JP7067302B2 - 重合性化合物及び光学異方体 - Google Patents
重合性化合物及び光学異方体 Download PDFInfo
- Publication number
- JP7067302B2 JP7067302B2 JP2018116098A JP2018116098A JP7067302B2 JP 7067302 B2 JP7067302 B2 JP 7067302B2 JP 2018116098 A JP2018116098 A JP 2018116098A JP 2018116098 A JP2018116098 A JP 2018116098A JP 7067302 B2 JP7067302 B2 JP 7067302B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- compound represented
- oco
- coo
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 308
- 230000003287 optical effect Effects 0.000 title description 15
- 239000000203 mixture Substances 0.000 claims description 119
- 125000004432 carbon atom Chemical group C* 0.000 claims description 114
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 94
- 229910052731 fluorine Inorganic materials 0.000 claims description 48
- 125000001153 fluoro group Chemical group F* 0.000 claims description 48
- -1 filters Substances 0.000 claims description 43
- 239000004973 liquid crystal related substance Substances 0.000 claims description 43
- 125000002947 alkylene group Chemical group 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 29
- 239000000463 material Substances 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 9
- 239000000853 adhesive Substances 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000003921 oil Substances 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 4
- 239000004566 building material Substances 0.000 claims description 3
- 238000004891 communication Methods 0.000 claims description 3
- 239000003599 detergent Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000012776 electronic material Substances 0.000 claims description 3
- 235000013305 food Nutrition 0.000 claims description 3
- 239000000976 ink Substances 0.000 claims description 3
- 239000011368 organic material Substances 0.000 claims description 3
- 239000005022 packaging material Substances 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- 239000004065 semiconductor Substances 0.000 claims description 3
- 239000003925 fat Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 228
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
- 238000006243 chemical reaction Methods 0.000 description 116
- 125000001424 substituent group Chemical group 0.000 description 93
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
- 239000002904 solvent Substances 0.000 description 63
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 58
- 238000004440 column chromatography Methods 0.000 description 53
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 48
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- 239000000741 silica gel Substances 0.000 description 48
- 229910002027 silica gel Inorganic materials 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- 238000000746 purification Methods 0.000 description 47
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 238000001953 recrystallisation Methods 0.000 description 40
- 239000010408 film Substances 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 238000006467 substitution reaction Methods 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 31
- 238000001816 cooling Methods 0.000 description 27
- 239000000758 substrate Substances 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000011780 sodium chloride Substances 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 20
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 20
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 19
- 239000012267 brine Substances 0.000 description 18
- 239000011248 coating agent Substances 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 17
- 238000000576 coating method Methods 0.000 description 17
- 229920000728 polyester Polymers 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 13
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 13
- 238000001035 drying Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 241000209094 Oryza Species 0.000 description 12
- 235000007164 Oryza sativa Nutrition 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
- 230000000379 polymerizing effect Effects 0.000 description 12
- 235000009566 rice Nutrition 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
- 230000007704 transition Effects 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 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 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 5
- KECMLGZOQMJIBM-UHFFFAOYSA-N 2-[2-(2-chloroethoxy)ethoxy]ethanol Chemical compound OCCOCCOCCCl KECMLGZOQMJIBM-UHFFFAOYSA-N 0.000 description 5
- 239000004642 Polyimide Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 description 4
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- JYSUYJCLUODSLN-UHFFFAOYSA-N 1,3-benzothiazol-2-ylhydrazine Chemical compound C1=CC=C2SC(NN)=NC2=C1 JYSUYJCLUODSLN-UHFFFAOYSA-N 0.000 description 3
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 description 3
- 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 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
- ZQJNPHCQABYENK-UHFFFAOYSA-N 4-methoxycarbonylcyclohexane-1-carboxylic acid Chemical compound COC(=O)C1CCC(C(O)=O)CC1 ZQJNPHCQABYENK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000012788 optical film Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000012719 thermal polymerization Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OGIBBHKFFODLIR-UHFFFAOYSA-N (2-propylphenoxy)boronic acid Chemical compound CCCC1=CC=CC=C1OB(O)O OGIBBHKFFODLIR-UHFFFAOYSA-N 0.000 description 2
- HUXJXNSHCKHFIL-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-methoxyethane Chemical compound COCCOCCBr HUXJXNSHCKHFIL-UHFFFAOYSA-N 0.000 description 2
- LECMBPWEOVZHKN-UHFFFAOYSA-N 2-(2-chloroethoxy)ethanol Chemical compound OCCOCCCl LECMBPWEOVZHKN-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
- CCZCXFHJMKINPE-UHFFFAOYSA-N 2-phenylmethoxyphenol Chemical compound OC1=CC=CC=C1OCC1=CC=CC=C1 CCZCXFHJMKINPE-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 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
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 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
- 150000002576 ketones Chemical class 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 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
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
- SCRQAWQJSSKCFN-UHFFFAOYSA-N 2-bromo-5-hydroxybenzaldehyde Chemical compound OC1=CC=C(Br)C(C=O)=C1 SCRQAWQJSSKCFN-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
- 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
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical group CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 1
- KWCPPCKBBRBYEE-UHFFFAOYSA-N 3-chloropropyl prop-2-enoate Chemical compound ClCCCOC(=O)C=C KWCPPCKBBRBYEE-UHFFFAOYSA-N 0.000 description 1
- AHAZEMSUUYFDMM-UHFFFAOYSA-N 4-(4-propylcyclohexyl)phenol Chemical compound C1CC(CCC)CCC1C1=CC=C(O)C=C1 AHAZEMSUUYFDMM-UHFFFAOYSA-N 0.000 description 1
