CN113214765A - Adhesive composition and adhesive sheet using the same - Google Patents
Adhesive composition and adhesive sheet using the same Download PDFInfo
- Publication number
- CN113214765A CN113214765A CN202110074380.3A CN202110074380A CN113214765A CN 113214765 A CN113214765 A CN 113214765A CN 202110074380 A CN202110074380 A CN 202110074380A CN 113214765 A CN113214765 A CN 113214765A
- Authority
- CN
- China
- Prior art keywords
- adhesive
- meth
- acrylate
- ultraviolet
- pressure
- 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.)
- Pending
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- 239000000853 adhesive Substances 0.000 title claims abstract description 154
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 154
- 239000000203 mixture Substances 0.000 title claims abstract description 69
- 239000010410 layer Substances 0.000 claims abstract description 65
- 125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 27
- 239000012790 adhesive layer Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 16
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 15
- 229910052710 silicon Inorganic materials 0.000 claims description 15
- 239000010703 silicon Substances 0.000 claims description 14
- 239000004642 Polyimide Substances 0.000 claims description 10
- 229920001721 polyimide Polymers 0.000 claims description 10
- 238000000227 grinding Methods 0.000 claims description 8
- 238000012545 processing Methods 0.000 claims description 8
- ZMDDERVSCYEKPQ-UHFFFAOYSA-N Ethyl (mesitylcarbonyl)phenylphosphinate Chemical group C=1C=CC=CC=1P(=O)(OCC)C(=O)C1=C(C)C=C(C)C=C1C ZMDDERVSCYEKPQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004065 semiconductor Substances 0.000 claims description 6
- 239000004820 Pressure-sensitive adhesive Substances 0.000 abstract description 78
- 239000000463 material Substances 0.000 abstract description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 84
- 239000000178 monomer Substances 0.000 description 59
- 239000003431 cross linking reagent Substances 0.000 description 39
- -1 polyimide Chemical compound 0.000 description 36
- 235000012431 wafers Nutrition 0.000 description 29
- 229920005989 resin Polymers 0.000 description 22
- 239000011347 resin Substances 0.000 description 22
- 229920000178 Acrylic resin Polymers 0.000 description 16
- 239000004925 Acrylic resin Substances 0.000 description 16
- 239000011254 layer-forming composition Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 239000003999 initiator Substances 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 14
- 239000010949 copper Substances 0.000 description 14
- 125000000524 functional group Chemical group 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 10
- 229920000058 polyacrylate Polymers 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 8
- 229940059574 pentaerithrityl Drugs 0.000 description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229920005601 base polymer Polymers 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 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 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 239000002216 antistatic agent Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- ZVEMLYIXBCTVOF-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-3-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC(C(C)(C)N=C=O)=C1 ZVEMLYIXBCTVOF-UHFFFAOYSA-N 0.000 description 2
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- VHFGGWSXGDWGOY-UHFFFAOYSA-N 2-isocyanatoethyl 2-methylprop-2-enoate 5-isocyanato-2-methylpent-2-enoic acid Chemical compound N(=C=O)CCC=C(C(=O)O)C.C(C(=C)C)(=O)OCCN=C=O VHFGGWSXGDWGOY-UHFFFAOYSA-N 0.000 description 2
- OZJJSQVLXHKGHV-UHFFFAOYSA-N 2-isocyanoethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC[N+]#[C-] OZJJSQVLXHKGHV-UHFFFAOYSA-N 0.000 description 2
- JEHFRMABGJJCPF-UHFFFAOYSA-N 2-methylprop-2-enoyl isocyanate Chemical compound CC(=C)C(=O)N=C=O JEHFRMABGJJCPF-UHFFFAOYSA-N 0.000 description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 230000000740 bleeding effect Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002500 ions Chemical class 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 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 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000001400 nonyl 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])[H] 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 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
- 125000002889 tridecyl 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])[H] 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- 125000002948 undecyl 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])[H] 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- IAUGBVWVWDTCJV-UHFFFAOYSA-N 1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound CCC(S(O)(=O)=O)NC(=O)C=C IAUGBVWVWDTCJV-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- UBPXWZDJZFZKGH-UHFFFAOYSA-N 1-ethenyl-3-methylpyrrolidin-2-one Chemical compound CC1CCN(C=C)C1=O UBPXWZDJZFZKGH-UHFFFAOYSA-N 0.000 description 1
- BMZZOWWYEBTMBX-UHFFFAOYSA-N 1-ethyl-3-methylidenepyrrolidine-2,5-dione Chemical compound CCN1C(=O)CC(=C)C1=O BMZZOWWYEBTMBX-UHFFFAOYSA-N 0.000 description 1
- QSWFISOPXPJUCT-UHFFFAOYSA-N 1-methyl-3-methylidenepyrrolidine-2,5-dione Chemical compound CN1C(=O)CC(=C)C1=O QSWFISOPXPJUCT-UHFFFAOYSA-N 0.000 description 1
- NQDOCLXQTQYUDH-UHFFFAOYSA-N 1-propan-2-ylpyrrole-2,5-dione Chemical compound CC(C)N1C(=O)C=CC1=O NQDOCLXQTQYUDH-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- WULAHPYSGCVQHM-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethanol Chemical compound OCCOCCOC=C WULAHPYSGCVQHM-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-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
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
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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
- 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
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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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
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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
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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
- C09J7/00—Adhesives in the form of films or foils
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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
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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
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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
- 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
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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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
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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
- 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
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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
- C09J2467/00—Presence of polyester
- C09J2467/006—Presence of polyester in the substrate
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2221/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof covered by H01L21/00
- H01L2221/67—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere
- H01L2221/683—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L2221/68304—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
- H01L2221/68327—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support used during dicing or grinding
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- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Power Engineering (AREA)
- Physics & Mathematics (AREA)
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Abstract
Provided are an adhesive composition and an adhesive sheet using the same. An ultraviolet-curable pressure-sensitive adhesive composition which has excellent adhesion to an adherend before ultraviolet irradiation and excellent peelability after ultraviolet irradiation regardless of the composition and structure of the adherend surface. The ultraviolet-curable adhesive composition of the present invention comprises an ultraviolet-curable adhesive and alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate. The pressure-sensitive adhesive sheet of the present invention comprises a pressure-sensitive adhesive layer and a base material layer, wherein the pressure-sensitive adhesive layer is formed from the above-mentioned ultraviolet-curable pressure-sensitive adhesive composition.
Description
Technical Field
The present invention relates to an adhesive composition and an adhesive sheet using the same.
