CN114555737A - Adhesive sheet for device - Google Patents
Adhesive sheet for device Download PDFInfo
- Publication number
- CN114555737A CN114555737A CN202080074914.6A CN202080074914A CN114555737A CN 114555737 A CN114555737 A CN 114555737A CN 202080074914 A CN202080074914 A CN 202080074914A CN 114555737 A CN114555737 A CN 114555737A
- Authority
- CN
- China
- Prior art keywords
- adhesive layer
- compound
- curable
- resin
- adhesive sheet
- 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.)
- Granted
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 85
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 85
- 239000012790 adhesive layer Substances 0.000 claims abstract description 118
- 150000001875 compounds Chemical class 0.000 claims abstract description 109
- 229920005989 resin Polymers 0.000 claims abstract description 94
- 239000011347 resin Substances 0.000 claims abstract description 94
- 229920001955 polyphenylene ether Polymers 0.000 claims abstract description 51
- 239000007788 liquid Substances 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- -1 alicyclic diglycidyl ether compound Chemical class 0.000 claims description 53
- 239000011230 binding agent Substances 0.000 claims description 22
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 17
- 239000003505 polymerization initiator Substances 0.000 claims description 17
- 239000004593 Epoxy Substances 0.000 claims description 14
- 125000002723 alicyclic group Chemical group 0.000 claims description 14
- 125000003700 epoxy group Chemical group 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 150000002430 hydrocarbons Chemical group 0.000 description 26
- 239000006087 Silane Coupling Agent Substances 0.000 description 23
- 239000000126 substance Substances 0.000 description 21
- 229920005672 polyolefin resin Polymers 0.000 description 19
- 150000001336 alkenes Chemical class 0.000 description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 239000000178 monomer Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 125000001033 ether group Chemical group 0.000 description 11
- 239000010408 film Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 229930195734 saturated hydrocarbon Natural products 0.000 description 6
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000010899 nucleation Methods 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-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
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical group C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 238000007667 floating Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 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
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 229920001684 low density polyethylene Polymers 0.000 description 2
- 239000004702 low-density polyethylene Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920001179 medium density polyethylene Polymers 0.000 description 2
- 239000004701 medium-density polyethylene Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000005065 mining Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920006287 phenoxy resin Polymers 0.000 description 2
- 239000013034 phenoxy resin Substances 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229920006132 styrene block copolymer Polymers 0.000 description 2
- 125000000101 thioether group Chemical group 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 1
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VUBUXALTYMBEQO-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-phenylpropan-1-one Chemical compound FC(F)(F)C(F)(F)C(=O)C1=CC=CC=C1 VUBUXALTYMBEQO-UHFFFAOYSA-N 0.000 description 1
- NQFUSWIGRKFAHK-UHFFFAOYSA-N 2,3-epoxypinane Chemical compound CC12OC1CC1C(C)(C)C2C1 NQFUSWIGRKFAHK-UHFFFAOYSA-N 0.000 description 1
- GVJRTUUUJYMTNQ-UHFFFAOYSA-N 2-(2,5-dioxofuran-3-yl)acetic acid Chemical compound OC(=O)CC1=CC(=O)OC1=O GVJRTUUUJYMTNQ-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- TZLVUWBGUNVFES-UHFFFAOYSA-N 2-ethyl-5-methylpyrazol-3-amine Chemical compound CCN1N=C(C)C=C1N TZLVUWBGUNVFES-UHFFFAOYSA-N 0.000 description 1
- VSKJLJHPAFKHBX-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 VSKJLJHPAFKHBX-UHFFFAOYSA-N 0.000 description 1
- GRWFFFOEIHGUBG-UHFFFAOYSA-N 3,4-Epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclo-hexanecarboxylate Chemical compound C1C2OC2CC(C)C1C(=O)OCC1CC2OC2CC1C GRWFFFOEIHGUBG-UHFFFAOYSA-N 0.000 description 1
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 description 1
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 1
- KPOXQAKDFUYNFA-UHFFFAOYSA-N 3-methyl-7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound C1C(C(O)=O)C(C)CC2OC21 KPOXQAKDFUYNFA-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- NMUBRRLYMADSGF-UHFFFAOYSA-N 3-triethoxysilylpropan-1-ol Chemical compound CCO[Si](OCC)(OCC)CCCO NMUBRRLYMADSGF-UHFFFAOYSA-N 0.000 description 1
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 1
- LVNLBBGBASVLLI-UHFFFAOYSA-N 3-triethoxysilylpropylurea Chemical compound CCO[Si](OCC)(OCC)CCCNC(N)=O LVNLBBGBASVLLI-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- YATIYDNBFHEOFA-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-ol Chemical compound CO[Si](OC)(OC)CCCO YATIYDNBFHEOFA-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- LVACOMKKELLCHJ-UHFFFAOYSA-N 3-trimethoxysilylpropylurea Chemical compound CO[Si](OC)(OC)CCCNC(N)=O LVACOMKKELLCHJ-UHFFFAOYSA-N 0.000 description 1
- HYYPKCMPDGCDHE-UHFFFAOYSA-N 4-(7-oxabicyclo[4.1.0]heptan-4-ylmethyl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1CC1CC2OC2CC1 HYYPKCMPDGCDHE-UHFFFAOYSA-N 0.000 description 1
- IMDQDSLAUVKLAO-UHFFFAOYSA-N 4-[2-(4-carboxy-7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]-7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound C1CC2OC2CC1(C(O)=O)CCC1(C(=O)O)CC2OC2CC1 IMDQDSLAUVKLAO-UHFFFAOYSA-N 0.000 description 1
- HVMHLMJYHBAOPL-UHFFFAOYSA-N 4-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propan-2-yl]-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1C(C)(C)C1CC2OC2CC1 HVMHLMJYHBAOPL-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- QKFFSWPNFCXGIQ-UHFFFAOYSA-M 4-methylbenzenesulfonate;tetraethylazanium Chemical compound CC[N+](CC)(CC)CC.CC1=CC=C(S([O-])(=O)=O)C=C1 QKFFSWPNFCXGIQ-UHFFFAOYSA-M 0.000 description 1
- WUKUJFNYTULCOP-UHFFFAOYSA-N 4-propyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(CCC)CCC2OC21 WUKUJFNYTULCOP-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- BMIOTMCWMGQPAA-UHFFFAOYSA-N 5-methyl-3-[(5-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)methyl]-7-oxabicyclo[4.1.0]heptane-3-carboxylic acid Chemical compound C1C2OC2C(C)CC1(C(O)=O)CC1CC(C)C2OC2C1 BMIOTMCWMGQPAA-UHFFFAOYSA-N 0.000 description 1
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 1
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 239000005047 Allyltrichlorosilane Substances 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical class C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- AJDPRSJBHBDFOZ-UHFFFAOYSA-N C1CC2OC2(C)CC1(C(O)=O)CC1CC(C)(O2)C2CC1 Chemical compound C1CC2OC2(C)CC1(C(O)=O)CC1CC(C)(O2)C2CC1 AJDPRSJBHBDFOZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
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- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
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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
- C09J7/10—Adhesives in the form of films or foils without carriers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- 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
- C09J201/00—Adhesives based on unspecified macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/35—Heat-activated
Abstract
The present invention provides an adhesive sheet for a device, which comprises a curable adhesive layer containing the following component (A) and component (B), wherein the content of the component (A) in the curable adhesive layer is more than 3.0 mass%. The adhesive sheet for a device has a curable adhesive layer which imparts a cured product having low dielectric characteristics in a high-frequency region and is excellent in adhesion suitability. (A) The components: a non-aromatic curable compound that is liquid at 25 ℃; (B) the components: a modified polyphenylene ether resin.
