TWI819053B - Resin and adhesive composition - Google Patents
Resin and adhesive composition Download PDFInfo
- Publication number
- TWI819053B TWI819053B TW108127926A TW108127926A TWI819053B TW I819053 B TWI819053 B TW I819053B TW 108127926 A TW108127926 A TW 108127926A TW 108127926 A TW108127926 A TW 108127926A TW I819053 B TWI819053 B TW I819053B
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- Taiwan
- Prior art keywords
- group
- formula
- resin
- carbon atoms
- meth
- Prior art date
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- 229920005989 resin Polymers 0.000 title claims abstract description 158
- 239000011347 resin Substances 0.000 title claims abstract description 158
- 239000000203 mixture Substances 0.000 title claims description 103
- 239000000853 adhesive Substances 0.000 title claims description 93
- 230000001070 adhesive effect Effects 0.000 title claims description 93
- 125000001041 indolyl group Chemical group 0.000 claims abstract description 59
- 230000009477 glass transition Effects 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 156
- 125000004432 carbon atom Chemical group C* 0.000 claims description 117
- 239000012790 adhesive layer Substances 0.000 claims description 112
- 230000003287 optical effect Effects 0.000 claims description 79
- 238000010521 absorption reaction Methods 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
- 239000000178 monomer Substances 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 239000012788 optical film Substances 0.000 claims description 30
- 238000002835 absorbance Methods 0.000 claims description 29
- 125000001931 aliphatic group Chemical group 0.000 claims description 28
- 239000003431 cross linking reagent Substances 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000006467 substitution reaction Methods 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 241001659321 ANME-2 cluster Species 0.000 claims 1
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 1
- 230000008033 biological extinction Effects 0.000 abstract 2
- -1 silane compound Chemical class 0.000 description 232
- 239000010408 film Substances 0.000 description 197
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 107
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 239000004973 liquid crystal related substance Substances 0.000 description 46
- 239000010410 layer Substances 0.000 description 38
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 30
- 230000001681 protective effect Effects 0.000 description 28
- 239000000243 solution Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 229910000077 silane Inorganic materials 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000012948 isocyanate Substances 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 12
- 150000002430 hydrocarbons Chemical group 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 229920002451 polyvinyl alcohol Polymers 0.000 description 12
- 239000004372 Polyvinyl alcohol Substances 0.000 description 11
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 11
- 230000008859 change Effects 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- 239000003505 polymerization initiator Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 229920005862 polyol Polymers 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 150000001925 cycloalkenes Chemical class 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 8
- 239000010453 quartz Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 150000008040 ionic compounds Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000004925 Acrylic resin Substances 0.000 description 6
- 229920000178 Acrylic resin Polymers 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 238000010030 laminating Methods 0.000 description 6
- 125000005647 linker group Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229920005672 polyolefin resin Polymers 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 230000006866 deterioration Effects 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000012719 thermal polymerization Methods 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- 239000002216 antistatic agent Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000000740 bleeding effect Effects 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 4
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- RSJKGSCJYJTIGS-UHFFFAOYSA-N N-undecane Natural products CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 235000010724 Wisteria floribunda Nutrition 0.000 description 3
- 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 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 210000002858 crystal cell Anatomy 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- GFKCWAROGHMSTC-UHFFFAOYSA-N trimethoxy(6-trimethoxysilylhexyl)silane Chemical compound CO[Si](OC)(OC)CCCCCC[Si](OC)(OC)OC GFKCWAROGHMSTC-UHFFFAOYSA-N 0.000 description 3
- SHCGUUKICQTMGF-UHFFFAOYSA-N trimethoxy(8-trimethoxysilyloctyl)silane Chemical compound CO[Si](OC)(OC)CCCCCCCC[Si](OC)(OC)OC SHCGUUKICQTMGF-UHFFFAOYSA-N 0.000 description 3
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical compound C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- CNSJBIWGZMUGKY-UHFFFAOYSA-N 4-methoxy-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(OC)CCC2OC21 CNSJBIWGZMUGKY-UHFFFAOYSA-N 0.000 description 2
- INRQKLGGIVSJRR-UHFFFAOYSA-N 5-hydroxypentyl prop-2-enoate Chemical compound OCCCCCOC(=O)C=C INRQKLGGIVSJRR-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- C08F226/06—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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Abstract
Description
本發明係關於樹脂、包含該樹脂的黏著劑組成物以及由該黏著劑組成物形成的黏著劑層所積層的光學積層體。 The present invention relates to an optical laminate in which an adhesive layer formed of a resin, an adhesive composition containing the resin, and the adhesive composition is laminated.
有機電激發光顯示器(有機EL顯示裝置)、液晶顯示裝置等顯示裝置(EPD:平面面板顯示器)中使用有機EL元件、液晶胞等顯示元件或偏光板等光學膜等的各種構件。該等構件中,由於有機EL發光元件及液晶化合物等為有機物,而容易產生因紫外線(UV)而劣化的問題。再者,已知使聚合性液晶化合物配向、光硬化而成的液晶系相位差膜及有機EL發光元件,不僅因紫外線劣化,更有在短波長的可見光中也劣化的傾向。為了解決前述課題,已知有設置含有吸收短波長的可見光的光之化合物的層。例如,在專利文獻1中,記載附有由黏著劑組成物所形成的黏著劑層的偏光板,該黏著劑組成物包含由丙烯酸正丁酯、丙烯酸2-羥基乙酯及N,N-二甲基丙烯醯胺所形成的共聚物及吲哚系紫外線吸收劑。
Various components such as organic EL elements, display elements such as liquid crystal cells, and optical films such as polarizing plates are used in display devices (EPD: flat panel displays) such as organic electroluminescence displays (organic EL display devices) and liquid crystal display devices. Among these components, organic EL light-emitting elements, liquid crystal compounds, and the like are organic substances and are prone to degradation due to ultraviolet rays (UV). Furthermore, it is known that liquid crystal retardation films and organic EL light-emitting elements formed by aligning and photocuring polymerizable liquid crystal compounds tend to deteriorate not only by ultraviolet rays but also by short-wavelength visible light. In order to solve the above-mentioned problems, it is known to provide a layer containing a light compound that absorbs short-wavelength visible light. For example,
[專利文獻1]日本特開2017-48340號公報 [Patent Document 1] Japanese Patent Application Publication No. 2017-48340
然而,將專利文獻1記載的包含紫外線吸收劑的黏著劑層作為光學積層體時,雖然可能抑制因紫外線、短波長的可見光造成的劣化,惟,已明白產生了因紫外線吸收劑遷移至其他層而損害光學特性的其他問題。其中,得知在具有液晶系相位差膜的積層體中,因紫外線吸收劑遷移至其他層導致的光學特性降低(相位差值的變化)變得顯著。
However, when the adhesive layer containing an ultraviolet absorber described in
本發明包含下述的發明。 The present invention includes the following inventions.
[1]一種樹脂,其係含有具有吲哚結構的結構單元的樹脂(A)。 [1] A resin (A) containing a structural unit having an indole structure.
[2]如[1]記載的樹脂,其中,樹脂(A)的玻璃轉移溫度為40℃以下。 [2] The resin according to [1], wherein the glass transition temperature of the resin (A) is 40°C or lower.
[3]如[1]或[2]記載的樹脂,其中,樹脂(A)是滿足下述式(1)的樹脂, [3] The resin according to [1] or [2], wherein the resin (A) satisfies the following formula (1),
ε(405)≧0.02 (1) ε(405)≧0.02 (1)
[式(1)中,ε(405)表示在波長405nm的樹脂(A)的克吸光係數,克吸光係數的單位為L/(g‧cm)]。 [In the formula (1), ε (405) represents the gram absorption coefficient of the resin (A) at a wavelength of 405 nm, and the unit of the gram absorption coefficient is L/(g·cm)].
[4]如[1]至[3]中任一項記載的樹脂,其中,樹脂(A)是滿足下述式(2)的樹脂, [4] The resin according to any one of [1] to [3], wherein the resin (A) satisfies the following formula (2),
ε(405)/ε(440)≧5 (2) ε(405)/ε(440)≧5 (2)
[式(2)中,ε(405)表示在波長405nm的樹脂(A)的克吸光係數,ε(440)表示在波長440nm的樹脂的克吸光係數]。 [In the formula (2), ε(405) represents the gram absorption coefficient of the resin (A) at a wavelength of 405 nm, and ε(440) represents the gram absorption coefficient of the resin at a wavelength of 440 nm].
[5]如[1]至[4]中任一項記載的樹脂,其中,樹脂(A)為包含在側鏈具有吲哚結構的結構單元的樹脂。 [5] The resin according to any one of [1] to [4], wherein the resin (A) is a resin containing a structural unit having an indole structure in a side chain.
[6]如[5]記載的樹脂,其中,在側鏈具有吲哚結構的結構單元係源自具有聚合性基及吲哚結構的光選擇性吸收化合物的結構單元。 [6] The resin according to [5], wherein the structural unit having an indole structure in the side chain is a structural unit derived from a light-selective absorbing compound having a polymerizable group and an indole structure.
[7]如[6]記載的樹脂,其中,具有聚合性基及吲哚結構的光選擇性吸收化合物為滿足下述式(1-a)的化合物, [7] The resin according to [6], wherein the light-selective absorbing compound having a polymerizable group and an indole structure is a compound satisfying the following formula (1-a),
ε(405)≧5 (1-a) ε(405)≧5 (1-a)
[式(1-a)中,ε(405)表示在波長405nm的具有聚合性基及吲哚結構的化合物的克吸光係數,克吸光係數的單位為L/(g‧cm)]。 [In formula (1-a), ε(405) represents the gram absorption coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm, and the unit of the gram absorption coefficient is L/(g·cm)].
[8]如[7]記載的樹脂,其中,具有聚合性基及吲哚結構的光選擇性吸收化合物為滿足下述式(2-a)的化合物; [8] The resin according to [7], wherein the light-selective absorbing compound having a polymerizable group and an indole structure is a compound satisfying the following formula (2-a);
ε(405)/ε(440)≧10 (2-a) ε(405)/ε(440)≧10 (2-a)
[式(2-a)中,ε(405)表示在波長405nm的具有聚合性基及吲哚結構的化合物的克吸光係數,ε(440)表示在波長440nm的具有聚合性基及吲哚結構的化合物的克吸光係數]。 [In formula (2-a), ε(405) represents the gram absorption coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm, and ε(440) represents a compound having a polymerizable group and an indole structure at a wavelength of 440 nm. gram absorption coefficient of the compound].
[9]如[5]記載的樹脂,其中,在側鏈具有吲哚結構的結構單元係源自式(I)表示的化合物的結構單元或源自式(II)表示的化合物的結構單元; [9] The resin according to [5], wherein the structural unit having an indole structure in the side chain is a structural unit derived from a compound represented by formula (I) or a structural unit derived from a compound represented by formula (II);
[式(I)中,R1、R2、R3、R4、R5及R6分別獨立地表示氫原子、雜環基、鹵原子、硝基、氰基、羥基、羧基、可具有取代基的碳數1至25的脂肪族烴基或可具有取代基的碳數6至18的芳香族烴基,該脂肪族烴基或芳香族烴基所包含的-CH2-可被-NR1A-、-SO2-、-CO-、-O-、-S-或-CF2-取代; [In formula (I), R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, and may have The substituent is an aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms that may have a substituent, and -CH 2 - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR 1A -, -SO 2 -, -CO-, -O-, -S- or -CF 2 -substitution;
R1A表示氫原子、碳數1至25的烷基或碳數6至18的芳香族烴基; R 1A represents a hydrogen atom, an alkyl group with 1 to 25 carbon atoms, or an aromatic hydrocarbon group with 6 to 18 carbon atoms;
E1表示吸電子基(Electron withdrawing group); E 1 represents electron withdrawing group;
Z表示連結基; Z represents the linking group;
A表示聚合性基; A represents a polymerizable group;
式(II)中,R12及R17分別獨立地表示氫原子、雜環基、鹵原子、硝基、氰基、羥基、羧基、可具有取代基的碳數1至25的脂肪族烴基或可具有取代基的碳數6至18的芳香族烴基,該脂肪族烴基或芳香族烴基所包含的-CH2-,可被-NR11A-、-SO2-、-CO-、-O-、-S-或-CF2-取代; In formula (II), R 12 and R 17 each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent, or An aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. -CH 2 - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR 11A -, -SO 2 -, -CO-, -O- , -S- or -CF 2 -substitution;
R11、R13、R14、R15及R16分別獨立地表示氫原子、雜環基、鹵原子、硝基、氰基、羥基、羧基、包含聚合性基的基、可具有取代基的碳數1至25的脂肪族烴基或可具有取代基的碳數6至18的芳香族烴基,該脂肪族烴基或芳香族烴基所包含的-CH2-可被-NR12A-、-SO2-、-CO-、-O-、-S-或-CF2-取代; R 11 , R 13 , R 14 , R 15 and R 16 each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, a group containing a polymerizable group, and may have a substituent. An aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH 2 - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR 12A -, -SO 2 -, -CO-, -O-, -S- or -CF 2 -substituted;
惟,R11、R13、R14、R15及R16中至少-者表示包含聚合性基的基; However, at least one of R 11 , R 13 , R 14 , R 15 and R 16 represents a group containing a polymerizable group;
R11A及R12A分別獨立地表示氫原子、碳數1至25的烷基或碳數6至18的芳香族烴基; R 11A and R 12A each independently represent a hydrogen atom, an alkyl group with 1 to 25 carbon atoms, or an aromatic hydrocarbon group with 6 to 18 carbon atoms;
E11表示吸電子基]。 E 11 represents an electron-withdrawing group].
[10]如[9]記載的樹脂,其中,R2為苯基。 [10] The resin according to [9], wherein R 2 is a phenyl group.
[11]如[9]記載的樹脂,其中,式(I)表示的化合物為式(III)表示的化合物; [11] The resin according to [9], wherein the compound represented by formula (I) is a compound represented by formula (III);
[R1、R3、R4、R5、R6及E1表示與上述相同意義; [R 1 , R 3 , R 4 , R 5 , R 6 and E 1 represent the same meanings as above;
R7表示氫原子、甲基或苯基; R 7 represents a hydrogen atom, methyl or phenyl;
Z1表示碳數1至12的烷二基、碳數6至18的2價芳香族烴基、-O-R2A-*1、-S-R2B-*1或-NR1D-R2C-*1; Z 1 represents an alkanediyl group having 1 to 12 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, -OR 2A -*1, -SR 2B -*1 or -NR 1D -R 2C -*1;
Z2表示單鍵、*2-CO-O-、*2-O-CO-、*2-S(=O)2-、*2-O-SO2-、*2-CO-NR1B-、*2-NR1C-CO-、*2-R2DO-P(=O)-OR2E-、*2-NR1E-CO-O-、*2-O-CO-NR1F-、*2-(OR2F)s1-、*2-CO-S-、*2-S-CO-或碳數1至4的全氟烷二基; Z 2 represents single bond, *2-CO-O-, *2-O-CO-, *2-S(=O) 2 -, *2-O-SO 2 -, *2-CO-NR 1B - ,*2-NR 1C -CO-,*2-R 2D OP(=O)-OR 2E -,*2-NR 1E -CO-O-,*2-O-CO-NR 1F -,*2- (OR 2F ) s1 -, *2-CO-S-, *2-S-CO- or perfluoroalkyldiyl with 1 to 4 carbon atoms;
R1B、R1C、R1D、R1E及R1F分別獨立地表示氫原子或碳數1至6的烷基; R 1B , R 1C , R 1D , R 1E and R 1F each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms;
R2A、R2B、R2C、R2D、R2E及R2F分別獨立地表示碳數1至18的2價烴基; R 2A , R 2B , R 2C , R 2D , R 2E and R 2F each independently represent a divalent hydrocarbon group having 1 to 18 carbon atoms;
*1表示與Z2的鍵結鍵; *1 indicates the bond with Z 2 ;
*2表示與Z1的鍵結鍵]。 *2 indicates the bonding bond with Z 1 ].
[12]如[1]至[11]中任一項記載的樹脂,其中,樹脂(A)更具有選自下述群A記載的結構單元中的至少1個結構單元; [12] The resin according to any one of [1] to [11], wherein the resin (A) further has at least one structural unit selected from the structural units described in the following group A;
群A:源自(甲基)丙烯酸酯的結構單元、源自苯乙烯系單體的結構單元、源自乙烯系單體的結構單元、源自環氧化合物的結構單元、式(a)表示的結構單元、式(b)表示的結構單元及式(c)表示的結構單元; Group A: Structural unit derived from (meth)acrylate, structural unit derived from styrenic monomer, structural unit derived from vinyl monomer, structural unit derived from epoxy compound, represented by formula (a) The structural unit, the structural unit represented by formula (b) and the structural unit represented by formula (c);
[式中,Ra1表示2價烴基; [In the formula, R a1 represents a divalent hydrocarbon group;
Rb1及Rb2分別獨立地表示氫原子或烴基; R b1 and R b2 each independently represent a hydrogen atom or a hydrocarbon group;
Rc1及Rc2分別獨立地表示2價烴基]。 R c1 and R c2 each independently represent a divalent hydrocarbon group].
[13]如[12]記載的樹脂,其中,相對於樹脂(A)的全部結構單元,來自選自群A記載的結構單元中的至少1個結構單元的含量為50質量%以上。 [13] The resin according to [12], wherein the content of at least one structural unit derived from the structural units selected from the group A is 50 mass % or more relative to all the structural units of the resin (A).
[14]一種黏著劑組成物,該黏著劑組成物包含[1]至[13]中任一項記載的樹脂。 [14] An adhesive composition containing the resin according to any one of [1] to [13].
[15]如[14]記載的黏著劑組成物,該黏著劑組成物更包含交聯劑(B)。 [15] The adhesive composition according to [14], further comprising a cross-linking agent (B).
[16]一種黏著劑層,該黏著劑層係由[14]或[15]記載的黏著劑組成物所形成者。 [16] An adhesive layer formed from the adhesive composition described in [14] or [15].
[17]如[16]記載的黏著劑層,該黏著劑層係滿足下述式(3)的黏著劑層, [17] The adhesive layer according to [16], which satisfies the following formula (3),
A(405)≧0.5 (3) A(405)≧0.5 (3)
[式(3)中,A(405)表示在波長405nm中的吸光度]。 [In formula (3), A (405) represents the absorbance at a wavelength of 405 nm].
[18]如[17]記載的黏著劑層,該黏著劑層滿足下述式(4), [18] The adhesive layer according to [17], which satisfies the following formula (4),
A(405)/A(440)≧5 (4) A(405)/A(440)≧5 (4)
[式(4)中,A(405)表示在波長405nm中的吸光度;A(440)表示在波長440nm中的吸光度]。 [In formula (4), A (405) represents the absorbance at a wavelength of 405 nm; A (440) represents the absorbance at a wavelength of 440 nm].
[19]一種光學積層體,該光學積層體在[16]至[18]中任一項記載的黏著劑層的至少一面積層光學膜。 [19] An optical laminate in which an optical film is laminated on at least one surface of the adhesive layer according to any one of [16] to [18].
[20]如[19]記載的光學積層體,其中,光學膜為偏光板。 [20] The optical laminate according to [19], wherein the optical film is a polarizing plate.
[21]一種影像顯示裝置,該影像顯示裝置包含[20]記載的光學積層體。 [21] An image display device including the optical laminate according to [20].
[22]一種化合物,該化合物係式(I)或式(IV)表示者, [22] A compound represented by formula (I) or formula (IV),
[式(I)中,R1、R2、R3、R4、R5及R6分別獨立地表示氫原子、雜環基、鹵原子、硝基、氰基、羥基、羧基、可具有取代基的碳數1至25的脂肪族烴基或可具有取代基的碳數6至18的芳香族烴基,該脂肪族烴基或芳香族烴基所包含的-CH2-可被-NR1A-、-SO2-、-CO-、-O-、-S-或-CF2-取代; [In formula (I), R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, and may have The substituent is an aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms that may have a substituent, and -CH 2 - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR 1A -, -SO 2 -, -CO-, -O-, -S- or -CF 2 -substitution;
R1A表示氫原子、碳數1至25的烷基或碳數6至18的芳香族烴基; R 1A represents a hydrogen atom, an alkyl group with 1 to 25 carbon atoms, or an aromatic hydrocarbon group with 6 to 18 carbon atoms;
E1表示吸電子基; E 1 represents an electron-withdrawing group;
Z表示連結基; Z represents the linking group;
A表示聚合性基; A represents a polymerizable group;
式(IV)中,R12及R17分別獨立地表示氫原子、雜環基、鹵原子、硝基、氰基、羥基、羧基、可具有取代基的碳數1至25的脂肪族烴基或可具有取 代基的碳數6至18的芳香族烴基,該脂肪族烴基或芳香族烴基所包含的-CH2-可被-NR11A-、-SO2-、-CO-、-O-、-S-或-CF2-取代; In formula (IV), R 12 and R 17 each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent, or An aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH 2 - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR 11A -, -SO 2 -, -CO-, -O-, -S- or -CF 2 -substitution;
R11、R13、R14、R15及R16,分別獨立地表示氫原子、雜環基、鹵原子、硝基、氰基、羥基、羧基、包含聚合性基的基、可具有取代基的碳數1至25的脂肪族烴基或可具有取代基的碳數6至18的芳香族烴基,該脂肪族烴基或芳香族烴基所包含的-CH2-,可被-NR12A-、-SO2-、-CO-、-O-、-S-或-CF2-取代; R 11 , R 13 , R 14 , R 15 and R 16 each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, a group containing a polymerizable group, and may have a substituent an aliphatic hydrocarbon group with 1 to 25 carbon atoms or an aromatic hydrocarbon group with 6 to 18 carbon atoms that may have a substituent, and -CH 2 - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR 12A -, - SO 2 -, -CO-, -O-, -S- or -CF 2 -substituted;
惟,R11、R13、R14、R15及R16中至少一者表示包含聚合性基的基; However, at least one of R 11 , R 13 , R 14 , R 15 and R 16 represents a group containing a polymerizable group;
R11A及R12A分別獨立地表示氫原子、碳數1至25的烷基或碳數6至18的芳香族烴基; R 11A and R 12A each independently represent a hydrogen atom, an alkyl group with 1 to 25 carbon atoms, or an aromatic hydrocarbon group with 6 to 18 carbon atoms;
E11表示吸電子基]。 E 11 represents an electron-withdrawing group].
[23]如[22]記載的化合物,其中,R2為苯基。 [23] The compound according to [22], wherein R 2 is phenyl.
[24]如[22]記載的化合物,其中,式(I)表示的化合物為式(III)表示的化合物; [24] The compound according to [22], wherein the compound represented by formula (I) is a compound represented by formula (III);
[R1、R3、R4、R5、R6及E1表示與上述相同意義; [R 1 , R 3 , R 4 , R 5 , R 6 and E 1 represent the same meanings as above;
R7表示氫原子、氰基、甲基或苯基; R 7 represents a hydrogen atom, cyano group, methyl group or phenyl group;
Z1表示碳數1至12的烷二基、碳數6至18的2價芳香族烴基、-O-R2A-*1、-S-R2B-*1或-NR1D-R2C-*1; Z 1 represents an alkanediyl group having 1 to 12 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, -OR 2A -*1, -SR 2B -*1 or -NR 1D -R 2C -*1;
Z2表示單鍵、*2-CO-O-、*2-O-CO-、*2-S(=O)2-、*2-O-SO2-、*2-CO-NR1B-、*2-NR1C-CO-、*2-R2DO-P(=O)-OR2E-、*2-NR1E-CO-O-、*2-O-CO-NR1F-、*2-(OR2F)s1-、*2-CO-S-、*2-S-CO-或碳數1至4的全氟烷二基; Z 2 represents single bond, *2-CO-O-, *2-O-CO-, *2-S(=O) 2 -, *2-O-SO 2 -, *2-CO-NR 1B - ,*2-NR 1C -CO-,*2-R 2D OP(=O)-OR 2E -,*2-NR 1E -CO-O-,*2-O-CO-NR 1F -,*2- (OR 2F ) s1 -, *2-CO-S-, *2-S-CO- or perfluoroalkyldiyl with 1 to 4 carbon atoms;
R1B、R1C、R1D、R1E及R1F分別獨立地表示氫原子或碳數1至6的烷基; R 1B , R 1C , R 1D , R 1E and R 1F each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms;
R2A、R2B、R2C、R2D、R2E及R2F分別獨立地表示碳數1至18的2價烴基; R 2A , R 2B , R 2C , R 2D , R 2E and R 2F each independently represent a divalent hydrocarbon group having 1 to 18 carbon atoms;
*1表示與Z2的鍵結鍵; *1 indicates the bond with Z 2 ;
*2表示與Z1的鍵結鍵]。 *2 indicates the bonding bond with Z 1 ].
[25]如[22]至[24]中任一項記載的化合物,其中,E1為氰基。 [25] The compound according to any one of [22] to [24], wherein E 1 is a cyano group.
本發明係提供一種可抑制有機EL發光元件及液晶系相位差膜的劣化之黏著劑層及形成該黏著劑層的黏著劑組成物。再者,提供一種可形成可良好地抑制有機EL發光元件及液晶系相位差膜的劣化的黏著劑組成物之樹脂。 The present invention provides an adhesive layer capable of suppressing deterioration of organic EL light-emitting elements and liquid crystal retardation films, and an adhesive composition forming the adhesive layer. Furthermore, the invention provides a resin capable of forming an adhesive composition that can effectively suppress deterioration of organic EL light-emitting elements and liquid crystal retardation films.
1‧‧‧黏著劑層 1‧‧‧Adhesive layer
2‧‧‧剝離膜 2‧‧‧Peel-off film
10A、10B、10C、10D‧‧‧光學積層體 10A, 10B, 10C, 10D‧‧‧Optical laminated body
8‧‧‧保護膜 8‧‧‧Protective film
7‧‧‧接著劑層 7‧‧‧Adhesive layer
7a‧‧‧黏著劑層 7a‧‧‧Adhesive layer
9‧‧‧偏光膜 9‧‧‧Polarizing film
30‧‧‧發光元件 30‧‧‧Light-emitting components
40‧‧‧光學膜 40‧‧‧Optical film
50、50a‧‧‧1/4波長相位差層 50, 50a‧‧‧1/4 wavelength phase difference layer
60‧‧‧接著劑層或黏著劑層 60‧‧‧Adhesive layer or adhesive layer
70‧‧‧1/2波長相位差層 70‧‧‧1/2 wavelength phase difference layer
80‧‧‧正C層 80‧‧‧C Floor
100‧‧‧偏光板 100‧‧‧Polarizing plate
110‧‧‧相位差膜 110‧‧‧Phase difference film
第1圖係表示本發明的黏著劑層的層構成之一例。 Figure 1 shows an example of the layer structure of the adhesive layer of the present invention.
第2圖係表示本發明的光學積層體的層構成之一例。 Figure 2 shows an example of the layer structure of the optical laminate of the present invention.
第3圖係表示本發明的光學積層體的層構成之一例。 Fig. 3 shows an example of the layer structure of the optical laminate of the present invention.
