KR20180006926A - 아조 화합물 및 그것들을 함유하는 염료계 편광막 그리고 편광판 - Google Patents

아조 화합물 및 그것들을 함유하는 염료계 편광막 그리고 편광판 Download PDF

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Publication number: KR20180006926A
Authority: KR; South Korea
Prior art keywords: group; carbon atoms; dye; polarizing plate; alkoxy group
Prior art date: 2015-05-20
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

KR1020177033441A

Other languages

English (en)

Korean (ko)

Inventor

다카히로 히게타

유 핫토리

미츠노리 나카무라

다쿠토 니시구치

Original Assignee

닛뽄 가야쿠 가부시키가이샤

가부시키가이샤 폴라테크노

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.)

2015-05-20

Filing date

2016-05-20

Publication date

2018-01-19

2016-05-20 Application filed by 닛뽄 가야쿠 가부시키가이샤, 가부시키가이샤 폴라테크노 filed Critical 닛뽄 가야쿠 가부시키가이샤

2018-01-19 Publication of KR20180006926A publication Critical patent/KR20180006926A/ko

Status Withdrawn legal-status Critical Current

Links

-1 azo compound Chemical class 0.000 claims abstract description 78
125000003545 alkoxy group Chemical group 0.000 claims abstract description 50
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 49
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 45
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 30
230000007935 neutral effect Effects 0.000 claims abstract description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
125000001624 naphthyl group Chemical group 0.000 claims abstract description 8
239000004973 liquid crystal related substance Substances 0.000 claims description 42
150000003839 salts Chemical class 0.000 claims description 39
239000000758 substrate Substances 0.000 claims description 25
238000000034 method Methods 0.000 claims description 24
239000000126 substance Substances 0.000 claims description 20
239000004372 Polyvinyl alcohol Substances 0.000 claims description 15
229920002451 polyvinyl alcohol Polymers 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
239000011241 protective layer Substances 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
229920005989 resin Polymers 0.000 claims description 3
239000011347 resin Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims 2
239000000975 dye Substances 0.000 description 70
150000001875 compounds Chemical class 0.000 description 53
230000010287 polarization Effects 0.000 description 42
238000010521 absorption reaction Methods 0.000 description 36
238000002834 transmittance Methods 0.000 description 34
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 19
VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 18
239000007864 aqueous solution Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
125000001424 substituent group Chemical group 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000000853 adhesive Substances 0.000 description 14
230000001070 adhesive effect Effects 0.000 description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 13
229920006254 polymer film Polymers 0.000 description 12
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
238000005859 coupling reaction Methods 0.000 description 11
210000002858 crystal cell Anatomy 0.000 description 11
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 10
239000010410 layer Substances 0.000 description 10
230000008878 coupling Effects 0.000 description 9
238000010168 coupling process Methods 0.000 description 9
229920002284 Cellulose triacetate Polymers 0.000 description 8
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 8
239000002253 acid Substances 0.000 description 8
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 8
239000004327 boric acid Substances 0.000 description 8
238000004043 dyeing Methods 0.000 description 8
230000001681 protective effect Effects 0.000 description 8
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
239000011630 iodine Substances 0.000 description 7
229910052740 iodine Inorganic materials 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
150000001448 anilines Chemical class 0.000 description 6
239000000463 material Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
235000010288 sodium nitrite Nutrition 0.000 description 6
238000003756 stirring Methods 0.000 description 6
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 5
238000006243 chemical reaction Methods 0.000 description 5
239000003086 colorant Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 5
238000005185 salting out Methods 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
238000006193 diazotization reaction Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000011521 glass Substances 0.000 description 4
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 4
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 3
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
235000010724 Wisteria floribunda Nutrition 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000002845 discoloration Methods 0.000 description 3
239000012528 membrane Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
BRWJTSYXNZYZRH-UHFFFAOYSA-N 2-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=C(S(O)(=O)=O)C=C21 BRWJTSYXNZYZRH-UHFFFAOYSA-N 0.000 description 2
MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
150000007945 N-acyl ureas Chemical class 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
150000003863 ammonium salts Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
230000006866 deterioration Effects 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
238000005259 measurement Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
150000005002 naphthylamines Chemical class 0.000 description 2
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000004417 polycarbonate Substances 0.000 description 2
150000004291 polyenes Chemical class 0.000 description 2
KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
OFHQVNFSKOBBGG-UHFFFAOYSA-N 1,2-difluoropropane Chemical compound CC(F)CF OFHQVNFSKOBBGG-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
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-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
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
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UFOQIJCVCSQKAL-UHFFFAOYSA-N 2-(3-aminophenoxy)butane-1-sulfonic acid Chemical compound NC=1C=C(OC(CS(=O)(=O)O)CC)C=CC=1 UFOQIJCVCSQKAL-UHFFFAOYSA-N 0.000 description 1
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AXXYMKMFXNCXGM-UHFFFAOYSA-N 2-propoxyaniline Chemical compound CCCOC1=CC=CC=C1N AXXYMKMFXNCXGM-UHFFFAOYSA-N 0.000 description 1
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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 1
ZIZHOYOBASUITD-UHFFFAOYSA-N 3-butoxyaniline Chemical compound CCCCOC1=CC=CC(N)=C1 ZIZHOYOBASUITD-UHFFFAOYSA-N 0.000 description 1
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239000003522 acrylic cement Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
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125000003277 amino group Chemical group 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
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239000001045 blue dye Substances 0.000 description 1
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238000006297 dehydration reaction Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 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
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
VILFVXYKHXVYAB-UHFFFAOYSA-N naphthalene-2,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 VILFVXYKHXVYAB-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-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
WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
230000035699 permeability Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin 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
229920000642 polymer 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
238000001556 precipitation Methods 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000010453 quartz Substances 0.000 description 1
WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
239000001044 red dye Substances 0.000 description 1
239000010980 sapphire Substances 0.000 description 1
229910052594 sapphire Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 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
125000001174 sulfone group Chemical group 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000010998 test method Methods 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
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
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
238000007740 vapor deposition Methods 0.000 description 1
239000001043 yellow dye Substances 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
- 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
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
- 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)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Chemical & Material Sciences (AREA)
Nonlinear Science (AREA)
Organic Chemistry (AREA)
Mathematical Physics (AREA)
Crystallography & Structural Chemistry (AREA)
Polarising Elements (AREA)
Liquid Crystal (AREA)

