWQGBZ-LGUFXXKBSA-N 0.000 description 1
- NCBFTYFOPLPRBX-AATRIKPKSA-N methyl (ne)-n-methoxycarbonyliminocarbamate Chemical compound COC(=O)\N=N\C(=O)OC NCBFTYFOPLPRBX-AATRIKPKSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000001402 nonanoyl group Chemical group O=C([*])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
- 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
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 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
- 238000000399 optical microscopy Methods 0.000 description 1
- SNICINPKMUFULT-UHFFFAOYSA-N pentyl 2,5-dihydroxybenzoate Chemical compound CCCCCOC(=O)C1=CC(O)=CC=C1O SNICINPKMUFULT-UHFFFAOYSA-N 0.000 description 1
- REXIUMRIVSPNPC-UHFFFAOYSA-N pentyl 2-hydroxy-5-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxybenzoate Chemical compound C1=C(O)C(C(=O)OCCCCC)=CC(OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)=C1 REXIUMRIVSPNPC-UHFFFAOYSA-N 0.000 description 1
- QKNZNUNCDJZTCH-UHFFFAOYSA-N pentyl benzoate Chemical compound CCCCCOC(=O)C1=CC=CC=C1 QKNZNUNCDJZTCH-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- AUJXJFHANFIVKH-GQCTYLIASA-N trans-methylferulate Chemical compound COC(=O)\C=C\C1=CC=C(O)C(OC)=C1 AUJXJFHANFIVKH-GQCTYLIASA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- QDUOESIXNVKNKB-UHFFFAOYSA-N trimethylsilyl hydrogen sulfate Chemical compound C[Si](C)(C)OS(O)(=O)=O QDUOESIXNVKNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])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
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
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- 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
- 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
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- 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
- C09K19/2014—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 containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n-
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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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
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- 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/326—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a decahydronaphthalene, e.g. -2,6-diyl (decalin)
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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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
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- 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)
- Liquid Crystal (AREA)
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| GB9908934.4 | 1999-04-19 | ||
| GBGB9908934.4A GB9908934D0 (en) | 1999-04-19 | 1999-04-19 | Liquid crystalline compounds |
| PCT/IB2000/000448 WO2000063154A1 (en) | 1999-04-19 | 2000-04-11 | Liquid crystal compounds |
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| JP2002542219A JP2002542219A (ja) | 2002-12-10 |
| JP2002542219A5 JP2002542219A5 (enExample) | 2011-03-17 |
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| JP2000612251A Expired - Fee Related JP5220969B2 (ja) | 1999-04-19 | 2000-04-11 | 液晶化合物 |
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| Country | Link |
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| US (1) | US6746729B1 (enExample) |
| EP (1) | EP1187802B1 (enExample) |
| JP (1) | JP5220969B2 (enExample) |
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| AT (1) | ATE382598T1 (enExample) |
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| DE (1) | DE60037659T2 (enExample) |
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| WO2023058369A1 (ja) * | 2021-10-06 | 2023-04-13 | Jsr株式会社 | 感放射線性樹脂組成物、樹脂、化合物及びパターン形成方法 |
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| JP5295471B2 (ja) * | 2000-11-13 | 2013-09-18 | Ｄｉｃ株式会社 | 重合性液晶化合物、該化合物を含有する重合性液晶組成物及びその重合体 |
| JP2002167360A (ja) * | 2000-11-29 | 2002-06-11 | Asahi Glass Co Ltd | メソゲン基を有する重合性単量体の製造方法 |
| 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 |
| ATE328050T1 (de) * | 2002-04-24 | 2006-06-15 | Merck Patent Gmbh | Reaktive mesogene benzodithiophene |
| US6699532B2 (en) | 2002-06-25 | 2004-03-02 | Mitsubishi Gas Chemical Company, Inc. | Optically active compound and liquid crystal composition containing the compound |
| WO2005054406A1 (en) * | 2003-12-04 | 2005-06-16 | Rolic Ag | Additive components for liquid crystalline materials |
| US20050261469A1 (en) * | 2004-05-21 | 2005-11-24 | Gangadhar Panambur | High performance polymer electrolyte with improved thermal and chemical characteristics |