第4圖係表示本發明的光學積層體的層構成之一例。 Fig. 4 shows an example of the layer structure of the optical laminate of the present invention.
第5圖係表示本發明的光學積層體的層構成之一例。 Fig. 5 shows an example of the layer structure of the optical laminate of the present invention.
〈黏著劑組成物〉 〈Adhesive composition〉
本發明的黏著劑組成物包含樹脂(A),該樹脂(A)含有具有吲哚結構的結構單元。本發明的黏著劑組成物更包含交聯劑(B)、矽烷化合物(D)、抗靜電劑等。 The adhesive composition of the present invention contains resin (A) containing a structural unit having an indole structure. The adhesive composition of the present invention further includes a cross-linking agent (B), a silane compound (D), an antistatic agent, etc.
〈樹脂(A)〉 〈Resin(A)〉
本發明的樹脂(A)係含有具有吲哚結構的結構單元的樹脂,較理想為含有源自具有吲哚結構的光選擇性吸收化合物的結構單元的樹脂。 The resin (A) of the present invention is a resin containing a structural unit having an indole structure, preferably a resin containing a structural unit derived from a light-selective absorbing compound having an indole structure.
樹脂(A)的玻璃轉移溫度(Tg)較理想為40℃以下,更理想為20℃以下,更加理想為10℃以下,特別理想為0℃以下。再者,樹脂(A)的玻璃轉移溫度(Tg)通常為-80℃以上,較理想為-60℃以上,更理想為-50℃以上。樹脂(A)的玻璃轉移溫度(Tg)為40℃以下時,在提升由包含樹脂(A)的黏著劑組成物所形成的黏著劑層對被黏著體的密著性上有利。再者,樹脂(A)的玻璃轉移溫度(Tg)為-80℃以上時,在提升由包含樹脂(A)的黏著劑組成物所形成的黏著劑層的耐熱性上有利。此外,玻璃轉移溫度可藉由示差掃描量熱計(DSC)測定。 The glass transition temperature (T g ) of the resin (A) is preferably 40°C or lower, more preferably 20°C or lower, even more preferably 10°C or lower, particularly preferably 0°C or lower. Furthermore, the glass transition temperature (T g ) of the resin (A) is usually -80°C or higher, preferably -60°C or higher, and more preferably -50°C or higher. When the glass transition temperature (T g ) of the resin (A) is 40° C. or lower, it is advantageous in improving the adhesion of the adhesive layer formed of the adhesive composition containing the resin (A) to the adherend. Furthermore, when the glass transition temperature (T g ) of the resin (A) is -80° C. or higher, it is advantageous in improving the heat resistance of the adhesive layer formed of the adhesive composition containing the resin (A). In addition, the glass transition temperature can be measured by a differential scanning calorimeter (DSC).
樹脂(A)較理想為滿足下述式(1)的樹脂。 The resin (A) is preferably a resin that satisfies the following formula (1).
ε(405)≧0.02 (1) ε(405)≧0.02 (1)
[式(1)中,ε(405)表示在波長405nm的樹脂的克吸光係數;克吸光係數的單位為L/(g‧cm)]。 [In formula (1), ε(405) represents the gram absorption coefficient of the resin at a wavelength of 405 nm; the unit of the gram absorption coefficient is L/(g‧cm)].
此外,樹脂(A)的克吸光係數可用實施例記載的方法測定。 In addition, the gram absorption coefficient of the resin (A) can be measured by the method described in the Examples.
樹脂(A)之ε(405)的值越大越容易吸收波長405nm的光。ε(405)的值較理想為0.02L/(g‧cm)以上,更理想為0.1L/(g‧cm)以上,更加理想為0.2L/(g‧cm)以上,通常為10L/(g‧cm)以下。 The larger the value of ε (405) of resin (A), the easier it is to absorb light with a wavelength of 405 nm. The value of ε(405) is preferably 0.02L/(g‧cm) or more, more preferably 0.1L/(g‧cm) or more, even more preferably 0.2L/(g‧cm) or more, usually 10L/( g‧cm) or less.
將包含樹脂(A)的黏著劑組成物應用於有機EL顯示裝置、液晶顯示裝置等顯示裝置時,樹脂(A)的ε(405)為0.02L/(g‧cm)以上時,由於400nm附近的可見光的吸收性能好,可抑制有機EL顯示裝置、液晶顯示裝置等顯示裝置所使用的相位差膜、有機EL發光元件因可見光導致的劣化。 When the adhesive composition containing resin (A) is applied to display devices such as organic EL display devices and liquid crystal display devices, when the ε(405) of the resin (A) is 0.02L/(g‧cm) or more, due to the near 400 nm It has good visible light absorption performance and can suppress deterioration caused by visible light in retardation films and organic EL light-emitting elements used in display devices such as organic EL displays and liquid crystal displays.
樹脂(A)較理想為滿足下述式(2)的樹脂。 The resin (A) is preferably a resin that satisfies the following formula (2).
ε(405)/ε(440)≧5 (2) ε(405)/ε(440)≧5 (2)
[式(2)中,ε(405)表示在波長405nm的樹脂的克吸光係數,ε(440)表示在波長440nm的樹脂的克吸光係數]。 [In the formula (2), ε(405) represents the gram absorption coefficient of the resin at a wavelength of 405 nm, and ε(440) represents the gram absorption coefficient of the resin at a wavelength of 440 nm].
樹脂(A)的ε(405)/ε(440)的值越大,越可選擇性地吸收400nm附近波長的光。ε(405)/ε(440)的值較理想為5以上,更理想為10以上,更加理想為30以上。 The larger the value of ε(405)/ε(440) of the resin (A), the more selectively it can absorb light with a wavelength near 400 nm. The value of ε(405)/ε(440) is preferably 5 or more, more preferably 10 or more, and still more preferably 30 or more.
樹脂(A)的ε(405)/ε(440)為5以上時,將含有樹脂(A)的黏著劑組成物應用於有機EL顯示裝置、液晶顯示裝置等顯示裝置時,不阻礙顯示裝置的色彩表現,且可吸收400nm附近的可見光抑制相位差膜的光劣化。 When ε(405)/ε(440) of resin (A) is 5 or more, when the adhesive composition containing resin (A) is applied to display devices such as organic EL display devices and liquid crystal display devices, it will not hinder the performance of the display device. Color expression, and can absorb visible light near 400nm to suppress photodegradation of the retardation film.
樹脂(A)可含有在主鏈具有吲哚結構的結構單元,亦可含有在側鏈具有吲哚結構的結構單元。樹脂(A)較理想為含有在側鏈具有吲哚結構的結構單元。 Resin (A) may contain a structural unit having an indole structure in the main chain, or may contain a structural unit having an indole structure in a side chain. The resin (A) preferably contains a structural unit having an indole structure in the side chain.
側鏈具有吲哚結構的結構單元無特別限制,較理想為源自具有聚合性基及吲哚結構的化合物的結構單元。源自具有聚合性基及吲哚結構的化合物的結構單元較理想為源自具有聚合性基及吲哚結構的光選擇性吸收化合物的結構單元。 The structural unit having an indole structure in the side chain is not particularly limited, but is preferably a structural unit derived from a compound having a polymerizable group and an indole structure. The structural unit derived from a compound having a polymerizable group and an indole structure is preferably a structural unit derived from a light-selective absorbing compound having a polymerizable group and an indole structure.
具有聚合性基及吲哚結構的光選擇性吸收化合物較理想為滿足下述式(1-a),又更理想為滿足下述式(2-a)。 The light-selective absorbing compound having a polymerizable group and an indole structure preferably satisfies the following formula (1-a), and more preferably satisfies the following formula (2-a).
ε(405)≧5 (1-a) ε(405)≧5 (1-a)
[式(1-a)中,ε(405)表示在波長405nm的具有聚合性基及吲哚結構的化合物的克吸光係數,克吸光係數的單位為L/(g‧cm)]。 [In formula (1-a), ε(405) represents the gram absorption coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm, and the unit of the gram absorption coefficient is L/(g·cm)].
ε(405)/ε(440)≧10 (2-a) ε(405)/ε(440)≧10 (2-a)
[式(2-a)中,ε(405)表示在波長405nm中的具有聚合性基及吲哚結構的化合物的克吸光係數,ε(440)表示在波長440nm中的具有聚合性基及吲哚結構的化合物的克吸光係數]。 [In formula (2-a), ε(405) represents the gram absorption coefficient of a compound having a polymerizable group and an indole structure at a wavelength of 405 nm, and ε(440) represents a compound having a polymerizable group and an indole structure at a wavelength of 440 nm. Gram absorption coefficient of compounds with indole structure].
具有聚合性基及吲哚結構的化合物,ε(405)的值較理想為5L/(g‧cm)以上,更理想為10L/(g‧cm)以上,更加理想為20L/(g‧cm)以上,又更加理想為30L/(g‧cm)以上,通常為500L/(g‧cm)以下。ε(405)的值越大,越容易吸收波長405nm的光,容易表現抑制因紫外線、短波長導致的可見光的劣化之功能。 For compounds with a polymerizable group and an indole structure, the value of ε(405) is preferably 5L/(g‧cm) or more, more preferably 10L/(g‧cm) or more, and even more preferably 20L/(g‧cm ) or more, more preferably 30L/(g‧cm) or more, usually 500L/(g‧cm) or less. The larger the value of ε (405), the easier it is to absorb light with a wavelength of 405 nm, and it is easier to suppress the degradation of visible light caused by ultraviolet rays and short wavelengths.
具有聚合性基及吲哚結構的化合物,ε(405)/ε(440)的值較理想為10以上,更理想為15以上。ε(405)/ε(440)的值越大的化合物,越不阻礙顯示裝置的色彩表現,可吸收波長405nm附近的光抑制相位差膜、有機EL元件等顯示裝置的光劣化。 For a compound having a polymerizable group and an indole structure, the value of ε(405)/ε(440) is preferably 10 or more, and more preferably 15 or more. A compound with a larger value of ε(405)/ε(440) does not hinder the color expression of a display device and can absorb light with a wavelength near 405 nm to suppress light degradation of display devices such as retardation films and organic EL elements.
在側鏈具有吲哚結構的結構單元較理想為源自式(I)表示的化合物的結構單元或源自式(II)表示的化合物的結構單元,更理想為源自式(I)表示的化合物的結構單元。 The structural unit having an indole structure in the side chain is preferably a structural unit derived from a compound represented by formula (I) or a structural unit derived from a compound represented by formula (II), and more preferably a structural unit derived from a compound represented by formula (I). The structural unit of a compound.
[式(I)中,R1、R2、R3、R4、R5及R6分別獨立地表示氫原子、雜環基、鹵原子、硝基、氰基、羥基、羧基、可具有取代基的碳數1至25的脂肪族烴基或可具有取代基的碳數6至18的芳香族烴基,該脂肪族烴基或芳香族烴基所包含的-CH2-可被-NR1A-、-SO2-、-CO-、-O-、-S-或-CF2-取代; [In formula (I), R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, and may have The substituent is an aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms that may have a substituent, and -CH 2 - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR 1A -, -SO 2 -, -CO-, -O-, -S- or -CF 2 -substitution;
R1A表示氫原子、碳數1至25的烷基或碳數6至18的芳香族烴基; R 1A represents a hydrogen atom, an alkyl group with 1 to 25 carbon atoms, or an aromatic hydrocarbon group with 6 to 18 carbon atoms;
E1表示吸電子基; E 1 represents an electron-withdrawing group;
Z表示連結基; Z represents the linking group;
A表示聚合性基; A represents a polymerizable group;
式(II)中,R12及R17分別獨立地表示氫原子、雜環基、鹵原子、硝基、氰基、羥基、羧基、可具有取代基的碳數1至25的脂肪族烴基或可具有取 代基的碳數6至18的芳香族烴基,該脂肪族烴基或芳香族烴基所包含的-CH2-可被-NR11A-、-SO2-、-CO-、-O-、-S-或-CF2-取代; In formula (II), R 12 and R 17 each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, an aliphatic hydrocarbon group having 1 to 25 carbon atoms which may have a substituent, or An aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH 2 - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR 11A -, -SO 2 -, -CO-, -O-, -S- or -CF 2 -substitution;
R11、R13、R14、R15及R16分別獨立地表示氫原子、雜環基、鹵原子、硝基、氰基、羥基、羧基、包含聚合性基的基、可具有取代基的碳數1至25的脂肪族烴基或可具有取代基的碳數6至18的芳香族烴基,該脂肪族烴基或芳香族烴基所包含的-CH2-可被-NR12A-、-SO2-、-CO-、-O-、-S-或-CF2-取代; R 11 , R 13 , R 14 , R 15 and R 16 each independently represent a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, a group containing a polymerizable group, and may have a substituent. An aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and -CH 2 - contained in the aliphatic hydrocarbon group or aromatic hydrocarbon group may be -NR 12A -, -SO 2 -, -CO-, -O-, -S- or -CF 2 -substituted;
惟,R11、R13、R14、R15及R16中至少一者表示包含聚合性基的基; However, at least one of R 11 , R 13 , R 14 , R 15 and R 16 represents a group containing a polymerizable group;
R11A及R12A分別獨立地表示氫原子、碳數1至25的烷基或碳數6至18的芳香族烴基; R 11A and R 12A each independently represent a hydrogen atom, an alkyl group with 1 to 25 carbon atoms, or an aromatic hydrocarbon group with 6 to 18 carbon atoms;
E11表示吸電子基]。 E 11 represents an electron-withdrawing group].
E1及E11表示的吸電子基可列舉例如:氰基、硝基、鹵原子、經鹵原子取代的烷基、式(I-1)表示的基等。 Examples of the electron-withdrawing group represented by E 1 and E 11 include a cyano group, a nitro group, a halogen atom, an alkyl group substituted with a halogen atom, and a group represented by formula (I-1).
*-X1-R111 (I-1) *-X 1 -R 111 (I-1)
[式中,R111表示氫原子或碳數1至25的烴基,該烷基所包含的亞甲基之至少一個可被氧原子取代。 [In the formula, R 111 represents a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms, and at least one of the methylene groups contained in the alkyl group may be substituted with an oxygen atom.
X1表示-CO-*3、-COO-*3、-CS-*3、-CSS-*3、-CSNR112-*3、-CONR113-*3、-CNR114-*3或-SO2-*3。 X 1 means -CO-*3, -COO-*3, -CS-*3, -CSS-*3, -CSNR 112 -*3, -CONR 113 -*3, -CNR 114 -*3 or -SO 2- *3.
R112、R113及R114分別獨立地表示氫原子、碳數1至6的烷基或苯基。 R 112 , R 113 and R 114 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
*3表示與R111的鍵結鍵。 *3 indicates the bond with R 111 .
*表示與碳原子的鍵結鍵。] * indicates a bond with a carbon atom. ]
鹵原子可列舉例如:氟原子、氯原子、溴原子、碘原子。 Examples of the halogen atom include fluorine atom, chlorine atom, bromine atom and iodine atom.
經鹵原子取代的烷基可列舉例如:單氟甲基、單氟乙基、單氯甲基、單氯乙基、單溴甲基、單溴乙基、單碘甲基、單碘乙基、二氟甲基、二氟乙基、二氯甲基、二氯乙基、二溴甲基、二溴乙基、二碘甲基、二碘乙基、三氟甲基、三氯甲基、三溴甲基、三碘甲基的鹵化烷基等。經鹵原子取代的烷基的碳數通常為1至25。 Examples of alkyl groups substituted by halogen atoms include: monofluoromethyl, monofluoroethyl, monochloromethyl, monochloroethyl, monobromomethyl, monobromoethyl, monoiodomethyl, and monoiodoethyl , difluoromethyl, difluoroethyl, dichloromethyl, dichloroethyl, dibromomethyl, dibromoethyl, diiodomethyl, diiodoethyl, trifluoromethyl, trichloromethyl , tribromomethyl, triiodomethyl halogenated alkyl, etc. The carbon number of the alkyl group substituted by a halogen atom is usually 1 to 25.
R111表示的碳數1至25的烴基可列舉例如:甲基、乙基、正丙基、異丙基、正丁基、第三丁基、第二丁基、正戊基、異戊基、正己基、異己基、正辛基、異辛基、正壬基、異壬基、正癸基、異癸基、正十二烷基、異十二烷基、十一烷基、肉荳蔻基、十六烷基、硬脂基等碳數1至25的直鏈或分支鏈的烷基;環丙基、環丁基、環戊基、環己基等碳數3至25的環烷基;環丙基甲基、環己基甲基等碳數4至25的環烷基烷基;苯基、萘基、蒽基、聯苯基等碳數6至25的芳香基;苄基、苯基乙基、萘基甲基、苯基等碳數7至25的芳烷基。 Examples of the hydrocarbon group having 1 to 25 carbon atoms represented by R 111 include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, and isopentyl. , n-hexyl, isohexyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, isodecyl, n-dodecyl, isododecanyl, undecyl, nutmeg Linear or branched chain alkyl groups with 1 to 25 carbon atoms such as hexadecyl, stearyl, etc.; cycloalkyl groups with 3 to 25 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. ; cycloalkylalkyl groups with 4 to 25 carbon atoms such as cyclopropylmethyl and cyclohexylmethyl; aryl groups with 6 to 25 carbon atoms such as phenyl, naphthyl, anthracenyl and biphenyl groups; benzyl, benzene Aralkyl groups with 7 to 25 carbon atoms such as ethyl group, naphthylmethyl group, and phenyl group.
R112、R113及R114表示的碳數1至6的烷基可列舉例如:甲基、乙基、正丙基、異丙基、正丁基、第三丁基、第二丁基等。 Examples of the alkyl group having 1 to 6 carbon atoms represented by R 112 , R 113 and R 114 include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, etc. .
Z表示的連結基只要是2價的連結基,則無特別限制。 The linking group represented by Z is not particularly limited as long as it is a divalent linking group.
A表示的聚合性基無特別限制。例如,可為陽離子聚合性基,亦可為陰離子聚合性基,也可為自由基聚合性基。更具體而言,可列舉:乙烯基等烯基;環氧基;氧雜環丁烷基;乙烯醚基;丙烯腈基;甲基丙烯腈基;乙烯基、α-甲基乙烯基、丙烯醯基、甲基丙烯醯基、烯丙基、苯乙烯基、丙烯醯胺基、甲基丙烯醯胺基等乙烯性不飽和基等。 The polymerizable group represented by A is not particularly limited. For example, it may be a cationic polymerizable group, an anionic polymerizable group, or a radical polymerizable group. More specifically, examples include: alkenyl groups such as vinyl; epoxy groups; oxetanyl groups; vinyl ether groups; acrylonitrile groups; methacrylonitrile groups; vinyl groups, α-methylvinyl groups, and propylene groups. Ethylenically unsaturated groups such as acyl group, methacrylyl group, allyl group, styryl group, acrylamide group, methacrylamide group, etc.
R1至R6、R11至R17表示的鹵原子可列舉例如:氟原子、氯原子、溴原子、碘原子。 Examples of the halogen atom represented by R 1 to R 6 and R 11 to R 17 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
R1至R6、R11至R17表示的雜環基可舉出從雜環除去1個氫原子而成的基。具體而言,可列舉:吡咯啶環、吡咯啉環基、咪唑啉啶環基、咪唑啉環基、噁唑啉環基、噻唑啉環基、哌啶環基、嗎啉環基、哌環基、吲哚環基、異吲哚環基、喹啉環基、噻吩環基、吡咯環基、噻唑啉環基、呋喃環基、吡啶環基、二噁烷環基、嗎啉環基、噻環基、三唑環基、四唑環基、二氧呋喃環基、吡環基、嘌呤環基等碳數4至30的脂肪族雜環基或碳數3至20的芳香族雜環基等。該等的雜環基可為不飽和鍵經氫化的結構,又,也可為環狀骨架經縮環的結構(例如苯,並咪唑環)、雜環上的氫原子更經雜環基、鹵原子、硝基、氰基、羥基、羧基等取代而成者。 Examples of the heterocyclic group represented by R 1 to R 6 and R 11 to R 17 include a group obtained by removing one hydrogen atom from the heterocyclic ring. Specific examples include: pyrrolidine ring, pyrroline ring group, imidazolinidine ring group, imidazoline ring group, oxazoline ring group, thiazoline ring group, piperidine ring group, morpholine ring group, piperazoline ring group Ring group, indole ring group, isoindole ring group, quinoline ring group, thiophene ring group, pyrrole ring group, thiazoline ring group, furan ring group, pyridine ring group, dioxane ring group, morpholine ring group , thiophene Ring group, triazole ring group, tetrazole ring group, dioxofuran ring group, pyridine An aliphatic heterocyclic group having 4 to 30 carbon atoms, such as a ring group or a purine ring group, or an aromatic heterocyclic group having 3 to 20 carbon atoms. Such heterocyclic groups can be structures in which unsaturated bonds are hydrogenated, and they can also be structures in which the cyclic skeleton is condensed (such as benzene, imidazole ring). It is formed by substitution of halogen atom, nitro group, cyano group, hydroxyl group, carboxyl group, etc.
R1至R6、R11至R17表示的碳數1至25的脂肪族烴基可列舉:甲基、乙基、正丙基、異丙基、正丁基、第三丁基、第二丁基、正戊基、異戊基、正己基、異己基、正辛基、異辛基、正壬基、異壬基、正癸基、異癸基、正十二烷基、異十二烷基、十一烷基、肉荳蔻基、十六烷基、硬脂基等碳數1至25的直鏈或分支鏈的烷基;環丙基、環丁基、環戊基、環己基等碳數3至25的環烷基;環丙基甲基、環己基甲基等碳數4至25的環烷基烷基等,從溶解性的觀點而言,較理想為2-乙基己基、2-丁基辛基等碳數3至25的分支鏈的烷基。 Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R 1 to R 6 and R 11 to R 17 include: methyl, ethyl, n-propyl, isopropyl, n-butyl, tertiary butyl, tertiary butyl, Butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, isodecyl, n-dodecyl, isododecanyl Alkyl, undecyl, myristyl, hexadecyl, stearyl and other linear or branched chain alkyl groups with 1 to 25 carbon atoms; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl cycloalkyl groups having 3 to 25 carbon atoms; cycloalkylalkyl groups having 4 to 25 carbon atoms, such as cyclopropylmethyl and cyclohexylmethyl; from the viewpoint of solubility, 2-ethyl is preferred Hexyl, 2-butyloctyl and other branched chain alkyl groups having 3 to 25 carbon atoms.
R1至R6、R11至R17表示的碳數1至25的脂肪族烴基可具有的取代基可列舉:雜環基、鹵原子、硝基、氰基、羥基、羧基、乙醯胺基、胺基、碳數1至12的烷基胺基等。雜環基可舉出與R1表示的雜環基相同者。 Examples of the substituents that the aliphatic hydrocarbon group having 1 to 25 carbon atoms represented by R 1 to R 6 and R 11 to R 17 may have include: heterocyclic group, halogen atom, nitro group, cyano group, hydroxyl group, carboxyl group, acetamide group, amine group, alkylamino group with 1 to 12 carbon atoms, etc. Examples of the heterocyclic group include the same ones as the heterocyclic group represented by R 1 .
R1至R6、R11至R17表示的碳數6至18的芳香族烴基可列舉:苯基、萘基、蒽基、聯苯基、甲基苯基等碳數6至18的芳香基;苄基、苯乙基、萘甲基、苯氧基等碳數7至18的芳烷基等。R1至R6、R11至R17表示的碳數6至18的芳香族烴基所包含的-CH2-經-SO2-、-CO-、-O-、-S-或-CF2-取代的基可列舉:苯氧基、萘氧基等芳香氧基等。從波長選擇性的觀點而言,R1至R6、R11至R17表示的碳數6至18的芳香族烴基較理想為碳數7至18的芳烷基或碳數6至18的芳香氧基,更理想為苄基或碳數6至18的芳香氧基。 Examples of the aromatic hydrocarbon groups having 6 to 18 carbon atoms represented by R 1 to R 6 and R 11 to R 17 include aromatic hydrocarbon groups having 6 to 18 carbon atoms such as phenyl, naphthyl, anthracenyl, biphenyl, and methylphenyl groups. groups; benzyl, phenethyl, naphthylmethyl, phenoxy and other aralkyl groups with 7 to 18 carbon atoms, etc. -CH 2 - in the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R 1 to R 6 and R 11 to R 17 via -SO 2 -, -CO-, -O-, -S- or -CF 2 - Examples of the substituted group include aryloxy groups such as phenoxy group and naphthyloxy group. From the viewpoint of wavelength selectivity, the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R 1 to R 6 and R 11 to R 17 is preferably an aralkyl group having 7 to 18 carbon atoms or an aralkyl group having 6 to 18 carbon atoms. The aromatic oxygen group is more preferably a benzyl group or an aromatic oxygen group having 6 to 18 carbon atoms.
R1至R6、R11至R17表示的碳數6至18的芳香族烴基可具有的取代基可列舉:雜環基、鹵原子、硝基、氰基、羥基、羧基、乙醯胺基、胺基、碳數1至12的烷基胺基等。雜環基可舉出與R1表示的雜環基相同者。 Examples of substituents that the aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R 1 to R 6 and R 11 to R 17 may have include heterocyclic group, halogen atom, nitro group, cyano group, hydroxyl group, carboxyl group, and acetamide. group, amine group, alkylamino group with 1 to 12 carbon atoms, etc. Examples of the heterocyclic group include the same ones as the heterocyclic group represented by R 1 .
R11、R13、R14、R15及R16表示的包含聚合性基的基只要是末端具有聚合性基的基即可,無特別限制,具體而言,可舉出式(I-2)表示的基。 The group containing a polymerizable group represented by R 11 , R 13 , R 14 , R 15 and R 16 is not particularly limited as long as it has a polymerizable group at its terminal. Specific examples include formula (I-2 ) represents the basis.
*-R115-X2 (I-2) *-R 115 -X 2 (I-2)
[式(I-2)中,X2表示聚合性基, [In formula (I-2), X 2 represents a polymerizable group,
R115表示碳數1至12的烷二基,該烷二基所包含的-CH2-可被-O-、-CO-、-CS-或-NR116-取代, R 115 represents an alkylenediyl group having 1 to 12 carbon atoms, and -CH 2 - contained in the alkylenediyl group may be substituted by -O-, -CO-, -CS- or -NR 116 -,
R116表示氫原子或碳數1至6的烷基, R 116 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
*表示與碳原子或氮原子的鍵結鍵]。 *Indicates a bond with a carbon atom or a nitrogen atom].
X2表示的聚合性基可舉出與A表示的聚合性基相同者,較理想為乙烯基、α-甲基乙烯基、丙烯醯基、甲基丙烯醯基、烯丙基、苯乙烯基、丙烯醯胺基、甲基丙烯醯胺基等乙烯性不飽和基等。 Examples of the polymerizable group represented by , acrylamide group, methacrylamide group and other ethylenically unsaturated groups.
