CN118019819A - Curable adhesive sheet and method for producing cured product - Google Patents
Curable adhesive sheet and method for producing cured product Download PDFInfo
- Publication number
- CN118019819A CN118019819A CN202280063975.1A CN202280063975A CN118019819A CN 118019819 A CN118019819 A CN 118019819A CN 202280063975 A CN202280063975 A CN 202280063975A CN 118019819 A CN118019819 A CN 118019819A
- Authority
- CN
- China
- Prior art keywords
- curable adhesive
- release film
- adhesive layer
- mass
- less
- 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 214
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 214
- 238000004519 manufacturing process Methods 0.000 title claims description 21
- 229920005989 resin Polymers 0.000 claims abstract description 196
- 239000011347 resin Substances 0.000 claims abstract description 196
- 239000012790 adhesive layer Substances 0.000 claims abstract description 155
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 37
- 239000010410 layer Substances 0.000 claims abstract description 33
- 239000000203 mixture Substances 0.000 claims description 145
- 229920001955 polyphenylene ether Polymers 0.000 claims description 29
- 239000000126 substance Substances 0.000 claims description 15
- 238000007689 inspection Methods 0.000 claims description 8
- 230000003287 optical effect Effects 0.000 claims description 8
- 239000010408 film Substances 0.000 description 283
- 150000001875 compounds Chemical class 0.000 description 59
- -1 polyethylene terephthalate Polymers 0.000 description 57
- 125000004432 carbon atom Chemical group C* 0.000 description 37
- 238000000034 method Methods 0.000 description 32
- 150000002430 hydrocarbons Chemical group 0.000 description 31
- 239000003431 cross linking reagent Substances 0.000 description 30
- 125000000217 alkyl group Chemical group 0.000 description 24
- 238000010538 cationic polymerization reaction Methods 0.000 description 24
- 239000003505 polymerization initiator Substances 0.000 description 24
- 239000006087 Silane Coupling Agent Substances 0.000 description 21
- 238000001723 curing Methods 0.000 description 19
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 229920001296 polysiloxane Polymers 0.000 description 14
- 239000011230 binding agent Substances 0.000 description 13
- 125000000524 functional group Chemical group 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 229920001187 thermosetting polymer Polymers 0.000 description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 229920005672 polyolefin resin Polymers 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 239000011256 inorganic filler Substances 0.000 description 8
- 229910003475 inorganic filler Inorganic materials 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
- 229930195734 saturated hydrocarbon Natural products 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229920000180 alkyd Polymers 0.000 description 7
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004840 adhesive resin Substances 0.000 description 6
- 229920006223 adhesive resin Polymers 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 238000011109 contamination Methods 0.000 description 6
- 238000007865 diluting Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000004450 alkenylene group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 239000013522 chelant Substances 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 125000005702 oxyalkylene group Chemical group 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000013039 cover film Substances 0.000 description 4
- 125000002993 cycloalkylene group Chemical group 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 238000000016 photochemical curing Methods 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000005370 alkoxysilyl group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 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 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
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- 238000004132 cross linking Methods 0.000 description 2
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
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- HASUCEDGKYJBDC-UHFFFAOYSA-N 1-[3-[[bis(oxiran-2-ylmethyl)amino]methyl]cyclohexyl]-n,n-bis(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CN(CC1CC(CN(CC2OC2)CC2OC2)CCC1)CC1CO1 HASUCEDGKYJBDC-UHFFFAOYSA-N 0.000 description 1
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- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
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- 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
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- HKFSBKQQYCMCKO-UHFFFAOYSA-N trichloro(prop-2-enyl)silane Chemical compound Cl[Si](Cl)(Cl)CC=C HKFSBKQQYCMCKO-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- JTTSZDBCLAKKAY-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSSSCCC[Si](OC)(OC)OC JTTSZDBCLAKKAY-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QYJYJTDXBIYRHH-UHFFFAOYSA-N trimethoxy-[8-(oxiran-2-ylmethoxy)octyl]silane Chemical compound C(C1CO1)OCCCCCCCC[Si](OC)(OC)OC QYJYJTDXBIYRHH-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- WUKMCKCDYKBLBG-UHFFFAOYSA-N tris(4-methoxyphenyl)sulfanium Chemical compound C1=CC(OC)=CC=C1[S+](C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WUKMCKCDYKBLBG-UHFFFAOYSA-N 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09J7/40—Adhesives in the form of films or foils characterised by release liners
-
- 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
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
-
- 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
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such 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
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
- C09J171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C09J171/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C09J171/12—Polyphenylene oxides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/35—Heat-activated
-
- 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
-
- 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
- C09J2301/50—Additional features of adhesives in the form of films or foils characterized by process specific features
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Laminated Bodies (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The present invention provides a curable adhesive sheet, which comprises: a curable adhesive layer capable of forming a cured product having a dielectric loss tangent of 0.01 or less at 23 ℃ and 1 GHz; and a 1 st release film and a 2 nd release film sandwiching both sides of the curable adhesive layer, the 1 st release film having: a colored resin film (i), and a release agent layer laminated on one surface of the colored resin film (i) and in contact with the surface of the curable adhesive layer, wherein the 2 nd release film comprises: a resin film (ii) visually distinguishable from the colored resin film (i), and a release agent layer laminated on one surface of the resin film (ii) and in contact with the surface of the curable adhesive layer, the curable adhesive sheet satisfying the following element (Ia). Element (Ia): the thickness ratio (T2)/(T1) of the thickness (T2) of the 2 nd release film to the thickness (T1) of the 1 st release film is 1.05 or more.
Description
Technical Field
The present invention relates to a curable adhesive sheet and a method for producing a cured product using the curable adhesive sheet.
Background
In recent years, with miniaturization and weight reduction of electronic devices, flexible printed wiring boards (FPCs) are being used as wiring members. The FPC may be manufactured by, for example, etching a copper foil of a copper-clad laminate in which a copper foil is bonded to an insulating resin film such as polyimide to form a circuit.
In addition, the following operations are performed for such FPC: a cover film (coverlay) sheet having an insulating resin base material and an adhesive layer is bonded to a copper foil on which a circuit is formed to protect the circuit.
As an example of such a cover film, patent document 1 discloses an invention relating to a thermosetting adhesive sheet in which a thermosetting adhesive layer composed of an adhesive composition containing a predetermined amount of a styrene-based elastomer, a modified polyphenylene ether resin having a polymerizable group at the terminal, an epoxy resin, and an epoxy resin curing agent is formed on a substrate.
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2019-135280.
Disclosure of Invention
Problems to be solved by the invention
However, a release sheet subjected to a release treatment is provided on the surface of the thermosetting adhesive layer of the thermosetting adhesive sheet described in patent document 1 to protect the surface.
As the release sheet, a release sheet having a release layer on a paper base is widely used, and dust or a foreign matter of dust is easily generated from the paper base, and when the thermosetting adhesive layer is adhered to an adherend, the foreign matter may be mixed between the adherend and the thermosetting adhesive layer. In particular, in FPC, the contamination of foreign matter also becomes a factor causing malfunction of electronic equipment.
In addition, in the case of using a release sheet other than the paper base material, there is a problem in that the release sheet is difficult to peel from the thermosetting adhesive layer.
Therefore, there is a need for a curable adhesive sheet that, when adhered to an adherend, suppresses the incorporation of foreign matter and has excellent handleability.
Means for solving the problems
The present invention provides a curable adhesive sheet, which comprises: a curable adhesive layer of a cured product having a dielectric loss tangent of a predetermined value or less, and a 1 st release film and a2 nd release film sandwiching both sides of the curable adhesive layer, wherein the 1 st release film has a colored resin film, the 2 nd release film has a resin film visually distinguishable from the colored resin film, and the ratio of the thickness of the 2 nd release film to the thickness of the 1 st release film is set to a predetermined value or more.
Specifically, as one embodiment provided by the present invention, the following is described.
[1] A curable adhesive sheet comprising: a curable adhesive layer capable of forming a cured product having a dielectric loss tangent of 0.01 or less at 23 ℃ and 1 GHz; a1 st release film and a2 nd release film sandwiching both sides of the curable adhesive layer,
The 1 st release film has: a colored resin film (i), and a release agent layer which is laminated on one surface of the colored resin film (i) and is in contact with the surface of the curable adhesive layer,
The 2 nd release film has: a resin film (ii) visually distinguishable from the colored resin film (i), and a release agent layer laminated on one surface of the resin film (ii) and in contact with the surface of the curable adhesive layer,
The curable adhesive sheet satisfies the following element (Ia).
Element (Ia): the thickness ratio [ (T2)/(T1) ] of the thickness (T2) of the 2 nd release film to the thickness (T1) of the 1 st release film is 1.05 or more.
[2] The curable adhesive sheet according to the item (1), which further satisfies the following item (Ib).
Element (Ib): the thickness ratio [ (T2)/(T1) ] of the thickness (T2) of the 2 nd release film to the thickness (T1) of the 1 st release film is 10.0 or less.
[3] The curable adhesive sheet according to the above [1] or [2], which further satisfies the following element (IIa).
The element (IIa) is that the difference between the thickness (T2) of the 2 nd release film and the thickness (T1) of the 1 st release film [ (T2) - (T1) ] is 5.0 μm or more.
[4] The curable adhesive sheet according to any one of the above [1] to [3], which further satisfies the following element (IIb).
Element (IIb): the difference in thickness [ (T2) - (T1) ] between the thickness (T2) of the 2 nd release film and the thickness (T1) of the 1 st release film is 165.0 μm or less.
[5] The curable adhesive sheet according to any one of the above [1] to [4], which further satisfies the following element (III).
Element (III): the ratio [ (R1)/(R2) ] of the peel force (R1) when the 1 st release film is peeled from the curable adhesive layer at 180 DEG peel angle and 300 mm/min to the peel force (R2) when the 2 nd release film is peeled from the curable adhesive layer at 180 DEG peel angle and 300 mm/min is 0.97 or less.
[6] The curable adhesive sheet according to any one of the above [1] to [5], which further satisfies the following element (IV).
Element (IV): the peel force (R2) when the 2 nd release film is peeled from the curable adhesive layer at a peel angle of 180 DEG at a peel speed of 300 mm/min is greater than the peel force (R1) when the 1 st release film is peeled from the curable adhesive layer at a peel angle of 180 DEG at a peel speed of 300 mm/min, and the peel force (R2) is 600mN/50mm or less.
[7] The curable adhesive sheet according to any one of [1] to [6], wherein the resin film (ii) is a transparent resin film.
[8] The curable adhesive sheet according to any one of the above [1] to [7], wherein the curable adhesive layer is a layer formed of a curable adhesive composition containing a polyphenylene ether resin.
[9] The curable adhesive sheet according to any one of [1] to [8], wherein when the curable adhesive layer exposed by peeling the 1 st release film is adhered to an adherend, it is possible to confirm whether or not a foreign substance is present at the interface between the curable adhesive layer and the adherend from the 2 nd release film side by an optical inspection means.
[10] A method for producing a cured product using the curable adhesive sheet according to any one of the above [1] to [9], comprising the following steps (1) to (3).
Step (1): and a step of adhering the curable adhesive layer exposed by peeling the 1 st release film to an adherend.
Step (2): and a step of confirming, by an optical inspection means, that no foreign matter is present at the interface between the curable adhesive layer and the adherend from the 2 nd release film side.
Step (3): and (2) curing the curable adhesive layer to obtain a cured product.
Effects of the invention
The curable adhesive sheet according to one preferred embodiment of the present invention can suppress the contamination of foreign matter when it is adhered to an adherend, and is excellent in handleability, while easily removing the release film.
Drawings
FIG. 1 is a schematic cross-sectional view of an example of the structure of a curable adhesive sheet according to the present invention in the thickness direction of the adhesive sheet.
Detailed Description
The numerical ranges recited herein can be arbitrarily combined with upper and lower limits. For example, when the numerical range is described as "preferably 20 to 120, more preferably 40 to 90", the numerical range of "20 to 90" or the numerical range of "40 to 120" is also included in the numerical range described in the present specification. For example, when the numerical range is "preferably 20 or more, more preferably 40 or more, and further preferably 120 or less, more preferably 90 or less," the range of "20 to 90" or the range of "40 to 120" is included in the numerical range described in the present specification.
The numerical ranges described in the present specification are, for example, "60 to 100" and "60 or more and 100 or less".
In the specification of the upper limit and the lower limit described in the present specification, the numerical ranges from the lower limit to the upper limit may be arbitrarily selected from the respective options, and may be arbitrarily combined.
In addition, as a preferred embodiment described in the present specification, a plurality of the various elements described may be combined.
In the present specification, for example, "(meth) acrylate" is used as a term indicating both "acrylate" and "methacrylate", and the same applies to other similar terms.
In the present specification, the "active ingredient" of the curable adhesive composition refers to a component from which a diluting solvent of water or an organic solvent is removed from the components contained in the curable adhesive composition.
In the present specification, the number average molecular weight (Mn) is a value in terms of standard polystyrene measured by Gel Permeation Chromatography (GPC), specifically, a value measured according to the method described in examples.
