WO2016194920A1 - 無溶剤型光硬化性接着剤用組成物 - Google Patents
無溶剤型光硬化性接着剤用組成物 Download PDFInfo
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- WO2016194920A1 WO2016194920A1 PCT/JP2016/066098 JP2016066098W WO2016194920A1 WO 2016194920 A1 WO2016194920 A1 WO 2016194920A1 JP 2016066098 W JP2016066098 W JP 2016066098W WO 2016194920 A1 WO2016194920 A1 WO 2016194920A1
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- WIPO (PCT)
- Prior art keywords
- acrylate
- group
- meth
- solvent
- adhesive
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 133
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 133
- 239000000203 mixture Substances 0.000 title claims abstract description 89
- 229920000642 polymer Polymers 0.000 claims abstract description 75
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims abstract description 50
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003085 diluting agent Substances 0.000 claims abstract description 21
- 239000000463 material Substances 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 18
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 tetrahydrofurfuryl Chemical group 0.000 claims description 179
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 239000000178 monomer Substances 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 14
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 230000003287 optical effect Effects 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000002313 adhesive film Substances 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 3
- QQAKULNNRFPQRK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;oxolane;prop-2-enoic acid Chemical compound C1CCOC1.OC(=O)C=C.OCC(CO)(CO)CO QQAKULNNRFPQRK-UHFFFAOYSA-N 0.000 claims description 3
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 3
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 3
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 claims description 3
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 claims description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 3
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 3
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 3
- 238000000016 photochemical curing Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 238000001723 curing Methods 0.000 claims description 2
- 229940065472 octyl acrylate Drugs 0.000 claims description 2
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 54
- 229920000587 hyperbranched polymer Polymers 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 34
- 150000001875 compounds Chemical class 0.000 description 30
- 239000010408 film Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 21
- 150000004820 halides Chemical class 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000002966 varnish Substances 0.000 description 18
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
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- 239000010453 quartz Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- 125000003282 alkyl amino group Chemical group 0.000 description 10
- 235000011114 ammonium hydroxide Nutrition 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 238000005227 gel permeation chromatography Methods 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 6
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 125000001769 aryl amino group Chemical group 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- GGMFNOCTRKKNSC-UHFFFAOYSA-N 1,2,4-trichloro-2h-1,3,5-triazine Chemical compound ClC1N=C(Cl)N=CN1Cl GGMFNOCTRKKNSC-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000012790 adhesive layer Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
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- 239000004065 semiconductor Substances 0.000 description 4
- 238000002076 thermal analysis method Methods 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000003848 UV Light-Curing Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000005370 alkoxysilyl group Chemical group 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229940018564 m-phenylenediamine Drugs 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YZVWKHVRBDQPMQ-UHFFFAOYSA-N 1-aminopyrene Chemical compound C1=C2C(N)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 YZVWKHVRBDQPMQ-UHFFFAOYSA-N 0.000 description 2
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000004147 Sorbitan trioleate Substances 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
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- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- AQBJGAUQEJFPKZ-UHFFFAOYSA-N methyl 4-(aminomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CN)C=C1 AQBJGAUQEJFPKZ-UHFFFAOYSA-N 0.000 description 1
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- GXMIHVHJTLPVKL-UHFFFAOYSA-N n,n,2-trimethylpropanamide Chemical compound CC(C)C(=O)N(C)C GXMIHVHJTLPVKL-UHFFFAOYSA-N 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- ZCOGQSHZVSZAHH-UHFFFAOYSA-N n,n-dimethylaziridine-1-carboxamide Chemical compound CN(C)C(=O)N1CC1 ZCOGQSHZVSZAHH-UHFFFAOYSA-N 0.000 description 1
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DVQCXAUFUOFSDW-UHFFFAOYSA-N n-prop-2-enylacetamide Chemical compound CC(=O)NCC=C DVQCXAUFUOFSDW-UHFFFAOYSA-N 0.000 description 1
- SHIGCAOWAAOWIG-UHFFFAOYSA-N n-prop-2-enylformamide Chemical compound C=CCNC=O SHIGCAOWAAOWIG-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- RZFODFPMOHAYIR-UHFFFAOYSA-N oxepan-2-one;prop-2-enoic acid Chemical compound OC(=O)C=C.O=C1CCCCCO1 RZFODFPMOHAYIR-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 description 1
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MFUFBSLEAGDECJ-UHFFFAOYSA-N pyren-2-ylamine Natural products C1=CC=C2C=CC3=CC(N)=CC4=CC=C1C2=C43 MFUFBSLEAGDECJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/02—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 single or double bond to nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
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- C08G73/02—Polyamines
- C08G73/0273—Polyamines containing heterocyclic moieties in the main chain
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/0644—Poly(1,3,5)triazines
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/34—Heterocyclic compounds having nitrogen in the ring
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- C08K5/3492—Triazines
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
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- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/10—Adhesives in the form of films or foils without carriers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/11—Anti-reflection coatings
- G02B1/111—Anti-reflection coatings using layers comprising organic materials
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/02—Details
- H01L31/0216—Coatings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2433/00—Presence of (meth)acrylic polymer
Definitions
- the present invention relates to a composition for a solventless photocurable adhesive, and more specifically, for a solventless photocurable adhesive that contains a triazine ring-containing polymer and a reactive diluent and does not contain a solvent. Relates to the composition.
- a solvent-free film-forming composition containing a triazine ring-containing polymer, which is a high refractive index material, already reported by the present applicant is photoadhered.
- a refractive index adjusting material such as an adhesive
- only an adhesive composition having poor compatibility with an acrylic material as an adhesive component and high viscosity and not suitable for practical use could be obtained.
- the present invention has been made in view of such circumstances, and is a composition for a photocurable adhesive having good compatibility with an acrylic material or the like as an adhesive component, although it does not contain a solvent. The purpose is to provide.
- the present inventors have determined that the molecular weight of the triazine ring-containing polymer is related to the compatibility with the acrylic material, and the molecular weight falls within a predetermined range. As a result, it is found that a composition having good compatibility with the acrylic material as the adhesive component can be obtained even though the solvent is not contained, and the composition is solvent-free photocurable adhesive.
- the present invention was completed by finding that it is suitable as a refractive index adjusting material for an agent.
- a solvent-free photocurable adhesive composition characterized by not containing a solvent, ⁇ Wherein, R and R 'each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or an aralkyl group, Ar represents at least one selected from the group represented by formulas (2) to (13).
- R 1 to R 92 are independently of each other a hydrogen atom, a halogen atom, a carboxyl group, a sulfo group, an alkyl group which may have a branched structure having 1 to 10 carbon atoms, or a carbon number of 1 Represents an alkoxy group which may have a branched structure of ⁇ 10, and R 93 and R 94 each independently represent a hydrogen atom or an alkyl group which may have a branched structure of 1 to 10 carbon atoms.
- W 1 and W 2 are each independently a single bond
- CR 95 R 96 R 95 and R 96 are each independently a hydrogen atom or a branched structure having 1 to 10 carbon atoms.
- An alkyl group (which may be combined to form a ring)), C ⁇ O, O, S, SO, SO 2 , or NR 97 (R 97 is hydrogen) It represents an alkyl group which may have an atom or a branched structure having 1 to 10 carbon atoms.
- X 1 and X 2 are each independently a single bond, an alkylene group which may have a branched structure having 1 to 10 carbon atoms, or a group represented by the formula (14) (Wherein R 98 to R 101 are each independently a hydrogen atom, a halogen atom, a carboxyl group, a sulfo group, an alkyl group which may have a branched structure having 1 to 10 carbon atoms, or 1 carbon atom) Represents an alkoxy group which may have a branched structure of ⁇ 10, and Y 1 and Y 2 each independently represent an alkylene group which may have a single bond or a branched structure of 1 to 10 carbon atoms.
- R 102 and R 104 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a polymerizable carbon-carbon double bond-containing group
- R 103 represents a hydrogen atom
- a solvent-free photocurable adhesive composition wherein R 102 and R 103 in the formula (A) are both hydrogen atoms, and R 104 is a polymerizable carbon-carbon double bond-containing group, 3. 1 or 2 solvent-free photocurable adhesive, wherein the reactive diluent is one or more selected from N-vinylformamide, 4-acryloylmorpholine, N-dimethylacrylamide, and N-diethylacrylamide Composition, 4).
- Ar is a solvent-free photocurable adhesive composition according to any one of 1 to 3 represented by formula (15): 5.
- the solvent-free photocurable adhesive composition according to any one of 1 to 4 which is used for a solventless photocurable adhesive having an acrylic material as an adhesive component; 6).
- a solvent-free type comprising the solvent-free photocurable adhesive composition according to any one of 1 to 5, and at least one selected from allyl monomers, (meth) acrylic monomers, and (meth) acrylic oligomers Light curable adhesive, 7).
- the (meth) acrylic monomer is methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2- (2-ethoxyethoxy) ethyl acrylate, tetrahydrofurfuryl (meth) acrylate, lauryl acrylate, Octyl acrylate, isodecyl acrylate, 2-phenoxyethyl acrylate, 2-ethylhexyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentadienyl (meth)
- 6 or 7 solvent-free photocurable adhesive containing a photo radical initiator 9.
- An optical device manufactured using the adhesive film of No. 9 is provided.
- the composition for an adhesive of the present invention has good compatibility with an acrylic material that is an adhesive component even though it does not contain an organic solvent, so that the refractive index adjustment of the solventless photocurable adhesive is adjusted. It can be suitably used as a material or the like.
- the adhesive containing the adhesive composition of the present invention includes a liquid crystal display, an organic electroluminescence (EL) display, a touch panel, an optical semiconductor (LED) element, a solid-state imaging element, an organic thin film solar cell, a dye-sensitized solar cell, an organic It is suitable as an adhesive for devices requiring transparency and a high refractive index, such as electronic devices and optical devices such as thin film transistors (TFTs), lenses, prisms, cameras, binoculars, microscopes, and semiconductor exposure apparatuses.
- TFTs thin film transistors
- FIG. 6 is a transmittance spectrum diagram of a cured film of HB-TmDAL-TN40 produced in Example 2-2.
- the solvent-free photocurable adhesive composition according to the present invention comprises a triazine ring-containing polymer having a repeating unit structure represented by the formula (1) and having a weight average molecular weight of 500 to 7,000, And a reactive diluent represented by A), which does not contain a solvent.
- the “adhesive” in the present invention is a concept including an adhesive.
- R and R ′ each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or an aralkyl group, and are both hydrogen atoms from the viewpoint of further increasing the refractive index. It is preferable.
- the number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 20, and more preferably 1 to 10 carbon atoms in view of further improving the heat resistance of the polymer. Is even more preferable.
- the structure may be any of a chain, a branch, and a ring.
- alkyl group examples include methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, s-butyl, t-butyl, cyclobutyl, 1-methyl-cyclopropyl, 2-methyl-cyclopropyl.
- N-pentyl 1-methyl-n-butyl, 2-methyl-n-butyl, 3-methyl-n-butyl, 1,1-dimethyl-n-propyl, 1,2-dimethyl-n-propyl, 2 , 2-dimethyl-n-propyl, 1-ethyl-n-propyl, cyclopentyl, 1-methyl-cyclobutyl, 2-methyl-cyclobutyl, 3-methyl-cyclobutyl, 1,2-dimethyl-cyclopropyl, 2,3- Dimethyl-cyclopropyl, 1-ethyl-cyclopropyl, 2-ethyl-cyclopropyl, n-hexyl, 1-methyl-n-pe Til, 2-methyl-n-pentyl, 3-methyl-n-pentyl, 4-methyl-n-pentyl, 1,1-dimethyl-n-butyl, 1,2-dimethyl-n-butyl, 1,3- Dimethyl-n-butyl, 2,2-di
- the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20, and more preferably 1 to 10 carbon atoms, more preferably 1 to 3 carbon atoms in view of further improving the heat resistance of the polymer. preferable.
- the structure of the alkyl moiety may be any of a chain, a branch, and a ring.
- alkoxy group examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, n-pentoxy, 1-methyl-n-butoxy, 2-methyl-n -Butoxy, 3-methyl-n-butoxy, 1,1-dimethyl-n-propoxy, 1,2-dimethyl-n-propoxy, 2,2-dimethyl-n-propoxy, 1-ethyl-n-propoxy, n -Hexyloxy, 1-methyl-n-pentyloxy, 2-methyl-n-pentyloxy, 3-methyl-n-pentyloxy, 4-methyl-n-pentyloxy, 1,1-dimethyl-n-butoxy, 1,2-dimethyl-n-butoxy, 1,3-dimethyl-n-butoxy, 2,2-dimethyl-n-butoxy, 2,3-dimethyl-n-butoxy 3,3-dimethyl-n-butoxy, 1-ethoxy,
- the number of carbon atoms of the aryl group is not particularly limited, but is preferably 6 to 40. In view of further improving the heat resistance of the polymer, 6 to 16 carbon atoms are more preferable, and 6 to 13 are even more preferable. preferable.
- aryl group examples include phenyl, o-chlorophenyl, m-chlorophenyl, p-chlorophenyl, o-fluorophenyl, p-fluorophenyl, o-methoxyphenyl, p-methoxyphenyl, p-nitrophenyl, p-cyanophenyl, ⁇ -naphthyl, ⁇ -naphthyl, o-biphenylyl, m-biphenylyl, p-biphenylyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4 -Phenanthryl, 9-phenanthryl group and the like.
- the number of carbon atoms of the aralkyl group is not particularly limited, but preferably 7 to 20 carbon atoms, and the alkyl portion may be linear, branched or cyclic. Specific examples thereof include benzyl, p-methylphenylmethyl, m-methylphenylmethyl, o-ethylphenylmethyl, m-ethylphenylmethyl, p-ethylphenylmethyl, 2-propylphenylmethyl, 4-isopropylphenylmethyl, Examples include 4-isobutylphenylmethyl, ⁇ -naphthylmethyl group and the like.
- Ar represents at least one selected from the group represented by formulas (2) to (13).
- R 1 to R 92 are independently of each other a hydrogen atom, a halogen atom, a carboxyl group, a sulfo group, an alkyl group that may have a branched structure having 1 to 10 carbon atoms, or a group having 1 to 10 carbon atoms.
- R 93 and R 94 each independently represent a hydrogen atom or an alkyl group which may have a branched structure having 1 to 10 carbon atoms; 1 and W 2 are each independently a single bond, CR 95 R 96 (R 95 and R 96 are each independently a hydrogen atom or an alkyl optionally having a branched structure of 1 to 10 carbon atoms) Group (however, these may be combined to form a ring)), C ⁇ O, O, S, SO, SO 2 , or NR 97 (R 97 is a hydrogen atom or a carbon atom) Represents an alkyl group which may have a branched structure of formula 1-10. To express.
- halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- alkyl group and alkoxy group are the same as those described above.
- X 1 and X 2 each independently represent a single bond, an alkylene group which may have a branched structure having 1 to 10 carbon atoms, or a group represented by the formula (14).
- R 98 to R 101 are each independently a hydrogen atom, a halogen atom, a carboxyl group, a sulfo group, an alkyl group which may have a branched structure having 1 to 10 carbon atoms, or a carbon atom having 1 to 10 carbon atoms.
- An alkoxy group which may have a branched structure is represented, and Y 1 and Y 2 each independently represent an alkylene group which may have a single bond or a branched structure having 1 to 10 carbon atoms.
- Examples of the halogen atom, alkyl group and alkoxy group are the same as those described above.
- Examples of the alkylene group that may have a branched structure having 1 to 10 carbon atoms include methylene, ethylene, propylene, trimethylene, tetramethylene, and pentamethylene groups.
- R 1 to R 92 and R 98 to R 101 a hydrogen atom, a halogen atom, a sulfo group, an alkyl group which may have a branched structure having 1 to 5 carbon atoms, or a carbon number of 1 to The alkoxy group which may have 5 branched structures is preferable, and a hydrogen atom is more preferable.
- Ar is preferably at least one of the formulas (2), (5) to (13), and the formulas (2), (5), (7), (8), (11) to (13) More preferably, at least one selected from Specific examples of the aryl group represented by the above formulas (2) to (13) include, but are not limited to, those represented by the following formulae.
- an aryl group represented by the following formula is more preferable because a polymer having a higher refractive index can be obtained.
- Ar is preferably an m-phenylene group represented by the formula (15).
- the triazine ring-containing polymer of the present invention preferably has a repeating unit structure represented by the formula (16), and more preferably has a repeating unit structure represented by the formula (17).
- a hyperbranched polymer (hyperbranched polymer) represented by the formula (18) is optimal.
- the weight average molecular weight of the triazine ring-containing polymer represented by the formula (1) is 500 to 7,000 from the viewpoint of compatibility with an adhesive component such as an acrylic material.
- the upper limit is preferably 6,000 or less, and most preferably 5,000 or less.
- 1,000 or more are preferable and 2,000 or more are more preferable from the point which improves heat resistance more and makes shrinkage
- the weight average molecular weight in this invention is an average molecular weight obtained by standard polystyrene conversion by gel permeation chromatography (henceforth GPC) analysis.
- the triazine ring-containing polymer of the present invention can be produced according to the technique of Patent Document 4 described above.
- a hyperbranched polymer (hyperbranched polymer) having a repeating structure (21) is obtained by mixing cyanuric halide (19) and m-phenylenediamine compound (20) in a suitable organic solvent. It can obtain by making it react.
- a hyperbranched polymer (hyperbranched polymer) having a repeating structure (21) is obtained by combining cyanuric halide (19) and m-phenylenediamine compound (20) in a suitable organic solvent. It can also be synthesized from the compound (22) obtained by reacting in an amount.
- the amount of each raw material charged is arbitrary as long as the target polymer is obtained, but the diamino compound (20) 0. 01 to 10 equivalents are preferred.
- the diamino compound (20) is used in an amount of less than 3 equivalents relative to 2 equivalents of cyanuric halide (19). Is preferred.
- cyanuric halide (19) is used in an amount of less than 2 equivalents with respect to 3 equivalents of diamino compound (20). It is preferable.
- the molecular weight of the resulting hyperbranched polymer (hyperbranched polymer) can be easily adjusted by appropriately adjusting the amounts of the diamino compound (20) and the cyanuric halide (19).
- the concentration in an organic solvent As a method for adjusting the molecular weight of the hyperbranched polymer (hyperbranched polymer), it is possible to control the concentration in an organic solvent.
- the reaction concentration solid content concentration
- the reaction concentration solid content concentration
- organic solvent various solvents usually used in this kind of reaction can be used, for example, tetrahydrofuran, dioxane, dimethyl sulfoxide; N, N-dimethylformamide, N-methyl-2-pyrrolidone, tetramethylurea.
- N, N-dimethylformamide, dimethyl sulfoxide, N-methyl-2-pyrrolidone, N, N-dimethylacetamide, and a mixed system thereof are preferable, and N, N-dimethylacetamide, N-methyl-2-pyrrolidone are particularly preferable. Is preferred.
- the reaction temperature may be appropriately set in the range from the melting point to the boiling point of the solvent used, and is preferably about 0 to 150 ° C., more preferably 60 to 100 ° C. preferable.
- the reaction temperature is preferably 60 to 150 ° C., more preferably 80 to 150 ° C., and even more preferably 80 to 120 ° C. from the viewpoint of suppressing linearity and increasing the degree of branching.
- the cyanuric halide (19) and the diamino compound (20) are preferably mixed at a low temperature. About 50 ° C.
- the reaction temperature may be appropriately set in the range from the melting point of the solvent used to the boiling point of the solvent, but is preferably about ⁇ 50 to 50 ° C., and preferably about ⁇ 20 to 50 ° C. Is more preferably about ⁇ 10 to 50 ° C., and further preferably ⁇ 10 to 10 ° C.
- it is preferable to employ a two-step process comprising a first step of reacting at ⁇ 50 to 50 ° C. and a second step of reacting at 60 to 150 ° C. following this step.
- the order of blending the components is arbitrary, but in the reaction of Scheme 1, the solution containing cyanuric halide (19) or diamino compound (20) and an organic solvent is cooled, A method of adding a diamino compound (20) or a cyanuric halide (19) is preferred. In this case, the component previously dissolved in the solvent and the component added later may be either. However, in consideration of obtaining the above-mentioned polymer having the weight average molecular weight, the internal temperature is increased in the diamino compound (20) solution. A technique in which cyanuric halide (19) is dropped or charged while keeping at a low temperature is preferable. After mixing the two compounds, it is preferable to carry out the reaction at the above low temperature for about 0.5 to 3 hours, and then to polymerize by heating at 60 to 150 ° C. all at once.
- a component previously dissolved in a solvent or a component added later may be used, but a method of adding a diamino compound (20) to a cooled solution of cyanuric halide (19) is preferable.
- the addition may be gradually added by dropping or the like, or may be added all at once.
- Components added later may be added neat or in a solution dissolved in an organic solvent as described above, but the latter method is preferred in view of ease of operation and ease of reaction control. It is.
- this base include potassium carbonate, potassium hydroxide, sodium carbonate, sodium hydroxide, sodium hydrogen carbonate, sodium ethoxide, sodium acetate, lithium carbonate, lithium hydroxide, lithium oxide, potassium acetate, magnesium oxide, oxidized Calcium, barium hydroxide, trilithium phosphate, trisodium phosphate, tripotassium phosphate, cesium fluoride, aluminum oxide, ammonia, trimethylamine, triethylamine, diisopropylamine, diisopropylethylamine, N-methylpiperidine, 2,2,6 , 6-tetramethyl-N-methylpiperidine, pyridine, 4-dimethylaminopyridine, N-methylmorpholine and the like.
- the addition amount of the base is preferably 1 to 100 equivalents, more preferably 1 to 10 equivalents per 1 equivalent of cyanuric halide (19). These bases may be used as an aqueous solution. In any of the scheme methods, after completion of the reaction, the product can be easily purified by a reprecipitation method or the like.
- a part of halogen atoms of at least one terminal triazine ring is substituted with alkyl, aralkyl, aryl, alkylamino, alkoxysilyl group-containing alkylamino, aralkylamino, arylamino, alkoxy, aralkyloxy, aryloxy.
- alkylamino, alkoxysilyl group-containing alkylamino, aralkylamino, and arylamino groups are preferable, alkylamino and arylamino groups are more preferable, and arylamino groups are more preferable. Examples of the alkyl group and alkoxy group are the same as those described above.
- ester group examples include methoxycarbonyl and ethoxycarbonyl groups.
- aryl group include phenyl, o-chlorophenyl, m-chlorophenyl, p-chlorophenyl, o-fluorophenyl, p-fluorophenyl, o-methoxyphenyl, p-methoxyphenyl, p-nitrophenyl, p-cyanophenyl, ⁇ -naphthyl, ⁇ -naphthyl, o-biphenylyl, m-biphenylyl, p-biphenylyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4 -Phenanthryl, 9-phenanthryl group and the like.
- aralkyl group examples include benzyl, p-methylphenylmethyl, m-methylphenylmethyl, o-ethylphenylmethyl, m-ethylphenylmethyl, p-ethylphenylmethyl, 2-propylphenylmethyl, 4-isopropylphenyl.
- examples include methyl, 4-isobutylphenylmethyl, ⁇ -naphthylmethyl group and the like.
- alkylamino group examples include methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, s-butylamino, t-butylamino, n-pentylamino, 1-methyl- n-butylamino, 2-methyl-n-butylamino, 3-methyl-n-butylamino, 1,1-dimethyl-n-propylamino, 1,2-dimethyl-n-propylamino, 2,2-dimethyl -N-propylamino, 1-ethyl-n-propylamino, n-hexylamino, 1-methyl-n-pentylamino, 2-methyl-n-pentylamino, 3-methyl-n-pentylamino, 4-methyl -N-pentylamino, 1,1-dimethyl-n-butylamino, 1,2-
- aralkylamino group examples include benzylamino, methoxycarbonylphenylmethylamino, ethoxycarbonylphenylmethylamino, p-methylphenylmethylamino, m-methylphenylmethylamino, o-ethylphenylmethylamino, m-ethylphenylmethyl.
- arylamino group examples include phenylamino, methoxycarbonylphenylamino, ethoxycarbonylphenylamino, naphthylamino, methoxycarbonylnaphthylamino, ethoxycarbonylnaphthylamino, anthranylamino, pyrenylamino, biphenylamino, terphenylamino, fluorenyl An amino group etc. are mentioned.
- the alkoxysilyl group-containing alkylamino group may be any of monoalkoxysilyl group-containing alkylamino, dialkoxysilyl group-containing alkylamino, trialkoxysilyl group-containing alkylamino group, and specific examples thereof include 3-trimethoxysilyl.
- aryloxy group examples include phenoxy, naphthoxy, anthranyloxy, pyrenyloxy, biphenyloxy, terphenyloxy, and fluorenyloxy groups.
- aralkyloxy group examples include benzyloxy, p-methylphenylmethyloxy, m-methylphenylmethyloxy, o-ethylphenylmethyloxy, m-ethylphenylmethyloxy, p-ethylphenylmethyloxy, 2-propyl Examples include phenylmethyloxy, 4-isopropylphenylmethyloxy, 4-isobutylphenylmethyloxy, ⁇ -naphthylmethyloxy groups and the like.
- the organic monoamine is simultaneously charged, that is, by reacting the cyanuric halide compound with the diaminoaryl compound in the presence of the organic monoamine, the rigidity of the hyperbranched polymer is reduced, and the degree of branching is reduced.
- a low soft hyperbranched polymer can be obtained.
- the hyperbranched polymer obtained by this method has excellent solubility in a reactive diluent (aggregation suppression) and crosslinkability.
- the organic monoamine any of alkyl monoamine, aralkyl monoamine, and aryl monoamine can be used as the organic monoamine.
- Alkyl monoamines include methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, s-butylamine, t-butylamine, n-pentylamine, 1-methyl-n-butylamine, 2-methyl- n-butylamine, 3-methyl-n-butylamine, 1,1-dimethyl-n-propylamine, 1,2-dimethyl-n-propylamine, 2,2-dimethyl-n-propylamine, 1-ethyl-n -Propylamine, n-hexylamine, 1-methyl-n-pentylamine, 2-methyl-n-pentylamine, 3-methyl-n-pentylamine, 4-methyl-n-pentylamine, 1,1-dimethyl -N-butylamine, 1,2-dimethyl-n-butylamine, 1,3-dimethyl-n Butylamine, 2,
- aralkyl monoamine examples include benzylamine, p-methoxycarbonylbenzylamine, p-ethoxycarbonylphenylbenzyl, p-methylbenzylamine, m-methylbenzylamine, o-methoxybenzylamine and the like.
- aryl monoamine examples include aniline, p-methoxycarbonylaniline, p-ethoxycarbonylaniline, p-methoxyaniline, 1-naphthylamine, 2-naphthylamine, anthranylamine, 1-aminopyrene, 4-biphenylylamine, o- And phenylaniline, 4-amino-p-terphenyl, 2-aminofluorene, and the like.
- the amount of the organic monoamine used is preferably 0.05 to 500 equivalents, more preferably 0.05 to 120 equivalents, and even more preferably 0.05 to 50 equivalents based on the halogenated cyanuric compound.
- the reaction temperature is preferably 60 to 150 ° C., more preferably 80 to 150 ° C., and still more preferably 80 to 120 ° C. from the viewpoint of suppressing linearity and increasing the degree of branching.
- the mixing of the three components of the organic monoamine, the halogenated cyanuric compound, and the diaminoaryl compound is preferably performed at the above-described low temperature. It is preferable to carry out the reaction at an elevated temperature.
- the organic monoamine is added at the low temperature, and the reaction is performed at a stretch (in one step) to the polymerization temperature. May be performed.
- R 102 and R 104 are independently of each other a hydrogen atom, an alkyl group optionally having a branched structure having 1 to 10 carbon atoms, or polymerization.
- sexual carbon - represents a carbon-carbon double bond-containing group
- R 103 is a hydrogen atom, or represents an alkyl group which may have a branched structure of 1 to 10 carbon atoms
- R 102 and R Any one of 104 is a polymerizable carbon-carbon double bond-containing group, and both R 102 and R 104 are not simultaneously a polymerizable carbon-carbon double bond-containing group.
- R 102 is preferably a hydrogen atom or a methyl group
- R 103 is preferably a hydrogen atom from the viewpoint of ensuring the ability to form a hydrogen bond with a triazine ring-containing polymer.
- alkyl group which may have a branched structure having 1 to 10 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, and n-pentyl.
- the polymerizable carbon-carbon double bond-containing group is not particularly limited, but a carbon-carbon double bond-containing hydrocarbon group (alkenyl group) having 2 to 10 carbon atoms, preferably 2 to 5 carbon atoms.
- ethenyl vinyl
- n-1-propenyl n-2-propenyl
- allyl group 1-methylethenyl, n-1-butenyl, n-2-butenyl, n-3-butenyl
- reactive diluent represented by the formula (A) include N-vinylformamide, N-vinylacetamide, N-allylformamide, N-allylacetamide, 4-acryloylmorpholine, (meth) acrylamide, N-methyl (Meth) acrylamide, N-dimethyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-diisopropyl (meth) acrylamide, etc.
- N-vinylformamide, 4-acryloylmorpholine, N-dimethylacrylamide, and N-diethyl (meth) acrylamide are preferred.
- the amount of the reactive diluent represented by the formula (A) is not particularly limited, and is preferably 1 to 200 parts by mass with respect to 100 parts by mass of the triazine ring-containing polymer. Considering the degree of improvement, the lower limit is preferably 5 parts by mass, more preferably 10 parts by mass, and the upper limit is preferably 150 parts by mass, more preferably 100 parts by mass.
- composition for adhesives of this invention contains the triazine ring containing polymer shown by Formula (1), and the reactive diluent shown by Formula (A), it is comprised only from these two components.
- other additives such as a leveling agent, a surfactant, and a silane coupling agent may be included.
- surfactant examples include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether; polyoxyethylene octylphenol ether, polyoxyethylene nonylphenol Polyoxyethylene alkyl allyl ethers such as ethers; polyoxyethylene / polyoxypropylene block copolymers; sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan tristearate Sorbitan fatty acid esters such as polyoxyethylene sorbitan monolaurate, polyoxyethyleneso Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as bitane monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate, trade name
- surfactants may be used alone or in combination of two or more.
- the amount of the surfactant used is preferably 0.0001 to 5 parts by mass, more preferably 0.001 to 1 part by mass, and 0.01 to 0.5 parts by mass with respect to 100 parts by mass of the triazine ring-containing polymer. Even more preferred.
- the composition of the present invention is used for the purpose of adjusting the refractive index of an adhesive film obtained from a solventless photocurable adhesive.
- the composition may be added to the adhesive (composition), the adhesive (composition) may be added to the composition, and further, the adhesive composition may be added to the adhesive composition.
- An adhesive (composition) may be prepared by blending adhesive components.
- the monomer constituting the adhesive component of the solventless photocurable adhesive is not particularly limited, and can be appropriately selected from known ones such as acrylic and allyl, but can be used in the present invention.
- the triazine ring-containing polymer used in the adhesive composition is particularly excellent in compatibility with (meth) acrylic monomers and oligomers, so that acrylic photocuring properties using such monomers as adhesive components It is preferable to apply to an adhesive.
- Specific examples of the allylic monomer include triallyl cyanurate and triallyl isocyanurate.
- the (meth) acrylic monomer is not particularly limited as long as it is a monomer conventionally used as an adhesive component.
- Examples of commercially available (meth) acrylic monomers include EBECRYL (registered trademark) 80, 436, 438, 446, 450, 505, 524, 525, 770, 800, 810, 811, 812, 830, 846, 851, 852, 853, 1870, 884, 885, 600, 605, 645, 648, 860, 1606, 3500, 3608, 3700, 3701, 3702, 3703, 3708, 6040, 303, 767 (Daicel Cytec Co., Ltd.) NK Ester A-200, A-400, A-600, A-1000, A-9300 (Tris (2-acryloyloxyethyl) isocyanurate), A-9300-1CL, A-DPH A-TMPT, A-DCP, A-HD-N, UA-53H, G, 2G, 3G, 4G, 9G, 14G, 23G, ABE-300, A-BPE-4, A-BPE-6, A-BPE
- Urethane acrylate is a compound having one or more polymerizable unsaturated bonds and two or more urethane bonds, and is also available as a commercial product. Specific examples thereof include the trade name Beam Set (registered trademark). 102, 502H, 505A-6, 510, 550B, 551B, 575, 575CB, EM-90, EM-92 (manufactured by Arakawa Chemical Industries, Ltd.); trade name Photomer (registered trademark) 6008, 6210 (San Nopco) Product name: NK Oligo U-2PPA, U-4HA, U-6HA, U-15HA, UA-32P, U-324A, U-4H, U-6H, UA-160TM (2-hydroxyethyl acrylate, isophorone) Reaction product of diisocyanate and polytetramethylene glycol), UA-122P, UA-2235PE, UA-340P UA-5201, UA-512 (manufactured by Shin-
- the use ratio of the adhesive composition to the allyl or (meth) acrylic monomer is within the concentration range of the triazine ring-containing polymer in the adhesive composition described above. It is not particularly limited as long as the (meth) acrylic monomer is compatible and a uniform solution can be prepared.
- triazine ring-containing polymer: allyl or (meth) acrylic monomer 1 : 10 to 10: 1, but in consideration of further increasing the refractive index of the resulting adhesive film, 1: 7 to 7: 1 is preferable, and 1: 5 to 5: 1 is more preferable.
- a ratio of 1: 3 to 3: 1 is even more preferable.
- a radical photopolymerization initiator may be added to the adhesive of the present invention containing the adhesive composition and the adhesive monomer.
- the radical photopolymerization initiator may be appropriately selected from known ones, such as acetophenones, benzophenones, Michler's benzoylbenzoate, amyloxime esters, oxime esters, tetramethylthiuram monosulfide, and thioxanthones. Is mentioned.
- photocleavable photoradical polymerization initiators are preferred.
- the photocleavable photoradical polymerization initiator is described in the latest UV curing technology (p. 159, publisher: Kazuhiro Takahisa, publisher: Technical Information Association, Inc., published in 1991).
- radical photopolymerization initiators examples include BASF Corporation trade names: Irgacure 127, 184, 369, 379, 379EG, 651, 500, 754, 819, 903, 907, 784, 2959, CGI 1700, CGI 1750, CGI 1850. , CG24-61, OXE01, OXE02, Darocur 1116, 1173, MBF, manufactured by BASF, Inc.
- Product name Lucirin TPO, manufactured by UCB, Inc. KT37, KT55, KTO46, KIP75 / B etc. are mentioned.
- radical photopolymerization initiator When a radical photopolymerization initiator is used, it is preferably used in the range of 0.1 to 200 parts by weight, preferably in the range of 1 to 150 parts by weight, with respect to 100 parts by weight of the (meth) acrylic monomer. More preferred.
- the adhesive of the present invention may contain known radical polymerizable monomers, oligomers and / or polymers other than the above-mentioned allyl or acrylic, and the above-described surfactants and antioxidants.
- Known additives such as an agent, an ultraviolet absorber, an adhesion promoter, a thickener, and a flame retardant may be contained.
- the adhesive of the present invention can be applied to a substrate, and further laminated with a material that adheres thereto, and irradiated with light to form an adhesive layer.
- the adhesive application method is arbitrary. For example, spin coating method, dip method, flow coating method, ink jet method, jet dispenser method, spray method, bar coating method, gravure coating method, slit coating method, roll coating method, transfer Methods such as printing, brush coating, blade coating, and air knife coating can be employed.
- ITO indium tin oxide
- IZO indium zinc oxide
- PET polyethylene terephthalate
- plastic glass, quartz, ceramics
- a flexible substrate having flexibility can be used.
- Conditions for the light irradiation are not particularly limited, and an appropriate irradiation energy and time may be adopted depending on the triazine ring-containing polymer and the (meth) acrylic monomer to be used.
- the adhesive layer of the present invention obtained as described above is not only excellent in transparency but also improved in refractive index. Therefore, by using this adhesive layer, the difference in refractive index from the adherend layer can be reduced. As a result, the visibility and light extraction efficiency of electronic devices and optical devices can be improved.
- the adhesive containing the adhesive composition of the present invention includes a liquid crystal display, an organic electroluminescence (EL) display, a touch panel, an optical semiconductor (LED) element, a solid-state imaging element, an organic thin film solar cell, a dye-sensitized solar cell, an organic It is suitable as an adhesive for devices requiring transparency and a high refractive index, such as electronic devices and optical devices such as thin film transistors (TFTs), lenses, prisms, cameras, binoculars, microscopes, and semiconductor exposure apparatuses.
- TFTs thin film transistors
- 1,3-phenylenediamine [1] (8.80 g, 81.3 mmol, manufactured by Aminochem), aniline (2.53 g, 27.1 mmol, manufactured by Junsei Chemical Co., Ltd.), N, N-dimethylacetamide (288.0 g, manufactured by Junsei Chemical Co., Ltd., hereinafter referred to as DMAc) was charged and cooled to ⁇ 15 ° C.
- aniline (26.9 g, 288.5 mmol, manufactured by Junsei Chemical Co., Ltd.) was added and stirred for 3 hours to complete the reaction.
- the reaction solution was reprecipitated into a mixed solution of 28% aqueous ammonia (65.9 g) and ion-exchanged water (1000 g).
- the precipitate was filtered to obtain a polymer wet product.
- the obtained polymer wet product was redissolved in a mixed solution of tetrahydrofuran (280 g, THF hereinafter) and 28% aqueous ammonia solution (65.9 g), stirred for 30 minutes, and then heated to 40 ° C. for liquid separation. .
- HB-TmDAL-T The weight average molecular weight Mw measured in terms of polystyrene by GPC of HB-TmDAL-T was 3330, and the polydispersity Mw / Mn was 2.68.
- Tg glass transition temperature
- Td 5% 5% weight loss temperature
- Synthesis Example 2 Synthesis of Polymer Compound [3] In a 1000 mL four-necked flask under nitrogen, 1,3-phenylenediamine (35.18 g, 32.5 mmol, manufactured by Aminochem), aniline (10.10 g, 108. 5 mmol, manufactured by Junsei Chemical Co., Ltd.) and DMAc (716.9 g, produced by Junsei Chemical Co., Ltd.) were charged and cooled to -15 ° C.
- aniline (107.4 g, 1154.0 mmol, manufactured by Junsei Chemical Co., Ltd.) was added and stirred for 3 hours to complete the reaction.
- the reaction solution was reprecipitated into a mixed solution of 28% aqueous ammonia (263.9 g) and ion-exchanged water (4000 g).
- the precipitate was filtered to obtain a polymer wet product.
- the obtained polymer wet product was redissolved in a mixed solution of THF (1120 g) and 28% aqueous ammonia solution (263.9 g), stirred for 30 minutes, and then heated to 40 ° C. for liquid separation.
- the organic layer was collected and reprecipitated with ion-exchanged water (6000 g) in which a small amount of ammonium acetate was dissolved.
- the resulting precipitate was filtered and dried at 130 ° C. for 8 hours with a vacuum dryer to obtain 53.0 g of the target polymer compound [3] (hereinafter, HB-TmDAL-T2).
- the weight average molecular weight Mw measured by GPC of HB-TmDAL-T2 in terms of polystyrene was 4855, and the polydispersity Mw / Mn was 2.31.
- Tg glass transition temperature
- Td 5% 5% weight loss temperature
- aniline (53.7 g, 576.9 mmol, manufactured by Junsei Chemical Co., Ltd.) was added and stirred for 3 hours to complete the reaction.
- the reaction solution was reprecipitated in a mixed solution of 28% aqueous ammonia (131.9 g) and ion-exchanged water (2000 g).
- the precipitate was filtered to obtain a polymer wet product.
- the obtained polymer wet product was redissolved in a mixed solution of THF (560 g) and 28% aqueous ammonia solution (131.9 g), stirred for 30 minutes, and then heated to 40 ° C. for liquid separation.
- the organic layer was collected and reprecipitated with ion-exchanged water (3000 g) in which a small amount of ammonium acetate was dissolved.
- the resulting precipitate was filtered and dried at 130 ° C. for 8 hours in a vacuum dryer to obtain 46.0 g of the target polymer compound [3] (hereinafter, HB-TmDAL-T3).
- the weight average molecular weight Mw measured by GPC of HB-TmDAL-T3 in terms of polystyrene was 4198, and the polydispersity Mw / Mn was 2.29.
- HB-TmDA target polymer compound [3]
- the weight average molecular weight Mw measured in terms of polystyrene by GPC of HB-TmDA was 10200, and the polydispersity Mw / Mn was 6.5.
- Tg glass transition temperature
- Td 5% 5% weight loss temperature
- the refractive index of the thin film is 1.764 for HB-TmDAL-T, 1.764 for HB-TmDAL-T2, and 1.756 for HB-TmDAL-T3 at a wavelength of 550 nm. It was shown that it was a high refractive index material.
- Examples 1-2 and 1-3 Each polymer varnish was obtained in the same manner as in Example 1-1 except that the mass ratio of 40% by mass of the adhesive composition to IBXA was 5: 5 and 8: 2, respectively.
- HB-TmDAL-TN30 was spin-coated on a quartz substrate using a spin coater under the condition of 7000 rpm (30 seconds), and then UV-cured with an integrated light quantity of 1000 mJ / cm 2 under nitrogen to obtain a highly branched polymer. (Thickness: 3.0 ⁇ m).
- Example 2-2 Under air, to a 10 mL sample bottle, add 4.0000 g of the triazine-based hyperbranched polymer HB-TmDAL-T obtained in Synthesis Example 1, add 6.0000 g of NVF as a reactive diluent, and mix rotor ( 110 rpm) until the polymer is completely dissolved and the solution is homogeneous. After stirring, a varnish containing 40% by mass of a triazine hyperbranched polymer was obtained as a pale yellow transparent solution in which the polymer was completely dissolved.
- HB-TmDAL-TN40 an adhesive composition having a triazine-based hyperbranched polymer of 39% by mass.
- a highly branched polymer thin film was obtained in the same manner as in Example 2-1 except that the obtained HB-TmDAL-TN40 was used (film thickness 4.3 ⁇ m).
- Examples 2-3 and 2-4 instead of the triazine-based hyperbranched polymer HB-TmDAL-T, the same procedure as in Examples 2-1 and 2-2 except that the triazine-based hyperbranched polymer HB-TmDAL-T2 obtained in Synthesis Example 2 was used.
- An adhesive composition hereinafter abbreviated as HB-TmDAL-T2N30
- HB-TmDAL-T2N40 an adhesive composition having a mass of 39% by mass. I got each.
- Examples 2-5 and 2-6 The same procedure as in Examples 2-1 and 2-2 except that the triazine-based highly branched polymer HB-TmDAL-T3 obtained in Synthesis Example 3 was used instead of the triazine-based highly branched polymer HB-TmDAL-T.
- An adhesive composition hereinafter abbreviated as HB-TmDAL-T3N30
- HB-TmDAL-T3N40 having a mass of 39% by mass. I got each.
- Example 2-7 Under air, to the 10 mL sample bottle was added 5.0000 g of the triazine-based hyperbranched polymer HB-TmDAL-T obtained in Synthesis Example 1, and 4.0000 g of NVF and 4-acryloylmorpholine (hereinafter referred to as ACMO) as reactive diluents. 1.0000 g was added, and the mixture was stirred at room temperature using a mix rotor (110 rpm) until the polymer was completely dissolved and the solution was uniform. After stirring, a varnish containing 50% by mass of a triazine hyperbranched polymer was obtained as a light yellow transparent solution in which the polymer was completely dissolved.
- ACMO 4-acryloylmorpholine
- HB-TmDAL-TNA50 is spin-coated on a quartz substrate under the condition of 2000 rpm (30 seconds) using a spin coater, and then UV-cured under nitrogen with an integrated light quantity of 1000 mJ / cm 2 to form a highly branched polymer. A thin film was obtained.
- the cured film has a refractive index of 1.64 to 1.65, which is high as a solvent-free cured product. I found out. Further, as shown in FIG. 1, it was found that HB-TmDAL-TN40 (film thickness: 4.3 ⁇ m) has a transmittance of 95% or more at 400 nm or more, and is very transparent.
- IBXA mass ratio 3: 7
- 0.002 g 50 by BYK-Japan Japan
- 100% by mass of the composition for mass% adhesive and IBXA was added, and 0.1 mass part was added thereto.
- 0.010 g of Irgacure-2959 (BASF) was added as a radical photopolymerization initiator (50 parts by mass of an adhesive composition and 100 parts by mass of IBXA, and 5.00 parts by mass of this). . These were stirred until the solute was completely dissolved and the solution was uniform to obtain an adhesive.
- the obtained adhesive was spin-coated on a quartz substrate under the condition of 2000 rpm (30 seconds) using a spin coater, and then UV-cured with an integrated light quantity of 1000 mJ / cm 2 under nitrogen to obtain a cured film.
- Examples 3-2 and 3-3, Comparative Example 3-1 Each adhesive was obtained in the same manner as in Example 3-1, except that the mass ratio of the 50% by weight adhesive composition to IBXA was 5: 5, 8: 2, and 0:10, respectively. It was. A cured film was obtained in the same manner as in Example 3-1, except that each obtained adhesive was used.
- Example 3-4 Under air, to the 10 mL sample bottle was added 5.0000 g of the triazine-based hyperbranched polymer HB-TmDAL-T obtained in Synthesis Example 1, and NVF 5.0000 g as a reactive diluent was added thereto. 110 rpm) until the polymer is completely dissolved and the solution is homogeneous. After stirring, a composition for adhesive having 50% by mass of triazine-based hyperbranched polymer was obtained as a light yellow transparent solution in which the polymer was completely dissolved.
- Examples 3-5, 3-6, Comparative Example 3-2 Each adhesive was treated in the same manner as in Example 3-3, except that the mass ratio of the 50% by mass adhesive composition to the urethane acrylate was 5: 5, 8: 2, and 0:10, respectively. Obtained. A cured film was obtained in the same manner as in Example 3-1, except that each obtained adhesive was used.
- the refractive index of a general acrylate resin is about 1.5, whereas the refractive index can be increased by adding HB-TmDAL-TN50. It was found that the refractive index can be increased to a level exceeding 1.6.
- Example 3-7 Under air, in a 10 mL sample bottle, 5.000 g of the triazine-based hyperbranched polymer HB-TmDAL-T obtained in Synthesis Example 1 was added, and N-dimethylacrylamide (hereinafter referred to as DMAA) 5.0000 g as a reactive diluent.
- DMAA N-dimethylacrylamide
- the mixture was stirred at 50 ° C. using a mix rotor (110 rpm) until the polymer was completely dissolved and the solution was uniform.
- an adhesive composition (HB-TmDAL-TD50) containing 50% by mass of a triazine-based hyperbranched polymer was obtained as a pale yellow transparent solution in which the polymer was completely dissolved.
- TAC triallyl cyanurate
- Example 3-8 To 0000 g of 50% by mass of the adhesive composition (HB-TmDAL-TD50) prepared in Example 3-7, 1.0000 g of NK ester A-DCP (manufactured by Shin-Nakamura Chemical Co., Ltd.) (mass ratio 4: 1) and 0.25 g of Irgacure-2959 (manufactured by BASF) as a radical photopolymerization initiator (100 mass parts of 50 mass% adhesive composition and A-DCP), and 5.00 mass parts relative to this ) was added. These were stirred until the solute was completely dissolved and the solution was uniform, to obtain an adhesive (TD50-DCP).
- NK ester A-DCP manufactured by Shin-Nakamura Chemical Co., Ltd.
- Irgacure-2959 manufactured by BASF
- Example 3-9 1.0000 g of NK ester A-LEN-10 (manufactured by Shin-Nakamura Chemical Co., Ltd.) to 4.00 g of the 50% by mass adhesive composition (HB-TmDAL-TD50) prepared in Example 3-7 4: 1) and 0.25 g of Irgacure-2959 (manufactured by BASF) as a radical photopolymerization initiator (100 mass parts of 50 mass% adhesive composition and A-LEN-10). 0.000 parts by mass) was added. These were stirred until the solute was completely dissolved and the solution was uniform to obtain an adhesive (TD50-LEN).