Rl15表示的碳數1至12的烷二基可列舉:亞甲基、伸乙基、丙烷-1,3-二基、丁烷-1,4-二基、戊烷-1,5-二基、己烷-1,6-二基、乙烷-1,1-二基、丙烷-1,2-二基、丁烷-1,3-二基、2-甲基丙烷-1,3-二基、2-甲基丙烷-1,2-二基、戊烷-1,4-二基及2-甲基丁烷-1,4-二基等。 Examples of the alkylenediyl group having 1 to 12 carbon atoms represented by R115 include methylene, ethylidene, propane-1,3-diyl, butane-1,4-diyl, and pentane-1,5- Diyl, hexane-1,6-diyl, ethane-1,1-diyl, propane-1,2-diyl, butane-1,3-diyl, 2-methylpropane-1, 3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl and 2-methylbutane-1,4-diyl, etc.
R116表示的碳數1至6的烷基可舉出與R112表示的碳數1至6的烷基相同者。 Examples of the alkyl group having 1 to 6 carbon atoms represented by R 116 include the same ones as the alkyl group having 1 to 6 carbon atoms represented by R 112 .
R11、R13、R14、R15及R16中至少一者表示包含聚合性基的基。 At least one of R 11 , R 13 , R 14 , R 15 and R 16 represents a group containing a polymerizable group.
較理想為R13、R14、R15及R16中至少一者為包含聚合性基的基,更理想為R13、R14、R15或R16中之任一者為包含聚合性基的基。 More preferably, at least one of R 13 , R 14 , R 15 and R 16 is a group containing a polymerizable group, and more preferably, any one of R 13 , R 14 , R 15 or R 16 is a group containing a polymerizable group. The base.
R2較理想為碳數6至18的芳香族烴基或雜環基,更理想為碳數6至18的芳香族烴基或碳數3至20的芳香族雜環基。 R 2 is preferably an aromatic hydrocarbon group or heterocyclic group having 6 to 18 carbon atoms, more preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms or an aromatic heterocyclic group having 3 to 20 carbon atoms.
A表示的聚合性基,較理想為乙烯性不飽和基。 The polymerizable group represented by A is preferably an ethylenically unsaturated group.
E1及E11較理想為分別獨立地為氰基。 E 1 and E 11 are preferably each independently a cyano group.
式(I)表示的化合物較理想為式(III)表示的化合物。 The compound represented by formula (I) is preferably a compound represented by formula (III).
[R1、R3、R4、R5、R6及E1表示與上述相同意義; [R 1 , R 3 , R 4 , R 5 , R 6 and E 1 represent the same meanings as above;
R7表示氫原子、氰基、甲基或苯基; R 7 represents a hydrogen atom, cyano group, methyl group or phenyl group;
Z1表示碳數1至12的烷二基、碳數6至18的2價芳香族烴基、-O-R2A-*1、-S-R2B-*1或-NR1D-R2C-*1; Z 1 represents an alkanediyl group having 1 to 12 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, -OR 2A -*1, -SR 2B -*1 or -NR 1D -R 2C -*1;
Z2表示單鍵、*2-CO-O-、*2-O-CO-、*2-S(=O)2-、*2-O-SO2-、*2-CO-NR1B-、*2-NR1C-CO-、*2-R2DO-P(=O)-OR2E-、*2-NR1E-CO-O-、*2-O-CO-NR1F-、*2-(OR2F)s1-、*2-CO-S-、*2-S-CO-或碳數1至4的全氟烷二基; Z 2 represents single bond, *2-CO-O-, *2-O-CO-, *2-S(=O) 2 -, *2-O-SO 2 -, *2-CO-NR 1B - ,*2-NR 1C -CO-,*2-R 2D OP(=O)-OR 2E -,*2-NR 1E -CO-O-,*2-O-CO-NR 1F -,*2- (OR 2F ) s1 -, *2-CO-S-, *2-S-CO- or perfluoroalkyldiyl with 1 to 4 carbon atoms;
R1B、R1C、R1D、R1E及R1F分別獨立地表示氫原子或碳數1至6的烷基; R 1B , R 1C , R 1D , R 1E and R 1F each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms;
R2A、R2B、R2C、R2D、R2E及R2F分別獨立地表示碳數1至18的2價烴基; R 2A , R 2B , R 2C , R 2D , R 2E and R 2F each independently represent a divalent hydrocarbon group having 1 to 18 carbon atoms;
*1表示與Z2的鍵結鍵; *1 indicates the bond with Z 2 ;
*2表示與Z1的鍵結鍵]。 *2 indicates the bonding bond with Z 1 ].
Z1表示的碳數1至12的烷二基可舉出與R115表示的碳數1至12的烷二基相同者。 Examples of the alkylenediyl group having 1 to 12 carbon atoms represented by Z 1 include the same ones as the alkylenediyl group having 1 to 12 carbon atoms represented by R 115 .
Z1表示的碳數6至18的2價芳香族烴基可列舉:伸苯基、伸萘基等。 Examples of the divalent aromatic hydrocarbon group having 6 to 18 carbon atoms represented by Z 1 include phenylene group, naphthylene group, and the like.
R1B、R1C、R1D、R1E及R1F表示的碳數1至6的烷基可舉出與R112表示的碳數1至6的烷基者。 Examples of the alkyl group having 1 to 6 carbon atoms represented by R 1B , R 1C , R 1D , R 1E and R 1F include the alkyl group having 1 to 6 carbon atoms represented by R 112 .
R2A、R2B、R2C、R2D、R2E及R2F表示的碳數1至18的2價烴基可列舉:亞甲基、伸乙基、丙烷-1,3-二基、丁烷-1,4-二基、戊烷-1,5-二基、己烷-1,6-二基、乙烷-1,1-二基、丙烷-1,2-二基、丁烷-1,3-二基、2-甲基丙烷 -1,3-二基、2-甲基丙烷-1,2-二基、戊烷-1,4-二基及2-甲基丁烷-1,4-二基等碳數1至18的烷二基;伸苯基、伸萘基等碳數6至18的2價芳香族烴基。 Examples of the divalent hydrocarbon group having 1 to 18 carbon atoms represented by R 2A , R 2B , R 2C , R 2D , R 2E and R 2F include: methylene, ethylidene, propane-1,3-diyl, butane -1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, ethane-1,1-diyl, propane-1,2-diyl, butane- 1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl and 2-methylbutane- Alkanediyl groups having 1 to 18 carbon atoms, such as 1,4-diyl; divalent aromatic hydrocarbon groups having 6 to 18 carbon atoms, such as phenylene group and naphthylene group.
Z1較理想為-O-R2A-*1(R2A更理想為碳數1至8的烷二基,更加理想為碳數4至8的烷二基)。 Z 1 is preferably -OR 2A -*1 (R 2A is more preferably an alkanediyl group having 1 to 8 carbon atoms, and even more preferably an alkanediyl group having 4 to 8 carbon atoms).
Z2較理想為*2-O-CO-、*2-O-SO2-、*2-NR1C-CO-(R1C更理想為氫原子)。 Z 2 is preferably *2-O-CO-, *2-O-SO 2 -, or *2-NR 1C -CO- (R 1C is more preferably a hydrogen atom).
式(II)表示的化合物較理想為式(IV)表示的化合物。 The compound represented by formula (II) is preferably a compound represented by formula (IV).
[R11、R12、R13、R14、R15、R16、R17及E11表示與上述相同的意義,惟,R13、R14、R15及R16中至少一者表示包含聚合性基的基]。 [R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and E 11 have the same meaning as above, but at least one of R 13 , R 14 , R 15 and R 16 means including polymerizable group].
式(I)表示的化合物可舉出下列記載的化合物。 Examples of the compound represented by formula (I) include the compounds described below.
式(II)表示的化合物可舉出下列記載的化合物。 Examples of the compound represented by formula (II) include the compounds described below.
A為乙烯性不飽和基的式(I)表示的化合物,例如可藉由使式(Ia)表示的化合物與式(c1)表示的化合物反應而獲得。 The compound represented by formula (I) in which A is an ethylenically unsaturated group can be obtained, for example, by reacting a compound represented by formula (Ia) and a compound represented by formula (c1).
[式(Ia)中的R1、R2、R3、R4、R5、R6及E1表示與上述相同意義,式(c1)中的Z3表示2價連結基,A1表示乙烯性聚合性基]。 [R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and E 1 in the formula (Ia) represent the same meanings as above, Z 3 in the formula (c1) represents a divalent linking group, and A 1 represents Ethylene polymerizable group].
相對於式(Ia)表示的化合物1莫耳,式(c1)表示的化合物的使用量較理想為0.5至5莫耳。 The usage amount of the compound represented by formula (c1) is preferably 0.5 to 5 moles relative to 1 mole of the compound represented by formula (Ia).
式(Ia)表示的化合物與式(c1)表示的化合物的反應可使用習知的酯化反應,較理想為在鹼及碳二亞胺縮合劑的存在下進行。鹼可列舉例如:三乙基胺、二異丙基乙基胺、吡啶、哌啶、吡咯啶、脯胺酸、N,N-二甲基胺基吡啶等。碳二亞胺縮合劑可列舉:N,N-二環己基碳二亞胺、N,N-二異丙基碳二亞胺、1-乙基-3-(3-二甲基胺基丙基)碳二亞胺鹽酸鹽等。相對於式(Ia)表示的化合物1莫耳,鹼的使用量較理想為0.001至0.5莫耳。相對於式(Ia)表示的化合物1莫耳,碳二亞胺縮合劑的使用量較理想為0.5至5莫耳。 The reaction between the compound represented by formula (Ia) and the compound represented by formula (c1) can be carried out using a conventional esterification reaction, and is preferably carried out in the presence of a base and a carbodiimide condensing agent. Examples of the base include triethylamine, diisopropylethylamine, pyridine, piperidine, pyrrolidine, proline, N,N-dimethylaminopyridine, and the like. Examples of carbodiimide condensing agents include: N,N-dicyclohexylcarbodiimide, N,N-diisopropylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropane) base) carbodiimide hydrochloride, etc. The usage amount of the base is preferably 0.001 to 0.5 mol relative to 1 mol of the compound represented by formula (Ia). The usage amount of the carbodiimide condensing agent is preferably 0.5 to 5 moles relative to 1 mole of the compound represented by formula (Ia).
式(Ia)表示的化合物與式(c1)表示的化合物的反應較理想為在有機溶劑中進行。有機溶劑可列舉:甲苯、乙腈、二氯甲烷、三氯甲烷等。 The reaction between the compound represented by formula (Ia) and the compound represented by formula (c1) is preferably carried out in an organic solvent. Examples of organic solvents include: toluene, acetonitrile, methylene chloride, chloroform, etc.
為了阻礙式(c1)表示的化合物所包含的乙烯性不飽和基彼此的反應亦可添加聚合抑制劑。聚合抑制劑可列舉:2,6-二第三丁基-4-甲基酚(BHT)、4-甲氧基酚等。 A polymerization inhibitor may be added in order to inhibit the reaction between the ethylenically unsaturated groups contained in the compound represented by formula (c1). Examples of polymerization inhibitors include 2,6-di-tert-butyl-4-methylphenol (BHT), 4-methoxyphenol, and the like.
式(Ia)表示的化合物與式(c1)表示的化合物的反應,係藉由混合式(Ia)表示的化合物與式(c1)表示的化合物而實施。 The reaction between the compound represented by formula (Ia) and the compound represented by formula (c1) is carried out by mixing the compound represented by formula (Ia) and the compound represented by formula (c1).
式(Ia)表示的化合物與式(c1)表示的化合物的反應溫度較理想為-20至120℃,反應時間通常以1至50小時較理想。 The reaction temperature of the compound represented by formula (Ia) and the compound represented by formula (c1) is preferably -20 to 120°C, and the reaction time is usually 1 to 50 hours.
式(Ia)表示的化合物可舉出下列記載的化合物。 Examples of the compound represented by formula (Ia) include the compounds described below.
式(c1)表示的化合物可列舉:丙烯酸4-羥基丁酯、丙烯酸2-羥基乙酯等。 Examples of the compound represented by formula (c1) include 4-hydroxybutyl acrylate, 2-hydroxyethyl acrylate, and the like.
式(Ia)表示的化合物係可藉由使式(Ib)表示的化合物與式(c2)表示的化合物反應而得到。 The compound represented by formula (Ia) can be obtained by reacting the compound represented by formula (Ib) and the compound represented by formula (c2).
[式中的R1、R2、R3、R4、R5、R6及E1表示與上述相同意義]。 [R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and E 1 in the formula have the same meanings as above].
相對於式(Ib)表示的化合物1莫耳,式(c2)表示的化合物的使用量較理想為0.5至5莫耳。 The usage amount of the compound represented by the formula (c2) is preferably 0.5 to 5 moles relative to 1 mole of the compound represented by the formula (Ib).
式(Ib)表示的化合物與式(c2)表示的化合物的反應較理想為在鹼的存在下進行。鹼可列舉例如:吡啶、吡咯啶、哌啶、三乙基胺、二異丙基乙基胺等。相對於式(Ib)表示的化合物1莫耳,鹼的使用量較理想為0.5至5莫耳。 The reaction between the compound represented by formula (Ib) and the compound represented by formula (c2) is preferably carried out in the presence of a base. Examples of the base include pyridine, pyrrolidine, piperidine, triethylamine, diisopropylethylamine, and the like. The usage amount of the base is preferably 0.5 to 5 moles relative to 1 mole of the compound represented by formula (Ib).
式(Ib)表示的化合物與式(c2)表示的化合物的反應較理想為在有機溶劑中進行。有機溶劑可列舉:乙腈、異丙醇、甲苯、三氯甲烷、二氯甲烷等。 The reaction between the compound represented by formula (Ib) and the compound represented by formula (c2) is preferably carried out in an organic solvent. Examples of organic solvents include: acetonitrile, isopropyl alcohol, toluene, chloroform, dichloromethane, etc.
式(Ib)表示的化合物與式(c2)表示的化合物的反應係藉由混合式(Ib)表示的化合物與式(c2)表示的化合物而實施。 The reaction between the compound represented by formula (Ib) and the compound represented by formula (c2) is carried out by mixing the compound represented by formula (Ib) and the compound represented by formula (c2).
式(Ib)表示的化合物與式(c2)表示的化合物的反應溫度較理想為0至120℃,反應時間通常以1至50小時較理想。 The reaction temperature of the compound represented by formula (Ib) and the compound represented by formula (c2) is preferably 0 to 120°C, and the reaction time is usually 1 to 50 hours.
樹脂(A)可為具有吲哚結構的結構單元的同元聚合物,亦可為包含具有吲哚結構的結構單元及其他結構單元的共聚物。樹脂(A)較理想為共聚物。 Resin (A) may be a homopolymer having a structural unit having an indole structure, or a copolymer including a structural unit having an indole structure and other structural units. The resin (A) is preferably a copolymer.
樹脂(A)可包含的具有吲哚結構的結構單元以外的結構單元可舉出例如下述群A記載的結構單元。 Examples of structural units other than the structural unit having an indole structure that the resin (A) may contain include structural units described in the following group A.
群A:源自(甲基)丙烯酸酯的結構單元、源自苯乙烯系單體的結構單元、源自乙烯系單體的結構單元、源自環氧化合物的結構單元、式(a)表示的結構單元、式(b)表示的結構單元及式(c)表示的結構單元; Group A: Structural unit derived from (meth)acrylate, structural unit derived from styrenic monomer, structural unit derived from vinyl monomer, structural unit derived from epoxy compound, represented by formula (a) The structural unit, the structural unit represented by formula (b) and the structural unit represented by formula (c);
[式中,Ra1表示2價烴基; [In the formula, R a1 represents a divalent hydrocarbon group;
Rb1及Rb2分別獨立地表示氫原子或烴基; R b1 and R b2 each independently represent a hydrogen atom or a hydrocarbon group;
Rc1及Rc2分別獨立地表示2價烴基]。 R c1 and R c2 each independently represent a divalent hydrocarbon group].
(甲基)丙烯酸酯可列舉:(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸正戊酯、(甲基)丙烯酸正己酯、(甲基)丙烯酸正庚酯、(甲基)丙烯酸正辛酯、(甲基)丙烯 酸正壬酯、(甲基)丙烯酸正癸酯、(甲基)丙烯酸正十二烷酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸硬脂酯等(甲基)丙烯酸的直鏈狀烷酯; (Meth)acrylic acid esters include: (meth)acrylic acid methyl ester, (meth)ethyl acrylate, (meth)acrylic acid n-propyl ester, (meth)acrylic acid n-butyl ester, (meth)acrylic acid n-pentyl ester Ester, n-hexyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, (meth)propylene Linear chain of (meth)acrylic acid such as n-nonyl acid, n-decyl (meth)acrylate, n-dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, etc. alkyl ester;
(甲基)丙烯酸異丙酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸異戊酯、(甲基)丙烯酸異己酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸異辛酯、(甲基)丙烯酸異壬酯、(甲基)丙烯酸異硬脂酯、(甲基)丙烯酸異戊酯等(甲基)丙烯酸的分支狀烷酯; Isopropyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, isopentyl (meth)acrylate, isohexyl (meth)acrylate, (meth)acrylic acid 2-Ethylhexyl, isooctyl (meth)acrylate, isononyl (meth)acrylate, isostearyl (meth)acrylate, isopentyl (meth)acrylate and other (meth)acrylic acids branched alkyl esters;
(甲基)丙烯酸環己酯、(甲基)丙烯酸異降莰酯、(甲基)丙烯酸金剛烷酯、(甲基)丙烯酸二環戊酯、(甲基)丙烯酸環十二烷基酯、(甲基)丙烯酸甲基環己酯、(甲基)丙烯酸三甲基環己酯、(甲基)丙烯酸第三丁基環己酯、α-乙氧基丙烯酸環己酯等(甲基)丙烯酸的含有脂環骨架的烷酯;(甲基)丙烯酸苯酯等(甲基)丙烯酸的含有芳香環骨架的酯;等。 Cyclohexyl (meth)acrylate, isonorbornyl (meth)acrylate, adamantyl (meth)acrylate, dicyclopentyl (meth)acrylate, cyclododecyl (meth)acrylate, Methylcyclohexyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, tert-butylcyclohexyl (meth)acrylate, α-ethoxycyclohexyl acrylate, etc. (Methyl) Alkyl esters of acrylic acid containing an alicyclic skeleton; esters of (meth)acrylic acid containing an aromatic ring skeleton such as phenyl (meth)acrylate; etc.
源自(甲基)丙烯酸酯的結構單元可舉出在(甲基)丙烯酸烷酯的烷基導入有取代基的含有取代基的(甲基)丙烯酸烷酯。含有取代基的(甲基)丙烯酸烷酯的取代基係取代烷基的氫原子的基,其具體例包含苯基、烷氧基、苯氧基。含有取代基的(甲基)丙烯酸烷酯,具體而言,可列舉:(甲基)丙烯酸2-甲氧基乙酯、(甲基)丙烯酸乙氧基甲酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸2-(2-苯氧基乙氧基)乙酯、(甲基)丙烯酸苯氧基二乙二醇酯、(甲基)丙烯酸苯氧基聚(乙二醇)酯等。 Examples of the structural unit derived from (meth)acrylate include substituent-containing (meth)acrylic acid alkyl ester in which a substituent is introduced into the alkyl group of (meth)acrylic acid alkyl ester. The substituent of the substituent-containing alkyl (meth)acrylate is a group that replaces the hydrogen atom of the alkyl group, and specific examples thereof include a phenyl group, an alkoxy group, and a phenoxy group. Specific examples of (meth)acrylic acid alkyl esters containing substituents include: (meth)acrylic acid 2-methoxyethyl ester, (meth)acrylic acid ethoxymethyl ester, (meth)acrylic acid phenoxy ethyl ester, 2-(2-phenoxyethoxy)ethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxy poly(ethylene glycol) (meth)acrylate Alcohol) ester, etc.
該等(甲基)丙烯酸酯可分別單獨地使用外,亦可使用不同的複數個。 These (meth)acrylates can be used individually or in plural different types.
本發明的樹脂(A)較佳為含有在(甲基)丙烯酸烷酯中,屬於同元聚合物的玻璃轉移溫度Tg未達0℃的源自(甲基)丙烯酸烷酯(a1)的結 構單元以及屬於同元聚合物的玻璃轉移溫度Tg為0℃以上的源自(甲基)丙烯酸烷酯(a2)的結構單元。此係提升有利於黏著層的高溫耐久性。(甲基)丙烯酸烷酯的同元聚合物的Tg可採用例如聚合物手冊(Polymer handbook;Wiley-Interscience)等的文獻值。 The resin (A) of the present invention preferably contains an alkyl (meth)acrylate (meth)acrylate and is a homopolymer having a glass transition temperature Tg of less than 0°C and is derived from the alkyl (meth)acrylate (a1). The structural unit and the structural unit derived from the alkyl (meth)acrylate (a2) belonging to the homopolymer have a glass transition temperature Tg of 0° C. or higher. This system improves the high-temperature durability of the adhesive layer. For the Tg of the homopolymer of the alkyl (meth)acrylate, the value from literature such as Polymer Handbook (Wiley-Interscience) can be used.
(甲基)丙烯酸烷酯(a1)的具體例包含:丙烯酸乙酯、丙烯酸正-及異-丙酯、丙烯酸正-及異-丁酯、丙烯酸正-戊酯、丙烯酸正-及異-己酯、丙烯酸正-庚酯、丙烯酸正-及異-辛酯、丙烯酸2-乙基己酯、丙烯酸正-及異-壬酯、丙烯酸正-及異-癸酯、丙烯酸正-十二烷基酯等烷基的碳數為2至12左右的(甲基)丙烯酸烷酯。 Specific examples of (meth)acrylic acid alkyl ester (a1) include: ethyl acrylate, n- and iso-propyl acrylate, n- and iso-butyl acrylate, n-pentyl acrylate, n- and iso-hexyl acrylate Esters, n-heptyl acrylate, n- and iso-octyl acrylate, 2-ethylhexyl acrylate, n- and iso-nonyl acrylate, n- and iso-decyl acrylate, n-dodecyl acrylate Alkyl (meth)acrylate, such as ester, has an alkyl group with a carbon number of about 2 to 12.
(甲基)丙烯酸烷酯(a1),可只使用1種,亦可併用2種以上。此外,從積層光學膜時的追隨性、重工性的觀點而言,較理想為丙烯酸正丁酯、丙烯酸正辛酯、丙烯酸2-乙基己酯等。 Only one type of (meth)acrylic acid alkyl ester (a1) may be used, or two or more types may be used in combination. In addition, from the viewpoint of followability and reworkability when laminating an optical film, n-butyl acrylate, n-octyl acrylate, 2-ethylhexyl acrylate, etc. are preferred.
(甲基)丙烯酸烷酯(a2)為(甲基)丙烯酸烷酯(a1)以外的(甲基)丙烯酸烷酯。(甲基)丙烯酸烷酯(a2)的具體例包含:丙烯酸甲酯、丙烯酸環己酯、丙烯酸異降莰酯、丙烯酸硬脂酯、丙烯酸第三丁酯等。 The (meth)acrylic acid alkyl ester (a2) is a (meth)acrylic acid alkyl ester other than the (meth)acrylic acid alkyl ester (a1). Specific examples of (meth)acrylic acid alkyl ester (a2) include methyl acrylate, cyclohexyl acrylate, isorbornyl acrylate, stearyl acrylate, tert-butyl acrylate, and the like.
(甲基)丙烯酸烷酯(a2)可只使用1種,亦可併用2種以上。此外,從高溫耐久性的觀點而言,(甲基)丙烯酸烷酯(a2)較理想為包含丙烯酸甲酯、丙烯酸環己酯、丙烯酸異降莰酯,更理想為包含丙烯酸甲酯。 Only one type of (meth)acrylic acid alkyl ester (a2) may be used, or two or more types may be used in combination. Furthermore, from the viewpoint of high-temperature durability, the (meth)acrylic acid alkyl ester (a2) preferably contains methyl acrylate, cyclohexyl acrylate, and isorbornyl acrylate, and more preferably contains methyl acrylate.
再者,源自(甲基)丙烯酸酯的結構單元亦可舉出源自具有極性官能基的(甲基)丙烯酸酯的結構單元。 In addition, the structural unit derived from (meth)acrylic acid ester may also include the structural unit derived from (meth)acrylic acid ester having a polar functional group.