In the present specification, the thickness of each layer constituting the curable adhesive sheet is a value measured in accordance with JIS K7130 (1999), and can be measured, for example, by using a constant pressure thickness measuring instrument (manufactured by the company TECLOCK, product name "PG-02J").
[ Composition of curable adhesive sheet ]
Fig. 1 is a schematic cross-sectional view of an example of the structure of the curable adhesive sheet of the present invention in the thickness direction.
As shown in fig. 1, the curable adhesive sheet 1 of the present invention includes: a curable adhesive layer 10, and a1 st release film 21 and a2 nd release film 22 which sandwich both sides of the curable adhesive layer 10.
The curable adhesive layer 10 can be cured to form a cured product having a dielectric loss tangent of 0.01 or less at 23 ℃ and 1 GHz.
The 1 st release film 21 has: a colored resin film (i) 212, and a release layer 211 laminated on one surface of the colored resin film (i) 212 and in contact with the surface 10a of the curable adhesive layer 10. The colored resin film includes a white resin film.
In addition, the 2 nd release film 22 has: resin film (ii) 222, and laminated on resin film (ii)
222 And a release layer 221 on one surface thereof in contact with the surface 10b of the curable adhesive layer 10.
In the curable adhesive sheet according to one embodiment of the present invention, the resin film (ii) of the 2 nd release film and the colored resin film (i) of the 1 st release film can be visually distinguished.
The curable adhesive sheet according to one embodiment of the present invention is used in the following applications: the 1 st release film 21 is peeled off, the surface 10a of the exposed curable adhesive layer 10 is stuck to the adherend, and the 2 nd release film 22 is peeled off.
As described above, the 1 st release film has the colored resin film (i), and the 2 nd release film has the resin film (ii) distinguishable from the colored resin film (i) by visual observation, so that the distinction between the 1 st release film and the 2 nd release film becomes clear. Therefore, in the curable adhesive sheet according to one embodiment of the present invention, the 1 st release film that is peeled first is easily recognized when used, and an error in peeling the 2 nd release film by mistake can be prevented. In addition, as described later, when the 2 nd release film is a colorless transparent resin film, the colored resin film (i) as the 1 st release film is released first, and the curable adhesive sheet as a whole has an appearance that is nearly colorless transparent, so that there is an advantage in that the colored resin film (i) is easily recognized as having been released by visual inspection.
Further, since the 1 st release film and the 2 nd release film each use a resin film as a base material, the release films are less likely to cause generation of foreign matters such as dust and dust. Therefore, the curable adhesive sheet according to one embodiment of the present invention can effectively suppress the contamination of foreign matter when it is adhered to an adherend, and thus can suppress the malfunction of electronic equipment caused by the contamination of foreign matter even when it is used in, for example, FPC.
The curable adhesive sheet according to one embodiment of the present invention is preferably configured as follows: when the curable adhesive layer exposed by peeling the 1 st release film is adhered to an adherend, the presence or absence of a foreign substance at the interface between the curable adhesive layer and the adherend can be confirmed from the 2 nd release film side by an optical inspection means.
With such a configuration, when the curable adhesive layer is adhered to the adherend, it is possible to confirm whether or not foreign matter is mixed between the adherend and the curable adhesive layer from the side of the 2 nd release film. Therefore, the curable adhesive sheet can be re-adhered, and the like, and the yield of the product can be improved.
The resin film of the 2 nd release film may be any transparent resin, for example.
However, in the adhesive sheet having a structure in which the adhesive layer is sandwiched between 2 release films, when the release film using a resin film as a base material is provided, there is a problem that it is easy to cause a problem in that it is difficult to peel one of the release films from the adhesive layer, as compared with the release film using a general paper base material.
In particular, as in the curable adhesive sheet of the present invention, the curable adhesive layer having a low dielectric loss tangent is often composed of a component having no polar group or a component having a low polarity, and the polarity of the surface of the curable adhesive layer is low. Therefore, in the case of a configuration in which 2 sheets of curable adhesive layers having low polarity are sandwiched between the release films having resin films, it becomes more difficult to peel one of the release films from the surface of the curable adhesive layer having low polarity when in use, and there is a problem in operability.
In order to solve the problem of difficulty in peeling the release film from the surface of the curable adhesive layer having low polarity, the curable adhesive sheet of the present invention is adjusted to satisfy the following element (Ia). Element (Ia): the thickness ratio [ (T2)/(T1) ] of the thickness (T2) of the 2 nd release film to the thickness (T1) of the 1 st release film is 1.05 or more.
By adjusting the thickness ratio of the 1 st release film to the 2 nd release film so as to satisfy the above-described element (I), the 1 st release film can be easily peeled off in a state where the 1 st release film and the 2 nd release film sandwich the curable adhesive layer, and a curable adhesive sheet excellent in handleability can be produced. This effect is considered to be that the 1 st release film is easily peeled from the curable adhesive layer by fixing the shape of the curable adhesive layer by the 2 nd release film as a support.
In the curable adhesive sheet according to one embodiment of the present invention, the thickness ratio [ (T2)/(T1) ] defined in the above element (I) is 1.05 or more, preferably 1.25 or more, more preferably 1.50 or more, still more preferably 1.70 or more, from the viewpoint that the 1 st release film is easily peeled from the curable adhesive layer in a state where the 1 st release film and the 2 nd release film sandwich the curable adhesive layer.
In the curable adhesive sheet according to one embodiment of the present invention, the following element (Ib) is preferably satisfied from the standpoint of easier peeling of the 1 st release film from the curable adhesive layer in a configuration in which the 1 st release film and the 2 nd release film sandwich the curable adhesive layer, and from the standpoint of easier winding even of a core having a small diameter when winding the long curable adhesive sheet.
Element (Ib): the thickness ratio [ (T2)/(T1) ] of the thickness (T2) of the 2 nd release film to the thickness (T1) of the 1 st release film is 10.0 or less.
From the above point of view, the thickness ratio [ (T2)/(T1) ] defined in the above-mentioned element (Ib) is 10.0 or less, preferably 7.0 or less, more preferably 4.0 or less, and still more preferably 3.0 or less.
In the curable adhesive sheet according to one embodiment of the present invention, the following element (IIa) is preferably satisfied from the viewpoint that the 1 st release film is more easily peeled from the curable adhesive layer in a configuration in which the 1 st release film and the 2 nd release film sandwich the curable adhesive layer.
Element (IIa): the difference in thickness [ (T2) - (T1) ] between the thickness (T2) of the 2 nd release film and the thickness (T1) of the 1 st release film is 5.0 μm or more.
From the above point of view, the thickness difference [ (T2) - (T1) ] defined in the above-mentioned element (IIa) is 5.0 μm or more, preferably 10.0 μm or more, more preferably 20.0 μm or more, still more preferably 30.0 μm or more.
In the curable adhesive sheet according to one embodiment of the present invention, the following element (IIb) is preferably satisfied from the viewpoint that the 1 st release film is more easily peeled from the curable adhesive layer in a configuration in which the 1 st release film and the 2 nd release film sandwich the curable adhesive layer.
Element (IIb): the difference in thickness [ (T2) - (T1) ] between the thickness (T2) of the 2 nd release film and the thickness (T1) of the 1 st release film is 165.0 μm or less.
From the above point of view, the thickness difference [ (T2) - (T1) ] defined in the above-mentioned element (IIb) is 165.0 μm or less, preferably 100.0 μm or less, more preferably 70.0 μm or less, still more preferably 50.0 μm or less.
In the curable adhesive sheet according to one embodiment of the present invention, the following element (III) is preferably satisfied from the viewpoint that the 1 st release film is more easily peeled from the curable adhesive layer in a configuration in which the 1 st release film and the 2 nd release film sandwich the curable adhesive layer.
Element (III): the ratio [ (R1)/(R2) ] of the peel force (R1) when the 1 st release film is peeled from the curable adhesive layer at 180 DEG peel angle and 300 mm/min to the peel force (R2) when the 2 nd release film is peeled from the curable adhesive layer at 180 DEG peel angle and 300 mm/min is 0.97 or less.
From the above point of view, the ratio [ (R1)/(R2) ] defined in the above-mentioned element (III) is 0.97 or less, preferably 0.95 or less, more preferably 0.88 or less, still more preferably 0.80 or less. The lower limit of the ratio [ (R1)/(R2) ] of the peeling force (R1) to the peeling force (R2) defined in the above-mentioned element (IIa) is not particularly limited, but is preferably 0.2 or more, more preferably 0.35 or more.
In the curable adhesive sheet according to one embodiment of the present invention, the following element (IV) is preferably satisfied from the viewpoint that the 1 st release film is more easily peeled from the curable adhesive layer in a configuration in which the 1 st release film and the 2 nd release film sandwich the curable adhesive layer.
Element (IV): the peel force (R2) when the 2 nd release film is peeled from the curable adhesive layer at a peel angle of 180 DEG at a peel speed of 300 mm/min is greater than the peel force (R1) when the 1 st release film is peeled from the curable adhesive layer at a peel angle of 180 DEG at a peel speed of 300 mm/min, and the peel force (R2) is 600mN/50mm or less.
From the above viewpoints, the peel force (R2) is 600mN/50mm or less, preferably 450mN/50mm or less, more preferably 250mN/50mm or less, and still more preferably 150mN/50mm or less.
In the curable adhesive sheet according to one embodiment of the present invention, the peel force (R1) is smaller than the peel force (R2), preferably 5mN/50mm or more, from the standpoint that the 1 st release film is more easily peeled from the curable adhesive layer in a configuration in which the 1 st release film and the 2 nd release film sandwich the curable adhesive layer.
The peel force (R2) is more preferably 10mN/50mm or more, still more preferably 20mN/50mm or more.
In view of the above, in the curable adhesive sheet according to an embodiment of the present invention, the following element (Va) is preferably satisfied, and the following element (Vb) is more preferably satisfied, from the standpoint that the 1 st release film is more easily peeled from the curable adhesive layer in a configuration in which the 1 st release film and the 2 nd release film sandwich the curable adhesive layer.
Element (Va): the stripping force (R1) is less than or equal to 5mN/50mm and less than or equal to 600mN/50mm;
Element (Vb): the peeling force (R1) is less than or equal to 5mN/50mm and less than or equal to 250mN/50mm.
The release force (R1) and the release force (R2) can be adjusted by appropriately setting the types of the resin films constituting the 1 st release film and the 2 nd release film and the release agent forming the release agent layer, and the types and the contents of the respective components contained in the curable adhesive composition forming the curable adhesive layer. The specific adjustment method is described in detail below in the description of each configuration.
In the present specification, the peel forces (R1) and (R2) are values measured by the method described in examples described below.
Hereinafter, each layer of the curable adhesive sheet and the material for forming the layer constituting one embodiment of the present invention will be described.
[1 St Release film, 2 nd Release film ]
The 1 st release film used in one embodiment of the present invention may be any film having a composition comprising the colored resin film (i) and a release layer formed of a release agent.
Examples of the resin component contained in the colored resin film (i) include: and polyester resins such as polyethylene terephthalate resin, polybutylene terephthalate resin and polyethylene naphthalate resin, polyolefin resins such as polypropylene resin and polyethylene resin, polycarbonate resins, and mixed resins obtained by using 2 or more of these resins in combination.
The colored resin film (i) may contain additives such as ultraviolet absorbers, antistatic agents, light stabilizers, antioxidants, resin stabilizers, fillers, and colorants (pigments, dyes, and the like) in addition to the resin component.
The colored resin film (i) may be a colored resin film that contains a resin component and a colorant such as a pigment or dye, and may be a foamed resin film that is foamed when formed into a film from a resin composition containing at least a resin component. The foamed resin film is generally a white and opaque colored resin film. In addition, a resin film formed from a resin composition containing both a resin component and a filler also has reduced transparency due to scattering of light, and becomes a colored resin film. A coloring agent may be further added to the foamed resin film or the colored resin film containing the filler.
Further, the resin film may be a colored resin film obtained by coloring a colorless resin film by means of printing or the like by providing a printed layer or the like on the surface of the resin film.
The front and back sides of the colored resin film (i) used in one embodiment of the present invention may have different colors.
The 2 nd release film used in one embodiment of the present invention may be any film having a composition comprising a resin film (ii) visually distinguishable from the colored resin film (i) and a release agent layer.
Examples of the resin film (ii) that can be visually distinguished from the colored resin film (i) include: the following schemes (a) to (h).
Scheme (a): in the case where the colored resin film (i) is opaque, a colorless transparent resin film is produced.
Scheme (b): in the case where the colored resin film (i) is opaque, a transparent resin film is produced, which is a colored resin film of a different color from the colored resin film (i).
Scheme (c): in the case where the colored resin film (i) is transparent, an opaque resin film is produced, which is a colored resin film of a different color from the colored resin film (i).
Scheme (d): a visually identifiable mark is attached to the surface of the resin film (ii).
Scheme (e): in the case where the colored resin film (i) is opaque, the resin film (ii) is made transparent, which is the same color as the colored resin film (i).
Scheme (f): in the case where the colored resin film (i) is transparent, the resin film (ii) is made into an opaque resin film which is the same color as the colored resin film (i).
Scheme (g): in the case where the colored resin film (i) is transparent, the resin film (ii) is made transparent, which is a colored resin film of a different color from the colored resin film (i).
