JP5505686B2 - 重合性ビフェニル化合物 - Google Patents
重合性ビフェニル化合物 Download PDFInfo
- Publication number
- JP5505686B2 JP5505686B2 JP2009047838A JP2009047838A JP5505686B2 JP 5505686 B2 JP5505686 B2 JP 5505686B2 JP 2009047838 A JP2009047838 A JP 2009047838A JP 2009047838 A JP2009047838 A JP 2009047838A JP 5505686 B2 JP5505686 B2 JP 5505686B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- diyl
- liquid crystal
- coo
- independently
- 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.)
- Active
Links
- -1 biphenyl compound Chemical class 0.000 title claims description 70
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title description 27
- 235000010290 biphenyl Nutrition 0.000 title description 4
- 239000004305 biphenyl Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 91
- 239000004973 liquid crystal related substance Substances 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 66
- 230000003287 optical effect Effects 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- YGGXZTQSGNFKPJ-UHFFFAOYSA-N methyl 2-naphthalen-1-ylacetate Chemical compound C1=CC=C2C(CC(=O)OC)=CC=CC2=C1 YGGXZTQSGNFKPJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000758 substrate Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- 239000010409 thin film Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000005886 esterification reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000004642 Polyimide Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 229920001721 polyimide Polymers 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 230000000379 polymerizing effect Effects 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 230000018044 dehydration Effects 0.000 description 7
- 238000006297 dehydration reaction Methods 0.000 description 7
- 229910001873 dinitrogen Inorganic materials 0.000 description 7
- 239000004988 Nematic liquid crystal Substances 0.000 description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 6
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 150000002921 oxetanes Chemical class 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- ARUBXNBYMCVENE-UHFFFAOYSA-N 4-(4-bromophenyl)phenol Chemical group C1=CC(O)=CC=C1C1=CC=C(Br)C=C1 ARUBXNBYMCVENE-UHFFFAOYSA-N 0.000 description 4
- 238000007341 Heck reaction Methods 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 0 Cc1cc(N)ccc1-c1ccc(*)cc1 Chemical compound Cc1cc(N)ccc1-c1ccc(*)cc1 0.000 description 3
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- HTRNHWBOBYFTQF-UHFFFAOYSA-N 4-bromo-2-fluoro-1-phenylbenzene Chemical group FC1=CC(Br)=CC=C1C1=CC=CC=C1 HTRNHWBOBYFTQF-UHFFFAOYSA-N 0.000 description 2