具有極性官能基的(甲基)丙烯酸酯單體可列舉:(甲基)丙烯酸1-羥基甲酯、(甲基)丙烯酸1-羥基乙酯、(甲基)丙烯酸1-羥基庚酯、(甲基)丙烯酸 1-羥基丁酯、(甲基)丙烯酸1-羥基戊酯、(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基丁酯、(甲基)丙烯酸2-羥基戊酯、(甲基)丙烯酸2-羥基己酯、(甲基)丙烯酸3-羥基丙酯、(甲基)丙烯酸3-羥基丁酯、(甲基)丙烯酸3-羥基戊酯、(甲基)丙烯酸3-羥基己酯、(甲基)丙烯酸3-羥基庚酯、(甲基)丙烯酸4-羥基丁酯、(甲基)丙烯酸4-羥基戊酯、(甲基)丙烯酸4-羥基己酯、(甲基)丙烯酸4-羥基庚酯、(甲基)丙烯酸4-羥基辛酯、(甲基)丙烯酸2-氯-2-羥基丙酯、(甲基)丙烯酸3-氯-2-羥基丙酯、(甲基)丙烯酸2-羥基-3-苯氧基丙酯、(甲基)丙烯酸5-羥基戊酯、(甲基)丙烯酸5-羥基己酯、(甲基)丙烯酸5-羥基庚酯、(甲基)丙烯酸5-羥基辛酯、(甲基)丙烯酸5-羥基壬酯、(甲基)丙烯酸6-羥基己酯、(甲基)丙烯酸6-羥基庚酯、(甲基)丙烯酸6-羥基辛酯、(甲基)丙烯酸6-羥基壬酯、(甲基)丙烯酸6-羥基癸酯、(甲基)丙烯酸7-羥基庚酯、(甲基)丙烯酸7-羥基辛酯、(甲基)丙烯酸7-羥基壬酯、(甲基)丙烯酸7-羥基癸酯、(甲基)丙烯酸7-羥基十一烷基酯、(甲基)丙烯酸8-羥基辛酯、(甲基)丙烯酸8-羥基壬酯、(甲基)丙烯酸8-羥基癸酯、(甲基)丙烯酸8-羥基十一烷基酯、(甲基)丙烯酸8-羥基十二烷基酯、(甲基)丙烯酸9-羥基壬酯、(甲基)丙烯酸9-羥基癸酯、(甲基)丙烯酸9-羥基十一烷基酯、(甲基)丙烯酸9-羥基十二烷基酯、(甲基)丙烯酸9-羥基十三烷基酯、(甲基)丙烯酸10-羥基癸酯、(甲基)丙烯酸10-羥基十一烷基酯、(甲基)丙烯酸10-羥基十二烷基酯、(甲基)丙烯酸10-羥基十三烷基酯、(甲基)丙烯酸10-羥基十四烷基酯、(甲基)丙烯酸11-羥基十一烷基酯、(甲基)丙烯酸11-羥基十二烷基酯、(甲基)丙烯酸11-羥基十三烷基酯、(甲基)丙烯酸11-羥基十四烷基酯、(甲基)丙烯酸11-羥基十五烷基酯、(甲基) 丙烯酸12-羥基十二烷基酯、(甲基)丙烯酸12-羥基十三烷基酯、(甲基)丙烯酸12-羥基十四烷基酯、(甲基)丙烯酸13-羥基十五烷基酯、(甲基)丙烯酸14-羥基十四烷基酯、(甲基)丙烯酸14-羥基十五烷基酯、(甲基)丙烯酸15-羥基十五烷基酯、(甲基)丙烯酸15-羥基十七烷基酯等具有羥基的(甲基)丙烯酸酯等。 Examples of (meth)acrylate monomers having polar functional groups include: (meth)acrylic acid 1-hydroxymethyl ester, (meth)acrylic acid 1-hydroxyethyl ester, (meth)acrylic acid 1-hydroxyheptyl ester, (meth)acrylic acid 1-hydroxyheptyl ester, Methacrylate 1-hydroxybutyl ester, 1-hydroxypentyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-hydroxypentyl (meth)acrylate, 2-hydroxyhexyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, (meth)acrylic acid 3 -Hydroxypentyl ester, 3-hydroxyhexyl (meth)acrylate, 3-hydroxyheptyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 4-hydroxypentyl (meth)acrylate, ( 4-hydroxyhexyl methacrylate, 4-hydroxyheptyl (meth)acrylate, 4-hydroxyoctyl (meth)acrylate, 2-chloro-2-hydroxypropyl (meth)acrylate, (meth)acrylate )3-chloro-2-hydroxypropyl acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 5-hydroxypentyl (meth)acrylate, 5-hydroxyhexyl (meth)acrylate , 5-hydroxyheptyl (meth)acrylate, 5-hydroxyoctyl (meth)acrylate, 5-hydroxynonyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, (meth)acrylic acid 6-hydroxyheptyl ester, 6-hydroxyoctyl (meth)acrylate, 6-hydroxynonyl (meth)acrylate, 6-hydroxydecyl (meth)acrylate, 7-hydroxyheptyl (meth)acrylate, 7-hydroxyoctyl (meth)acrylate, 7-hydroxynonyl (meth)acrylate, 7-hydroxydecyl (meth)acrylate, 7-hydroxyundecyl (meth)acrylate, (meth)acrylate ) 8-hydroxyoctyl acrylate, 8-hydroxynonyl (meth)acrylate, 8-hydroxydecyl (meth)acrylate, 8-hydroxyundecyl (meth)acrylate, 8-(meth)acrylate -Hydroxydodecyl ester, 9-hydroxynonyl (meth)acrylate, 9-hydroxydecyl (meth)acrylate, 9-hydroxyundecyl (meth)acrylate, (meth)acrylic acid 9 -Hydroxydodecyl ester, 9-hydroxytridecyl (meth)acrylate, 10-hydroxydecyl (meth)acrylate, 10-hydroxyundecyl (meth)acrylate, (meth)acrylate ) 10-hydroxydodecyl acrylate, 10-hydroxytridecyl (meth)acrylate, 10-hydroxytetradecyl (meth)acrylate, 11-hydroxyundecane (meth)acrylate ester, 11-hydroxydodecyl (meth)acrylate, 11-hydroxytridecyl (meth)acrylate, 11-hydroxytetradecyl (meth)acrylate, (meth)acrylic acid 11-Hydroxypentadecyl ester, (methyl) 12-hydroxydodecyl acrylate, 12-hydroxytridecyl (meth)acrylate, 12-hydroxytetradecyl (meth)acrylate, 13-hydroxypentadecyl (meth)acrylate Ester, 14-hydroxytetradecyl (meth)acrylate, 14-hydroxypentadecyl (meth)acrylate, 15-hydroxypentadecyl (meth)acrylate, (meth)acrylic acid 15 - (Meth)acrylate having a hydroxyl group such as hydroxyheptadecyl ester and the like.
苯乙烯系單體可列舉:苯乙烯;甲基苯乙烯、二甲基苯乙烯、三甲基苯乙烯、乙基苯乙烯、二乙基苯乙烯、三乙基苯乙烯、丙基苯乙烯、丁基苯乙烯、己基苯乙烯、庚基苯乙烯、辛基苯乙烯等烷基苯乙烯;氟苯乙烯、氯苯乙烯、溴苯乙烯、二溴苯乙烯、碘苯乙烯等鹵化苯乙烯;硝基苯乙烯;乙醯基苯乙烯;甲氧基苯乙烯;以及二乙烯基苯。 Examples of styrenic monomers include: styrene; methylstyrene, dimethylstyrene, trimethylstyrene, ethylstyrene, diethylstyrene, triethylstyrene, propylstyrene, Alkyl styrenes such as butylstyrene, hexylstyrene, heptylstyrene, and octylstyrene; halogenated styrenes such as fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, and iodostyrene; nitrate styrene; acetyl styrene; methoxystyrene; and divinylbenzene.
乙烯系單體可列舉:乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯、2-乙基己酸乙烯酯、月桂酸乙烯酯等脂肪酸乙烯酯;氯乙烯、溴乙烯等鹵化乙烯;偏二氯乙烯等亞乙烯基鹵化物;乙烯基吡啶、乙烯基吡咯烷酮、乙烯基味唑等含氮雜芳香族乙烯;丁二烯、異戊二烯氯丁二烯等共軛二烯;以及丙烯腈、甲基丙烯腈等不飽和腈。 Examples of vinyl monomers include: vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, vinyl laurate and other fatty acid vinyl esters; vinyl chloride, vinyl bromide and other halogenated ethylenes; Vinylidene halides such as vinyl chloride; nitrogen-containing heteroaromatic vinyls such as vinylpyridine, vinylpyrrolidone, and vinylpyrrolidone; conjugated dienes such as butadiene, isoprene, chloroprene, etc.; and acrylonitrile , methacrylonitrile and other unsaturated nitriles.
所謂環氧化合物係指分子內具有環氧基的化合物。環氧基亦可為環氧基環戊烷結構、環氧基環己烷結構等與脂環式環鍵結的環氧基。 The so-called epoxy compound refers to a compound having an epoxy group in the molecule. The epoxy group may also be an epoxy group bonded to an alicyclic ring such as an epoxycyclopentane structure or an epoxycyclohexane structure.
環氧化合物可列舉:3,4-環氧基環己烷羧酸3,4-環氧基環己基甲酯、3,4-環氧基-6-甲基環己烷羧酸3,4-環氧基-6-甲基環己基甲酯、伸乙烯基雙(3,4-環氧基環己烷羧酸酯)、己二酸雙(3,4-環氧基環己基甲酯)、己二酸雙(3,4-環氧基-6-甲基環己基甲酯)、二乙二醇雙(3,4-環氧基環己基甲基醚)、乙二醇雙(3,4-環氧基環己基甲基醚)、2,3,14,15-二環氧基-7,11,18,21-四氧 三螺環[5.2.2.5.2.2]二十一烷、3-(3,4-環氧基環己基)-8,9-環氧基-1,5二氧螺環[5.5]十一烷、4-乙烯基環己烯二氧化物、檸檬烯二氧化物、雙(2,3-環氧基環戊基醚)、二環戊二烯二氧化物、1,4-丁二醇二環氧丙基醚、1,6-己二醇二環氧丙基醚、新戊二醇二環氧丙基醚、三羥甲基丙烷三環氧丙基醚、季戊四醇四環氧丙基醚等。 Epoxy compounds include: 3,4-epoxycyclohexanecarboxylic acid 3,4-epoxycyclohexylmethyl ester, 3,4-epoxy-6-methylcyclohexanecarboxylic acid 3,4 -Epoxy-6-methylcyclohexylmethyl ester, vinylene bis(3,4-epoxycyclohexanecarboxylate), adipate bis(3,4-epoxycyclohexylmethyl ester) ), adipate bis(3,4-epoxy-6-methylcyclohexylmethyl ester), diethylene glycol bis(3,4-epoxycyclohexylmethyl ether), ethylene glycol bis( 3,4-epoxycyclohexyl methyl ether), 2,3,14,15-diepoxy-7,11,18,21-tetraoxy Trispiro[5.2.2.5.2.2]undecane, 3-(3,4-epoxycyclohexyl)-8,9-epoxy-1,5dioxspiro[5.5]undecan , 4-vinylcyclohexene dioxide, limonene dioxide, bis(2,3-epoxycyclopentyl ether), dicyclopentadiene dioxide, 1,4-butanediol bicyclo Oxypropyl ether, 1,6-hexanediol diepoxypropyl ether, neopentyl glycol diepoxypropyl ether, trimethylolpropane triepoxypropyl ether, pentaerythritol tetraepoxypropyl ether, etc. .
衍生式(a)表示的結構單元的化合物,例如,可藉由二異氰酸酯化合物與聚醇的反應而合成。 The compound derived from the structural unit represented by formula (a) can be synthesized, for example, by the reaction of a diisocyanate compound and a polyol.
衍生式(b)表示的結構單元的化合物,例如,可藉由使鹵化矽烷、具有羥基的矽烷反應而合成。 The compound of the structural unit represented by the derivative formula (b) can be synthesized, for example, by reacting a halogenated silane or a silane having a hydroxyl group.
衍生式(c)表示的結構單元的化合物,例如,可藉由聚羧酸與聚醇的反應等而合成。 The compound derived from the structural unit represented by formula (c) can be synthesized, for example, by reaction of polycarboxylic acid and polyol.
選自群A記載的結構單元中之結構單元較理想為源自(甲基)丙烯酸酯的結構單元。源自(甲基)丙烯酸酯的結構單元較理想為(甲基)丙烯酸烷酯及具有羥基的(甲基)丙烯酸烷酯。 The structural unit selected from the structural units described in Group A is preferably a structural unit derived from (meth)acrylate. The structural unit derived from (meth)acrylate is preferably an alkyl (meth)acrylate and an alkyl (meth)acrylate having a hydroxyl group.
本發明的樹脂(A)亦可更包含其他結構單元(有稱為結構單元(aa)的情況)。具體而言,可列舉:源自(甲基)丙烯醯胺系單體的結構單元、源自具有羧基的單體的結構單元、源自具有雜環基的單體的結構單元、源自具有取代或無取代的胺基的單體的結構單元等。 The resin (A) of the present invention may further contain other structural units (sometimes called structural units (aa)). Specifically, structural units derived from a (meth)acrylamide-based monomer, structural units derived from a monomer having a carboxyl group, structural units derived from a monomer having a heterocyclic group, structural units derived from a monomer having a carboxyl group, Structural units of monomers with substituted or unsubstituted amine groups, etc.
(甲基)丙烯醯胺系單體可列舉:N-羥甲基(甲基)丙烯醯胺、N-(2-羥基乙基)(甲基)丙烯醯胺、N-(3-羥基丙基)(甲基)丙烯醯胺、N-(4-羥基丁基)(甲基)丙烯醯胺、N-(5-羥基戊基)(甲基)丙烯醯胺、N-(6-羥基己基)(甲基)丙烯醯胺、N,N-二甲基(甲基)丙烯醯胺、N,N-二乙基(甲基)丙烯 醯胺、N-異丙基(甲基)丙烯醯胺、N-(3-二甲基胺基丙基)(甲基)丙烯醯胺、N-(1,1-二甲基-3-氧丁基)(甲基)丙烯醯胺、N-[2-(2-氧-1-咪唑啉基)乙基](甲基)丙烯醯胺、2-丙烯醯基胺基-2-甲基-1-丙烷磺酸、N-(甲氧基甲基)丙烯醯胺、N-(乙氧基甲基)(甲基)丙烯醯胺、N-(丙氧基甲基)(甲基)丙烯醯胺、N-(1-甲基乙氧基甲基)(甲基)丙烯醯胺、N-(1-甲基丙氧基甲基)(甲基)丙烯醯胺、N-(2-甲基丙氧基甲基)(甲基)丙烯醯胺、N-(丁氧基甲基)(甲基)丙烯醯胺、N-(1,1-二甲基乙氧基甲基)(甲基)丙烯醯胺、N-(2-甲氧基乙基)(甲基)丙烯醯胺、N-(2-乙氧基乙基)(甲基)丙烯醯胺、N-(2-丙氧基乙基)(甲基)丙烯醯胺、N-[2-(1-甲基乙氧基)乙基](甲基)丙烯醯胺、N-[2-(1-甲基丙氧基)乙基](甲基)丙烯醯胺、N-[2-(2-甲基丙氧基)乙基](甲基)丙烯醯胺、N-(2-丁氧基乙基)(甲基)丙烯醯胺、N-[2-(1,1-二甲基乙氧基)乙基](甲基)丙烯醯胺等。其中,較理想為N-(甲氧基甲基)丙烯醯胺、N-(乙氧基甲基)丙烯醯胺、N-(丙氧基甲基)丙烯醯胺、N-(丁氧基甲基)丙烯醯胺以及N-(2-甲基丙氧基甲基)丙烯醯胺。 Examples of (meth)acrylamide-based monomers include: N-hydroxymethyl(meth)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, N-(3-hydroxypropyl) (meth)acrylamide, N-(4-hydroxybutyl)(meth)acrylamide, N-(5-hydroxypentyl)(meth)acrylamide, N-(6-hydroxy Hexyl)(meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)propylene Amide, N-isopropyl(meth)acrylamide, N-(3-dimethylaminopropyl)(meth)acrylamide, N-(1,1-dimethyl-3- Oxybutyl)(meth)acrylamide, N-[2-(2-oxo-1-imidazolinyl)ethyl](meth)acrylamide, 2-acrylamide-2-methyl Propane-1-propanesulfonic acid, N-(methoxymethyl)acrylamide, N-(ethoxymethyl)(meth)acrylamide, N-(propoxymethyl)(methyl )Acrylamide, N-(1-methylethoxymethyl)(meth)acrylamide, N-(1-methylpropoxymethyl)(meth)acrylamide, N-( 2-Methylpropoxymethyl)(meth)acrylamide, N-(butoxymethyl)(meth)acrylamide, N-(1,1-dimethylethoxymethyl )(meth)acrylamide, N-(2-methoxyethyl)(meth)acrylamide, N-(2-ethoxyethyl)(meth)acrylamide, N-( 2-propoxyethyl)(meth)acrylamide, N-[2-(1-methylethoxy)ethyl](meth)acrylamide, N-[2-(1-methyl Propoxy)ethyl](meth)acrylamide, N-[2-(2-methylpropoxy)ethyl](meth)acrylamide, N-(2-butoxyethyl) (meth)acrylamide, N-[2-(1,1-dimethylethoxy)ethyl](meth)acrylamide, etc. Among them, N-(methoxymethyl)acrylamide, N-(ethoxymethyl)acrylamide, N-(propoxymethyl)acrylamide, N-(butoxymethyl)acrylamide Meth)acrylamide and N-(2-methylpropoxymethyl)acrylamide.
具有羧基的單體可列舉:(甲基)丙烯酸、(甲基)丙烯酸羧基烷酯(例如,(甲基)丙烯酸羧基乙酯、(甲基)丙烯酸羧基戊酯)、順丁烯二酸、順丁烯二酸酐、反丁烯二酸、巴豆酸,較理想為丙烯酸。 Examples of the monomer having a carboxyl group include: (meth)acrylic acid, carboxyalkyl (meth)acrylate (for example, carboxyethyl (meth)acrylate, carboxypentyl (meth)acrylate), maleic acid, Maleic anhydride, fumaric acid, crotonic acid, preferably acrylic acid.
具有雜環基的單體可列舉:丙烯醯基嗎啉、乙烯基己內醯胺、N-乙烯基-2-吡咯烷酮、乙烯基吡啶、(甲基)丙烯酸四氫糠酯、己內酯改性丙烯酸四氫糠酯、(甲基)丙烯酸3,4-環氧基環己基甲酯、(甲基)丙烯酸環氧丙酯、2,5-二氫呋喃等。 Monomers with heterocyclic groups include: acryloylmorpholine, vinylcaprolactam, N-vinyl-2-pyrrolidone, vinylpyridine, (meth)acrylic acid tetrahydrofurfuryl ester, caprolactone modified Tetrahydrofurfuryl acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, glycidyl (meth)acrylate, 2,5-dihydrofuran, etc.
具有取代或無取代的胺基的單體可列舉:(甲基)丙烯酸胺基乙酯、(甲基)丙烯酸N,N-二甲基胺基乙酯、(甲基)丙烯酸二甲基胺基丙酯等。 Examples of the monomer having a substituted or unsubstituted amine group include: (meth)aminoethyl acrylate, (meth)acrylic acid N,N-dimethylaminoethyl, (meth)acrylic acid dimethylamine Propyl ester, etc.
具有吲哚結構的結構單元及選自群A的結構單元以外的結構單元(aa)較理想為具有羧基的單體。 The structural unit having an indole structure and the structural unit (aa) selected from other than the structural units of Group A are preferably monomers having a carboxyl group.
相對於樹脂(A)所包含的全部結構單元100質量份,具有吲哚結構的結構單元的含量較理想為0.01至50質量份,更理想為0.1至20質量份,更加理想為0.5至15質量份。 The content of the structural unit having an indole structure is preferably 0.01 to 50 parts by mass, more preferably 0.1 to 20 parts by mass, and even more preferably 0.5 to 15 parts by mass relative to 100 parts by mass of all structural units contained in the resin (A) share.
相對於樹脂(A)的全部結構單元100質量份,選自群A記載的結構單元中至少一者的結構單元的含量較理想為50質量份以上,更理想為55至99.99質量份,更加理想為60至85質量份。 The content of at least one structural unit selected from the structural units described in Group A is preferably 50 parts by mass or more, more preferably 55 to 99.99 parts by mass, based on 100 parts by mass of all structural units of the resin (A), and even more preferably 60 to 85 parts by mass.
樹脂(A)含有結構單元(aa)時,相對於樹脂(A)的全部結構單元100質量份,較理想為20質量份以下,更理想為0.5質量份以上15質量份以下,更加理想為0.5質量份以上10質量份以下,特別理想為1質量份以上7質量份以下。 When the resin (A) contains the structural unit (aa), it is preferably 20 parts by mass or less, more preferably 0.5 parts by mass or more and 15 parts by mass or less, still more preferably 0.5, relative to 100 parts by mass of all the structural units of the resin (A). The amount is not less than 10 parts by mass and not more than 10 parts by mass, particularly preferably not less than 1 part by mass and not more than 7 parts by mass.
樹脂(A)含有源自具有羥基的(甲基)丙烯酸烷酯的結構單元時,相對於樹脂(A)的全部結構單元100質量份,該結構單元的含量較理想為20質量份以下,更理想為0.5質量份以上15質量份以下,更加理想為0.5質量份以上10質量份以下,特別理想為1質量份以上7質量份以下。 When the resin (A) contains a structural unit derived from an alkyl (meth)acrylate having a hydroxyl group, the content of the structural unit is preferably 20 parts by mass or less based on 100 parts by mass of all the structural units of the resin (A), and more preferably It is ideally 0.5 parts by mass or more and 15 parts by mass or less, more preferably 0.5 parts by mass or more and 10 parts by mass or less, particularly preferably 1 part by mass or more and 7 parts by mass or less.
從防止可積層於由黏著劑組成物形成的黏著劑層的外面之分隔膜的剝離力亢進的觀點而言,較理想為實質上不包含具有胺基的單體。在此,所 謂實質上不包含具有胺基的單體係指在構成樹脂(A)的全部結構單元100質量份中,源自具有胺基的單體的結構單元的含量為0.1質量份以下。 From the viewpoint of preventing an increase in the peeling force of a separator film that can be laminated on the outer surface of an adhesive layer formed of an adhesive composition, it is preferable that the monomer having an amine group is not substantially included. Here, all To say that the monomer having an amine group is not substantially included means that the content of the structural unit derived from the monomer having an amine group is 0.1 parts by mass or less in 100 parts by mass of all the structural units constituting the resin (A).
由樹脂(A)與後述交聯劑(B)的反應性的點而言,樹脂(A)較理想為包含源自具有羥基的(甲基)丙烯酸烷酯的結構單元或源自具有羧基的(甲基)丙烯酸烷酯的結構單元,更理想為包含源自具有羥基的(甲基)丙烯酸烷酯的結構單元及源自具有羧基的(甲基)丙烯酸烷酯的結構單元中之一。具有羥基的(甲基)丙烯酸烷酯較理想為丙烯酸2-羥基乙酯、丙烯酸3-羥基丙酯、丙烯酸4-羥基丁酯、丙烯酸5-羥基戊酯、丙烯酸6-羥基己酯。特別是,藉由使用丙烯酸2-羥基乙酯、丙烯酸4-羥基丁酯及丙烯酸5-羥基戊酯,可得到良好的耐久性。具有羧基的單體較理想為使用丙烯酸。 From the viewpoint of the reactivity of the resin (A) and the cross-linking agent (B) described below, the resin (A) preferably contains a structural unit derived from an alkyl (meth)acrylate having a hydroxyl group or a structural unit derived from an alkyl (meth)acrylate having a carboxyl group. The structural unit of the (meth)acrylic acid alkyl ester more preferably contains one of a structural unit derived from the (meth)acrylic acid alkyl ester having a hydroxyl group and a structural unit derived from the (meth)acrylic acid alkyl ester having a carboxyl group. The (meth)acrylic acid alkyl ester having a hydroxyl group is preferably 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 5-hydroxypentyl acrylate, or 6-hydroxyhexyl acrylate. In particular, good durability can be obtained by using 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate, and 5-hydroxypentyl acrylate. As the monomer having a carboxyl group, acrylic acid is preferably used.
本發明的樹脂(A)的重量平均分子量(Mw),較理想為30萬至250萬,更理想為50萬至200萬。重量平均分子量為30萬以上時,提升高溫環境的黏著劑層的耐久性,容易抑制被黏著物與黏著劑層之間的浮起剝離、黏著劑層的聚集破壞等不良情形。重量平均分子量為250萬以下時,就將加工黏著劑組成物例如製成片狀(塗佈於基材)時的塗佈性的觀點而言為有利。從兼具黏著劑層的耐久性及黏著劑組成物的塗佈性的觀點而言,重量平均分子量較理想為60萬至180萬,更理想為70萬至170萬,更加理想為100萬至160萬。再者,以重量平均分子量(Mw)與數量平均分子量(Mn)的比表示的分子量分佈(Mw/Mn),通常為2至10,較理想為3至8。重量平均分子量可藉由凝膠滲透層析儀分析,並且為換算成聚苯乙烯的值。 The weight average molecular weight (Mw) of the resin (A) of the present invention is preferably 300,000 to 2.5 million, more preferably 500,000 to 2,000,000. When the weight average molecular weight is 300,000 or more, the durability of the adhesive layer in high-temperature environments is improved, and undesirable phenomena such as floating and peeling between the adherend and the adhesive layer and aggregation and damage of the adhesive layer are easily suppressed. When the weight average molecular weight is 2.5 million or less, it is advantageous from the viewpoint of applicability when the processing adhesive composition is formed into a sheet (coated on a base material), for example. From the viewpoint of achieving both the durability of the adhesive layer and the coating properties of the adhesive composition, the weight average molecular weight is preferably 600,000 to 1.8 million, more preferably 700,000 to 1.7 million, and even more preferably 1 million to 1.8 million. 1.6 million. Furthermore, the molecular weight distribution (Mw/Mn) expressed as the ratio of the weight average molecular weight (Mw) and the number average molecular weight (Mn) is usually 2 to 10, and preferably 3 to 8. The weight average molecular weight can be analyzed by gel permeation chromatography and is a value converted to polystyrene.
本發明的樹脂(A)在使其溶解於乙酸乙酯並且成為濃度20質量%的溶液時,25℃下的黏度較理想為20Pa‧s以下,更理想為0.1至15Pa‧s。該範圍的黏度時,從於基材塗佈黏著劑組成物時的塗佈性的觀點而言為有利。此外,黏度可藉由布魯克菲爾德黏度計測定。 When the resin (A) of the present invention is dissolved in ethyl acetate and becomes a solution with a concentration of 20% by mass, the viscosity at 25°C is preferably 20 Pa‧s or less, and more preferably 0.1 to 15 Pa‧s. A viscosity within this range is advantageous from the viewpoint of coating properties when applying the adhesive composition to a base material. Additionally, viscosity can be measured with a Brookfield viscometer.
本發明的樹脂(A)可藉由例如溶液聚合法、總體聚合法、懸浮聚合法、乳化聚合法等習知方法製造,特別理想是溶液聚合法。溶液聚合法可舉出混合具有吲哚結構的單體、因應所需的衍生為群A記載的結構單元之單體及有機溶劑,在氮環境下,添加熱聚合起始劑,在40至90℃,較理想為50至80℃左右的溫度條件下,攪拌3至15小時的方法。為了控制反應,亦可在聚合中連續地或間歇地添加單體、熱聚合起始劑。該單體、熱聚合起始劑亦可為添加於有機溶劑的狀態。 The resin (A) of the present invention can be produced by conventional methods such as solution polymerization, bulk polymerization, suspension polymerization, and emulsion polymerization. The solution polymerization is particularly preferred. Examples of the solution polymerization method include mixing a monomer having an indole structure, a monomer derived into a structural unit described in Group A as required, and an organic solvent, adding a thermal polymerization initiator in a nitrogen environment, and heating at 40 to 90 ℃, preferably about 50 to 80 ℃, stirring for 3 to 15 hours. In order to control the reaction, monomers and thermal polymerization initiators can also be added continuously or intermittently during polymerization. The monomer and thermal polymerization initiator may be added to an organic solvent.
聚合起始劑可使用熱聚合起始劑、光聚合起始劑。光聚合起始劑可舉出4-(2-羥基乙氧基)苯基(2-羥基-2-丙基)酮等。熱聚合起始劑可列舉:2,2’-偶氮雙異丁腈、2,2’-偶氮雙(2-甲基丁腈)、1,1’-偶氮雙(環己烷-1-甲腈)、2,2’-偶氮雙(2,4-二甲基戊腈)、2,2’-偶氮雙(2,4-二甲基-4-甲氧基戊腈)、二甲基-2,2’-偶氮雙(2-甲基丙酸酯)、2,2’-偶氮雙(2-羥基甲基丙腈)等偶氮系化合物;十二烷基過氧化物、第三丁基過氧化氫、過氧化苯甲醯、過氧化苯甲酸第三丁酯、氫過氧化異丙苯、過氧化二碳酸二異丙酯、過氧化二碳酸二丙酯、過氧化新癸酸第三丁酯、過氧化新戊酸第三丁酯、(3,5,5-三甲基己醯基)過氧化物等有機過氧化物;過硫酸鉀、過硫酸銨、過氧化氫等無機過氧化物等。再者,亦可使用併用了過氧化物與還原劑的氧化還原系引發劑等。 As the polymerization initiator, a thermal polymerization initiator or a photopolymerization initiator can be used. Examples of the photopolymerization initiator include 4-(2-hydroxyethoxy)phenyl(2-hydroxy-2-propyl)one and the like. Examples of thermal polymerization initiators include: 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane- 1-carbonitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile) ), dimethyl-2,2'-azobis(2-methylpropionate), 2,2'-azobis(2-hydroxymethylpropionitrile) and other azo compounds; dodecane Hydroperoxide, tert-butyl hydroperoxide, benzoyl peroxide, tert-butyl peroxybenzoate, cumene hydroperoxide, diisopropyl peroxydicarbonate, dipropylene peroxydicarbonate ester, tert-butyl peroxyneodecanoate, tert-butyl peroxypivalate, (3,5,5-trimethylhexyl) peroxide and other organic peroxides; potassium persulfate, peroxyperoxide Inorganic peroxides such as ammonium sulfate and hydrogen peroxide. Furthermore, a redox-based initiator using a peroxide and a reducing agent in combination can also be used.