Scheme (h): in the case where the colored resin film (i) is transparent, the resin film (ii) is made into a colorless transparent resin film.
Among these, the resin film (ii) is preferably any one of the above-mentioned (a) to (d) from the viewpoint of being visually distinguishable from the colored resin film (i).
The resin film (ii) is preferably a transparent resin film that can be visually distinguished from the colored resin film (i), and more preferably a colorless transparent resin film.
In the case of the curable adhesive sheet using the 2 nd release film having the transparent resin film, the 1 st release film was released, the curable adhesive layer was adhered to the adherend, and then, from the transparent resin film side of the 2 nd release film, it was confirmed whether or not the interface state of the adherend such as a foreign matter and the curable adhesive layer was mixed between the adherend and the curable adhesive layer. If foreign matter is found to be mixed, the product yield can be improved by re-attaching the curable adhesive sheet.
When the resin film (ii) is a transparent resin film, the colored resin film (i) is preferably opaque, so that it is easy to distinguish the resin film (ii) from the colored resin film (i) by visual observation.
The haze of the transparent resin film (i) used in one embodiment of the present invention is not more than 10.0%, more preferably not more than 3.0%, still more preferably not more than 1.0%, still more preferably not more than 0.6%, as long as it is transparent to the extent that foreign matter can be mixed between the adherend and the curable adhesive layer after the curable adhesive layer is adhered to the adherend.
In the case where the colored resin film (i) is opaque and the resin film (ii) is transparent, the haze of the colored resin film (i) is preferably 30.0% or more, more preferably 45.0% or more, still more preferably 60.0% or more, and still more preferably 80% or more, from the viewpoint that the distinction between the two resin films becomes clear.
The haze of the resin film can be measured using a commercially available haze meter.
The resin component contained in the resin film (ii) includes: the same resin as exemplified as the resin component contained in the colored resin film (i) is used.
The additives other than the resin component contained in the resin film (ii) may be: the same substances as the additives contained in the colored resin film (i).
The release layers included in the 1 st release film and the 2 nd release film may be formed of various release agents.
Examples of such a release agent include silicone release agents, and examples thereof include rubber-based elastomer release agents such as olefin release agents, isoprene release agents and butadiene release agents, and non-silicone release agents such as long-chain alkyl release agents, alkyd release agents and fluorine release agents.
Among these, from the viewpoint of suppressing the transfer of the silicon component to the adherend and occurrence of defective operation of the electronic device due to silicon contamination, the release agent as the material for forming the release layer is preferably a non-silicone release agent.
In addition, from the viewpoint of adjusting the peeling forces (R1) and (R2), it is preferable that at least one of the 1 st peeling film and the 2 nd peeling film is a layer formed of an alkyd-based peeling agent, and it is more preferable that both of the 1 st peeling film and the 2 nd peeling film are layers formed of an alkyd-based peeling agent.
The thickness (T1) of the 1 st release film of the curable adhesive sheet according to one embodiment of the present invention is preferably 10 μm or more, more preferably 20 μm or more, still more preferably 30 μm or more, and further preferably 200 μm or less, more preferably 100 μm or less, still more preferably 70 μm or less, still more preferably 45 μm or less, from the viewpoint of adjusting the release force (R1).
The thickness (T2) of the 2 nd release film of the curable adhesive sheet according to one embodiment of the present invention is preferably 33 μm or more, more preferably 47 μm or more, still more preferably 55 μm or more, still more preferably 65 μm or more, and further preferably 270 μm or less, more preferably 210 μm or less, still more preferably 140 μm or less, from the viewpoint of adjusting the release force (R2).
[ Curable adhesive layer ]
The curable adhesive layer of the curable adhesive sheet according to one embodiment of the present invention can form a cured product having a dielectric loss tangent of 0.01 or less at 23 ℃ and 1 GHz.
The dielectric loss tangent of the cured product at 23 ℃ and 1GHz is 0.01 or less, preferably 0.005 or less, and more preferably 0.002 or less.
The lower limit of the dielectric loss tangent of the cured product at 23℃and 1GHz is not particularly limited, but is preferably 0.00005 or more, more preferably 0.0001 or more.
In the present specification, the dielectric loss tangent of the cured product refers to a value measured by a method described in examples described below.
The method of curing the curable adhesive layer may be a thermosetting method or a photo-curing method, and may be appropriately selected depending on the application. For example, if the curable adhesive sheet according to one embodiment of the present invention is used as a cover film to form a cured product for protecting a circuit board, the thermosetting method is preferable.
In the curable adhesive sheet according to one embodiment of the present invention, the thickness of the curable adhesive layer is preferably 3.0 μm or more, more preferably 5.0 μm or more, still more preferably 10 μm or more, still more preferably 15 μm or more, and still more preferably 60 μm or less, more preferably 45 μm or less, from the viewpoint of forming a cured product having a thickness to such an extent that the circuit board can be protected.
The curable adhesive layer of the curable adhesive sheet according to one embodiment of the present invention may be formed of a curable adhesive composition containing the adhesive resin (a) (hereinafter, also referred to as "component (a)").
The curable adhesive composition used in one embodiment of the present invention preferably further contains a polyphenylene ether resin (B) (hereinafter also referred to as "component (B)") from the viewpoint of adjusting the peel force (R1) or (R2) and from the viewpoint of producing a composition capable of forming a cured product having improved adhesive strength and low dielectric characteristics, and more preferably contains a polyfunctional compound (C) (hereinafter also referred to as "component (C)") in addition to components (a) and (B), the component (C) having 2 or more unsaturated hydrocarbon groups having a double bond at the terminal.
The curable adhesive composition used in one embodiment of the present invention preferably further contains 1 or more selected from the group consisting of a cationic polymerization initiator (D) (hereinafter, also referred to as "component (D)"), a crosslinking agent (E) (hereinafter, also referred to as "component (E)") which is reactive with the above-described reactive functional group of component (a), and a silane coupling agent (F) (hereinafter, also referred to as "component (F)").
The curable adhesive composition used in one embodiment of the present invention may contain additives other than these components (a) to (F) within a range that does not impair the effects of the present invention.
In the curable adhesive composition used in one embodiment of the present invention, the total content of the component (a) and the component (B) is preferably 50% by mass or more, more preferably 60% by mass or more, still more preferably 70% by mass or more, still more preferably 75% by mass or more, and is usually 100% by mass or less, preferably 99.90% by mass or less, more preferably 99.00% by mass or less, still more preferably 95.00% by mass or less, relative to the total amount (100% by mass) of the active components of the curable adhesive composition, from the viewpoint of adjusting the release force (R1) or (R2) and from the viewpoint of producing a composition capable of forming a curable adhesive layer or a cured product thereof having improved adhesive strength and low dielectric characteristics.
From the above point of view, in the curable adhesive composition used in one embodiment of the present invention, the total content of the component (a), the component (B), the component (C) and the component (D) is preferably 60% by mass or more, more preferably 75% by mass or more, still more preferably 90% by mass or more, and in addition, is usually 100% by mass or less, 99.70% by mass or less, or 90% by mass or less, relative to the total amount (100% by mass) of the active ingredients of the curable adhesive composition.
From the above point of view, in the curable adhesive composition used in one embodiment of the present invention, the total content of the component (a), the component (B), the component (C), the component (D), the component (E) and the component (F) is preferably 60% by mass or more, more preferably 75% by mass or more, still more preferably 90% by mass or more, and in addition, is usually 100% by mass or less, 99.70% by mass or less, or 90% by mass or less, relative to the total amount (100% by mass) of the active ingredients of the curable adhesive composition.
Details of the components contained in the curable adhesive composition used in one embodiment of the present invention will be described below.
< Component (A): adhesive resin >, adhesive resin
The curable adhesive composition used in one embodiment of the present invention preferably contains the adhesive resin (a). The composition containing the binder resin (a) can form a curable adhesive layer having excellent adhesive strength and good shape stability when a cured product is produced.
The binder resin (A) may be used alone or in combination of 2 or more.
In the curable adhesive composition used in one embodiment of the present invention, the content of the component (a) is preferably 35% by mass or more, more preferably 45% by mass or more, further preferably 55% by mass or more, and further preferably 90% by mass or less, more preferably 80% by mass or less, further preferably 75% by mass or less, relative to the total amount (100% by mass) of the active ingredients of the curable adhesive composition.
The number average molecular weight (Mn) of the binder resin (a) used in one embodiment of the present invention is preferably 10,000 or more, more preferably 25,000 or more, still more preferably 35,000 or more from the viewpoint of improving film forming property and forming a composition capable of forming a curable adhesive layer having good shape stability, and is preferably 150,000 or less, more preferably 100,000 or less, still more preferably 70,000 or less from the viewpoint of improving solubility of the component (a) with a diluting solvent and forming a composition having excellent coatability when the composition is brought into a solution state.
Examples of the binder resin (a) include: polyolefin-based resins, phenoxy-based resins, polyimide-based resins, polyamideimide-based resins, polyvinyl butyral-based resins, polycarbonate-based resins, styrene-based resins, and the like.
Among these, the binder resin (a) used in one embodiment of the present invention preferably contains a polyolefin resin from the viewpoint of being a composition that can form a cured product excellent in dielectric characteristics in a high frequency region (for example, 1GHz or more).
The polyolefin resin may be a polymer having a constituent unit derived from an olefin monomer, a polymer having a constituent unit derived from an olefin monomer alone, or a copolymer having a constituent unit derived from an olefin monomer and a constituent unit derived from a monomer copolymerizable with an olefin monomer.
Examples of the olefin monomer constituting the polyolefin resin include: the alpha-olefin having 2 or more carbon atoms is preferably an alpha-olefin having 2 to 8 carbon atoms, more preferably at least 1 selected from ethylene, propylene, 1-butene, isobutylene and 1-hexene, and still more preferably at least 1 selected from ethylene and propylene.
These olefin monomers may be used alone or in combination of 2 or more.
Examples of the monomer copolymerizable with the olefin monomer constituting the polyolefin resin include: vinyl acetate, (meth) acrylate, styrene, and the like. These monomers may be used alone or in combination of 2 or more.
Specifically, examples of the polyolefin-based resin used in one embodiment of the present invention include: ultra low density polyethylene (VLDPE), low Density Polyethylene (LDPE), medium Density Polyethylene (MDPE), high Density Polyethylene (HDPE), linear low density polyethylene, polypropylene (PP), ethylene-propylene copolymers, olefin-based elastomers (TPO), ethylene-vinyl acetate copolymers (EVA), ethylene- (meth) acrylic acid copolymers, ethylene- (meth) acrylate copolymers, and the like.
The binder resin (a) used in one embodiment of the present invention preferably contains a binder resin having a reactive functional group, more preferably contains 1 or more selected from a polyolefin resin having a reactive functional group and a styrene resin having a reactive functional group, and even more preferably contains at least a polyolefin resin (A1) having a reactive functional group, from the viewpoints of improving film forming properties, forming a composition capable of forming a curable adhesive layer having good shape stability, forming a composition capable of forming a cured product having further improved low dielectric characteristics, and reducing peeling force at the time of peeling the 1 st or 2 nd release film from the curable adhesive layer.
In the curable adhesive composition used in one embodiment of the present invention, the content of the polyolefin resin (A1) is preferably 50 to 100 mass%, more preferably 70 to 100 mass%, and even more preferably 85 to 100 mass% with respect to the total amount (100 mass%) of the component (a) contained in the curable adhesive composition, from the viewpoint of a composition capable of forming a cured product having more excellent low dielectric characteristics.
Examples of the reactive functional group of the binder resin (a) include: carboxyl group, group having carboxylic anhydride structure, group having carboxylic ester structure, hydroxyl group, epoxy group, amide group, ammonium group, nitrile group, amino group, imide group, isocyanate group, acetyl group, thiol group, sulfo group, phosphine group, nitro group, halogen atom, alkoxysilyl group, and the like.
The reactive functional group of the binder resin (a) may be composed of 1 kind alone or 2 or more kinds in combination.
Among these, the reactive functional group of the binder resin (a) is preferably selected from a group consisting of a carboxyl group, a group having a carboxylic anhydride structure, an epoxy group, an amide group, an ammonium group, a nitrile group, an amino group, an imide group, an isocyanate group, an acetyl group, a thiol group, an ether group, a thioether group, a sulfo group, a phosphine group, a nitro group, a urethane group, a halogen atom and an alkoxysilyl group, and a group having a carboxylic anhydride structure is more preferably selected from a group consisting of a carboxyl group and a group having a carboxylic anhydride structure from the viewpoint of reducing the peeling force at the time of peeling the 1 st release film or the 2 nd release film from the curable adhesive layer, and a group having a carboxylic anhydride structure is more preferably selected from the viewpoint of forming a composition capable of forming a cured product having more excellent adhesive strength and further excellent low dielectric characteristics.
The binder resin (a) used in one embodiment of the present invention may be a modified resin obtained by modifying a resin as a main chain with a modifier to introduce the above-described reactive functional group.