- MKKSTJKBKNCMRV-UHFFFAOYSA-N 5-bromo-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Br)C=C1C=O MKKSTJKBKNCMRV-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 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
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 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
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000006959 Williamson synthesis reaction Methods 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 125000002521 alkyl halide group Chemical group 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 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
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002999 depolarising effect Effects 0.000 description 1
- 238000000151 deposition Methods 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
- 230000006866 deterioration Effects 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- 238000004299 exfoliation Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 238000007765 extrusion coating Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011737 fluorine Substances 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
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 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
- 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
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 150000003232 pyrogallols Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
- C09K19/3497—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/10—Esters
- C08F22/12—Esters of phenols or saturated alcohols
- C08F22/24—Esters containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
- C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
- C08F222/1035—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate of aromatic trialcohols
-
- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
- C09K19/3804—Polymers with mesogenic groups in the main chain
- C09K19/3814—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
-
- 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
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/122—Ph-Ph
-
- 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
- C09K2019/2035—Ph-COO-Ph
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3004—Cy-Cy
-
- 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/542—Macromolecular compounds
- C09K2019/548—Macromolecular compounds stabilizing the alignment; Polymer stabilized alignment
-
- 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
- C09K2219/00—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used
- C09K2219/03—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used in the form of films, e.g. films after polymerisation of LC precursor
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/13363—Birefringent elements, e.g. for optical compensation
- G02F1/133633—Birefringent elements, e.g. for optical compensation using mesogenic materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Cosmetics (AREA)
- Liquid Crystal Substances (AREA)
- Polarising Elements (AREA)
- Polymerisation Methods In General (AREA)
Description
《位相差の測定》
配向膜用ポリイミド溶液を厚さ0.7mmのガラス基材にスピンコート法を用いて塗布し、100℃で10分乾燥した後、200℃で60分焼成することにより塗膜を得る。得られた塗膜を市販のラビング装置を用いてラビング処理する。
A1及びA2は各々独立して1,4-フェニレン基、1,4-シクロヘキシレン基、ピリジン-2,5-ジイル基、ピリミジン-2,5-ジイル基、ナフタレン-2,6-ジイル基、ナフタレン-1,4-ジイル基、テトラヒドロナフタレン-2,6-ジイル基、デカヒドロナフタレン-2,6-ジイル基又は1,3-ジオキサン-2,5-ジイル基を表すが、これらの基は無置換であるか又は1つ以上の置換基Lによって置換されても良く、Lはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LはPL-(SpL-XL)kL-で表される基を表しても良く、ここでPLは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpLは1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表すが、SpLが複数存在する場合それらは同一であっても異なっていても良く、XLは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XLが複数存在する場合それらは同一であっても異なっていても良く(ただし、PL-(SpL-XL)kL-には-O-O-結合を含まない。)、kLは0から10の整数を表すが、化合物内にLが複数存在する場合それらは同一であっても異なっていても良く、置換基Lはフッ素原子、塩素原子、ペンタフルオロスルフラニル基、ニトロ基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、又は、任意の水素原子はフッ素原子に置換されても良く、1個の-CH2-又は隣接していない2個以上の-CH2-は各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-O-CO-O-、-CH=CH-、-CF=CF-又は-C≡C-から選択される基によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すことが好ましく、フッ素原子、塩素原子、又は、任意の水素原子はフッ素原子に置換されても良く、1個の-CH2-又は隣接していない2個以上の-CH2-は各々独立して-O-、-COO-又は-OCO-から選択される基によって置換されても良い炭素原子数1から12の直鎖状又は分岐状アルキル基を表すことがより好ましく、フッ素原子、塩素原子、又は、任意の水素原子はフッ素原子に置換されても良い炭素原子数1から12の直鎖状又は分岐状アルキル基若しくはアルコキシ基を表すことがさらに好ましく、フッ素原子、塩素原子、又は、炭素原子数1から8の直鎖アルキル基若しくは直鎖アルコキシ基を表すことが特に好ましい。
Z1及びZ2は各々独立して-O-、-S-、-OCH2-、-CH2O-、-CH2CH2-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-OCO-NH-、-NH-COO-、-NH-CO-NH-、-NH-O-、-O-NH-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-、-N=CH-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、Z1が複数存在する場合それらは同一であっても異なっていても良く、Z2が複数存在する場合それらは同一であっても異なっていても良く、
G1は芳香族炭化水素環又は芳香族複素環からなる群から選ばれる少なくとも1つの芳香族環を有する2価の基を表すが、G1で表される基中の芳香族環に含まれるπ電子の数は12以上であり、G1で表される基は無置換であるか又は1つ以上の置換基LGによって置換されても良く、置換基LGはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LGはPLG-(SpLG-XLG)kLG-で表される基を表しても良く、ここでPLGは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpLGは1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表すが、SpLGが複数存在する場合それらは同一であっても異なっていても良く、XLGは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XLGが複数存在する場合それらは同一であっても異なっていても良く(ただし、PLG-(SpLG-XLG)kLG-には-O-O-結合を含まない。)、kLGは0から10の整数を表すが、化合物内にLGが複数存在する場合それらは同一であっても異なっていても良く、m1及びm2は各々独立して0から6の整数を表すが、m1+m2は0から6の整数を表す。)で表される化合物であることが好ましい。
W2は水素原子、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、W2は少なくとも1つの芳香族基を有する、炭素原子数2から30の基を表しても良いが、当該基は無置換であるか又は1つ以上の置換基LWによって置換されても良く、若しくは、W2はPW-(SpW-XW)kW-で表される基を表しても良く、ここでPWは重合性基を表し、SpWはスペーサー基又は単結合を表し、SpWが複数存在する場合それらは同一であっても異なっていても良く、XWは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XWが複数存在する場合それらは同一であっても異なっていても良く(ただし、PW-(SpW-XW)kW-には-O-O-結合を含まない。)、kWは0から10の整数を表し、
置換基LWはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LWはPLW-(SpLW-XLW)kLW-で表される基を表しても良く、ここでPLWは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpLWは1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表すが、SpLWが複数存在する場合それらは同一であっても異なっていても良く、XLWは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XLWが複数存在する場合それらは同一であっても異なっていても良く(ただし、PLW-(SpLW-XLW)kLW-には-O-O-結合を含まない。)、kLWは0から10の整数を表すが、化合物内に置換基LWが複数存在する場合それらは同一であっても異なっていても良く、
Yは水素原子、フッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基又は1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくはYはPY-(SpY-XY)kY-で表される基を表しても良く、PYは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpYは上述の1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表し、SpYが複数存在する場合それらは同一であっても異なっていても良く、XYは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XYが複数存在する場合それらは同一であっても異なっていても良く(ただし、PY-(SpY-XY)kY-には-O-O-結合を含まない。)、kYは0から10の整数を表すが、W1及びW2は一緒になって環構造を形成しても良い。)から選ばれる基を表す。)から選ばれる基を表すことがより好ましい。溶媒への溶解性、合成の容易さの観点から、G1は上記の式(M-1)、式(M-3)、式(M-4)、式(M-7)、式(M-8)から選ばれる基を表すことがさらに好ましく、式(M-1)、式(M-7)、式(M-8)から選ばれる基を表すことがさらにより好ましく、式(M-7)、式(M-8)から選ばれる基を表すことが特に好ましい。
(実施例1)式(I-1)で表される化合物の製造
転移温度(昇温5℃/分):C 89-123 I
1H NMR(CDCl3)δ 1.05(t,3H),1.70(m,2H),2.70(t,2H),3.58-3.73(m,6H),3.75(t,2H),4.02(t,2H),4.27(t,2H),5.84(dd,1H),6.12(dd,1H),6.42(dd,1H),6.65(d,2H),7.00(d,2H),7.15-7.45(m,5H),7.51-7.70(m,5H),7.78(dd,1H),8.17(s,1H),11.7(s,1H)ppm.