相對於構成樹脂(A)的單體的總量100質量份,聚合起始劑的比例為0.001至5質量份左右。樹脂(A)的聚合亦可使用藉由活性能量線(例如,紫外線等)進行的聚合法。 The proportion of the polymerization initiator is approximately 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of monomers constituting the resin (A). The polymerization method using active energy rays (for example, ultraviolet rays, etc.) can also be used for the polymerization of the resin (A).
有機溶劑可列舉:甲苯、二甲苯等芳香族烴類;乙酸乙酯、乙酸丁酯等酯類;丙醇、異丙醇等脂肪族醇類;丙酮、甲基乙基酮、甲基異丁基酮等酮類等。 Examples of organic solvents include: aromatic hydrocarbons such as toluene and xylene; esters such as ethyl acetate and butyl acetate; aliphatic alcohols such as propanol and isopropyl alcohol; acetone, methyl ethyl ketone, and methyl isobutyl Ketones, etc.
在黏著劑組成物的固體成分100質量%中,樹脂(A)的含量通常為60質量%至99.99質量%,較理想為70質量%至99.9質量%,更理想為80質量%至99.7質量%。 In 100 mass % of the solid content of the adhesive composition, the content of the resin (A) is usually 60 mass % to 99.99 mass %, more preferably 70 mass % to 99.9 mass %, more preferably 80 mass % to 99.7 mass % .
〈交聯劑(B)〉 〈Crosslinking agent (B)〉
本發明的黏著劑組成物可包含交聯劑(B)。 The adhesive composition of the present invention may contain a cross-linking agent (B).
交聯劑(B)可列舉:異氰酸酯系交聯劑、環氧系交聯劑、氮丙啶系交聯劑、金屬螫合物系交聯劑等,特別是,從黏著劑組成物的適用期及黏著劑層的耐久性、交聯速度等觀點而言,較理想為異氰酸酯系交聯劑。 Examples of the cross-linking agent (B) include: isocyanate-based cross-linking agents, epoxy-based cross-linking agents, aziridine-based cross-linking agents, metal chelate-based cross-linking agents, etc., especially from the application of adhesive compositions From the viewpoint of the life span, durability of the adhesive layer, and cross-linking speed, an isocyanate-based cross-linking agent is preferred.
異氰酸酯系化合物較理想為在分子內具有至少2個異氰酸酯基(-NCO)的化合物,可列舉例如:脂肪族異氰酸酯系化合物(例如,六亞甲基二異氰酸酯等)、脂環族異氰酸酯系化合物(例如,異佛酮二異氰酸酯、氫化二苯基甲烷二異氰酸酯、氫化伸二甲苯基二異氰酸酯等)、芳香族異氰酸酯系化合物(例如,伸甲苯基二異氰酸酯、伸二甲苯基二異氰酸酯、二甲苯基甲烷二異氰酸酯、伸萘基二異氰酸酯、三苯基甲烷三異氰酸酯等)等。再者,交聯劑(B)亦可為前述異氰酸酯化合物與多元醇化合物的加成物(加合物)[例如,丙三醇、三羥甲基丙烷等的加成物]、與異氰脲酸酯化合物、 縮二脲型化合物、聚醚聚醇、聚酯聚醇、丙烯酸聚醇、聚丁二烯聚醇、聚異戊二烯聚醇等進行加成反應而成的胺甲酸乙酯預聚物型異氰酸酯化合物等的衍生物。交聯劑(B)可單獨或組合2種以上使用。該等之中,代表性者可列舉:由芳香族異氰酸酯系化合物(例如,伸甲苯基二異氰酸酯、伸二甲苯基二異氰酸酯)、脂肪族異氰酸酯系化合物(例如,六亞甲基二異氰酸酯)或該等多元醇化合物(例如,丙三醇、三羥甲基丙烷)而來的加成物或異氰脲酸酯。交聯劑(B)為由芳香族異氰酸酯系化合物及/或該等的多元醇化合物或異氰脲酸酯而來的加成物時,由於在最適合的交聯密度(或交聯結構)的形成上有利,故,可提升黏著劑層的耐久性。特別是,由伸甲苯基二異氰酸酯及/或該等的多元醇化合物而來的加成物時,例如即使將黏著劑層適用於偏光板時等,亦可提升耐久性。 The isocyanate compound is preferably a compound having at least two isocyanate groups (-NCO) in the molecule. Examples thereof include: aliphatic isocyanate compounds (for example, hexamethylene diisocyanate, etc.), alicyclic isocyanate compounds ( For example, isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate, etc.), aromatic isocyanate compounds (for example, tolylene diisocyanate, xylylene diisocyanate, xylylenemethane diisocyanate, etc.) Isocyanate, naphthyl diisocyanate, triphenylmethane triisocyanate, etc.). Furthermore, the cross-linking agent (B) may be an adduct (adduct) of the aforementioned isocyanate compound and a polyol compound [for example, an adduct of glycerol, trimethylolpropane, etc.], and an isocyanate compound. Urea ester compounds, Urethane prepolymer type formed by addition reaction of biuret type compound, polyether polyol, polyester polyol, acrylic polyol, polybutadiene polyol, polyisoprene polyol, etc. Derivatives of isocyanate compounds, etc. The cross-linking agent (B) can be used alone or in combination of two or more types. Among these, representative ones include aromatic isocyanate-based compounds (for example, tolylene diisocyanate, xylylene diisocyanate), aliphatic isocyanate-based compounds (for example, hexamethylene diisocyanate), or the Adducts or isocyanurates derived from polyol compounds such as glycerol and trimethylolpropane. When the cross-linking agent (B) is an adduct derived from an aromatic isocyanate compound and/or the polyol compound or isocyanurate, the optimal cross-linking density (or cross-linked structure) It is beneficial to the formation of the adhesive layer, so it can improve the durability of the adhesive layer. In particular, when the adducts are derived from tolyl diisocyanate and/or these polyol compounds, for example, even when the adhesive layer is applied to a polarizing plate, the durability can be improved.
相對於樹脂(A)100質量份,交聯劑(B)的含量通常為0.01至15質量份,較理想為0.05至10質量份,更理想為0.1至5質量份。 The content of the cross-linking agent (B) is usually 0.01 to 15 parts by mass, preferably 0.05 to 10 parts by mass, and more preferably 0.1 to 5 parts by mass relative to 100 parts by mass of the resin (A).
本發明的黏著劑組成物可更含有矽烷化合物(D)。 The adhesive composition of the present invention may further contain a silane compound (D).
矽烷化合物(D)可列舉例如:乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基三(2-甲氧基乙氧基)矽烷、3-環氧丙基丙基三甲氧基矽烷、3-環氧丙基丙基三乙氧基矽烷、3-環氧丙基丙基甲基二甲氧基矽烷、3-環氧丙基丙基乙氧基二甲基矽烷、2-(3,4-環氧基環己基)乙基三甲氧基矽烷、3-氯丙基甲基二甲氧基矽烷、3-氯丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-巰基丙基三甲氧基矽烷等。 Examples of the silane compound (D) include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, and 3-epoxypropylpropyltrimethoxysilane. Silane, 3-epoxypropylpropyltriethoxysilane, 3-epoxypropylpropylmethyldimethoxysilane, 3-epoxypropylpropylethoxydimethylsilane, 2- (3,4-Epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyl Trimethoxysilane, 3-mercaptopropyltrimethoxysilane, etc.
矽烷化合物(D)亦可為聚矽氧寡聚物。以單體彼此組合的形態表示聚矽氧寡聚物的具體例時,係如下所述。 The silane compound (D) may also be a polysiloxane oligomer. Specific examples of polysiloxane oligomers in the form of a combination of monomers are as follows.
3-巰基丙基三甲氧基矽烷-四甲氧基矽烷寡聚物、3-巰基丙基三甲氧基矽烷-四乙氧基矽烷寡聚物、3-巰基丙基三乙氧基矽烷-四甲氧基矽烷寡聚物、3-巰基丙基三乙氧基矽烷-四乙氧基矽烷寡聚物等的含有巰基丙基的寡聚物;巰基甲基三甲氧基矽烷-四甲氧基矽烷寡聚物、巰基甲基三甲氧基矽烷-四乙氧基矽烷寡聚物、統基甲基三乙氧基矽烷-四甲氧基矽烷寡聚物、巰基甲基三乙氧基矽烷-四乙氧基矽烷寡聚物等的含有巰基甲基的寡聚物;3-環氧丙氧基丙基三甲氧基矽烷-四甲氧基矽烷寡聚物、3-環氧丙氧基丙基三甲氧基矽烷-四乙氧基矽烷寡聚物、3-環氧丙氧基丙基三乙氧基矽烷-四甲氧基矽烷寡聚物、3-環氧丙氧基丙基三乙氧基矽烷-四乙氧基矽烷寡聚物、3-環氧丙氧基丙基甲基二甲氧基矽烷-四甲氧基矽烷寡聚物、3-環氧丙氧基丙基甲基二甲氧基矽烷-四乙氧基矽烷寡聚物、3-環氧丙氧基丙基甲基二乙氧基矽烷-四甲氧基矽烷寡聚物、3-環氧丙氧基丙基甲基二乙氧基矽烷-四乙氧基矽烷寡聚物等的含有3-環氧丙氧基丙基的寡聚物;3-甲基丙烯醯氧基丙基三甲氧基矽烷-四甲氧基矽烷寡聚物、3-甲基丙烯醯氧基丙基三甲氧基矽烷-四乙氧基矽烷寡聚物、3-甲基丙烯醯氧基丙基三乙氧基矽烷-四甲氧基矽烷寡聚物、3-甲基丙烯醯氧基丙基三乙氧基矽烷-四乙氧基矽烷寡聚物、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷-四甲氧基矽烷寡聚物、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷-四乙氧基矽烷寡聚物、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷-四甲氧基矽烷寡聚物、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷-四乙氧基矽烷寡聚物等含有甲基丙烯醯氧基丙基的寡聚物;3-丙烯醯氧基丙基三甲氧基矽烷-四甲氧基矽烷寡聚物、3-丙烯醯氧基丙基三甲氧基矽烷-四乙氧基矽烷寡聚物、3-丙烯醯氧基丙基 三乙氧基矽烷-四甲氧基矽烷寡聚物、3-丙烯醯氧基丙基三乙氧基矽烷-四乙氧基矽烷寡聚物、3-丙烯醯氧基丙基甲基二甲氧基矽烷-四甲氧基矽烷寡聚物、3-丙烯醯氧基丙基甲基二甲氧基矽烷-四乙氧基矽烷寡聚物、3-丙烯醯氧基丙基甲基二乙氧基矽烷-四甲氧基矽烷寡聚物、3-丙烯醯氧基丙基甲基二乙氧基矽烷-四乙氧基矽烷寡聚物等的含有丙烯醯氧基丙基的寡聚物;乙烯基三甲氧基矽烷-四甲氧基矽烷寡聚物、乙烯基三甲氧基矽烷-四乙氧基矽烷寡聚物、乙烯基三乙氧基矽烷-四甲氧基矽烷寡聚物、乙烯基三乙氧基矽烷-四乙氧基矽烷寡聚物、乙烯基甲基二甲氧基矽烷-四甲氧基矽烷寡聚物、乙烯基甲基二甲氧基矽烷-四乙氧基矽烷寡聚物、乙烯基甲基二乙氧基矽烷-四甲氧基矽烷寡聚物、乙烯基甲基二乙氧基矽烷-四乙氧基矽烷寡聚物等的含有乙烯基的寡聚物;3-胺基丙基三甲氧基矽烷-四甲氧基矽烷寡聚物、3-胺基丙基三甲氧基矽烷-四乙氧基矽烷寡聚物、3-胺基丙基三乙氧基矽烷-四甲氧基矽烷寡聚物、3-胺基丙基三乙氧基矽烷-四乙氧基矽烷寡聚物、3-胺基丙基甲基二甲氧基矽烷-四甲氧基矽烷寡聚物、3-胺基丙基甲基二甲氧基矽烷-四乙氧基矽烷寡聚物、3-胺基丙基甲基二乙氧基矽烷-四甲氧基矽烷寡聚物、3-胺基丙基甲基二乙氧基矽烷-四乙氧基矽烷寡聚物等含有胺基的寡聚物等。 3-Mercaptopropyltrimethoxysilane-tetramethoxysilane oligomer, 3-Mercaptopropyltrimethoxysilane-tetraethoxysilane oligomer, 3-Mercaptopropyltriethoxysilane-tetraethoxysilane Methoxypropyl-containing oligomers such as methoxysilane oligomer and 3-mercaptopropyltriethoxysilane-tetraethoxysilane oligomer; mercaptomethyltrimethoxysilane-tetramethoxy Silane oligomer, mercaptomethyltrimethoxysilane-tetraethoxysilane oligomer, methyltriethoxysilane-tetramethoxysilane oligomer, mercaptomethyltriethoxysilane- Tetraethoxysilane oligomer and other mercaptomethyl-containing oligomers; 3-glycidoxypropyltrimethoxysilane-tetramethoxysilane oligomer, 3-glycidoxypropyl Trimethoxysilane-tetraethoxysilane oligomer, 3-glycidoxypropyltriethoxysilane-tetramethoxysilane oligomer, 3-glycidoxypropyltriethyl Oxysilane-tetraethoxysilane oligomer, 3-glycidoxypropylmethyldimethoxysilane-tetramethoxysilane oligomer, 3-glycidoxypropylmethyl Dimethoxysilane-tetraethoxysilane oligomer, 3-glycidoxypropylmethyldiethoxysilane-tetramethoxysilane oligomer, 3-glycidoxypropyl Methyldiethoxysilane-tetraethoxysilane oligomer and other oligomers containing 3-glycidoxypropyl; 3-methacryloxypropyltrimethoxysilane-tetramethyl Oxysilane oligomer, 3-methacryloxypropyltrimethoxysilane-tetraethoxysilane oligomer, 3-methacryloxypropyltriethoxysilane-tetramethoxysilane Silane oligomer, 3-methacryloxypropyltriethoxysilane-tetraethoxysilane oligomer, 3-methacryloxypropylmethyldimethoxysilane-tetraethoxysilane Methoxysilane oligomer, 3-methacryloxypropylmethyldimethoxysilane-tetraethoxysilane oligomer, 3-methacryloxypropylmethyldiethoxy Silane-tetramethoxysilane oligomer, 3-methacryloxypropylmethyldiethoxysilane-tetraethoxysilane oligomer and other oligos containing methacryloxypropyl Polymer; 3-acryloxypropyltrimethoxysilane-tetramethoxysilane oligomer, 3-acryloxypropyltrimethoxysilane-tetraethoxysilane oligomer, 3-propylene acyloxypropyl Triethoxysilane-tetramethoxysilane oligomer, 3-acryloxypropyltriethoxysilane-tetraethoxysilane oligomer, 3-acryloxypropylmethyldimethyl Oxysilane-tetramethoxysilane oligomer, 3-acryloxypropylmethyldimethoxysilane-tetraethoxysilane oligomer, 3-acryloxypropylmethyldiethyl Oxysilane-tetramethoxysilane oligomer, 3-acryloxypropylmethyldiethoxysilane-tetraethoxysilane oligomer, and other acryloxypropyl-containing oligomers ; Vinyltrimethoxysilane-tetramethoxysilane oligomer, vinyltrimethoxysilane-tetraethoxysilane oligomer, vinyltriethoxysilane-tetramethoxysilane oligomer, Vinyltriethoxysilane-tetraethoxysilane oligomer, vinylmethyldimethoxysilane-tetramethoxysilane oligomer, vinylmethyldimethoxysilane-tetraethoxy Vinyl-containing oligomers such as silane oligomers, vinylmethyldiethoxysilane-tetramethoxysilane oligomers, vinylmethyldiethoxysilane-tetraethoxysilane oligomers, etc. Material; 3-aminopropyltrimethoxysilane-tetramethoxysilane oligomer, 3-aminopropyltrimethoxysilane-tetraethoxysilane oligomer, 3-aminopropyltriethyl Oxysilane-tetramethoxysilane oligomer, 3-aminopropyltriethoxysilane-tetraethoxysilane oligomer, 3-aminopropylmethyldimethoxysilane-tetramethyl Oxysilane oligomer, 3-aminopropylmethyldimethoxysilane-tetraethoxysilane oligomer, 3-aminopropylmethyldiethoxysilane-tetramethoxysilane oligomer Polymers, amine group-containing oligomers such as 3-aminopropylmethyldiethoxysilane-tetraethoxysilane oligomers, etc.
矽烷化合物(D)亦可為下述式(d1)表示的矽烷化合物。 The silane compound (D) may be a silane compound represented by the following formula (d1).
(式中,A1表示碳數1至20的烷二基或碳數3至20的2價脂環式烴基,構成該烷二基及該脂環式烴基的-CH2-可被-O-或-CO-取代,R41表示碳數1至5的烷基,R42、R43、R44、R45及R46分別獨立地表示碳數1至5的烷基或碳數1至5的烷氧基)。 (In the formula, A 1 represents an alkanediyl group with 1 to 20 carbon atoms or a divalent alicyclic hydrocarbon group with 3 to 20 carbon atoms. -CH 2 - constituting the alkanediyl group and the alicyclic hydrocarbon group can be -O - or -CO-substitution, R 41 represents an alkyl group having 1 to 5 carbon atoms, R 42 , R 43 , R 44 , R 45 and R 46 respectively independently represent an alkyl group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms. 5 alkoxy group).
A1表示的碳數1至20的烷二基可列舉:亞甲基、1,2-乙烷二基、1,3-丙烷二基、1,4-丁烷二基、1,5-戊烷二基、1,6-己烷二基、1,7-庚烷二基、1,8-辛烷二基、1,9-壬烷二基、1,10-癸烷二基、1,12-十二烷二基、1,14-十四烷二基、1,16-十六烷二基、1,18-十八烷二基、1,20-二十烷二基。碳數3至20的2價脂環式烴基可列舉:1,3-環戊烷二基及1,4-環己烷二基。構成該烷二基及該脂環式烴基的-CH2-被-O-或-CO-取代的基可列舉:-CH2CH2-O-CH2CH2-、-CH2CH2-O-CH2CH2-O-CH2CH2-、-CH2CH2-O-CH2CH2-O-CH2CH2-O-CH2CH2-、-CH2CH2-CO-O-CH2CH2-、-CH2CH2-O-CH2CH2-CO-O-CH2CH2-、-CH2CH2CH2CH2-O-CH2CH2-以及-CH2CH2CH2CH2-O-CH2CH2CH2CH2-。 Examples of the alkanediyl group having 1 to 20 carbon atoms represented by A 1 include: methylene, 1,2-ethanediyl, 1,3-propanediyl, 1,4-butanediyl, 1,5- Pentanediyl, 1,6-hexanediyl, 1,7-heptanediyl, 1,8-octanediyl, 1,9-nonanediyl, 1,10-decanediyl, 1,12-dodecanediyl, 1,14-tetradecanediyl, 1,16-hexadecanediyl, 1,18-octadecanediyl, 1,20-eicosanediyl. Examples of the divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include 1,3-cyclopentanediyl and 1,4-cyclohexanediyl. The -CH 2 - constituting the alkanediyl group and the alicyclic hydrocarbon group substituted by -O- or -CO- may include: -CH 2 CH 2 -O-CH 2 CH 2 -, -CH 2 CH 2 - O-CH 2 CH 2 -O-CH 2 CH 2 -, -CH 2 CH 2 -O-CH 2 CH 2 -O-CH 2 CH 2 -O-CH 2 CH 2 -, -CH 2 CH 2 -CO -O-CH 2 CH 2 -, -CH 2 CH 2 -O-CH 2 CH 2 -CO-O-CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 -O-CH 2 CH 2 - and -CH 2 CH 2 CH 2 CH 2 -O-CH 2 CH 2 CH 2 CH 2 -.
R41至R45表示的碳數1至5的烷基可列舉:甲基、乙基、丙基、異丙基、丁基、異丁基、第三丁基及戊基,R42至R45表示的碳數1至5的烷氧基可列舉:甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、異丁氧基、第三丁氧基及戊氧基。 Examples of alkyl groups with 1 to 5 carbon atoms represented by R 41 to R 45 include: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl and pentyl, R 42 to R Examples of alkoxy groups with 1 to 5 carbon atoms represented by 45 include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy and pentyloxy .
式(d1)表示的矽烷化合物可列舉例如:(三甲氧基矽基)甲烷、1,2-雙(三甲氧基矽基)乙烷、1,2-雙(三乙氧基矽基)乙烷、1,3-雙(三甲氧基矽基)丙烷、1,3-雙(三乙氧基矽基)丙烷、1,4-雙(三甲氧基矽基)丁烷、1,4-雙(三乙氧基矽基)丁烷、1,5-雙(三甲氧基矽基)戊烷、1,5-雙(三乙氧基矽基) 戊烷、1,6-雙(三甲氧基矽基)己烷、1,6-雙(三乙氧基矽基)己烷、1,6-雙(三丙氧基矽基)己烷、1,8-雙(三甲氧基矽基)辛烷、1,8-雙(三乙氧基矽基)辛烷、1,8-雙(三丙氧基矽基)辛烷等雙(三C1-5烷氧基矽基)C1-10烷;雙(二甲氧基甲基矽基)甲烷、1,2-雙(二甲氧基甲基矽基)乙烷、1,2-雙(二甲氧基乙基矽基)乙烷、1,4-雙(二甲氧基甲基矽基)丁烷、1,4-雙(二甲氧基乙基矽基)丁烷、1,6-雙(二甲氧基甲基矽基)己烷、1,6-雙(二甲氧基乙基矽基)己烷、1,8-雙(二甲氧基甲基矽基)辛烷、1,8-雙(二甲氧基乙基矽基)辛烷等雙(二C1-5烷氧基C1-5烷基矽基)C1-10烷;1,6-雙(甲氧基二甲基矽基)己烷、1,8-雙(甲氧基二甲基矽基)辛烷等雙(單C1-5烷氧基二C1-5烷基矽基)C1-10烷等。該等之中,較理想為1,2-雙(三甲氧基矽基)乙烷、1,3-雙(三甲氧基矽基)丙烷、1,4-雙(三甲氧基矽基)丁烷、1,5-雙(三甲氧基矽基)戊烷、1,6-雙(三甲氧基矽基)己烷、1,8-雙(三甲氧基矽基)辛烷等的雙(三甲氧基矽基)C1-10烷,特別理想為1,6-雙(三甲氧基矽基)己烷、1,8-雙(三甲氧基矽基)辛烷。 Examples of the silane compound represented by formula (d1) include: (trimethoxysilyl)methane, 1,2-bis(trimethoxysilyl)ethane, and 1,2-bis(triethoxysilyl)ethane. alkane, 1,3-bis(trimethoxysilyl)propane, 1,3-bis(triethoxysilyl)propane, 1,4-bis(trimethoxysilyl)butane, 1,4- Bis(triethoxysilyl)butane, 1,5-bis(trimethoxysilyl)pentane, 1,5-bis(triethoxysilyl) Pentane, 1,6-bis(trimethoxysilyl)hexane, 1,6-bis(triethoxysilyl)hexane, 1,6-bis(tripropoxysilyl)hexane, 1,8-bis(trimethoxysilyl)octane, 1,8-bis(triethoxysilyl)octane, 1,8-bis(tripropoxysilyl)octane and other bis(trimethoxysilyl)octane C1-5 alkoxysilyl) C1-10 alkane; bis(dimethoxymethylsilyl)methane, 1,2-bis(dimethoxymethylsilyl)ethane, 1,2-bis(dimethoxymethylsilyl)ethane (Dimethoxyethylsilyl)ethane, 1,4-bis(dimethoxymethylsilyl)butane, 1,4-bis(dimethoxyethylsilyl)butane, 1 ,6-bis(dimethoxymethylsilyl)hexane, 1,6-bis(dimethoxyethylsilyl)hexane, 1,8-bis(dimethoxymethylsilyl) Octane, 1,8-bis(dimethoxyethylsilyl)octane and other bis(diC1-5alkoxyC1-5alkylsilyl)C1-10alkanes; 1,6-bis(methane Oxydimethylsilyl)hexane, 1,8-bis(methoxydimethylsilyl)octane and other bis(monoC1-5alkoxydiC1-5alkylsilyl)C1-10 Alkane etc. Among these, 1,2-bis(trimethoxysilyl)ethane, 1,3-bis(trimethoxysilyl)propane, and 1,4-bis(trimethoxysilyl)butane are preferred. alkane, 1,5-bis(trimethoxysilyl)pentane, 1,6-bis(trimethoxysilyl)hexane, 1,8-bis(trimethoxysilyl)octane, etc. Trimethoxysilyl) C1-10 alkane, particularly preferably 1,6-bis(trimethoxysilyl)hexane or 1,8-bis(trimethoxysilyl)octane.
相對於樹脂(A)100質量份,矽烷化合物(D)的含量通常為0.01至10質量份,較理想為0.03至5質量份,更理想為0.05至2質量份,更加理想為0.1至1質量份。 The content of the silane compound (D) is usually 0.01 to 10 parts by mass, preferably 0.03 to 5 parts by mass, more preferably 0.05 to 2 parts by mass, and even more preferably 0.1 to 1 part by mass relative to 100 parts by mass of the resin (A). share.
黏著劑組成物,可更含有抗靜電劑。 The adhesive composition may further contain an antistatic agent.