Description
Technical Field
The present invention relates to an adhesive sheet for a device, which has a curable adhesive layer that imparts a cured product having low dielectric characteristics in a high-frequency region and has excellent adhesion suitability. In the present specification, the high frequency region refers to a region of 300MHz to 300 GHz.
Background
In recent years, with the miniaturization and weight reduction of electronic devices, flexible printed wiring boards (FPCs) have been increasingly used as wiring members.
The FPC can be obtained by, for example, etching a copper foil of a copper clad laminate obtained by laminating a copper foil on an insulating resin film such as polyimide to form a circuit (electric circuit).
In general, a cover film 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.
Accordingly, in recent years, with respect to communication devices such as smartphones, electric signals have become higher in frequency to process data of larger capacity.
However, since an electric signal in a high frequency range is easily converted into heat, when the electric signal is increased in frequency, transmission loss tends to increase.
In order to transmit an electric signal in a high frequency region at a high speed and suppress transmission loss, dielectric characteristics (reduction in dielectric constant and reduction in dielectric loss tangent) of an insulator (a base material, an adhesive, or the like) constituting a wiring member are improved.
Patent document 1 describes: an adhesive composition containing 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, or a thermosetting adhesive sheet having a thermosetting adhesive layer formed using the adhesive composition.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2019-135280 (WO 2019/151014).
Disclosure of Invention
Problems to be solved by the invention
The cured product of the thermosetting adhesive layer described in patent document 1 has low dielectric characteristics (in the present specification, "having low dielectric characteristics" means "having a low dielectric constant and a low dielectric loss tangent").
However, the thermosetting adhesive layer described in patent document 1 tends to have poor suitability for adhesion, and in addition to heating for performing a curing reaction, it is necessary to temporarily fix the object to be adhered by overlapping the thermosetting adhesive layer in the previous stage with the object to be adhered, and to heat and soften the curable adhesive layer.
Therefore, an adhesive sheet for devices having a curable adhesive layer with excellent adhesion suitability is desired.
The present invention has been made in view of the above circumstances, and an object thereof is to provide: an adhesive sheet for devices, which is provided with a curable adhesive layer that imparts a cured product having low dielectric characteristics in a high-frequency region and has excellent adhesion suitability.
Means for solving the problems
In order to solve the above problems, the present inventors have conducted intensive studies on a curable adhesive layer.
As a result, the following were found: 1) polyphenylene ether resins are excellent as resins having low dielectric characteristics, but have a very high melting point (softening point) and have hard properties at normal temperature, and therefore, when the thermosetting adhesive layer described in patent document 1 is used, it is necessary to reach a high temperature to exhibit sufficient adhesion force; and 2) a non-aromatic curable compound which is liquid at 25 ℃ is a useful component from the viewpoint of the adhesion suitability of the curable adhesive layer and from the viewpoint of the low dielectric characteristics of the cured product, and the present invention has been completed.
Accordingly, the present invention provides the following adhesive sheets for devices [1] to [6 ].
[1] An adhesive sheet for devices, which comprises a curable adhesive layer containing the following components (A) and (B), wherein the content of the component (A) is 3.0% by mass or more relative to the entire curable adhesive layer,
(A) the components: a non-aromatic curable compound that is liquid at 25 ℃;
(B) the components: a modified polyphenylene ether resin.
[2] [1] the adhesive sheet for a device, wherein the non-aromatic curable compound that is liquid at 25 ℃ is an alicyclic polyfunctional epoxy compound or a compound having 2 or more hydrocarbon groups having a double bond at the terminal.
[3] [2] the adhesive sheet for a device, wherein the non-aromatic curable compound that is liquid at 25 ℃ is an alicyclic epoxy compound having 2 epoxy groups or a compound having 2 hydrocarbon groups having a double bond at the terminal.
[4] [3] the adhesive sheet for devices, wherein the alicyclic polyfunctional epoxy compound is an alicyclic polyfunctional diglycidyl ether compound.
[5] The adhesive sheet for devices according to any one of [1] to [4], further comprising the following component (C),
(C) the components: a binder resin having a reactive group.
[6] The adhesive sheet for devices according to any one of [1] to [5], further comprising the following component (D),
(D) the components: a cationic polymerization initiator.
[7] The adhesive sheet for devices according to any one of [1] to [6], wherein a cured product of the curable adhesive layer has a dielectric loss tangent of less than 0.0050 at 23 ℃ and a frequency of 1 GHz.
Effects of the invention
Provided is an adhesive sheet for a device, which has a curable adhesive layer that imparts a cured product having low dielectric characteristics in a high-frequency region and has excellent adhesion suitability.
Detailed Description
The adhesive sheet for devices of the present invention has a curable adhesive layer containing the following components (A) and (B), wherein the content of the component (A) is 3.0% by mass or more relative to the entire curable adhesive layer,
(A) the components: a non-aromatic curable compound that is liquid at 25 ℃;
(B) the components: a modified polyphenylene ether resin.
[ (A) ingredient: non-aromatic curable Compound that is liquid at 25 ]
The curable adhesive layer constituting the adhesive sheet for devices of the present invention contains a non-aromatic curable compound that is liquid at 25 ℃ as the component (a) (hereinafter, may be referred to as "curable compound (a)").
By "liquid at 25" is meant that it has fluidity at 25 ℃. The curable compound (A) preferably has a viscosity of 2 to 10000mPa as measured with an E-type viscometer at 25 ℃ and 1.0 rpm.
As described later, the curable adhesive layer contains a modified polyphenylene ether resin. Since the modified polyphenylene ether resin has a relatively rigid molecular structure, the curable adhesive layer containing the modified polyphenylene ether resin tends to have poor adhesion suitability.
In this regard, by including the curable compound (a), which is a compound that is liquid at 25 ℃, in the curable adhesive layer, the adhesiveness or tackiness of the curable adhesive layer can be effectively improved, and a curable adhesive layer that can be adhered to an adherend without being excessively heated can be obtained.
The curable compound (a) is a non-aromatic compound. "non-aromatic compound" means a compound having no aromatic structure in the molecule. By using a non-aromatic compound as the curable compound (a), a cured product having low dielectric characteristics can be easily formed.
The curable compound (a) is a curable compound. The "curable compound" is a compound having a reactive group and converting a curable adhesive layer into a cured product by increasing the molecular weight or forming a crosslinked structure. By containing a curable compound in the curable adhesive layer, a cured product having excellent adhesive strength can be formed.
The molecular weight of the curable compound (A) is usually 100 to 5,000, preferably 200 to 3,000.
By setting the molecular weight to 100 or more, volatilization of the curable compound (a) can be suppressed in a drying step or the like in forming the curable adhesive layer.
By making the molecular weight 1,000 or less, the requirement of being liquid at 25 ℃ is easily satisfied.
The content of the curable compound (a) is 3.0% by mass or more, preferably 5.0 to 30% by mass, and more preferably 6.0 to 20% by mass, based on the entire curable adhesive layer. By setting the content of the curable compound (a) to 3.0 mass% or more based on the entire curable adhesive layer, a curable adhesive layer can be formed which provides a cured product having low dielectric characteristics in a high frequency range and which has excellent adhesion suitability. In addition, if the content of the curable compound (a) is 6.0 to 20% by mass, a cured product having sufficient adhesive strength can be easily formed even for a substrate which is difficult to adhere to.
Examples of the curable compound (a) include: alicyclic polyfunctional epoxy compound [ curable compound (A) ]α)]Or a compound having 2 or more hydrocarbon groups each having a double bond at a terminal [ curable compound (A)β)]. Among these, a compound having 2 or more hydrocarbon groups having a double bond at the end [ curable compound (a) (curable compound (a)) is preferable from the viewpoint that it is difficult to improve the dielectric properties compared with the functional group derived from polymerization of an epoxy group, and a cured product having excellent low dielectric properties can be easily obtainedβ)]。
Curable compound (A)α) The compound has an alicyclic skeleton in the molecule and has 2 or more epoxy groups in the molecule.
In the present specification, the epoxy group includes a group having an oxirane structure such as a glycidyl group, a glycidyl ether group, and an epoxycyclohexyl group.
Curable compound (A)α) Since the curable compound (A) has an alicyclic skeleton in the molecule, the curable compound (A) is usedα) A curable adhesive layer which can give a cured product having low dielectric characteristics in a high-frequency region can be easily obtained.
Curable compound (A)α) Since the curable adhesive layer has 2 or more epoxy groups in the molecule, it is easy to obtain a curable adhesive layer that provides a cured product having more excellent adhesive strength. Curable compound (A)α) The number of epoxy groups in the molecule is preferably 2 to 6, more preferably 2 to 4, and further preferably 2. By using a curable compound (A)α) An alicyclic epoxy compound having 2 epoxy groups, even when the compound (A) exhibits curabilityα) When the amount of (b) is large, curing shrinkage of the curable adhesive layer can be suppressed. Therefore, for example, when the device adhesive sheet is used for bonding a plate-like member such as a circuit board, warpage of the plate-like member can be reduced.
Curable compound (A)α) The epoxy equivalent of (A) is preferably 50 to 1000g/eq, more preferably 100 to 800 g/eq.
By making the epoxy equivalent of the curable compound (A) in the above rangeα) The curable adhesive layer of (3) is cured, and a cured product having a further excellent adhesive strength can be formed more efficiently.
The epoxy equivalent in the present invention means a value obtained by dividing the molecular weight by the number of epoxy groups.
As the curable compound (A)α) Examples thereof include: a polyglycidyl ether compound of a polyhydric alcohol having at least 1 or more alicyclic structures, or a cycloolefin oxide compound such as a cyclohexene oxide or cyclopentene oxide-containing compound obtained by epoxidizing a cyclohexene ring-or cyclopentene ring-containing compound with an oxidizing agent.
Among these, when used in combination with a thermal cationic polymerization initiator, the compound is used as the curable compound (A)α) Alicyclic polyfunctional diglycidyl ether compounds are preferred.
When an epoxy compound having high reactivity such as cyclohexene oxide is used, a curing reaction proceeds in the step of forming the curable adhesive layer, and there is a possibility that a curable adhesive layer having poor adhesion suitability is formed.
On the other hand, since the alicyclic polyfunctional diglycidyl ether compound is not highly reactive, even when used in combination with a thermal cationic polymerization initiator, the progress of the curing reaction can be suppressed in the step of forming the curable adhesive layer.
As the curable compound (A)α) Representative examples of (a) include: hydrogenated bisphenol A diglycidyl ether, 3, 4-epoxycyclohexylmethyl-3, 4-epoxycyclohexanecarboxylate, 3, 4-epoxy-1-methylcyclohexyl-3, 4-epoxy-1-methylcyclohexyl formate, 6-methyl-3, 4-epoxycyclohexylmethyl-6-methyl-3, 4-epoxycyclohexanecarboxylate, 3, 4-epoxy-3-methylcyclohexylmethyl-3, 4-epoxy-3-methylcyclohexaneformate, 3, 4-epoxy-5-methylcyclohexylmethyl-3, 4-epoxy-5-methylcyclohexaneformate, bis (3, 4-epoxycyclohexylmethyl) adipate, a polymer of the formula, 3, 4-epoxy-6-methylcyclohexaneformate, methylenebis (3, 4-epoxycyclohexane), propane-2, 2-diyl-bis (3, 4-epoxycyclohexane), 2-bis (3, 4-epoxycyclohexyl) propane, dicyclopentadiene diepoxide, ethylenebis (3, 4-epoxycyclohexane formate), dioctylphthalate, di-2-ethylhexyl hexahydrophthalate, 1-epoxyethyl-3, 4-epoxycyclohexane, 1, 2-epoxy-2-epoxyethylcyclohexane,αPinene oxide, limonene dioxide, and the like.
In addition, as the curable compound (A)α) Commercially available products may also be used. Examples of commercially available products include: celloxide 2021P, Celloxide 2081, Celloxide 2000, and Celloxide 8010 (manufactured by Daicel corporation, supra); eplight 4000 (manufactured by Kyoeisha chemical Co.); YX8000 and YX8034 (manufactured by Mitsubishi Chemical Co., Ltd.); adeka Resin EP-4088S, Adeka Resin EP-4088L, Adeka Resin EP-4080E (manufactured by ADEKA Co., Ltd.).
Curable compound (A)α) The use of 1 kind alone, or a combination of 2 or more.
Curable compound (A)β) Is a compound having 2 or more hydrocarbon groups having a double bond at the terminal.
Curable compound (A)β) Since the resin composition has 2 or more hydrocarbon groups having a double bond at the terminal, it is easy to obtain a cured product having more excellent adhesive strengthAnd a chemical adhesive layer.
The number of carbon atoms of the hydrocarbon group having a double bond at the terminal is preferably 2 to 10, more preferably 2 to 5.
Examples of the hydrocarbon group having a double bond at the terminal include: vinyl, allyl, 3-butenyl, 4-pentenyl, 5-hexenyl, isopropenyl, 1-methyl-2-propenyl, and the like. Among these, allyl is preferred.
Curable compound (A)β) The number of the hydrocarbon groups having a double bond at the terminal contained in (1) is 2 or more. When the number of hydrocarbon groups having a double bond at the terminal is 2 or more, a crosslinked structure is formed in the cured product, and a cured product having more excellent adhesive strength and heat resistance can be formed.
In addition, by appropriately dispersing the crosslinked structure formed in the cured product, the number of hydrocarbon groups having a double bond at the terminal is preferably 2 to 4 from the viewpoint of suppressing the occurrence of cracks in the cured product of the curable adhesive layer, even when the curable compound (a) exhibits curability and is curableβ) When the blending amount of (3) is large, curing shrinkage of the curable adhesive layer can be suppressed, and when the device adhesive sheet is used for bonding a plate-shaped member such as a circuit board, 2 is more preferable from the viewpoint of reducing warpage of the plate-shaped member. In the case of polymerizing a hydrocarbon group having a double bond, the distance between the monomers before polymerization (i.e., the distance between the double bonds represented by the Van der Waals distance) is shortened by polymerization, and therefore, the curing shrinkage of the curable adhesive layer tends to become larger as the number of hydrocarbon groups having a double bond at the terminal increases. By using a curable compound (A)β) The number of the hydrocarbon groups having a double bond at the terminal contained in (1) is 2, and curing shrinkage can be effectively suppressed.
Curable compound (A)β) Preferably having a heterocyclic skeleton. By using a curable compound (A)β) The curable adhesive layer has a heterocyclic skeleton and can easily provide a cured product having excellent adhesive strength and low dielectric characteristics.
Examples of the heterocyclic skeleton include: an isocyanurate skeleton or a glycoluril skeleton.
AsCurable compound having isocyanurate skeleton (A)β) Examples thereof include: a compound represented by the following formula (1) or (2).
[ chemical formula 1]
[ chemical formula 2]
In the formula (1), R1、R2Each independently represents a hydrocarbon group having a double bond at the terminal, R3Represents a C1-15 saturated hydrocarbon group or a C1-15 alkoxy-substituted alkyl group.
In the formula (2), R4～R6Each independently represents a hydrocarbon group having a double bond at the terminal.
R1、R2、R4、R5、R6The hydrocarbon group having a double bond at the terminal is as described above.
R3The carbon number of the saturated hydrocarbon group is 1 to 15, preferably 5 to 15, and more preferably 8 to 15. As R3Examples of the saturated hydrocarbon group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-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.
R3The number of carbon atoms of the alkoxy-substituted alkyl group is 2 to 15, preferably 2 to 12, and more preferably 3 to 10. As R23Examples of the alkoxy-substituted alkyl group include: methoxymethyl, ethoxymethyl, 2-methoxyethoxymethyl, benzyloxymethyl and the like.
As the curable compound (A) having a glycoluril skeletonβ) Examples thereof include: a compound represented by the following formula (3).
[ chemical formula 3]
In the formula (3), R7～R10Each independently represents a hydrocarbon group having 1 to 15 carbon atoms, and at least 2 of them are hydrocarbon groups having a double bond at the terminal. R11、R12Represents a hydrogen atom or a C1-15 saturated hydrocarbon group.
Among these, the curable compound (A) is considered to be a curable compound in that a cured product having an appropriate crosslinking density can be easily obtainedβ) The compound having an isocyanurate skeleton is preferable, and the compound represented by formula (1) is more preferable. In particular, the compound represented by the following formula is preferable in terms of easily obtaining a curable adhesive layer that provides a cured product having more excellent low dielectric characteristics.
[ chemical formula 4]
Wherein R represents a C5-15 saturated hydrocarbon group, preferably a C8-15 saturated hydrocarbon group.
As the curable compound (A)β) Commercially available products can be used.
For example, examples of the compound represented by the formula (1) include: L-DAIC (manufactured by four chemical industries, Ltd.). Examples of the compound represented by the formula (2) include: TAIC (manufactured by Mitsubishi Chemical corporation). Examples of the compound represented by the formula (3) include: TA-G (manufactured by four chemical industries, Ltd.).
Curable compound (A)β) The boiling point of (B) is preferably 175 to 350 ℃, more preferably 200 to 300 ℃. Further, a curable compound (A)β) The 5% weight loss temperature is preferably 175-350 ℃, and more preferably 200-300 ℃.
Curable compound (A)β) The use of 1 kind alone, or a combination of 2 or more.
The curable adhesive layer may contain a curable compound that is liquid at 25 ℃, that is, an aromatic curable compound that is liquid at 25 ℃, other than the curable compound (a), but the amount used is preferably reduced in order to further reduce the dielectric constant and dielectric loss tangent of a cured product of the curable adhesive layer. From such a viewpoint, the mass ratio of the curable compound (a) to the mass of the curable compound which is liquid at 25 ℃ contained in the curable adhesive layer is preferably 90 mass% or more, and more preferably 95 mass% or more.
[ (B) ingredient: modified polyphenylene ether resin
The curable adhesive layer constituting the adhesive sheet for devices of the present invention contains a modified polyphenylene ether resin as the component (B).
The modified polyphenylene ether resin is obtained by modifying a polyphenylene ether resin as a precursor with a modifier and introducing a reactive group.
The polyphenylene ether resin is a resin having a polyphenylene ether skeleton in the main chain.
The polyphenylene ether skeleton is a polyphenylene ether skeleton having a repeating unit represented by the following formula,
[ chemical formula 5]
Or a skeleton having a repeating unit in which a hydrogen atom in the above formula is substituted.
Since the modified polyphenylene ether resin has a polyphenylene ether skeleton, a cured product of the curable adhesive layer containing the modified polyphenylene ether resin has low dielectric characteristics.
Further, since the modified polyphenylene ether resin has a reactive group, a cured product of the curable adhesive layer containing the modified polyphenylene ether resin is excellent in adhesive strength and heat resistance.
Examples of the polyphenylene ether skeleton in the modified polyphenylene ether resin include: a polyphenylene ether skeleton represented by the following formula (4).
[ chemical formula 6]
In the formula (4), X is a 2-valent group represented by the following formula (5) or formula (6), Y is a 2-valent group represented by the following formula (7), a and b are integers of 0-100, and at least one of a and b is more than 1. Each represents a bond (hereinafter, the same applies).
[ chemical formula 7]
In the formula (2), R13～R20Each independently represents a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, and preferably a hydrogen atom or a methyl group.
[ chemical formula 8]
In the formula (6), R21～R28Each independently represents a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, and preferably a hydrogen atom or a methyl group. A represents a linear, branched or cyclic 2-valent hydrocarbon group having 20 or less carbon atoms.
[ chemical formula 9]
In the formula (7), R29～R32Each independently represents a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, and preferably a hydrogen atom or a methyl group.
Examples of the polyphenylene ether skeleton in the modified polyphenylene ether resin include: a polyphenylene ether skeleton represented by the following formula (8).
[ chemical formula 10]
Examples of the reactive group in the modified polyphenylene ether resin include: groups having an ethylenically unsaturated bond such as vinyl, allyl, acryloyl, methacryloyl, cyclopentenyl, vinylbenzyl, and vinylnaphthyl; an epoxy group; hydroxyl groups, and the like.
Among these, the reactive group is preferably a group having an ethylenically unsaturated bond, and more preferably a vinylbenzyl group, from the viewpoint of easily obtaining a cured product having low dielectric characteristics.
As the modified polyphenylene ether resin, a modified polyphenylene ether resin having reactive groups at both ends of the polyphenylene ether skeleton is preferable from the viewpoint of easily obtaining a cured product having low dielectric characteristics.
The modified polyphenylene ether resin can be obtained by introducing a reactive group into the terminal after the polyphenylene ether skeleton is formed.
For example, a modified polyphenylene ether resin having vinylbenzyl groups as reactive groups at both terminals can be obtained by reacting a bifunctional phenol compound with a monofunctional phenol compound to obtain a polymer having phenolic hydroxyl groups at both terminals, and then performing vinylbenzyl etherification of the phenolic hydroxyl groups at the terminals using 4- (chloromethyl) styrene.
Examples of the modified polyphenylene ether resin include: a modified polyphenylene ether resin represented by the following formula (9).
[ chemical formula 11]
As the modified polyphenylene ether resin, commercially available products can be used. Examples of commercially available products include: OPE-2St (modified polyphenylene ether resin having vinylbenzyl groups at both ends), OPE-2Gly (modified polyphenylene ether resin having epoxy groups at both ends), OPE-2EA (modified polyphenylene ether resin having acryloyl groups at both ends, Mitsubishi GAS chemical Co., Ltd., or more), Noryl SA9000 (modified polyphenylene ether resin having methacryloyl groups at both ends, SABIC Co., Ltd.), and the like.
The modified polyphenylene ether resin preferably has a weight average molecular weight (Mw) of 500 to 5,000, more preferably 500 to 3,000.