LCMS:694[M+1]
(実施例2)式(I-2)で表される化合物の製造
転移温度(昇温5℃/分):C 75-108 N 180 I
1H NMR(CDCl3)δ 0.94(t,3H),1.10(m,2H),1.25(m,2H),1.29-1.57(m,11H),1.80-2.08(m,6H),2.30(m,2H),2.54(m,1H),3.67-3.78(m,6H),3.85(t,2H),4.11(t,2H),4.32(t,2H),5.84(dd,1H),6.15(dd,1H),6.40(dd,1H),6.82-7.00(m,4H),7.08-7.60(m,4H),7.65-8.10(m,3H)、8.40(s,1H)、11.6(s,1H)ppm.
LCMS:826[M+1]
(実施例3)式(I-3)で表される化合物の製造
転移温度(昇温5℃/分):C 131 I
1H NMR(CDCl3)δ 0.88-0.94(m,6H),1.10(m,2H),1.22-1.52(m,13H),1.72(m,6H),1.94(t,4H),2.32(m,4H),2.53-2.62(m,3H),3.69-3.77(m,6H),3.86(t,2H),4.12(t,2H),4.27-4.34(m,4H),5.83(dd,1H),6.16(dd,1H),6.43(dd,1H),6.91(d,2H),6.97-7.02(m,3H),7.16(t,1H),7.23(dd,1H),7.33(t,1H),6.66-7.72(m,3H),7.90(d,1H)ppm.
LCMS:910[M+1]
(実施例4)式(I-4)で表される化合物の製造
転移温度(昇温5℃/分):C 90 Sm 218 N 265 I
1H NMR(CDCl3)δ 0.88(m,6H),1.01-1.19(m,8H),1.32-1.45(m,6H),1.71-1.76(m,6H),1.88-1.99(m,3H),2.17(m,12H),2.31(m,4H),2.53(m,2H),2.67(m,1H),3.70-3.76(m,6H),3.85(t,2H),4.11(t,2H),4.31(m,4H),5.82(d,2H),6.15(q,2H),6.43(d,2H),6.92(m,5H),7.14-7.26(m,2H),7.33(t,1H),7.68(m,3H),7.88(s,1H)ppm.
(実施例5)式(I-5)で表される化合物の製造
転移温度(昇温5℃/分):C 77 S 90 N 109 I
1H NMR(CDCl3)δ 0.89(t,3H),1.20-1.35(m,10H),1.61-1.69(m,6H),1.78(m,2H),1.90(m,2H),2.07(t,4H),2.23(d,4H),2.50(m,2H),3.69-3.76(m,12H),3.83-3.87(m,8H),4.11(t,4H),4.32(t,6H),5.82(d,2H),6.15(q,2H),6.42(d,2H),6.83-6.98(m,10H),7.13(t,1H),7.32(t,1H),7.53(t,1H),7.66(t,2H),8.13(s,1H)ppm.
(実施例6)式(I-6)で表される化合物の製造
転移温度(昇温5℃/分):C 85 N 128 I
1H NMR(CDCl3)δ 1.22-1.28(m,4H),1.44-1.47(m,8H),1.60-1.82(m,12H),1.90(m,2H),2.07(t,4H),2.24(d,4H),2.53(m,2H),3.30(s,3H),3.50(t,2H),3.66(t,2H),3.85-3.89(m,6H),3.93(t,4H),4.17(t,4H),4.53(t,2H),5.82(d,2H),6.13(q,2H),6.40(d,2H),6.83-6.90(m,6H),6.95-6.98(m,4H),7.14(t,1H),7.32(t,1H),7.52(t,1H),7.67(t,2H),8.33(s,1H)ppm.
(実施例7)式(I-7)で表される化合物の製造
転移温度(昇温5℃/分):C 106 N 125 I
1H NMR(CDCl3)δ 0.92(t,3H),1.11(q,2H),1.25(m,2H),1.36(m,2H),1.48(m,4H),1.68-1.81(m,12H),1.93(t,4H),2.32(m,3H),2.58(m,2H),2.71(m,1H),3.30(s,3H),3.48(m,2H),3.62(m,2H),3.85(t,2H),3.94(t,2H),4.17(t,2H),4.47(t,2H),5.82(d,2H),6.12(q,2H),6.40(d,2H),6.87(d,2H),6.96(m,3H),7.16(t,1H),7.22(m,1H),7.33(t,1H),7.70(q,2H),7.88(d,1H),8.01(s,1H)ppm.