| TWI305287B (en) * | 2005-09-22 | 2009-01-11 | Lg Chemical Ltd | Multi-functional monomer having a photoreactive group, alignment film for lcd using the monomer, and lcd comprising the alignment film |
| US7910179B2 (en) * | 2005-11-23 | 2011-03-22 | Lg Chem, Ltd. | Vinylsulfone derivative, liquid crystal composition comprising the same and compensation film using the same liquid crystal composition |
| US7785488B2 (en) | 2005-12-08 | 2010-08-31 | Chisso Corporation | Lateral oxirane compound and polymer thereof |
| US7919648B2 (en) | 2005-12-08 | 2011-04-05 | Chisso Corporation | Lateral α-substituted acrylate compound and polymer thereof |
| ES2494293T3 (es) | 2006-09-13 | 2014-09-15 | Rolic Ag | Retardador fotoalineado por volumen |
| US7927671B2 (en) | 2006-09-21 | 2011-04-19 | Chisso Corporation | Trifunctional compound, composition and polymer thereof |
| US8574454B2 (en) | 2006-12-22 | 2013-11-05 | Rolic Ag | Patternable liquid crystal polymer comprising thio-ether units |
| 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 |
| US9499649B2 (en) * | 2007-12-21 | 2016-11-22 | Rolic Ag | Functionalized photoreactive compounds |
| CN105733606B (zh) | 2007-12-21 | 2018-04-03 | 罗利克有限公司 | 光校准组合物 |
| EA019882B1 (ru) | 2008-03-18 | 2014-07-30 | Арена Фармасьютикалз, Инк. | Модуляторы рецептора простациклина (pgi2), пригодные для лечения связанных с ним расстройств |
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| DK2370413T3 (en) | 2008-12-08 | 2015-11-02 | Arena Pharm Inc | Modulators of prostacyclin (PG12) receptor, which can be used for the treatment of disorders related to this |
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| 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 |
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| WO2023158634A1 (en) | 2022-02-15 | 2023-08-24 | United Therapeutics Corporation | Crystalline prostacyclin (ip) receptor agonist and uses thereof |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4405316A1 (de) | 1994-02-19 | 1995-08-24 | Basf Ag | Neue polymerisierbare flüssigkristalline Verbindungen |
| US5593617A (en) * | 1994-09-12 | 1997-01-14 | Hoffmann-Laroche Inc. | Photochemically polymerizable liquid crystals |
| EP0755918B1 (de) * | 1995-07-28 | 2000-09-06 | Rolic AG | Photovernetzbare flüssigkristalline 1,2-Phenylen-Derivate |
| DE19532408A1 (de) * | 1995-09-01 | 1997-03-06 | Basf Ag | Polymerisierbare flüssigkristalline Verbindungen |
| TW373100B (en) * | 1996-07-01 | 1999-11-01 | Merck Patent Gmbh | Compensation film and liquid crystal display device containing the same |
| DE19714119A1 (de) * | 1997-04-05 | 1998-10-08 | Daimler Benz Ag | Verbindungen, Verfahren zu deren Herstellung sowie Verfahren zur Herstellung flüssigkristalliner Polymere unter Verwendung dieser Verbindungen |
| WO1998052905A1 (en) * | 1997-05-22 | 1998-11-26 | Rolic Ag | New polymerisable liquid crystalline compounds |
| DE19843724A1 (de) * | 1997-10-08 | 1999-04-15 | Basf Ag | Polymerisierbare chirale Verbindungen und deren Verwendung |
| JP3945790B2 (ja) * | 1997-12-25 | 2007-07-18 | 林テレンプ株式会社 | 複屈折フィルムとその製造方法 |
| GB9903670D0 (en) * | 1999-02-17 | 1999-04-14 | Rolic Ag | Liquid crystal compounds |
| GB9906168D0 (en) * | 1999-03-17 | 1999-05-12 | Rolic Ag | Liquid crystal compounds |
-
1999
- 1999-04-19 GB GBGB9908934.4A patent/GB9908934D0/en not_active Ceased
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2000
- 2000-04-11 DE DE60037659T patent/DE60037659T2/de not_active Expired - Lifetime
- 2000-04-11 JP JP2000612251A patent/JP5220969B2/ja not_active Expired - Fee Related
- 2000-04-11 US US09/959,013 patent/US6746729B1/en not_active Expired - Lifetime
- 2000-04-11 AU AU35723/00A patent/AU3572300A/en not_active Abandoned
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- 2000-04-11 EP EP00914329A patent/EP1187802B1/en not_active Expired - Lifetime
- 2000-04-11 HK HK02104006.2A patent/HK1042688A1/zh unknown
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023058369A1 (ja) * | 2021-10-06 | 2023-04-13 | Jsr株式会社 | 感放射線性樹脂組成物、樹脂、化合物及びパターン形成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1347401A (zh) | 2002-05-01 |
| CN1170808C (zh) | 2004-10-13 |
| AU3572300A (en) | 2000-11-02 |
| KR100726265B1 (ko) | 2007-06-12 |
| HK1042688A1 (zh) | 2002-08-23 |
| DE60037659D1 (de) | 2008-02-14 |
| US6746729B1 (en) | 2004-06-08 |
| GB9908934D0 (en) | 1999-06-16 |
| KR20020005004A (ko) | 2002-01-16 |
| WO2000063154A1 (en) | 2000-10-26 |
| EP1187802A1 (en) | 2002-03-20 |
| EP1187802B1 (en) | 2008-01-02 |
| ATE382598T1 (de) | 2008-01-15 |
| JP2002542219A (ja) | 2002-12-10 |
| DE60037659T2 (de) | 2009-01-08 |
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