The weight average molecular weight (Mw) of the modified polyphenylene ether resin was determined as a standard polystyrene equivalent value by Gel Permeation Chromatography (GPC) using Tetrahydrofuran (THF) as a solvent.
The modified polyphenylene ether resin may be used alone in 1 kind, or in combination of 2 or more kinds.
The content of the modified polyphenylene ether resin is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, based on the entire curable adhesive layer.
By setting the content of the modified polyphenylene ether resin to 5 to 50 mass% with respect to the entire curable adhesive layer, a cured product having low dielectric characteristics can be easily obtained.
[ (C) ingredient: adhesive resin having reactive group ]
The curable adhesive layer constituting the adhesive sheet for devices of the present invention may contain a binder resin having a reactive group as the component (C) (hereinafter, may be referred to as "binder resin (C)").
The curable adhesive layer constituting the adhesive sheet for devices of the present invention contains component (a), which is a compound that is liquid at 25 ℃. By containing the binder resin (C) in the curable adhesive layer, the shape of the adhesive layer can be easily maintained.
Further, since the binder resin (C) has a reactive group, a crosslinked structure in which the binder resin (C) participates can be formed in the cured product of the curable adhesive layer, and a cured product having excellent heat resistance can be formed. Further, by using a resin having a reactive group as a binder resin, a cured product having sufficient adhesive strength can be formed even for a substrate which is difficult to adhere to.
Examples of the reactive group include: carboxyl groups, carboxylic anhydride groups, carboxylic ester groups, hydroxyl groups, epoxy groups, amide groups, ammonium groups, nitrile groups, amino groups, imide groups, isocyanate groups, acetyl groups, thiol groups, ether groups, thioether groups, sulfone groups, phosphine groups, nitro groups, urethane groups, alkoxysilyl groups, silanol groups, halogen atoms and the like. The compound having a reactive group may have 2 or more reactive groups in the molecule.
The number average molecular weight (Mn) of the binder resin (C) is preferably 10,000 to 150,000, more preferably 30,000 to 100,000.
The number average molecular weight (Mn) of the binder resin (C) was determined as a standard polystyrene equivalent by Gel Permeation Chromatography (GPC) using Tetrahydrofuran (THF) as a solvent.
When the curable adhesive layer contains the binder resin (C), the content of the binder resin (C) is preferably 40 to 90% by mass, and more preferably 45 to 80% by mass, based on the entire curable adhesive layer.
By setting the content of the binder resin (C) to 40 to 90% by mass in the curable adhesive layer, a curable adhesive layer having both shape retention and tackiness can be easily obtained.
The type of the binder resin (C) is not particularly limited as long as it is a polymer component that imparts film formability and flexibility to the curable adhesive layer.
Examples of the type of the binder resin (C) include: olefin-based resins, styrene-based elastomers (block copolymers having a hard segment of styrene such as styrene/butadiene/styrene block copolymers and styrene/isoprene/styrene block copolymers and a soft segment of a conjugated diene), phenoxy resins (polymers having a main chain of a polyaddition structure of an aromatic diol and an aromatic diglycidyl ether), indene benzofuran resins (copolymers of indene and benzofuran, copolymers of indene, benzofuran, and styrene, and the like), acrylic polymers, polyester resins, polyvinyl alcohol resins, polyvinyl butyral, polyvinyl chloride, polyamide resins, cellulosic materials, polyvinyl ethers, polyimide resins, and the like.
Among these, olefin-based resins, styrene-based elastomers, phenoxy resins, and indene benzofuran resins are preferable as the type of the binder resin (C) from the viewpoint of easily obtaining a cured product excellent in low dielectric characteristics.
Among the above resins, a resin having a reactive group may be directly used as the binder resin (C). On the other hand, as the resin having no reactive group, for example, a modified resin obtained by modification treatment can be used as the binder resin (C).
The binder resin (C) may be used alone in 1 kind, or in combination of 2 or more kinds.
The modified polyolefin resin is preferable as the binder resin (C) because a cured product having excellent low dielectric characteristics and a cured product having excellent heat resistance can be easily obtained.
The modified polyolefin resin is an olefin resin having a reactive group introduced therein, which is obtained by modifying an olefin resin as a precursor with a modifier (a compound having a reactive group in the molecule).
The olefin-based resin is a polymer containing a repeating unit derived from an olefin-based monomer. The olefin-based resin may be a polymer composed only of repeating units derived from an olefin-based monomer, or may be a polymer composed of repeating units derived from an olefin-based monomer and repeating units derived from a monomer copolymerizable with an olefin-based monomer, but from the viewpoint of easily obtaining a cured product excellent in low dielectric characteristics, a polymer composed only of repeating units derived from an olefin-based monomer is preferable.
The olefin monomer is preferably one having 2 to 8 carbon atomsαAn olefin, more preferably ethylene, propylene, 1-butene, isobutylene, or 1-hexene, further preferably ethylene or propylene. These olefinic monomers may be used alone in 1 kind, or in combination of 2 or more kinds.
Examples of the monomer copolymerizable with the olefin-based monomer include: vinyl acetate, (meth) acrylates, styrene, and the like. Here, "(meth) acrylic" means acrylic or methacrylic (hereinafter, the same applies).
The olefin-based monomer copolymerizable with these monomers may be used alone in 1 kind or in combination with 2 or more kinds.
Examples of the olefin resin include: very Low Density Polyethylene (VLDPE), Low Density Polyethylene (LDPE), Medium Density Polyethylene (MDPE), High Density Polyethylene (HDPE), linear low density polyethylene, polypropylene (PP), ethylene-propylene copolymer, olefin elastomer (TPO), ethylene-vinyl acetate copolymer (EVA), ethylene- (meth) acrylic acid copolymer, ethylene- (meth) acrylate copolymer, and the like.
The modified polyolefin resin is preferably an acid-modified polyolefin resin from the viewpoint of forming a cured product having more excellent adhesive strength.
The acid-modified polyolefin resin is a resin obtained by graft-modifying an olefin resin with an acid or an acid anhydride. Examples thereof include: a resin obtained by introducing a carboxyl group or a carboxylic anhydride group (graft modification) by reacting an unsaturated carboxylic acid or an unsaturated carboxylic anhydride (hereinafter, sometimes referred to as "unsaturated carboxylic acid or the like") with an olefin resin.
Examples of the unsaturated carboxylic acid to be reacted with the olefin resin include: unsaturated carboxylic acids such as maleic acid, fumaric acid, itaconic acid, citraconic acid, glutaric acid, tetrahydrophthalic acid, and aconitic acid; unsaturated carboxylic acid anhydrides such as maleic anhydride, itaconic anhydride, glutaric anhydride, citraconic anhydride, aconitic anhydride, norbomene dicarboxylic anhydride and tetrahydrophthalic anhydride.
These can be used alone in 1 kind, or in combination of 2 or more. Among these, maleic anhydride is preferable because a cured product having more excellent adhesive strength can be easily obtained.
The amount of the unsaturated carboxylic acid or the like to be reacted with the olefin-based resin is preferably 0.1 to 5 parts by mass, more preferably 0.2 to 3 parts by mass, and still more preferably 0.2 to 1 part by mass, based on 100 parts by mass of the olefin-based resin. By curing the curable adhesive layer containing the acid-modified polyolefin resin thus obtained, a cured product having more excellent adhesive strength can be formed.
The method for introducing the unsaturated carboxylic acid unit or the unsaturated carboxylic acid anhydride unit into the olefin-based resin is not particularly limited. Examples thereof include: a method of reacting an olefin resin with an unsaturated carboxylic acid or the like by heating and melting the olefin resin to a temperature higher than the melting point of the olefin resin in the presence of a radical generator such as an organic peroxide or azonitrile; or a method in which an olefin resin and an unsaturated carboxylic acid are dissolved in an organic solvent, and then the mixture is heated and stirred in the presence of a radical generator to react the mixture, thereby graft-copolymerizing an unsaturated carboxylic acid and the like with an olefin resin.
As the acid-modified polyolefin resin, commercially available products can also be used. Examples of commercially available products include: admer (registered trademark) (manufactured by mitsui Chemical company), Unistole (registered trademark) (manufactured by mitsui Chemical company), BondyRam (manufactured by Polyram), orevac (registered trademark) (manufactured by ARKEMA company), Modic (registered trademark) (manufactured by mitsubishi Chemical company), and the like.
[ (D) ingredient: cationic polymerization initiator
The curable adhesive layer constituting the adhesive sheet for devices of the present invention may contain a cationic polymerization initiator as the component (D).
A curable adhesive layer containing a cationic polymerization initiator is preferable because the curing reaction can be more efficiently performed.
When the curable adhesive layer contains a cationic polymerization initiator, the content of the cationic polymerization initiator is preferably 0.1 to 6 parts by mass, more preferably 0.3 to 5 parts by mass, and still more preferably 0.5 to 4 parts by mass, based on 100 parts by mass of the total amount of the non-aromatic curable compound [ (a) component ] and the modified polyphenylene ether resin [ (B) component ] which are liquid at 25 ℃.
The cationic polymerization initiator is preferably a thermal cationic polymerization initiator because it has excellent stability over time and does not require an ultraviolet irradiation device or the like.
The thermal cationic polymerization initiator is a compound capable of generating a cationic species that initiates polymerization by heating.
Examples of the thermal cationic polymerization initiator include: sulfonium salts, quaternary ammonium salts, phosphonium salts, diazonium salts, iodonium salts, and the like.
Examples of sulfonium salts include: triphenylsulfonium tetrafluoroborate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium hexafluoroarsenate, tris (4-methoxyphenyl) sulfonium hexafluoroarsenate, diphenyl (4-phenylthiophenyl) sulfonium hexafluoroarsenate, and the like.
As the sulfonium salt, commercially available ones can also be used. Examples of commercially available products include: adeka Opton SP-150, Adeka Opton SP-170, Adeka Opton CP-66, Adeka Opton CP-77 (manufactured by ADEKA Co., Ltd.), San-Aid SI-60L, San-Aid SI-80L, San-Aid SI-100L, San-Aid SI-B2A, San-Aid SI-B3 (manufactured by Sanxin chemical Co., Ltd.), CYRACURE UVI-6974, CYRACURE UVI-6990 (manufactured by Union Carbide Co., Ltd.), UVI-508, UVI-509 (manufactured by General Electric Co., Ltd.), FC-508, FC-509 (manufactured by Minnesota Mining & Manufacturing Co., Ltd.), CD-1010, CD-1011 (manufactured by Sartomer Co., Ltd.), CI series products (manufactured by Nippon Dada Co., Ltd.), and the like.
Examples of the quaternary ammonium salt include: tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium hydrogensulfate, tetraethylammonium tetrafluoroborate, tetraethylammonium p-toluenesulfonate, N-dimethyl-N-benzylanilinium hexafluoroantimonate, N-dimethyl-N-benzylanilinium tetrafluoroborate, N-dimethyl-N-benzylpyridinium hexafluoroantimonate, N-diethyl-N-benzyltrifluoromethanesulfonate, N-dimethyl-N- (4-methoxybenzyl) pyridinium hexafluoroantimonate, N-diethyl-N- (4-methoxybenzyl) toluidinium hexafluoroantimonate and the like.
Examples of the phosphonium salt include: ethyltriphenylphosphonium hexafluoroantimonate, tetrabutylphosphonium hexafluoroantimonate, and the like.
Examples of the diazonium salt include: AMERICURE (manufactured by American Can corporation), ULTRASET (manufactured by ADEKA corporation), 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, as a commercially available product, there can be used: UV-9310C (Toshiba Silicones Co., Ltd.), Photonitiator 2074 (Rhone-Poulenc Co., Ltd.), UVE series products (General Electric Co., Ltd.), FC series products (Minnesota Mining & Manufacturing Co., Ltd.), and the like.
The thermal cationic polymerization initiator may be used alone in 1 kind, or in combination of 2 or more kinds.
[ (E) ingredient: silane coupling agent
The curable adhesive layer constituting the adhesive sheet for devices of the present invention may further contain a silane coupling agent as the component (E).
A curable adhesive layer containing a silane coupling agent is preferable because it tends to provide a cured product having more excellent adhesive strength.
When the curable adhesive layer contains a silane coupling agent, the content of the silane coupling agent is preferably 0.01 to 5% by mass, more preferably 0.05 to 1% by mass, based on the entire curable adhesive layer.
As the silane coupling agent, known silane coupling agents can be used. Among them, an organosilicon compound having at least 1 alkoxysilyl group in the molecule is preferable.
Examples of the silane coupling agent include: silane coupling agents having a (meth) acryloyl group such as 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, and 3-acryloxypropyltrimethoxysilane;
silane coupling agents having a vinyl group such as vinyltrimethoxysilane, vinyltriethoxysilane, dimethoxymethylvinylsilane, diethoxymethylvinylsilane, trichloroethylsilane, and vinyltris (2-methoxyethoxy) silane;
silane coupling agents having an epoxy group such as 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, and 8-glycidoxypropyloctyltrimethoxysilane;
styrene-based silane coupling agents such as p-styryltrimethoxysilane and p-styryltriethoxysilane;
silane coupling agents having an amino group such as N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N- (1, 3-dimethyl/butylene) propylamine, N-phenyl-3-aminopropyltrimethoxysilane, and hydrochloride of N- (vinylbenzyl) -2-aminoethyl-3-aminopropyltrimethoxysilane;
silane coupling agents having a ureido group such as 3-ureidopropyltrimethoxysilane and 3-ureidopropyltriethoxysilane;
silane coupling agents having a halogen atom such as 3-chloropropyltrimethoxysilane and 3-chloropropyltriethoxysilane;
silane coupling agents having a mercapto group such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane;
silane coupling agents having a sulfide group such as bis (trimethoxysilylpropyl) tetrasulfide and bis (triethoxysilylpropyl) tetrasulfide;
silane coupling agents having an isocyanate group such as 3-isocyanatopropyltrimethoxysilane and 3-isocyanatopropyltriethoxysilane;
silane coupling agents having allyl groups such as allyl trichlorosilane, allyl triethoxysilane, and allyl trimethoxysilane;
and silane coupling agents having a hydroxyl group such as 3-hydroxypropyltrimethoxysilane and 3-hydroxypropyltriethoxysilane.
These silane coupling agents may be used alone in 1 kind, or in combination with 2 or more kinds.
[ other ingredients ]
The curable adhesive layer constituting the adhesive sheet for devices of the present invention may contain other components within a range not to impair the effects of the present invention.
Examples of other components include: additives such as ultraviolet absorbers, antistatic agents, light stabilizers, antioxidants, resin stabilizers, fillers, pigments, extenders, and softeners.
These can be used alone in 1 kind, or in combination of 2 or more.
When the curable adhesive layer contains these additives, the content thereof can be determined as appropriate according to the purpose.
[ adhesive sheet for device ]
The adhesive sheet for devices of the present invention is an adhesive sheet having a curable adhesive layer containing the component (a) and the component (B).
The thickness of the curable adhesive layer is not particularly limited, but is usually 1 to 50μm, preferably 1 to 25μm, more preferably 5 to 25μAnd m is selected. The curable adhesive layer having a thickness within the above range is suitable as a material for forming a product related to a flexible printed wiring board.
The thickness of the curable adhesive layer can be measured by a known thickness meter in accordance with JIS K7130 (1999).
The adhesive sheet for a device of the present invention may have a base material in addition to the curable adhesive layer.
As the substrate, a resin film is generally available.
Examples of the resin component of the resin film include: polyimide, polyamide, polyamideimide, polyphenylene oxide, polyether ketone, polyether ether ketone, polyolefin, polyester, polycarbonate, polysulfone, polyether sulfone, polyphenylene sulfide, polyarylate, acrylic resin, cycloolefin polymer, aromatic polymer, polyurethane polymer, liquid crystal polymer film, and the like.
The thickness of the base material is not particularly limited, but is preferably 10 to 500μm, more preferably 10 to 300μm, more preferably 15 to 200μm。
The adhesive sheet for a device of the present invention may have a release sheet in addition to the curable adhesive layer.
The release sheet functions as a protective sheet for the curable adhesive layer before the device adhesive sheet is used. In the case where the device adhesive sheet does not have a substrate, the release sheet functions as a support in the production process of the device adhesive sheet.
When the device adhesive sheet of the present invention is used, the release sheet is usually peeled off and removed.
As the release sheet, a conventionally known release sheet can be used. Examples thereof include: a release sheet having a release layer subjected to a release treatment with a release agent on a release sheet base material.
Examples of the base material for the release sheet include: paper substrates such as cellophane, coated paper, high-quality paper, and the like; laminated paper obtained by laminating thermoplastic resin such as polyethylene on these paper substrates; plastic films such as polyethylene terephthalate resins, polybutylene terephthalate resins, polyethylene naphthalate resins, polypropylene resins, and polyethylene resins.
Examples of the release agent include: silicone resins, olefin resins, isoprene resins, butadiene resins, and other rubber elastomers, long-chain alkyl resins, alkyd resins, fluorine resins, and the like.
The thickness of the release sheet is not particularly limited, but is usually 20 to 250μAnd m is about.
When the device adhesive sheet of the present invention has a release sheet, the curable adhesive layer may have 1 release sheet and 2 release sheets in total on both sides, or may have a release sheet only on one side.
The method for producing the device adhesive sheet is not particularly limited. For example, the adhesive sheet for devices can be manufactured using a casting method.
When the adhesive sheet for a device is produced by a casting method, an adhesive composition containing a component of a curable adhesive layer is prepared, the obtained adhesive composition is applied to a release layer surface of a substrate or a release sheet subjected to a release treatment by a known method, and the obtained coating film is dried, whereby the adhesive sheet for a device can be produced.
The adhesive composition may also contain a solvent.
Examples of the solvent include: aromatic hydrocarbon solvents such as benzene and toluene; ester solvents such as ethyl acetate and butyl acetate; ketone solvents such as acetone, methyl ethyl ketone, 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 solvents may be used alone in 1 kind, or in combination of 2 or more kinds.
The content of the solvent may be determined as appropriate in consideration of coatability and the like.
Examples of the method of applying the adhesive composition include: spin coating, spray coating, bar coating, knife coating, roll coating, blade coating, die coating, gravure coating, and the like.
Examples of the method for drying the coating film include: conventionally known drying methods such as hot air drying, hot roll drying, and infrared ray irradiation.
The coating film is dried at 80 to 150 ℃ for 30 seconds to 5 minutes, for example.
The curable adhesive layer has excellent adhesion suitability. Therefore, when the adhesive sheet for a device of the present invention is used, the curable adhesive layer and the adherend are bonded, and excessive heating is not necessary for temporarily fixing them.
The temperature at which the curable adhesive layer and the adherend are bonded is usually 15 to 75 ℃, preferably 20 to 45 ℃.
When the curable adhesive layer is thermosetting, the curable adhesive layer is cured by heating the curable adhesive layer.
The conditions for thermally curing the curable adhesive layer are not particularly limited.
The heating temperature is usually 80 to 200 ℃ and preferably 90 to 175 ℃.
The heating time is usually 30 minutes to 12 hours, preferably 1 to 6 hours.
The cured product of the curable adhesive layer has low dielectric properties in a high-frequency region.
The specific dielectric constant of the cured product of the curable adhesive layer at 23 ℃ and a frequency of 1GHz (hereinafter, the specific dielectric constant may be referred to as "specific dielectric constant: (α) ") is preferably 2.7 or less, more preferably 2.6 or less, and particularly preferably 2.5 or less.
Contrast dielectric constant: (α) The lower limit of (b) is not particularly limited, but is usually 2.2 or more.
Can form a specific dielectric constant ofα) A curable adhesive layer of a cured product having a curing value of 2.7 or less is suitably used as an adhesive for closing a flexible printed wiring board.
Specific dielectric constant: (α) The measurement sample of (3) is not particularly limited as long as it can sufficiently cure the curable adhesive layer.
For example, when the measured curable adhesive layer has recommended curing conditions, a cured product of the curable adhesive layer cured under the recommended conditions is used as the specific dielectric constant: (α) The measurement sample of (1). In the case where the curing conditions are not recommended or unknown for the curable adhesive layer, a cured product obtained under curing conditions of, for example, 160 ℃ for 1 hour may be used as the specific dielectric constant: (α) The measurement sample of (1).
Specific dielectric constant: (α) The measurement can be carried out according to the method described in examples.
The dielectric loss tangent of the cured product of the curable adhesive layer at 23 ℃ and a frequency of 1GHz (hereinafter, this dielectric loss tangent may be referred to as "dielectric loss tangent: (β) ") is preferably 0.0050 or less, more preferably 0.0020 or less, and still more preferably 0.0015 or less.
For dielectric loss tangent of (β) The lower limit of (b) is not particularly limited, but is usually 0.0001 or more.
Can form a dielectric loss tangent ofβ) A curable adhesive layer of a cured product of 0.0050 or less is suitably used as an adhesive for flexible printed wiring board sealing.
Dielectric loss tangent of (β) The measurement can be carried out according to the method described in examples.
As described above, the curable adhesive layer constituting the adhesive sheet for devices of the present invention is excellent in adhesion suitability, and the cured product thereof has low dielectric properties in a high-frequency region.
Therefore, the curable adhesive layer constituting the adhesive sheet for a device of the present invention is suitably used for forming a member in a device which requires low dielectric characteristics.
For example, by using the adhesive sheet for a device of the present invention, an adhesive cured layer constituting a circuit board can be efficiently formed. Examples of the circuit board include: flexible printed wiring boards, and the like.
Examples
The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to the following examples.
[ Compounds used in examples or comparative examples ]
Seeding curable compound (a 1): hydrogenated bisphenol a epoxy resin [ product name: YX8000, epoxy equivalent: 205g/eq, liquid at 25 ];
seeding curable compound (a 2): a diallyl compound having an isocyanurate skeleton (product name: L-DAIC, manufactured by Sicountry chemical industry Co.);
seeding curable compound (AX 1): bisphenol a epoxy resin [ product name: jER828, epoxy equivalent: 184-194 g/eq, liquid at 25 ℃;
seed polyphenylene ether resin (B1): vinylbenzyl-modified polyphenylene ether [ product name, manufactured by mitsubishi GAS chemical corporation: OPE-2St 1200, number average molecular weight: 1200 ];
seed binder resins (C1): acid modificationαOlefin polymers [ manufactured by mitsui chemical company, trade name: unistole H-200, number average molecular weight: 47,000]；
Seeding cationic polymerization initiator (D1): thermal cationic polymerization initiator [ trade name: San-Aid SI-B3 ];
seeding of silane coupling agent (E1): 8-glycidoxy octyltrimethoxysilane [ trade name: KBM4803 ].
[ example 1]
An adhesive composition was prepared by dissolving 3 parts by mass of a liquid curable compound (a1), 50 parts by mass of a polyphenylene ether resin (B1), 100 parts by mass of a binder resin (C1), 0.15 parts by mass of a cationic polymerization initiator (D1), and 0.2 parts by mass of a silane coupling agent (E1) in toluene.
The adhesive composition was applied to the release-treated surface of a release sheet (No. 1 release sheet, product name: SP-PET752150 manufactured by Lintec Co., Ltd.), and the obtained coating film was dried at 100 ℃ for 2 minutes to give a coating film having a thickness of 15μm, an adhesive layer. To the adhesive layer, another 1-piece release sheet (No. 2 release sheet, manufactured by Lintec Co., Ltd.) was bondedTrade names of manufacturers and producers: SP-PET381130) to obtain an adhesive sheet.
Examples 1 to 4 and comparative examples 1 to 3
An adhesive composition and an adhesive sheet were obtained in the same manner as in example 1, except that the kinds and amounts of the respective active ingredients constituting the adhesive composition were changed to those shown in table 1.
The following tests were performed on the adhesive sheets obtained in examples 1 to 4 and comparative examples 1 to 3. The results are shown in Table 1.
[ specific dielectric constant, dielectric loss tangent ]
A plurality of adhesive sheets were laminated by a thermal laminating machine heated to 100 ℃ so that the adhesive layers of the adhesive sheets obtained in examples and comparative examples had a thickness of 1mm, to obtain a laminate having a structure of a release sheet/adhesive layer/release sheet having a thickness of 1 mm. The laminate was heated at 160 ℃ for 1 hour to cure the adhesive layer having a thickness of 1mm, and then the release sheets on both sides were peeled off to obtain a sample for measurement.
The specific dielectric constant and the dielectric loss tangent at 23 ℃ and 1GHz were measured with respect to the obtained measurement sample using an RF impedance/material analyzer (manufactured by Keysight, Inc., E4991A). In the examples and comparative examples, 1GHz was used as an example of the high frequency region.
[ Adaptation for attachment ]
The adhesive sheets obtained in examples and comparative examples were cut to obtain test pieces having a width of 50mm and a length of 150 mm. The adhesive layer exposed by peeling the 2 nd release film of the test piece obtained was laminated on the alkali-free glass at a temperature of 23 ℃ and a relative humidity of 50%, and a pressure was applied thereto at a pressure of 0.5MPa using a pressure-sensitive roller. The sticking test was performed under both conditions of the case where the pressure bonding roller was not heated and the case where the temperature was set to 60 ℃. The adhesive layer was observed to float from the alkali-free glass, and the one without floating was evaluated as a, and the one with floating was evaluated as B.
[ Table 1]
The following results are shown in Table 1.
The cured products of the curable adhesive layers obtained in examples 1 to 4 had low dielectric properties in a high frequency region. Further, these curable adhesive layers have good adhesion suitability.
On the other hand, the curable adhesive layer obtained in comparative example 1 is a layer containing an aromatic curable compound in place of the component (a) of the present invention, and has poor suitability for adhesion, and the specific permittivity and dielectric loss tangent of the cured product thereof have large values.
As shown in comparative example 2, when the aromatic curable compound is contained more than in comparative example 1, the adhesion suitability of the curable adhesive layer is improved, but the low dielectric characteristics are deteriorated.
As shown in comparative example 3, even when the curable adhesive layer contains the component (a) and the component (B), the curable adhesive layer containing the component (a) in an amount of less than 3.0 mass% does not have sufficient adhesion suitability.
Claims (7)
1. An adhesive sheet for devices, which comprises a curable adhesive layer containing the following components (A) and (B), wherein the content of the component (A) is 3.0% by mass or more relative to the entire curable adhesive layer,
(A) the components: a non-aromatic curable compound that is liquid at 25 ℃;
(B) the components: a modified polyphenylene ether resin.
2. The adhesive sheet for devices according to claim 1, wherein the non-aromatic curable compound that is liquid at 25 ℃ is an alicyclic epoxy compound having 2 or more epoxy groups or a compound having 2 or more hydrocarbon groups having a double bond at a terminal.
3. The adhesive sheet for devices according to claim 2, wherein the non-aromatic curable compound which is liquid at 25 ℃ is an alicyclic epoxy compound having 2 epoxy groups or a compound having 2 hydrocarbon groups having a double bond at the terminal.
4. The device adhesive sheet according to claim 3, wherein the alicyclic epoxy compound is an alicyclic diglycidyl ether compound.
5. The adhesive sheet for a device according to any one of claims 1 to 4, further comprising the following component (C),
(C) the components: a binder resin having a reactive group.
6. The adhesive sheet for a device according to any one of claims 1 to 5, further comprising the following component (D),
(D) the components: a cationic polymerization initiator.
7. The adhesive sheet for devices according to any one of claims 1 to 6, wherein a cured product of the curable adhesive layer has a dielectric loss tangent of less than 0.0050 at 23 ℃ and a frequency of 1 GHz.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| JP2019196917 | 2019-10-30 | ||
| JP2019-196917 | 2019-10-30 | ||
| JP2020-043698 | 2020-03-13 | ||
| JP2020043698 | 2020-03-13 | ||
| PCT/JP2020/036882 WO2021085008A1 (en) | 2019-10-30 | 2020-09-29 | Adhesive sheet for devices |
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| CN114555737A true CN114555737A (en) | 2022-05-27 |
| CN114555737B CN114555737B (en) | 2024-03-01 |
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| CN202080074914.6A Active CN114555737B (en) | 2019-10-30 | 2020-09-29 | Adhesive sheet for device |
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| JP (2) | JP6980153B2 (en) |
| KR (1) | KR20220091463A (en) |
| CN (1) | CN114555737B (en) |
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| JP2023127822A (en) | 2022-03-02 | 2023-09-14 | 株式会社リコー | Liquid discharge head, head unit and liquid discharge device |
| TW202346527A (en) * | 2022-03-03 | 2023-12-01 | 日商東洋紡Ｍｃ股份有限公司 | Adhesive agent composition, adhesive sheet containing same, layered body, and printed circuit board |
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2020
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- 2020-09-29 CN CN202080074914.6A patent/CN114555737B/en active Active
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| Publication number | Publication date |
|---|---|
| JPWO2021085008A1 (en) | 2021-11-25 |
| CN114555737B (en) | 2024-03-01 |
| JP6980153B2 (en) | 2021-12-15 |
| KR20220091463A (en) | 2022-06-30 |
| JP2022031739A (en) | 2022-02-22 |
| TW202124636A (en) | 2021-07-01 |
| WO2021085008A1 (en) | 2021-05-06 |
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