(実施例8)式(I-8)で表される化合物の製造
転移温度(昇温5℃/分):C 89-95 N 145 I
1H NMR(CDCl3)δ 1.24(m,4H),1.65(m,4H),1.91(m,2H),2.05-2.25(m,12H),2.55(m,2H),3.30(s,3H),3.51(m,2H),3.67(m,2H),3.84-3.89(m,6H),4.05(t,4H),4.36(t,4H),4.54(t,2H),5.84(dd,2H),6.13(dd,2H),6.41(dd,2H),6.84-6.89(m,6H),6.97-7.00(m,4H),7.14(t,1H),7.33(t,1H),7.52(d,1H),7.67(dd,2H),8.34(s,1H)ppm.
LCMS:1076[M+1]
(実施例9)式(I-9)で表される化合物の製造
転移温度(昇温5℃/分)C 71 N 115 I
1H NMR(CDCl3)δ 1.19-1.29(m,4H),1.41-1.82(m,22H),1.91(m,2H),2.08(m,4H),2.24(m,4H),2.53(m,2H),3.62(m,3H),3.67(m,2H),3.84-3.90(m,5H),3.94(t,4H),4.15-4.19(m,6H),4.53(t,2H),5.76(dd,1H),5.82(dd,2H),6.08(dd,1H),6.12(dd,2H),6.37(dd,1H),6.40(dd,2H),6.84-6.90(m,6H),6.95-6.98(m,4H),7.14(t,1H),7.32(t,1H),7.53(d,1H),7.65(d,1H),7.69(d,1H),8.34(s,1H)ppm.
LCMS:1244[M+1]
(実施例10)式(I-10)で表される化合物の製造
転移温度(昇温5℃/分、降温5℃/分):C 101-105(N 82)I
1H NMR(CDCl3)δ 0.92(t,3H),1.08-1.91(m,26H),2.06(d,2H),2.24(d,2H),2.51(m,2H),3.30(s,3H),3.51(dd,2H),3.67(dd,2H),3.87(quin,4H),3.94(t,2H),4.17(t,2H),4.54(t,2H),5.82(dd,1H),6.12(dd,1H),6.40(dd,1H),6.86(m,3H),6.97(m,2H),7.16(m,2H),7.32(t,1H),7.65(d,1H),7.70(d,1H),7.82(d,1H),8.36(s,1H)ppm.
(実施例11)式(I-11)で表される化合物の製造
転移温度(昇温5℃/分):C 67-100 I
1H NMR(CDCl3)δ 1.00(t,3H),1.28(m,2H),1.45-1.81(m,12H),1.97(br,1H),2.13(m,2H),2.26(m,2H),2.57(tt,1H),2.65(t,2H),3.27(s,3H),3.37(m,2H),3.50(m,2H),3.70(t,2H),3.95(q,4H),4.17(t,2H),4.33(t,2H),5.82(dd,1H),6.12(dd,1H),6.40(dd,1H),6.87(d,2H),6.98(m,3H),7.15(t,1H),7.25(m,5H),7.32(t,1H),7.64(m,2H),7.69(d,1H),7.91(s,1H)ppm.
(実施例12)式(I-12)で表される化合物の製造
LCMS:1153[M+1]
(実施例13)式(I-13)で表される化合物の製造
LCMS:1088[M+1]
(実施例14)式(I-14)で表される化合物の製造
LCMS:1259[M+1]
(実施例15)式(I-15)で表される化合物の製造
LCMS:1222[M+1]
(実施例16)式(I-16)で表される化合物の製造
LCMS:1188[M+1]
(実施例17)式(I-17)で表される化合物の製造
1H NMR(CDCl3)δ 0.92(t,3H),1.05-1.83(m,32H),1.93(t,5H),2.33(m,4H),2.55(m,2H),2.71(m、1H),3.30(s,3H),3.62(m,2H),3.85(t,2H),3.94(t,2H),4.17(t,2H),4.48(t,2H),5.82(dd,1H),6.12(dd,1H),6.40(dd,1H),6.88(d,2H),6.99(m,3H),7.17(t,1H),7.23(dd,1H),7.34(t,1H),7.66(d,1H),7.71(d,1H),7.89(d,1H),8.02(s,1H)ppm.