- AUZPKZGIOYCYNV-UHFFFAOYSA-N 6-chlorohexyl prop-2-enoate Chemical compound ClCCCCCCOC(=O)C=C AUZPKZGIOYCYNV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 230000001678 irradiating effect 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
- 239000011368 organic material Substances 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XIHBGPUCYCLLTO-UHFFFAOYSA-N (3-ethyl-4-hydroxyphenyl) 3-chloropropanoate Chemical compound ClCCC(=O)OC1=CC(=C(C=C1)O)CC XIHBGPUCYCLLTO-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- QSVXXQNLMJMOPL-UHFFFAOYSA-N 1-bromo-2-fluoro-4-phenylbenzene Chemical group C1=C(Br)C(F)=CC(C=2C=CC=CC=2)=C1 QSVXXQNLMJMOPL-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- 150000004786 2-naphthols Chemical class 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical class C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical class CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- WJRHSYCQNCDYMN-UHFFFAOYSA-N 4'-Hydroxy-2-biphenylcarboxylic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=C(O)C=C1 WJRHSYCQNCDYMN-UHFFFAOYSA-N 0.000 description 1
- GFBCWCDNXDKFRH-UHFFFAOYSA-N 4-(oxan-2-yloxy)phenol Chemical compound C1=CC(O)=CC=C1OC1OCCCC1 GFBCWCDNXDKFRH-UHFFFAOYSA-N 0.000 description 1
- AQSCHALQLXXKKC-UHFFFAOYSA-N 4-phenylmethoxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCC1=CC=CC=C1 AQSCHALQLXXKKC-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical class CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002999 depolarising effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000007765 extrusion coating Methods 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000011907 photodimerization Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003232 pyrogallols Chemical class 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Description
(製法1) 一般式(I-1)で表される化合物の製造
4-ブロモ-4’-ヒドロキシビフェニルとアクリル酸ターシャリーブチルとのパラジウム触媒による溝呂木−ヘック反応により、ビフェニル誘導体(S-1)を得て、更に塩化メタアクリロイルとのエステル化反応により、メタアクリロイル基を有するビフェニル誘導体(S-2)を得る。更にトリフルオロ酢酸により、ターシャリーブチル基を脱離させてカルボン酸基に変換したビフェニル誘導体(S-3)を得る。
4-ブロモ-4’-ヒドロキシビフェニルとアクリル酸ターシャリーブチルとのパラジウム触媒による溝呂木−ヘック反応により、ビフェニル誘導体(S-1)を得て、更に6-クロロヘキシルアクリレートとを炭酸カリウム等の塩基存在下でエーテル化反応させて、アクリロイル基を有するビフェニル誘導体(S-4)を得る。更にトリフルオロ酢酸により、ターシャリーブチル基を脱離させてカルボン酸基に変換したビフェニル誘導体(S-5)を得る。
4-ブロモ-4’-ヒドロキシビフェニルとアクリル酸ターシャリーブチルとのパラジウム触媒による溝呂木−ヘック反応により、ビフェニル誘導体(S-1)を得て、更に塩化アクリロイルとのエステル化反応により、アクリロイル基を有するビフェニル誘導体(S-6)を得る。更にトリフルオロ酢酸により、ターシャリーブチル基を脱離させてカルボン酸基に変換したビフェニル誘導体(S-7)を得る。
2-フルオロ-4-ブロモビフェニルと塩化アセチルとを塩化アルミニム(III)を用いたフリーデルクラフト反応を行い、更にギ酸と過酸化水素水による過ギ酸によりフッ素原子により置換したヒドロキシビフェニル化合物(S-10)を得る。更にアクリル酸ターシャリーブチルとのパラジウム触媒による溝呂木−ヘック反応により、ビフェニル誘導体(S-11)を得て、更にパラジウムカーボンを用いた接触水素還元により、ビフェニル誘導体(S-12)を得る。次いで6-クロロヘキシルアクリレートと炭酸カリウム等の塩基存在下でエーテル化反応させて、アクリロイル基を有するビフェニル誘導体(S-13)を得る。更にトリフルオロ酢酸により、ターシャリーブチル基を脱離させてカルボン酸基に変換したビフェニル誘導体(S-14)を得る。