Background
Large scale integrated circuits (LSIs) have been used in various applications such as personal computers, smart phones, and automobiles. In the production of integrated circuits such as LSIs, an adhesive sheet is used to protect the surface during processing. In recent years, miniaturization and high functionality of LSIs have been advanced, and the surface structure of a wafer has become complicated. For example, the wafer surface is formed of various materials such as metal wiring such as copper and aluminum, and resin such as polyimide, and the structure of the wafer surface is also complicated by solder bumps and the like. Therefore, there is a case where a difference in adhesive force occurs due to the material and structure of the wafer surface, and thereby residual glue is generated. In order to prevent adhesive residue, adhesive sheets using an ultraviolet-curable adhesive have been proposed (patent documents 1 and 2). When an ultraviolet-curable adhesive is used, there is also a case where a difference in adhesive force occurs after ultraviolet irradiation due to a difference in composition and structure of the wafer surface.
In addition, various methods have been proposed as a wafer processing technique. For example, a technique of introducing a slit on a wafer with a laser, Grinding the back surface to reduce the thickness, and singulating the wafer (step Dicing Before Grinding, SDBG, Stealth Dicing and polishing) has been proposed (for example, patent document 3). Although SDBG can reduce the load on semiconductor chips, it is necessary to use an adhesive sheet having an adhesive force capable of holding chips after singulation during processing. In the case of a wafer having a complicated surface, a difference in adhesive force is likely to occur, and thus it is sometimes difficult to appropriately hold the singulated chips. Therefore, an adhesive composition capable of exerting adhesive force without being affected by the material and structure of the wafer surface is required.
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent publication No. 6-49420
Patent document 2: japanese patent laid-open publication No. 62-153376
Patent document 3: japanese patent laid-open publication No. 2004-111428
Disclosure of Invention
The problem to be solved by the inventionQuestion (I)
The present invention has been made to solve the above conventional problems, and provides an ultraviolet-curable pressure-sensitive adhesive composition having excellent adhesion to an adherend before ultraviolet irradiation and excellent releasability after ultraviolet irradiation, regardless of the composition and structure of the surface of the adherend; and an adhesive sheet using the adhesive composition.
Means for solving the problems
In one embodiment, the ultraviolet curable adhesive composition of the present invention comprises an ultraviolet curable adhesive and an alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate.
In one embodiment, the alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate is ethyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate.
Another aspect of the present invention provides an adhesive sheet. The adhesive sheet comprises a substrate and an adhesive layer. The pressure-sensitive adhesive layer is formed from the ultraviolet-curable pressure-sensitive adhesive composition.
In one embodiment, the adhesive sheet comprises at least 1 adhesive layer as described above.
In one embodiment, the ratio of the polyimide adhesive force to the silicon adhesive force of the pressure-sensitive adhesive layer after the ultraviolet irradiation is 2 or less.
In one embodiment, the adhesive sheet further comprises an intermediate layer.
In one embodiment, the intermediate layer includes the same alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate as the adhesive layer.
In one embodiment, the adhesive sheet is used in a semiconductor wafer processing process.
In one embodiment, the adhesive sheet is used as a back grinding sheet.
ADVANTAGEOUS EFFECTS OF INVENTION
The ultraviolet-curable adhesive composition of the present invention comprises an ultraviolet-curable adhesive and alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate. Alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate can function as a photopolymerization initiator. The ultraviolet-curable pressure-sensitive adhesive composition of the present invention can exhibit excellent adhesive strength before ultraviolet irradiation even when the surface of an adherend has portions having different compositions (for example, inorganic substances such as metals, organic substances such as resins, etc.). Further, since the adhesive composition has excellent followability to irregularities, it can exhibit excellent adhesive force even when the structure (for example, irregularities) of the surface of an adherend is complicated. The ultraviolet-curable pressure-sensitive adhesive composition can exhibit light peelability without being affected by the composition and structure of the surface of an adherend after ultraviolet irradiation. Therefore, when the composition is used as a composition for forming a pressure-sensitive adhesive layer of a pressure-sensitive adhesive sheet, a pressure-sensitive adhesive sheet can be obtained which can achieve both excellent adhesive strength to an adherend surface and light peelability. The adhesive sheet can be suitably used in the process of processing a semiconductor wafer which may have a complicated composition and structure.
Drawings
Fig. 1 is a schematic cross-sectional view of a pressure-sensitive adhesive sheet according to an embodiment of the present invention.
Description of the reference numerals
10 base material
20 adhesive layer
100 adhesive sheet
Detailed Description
A. Ultraviolet-curable adhesive composition
In one embodiment, the ultraviolet curable adhesive composition of the present invention comprises an ultraviolet curable adhesive and an alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate. Alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate can function as a photopolymerization initiator. When the alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate is contained as a photopolymerization initiator, excellent adhesive force can be exhibited even before ultraviolet irradiation when the adherend surface has portions having different compositions (for example, inorganic substances such as metals, organic substances such as resins, etc.). Further, since the adhesive composition has excellent followability to irregularities, it can exhibit excellent adhesive force even when the structure (for example, irregularities) of the surface of an adherend is complicated. The ultraviolet-curable pressure-sensitive adhesive composition can exhibit light peelability without decreasing the adhesive strength after ultraviolet irradiation, regardless of the composition and structure of the surface of the adherend. Therefore, adhesive residue on the surface of the adherend can be prevented.
A-1. ultraviolet-curable adhesive
As the ultraviolet-curable adhesive, any suitable adhesive can be used. For example, the adhesive may be one obtained by adding an ultraviolet-curable monomer and/or oligomer to any suitable adhesive such as an acrylic adhesive, a rubber adhesive, a silicone adhesive, or a polyvinyl ether adhesive, or may be one obtained by using a polymer having a carbon-carbon double bond in a side chain or a terminal as a base polymer.
As the ultraviolet-curable monomer and oligomer, any suitable monomer or oligomer can be used. Examples of the ultraviolet-curable monomer include urethane (meth) acrylate, trimethylolpropane tri (meth) acrylate, tetramethylolmethane tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol monohydroxypenta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and 1, 4-butanediol di (meth) acrylate. Examples of the radiation curable oligomer include urethane oligomers, polyether oligomers, polyester oligomers, polycarbonate oligomers, and polybutadiene oligomers. The oligomer preferably has a molecular weight of about 100 to 30000. The monomer and oligomer may be used alone or in combination of two or more.
The monomers and/or oligomers may be used in any suitable amount depending on the type of binder used. For example, the amount is preferably 5 to 500 parts by weight, more preferably 40 to 150 parts by weight, based on 100 parts by weight of the base polymer constituting the binder.
When a binder using a polymer having a carbon-carbon double bond in a side chain or a terminal is used, a polymer having a polymerizable carbon-carbon double bond in a side chain or a terminal and having a binding property is used as a base polymer. Examples of such polymers include polymers having polymerizable carbon-carbon double bonds introduced into resins such as (meth) acrylic resins, vinyl alkyl ether resins, silicone resins, polyester resins, polyamide resins, urethane resins, and styrene-diene block copolymers. It is preferable to use a (meth) acrylic polymer obtained by introducing a polymerizable carbon-carbon double bond into a (meth) acrylic resin. By using the (meth) acrylic polymer, a pressure-sensitive adhesive sheet can be obtained in which the storage modulus and tensile modulus of the pressure-sensitive adhesive layer are easily adjusted and which has an excellent balance between adhesive strength and peelability. In addition, "(meth) acryl" means acryl and/or methacryl.