KR1020177033441A 2015-05-20 2016-05-20 아조 화합물 및 그것들을 함유하는 염료계 편광막 그리고 편광판 Withdrawn KR20180006926A (ko)

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JPJP-P-2015-102405		2015-05-20
JP2015102403		2015-05-20
JP2015102404		2015-05-20
JPJP-P-2015-102403		2015-05-20
JPJP-P-2015-102404		2015-05-20
JP2015102405		2015-05-20
PCT/JP2016/064988 WO2016186196A1 (ja)	2015-05-20	2016-05-20	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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KR20180006926A true KR20180006926A (ko)	2018-01-19

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JP (1)	JP6736549B2 (ja)
KR (1)	KR20180006926A (ja)
CN (1)	CN107614623B (ja)
TW (1)	TWI715585B (ja)
WO (1)	WO2016186196A1 (ja)

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KR20190134615A (ko) *	2017-03-31	2019-12-04	닛뽄 가야쿠 가부시키가이샤	아조 화합물 또는 그 염, 그리고 이것을 함유하는 염료계 편광막, 염료계 편광판, 및 액정 표시 장치
CN110945394B (zh)	2017-08-31	2023-06-27	三菱化学株式会社	偏光板、液晶显示装置和其制造方法、以及聚乙烯醇系偏光膜
KR20210057027A (ko) *	2018-09-05	2021-05-20	닛뽄 가야쿠 가부시키가이샤	편광 소자 그리고 그것을 사용한 편광판 및 광학 부재 등