抗靜電劑可列舉:界面活性劑、矽氧烷化合物、導電性高分子、離子性化合物等,較理想為離子性化合物。離子性化合物可舉出慣用者。構成離子性化合物的陽離子成分可舉出有機陽離子、無機陽離子等。有機陽離子可列舉例如:吡啶陽離子、吡咯啶陽離子、哌啶陽離子、咪唑陽離子、銨陽離子、鋶陽離子、鏻陽離子等。無機陽離子可列舉例如:鋰陽離子、 鉀陽離子、鈉陽離子、銫陽離子等鹼金屬陽離子;鎂陽離子、鈣陽離子等鹼土金屬陽離子等。特別是,從與(甲基)丙烯酸系樹脂的相溶性的觀點而言,較理想為吡啶陽離子、咪唑陽離子、吡咯啶陽離子、鋰陽離子、鉀陽離子。構成離子性化合物的陰離子成分可為無機陰離子及有機陰離子的任一者,惟,從抗靜電的點而言,較理想為包含氟原子的陰離子成分。包含氟原子的陰離子成分可列舉例如:六氟磷酸鹽陰離子(PF6 -)、雙(三氟甲烷磺醯基)醯亞胺陰離子[(CF3SO2)2N-]、雙(氟磺醯基)醯亞胺陰離子[(FSO2)2N-]、四(五氟苯基)硼酸鹽陰離子[(C6F5)4B-]等。該等的離子性化合物可單獨或組合2種以上使用。特別理想為雙(三氟甲烷磺醯基)醯亞胺陰離子[(CF3SO2)2N-]、雙(氟磺醯基)醯亞胺陰離子[(FSO2)2N-]、四(五氟苯基)硼酸鹽陰離子[(C6F5)4B-]。 Examples of the antistatic agent include surfactants, siloxane compounds, conductive polymers, ionic compounds, etc., and preferably ionic compounds. Examples of ionic compounds include commonly used ones. Examples of the cation component constituting the ionic compound include organic cations, inorganic cations, and the like. Examples of organic cations include pyridinium cations, pyrrolidine cations, piperidinium cations, imidazole cations, ammonium cations, sulfonium cations, and phosphonium cations. Examples of inorganic cations include alkali metal cations such as lithium cations, potassium cations, sodium cations, and cesium cations; and alkaline earth metal cations such as magnesium cations and calcium cations. In particular, from the viewpoint of compatibility with (meth)acrylic resin, pyridine cations, imidazole cations, pyrrolidine cations, lithium cations, and potassium cations are preferred. The anion component constituting the ionic compound may be either an inorganic anion or an organic anion. However, from an antistatic point of view, an anion component containing a fluorine atom is more preferred. Examples of anionic components containing fluorine atoms include: hexafluorophosphate anion (PF 6 - ), bis(trifluoromethanesulfonyl)imide anion [(CF 3 SO 2 ) 2 N - ], bis(fluorosulfonate) acyl)acyl imine anion [(FSO 2 ) 2 N - ], tetrakis (pentafluorophenyl) borate anion [(C 6 F 5 ) 4 B - ], etc. These ionic compounds can be used individually or in combination of 2 or more types. Particularly preferred are bis(trifluoromethanesulfonyl)imide anion [(CF 3 SO 2 ) 2 N - ], bis(fluorosulfonyl)imide anion [(FSO 2 ) 2 N - ], tetrafluoromethanesulfonyl imide anion [(FSO 2 ) 2 N - ], (Pentafluorophenyl)borate anion [(C 6 F 5 ) 4 B - ].
在由黏著劑組成物形成的黏著劑層的抗靜電功能的歷時安定性的點而言,較理想為室溫下為固體的離子性化合物。 In terms of the stability of the antistatic function of the adhesive layer formed of the adhesive composition over time, an ionic compound that is solid at room temperature is more desirable.
相對於樹脂(A)100質量份,抗靜電劑的含量例如為0.01至20質量份,較理想為0.1至10質量份,更理想為1至7質量份。 The content of the antistatic agent is, for example, 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, and more preferably 1 to 7 parts by mass relative to 100 parts by mass of the resin (A).
黏著劑組成物可含有1種或2種以上的溶劑、交聯觸媒、增黏劑、塑化劑、柔軟劑、顏料、防鏽劑、無機填充劑、光散射性微粒子等添加劑。 The adhesive composition may contain one or more solvents, cross-linking catalysts, tackifiers, plasticizers, softeners, pigments, anti-rust agents, inorganic fillers, light-scattering particles and other additives.
〈黏著劑層〉 〈Adhesive layer〉
本發明的黏著劑層可藉由例如於溶劑溶解或分散前述黏著劑組成物製成含有溶劑的黏著劑組成物,然後,將其塗佈於基材表面,並使其乾燥而形成。 The adhesive layer of the present invention can be formed by, for example, dissolving or dispersing the aforementioned adhesive composition in a solvent to prepare an adhesive composition containing a solvent, and then coating the adhesive composition on the surface of the substrate and drying it.
合適的基材是塑膠膜,具體而言,可舉出實施過離型處理的剝離膜。剝離膜可列舉在游聚對苯二甲酸乙二酯、聚對苯二甲酸丁二酯、聚碳酸酯、聚芳酯等樹脂所構成的膜的一側面,實施過聚矽氧處理等離型處理者。 A suitable base material is a plastic film, and specifically, a release film subjected to a release treatment can be cited. Examples of the release film include a film made of resin such as polyethylene terephthalate, polybutylene terephthalate, polycarbonate, polyarylate, etc., which has been subjected to polysiloxane plasma treatment on one side. handler.
本發明的黏著劑層較理想為滿足下述式(3)的黏著劑層,更理想為滿足下述式(4)的黏著劑層。 The adhesive layer of the present invention is preferably an adhesive layer that satisfies the following formula (3), and is more preferably an adhesive layer that satisfies the following formula (4).
A(405)≧0.5 (3) A(405)≧0.5 (3)
[式(3)中,A(405)表示在波長405nm中的吸光度]。 [In formula (3), A (405) represents the absorbance at a wavelength of 405 nm].
A(405)/A(440)≧5 (4) A(405)/A(440)≧5 (4)
[式(4)中,A(405)表示在波長405nm中的吸光度;A(440)表示在波長440nm中的吸光度]。 [In formula (4), A (405) represents the absorbance at a wavelength of 405 nm; A (440) represents the absorbance at a wavelength of 440 nm].
A(405)的值越大,表示在波長405nm的吸收越高。A(405)的值未達0.5時,波長405nm的吸收低,容易引起因400nm波長附近的光導致的有機EL發光元件及液晶系相位差膜劣化。A(405)的值較理想為0.6以上,更理想為0.8以上,特別理想為1.0以上。上限沒有特別限制,通常為10以下。 The larger the value of A(405), the higher the absorption at the wavelength of 405nm. When the value of A(405) is less than 0.5, the absorption at a wavelength of 405 nm is low, and the organic EL light-emitting element and the liquid crystal retardation film are likely to be deteriorated by light having a wavelength near 400 nm. The value of A(405) is preferably 0.6 or more, more preferably 0.8 or more, and particularly preferably 1.0 or more. The upper limit is not particularly limited, but is usually 10 or less.
A(405)/A(440)的值表示在波長405nm的吸收的大小相對於波長440nm的吸收的大小。A(405)/A(440)的值越大,表示在波長405nm附近的波長區域具有特異性吸收,將本發明的黏著劑層適用於有機EL顯示裝置、液晶顯示裝置等顯示裝置時,不會阻礙顯示裝置的色彩表現,並且,可吸收400nm附近的光抑制有機EL發光元件及液晶系相位差膜的光劣化。A(405)/A(440)的值較理想為10以上,更理想為30以上,更加理想為60以上。 The value of A(405)/A(440) represents the magnitude of absorption at a wavelength of 405 nm relative to the magnitude of absorption at a wavelength of 440 nm. The larger the value of A(405)/A(440), the greater the specific absorption in the wavelength region near 405 nm. When the adhesive layer of the present invention is applied to display devices such as organic EL display devices and liquid crystal display devices, it will not It hinders the color expression of the display device, and absorbs light near 400nm to suppress light degradation of organic EL light-emitting elements and liquid crystal retardation films. The value of A(405)/A(440) is preferably 10 or more, more preferably 30 or more, and even more preferably 60 or more.
本發明的黏著劑層的厚度通常為0.1至100μm,較理想為3至50μm,更理想為4至25μm。 The thickness of the adhesive layer of the present invention is usually 0.1 to 100 μm, preferably 3 to 50 μm, and more preferably 4 to 25 μm.
〈光學積層體〉 〈Optical laminated body〉
本發明的黏著劑組成物及由該黏著劑組成物形成的黏著劑層例如可使用於光學膜的貼合等。 The adhesive composition of the present invention and the adhesive layer formed from the adhesive composition can be used, for example, for laminating optical films.
在本發明的黏著劑層的至少一側面積層有光學膜的光學積層體也包含在本發明中。 An optical laminate in which an optical film is laminated on at least one side of the adhesive layer of the present invention is also included in the present invention.
本發明的光學積層體係可藉由將前述黏著劑組成物溶解或分散於溶劑成為含有溶劑的黏著劑組成物,然後,將其塗佈於光學膜的表面,並使其乾燥而形成。再者,也可藉由在剝離膜上同樣地形成黏著劑層,將該黏著劑層積層(轉印)至光學膜的表面而得。 The optical laminate system of the present invention can be formed by dissolving or dispersing the aforementioned adhesive composition in a solvent to form an adhesive composition containing a solvent, and then coating the composition on the surface of the optical film and drying it. Furthermore, it can also be obtained by forming an adhesive layer on a release film in the same manner and laminating (transferring) the adhesive layer to the surface of the optical film.
針對包含本發明的黏著劑層之光學積層體一邊使用圖一邊說明。 The optical laminate including the adhesive layer of the present invention will be described using the drawings.
於第1圖至第5圖表示本發明的黏著劑層及本發明的光學積層體的層構成的一例。 An example of the layer structure of the adhesive layer of the present invention and the optical laminate of the present invention is shown in FIGS. 1 to 5 .
第1圖記載的黏著劑層1係為了暫時保護黏著劑層面,而為在黏著劑層面1貼附於著剝離膜2的狀態。
The
第2圖記載的光學積層體10A係包含光學膜40、本發明的黏著劑層1、剝離膜2的光學積層體。
The optical
第3圖記載的光學積層體10B係包含保護膜8、接著劑層7、偏光膜9、接著劑層7、保護膜8、本發明的黏著劑層1、剝離膜2的光學積層體。
The optical
第4圖記載的光學積層體10C及第5圖記載的光學積層體10D係包含保護膜8、接著劑層7、偏光膜9、接著劑層7、保護膜8、本發明的黏著劑層1、相位差膜110、黏著劑層7a、發光元件30(液晶胞、有機EL胞)的光學積層體。
The optical
光學膜40係具有穿透、反射、吸收光線等光學功能的膜。光學膜40可為單層膜,亦可為多層膜。光學膜40可列舉例如:偏光膜、相位差膜、增亮膜、防眩膜、抗反射膜、擴散膜、聚光膜、窗膜等,較理想為偏光膜、相位差膜、窗膜或該等的積層膜。
The
聚光膜係使用於光徑控制等目的,故,可為稜鏡陣列片、透鏡陣列片、附設點的片等。 The light-condensing film is used for light path control and other purposes, so it can be a lens array sheet, a lens array sheet, a sheet with dots, etc.
增亮膜係為了提升適用了偏光板的液晶顯示裝置之亮度的目的而使用。具體而言,可列舉:以將複數片折射率的異方性互為不同的薄膜積層而使反射率產生異方性之方式設計成的反射型偏光分離片、膽固醇液晶聚合物的配向膜、在基材膜上支撐了該配向液晶層的圓偏光分離片。 The brightness enhancement film is used for the purpose of improving the brightness of a liquid crystal display device to which a polarizing plate is applied. Specific examples include: a reflective polarizing separator sheet designed to produce anisotropy in reflectance by laminating a plurality of films with mutually different refractive index anisotropies; an alignment film of a cholesteric liquid crystal polymer; The circularly polarized light separator of the aligned liquid crystal layer is supported on the base film.
窗膜係指可撓性顯示器等可撓性顯示裝置中之前面板,一般配置於顯示裝置的最表面。窗膜例如可舉出由聚醯亞胺樹脂所構成的樹脂膜。窗膜可為例如包含聚醯亞胺及氧化矽的樹脂膜之有機材料與無機材料的混合膜。再者,窗膜亦可在其表面配置用以賦予表面硬度、防污性、耐指紋性功能的硬塗層。窗膜可舉出日本特開2017-94488號記載的膜等。 Window film refers to the front panel of flexible display devices such as flexible displays, and is generally placed on the outermost surface of the display device. Examples of window films include resin films made of polyimide resin. The window film may be a mixed film of organic and inorganic materials, such as a resin film including polyimide and silicon oxide. Furthermore, the window film can also be equipped with a hard coating on its surface to provide surface hardness, antifouling properties, and fingerprint resistance. Examples of window films include those described in Japanese Patent Application Laid-Open No. 2017-94488.
偏光膜係具有將具有於其吸收軸平行的振動面的直線偏光吸收,將具有與吸收軸(平行穿透軸)直交的振動面的直線偏光穿透的性質的膜,可使用例如於聚乙烯醇系膜吸附配向有二色性色素的膜。 The polarizing film is a film that has the property of absorbing linearly polarized light having a vibration plane parallel to its absorption axis and transmitting linearly polarized light having a vibration plane perpendicular to the absorption axis (parallel transmission axis). It can be used, for example, in polyethylene. The alcohol-based film is a film in which dichroic pigments are adsorbed and aligned.
二色性色素可列舉例如:碘、二色性有機染料等。 Examples of dichroic dyes include iodine, dichroic organic dyes, and the like.
聚乙烯醇系樹脂的皂化度通常為85莫耳%以上100莫耳%以下,較理想為98莫耳%以上。聚乙烯醇系樹脂可被改性,亦可使用例如經醛類改性的聚乙烯醇縮甲醛或聚乙烯醇縮乙醛等。聚乙烯醇系樹脂的聚合度通常為1,000以上10,000以下,較理想為1,500以上5,000以下。 The degree of saponification of the polyvinyl alcohol-based resin is usually 85 mol% or more and 100 mol% or less, preferably 98 mol% or more. The polyvinyl alcohol-based resin may be modified, and for example, aldehyde-modified polyvinyl formal or polyvinyl acetal may be used. The degree of polymerization of the polyvinyl alcohol-based resin is usually from 1,000 to 10,000, preferably from 1,500 to 5,000.
通常,將聚乙烯醇系樹脂製膜而成者被使用為偏光膜的原料膜。聚乙烯醇系樹脂可用習知的方法進行製膜。原料膜的厚度通常為1至150μm,考慮延伸容易度等,較理想為10μm以上。 Generally, a film formed of a polyvinyl alcohol-based resin is used as a raw material film for a polarizing film. The polyvinyl alcohol-based resin can be formed into a film by a conventional method. The thickness of the raw material film is usually 1 to 150 μm, but is preferably 10 μm or more in consideration of ease of stretching and the like.
偏光膜係例如對原料膜實施下列步驟:單軸延伸的步驟、用二色性色素將膜染色而使該二色性色素吸附的步驟、用硼酸水溶液處理膜的步驟以及水洗膜的步驟,最後,進行乾燥而製造。偏光膜的厚度通常為1至30μm,從附黏著劑層的光學積層體的薄膜化的觀點而言,較理想為20μm以下,更理想為15μm以下,特別理想為10μm以下。 The polarizing film system, for example, performs the following steps on the raw film: a step of uniaxial stretching, a step of dyeing the film with a dichroic dye to adsorb the dichroic dye, a step of treating the film with a boric acid aqueous solution, and a step of washing the film with water, and finally , dried and manufactured. The thickness of the polarizing film is usually 1 to 30 μm. From the viewpoint of thinning the optical laminate with an adhesive layer, it is preferably 20 μm or less, more preferably 15 μm or less, and particularly preferably 10 μm or less.
偏光膜的至少一側面較理想為隔著接著劑設置有保護膜。 It is preferable that at least one side surface of the polarizing film is provided with a protective film via an adhesive.
接著劑可使用習知的接著劑,可為水系接著劑,亦可為活性能量線硬化型接著劑。 The adhesive can use a conventional adhesive, and it can be a water-based adhesive or an active energy ray-hardening adhesive.
水系接著劑可舉出慣用的水系接著劑(例如,由聚乙烯醇系樹脂水溶液所構成的接著劑、水系二液型胺酯系乳化接著劑、醛化合物、環氧化合物、三聚氰胺系化合物、羥甲基化合物、異氰酸酯化合物、胺化合物、多價金屬鹽等的交聯劑等)。該等之中,可適合地使用由聚乙烯醇系樹脂水溶液所構成的水系接著劑。此外,使用水系接著劑時,將偏光膜與保護膜貼合後,為了除去水系接著劑中所包含有的水,較理想為實施乾燥 步驟。乾燥步驟後,可設置在例如20至45℃左右的溫度下熟化之熟化步驟。由水系接著劑形成的接著劑層通常為0.001至5μm。 Examples of the water-based adhesive include commonly used water-based adhesives (for example, adhesives composed of polyvinyl alcohol-based resin aqueous solutions, water-based two-component urethane-based emulsion adhesives, aldehyde compounds, epoxy compounds, melamine-based compounds, hydroxyl compounds, etc. Cross-linking agents such as methyl compounds, isocyanate compounds, amine compounds, polyvalent metal salts, etc.). Among these, a water-based adhesive composed of a polyvinyl alcohol-based resin aqueous solution can be suitably used. In addition, when using a water-based adhesive, it is preferable to dry the polarizing film and the protective film in order to remove the water contained in the water-based adhesive. steps. After the drying step, an aging step of aging at a temperature of about 20 to 45° C. may be provided. The adhesive layer formed of a water-based adhesive is usually 0.001 to 5 μm.
所謂活性能量線硬化型接著劑係指藉由照射紫外線、電子線等活性能量線而硬化的接著劑,可列舉例如:包含聚合性化合物及光聚合起始劑的硬化性組成物、包含光反應性樹脂的硬化性組成物、包含黏結劑樹脂及光反應性交聯劑的硬化性組成物等,較理想為紫外線硬化性接著劑。 The so-called active energy ray curable adhesive refers to an adhesive that is cured by irradiation with active energy rays such as ultraviolet rays and electron rays. Examples include curable compositions containing a polymerizable compound and a photopolymerization initiator, and adhesives containing photoreaction A curable composition of a flexible resin, a curable composition containing a binder resin and a photoreactive cross-linking agent, etc. are preferably ultraviolet curable adhesives.
將偏光膜與保護膜貼合的方法,可舉出對該等的至少一者的貼合面實施皂化處理、電暈處理、電漿處理等表面活化處理的方法等。在偏光膜的兩面貼合保護膜時,用以貼合該等的樹脂膜的接著劑可為相同種類的接著劑,亦可為不同種類的接著劑。 Examples of methods for bonding the polarizing film and the protective film include subjecting at least one of the bonded surfaces to surface activation treatments such as saponification treatment, corona treatment, and plasma treatment. When the protective films are bonded to both sides of the polarizing film, the adhesives used to bond the resin films may be the same type of adhesive or different types of adhesives.
保護膜較理想為由具有透光性的熱塑性樹脂所形成的膜。具體而言,可舉出由聚烯烴系樹脂;纖維素系樹脂;聚酯系樹脂;(甲基)丙烯酸系樹脂;或該等的混合物、共聚物等所購成的膜。於偏光膜的兩面貼合保護膜時,所使用的保護膜可為由不同的熱塑性樹脂所構成的膜,亦可為由相同的熱塑性樹脂所構成的膜。 The protective film is preferably a film formed of a translucent thermoplastic resin. Specific examples include commercially available films made of polyolefin-based resins; cellulose-based resins; polyester-based resins; (meth)acrylic resins; or mixtures and copolymers thereof. When laminating protective films on both sides of the polarizing film, the protective films used may be films composed of different thermoplastic resins, or may be films composed of the same thermoplastic resin.
保護膜積層於偏光膜的至少一側面時,保護膜較理想為聚烯烴系樹脂、纖維素系樹脂所構成的保護膜。藉由使用該等膜,可不損害偏光膜的光學特性,並且,有效地抑制高溫環境之偏光膜的收縮。此外,保護膜也可為氧屏蔽層。 When the protective film is laminated on at least one side surface of the polarizing film, the protective film is preferably a protective film composed of polyolefin-based resin or cellulose-based resin. By using these films, the optical properties of the polarizing film are not impaired, and the shrinkage of the polarizing film in high-temperature environments can be effectively suppressed. In addition, the protective film may also be an oxygen shielding layer.
偏光板之較理想構成係在偏光膜的至少一側面,隔著接著劑層有積層保護膜的偏光板。保護膜只積層於偏光膜的一側面時,較理想為積層於觀看側。積層於觀看側的保護膜,較理想為由三乙醯基纖維素系樹 脂或環烯烴系樹脂所構成的保護膜。在觀看側積層有保護膜的表面亦可設置硬塗層、防眩光層等表面處理層。 A preferred configuration of the polarizing plate is one in which a protective film is laminated on at least one side of the polarizing film via an adhesive layer. When the protective film is laminated on only one side of the polarizing film, it is preferably laminated on the viewing side. The protective film laminated on the viewing side is preferably made of triacetyl cellulose. Protective film composed of aliphatic or cycloolefin resin. The surface with a protective film on the viewing side can also be provided with surface treatment layers such as a hard coating layer and an anti-glare layer.
保護膜積層於偏光膜的兩面時,面板側(與觀看側相反之側)的保護膜較理想為由三乙醯基纖維素系樹脂、環烯烴系樹脂或丙烯酸系樹脂所構成的保護膜或相位差膜。相位差膜亦可為後述的零延遲膜。 When the protective film is laminated on both sides of the polarizing film, the protective film on the panel side (the side opposite to the viewing side) is preferably a protective film composed of triacetyl cellulose-based resin, cycloolefin-based resin, or acrylic resin, or Retardation film. The retardation film may be a zero-retardation film described below.
所謂相位差膜為顯示光學異方性的光學膜,可舉出例如:將聚乙烯醇、聚碳酸酯、聚酯、聚芳酯、聚醯亞胺、聚烯烴、聚環烯烴、聚苯乙烯、聚碸、聚醚碸、聚偏二氟乙烯/聚甲基丙烯酸甲酯、乙醯基纖維素、乙烯-乙酸乙烯酯共聚物的皂化物、聚氯乙烯等所構成的高分子膜延伸1.01至6倍左右所得之延伸膜等。延伸膜中,較理想為將乙醯基纖維素、聚酯、聚碳酸酯膜、環烯烴系樹脂膜進行單軸延伸或二軸延伸而成的高分子膜。再者,相位差膜可為液晶性化合物藉由塗佈/配向於基材而表現光學異方性的相位差膜。 The retardation film is an optical film showing optical anisotropy, and examples thereof include polyvinyl alcohol, polycarbonate, polyester, polyarylate, polyimide, polyolefin, polycycloolefin, and polystyrene. , polymer membranes composed of polystyrene, polyether styrene, polyvinylidene fluoride/polymethyl methacrylate, acetyl cellulose, saponified products of ethylene-vinyl acetate copolymer, polyvinyl chloride, etc. 1.01 to about 6 times the obtained stretched film, etc. Among the stretched films, preferred ones are polymer films obtained by uniaxially or biaxially stretching acetyl cellulose, polyester, polycarbonate films, and cycloolefin resin films. Furthermore, the retardation film may be a retardation film in which a liquid crystalline compound exhibits optical anisotropy by coating/aligning it on a substrate.
此外,於本說明書中,相位差膜包含零延遲膜,亦包含被稱為單軸性相位差膜、低光彈性模數相位差膜、廣視角相位差膜等膜。 In addition, in this specification, the retardation film includes a zero-retardation film, and also includes films called uniaxial retardation film, low photoelastic modulus retardation film, wide viewing angle retardation film, and the like.
所謂零延遲膜係指正面的延遲Re與厚度方向的延遲Rth皆為-15至15nm,光學等方性的膜。零延遲膜可舉出由纖維素系樹脂、聚烯烴系樹脂(鏈狀聚烯烴系樹脂、聚環烯烴系樹脂等)或聚對苯二甲酸乙二酯系樹脂所構成的樹脂膜,由容易控制延遲值、容易取得的點而言,較理想為纖維素系樹脂或聚烯烴系樹脂。零延遲膜亦可使用為保護膜。零延遲膜可列舉:富士膜(FUJI FILM(股))販售的”Z-TAC”(商品名)、日本ZEON(股)販售的”ZF-14”(商品名)等。 The so-called zero-retardation film refers to a film whose front-side retardation R e and thickness direction retardation R th are both -15 to 15 nm, and which is optically isotropic. Examples of the zero-retardation film include resin films composed of cellulose-based resins, polyolefin-based resins (chain polyolefin-based resins, polycycloolefin-based resins, etc.) or polyethylene terephthalate-based resins. In terms of controlling the retardation value and making it easy to obtain, a cellulose-based resin or a polyolefin-based resin is preferred. Zero retardation film can also be used as a protective film. Examples of zero-retardation films include "Z-TAC" (trade name) sold by FUJI FILM Co., Ltd., "ZF-14" (trade name) sold by Japan ZEON Co., Ltd., etc.
於本發明的光學膜中,相位差膜較理想為藉由塗佈/配向液晶性化合物而表現光學異方性的相位差膜。 In the optical film of the present invention, the retardation film is preferably one that expresses optical anisotropy by coating/aligning a liquid crystal compound.
藉由液晶性化合物的塗佈/配向而表現光學異方性的相位差膜,可列舉下述第一形態至第五形態。 Examples of retardation films that exhibit optical anisotropy by coating/alignment of liquid crystal compounds include the following first to fifth aspects.
第一形態:相對於支撐基材,棒狀液晶化合物在水平方向配向而成的相位差膜; The first form: a retardation film in which rod-shaped liquid crystal compounds are aligned in the horizontal direction relative to the supporting substrate;
第二形態:相對於支撐基材,棒狀液晶化合物在垂直方向配向而成的相位差膜; Second form: a retardation film in which rod-shaped liquid crystal compounds are aligned in the vertical direction relative to the supporting substrate;
第三形態:棒狀液晶化合物在面內呈螺旋狀變化配向方向的相位差膜; The third form: a retardation film in which the rod-shaped liquid crystal compound changes the alignment direction in a spiral manner within the plane;
第四形態:圓盤狀液晶化合物呈傾斜配向的相位差膜; The fourth form: a retardation film in which a disk-shaped liquid crystal compound is tilted and aligned;
第五形態:相對於支撐基材,圓盤狀液晶化合物在垂直方向配向而成的二軸性相位差膜。 Fifth form: a biaxial retardation film in which a disc-shaped liquid crystal compound is aligned in a vertical direction with respect to a supporting base material.
例如,於有機電激發光顯示器所使用的光學膜適合使用第一形態、第二形態、第五形態。再者,亦可使該等的形態的相位差膜積層使用。 For example, the first form, the second form, and the fifth form are suitable for the optical film used in the organic electroluminescence display. Furthermore, retardation films of these forms may be laminated and used.
相位差膜為由聚合性液晶化合物的配向狀態中之聚合物所構成的層(以下,也有稱為「光學異方性層」的情況)時,相位差膜較理想為具有反波長分散性。所謂反波長分散性係指在短波長的液晶配向面內相位差值小於在長波長的液晶配向面內相位差值的光學特性,較理想為光學膜滿足下述式(7)及式(8)。此外,Re(λ)表示為相對於波長λ nm的光之面內相位差值。 When the retardation film is a layer composed of a polymer in an aligned state of a polymerizable liquid crystal compound (hereinafter, may be referred to as an "optically anisotropic layer"), the retardation film preferably has reverse wavelength dispersion. The so-called reverse wavelength dispersion refers to the optical property that the phase difference value in the short-wavelength liquid crystal alignment plane is smaller than the phase difference value in the long-wavelength liquid crystal alignment plane. Ideally, the optical film satisfies the following formulas (7) and (8). ). In addition, R e (λ) is expressed as the in-plane phase difference value of light with respect to the wavelength λ nm.
Re(450)/Re(550)≦1 (7) Re(450)/Re(550)≦1 (7)
1≦Re(630)/Re(550) (8) 1≦Re(630)/Re(550) (8)
於本發明的光學膜中,向相位差膜為第一形態且具有反波長分散性時,因減少顯示裝置的黑色顯示時的著色,所以較理想,在前述式(7),更理想為0.82≦Re(450)/Re(550)≦0.93。更理想120≦Re(550)≦150。 In the optical film of the present invention, when the retardation film is in the first form and has reverse wavelength dispersion, it is preferable because it reduces coloration during black display of the display device. In the above formula (7), it is more preferable that it is 0.82 ≦Re(450)/Re(550)≦0.93. More ideally, 120≦Re(550)≦150.
相位差膜為具有光學異方性層時的聚合性液晶化合物可列舉:液晶手冊(液晶手冊編輯委員會編,丸善(股),平成12年10月30日發行)的「3.8.6交聯(完全交聯型)」、「6.5.1液晶材料b.聚合性向列型液晶材料」記載的化合物中具有聚合性基的化合物、以及日本特開2010-31223號公報、日本特開2010-270108號公報、日本特開2011-6360號公報、日本特開2011-207765號公報、日本特開2011-162678號公報、日本特開2016-81035號公報、國際公開第2017/043438號及日本特表2011-207765號公報記載的聚合性液晶化合物等。 Examples of polymerizable liquid crystal compounds when the retardation film has an optically anisotropic layer include: "3.8.6 Cross-linking (Compiled by the Liquid Crystal Handbook Editorial Committee, Maruzen Co., Ltd., issued on October 30, 2012)" Compounds having a polymerizable group among the compounds described in "6.5.1 Liquid crystal material b. Polymerizable nematic liquid crystal material", and Japanese Patent Application Laid-Open No. 2010-31223, Japanese Patent Application Laid-Open No. 2010-270108 Gazette, Japanese Patent Application Publication No. 2011-6360, Japanese Patent Application Publication No. 2011-207765, Japanese Patent Application Publication No. 2011-162678, Japanese Patent Application Publication No. 2016-81035, International Publication No. 2017/043438 and Japanese Patent Application Publication No. 2011 -Polymerizable liquid crystal compounds described in Publication No. 207765, etc.
從液晶性化合物的配向狀態中的聚合物製造相位差膜的方法可舉出例如日本特開2010-31223號公報記載的方法等。 Examples of a method for producing a retardation film from a polymer in an aligned state of a liquid crystal compound include the method described in Japanese Patent Application Laid-Open No. 2010-31223.
於第二形態時,面內相位差值Re(550)可調整為0至10nm的範圍,較理想為0至5nm的範圍,厚度方向的相位差值Rth可調整為-10至-300nm的範圍,較理想為-20至-200nm的範圍。意指厚度方向的折射率異方性之厚度方向的相位差值Rth,係可從將面內的前進軸作為傾斜軸並使其傾斜50度所測定的相位差值R50與面內相位差值R0算出。亦即,厚度方向的相位差值Rth,係可從面內相位差值R0、將面內的前進軸作為傾斜軸並使其傾斜50度所測定的相位差值R50、相位差膜的厚度d及相位差
膜的平均折射率n0,藉由下列式(10)至(12)求得nx、ny及nz,將此等帶入式(9)而算出。
In the second form, the in-plane retardation value Re(550) can be adjusted to the range of 0 to 10nm, preferably 0 to 5nm, and the thickness direction retardation value Rth can be adjusted to -10 to -300nm. The range is preferably -20 to -200nm. The phase difference value R th in the thickness direction, which means the refractive index anisotropy in the thickness direction, can be measured from the phase
Rth=[(nx+ny)/2-nz]×d (9) R th =[(n x +n y )/2-n z ]×d (9)
R0=(nx-ny)×d (10) R 0 =(n x -n y )×d (10)
(nx+ny+nz)/3=n0 (12) (n x +n y +n z )/3=n 0 (12)
此處, Here,
藉由液晶性化合物的塗佈/配向而表現光學異方性的相位差膜、藉由無機層狀化合物的塗佈而表現光學異方性的相位差膜可列舉:被稱為溫度補償型相位差膜的膜、JX日礦日石能源(股)販售的”NH FILM”(商品名,棒狀液晶為傾斜配向的膜)、富士薄膜(FUJI FILM(股))販售的”WV FILM”(商品名,圓盤狀液晶為傾斜配向的膜)、住友化學(股)販售的”VAC FILM”(商品名,完全二軸配向型的膜)、住友化學(股)販售的”new VAC FILM”(商品名,二軸配向型的膜)等。 Examples of retardation films that express optical anisotropy by coating/aligning liquid crystalline compounds and retardation films that express optical anisotropy by coating with inorganic layered compounds are called temperature-compensated retardation. Poor film, "NH FILM" (trade name, rod-shaped liquid crystal is a tilt-aligned film) sold by JX Nippon Oil & Energy Co., Ltd., "WV FILM" sold by Fuji Film (FUJI FILM Co., Ltd.) "(trade name, disc-shaped liquid crystal is tilt-aligned film), "VAC FILM" sold by Sumitomo Chemical Co., Ltd. (trade name, completely biaxially aligned film), "VAC FILM" sold by Sumitomo Chemical Co., Ltd. new VAC FILM" (trade name, biaxially aligned film), etc.
相位差膜亦可為具有2層以上的多層膜。例如,相位差膜的單面或兩面積層有保護膜者、2個以上相位差膜隔著黏著劑或接著劑積層而成者。 The retardation film may be a multilayer film having two or more layers. For example, a retardation film has a protective film laminated on one or both sides, or two or more retardation films are laminated via an adhesive or adhesive.
相位差膜為多層膜時,包含本發明的光學膜的光學積層體的構成可舉出如第4圖所示,包含將賦予穿過光1/4波長份的相位差之1/4
波長相位差層50及賦予穿過光1/2波長份的相位差之1/2波長相位差層70,隔著接著劑層或黏著劑層60積層而成的相位差膜110的構成。再者,亦可舉出如第5圖所示,包含將1/4波長相位差層50a及正C層80隔著接著劑層或黏著劑層60積層而成的光學膜40的構成。
When the retardation film is a multilayer film, the structure of the optical laminated body including the optical film of the present invention can be exemplified as shown in Figure 4, including a phase difference that imparts 1/4 of the wavelength of the transmitted light.
The
第4圖的賦予1/4波長份的相位差之1/4波長相位差層50以及賦予穿過光1/2波長份的相位差之1/2波長相位差層70,可為上述第一形態的光學膜,亦可為第五形態的光學膜。第4圖的構成時,更理想為至少一者為第五形態。
The 1/4-
第5圖的構成時,1/4波長相位差層50a較理想為上述第一形態的光學膜,又更理想為滿足式(7)、式(8)。
In the configuration of FIG. 5 , the quarter-
第4圖及第5圖中的黏著劑層7a係由黏著劑組成物所形成的層。黏著劑層7a可使用習知的黏著劑組成物,亦可使用本發明的黏著劑組成物。
The
〈液晶顯示裝置〉 〈Liquid crystal display device〉
本發明的樹脂、包含該樹脂的黏著劑組成物以及包含由前述黏著劑組成物所形成的黏著劑層的光學積層體,係可積層於有機EL元件、液晶胞等顯示元件,可使用於有機EL顯示裝置、液晶顯示裝置等顯示裝置(FPD:平面面板顯示器)。 The resin of the present invention, the adhesive composition containing the resin, and the optical laminate containing the adhesive layer formed from the adhesive composition can be laminated on display elements such as organic EL elements and liquid crystal cells, and can be used in organic Display devices (FPD: flat panel display) such as EL display devices and liquid crystal display devices.
以下,藉由實施例及比較例更詳細地說明本發明。實施例、比較例、聚合例中的「%」及「份」,在無特別說明下為「質量%」及「質量份」。 Hereinafter, the present invention will be described in more detail through Examples and Comparative Examples. "%" and "parts" in Examples, Comparative Examples, and Polymerization Examples are "mass %" and "mass parts" unless otherwise specified.
[實施例1]:具有吲哚結構及聚合性基的光選擇性吸收化合物的合成 [Example 1]: Synthesis of a light-selective absorbing compound having an indole structure and a polymerizable group
將設置有吉姆羅斯(Dimroth)冷卻管及溫度計的1000mL四頸燒瓶內置換為氮環境後,饋入式(1)表示的化合物(1-甲基-2-苯基-1H-吲哚-3-甲醛)100份、氰基乙酸40份、哌啶76份及乙腈300份,一邊攪拌一邊在80℃下保溫4小時。從所得之混合物將析出的結晶過濾、取出。混合所得之結晶與5%硫酸500份,一邊攪拌一邊在80℃下保溫1小時。過濾所得之混合物而得到固體。將所得之固體用水300份洗淨,並使其乾燥,得到式(2)表示的化合物(2-氰基-3-(1-甲基-2-苯基-1H-吲哚-3-基)-2-丙烯酸)116份。 After replacing the inside of a 1000 mL four-necked flask equipped with a Dimroth cooling tube and a thermometer with a nitrogen environment, the compound represented by formula (1) (1-methyl-2-phenyl-1H-indole-3) was fed -100 parts of formaldehyde), 40 parts of cyanoacetic acid, 76 parts of piperidine and 300 parts of acetonitrile were stirred and kept at 80°C for 4 hours. The precipitated crystals were filtered and taken out from the obtained mixture. The obtained crystals were mixed with 500 parts of 5% sulfuric acid, and the mixture was kept at 80°C for 1 hour while stirring. The resulting mixture was filtered to obtain a solid. The obtained solid was washed with 300 parts of water and dried to obtain the compound represented by formula (2) (2-cyano-3-(1-methyl-2-phenyl-1H-indol-3-yl) )-2-acrylic acid) 116 parts.
式(2)表示的化合物的鑑定 Identification of compounds represented by formula (2)
1H-NMR(CDCl3)δ:3.70(s,3H),7.30-7.42(dt,2H),7.50-7.55(m,2H),7.60-7.64(m,3H),7.68(d,1H),7.93(s,1H),8.26(d,1H) 1 H-NMR (CDCl 3 ) δ: 3.70 (s, 3H), 7.30-7.42 (dt, 2H), 7.50-7.55 (m, 2H), 7.60-7.64 (m, 3H), 7.68 (d, 1H) ,7.93(s,1H),8.26(d,1H)
將設置有溫度計的100mL四頸燒瓶內置換為氮環境後,饋入式(2)表示的化合物5份、丙烯酸-4-羥基丁酯2.3份、N,N-二甲基-4-胺基吡啶0.4份、2,6-二第三丁基-4-甲基酚0.2份及三氯甲烷50份並冷卻至0℃。一邊在所得之混合物中滴入N,N’-二異丙基碳二亞胺2.2份,一邊保持在0至5℃。滴入後,將所得之混合物在10℃下保溫4小時。過濾所得之混合物,得到濾液。濃縮所得之濾液而得到油。在所得之油中混合甲苯50份及水50份,進行分液而得到甲苯層。濃縮所得之甲苯層,得到黃色粗結晶。粗結晶用異丙醇進行再結晶,得到式(3)表示的化合物(2-氰基-3-(1-甲基-2-苯基-1H-吲哚-3-基)-2-丙烯酸-4-丙烯醯氧基丁酯)4.9份。式(3)表示的化合物的最大吸收波長為386nm。 After replacing the inside of a 100 mL four-necked flask equipped with a thermometer with a nitrogen environment, 5 parts of the compound represented by formula (2), 2.3 parts of 4-hydroxybutyl acrylate, and N,N-dimethyl-4-amino were fed. 0.4 parts of pyridine, 0.2 parts of 2,6-di-tert-butyl-4-methylphenol and 50 parts of chloroform and cooled to 0°C. While adding 2.2 parts of N,N'-diisopropylcarbodiimide dropwise to the obtained mixture, the temperature was maintained at 0 to 5°C. After the dropwise addition, the resulting mixture was kept at 10°C for 4 hours. The resulting mixture was filtered to obtain a filtrate. The resulting filtrate was concentrated to obtain oil. 50 parts of toluene and 50 parts of water were mixed with the obtained oil, and the liquid was separated to obtain a toluene layer. The obtained toluene layer was concentrated to obtain yellow crude crystals. The crude crystal is recrystallized with isopropanol to obtain the compound represented by formula (3) (2-cyano-3-(1-methyl-2-phenyl-1H-indol-3-yl)-2-acrylic acid -4-propenyloxybutyl ester) 4.9 parts. The maximum absorption wavelength of the compound represented by formula (3) is 386 nm.
式(3)表示的化合物的鑑定 Identification of the compound represented by formula (3)
1H-NMR(CDCl3)δ:1.75-1.80(m,4H),3.70(s,3H),4.15-4.20(t,2H),4.23-4.27(t,2H),5.78-5.82(dd,1H),6.06-6.14(dd,1H),6.36-6.41(dd,1H),7.35-7.43(m,5H),7.54-7.57(m,3H),8.12(s,1H),8.42-8.45(m,1H) 1 H-NMR (CDCl 3 ) δ: 1.75-1.80 (m, 4H), 3.70 (s, 3H), 4.15-4.20 (t, 2H), 4.23-4.27 (t, 2H), 5.78-5.82 (dd, 1H),6.06-6.14(dd,1H),6.36-6.41(dd,1H),7.35-7.43(m,5H),7.54-7.57(m,3H),8.12(s,1H),8.42-8.45( m,1H)
在1cm的石英皿中饋入所得之式(3)表示的化合物的甲基乙基酮溶液(0.006g/L),將石英皿設置於分光光度計UV-2450(島津製作所製),藉由雙光束法,以步長1nm在300至800nm的波長範圍測定吸光度。從所得之吸光度的值、溶液中化合物的濃度、石英皿的光徑長度,算出每個波長的克吸光係數。其結果,ε(405)=34.9L/(g‧cm),ε(440)=2.0L/(g‧cm),ε(405)/ε(440)=17.5。 The methyl ethyl ketone solution (0.006 g/L) of the obtained compound represented by formula (3) was poured into a 1 cm quartz dish, and the quartz dish was set on a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation). Double-beam method, measuring absorbance in the wavelength range from 300 to 800 nm with a step size of 1 nm. From the obtained absorbance value, the concentration of the compound in the solution, and the optical path length of the quartz dish, the gram absorption coefficient for each wavelength is calculated. As a result, ε(405)=34.9L/(g‧cm), ε(440)=2.0L/(g‧cm), ε(405)/ε(440)=17.5.
ε(λ)=A(λ)/CL ε(λ)=A(λ)/CL
〔式中,ε(λ)表示在波長λ nm中的式(3)表示的化合物的克吸光係數,A(λ)表示在波長λ nm中的吸光度,C表示濃度g/L,L表示石英皿的光徑長度cm。〕 [In the formula, ε(λ) represents the gram absorption coefficient of the compound represented by formula (3) at the wavelength λ nm, A(λ) represents the absorbance at the wavelength λ nm, C represents the concentration g/L, and L represents quartz. The optical path length of the dish is cm. 〕
[實施例2]:具有吲哚結構及聚合性基的光選擇性吸收化合物的合成 [Example 2]: Synthesis of a light-selective absorbing compound having an indole structure and a polymerizable group
除了使用丙烯酸-2-羥基乙酯2份取代丙烯酸-4-羥基丁酯2.3份外,其餘與實施例1同樣地施作,而得到式(4)表示的化合物(2-氰基-3-(1-甲基-2-苯基-1H-吲哚-3-基)-2-丙烯酸-2-丙烯醯氧基乙酯)4.3份。式(4)表示的化合物的最大吸收波長為388nm。與實施例1同樣地施作,求得克吸光係數,ε(405)=45.4L/(g‧cm),ε(440)=1.0L/(g‧cm),ε(405)/ε(440)=445.4。 Except using 2 parts of 2-hydroxyethyl acrylate instead of 2.3 parts of 4-hydroxybutyl acrylate, the same procedure as in Example 1 was carried out to obtain the compound represented by formula (4) (2-cyano-3- (1-methyl-2-phenyl-1H-indol-3-yl)-2-acrylic acid-2-propenyloxyethyl ester) 4.3 parts. The maximum absorption wavelength of the compound represented by formula (4) is 388 nm. Perform the same procedure as Example 1 to obtain the gram absorption coefficient, ε(405)=45.4L/(g‧cm), ε(440)=1.0L/(g‧cm), ε(405)/ε( 440)=445.4.
式(4)表示的化合物的鑑定 Identification of the compound represented by formula (4)
1H-NMR(CDCl3)δ:3.70(s,3H),4.38-4.43(dt,2H),4.43-4.48(dt,2H),5.83-5.86(dd,1H),6.09-6.17(dd,1H),6.4-6.45(dd,1H),7.35-7.45(m,5H),7.52-7.58(m,3H),8.12(s,1H),8.42-8.45(m,1H) 1 H-NMR (CDCl 3 ) δ: 3.70 (s, 3H), 4.38-4.43 (dt, 2H), 4.43-4.48 (dt, 2H), 5.83-5.86 (dd, 1H), 6.09-6.17 (dd, 1H),6.4-6.45(dd,1H),7.35-7.45(m,5H),7.52-7.58(m,3H),8.12(s,1H),8.42-8.45(m,1H)
[實施例3]:含有具有吲哚結構的結構單元的樹脂(A-1)的合成 [Example 3]: Synthesis of resin (A-1) containing a structural unit having an indole structure
在具備冷卻管、氮導入管、溫度計及攪拌機的反應容器中,饋入作為溶劑的乙酸乙酯141份、丙烯酸丁酯94份、丙烯酸2-羥基乙酯3份、式 Into a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer, and a stirrer, 141 parts of ethyl acetate, 94 parts of butyl acrylate, and 3 parts of 2-hydroxyethyl acrylate as solvents were fed, and the formula
(3)表示的化合物3份的混合溶液,用氮氣置換裝置內的空氣,成為不含氧並且將內溫設為60℃。於所得之混合物中,將在乙酸乙酯10份中溶解有偶氮異丁腈(聚合起始劑)0.63份的溶液全量添加。將所得之混合物保持在60℃下7小時,然後,於所得之混合物中,將於乙酸乙酯5份中溶解有4-甲氧基酚(聚合抑制劑)0.0012份的溶液全量添加量。於所得之混合物中添加乙酸乙酯,以使具有吲哚結構的樹脂(A-1)的濃度成為20%之方式調整,而調製出具有吲哚結構的樹脂(A-1)的乙酸乙酯溶液。所得之具有吲哚結構的樹脂(A-1),藉由GPC並換算聚苯乙烯的重量平均分子量Mw為74萬,Mw/Mn為5.2。藉由DSC的玻璃轉移溫度為-51℃。 (3) For a mixed solution of 3 parts of the compound shown in (3), the air in the device was replaced with nitrogen so that it did not contain oxygen, and the internal temperature was set to 60°C. To the obtained mixture, the entire amount of a solution in which 0.63 parts of azoisobutyronitrile (polymerization initiator) was dissolved in 10 parts of ethyl acetate was added. The obtained mixture was maintained at 60° C. for 7 hours, and then the entire amount of a solution containing 0.0012 parts of 4-methoxyphenol (polymerization inhibitor) dissolved in 5 parts of ethyl acetate was added to the obtained mixture. Ethyl acetate was added to the obtained mixture, and the concentration of the resin (A-1) having an indole structure was adjusted so that it became 20%, thereby preparing ethyl acetate of the resin (A-1) having an indole structure. solution. The obtained resin (A-1) having an indole structure had a polystyrene-converted weight average molecular weight Mw of 740,000 by GPC, and Mw/Mn was 5.2. The glass transition temperature by DSC was -51°C.
〈克吸光係數ε的測定〉 <Measurement of Gram Absorption Coefficient ε>
將所得之樹脂(A-1)的甲基乙基酮溶液(0.11g/L)饋入1cm的石英皿中,將石英皿設置於分光光度計UV-2450(島津製作所製),藉由雙光束法,以步長1nm在300至800nm的波長範圍測定吸光度。從所得之吸光度的值、溶液中樹脂(A)的濃度、石英皿的光徑長度,算出每個波長的克吸光係數。結果,樹脂(A-1)的ε(405)=0.442L/(g‧cm)、ε(440)=0.008L/(g‧cm)、ε(405)/ε(440)=53.3。 The obtained methyl ethyl ketone solution (0.11 g/L) of the resin (A-1) was poured into a 1 cm quartz dish, and the quartz dish was set on a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation). Beam method, measuring absorbance in the wavelength range from 300 to 800 nm with a step size of 1 nm. From the obtained absorbance value, the concentration of the resin (A) in the solution, and the optical path length of the quartz cell, the gram absorption coefficient for each wavelength was calculated. As a result, the resin (A-1) has ε(405)=0.442L/(g‧cm), ε(440)=0.008L/(g‧cm), and ε(405)/ε(440)=53.3.
ε(λ)=A(λ)/CL ε(λ)=A(λ)/CL
〔式中,ε(λ)表示在波長λ nm中的樹脂(A)的克吸光係數,A(λ)表示在波長λ nm中的吸光度,C表示濃度g/L,L表示石英皿的光徑長度cm。〕 [In the formula, ε(λ) represents the gram absorption coefficient of the resin (A) at the wavelength λ nm, A(λ) represents the absorbance at the wavelength λ nm, C represents the concentration g/L, and L represents the light of the quartz dish. Diameter length cm. 〕
[實施例4]:含有具有吲哚結構的結構單元的樹脂(A-2)的合成 [Example 4]: Synthesis of resin (A-2) containing a structural unit having an indole structure
在具備冷卻管、氮氣導入管、溫度計及攪拌機的反應容器中,饋入作為溶劑的乙酸乙酯141份、丙烯酸丁酯94份、丙烯酸2-羥基乙酯3份、式(4)表示的化合物3份的混合溶液,用氮氣置換裝置內的空氣,成為不含氧並且將內溫設為60℃。於所得之混合物中,將於乙酸乙酯10份中溶解有偶氮異丁腈(聚合起始劑)0.63份的溶液全量添加。將所得之混合物保持在60℃下7小時,然後,於所得之混合物中,將於乙酸乙酯5份中溶解有4-甲氧基酚(聚合抑制劑)0.0012份的溶液全量量。於所得之混合物中添加乙酸乙酯,以使具有吲除結構的樹脂(A-2)的濃度成為20%之方式調整,而調製出具有吲哚結構的樹脂(A-2)的乙酸乙酯溶液。所得之具有吲哚結構的樹脂(A-2)藉由GPC並且換算聚苯乙烯的重量平均分子量Mw為67萬,Mw/Mn為4.9。藉由DSC的玻璃轉移溫度為-50℃。再者,以與實施例3相同的方法,測定樹脂(A-2)的克吸光係數的結果,ε(405)=0.336L/(g‧cm)、ε(440)=0.035L/(g‧cm)、ε(405)/ε(440)=9.5。 Into a reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer, and a stirrer, 141 parts of ethyl acetate, 94 parts of butyl acrylate, 3 parts of 2-hydroxyethyl acrylate, and the compound represented by formula (4) were fed as solvents. 3 parts of the mixed solution were replaced with nitrogen gas to make the air in the device free of oxygen, and the internal temperature was set to 60°C. To the obtained mixture, the entire amount of a solution containing 0.63 parts of azoisobutyronitrile (polymerization initiator) dissolved in 10 parts of ethyl acetate was added. The obtained mixture was maintained at 60° C. for 7 hours, and then the entire amount of a solution containing 0.0012 parts of 4-methoxyphenol (polymerization inhibitor) was dissolved in 5 parts of ethyl acetate in the obtained mixture. Ethyl acetate was added to the obtained mixture, and the concentration of the resin (A-2) having an indole structure was adjusted so that the concentration thereof became 20%, thereby preparing ethyl acetate of the resin (A-2) having an indole structure. solution. The obtained resin (A-2) having an indole structure had a polystyrene-converted weight average molecular weight Mw of 670,000 by GPC, and Mw/Mn was 4.9. The glass transition temperature by DSC is -50°C. Furthermore, the gram absorption coefficient of resin (A-2) was measured using the same method as Example 3. The results showed that ε(405)=0.336L/(g·cm), ε(440)=0.035L/(g ‧cm), ε(405)/ε(440)=9.5.
[聚合例1]:丙烯酸樹脂(A-3)的調製 [Polymerization Example 1]: Preparation of acrylic resin (A-3)
饋入乙酸乙酯141份、丙烯酸丁酯94份、丙烯酸2-羥基乙酯3份,用氮氣置換裝置內的空氣成為不含氧,並且將內溫設為60℃。於所得之混合物中,將於乙酸乙酯10份溶解有偶氮異丁腈(聚合起始劑)0.63份的溶液全量添加。將所得之混合物保持在60℃下7小時,然後,於所得之混合物中,將於乙酸乙酯5份中溶解有4-甲氧基酚(聚合抑制劑)0.0012份的溶液全量添加。於所得之混合物中添加乙酸乙酯,以使具有吲哚結構的樹脂(A-3)的濃度成為20%之方式調整,而調製出具有吲哚結構的樹脂(A-3)的乙酸乙酯溶液。所得之具有吲哚結構的樹脂(A-3),藉由GPC並換算聚苯乙烯 的重量平均分子量Mw為60萬,Mw/Mn為6.0。藉由DSC的玻璃轉移溫度為-49℃。再者,使用與實施例3相同的方法,測定樹脂(A-3)的克吸光係數的結果,在波長405nm及在波長440nm中沒有吸收,任一者吸光度皆為0。 141 parts of ethyl acetate, 94 parts of butyl acrylate, and 3 parts of 2-hydroxyethyl acrylate were fed, the air in the device was replaced with nitrogen so that it did not contain oxygen, and the internal temperature was set to 60°C. To the obtained mixture, the entire amount of a solution containing 0.63 parts of azoisobutyronitrile (polymerization initiator) dissolved in 10 parts of ethyl acetate was added. The obtained mixture was maintained at 60° C. for 7 hours, and then, the entire amount of a solution containing 0.0012 parts of 4-methoxyphenol (polymerization inhibitor) dissolved in 5 parts of ethyl acetate was added to the obtained mixture. Ethyl acetate was added to the obtained mixture, and the concentration of the resin (A-3) having an indole structure was adjusted so that it became 20%, thereby preparing ethyl acetate of the resin (A-3) having an indole structure. solution. The obtained resin (A-3) having an indole structure was converted into polystyrene by GPC. The weight average molecular weight Mw is 600,000, and Mw/Mn is 6.0. The glass transition temperature by DSC is -49°C. Furthermore, when the gram absorption coefficient of the resin (A-3) was measured using the same method as in Example 3, it was found that there was no absorption at a wavelength of 405 nm and a wavelength of 440 nm, and the absorbance was 0 in both cases.