As the (meth) acrylic resin, any suitable (meth) acrylic resin can be used. Examples of the (meth) acrylic resin include: a polymer obtained by polymerizing a monomer composition containing one or more esters of acrylic acid or methacrylic acid having a straight-chain or branched-chain alkyl group.
The linear alkyl group or branched alkyl group is preferably an alkyl group having 30 or less carbon atoms, more preferably an alkyl group having 1 to 20 carbon atoms, and still more preferably an alkyl group having 4 to 18 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, an isobutyl group, a pentyl group, an isopentyl group, a hexyl group, a heptyl group, a cyclohexyl group, a 2-ethylhexyl group, an octyl group, an isooctyl group, a nonyl group, an isononyl group, a decyl group, an isodecyl group, an undecyl group, a lauryl group, a tridecyl group, a tetradecyl group, a stearyl group, an octadecyl group, and a dodecyl group.
The monomer composition for forming the (meth) acrylic resin may contain any suitable other monomer. Examples of the other monomers include: carboxyl group-containing monomers such as acrylic acid, methacrylic acid, carboxyethyl acrylate, carboxypentyl acrylate, itaconic acid, maleic acid, fumaric acid, and crotonic acid; anhydride monomers such as maleic anhydride and itaconic anhydride; hydroxyl group-containing monomers such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, 12-hydroxylauryl (meth) acrylate, 4-hydroxymethylcyclohexyl) methyl acrylate, 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, and diethylene glycol monovinyl ether; sulfonic acid group-containing monomers such as styrenesulfonic acid, allylsulfonic acid, 2- (meth) acrylamido-2-methylpropanesulfonic acid, (meth) acrylamidopropanesulfonic acid, sulfopropyl (meth) acrylate, and (meth) acryloyloxynaphthalenesulfonic acid; a monomer having a functional group such as a phosphoric acid group-containing monomer such as 2-hydroxyethylacryloyl phosphate. By including a monomer having a functional group, a (meth) acrylic resin in which a polymerizable carbon-carbon double bond is easily introduced can be obtained. The content of the functional group-containing monomer is preferably 4 to 30 parts by weight, more preferably 6 to 20 parts by weight, based on 100 parts by weight of the total monomers in the monomer composition.
As the other monomer, a polyfunctional monomer may be used. By using a polyfunctional monomer, the cohesive force, heat resistance, adhesiveness, and the like of the adhesive can be improved. In addition, since the low-molecular-weight component in the pressure-sensitive adhesive layer is reduced, a pressure-sensitive adhesive sheet which is less likely to stain an adherend can be obtained. Examples of the polyfunctional monomer include hexanediol (meth) acrylate, (poly) ethylene glycol di (meth) acrylate, (poly) propylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, pentaerythritol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, epoxy (meth) acrylate, polyester (meth) acrylate, and urethane (meth) acrylate. The content of the polyfunctional monomer is preferably 1 to 100 parts by weight, more preferably 5 to 50 parts by weight, based on 100 parts by weight of all the monomers in the monomer composition.
The weight average molecular weight of the (meth) acrylic resin is preferably 30 ten thousand or more, more preferably 50 ten thousand or more, and further preferably 80 to 300 ten thousand. Within such a range, bleeding of low-molecular-weight components can be prevented, and a pressure-sensitive adhesive sheet with low staining properties can be obtained. The molecular weight distribution (weight average molecular weight/number average molecular weight) of the (meth) acrylic resin is preferably 1 to 20, more preferably 3 to 10. By using a (meth) acrylic resin having a narrow molecular weight distribution, bleeding of low molecular weight components can be prevented, and a pressure-sensitive adhesive sheet having low staining properties can be obtained. The weight average molecular weight and the number average molecular weight can be determined by gel permeation chromatography (solvent: tetrahydrofuran, polystyrene equivalent).
The polymer having a polymerizable carbon-carbon double bond in a side chain or a terminal thereof can be obtained by any suitable method. For example, the resin can be obtained by reacting a compound having a polymerizable carbon-carbon double bond with a resin obtained by any suitable polymerization method (for example, condensation reaction or addition reaction). Specifically, when a (meth) acrylic resin is used, the polymer can be obtained by polymerizing a (meth) acrylic resin (copolymer) containing a constituent unit derived from a monomer having an arbitrary appropriate functional group in an arbitrary appropriate solvent, and then reacting the functional group of the acrylic resin with a compound having a polymerizable carbon-carbon double bond capable of reacting with the functional group. The amount of the compound having a polymerizable carbon-carbon double bond to be reacted is preferably 4 to 30 parts by weight, more preferably 4 to 20 parts by weight, based on 100 parts by weight of the resin. As the solvent, any suitable solvent can be used, and examples thereof include various organic solvents such as ethyl acetate, methyl ethyl ketone, and toluene.
When the resin is reacted with the compound having a polymerizable carbon-carbon double bond as described above, the resin and the compound having a polymerizable carbon-carbon double bond preferably have functional groups capable of reacting with each other. Examples of the combination of the functional groups include carboxyl group/epoxy group, carboxyl group/aziridine group, hydroxyl group/isocyanate group, and the like. Among these combinations of functional groups, a combination of a hydroxyl group and an isocyanate group is preferable from the viewpoint of easiness of tracing the reaction.
Examples of the compound having a polymerizable carbon-carbon double bond include 2-isocyanoethyl methacrylate, methacryloyl isocyanate, 2-methacryloyloxyethyl isocyanate (2-isocyanatoethyl methacrylate), and m-isopropenyl- α, α -dimethylbenzyl isocyanate.
A-2 alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate
The alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate acts as a photopolymerization initiator, and the ultraviolet-curable adhesive can be cured by irradiation with ultraviolet rays, thereby reducing the adhesive force. Alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate is a liquid at room temperature. Therefore, the dispersion in the adhesive composition is more uniform, and an adhesive layer in which the photopolymerization initiator is more uniformly dispersed is formed. This suppresses unevenness of the curing reaction of the pressure-sensitive adhesive layer after the ultraviolet irradiation, and exhibits light peelability, and as a result, can prevent adhesive residue on the surface of the adherend.
As the alkyl group of the alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate, any suitable alkyl group can be exemplified. The alkyl group having 1 to 5 carbon atoms is preferable, and a methyl group or an ethyl group is more preferable. That is, as the alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate, methyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate or ethyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate may be preferably used, and ethyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate may be more preferably used. By using such alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate, an ultraviolet curable adhesive composition in which the photopolymerization initiator is dispersed more uniformly can be obtained. The alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate may be used alone or in combination of two or more.
Alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate is used in any suitable amount. The content of the alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate is preferably 0.5 to 10 parts by weight, and more preferably 1 to 7 parts by weight, based on 100 parts by weight of the ultraviolet-curable adhesive.
A-3. crosslinking agent
The ultraviolet-curable adhesive composition preferably further contains a crosslinking agent. Examples of the crosslinking agent include isocyanate crosslinking agents, epoxy crosslinking agents, oxazoline crosslinking agents, aziridine crosslinking agents, melamine crosslinking agents, peroxide crosslinking agents, urea crosslinking agents, metal alkoxide crosslinking agents, metal chelate crosslinking agents, metal salt crosslinking agents, carbodiimide crosslinking agents, and amine crosslinking agents.
In one embodiment, an isocyanate-based crosslinking agent is preferably used. The isocyanate-based crosslinking agent is preferable from the viewpoint of being capable of reacting with various functional groups. Specific examples of the isocyanate-based crosslinking agent include: lower aliphatic polyisocyanates such as butylene diisocyanate and hexamethylene diisocyanate; alicyclic isocyanates such as cyclopentylene diisocyanate, cyclohexylene diisocyanate and isophorone diisocyanate; aromatic isocyanates such as 2, 4-tolylene diisocyanate, 4' -diphenylmethane diisocyanate, and xylylene diisocyanate; isocyanate adducts such as trimethylolpropane/tolylene diisocyanate trimer adduct (specifically, product name "Coronate L" manufactured by tokyo corporation), trimethylolpropane/hexamethylene diisocyanate trimer adduct (specifically, product name "Coronate HL" manufactured by japan polyurethane industries), isocyanurate body of hexamethylene diisocyanate (specifically, product name "Coronate HX" manufactured by japan polyurethane industries), and the like; and the like. It is preferable to use a crosslinking agent having 3 or more isocyanate groups.
The amount of the crosslinking agent can be adjusted to any suitable amount. For example, the amount is preferably 0.005 to 20 parts by weight, more preferably 0.02 to 10 parts by weight, based on 100 parts by weight of the ultraviolet-curable pressure-sensitive adhesive.
A-4. other ingredients
The ultraviolet curable adhesive composition may further contain any suitable additive. Examples of the additives include a polymerization initiator other than alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate, an active energy ray polymerization accelerator, a radical scavenger, a tackifier, a plasticizer (e.g., a trimellitate-based plasticizer and a pyromellitate-based plasticizer), a pigment, a dye, a filler, an antioxidant, a conductive material, an antistatic agent, an ultraviolet absorber, a light stabilizer, a release control agent, a softening agent, a surfactant, a flame retardant, and an antioxidant. Other additives may be used in any suitable amount.
B. Adhesive sheet
B-1 summary of adhesive sheets
Fig. 1 is a schematic cross-sectional view of a pressure-sensitive adhesive sheet according to an embodiment of the present invention. The pressure-sensitive adhesive sheet 100 illustrated in the figure includes a substrate 10 and a pressure-sensitive adhesive layer 20 disposed on one surface of the substrate 10. The pressure-sensitive adhesive layer is formed from the ultraviolet-curable pressure-sensitive adhesive composition. In actual use, a separator is temporarily bonded in a peelable manner to the adhesive layer 20 until the time of use, to suitably protect the adhesive layer 20. In one embodiment, the adhesive sheet 100 may be formed with an intermediate layer (not shown) between the substrate 10 and the adhesive layer 20.
In another embodiment of the present invention, the pressure-sensitive adhesive layer is composed of two layers, and the pressure-sensitive adhesive sheet includes a substrate, a 1 st pressure-sensitive adhesive layer, and a 2 nd pressure-sensitive adhesive layer (not shown) in this order.
The thickness of the adhesive sheet can be set to any suitable range. Preferably 5 to 1000. mu.m, more preferably 20 to 300. mu.m, and still more preferably 50 to 300. mu.m.
B-2. base Material
The base material can be made of any suitable resin. Specific examples of the resin constituting the base material include polyester resins (polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, polybutylene naphthalate, and the like), ethylene-vinyl acetate copolymers, ethylene-methyl methacrylate copolymers, polyolefin resins (polyethylene, polypropylene, ethylene-propylene copolymers, and the like), polyvinyl alcohol, polyvinylidene chloride, polyvinyl chloride, vinyl chloride-vinyl acetate copolymers, polyvinyl acetate, polyamides, polyimides, celluloses, fluorine resins, polyethers, polystyrene resins (polystyrene and the like), polycarbonates, polyether sulfones, and the like.
The substrate may further contain other components within a range not impairing the effects of the present invention. Examples of the other components include antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, and antistatic agents. The kind and the amount of the other components used may be any appropriate amount according to the purpose.
The thickness of the substrate can be set to any suitable value. The thickness of the substrate is preferably 10 to 200. mu.m, more preferably 20 to 150. mu.m.
The modulus of elasticity of the substrate can be set to any suitable value. The elastic modulus of the base material is preferably 50MPa to 6000MPa, more preferably 70MPa to 5000 MPa. When the elastic modulus is in the above range, a pressure-sensitive adhesive sheet that can appropriately follow the unevenness of the surface of an adherend can be obtained.
B-3 adhesive layer
The pressure-sensitive adhesive layer can be formed using the above-described ultraviolet-curable pressure-sensitive adhesive composition. The ultraviolet-curable pressure-sensitive adhesive composition can exhibit excellent adhesive force before ultraviolet irradiation without being affected by the composition and structure of the surface of an adherend. Further, after the ultraviolet irradiation, the adhesive layer can exhibit a light peelability by suppressing unevenness of the curing reaction of the adhesive layer. As a result, adhesive residue on the surface of the adherend can be prevented. Further, the pressure-sensitive adhesive layer formed using the ultraviolet-curable pressure-sensitive adhesive composition is soft and has excellent conformability even when irregularities are present on the surface of an adherend. Therefore, even an adherend having irregularities on the surface can exhibit good adhesion.
The thickness of the adhesive layer can be set to any suitable value. The thickness of the pressure-sensitive adhesive layer is preferably 1 to 50 μm, more preferably 2 to 20 μm, and still more preferably 3 to 10 μm.
The pressure-sensitive adhesive layer may be 1 layer or 2 or more layers. When the pressure-sensitive adhesive layer is 2 or more layers, the pressure-sensitive adhesive layer may contain at least 1 layer of the above-mentioned ultraviolet-curable pressure-sensitive adhesive composition. When the pressure-sensitive adhesive layer is 2 or more layers, it is preferable to form the pressure-sensitive adhesive layer formed of the ultraviolet-curable pressure-sensitive adhesive composition on the surface of the pressure-sensitive adhesive sheet that is in contact with the adherend. The pressure-sensitive adhesive layer not containing the above-mentioned ultraviolet-curable pressure-sensitive adhesive composition may be formed of any suitable pressure-sensitive adhesive composition. The adhesive composition may be an ultraviolet-curable adhesive or a pressure-sensitive adhesive.
The ratio of the polyimide adhesion to the silicon adhesion (polyimide adhesion/silicon adhesion, hereinafter also referred to as PI adhesion/Si adhesion) after ultraviolet irradiation of the pressure-sensitive adhesive layer is preferably 2 or less, more preferably 1.9 or less, and even more preferably 1.8 or less. When the ratio of the polyimide adhesive force to the silicon adhesive force is in the above range, the adhesive residue on the adherend can be prevented when the pressure-sensitive adhesive sheet is peeled off. In the present specification, the polyimide adhesion and the silicon adhesion after ultraviolet irradiation refer to: the adhesive force obtained was measured by the method described in the examples described later.
The ratio of the copper adhesion to the silicon adhesion (copper (Cu) adhesion/silicon adhesion, hereinafter also referred to as Cu adhesion/Si adhesion) of the pressure-sensitive adhesive layer after ultraviolet irradiation is preferably 1.9 or less, more preferably 1.8 or less, and even more preferably 1.7 or less. When the ratio of the copper adhesive force to the silicon adhesive force is in the above range, the adhesive residue on the adherend can be prevented when the adhesive sheet is peeled off. In the present specification, the copper adhesion and the silicon adhesion after ultraviolet irradiation refer to: the adhesive force obtained was measured by the method described in the examples described later.
The ratio of the adhesive force to organic substances to the adhesive force to silicon wafers (for example, PI adhesive force/Si adhesive force) and the ratio of the adhesive force to inorganic substances to the adhesive force to silicon wafers (for example, Cu adhesive force/Si adhesive force) of the adhesive layer after ultraviolet irradiation are preferably the same. By making the above ratio equal, the pressure-sensitive adhesive sheet can be easily peeled even when the composition of the adherend surface is complicated. Specifically, the ratio of the PI adhesion/Si adhesion to the Cu adhesion/Si adhesion ((PI adhesion/Si adhesion)/(Cu adhesion/Si adhesion)) is, for example, 0.75 to 1.10, and is preferably as close to 1 (that is, the same value).
The elastic modulus of the pressure-sensitive adhesive layer before ultraviolet irradiation is preferably 0.05 to 2.0MPa, more preferably 0.075 to 1.0MPa, still more preferably 0.08 to 0.80MPa, and particularly preferably 0.1 to less than 0.7 MPa. Within such a range, a pressure-sensitive adhesive sheet having a sufficient adhesive force for holding an adherend can be obtained. In the present specification, the elastic modulus of the adhesive layer means: the obtained elastic modulus (young's modulus) was measured by the following method.
The adhesive layer-forming composition was applied to a separator so as to have a coating thickness of 5 μm, and dried at 130 ℃ for 2 minutes. Next, a rod-shaped sample was prepared by rolling up only the adhesive layer after application and drying from the end, and the thickness (cross-sectional area) was measured. The initial slope (Young's modulus) of the obtained sample when it was stretched in a tensile tester (trade name "AG-IS" manufactured by SHIMADZU) under conditions of an inter-chuck distance of 10mm, a stretching speed of 50 mm/min and room temperature was taken as the elastic modulus.
The elastic modulus of the pressure-sensitive adhesive layer after ultraviolet irradiation is preferably 1MPa or more, more preferably 5MPa or more, and still more preferably 10MPa or more. Within such a range, a pressure-sensitive adhesive sheet having excellent peelability after a predetermined step (for example, a back grinding step) can be obtained. The elastic modulus of the pressure-sensitive adhesive layer after ultraviolet irradiation is, for example, 1000MPa or less, preferably 500MPa or less, and more preferably 400MPa or less.
B-4. intermediate layer
In one embodiment, the adhesive sheet has an intermediate layer between the substrate and the adhesive layer. The intermediate layer can be formed of any suitable material. The intermediate layer can be formed of a resin such as an acrylic resin, a polyethylene resin, an ethylene-vinyl alcohol copolymer, an ethylene-vinyl acetate resin, or an ethylene-methyl methacrylate resin, or a binder. In the case of forming the intermediate layer with an adhesive, the adhesive may be an ultraviolet-curable adhesive or a pressure-sensitive adhesive.
In one embodiment, the intermediate layer is formed from an intermediate layer-forming composition comprising a (meth) acrylic polymer. The (meth) acrylic polymer preferably contains a constituent derived from an alkyl (meth) acrylate. Examples of the alkyl (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, pentyl (meth) acrylate, isoamyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, and mixtures thereof, C1-C20 alkyl (meth) acrylates such as pentadecyl (meth) acrylate, hexadecyl (meth) acrylate, heptadecyl (meth) acrylate, octadecyl (meth) acrylate, nonadecyl (meth) acrylate, and eicosyl (meth) acrylate.
The (meth) acrylic polymer may contain a constituent unit corresponding to another monomer copolymerizable with the alkyl (meth) acrylate, as necessary, for the purpose of improving cohesive force, heat resistance, crosslinking property, and the like. Examples of such monomers include: carboxyl group-containing monomers such as acrylic acid and methacrylic acid; anhydride monomers such as maleic anhydride and itaconic anhydride; hydroxyl group-containing monomers such as hydroxyethyl (meth) acrylate and hydroxypropyl (meth) acrylate; sulfonic acid group-containing monomers such as styrenesulfonic acid and allylsulfonic acid; nitrogen-containing monomers such as (meth) acrylamide, N-dimethyl (meth) acrylamide, and acryloylmorpholine; aminoalkyl (meth) acrylate monomers such as aminoethyl (meth) acrylate; alkoxyalkyl (meth) acrylate monomers such as methoxyethyl (meth) acrylate; maleimide monomers such as N-cyclohexylmaleimide and N-isopropylmaleimide; itaconimide monomers such as N-methylitaconimide and N-ethylitaconimide; a succinimide-based monomer; vinyl monomers such as vinyl acetate, vinyl propionate, N-vinylpyrrolidone and methyl-vinylpyrrolidone; cyanoacrylate monomers such as acrylonitrile and methacrylonitrile; epoxy group-containing acrylic monomers such as glycidyl (meth) acrylate; glycol-based acrylate monomers such as polyethylene glycol (meth) acrylate and polypropylene glycol (meth) acrylate; acrylate monomers having a heterocyclic ring, a halogen atom, a silicon atom, and the like, such as tetrahydrofurfuryl (meth) acrylate, fluoro (meth) acrylate, and silicone (meth) acrylate; olefin monomers such as isoprene, butadiene, and isobutylene; vinyl ether monomers such as vinyl ether. These monomer components may be used alone or in combination of two or more. The content ratio of the constituent unit derived from the other monomer is preferably 1 to 30 parts by weight, more preferably 3 to 25 parts by weight, based on 100 parts by weight of the acrylic polymer.
The intermediate layer-forming composition may further contain an active energy ray-reactive compound (monomer or oligomer). Examples of the active energy ray-reactive compound include photoreactive monomers or oligomers having a functional group having a polymerizable carbon-carbon multiple bond, such as an acryloyl group, a methacryloyl group, a vinyl group, an allyl group, or an ethynyl group. When a polyfunctional monomer such as a polyfunctional acrylate having 2 or more functional groups is used, a high molecular weight UV-polymerizable (meth) acrylic polymer can be obtained by bonding with the above-mentioned alkyl (meth) acrylate. Specific examples of the photoreactive monomer include (meth) acrylic acid and polyol esters such as trimethylolpropane tri (meth) acrylate, tetramethylolmethane tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol monohydroxypenta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, and polyethylene glycol di (meth) acrylate; a polyfunctional urethane (meth) acrylate; epoxy (meth) acrylates; oligoester (meth) acrylates, and the like. Further, monomers such as methacryloyl isocyanate, 2-methacryloyloxyethyl isocyanate (2-isocyanatoethyl methacrylate), and m-isopropenyl- α, α -dimethylbenzyl isocyanate can be used. Specific examples of the photoreactive oligomer include dimers, pentamers, and the like of the above-mentioned monomers.
As the active energy ray-reactive compound, there can be used: monomers such as epoxidized butadiene, glycidyl methacrylate, acrylamide, and vinyl siloxane; or an oligomer composed of the monomer.
As the active energy ray-reactive compound, a mixture of an organic salt such as an onium salt and a compound having a plurality of heterocyclic rings in the molecule can be used. The mixture can be subjected to organic salt cleavage by irradiation with active energy rays (e.g., ultraviolet rays, electron beams), generate ions, and initiate a ring-opening reaction of the heterocyclic ring using the ions as a starting species, thereby forming a three-dimensional network structure. Examples of the organic salts include iodonium salts, phosphonium salts, antimonium salts, sulfonium salts, and borate salts. Examples of the heterocyclic ring in the compound having a plurality of heterocyclic rings in the molecule include ethylene oxide, oxetane, tetrahydrofuran, thiirane, aziridine, and the like.
When the composition for forming an intermediate layer contains the active energy ray-reactive compound, the content of the active energy ray-reactive compound is preferably 0.1 to 100 parts by weight, more preferably 0.1 to 50 parts by weight, and still more preferably 0.1 to 10 parts by weight, based on 100 parts by weight of the base polymer.
The intermediate layer-forming composition may contain a photopolymerization initiator. In one embodiment, the intermediate layer comprises alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate as a photopolymerization initiator. Preferably, the intermediate layer comprises the same alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate as the adhesive layer described above. By making the intermediate layer and the adhesive layer contain the same alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate, residual glue on an adherend can be prevented after ultraviolet irradiation regardless of the composition and structure of the adherend.
As the photopolymerization initiator other than alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate, any suitable photopolymerization initiator can be used. Examples thereof include trade names "Irgacure 184", "Irgacure 651", "Irgacure 369", "Irgacure 379 ex", "Irgacure 819", "Irgacure OXE 2", "Irgacure 127" manufactured by BASF corporation; trade names "Esacure one", "Esacure 1001 m" manufactured by Lamberti corporation; the trade names "Adeka Optomer N-1414", "Adeka Optomer N-1606" and "Adeka Optomer N-1717" manufactured by Asahi Denka Kogyo Co. The content of the photopolymerization initiator is preferably 0.1 to 20 parts by weight, and more preferably 1 to 10 parts by weight, based on 100 parts by weight of the polymer components in the intermediate layer-forming composition.
In one embodiment, the intermediate layer-forming composition further includes a crosslinking agent. Examples of the crosslinking agent include isocyanate crosslinking agents, epoxy crosslinking agents, oxazoline crosslinking agents, aziridine crosslinking agents, melamine crosslinking agents, peroxide crosslinking agents, urea crosslinking agents, metal alkoxide crosslinking agents, metal chelate crosslinking agents, metal salt crosslinking agents, carbodiimide crosslinking agents, and amine crosslinking agents.
When the intermediate layer-forming composition contains a crosslinking agent, the content of the crosslinking agent is preferably 0.5 to 10 parts by weight, and more preferably 1 to 8 parts by weight, based on 100 parts by weight of the polymer components in the intermediate layer-forming composition.
The intermediate layer-forming composition may further contain any suitable additive as needed. Examples of the additives include an active energy ray polymerization accelerator, a radical scavenger, a thickener, a plasticizer (e.g., a trimellitate ester plasticizer or a pyromellitic ester plasticizer), a pigment, a dye, a filler, an antioxidant, a conductive material, an antistatic agent, an ultraviolet absorber, a light stabilizer, a release modifier, a softener, a surfactant, a flame retardant, and an antioxidant.
The weight average molecular weight of the (meth) acrylic polymer is preferably 30 to 1500 ten thousand, and more preferably 50 to 150 ten thousand. The weight average molecular weight can be measured by GPC (solvent: THF).
The glass transition temperature of the (meth) acrylic polymer is preferably-50 to 30 ℃ and more preferably-40 to 20 ℃. Within such a range, a psa sheet having excellent heat resistance and suitable for use in a heating process can be obtained.
The thickness of the intermediate layer is, for example, 10 to 500. mu.m. By forming the intermediate layer having such a thickness, an adhesive sheet in which the uneven surface can be satisfactorily filled can be obtained. The thickness of the intermediate layer is preferably 20 to 300. mu.m, more preferably 20 to 200. mu.m, still more preferably 20 to 150. mu.m, and particularly preferably 20 to 100. mu.m.
When the intermediate layer contains alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate, the ultraviolet-curable adhesive exemplified in the above item a-1 can be used as the resin forming the intermediate layer. When the intermediate layer is formed of an ultraviolet-curable adhesive, the ultraviolet-curable adhesive used may be the same as or different from the adhesive layer.
The elastic modulus of the intermediate layer is preferably 0.05 to 10MPa, more preferably 0.075 to 5MPa, and still more preferably 0.10 to 0.50 MPa. Within such a range, a pressure-sensitive adhesive sheet can be obtained which can satisfactorily fill in irregularities on the surface of an adherend. In addition, the adherend holding force of the pressure-sensitive adhesive sheet can be improved.
C. Method for producing adhesive sheet
The adhesive sheet can be produced by any suitable method. The pressure-sensitive adhesive sheet can be obtained by, for example, applying the above-mentioned ultraviolet-curable pressure-sensitive adhesive composition to a substrate. As the coating method, various methods such as bar coater coating, air knife coating, gravure reverse coating, reverse roll coating, lip coating, die coating, dip coating, offset printing, flexo printing, screen printing, and the like can be used. In addition, a method of separately forming an adhesive layer on the separator and then bonding the adhesive layer to the substrate may be employed.