3-エチル-3-ヒドロキシメチルオキセタン(商品名EOXA,東亜合成社製)と1-ブロモ-3-クロロプロパンとを水酸化ナトリウム等の塩基の存在下でエーテル化反応させ、オキセタン誘導体(S-16)を得る。更にビフェニル誘導体(S-12)を得る。次いでビフェニル誘導体(S-1)とオキセタン誘導体(S-16)を炭酸カリウム等の塩基存在下でエーテル化反応させて、更にトリフルオロ酢酸によりターシャリーブチル基を脱離させて、オキセタン基及びカルボキシル基を有するビフェニル誘導体(S-18)を得る。
4-ベンジルオキシ安息香酸と4-(3-クロロプロピオニルオキシ)エチルフェノールとのジシクロヘキシルカルボジイミド等の脱水縮合剤を用いたエステル化反応によりフェニルベンゾアート誘導体(S-20)を得る。次いでパラジウムカーボンを用いた接触水素還元により、フェノール誘導体(S-21)を得る。更に、過剰のトリエチルアミンを用いた脱HCl反応によりアクリロイルを有するフェノール誘導体(S-22)を得る。
(実施例1)
撹拌装置、冷却器、及び温度計を備えた反応容器に4−ブロモ−4’−ヒドロキシビフェニル 10g(40.1ミリモル)、ターシャリーブチルアクリレート 6.2g(48.2ミリモル)、トリエチルアミン 4.8g(48ミリモル)、酢酸パラジウム 530mg、ジメチルホルムアミド 300mlを仕込み、窒素ガス雰囲気下で反応器を100℃に加熱し反応させた。反応終了後、酢酸エチル、THFを加え、10%塩酸水溶液、純水、飽和食塩水で有機層を洗浄した。溶媒を留去した後、2倍量(重量比)のシリカゲルカラムにより精製を行い式(1)に示す化合物11gを得た。
H−NMR(溶媒:重クロロホルム):δ:2.98(t,2H), 4.36(t,2H),5.82(d,1H),6.03−6.18(m,2H),6.32−6.44(m,2H),6.62−6.66(m,2H),7.12(d,2H),7.22−7.33(m,4H),7.65(m,6H),7.88(d,1H)
13C−NMR(溶媒:重クロロホルム):δ:34.6,64.8,117.0,121.5,127.4,127.9,128.2,128.6,129.7,130.7,132.7,133.0,135.1,137.6,142.3,145.7,149.2,150.2,165.2
赤外吸収スペクトル(IR)(KBr):2925,2855,1760,1652−1622,809 cm−1
融点:113℃
(実施例2)
撹拌装置備えたオートクレーブ容器に、式(1)に示される実施例1で合成した中間体4.5g(15.2ミリモル)、5%パラジウムカーボン 250mg、テトラヒドロフラン50ml、エタノール5mlを仕込み、0.3MPaの水素にて還元反応(室温、8時間)を行った。反応液をろ過した後、反応溶媒を留去して式(5)に示す化合物4.5gを得た。
H−NMR(溶媒:重クロロホルム):δ:2.89−2.98(m,4H), 3.11(t,2H),4.33(t,2H),5.80(dd,1H),6.02−6.12(m,2H),6.32−6.40(m,2H),6.61(dd,1H),6.95(d,2H),7.20−7.28(m,4H),7.32(d,2H),7.52(d,2H),7.59(d,2H)
13C−NMR(溶媒:重クロロホルム):δ:30.6,34.5,35.9,64.8,121.4,121.6,127.1,127.7,128.2,128.7,129.7,130.7,132.5,135.2,138.3,139.1,149.0,149.7,164.3,165.8,171.1
赤外吸収スペクトル(IR)(KBr):2925,2855,1760,1652−1622,809 cm−1
融点:87℃
(実施例3)
撹拌装置、冷却器、及び温度計を備えた反応容器に塩化アルミニウム(III)を12.8g(96ミリモル)、ジクロロメタン100mlを加え攪拌した。次いで塩化アセチル 8.4g(110ミリモル)を90分かけてゆっくり滴下し、更に4−ブロモ−2−フルオロビフェニル 20g(80ミリモル)のジクロロメタン溶液80mlを2時間かけてゆっくり滴下した。滴下終了後、更に2時間攪拌し、反応を終了させた。反応液を500mlの氷水にゆっくり注ぎ、ジクロロメタンで抽出し、純水、飽和食塩水で有機層を洗浄した。溶媒を留去した後、乾燥を行いアセチル基を導入した化合物を23g得た。次いで、撹拌装置、冷却器、及び温度計を備えた反応容器にアセチル基を導入した化合物23g、ギ酸300mlを仕込み、34.5%の過酸化水素水20mlを加え、加熱還流を6時間行った。反応終了後、10%の亜硫酸水素ナトリウム水溶液450ml行い、過酸化物を分解した。析出した固体をろ過し酢酸エチルで溶解させ水、飽和食塩水で有機層を洗浄した。溶媒を留去した後、2倍量(重量比)のシリカゲルカラムにより精製を行い式(9)に示す化合物18gを得た。
H−NMR(溶媒:重クロロホルム):δ:6.04(d,1H),6.32−6.44(m,1H),6.62−6.67(m,2H),7.25−7.28(m,4H),7.34−7.49(m,6H),7.61−7.65(m,6H),7.88(d,1H)
13C−NMR(溶媒:重クロロホルム):δ:115.2,118.2,121.4,121.5,126.8,127.0,127.4,127.8,128.4,129.7,132.5,132.0,135.1,142.3,145.7,149.2,150.2,165.2
赤外吸収スペクトル(IR)(KBr):1760,1652−1622,809 cm−1
融点:164℃
(実施例4)
以下に示す組成の重合性液晶組成物(組成物1)を調製した。
(比較例1)
以下に示す組成の重合性液晶組成物(組成物3)を調製した。
(比較例2)
以下に示す組成の重合性液晶組成物(組成物4)を調製した。
Claims (9)
- 一般式(I)