〈黏著劑組成物及黏著劑層的製作〉 〈Preparation of adhesive composition and adhesive layer〉
(a)黏著劑組成物的調製 (a) Preparation of adhesive composition
[實施例5]黏著劑組成物(1)的調製 [Example 5] Preparation of adhesive composition (1)
在所得之具有吲哚結構的樹脂(A-1)的乙酸乙酯溶液(樹脂濃度:20%)中,相對於該溶液的固形份100份,混合交聯劑(CORONATE L,固形份75%:TOSOH公司製)0.5份及矽烷化合物(信越化學工業公司製:KBM-403)0.5份,進一步以使固形份濃度成為14%之方式添加2-丁酮,而得到黏著劑組成物(1)。此外,上述交聯劑(CORONATE L)的調配量,為作為有效成分的質量份數。 In the obtained ethyl acetate solution (resin concentration: 20%) of the resin (A-1) having an indole structure, a cross-linking agent (CORONATE L, solid content 75%) was mixed with respect to 100 parts of the solid content of the solution. : TOSOH Co., Ltd.) and 0.5 part of a silane compound (KBM-403, produced by Shin-Etsu Chemical Industry Co., Ltd.), and further added 2-butanone so that the solid content concentration became 14%, to obtain an adhesive composition (1). . In addition, the compounding amount of the above-mentioned cross-linking agent (CORONATE L) is the mass part as the active ingredient.
[實施例6]黏著劑組成物(2)的調製 [Example 6] Preparation of adhesive composition (2)
在所得之具有吲哚結構的樹脂(A-2)的乙酸乙酯溶液(樹脂濃度:20%)中,相對於該溶液的固形份100份,混合交聯劑(CORONATE L,固形份75%:TOSOH公司製)0.5份及矽烷化合物(信越化學工業公司製:KBM-403)0.5份,進一步以使固形份濃度成為14%之方式添加2-丁酮,而得到黏著劑組成物(2)。此外,上述交聯劑(CORONATE L)的調配量,為作為有效成分的質量份數。 In the obtained ethyl acetate solution (resin concentration: 20%) of the resin (A-2) having an indole structure, a cross-linking agent (CORONATE L, solid content 75%) was mixed with respect to 100 parts of the solid content of the solution. : TOSOH Co., Ltd.) and 0.5 part of a silane compound (KBM-403, produced by Shin-Etsu Chemical Industry Co., Ltd.), and further added 2-butanone so that the solid content concentration became 14%, to obtain an adhesive composition (2). . In addition, the compounding amount of the above-mentioned cross-linking agent (CORONATE L) is the mass part as the active ingredient.
[比較例1]:黏著劑組成物(3)的調製 [Comparative Example 1]: Preparation of adhesive composition (3)
在丙烯酸樹脂(A-3)的乙酸乙酯溶液(樹脂濃度:20%)中,相對於該溶液的固形份100份,混合交聯劑(CORONATE L,固形份75%:TOSOH公司製)0.5份、矽烷化合物(信越化學工業公司製:KBM-403)0.5份及光吸收性化合物(紫外線吸收劑;東方化學(ORIENT Chemical)工業公司製BONASORB UA-3911)3份,進一步以使固形份濃度成為14%之方式添加2-丁酮,而得到黏著劑組成物(3)。此外,上述交聯劑(CORONATE L)的調配量,為作為有效成分的質量份數。 To an ethyl acetate solution of acrylic resin (A-3) (resin concentration: 20%), 0.5 of a cross-linking agent (CORONATE L, solid content 75%: manufactured by TOSOH Co., Ltd.) was mixed with respect to 100 parts of the solid content of the solution. parts, 0.5 parts of a silane compound (KBM-403 manufactured by Shin-Etsu Chemical Industries, Ltd.) and 3 parts of a light-absorbing compound (UV absorber; BONASORB UA-3911 manufactured by ORIENT Chemical Industries, Ltd.), and further adjust the solid content concentration to 2-Butanone was added so that it would become 14%, and the adhesive composition (3) was obtained. In addition, the compounding amount of the above-mentioned cross-linking agent (CORONATE L) is the mass part as the active ingredient.
[製作例1]:黏著劑組成物(4)的調製 [Preparation Example 1]: Preparation of adhesive composition (4)
在丙烯酸樹脂(A-3)的乙酸乙酯溶液(樹脂濃度:20%)中,相對於該溶液的固形份100份,混合交聯劑(CORONATE L,固形份75%:TOSOH公司製)0.5份、矽烷化合物(信越化學工業公司製:KBM-403)0.5份,進一步以使固形份濃度成為14%之方式添加2-丁酮,而得到黏著劑組成物(4)。 To an ethyl acetate solution of acrylic resin (A-3) (resin concentration: 20%), 0.5 of a cross-linking agent (CORONATE L, solid content 75%: manufactured by TOSOH Co., Ltd.) was mixed with respect to 100 parts of the solid content of the solution. parts and 0.5 parts of a silane compound (KBM-403 manufactured by Shin-Etsu Chemical Industry Co., Ltd.), and 2-butanone was further added so that the solid content concentration became 14%, thereby obtaining an adhesive composition (4).
(b)黏著劑層的製作 (b) Preparation of adhesive layer
在離型處理過的聚對苯二甲酸乙二酯(Lintec公司製SP-PLR382050、以下簡稱為「分隔膜」)的離型處理面,使用塗佈器塗佈前述調製的各黏著劑組成物,100℃下乾燥1分鐘,製作出黏著劑層。所得之黏著劑層的厚度為15μm。 On the release-treated surface of release-treated polyethylene terephthalate (SP-PLR382050 manufactured by Lintec Corporation, hereinafter referred to as "separator film"), use an applicator to apply each of the adhesive compositions prepared above , dry at 100°C for 1 minute to create an adhesive layer. The thickness of the adhesive layer obtained was 15 μm.
此外,將由實施例5所得之黏著劑組成物形成的黏著劑層作為黏著劑層(1),由實施例6所得之黏著劑組成物形成的黏著劑層作為黏著劑層(2),由比較例1所得之黏著劑組成物形成的黏著劑層作為黏著劑層(3),由製作例1所得之黏著劑組成物形成的黏著劑層作為黏著劑層(4)。 In addition, the adhesive layer formed of the adhesive composition obtained in Example 5 was used as the adhesive layer (1), and the adhesive layer formed of the adhesive composition obtained in Example 6 was used as the adhesive layer (2). From the comparison The adhesive layer formed from the adhesive composition obtained in Example 1 is used as the adhesive layer (3), and the adhesive layer formed from the adhesive composition obtained in Example 1 is used as the adhesive layer (4).
〈黏著劑層的吸光度測定〉 〈Measurement of absorbance of adhesive layer〉
將所得之黏著劑層(1)貼合於無鹼玻璃〔康寧公司製的商品名”EAGLE XG”〕,剝離分隔膜後,在黏著劑層(1)貼合環烯烴系樹脂膜(日本ZEON公司製ZF-14),製作出黏著劑層評估用積層體。將製成的黏著劑層評估用積層體,設置於分光光度計UV-2450(島津製作所製),藉由雙光束法,以步長1nm在300至800nm的波長範圍測定吸光度。此外,無鹼玻璃單純物質及環烯烴系樹脂膜單純物質的波長405nm及波長440nm的吸光度皆為0。 The obtained adhesive layer (1) was bonded to an alkali-free glass [trade name "EAGLE The company manufactures ZF-14) and produces laminates for adhesive layer evaluation. The prepared laminate for adhesive layer evaluation was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation), and the absorbance was measured in the wavelength range of 300 to 800 nm with a step size of 1 nm by the double-beam method. In addition, the absorbance of the alkali-free glass simple substance and the cycloolefin-based resin film simple substance is both 0 at the wavelength of 405 nm and the wavelength of 440 nm.
同樣地,也測定黏著劑層(2)及黏著劑層(3)的吸光度。將黏著劑層(1)至黏著劑層(3)的吸光度表示於表1。 Similarly, the absorbance of the adhesive layer (2) and the adhesive layer (3) was also measured. The absorbance of the adhesive layer (1) to the adhesive layer (3) is shown in Table 1.
[表1]
〈光學積層體的製作〉 〈Production of optical laminate〉
(i)偏光膜的製作 (i) Production of polarizing film
將平均聚合度約2400、皂化度99.9莫耳%以上、厚度30μm的聚乙烯醇膜(「Kuraray Poval film VF-PE#3000」、Kuraray(股)公司製)浸漬於37℃的純水後,在30℃下浸漬於包含碘及碘化鉀的水溶液(碘/碘化鉀/水(重量比)=0.04/1.5/100)。然後,在56.5℃下浸漬於包含碘化鉀及硼酸的水溶液(碘化鉀/硼酸/水(重量比)=12/3.6/100)。然後,將膜以10℃的純水 洗淨後,在85℃下乾燥,得到碘吸附配向於聚乙烯醇的厚度約12μm的偏光膜A。延伸主要在碘染色及硼酸處理的步驟進行,全部的延伸倍率為5.3倍。 After immersing a polyvinyl alcohol film ("Kuraray Poval film VF-PE#3000", manufactured by Kuraray Co., Ltd.) with an average degree of polymerization of about 2400, a saponification degree of 99.9 mol% or more, and a thickness of 30 μm in pure water at 37°C, It was immersed in an aqueous solution containing iodine and potassium iodide (iodine/potassium iodide/water (weight ratio)=0.04/1.5/100) at 30°C. Then, it was immersed in an aqueous solution containing potassium iodide and boric acid (potassium iodide/boric acid/water (weight ratio)=12/3.6/100) at 56.5°C. Then, the membrane was treated with pure water at 10°C After washing, it was dried at 85° C. to obtain a polarizing film A with a thickness of about 12 μm in which iodine is adsorbed and aligned with polyvinyl alcohol. Extension is mainly performed in the steps of iodine staining and boric acid treatment, and the total extension magnification is 5.3 times.
(ii)偏光板的製作 (ii) Production of polarizing plates
在(i)所得之偏光膜的單面,隔著由聚乙烯醇系樹脂水溶液所構成的接著劑,貼合厚度25μm的對三乙醯基纖維素膜賦予7μm的硬塗層而得之透明保護膜(「25KCHCN-TC」、凸版印刷(股)製),在與前述透明保護膜相反側的面貼合厚度23μm的環烯烴系樹脂膜(日本ZEON公司製「ZF14-023」),製作出光學膜A(偏光板、厚度67μm)。 On one side of the polarizing film obtained in (i), a triacetyl cellulose film with a thickness of 25 μm was laminated via an adhesive composed of an aqueous polyvinyl alcohol resin solution and a transparent hard coat layer of 7 μm was provided. The protective film ("25KCHCN-TC", manufactured by Toppan Printing Co., Ltd.) is produced by laminating a 23 μm-thick cyclic olefin resin film ("ZF14-023" manufactured by Japan ZEON Corporation) on the side opposite to the transparent protective film. Output optical film A (polarizing plate, thickness 67 μm).
(iii)光配向膜形成用組成物的調製 (iii) Preparation of composition for forming photo-alignment film
使用日本特開2013-33248號公報記載的方法,合成出下述結構的化合物。將下述化合物5份及環己酮95份作為成分並混合,將所得之混合物在80℃下攪拌1小時,藉此,得到光配向膜形成用組成物。 The compound having the following structure was synthesized using the method described in Japanese Patent Application Laid-Open No. 2013-33248. 5 parts of the following compound and 95 parts of cyclohexanone were mixed as components, and the resulting mixture was stirred at 80° C. for 1 hour, thereby obtaining a composition for forming a photo-alignment film.
(iv)包含聚合性液晶化合物的組成物的調製。 (iv) Preparation of a composition containing a polymerizable liquid crystal compound.
使用日本特開2010-31223號公報記載的方法,合成出下述結構的聚合性液晶化合物A。聚合性液晶化合物A的最大吸收波長λmax(LC)為350nm。 The polymerizable liquid crystal compound A having the following structure was synthesized using the method described in Japanese Patent Application Laid-Open No. 2010-31223. The maximum absorption wavelength λ max (LC) of the polymerizable liquid crystal compound A is 350 nm.
混合下述結構的聚合性液晶化合物A 12份、聚丙烯酸酯化合物(調平劑;BYK-Chemie公司製BYK-361N)0.12份、聚合起始劑(CIBA特殊化 學公司製Irgacure 369)0.72份及環戊酮100份,得到包含聚合性液晶化合物的組成物。 Mix 12 parts of polymerizable liquid crystal compound A with the following structure, 0.12 parts of polyacrylate compound (leveling agent; BYK-361N manufactured by BYK-Chemie Co., Ltd.), and polymerization initiator (CIBA special 0.72 parts of Irgacure 369 (manufactured by the company) and 100 parts of cyclopentanone were added to obtain a composition containing a polymerizable liquid crystal compound.
(v)光學異方性層的製造 (v) Fabrication of optically anisotropic layer
將環烯烴系樹脂膜(日本ZEON公司製ZF-14),使用電暈處理裝置(AGF-B10、春日電機(股)公司製),以輸出0.3kW、處理速度3m/分鐘的條件,處理1次。在實施過電暈處理的表面,用棒塗器塗佈(iii)所得之光配向膜形成用組成物,80℃下乾燥1分鐘,使用偏光UV照射裝置(SPOT CURE SP-7;USHIO電機公司製),以100mJ/cm2的累積光量實施偏光UV曝光。所得之配向膜的膜厚以橢圓儀測定時為100nm。 The cycloolefin-based resin film (ZF-14 manufactured by Japan ZEON Co., Ltd.) was treated with a corona treatment device (AGF-B10, manufactured by Kasuga Electric Co., Ltd.) at an output of 0.3kW and a processing speed of 3m/min. 1 Second-rate. The photo-alignment film forming composition obtained in (iii) was applied with a bar coater on the corona-treated surface, dried at 80°C for 1 minute, and then used a polarized UV irradiation device (SPOT CURE SP-7; USHIO Electric Co., Ltd. (made), polarized UV exposure was carried out with a cumulative light amount of 100mJ/ cm2 . The film thickness of the obtained alignment film was 100 nm when measured with an ellipsometer.
然後,在配向膜上,用棒塗器塗佈(iv)所得之包含聚合性液晶化合物的組成物A所構成的塗佈液,120℃下乾燥1分鐘,使用高壓水銀燈(UNICURE VB-15201BY-A、USHIO電機公司製),從塗佈有包含聚合性液晶化合物的組成物的面側,照射紫外線(氮環境下、波長313nm的累積光量:500mJ/cm2),形成包含光學異方性層1的光學膜。所得之光學異方性層1的膜厚以雷射顯微鏡測定時為2μm。
Then, the coating liquid composed of the composition A containing the polymerizable liquid crystal compound obtained in (iv) was applied on the alignment film with a bar coater, dried at 120° C. for 1 minute, and a high-pressure mercury lamp (UNICURE VB-15201BY- A. Manufactured by USHIO Denki Co., Ltd.), irradiate ultraviolet light (accumulated light intensity at wavelength 313 nm in a nitrogen environment: 500 mJ/cm 2 ) from the surface side coated with a composition containing a polymerizable liquid crystal compound to form a layer containing
[實施例7]:光學積層體(1)的製作 [Example 7]: Preparation of optical laminate (1)
在上述(ii)製作的偏光板的環烯烴系樹脂膜面貼合黏著劑層(1),並且剝離分隔膜。再將黏著劑層(1)的剝離分隔膜後的面與(v)製作的光學異方性 層的環烯烴系樹脂膜面的相反面貼合,剝離環烯烴系樹脂膜。在光學異方性層的剝離環烯烴系樹脂膜後的面,貼合附分隔膜的黏著劑層(4),而得到光學積層體(1)。 The adhesive layer (1) is bonded to the cycloolefin-based resin film surface of the polarizing plate produced in the above (ii), and the separator film is peeled off. Then compare the surface of the adhesive layer (1) after peeling off the separator film with the optical anisotropy produced by (v). The opposite side of the cycloolefin-based resin film surface of the layer is bonded, and the cycloolefin-based resin film is peeled off. An adhesive layer (4) with a separator film is bonded to the surface of the optically anisotropic layer from which the cycloolefin-based resin film has been peeled off, thereby obtaining an optical laminate (1).
[實施例8]:光學積層體(2)的製作 [Example 8]: Preparation of optical laminate (2)
除了使用黏著劑層(2)取代黏著劑層(1)外,其餘與實施例7同樣地,得到光學積層體(2)。 The optical laminated body (2) was obtained in the same manner as in Example 7 except that the adhesive layer (2) was used instead of the adhesive layer (1).
[比較例2]:光學積層體(3)的製作 [Comparative Example 2]: Production of optical laminate (3)
除了使用黏著劑層(3)取代黏著劑層(1)外,其餘與實施例7同樣地,得到光學積層體(3)。 An optical laminated body (3) was obtained in the same manner as in Example 7 except that the adhesive layer (3) was used instead of the adhesive layer (1).
[製作例2]:光學積層體(4)的製作 [Preparation Example 2]: Preparation of optical laminate (4)
除了使用黏著劑層(4)取代黏著劑層(1)外,其餘與實施例5同樣地,得到光學積層體(4)。 An optical laminated body (4) was obtained in the same manner as in Example 5 except that the adhesive layer (4) was used instead of the adhesive layer (1).
〈黏著劑層的耐滲出性評估〉 〈Evaluation of Bleeding Resistance of Adhesive Layer〉
將所得之光學積層體(1)裁切為40mm×40mm的大小,剝離積層於黏著劑層(4)的分隔膜後,將其與無鹼玻璃〔康寧公司製的商品名“EAGLE XG”〕貼合。將所得之附玻璃的光學積層體使用顯微鏡確認面內的化合物的結晶的析出。然後,將所得之附玻璃的光學積層體,投入溫度23℃、60%的烤箱500小時,使用顯微鏡確認面內的化合物的結晶的析出,確認到化合物的結晶的析出沒有增加。評估結果表示於表2。 The obtained optical laminate (1) was cut into a size of 40 mm × 40 mm, and the separator film laminated on the adhesive layer (4) was peeled off, and then combined with alkali-free glass [trade name "EAGLE XG" manufactured by Corning Corporation] Fit. The obtained glass-attached optical laminate was used to confirm the precipitation of compound crystals in the plane using a microscope. Then, the obtained glass-coated optical laminate was put into an oven at a temperature of 23° C. and 60% for 500 hours, and the precipitation of compound crystals in the surface was confirmed using a microscope. It was confirmed that there was no increase in the precipitation of compound crystals. The evaluation results are shown in Table 2.
除了使用光學積層體(2)取代光學積層體(1)外,其餘與上述同樣地進行黏著劑層的耐滲出性評估。評估結果表示於表2。 The bleeding resistance of the adhesive layer was evaluated in the same manner as above except that the optical laminate (2) was used instead of the optical laminate (1). The evaluation results are shown in Table 2.
除了使用光學積層體(3)取代光學積層體(1)外,其餘與上述同樣地進行黏著劑層的耐滲出性評估。評估結果表示於表2。 The bleeding resistance of the adhesive layer was evaluated in the same manner as above except that the optical laminate (3) was used instead of the optical laminate (1). The evaluation results are shown in Table 2.
〈因黏著劑層所致之對光學異方性層的相位差變化影響的確認〉 〈Confirmation of the influence of the phase difference change on the optical anisotropy layer due to the adhesive layer〉
將所得之光學積層體(1)裁切為40mm×40mm的大小,剝離積層於黏著劑層(4)的分隔膜將其與無鹼玻璃〔康寧公司製的商品名“EAGLE XG”〕貼合。將所得之附玻璃的光學積層體的波長450nm的相位差值,藉由複折射測定裝置(KOBRA-WR;王子計測機器(股)公司製)進行測定。然後,將附玻璃的光學積層體,投入溫度80℃的烤箱120小時,取出並放置在23℃、50%的環境24小時後,再次測定波長450nm的相位差值。 The obtained optical laminate (1) was cut into a size of 40 mm × 40 mm, and the separator film laminated on the adhesive layer (4) was peeled off and laminated to alkali-free glass (trade name "EAGLE XG" manufactured by Corning Corporation). . The phase difference value at a wavelength of 450 nm of the obtained glass-attached optical laminate was measured with a birefringence measuring device (KOBRA-WR; manufactured by Oji Scientific Instruments Co., Ltd.). Then, the glass-coated optical laminate was put into an oven at a temperature of 80°C for 120 hours, taken out and left in an environment of 23°C and 50% for 24 hours, and then the phase difference value at a wavelength of 450 nm was measured again.
與上述同樣地,使用光學積層體(4)取代光學積層體(1),進行測定。 In the same manner as above, measurement was performed using the optical laminated body (4) instead of the optical laminated body (1).
光學積層體(1)的相位差變化,係從光學積層體(1)的耐久前後的波長450nm的相位差值的變化量,減去光學積層體(4)的耐久前後的波長450nm的相位差值的變化量而求得。相位差值變化值表示於表2。 The phase difference change of the optical laminated body (1) is calculated by subtracting the phase difference of the wavelength 450 nm of the optical laminated body (4) before and after the durability from the change amount of the phase difference value of the wavelength 450 nm before and after the durability of the optical laminated body (1). Calculated by the change in value. The phase difference change values are shown in Table 2.
除了使用光學積層體(2)取代光學積層體(1)外,其餘與上述同樣地,進行因黏著劑層所致之對光學異方性層的相位差變化影響的確認。耐久前後的相位差值變化值表示於表2。 The influence of the adhesive layer on the phase difference change of the optically anisotropic layer was confirmed in the same manner as above except that the optical laminated body (2) was used instead of the optical laminated body (1). The change value of the phase difference before and after durability is shown in Table 2.
除了使用光學積層體(3)取代光學積層體(1)外,其餘與上述同樣地,進行因黏著劑層所致之對光學異方性層的相位差變化影響的確認。耐久前後的相位差值變化值表示於表2。 The influence of the adhesive layer on the phase difference change of the optically anisotropic layer was confirmed in the same manner as above except that the optical laminated body (3) was used instead of the optical laminated body (1). The change value of the phase difference before and after durability is shown in Table 2.
〈光學膜的吸光度測定〉 〈Measurement of absorbance of optical films〉
將所得之光學積層體(1)裁切為40mm×40mm的大小,剝離積層於黏著劑層(4)的分隔膜,將其與無鹼玻璃〔康寧公司製的商品名”EAGLE XG”〕貼合。對測定樣品使用附積分球的分光光度計〔日本分光(股)製的製品名「V7100」〕,測定波長380至780nm範圍的光學積層體(1)的穿透軸方向及吸收軸方向的穿透光譜,由光學積層體(1)的透過軸方向的透過光譜,算出光學積層體(1)的波長405nm的吸光度。此外,TAC膜單體、COP膜單體及無鹼玻璃單體在波長350nm、波長405nm及波長440nm的吸光度皆為0。 The obtained optical laminate (1) was cut into a size of 40 mm × 40 mm, the separator film laminated on the adhesive layer (4) was peeled off, and the alkali-free glass (trade name "EAGLE XG" manufactured by Corning Incorporated) was attached to it. combine. Using a spectrophotometer with an integrating sphere (product name "V7100" manufactured by JASCO Corporation) on the measurement sample, the transmission axis direction and absorption axis direction of the optical layered body (1) in the wavelength range of 380 to 780 nm are measured. The transmittance spectrum was calculated from the transmission spectrum of the optical laminate (1) in the transmission axis direction, and the absorbance of the optical laminate (1) at a wavelength of 405 nm was calculated. In addition, the absorbance of TAC film monomer, COP film monomer and alkali-free glass monomer at wavelength 350nm, wavelength 405nm and wavelength 440nm are all 0.
〈耐候性的評估〉 〈Evaluation of weather resistance〉
在63℃、50%濕度條件下,將光學積層體(1)投入陽光氣候計(Suga測試機(股)公司製:型號SUNSHINE WEATHER METER S80)24小時,實施24小時的耐候性測試。將取出的樣品的吸光度利用與上述〈光學膜的吸光度測定〉相同的方法測定。從測定的吸光度,根據下述式,求得在波長405nm中的樣品的吸光度保持率。結果表示於表1。吸光度保持率越高,表示沒有光選擇性吸收功能劣化之良好的耐候性。 Under the conditions of 63° C. and 50% humidity, the optical laminated body (1) was placed in a solar climate meter (model SUNSHINE WEATHER METER S80 manufactured by Suga Test Machine Co., Ltd.) for 24 hours, and a 24-hour weather resistance test was performed. The absorbance of the taken out sample was measured by the same method as the above-mentioned "Absorbance Measurement of Optical Film". From the measured absorbance, the absorbance retention rate of the sample at a wavelength of 405 nm was determined according to the following formula. The results are shown in Table 1. The higher the absorbance retention rate, the better the weather resistance without deterioration of the light selective absorption function.
吸光度保持率=(耐久測試後的A(405)/耐久測試前的A(405))×100 Absorbance retention rate = (A(405) after durability test/A(405) before durability test)×100
[表2]
將由包含本發明的樹脂(A)的黏著劑組成物所形成的黏著劑層積層於光學膜時,相位差變化被抑制。此係認為,相較於單獨含有具有吲哚結構的光選擇性吸收化合物的黏著劑組成物,藉由將具有聚合性基及吲哚結構的光選擇性吸收化合物摻入樹脂中,可抑制具有吲哚結構的光選擇性吸收化合物的遷移。 When an adhesive layer composed of an adhesive composition containing the resin (A) of the present invention is laminated on an optical film, a change in phase difference is suppressed. This is considered that, compared to an adhesive composition containing a light-selective absorbing compound having an indole structure alone, by incorporating a light-selective absorbing compound having a polymerizable group and an indole structure into a resin, it is possible to suppress Migration of photoselectively absorbing compounds with indole structures.
再者,由包含本發明的樹脂(A)的黏著劑組成物所形成的黏著劑層,即使在85下進行120小時的耐熱測試後,不會增加化合物的析出,具有良好的耐滲出性。再者,由包含本發明的樹脂(A)的黏著劑組成物所形成的黏著劑層係具有良好的A(405)/A(440)的值。 Furthermore, the adhesive layer formed from the adhesive composition containing the resin (A) of the present invention does not increase the precipitation of compounds and has good bleeding resistance even after a heat resistance test at 85°C for 120 hours. Furthermore, the adhesive layer formed from the adhesive composition containing the resin (A) of the present invention has a good A(405)/A(440) value.
本發明的樹脂、包含該樹脂的黏著劑組成物、由前述黏著劑組成物所形成的黏著劑層及包含前述黏著劑層的光學積層體適合使用於液晶面板及液晶顯示裝置。 The resin of the present invention, the adhesive composition containing the resin, the adhesive layer formed from the adhesive composition, and the optical laminate containing the adhesive layer are suitable for use in liquid crystal panels and liquid crystal display devices.
1‧‧‧黏著劑層 1‧‧‧Adhesive layer
2‧‧‧剝離膜 2‧‧‧Peel-off film
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KR20220137930A (en) * | 2020-02-18 | 2022-10-12 | 스미또모 가가꾸 가부시키가이샤 | optical laminate |
JP7193559B2 (en) * | 2020-02-18 | 2022-12-20 | 住友化学株式会社 | optical laminate |
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TW201738349A (en) * | 2015-12-28 | 2017-11-01 | 住友化學股份有限公司 | Optical laminate |
TW201908353A (en) * | 2017-07-21 | 2019-03-01 | 南韓商三星Sdi股份有限公司 | Composition for encapsulating organic light-emitting diode element and organic light-emitting diode display prepared using same |
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KR101475102B1 (en) * | 2007-09-26 | 2014-12-22 | 덴끼 가가꾸 고교 가부시키가이샤 | Adhesive compositions and jointing method |
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