TWI734905B - 偶氮化合物或其鹽，以及含有此之染料系偏光膜、染料系偏光板及液晶顯示裝置 - Google Patents

偶氮化合物或其鹽，以及含有此之染料系偏光膜、染料系偏光板及液晶顯示裝置 Download PDF

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Publication number: TWI734905B
Authority: TW; Taiwan
Prior art keywords: group; azo compound; dye; patent application; salt
Prior art date: 2017-03-31

Application number

TW107111286A

Other languages

English (en)

Chinese (zh)

Other versions

TW201843245A (zh

Inventor

服部由侑

樋下田貴大

中村光則

Original Assignee

日商日本化藥股份有限公司

日商寶來技術有限公司

Priority date (The priority date 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 date listed.)

2017-03-31

Filing date

2018-03-30

Publication date

2021-08-01

2018-03-30 Application filed by 日商日本化藥股份有限公司, 日商寶來技術有限公司 filed Critical 日商日本化藥股份有限公司

2018-12-16 Publication of TW201843245A publication Critical patent/TW201843245A/zh

2021-08-01 Application granted granted Critical

2021-08-01 Publication of TWI734905B publication Critical patent/TWI734905B/zh

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-1 Azo compound Chemical class 0.000 title claims abstract description 142
150000003839 salts Chemical class 0.000 title claims abstract description 61
239000004973 liquid crystal related substance Substances 0.000 title claims description 53
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 100
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 48
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 37
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 34
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 33
125000001424 substituent group Chemical group 0.000 claims abstract description 32
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
125000001624 naphthyl group Chemical group 0.000 claims abstract description 17
125000004442 acylamino group Chemical group 0.000 claims abstract description 15
125000005843 halogen group Chemical group 0.000 claims abstract description 14
239000000975 dye Substances 0.000 claims description 126
230000007935 neutral effect Effects 0.000 claims description 50
239000000758 substrate Substances 0.000 claims description 26
239000004372 Polyvinyl alcohol Substances 0.000 claims description 23
229920002451 polyvinyl alcohol Polymers 0.000 claims description 23
125000003277 amino group Chemical group 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
239000011241 protective layer Substances 0.000 claims description 7
229920005989 resin Polymers 0.000 claims description 7
239000011347 resin Substances 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000006309 butyl amino group Chemical group 0.000 claims description 2
ZXDZVVSOWQEMOD-UHFFFAOYSA-N nitric hydrazide Chemical group NN[N+]([O-])=O ZXDZVVSOWQEMOD-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 85
238000002834 transmittance Methods 0.000 description 58
239000007864 aqueous solution Substances 0.000 description 54
230000010287 polarization Effects 0.000 description 52
229920002284 Cellulose triacetate Polymers 0.000 description 50
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 50
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 44
0 CC1C=C(*C(Nc(ccc(NNc2ccc(cc(*)cc3*)c3c2)c2)c2OC)=O)C(OCCC*)=C[C@@]1N=Nc(cc1)c(C)cc1NNc(cc1)cc2c1cc(*)cc2* Chemical compound CC1C=C(*C(Nc(ccc(NNc2ccc(cc(*)cc3*)c3c2)c2)c2OC)=O)C(OCCC*)=C[C@@]1N=Nc(cc1)c(C)cc1NNc(cc1)cc2c1cc(*)cc2* 0.000 description 37
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
238000010521 absorption reaction Methods 0.000 description 36
239000000853 adhesive Substances 0.000 description 36
230000001070 adhesive effect Effects 0.000 description 36
238000003756 stirring Methods 0.000 description 35
125000003545 alkoxy group Chemical group 0.000 description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
239000010410 layer Substances 0.000 description 28
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 26
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
230000015572 biosynthetic process Effects 0.000 description 22
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 22
238000003786 synthesis reaction Methods 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
238000000034 method Methods 0.000 description 21
238000004519 manufacturing process Methods 0.000 description 18
VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 16
238000005859 coupling reaction Methods 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
238000006193 diazotization reaction Methods 0.000 description 14
239000010446 mirabilite Substances 0.000 description 14
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 14
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 14
UFUQRRYHIHJMPB-DUCFOALUSA-L Sirius red 4B Chemical compound [Na+].[Na+].OS(=O)(=O)c1cc2cc(NC(=O)c3ccccc3)ccc2c([O-])c1\N=N\c1ccc(cc1)\N=N\c1ccc(cc1)S([O-])(=O)=O UFUQRRYHIHJMPB-DUCFOALUSA-L 0.000 description 13
125000000217 alkyl group Chemical group 0.000 description 13
238000004043 dyeing Methods 0.000 description 13
235000010288 sodium nitrite Nutrition 0.000 description 13
235000010724 Wisteria floribunda Nutrition 0.000 description 12
210000002858 crystal cell Anatomy 0.000 description 12
229920006254 polymer film Polymers 0.000 description 12
229910000029 sodium carbonate Inorganic materials 0.000 description 12
XPVVBMXZTSOIQD-UHFFFAOYSA-N 3-(2-amino-4-methylphenoxy)propane-1-sulfonic acid Chemical compound CC1=CC=C(OCCCS(O)(=O)=O)C(N)=C1 XPVVBMXZTSOIQD-UHFFFAOYSA-N 0.000 description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 9
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 9
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 8
238000001914 filtration Methods 0.000 description 8
229910052740 iodine Inorganic materials 0.000 description 8
239000011630 iodine Substances 0.000 description 8
239000002253 acid Substances 0.000 description 7
230000001681 protective effect Effects 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 6
150000001448 anilines Chemical class 0.000 description 6
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
239000004327 boric acid Substances 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 5
IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
150000005002 naphthylamines Chemical class 0.000 description 5
WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 5
238000005185 salting out Methods 0.000 description 5
NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 4
MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 4
NTFVRNCDLGFPFA-UHFFFAOYSA-N 3-(2-aminophenoxy)propane-1-sulfonic acid Chemical compound NC1=CC=CC=C1OCCCS(O)(=O)=O NTFVRNCDLGFPFA-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
150000004982 aromatic amines Chemical class 0.000 description 4
239000004202 carbamide Substances 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
239000012954 diazonium Substances 0.000 description 4
238000002845 discoloration Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 4
238000011282 treatment Methods 0.000 description 4
ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 3
GVCFFVPEOLCYNN-UHFFFAOYSA-N 5-amino-2-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C(C(O)=O)=C1 GVCFFVPEOLCYNN-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229960004050 aminobenzoic acid Drugs 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
238000000576 coating method Methods 0.000 description 3
239000003086 colorant Substances 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000006731 degradation reaction Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
RYWGPCLTVXMMHO-UHFFFAOYSA-N (4-chlorophenyl) carbonochloridate Chemical compound ClC(=O)OC1=CC=C(Cl)C=C1 RYWGPCLTVXMMHO-UHFFFAOYSA-N 0.000 description 2
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 2
JBKKUOHYDLSZSS-UHFFFAOYSA-N 3-(2-amino-4-chlorophenoxy)propane-1-sulfonic acid Chemical compound NC1=CC(Cl)=CC=C1OCCCS(O)(=O)=O JBKKUOHYDLSZSS-UHFFFAOYSA-N 0.000 description 2
QJRKEOVWSVLHPM-UHFFFAOYSA-N 3-(3-aminophenoxy)propane-1-sulfonic acid Chemical compound NC1=CC=CC(OCCCS(O)(=O)=O)=C1 QJRKEOVWSVLHPM-UHFFFAOYSA-N 0.000 description 2
MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 2
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
NPNQZOLAVNJYIJ-UHFFFAOYSA-N 4-(3-aminophenoxy)butane-1-sulfonic acid Chemical compound NC1=CC=CC(OCCCCS(O)(=O)=O)=C1 NPNQZOLAVNJYIJ-UHFFFAOYSA-N 0.000 description 2
STOOUUMSJPLRNI-UHFFFAOYSA-N 5-amino-4-hydroxy-3-[[4-[4-[(4-hydroxyphenyl)diazenyl]phenyl]phenyl]diazenyl]-6-[(4-nitrophenyl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=C(N=NC=3C=CC(=CC=3)C=3C=CC(=CC=3)N=NC=3C=CC(O)=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 STOOUUMSJPLRNI-UHFFFAOYSA-N 0.000 description 2
KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 2
SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-UHFFFAOYSA-N 0.000 description 2
CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000010306 acid treatment Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001412 amines Chemical group 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 2
PBOIUUROGJVVNC-UHFFFAOYSA-L disodium 2-hydroxy-5-[[4-[[2-methoxy-4-[(3-sulfonatophenyl)diazenyl]phenyl]carbamoylamino]phenyl]diazenyl]benzoate Chemical compound [Na+].[Na+].COc1cc(ccc1NC(=O)Nc1ccc(cc1)N=Nc1ccc(O)c(c1)C([O-])=O)N=Nc1cccc(c1)S([O-])(=O)=O PBOIUUROGJVVNC-UHFFFAOYSA-L 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
239000002994 raw material Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
IKMNJYGTSSQNSE-UHFFFAOYSA-N (4-bromophenyl) carbonochloridate Chemical compound ClC(=O)OC1=CC=C(Br)C=C1 IKMNJYGTSSQNSE-UHFFFAOYSA-N 0.000 description 1
ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 1
HEAHMJLHQCESBZ-UHFFFAOYSA-N 2,5-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(N)C(S(O)(=O)=O)=C1 HEAHMJLHQCESBZ-UHFFFAOYSA-N 0.000 description 1
VBUBGTCJRMYYRA-UHFFFAOYSA-N 2,5-diethylaniline Chemical compound CCC1=CC=C(CC)C(N)=C1 VBUBGTCJRMYYRA-UHFFFAOYSA-N 0.000 description 1
NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
KYIFCPDQDOQKDD-UHFFFAOYSA-N 2-(2-amino-4-chlorophenoxy)ethanesulfonic acid Chemical compound S(=O)(=O)(O)CCOC1=C(N)C=C(C=C1)Cl KYIFCPDQDOQKDD-UHFFFAOYSA-N 0.000 description 1
VVCSWHXHCRYMEQ-UHFFFAOYSA-N 2-(2-amino-4-ethoxyphenoxy)ethanesulfonic acid Chemical compound NC1=C(OCCS(=O)(=O)O)C=CC(=C1)OCC VVCSWHXHCRYMEQ-UHFFFAOYSA-N 0.000 description 1
YTNUVZMZHFDHPB-UHFFFAOYSA-N 2-(2-amino-4-fluorophenoxy)ethanesulfonic acid Chemical compound NC1=C(OCCS(=O)(=O)O)C=CC(=C1)F YTNUVZMZHFDHPB-UHFFFAOYSA-N 0.000 description 1
VWBJCPJHSNFOQW-UHFFFAOYSA-N 2-(2-amino-4-methoxyphenoxy)ethanesulfonic acid Chemical compound NC1=C(OCCS(=O)(=O)O)C=CC(=C1)OC VWBJCPJHSNFOQW-UHFFFAOYSA-N 0.000 description 1
KYYPTYMKGTUKGI-UHFFFAOYSA-N 2-(2-amino-4-methylphenoxy)ethanesulfonic acid Chemical compound CC1=CC=C(OCCS(O)(=O)=O)C(N)=C1 KYYPTYMKGTUKGI-UHFFFAOYSA-N 0.000 description 1
BUUCBTMQOJUSCQ-UHFFFAOYSA-N 2-(2-aminophenoxy)ethanesulfonic acid Chemical compound NC1=CC=CC=C1OCCS(O)(=O)=O BUUCBTMQOJUSCQ-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
DAVJYXOEESAIOI-UHFFFAOYSA-N 2-(3-amino-4-ethoxyphenoxy)ethanesulfonic acid Chemical compound NC=1C=C(OCCS(=O)(=O)O)C=CC=1OCC DAVJYXOEESAIOI-UHFFFAOYSA-N 0.000 description 1
RIWWMQHVFYAGGZ-UHFFFAOYSA-N 2-(3-amino-4-methoxyphenoxy)ethanesulfonic acid Chemical compound NC=1C=C(OCCS(=O)(=O)O)C=CC=1OC RIWWMQHVFYAGGZ-UHFFFAOYSA-N 0.000 description 1
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150000001989 diazonium salts Chemical class 0.000 description 1
125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
OYUZMQYZGSMPII-UHFFFAOYSA-L disodium 4-hydroxy-7-[(5-hydroxy-6-phenyldiazenyl-7-sulfonatonaphthalen-2-yl)amino]-3-phenyldiazenylnaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Oc1c(N=Nc2ccccc2)c(cc2cc(Nc3ccc4c(O)c(N=Nc5ccccc5)c(cc4c3)S([O-])(=O)=O)ccc12)S([O-])(=O)=O OYUZMQYZGSMPII-UHFFFAOYSA-L 0.000 description 1
DSARWKALPGYFTA-UHFFFAOYSA-L disodium 4-hydroxy-7-[(5-hydroxy-6-phenyldiazenyl-7-sulfonatonaphthalen-2-yl)carbamoylamino]-3-phenyldiazenylnaphthalene-2-sulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(NC(=O)NC=3C=C4C=C(C(N=NC=5C=CC=CC=5)=C(O)C4=CC=3)S([O-])(=O)=O)=CC=C2C(O)=C1N=NC1=CC=CC=C1 DSARWKALPGYFTA-UHFFFAOYSA-L 0.000 description 1
SUXCALIDMIIJCK-UHFFFAOYSA-L disodium;4-amino-3-[[4-[4-[(1-amino-4-sulfonatonaphthalen-2-yl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(N=NC3=CC=C(C=C3C)C=3C=C(C(=CC=3)N=NC=3C(=C4C=CC=CC4=C(C=3)S([O-])(=O)=O)N)C)=CC(S([O-])(=O)=O)=C21 SUXCALIDMIIJCK-UHFFFAOYSA-L 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
ORUJFMPWKPVXLZ-UHFFFAOYSA-N guaiacol carbonate Chemical compound COC1=CC=CC=C1OC(=O)OC1=CC=CC=C1OC ORUJFMPWKPVXLZ-UHFFFAOYSA-N 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000010030 laminating Methods 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
230000007774 longterm Effects 0.000 description 1
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000003607 modifier Substances 0.000 description 1
SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 description 1
125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002120 nanofilm Substances 0.000 description 1
FKORGLNGEASTQE-UHFFFAOYSA-N naphthalene-1,3-disulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC(S(O)(=O)=O)=C21 FKORGLNGEASTQE-UHFFFAOYSA-N 0.000 description 1
NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical group N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
230000035699 permeability Effects 0.000 description 1
229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
229920006122 polyamide resin Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
239000011112 polyethylene naphthalate Substances 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920005672 polyolefin resin Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
238000012805 post-processing Methods 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000010453 quartz Substances 0.000 description 1
238000007670 refining Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
239000010980 sapphire Substances 0.000 description 1
229910052594 sapphire Inorganic materials 0.000 description 1
238000007789 sealing Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000005361 soda-lime glass Substances 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
FIXVWFINKCQNFG-UHFFFAOYSA-M sodium;4-[(4-aminophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FIXVWFINKCQNFG-UHFFFAOYSA-M 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000011029 spinel Substances 0.000 description 1
229910052596 spinel Inorganic materials 0.000 description 1
238000004544 sputter deposition Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000012360 testing method Methods 0.000 description 1
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
WNQPPENQFWLADQ-UHFFFAOYSA-J tetrasodium;4-hydroxy-5-[[4-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]carbamoylamino]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(O)=C2C(N=NC3=C(C)C=C(C(=C3)OC)NC(=O)NC3=CC(C)=C(N=NC=4C5=C(O)C=C(C=C5C=C(C=4)S([O-])(=O)=O)S([O-])(=O)=O)C=C3OC)=CC(S([O-])(=O)=O)=CC2=C1 WNQPPENQFWLADQ-UHFFFAOYSA-J 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
238000007740 vapor deposition Methods 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
239000001043 yellow dye Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- 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

Landscapes

Physics & Mathematics (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Nonlinear Science (AREA)
Mathematical Physics (AREA)
Crystallography & Structural Chemistry (AREA)
Polarising Elements (AREA)
Liquid Crystal (AREA)

TW107111286A 2017-03-31 2018-03-30 偶氮化合物或其鹽，以及含有此之染料系偏光膜、染料系偏光板及液晶顯示裝置 TWI734905B (zh)

Applications Claiming Priority (6)

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JP2017069709		2017-03-31
JP2017069711		2017-03-31
JP2017-069710		2017-03-31
JP2017069710		2017-03-31
JP2017-069709		2017-03-31
JP2017-069711		2017-03-31

Publications (2)

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TW201843245A TW201843245A (zh)	2018-12-16
TWI734905B true TWI734905B (zh)	2021-08-01

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JP (1)	JP7035018B2 (ja)
KR (1)	KR20190134615A (ja)
CN (1)	CN110249008B (ja)
TW (1)	TWI734905B (ja)
WO (1)	WO2018181470A1 (ja)

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TWI859278B (zh) *	2019-07-22	2024-10-21	日商日本化藥股份有限公司	偶氮化合物，及含有該偶氮化合物之偏光膜，以及偏光板
WO2021153374A1 (ja) *	2020-01-29	2021-08-05	日本化薬株式会社	アゾ化合物又はその塩、並びにこれを含有する染料系偏光膜、染料系偏光板、及び表示装置

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- 2018-03-28 KR KR1020197027526A patent/KR20190134615A/ko not_active Withdrawn
- 2018-03-28 WO PCT/JP2018/012737 patent/WO2018181470A1/ja not_active Ceased
- 2018-03-28 CN CN201880009570.3A patent/CN110249008B/zh active Active
- 2018-03-28 JP JP2019509971A patent/JP7035018B2/ja active Active
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WO2018181470A1 (ja)	2018-10-04
CN110249008B (zh)	2021-06-11
KR20190134615A (ko)	2019-12-04
JPWO2018181470A1 (ja)	2020-02-06
TW201843245A (zh)	2018-12-16
CN110249008A (zh)	2019-09-17
JP7035018B2 (ja)	2022-03-14

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RU2421488C2 (ru)	2011-06-20	Азосоединение и его соль и содержащая краситель поляризационная пленка, включающая данное соединение или его соль
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JP7230079B2 (ja)	2023-02-28	アゾ化合物又はその塩及びこれを含有する偏光膜
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KR20110018362A (ko)	2011-02-23	아조 화합물 및 그 염, 및 그것들을 함유하는 염료계 편광막 및 편광판
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JPWO2016186194A1 (ja)	2018-03-08	アゾ化合物及びそれらを含有する染料系偏光膜並びに偏光板
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JP2023119333A (ja)	2023-08-28	水溶性ナフタルイミド系化合物又はその塩を含有する偏光膜、偏光発光膜、偏光発光板及び表示装置
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