- Example 3-10 1.4000 g of IBXA (mass ratio 4: 1) was added to 4.0000 g of the 50% by weight adhesive composition (HB-TmDAL-TD50) prepared in Example 3-7, and Irgacure-2959 as a photoradical polymerization initiator. (BASF) 0.25g (50 mass% adhesive composition and IBXA were 100 mass parts, and 5.00 mass parts with respect to this) was added. These were stirred until the solute was completely dissolved and the solution was uniform to obtain an adhesive (TD50-IB).
- BASF 0.25g (50 mass% adhesive composition and IBXA were 100 mass parts, and 5.00 mass parts with respect to this) was added.
- Example 3-11 1.0000 g of adamantyl acrylate (M-104, manufactured by Idemitsu Kosan Co., Ltd.) was added to 4.0000 g of the 50% by mass adhesive composition (HB-TmDAL-TD50) prepared in Example 3-7 (mass ratio 4: 1).
- Irgacure-2959 manufactured by BASF 0.25 g (50 mass% adhesive composition and M-104 as 100 mass parts, 5.00 mass parts relative to this) as a radical photopolymerization initiator added. These were stirred until the solute was completely dissolved and the solution was uniform to obtain an adhesive (TD50-104).
- the tensile shear on the glass substrate was evaluated according to JIS K6850.
- the glass substrate had a thickness of 3 mm, and the adhesive was a cured film in the same manner as when measuring the refractive index, and the thickness was 100 ⁇ m.
- the moving speed of the crosshead was 5 mm / min, and the value obtained by dividing the maximum load (N) when the test piece was broken by the bonding area (mm 2 ) was taken as the tensile shear bond strength.
- the glass / glass tensile shear bond strength of the adhesive TD50-TAC was 1.6 MPa.
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Abstract
Description
このディスプレイを構成する各部材を組み立てる際の光学粘着剤や光学接着剤の主成分としては、一般的にアクリル系材料が用いられる(特許文献1,2参照)。アクリル系材料は、透明性が高いものの、その屈折率と各部材表面の屈折率との間に差が生じる結果、界面で光が反射して光の取り出し効率が低下するという問題があった。
しかし、特許文献3の屈折率調整材料は有機溶媒を含んでいるため、加熱乾燥工程が必要であるうえ、溶媒によって接着時に被接着部材表面が劣化する場合がある。
本発明は、このような事情に鑑みてなされたものであり、溶媒を含まないにもかかわらず、接着剤成分であるアクリル系材料等との相溶性の良好な光硬化性接着剤用組成物を提供することを目的とする。
1. 下記式(1)で表される繰り返し単位構造を含み、重量平均分子量が500~7,000のトリアジン環含有重合体と、下記式(A)で表される反応性希釈剤と、を含み、溶媒を含まないことを特徴とする無溶剤型光硬化性接着剤用組成物、
Arは、式(2)~(13)で示される群から選ばれる少なくとも1種を表す。
2. 前記式(A)におけるR102およびR103が、ともに水素原子であり、R104が、重合性炭素-炭素二重結合含有基である1の無溶剤型光硬化性接着剤用組成物、
3. 前記反応性希釈剤が、N-ビニルホルムアミド、4-アクリロイルモルホリン、N-ジメチルアクリルアミド、およびN-ジエチルアクリルアミドから選ばれる1種または2種以上である1または2の無溶剤型光硬化性接着剤用組成物、
4. 前記Arが、式(15)で表される1~3のいずれかの無溶剤型光硬化性接着剤用組成物、
6. 1~5のいずれかの無溶剤型光硬化性接着剤用組成物と、アリル系モノマー、(メタ)アクリル系モノマーおよび(メタ)アクリル系オリゴマーから選ばれる少なくとも1種と、を含む無溶剤型光硬化性接着剤、
7. 前記(メタ)アクリル系モノマーが、メチル(メタ)アクリレート、エチル(メタ)アクリレート、ブチル(メタ)アクリレート、2-(2-エトキシエトキシ)エチルアクリレート、テトラヒドロフルフリル(メタ)アクリレート、ラウリルアクリレート、イソオクチルアクリレート、イソデシルアクリレート、2-フェノキシエチルアクリレート、2-エチルヘキシル(メタ)アクリレート、イソボルニル(メタ)アクリレート、アダマンチル(メタ)アクリレート、ジシクロペンテニルオキシエチル(メタ)アクリレート、ジシクロペンタジエニル(メタ)アクリレート、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、2-ヒドロキシブチル(メタ)アクリレート、カプロラクトンアクリレート、モルホリン(メタ)アクリレート、ヘキサンジオールジ(メタ)アクリレート、エチレングリコールジメタクリレート、トリメチロールプロパントリアクリレート、ペンタエリスリトールテトラヒドロフランアクリレートおよびウレタンアクリレートから選ばれる1種または2種以上である6の無溶剤型光硬化性接着剤、
8. さらに、光ラジカル開始剤を含む6または7の無溶剤型光硬化性接着剤、
9. 6~8のいずれかの無溶剤型光硬化性接着剤を硬化させて得られる接着膜、
10. 9の接着膜を用いて作製される電子デバイス、
11. 9の接着膜を用いて作製される光学デバイス
を提供する。
本発明の接着剤用組成物を光学接着剤に添加することで、透明性に優れた接着層を形成できるだけでなく、その屈折率をも高め、被接着層との屈折率差を少なくできる結果、視認性や光取り出し効率を向上させることができる。
本発明の接着剤用組成物を含む接着剤は、液晶ディスプレイ、有機エレクトロルミネッセンス(EL)ディスプレイ、タッチパネル、光半導体(LED)素子、固体撮像素子、有機薄膜太陽電池、色素増感太陽電池、有機薄膜トランジスタ(TFT)、レンズ、プリズム、カメラ、双眼鏡、顕微鏡、半導体露光装置等の電子デバイスや光学デバイスなどの透明性および高屈折率が要求されるデバイスの接着剤として好適である。
本発明に係る無溶剤型光硬化性接着剤用組成物は、式(1)で表される繰り返し単位構造を含み、重量平均分子量が500~7,000のトリアジン環含有重合体と、式(A)で表される反応性希釈剤と、を含み、溶媒を含まないものである。
なお、本発明における「接着剤」は、粘着剤をも含む概念である。
本発明において、アルキル基の炭素数としては特に限定されるものではないが、1~20が好ましく、ポリマーの耐熱性をより高めることを考慮すると、炭素数1~10がより好ましく、1~3がより一層好ましい。また、その構造は、鎖状、分岐状、環状のいずれでもよい。
アリール基の具体例としては、フェニル、o-クロルフェニル、m-クロルフェニル、p-クロルフェニル、o-フルオロフェニル、p-フルオロフェニル、o-メトキシフェニル、p-メトキシフェニル、p-ニトロフェニル、p-シアノフェニル、α-ナフチル、β-ナフチル、o-ビフェニリル、m-ビフェニリル、p-ビフェニリル、1-アントリル、2-アントリル、9-アントリル、1-フェナントリル、2-フェナントリル、3-フェナントリル、4-フェナントリル、9-フェナントリル基等が挙げられる。
その具体例としては、ベンジル、p-メチルフェニルメチル、m-メチルフェニルメチル、o-エチルフェニルメチル、m-エチルフェニルメチル、p-エチルフェニルメチル、2-プロピルフェニルメチル、4-イソプロピルフェニルメチル、4-イソブチルフェニルメチル、α-ナフチルメチル基等が挙げられる。
ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられる。
なお、アルキル基、アルコキシ基としては上記と同様のものが挙げられる。
また、X1およびX2は、互いに独立して、単結合、炭素数1~10の分岐構造を有していてもよいアルキレン基、または式(14)で示される基を表す。
炭素数1~10の分岐構造を有していてもよいアルキレン基としては、メチレン、エチレン、プロピレン、トリメチレン、テトラメチレン、ペンタメチレン基等が挙げられる。
なお、本発明における重量平均分子量は、ゲルパーミエーションクロマトグラフィー(以下、GPCという)分析による標準ポリスチレン換算で得られる平均分子量である。
例えば、下記スキーム1に示されるように、繰り返し構造(21)を有する高分岐重合体(ハイパーブランチポリマー)は、ハロゲン化シアヌル(19)およびm-フェニレンジアミン化合物(20)を適当な有機溶媒中で反応させて得ることができる。
特に、スキーム1の方法の場合、ハロゲン化シアヌル(19)2当量に対して、ジアミノ化合物(20)を3当量用いることを避けることが好ましい。官能基の当量をずらすことで、ゲル化物の生成を防ぐことができる。
種々の分子量のトリアジン環末端を多く有する高分岐重合体(ハイパーブランチポリマー)を得るために、ハロゲン化シアヌル(19)2当量に対して、ジアミノ化合物(20)を3当量未満の量で用いることが好ましい。
一方、種々の分子量のアミン末端を多く有する高分岐重合体(ハイパーブランチポリマー)を得るために、ジアミノ化合物(20)3当量に対して、ハロゲン化シアヌル(19)を2当量未満の量で用いることが好ましい。
このように、ジアミノ化合物(20)やハロゲン化シアヌル(19)の量を適宜調節することで、得られる高分岐重合体(ハイパーブランチポリマー)の分子量を容易に調節することができる。
なお、高分岐重合体(ハイパーブランチポリマー)の分子量を調節する手法としては、有機溶媒中の濃度制御によっても可能であり、その場合の反応濃度(固形分濃度)は、1~100質量%が好ましく、5~50質量%がより好ましく、10~25質量%がより一層好ましい。
中でもN,N-ジメチルホルムアミド、ジメチルスルホキシド、N-メチル-2-ピロリドン、N,N-ジメチルアセトアミド、およびそれらの混合系が好ましく、特に、N,N-ジメチルアセトアミド、N-メチル-2-ピロリドンが好適である。
特にスキーム1の反応では、リニア性を抑え、分岐度を高めるという点から、反応温度は60~150℃が好ましく、80~150℃がより好ましく、80~120℃がより一層好ましい。
ただし、上述した重量平均分子量の重合体を得るという観点から、ハロゲン化シアヌル(19)、ジアミノ化合物(20)の混合は、低温下で行うことが好ましく、その場合の温度としては、-50~50℃程度が好ましく、-20~50℃程度がより好ましく、-20~10℃がさらに好ましい。低温仕込み後は、その温度で所定時間反応させた後、重合させる温度まで一気に(一段階で)昇温して反応を行うことが好ましい。
スキーム2の第1段階の方法において、反応温度は、用いる溶媒の融点から溶媒の沸点までの範囲で適宜設定すればよいが、特に、-50~50℃程度が好ましく、-20~50℃程度がより好ましく、-10~50℃程度がより一層好ましく、-10~10℃がさらに好ましい。
特にスキーム2の方法では、-50~50℃で反応させる第1工程と、この工程に続いて60~150℃で反応させる第2工程とからなる2段階工程を採用することが好ましい。
この場合、予め溶媒に溶かしておく成分および後から加える成分はどちらでもよいが、上述した重量平均分子量の重合体を得ることを考慮すると、ジアミノ化合物(20)の溶液中に、内温を上記低温下に保ちながらハロゲン化シアヌル(19)を滴下または粉末投入する手法が好ましい。
両化合物の混合後は、上記低温下で0.5~3時間程度反応させた後、60~150℃に一気に加熱して重合させることが好ましい。
後から加える成分は、ニートで加えても、上述したような有機溶媒に溶かした溶液で加えてもよいが、操作の容易さや反応のコントロールのし易さなどを考慮すると、後者の手法が好適である。
この塩基の具体例としては、炭酸カリウム、水酸化カリウム、炭酸ナトリウム、水酸化ナトリウム、炭酸水素ナトリウム、ナトリウムエトキシド、酢酸ナトリウム、炭酸リチウム、水酸化リチウム、酸化リチウム、酢酸カリウム、酸化マグネシウム、酸化カルシウム、水酸化バリウム、リン酸三リチウム、リン酸三ナトリウム、リン酸三カリウム、フッ化セシウム、酸化アルミニウム、アンモニア、トリメチルアミン、トリエチルアミン、ジイソプロピルアミン、ジイソプロピルエチルアミン、N-メチルピペリジン、2,2,6,6-テトラメチル-N-メチルピペリジン、ピリジン、4-ジメチルアミノピリジン、N-メチルモルホリン等が挙げられる。
塩基の添加量は、ハロゲン化シアヌル(19)1当量に対して1~100当量が好ましく、1~10当量がより好ましい。なお、これらの塩基は水溶液にして用いてもよい。
いずれのスキームの方法においても、反応終了後、生成物は再沈法等によって容易に精製できる。
これらの中でも、アルキルアミノ、アルコキシシリル基含有アルキルアミノ、アラルキルアミノ、アリールアミノ基が好ましく、アルキルアミノ、アリールアミノ基がより好ましく、アリールアミノ基がさらに好ましい。
上記アルキル基、アルコキシ基としては上記と同様のものが挙げられる。
アリール基の具体例としては、フェニル、o-クロルフェニル、m-クロルフェニル、p-クロルフェニル、o-フルオロフェニル、p-フルオロフェニル、o-メトキシフェニル、p-メトキシフェニル、p-ニトロフェニル、p-シアノフェニル、α-ナフチル、β-ナフチル、o-ビフェニリル、m-ビフェニリル、p-ビフェニリル、1-アントリル、2-アントリル、9-アントリル、1-フェナントリル、2-フェナントリル、3-フェナントリル、4-フェナントリル、9-フェナントリル基等が挙げられる。
アラルキル基の具体例としては、ベンジル、p-メチルフェニルメチル、m-メチルフェニルメチル、o-エチルフェニルメチル、m-エチルフェニルメチル、p-エチルフェニルメチル、2-プロピルフェニルメチル、4-イソプロピルフェニルメチル、4-イソブチルフェニルメチル、α-ナフチルメチル基等が挙げられる。
アリールアミノ基の具体例としては、フェニルアミノ、メトキシカルボニルフェニルアミノ、エトキシカルボニルフェニルアミノ、ナフチルアミノ、メトキシカルボニルナフチルアミノ、エトキシカルボニルナフチルアミノ、アントラニルアミノ、ピレニルアミノ、ビフェニルアミノ、ターフェニルアミノ、フルオレニルアミノ基等が挙げられる。
アラルキルオキシ基の具体例としては、ベンジルオキシ、p-メチルフェニルメチルオキシ、m-メチルフェニルメチルオキシ、o-エチルフェニルメチルオキシ、m-エチルフェニルメチルオキシ、p-エチルフェニルメチルオキシ、2-プロピルフェニルメチルオキシ、4-イソプロピルフェニルメチルオキシ、4-イソブチルフェニルメチルオキシ、α-ナフチルメチルオキシ基等が挙げられる。
この手法によって得られたハイパーブランチポリマーは、反応性希釈剤への溶解性(凝集抑制)や、架橋性に優れたものとなる。
ここで、有機モノアミンとしては、アルキルモノアミン、アラルキルモノアミン、アリールモノアミンのいずれを用いることもできる。
アリールモノアミンの具体例としては、アニリン、p-メトキシカルボニルアニリン、p-エトキシカルボニルアニリン、p-メトキシアニリン、1-ナフチルアミン、2-ナフチルアミン、アントラニルアミン、1-アミノピレン、4-ビフェニリルアミン、o-フェニルアニリン、4-アミノ-p-ターフェニル、2-アミノフルオレン等が挙げられる。
この場合の反応温度は、リニア性を抑え、分岐度を高めるという点から、反応温度は60~150℃が好ましく、80~150℃がより好ましく、80~120℃がより一層好ましい。
ただし、上述のとおり、有機モノアミン、ハロゲン化シアヌル化合物、ジアミノアリール化合物の3成分の混合は、上述した低温下で行うことが好ましく、また、低温仕込み後は、重合させる温度まで一気に(一段階で)昇温して反応を行うことが好ましい。
また、ハロゲン化シアヌル化合物とジアミノアリール化合物の2成分の混合を上述した低温下で行った後、当該低温下で、有機モノアミンを加え、重合させる温度まで一気に(一段階で)昇温して反応を行ってもよい。
また、このような有機モノアミンの存在下で、ハロゲン化シアヌル化合物と、ジアミノアリール化合物とを反応させる反応は、上述と同様の有機溶媒を用いて行ってもよい。
中でもR102としては、水素原子、メチル基が好ましく、R103としては、トリアジン環含有重合体との水素結合形成能を確保するという点から、水素原子が好ましい。
好ましくは、炭素数1~5のアルキル基である。
なお、反応性希釈剤は、2種以上を組み合わせて用いてもよい。
これらの界面活性剤は、単独で使用しても、2種以上組み合わせて使用してもよい。界面活性剤の使用量は、トリアジン環含有重合体100質量部に対して0.0001~5質量部が好ましく、0.001~1質量部がより好ましく、0.01~0.5質量部がより一層好ましい。
その使用方法としては、組成物を接着剤(組成物)中に添加しても、組成物中に、接着剤(組成物)を添加してもよく、さらには、接着剤用組成物中に接着成分を配合して接着剤(組成物)を調製してもよい。
アリル系モノマーの具体例としては、トリアリルシアヌレート、トリアリルイソシアヌレート等が挙げられる。
(メタ)アクリル系モノマーとしては、従来接着剤成分として汎用されるモノマーであれば特に限定されるものではなく、例えば、メチル(メタ)アクリレート、エチル(メタ)アクリレート、ブチル(メタ)アクリレート、2-(2-エトキシエトキシ)エチルアクリレート、テトラヒドロフルフリル(メタ)アクリレート、ラウリルアクリレート、イソオクチルアクリレート、イソデシルアクリレート、2-フェノキシエチルアクリレート、2-エチルヘキシル(メタ)アクリレート、イソボルニル(メタ)アクリレート、アダマンチル(メタ)アクリレート、ジシクロペンテニルオキシエチル(メタ)アクリレート、ジシクロペンタジエニル(メタ)アクリレート、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、2-ヒドロキシブチル(メタ)アクリレート、カプロラクトンアクリレート、モルホリン(メタ)アクリレート、ヘキサンジオールジ(メタ)アクリレート、エチレングリコールジメタクリレート、トリメチロールプロパントリアクリレート、ペンタエリスリトールテトラヒドロフランアクリレート、ウレタンアクリレート等が挙げられる。
光ラジカル重合開始剤としても、公知のものから適宜選択して用いればよく、例えば、アセトフェノン類、ベンゾフェノン類、ミヒラーのベンゾイルベンゾエート、アミロキシムエステル、オキシムエステル類、テトラメチルチウラムモノサルファイドおよびチオキサントン類等が挙げられる。
特に、光開裂型の光ラジカル重合開始剤が好ましい。光開裂型の光ラジカル重合開始剤については、最新UV硬化技術(159頁、発行人:高薄一弘、発行所:(株)技術情報協会、1991年発行)に記載されている。
市販の光ラジカル重合開始剤としては、例えば、BASF社製 商品名:イルガキュア 127、184、369、379、379EG、651、500、754、819、903、907、784、2959、CGI1700、CGI1750、CGI1850、CG24-61、OXE01、OXE02、ダロキュア 1116、1173、MBF、BASF社製 商品名:ルシリン TPO、UCB社製 商品名:ユベクリル P36、フラテツリ・ランベルティ社製 商品名:エザキュアー KIP150、KIP65LT、KIP100F、KT37、KT55、KTO46、KIP75/B等が挙げられる。
光ラジカル重合開始剤を用いる場合、(メタ)アクリル系モノマー100質量部に対して、0.1~200質量部の範囲で使用することが好ましく、1~150質量部の範囲で使用することがより好ましい。
接着剤の塗布方法は任意であり、例えば、スピンコート法、ディップ法、フローコート法、インクジェット法、ジェットディスペンサー法、スプレー法、バーコート法、グラビアコート法、スリットコート法、ロールコート法、転写印刷法、刷毛塗り、ブレードコート法、エアーナイフコート法等の方法を採用できる。
光照射する場合の条件は、特に限定されるものではなく、用いるトリアジン環含有重合体および(メタ)アクリル系モノマーに応じて、適宜な照射エネルギーおよび時間を採用すればよい。
本発明の接着剤用組成物を含む接着剤は、液晶ディスプレイ、有機エレクトロルミネッセンス(EL)ディスプレイ、タッチパネル、光半導体(LED)素子、固体撮像素子、有機薄膜太陽電池、色素増感太陽電池、有機薄膜トランジスタ(TFT)、レンズ、プリズム、カメラ、双眼鏡、顕微鏡、半導体露光装置等の電子デバイスや光学デバイスなどの透明性および高屈折率が要求されるデバイスの接着剤として好適である。
(1)GPC(ゲル浸透クロマトグラフィ)
装置:SHIMADZU社製 SCL-10Avp GPCに改造
カラム:Shodex K-804L+K-805L
カラム温度:60℃
溶媒: N-メチル-2-ピロリドン(0.1%LiCl添加)
検出器:UV(254nm)
検量線:標準ポリスチレン
(2)全光線透過率,ヘイズ
装置:日本電色工業(株)製 NDH5000
(3)屈折率(薄膜)
装置:ジェー・エー・ウーラム・ジャパン製 多入射角分光エリプソメーターVASE
(4)屈折率(厚膜)
装置:Metricon社製 Metricon 2010/M プリズムカプラ
(5)紫外・可視・近赤外分光光度計
装置:(株)島津製作所製 UV-3600
(6)示差熱天秤(TG-DTA)
装置:(株)リガク製 TG-8120
昇温速度:10℃/分
測定温度:20~500℃
(7)DSC
装置:NETZSCH製 DSC 204F1 Phoenix
昇温速度:30℃/分
測定温度:25~300℃
(8)液屈折率測定
装置:(株)ATAGO製 多波長アッベ屈折計 DR-M4
測定波長:589nm
測定温度:20℃
(9)引張せん断接着強度測定
装置:(株)島津製作所製 島津精密万能試験機オートグラフ
その後、アニリン(26.9g、288.5mmol、純正化学(株)製)を加え、3時間撹拌して反応を終了した。氷浴により室温まで冷却後、反応溶液を28%アンモニア水溶液(65.9g)とイオン交換水(1000g)との混合溶液に再沈殿させた。沈殿物をろ過し、ポリマーの湿品を得た。得られたポリマーの湿品を、テトラヒドロフラン(280g、以下THF)と28%アンモニア水溶液(65.9g)の混合溶液に再溶解させ、30分間撹拌した後、40℃まで昇温して分液した。有機層を回収し、酢酸アンモニウムを少量溶かしたイオン交換水(1500g)にて再沈殿させた。得られた沈殿物をろ過して減圧乾燥機で130℃、8時間乾燥し、目的とする高分子化合物[3](以下、HB-TmDAL-T)23.2gを得た。
HB-TmDAL-TのGPCによるポリスチレン換算で測定される重量平均分子量Mwは3330、多分散度Mw/Mnは2.68であった。
HB-TmDAL-Tについて、DSCによりガラス転移温度(Tg)を、TG-DTAにより5%重量減少温度(Td5%)を、それぞれ測定したところ、Tgは131.5℃であり、Td5%は360.5℃であった。
窒素下、1000mL四口フラスコに、1,3-フェニレンジアミン(35.18g、32.5mmol、アミノケム社製)、アニリン(10.10g、108.5mmol、純正化学(株)製)、およびDMAc(716.9g、純正化学(株)製)を仕込み、-15℃まで冷却した。このアミン溶液に、内温-15~-10℃を維持したまま2,4,5-トリクロロ-1,3,5-トリアジン(80g、433.8mmol、エポニックデグザ社製)を30分かけて粉末投入した。その後、-10℃で1時間撹拌し、この反応溶液を、予め2000mL四口フラスコにDMAc(586.4g、純正化学(株)製)を加えてオイルバスで85℃に加熱してある槽へ送液ポンプにより45分間かけて滴下し、2時間撹拌して重合した。
その後、アニリン(107.4g、1154.0mmol、純正化学(株)製)を加え、3時間撹拌して反応を終了した。氷浴により室温まで冷却後、反応溶液を28%アンモニア水溶液(263.9g)とイオン交換水(4000g)との混合溶液に再沈殿させた。沈殿物をろ過し、ポリマーの湿品を得た。得られたポリマーの湿品を、THF(1120g)と28%アンモニア水溶液(263.9g)との混合溶液に再溶解させ、30分間撹拌した後、40℃まで昇温して分液した。有機層を回収し、酢酸アンモニウムを少量溶かしたイオン交換水(6000g)にて再沈殿させた。得られた沈殿物をろ過して減圧乾燥機で130℃、8時間乾燥し、目的とする高分子化合物[3](以下、HB-TmDAL-T2)53.0gを得た。
HB-TmDAL-T2のGPCによるポリスチレン換算で測定される重量平均分子量Mwは4855、多分散度Mw/Mnは2.31であった。
HB-TmDAL-T2について、DSCによりガラス転移温度(Tg)を、TG-DTAにより5%重量減少温度(Td5%)を、それぞれ測定したところ、Tgは169.3℃であり、Td5%は394.5℃であった。
窒素下、500mL四口フラスコに、1,3-フェニレンジアミン(17.59g、162.7mmol、アミノケム社製)、アニリン(5.05g、54.2mmol、純正化学(株)製)、およびDMAc(358.4g、純正化学(株)製)を仕込み、-15℃まで冷却した。このアミン溶液に、内温-15~-10℃を維持したまま2,4,5-トリクロロ-1,3,5-トリアジン(40g、216.9mmol、エポニックデグザ社製)を10分かけて粉末投入した。その後、-10℃で1時間撹拌し、この反応溶液を、予め1000mL四口フラスコにDMAc(293.2g、純正化学(株)製)を加えてオイルバスで85℃に加熱してある槽へ送液ポンプにより30分間かけて滴下し、2時間撹拌して重合した。
その後、アニリン(53.7g、576.9mmol、純正化学(株)製)を加え、3時間撹拌して反応を終了した。氷浴により室温まで冷却後、反応溶液を28%アンモニア水溶液(131.9g)とイオン交換水(2000g)の混合溶液に再沈殿させた。沈殿物をろ過し、ポリマーの湿品を得た。得られたポリマーの湿品を、THF(560g)と28%アンモニア水溶液(131.9g)との混合溶液に再溶解させ、30分間撹拌した後、40℃まで昇温して分液した。有機層を回収し、酢酸アンモニウムを少量溶かしたイオン交換水(3000g)にて再沈殿させた。得られた沈殿物をろ過して減圧乾燥機で130℃、8時間乾燥し、目的とする高分子化合物[3](以下、HB-TmDAL-T3)46.0gを得た。
HB-TmDAL-T3のGPCによるポリスチレン換算で測定される重量平均分子量Mwは4198、多分散度Mw/Mnは2.29であった。
HB-TmDAL-T3について、DSCによりガラス転移温度(Tg)を、TG-DTAにより5%重量減少温度(Td5%)を、それぞれ測定したところ、Tgは152.6℃であり、Td5%は393.3℃であった。
窒素下、200mL四口フラスコに、DMAc(66.1g)をアセトン/ドライアイス浴で-15℃まで冷却し、2,4,6-トリクロロ-1,3,5-トリアジン(18.44g、0.1mol、エポニックデグザ社製)を加えて溶解した。その後、300mL四口フラスコに、DMAc99.14gに溶解したm-フェニレンジアミン(13.52g、0.125mol、デュポン社製)を-15℃に冷却し、予め-15℃に冷却した2,4,6-トリクロロ-1,3,5-トリアジンのDMAc溶液を120分かけて滴下した。滴下後30分撹拌した後、アニリン(3.17g、0.034mol)を15分かけて滴下した。滴下後30分撹拌し、この反応溶液を、予め500mL四口フラスコにDMAc135.18gを加え、オイルバスで90℃に加熱してある槽へ、送液ポンプを用いて30分かけて滴下し、2時間撹拌して重合した。
その後、アニリン(24.77g、0.266mol)を加え、3時間撹拌して反応を停止した。室温まで放冷後、28%アンモニア水溶液(60.71g)とイオン交換水(922.1g)との混合溶液に再沈殿させた。沈殿物をろ過し、得られたポリマーの湿品をTHF(258.2g)と28%アンモニア水溶液(60.71g)との混合溶液に加えて40℃で30分撹拌した。撹拌後、30分静置することで分液し、有機層を取り出した。取り出した有機層の濃度調整をTHFにて行った後、再度、28%アンモニア水溶液(60.71g)を加え、40℃で撹拌した後、分液し、有機層を取り出した。有機層の濃度調整を行い、この溶液を28%アンモニア水溶液(94.11g)とイオン交換水(1383g)との混合溶液中に再沈殿させた。沈殿物をろ過し、減圧乾燥機で150℃、20時間乾燥し、目的とする高分子化合物[3](以下、HB-TmDAと略す)25.7gを得た。
HB-TmDAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは10200、多分散度Mw/Mnは6.5であった。
HB-TmDAについて、DSCによりガラス転移温度(Tg)を、TG-DTAにより5%重量減少温度(Td5%)を、それぞれ測定したところ、Tgは200.0℃であり、Td418.5℃であった。
空気下、10mLサンプル瓶に上記合成例1~3で得られた高分子化合物0.4000gを加え、溶媒としてシクロペンタノン1.6000gを加え、ミックスローター(110rpm)を用いて室温にて完全に溶解させ、溶液が均一になるまで1時間撹拌した。撹拌後、溶質は完全に溶解し、薄黄色透明溶液として、固形分20質量%のポリマーワニスを得た。
各ポリマーワニスを石英基板上にスピンコーターを用いて1000rpm(30秒)の条件でスピンコートし、大気下、130℃のホットプレートで3分間の焼成を行い、薄膜を得た。薄膜の屈折率は、550nmの波長において、HB-TmDAL-Tが1.764、HB-TmDAL-T2が1.764、HB-TmDAL-T3が1.756であり、いずれも1.75以上を示し、高屈折率材料であることがわかった。
[実施例1-1]
空気下、10mLサンプル瓶に、合成例1で得られたトリアジン系高分岐ポリマーHB-TmDAL-T4.0000gを加え、これに反応性希釈剤であるN-ビニルホルムアミド(以下、NVF)6.0000gを加え、室温にて、ミックスローター(110rpm)を用いてポリマーが完全に溶解して溶液が均一になるまで撹拌した。撹拌後、ポリマーが完全に溶解した薄黄色透明溶液として、トリアジン系高分岐ポリマーが40質量%の接着剤用組成物を得た。
次いで、この40質量%の接着剤用組成物0.6000gにイソボルニルアクリレート(大阪有機化学工業(株)製)、以下IBXA)1.4000g(質量比3:7)を加え、これらを溶質が完全に溶解して溶液が均一になるまで撹拌し、ポリマーワニスを得た。
40質量%の接着剤用組成物とIBXAの質量比が、それぞれ5:5、8:2となるようにした以外は、実施例1-1と同様にして各ポリマーワニスを得た。
比較合成例1で得られたトリアジン系高分岐ポリマーHB-TmDAを用いた以外は、実施例1-1~1-3と同様にして、40質量%の接着剤用組成物と、IBXAとの質量比が、3:7、5:5、8:2の各ポリマーワニスを得た。
[実施例2-1]
空気下、10mLサンプル瓶に、合成例1で得られたトリアジン系高分岐ポリマーHB-TmDAL-T3.0000gを加え、これに反応性希釈剤としてNVF7.0000gを加え、室温にて、ミックスローター(110rpm)を用い、ポリマーが完全に溶解して溶液が均一になるまで撹拌した。撹拌後、ポリマーが完全に溶解した薄黄色透明溶液として、トリアジン系高分岐ポリマーが30質量%のワニスを得た。
次いで、この30質量%のワニス10.0000gにレベリング剤としてBYK-333(ビックケミー・ジャパン(株)製)0.010g(30質量%ワニス100質量部に対して0.1質量部)を加えた。最後に光ラジカル重合開始剤としてイルガキュア-2959(BASF社製)0.500g(30質量%ワニス100質量部に対して5.00質量部)を加えた。これらを溶質が完全に溶解して溶液が均一になるまで撹拌し、トリアジン系高分岐ポリマーが29質量%の接着剤用組成物(以下、HB-TmDAL-TN30と略す)を得た。
得られたHB-TmDAL-TN30を、石英基板上にスピンコーターを用いて7000rpm(30秒)の条件でスピンコートし、その後、窒素下、積算光量1000mJ/cm2でUV硬化し、高分岐ポリマーの薄膜を得た(膜厚3.0μm)。
空気下、10mLサンプル瓶に、合成例1で得られたトリアジン系高分岐ポリマーHB-TmDAL-T4.0000gを加え、これに反応性希釈剤としてNVF6.0000gを加え、室温にて、ミックスローター(110rpm)を用いてポリマーが完全に溶解して溶液が均一になるまで撹拌した。撹拌後、ポリマーが完全に溶解した薄黄色透明溶液として、トリアジン系高分岐ポリマーが40質量%のワニスを得た。
次いで、この40質量%のワニス10.0000gにレベリング剤としてBYK-333(ビックケミー・ジャパン(株)製)0.010g(40質量%ワニス100質量部に対して0.1質量部)を加えた。最後に光ラジカル重合開始剤としてイルガキュア-2959(BASF社製)0.500g(40質量%ワニス100質量部に対して5.00質量部)を加えた。これらを溶質が完全に溶解して溶液が均一になるまで撹拌し、トリアジン系高分岐ポリマーが39質量%の接着剤用組成物(以下、HB-TmDAL-TN40と略す)を得た。
得られたHB-TmDAL-TN40を用いた以外は、実施例2-1と同様にして高分岐ポリマーの薄膜を得た(膜厚4.3μm)。
トリアジン系高分岐ポリマーHB-TmDAL-Tに代えて、合成例2で得られたトリアジン系高分岐ポリマーHB-TmDAL-T2を用いた以外は、実施例2-1,2-2と同様にして、トリアジン系高分岐ポリマーが29質量%の接着剤用組成物(以下、HB-TmDAL-T2N30と略す)、同39質量%の接着剤用組成物(以下、HB-TmDAL-T2N40と略す)をそれぞれ得た。
トリアジン系高分岐ポリマーHB-TmDAL-Tに代えて、合成例3で得られたトリアジン系高分岐ポリマーHB-TmDAL-T3を用いた以外は、実施例2-1,2-2と同様にして、トリアジン系高分岐ポリマーが29質量%の接着剤用組成物(以下、HB-TmDAL-T3N30と略す)、同39質量%の接着剤用組成物(以下、HB-TmDAL-T3N40と略す)をそれぞれ得た。
空気下、10mLサンプル瓶に、合成例1で得られたトリアジン系高分岐ポリマーHB-TmDAL-T5.0000gを加え、これに反応性希釈剤としてNVF4.0000gと4-アクリロイルモルホリン(以下、ACMO)1.0000gとを加え、室温にて、ミックスローター(110rpm)を用いてポリマーが完全に溶解して溶液が均一になるまで撹拌した。撹拌後、ポリマーが完全に溶解した薄黄色透明溶液として、トリアジン系高分岐ポリマーが50質量%のワニスを得た。
次いで、この50質量%のワニス5.0000gにレベリング剤としてBYK-333(ビックケミー・ジャパン(株)製)0.005g(50質量%ワニス100質量部に対して0.1質量部)を加え、光ラジカル重合開始剤としてイルガキュア-2959(BASF社製)0.2500g(50質量%ワニスを100質量部に対して5.00質量部)を加えた。これらを溶質が完全に溶解して溶液が均一になるまで撹拌し、トリアジン系高分岐ポリマーが49質量%の接着剤用組成物(HB-TmDAL-TNA50)を得た。
得られたHB-TmDAL-TNA50を、石英基板上にスピンコーターを用いて2000rpm(30秒)の条件でスピンコートし、その後、窒素下、積算光量1000mJ/cm2でUV硬化し、高分岐ポリマーの薄膜を得た。
上記実施例2-1~2-6で調製した各接着剤用組成物について、溶液での屈折率(測定温度20℃)を測定した。結果を表3に示す。
上記実施例2-1,2-2および2-7で作製した硬化膜の屈折率を測定した。また、上記実施例2-1および2-2で作製した硬化膜について、全光線透過率およびヘイズ値を測定した。結果を併せて表4に示す。さらに、実施例2-2で作製した硬化膜の透過率スペクトルを測定した。結果を図1に示す。
[実施例3-1]
空気下、10mLサンプル瓶に、合成例1で得られたトリアジン系高分岐ポリマーHB-TmDAL-T5.0000gを加え、これに反応性希釈剤としてNVF5.0000gを加え、室温にて、ミックスローター(110rpm)を用いてポリマーが完全に溶解して溶液が均一になるまで撹拌した。撹拌後、ポリマーが完全に溶解した薄黄色透明溶液として、トリアジン系高分岐ポリマーが50質量%の接着剤用組成物(HB-TmDAL-TN50)を得た。
次いで、この50質量%の接着剤用組成物0.6000gにIBXA1.4000g(質量比3:7)を加え、さらにレベリング剤としてBYK-333(ビックケミー・ジャパン(株)製)0.002g(50質量%接着剤用組成物とIBXAを100質量部とし、これに対して0.1質量部)を加えた。最後に光ラジカル重合開始剤としてイルガキュア-2959(BASF社製)を0.010g(50質量%接着剤用組成物とIBXAを100質量部とし、これに対して5.00質量部)を加えた。これらを溶質が完全に溶解して溶液が均一になるまで撹拌し、接着剤を得た。
得られた接着剤を、石英基板上にスピンコーターを用いて2000rpm(30秒)の条件でスピンコートし、その後、窒素下、積算光量1000mJ/cm2でUV硬化し、硬化膜を得た。
50質量%の接着剤用組成物とIBXAの質量比が、それぞれ5:5、8:2、0:10となるようにした以外は、実施例3-1と同様にして各接着剤を得た。
得られた各接着剤を用いた以外は、実施例3-1と同様にして硬化膜を得た。
空気下、10mLサンプル瓶に、合成例1で得られたトリアジン系高分岐ポリマーHB-TmDAL-T5.0000gを加え、これに反応性希釈剤としてNVF5.0000gを加え、室温にて、ミックスローター(110rpm)を用いてポリマーが完全に溶解して溶液が均一になるまで撹拌した。撹拌後、ポリマーが完全に溶解した薄黄色透明溶液として、トリアジン系高分岐ポリマーが50質量%の接着剤用組成物を得た。
次いで、この50質量%の接着剤用組成物0.6000gにウレタンアクリレート(8UX-015A、大成ファインケミカル(株)製)1.4000g(質量比3:7)を加え、さらにレベリング剤としてBYK-333(ビックケミー・ジャパン(株)製)0.002g(50質量%接着剤用組成物とIBXAを100質量部とし、これに対して0.1質量部)を加えた。最後に光ラジカル重合開始剤としてイルガキュア-2959(BASF社製)を0.010g(50質量%接着剤用組成物とIBXAを100質量部とし、これに対して5.00質量部)を加えた。これらを溶質が完全に溶解して溶液が均一になるまで撹拌し、接着剤を得た。
得られた接着剤を用いた以外は、実施例3-1と同様にして硬化膜を得た。
50質量%の接着剤用組成物とウレタンアクリレートの質量比が、それぞれ5:5、8:2、0:10となるようにした以外は、実施例3-3と同様にして各接着剤を得た。
得られた各接着剤を用いた以外は、実施例3-1と同様にして硬化膜を得た。
上記実施例3-1~3-6および比較例3-1,3-2で調製した各接着剤について、溶液での屈折率(測定温度20℃)を測定した。結果を表5に示す。
[硬化膜の屈折率]
上記実施例3-1~3-6および比較例3-1,3-2で得られた硬化膜の屈折率を測定した。結果を表5に併せて示す。
空気下、10mLサンプル瓶に、合成例1で得られたトリアジン系高分岐ポリマーHB-TmDAL-T5.0000gを加え、これに反応性希釈剤としてN-ジメチルアクリルアミド(以下、DMAA)5.0000gを加え、50℃にて、ミックスローター(110rpm)を用いてポリマーが完全に溶解して溶液が均一になるまで撹拌した。撹拌後、ポリマーが完全に溶解した薄黄色透明溶液として、トリアジン系高分岐ポリマーが50質量%の接着剤組成物(HB-TmDAL-TD50)を得た。
次いで、この50質量%の接着剤組成物4.0000gにトリアリルシアヌレート(TAC、エボニック社製)1.0000g(質量比4:1)を加え、さらに光ラジカル重合開始剤としてイルガキュア-2959(BASF社製)0.25g(50質量%接着剤組成物とTACを100質量部とし、これに対して5.00質量部)を加えた。これらを溶質が完全に溶解して溶液が均一になるまで撹拌し、接着剤(TD50-TAC)を得た。
実施例3-7で調製した50質量%の接着剤組成物(HB-TmDAL-TD50)4.0000gにNKエステル A-DCP(新中村化学工業(株)製)1.0000g(質量比4:1)を加え、さらに光ラジカル重合開始剤としてイルガキュア-2959(BASF社製)0.25g(50質量%接着剤組成物とA-DCPを100質量部とし、これに対して5.00質量部)を加えた。これらを溶質が完全に溶解して溶液が均一になるまで撹拌し、接着剤(TD50-DCP)を得た。
実施例3-7で調製した50質量%の接着剤組成物(HB-TmDAL-TD50)4.0000gにNKエステル A-LEN-10(新中村化学工業(株)製)1.0000g(質量比4:1)を加え、さらに光ラジカル重合開始剤としてイルガキュア-2959(BASF社製)0.25g(50質量%接着剤組成物とA-LEN-10を100質量部とし、これに対して5.00質量部)を加えた。これらを溶質が完全に溶解して溶液が均一になるまで撹拌し、接着剤(TD50-LEN)を得た。
実施例3-7で調製した50質量%の接着剤組成物(HB-TmDAL-TD50)4.0000gにIBXA1.0000g(質量比4:1)を加え、さらに光ラジカル重合開始剤としてイルガキュア-2959(BASF社製)0.25g(50質量%接着剤組成物とIBXAを100質量部とし、これに対して5.00質量部)を加えた。これらを溶質が完全に溶解して溶液が均一になるまで撹拌し、接着剤(TD50-IB)を得た。
実施例3-7で調製した50質量%の接着剤組成物(HB-TmDAL-TD50)4.0000gにアダマンチルアクリレート(M-104、出光興産(株)製)1.0000g(質量比4:1)加え、さらに光ラジカル重合開始剤としてイルガキュア-2959(BASF社製)0.25g(50質量%接着剤組成物とM-104を100質量部とし、これに対して5.00質量部)を加えた。これらを溶質が完全に溶解して溶液が均一になるまで撹拌し、接着剤(TD50-104)を得た。
上記実施例3-7~3-11で調製した各種接着剤0.5000gを、Novec1720(3M社製)を用いて離型処理した石英基板上に載せ、同石英基板で挟み込んだ。硬化膜の膜厚は、厚み100μmのシリコンスペーサーを用いて統一した。その後、窒素下、積算光量1000mJ/cm2でUV硬化し、120℃で10分間ポストベイクした後、離型処理した石英基板を剥すことで、硬化膜を得た。
作製した各硬化膜の屈折率をプリズムカプラにより測定した。結果を表6に示す。
上記実施例3-7~3-11で調製した各種接着剤1.0000gを、Novec1720(3M社製)を用いて離型処理した石英基板上に載せ、同石英基板で挟み込んだ。硬化膜の膜厚は、厚み1mmのシリコンスペーサーを用いて統一した。その後、窒素下、積算光量1000mJ/cm2でUV硬化し、120℃で10分間ポストベイクした後、離型処理した石英基板を剥すことで、硬化膜を得た。
作製した各硬化膜を室温下で水中に24時間浸漬し、浸漬前後の質量変化から吸水率を算出した。結果を表7に示す。
上記実施例3-7で調製した接着剤TD50-TACを用いて、JIS K6850に準拠してガラス基材に対する引張せん断を評価した。
ガラス基材は、厚み3mmを使用し、接着剤は、屈折率測定時と同様の方法で硬化膜とし、その厚みは100μmとした。クロスヘッドの移動速度は、5mm/分とし、試験片が破断した際の最大荷重(N)を接着面積(mm2)で割った値を引張せん断接着強度とした。
接着剤TD50-TACのガラス/ガラス引張せん断接着強度は、1.6MPaであった。
Claims (11)
- 下記式(1)で表される繰り返し単位構造を含み、重量平均分子量が500~7,000のトリアジン環含有重合体と、下記式(A)で表される反応性希釈剤と、を含み、溶媒を含まないことを特徴とする無溶剤型光硬化性接着剤用組成物。
Arは、式(2)~(13)で示される群から選ばれる少なくとも1種を表す。
R93およびR94は、互いに独立して、水素原子または炭素数1~10の分岐構造を有していてもよいアルキル基を表し、
W1およびW2は、互いに独立して、単結合、CR95R96(R95およびR96は、互いに独立して、水素原子または炭素数1~10の分岐構造を有していてもよいアルキル基(ただし、これらは一緒になって環を形成していてもよい。)を表す。)、C=O、O、S、SO、SO2、またはNR97(R97は、水素原子または炭素数1~10の分岐構造を有していてもよいアルキル基を表す。)を表し、
X1およびX2は、互いに独立して、単結合、炭素数1~10の分岐構造を有していてもよいアルキレン基、または式(14)
Y1およびY2は、互いに独立して、単結合または炭素数1~10の分岐構造を有していてもよいアルキレン基を表す。)で示される基を表す。〕}
- 前記式(A)におけるR102およびR103が、ともに水素原子であり、R104が、重合性炭素-炭素二重結合含有基である請求項1記載の無溶剤型光硬化性接着剤用組成物。
- 前記反応性希釈剤が、N-ビニルホルムアミド、4-アクリロイルモルホリン、N-ジメチルアクリルアミド、およびN-ジエチルアクリルアミドから選ばれる1種または2種以上である請求項1または2記載の無溶剤型光硬化性接着剤用組成物。
- アクリル系材料を接着成分とする無溶剤型光硬化性接着剤用である請求項1~4のいずれか1項記載の無溶剤型光硬化性接着剤用組成物。
- 請求項1~5のいずれか1項記載の無溶剤型光硬化性接着剤用組成物と、アリル系モノマー、(メタ)アクリル系モノマーおよび(メタ)アクリル系オリゴマーから選ばれる少なくとも1種と、を含む無溶剤型光硬化性接着剤。
- 前記(メタ)アクリル系モノマーが、メチル(メタ)アクリレート、エチル(メタ)アクリレート、ブチル(メタ)アクリレート、2-(2-エトキシエトキシ)エチルアクリレート、テトラヒドロフルフリル(メタ)アクリレート、ラウリルアクリレート、イソオクチルアクリレート、イソデシルアクリレート、2-フェノキシエチルアクリレート、2-エチルヘキシル(メタ)アクリレート、イソボルニル(メタ)アクリレート、アダマンチル(メタ)アクリレート、ジシクロペンテニルオキシエチル(メタ)アクリレート、ジシクロペンタジエニル(メタ)アクリレート、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、2-ヒドロキシブチル(メタ)アクリレート、カプロラクトンアクリレート、モルホリン(メタ)アクリレート、ヘキサンジオールジ(メタ)アクリレート、エチレングリコールジメタクリレート、トリメチロールプロパントリアクリレート、ペンタエリスリトールテトラヒドロフランアクリレートおよびウレタンアクリレートから選ばれる1種または2種以上である請求項6記載の無溶剤型光硬化性接着剤。
- さらに、光ラジカル開始剤を含む請求項6または7記載の無溶剤型光硬化性接着剤。
- 請求項6~8のいずれか1項記載の無溶剤型光硬化性接着剤を硬化させて得られる接着膜。
- 請求項9記載の接着膜を用いて作製される電子デバイス。
- 請求項9記載の接着膜を用いて作製される光学デバイス。
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