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US2519651A (en) *	1945-07-26	1950-08-22	Ciba Ltd	Polyazo dyestuffs
JP4078476B2 (ja) *	1999-12-24	2008-04-23	住友化学株式会社	アゾ化合物又はその塩及びそれらを含有する染料系偏光膜
TW555812B (en) *	1999-12-24	2003-10-01	Sumitomo Chemical Co	Azo-compounds and dye polarizing films containing them
WO2004013232A1 (ja) *	2002-08-05	2004-02-12	Nippon Kayaku Kabushiki Kaisha	トリスアゾ化合物、水性インク組成物および着色体
JP5204944B2 (ja) *	2004-06-07	2013-06-05	富士フイルム株式会社	黒インク組成物、およびインクジェット記録方法。
JP4736424B2 (ja) *	2004-12-27	2011-07-27	住友化学株式会社	アゾ化合物又はその塩、及び該化合物又はその塩を含有する偏光膜
WO2007023733A1 (ja) *	2005-08-22	2007-03-01	Sumitomo Chemical Company, Limited	アゾ化合物及び該化合物を含有する偏光膜
JP5017961B2 (ja) *	2005-08-22	2012-09-05	住友化学株式会社	アゾ化合物及び該化合物を含有する偏光膜
JP2009132794A (ja) *	2007-11-30	2009-06-18	Nippon Kayaku Co Ltd	アゾ化合物、インク組成物、記録方法及び着色体
JP2009155364A (ja) *	2007-12-25	2009-07-16	Sumitomo Chemical Co Ltd	アゾ化合物及び該アゾ化合物を含有する偏光膜
EP2554606B1 (en) *	2010-03-30	2014-04-23	Nippon Kayaku Kabushiki Kaisha	Water-soluble azo compound or salt thereof, ink composition and colored body
JP2014148592A (ja) *	2013-01-31	2014-08-21	Ricoh Co Ltd	インクジェットインクセット、画像形成方法、画像形成装置
WO2016021730A1 (ja) *	2014-08-08	2016-02-11	日本化薬株式会社	水溶性アゾ化合物又はその塩、インク組成物及び着色体

2016
- 2016-05-20 TW TW105115805A patent/TWI715585B/zh active
- 2016-05-20 WO PCT/JP2016/064988 patent/WO2016186196A1/ja not_active Ceased
- 2016-05-20 JP JP2017519413A patent/JP6736549B2/ja active Active
- 2016-05-20 CN CN201680029177.1A patent/CN107614623B/zh active Active
- 2016-05-20 KR KR1020177033441A patent/KR20180006926A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
CN107614623A (zh)	2018-01-19
WO2016186196A1 (ja)	2016-11-24
TWI715585B (zh)	2021-01-11
HK1243449A1 (zh)	2018-07-13
JPWO2016186196A1 (ja)	2018-03-08
CN107614623B (zh)	2019-11-08
TW201708412A (zh)	2017-03-01
JP6736549B2 (ja)	2020-08-05

Publication	Publication Date	Title
JP5296536B2 (ja)	2013-09-25	アゾ化合物及びその塩並びにそれらを含有する染料系偏光膜
JP5899122B2 (ja)	2016-04-06	アゾ化合物、染料系偏光膜及び偏光板
JP5366947B2 (ja)	2013-12-11	アゾ化合物及びその塩、並びにそれらを含有する染料系偏光膜並びに偏光板
JP5899123B2 (ja)	2016-04-06	アゾ化合物及びその塩、並びにそれらを含有する染料系偏光膜並びに偏光板
JP6617098B2 (ja)	2019-12-04	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
HK1226428A1 (en)	2017-09-29	Azo compound, dye-based polarizing film containing same, and polarizing plate
JP6736549B2 (ja)	2020-08-05	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
WO2018181470A1 (ja)	2018-10-04	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、及び液晶表示装置
JP6824160B2 (ja)	2021-02-03	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
JP6702622B2 (ja)	2020-06-03	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
HK1243449B (zh)	2020-07-24	偶氮化合物和含有偶氮化合物的染料型偏振膜以及偏振板
HK1187939B (en)	2015-06-26	Azo compound, salt thereof, and dye-based polarizing film and polarizing plate containing same

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