Specific examples of the modified resin include: the acid-modified resin having an acid group and the resin having a hydroxyl group are preferable from the viewpoint of forming a composition capable of forming a cured product having more excellent adhesive strength and from the viewpoint of reducing the peeling force when peeling the 1 st release film or the 2 nd release film from the curable adhesive layer, and the acid-modified resin having an acid group is more preferable from the viewpoint of forming a composition capable of forming a cured product having more excellent adhesive strength and further more excellent low dielectric characteristics.
The acid-modified resin or acid anhydride-modified resin (hereinafter also referred to as "unsaturated carboxylic acid or the like") is obtained, for example, by reacting an unsaturated carboxylic acid or the like with a resin as a main chain to introduce a carboxyl group or carboxylic acid anhydride structure for graft modification.
The method for introducing an unsaturated carboxylic acid or the like into the resin is not particularly limited, and examples thereof include: a method in which a resin, an unsaturated carboxylic acid, and the like are heated to a temperature equal to or higher than the melting point of the resin in the presence of a radical generator such as an organic peroxide or an azonitrile, and melted to react the resin and the unsaturated carboxylic acid; or a method in which a resin, an unsaturated carboxylic acid or the like is dissolved in an organic solvent, and then heated and stirred in the presence of a radical generator to react.
Examples of the unsaturated carboxylic acid include: maleic acid, fumaric acid, itaconic acid, citraconic acid, glutaconic acid (glutaconic acid), tetrahydrophthalic acid, aconitic acid, and the like.
Examples of the unsaturated carboxylic acid anhydride include: maleic anhydride, itaconic anhydride, glutaconic anhydride, citraconic anhydride, aconitic anhydride, norbornene dicarboxylic anhydride, tetrahydrophthalic anhydride, and the like.
These may be used alone or in combination of 2 or more.
Among these, maleic anhydride is preferable from the viewpoint of forming a composition that can form a cured product having more excellent adhesive strength and low dielectric characteristics.
From the viewpoint of forming a composition that can form a cured product having more excellent adhesive strength and low dielectric characteristics, the amount of unsaturated carboxylic acid or the like to be added to the resin is preferably 0.1 to 5 parts by mass, more preferably 0.2 to 3 parts by mass, and even more preferably 0.2 to 1 part by mass, relative to 100 parts by mass of the resin.
< Component (B): polyphenylene ether resin
The curable adhesive composition used in one embodiment of the present invention preferably contains the polyphenylene ether resin (B) from the viewpoint of adjusting the peel force (R1) or (R2) and from the viewpoint of being a composition capable of forming a cured product having improved adhesive strength and low dielectric characteristics.
The polyphenylene ether resin (B) may be used alone or in combination of 2 or more.
In the curable adhesive composition used in one embodiment of the present invention, the content of the component (B) is preferably 5 parts by mass or more, more preferably 12 parts by mass or more, still more preferably 17 parts by mass or more, and further preferably 80 parts by mass or less, more preferably 60 parts by mass or less, still more preferably 40 parts by mass or less, based on 100 parts by mass of the total amount of the component (a).
The number average molecular weight (Mn) of the polyphenylene ether resin (B) used in one embodiment of the present invention is preferably 1500 or more, more preferably 1700 or more, still more preferably 1900 or more from the viewpoint of adjusting the peeling force (R1) or (R2) and from the viewpoint of forming a composition capable of forming a cured product having improved adhesive strength and low dielectric characteristics, and from the viewpoint of making the composition into a solution form, the composition is preferably 7000 or less, more preferably 5500 or less, still more preferably 4000 or less from the viewpoint of making the solubility of the component (B) with a diluting solvent good and forming a composition excellent in coatability.
The polyphenylene ether resin (B) used in one embodiment of the present invention may be any resin having a main chain having a constituent unit represented by at least one of the following general formulae (B-i) and (B-ii).
[ Chemical formula 1]
In the above general formula (b-i) or formula (b-ii), R a1 and R a2 are each independently a halogen atom (fluorine atom, chlorine atom, bromine atom or iodine atom), an alkyl group having 1 to 6 carbon atoms, or a phenyl group, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, further preferably an alkyl group having 1 to 3 carbon atoms, further preferably a methyl group or an ethyl group, and particularly preferably a methyl group.
Examples of the alkyl group having 1 to 6 carbon atoms which may be selected as R a1 and R a2 include: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, sec-butyl, isobutyl, n-pentyl, n-hexyl and the like.
M1 and m2 each independently represent an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and even more preferably 2.
The polyphenylene ether resin (B) used in one embodiment of the present invention is preferably a resin having a skeleton represented by the following formula (B-1) as a main chain, from the viewpoints of adjusting the peeling force (R1) or (R2) and forming a composition capable of forming a cured product having excellent low dielectric characteristics and further improved adhesive strength.
[ Chemical formula 2]
In the above general formula (b-1), R a1 and R a2, and m1 and m2 are the same as defined in the above general formula (b-i) or formula (b-ii), and the kinds and numerical ranges for the suitable groups are also the same.
X is a divalent organic group, at least 1 hydrogen atom of which may be substituted with a substituent.
P1 and p2 are each independently an integer of 0 or more, and p1+p2 is an integer of 1 or more.
* Represents the bonding position to the terminal group.
Examples of the divalent hydrocarbon group optionally used as X include: alkylene having 1 to 20 carbon atoms, oxyalkylene having 1 to 20 carbon atoms, alkenylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 10 ring-forming carbon atoms, phenylene, biphenylene, naphthylene, a group formed by combining 2 or more of these groups, and the like.
The alkylene group, the oxyalkylene group, and the alkenylene group may be linear or branched.
The alkylene group, the oxyalkylene group and the alkenylene group may have a substituent selected from the group consisting of a halogen atom, a phenyl group, a biphenyl group, a naphthyl group and a cycloalkyl group having 3 to 10 carbon atoms.
The cycloalkylene group, the cycloalkenylene group, the phenylene group, the biphenylene group, and the naphthylene group may have a substituent selected from the group consisting of a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group (oxyalkyl) having 1 to 6 carbon atoms, and an alkenyl group having 1 to 6 carbon atoms.
Among these, X is preferably a group represented by the following formula (b-2) from the viewpoint of adjusting the peeling force (R1) or (R2) and from the viewpoint of forming a composition that can form a cured product with further improved adhesive strength.
[ Chemical formula 3]
In the above general formula (b-2), R b1 and R b2 are each independently a halogen atom (fluorine atom, chlorine atom, bromine atom or iodine atom), an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or an alkenyl group having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, further preferably an alkyl group having 1 to 3 carbon atoms, further preferably a methyl group or an ethyl group, particularly preferably a methyl group.
Examples of the alkyl group having 1 to 6 carbon atoms which may be selected as R b1 and R b2 include: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, sec-butyl, isobutyl, n-pentyl, n-hexyl and the like.
N1 and n2 are each independently an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 1 to 3, and still more preferably 3.
In the above general formula (b-2), A is a single bond or a divalent hydrocarbon group.
Examples of the divalent hydrocarbon group which may be selected as A include: alkylene having 1 to 20 carbon atoms, oxyalkylene having 1 to 20 carbon atoms, alkenylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 10 ring-forming carbon atoms, or cycloalkylene having 3 to 10 ring-forming carbon atoms.
The alkylene group, the oxyalkylene group, and the alkenylene group may be linear or branched.
Further, the hydrocarbon group optionally used as A may have a substituent selected from the group consisting of a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms and an alkenyl group having 1 to 6 carbon atoms.
Among these, from the viewpoint of adjusting the peeling force (R1) or (R2) and from the viewpoint of forming a composition that can form a cured product having further improved adhesive strength, a is preferably a single bond or an alkylene group having 1 to 20 carbon atoms, more preferably a single bond.
The polyphenylene ether resin (B) used in one embodiment of the present invention is more preferably a resin having a skeleton represented by the following formula (B-3) as a main chain, from the viewpoints of adjusting the peel force (R1) or (R2) and forming a composition capable of forming a cured product having further improved adhesive strength.
[ Chemical formula 4]
In the above general formula (b-3), R a1 and R a2 are the same as defined in the above general formula (b-i) or formula (b-ii), and the kinds and numerical ranges for the suitable groups are also the same.
R b1 and R b2 are as defined in the above general formula (b-2), and the types and numerical ranges of the suitable groups are the same.
P1 and p2 are each independently an integer of 0 or more, and p1+p2 is an integer of 1 or more.
* Represents the bonding position to the terminal group.
R a1、Ra2、Rb1 and R b2 in the general formula (b-3) are each independently preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, still more preferably an alkyl group having 1 to 3 carbon atoms, still more preferably a methyl group or an ethyl group, and particularly preferably a methyl group.
The polyphenylene ether resin (B) used in one embodiment of the present invention is preferably a polyphenylene ether resin having a vinyl group from the viewpoint of adjusting the peel force (R1) or (R2) and from the viewpoint of forming a composition which can form a cured product having further improved low dielectric characteristics, crosslinkability and heat resistance.
The vinyl group contained in the polyphenylene ether resin (B) may be a group constituting a part of a hydrocarbon substituent such as a vinylbenzyl group and a vinylnaphthyl group. That is, the polyphenylene ether resin (B) is formed by bonding a vinyl group or a hydrocarbon group containing a vinyl group to a polyphenylene ether skeleton.
The polyphenylene ether resin (B) used in one embodiment of the present invention is preferably a resin having vinyl groups or vinyl-containing hydrocarbon groups at both ends of the main chain, from the viewpoint of adjusting the peeling force (R1) or (R2) and from the viewpoint of being a composition capable of forming a cured product excellent in low dielectric characteristics, crosslinkability and heat resistance.
The polyphenylene ether resin (B) having vinyl groups or vinyl-containing hydrocarbon groups at both terminals of the main chain can be obtained by introducing vinyl groups or vinyl-containing hydrocarbon groups to both terminals after forming a polyphenylene ether skeleton as the main chain.
Specifically, a 2-functional phenol compound is reacted with a monofunctional phenol compound to obtain a polymer having phenolic hydroxyl groups at both terminals, and then the terminal phenolic hydroxyl groups are subjected to vinylbenzyl etherification with 4- (chloromethyl) styrene, whereby a polyphenylene ether resin (B) having vinylbenzyl groups at both terminals of the polyphenylene ether skeleton can be obtained.
The polyphenylene ether resin (B) used in one embodiment of the present invention is preferably a compound represented by the following general formula (B-4).
[ Chemical formula 5]
P1 and p2 are each independently an integer of 0 or more, and p1+p2 is an integer of 1 or more.
As the polyphenylene ether resin (B) used in one embodiment of the present invention, commercially available ones can be used. Examples of the commercial products include: OPE-2St (a compound represented by the above general formula (b-4)) manufactured by Mitsubishi gas chemical corporation, etc.
< Component (C): polyfunctional Compound
The curable adhesive composition used in one embodiment of the present invention preferably contains a polyfunctional compound (C) having 2 or more unsaturated hydrocarbon groups having a double bond at the terminal. The polyfunctional compound (C) in the present invention does not include compounds corresponding to the component (a) and the component (B).
By forming a composition containing both the polyphenylene ether resin (B) and the polyfunctional compound (C), a cured product having improved low dielectric characteristics and adhesive strength in a balanced manner can be formed. In particular, since the polyfunctional compound (C) has 2 or more unsaturated hydrocarbon groups, a crosslinked structure is formed in the obtained cured product, and a cured product having further improved adhesive strength can be formed.
The polyfunctional compound (C) may be used alone or in combination of 2 or more.
In the curable adhesive composition used in one embodiment of the present invention, the content of the component (C) is preferably 10 parts by mass or more, more preferably 15 parts by mass or more, still more preferably 20 parts by mass or more, relative to 100 parts by mass of the total amount of the component (a), from the viewpoint of forming a composition capable of forming a cured product excellent in low dielectric characteristics and also of improving adhesion, and the release force (R1) and the release force (R2) tend to increase when the content of the component (C) increases, so that 80 parts by mass or less, more preferably 60 parts by mass or less, still more preferably 40 parts by mass or less are preferable from the viewpoint of forming a curable adhesive sheet adjusted so as to reduce the release force (R1) or the release force (R2).
In the curable adhesive composition used in one embodiment of the present invention, the content ratio [ (B)/(C) ] of the component (B) to the component (C) is preferably 15/85 or more, more preferably 30/70 or more, and further preferably 85/15 or less, more preferably 70/30 or less, from the viewpoint that a cured product having well-balanced low dielectric characteristics, adhesive strength and heat resistance can be formed.
In the curable adhesive composition used in one embodiment of the present invention, the total content of the component (B) and the component (C) is preferably 85 parts by mass or less, more preferably 75 parts by mass or less, further preferably 65 parts by mass or less, and further preferably 15 parts by mass or more, more preferably 25 parts by mass or more, further preferably 35 parts by mass or more, relative to 100 parts by mass of the total amount of the component (a), from the viewpoint of being a curable adhesive sheet adjusted to reduce the peel force (R1) or (R2), and also from the viewpoint of being a curable adhesive sheet excellent in adhesion, and being a composition capable of forming a cured product excellent in adhesive strength.
The number of carbon atoms of each of the unsaturated hydrocarbon groups of the polyfunctional compound (C) used in one embodiment of the present invention is preferably 2 to 7, more preferably 2 to 4, and still more preferably 2 to 3.
Examples of the unsaturated hydrocarbon group include: vinyl, allyl, 3-butenyl, 4-pentenyl, 5-hexenyl, isopropenyl, 1-methyl-2-propenyl, vinylbenzyl, vinylnaphthyl, and the like.
Among these, the unsaturated hydrocarbon group of the polyfunctional compound (C) is preferably an allyl group.
The number of unsaturated hydrocarbons in the polyfunctional compound (C) used in one embodiment of the present invention is 2 or more, but is preferably 2 to 4, more preferably 2 to 3, and even more preferably 2 from the viewpoint of a composition which can form a cured product having a moderately dispersed cross-linked structure and suppress occurrence of cracks, and a composition which can suppress curing shrinkage in a bonding step of forming a cured product from a curable adhesive layer and can reduce warpage of a plate-like member such as a circuit board as an adherend.
From the viewpoint of forming a composition capable of forming a cured product having more uniformly improved low dielectric characteristics and adhesive strength, the polyfunctional compound (C) used in one embodiment of the present invention is preferably a polyfunctional compound having 2 or more unsaturated hydrocarbon groups as well as a saturated hydrocarbon group.
From the above point of view, the saturated hydrocarbon number of the polyfunctional compound (C) used in one embodiment of the present invention is preferably 1 to 4, more preferably 1 to 2, and still more preferably 1.
Examples of the saturated hydrocarbon group include: alkyl, alkyl substituted with alkoxy, and the like.
Examples of the alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, sec-butyl, isobutyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, and the like.
The carbon number of the alkyl group is preferably 1 to 20, more preferably 4 to 18, still more preferably 6 to 16, still more preferably 8 to 15.
Examples of the alkyl group substituted with an alkoxy group include: methoxymethyl, ethoxymethyl, 2-methoxyethoxymethyl, benzyloxymethyl, and the like.
The number of carbon atoms of the alkoxy-substituted alkyl group is preferably 2 to 15, more preferably 2 to 12, and still more preferably 3 to 10.
The polyfunctional compound (C) used in one embodiment of the present invention preferably contains the polyfunctional compound (C1) having 2 unsaturated hydrocarbon groups described above.
As described above, the composition containing the polyfunctional compound (C1) having 2 unsaturated hydrocarbon groups can be a composition capable of forming a cured product in which occurrence of cracks is suppressed and warpage of a plate-like member such as a circuit board as an adherend is reduced, and can be a composition capable of forming a cured product in which low dielectric characteristics and adhesive strength are further improved.
From the above viewpoint, the polyfunctional compound (C1) is more preferably the polyfunctional compound having 2 unsaturated hydrocarbon groups and at least 1 saturated hydrocarbon group.
From the above point of view, in the curable adhesive composition used in one embodiment of the present invention, the content ratio of the polyfunctional compound (C1) is preferably 50 to 100% by mass, more preferably 70 to 100% by mass, still more preferably 80 to 100% by mass, and still more preferably 90 to 100% by mass, relative to the total amount (100% by mass) of the component (C) contained in the curable adhesive composition.
The polyfunctional compound (C) used in one embodiment of the present invention is preferably a polyfunctional compound having a heterocyclic skeleton. By containing the polyfunctional compound having a heterocyclic skeleton, a composition which can form a cured product having further improved low dielectric characteristics and adhesive strength can be obtained.
Specific examples of the heterocyclic skeleton include: isocyanurate or glycoluril backbones.
The polyfunctional compound (C) used in one embodiment of the present invention includes: a compound having an isocyanurate skeleton represented by the following general formula (c-1), and a compound having a glycoluril skeleton represented by the following general formula (c-2).
[ Chemical formula 6]
In the above general formula (c-1), R 11～R13 is an unsaturated hydrocarbon group having a double bond at the terminal, or a saturated hydrocarbon group, and at least 2 of R 11～R13 are the above unsaturated hydrocarbon groups.
In the general formula (c-2), R 21～R26 is a hydrogen atom, an unsaturated hydrocarbon group having a double bond at the terminal, or a saturated hydrocarbon group, and at least 2 of R 21～R26 are the unsaturated hydrocarbon groups.
Specific examples of the unsaturated hydrocarbon groups and saturated hydrocarbon groups which may be selected as R 11～R13 and R 21～R26 are as described above, and ranges of suitable carbon numbers are also as described above.
From the viewpoint of being able to form a composition capable of forming a cured product that suppresses the occurrence of cracks and reduces warpage of a plate-like member such as a circuit board as an adherend, and at the same time, being able to form a cured product that further improves low dielectric characteristics and adhesive strength, the polyfunctional compound (C) used in one embodiment of the present invention preferably contains a compound having an isocyanurate skeleton represented by the above general formula (C-1), and more preferably contains a compound (C11) having an isocyanurate skeleton represented by the following general formula (C-11).
[ Chemical formula 7]
In the above general formula (c-11), R a is a saturated hydrocarbon group, and specific examples are as described above.
Among these, R a is preferably an alkyl group. The carbon number of the alkyl group is preferably 1 to 20, more preferably 4 to 18, still more preferably 6 to 16, still more preferably 8 to 15.
From the above point of view, in the curable adhesive composition used in one embodiment of the present invention, the content of the compound (C11) is preferably 50 to 100% by mass, more preferably 70 to 100% by mass, still more preferably 80 to 100% by mass, and still more preferably 90 to 100% by mass, relative to the total amount (100% by mass) of the component (C) contained in the curable adhesive composition.
The polyfunctional compound (C) used in one embodiment of the present invention may be commercially available.
Specific commercial products include, for example: L-DAIC (product name, manufactured by Shimadzu chemical Co., ltd., compound represented by the above general formula (c-11)), TAIC (registered trademark) (product name, manufactured by Mitsubishi chemical Co., ltd., compound in which R 11～R13 in the above general formula (c-1) is an allyl group), TA-G (product name, manufactured by Shimadzu chemical Co., ltd., compound represented by the above general formula (c-2)), and the like.
The molecular weight (formula weight) of the polyfunctional compound (C) used in one embodiment of the present invention is preferably 200 or more, more preferably 230 or more, still more preferably 270 or more from the viewpoint of a composition that is easy to form a cured product having desired physical properties, and the peeling force (R1) and the peeling force (R2) tend to increase as the molecular weight of the component (C) decreases, so that a curable adhesive sheet adjusted so as to reduce the peeling force (R1) or the peeling force (R2) is produced, and is preferably 1000 or less, more preferably 800 or less, still more preferably 500 or less from the viewpoint of a composition that is easy to form a curable adhesive layer that is easy to adhere at normal temperature.
The boiling point of the polyfunctional compound (C) used in one embodiment of the present invention is preferably 175 to 350℃and more preferably 200 to 300 ℃.
The temperature for 5% weight reduction of the polyfunctional compound (C) used in one embodiment of the present invention is preferably 175 to 350℃and more preferably 200 to 300 ℃.
Further, the polyfunctional compound (C) used in one embodiment of the present invention is preferably a compound which is liquid (liquid) at 25 ℃ from the viewpoint of being a composition capable of forming a cured product excellent in low dielectric characteristics and also being a composition capable of easily forming a curable adhesive layer which is easily adhered at ordinary temperature.
In the present specification, the term "compound which is liquid at 25℃means a compound having fluidity at 25℃and specifically means a compound having a viscosity of 2 to 10000 mPas measured at 25℃and 1.0rpm using an E-type viscometer.
< Component (D): cationic polymerization initiator >, and
The curable adhesive composition used in one embodiment of the present invention preferably further contains a cationic polymerization initiator (D).
The polymerization reaction of the component (B) and the component (C) can be sufficiently performed by preparing a curable adhesive composition containing the cationic polymerization initiator (D), and the storage stability of the resulting curable adhesive layer can be improved. The cationic polymerization initiator (D) may be used alone or in combination of 2 or more.
In the curable adhesive composition used in one embodiment of the present invention, the content of the component (D) is preferably 0.01 part by mass or more, more preferably 0.05 part by mass or more, still more preferably 0.10 part by mass or more, still more preferably 0.15 part by mass or more, still more preferably 0.20 part by mass or more, still more preferably 0.25 part by mass or more, particularly preferably 0.30 part by mass or more, and further preferably 6.0 parts by mass or less, more preferably 5.0 parts by mass or less, still more preferably 3.0 parts by mass or less, still more preferably 2.0 parts by mass or less, still more preferably 1.5 parts by mass or less, still more preferably 1.0 part by mass or less, particularly preferably 0.70 part by mass, from the viewpoint of forming a curable adhesive layer that can sufficiently proceed the polymerization reaction of the component (B) and the component (C) and that improves the storage stability.
The cationic polymerization initiator (D) used in one embodiment of the present invention may be a thermal cationic polymerization initiator or a photo cationic polymerization initiator, but is preferably a thermal cationic polymerization initiator from the viewpoint of enabling polymerization in a simple process.
The thermal cationic polymerization initiator used in one embodiment of the present invention is a compound that can generate a cationic species that initiates polymerization by heating, and examples thereof include: sulfonium salts, quaternary ammonium salts, phosphonium salts, diazonium salts, iodonium salts, and the like.
These thermal cationic polymerization initiators may be used alone or in combination of 2 or more.
Examples of the sulfonium salt include: triphenylsulfonium tetrafluoroborate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium hexafluoroarsonate, tris (4-methoxyphenyl) sulfonium hexafluoroarsonate, diphenyl (4-thiophenylphenyl) sulfonium hexafluoroarsonate, and the like.
Further, commercially available sulfonium salts can be used, and examples thereof include: adeka Opton SP-150, adeka Opton SP-170, adeka Opton CP-66, adeka Opton CP-77 (manufactured by ADEKA, inc. above); san-Aid SI-60L, san-Aid SI-80L, san-Aid SI-100L, san-Aid SI-B2A, san-Aid SI-B3 (manufactured by Sanxinshi chemical Co., ltd.); CYRACURE UVI-6974, CYRACURE UVI-6990 (manufactured by Union Carbide company, supra); UVI-508, UVI-509 (manufactured by GENERAL ELECTRIC, supra); FC-508, FC-509 (manufactured by Minnesota Mining & Manufacturing company, supra); CD-1010, CD-1011 (manufactured by Sartomer Corp., above); CI series products (manufactured by Nippon Caesada Co., ltd.).
Examples of the quaternary ammonium salt include: tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium bisulfate, tetraethylammonium tetrafluoroborate, tetraethylammonium p-toluenesulfonate, N-dimethyl-N-benzylanilinium hexafluoroantimonate, N-dimethyl-N-benzylanilinium tetrafluoroborate, N, N-dimethyl-N-benzylpyridinium hexafluoroantimonate, N-diethyl-N-benzyltriflate, N-dimethyl-N- (4-methoxybenzyl) pyridinium hexafluoroantimonate, N-diethyl-N- (4-methoxybenzyl) toluidinium hexafluoroantimonate, and the like.
Examples of phosphonium salts include: ethyl triphenyl phosphonium hexafluoroantimonate, tetrabutylphosphonium hexafluoroantimonate, and the like.
Examples of diazonium salts include: AMERICURE (manufactured by AMERICAN CAN), ULTRASET (manufactured by Adeka), and the like.
Examples of the iodonium salt include: diphenyliodonium hexafluoroarsenate, bis (4-chlorophenyl) iodonium hexafluoroarsenate, bis (4-bromophenyl) iodonium hexafluoroarsenate, phenyl (4-methoxyphenyl) iodonium hexafluoroarsenate, and the like.
Further, commercially available iodonium salts can be used, and examples thereof include: UV-9310C (manufactured by Toshiba silicone Co., ltd.) Photoinitiator 2074%Manufactured by Poulenc corporation), the UVE series of products (manufactured by GENERAL ELECTRIC corporation), the FC series of products (manufactured by Minnesota Mining & Manufacturing corporation), and the like.
In the case where the curable adhesive composition according to one embodiment of the present invention contains the cationic polymerization initiator (D), at least a part of the cationic polymerization initiator (D) may be a high-temperature reactive thermal cationic polymerization initiator having a peak top temperature of a heat generation peak obtained by differential scanning calorimetric measurement under the following conditions exceeding 120 ℃.
(Differential scanning calorimetric conditions)
A mixture of 0.1 part by mass of a cationic polymerization initiator to be measured, 100 parts by mass of bisphenol A diglycidyl ether, and 0.1 part by mass of gamma-butyrolactone was mixed as a measurement sample, and differential scanning calorimetric measurement was performed at a heating rate of 10 ℃/min from 30℃to 300℃to measure the peak temperature of a heat generation peak.
Examples of commercial products of the high-temperature reactive thermal cationic polymerization initiator include: san-Aid SI-B3, san-Aid SI-B4, san-Aid SI-B5, san-Aid SI-150 (all manufactured by Sanxinshi chemical Co., ltd.), and the like.
< Other reactive curing agent other than cationic polymerization initiator (D) >)
The curable adhesive composition used in one embodiment of the present invention may contain a reactive curing agent other than the cationic polymerization initiator (D) in place of or together with the cationic polymerization initiator (D) within a range that does not impair the effects of the present invention.
In the curable adhesive composition used in one embodiment of the present invention, the content of the other reactive curing agent may be set to 0 to 90 parts by mass, 0 to 50 parts by mass, 0 to 40 parts by mass, 0 to 30 parts by mass, 0 to 20 parts by mass, 0 to 10 parts by mass, 0 to 5.0 parts by mass, 0 to 2.0 parts by mass, 0 to 1.0 parts by mass, 0 to 0.10 parts by mass, 0 to 0.010 parts by mass, or 0 to 0.0010 parts by mass, based on 100 parts by mass of the total amount of the component (D).
On the other hand, in the case where the curable adhesive composition according to one embodiment of the present invention does not contain the cationic polymerization initiator (D), the content of the other reactive curing agent may be 0.01 part by mass or more, 0.05 part by mass or more, 0.10 part by mass or more, 0.15 part by mass or more, 0.20 part by mass or more, 0.25 part by mass or more, or 0.30 part by mass or more, or 6.0 parts by mass or less, 5.0 parts by mass or less, 3.0 parts by mass or less, 2.0 parts by mass or less, 1.5 parts by mass or less, 1.0 parts by mass or less, or 0.70 parts by mass or less, based on 100 parts by mass of the total amount of the component (B) and the component (C).
Examples of the reactive curing agent other than the cationic polymerization initiator (D) include: amine compounds such as benzyl methylamine and 2,4, 6-tris (dimethylaminomethyl) phenol; imidazole compounds such as 2-methylimidazole, 2-ethyl-4-methylimidazole and 2-heptadecylimidazole; lewis acids such as boron trifluoride/monoethylamine complex, boron trifluoride/piperazine complex, and the like; peroxides such as di (t-butylperoxy) diisopropylbenzene, and the like.
< Ingredient (E): crosslinking agent >
In the case where the curable adhesive composition used in one embodiment of the present invention contains a binder resin having a reactive functional group as the component (a), it is preferable to further contain a crosslinking agent (E) that can react with the reactive functional group.
The composition containing the component (A) and the crosslinking agent (E) can form a curable adhesive layer having a high effect of suppressing the bleeding of the adhesive component. That is, in the process of forming the curable adhesive layer from the coating film formed from the curable adhesive composition, the crosslinking agent (E) reacts with the reactive functional group of the binder resin (a) to form a crosslinked structure in the coating film, whereby the curable adhesive layer which is not easily flowable even when heated can be formed. As a result, the formed curable adhesive layer is less likely to cause a phenomenon in which the adhesive component oozes out from the end portion in the bonding step of bonding the curable adhesive layer to an adherend such as a circuit board by curing the curable adhesive layer to adhere to the adherend. In addition, from the viewpoint of adjusting the peeling force (R1) or (R2), the composition containing the crosslinking agent (E) is also preferable.
The crosslinking agent (E) may be used alone or in combination of 2 or more.
In the curable adhesive composition used in one embodiment of the present invention, the content of the component (E) is preferably 0.01 part by mass or more, more preferably 0.03 part by mass or more, more preferably 0.05 part by mass or more, more preferably 0.07 part by mass or more, more preferably 0.10 part by mass or more, more preferably 0.15 part by mass or more, more preferably 0.20 part by mass or more, more preferably 0.25 part by mass or more, particularly preferably 0.30 part by mass or more, and further preferably 10.0 parts by mass or less, more preferably 8.0 parts by mass or less, more preferably 6.0 parts by mass or less, more preferably 5.0 parts by mass or less, more preferably 4.0 parts by mass or less, more preferably 3.0 parts by mass or less, more preferably 2.5 parts by mass or less, more preferably 2.0 parts by mass or less, particularly preferably 1.5 parts by mass or less, relative to 100 parts by mass of the total amount of the component (a).
The molecular weight of the crosslinking agent (E) used in one embodiment of the present invention is preferably 1000 or less, more preferably 800 or less, still more preferably 700 or less, still more preferably 600 or less, particularly preferably 500 or less, from the viewpoint of being a composition that can enhance the reaction probability with the component (a), can easily form a crosslinked structure, and can form a curable adhesive layer having a higher effect of inhibiting bleeding of the adhesive component, and is preferably 100 or more, more preferably 150 or more, still more preferably 200 or more, still more preferably 250 or more, particularly preferably 300 or more, from the viewpoint of being a composition that can be adjusted to have the crosslinking agent (E) retained in the curable adhesive layer by heating in a drying step for forming the curable adhesive layer, and can exhibit the effect obtained by adding the crosslinking agent (E).
The crosslinking agent (E) used in one embodiment of the present invention is suitably selected according to the kind of the reactive functional group contained in the component (a), and examples thereof include: isocyanate-based crosslinking agents, epoxy-based crosslinking agents, metal chelate-based crosslinking agents, aziridine-based crosslinking agents, and the like.
Of these, the crosslinking agent (E) used in one embodiment of the present invention is preferably at least 1 selected from the group consisting of an isocyanate-based crosslinking agent, an epoxy-based crosslinking agent and a metal chelate-based crosslinking agent from the viewpoint of storage stability.
In addition, the crosslinking agent (E) used in one embodiment of the present invention is preferably a crosslinking agent having an isocyanurate skeleton from the viewpoint of being a composition capable of forming a cured product having further improved low dielectric characteristics.
The isocyanate-based crosslinking agent is preferably a compound having 2 or more isocyanate groups in the molecule, and examples thereof include: 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, hydrogenated xylene diisocyanate, 1, 5-pentamethylene diisocyanate, 1, 6-hexamethylene diisocyanate, diphenylmethane-4, 4-diisocyanate, isophorone diisocyanate, 1, 3-bis (isocyanatomethyl) cyclohexane, tetramethylxylylene diisocyanate, 1, 5-naphthalene diisocyanate, triphenylmethane triisocyanate, adducts of these polyisocyanate compounds with polyol compounds such as trimethylolpropane, biuret or isocyanurate of these polyisocyanate compounds, and the like.
The epoxy crosslinking agent is preferably a compound having 2 or more epoxy groups in the molecule, and examples thereof include: 1, 3-bis (N, N-diglycidyl aminomethyl) cyclohexane, N, N, N ', N' -tetraglycidyl m-xylylenediamine, ethylene glycol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, trimethylolpropane diglycidyl ether, diglycidyl aniline, diglycidyl amine, and the like.
Examples of the metal chelate-based crosslinking agent include: chelating compounds having metal ions that act as crosslinking points. Examples of the metal ion include: aluminum ion, zirconium ion, titanium ion, zinc ion, iron ion, tin ion, and the like.
Among these, the metal chelate crosslinking agent is preferably an aluminum chelate compound, and examples thereof include: aluminum tris (acetylacetonate), aluminum bis (ethylacetoacetate), diisopropoxyaluminum monooleyl acetoacetate, monoisopropoxyaluminum dioleylacetoacetate, and the like.
Among these, the crosslinking agent (E) used in one embodiment of the present invention is preferably an isocyanate-based crosslinking agent, more preferably an isocyanurate of a polyisocyanate compound, and further preferably 1 or more selected from the group consisting of an isocyanurate of 1, 5-pentamethylene diisocyanate [1,3, 5-tris (5-isocyanatopentyl) -1,3, 5-triazine-2, 4, 6-trione ] and an isocyanurate of 1, 6-hexamethylene diisocyanate [1,3, 5-tris (6-isocyanatohexyl) -1,3, 5-triazine-2, 4, 6-trione ] from the viewpoint of a composition which becomes a curable adhesive layer having a higher effect of suppressing bleeding of an adhesive component and a composition which becomes a cured product having further improved low dielectric characteristics.
< Component (F): silane coupling agent >, and method for producing the same
The curable adhesive composition used in one embodiment of the present invention preferably further contains a silane coupling agent (F).
By forming the composition containing the silane coupling agent, a cured product having further improved adhesive strength can be formed.
The silane coupling agent (F) may be used alone or in combination of 2 or more.
In the curable adhesive composition used in one embodiment of the present invention, the content of the component (F) is preferably 0.001 part by mass or more, more preferably 0.005 part by mass or more, more preferably 0.01 part by mass or more, more preferably 0.03 part by mass or more, more preferably 0.05 part by mass or more, more preferably 0.07 part by mass or more, more preferably 0.10 part by mass or more, more preferably 0.12 part by mass or more, particularly preferably 0.15 part by mass or more, and further preferably 6.0 parts by mass or less, more preferably 5.0 parts by mass or less, more preferably 4.0 parts by mass or less, more preferably 3.0 parts by mass or less, more preferably 2.0 parts by mass or less, more preferably 1.5 parts by mass or less, more preferably 1.0 parts by mass or less, more preferably 0.80 parts by mass or less, particularly preferably 0.60 parts by mass or less, based on 100 parts by mass of the total amount of the component (a).
The silane coupling agent (E) used in one embodiment of the present invention is preferably an organosilicon compound having at least 1 alkoxysilyl group in the molecule.
Specific examples of the silane coupling agent include: silane coupling agents having a (meth) acryloyl group, such as 3-methacryloxypropyl methyl dimethoxy silane, 3-methacryloxypropyl trimethoxy silane, 3-methacryloxypropyl methyl diethoxy silane, 3-methacryloxypropyl triethoxy silane, and 3-acryloxypropyl trimethoxy silane; silane coupling agents having a vinyl group such as vinyltrimethoxysilane, vinyltriethoxysilane, dimethoxymethylvinylsilane, diethoxymethylvinylsilane, trichlorovinylsilane, and vinyltris (2-methoxyethoxy) silane; silane coupling agents having an epoxy group, such as 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropyl trimethoxysilane, 3-glycidoxypropyl methyldiethoxysilane, 3-glycidoxypropyl triethoxysilane, and 8-glycidoxypropyl trimethoxysilane; silane coupling agents having a styrene group such as p-styryl trimethoxysilane and p-styryl triethoxysilane; silane coupling agents having an amino group such as hydrochloride salts of N- (2-aminoethyl) -3-aminopropyl methyldimethoxy silane, N- (2-aminoethyl) -3-aminopropyl trimethoxy silane, N- (2-aminoethyl) -3-aminopropyl triethoxy silane, 3-aminopropyl trimethoxy silane, 3-triethoxysilyl-N- (1, 3-dimethyl/butylene) propylamine, N-phenyl-3-aminopropyl trimethoxy silane, N- (vinylbenzyl) -2-aminoethyl-3-aminopropyl trimethoxy silane; silane coupling agents having an ureido group such as 3-ureidopropyltrimethoxysilane and 3-ureidopropyltriethoxysilane; silane coupling agents having halogen atoms such as 3-chloropropyl trimethoxysilane and 3-chloropropyl triethoxysilane; mercapto silane coupling agents such as 3-mercaptopropyl methyl dimethoxy silane and 3-mercaptopropyl trimethoxy silane; silane coupling agents having a thioether group, such as bis (trimethoxysilylpropyl) tetrasulfide and bis (triethoxysilylpropyl) tetrasulfide; silane coupling agents having an isocyanate group, such as 3-isocyanatopropyl trimethoxysilane and 3-isocyanatopropyl triethoxysilane; silane coupling agents having an allyl group, such as allyl trichlorosilane, allyl triethoxysilane, and allyl trimethoxysilane; and silane coupling agents having a hydroxyl group such as 3-hydroxypropyl trimethoxysilane and 3-hydroxypropyl triethoxysilane.
< Cyclic Ether Compounds >
The curable adhesive composition used in one embodiment of the present invention may be a composition further containing a cyclic ether compound.
The cyclic ether compound may be any compound having a cyclic ether group.
Examples of the cyclic ether group include: ethylene oxide (epoxy), propylene oxide (oxetanyl), tetrahydrofuran, tetrahydropyranyl, and the like.
In the present specification, the ethylene oxide group includes groups having an ethylene oxide structure such as a glycidyl group, a glycidyl ether group, and an epoxycyclohexyl group.
The cyclic ether compound may be used alone or in combination of 2 or more kinds.
The cyclic ether compound-containing composition has a property of forming a cured product excellent in adhesive strength, but on the other hand, the cured product tends to have a large relative dielectric constant or dielectric loss tangent, and low dielectric characteristics tend to be inferior to those of a composition containing the above-mentioned component (B) or component (C) and not containing the cyclic ether compound.
In the curable adhesive composition used in one embodiment of the present invention, the content of the cyclic ether compound may be set to less than 5.0 mass%, less than 3.0 mass%, less than 1.0 mass%, less than 0.50 mass%, less than 0.10 mass%, less than 0.010 mass%, less than 0.0010 mass%, less than 0.00010 mass%, or less than 0.000010 mass% with respect to the total amount (100 mass%) of the active ingredients of the curable adhesive composition.
In the curable adhesive composition used in one embodiment of the present invention, the content of the cyclic ether compound may be set to less than 5.0 parts by mass, less than 3.0 parts by mass, less than 1.0 parts by mass, less than 0.50 parts by mass, less than 0.10 parts by mass, less than 0.010 parts by mass, less than 0.0010 parts by mass, less than 0.00010 parts by mass, or less than 0.000010 parts by mass, relative to 100 parts by mass of the total amount of the components (a) to (C) contained in the curable adhesive composition.
< Inorganic filler >)
The curable adhesive composition used in one embodiment of the present invention may further contain an inorganic filler, or may be a composition containing no inorganic filler.
Examples of the inorganic filler include: silica, alumina, talc, aluminum hydroxide, magnesium hydroxide, titanium oxide, mica, aluminum borate, barium sulfate, boron nitride, forsterite, zinc oxide, magnesium oxide, calcium carbonate, and the like.
These inorganic fillers may be used alone or in combination of 2 or more.
However, in the curable adhesive composition used in one embodiment of the present invention, the smaller the content of the inorganic filler is, the more preferable.
In the curable adhesive composition used in one embodiment of the present invention, the content of the inorganic filler may be set to 0 to 30 mass%, 0 to 20 mass%, 0 to 10 mass%, 0 to 5.0 mass%, 0 to 2.0 mass%, 0 to 1.0 mass%, 0 to 0.1 mass%, 0 to 0.01 mass%, or 0 to 0.001 mass% with respect to the total amount (100 mass%) of the active ingredients of the curable adhesive composition.
In the curable adhesive composition used in one embodiment of the present invention, the content of the inorganic filler may be set to less than 50 parts by mass, less than 30 parts by mass, less than 10 parts by mass, less than 5.0 parts by mass, less than 1.0 parts by mass, less than 0.1 parts by mass, less than 0.01 parts by mass, less than 0.001 parts by mass, or less than 0.0001 parts by mass, relative to 100 parts by mass of the total amount of the components (a) to (C) contained in the curable adhesive composition.
< Other additives >)
The curable adhesive composition used in one embodiment of the present invention may contain other additives than the above components within a range that does not hinder the effects of the present invention.
Examples of other additives include: ultraviolet light absorbers, antistatic agents, light stabilizers, antioxidants, resin stabilizers, pigments, extenders, softeners, and the like.
These additives may be used alone or in combination of 2 or more.
The content of these additives may be appropriately set according to the kind of the additive.
For example, the content of each additive may be set to 0.001 to 30 parts by mass, 0.005 to 20 parts by mass, 0.01 to 10 parts by mass, or 0.03 to 5 parts by mass, relative to 100 parts by mass of the total amount of the component (a) contained in the curable adhesive composition.
< Active ingredient of liquid >
The curable adhesive composition used in one embodiment of the present invention preferably contains an active ingredient that is liquid at 25 ℃. The adhesiveness of the curable adhesive layer formed can be improved by preparing a composition containing a liquid active ingredient.
In the curable adhesive composition used in one embodiment of the present invention, the content of the active ingredient which is liquid at 25 ℃ is preferably 7.0% by mass or more, more preferably 10% by mass or more, still more preferably 12% by mass or more, and the content of the active ingredient which is liquid at 25 ℃ is more, and the peel force (R1) and the peel force (R2) tend to increase from the viewpoint of the composition forming a curable adhesive layer excellent in adhesiveness, so that the curable adhesive sheet adjusted so as to reduce the peel force (R1) or the peel force (R2) is preferably 50% by mass or less, more preferably 35% by mass or less, still more preferably 25% by mass or less, from the viewpoint of the total amount (100% by mass) of the active ingredient of the curable adhesive composition.
From the standpoint of forming a composition capable of forming a curable adhesive layer excellent in adhesion and forming a composition capable of forming a cured product having further improved low dielectric characteristics and adhesive strength, at least 1 of the polyfunctional compounds (C) contained in the curable adhesive composition used in one embodiment of the present invention is preferably an active ingredient that is liquid at 25 ℃.
In the curable adhesive composition used in one embodiment of the present invention, the content of the polyfunctional compound (C) is preferably 70 mass% or more, more preferably 80 mass% or more, still more preferably 85 mass% or more, based on the total amount (100 mass%) of the active ingredient that is liquid at 25 ℃, and may be generally 100 mass% or less, preferably 99.0 mass% or less, more preferably 98.0 mass% or less.
< Dilution solvent >)
The curable adhesive composition used in one embodiment of the present invention may be further added with a diluting solvent to be in the form of a solution.
Examples of the diluent solvent used in one embodiment of the present invention include: aromatic hydrocarbon solvents such as benzene and toluene; ester solvents such as ethyl acetate and butyl acetate; ketone solvents such as acetone, butanone, and methyl isobutyl ketone; aliphatic hydrocarbon solvents such as n-pentane, n-hexane and n-heptane; alicyclic hydrocarbon solvents such as cyclopentane, cyclohexane and methylcyclohexane.
These diluting solvents may be used alone or in combination of 2 or more.
The diluent solvent may be used as it is for the synthesis of the component (A) or (B), or may be added with 1 or more solvents other than the solvent used for the synthesis of the component (A) or (B).
In the case where the curable adhesive composition used in one embodiment of the present invention is in the form of a solution, the concentration of the active ingredient of the curable adhesive composition is suitably set to a desired viscosity in view of coatability and the like, and is preferably 3.0% by mass or more, more preferably 10% by mass or more, and is preferably 70% by mass or less, more preferably 50% by mass or less, relative to the total amount (100% by mass) of the curable adhesive composition.
[ Method for producing curable adhesive sheet ]
As a method for producing a curable adhesive sheet according to an embodiment of the present invention, the curable adhesive composition described above can be applied to a release layer of a1 st release film or a2 nd release film by a known application method.
From the viewpoint of improving the coating property on the release film, the curable adhesive composition is preferably diluted with a diluting solvent to be in the form of a solution.
Examples of the method for applying the curable adhesive composition include: spin coating, spray coating, bar coating, blade coating, roll coating, blade coating, die coating, gravure coating, and the like.
It is preferable to perform a drying treatment after the curable adhesive composition is applied to form a coating film.
Examples of the drying treatment method include: hot air drying, hot roller drying, infrared irradiation, and the like.
The drying condition of the formed coating film is preferably to heat at a temperature of 80 to 150 ℃ for 30 seconds to 5 minutes (preferably 40 seconds to 3 minutes, more preferably 45 seconds to 2 minutes) and dry. Through this drying step, a curable adhesive layer can be formed on the release layer of the 1 st release film or the 2 nd release film. Further, another release film is laminated on the exposed surface of the formed curable adhesive layer, thereby forming a curable adhesive sheet according to an embodiment of the present invention. From the viewpoint of easy obtaining of a curable adhesive sheet satisfying the above element (III) or element (IV), it is preferable to apply a curable adhesive composition to the 2 nd release film and laminate the 1 st release film on the exposed surface of the formed curable adhesive layer.
When the curable adhesive composition for forming the curable adhesive layer contains the crosslinking agent (E), it is preferable to perform the air-drying step for a predetermined period of time (for example, about 1 to 14 days) in order to complete the crosslinking reaction.
[ Method for producing cured product ]
The present invention also provides a method for producing a cured product, which uses the curable adhesive sheet according to one aspect of the present invention. The method for producing a cured product of the present invention preferably includes the following steps (1) to (3).
Step (1): and a step of adhering the curable adhesive layer exposed by peeling the 1 st release film to an adherend.
Step (2): and a step of confirming, by an optical inspection means, that no foreign matter is present at the interface between the curable adhesive layer and the adherend from the 2 nd release film side.
Step (3): and (2) curing the curable adhesive layer to obtain a cured product.
The step (1) is a step of adhering the curable adhesive layer exposed by peeling the 1 st release film to the adherend. In the curable adhesive sheet according to one embodiment of the present invention, even in a configuration in which the 1 st release film and the 2 nd release film sandwich the curable adhesive layer, the 1 st release film is easily peeled from the curable adhesive layer, so that the workability is excellent. In addition, the 1 st release film and the 2 nd release film are visually distinguishable, and are excellent in handleability.
The step (2) is a step of confirming that no foreign matter is present at the interface between the curable adhesive layer and the adherend from the side of the 2 nd release film by means of optical inspection. To confirm whether or not foreign matter is mixed, thereby improving the yield of the product.
The step (3) is a step of curing the curable adhesive layer after the step (2) to obtain a cured product.
The method for curing the adhesive layer may be a thermosetting method or a photo-curing method, and is preferably a thermosetting method from the viewpoint of productivity, since the method is selected according to the kind of the component contained in the curable adhesive composition as the material for forming the curable adhesive layer.
The heating temperature in the heat curing is preferably 80 to 200 ℃, more preferably 90 to 190 ℃, still more preferably 100 to 180 ℃, and the heating time is preferably 10 minutes to 12 hours, more preferably 30 minutes to 6 hours, still more preferably 40 minutes to 3 hours.
In addition, when heat curing is performed, heat pressing is preferably performed. The pressure at the time of hot pressing is preferably 0.1 to 10MPa, more preferably 0.5 to 8.0MPa, and still more preferably 1.0 to 5.0MPa.
In the case of curing the curable adhesive layer by the photo-curing method, the curable adhesive layer is irradiated with energy rays such as ultraviolet rays, whereby a cured product can be produced.
The method for producing a cured product using the curable adhesive sheet according to one embodiment of the present invention is not limited to the method having the step (2), and the step (2) may not be performed between the step (1) and the step (3).
[ Method for Using curable adhesive sheet, method for producing Circuit Board with cured product ]
The cured product obtained by curing the curable adhesive layer of the curable adhesive sheet according to one embodiment of the present invention has excellent low dielectric characteristics in a high frequency range.
Therefore, the curable adhesive sheet according to an embodiment of the present invention is suitable for use in forming a member in a device requiring low dielectric characteristics, and is particularly suitable for use as a cover film for protecting a circuit board.
Examples of the circuit board include: flexible printed wiring boards (FPCs), and the like.
Since the curable adhesive layer of the curable adhesive sheet according to one embodiment of the present invention has the above-described characteristics, the present invention can also provide the following [1] and [2].
[1] A method for using a curable adhesive sheet, comprising the following bonding steps: the curable adhesive layer of the curable adhesive sheet according to one aspect of the present invention is bonded to a circuit board, and the curable adhesive layer is cured to form a cured product, and the cured product is bonded to the circuit board.
[2] A method for manufacturing a circuit board with a cured product, comprising the following bonding steps: the curable adhesive layer of the curable adhesive sheet according to one aspect of the present invention is bonded to a circuit board, and the curable adhesive layer is cured to form a cured product, and the cured product is bonded to the circuit board.
In the above-mentioned [1] and [2], it is preferable that after the curable adhesive layer is bonded to the circuit board, it is confirmed that no foreign matter exists at the interface between the curable adhesive layer and the circuit board from the side of the 2 nd release film by an optical inspection means with respect to the curable adhesive layer.
In addition, in the above-mentioned [1] and [2], as a method for curing the curable adhesive layer into a cured product, the type of the reactive curing agent such as component (D) may be adjusted, and the curing method may be a thermosetting method or a photo-curing method, and specifically, examples thereof include: the method is the same as the step (3) of the method for producing a cured product according to one embodiment of the present invention.
Examples
The present invention will be described in more detail with reference to the following examples. The present invention is not limited to the following examples.
The physical properties are measured by the following methods.
[ Number average molecular weight (Mn) ]
The measurement was performed under the following conditions using a gel permeation chromatography apparatus (product name "HLC-8320GPC" manufactured by Tosoh Co., ltd.) and the value measured by conversion into standard polystyrene was used.
(Measurement conditions)
Column: "TSK gel guard column super H-H", "TSK gel super HM-H" and "TSK gel super H2000" were connected in this order (all manufactured by Tosoh Co., ltd.);
column temperature: 40 ℃;
Developing solvent: tetrahydrofuran;
Flow rate: 1.0 mL/min.
[ Thickness of layers ]
The thickness was measured by a constant pressure thickness measuring instrument (product name "PG-02J", manufactured by Kyowa Co., ltd.) in accordance with JIS K6783, Z1702 and Z1709.
[ Release force (R1) ]
The curable adhesive sheet to be measured was cut into a size of 150m×50mm in the vertical direction, and a test sample was prepared.
Then, one adhesive surface of the double-sided tape was stuck to the surface of the test sample 2 nd release film opposite to the surface in contact with the curable adhesive layer, and the other adhesive surface of the double-sided tape was laminated on the surface of the metal plate, and press-bonding was performed.
Then, the 1 st release film to be measured as a release force was peeled from the test sample fixed to the metal plate at a peeling angle of 180℃and a peeling speed of 300 mm/min using a precision universal tester (product name "Autograph AG-IS" manufactured by Shimadzu corporation) at a temperature of 23℃and a relative humidity of 50%, and the value measured at this time was defined as "peeling force (R1)".
[ Peel force (R2) ]
The 1 st release film was removed from the curable adhesive sheet to be measured, and the exposed adhesive surface was laminated on the surface of an alkali-free glass having a thickness of 25 μm (Kapton 100H, manufactured by dolby eastern corporation), and the resultant laminate was pressed at 100℃using a heat laminator. Then, the curable adhesive sheet was cut into a size of 150m×50mm in the longitudinal direction and 50mm in the transverse direction together with the polyimide film, and test samples were produced. One adhesive surface of the double-sided tape was adhered to the surface of the polyimide film of the test sample opposite to the surface on which the curable adhesive layer was laminated, and the other adhesive surface of the double-sided tape was laminated on the surface of the metal plate, and the laminated film was pressed. The test sample was subjected to a peel test in the same manner as in the measurement of the peel force (R1). That is, the 2 nd release film to be measured as a release force was peeled from the test sample fixed to the metal plate under conditions of a release angle of 180℃and a release speed of 300 mm/min using the precision universal tester under an environment having a temperature of 23℃and a relative humidity of 50%, and the value measured at this time was defined as "release force (R2)".
Production examples 1 to 2
(1) Preparation of curable adhesive composition
The components shown in table 1 were mixed in the amounts (effective component ratios) shown in table 1 and dissolved in toluene to prepare curable adhesive compositions (1) to (2) so as to achieve the predetermined effective component concentrations.
Details of the components used for preparing the curable adhesive compositions (1) to (2) are as follows.
< Component (A): adhesive resin >, adhesive resin
"Modified polyolefin": a solution (product name "Unistole H-200" manufactured by mitsunobu chemical company) containing a maleic anhydride-modified alpha-olefin polymer (solid at 25 ℃) with mn=47,000.
< Component (B): polyphenylene ether resin
"Polyphenylene ether resin (b 1)": a solution (product name "OPE-2St 2200", manufactured by Mitsubishi gas chemical Co., ltd.) containing a vinylbenzyl-modified polyphenylene ether (compound represented by the above general formula (b-4), which is a solid at 25 ℃ C.) having Mn=2,200.
"Polyphenylene ether resin (b 2)": a solution (product name "OPE-2St 1200", manufactured by Mitsubishi gas chemical Co., ltd.) containing a vinylbenzyl-modified polyphenylene ether (compound represented by the above general formula (b-4), which is a solid at 25 ℃).
< Component (C): polyfunctional Compound
"Polyfunctional Compound": r a in the general formula (c-11) is an alkyl group having 8 to 15 carbon atoms, and has an isocyanurate skeleton. The product name "L-DAIC", manufactured by four chemical industry co., ltd, molecular weight= 377.27, is a liquid at 25 ℃.
< Component (D): cationic polymerization initiator >, and
"Thermal cationic polymerization initiator": the thermal cationic polymerization initiator (product name "San-Aid SI-B3" manufactured by Sannew chemical industry Co., ltd.) was a solid at 25 ℃.
< Ingredient (E): crosslinking agent >
"Isocyanate-based crosslinking agent": 1,3, 5-tris (5-isocyanatopentyl) -1,3, 5-triazine-2, 4, 6-trione (product name "Stabio D-370N", manufactured by Mitsui chemical Co., ltd.), molecular weight=462, being liquid at 25 ℃.
< Component (F): silane coupling agent >, and method for producing the same
"Silane coupling agent": 8-glycidoxy-octyl trimethoxysilane (product name "KBM4803", xinyue chemical Co., ltd.) is a liquid at 25 ℃.
TABLE 1
TABLE 1
Examples 1 to 4 and comparative example 1
The release films used in the following examples and comparative examples and curable adhesive compositions as materials for forming the curable adhesive layers are as follows.
< 1 St Release film >
Non-silicone release film (1): product names "PC38 AL-5", manufactured by Lintec corporation, a non-silicone release film having a release layer formed of an alkyd-based release agent on a polyethylene terephthalate (PET) film foamed to be white, thickness: 38 μm.
< 2 Nd Release film >
Non-silicone release film (2): product names "SP-PET50 AL-5", manufactured by Lintec corporation, a non-silicone release film having a release layer formed of an alkyd-based release agent on a colorless PET film, thickness: 50 μm.
Non-silicone release film (3): product names "SP-PET75 AL-5", manufactured by Lintec corporation, a non-silicone release film having a release layer formed of an alkyd-based release agent on a colorless PET film, thickness: 75 μm.
A non-silicone release film (4): product names "SP-PET38 AL-5", manufactured by Lintec corporation, a non-silicone release film having a release layer formed of an alkyd-based release agent on a colorless PET film, thickness: 38 μm.
Material for forming curable adhesive layer
Curable adhesive composition (1): the curable adhesive composition (1) prepared in production example 1 was prepared with the composition shown in table 1.
Curable adhesive composition (2): the curable adhesive composition (2) prepared in production example 2 with the composition shown in table 1.
The curable adhesive composition described in table 1 was applied to the release layer of the 2 nd release film described in table 2 to form a coating film, and the coating film was dried to form a curable adhesive layer having a thickness of 25 μm.
The exposed surface of the formed curable adhesive layer was then bonded to the release layer of the 1 st release film described in table 2, to prepare a curable adhesive sheet.
The peel forces (R1) and (R2) were measured by the above-described method using the prepared curable adhesive sheet. The results are shown in Table 2.
The dielectric loss tangent of the cured product obtained by curing the curable adhesive layer and the peelability of the 1 st peeling film were evaluated according to the following evaluation methods. These results are also shown in Table 2.
[ Dielectric loss tangent of cured product ]
A plurality of the produced curable adhesive sheets were prepared, and a plurality of the curable adhesive layers were stacked to form a curable adhesive layer having a thickness of about 1mm, thereby obtaining a laminate in which a 2 nd release film, a curable adhesive layer having a thickness of about 1mm, and a1 st release film were stacked in this order.
Then, the laminate was heated at 160 ℃ for 1 hour to cure the curable adhesive layer to obtain a cured product, and the 1 st release film and the 2 nd release film were removed to obtain a cured product as a sample for measurement.
For the obtained measurement sample, the dielectric loss tangent of the cured product at 23℃and 1GHz was measured using RF IMPEDANCE MATERIAL Analyzer (product name "E4991A", manufactured by Keysight Technologies). In the present specification, 1GHz is used as an example of the high frequency region.
[ Evaluation of peelability of the 1 st peeling film ]
The ease of peeling when only the 1 st release film was to be peeled off in a state where the curable adhesive layer of the produced curable adhesive sheet was sandwiched between the 1 st release film and the 2 nd release film was evaluated on the basis of the case of the curable adhesive sheet of comparative example 1 in 5 grades of 5 (maximum value) to 1 (minimum value). The criteria for ease of peeling at each reference are as follows.
"5": Compared with comparative example 1, the peeling was perceived to be very easy, with a large difference.
"4": Compared with comparative example 1, a sufficient peeling easiness was perceived, and the difference was remarkable.
"3": The peeling was perceived to be easier than that of comparative example 1.
"2": The peeling was more or less felt than in comparative example 1.
"1": The same degree as in the case of comparative example 1, or the peeling easiness inferior to that of comparative example 1.
As can be seen from table 2: in the curable adhesive sheets produced in examples 1 to 4, the 1 st release film was easily peeled off and the handleability was excellent as compared with comparative example 1. Further, since the curable adhesive sheets produced in examples 1 to 4 use a non-silicone release agent, the transfer of the silicone component to the adherend is not caused, and thus contamination of the adherend can be suppressed.
Symbol description
1: A curable adhesive sheet;
10: a curable adhesive layer;
10a, 10b: a surface;
21: 1 st release film;
211: a peeling layer;
212: a resin film;
22: a2 nd release film;
221: a peeling layer;
222: and (3) a resin film.
Claims (10)
1. A curable adhesive sheet comprising: a curable adhesive layer capable of forming a cured product having a dielectric loss tangent of 0.01 or less at 23 ℃ and 1 GHz; a 1 st release film and a2 nd release film sandwiching both sides of the curable adhesive layer,
The 1 st release film has: a colored resin film (i), and a release agent layer which is laminated on one surface of the colored resin film (i) and is in contact with the surface of the curable adhesive layer,
The 2 nd release film has: a resin film (ii) visually distinguishable from the colored resin film (i), and a release agent layer laminated on one surface of the resin film (ii) and in contact with the surface of the curable adhesive layer,
The curable adhesive sheet satisfies the following element (Ia):
Element (Ia): the thickness ratio (T2)/(T1) of the thickness (T2) of the 2 nd release film to the thickness (T1) of the 1 st release film is 1.05 or more.
2. The curable adhesive sheet according to claim 1, which further satisfies the following element (Ib):
Element (Ib): the thickness ratio (T2)/(T1) of the thickness (T2) of the 2 nd release film to the thickness (T1) of the 1 st release film is 10.0 or less.
3. The curable adhesive sheet according to claim 1 or 2, which further satisfies the following element (IIa): element (IIa) wherein the difference (T2) - (T1) between the thickness (T2) of the 2 nd release film and the thickness (T1) of the 1 st release film is 5.0 μm or more.
4. The curable adhesive sheet according to any one of claims 1 to 3, which further satisfies the following element (IIb):
element (IIb): the difference (T2) - (T1) between the thickness (T2) of the 2 nd release film and the thickness (T1) of the 1 st release film is 165.0 μm or less.
5. The curable adhesive sheet according to any one of claims 1 to 4, which further satisfies the following element (III):
element (III): the ratio (R1)/(R2) of the peel force (R1) when the 1 st release film is peeled from the curable adhesive layer at 180 DEG peel angle and 300 mm/min peel speed to the peel force (R2) when the 2 nd release film is peeled from the curable adhesive layer at 180 DEG peel angle and 300 mm/min peel speed is 0.97 or less.
6. The curable adhesive sheet according to any one of claims 1 to 5, which further satisfies the following element (IV):
Element (IV): the peel force (R2) when the 2 nd release film is peeled from the curable adhesive layer at a peel angle of 180 DEG at a peel speed of 300 mm/min is greater than the peel force (R1) when the 1 st release film is peeled from the curable adhesive layer at a peel angle of 180 DEG at a peel speed of 300 mm/min, and the peel force (R2) is 600mN/50mm or less.
7. The curable adhesive sheet according to any one of claims 1 to 6, wherein the resin film (ii) is a transparent resin film.
8. The curable adhesive sheet according to any one of claims 1 to 7, wherein the curable adhesive layer is a layer formed of a curable adhesive composition containing a polyphenylene ether resin.
9. The curable adhesive sheet according to any one of claims 1 to 8, wherein when the curable adhesive layer exposed by peeling the 1 st release film is adhered to an adherend, it is confirmed by an optical inspection means whether or not a foreign substance is present at the interface between the curable adhesive layer and the adherend from the 2 nd release film side.
10. A method for producing a cured product using the curable adhesive sheet according to any one of claims 1 to 9, comprising the following steps (1) to (3):
Step (1): a step of adhering the curable adhesive layer exposed by peeling the 1 st release film to an adherend;
step (2): a step of confirming, by an optical inspection means, that no foreign matter is present at the interface between the curable adhesive layer and the adherend from the 2 nd release film side;
step (3): and (2) curing the curable adhesive layer to obtain a cured product.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021161705 | 2021-09-30 | ||
| JP2021-161705 | 2021-09-30 | ||
| PCT/JP2022/036717 WO2023054677A1 (en) | 2021-09-30 | 2022-09-30 | Curable adhesive sheet, and method for producing cured product |
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| Publication Number | Publication Date |
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| CN118019819A true CN118019819A (en) | 2024-05-10 |
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| CN202280063975.1A Pending CN118019819A (en) | 2021-09-30 | 2022-09-30 | Curable adhesive sheet and method for producing cured product |
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| Country | Link |
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| JP (1) | JPWO2023054677A1 (en) |
| KR (1) | KR20240070534A (en) |
| CN (1) | CN118019819A (en) |
| TW (1) | TW202332750A (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5129204B2 (en) * | 2009-07-16 | 2013-01-30 | 日東電工株式会社 | Double-sided adhesive tape |
| JP2013067743A (en) * | 2011-09-26 | 2013-04-18 | Mitsubishi Plastics Inc | Substrate-less double-sided adhesive sheet |
| JP2018168234A (en) * | 2017-03-29 | 2018-11-01 | 東レ株式会社 | Adhesive sheet for electronic component protection |
| JP7241465B2 (en) * | 2018-01-30 | 2023-03-17 | 日東電工株式会社 | Adhesive, curable adhesive composition, adhesive sheet and method for producing same |
| JP7090428B2 (en) | 2018-02-05 | 2022-06-24 | デクセリアルズ株式会社 | Adhesive composition, thermosetting adhesive sheet and printed wiring board |
| JP2019176146A (en) * | 2018-03-26 | 2019-10-10 | 大日本印刷株式会社 | Method for manufacturing component built-in board, component built-in board, adhesive sheet, and resin composition |
| KR102710152B1 (en) * | 2018-06-15 | 2024-09-25 | 린텍 가부시키가이샤 | Bag composition, bag sheet and bag body |
| CN212076918U (en) * | 2020-04-25 | 2020-12-04 | 东莞市星勤胶粘制品有限公司 | Double-sided adhesive tape full-page sheet stock for flexible circuit board |
-
2022
- 2022-09-30 CN CN202280063975.1A patent/CN118019819A/en active Pending
- 2022-09-30 KR KR1020247009260A patent/KR20240070534A/en unknown
- 2022-09-30 JP JP2023551901A patent/JPWO2023054677A1/ja active Pending
- 2022-09-30 TW TW111137198A patent/TW202332750A/en unknown
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| TW202332750A (en) | 2023-08-16 |
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