When the pressure-sensitive adhesive sheet includes an intermediate layer, the pressure-sensitive adhesive sheet can be produced by, for example, forming the intermediate layer on a substrate and then forming a pressure-sensitive adhesive layer. The intermediate layer may be formed by any suitable method. Specifically, the adhesive layer can be formed by the same method as that for the adhesive layer described above.
D. Use of adhesive sheet
The pressure-sensitive adhesive sheet of the present invention is not affected by the composition of the surface of an adherend (for example, an inorganic substance such as a metal or an organic substance such as a resin), and can exhibit excellent adhesive force before irradiation with ultraviolet light. Further, since the adhesive composition has excellent followability to irregularities, it can exhibit excellent adhesive force even when the structure (for example, irregularities) of the surface of an adherend is complicated. The pressure-sensitive adhesive sheet is not affected by the composition and structure of the surface of the adherend, and can exhibit a light peelability by reducing the adhesive strength after ultraviolet irradiation. Therefore, adhesive residue on the surface of the adherend can be prevented. Therefore, the resin composition can be suitably used for applications requiring these properties.
In one embodiment, the adhesive sheet of the present invention can be suitably used in a semiconductor wafer processing step. The pressure-sensitive adhesive sheet can exhibit excellent adhesive force without being affected by the composition and structure of the surface of an adherend, and therefore can be suitably used also in the processing of semiconductor wafers having a complicated surface structure due to metal wiring, solder bumps, and the like. In addition, the back grinding tape can be suitably used as a back grinding tape in a step requiring a stronger adhesive force such as the SDBG process. The pressure-sensitive adhesive sheet can exhibit excellent light peelability after ultraviolet irradiation. Therefore, the adhesive can be easily peeled off from the adherend after the back grinding step, and adhesive residue on the adherend can be prevented.
Examples
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. The test and evaluation methods in the examples are as follows. Unless otherwise specified, "parts" and "%" are based on weight.
< production example 1 > preparation of adhesive base Polymer solution
100 parts by weight of 2-ethylhexyl acrylate, 25.5 parts by weight of acryloyl morpholine, 18.5 parts by weight of 2-hydroxyethyl acrylate, 0.2 parts by weight of a polymerization initiator (benzoyl peroxide (BPO)), and a solvent (toluene) were mixed, thereby preparing a monomer composition. The monomer composition was put into a polymerization experimental apparatus equipped with a removable lid, a separatory funnel, a thermometer, a nitrogen inlet, a Liebig condenser, a vacuum seal, a stirring bar, and a stirring blade in a 1L separable round-bottomed flask, and nitrogen substitution was carried out at room temperature for 6 hours while stirring. Thereafter, the mixture was kept at 60 ℃ for 8 hours while stirring and polymerized while introducing nitrogen gas, thereby obtaining a resin solution.
The obtained resin solution was cooled to room temperature, and then 22.4 parts by weight of 2-isocyanoethyl methacrylate (product name "Karenz MOI" manufactured by SHOWA AND ELECTRICAL CO., LTD.) as a compound having a polymerizable carbon-carbon double bond was added to the resin solution. Further, 0.11 part by weight of dibutyltin dilaurate IV (manufactured by Wako pure chemical industries, Ltd.) was added thereto, and the mixture was stirred at 50 ℃ for 24 hours under an air atmosphere to obtain a polymer solution.
Production example 2 preparation of intermediate layer base Polymer
Butyl acrylate 50 parts by weight, ethyl acrylate 50 parts by weight, acrylic acid 5 parts by weight, and azobisisobutyronitrile 0.1 parts by weight were polymerized in toluene at 60 ℃ for 6 hours in a nitrogen atmosphere to obtain an acrylic resin having a weight average molecular weight of 65 ten thousand.
[ example 1]
(preparation of adhesive layer-Forming composition)
To 100 parts by weight of the polymer solution obtained in production example 1, 2 parts by weight of a crosslinking agent (trade name: Coronate L, manufactured by Tosoh corporation) and 3 parts by weight of ethyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate (photopolymerization initiator, trade name: Omnirad TPO-L, manufactured by IGM Resins corporation) were added and stirred to obtain an ultraviolet-curable pressure-sensitive adhesive composition.
(preparation of intermediate layer Forming composition)
To 100 parts by weight of the acrylic resin obtained in production example 2 were added 1 part by weight of a crosslinking agent (trade name: Coronate L, manufactured by Tosoh corporation) and 3 parts by weight of ethyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate (photopolymerization initiator, trade name: Omnirad TPO-L, manufactured by IGM Resins corporation) and the mixture was stirred to obtain an intermediate layer-forming composition.
(preparation of adhesive sheet)
As the substrate, a polyethylene terephthalate film (product name: Lumiror S10# 100, thickness: 100 μm, manufactured by Toray corporation) was subjected to corona treatment on one surface thereof. The intermediate layer-forming composition was applied to the corona-treated surface of the substrate and dried to form an intermediate layer having a thickness of 95 μm. Next, the adhesive layer forming composition was applied to the formed intermediate layer so that the thickness after drying became 5 μm, and dried, thereby obtaining an adhesive sheet 1.
Comparative examples 1 to 6
Adhesive sheets C1 to C6 were produced in the same manner as in example 1, except that the type and content of the photopolymerization initiator and the content of the crosslinking agent in the adhesive layer-forming composition and the content of the photopolymerization initiator in the intermediate layer-forming composition were changed as described in table 1.
[ Table 1]
The pressure-sensitive adhesive sheets obtained in examples and comparative examples were used for the following evaluations. The results are shown in Table 2.
(1) Adhesive force
The silicon adhesive force (Si adhesive force), the polyimide adhesive force (PI adhesive force), and the copper adhesive force (Cu adhesive force) were measured using a Si mirror wafer (manufactured by shin-Etsu chemical), a wafer coated with a non-photosensitive polyimide (manufactured by KST WORLD), and a copper plate (manufactured by Kobe Steel Co., Ltd., trade name: KLH-194-H) as adherends, respectively. The adherend was pretreated by washing and drying with toluene, methanol, and toluene in this order, and then the pressure-sensitive adhesive sheets of examples and comparative examples were bonded thereto and stored at room temperature for 30 minutes. Thereafter, before UV irradiation, and with a high-pressure mercury lamp (70 mW/cm)2Manufactured by rituji corporation, product name: UM-810) for about 12 seconds and UV irradiation (1000 mJ/cm)2) Thereafter (after UV irradiation), the adhesive force (N/20mm) was measured under the following conditions, respectively. Further, the presence or absence of yellowing and the presence or absence of adhesive residue in the pressure-sensitive adhesive layer were visually confirmed.
< adhesion measurement Condition >
Stretching speed: 300 mm/min
Peeling angle: 180 degree
Temperature: 23 deg.C
Humidity: 50% RH
Bandwidth: 20mm
(2) Modulus of elasticity
The adhesive layer-forming composition used in each of examples and comparative examples was coated on a separator so that the coating thickness reached 5 μm, and dried under conditions of 130 ℃. Next, a rod-shaped sample was prepared by rolling up only the adhesive layer after application and drying from the end, and the thickness (cross-sectional area) was measured. The initial slope (Young's modulus) of the obtained sample when it was stretched in a tensile tester (trade name "AG-IS" manufactured by SHIMADZU) under conditions of a chuck-to-chuck distance of 10mm, a stretching speed of 50 mm/min and room temperature was taken as the elastic modulus.
(3) Bump wafer evaluation
The wafer (uniform, 45 μm height, 25 μm diameter, 55 μm pitch) on which the dummy bumps are formed
The pressure-sensitive adhesive sheets obtained in examples and comparative examples were bonded to a wafer under the following conditions. Using this sample, the peeling force, landfill property, and presence/absence of residual gum were evaluated by the following methods.
Bonding conditions
The device comprises the following steps: manufactured by rituximab, trade name: DR-3000III
Pressure: 0.5MPa
Bonding speed: 10 mm/sec
Temperature: at room temperature
< bump wafer peeling force >
As a sample, an adhesive sheet obtained in each of examples and comparative examples was used, in which a slit (20mm wide) was formed along the tape running direction (MD direction). The sample was bonded to a wafer on which dummy bump wafers were formed under the above conditions. After the application, the film was stored at room temperature for 30 minutes. Then, a high-pressure mercury lamp (70 mW/cm) was used2Manufactured by rituji corporation, product name: UM-810) was subjected to UV irradiation for 12 seconds (1000 mJ/cm)2). Subsequently, the adhesive tape was peeled at a tensile rate of 300 mm/min and a peel angle of 180 ℃ at room temperature, and the peel force (N/mm) was measured.
< landfill and residual gum >
Will be adhered withThe bump wafer of the adhesive sheet was left standing with the V notch of the wafer in the 0 point direction. Next, each portion was observed with an optical microscope (magnification of 250 times) in the 0-point direction, 3-point direction, 6-point direction, 9-point direction, and center portion of the wafer, and evaluated according to the following criteria. Then, a high-pressure mercury lamp (70 mW/cm) was used2Manufactured by rituji corporation, product name: UM-810) was subjected to UV irradiation for 12 seconds (1000 mJ/cm)2). After that, the adhesive sheet was peeled, and the surface of the bump wafer after peeling was observed with an optical microscope (magnification: 250 times), and evaluated according to the following criteria.
Landfill evaluation criterion
3: the adhesive layer is filled between the bumps in a bubble-free form in all portions
2: although some air bubbles are observed between the bumps, the adhesive layer is substantially filled in a bubble-free form
1: in all portions, air bubbles were observed between the bumps
Residual gum evaluation standard
3: no adhesive residue
2: tiny residual gum
1: severe gum residue
0: cannot be peeled off
[ Table 2]
As is clear from table 2, the psa sheet of example 1 has a comparable adhesive strength to that of a silicon wafer, regardless of whether the adherend surface is organic (PI adhesive strength) or inorganic (Cu adhesive strength). In addition, the adhesive has excellent stripping performance after ultraviolet irradiation, and can prevent adhesive residue on an adherend. In addition, even when the adherend surface has irregularities, both the filling-in property for the irregularities and the prevention of adhesive residue can be achieved. On the other hand, in the comparative example, when the filling property is excellent, there is a residual gum, and when the residual gum preventing property is excellent, there is a room for improvement in the filling property, and it is difficult to achieve both of them.
Claims (9)
1. An ultraviolet-curable adhesive composition comprising an ultraviolet-curable adhesive and an alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate.
2. The ultraviolet-curable adhesive composition according to claim 1, wherein the alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate is ethyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate.
3. An adhesive sheet comprising a substrate and an adhesive layer,
the adhesive layer is formed from the ultraviolet-curable adhesive composition according to claim 1.
4. The adhesive sheet according to claim 3, comprising at least 1 layer of the adhesive layer.
5. The adhesive sheet according to claim 3, wherein the adhesive layer has a ratio of polyimide adhesive force to silicon adhesive force after ultraviolet irradiation of 2 or less.
6. The adhesive sheet according to claim 3, further comprising an intermediate layer.
7. The adhesive sheet according to claim 6, wherein the intermediate layer comprises the same alkyl phenyl (2,4, 6-trimethylbenzoyl) phosphinate as the adhesive layer.
8. The adhesive sheet according to claim 3, which is used in a semiconductor wafer processing process.
9. The adhesive sheet according to claim 8, which is used as a back grinding sheet.
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| JP2020007711A JP7386088B2 (en) | 2020-01-21 | 2020-01-21 | Adhesive composition and adhesive sheet using the adhesive composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004204090A (en) * | 2002-12-26 | 2004-07-22 | C I Kasei Co Ltd | Film with pressure sensitive adhesive layer and its manufacturing method |
| CN104449442A (en) * | 2013-09-19 | 2015-03-25 | 日东电工株式会社 | Adhesive sheet |
| KR20180126761A (en) * | 2017-05-18 | 2018-11-28 | 동우 화인켐 주식회사 | Adhesive Composition and Adhesive Sheet Using the Same |
| JP2019156967A (en) * | 2018-03-13 | 2019-09-19 | 日東電工株式会社 | Semiconductor protective adhesive tape |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS62153376A (en) | 1985-12-27 | 1987-07-08 | F S K Kk | Pressure-sensitive adhesive sheet |
| JP3491911B2 (en) | 1992-07-29 | 2004-02-03 | リンテック株式会社 | Adhesive sheet for semiconductor wafer processing |
| JP2004111428A (en) | 2002-09-13 | 2004-04-08 | Tokyo Seimitsu Co Ltd | Chip manufacturing method |
| US20090017323A1 (en) * | 2007-07-13 | 2009-01-15 | 3M Innovative Properties Company | Layered body and method for manufacturing thin substrate using the layered body |
| JP6611252B2 (en) * | 2016-03-28 | 2019-11-27 | リンテック株式会社 | Semiconductor processing sheet |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004204090A (en) * | 2002-12-26 | 2004-07-22 | C I Kasei Co Ltd | Film with pressure sensitive adhesive layer and its manufacturing method |
| CN104449442A (en) * | 2013-09-19 | 2015-03-25 | 日东电工株式会社 | Adhesive sheet |
| KR20180126761A (en) * | 2017-05-18 | 2018-11-28 | 동우 화인켐 주식회사 | Adhesive Composition and Adhesive Sheet Using the Same |
| JP2019156967A (en) * | 2018-03-13 | 2019-09-19 | 日東電工株式会社 | Semiconductor protective adhesive tape |
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| JP2021113298A (en) | 2021-08-05 |
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