- 一般式 (I) において、L2及びL3はお互い独立して、−O−、−OCH2−、−CH2O−、―COO−、−OCO−、−C2H4−、−C≡C−、又は単結合を表し、M1は、1,4−シクロヘキシレン基、1,4−フェニレン基、ナフタレン−2,6−ジイル基又は、テトラヒドロナフタレン−2,6−ジイル基を表し、M2は1,4−フェニレン基、1,4−シクロヘキシレン基、ナフタレン−2,6−ジイル基、テトラヒドロナフタレン−2,6−ジイル基、1,3−ジオキサン−2,5−ジイル基、1,3,5−ベンゼントリイル基、1,3,4−ベンゼントリイル基、1,3,4,5−ベンゼンテトライル基、1,4−シクロヘキシレン基、1,3,5−シクロヘキサントリイル基又は1,3,4−シクロヘキサントリイル基を表わし、M1及びM2はお互い独立してアルキル基、ハロゲン化アルキル基、アルコキシ基、ハロゲン化アルコキシ基、ハロゲン、シアノ基又はニトロ基により置換されていても良く、qは1又は2を表す請求項1記載の重合性化合物。
- 一般式 (I) において、M2が無置換であるかアルキル基、ハロゲン化アルキル基、アルコキシ基、ハロゲン化アルコキシ基、ハロゲン、シアノ基又はニトロ基により置換されていても良い1,4−フェニレン基、1,3,5−ベンゼントリイル基、1,3,4−ベンゼントリイル基又は1,3,4,5−ベンゼンテトライル基を表す請求項1又は2記載の重合性化合物。
- 一般式 (I) において、R1及びR2がお互いに独立して式(R-1)又は式(R-2)を表す請求項1、2又は3記載の重合性化合物。
- pが0を表す請求項1、2、3又は4記載の重合性化合物。
- S1が単結合を表す請求項1、2、3、4又は5記載の重合性化合物。
- 請求項1から6の何れかに記載される重合性化合物を含有する液晶組成物。
- 請求項7記載の重合性化合物を含有する液晶組成物の重合体により構成される光学異方体。
- 請求項8記載の光学異方体を用いることを特徴とする液晶表示素子。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009047838A JP5505686B2 (ja) | 2009-01-23 | 2009-03-02 | 重合性ビフェニル化合物 |
KR1020090099182A KR101563574B1 (ko) | 2009-01-23 | 2009-10-19 | 중합성 비페닐 화합물 |
CN201010003321.9A CN101792391B (zh) | 2009-01-23 | 2010-01-21 | 聚合性联苯化合物 |
CN201310283703.5A CN103360257B (zh) | 2009-01-23 | 2010-01-21 | 聚合性联苯化合物 |
TW099101710A TWI454456B (zh) | 2009-01-23 | 2010-01-22 | 聚合性聯苯化合物 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009012907 | 2009-01-23 | ||
JP2009012907 | 2009-01-23 | ||
JP2009047838A JP5505686B2 (ja) | 2009-01-23 | 2009-03-02 | 重合性ビフェニル化合物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010189615A JP2010189615A (ja) | 2010-09-02 |
JP5505686B2 true JP5505686B2 (ja) | 2014-05-28 |
Family
ID=42815982
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009047838A Active JP5505686B2 (ja) | 2009-01-23 | 2009-03-02 | 重合性ビフェニル化合物 |
Country Status (3)
Country | Link |
---|---|
JP (1) | JP5505686B2 (ja) |
CN (1) | CN103360257B (ja) |
TW (1) | TWI454456B (ja) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5545516B2 (ja) * | 2009-09-25 | 2014-07-09 | Dic株式会社 | 重合性化合物 |
CN102093220B (zh) * | 2009-12-11 | 2014-12-10 | Dic株式会社 | 羧酸的制备方法、羧酸烯丙酯 |
JP5751466B2 (ja) * | 2010-10-13 | 2015-07-22 | Dic株式会社 | 重合性化合物含有液晶組成物及びそれを使用した液晶表示素子 |
JP5733097B2 (ja) * | 2010-10-28 | 2015-06-10 | Jnc株式会社 | 光配向法に適した化合物および該化合物からなる感光性ポリマー |
KR101749768B1 (ko) | 2010-10-28 | 2017-06-21 | 제이엔씨 주식회사 | 광 배향법에 적합한 화합물 및 그 화합물로 이루어지는 감광성 폴리머 |
CN104557545B (zh) * | 2013-10-10 | 2016-09-21 | 江苏和成显示科技股份有限公司 | 可聚合性化合物及其在光学各向异性体和液晶显示元件中的应用 |
JP6304529B2 (ja) * | 2013-12-06 | 2018-04-04 | Dic株式会社 | 重合性化合物及び光学異方体 |
CN104099104A (zh) * | 2014-08-04 | 2014-10-15 | 石家庄诚志永华显示材料有限公司 | 液晶组合物 |
JP2016169218A (ja) * | 2016-04-20 | 2016-09-23 | Dic株式会社 | 重合性化合物及びそれを用いた液晶組成物 |
KR102429339B1 (ko) * | 2018-02-14 | 2022-08-03 | 후지필름 가부시키가이샤 | 광학 필름, 편광판 및 화상 표시 장치 |