LCMS:978[M+1]
実施例1から実施例17と同様の方法及び公知の方法を用いて、上述の式(I-18)から式(I-99)で表される化合物を製造した。
(実施例18~34、比較例1~3)
実施例1から実施例17記載の式(I-1)から式(I-17)で表される化合物及び特許文献1記載の化合物(R-1)、特許文献2記載の化合物(R-2)、特許文献3記載の化合物(R-3)を評価対象の化合物とした。
(実施例35~51、比較例4~6)
配向膜用ポリイミド溶液をシクロオレフィンポリマー基材にスピンコート法を用いて塗布し、60℃で10分乾燥した後、100℃で60分焼成することにより塗膜を得た。得られた塗膜をラビング処理した。ラビング処理は、市販のラビング装置を用いて行った。
分類0:いずれの基盤目にもはがれがない。
分類1:カットの交差点における塗膜の小さなはがれが確認される(5%未満)。
分類2:塗膜がカットの線に沿って、交差点においてはがれている(5%以上15%未満)。
分類3:塗膜がカットの線に沿って部分的、全面的にはがれている(15%以上35%未満)。
分類4:塗膜がカットの線に沿って部分的、全面的に大きくはがれを生じている(35%以上65%未満)。
分類5:分類4以上(65%以上)。
Claims (6)
- 一般式(I)
R2は水素原子、フッ素原子、塩素原子、若しくは、炭素原子数1から12の直鎖アルキル基又は直鎖アルコキシ基を表し、
A1及びA2は式(A-1)から式(A-4)
Z1及びZ2は各々独立して-OCH2-、-CH2O-、-COO-、-OCO-又は単結合を表すが、Z1が複数存在する場合それらは同一であっても異なっていても良く、Z2が複数存在する場合それらは同一であっても異なっていても良く、
G1は下記の一般式(M-7)又は一般式(M-8)
W2は水素原子、若しくは、炭素原子数1から20の直鎖状又は分岐状アルキル基を表し、
Yは水素原子を表し、
m1は1又は2の整数を表し、m2は1の整数を表す。)で表される重合性低波長分散性又は重合性逆波長分散性化合物。 - 請求項1に記載の化合物を含有する組成物。
- 請求項1に記載の化合物を含有する液晶組成物。
- 請求項2又は請求項3に記載の組成物を用いた重合体。
- 請求項4記載の重合体を用いた光学異方体。
- 請求項1に記載の化合物を用いた樹脂、樹脂添加剤、オイル、フィルター、接着剤、粘着剤、油脂、インキ、医薬品、化粧品、洗剤、建築材料、包装材、液晶材料、有機EL材料、有機半導体材料、電子材料、表示素子、電子デバイス、通信機器、自動車部品、航空機部品、機械部品、農薬及び食品並びにそれらを使用した製品。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015239359 | 2015-12-08 | ||
JP2015239359 | 2015-12-08 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017549348A Division JP6624696B2 (ja) | 2015-12-08 | 2016-12-01 | 重合性化合物及び光学異方体 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2018154658A JP2018154658A (ja) | 2018-10-04 |
JP7067302B2 true JP7067302B2 (ja) | 2022-05-16 |
Family
ID=59014099
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017549348A Active JP6624696B2 (ja) | 2015-12-08 | 2016-12-01 | 重合性化合物及び光学異方体 |
JP2018116098A Active JP7067302B2 (ja) | 2015-12-08 | 2018-06-19 | 重合性化合物及び光学異方体 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017549348A Active JP6624696B2 (ja) | 2015-12-08 | 2016-12-01 | 重合性化合物及び光学異方体 |
Country Status (5)
Country | Link |
---|---|
US (1) | US11046889B2 (ja) |
JP (2) | JP6624696B2 (ja) |
KR (1) | KR102614432B1 (ja) |
CN (1) | CN108368070B (ja) |
WO (1) | WO2017098988A1 (ja) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017098988A1 (ja) * | 2015-12-08 | 2017-06-15 | Dic株式会社 | 重合性化合物及び光学異方体 |
WO2018096938A1 (ja) * | 2016-11-22 | 2018-05-31 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、光学フィルム、光学異方体、偏光板、フラットパネル表示装置、有機エレクトロルミネッセンス表示装置、反射防止フィルム、および化合物 |
JP7270603B2 (ja) * | 2017-08-15 | 2023-05-10 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 重合性lc媒体およびフラット光学分散を有するポリマーフィルム |
JP6949124B2 (ja) * | 2017-08-30 | 2021-10-13 | 富士フイルム株式会社 | 硬化物、光学部材、レンズ、化合物、及び硬化性組成物 |
JP6675596B2 (ja) * | 2017-12-22 | 2020-04-01 | Dic株式会社 | 重合性液晶組成物、光学異方体及びその製造方法 |
WO2019131572A1 (ja) | 2017-12-26 | 2019-07-04 | 富士フイルム株式会社 | レンズ用接着剤、接合レンズ、および撮像モジュール |
JP6910527B2 (ja) * | 2018-02-14 | 2021-07-28 | 富士フイルム株式会社 | 重合性液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置 |
JP6913226B2 (ja) * | 2018-02-14 | 2021-08-04 | 富士フイルム株式会社 | 重合性液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置 |
KR102426523B1 (ko) * | 2018-02-14 | 2022-07-27 | 후지필름 가부시키가이샤 | 중합성 액정 조성물, 광학 이방성막, 광학 필름, 편광판 및 화상 표시 장치 |
CN111989317B (zh) * | 2018-04-27 | 2023-12-01 | 日本瑞翁株式会社 | 聚合性液晶化合物、聚合性液晶组合物、高分子、光学膜、光学各向异性体以及偏振片 |
KR102195455B1 (ko) | 2018-05-03 | 2020-12-28 | 주식회사 엘지화학 | 중합성 액정 화합물, 광학 소자용 액정 조성물, 중합체, 광학 이방체 및 디스플레이 장치용 광학 소자 |
WO2020022429A1 (ja) * | 2018-07-25 | 2020-01-30 | 富士フイルム株式会社 | 液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置 |
TW202035380A (zh) * | 2018-12-11 | 2020-10-01 | 日商Dic股份有限公司 | 液晶組成物及顯示元件、以及化合物 |
JP7214828B2 (ja) * | 2019-02-22 | 2023-01-30 | 富士フイルム株式会社 | 樹脂組成物、硬化物、回折光学素子、多層型回折光学素子 |
CN112480027B (zh) * | 2019-09-12 | 2023-08-29 | 石家庄诚志永华显示材料有限公司 | 聚合性化合物、聚合性组合物、聚合物、光学各向异性体、液晶显示器件 |
JP7274040B2 (ja) * | 2020-02-28 | 2023-05-15 | 富士フイルム株式会社 | 硬化物、硬化性樹脂組成物、光学部材、レンズ、回折光学素子及び多層型回折光学素子、並びに、化合物 |
CN113861128B (zh) * | 2021-10-28 | 2023-08-01 | 江苏创拓新材料有限公司 | 可聚合化合物及光学各向异性体 |
CN114560828B (zh) * | 2022-03-25 | 2024-01-26 | 江苏创拓新材料有限公司 | 可聚合化合物及其形成的光学各向异性体 |
CN114805328B (zh) * | 2022-04-29 | 2023-08-08 | 石家庄诚志永华显示材料有限公司 | 聚合性化合物、聚合性组合物、聚合物、光学各向异性体、液晶显示器件 |
Citations (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005289980A (ja) | 2004-03-08 | 2005-10-20 | Fuji Photo Film Co Ltd | 液晶化合物、液晶組成物、重合体、位相差板、及び楕円偏光板 |
JP2008127336A (ja) | 2006-11-21 | 2008-06-05 | Fujifilm Corp | 重合性液晶化合物並びにそれを用いた位相差フィルムおよび液晶表示装置 |
JP2008239567A (ja) | 2007-03-28 | 2008-10-09 | Dic Corp | 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 |
JP2008239873A (ja) | 2007-03-28 | 2008-10-09 | Dic Corp | 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 |
JP2008273925A (ja) | 2006-12-15 | 2008-11-13 | Fujifilm Corp | 光学フィルムおよび位相差板、並びに液晶化合物 |
JP2009179563A (ja) | 2008-01-29 | 2009-08-13 | Fujifilm Corp | 化合物、液晶組成物及び異方性材料 |
JP2009210688A (ja) | 2008-03-03 | 2009-09-17 | Fujifilm Corp | 着色硬化性組成物、カラーフィルタ、カラーフィルタの製造方法、及び液晶表示装置 |
JP2010159324A (ja) | 2009-01-06 | 2010-07-22 | Adeka Corp | 重合性液晶化合物を含有する重合性液晶組成物及び該重合性液晶組成物の重合物を含有する光学異方性膜 |
JP2011012199A (ja) | 2009-07-03 | 2011-01-20 | Chisso Corp | 重合性液晶化合物、組成物および重合体 |
JP2011195588A (ja) | 2005-03-15 | 2011-10-06 | Fujifilm Corp | 化合物、組成物、位相差板、楕円偏光板および液晶表示装置 |
JP2011213610A (ja) | 2010-03-31 | 2011-10-27 | Fujifilm Corp | 液晶性化合物、液晶性組成物、光吸収異方性膜、及び液晶表示装置 |
JP2011225520A (ja) | 2010-04-02 | 2011-11-10 | Jnc Corp | 重合性基を有する光学活性化合物ならびにその重合体 |
JP2012008525A (ja) | 2010-02-18 | 2012-01-12 | Sumitomo Chemical Co Ltd | 立体表示システム |
WO2014010325A1 (ja) | 2012-07-09 | 2014-01-16 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、光学異方体、及び重合性化合物の製造方法 |
JP2015110532A (ja) | 2013-12-06 | 2015-06-18 | Dic株式会社 | 重合性化合物及び光学異方体 |
JP2015110531A (ja) | 2013-12-06 | 2015-06-18 | Dic株式会社 | 重合性化合物及び光学異方体 |
JP2015151383A (ja) | 2014-02-18 | 2015-08-24 | Dic株式会社 | 重合性化合物及び光学異方体 |
JP2015200861A (ja) | 2013-09-11 | 2015-11-12 | 富士フイルム株式会社 | 光学異方性層とその製造方法、積層体とその製造方法、偏光板、液晶表示装置及び有機el表示装置 |
WO2017098988A1 (ja) | 2015-12-08 | 2017-06-15 | Dic株式会社 | 重合性化合物及び光学異方体 |
JP6217999B2 (ja) | 2014-10-09 | 2017-10-25 | Dic株式会社 | 重合性化合物及び光学異方体 |
Family Cites Families (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1218635B (de) | 1962-07-24 | 1966-06-08 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von wasserunloeslichen, Arylhydrazonreste enthaltenden Azofarbstoffen |
JPS6355543A (ja) | 1986-08-26 | 1988-03-10 | Konica Corp | 発汗現象及びスタチツクマ−ク発生を防止したハロゲン化銀写真感光材料 |
US5445854A (en) | 1993-11-29 | 1995-08-29 | The Dow Chemical Company | Nonlinear optical epoxy-containing compositions and crosslinked nonlinear optical polymeric composition therefrom |
WO2005112540A2 (en) | 2004-05-21 | 2005-12-01 | Merck Patent Gmbh | Liquid crystal compounds, liquid crystal medium and liquid crystal display |
US8431110B2 (en) | 2005-05-23 | 2013-04-30 | Hmi Medical Innovations, Llc. | Compounds and method of identifying, synthesizing, optimizing and profiling protein modulators |
KR20080090381A (ko) | 2005-08-29 | 2008-10-08 | 제라드 엠. 하우지 | 테라뮤틴 조절물질 |
JP5084293B2 (ja) | 2006-02-07 | 2012-11-28 | 富士フイルム株式会社 | 光学フィルムおよび位相差板、並びに液晶化合物 |
JP2007328053A (ja) | 2006-06-06 | 2007-12-20 | Dainippon Printing Co Ltd | 位相差フィルム、および、位相差フィルムの製造方法 |
EP2129742B1 (en) | 2007-03-30 | 2012-01-25 | Merck Patent GmbH | Birefingent layer with negative optical dispersion |
JP5504585B2 (ja) | 2007-06-29 | 2014-05-28 | 住友化学株式会社 | 重合性化合物および光学フィルム |
JP2009062508A (ja) | 2007-08-14 | 2009-03-26 | Fujifilm Corp | 液晶組成物、及び光学異方性膜 |
CN101279901B (zh) | 2007-12-25 | 2011-08-17 | 四川大学 | 和厚朴酚系列衍生物及其制备方法和用途 |
JP5463666B2 (ja) | 2007-12-28 | 2014-04-09 | 住友化学株式会社 | 化合物、光学フィルム及び光学フィルムの製造方法 |
JP2010100541A (ja) | 2008-10-21 | 2010-05-06 | Asahi Glass Co Ltd | アクリル酸誘導体化合物、液晶性組成物、高分子液晶、光学素子および光ヘッド装置 |
JP5899607B2 (ja) | 2009-03-16 | 2016-04-06 | 住友化学株式会社 | 化合物、光学フィルム及び光学フィルムの製造方法 |
JP5453956B2 (ja) | 2009-06-26 | 2014-03-26 | 住友化学株式会社 | 化合物、光学フィルム及び光学フィルムの製造方法 |
WO2011050896A1 (en) | 2009-10-30 | 2011-05-05 | Merck Patent Gmbh | Polymerisable lc material and polymer film with negative optical dispersion |
JP5703594B2 (ja) | 2010-05-26 | 2015-04-22 | 住友化学株式会社 | 化合物、光学フィルム及び光学フィルムの製造方法 |
JP2012077055A (ja) | 2010-10-06 | 2012-04-19 | Sumitomo Chemical Co Ltd | 化合物、光学フィルム及び光学フィルムの製造方法 |
WO2012141245A1 (ja) | 2011-04-15 | 2012-10-18 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、及び光学異方体 |
JP5979136B2 (ja) * | 2011-04-27 | 2016-08-24 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、及び光学異方体 |
US9029490B2 (en) | 2011-06-10 | 2015-05-12 | Zeon Corporation | Polymerizable compound, polymerizable composition, polymer, and optically anisotropic body |
EP2727904B1 (en) | 2011-06-24 | 2016-08-10 | Zeon Corporation | Polymerizable compounds, polymerizable composition, polymer, and optically anisotropic body |
JP5772529B2 (ja) * | 2011-11-15 | 2015-09-02 | コニカミノルタ株式会社 | 光学フィルム、偏光板および液晶表示装置 |
KR101363479B1 (ko) | 2012-04-20 | 2014-02-17 | 주식회사 엘지화학 | 중합성 액정 화합물, 중합성 액정 조성물 및 광학 이방체 |
KR102231711B1 (ko) | 2012-05-30 | 2021-03-23 | 제온 코포레이션 | 중합성 화합물, 중합성 조성물, 고분자, 및 광학 이방체 |
KR102128555B1 (ko) | 2012-10-19 | 2020-06-30 | 제온 코포레이션 | 중합성 화합물, 중합성 조성물, 고분자, 및 광학 이방체 |
JP6476862B2 (ja) | 2012-10-22 | 2019-03-06 | 日本ゼオン株式会社 | 位相差板、円偏光板、及び画像表示装置 |
WO2014065176A1 (ja) | 2012-10-23 | 2014-05-01 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、及び光学異方体 |
JP6428265B2 (ja) | 2012-10-30 | 2018-11-28 | 日本ゼオン株式会社 | 液晶組成物、位相差板、画像表示装置、および光学異方性層の波長分散制御方法 |
CN104995219B (zh) | 2013-02-15 | 2017-06-06 | 日本瑞翁株式会社 | 聚合性化合物、聚合性组合物、高分子、以及光学各向异性体 |
JP6270812B2 (ja) | 2013-02-28 | 2018-01-31 | 富士フイルム株式会社 | 位相差板、反射防止板、画像表示装置、および位相差板の製造方法 |
EP3037444A4 (en) | 2013-08-22 | 2017-05-24 | Zeon Corporation | Polymerizable compound, polymerizable composition, polymer, and optical anisotropic body |
CN105745233B (zh) | 2013-10-31 | 2018-06-12 | 日本瑞翁株式会社 | 聚合性化合物、聚合性组合物、高分子、及光学各向异性体 |
KR101910438B1 (ko) | 2013-12-25 | 2018-10-22 | 디아이씨 가부시끼가이샤 | 메소겐기를 함유하는 화합물, 그것을 사용한 혼합물, 조성물, 및, 광학 이방체 |
KR102273081B1 (ko) | 2014-02-12 | 2021-07-02 | 제온 코포레이션 | 중합성 화합물, 중합성 조성물, 고분자, 및 광학 이방체 |
JP6672796B2 (ja) | 2014-02-14 | 2020-03-25 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、及び光学異方体 |
JP6047604B2 (ja) | 2014-03-31 | 2016-12-21 | 富士フイルム株式会社 | 液晶化合物および光学フィルム、ならびに光学フィルムの製造方法 |
KR20150113886A (ko) * | 2014-03-31 | 2015-10-08 | 후지필름 가부시키가이샤 | 광학 필름, 편광판, 및 광학 필름의 제조 방법 |
JP6363566B2 (ja) * | 2014-10-21 | 2018-07-25 | 富士フイルム株式会社 | 光学異方性層とその製造方法、積層体、偏光板、表示装置、液晶化合物とその製造方法、カルボン酸化合物 |
WO2016088749A1 (ja) * | 2014-12-04 | 2016-06-09 | Dic株式会社 | 重合性化合物、組成物、重合体、光学異方体、液晶表示素子及び有機el素子 |
JP6531935B2 (ja) | 2014-12-17 | 2019-06-19 | Dic株式会社 | 重合性化合物及び光学異方体 |
KR102573091B1 (ko) * | 2014-12-25 | 2023-09-01 | 디아이씨 가부시끼가이샤 | 중합성 화합물 및 광학 이방체 |
WO2016114211A1 (ja) * | 2015-01-16 | 2016-07-21 | Dic株式会社 | 重合性化合物及び光学異方体 |
KR20170121174A (ko) * | 2015-02-24 | 2017-11-01 | 디아이씨 가부시끼가이샤 | 중합성 화합물 및 광학 이방체 |
CN108137486B (zh) | 2015-10-23 | 2019-08-13 | Dic株式会社 | 聚合性化合物和光学各向异性体 |
CN108349925B (zh) * | 2015-11-09 | 2022-08-16 | Dic株式会社 | 聚合性化合物和光学各向异性体 |
-
2016
- 2016-12-01 WO PCT/JP2016/085717 patent/WO2017098988A1/ja active Application Filing
- 2016-12-01 US US16/060,265 patent/US11046889B2/en active Active
- 2016-12-01 KR KR1020187016825A patent/KR102614432B1/ko active IP Right Grant
- 2016-12-01 JP JP2017549348A patent/JP6624696B2/ja active Active
- 2016-12-01 CN CN201680070778.7A patent/CN108368070B/zh active Active
-
2018
- 2018-06-19 JP JP2018116098A patent/JP7067302B2/ja active Active
Patent Citations (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005289980A (ja) | 2004-03-08 | 2005-10-20 | Fuji Photo Film Co Ltd | 液晶化合物、液晶組成物、重合体、位相差板、及び楕円偏光板 |
JP2011195588A (ja) | 2005-03-15 | 2011-10-06 | Fujifilm Corp | 化合物、組成物、位相差板、楕円偏光板および液晶表示装置 |
JP2008127336A (ja) | 2006-11-21 | 2008-06-05 | Fujifilm Corp | 重合性液晶化合物並びにそれを用いた位相差フィルムおよび液晶表示装置 |
JP2008273925A (ja) | 2006-12-15 | 2008-11-13 | Fujifilm Corp | 光学フィルムおよび位相差板、並びに液晶化合物 |
JP2008239567A (ja) | 2007-03-28 | 2008-10-09 | Dic Corp | 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 |
JP2008239873A (ja) | 2007-03-28 | 2008-10-09 | Dic Corp | 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 |
JP2009179563A (ja) | 2008-01-29 | 2009-08-13 | Fujifilm Corp | 化合物、液晶組成物及び異方性材料 |
JP2009210688A (ja) | 2008-03-03 | 2009-09-17 | Fujifilm Corp | 着色硬化性組成物、カラーフィルタ、カラーフィルタの製造方法、及び液晶表示装置 |
JP2010159324A (ja) | 2009-01-06 | 2010-07-22 | Adeka Corp | 重合性液晶化合物を含有する重合性液晶組成物及び該重合性液晶組成物の重合物を含有する光学異方性膜 |
JP2011012199A (ja) | 2009-07-03 | 2011-01-20 | Chisso Corp | 重合性液晶化合物、組成物および重合体 |
JP2012008525A (ja) | 2010-02-18 | 2012-01-12 | Sumitomo Chemical Co Ltd | 立体表示システム |
JP2011213610A (ja) | 2010-03-31 | 2011-10-27 | Fujifilm Corp | 液晶性化合物、液晶性組成物、光吸収異方性膜、及び液晶表示装置 |
JP2011225520A (ja) | 2010-04-02 | 2011-11-10 | Jnc Corp | 重合性基を有する光学活性化合物ならびにその重合体 |
WO2014010325A1 (ja) | 2012-07-09 | 2014-01-16 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、光学異方体、及び重合性化合物の製造方法 |
JP2015200861A (ja) | 2013-09-11 | 2015-11-12 | 富士フイルム株式会社 | 光学異方性層とその製造方法、積層体とその製造方法、偏光板、液晶表示装置及び有機el表示装置 |
JP2015110532A (ja) | 2013-12-06 | 2015-06-18 | Dic株式会社 | 重合性化合物及び光学異方体 |
JP2015110531A (ja) | 2013-12-06 | 2015-06-18 | Dic株式会社 | 重合性化合物及び光学異方体 |
JP2015151383A (ja) | 2014-02-18 | 2015-08-24 | Dic株式会社 | 重合性化合物及び光学異方体 |
JP6217999B2 (ja) | 2014-10-09 | 2017-10-25 | Dic株式会社 | 重合性化合物及び光学異方体 |
WO2017098988A1 (ja) | 2015-12-08 | 2017-06-15 | Dic株式会社 | 重合性化合物及び光学異方体 |
Also Published As
Publication number | Publication date |
---|---|
US20180362847A1 (en) | 2018-12-20 |
CN108368070A (zh) | 2018-08-03 |
JP2018154658A (ja) | 2018-10-04 |
KR20180090286A (ko) | 2018-08-10 |
JPWO2017098988A1 (ja) | 2018-01-25 |
WO2017098988A1 (ja) | 2017-06-15 |
CN108368070B (zh) | 2023-04-28 |
JP6624696B2 (ja) | 2019-12-25 |
US11046889B2 (en) | 2021-06-29 |
KR102614432B1 (ko) | 2023-12-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7067302B2 (ja) | 重合性化合物及び光学異方体 | |
JP6540849B2 (ja) | 重合性化合物及び光学異方体 | |
JP6164509B2 (ja) | 重合性化合物及び光学異方体 | |
KR102573091B1 (ko) | 중합성 화합물 및 광학 이방체 | |
JP5754078B2 (ja) | 化合物 | |
JP5510045B2 (ja) | 重合性化合物およびその重合体 | |
KR20170086047A (ko) | 중합성 화합물, 조성물, 중합체, 광학 이방체, 액정 표시 소자 및 유기 el 소자 | |
JP4576832B2 (ja) | 重合性化合物およびその重合体 | |
KR20170102242A (ko) | 중합성 화합물 및 광학 이방체 | |
JP6634692B2 (ja) | 重合性化合物及び光学異方体 | |
WO2017068860A1 (ja) | 重合性化合物及び光学異方体 | |
KR20170068529A (ko) | 중합성 화합물 및 광학 이방체 | |
JP6769131B2 (ja) | 重合性化合物及び光学異方体 | |
JP6529519B2 (ja) | 重合性化合物及び光学異方体 | |
JP2016017034A (ja) | 重合性化合物及び光学異方体 | |
JP2008239567A (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 | |
JP6418476B1 (ja) | 重合性化合物及び光学異方体 | |
JP2018035126A (ja) | 重合性化合物及び光学異方体 | |
JP2017218391A (ja) | 重合性化合物及び光学異方体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20190620 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20191018 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20200910 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200929 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20201110 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A132 Effective date: 20210427 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210622 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20211102 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20220127 |
|
C60 | Trial request (containing other claim documents, opposition documents) |
Free format text: JAPANESE INTERMEDIATE CODE: C60 Effective date: 20220127 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20220203 |
|
C21 | Notice of transfer of a case for reconsideration by examiners before appeal proceedings |
Free format text: JAPANESE INTERMEDIATE CODE: C21 Effective date: 20220208 |
|
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: 20220329 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20220411 |
|
R151 | Written notification of patent or utility model registration |
Ref document number: 7067302 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |
|
R154 | Certificate of patent or utility model (reissue) |
Free format text: JAPANESE INTERMEDIATE CODE: R154 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |