CN107001872B - Adhesive sheet - Google Patents
Adhesive sheet Download PDFInfo
- Publication number
- CN107001872B CN107001872B CN201580064807.4A CN201580064807A CN107001872B CN 107001872 B CN107001872 B CN 107001872B CN 201580064807 A CN201580064807 A CN 201580064807A CN 107001872 B CN107001872 B CN 107001872B
- Authority
- CN
- China
- Prior art keywords
- adhesive sheet
- intermediate layer
- sheet according
- meth
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000853 adhesive Substances 0.000 title claims abstract description 91
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 89
- 239000010410 layer Substances 0.000 claims abstract description 132
- 239000000178 monomer Substances 0.000 claims abstract description 90
- 239000000203 mixture Substances 0.000 claims abstract description 68
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 125000000524 functional group Chemical group 0.000 claims abstract description 20
- 239000012790 adhesive layer Substances 0.000 claims abstract description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 100
- 229920005989 resin Polymers 0.000 claims description 35
- 239000011347 resin Substances 0.000 claims description 35
- 239000004065 semiconductor Substances 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 21
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 18
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000012943 hotmelt Substances 0.000 claims description 12
- 229920000058 polyacrylate Polymers 0.000 claims description 9
- -1 polyol compound Chemical class 0.000 description 52
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 32
- 125000000217 alkyl group Chemical group 0.000 description 24
- 239000000463 material Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 14
- 238000000576 coating method Methods 0.000 description 14
- 229920005862 polyol Polymers 0.000 description 14
- 239000003999 initiator Substances 0.000 description 13
- 230000000740 bleeding effect Effects 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 8
- 238000000227 grinding Methods 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 description 7
- 239000005020 polyethylene terephthalate Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- 150000007519 polyprotic acids Polymers 0.000 description 5
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- 229920006243 acrylic copolymer Polymers 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229920005601 base polymer Polymers 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- 238000003475 lamination Methods 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical compound [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 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
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- 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 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920005672 polyolefin resin Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- WNWYHISZSSPWKL-UHFFFAOYSA-N 1-[(4-chlorophenoxy)methyl]-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1COC1=CC=C(Cl)C=C1 WNWYHISZSSPWKL-UHFFFAOYSA-N 0.000 description 1
- PSYZZPZSAKLGJZ-UHFFFAOYSA-N 1-ethenoxydocosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC=C PSYZZPZSAKLGJZ-UHFFFAOYSA-N 0.000 description 1
- UKDKWYQGLUUPBF-UHFFFAOYSA-N 1-ethenoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOC=C UKDKWYQGLUUPBF-UHFFFAOYSA-N 0.000 description 1
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 1
- LPYHXIHXJREIMY-UHFFFAOYSA-N 1-ethenoxytetradecane Chemical compound CCCCCCCCCCCCCCOC=C LPYHXIHXJREIMY-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Images
Classifications
-
- 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
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
-
- 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
- C09J201/00—Adhesives based on unspecified macromolecular compounds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/304—Mechanical treatment, e.g. grinding, polishing, cutting
-
- 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
Landscapes
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Mechanical Treatment Of Semiconductor (AREA)
Abstract
The adhesive sheet (10A) of the present invention comprises, in order: the adhesive layer comprises a base (11), an intermediate layer (12), and an adhesive layer (13), wherein the intermediate layer (12) is obtained by curing an intermediate layer composition containing a polyfunctional compound and a monofunctional monomer, the polyfunctional compound has at least 2 polymerizable functional groups, the monofunctional monomer contains at least a crystalline monomer having a linear carbon chain of 14-22 carbon atoms, and the intermediate layer composition contains the polyfunctional compound in an amount of more than 25 mass% relative to the monofunctional monomer.
Description
Technical Field
The present invention relates to an adhesive sheet to be attached to an adherend such as a semiconductor wafer or the like for protecting the adherend, and particularly relates to a back grinding piece.
Background
In the rapid progress of the reduction in thickness, size, and multi-functionalization of information terminal devices, semiconductor devices mounted therein are also required to be reduced in thickness and increased in density. For the thinning of the device, the thinning of the semiconductor wafer into which the semiconductor is integrated is desired. In order to meet this demand, a study is being made to reduce the thickness of the back surface of the semiconductor wafer by grinding the back surface.
In recent years, bumps made of solder or the like having a height of about 30 to 100 μm are formed on the wafer surface, and the back surface of the semiconductor wafer having the bumps is ground. In the case of back grinding such a bumped semiconductor wafer, an adhesive sheet called a back grinding chip is attached to the surface of the wafer on which the bumps are formed in order to protect the bump portions.
In the adhesive sheet used for the back grinding sheet, an intermediate layer may be provided between the base material and the adhesive layer in order to embed the bumps and absorb and mitigate the level difference on the surface of the semiconductor wafer. It is known that an energy ray curable resin having a storage modulus which decreases at a high temperature and increases at a room temperature can be used for the intermediate layer in order to improve the embedding property of the bump at the bonding temperature, to improve the holding property of the wafer surface at a room temperature, and to improve the form stability when the intermediate layer is formed into a roll.
However, when only the energy ray curable resin is used, the intermediate layer may be softened excessively at the bonding temperature, and the intermediate layer may bleed out at the time of bonding, and the difference in level of the bump may not be sufficiently absorbed by the intermediate layer. In order to solve these problems, an intermediate layer in which a crystalline hot-melt resin is dispersed in a matrix resin made of an energy ray curable resin is known as disclosed in patent document 1.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2013-87131
Disclosure of Invention
Problems to be solved by the invention
However, when a crystalline hot-melt resin is dispersed in the intermediate layer as in patent document 1, the film forming property of the intermediate layer may be reduced. Therefore, there is a demand for an intermediate layer that can adequately embed bumps without using a heat-fusible resin, sufficiently alleviate the difference in level, and prevent bleeding at the time of attachment.
The present invention has been made in view of the above problems, and an object of the present invention is to provide an adhesive sheet which, even when the intermediate layer does not contain a crystalline hot-melt resin, can have good embeddability in irregularities formed on an adherend such as a semiconductor wafer when the adhesive sheet is attached to the adherend, and can prevent the intermediate layer from bleeding out when the adhesive sheet is attached.
Means for solving the problems
As a result of intensive studies, the present inventors have found that the above problems can be solved by forming an intermediate layer by curing a monofunctional monomer containing a crystalline monomer and a polyfunctional compound contained in a predetermined ratio or more with respect to the monofunctional monomer, and have completed the following invention.
(1) An adhesive sheet comprising, in order: a substrate, an intermediate layer, and an adhesive layer, wherein,
the intermediate layer is obtained by curing an intermediate layer composition containing a polyfunctional compound and a monofunctional monomer, wherein the polyfunctional compound has at least 2 polymerizable functional groups, and the monofunctional monomer at least contains a crystalline monomer having a linear carbon chain with 14-22 carbon atoms,
the composition for an intermediate layer contains the polyfunctional compound in an amount of more than 25 mass% relative to the monofunctional monomer.
(2) The adhesive sheet according to the item (1), wherein 40% by mass or more of the monofunctional monomer is the crystalline monomer.
(3) The adhesive sheet according to (1) or (2), wherein the polyfunctional compound is a polyfunctional oligomer having a weight average molecular weight of 3000 to 60000.
(4) The adhesive sheet according to any one of (1) to (3) above, wherein the polymerizable functional group of the polyfunctional compound is a group having an olefinic double bond.
(5) The adhesive sheet according to any one of (1) to (4) above, wherein the polyfunctional compound is at least 1 selected from a urethane (meth) acrylate oligomer, an acrylic polymer, and a butadiene-based polymer.
(6) The adhesive sheet according to any one of the above (1) to (5), wherein the crystalline monomer is contained in an amount of 25 to 70 mass% based on the total amount of the composition for an intermediate layer.
(7) The adhesive sheet according to any one of (1) to (6), wherein the composition for an intermediate layer is an energy ray-curable type.
(8) The adhesive sheet according to any one of (1) to (7), wherein the thickness of the intermediate layer is 150 to 700 μm.
(9) The adhesive sheet according to any one of the above (1) to (8), which is a semiconductor wafer protection tape.
Effects of the invention
The present invention can provide an adhesive sheet that, when the adhesive sheet is attached to an adherend such as a semiconductor wafer, can provide good embeddability of irregularities in the adherend and can prevent bleeding of the intermediate layer during attachment.
Drawings
Fig. 1 is a sectional view showing an adhesive sheet according to an embodiment of the present invention.
Fig. 2 is a sectional view showing an adhesive sheet according to another embodiment of the present invention.
Description of the symbols
10A, 10B adhesive sheet
11 base material
12 intermediate layer
13 adhesive layer
14 Release Material
Detailed Description
The present invention will be described below with reference to embodiments. In the following description, "weight average molecular weight (Mw)" is a value in terms of polystyrene measured by a Gel Permeation Chromatography (GPC) method, specifically, a value measured by the method described in examples.
In the description of the present specification, for example, "(meth) acrylate" is used as a term indicating both "acrylate" and "methacrylate", and other similar terms are treated in the same manner.
Fig. 1 and 2 show an adhesive sheet according to an embodiment of the present invention. The pressure-sensitive adhesive sheet of the present invention is not particularly limited as long as it is formed by providing an intermediate layer 12 on a substrate 11 and further providing a pressure-sensitive adhesive layer 13 on the intermediate layer 12, as in the pressure-sensitive adhesive sheet 10A shown in fig. 1. The adhesive sheet may be composed of these 3 layers, or may be further provided with another layer. For example, as in the case of the pressure-sensitive adhesive sheet 10B shown in fig. 2, the pressure-sensitive adhesive layer 13 may further include a release agent 14.
Hereinafter, each member constituting the adhesive sheet will be described in more detail.
[ intermediate layer ]
The intermediate layer is formed by curing an intermediate layer composition containing a polyfunctional compound and a monofunctional monomer, wherein the polyfunctional compound has at least 2 polymerizable functional groups, and the monofunctional monomer at least contains a crystalline monomer having a linear carbon chain with 14-22 carbon atoms.
In the present invention, the composition for an intermediate layer forming the intermediate layer contains a polyfunctional compound and a monofunctional monomer, and at least a part of the monofunctional monomer is a crystalline monomer, whereby the adhesive sheet can have good embeddability in irregularities on the surface of an adherend such as a bump of a semiconductor wafer. Further, when the adhesive sheet is attached to an adherend such as a semiconductor wafer at high temperature, the intermediate layer can be prevented from bleeding out.
The composition for the intermediate layer is cured by polymerization of a polyfunctional compound and a monofunctional monomer to form the intermediate layer. The composition for the intermediate layer is preferably an energy ray-curable type that is cured by an energy ray. The energy ray is a ray having an energy quantum in an electromagnetic wave or a charged particle beam, and refers to an active light such as ultraviolet ray, an electron beam, or the like.
< polyfunctional Compound >
In the composition for an intermediate layer, the polyfunctional compound is contained in an amount of more than 25 mass% relative to the total amount of the monofunctional monomers. When the content of the polyfunctional compound is 25% by mass or less, it is difficult to ensure embeddability. The content of the polyfunctional compound is preferably 30% by mass or more, and more preferably 50% by mass or more. When the content is 30% by mass or more, the embeddability is easily further improved. In order to secure a certain content of the monofunctional monomer, the upper limit of the content is preferably 250 mass% or less, and more preferably 200 mass% or less.
The polymerizable functional group contained in the polyfunctional compound is preferably a group having an olefinic double bond. Having an olefinic double bond enables the polyfunctional compound to be cured by energy rays such as ultraviolet rays. Specific examples of the group having an ethylenic double bond include a (meth) acryloyl group, a vinyl group and the like, and a (meth) acryloyl group is preferable.
The polyfunctional compound may be either a polyfunctional monomer or a polyfunctional oligomer, and is preferably used because it interacts strongly with the crystalline monomer during curing. The polyfunctional compound may be used alone in 1 kind, or may be used in combination with 2 or more kinds. When 2 or more kinds of polyfunctional compounds are used, 2 kinds of either polyfunctional monomers or polyfunctional oligomers may be used, or both polyfunctional monomers and polyfunctional oligomers may be used.
(polyfunctional oligomer)
The weight average molecular weight of the multifunctional oligomer is preferably 3000 to 60000, and more preferably 5000 to 50000. By setting the weight average molecular weight to the range of more than this, the embeddability of the intermediate layer can be further improved, and the bleeding of the intermediate layer can be easily prevented. Further, the polyfunctional oligomer is in a liquid state and has a viscosity in an appropriate range, and thus the film-forming property is easily improved.
As the polyfunctional oligomer that can be used in the intermediate layer, specifically, there can be mentioned: urethane (meth) acrylate oligomer, acrylic polymer, butadiene-based polymer, polyisoprene, and the like. Among them, urethane (meth) acrylate oligomers, acrylic polymers, and butadiene polymers are preferable. Although monofunctional oligomers having only 1 polymerizable functional group are known as oligomers, in the present invention, when monofunctional oligomers are used instead of polyfunctional oligomers, the intermediate layer is too softened at high temperatures, and it is difficult to prevent bleeding of the intermediate layer.
The urethane (meth) acrylate oligomer, the acrylic polymer and the butadiene-based polymer that can be used for the polyfunctional oligomer will be specifically described below.
Urethane (meth) acrylate oligomer
The urethane (meth) acrylate oligomer is a compound having at least a (meth) acryloyl group and a urethane bond, and has a property of being polymerized by irradiation with an energy ray.
The number of (meth) acryloyl groups (i.e., polymerizable functional groups) in the urethane (meth) acrylate oligomer may be 2 or 3 or more, preferably 2. The urethane (meth) acrylate oligomer can be obtained, for example, by reacting a hydroxyl group-containing (meth) acrylate with an isocyanate-terminated urethane prepolymer obtained by reacting a polyol compound with a polyisocyanate compound.
The urethane (meth) acrylate oligomer may be used alone or in combination of 2 or more.
a. Polyol compounds
The polyol compound is a compound having 2 or more hydroxyl groups, and specific examples of the polyol compound include: polyether polyols, polyester polyols, polycarbonate polyols and the like, and among them, polyether polyols are preferred. The polyol compound may be any of a 2-functional diol, a 3-functional triol, and a 4-or higher-functional polyol, and is preferably a 2-functional diol.
For example, the polyether polyol is preferably a compound represented by the following formula (1).
[ chemical formula 1]
In the formula (1), R is a 2-valent hydrocarbon group, preferably an alkylene group, and more preferably an alkylene group having 1 to 6 carbon atoms. Among alkylene groups having 1 to 6 carbon atoms, ethylene, propylene and tetramethylene groups are preferable, and propylene and tetramethylene groups are more preferable.
In addition, n is the number of repeating units of alkylene oxide, and is usually 10 to 250, preferably 25 to 205, and more preferably 40 to 185. When n is in the above range, the urethane bond concentration of the resulting urethane (meth) acrylate oligomer is appropriate, and the flexibility of the intermediate layer is easily improved.
Among the compounds represented by the above formula (1), polyethylene glycol, polypropylene glycol and polytetramethylene glycol are preferable, and polypropylene glycol and polytetramethylene glycol are more preferable.
The polyester polyol is obtained by polycondensing a polyol component with a polybasic acid component. As the polyol component, there can be mentioned: and known various glycols such as ethylene glycol, diethylene glycol, triethylene glycol, 1, 2-propanediol, 1, 3-butanediol, 1, 4-butanediol, neopentyl glycol, pentanediol, 3-methyl-1, 5-pentanediol, 2, 4-trimethyl-1, 3-pentanediol, hexanediol, octanediol, 2-diethyl-1, 3-propanediol, 2-ethyl-2-butyl-1, 3-propanediol, 1, 4-cyclohexanedimethanol, and ethylene glycol or propylene glycol adducts of bisphenol a.
As the polybasic acid component used for the production of the polyester polyol, a compound generally known as a polybasic acid component of a polyester can be used.
Specific examples of the polybasic acid component include: aliphatic dibasic acids such as adipic acid, maleic acid, succinic acid, oxalic acid, fumaric acid, malonic acid, glutaric acid, pimelic acid, azelaic acid, sebacic acid, and suberic acid; dibasic acids such as phthalic acid, isophthalic acid, terephthalic acid, and 2, 6-naphthalenedicarboxylic acid, aromatic polybasic acids such as trimellitic acid and pyromellitic acid, anhydrides corresponding to these acids, derivatives thereof, dimer acid, and hydrogenated dimer acid.
The polycarbonate-type polyol is not particularly limited, and polyalkylene carbonate diol can be exemplified. Polyalkylene carbonate glycols can be listed: and a polymer having a repeating unit of a linear alkylene group having about 4 to 8 carbon atoms, which is represented by polybutylene carbonate glycol, polypentylene carbonate glycol, polyhexamethylene carbonate glycol, or a copolymer having a mixed alkylene chain of two or more members selected from tetramethylene, pentamethylene, and hexamethylene.
b. Polyisocyanate compound
As the polyisocyanate compound, for example: aliphatic polyisocyanates such as tetramethylene diisocyanate, hexamethylene diisocyanate, and trimethylhexamethylene diisocyanate; alicyclic diisocyanates such as isophorone diisocyanate, norbornane diisocyanate, dicyclohexylmethane-4, 4 ' -diisocyanate, dicyclohexylmethane-2, 4 ' -diisocyanate, and ω, ω ' -diisocyanate dimethylcyclohexane; aromatic diisocyanates such as 4, 4' -diphenylmethane diisocyanate, tolylene diisocyanate, xylylene diisocyanate, tolidine diisocyanate, tetramethylene xylylene diisocyanate, and naphthalene-1, 5-diisocyanate.
Among them, isophorone diisocyanate, hexamethylene diisocyanate, and xylylene diisocyanate are preferable from the viewpoint of handling properties.
c. (meth) acrylate having hydroxyl group
The urethane (meth) acrylate oligomer can be obtained by reacting a hydroxyl group-containing (meth) acrylate with an isocyanate-terminated urethane prepolymer obtained by reacting the above polyol compound with a polyisocyanate compound.
The (meth) acrylate having a hydroxyl group is not particularly limited as long as it is a compound having a hydroxyl group and a (meth) acryloyl group in at least 1 molecule.
Specific examples of the (meth) acrylate having a hydroxyl group include: hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 4-hydroxycyclohexyl (meth) acrylate, 5-hydroxycyclooctyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, pentaerythritol tri (meth) acrylate, polyethylene glycol mono (meth) acrylate, and polypropylene glycol mono (meth) acrylate; hydroxyl group-containing (meth) acrylamides such as N-methylol (meth) acrylamide; and a reaction product obtained by reacting (meth) acrylic acid with vinyl alcohol, vinylphenol, and diglycidyl ester of bisphenol a.
Among them, hydroxyalkyl (meth) acrylates are preferable, and 2-hydroxyethyl (meth) acrylate is more preferable.
Acrylic Polymer
The acrylic polymer used as the polyfunctional compound includes polymers obtained by polymerizing (meth) acrylic acid esters, and includes: the polymer is preferably a polymer obtained by polymerizing an alkyl (meth) acrylate having an alkyl group with 1 to 10 carbon atoms, and more preferably a polymer obtained by polymerizing an alkyl (meth) acrylate having an alkyl group with 3 to 8 carbon atoms.
Here, the alkyl group in the alkyl (meth) acrylate may be branched or linear. As the alkyl (meth) acrylate, there may be mentioned: methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, and the like. The acrylic polymer has a polymerizable functional group, which is usually a (meth) acryloyl group, at both ends.
Butadiene-based Polymer
Examples of the butadiene-based polymer include polymers having 2 or more vinyl groups in the side chain. The butadiene-based polymer has a side chain vinyl group as a polymerizable functional group and can be cured by reacting with a monofunctional monomer. The butadiene-based polymer is a polymer obtained by polymerizing butadiene as a monomer unit, and generally contains a1, 4-bonding unit and a1, 2-vinyl bonding unit.
(polyfunctional monomer)
Examples of the polyfunctional monomer usable as the polyfunctional compound include (meth) acrylic polyfunctional monomers, specifically pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, ethylene oxide addition glycerin (meth) acrylate, and dipropylene glycol di (meth) acrylate.
< monofunctional monomer >
(crystalline monomer)
Monofunctional monomers are monomers having 1 olefinic double bond. The monofunctional monomer contained in the composition for an intermediate layer contains at least a crystalline monomer. The crystalline monomer is a monomer having a linear carbon chain having 14 to 22 carbon atoms, and when the composition for an intermediate layer is polymerized by a curing reaction, crystallinity is imparted to the side chain of the resulting polymer. In the present invention, by containing a crystalline monomer in the composition for an intermediate layer, the elastic modulus of the intermediate layer is reduced and deformed when the intermediate layer is heated and bonded, and the embedding property is easily improved. The crystalline monomer has an ethylenic double bond and has crystallinity in the side chain due to the above-mentioned linear carbon chain having 14 to 22 carbon atoms when forming a polymer.
The monofunctional monomer contained in the composition for an intermediate layer is preferably a crystalline monomer in an amount of 40% by mass or more. In the present invention, by setting the crystalline monomer to 40 mass% or more, the elastic modulus at the time of heat bonding becomes better, and the bleeding of the intermediate layer at the time of bonding the adhesive sheet can be prevented and the embeddability is good.
Further, the monofunctional monomer is more preferably a crystalline monomer in an amount of 45 to 100% by mass, and still more preferably a crystalline monomer in an amount of 77 to 100% by mass. In this way, when the content of the crystalline monomer in the monofunctional monomer is increased, the elastic modulus of the intermediate layer is remarkably decreased during heating and bonding, and therefore, a more favorable embeddability can be exhibited, and the bleeding of resin from the intermediate layer of the adhesive sheet during storage can be suppressed.
The crystalline monomer is a monomer having 1 olefinic double bond, specifically, preferably has a (meth) acryloyl group or a vinyl group as a functional group, more preferably has a (meth) acryloyl group. When the crystalline monomer has an olefinic double bond, the polymerization can be easily performed by irradiation with an energy ray. Further, the (meth) acryloyl group makes it easy to smoothly progress the curing reaction.
The crystalline monomer preferably has a linear alkyl group having 14 to 22 carbon atoms. By providing the crystalline monomer with such a long-carbon-chain straight-chain alkyl group, crystallinity can be imparted to the side chain of the polymer obtained by curing the composition for an intermediate layer. The number of carbon atoms of the linear alkyl group is more preferably 16 to 20.
Specific crystalline monomers include: and (b) an alkyl (meth) acrylate having a linear alkyl group having 14 to 22 carbon atoms, an alkyl vinyl ether having a linear alkyl group having 14 to 22 carbon atoms, and the like, preferably an alkyl (meth) acrylate having a linear alkyl group having 14 to 22 carbon atoms. By using the alkyl (meth) acrylate, the curing reaction can be easily smoothly performed.
Examples of the alkyl (meth) acrylate having a straight-chain alkyl group having 14 to 22 carbon atoms include: tetradecyl (meth) acrylate, hexadecyl (meth) acrylate, octadecyl (meth) acrylate, eicosyl (meth) acrylate, and docosyl (meth) acrylate, among which octadecyl (meth) acrylate is preferable from the viewpoint of easy availability and the like.
Examples of the alkyl vinyl ether having a straight-chain alkyl group having 14 to 22 carbon atoms include: tetradecyl vinyl ether, hexadecyl vinyl ether, octadecyl vinyl ether, eicosyl vinyl ether, docosyl vinyl ether, and the like.
The crystalline monomer is preferably contained in an amount of 25 to 70% by mass, more preferably 40 to 60% by mass, based on the total amount of the composition for the intermediate layer. When the content is 25 mass% or more, the amount of the crystalline portion in the intermediate layer increases, and when the intermediate layer is heated to a high temperature, the elastic modulus of the intermediate layer decreases, and the embeddability is easily improved. When the content is 70% by mass or less, flexibility required as an intermediate layer can be easily secured.
(other monofunctional monomers)
The monofunctional monomer contained in the composition for an intermediate layer may be composed of only the above crystalline monomer, or may contain a monofunctional monomer other than the crystalline monomer.
The monofunctional monomer other than the crystalline monomer is a monomer containing a group having an ethylenic double bond such as a (meth) acryloyl group or a vinyl group, and specific examples thereof include: examples of the (meth) acrylate include (meth) acrylates having an alicyclic structure, (meth) acrylates having a functional group, alkyl (meth) acrylates having an alkyl group having a carbon number of less than 14, amide group-containing compounds, (meth) acrylates having an aromatic structure, (meth) acrylates having a heterocyclic structure, and other vinyl compounds.
Examples of the (meth) acrylate having an alicyclic structure include: isobornyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxy (meth) acrylate, cyclohexyl (meth) acrylate, adamantyl (meth) acrylate, and the like, and among them, isobornyl (meth) acrylate is preferable.
Examples of the functional group used in the functional group-containing (meth) acrylate include a hydroxyl group, an amino group, and an epoxy group. Specific examples of the functional group-containing (meth) acrylate include: hydroxyl group-containing (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and 2-hydroxy-3-phenoxypropyl (meth) acrylate; amino group-containing (meth) acrylates such as primary amino group-containing (meth) acrylates, secondary amino group-containing (meth) acrylates, and tertiary amino group-containing (meth) acrylates; epoxy group-containing (meth) acrylates such as glycidyl (meth) acrylate, methyl glycidyl (meth) acrylate, and allyl glycidyl ether. Among these, hydroxyl group-containing (meth) acrylates are preferable, and among these, 2-hydroxy-3-phenoxypropyl (meth) acrylate is more preferable.
Examples of the alkyl (meth) acrylate having an alkyl group with less than 14 carbon atoms include: methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, n-nonyl (meth) acrylate, n-decyl (meth) acrylate, and the like.
As the amide group-containing compound, there may be mentioned: (meth) acrylamide compounds such as (meth) acrylamide, N-dimethyl (meth) acrylamide, N-butyl (meth) acrylamide, N-methylol (meth) acrylamide, N-methylolpropane (meth) acrylamide, N-methoxymethyl (meth) acrylamide and N-butoxymethyl (meth) acrylamide.
Examples of the (meth) acrylate having an aromatic structure include benzyl (meth) acrylate and the like. Examples of the (meth) acrylate having a heterocyclic structure include: tetrahydrofurfuryl (meth) acrylate, morpholinyl acrylate, and the like. Further, as other vinyl compounds, there may be mentioned: styrene, hydroxyethyl vinyl ether, hydroxybutyl vinyl ether, N-vinylformamide, N-vinylpyrrolidone, N-vinylcaprolactam, and the like.
< photopolymerization initiator >
The composition for the intermediate layer preferably contains a photopolymerization initiator, and can be easily cured by irradiation with active light such as ultraviolet light.
Examples of the photopolymerization initiator include: photopolymerization initiators such as benzoin compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene (titanocene) compounds, thioxanthone compounds, and peroxide compounds, and more specifically, for example: 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl propane-1-one, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, 2,4, 6-trimethylbenzoyldiphenylphosphine oxide, and the like. In addition, depending on the kinds of the polyfunctional compound and the monofunctional monomer, an aromatic diazonium salt or an aromatic halogen may be used in addition to the above
Salts, aromatic sulfonium salts and the like
Cationic photopolymerization initiators such as salts, nitrobenzyl esters, sulfonic acid derivatives, phosphoric esters and sulfonic acid derivatives, and anionic photopolymerization initiators such as catalysts such as titanium alkoxides and p-chlorophenyl o-nitrobenzyl ether. The photopolymerization initiator may be used alone or in combination of 2 or more.
The content of the photopolymerization initiator is preferably 0.05 to 15 parts by mass, more preferably 0.1 to 10 parts by mass, and still more preferably 0.3 to 5 parts by mass, based on 100 parts by mass of the total of the polyfunctional compound and the monofunctional monomer. The composition for an intermediate layer may contain a photosensitizer such as an amine or quinone.
The composition for an intermediate layer may contain other additives within a range not impairing the effects of the present invention. As other additives, for example: antioxidants, antistatic agents, softeners (plasticizers), fillers, rust inhibitors, pigments, dyes, and the like.
The composition for an intermediate layer of the present invention contains a crystalline monomer component, and thus can prevent bleeding out of the intermediate layer at the time of adhesion and can improve embeddability even if the composition for an intermediate layer contains substantially no hot-melt resin, and the hot-melt resin is a resin in which a clear and sharp melting peak is observed in DSC measurement, specifically, a resin in which the difference between the melting start temperature and the melting peak temperature (melting point (Tm)) is 8 ℃ or less and the melting point (Tm) is 45 to 90 ℃, for example, and examples of the hot-melt resin include acrylic polymers that are waxy at room temperature, and polymers of α -olefins having 14 to 30 carbon atoms.
The term "substantially free of a hot-melt resin" means that the composition for an intermediate layer may contain a hot-melt resin to the extent that the film-forming property of the intermediate layer is not affected, and for example, the composition for an intermediate layer may contain a hot-melt resin to the extent of less than 2 mass% relative to the total amount of the composition for an intermediate layer, and the content thereof is preferably less than 1 mass%, and more preferably is not contained. By not substantially containing the hot-melt resin, aggregation and increase in viscosity due to the solid polymer material in the composition for an intermediate layer can be suppressed.
The composition for an intermediate layer usually contains the above-mentioned polyfunctional compound and monofunctional monomer as main components, and the total amount thereof is usually 70% by mass or more, preferably 80% by mass or more, and more preferably 90% by mass or more, relative to the total amount of the composition for an intermediate layer. The total amount of these components may be 100 mass% or less based on the total amount of the composition for the intermediate layer, and is preferably 99.9 mass% or less, more preferably 99.7 mass% or less for the purpose of blending an additive such as a photopolymerization initiator. The total amount of the composition for the intermediate layer means an amount obtained by removing volatile components such as a diluting solvent when the composition is diluted with a solvent or the like volatilized in the production process thereof.
The thickness of the intermediate layer can be adjusted as appropriate according to the height of the bump or the like to be protected, and is preferably 150 to 700 μm, and more preferably 200 to 300 μm. When the thickness of the intermediate layer is 150 μm or more, even an adherend such as a wafer having a bump height and a relative step can be protected appropriately. When the thickness is 700 μm or less, deformation of the pressure-sensitive adhesive sheet caused by bending can be reduced.
[ base Material ]
The substrate used for the pressure-sensitive adhesive sheet is not particularly limited, and is preferably a resin film. The resin film is suitable for a processing member of an electronic component because it generates less dust than paper and nonwoven fabric, and is therefore preferable because it is easily available. The substrate may be a single-layer film formed of 1 type of resin film or a multilayer film formed by laminating a plurality of resin films.
As the resin film used as the substrate, for example: polyolefin film, vinyl halide polymer film, acrylic resin film, rubber film, cellulose film, polyester film, polycarbonate film, polystyrene film, polyphenylene sulfide film, cycloolefin polymer film, and the like.
Among them, a polyester-based film is preferable from the viewpoint of stably holding the wafer even when the wafer is ground to be extremely thin and from the viewpoint of forming a film with high thickness accuracy, and among the polyester-based films, a polyethylene terephthalate film is preferable from the viewpoint of easy availability and high thickness accuracy.
The thickness of the base material is not particularly limited, but is preferably 10 to 250 μm, and more preferably 20 to 200 μm.
In view of improving the adhesion between the substrate and the intermediate layer, a substrate in which an easy-adhesion layer or the like is further laminated on the surface of the resin film may be used. The base material may contain a filler, a colorant, an antistatic agent, an antioxidant, an organic lubricant, a catalyst, and the like, as long as the effects of the present invention are not impaired.
The substrate may be a transparent substrate or an opaque substrate. Among them, when the adhesive agent constituting the adhesive agent layer and the composition for an intermediate layer are energy ray-curable, the substrate is preferably a substrate that transmits energy rays.
[ adhesive layer ]
Examples of the adhesive for forming the adhesive layer include: acrylic adhesives, rubber adhesives, silicone adhesives, polyvinyl ether adhesives, urethane adhesives, and the like, among which acrylic adhesives are preferable. In addition, as the binder, there can be mentioned: the pressure-sensitive adhesive composition of the present invention is not particularly limited, and may be any of those curable by ultraviolet rays, electron beams, and the like, and may be any of those curable by ultraviolet rays, ultraviolet.
By using an energy ray-curable adhesive, the adhesive sheet can be reliably adhered to a semiconductor wafer before irradiation with energy rays, and an adherend such as a semiconductor wafer can be reliably protected. On the other hand, since the adhesive strength of the adhesive layer can be reduced by irradiation with energy rays when the adhesive sheet is peeled, the adhesive sheet can be peeled from an adherend without damaging the adherend such as a semiconductor wafer and without leaving an adhesive on the adherend.
The energy ray-curable pressure-sensitive adhesive may be an additive type energy ray-curable pressure-sensitive adhesive containing a base polymer such as an acrylic copolymer and an energy ray-curable resin, or may be an internal type energy ray-curable pressure-sensitive adhesive in which a polymer having a radically reactive carbon-carbon double bond in a polymer side chain or a main chain or at a terminal of the main chain is used as a base polymer such as an acrylic copolymer.
The pressure-sensitive adhesive may contain not only a base polymer such as an acrylic copolymer but also a crosslinking agent, a photopolymerization initiator, and the like as necessary.
The thickness of the adhesive layer can be adjusted depending on the difference in height of the surface of an adherend such as a semiconductor wafer, the performance required for the adhesive sheet, etc., and is usually 3 to 200. mu.m, preferably 7 to 150. mu.m, and more preferably 10 to 100. mu.m.
[ Release Material ]
The release agent constituting the pressure-sensitive adhesive sheet and the release agent used in the steps of the production method described below may be a release sheet subjected to a single-sided release treatment, a release sheet subjected to a double-sided release treatment, or the like, and examples thereof include a material obtained by applying a release agent to a substrate used for a release material.
Examples of the base material for release material include: and plastic films such as polyester resin films including polyethylene terephthalate resins, polybutylene terephthalate resins, and polyethylene naphthalate resins, and polyolefin resin films including polypropylene resins and polyethylene resins.
Examples of the release agent include: rubber elastomers such as silicone resins, olefin resins, isoprene resins, and butadiene resins, long-chain alkyl resins, alkyd resins, and fluorine-containing resins.
The thickness of the release agent is not particularly limited, but is preferably 5 to 200 μm, and more preferably 10 to 120 μm.
[ method for producing adhesive sheet ]
The method for producing the pressure-sensitive adhesive sheet of the present invention is not particularly limited, and the pressure-sensitive adhesive sheet can be produced by a known method.
For example, the intermediate layer may be formed by: the composition for an intermediate layer is directly applied to one surface of a substrate to form a coating film, and then, is subjected to curing treatment. In addition, the intermediate layer may also be formed by: the composition for an intermediate layer is directly applied to the release-treated surface of the release material, and cured, and the substrate is bonded to the applied film. In this case, the release material may be appropriately released, for example, after the curing process is completed. In the curing of the intermediate layer, the formed coating film is preferably polymerized and cured by irradiation with energy rays such as ultraviolet rays. In this case, the amount of energy ray irradiation may be determined by the type of energy ray, the thickness of the coating film, and the likeAnd appropriately changed. For example, when ultraviolet light is used, the illuminance of the ultraviolet light to be irradiated is preferably 50 to 500mW/cm2. The amount of ultraviolet light is preferably 100 to 2500mJ/cm2。
The pressure-sensitive adhesive layer can be formed by, for example, directly applying the pressure-sensitive adhesive composition to the intermediate layer formed as described above and drying the applied pressure-sensitive adhesive composition. Alternatively, the pressure-sensitive adhesive composition may be applied to the release-treated surface of the release material, dried to form a pressure-sensitive adhesive layer on the release material, and then the pressure-sensitive adhesive layer on the release material may be bonded to the intermediate layer to form a pressure-sensitive adhesive sheet having the intermediate layer, the pressure-sensitive adhesive layer, and the release material provided on the substrate. Then, the release material in the adhesive sheet may be peeled off as necessary.
In forming the intermediate layer and the pressure-sensitive adhesive layer, an organic solvent may be further added to the composition for an intermediate layer or the pressure-sensitive adhesive composition to prepare a diluted solution of the composition for an intermediate layer or the pressure-sensitive adhesive composition.
Examples of the organic solvent to be used include: methyl ethyl ketone, acetone, ethyl acetate, tetrahydrofuran, dimethyl ethyl ketone, dimethyl ethyl acetate, dimethyl ethyl ketone
Alkanes, cyclohexane, n-hexane, toluene, xylene, n-propanol, isopropanol, and the like.
The organic solvent used in the synthesis of each component contained in the intermediate layer composition or the adhesive composition may be used as it is, or 1 or more organic solvents other than the above may be added.
The composition for an intermediate layer or the adhesive composition can be applied by a known coating method. Examples of the coating method include: spin coating, spray coating, bar coating, blade coating, roll coating, blade coating, die coating, gravure coating, and the like.
When the composition for an intermediate layer or the adhesive composition contains an organic solvent, it is preferable to apply the composition or the adhesive composition and then heat and dry the composition or the adhesive composition.
[ method of Using adhesive sheet ]
The adhesive sheet of the present invention can be used for various applications, and is preferably used as a tape for protecting a semiconductor wafer by being attached to a semiconductor wafer. Further, it is more preferable that the adhesive sheet is adhered to the front surface of the semiconductor wafer and used as a back grinding tape for protecting a circuit formed on the front surface of the wafer in the subsequent back grinding of the wafer.
The pressure-sensitive adhesive sheet of the present invention has good embeddability even when the wafer surface has a level difference due to bumps or the like, and therefore has good wafer surface protective performance. Further, although the adhesive sheet is heated when the adhesive sheet is bonded to the wafer, the intermediate layer does not bleed out even when the adhesive sheet is heated and bonded.
The height of the bumps formed on the wafer surface is not particularly limited, and the thickness of the intermediate layer and the adhesive layer of the adhesive sheet of the present invention can be appropriately selected to improve embeddability into bumps of various heights.
The temperature of the adhesive sheet when the adhesive sheet is attached to the semiconductor wafer is, for example, about 40 to 80 ℃, preferably 50 to 60 ℃.
The pressure-sensitive adhesive sheet is not limited to the back grinding sheet, and may be used for other applications. For example, the adhesive sheet is attached to the back surface of the wafer, and can be used as a dicing sheet for protecting the back surface of the wafer when dicing the wafer.
Examples
The present invention will be described in further detail below with reference to examples, but the present invention is not limited to these examples.
The measurement method and evaluation method in the present invention are as follows.
[ weight average molecular weight (Mw) ]
The measurement was performed under the following conditions using a gel permeation chromatography apparatus (product name "HLC-8020", manufactured by Tosoh corporation), and the value converted to standard polystyrene was used.
(measurement conditions)
A chromatographic column: "TSK guard column HXL-H", "TSK gel GMHXL (. times.2)" "TSK gel G2000 HXL" (all manufactured by Tosoh Corp.)
Column temperature: 40 deg.C
Eluting solvent: tetrahydrofuran (THF)
Flow rate: 1.0mL/min
[ evaluation of embeddability ]
After the release material was peeled off, the adhesive sheets prepared in examples and comparative examples were attached to a bumped wafer (8-inch wafer manufactured by Waltz corporation) having a bump height of 80 μm, a pitch of 200 μm, and a diameter of 100 μm using a laminator RAD-3510F/12 manufactured by Lineko corporation. In the pasting, the laminating table of the apparatus was set at 60 ℃ and the laminating roller was set at 60 ℃. After the lamination, the diameter of the circular voids generated in the vicinity of the bumps was measured from the substrate side using a digital optical microscope (product name "VHX-1000", manufactured by KEYENCE corporation). The smaller the diameter of the void, the higher the embeddability of the bump by the adhesive sheet. The embedding property of the bump was evaluated according to the following criteria. The results are shown in Table 1.
A: the diameter of the voids is less than 120 μm.
B: the diameter of the gap is 120-130 μm.
C: the air bubbles are connected with the adjacent bumps.
[ evaluation of bleeding ]
A25 mm by 50mm adhesive sheet was laminated on a silicon mirror wafer. The same conditions as those used for the embeddability evaluation were used for the lamination conditions. When the laminate was visually observed after lamination, a was assumed to be a when no interlayer resin was oozed out, and C was assumed to be a when oozing was observed.
[ example 1]
(formation of intermediate layer)
A UV curable composition for an intermediate layer was obtained by mixing 40 parts by mass (solid content ratio) of a 2-functional urethane acrylate oligomer (product name "CN 9018", manufactured by Arkema, having a weight average molecular weight of 45000) as a polyfunctional compound, 60 parts by mass (solid content ratio) of octadecyl acrylate (STA) as a crystalline monomer, and 2.0 parts by mass (solid content ratio) of 2,4, 6-trimethylbenzoyldiphenylphosphine oxide (product name "DAROCUR TPO", manufactured by BASF) as a photopolymerization initiator. The composition for an intermediate layer was applied to a release film (product name "SP-PET 381031", manufactured by Linekuke corporation, having a thickness of 38 μm) of polyethylene terephthalate (PET) film type by means of a jet die (fountain die) to form a coating film so that the thickness after curing was 200 μm.
Then, the coating film was cured by irradiating ultraviolet light from the coating film side, and a base material formed of a polyethylene terephthalate (PET) film having a thickness of 50 μm was laminated on the coating film, to form an intermediate layer having a thickness of 200 μm on the base material. The ultraviolet irradiation device used was a conveyor type ultraviolet irradiation device (product name "ECS-401 GX", manufactured by Eyegraphics Co., Ltd.), and the ultraviolet irradiation device used was a high pressure mercury lamp (product name "H04-L41", manufactured by Eyegraphics Co., Ltd.), and the irradiation conditions were 190mW/cm of illuminance at a wavelength of 365nm2Light quantity 113mJ/cm2Ultraviolet irradiation was performed under the conditions of ultraviolet light amount measurement (product name "UVPF-A1", manufactured by Eyegraphics Co., Ltd.).
(formation of adhesive sheet)
An acrylic adhesive coating liquid was prepared by mixing 100 parts by mass (solid content ratio) of an acrylic copolymer obtained by reacting 2-isocyanatoethyl methacrylate at 50 mol% relative to all hydroxyl groups with a copolymer (Mw: 130 ten thousand) obtained by copolymerizing 94% by mass of 2-ethylhexyl acrylate and 6% by mass of 2-hydroxyethyl acrylate, 0.19 parts by mass (solid content ratio) of a TDI-based isocyanate crosslinking agent (product name "BHS-8515", manufactured by TOYOCHEM) and 0.748 parts by mass (solid content ratio) of a photopolymerization initiator (product name "IRGACURE 184", manufactured by BASF) in a solvent.
This was applied to a release film, and the film was dried by heating to obtain a pressure-sensitive adhesive layer having a thickness of 10 μm on the release film. A pressure-sensitive adhesive sheet was obtained by bonding the pressure-sensitive adhesive sheet to the intermediate layer obtained above.
[ example 2]
A pressure-sensitive adhesive sheet was obtained in the same manner as in example 1, except that a liquid butadiene polymer having a plurality of vinyl groups in the side chain (product name "Ricon 154", manufactured by Crayvalley, having a weight-average molecular weight of 5200) was used as the polyfunctional compound.
[ example 3]
The procedure was carried out in the same manner as in example 1 except that a 2-functional polyalkyl acrylate having polymerizable functional groups at both ends (product name "RC 100C", manufactured by kokkiso co., ltd., having a weight average molecular weight of 20000) was used as the polyfunctional compound.
[ examples 4 to 6]
The procedure was carried out in the same manner as in example 1 except that the kind of the polyfunctional compound and the parts by mass of the polyfunctional compound and the monofunctional monomer were changed as shown in table 1.
[ examples 7 to 9]
The procedure of example 1 was repeated except that not only octadecyl acrylate but also isobornyl acrylate (IBXA) or 2-hydroxy-3-phenoxypropyl acrylate (HPPA) were blended as the monofunctional monomer in the composition for the intermediate layer, and the blending amounts of the polyfunctional compound and the monofunctional monomer were changed as shown in table 1.
Comparative example 1
The procedure was carried out in the same manner as in example 1 except that a monofunctional acrylate resin (product name "MM 110C", manufactured by kojic corporation, weight-average molecular weight 9930) was used in place of the 2-functional urethane acrylate shown in table 1.
Comparative example 2
The procedure was carried out in the same manner as in example 1 except that octadecyl acrylate was not blended in the composition for an intermediate layer, and the blending amounts of the 2-functional urethane acrylate oligomer and the photopolymerization initiator were changed as shown in table 1.
Comparative examples 3 and 4
The procedure of example 1 was repeated except that not only octadecyl acrylate but also isobornyl acrylate (IBXA) was added as a monofunctional monomer to the composition for an intermediate layer, and the amounts of the polyfunctional compound and the monofunctional monomer were changed as shown in table 1.
TABLE 1
In table 1, the mass parts of the respective compounds are indicated by the solid content. In addition, the blank column indicates no fit.
The compounds in the respective tables are as follows.
(1) Polyfunctional compound
UA: 2-functional urethane acrylate oligomer (product name "CN 9018", manufactured by Arkema corporation)
PB: liquid butadiene Polymer (product name "Ricon 154", manufactured by Crayvalley Co., Ltd.)
PAA: 2-functional polyalkyl acrylate (product name "RC 100C", manufactured by Kazuki Kaisha)
(2) Monofunctional A
Monofunctional acrylate resin (product name "MM 110C", manufactured by Kabushiki Kaisha)
(3) Monofunctional monomers
STA: octadecyl acrylate
IBXA: acrylic acid isobornyl ester
HPPA: acrylic acid 2-hydroxy-3-phenoxypropyl ester
In each of the above examples, the composition for an intermediate layer contains at least a polyfunctional compound and a crystalline monomer, and the content of the polyfunctional compound is more than 25% by mass and 40% by mass or more of the monofunctional monomer is the crystalline monomer with respect to the monofunctional monomer, whereby the bumps formed on the wafer surface can be embedded appropriately by the adhesive sheet, and bleeding does not occur when the adhesive sheet is attached to the wafer.
In contrast, in comparative example 1, although the composition for an intermediate layer contains a crystalline monomer, a monofunctional acrylate resin is used instead of a polyfunctional compound, and therefore, although the embedding property into the bump is sufficient, the bleeding of the intermediate layer cannot be prevented. In addition, as in comparative examples 2 to 4, when a monofunctional monomer is not blended and the content of the polyfunctional compound is small, the embeddability into the bump is insufficient.
Claims (23)
1. An adhesive sheet comprising, in order: a substrate, an intermediate layer, and an adhesive layer, wherein,
the intermediate layer is obtained by curing an intermediate layer composition containing a polyfunctional compound and a monofunctional monomer, wherein the polyfunctional compound has at least 2 polymerizable functional groups, and the monofunctional monomer at least contains a crystalline monomer having a linear carbon chain with 14-22 carbon atoms,
the composition for an intermediate layer contains the polyfunctional compound in an amount of more than 25 mass% relative to the monofunctional monomer,
the composition for an intermediate layer contains no hot-melt resin or contains less than 2 mass% of a hot-melt resin.
2. The adhesive sheet according to claim 1, wherein 40% by mass or more of the monofunctional monomer is the crystalline monomer.
3. The adhesive sheet according to claim 1, wherein the polyfunctional compound is a polyfunctional oligomer having a weight average molecular weight of 3000 to 60000.
4. The adhesive sheet according to claim 2, wherein the polyfunctional compound is a polyfunctional oligomer having a weight average molecular weight of 3000 to 60000.
5. The adhesive sheet according to claim 1, wherein the polymerizable functional group of the polyfunctional compound is a group having an olefinic double bond.
6. The adhesive sheet according to claim 2, wherein the polymerizable functional group of the polyfunctional compound is a group having an olefinic double bond.
7. The adhesive sheet according to claim 3, wherein the polymerizable functional group of the polyfunctional compound is a group having an olefinic double bond.
8. The adhesive sheet according to claim 4, wherein the polymerizable functional group of the polyfunctional compound is a group having an olefinic double bond.
9. The adhesive sheet according to any one of claims 1 to 8, wherein the polyfunctional compound is at least 1 selected from the group consisting of a urethane (meth) acrylate oligomer, an acrylic polymer, and a butadiene-based polymer.
10. The adhesive sheet according to any one of claims 1 to 8, wherein the crystalline monomer is contained in an amount of 25 to 70 mass% based on the total amount of the composition for an intermediate layer.
11. The adhesive sheet according to claim 9, wherein the crystalline monomer is contained in an amount of 25 to 70 mass% based on the total amount of the composition for an intermediate layer.
12. The adhesive sheet according to any one of claims 1 to 8, wherein the composition for an intermediate layer is of an energy ray-curable type.
13. The adhesive sheet according to claim 9, wherein the composition for an intermediate layer is an energy ray-curable type.
14. The adhesive sheet according to claim 10, wherein the composition for an intermediate layer is an energy ray-curable type.
15. The adhesive sheet according to any one of claims 1 to 8, wherein the thickness of the intermediate layer is 150 to 700 μm.
16. The adhesive sheet according to claim 9, wherein the thickness of the intermediate layer is 150 to 700 μm.
17. The adhesive sheet according to claim 10, wherein the thickness of the intermediate layer is 150 to 700 μm.
18. The adhesive sheet according to claim 12, wherein the thickness of the intermediate layer is 150 to 700 μm.
19. The adhesive sheet according to any one of claims 1 to 8, which is a semiconductor wafer protection tape.
20. The adhesive sheet according to claim 9, which is a semiconductor wafer protection tape.
21. The adhesive sheet according to claim 10, which is a semiconductor wafer protection tape.
22. The adhesive sheet according to claim 12, which is a semiconductor wafer protection tape.
23. The adhesive sheet according to claim 15, which is a semiconductor wafer protection tape.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014-260561 | 2014-12-24 | ||
| JP2014260561 | 2014-12-24 | ||
| PCT/JP2015/085354 WO2016104322A1 (en) | 2014-12-24 | 2015-12-17 | Pressure-sensitive adhesive sheet |
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| Publication Number | Publication Date |
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| CN107001872A CN107001872A (en) | 2017-08-01 |
| CN107001872B true CN107001872B (en) | 2020-04-07 |
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| CN201580064807.4A Active CN107001872B (en) | 2014-12-24 | 2015-12-17 | Adhesive sheet |
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| JP (1) | JP6717484B2 (en) |
| KR (1) | KR102460037B1 (en) |
| CN (1) | CN107001872B (en) |
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| JP7340323B2 (en) * | 2017-12-27 | 2023-09-07 | 株式会社レゾナック・パッケージング | Exterior material for power storage devices and power storage devices |
| KR20210143153A (en) * | 2019-03-22 | 2021-11-26 | 린텍 가부시키가이샤 | Adhesive sheet for work processing and manufacturing method therefor |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1254743A (en) * | 1998-11-20 | 2000-05-31 | 琳得科株式会社 | Pressure-sensitive adhesive piece and its application method |
| JP2013087131A (en) * | 2011-10-13 | 2013-05-13 | Lintec Corp | Pressure-sensitive adhesive sheet and method for using the same |
| CN103320033A (en) * | 2012-03-23 | 2013-09-25 | 古河电气工业株式会社 | Bonding belt used for protecting semiconductor wafer surface |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP4369584B2 (en) * | 2000-01-21 | 2009-11-25 | 日東電工株式会社 | Adhesive sheet for semiconductor wafer holding protection |
| JP4413551B2 (en) * | 2003-07-28 | 2010-02-10 | 古河電気工業株式会社 | Adhesive tape for semiconductor wafer surface protection |
| JP2006282794A (en) * | 2005-03-31 | 2006-10-19 | Furukawa Electric Co Ltd:The | Adhesive tape for wafer dicing |
-
2015
- 2015-12-17 CN CN201580064807.4A patent/CN107001872B/en active Active
- 2015-12-17 WO PCT/JP2015/085354 patent/WO2016104322A1/en active Application Filing
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- 2015-12-17 KR KR1020177007114A patent/KR102460037B1/en active IP Right Grant
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1254743A (en) * | 1998-11-20 | 2000-05-31 | 琳得科株式会社 | Pressure-sensitive adhesive piece and its application method |
| JP2013087131A (en) * | 2011-10-13 | 2013-05-13 | Lintec Corp | Pressure-sensitive adhesive sheet and method for using the same |
| CN103320033A (en) * | 2012-03-23 | 2013-09-25 | 古河电气工业株式会社 | Bonding belt used for protecting semiconductor wafer surface |
Also Published As
| Publication number | Publication date |
|---|---|
| KR102460037B1 (en) | 2022-10-27 |
| JP6717484B2 (en) | 2020-07-01 |
| CN107001872A (en) | 2017-08-01 |
| WO2016104322A1 (en) | 2016-06-30 |
| KR20170101183A (en) | 2017-09-05 |
| TWI697537B (en) | 2020-07-01 |
| JPWO2016104322A1 (en) | 2017-10-05 |
| TW201629174A (en) | 2016-08-16 |
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