CN114805752B (zh) * | 2022-05-26 | 2024-04-09 | 浙江亚厦装饰股份有限公司 | 一种导热液晶环氧树脂的制备方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4200195B2 (ja) * | 1998-10-09 | 2008-12-24 | Dic株式会社 | 液晶性(メタ)アクリレート化合物、該化合物を含有する液晶組成物及びこれを用いた光学異方体 |
JP4208058B2 (ja) * | 1998-10-09 | 2009-01-14 | Dic株式会社 | 液晶性(メタ)アクリレート化合物及び該化合物を含有する液晶組成物 |
JP4924865B2 (ja) * | 2006-01-20 | 2012-04-25 | Dic株式会社 | 重合性液晶化合物、重合性液晶組成物及びこれの重合体 |
WO2008026482A1 (fr) * | 2006-08-29 | 2008-03-06 | Asahi Glass Company, Limited | Esters d'acides gras insaturés, et compositions de cristaux liquides polymérisables, matériaux optiquement anisotropes et éléments optiques, fabriqués en utilisant les esters |
US7862867B2 (en) * | 2006-10-05 | 2011-01-04 | Nissan Chemical Industries, Ltd. | Bifunctional polymerizable compound, polymerizable liquid crystal composition, and oriented film |
JP5546093B2 (ja) * | 2006-12-26 | 2014-07-09 | 株式会社Adeka | 重合性化合物及び重合性組成物 |
-
2009
- 2009-03-02 JP JP2009047838A patent/JP5505686B2/ja active Active
-
2010
- 2010-01-21 CN CN201310283703.5A patent/CN103360257B/zh active Active
- 2010-01-22 TW TW099101710A patent/TWI454456B/zh active
Also Published As
Publication number | Publication date |
---|---|
CN103360257A (zh) | 2013-10-23 |
TW201033171A (en) | 2010-09-16 |
CN103360257B (zh) | 2015-06-10 |
TWI454456B (zh) | 2014-10-01 |
JP2010189615A (ja) | 2010-09-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5505686B2 (ja) | 重合性ビフェニル化合物 | |
JP5549174B2 (ja) | 重合性ナフタレン化合物 | |
JP5103774B2 (ja) | 重合性キラル化合物 | |
JP5168976B2 (ja) | ビフェニル及びテルフェニル化合物、該化合物を含有する重合性液晶組成物 | |
JP5531475B2 (ja) | 重合性キラル化合物 | |
JP5103981B2 (ja) | 5、6及び7環を有する重合性化合物、該化合物を含有する重合性液晶組成物 | |
JP4961795B2 (ja) | 重合性キラル化合物 | |
JP5125171B2 (ja) | 重合性化合物 | |
JP5509678B2 (ja) | 重合性化合物及び該化合物を用いた重合性組成物 | |
JP6031781B2 (ja) | 重合性化合物及びそれを用いた液晶組成物 | |
JP5545519B2 (ja) | 重合性化合物 | |
JP6308415B2 (ja) | 重合性化合物及びそれを用いた液晶組成物 | |
JP5288156B2 (ja) | 重合性キラル化合物 | |
JP4924865B2 (ja) | 重合性液晶化合物、重合性液晶組成物及びこれの重合体 | |
JP5493416B2 (ja) | 重合性ビフェニル化合物 | |
JP5545516B2 (ja) | 重合性化合物 | |
KR101563574B1 (ko) | 중합성 비페닐 화합물 | |
JP2011184417A (ja) | 重合性アセチレン化合物 | |
JP5787466B2 (ja) | 多官能重合性化合物 | |
JP6270016B2 (ja) | 重合性化合物 | |
TWI477589B (zh) | Polymerizable compounds | |
JP5051417B2 (ja) | 光開始剤及び重合性組成物 | |
JP2016169218A (ja) | 重合性化合物及びそれを用いた液晶組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120213 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130307 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130418 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130523 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140220 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140305 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5505686 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |