JP4834226B2 - 液晶化合物 - Google Patents
液晶化合物 Download PDFInfo
- Publication number
- JP4834226B2 JP4834226B2 JP2000605541A JP2000605541A JP4834226B2 JP 4834226 B2 JP4834226 B2 JP 4834226B2 JP 2000605541 A JP2000605541 A JP 2000605541A JP 2000605541 A JP2000605541 A JP 2000605541A JP 4834226 B2 JP4834226 B2 JP 4834226B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- coo
- alkenyl
- diyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 61
- 239000004973 liquid crystal related substance Substances 0.000 title description 14
- -1 Naphthalenediyl Chemical group 0.000 claims description 96
- 229920000106 Liquid crystal polymer Polymers 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 22
- 230000003287 optical effect Effects 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 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 8
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 125000001543 furan-2,5-diyl group Chemical group O1C(=CC=C1*)* 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical group O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000010408 film Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000010410 layer Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 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 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-Dihydroxybenzoic acid Natural products OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 6
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 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 6
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 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 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MINXWEHZDLGNAB-UHFFFAOYSA-N 2-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxybenzoic acid Chemical compound OC(=O)c1ccccc1OC(=O)c1ccc(OCCCCCCOC(=O)C=C)cc1 MINXWEHZDLGNAB-UHFFFAOYSA-N 0.000 description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 3
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- KCLBLDDJJJNGBC-UHFFFAOYSA-N 1-octyl-4-phenylbenzene Chemical group C1=CC(CCCCCCCC)=CC=C1C1=CC=CC=C1 KCLBLDDJJJNGBC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- YDFAJMDFCCJZSI-UHFFFAOYSA-N 8-chlorooctan-1-ol Chemical compound OCCCCCCCCCl YDFAJMDFCCJZSI-UHFFFAOYSA-N 0.000 description 2
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 229960002836 biphenylol Drugs 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 235000010292 orthophenyl phenol Nutrition 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000004781 supercooling Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SMNGQGWPUVVORF-UHFFFAOYSA-N 3,5-ditert-butyl-4-methylphenol Chemical compound CC1=C(C(C)(C)C)C=C(O)C=C1C(C)(C)C SMNGQGWPUVVORF-UHFFFAOYSA-N 0.000 description 1
- CFZHLPRNWAVFAH-UHFFFAOYSA-N 3-(8-chlorooctoxy)-3-(2-phenylphenyl)-2H-furan-5-carboxylic acid Chemical compound C1OC(C(=O)O)=CC1(OCCCCCCCCCl)C1=CC=CC=C1C1=CC=CC=C1 CFZHLPRNWAVFAH-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 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
- VRSLSMSXIFJONL-UHFFFAOYSA-N 3-octylpyridine Chemical compound CCCCCCCCC1=CC=CN=C1 VRSLSMSXIFJONL-UHFFFAOYSA-N 0.000 description 1
- JDCUQPSPITUXGL-UHFFFAOYSA-N 4-(4-octylphenyl)phenol Chemical group C1=CC(CCCCCCCC)=CC=C1C1=CC=C(O)C=C1 JDCUQPSPITUXGL-UHFFFAOYSA-N 0.000 description 1
- POJXUBGZBJKVTC-UHFFFAOYSA-N 4-[2-[4-[8-(2,5-dihydroxybenzoyl)oxyoctoxy]phenyl]phenyl]furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC(C=2C(=CC=CC=2)C=2C=CC(OCCCCCCCCOC(=O)C=3C(=CC=C(O)C=3)O)=CC=2)=C1 POJXUBGZBJKVTC-UHFFFAOYSA-N 0.000 description 1
- LAOMIFMZSCPPJB-UHFFFAOYSA-N 4-[4-(8-chlorooctoxy)phenyl]phenol Chemical compound C1=CC(O)=CC=C1C1=CC=C(OCCCCCCCCCl)C=C1 LAOMIFMZSCPPJB-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- YJQYPCMVXMQESN-UHFFFAOYSA-N C=CC(OCCCCCCOc(cc1)ccc1C(Oc(cc1C(OCCCCCCCCOc(cc2)ccc2-c(cc2)ccc2C#N)=O)ccc1OC(c(cc1)ccc1OCCCCCCOC(C=C)=O)=O)=O)=O Chemical compound C=CC(OCCCCCCOc(cc1)ccc1C(Oc(cc1C(OCCCCCCCCOc(cc2)ccc2-c(cc2)ccc2C#N)=O)ccc1OC(c(cc1)ccc1OCCCCCCOC(C=C)=O)=O)=O)=O YJQYPCMVXMQESN-UHFFFAOYSA-N 0.000 description 1
- UAMBWKCDVMBNAO-UHFFFAOYSA-N C=CC(OCCCCCCOc(cc1)ccc1C(Oc(cc1C(OCCOCCOc(cc2)ccc2-c(cc2)ccc2C#N)=O)ccc1OC(c(cc1)ccc1OCCCCCCOC(C=C)=O)=O)=O)=O Chemical compound C=CC(OCCCCCCOc(cc1)ccc1C(Oc(cc1C(OCCOCCOc(cc2)ccc2-c(cc2)ccc2C#N)=O)ccc1OC(c(cc1)ccc1OCCCCCCOC(C=C)=O)=O)=O)=O UAMBWKCDVMBNAO-UHFFFAOYSA-N 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N CC1CCCC1 Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-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
- UCNZTEVEBRKSQD-UHFFFAOYSA-N O1C(=CC=C1)C(=O)O.C1(=CC=CC=C1)C1=CC=CC=C1 Chemical compound O1C(=CC=C1)C(=O)O.C1(=CC=CC=C1)C1=CC=CC=C1 UCNZTEVEBRKSQD-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000005604 azodicarboxylate group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001246 bromo group Chemical group Br* 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
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method 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
- DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000005259 measurement Methods 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 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
- IPWWPDBOOLRAJL-UHFFFAOYSA-N octyl 2,5-dihydroxybenzoate Chemical compound CCCCCCCCOC(=O)C1=CC(O)=CC=C1O IPWWPDBOOLRAJL-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000011295 pitch Substances 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
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 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 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
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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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
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- 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
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- 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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- 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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- 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
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- 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
- C09K2019/2078—Ph-COO-Ph-COO-Ph
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- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9906168.1A GB9906168D0 (en) | 1999-03-17 | 1999-03-17 | Liquid crystal compounds |
| GB9906168.1 | 1999-03-17 | ||
| PCT/IB2000/000158 WO2000055110A1 (en) | 1999-03-17 | 2000-02-15 | Liquid crystal compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002539182A JP2002539182A (ja) | 2002-11-19 |
| JP2002539182A5 JP2002539182A5 (enExample) | 2010-09-02 |
| JP4834226B2 true JP4834226B2 (ja) | 2011-12-14 |
Family
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|---|---|---|---|
| JP2000605541A Expired - Lifetime JP4834226B2 (ja) | 1999-03-17 | 2000-02-15 | 液晶化合物 |
Country Status (10)
| Country | Link |
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| US (1) | US6733690B1 (enExample) |
| EP (1) | EP1169293B1 (enExample) |
| JP (1) | JP4834226B2 (enExample) |
| KR (1) | KR100750822B1 (enExample) |
| CN (1) | CN1213018C (enExample) |
| AU (1) | AU2456500A (enExample) |
| DE (1) | DE60042589D1 (enExample) |
| GB (1) | GB9906168D0 (enExample) |
| HK (1) | HK1039318A1 (enExample) |
| WO (1) | WO2000055110A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9908934D0 (en) * | 1999-04-19 | 1999-06-16 | Rolic Ag | Liquid crystalline compounds |
| GB9930557D0 (en) * | 1999-12-23 | 2000-02-16 | Rolic Ag | Optically active materials |
| 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 |
| JP2006282579A (ja) * | 2005-03-31 | 2006-10-19 | Nippon Oil Corp | アルコキシナフチル基を有する液晶性（メタ）アクリル化合物およびその重合体 |
| 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 |
| ES2494293T3 (es) | 2006-09-13 | 2014-09-15 | Rolic Ag | Retardador fotoalineado por volumen |
| WO2008077261A1 (en) | 2006-12-22 | 2008-07-03 | Rolic Ag | Patternable liquid crystal polymer comprising thio-ether units |
| JP5726531B2 (ja) | 2007-12-21 | 2015-06-03 | ロリク リミテッドＲｏｌｉｃ Ｌｔｄ． | 光配向組成物 |
| WO2009080147A1 (en) | 2007-12-21 | 2009-07-02 | Rolic Ag | Functionalized photoreactive compounds |
| US8349210B2 (en) | 2008-06-27 | 2013-01-08 | Transitions Optical, Inc. | Mesogenic stabilizers |
| US7910019B2 (en) * | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Mesogen containing compounds |
| US8628685B2 (en) * | 2008-06-27 | 2014-01-14 | Transitions Optical, Inc | Mesogen-containing compounds |
| US8623238B2 (en) | 2008-06-27 | 2014-01-07 | Transitions Optical, Inc. | Mesogenic stabilizers |
| US8431039B2 (en) | 2008-06-27 | 2013-04-30 | Transitions Optical, Inc. | Mesogenic stabilizers |
| US7910020B2 (en) * | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Liquid crystal compositions comprising mesogen containing compounds |
| US8613868B2 (en) | 2008-06-27 | 2013-12-24 | Transitions Optical, Inc | Mesogenic stabilizers |
| AU2010270797B2 (en) | 2009-07-08 | 2015-03-19 | Dermira (Canada), Inc. | TOFA analogs useful in treating dermatological disorders or conditions |
| 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 |
| 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 |
| 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 |
| WO2019206846A1 (en) | 2018-04-25 | 2019-10-31 | Basf Se | Process for the production of strongly adherent liquid crystal films on flexible substrates |
| WO2020207709A1 (en) | 2019-04-08 | 2020-10-15 | Rolic Technologies AG | Liquid crystal compounds |
| KR20220038353A (ko) | 2019-07-24 | 2022-03-28 | 롤릭 테크놀로지스 아게 | 광-정렬성 포지티브 c-플레이트 리타더 |
| EP4017938A1 (en) | 2019-08-19 | 2022-06-29 | Basf Se | A process for the production of fingerprint texture free liquid crystal films |
| WO2025214825A1 (en) | 2024-04-10 | 2025-10-16 | Basf Se | Process for the production of a colored level 2 feature |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0873409A (ja) * | 1994-08-31 | 1996-03-19 | F Hoffmann La Roche Ag | 光学活性スメクチック光架橋性液晶 |
| JPH08104870A (ja) * | 1994-09-12 | 1996-04-23 | F Hoffmann La Roche Ag | 光重合性液晶 |
| JPH08333320A (ja) * | 1995-06-07 | 1996-12-17 | F Hoffmann La Roche Ag | 光架橋性液晶染料 |
| JP2002520472A (ja) * | 1998-07-14 | 2002-07-09 | ロリク アーゲー | 組成物 |
| JP2002522410A (ja) * | 1998-08-07 | 2002-07-23 | ロリク アーゲー | 液晶化合物 |
| JP2002537280A (ja) * | 1999-02-17 | 2002-11-05 | ロリク アーゲー | 液晶化合物 |
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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 |
| JP4832639B2 (ja) * | 1998-01-27 | 2011-12-07 | ロリク アーゲー | 液晶光架橋性混合物 |
| GB9812636D0 (en) * | 1998-06-11 | 1998-08-12 | Rolic Ag | Optical component orientation layer and layerable polymerisable mixture |
| TW394852B (en) * | 1998-08-26 | 2000-06-21 | Merck Patent Gmbh | Reflective film |
-
1999
- 1999-03-17 GB GBGB9906168.1A patent/GB9906168D0/en not_active Ceased
-
2000
- 2000-02-15 JP JP2000605541A patent/JP4834226B2/ja not_active Expired - Lifetime
- 2000-02-15 DE DE60042589T patent/DE60042589D1/de not_active Expired - Lifetime
- 2000-02-15 US US09/936,725 patent/US6733690B1/en not_active Expired - Lifetime
- 2000-02-15 HK HK02100917.8A patent/HK1039318A1/zh unknown
- 2000-02-15 CN CNB008051003A patent/CN1213018C/zh not_active Expired - Lifetime
- 2000-02-15 EP EP00902824A patent/EP1169293B1/en not_active Expired - Lifetime
- 2000-02-15 AU AU24565/00A patent/AU2456500A/en not_active Abandoned
- 2000-02-15 WO PCT/IB2000/000158 patent/WO2000055110A1/en not_active Ceased
- 2000-02-15 KR KR1020017011671A patent/KR100750822B1/ko not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0873409A (ja) * | 1994-08-31 | 1996-03-19 | F Hoffmann La Roche Ag | 光学活性スメクチック光架橋性液晶 |
| JPH08104870A (ja) * | 1994-09-12 | 1996-04-23 | F Hoffmann La Roche Ag | 光重合性液晶 |
| JPH08333320A (ja) * | 1995-06-07 | 1996-12-17 | F Hoffmann La Roche Ag | 光架橋性液晶染料 |
| JP2002520472A (ja) * | 1998-07-14 | 2002-07-09 | ロリク アーゲー | 組成物 |
| JP2002522410A (ja) * | 1998-08-07 | 2002-07-23 | ロリク アーゲー | 液晶化合物 |
| JP2002537280A (ja) * | 1999-02-17 | 2002-11-05 | ロリク アーゲー | 液晶化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR100750822B1 (ko) | 2007-08-22 |
| EP1169293B1 (en) | 2009-07-22 |
| DE60042589D1 (de) | 2009-09-03 |
| KR20020004966A (ko) | 2002-01-16 |
| HK1039318A1 (zh) | 2002-04-19 |
| EP1169293A1 (en) | 2002-01-09 |
| CN1213018C (zh) | 2005-08-03 |
| GB9906168D0 (en) | 1999-05-12 |
| US6733690B1 (en) | 2004-05-11 |
| AU2456500A (en) | 2000-10-04 |
| JP2002539182A (ja) | 2002-11-19 |
| WO2000055110A1 (en) | 2000-09-21 |
| CN1344243A (zh) | 2002-04-10 |
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