CN111051455B - Film-like transparent adhesive and infrared sensor module - Google Patents
Film-like transparent adhesive and infrared sensor module Download PDFInfo
- Publication number
- CN111051455B CN111051455B CN201880055290.6A CN201880055290A CN111051455B CN 111051455 B CN111051455 B CN 111051455B CN 201880055290 A CN201880055290 A CN 201880055290A CN 111051455 B CN111051455 B CN 111051455B
- Authority
- CN
- China
- Prior art keywords
- meth
- acrylate
- film
- transparent adhesive
- group
- 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.)
- Active
Links
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 253
- 239000000853 adhesive Substances 0.000 title claims abstract description 252
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 143
- 238000002834 transmittance Methods 0.000 claims abstract description 31
- 229920000642 polymer Polymers 0.000 claims description 78
- 239000004925 Acrylic resin Substances 0.000 claims description 45
- 229920000178 Acrylic resin Polymers 0.000 claims description 45
- 239000000945 filler Substances 0.000 claims description 38
- 239000011521 glass Substances 0.000 claims description 30
- 239000002245 particle Substances 0.000 claims description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 203
- 239000000203 mixture Substances 0.000 description 112
- 150000001875 compounds Chemical class 0.000 description 85
- -1 and the like Polymers 0.000 description 64
- 229920005989 resin Polymers 0.000 description 58
- 239000011347 resin Substances 0.000 description 58
- 239000000178 monomer Substances 0.000 description 49
- 239000003431 cross linking reagent Substances 0.000 description 44
- 125000000524 functional group Chemical group 0.000 description 43
- 238000001723 curing Methods 0.000 description 40
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 37
- 239000003822 epoxy resin Substances 0.000 description 35
- 229920000647 polyepoxide Polymers 0.000 description 35
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 32
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 31
- 239000003795 chemical substances by application Substances 0.000 description 27
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 26
- 229920000058 polyacrylate Polymers 0.000 description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 23
- 125000003277 amino group Chemical group 0.000 description 19
- 239000005011 phenolic resin Substances 0.000 description 18
- 239000007822 coupling agent Substances 0.000 description 17
- 150000002430 hydrocarbons Chemical group 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- 238000002156 mixing Methods 0.000 description 16
- 239000005056 polyisocyanate Substances 0.000 description 16
- 229920001228 polyisocyanate Polymers 0.000 description 16
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 16
- 239000004593 Epoxy Substances 0.000 description 15
- 239000003999 initiator Substances 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 10
- 230000000996 additive effect Effects 0.000 description 10
- 229920001296 polysiloxane Polymers 0.000 description 10
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 229920000139 polyethylene terephthalate Polymers 0.000 description 9
- 239000005020 polyethylene terephthalate Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 229920005992 thermoplastic resin Polymers 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 125000003700 epoxy group Chemical group 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 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
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000011256 inorganic filler Substances 0.000 description 6
- 229910003475 inorganic filler Inorganic materials 0.000 description 6
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 5
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 238000013007 heat curing Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229940059574 pentaerithrityl Drugs 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 3
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000006059 cover glass Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-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
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 3
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 239000013034 phenoxy resin Substances 0.000 description 3
- 229920006287 phenoxy resin Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 239000005060 rubber Substances 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
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-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
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 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
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- FFBZKUHRIXKOSY-UHFFFAOYSA-N aziridine-1-carboxamide Chemical compound NC(=O)N1CC1 FFBZKUHRIXKOSY-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 125000006841 cyclic skeleton Chemical group 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical class [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000012766 organic filler Substances 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- FWWWRCRHNMOYQY-UHFFFAOYSA-N 1,5-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC(C)=C(N=C=O)C=C1N=C=O FWWWRCRHNMOYQY-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- ZVEMLYIXBCTVOF-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-3-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC(C(C)(C)N=C=O)=C1 ZVEMLYIXBCTVOF-UHFFFAOYSA-N 0.000 description 1
- KSYQGOYOIKQFNA-UHFFFAOYSA-N 1-benzyl-3-methylbenzene Chemical compound CC1=CC=CC(CC=2C=CC=CC=2)=C1 KSYQGOYOIKQFNA-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- 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
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- FKJNJZAGYPPJKZ-UHFFFAOYSA-N 2-hydroxy-1,2-diphenylethanone;methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1.C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 FKJNJZAGYPPJKZ-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- JEHFRMABGJJCPF-UHFFFAOYSA-N 2-methylprop-2-enoyl isocyanate Chemical compound CC(=C)C(=O)N=C=O JEHFRMABGJJCPF-UHFFFAOYSA-N 0.000 description 1
- LOUORYQQOPCXGD-UHFFFAOYSA-N 2-methylpropan-1-ol Chemical compound CC(C)CO.CC(C)CO LOUORYQQOPCXGD-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- SBWOBTUYQXLKSS-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propanoic acid Chemical compound CC(=C)C(=O)OCCC(O)=O SBWOBTUYQXLKSS-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
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 1
- HZHPOJPIGFWDTD-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOC(=O)C=C HZHPOJPIGFWDTD-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
- 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
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- 241001050985 Disco Species 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- GWGWXYUPRTXVSY-UHFFFAOYSA-N N=C=O.N=C=O.CC1=CC=C(C)C=C1 Chemical compound N=C=O.N=C=O.CC1=CC=C(C)C=C1 GWGWXYUPRTXVSY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- UUQQGGWZVKUCBD-UHFFFAOYSA-N [4-(hydroxymethyl)-2-phenyl-1h-imidazol-5-yl]methanol Chemical compound N1C(CO)=C(CO)N=C1C1=CC=CC=C1 UUQQGGWZVKUCBD-UHFFFAOYSA-N 0.000 description 1
- NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- CSNNWDJQKGMZPO-UHFFFAOYSA-N benzoic acid;2-hydroxy-1,2-diphenylethanone Chemical compound OC(=O)C1=CC=CC=C1.C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 CSNNWDJQKGMZPO-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- LKMCJXXOBRCATQ-UHFFFAOYSA-N benzylsulfanylbenzene Chemical compound C=1C=CC=CC=1CSC1=CC=CC=C1 LKMCJXXOBRCATQ-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 238000005247 gettering Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 229940086559 methyl benzoin Drugs 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- YLBPOJLDZXHVRR-UHFFFAOYSA-N n'-[3-[diethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CCO[Si](C)(OCC)CCCNCCN YLBPOJLDZXHVRR-UHFFFAOYSA-N 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 229920002601 oligoester Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 235000010215 titanium dioxide Nutrition 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
- 229950001353 tretamine Drugs 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 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
- 238000001392 ultraviolet--visible--near infrared spectroscopy Methods 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- 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
-
- 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01J—MEASUREMENT OF INTENSITY, VELOCITY, SPECTRAL CONTENT, POLARISATION, PHASE OR PULSE CHARACTERISTICS OF INFRARED, VISIBLE OR ULTRAVIOLET LIGHT; COLORIMETRY; RADIATION PYROMETRY
- G01J1/00—Photometry, e.g. photographic exposure meter
- G01J1/02—Details
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
- Photometry And Measurement Of Optical Pulse Characteristics (AREA)
Abstract
The present invention relates to a film-like transparent adhesive which is thermosetting or energy ray-curable and has a light transmittance of 80% or more at a wavelength of 800nm after curing. Preferably, the light transmittance at the wavelength of 800-2000 nm after curing is more than 80%, and the light transmittance at the wavelength of 850nm after curing is more than 90%.
Description
Technical Field
The present invention relates to a film-like transparent adhesive and an infrared sensor module.
The present application claims priority based on japanese patent application No. 2017-163632 filed in japan on 8/28/2017, and the contents thereof are incorporated herein.
Background
As a covering member for an infrared sensor such as a motion sensor, a cover glass (coverglass) member having high light transmittance in an infrared region has been proposed (patent document 1). In the infrared sensor, the cover glass member is provided with a recess and fixed to a frame portion of the infrared sensor, as in patent document 2, for example.
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent publication No. 2016-040220
Patent document 2: japanese patent laid-open publication No. 2011-037694
Disclosure of Invention
Technical problem to be solved by the invention
If a film-like adhesive having transparency in a wide range of infrared wavelength regions can be used, and a glass wafer having infrared transparency can be directly bonded to an infrared receiving element, the infrared sensor can be further miniaturized.
Accordingly, an object of the present invention is to provide a film-like transparent adhesive that can directly bond a glass wafer to an infrared-receiving element and has translucency in a wide range of infrared wavelengths, and an infrared sensor module using the film-like transparent adhesive.
Means for solving the problems
In order to solve the above-mentioned problems, the present invention provides a film-like transparent adhesive which is thermosetting or energy ray-curable and has a light transmittance of 80% or more at a wavelength of 800nm after curing.
The film-like transparent adhesive of the present invention preferably has a light transmittance of 80% or more at a wavelength of 800 to 2000nm after curing.
The film-like transparent adhesive of the present invention preferably has a light transmittance of 90% or more at a wavelength of 850nm after curing.
The film-like transparent adhesive of the present invention preferably contains a filler, and the filler has an average particle diameter of 450nm or less.
The present invention provides an infrared sensor module in which an infrared receiving element having an infrared receiving portion and a glass wafer are cured and bonded by the film-like transparent adhesive, and the infrared receiving portion is provided so as to receive infrared rays transmitted through the glass wafer and the cured film-like transparent adhesive.
Effects of the invention
According to the present invention, a film-like transparent adhesive capable of bonding a glass wafer to an infrared receiving element, and an infrared sensor module using the film-like transparent adhesive can be provided.
Detailed Description
< film-shaped transparent adhesive >
The film-shaped transparent adhesive of the present invention is a thermosetting or energy ray-curable film-shaped transparent adhesive, and has a light transmittance of 80% or more at a wavelength of 800nm after curing. The film-like transparent adhesive of the present invention has a light transmittance of 80% or more at a wavelength of 800nm of the cured transparent resin film, and therefore can have a light transmittance in an infrared wavelength region in a wide range around the wavelength of 800 nm. The film-like transparent adhesive of the present invention preferably has a light transmittance of 80% or more at a wavelength of 800 to 2000nm after curing, and more preferably has a light transmittance of 90% or more at a wavelength of 850nm after curing. Since the film-like transparent adhesive of the present invention has high transmittance of infrared rays after curing, when the film-like transparent adhesive of the present invention is cured and a glass wafer is bonded to an infrared ray receiving element, the infrared ray receiving element can effectively receive infrared rays transmitted through the glass wafer.
The upper limit of the light transmittance at a wavelength of 800nm after curing of the film-like transparent adhesive is not limited, and may be 95% or 93%. The upper limit of the light transmittance of the film-like transparent adhesive at a wavelength of 800 to 2000nm after curing is not limited, and may be 95% or 93%. The upper limit of the light transmittance at a wavelength of 850nm after curing of the film-like transparent adhesive is not limited, and may be 95% or 93%.
The film-like transparent adhesive of the present invention has thermosetting properties or energy ray-curable properties, and may have both thermosetting properties and energy ray-curable properties. Hereinafter, the film-like transparent adhesive having thermosetting properties is referred to as "thermosetting film-like transparent adhesive", and the film-like transparent adhesive having energy ray-curing properties is referred to as "energy ray-curable film-like transparent adhesive".
It is preferable that the film-like transparent adhesive has pressure-sensitive adhesiveness. A film-like transparent adhesive having both curability and pressure-sensitive adhesiveness can be attached by lightly pressing the adhesive in an uncured state against various adherends. The film-like transparent adhesive may be heated to soften it and attached to various adherends. The film-shaped transparent adhesive is cured to finally obtain a cured product having high impact resistance, and the cured product can maintain sufficient adhesive properties even under severe conditions of high temperature and high humidity.
Since the film-like transparent adhesive of the present invention is in the form of a film, there is no fear of generation of droplets when the infrared ray receiving element and the glass wafer are bonded by curing, and the infrared ray receiving element and the glass wafer can be simultaneously bonded by heat treatment in the production of the infrared ray sensor module using the thermosetting film-like transparent adhesive.
The film-like transparent adhesive may be composed of one layer (single layer) or may be composed of a plurality of layers of two or more layers. When the film-like transparent adhesive is composed of a plurality of layers, the plurality of layers may be the same as or different from each other, and the combination of the plurality of layers is not particularly limited as long as the effect of the present invention is not impaired.
In the present specification, not limited to the case of the film-shaped transparent adhesive, the phrase "a plurality of layers may be the same or different from each other" means "all layers may be the same or different from each other, or only a part of layers may be the same", and "a plurality of layers are different from each other" means "at least one of the constituent material and the thickness of each layer is different from each other".
The thickness of the film-like transparent adhesive is not particularly limited, but is preferably 1 to 50 μm, and more preferably 3 to 40 μm. By setting the thickness of the film-like transparent pressure-sensitive adhesive to the lower limit or more, higher adhesive force to an adherend (i.e., a glass wafer and an infrared ray receiving element) can be obtained.
Here, the "thickness of the film-like transparent adhesive" refers to the thickness of the entire film-like transparent adhesive, and for example, the thickness of the film-like transparent adhesive composed of a plurality of layers refers to the total thickness of all the layers constituting the film-like transparent adhesive.
In the present specification, the "energy ray" refers to a ray having an energy quantum in an electromagnetic wave or a charged particle beam, and examples thereof include ultraviolet rays, radiation, an electron beam, and the like. The ultraviolet rays can be irradiated by using, for example, a high-pressure mercury lamp, fusion H lamp (fusion H lamp), xenon lamp, black light lamp, LED lamp, or the like as an ultraviolet ray source. The electron beam can be irradiated with an electron beam generated by an electron beam accelerator or the like.
In the present specification, "energy ray-curable property" refers to a property of curing by irradiation with an energy ray, and "non-energy ray-curable property" refers to a property of not curing even by irradiation with an energy ray.
O thermosetting film-like transparent adhesive
When the film-like transparent adhesive of the present invention has thermosetting properties, examples of preferable thermosetting film-like transparent adhesives include film-like transparent adhesives containing a polymer component and a thermosetting component, and more preferably film-like transparent adhesives containing a polymer component, a thermosetting component and a filler. The polymer component is a component formed by polymerization reaction of a polymerizable compound. The thermosetting component is a component that can undergo a curing (i.e., superposing) reaction using heat as a trigger for the reaction. In the present invention, the polymerization reaction also includes a polycondensation reaction.
[ thermosetting adhesive composition ]
The thermosetting film-like transparent adhesive can be formed using a thermosetting adhesive composition containing the constituent materials thereof. For example, a film-like transparent adhesive can be formed at a target site by applying a thermosetting adhesive composition to a surface to be formed of a thermosetting film-like transparent adhesive and drying the composition as needed. The content ratio of the components that do not vaporize at ordinary temperature in the thermosetting adhesive composition is generally the same as the content ratio of the components of the thermosetting film-like transparent adhesive. In the present specification, "normal temperature" means a temperature at which cooling or heating is not particularly performed, that is, a normal temperature, and includes, for example, a temperature of 15 to 25 ℃.
The thermosetting adhesive composition may be applied by a known method, and examples thereof include a method using various coaters such as a knife coater, a blade coater, a bar coater, a gravure coater, a comma coater (comma coater), a roll coater, a curtain coater, a die coater, a knife coater, a screen coater (screen coater), a meyer bar coater, and a kiss coater.
The drying conditions of the thermosetting adhesive composition are not particularly limited, but when the thermosetting adhesive composition contains a solvent described later, it is preferable to perform heat drying, and in this case, it is preferable to perform drying at 70 to 130 ℃ for 10 seconds to 5 minutes, for example.
Examples of the preferable thermosetting adhesive composition include a thermosetting adhesive composition containing a polymer component (a) and an epoxy thermosetting resin (b). Hereinafter, each component will be described.
(Polymer component (a))
The polymer component (a) is a component formed by polymerization reaction of a polymerizable compound, and is a polymer compound for imparting film formability, flexibility, and the like to a film-like transparent adhesive and for improving adhesiveness (sticking property) to an adhesive object such as a glass wafer. The polymer component (a) is also a component that does not correspond to the epoxy resin (b1) and the thermosetting agent (b2) described below.
The thermosetting adhesive composition and the thermosetting film-shaped transparent adhesive may contain only one kind of the polymer component (a), or two or more kinds of the polymer component (a), and when two or more kinds of the polymer component (a) are contained, the combination and ratio of the two or more kinds of the polymer component (a) may be arbitrarily selected.
Examples of the polymer component (a) include acrylic resins (resins having a (meth) acryloyl group), polyesters, urethane resins (i.e., resins having a urethane bond), acrylic urethane resins, silicone resins (i.e., resins having a siloxane bond), rubber resins (i.e., resins having a rubber structure), phenoxy resins, thermosetting polyimides, and the like, and acrylic resins are preferable.
As the acrylic resin in the polymer component (a), a known acrylic polymer can be mentioned.
The weight average molecular weight (Mw) of the acrylic resin is preferably 10000 to 2000000, more preferably 100000 to 1500000.
By making the weight average molecular weight of the acrylic resin be not less than the lower limit, the shape stability of the film-like transparent adhesive (i.e., the stability with time during storage) is improved. When the weight average molecular weight of the acrylic resin is not more than the upper limit, the film-like transparent pressure-sensitive adhesive can easily follow the uneven surface of the adherend, and generation of voids (void) between the adherend and the film-like transparent pressure-sensitive adhesive can be further suppressed.
In the present specification, unless otherwise specified, "weight average molecular weight" means a polystyrene equivalent value measured by a Gel Permeation Chromatography (GPC) method.
The glass transition temperature (Tg) of the acrylic resin is preferably-60 to 70 ℃, more preferably-30 to 50 ℃. When the Tg of the acrylic resin is not less than the lower limit, the adhesive strength between the film-like transparent adhesive and the support sheet is suppressed, and the glass wafer having the film-like transparent adhesive is more easily separated from the support sheet. When the Tg of the acrylic resin is not more than the upper limit, the adhesive strength between the film-like transparent adhesive and the glass wafer is improved.
Examples of the (meth) acrylic ester constituting the acrylic resin include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, n-octyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, dodecyl (meth) acrylate, and the like, Alkyl (meth) acrylates having a chain structure in which the number of carbon atoms in the alkyl group constituting the alkyl ester is 1 to 18, such as tetradecyl (meth) acrylate (myristyl (meth) acrylate), pentadecyl (meth) acrylate, hexadecyl (meth) acrylate (palmityl (meth) acrylate), heptadecyl (meth) acrylate, and octadecyl (meth) acrylate (stearyl (meth) acrylate);
cycloalkyl (meth) acrylates such as isobornyl (meth) acrylate and dicyclopentanyl (meth) acrylate;
aralkyl (meth) acrylates such as benzyl (meth) acrylate;
cycloalkenyl (meth) acrylates such as dicyclopentenyl (meth) acrylate;
cycloalkenyloxyalkyl (meth) acrylates such as dicyclopentenyloxyethyl (meth) acrylate;
(meth) acrylimide;
glycidyl group-containing (meth) acrylates such as glycidyl (meth) acrylate;
hydroxyl group-containing (meth) acrylates such as hydroxymethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate;
and substituted amino group-containing (meth) acrylates such as N-methylaminoethyl (meth) acrylate. Here, the "substituted amino group" refers to a group in which one or two hydrogen atoms of an amino group are substituted with a group other than a hydrogen atom.
In the present specification, "(meth) acrylic acid" is a concept including "acrylic acid" and "methacrylic acid". Similar terms to (meth) acrylic acid are also the same, for example, "(meth) acrylate" is a concept including "acrylate" and "methacrylate", and "(meth) acryl" is a concept including "acryl" and "methacryl".
The acrylic resin may be copolymerized with one or two or more monomers selected from (meth) acrylic acid, itaconic acid, vinyl acetate, acrylonitrile, styrene, N-methylol acrylamide, and the like, for example, in addition to the (meth) acrylate.
The acrylic resin may be composed of only one monomer, or two or more monomers, and when two or more monomers are used, the combination and ratio of the monomers can be arbitrarily selected.
The acrylic resin may have, in addition to the above hydroxyl group, a functional group capable of bonding to another compound, such as a vinyl group, (meth) acryloyl group, amino group, carboxyl group, or isocyanate group. These functional groups represented by hydroxyl groups of the acrylic resin may be bonded to other compounds via a crosslinking agent (f) described later, or may be directly bonded to other compounds without the crosslinking agent (f). By bonding the acrylic resin to another compound through the functional group, the reliability of a package (package) obtained using the film-like transparent adhesive tends to be improved.
In the present invention, as the polymer component (a), a thermoplastic resin other than the acrylic resin (hereinafter, simply referred to as "thermoplastic resin") may be used alone without using the acrylic resin, or the thermoplastic resin and the acrylic resin may be used together. By using the thermoplastic resin, the glass wafer provided with the film-like transparent pressure-sensitive adhesive can be more easily separated from the support sheet, or the film-like transparent pressure-sensitive adhesive can easily follow the uneven surface of the adherend, and the occurrence of voids and the like between the adherend and the film-like transparent pressure-sensitive adhesive can be further suppressed.
The weight average molecular weight of the thermoplastic resin is preferably 1000 to 100000, and more preferably 3000 to 80000.
The glass transition temperature (Tg) of the thermoplastic resin is preferably-30 to 150 ℃, and more preferably-20 to 120 ℃.
Examples of the thermoplastic resin include polyester, polyurethane, phenoxy resin, polybutylene, polybutadiene, and polystyrene.
The thermoplastic resin contained in the thermosetting adhesive composition and the film-shaped transparent adhesive may be one kind or two or more kinds, and in the case of two or more kinds, the combination and ratio thereof may be arbitrarily selected.
In the thermosetting adhesive composition, regardless of the kind of the polymer component (a), the proportion of the content of the polymer component (a) to the total content of all the components except the solvent (i.e., the content of the polymer component (a) of the film-shaped transparent adhesive) is preferably 20 to 75% by mass, more preferably 30 to 65% by mass.
(epoxy thermosetting resin (b))
The epoxy thermosetting resin (b) is composed of an epoxy resin (b1) and a thermosetting agent (b 2).
The epoxy thermosetting resin (b) contained in the thermosetting adhesive composition and the thermosetting film-like transparent adhesive may be one kind or two or more kinds, and when two or more kinds are contained, the combination and ratio of these may be arbitrarily selected.
Epoxy resin (b1)
Examples of the epoxy resin (b1) include known epoxy resins, and examples thereof include polyfunctional epoxy resins, biphenyl compounds, bisphenol a diglycidyl ether and hydrogenated products thereof, o-cresol novolac epoxy resins, dicyclopentadiene epoxy resins, biphenyl epoxy resins, bisphenol a epoxy resins, bisphenol F epoxy resins, and epoxy resins having a phenylene skeleton.
As the epoxy resin (b1), an epoxy resin having an unsaturated hydrocarbon group can also be used. The compatibility of the epoxy resin having an unsaturated hydrocarbon group with the acrylic resin is higher than that of the epoxy resin having no unsaturated hydrocarbon group with the acrylic resin. Therefore, by using the epoxy resin having an unsaturated hydrocarbon group, the reliability of the package obtained by using the film-like transparent adhesive is improved.
Examples of the epoxy resin having an unsaturated hydrocarbon group include compounds in which a part of the epoxy group of a polyfunctional epoxy resin is converted into a group having an unsaturated hydrocarbon group. Such a compound can be obtained, for example, by addition reaction of (meth) acrylic acid or a derivative thereof with an epoxy group. In the present specification, unless otherwise specified, "derivative" refers to a compound in which one or more groups of an original compound are substituted with other groups (substituents). Here, the "group" is not only an atomic group in which a plurality of atoms are bonded, but also a group including one atom.
Examples of the epoxy resin having an unsaturated hydrocarbon group include compounds in which a group having an unsaturated hydrocarbon group is directly bonded to an aromatic ring or the like constituting the epoxy resin.
The unsaturated hydrocarbon group is a polymerizable unsaturated group, and specific examples thereof include an ethylene group (vinyl group), a 2-propenyl group (allyl group), (meth) acryloyl group, and (meth) acrylamido group, with acryloyl group being preferred.
The number average molecular weight of the epoxy resin (b1) is not particularly limited, but is preferably 300 to 30000, more preferably 400 to 10000, and particularly preferably 500 to 3000 in view of curability of the film-like transparent adhesive and strength and heat resistance of the film-like transparent adhesive after heat curing.
The epoxy equivalent of the epoxy resin (b1) is preferably 100 to 1000g/eq, more preferably 150 to 800 g/eq.
The epoxy resin (b1) contained in the thermosetting adhesive composition and the thermosetting film-like transparent adhesive may be one kind or two or more kinds, and when two or more kinds are contained, the combination and ratio thereof may be arbitrarily selected.
Heat-curing agent (b2)
The thermosetting agent (b2) functions as a curing agent for the epoxy resin (b 1).
Examples of the thermosetting agent (b2) include compounds having two or more functional groups reactive with epoxy groups in one molecule. Examples of the functional group include a phenolic hydroxyl group, an alcoholic hydroxyl group, an amino group, a carboxyl group, and a group obtained by anhydrizing an acid group, and the like, and a phenolic hydroxyl group, an amino group, or a group obtained by anhydrizing an acid group are preferable, and a phenolic hydroxyl group or an amino group is more preferable.
Examples of the phenol curing agent having a phenolic hydroxyl group in the heat curing agent (b2) include polyfunctional phenol resins, biphenol, novolak-type phenol resins, dicyclopentadiene-type phenol resins, and aralkyl-type phenol resins.
Examples of the amine-based curing agent having an amino group in the thermosetting agent (b2) include Dicyandiamide (DICY).
The thermosetting agent (b2) may have an unsaturated hydrocarbon group.
Examples of the unsaturated hydrocarbon group-containing thermosetting agent (b2) include a compound in which a part of the hydroxyl groups of the phenol resin is substituted with an unsaturated hydrocarbon group-containing group, a compound in which an unsaturated hydrocarbon group-containing group is directly bonded to an aromatic ring of the phenol resin, and the like.
The unsaturated hydrocarbon group in the thermosetting agent (b2) is the same as the unsaturated hydrocarbon group in the above-mentioned epoxy resin having an unsaturated hydrocarbon group.
When a phenol-based curing agent is used as the thermosetting agent (b2), the thermosetting agent (b2) is preferably a thermosetting agent having a high softening point or glass transition temperature.
Among the thermosetting agents (b2), for example, the number average molecular weight of the resin component such as a polyfunctional phenol resin, a novolak-type phenol resin, a dicyclopentadiene-type phenol resin, an aralkyl-type phenol resin is preferably 300 to 30000, more preferably 400 to 10000, and particularly preferably 500 to 3000.
In the thermosetting agent (b2), the molecular weight of the non-resin component such as biphenol and dicyandiamide is not particularly limited, and is preferably 60 to 500, for example.
The thermosetting adhesive composition and the thermosetting film-like transparent adhesive may contain only one kind of the thermosetting agent (b2), or two or more kinds thereof, and when two or more kinds thereof are contained, the combination and ratio thereof may be arbitrarily selected.
In the thermosetting adhesive composition and the thermosetting film-shaped transparent adhesive, the content of the thermosetting agent (b2) is preferably 0.1 to 500 parts by mass, more preferably 1 to 200 parts by mass, relative to 100 parts by mass of the content of the epoxy resin (b 1). When the content of the thermosetting agent (b2) is not less than the lower limit value, curing of the film-shaped transparent adhesive is more easily performed. When the content of the thermosetting agent (b2) is not more than the upper limit, the moisture absorption rate of the film-like transparent adhesive is reduced, and the reliability of the package obtained using the film-like transparent adhesive is further improved.
In the thermosetting adhesive composition and the thermosetting film-shaped transparent adhesive, the content of the epoxy thermosetting resin (b) (the total content of the epoxy resin (b1) and the thermosetting agent (b 2)) is preferably 5 to 100 parts by mass, more preferably 6 to 90 parts by mass, and particularly preferably 7 to 80 parts by mass, relative to 100 parts by mass of the content of the polymer component (a).
In order to improve various physical properties of the thermosetting film-like transparent adhesive, the thermosetting film-like transparent adhesive may further contain, in addition to the polymer component (a) and the epoxy thermosetting resin (b), other components not corresponding to the polymer component (a) and the epoxy thermosetting resin (b) as required.
Preferable examples of the other components contained in the thermosetting film-like transparent adhesive include a curing accelerator (c), a filler (d), a coupling agent (e), a crosslinking agent (f), an energy ray-curable resin (g), a photopolymerization initiator (h), and a general-purpose additive (i).
(curing Accelerator (c))
The curing accelerator (c) is a component for adjusting the curing speed of the thermosetting adhesive composition.
Examples of the preferable curing accelerator (c) include tertiary amines such as triethylenediamine, benzyldimethylamine, triethanolamine, dimethylaminoethanol, and tris (dimethylaminomethyl) phenol; imidazoles (imidazole in which 1 or more hydrogen atoms are substituted with a group other than a hydrogen atom) such as 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2-phenyl-4, 5-dihydroxymethylimidazole and 2-phenyl-4-methyl-5-hydroxymethylimidazole; organophosphines (phosphines in which 1 or more hydrogen atoms are substituted with an organic group), such as tributylphosphine, diphenylphosphine, and triphenylphosphine; tetraphenylboron salts such as tetraphenylphosphonium tetraphenylborate and triphenylphosphine tetraphenylboron ester.
The curing accelerator (c) contained in the thermosetting adhesive composition and the thermosetting film-like transparent adhesive may be one kind or two or more kinds, and in the case of two or more kinds, the combination and ratio thereof may be arbitrarily selected.
When the curing accelerator (c) is used, the content of the curing accelerator (c) is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, based on 100 parts by mass of the content of the epoxy thermosetting resin (b) in the thermosetting adhesive composition and the thermosetting film-like transparent adhesive. By setting the content of the curing accelerator (c) to the lower limit or more, the effect of using the curing accelerator (c) can be more remarkably obtained. When the content of the curing accelerator (c) is not more than the above upper limit, for example, the effect of suppressing the segregation of the highly polar curing accelerator (c) by moving to the side of the pressure-sensitive adhesive surface with the adherend in the film-like transparent pressure-sensitive adhesive under high temperature and high humidity conditions is increased, and the reliability of the infrared sensor module obtained by using the film-like transparent pressure-sensitive adhesive is further improved.
(Filler (d))
By containing the filler (d) in the thermosetting film-like transparent adhesive, the thermal expansion coefficient of the thermosetting film-like transparent adhesive can be easily adjusted, and by optimizing the thermal expansion coefficient with respect to the target to which the thermosetting film-like transparent adhesive is attached, the reliability of the package obtained using the thermosetting film-like transparent adhesive can be further improved. By incorporating the filler (d) into the thermosetting film-like transparent adhesive, the moisture absorption rate of the cured film-like transparent adhesive can be reduced, and the heat dissipation property can be improved.
The filler (d) may be any of an organic filler and an inorganic filler.
Examples of preferable organic fillers include acrylic particles and silicone particles. Among them, acrylic particles are preferable from the viewpoint of light transmittance or compatibility with other materials.
Examples of preferable inorganic fillers include powders of silica, alumina, talc, calcium carbonate, titanium white, red iron oxide, silicon carbide, boron nitride, and the like; beads obtained by spheroidizing these inorganic fillers; surface-modified products of these inorganic fillers; single crystal fibers of these inorganic filler materials; glass fibers, and the like. Among them, the inorganic filler is preferably silica or alumina, and more preferably spherical silica.
The filler (d) contained in the thermosetting adhesive composition and the thermosetting film-like transparent adhesive may be one kind or two or more kinds, and in the case of two or more kinds, the combination and ratio thereof may be arbitrarily selected.
When acrylic fine particles are used as the filler (d), the average particle diameter of the acrylic fine particles is preferably 1 to 450nm, more preferably 1 to 400 nm.
When spherical silica is used as the filler (d), the average particle diameter of the spherical silica is preferably 1 to 250nm, more preferably 5 to 200 nm.
When the filler (d) is used, the content of the filler (d) in the thermosetting adhesive composition is preferably 5 to 80% by mass, and more preferably 7 to 60% by mass, based on the total content of all the components except the solvent (i.e., the content of the filler (d) in the film-shaped transparent adhesive). By setting the content of the filler (d) in such a range, the adjustment of the thermal expansion coefficient described above becomes easier.
(coupling agent (e))
When the film-shaped transparent pressure-sensitive adhesive contains the coupling agent (e), the adhesiveness to an adherend and the adhesion are improved. By incorporating the coupling agent (e) into the film-like transparent adhesive, the water resistance of the cured product is improved without impairing the heat resistance. The coupling agent (e) is a compound having a functional group reactive with an inorganic compound or an organic compound.
The coupling agent (e) is preferably a compound having a functional group reactive with the functional group of the polymer component (a), the epoxy thermosetting resin (b), or the like, and more preferably a silane coupling agent.
Examples of the preferable silane coupling agent include 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropylmethyldiethoxysilane, 3-glycidyloxypropyltriethoxysilane, 3-glycidyloxymethyldiethoxysilane, 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3- (2-aminoethylamino) propyltrimethoxysilane, 3- (2-aminoethylamino) propylmethyldiethoxysilane, 3- (phenylamino) propyltrimethoxysilane, 3-anilinopropyltrimethoxysilane, 3-ureopropyltriethoxysilane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropyltriethoxysilane, and the like, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, bis (3-triethoxysilylpropyl) tetrasulfide, methyltrimethoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, vinyltriacetoxysilane, imidazolesilane and the like.
The coupling agent (e) contained in the thermosetting adhesive composition and the thermosetting film-shaped transparent adhesive may be one kind or two or more kinds, and when two or more kinds are contained, the combination and ratio thereof may be arbitrarily selected.
When the coupling agent (e) is used, the content of the coupling agent (e) is preferably 0.03 to 20 parts by mass, more preferably 0.05 to 10 parts by mass, and particularly preferably 0.1 to 5 parts by mass, based on 100 parts by mass of the total content of the polymer component (a) and the epoxy thermosetting resin (b). By setting the content of the coupling agent (e) to the lower limit or more, effects by the use of the coupling agent (e) can be more remarkably obtained, such as improvement in dispersibility of the filler (d) in the resin and improvement in adhesiveness of the thermosetting film-like transparent adhesive to an adherend. By setting the content of the coupling agent (e) to the upper limit value or less, the occurrence of degassing can be further suppressed.
(crosslinking agent (f))
When a compound having a functional group such as a vinyl group, (meth) acryloyl group, amino group, hydroxyl group, carboxyl group, or isocyanate group, which is capable of bonding to another compound, such as the acrylic resin, is used as the polymer component (a), the thermosetting adhesive composition and the thermosetting film-shaped transparent adhesive may contain a crosslinking agent (f) for bonding and crosslinking the functional group to another compound. By crosslinking with the crosslinking agent (f), the initial adhesive force and cohesive force of the film-like transparent adhesive can be adjusted.
Examples of the crosslinking agent (f) include an organic polyisocyanate compound, an organic polyimine compound, a metal chelate crosslinking agent (a crosslinking agent having a metal chelate structure), an aziridine crosslinking agent (a crosslinking agent having an aziridine group), and the like.
Examples of the organic polyisocyanate compound include an aromatic polyisocyanate compound, an aliphatic polyisocyanate compound, and an alicyclic polyisocyanate compound (hereinafter, these compounds may be collectively abbreviated as "aromatic polyisocyanate compound, etc.); trimers, isocyanurate bodies and adducts of the aromatic polyisocyanate compounds and the like; and isocyanate-terminated urethane prepolymers obtained by reacting the aromatic polyisocyanate compound and the like with a polyol compound. The "adduct" refers to a reaction product of the aromatic polyisocyanate compound, the aliphatic polyisocyanate compound or the alicyclic polyisocyanate compound with a low molecular weight active hydrogen-containing compound such as ethylene glycol, propylene glycol, neopentyl glycol, trimethylolpropane or castor oil, and examples thereof include a xylylene diisocyanate adduct of trimethylolpropane described later. The "isocyanate-terminated urethane prepolymer" is the same as described above.
More specific examples of the organic polyisocyanate compound include 2, 4-tolylene diisocyanate; 2, 6-toluene diisocyanate; 1, 3-xylylene diisocyanate; 1, 4-xylene diisocyanate; diphenylmethane-4, 4' -diisocyanate; diphenylmethane-2, 4' -diisocyanate; 3-methyl diphenylmethane diisocyanate; hexamethylene diisocyanate; isophorone diisocyanate; dicyclohexylmethane-4, 4' -diisocyanate; dicyclohexylmethane-2, 4' -diisocyanate; a compound obtained by adding one or more of tolylene diisocyanate, hexamethylene diisocyanate and xylylene diisocyanate to all or a part of the hydroxyl groups of a polyol such as trimethylolpropane; lysine diisocyanate, and the like.
Examples of the organic polyimine compound include N, N ' -diphenylmethane-4, 4 ' -bis (1-aziridinecarboxamide), trimethylolpropane-tri- β -aziridinylpropionate, tetramethylolmethane-tri- β -aziridinylpropionate, and N, N ' -toluene-2, 4-bis (1-aziridinecarboxamide) triethylenemelamine.
When an organic polyisocyanate compound is used as the crosslinking agent (f), a hydroxyl group-containing polymer is preferably used as the polymer component (a). When the crosslinking agent (f) has an isocyanate group and the polymer component (a) has a hydroxyl group, the crosslinked structure can be easily introduced into the film-like transparent adhesive by the reaction of the crosslinking agent (f) with the polymer component (a).
The crosslinking agent (f) contained in the thermosetting adhesive composition and the thermosetting film-like transparent adhesive may be one kind or two or more kinds, and in the case of two or more kinds, the combination and ratio thereof may be arbitrarily selected.
When the crosslinking agent (f) is used, the content of the crosslinking agent (f) in the thermosetting adhesive composition is preferably 0.01 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, and particularly preferably 0.3 to 5 parts by mass, relative to 100 parts by mass of the content of the polymer component (a). By setting the content of the crosslinking agent (f) to the lower limit or more, the effect brought by the use of the crosslinking agent (f) can be more remarkably obtained. By making the content of the crosslinking agent (f) the upper limit value or less, the excessive use of the crosslinking agent (f) is suppressed.
(energy ray-curable resin (g))
By containing the energy ray-curable resin (g) in the film-like transparent adhesive, the properties can be changed by irradiation with an energy ray.
The energy ray-curable resin (g) is obtained by polymerizing (curing) an energy ray-curable compound.
Examples of the energy ray-curable compound include compounds having at least one polymerizable double bond in the molecule, and acrylate compounds having a (meth) acryloyl group are preferable.
Examples of the acrylic ester-based compound include (meth) acrylates having a chain-like aliphatic skeleton such as trimethylolpropane tri (meth) acrylate, tetramethylolmethane tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol monohydroxypenta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, 1, 4-butanediol di (meth) acrylate, and 1, 6-hexanediol di (meth) acrylate; cyclic aliphatic skeleton-containing (meth) acrylates such as dicyclopentyl di (meth) acrylate; polyalkylene glycol (meth) acrylates such as polyethylene glycol di (meth) acrylate; an oligoester (meth) acrylate; a urethane (meth) acrylate oligomer; epoxy-modified (meth) acrylates; a polyether (meth) acrylate other than the polyalkylene glycol (meth) acrylate; itaconic acid oligomers, and the like.
The weight average molecular weight of the energy ray curable resin (g) is preferably 100 to 30000, more preferably 300 to 10000.
The energy ray-curable resin (g) contained in the thermosetting adhesive composition may be one kind only, or two or more kinds, and in the case of two or more kinds, the combination and ratio thereof may be arbitrarily selected.
When the energy ray-curable resin (g) is used, the content of the energy ray-curable resin (g) in the thermosetting adhesive composition is preferably 1 to 95% by mass, more preferably 1.5 to 90% by mass, and particularly preferably 2 to 85% by mass.
(photopolymerization initiator (h))
When the thermosetting adhesive composition contains the energy ray-curable resin (g), a photopolymerization initiator (h) may be contained in order to efficiently advance the polymerization reaction of the energy ray-curable resin (g).
Examples of the photopolymerization initiator (h) in the thermosetting adhesive composition include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin benzoic acid, benzoin methyl benzoate, and benzoin dimethyl ketal; acetophenone compounds such as acetophenone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, and 2, 2-dimethoxy-1, 2-diphenylethan-1-one; acylphosphine oxide compounds such as phenylbis (2,4, 6-trimethylbenzoyl) phosphine oxide and 2,4, 6-trimethylbenzoyl diphenylphosphine oxide; sulfide compounds such as benzylphenylsulfide, tetramethylthiuram monosulfide and the like; α -ketol compounds such as 1-hydroxycyclohexyl phenyl ketone; azo compounds such as azobisisobutyronitrile; titanocene compounds such as titanocene; thioxanthone compounds such as thioxanthone; a peroxide compound; diketone compounds such as butanedione; benzil; dibenzoyl; benzophenone; 2, 4-diethylthioxanthone; 1, 2-diphenylmethane; 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl ] propanone; quinone compounds such as 1-chloroanthraquinone and 2-chloroanthraquinone.
As the photopolymerization initiator (h), for example, a photosensitizer such as amine may be used.
The photopolymerization initiator (h) contained in the thermosetting adhesive composition may be one kind only, or two or more kinds, and in the case of two or more kinds, the combination and ratio thereof may be arbitrarily selected.
When the photopolymerization initiator (h) is used, the content of the photopolymerization initiator (h) in the thermosetting adhesive composition is preferably 0.1 to 20 parts by mass, more preferably 1 to 10 parts by mass, and particularly preferably 2 to 5 parts by mass, relative to 100 parts by mass of the energy ray-curable resin (g).
(general additive (i))
The general-purpose additive (i) may be any known additive, and may be arbitrarily selected according to the purpose, and is not particularly limited, but preferable additives include, for example, a plasticizer, an antistatic agent, an antioxidant, a colorant (dye, pigment), a gettering agent (gelling agent), and the like.
The general-purpose additive (i) contained in the thermosetting adhesive composition and the thermosetting film-like transparent adhesive may be one kind or two or more kinds, and when two or more kinds are contained, the combination and ratio thereof may be arbitrarily selected.
The content of the thermosetting adhesive composition and the thermosetting film-shaped transparent adhesive is not particularly limited, and may be appropriately selected according to the purpose.
In the thermosetting adhesive composition and the thermosetting film-shaped transparent adhesive, the content of the polymer component (a) is preferably 30 parts by mass or more, and more preferably 38 parts by mass or more, per 100 parts by mass of the total content of the polymer component (a), the epoxy thermosetting resin (b), and the filler (d) (the total content of the polymer component (a), the epoxy resin (b1), the thermosetting agent (b2), and the filler (d)), in order to improve the film-forming property such as to improve the surface state of the film-shaped transparent adhesive. In this regard, the upper limit of the content of the polymer component (a) is not particularly limited, but is preferably 65 parts by mass.
On the other hand, in the thermosetting adhesive composition and the thermosetting film-shaped transparent adhesive, in order to improve the reliability of the film-shaped transparent adhesive, the content of the polymer component (a) is preferably 45 parts by mass or more per 100 parts by mass of the total content of the polymer component (a), the epoxy thermosetting resin (b), and the filler (d) (that is, the total content of the polymer component (a), the epoxy resin (b1), the thermosetting agent (b2), and the filler (d)). In this regard, the upper limit of the content of the polymer component (a) is not particularly limited, but is preferably 65 parts by mass.
(solvent)
Preferably, the thermosetting adhesive composition further contains a solvent. The thermosetting adhesive composition containing a solvent is excellent in workability.
The solvent is not particularly limited, and preferable examples thereof include hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol, 2-propanol, isobutanol (2-methylpropane-1-ol), and 1-butanol; esters such as ethyl acetate; ketones such as acetone and methyl ethyl ketone; ethers such as tetrahydrofuran; amides (i.e., compounds having an amide bond) such as dimethylformamide and N-methylpyrrolidone, and the like.
The binder composition may contain only one kind of solvent, or two or more kinds of solvents, and in the case of two or more kinds of solvents, the combination and ratio of the solvents can be arbitrarily selected.
The solvent contained in the thermosetting adhesive composition is preferably methyl ethyl ketone or the like, since the components contained in the thermosetting adhesive composition can be more uniformly mixed.
[ Process for producing thermosetting adhesive composition ]
The thermosetting adhesive composition is obtained by blending the components for constituting it.
The order of addition of the components in blending is not particularly limited, and two or more components may be added simultaneously.
When a solvent is used, the solvent may be mixed with any of the components other than the solvent to preliminarily dilute the components, or the solvent may be mixed with the components without preliminarily diluting any of the components other than the solvent to use the mixture.
The method for mixing the components at the time of blending is not particularly limited, and may be appropriately selected from the following known methods: a method of mixing by rotating a stirrer, a stirring blade, or the like; a method of mixing using a stirrer; a method of mixing by applying ultrasonic waves, and the like.
The temperature and time for adding and mixing the components are not particularly limited and may be appropriately adjusted as long as the components are not deteriorated, but the temperature is preferably 15 to 30 ℃.
Energy ray-curable film-like transparent adhesive
When the film-shaped transparent adhesive of the present invention is energy-ray curable, examples of the energy-ray curable film-shaped transparent adhesive include an energy-ray curable film-shaped transparent adhesive containing an energy-ray curable component (a), and preferably an energy-ray curable film-shaped transparent adhesive containing an energy-ray curable component (a) and a filler.
In the energy ray-curable film-like transparent adhesive, the energy ray-curable component (a) is preferably uncured, and preferably has tackiness, and more preferably is uncured and has tackiness. Here, "energy ray" and "energy ray curability" are the same as those described above.
The curing conditions for curing the energy ray-curable film-like transparent adhesive after the energy ray-curable film-like transparent adhesive is attached to a glass wafer and further attached to an infrared ray-receiving element are not particularly limited as long as the cured product has a degree of cure sufficient to exhibit its function, and can be appropriately selected depending on the type of the energy ray-curable film-like transparent adhesive.
For example, when the energy ray-curable film-like transparent adhesive is cured, the illuminance of the energy ray is preferably 120 to 280mW/cm2. The amount of the energy ray during curing is preferably 100 to 1000mJ/cm2。
[ energy ray-curable adhesive composition ]
The energy ray-curable film-like transparent adhesive can be formed using an energy ray-curable adhesive composition containing the constituent materials thereof. For example, an energy ray-curable film-shaped transparent adhesive can be formed at a target site by applying an energy ray-curable adhesive composition to a formation target surface of an energy ray-curable film-shaped transparent adhesive and drying the composition as necessary.
The energy ray-curable adhesive composition can be applied, for example, by the same method as in the case of applying the thermosetting adhesive composition.
The drying conditions of the energy ray-curable adhesive composition are not particularly limited, but when the energy ray-curable adhesive composition contains a solvent described later, it is preferably dried by heating. The solvent-containing energy ray-curable adhesive composition is preferably dried at 70 to 130 ℃ for 10 seconds to 5 minutes, for example. However, in the present invention, it is preferable to dry the energy ray-curable adhesive composition so that the formed energy ray-curable film-like transparent adhesive is not thermally cured.
< energy ray-curable adhesive composition (IV-1) >)
Examples of a preferable energy ray-curable adhesive composition include an energy ray-curable adhesive composition (IV-1) (in the present specification, the composition may be simply referred to as "composition (IV-1)") containing the energy ray-curable component (a) and a filler.
[ energy ray-curable component (a) ]
The energy ray-curable component (a) is a component that is cured by irradiation with an energy ray, and is also a component for imparting film formability, flexibility, and the like to the energy ray-curable film-shaped transparent adhesive and for forming a hard transparent resin film after curing.
Examples of the energy ray-curable component (a) include a polymer (a1) having an energy ray-curable group and a weight-average molecular weight of 80000 to 2000000, and a compound (a2) having an energy ray-curable group and a molecular weight of 100 to 80000. At least a portion of the polymer (a1) may or may not be crosslinked by a crosslinking agent.
(a polymer (a1) having an energy ray-curable group and a weight-average molecular weight of 80000 to 2000000.)
Examples of the polymer (a1) having energy ray-curable groups and a weight average molecular weight of 80000 to 2000000 include an acrylic resin (a1-1) obtained by reacting an acrylic polymer (a11) having a functional group reactive with a group of another compound with an energy ray-curable compound (a12) (a11) having an energy ray-curable group such as a group reactive with the functional group and an energy ray-curable double bond.
Examples of the functional group that can react with a group of another compound include a hydroxyl group, a carboxyl group, an amino group, a substituted amino group (i.e., a group in which one or two hydrogen atoms of an amino group are substituted with a group other than a hydrogen atom), an epoxy group, and the like. However, the functional group is preferably a group other than a carboxyl group in terms of a point of preventing corrosion of a circuit of a semiconductor wafer, a semiconductor chip, or the like.
Among them, the functional group is preferably a hydroxyl group.
Acrylic Polymer having functional group (a11)
Examples of the acrylic polymer having a functional group (a11) include a polymer obtained by copolymerizing an acrylic monomer having the functional group and an acrylic monomer having no functional group, and a polymer obtained by copolymerizing a monomer other than the acrylic monomer (i.e., a non-acrylic monomer) in addition to these monomers.
The acrylic polymer (a11) may be a random copolymer or a block copolymer, and a known polymerization method may be used.
Examples of the acrylic monomer having the functional group include a hydroxyl group-containing monomer, a carboxyl group-containing monomer, an amino group-containing monomer, a substituted amino group-containing monomer, and an epoxy group-containing monomer.
Examples of the hydroxyl group-containing monomer include hydroxyalkyl (meth) acrylates such as hydroxymethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate; and non (meth) acrylic unsaturated alcohols (unsaturated alcohols having no (meth) acryloyl skeleton) such as vinyl alcohol and allyl alcohol.
Examples of the carboxyl group-containing monomer include ethylenically unsaturated monocarboxylic acids (i.e., monocarboxylic acids having an ethylenically unsaturated bond) such as (meth) acrylic acid and crotonic acid; ethylenically unsaturated dicarboxylic acids (dicarboxylic acids having an ethylenically unsaturated bond) such as fumaric acid, itaconic acid, maleic acid, and citraconic acid; anhydrides of said ethylenically unsaturated dicarboxylic acids; and carboxyalkyl (meth) acrylates such as 2-carboxyethyl methacrylate.
The acrylic monomer having the functional group is preferably a hydroxyl group-containing monomer.
The acrylic monomer having the functional group constituting the acrylic polymer (a11) may be one type only, or two or more types, and when two or more types are used, the combination and ratio thereof may be arbitrarily selected.
Examples of the acrylic monomer having no functional group include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, n-octyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, dodecyl (meth) acrylate, n-butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, and the like, And alkyl (meth) acrylates having a chain structure in which the alkyl group constituting the alkyl ester has 1 to 18 carbon atoms, such as tetradecyl (meth) acrylate, myristyl (meth) acrylate, pentadecyl (meth) acrylate, hexadecyl (meth) acrylate, that is, palmityl (meth) acrylate, heptadecyl (meth) acrylate, and octadecyl (meth) acrylate, that is, stearyl (meth) acrylate.
Examples of the acrylic monomer having no functional group include (meth) acrylates containing an alkoxyalkyl group such as methoxymethyl (meth) acrylate, methoxyethyl (meth) acrylate, ethoxymethyl (meth) acrylate, and ethoxyethyl (meth) acrylate; aromatic group-containing (meth) acrylates such as aryl (meth) acrylates including phenyl (meth) acrylate; non-crosslinkable (meth) acrylamide and derivatives thereof; and non-crosslinkable (meth) acrylic esters having a tertiary amino group such as N, N-dimethylaminoethyl (meth) acrylate and N, N-dimethylaminopropyl (meth) acrylate.
The acrylic monomer having no functional group constituting the acrylic polymer (a11) may be one type only, or two or more types, and when two or more types are used, the combination and ratio thereof may be arbitrarily selected.
Examples of the non-acrylic monomer include olefins such as ethylene and norbornene; vinyl acetate; styrene, and the like.
The non-acrylic monomer constituting the acrylic polymer (a11) may be one kind only, or two or more kinds, and when two or more kinds are used, the combination and ratio thereof may be arbitrarily selected.
In the acrylic polymer (a11), the proportion (content) of the amount of the structural unit derived from the acrylic monomer having the functional group to the total amount of the structural units constituting the acrylic polymer (a11) is preferably 0.1 to 50% by mass, more preferably 1 to 40% by mass, and particularly preferably 3 to 30% by mass. By making the ratio in such a range, the degree of curing of the transparent resin film can be easily adjusted to a preferable range by the content of the energy ray-curable group in the acrylic resin (a1-1) obtained by copolymerization of the acrylic polymer (a11) and the energy ray-curable compound (a 12).
The acrylic polymer (a11) constituting the acrylic resin (a1-1) may be one type or two or more types, and when two or more types are used, the combination and ratio thereof may be arbitrarily selected.
In the composition (IV-1), the proportion of the content of the acrylic resin (a1-1) to the total content of the components other than the solvent (i.e., the content of the acrylic resin (a1-1) of the energy ray-curable film-like transparent adhesive) is preferably 1 to 70% by mass, more preferably 5 to 60% by mass, and particularly preferably 10 to 50% by mass.
Energy ray-curable compound (a12)
The energy ray-curable compound (a12) preferably has one or more selected from the group consisting of an isocyanate group, an epoxy group, and a carboxyl group as a group that can react with the functional group of the acrylic polymer (a11), and more preferably the energy ray-curable compound (a12) has an isocyanate group as the group. For example, when the energy ray-curable compound (a12) has an isocyanate group as the group, the isocyanate group easily reacts with a hydroxyl group of the acrylic polymer (a11) having the hydroxyl group as the functional group.
The energy ray-curable compound (a12) preferably has 1 to 5 energy ray-curable groups in one molecule, and more preferably has 1 to 3 energy ray-curable groups.
Examples of the energy ray-curable compound (a12) include 2-methacryloyloxyethyl isocyanate, m-isopropenyl- α, α -dimethylbenzyl isocyanate, methacryloyl isocyanate, allyl isocyanate, and 1,1- (bisacryloxymethyl) ethyl isocyanate;
an acryloyl monoisocyanate compound obtained by the reaction of a diisocyanate compound or a polyisocyanate compound with hydroxyethyl (meth) acrylate;
and an acryloyl monoisocyanate compound obtained by the reaction of a diisocyanate compound or a polyisocyanate compound, a polyol compound, and hydroxyethyl (meth) acrylate.
Among them, the energy ray-curable compound (a12) is preferably 2-methacryloyloxyethyl isocyanate.
The energy ray-curable compound (a12) constituting the acrylic resin (a1-1) may be one kind or two or more kinds, and when two or more kinds are used, the combination and ratio thereof may be arbitrarily selected.
In the acrylic resin (a1-1), the ratio of the content of the energy ray-curable group derived from the energy ray-curable compound (a12) to the content of the functional group derived from the acrylic polymer (a11) is preferably 20 to 120 mol%, more preferably 35 to 100 mol%, and particularly preferably 50 to 100 mol%. When the content ratio is in such a range, the adhesive force of the transparent resin film after curing becomes larger. The upper limit of the proportion of the energy ray-curable compound (a12) is 100 mol% when the compound is a monofunctional compound (having one of the groups in one molecule), and sometimes more than 100 mol% when the compound (a12) is a polyfunctional compound (having two or more of the groups in one molecule).
The weight average molecular weight (Mw) of the polymer (a1) is preferably 100000 to 2000000, more preferably 300000 to 1500000.
Here, "weight average molecular weight" is the same as that explained above.
When at least a part of the polymer (a1) is crosslinked by a crosslinking agent, the polymer (a1) may be a polymer which is polymerized from a monomer having a group which reacts with the crosslinking agent and is not one of the monomers described above as monomers constituting the acrylic polymer (a11) and which is crosslinked at a group which reacts with the crosslinking agent, or may be a polymer which is crosslinked at a group which reacts with the functional group from the energy ray-curable compound (a 12).
The polymer (a1) contained in the composition (IV-1) and the energy ray-curable film-like transparent adhesive may be one type or two or more types, and when two or more types are used, the combination and ratio thereof may be arbitrarily selected.
(Compound (a2) having an energy ray-curable group and a molecular weight of 100 to 80000.)
Examples of the energy ray-curable group of the compound (a2) having an energy ray-curable group and a molecular weight of 100 to 80000 include groups containing an energy ray-curable double bond, and preferable examples thereof include a (meth) acryloyl group, a vinyl group and the like.
The compound (a2) is not particularly limited if it satisfies the above conditions, and examples thereof include low molecular weight compounds having an energy ray-curable group, epoxy resins having an energy ray-curable group, and phenol resins having an energy ray-curable group.
Examples of the low molecular weight compound having an energy ray-curable group in the compound (a2) include polyfunctional monomers and oligomers, and an acrylate compound having a (meth) acryloyl group is preferable.
Examples of the acrylate-based compound include 2-hydroxy-3- (meth) acryloyloxypropyl methacrylate, polyethylene glycol di (meth) acrylate, propoxylated ethoxylated bisphenol A di (meth) acrylate, 2-bis [4- ((meth) acryloyloxypolyethoxy) phenyl ] propane, ethoxylated bisphenol A di (meth) acrylate, 2-bis [4- ((meth) acryloyloxydiethoxy) phenyl ] propane, 9-bis [4- (2- (meth) acryloyloxyethoxy) phenyl ] fluorene, 2-bis [4- ((meth) acryloyloxypropyloxy) phenyl ] propane, tricyclodecanedimethanol di (meth) acrylate, 1, 10-decanediol di (meth) acrylate, and mixtures thereof, Bifunctional (meth) acrylates such as 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, polytetramethylene glycol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, 2-bis [4- ((meth) acryloyloxyethoxy) phenyl ] propane, neopentyl glycol di (meth) acrylate, ethoxylated polypropylene glycol di (meth) acrylate, and 2-hydroxy-1, 3-di (meth) acryloyloxypropane;
polyfunctional (meth) acrylates such as tris (2- (meth) acryloyloxyethyl) isocyanurate, epsilon-caprolactone-modified tris- (2- (meth) acryloyloxyethyl) isocyanurate, ethoxylated glycerol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, ethoxylated pentaerythritol tetra (meth) acrylate, dipentaerythritol poly (meth) acrylate, and dipentaerythritol hexa (meth) acrylate;
and polyfunctional (meth) acrylate oligomers such as urethane (meth) acrylate oligomers.
As the epoxy resin having an energy ray-curable group and the phenol resin having an energy ray-curable group in the compound (a2), for example, the resins described in paragraph 0043 and the like of japanese patent application laid-open No. 2013-194102 can be used. Such a resin also corresponds to a resin constituting a thermosetting component described later, but in the present invention, it is regarded as the above-mentioned compound (a 2).
The weight average molecular weight (Mw) of the compound (a2) is preferably 100 to 30000, more preferably 300 to 10000.
The compound (a2) contained in the composition (IV-1) and the energy ray-curable film-like transparent adhesive may be one kind or two or more kinds, and when two or more kinds are contained, the combination and ratio thereof may be arbitrarily selected.
[ Polymer (b) having no energy ray-curable group ]
When the composition (IV-1) and the energy ray-curable film-like transparent adhesive contain the compound (a2) as the energy ray-curable component (a), it is preferable that the composition further contains a polymer (b) having no energy ray-curable group.
At least a portion of the polymer (b) may or may not be crosslinked by a crosslinking agent.
Examples of the polymer (b) having no energy ray-curable group include acrylic polymers, phenoxy resins, urethane resins, polyesters, rubber resins, and acrylic urethane resins.
Among them, the polymer (b) is preferably an acrylic polymer (hereinafter, may be abbreviated as "acrylic polymer (b-1)").
The acrylic polymer (b-1) may be a known acrylic polymer, and may be, for example, a homopolymer of one acrylic monomer, a copolymer of two or more acrylic monomers, or a copolymer of one or more acrylic monomers and one or more monomers (non-acrylic monomers) other than the acrylic monomers.
Examples of the acrylic monomer constituting the acrylic polymer (b-1) include alkyl (meth) acrylates, (meth) acrylates having a cyclic skeleton, glycidyl group-containing (meth) acrylates, hydroxyl group-containing (meth) acrylates, and substituted amino group-containing (meth) acrylates. Here, "substituted amino group" is the same as described above.
Examples of the alkyl (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, n-octyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, dodecyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, hexyl (meth) acrylate, dodecyl (ethyl (meth) acrylate, dodecyl (ethyl (meth) acrylate, dodecyl (ethyl acrylate, dodecyl (dodecyl acrylate, dodecyl (dodecyl) acrylate, dodecyl (dodecyl) acrylate, dodecyl) acrylate, dodecyl (dodecyl) acrylate, dodecyl) acrylate, dodecyl (dodecyl acrylate, dodecyl) and dodecyl (dodecyl) and dodecyl (ethyl acrylate, dodecyl) acrylate, dodecyl) and dodecyl (ethyl acrylate, dodecyl) acrylate, dodecyl (butyl acrylate, dodecyl) acrylate, dodecyl) acrylate, dodecyl acrylate, dodecyl, And alkyl (meth) acrylates having a chain structure in which the alkyl group constituting the alkyl ester has 1 to 18 carbon atoms, such as tetradecyl (meth) acrylate (myristyl (meth) acrylate), pentadecyl (meth) acrylate, hexadecyl (meth) acrylate (palmityl (meth) acrylate), heptadecyl (meth) acrylate, and octadecyl (meth) acrylate (stearyl (meth) acrylate).
Examples of the (meth) acrylate having a cyclic skeleton include cycloalkyl (meth) acrylates such as isobornyl (meth) acrylate and dicyclopentanyl (meth) acrylate;
aralkyl (meth) acrylates such as benzyl (meth) acrylate;
cycloalkenyl (meth) acrylates such as dicyclopentenyl (meth) acrylate;
cycloalkenyloxyalkyl (meth) acrylates such as dicyclopentenyloxyethyl (meth) acrylate, and the like.
Examples of the glycidyl group-containing (meth) acrylate include glycidyl (meth) acrylate and the like.
Examples of the hydroxyl group-containing (meth) acrylate include hydroxymethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
Examples of the substituted amino group-containing (meth) acrylate include N-methylaminoethyl (meth) acrylate and the like.
Examples of the non-acrylic monomer constituting the acrylic polymer (b-1) include olefins such as ethylene and norbornene; vinyl acetate; styrene, and the like.
Examples of the polymer (b) having no energy ray-curable group, at least a part of which is crosslinked by a crosslinking agent, include polymers obtained by reacting a reactive functional group in the polymer (b) with a crosslinking agent.
The reactive functional group is not particularly limited as long as it is appropriately selected according to the kind of the crosslinking agent and the like. For example, when the crosslinking agent is a polyisocyanate compound, the reactive functional group includes a hydroxyl group, a carboxyl group, an amino group, and the like, and among them, a hydroxyl group having a high reactivity with an isocyanate group is preferable. When the crosslinking agent is an epoxy compound, examples of the reactive functional group include a carboxyl group, an amino group, and an amide group, and among them, a carboxyl group having high reactivity with an epoxy group is preferable. However, from the viewpoint of preventing corrosion of the circuit of the semiconductor wafer or the semiconductor chip, it is preferable that the reactive functional group is a group other than a carboxyl group.
Examples of the polymer (b) having the reactive functional group and not having an energy ray-curable group include polymers obtained by polymerizing a monomer having at least the reactive functional group. When it is the acrylic polymer (b-1), a monomer having the reactive functional group may be used as either one or both of the acrylic monomer and the non-acrylic monomer exemplified as the monomer constituting the acrylic polymer (b-1). Examples of the polymer (b) having a hydroxyl group as a reactive functional group include, for example, a polymer obtained by polymerizing a hydroxyl group-containing (meth) acrylate, and in addition to this, a polymer obtained by polymerizing a monomer in which one or two or more hydrogen atoms of the above-mentioned acrylic monomer or non-acrylic monomer are substituted with the reactive functional group.
In the polymer (b) having a reactive functional group, the proportion (content) of the amount of the structural unit derived from the monomer having a reactive functional group to the total amount of the structural units constituting the polymer (b) having a reactive functional group is preferably 1 to 20% by mass, and more preferably 2 to 10% by mass. By setting the ratio in such a range, the degree of crosslinking in the polymer (b) becomes a more preferable range.
The weight average molecular weight (Mw) of the polymer (b) having no energy ray-curable group is preferably 10000 to 2000000, more preferably 100000 to 1500000, from the viewpoint of improving the film-forming property of the composition (IV-1). Here, "weight average molecular weight" is the same as that explained above.
The number of the polymers (b) having no energy ray-curable group contained in the composition (IV-1) and the energy ray-curable film-like transparent adhesive may be only one, two or more, and in the case of two or more, the combination and ratio thereof may be arbitrarily selected.
The composition (IV-1) may be a composition containing either one or both of the polymer (a1) and the compound (a 2). When the composition (IV-1) contains the compound (a2), it preferably further contains a polymer (b) having no energy ray-curable group, and in this case, it preferably further contains the compound (a 1). The composition (IV-1) may contain the polymer (a1) and the polymer (b) having no energy ray-curable group, in addition to the compound (a 2).
When the composition (IV-1) contains the polymer (a1), the compound (a2), and the polymer (b) having no energy ray-curable group, the content of the compound (a2) in the composition (IV-1) is preferably 10 to 400 parts by mass, more preferably 30 to 350 parts by mass, relative to 100 parts by mass of the total content of the polymer (a1) and the polymer (b) having no energy ray-curable group.
In the composition (IV-1), the ratio of the total content of the energy ray-curable component (a) and the polymer (b) having no energy ray-curable group to the total content of components other than the solvent (i.e., the total content of the energy ray-curable component (a) and the polymer (b) having no energy ray-curable group of the energy ray-curable film-shaped transparent adhesive) is preferably 5 to 90% by mass, more preferably 10 to 80% by mass, and particularly preferably 20 to 70% by mass. When the ratio of the content of the energy ray-curable component is in such a range, the energy ray-curability of the energy ray-curable film-shaped transparent adhesive becomes more favorable.
[ Filler ]
The energy ray-curable film-shaped transparent adhesive containing a filler exhibits the same effects as those of the thermosetting film-shaped transparent adhesive containing a filler (d).
Examples of the filler contained in the composition (IV-1) and the energy ray-curable film-like transparent adhesive include the same fillers as the fillers (d) contained in the thermosetting adhesive composition and the thermosetting film-like transparent adhesive.
The filler contained in the composition (IV-1) and the energy ray-curable film-like transparent adhesive may be one type or two or more types, and when two or more types are used, the combination and ratio thereof may be arbitrarily selected.
In the composition (IV-1), the proportion of the content of the filler with respect to the total content of all the components except the solvent (i.e., the content of the filler of the energy ray-curable film-like transparent adhesive) is preferably 25 to 75% by mass, and more preferably 28 to 72% by mass.
Since the filler absorbs water significantly less than other components, the water absorption rate can be made 0.55% or less more easily by setting the ratio to the lower limit value or more, and the effect of suppressing the transparent resin film from remaining on the support sheet is further enhanced when the glass wafer with the transparent resin film having a small size is picked up from the support sheet. When the ratio is not more than the upper limit, the strength of the film-like transparent adhesive and the transparent resin film as a cured product thereof can be further improved.
In addition to the energy ray-curable component and the filler, the composition (IV-1) may contain one or more selected from the group consisting of a thermosetting component, a coupling agent, a crosslinking agent, a photopolymerization initiator, and a general-purpose additive, depending on the purpose.
Examples of the thermosetting component, the coupling agent, the crosslinking agent, the photopolymerization initiator and the general-purpose additive in the composition (IV-1) include those similar to the epoxy thermosetting resin (b), the coupling agent (e), the crosslinking agent (f), the photopolymerization initiator (h) and the general-purpose additive (i) in the thermosetting adhesive composition.
For example, by using the composition (IV-1) containing the energy ray-curable component and the thermosetting component, the adhesive force of the formed energy ray-curable film-shaped transparent adhesive to an adherend is improved by heating, and the strength of the transparent resin film formed from the energy ray-curable film-shaped transparent adhesive is also improved.
In the composition (IV-1), the thermosetting component, the coupling agent, the crosslinking agent, the photopolymerization initiator and the general-purpose additive may be used singly or in combination of two or more, and when two or more are used simultaneously, the combination and ratio thereof may be arbitrarily selected.
The content of the thermosetting component, the coupling agent, the crosslinking agent, the photopolymerization initiator and the general-purpose additive in the composition (IV-1) is not particularly limited as long as it is appropriately adjusted according to the purpose.
Since the handling properties of the composition (IV-1) are improved by dilution, it is preferable that the composition (IV-1) further contains a solvent.
Examples of the solvent contained in the composition (IV-1) include the same solvents as those used for the thermosetting adhesive composition.
The composition (IV-1) may contain only one solvent, or may contain two or more solvents.
Method for producing energy ray-curable adhesive composition
The energy ray-curable adhesive composition such as the composition (IV-1) can be obtained by blending the components constituting it.
The order of addition of the components in blending is not particularly limited, and two or more components may be added simultaneously.
When a solvent is used, the solvent may be mixed with any of the components other than the solvent to preliminarily dilute the components, or the solvent may be mixed with the components without preliminarily diluting any of the components other than the solvent to use.
The method for mixing the components at the time of blending is not particularly limited, and may be appropriately selected from the following known methods: a method of mixing by rotating a stirrer, a stirring blade, or the like; a method of mixing using a stirrer; a method of mixing by applying ultrasonic waves, and the like.
The temperature and time for adding and mixing the components are not particularly limited and may be appropriately adjusted as long as the components are not deteriorated, but the temperature is preferably 15 to 30 ℃.
Infrared sensor module
In the infrared sensor module of the present invention, the infrared receiving element and the glass wafer are cured and bonded by the film-like transparent adhesive of the present invention. Since the glass wafer having a high infrared transmittance and the cured film-like transparent adhesive have a high infrared transmittance, the infrared receiving element can effectively receive infrared rays transmitted through the glass wafer and the cured film-like transparent adhesive. Since the glass wafer is firmly bonded to the infrared receiving element by the film-like transparent adhesive, the infrared receiving element can be protected and an infrared sensor module with high reliability can be manufactured.
The infrared sensor module of the present invention can be manufactured by curing and bonding an infrared receiving element and a glass wafer using the film-like transparent adhesive of the present invention.
Examples
The present invention will be described in more detail below with reference to specific examples. However, the present invention is not limited to the examples shown below.
< preparation of acrylic resin >
Acrylic resin (1): an acrylic resin (having a weight-average molecular weight (Mw) of 60 ten thousand) obtained by copolymerizing 85 parts by mass of methyl acrylate (hereinafter abbreviated as "MA") and 15 parts by mass of 2-hydroxyethyl acrylate (hereinafter abbreviated as "HEA").
Acrylic resin (2): an acrylic resin (weight average molecular weight (Mw) of 70 ten thousand) obtained by copolymerizing 85 parts by mass of methyl acrylate (hereinafter abbreviated as "MA") and 15 parts by mass of 2-hydroxyethyl acrylate (hereinafter abbreviated as "HEA").
Acrylic resin (3): an acrylic resin (weight average molecular weight (Mw)80 ten thousand) obtained by copolymerizing 55 parts by mass of butyl acrylate (hereinafter abbreviated as "BA"), 15 parts by mass of methyl acrylate (hereinafter abbreviated as "MA"), 20 parts by mass of glycidyl methacrylate (hereinafter abbreviated as "GMA"), and 10 parts by mass of 2-hydroxyethyl acrylate (hereinafter abbreviated as "HEA").
< preparation of film-shaped transparent adhesive >
[ example 1]
With respect to 100 parts by mass of the acrylic resin (1) (MA/HEA ═ 85/15), 15 parts by mass of an epoxy resin (trade name "CNA-147" Nippon Kayaku co., manufactured by ltd.), 12 parts by mass of a phenol resin (trade name "millex XLC-4L" manufactured by Mitsui Chemicals, inc.), 90 parts by mass of spherical silica (average particle diameter 0.05 μm, trade name "YA 050C-SV 2" manufactured by Admatechs corporation), 1 part by mass of a crosslinking agent (trade name "BHS 8515" TOYOCHEM co., manufactured by ltd.), were dissolved or dispersed in methyl ethyl ketone, and stirred at 23 ℃, whereby an adhesive composition having a solid content concentration of 20 mass% was obtained.
The obtained adhesive composition was applied to the release-treated surface of a release film obtained by subjecting one surface of a polyethylene terephthalate film (thickness: 38 μm) to a release treatment by a silicone treatment, and dried at 100 ℃ for 2 minutes to obtain a film-shaped transparent adhesive having a thickness of 10 μm.
[ example 2]
With respect to 100 parts by mass of the acrylic resin (1) (MA/HEA ═ 85/15), 15 parts by mass of an epoxy resin (trade name "CNA-147" Nippon Kayaku co., manufactured by ltd.), 12 parts by mass of a phenol resin (trade name "millex XLC-4L" manufactured by Mitsui Chemicals, inc.), 90 parts by mass of spherical silica (average particle diameter 0.05 μm, trade name "YA 050C-SV 2" manufactured by Admatechs corporation), 1 part by mass of a crosslinking agent (trade name "BHS 8515" TOYOCHEM co., manufactured by ltd.), were dissolved or dispersed in methyl ethyl ketone, and stirred at 23 ℃, whereby an adhesive composition having a solid content concentration of 20 mass% was obtained.
The obtained adhesive composition was applied to the release-treated surface of a release film obtained by subjecting one surface of a polyethylene terephthalate film (thickness: 38 μm) to a release treatment by a silicone treatment, and dried at 100 ℃ for 2 minutes to obtain a film-shaped transparent adhesive having a thickness of 20 μm.
[ example 3]
With respect to 100 parts by mass of the acrylic resin (2) (MA/HEA ═ 85/15), 29 parts by mass of an epoxy resin (trade name "CNA-147" Nippon Kayaku co., manufactured by ltd.), 14 parts by mass of a phenol resin (trade name "millex XLC-4L" Mitsui Chemicals, manufactured by inc.), 4 parts by mass of an energy ray-curable resin (trade name "Seikaseven SS 02-165" dainicoseika Color & Chemicals mfg.co., manufactured by ltd.), 1 part by mass of a crosslinking agent (trade name "BHS 8515" TOYOCHEM co., ltd., manufactured) were dissolved or dispersed in methyl ethyl ketone, and stirred at 23 ℃, thereby preparing an adhesive composition having a solid content concentration of 30 mass%.
The obtained adhesive composition was applied to the release-treated surface of a release film obtained by subjecting one surface of a polyethylene terephthalate film (thickness: 38 μm) to a release treatment by a silicone treatment, and dried at 100 ℃ for 2 minutes to obtain a film-shaped transparent adhesive having a thickness of 20 μm.
[ example 4]
With respect to 100 parts by mass of the acrylic resin (1) (MA/HEA ═ 85/15), 15 parts by mass of an epoxy resin (trade name "CNA-147" Nippon Kayaku co., manufactured by ltd.), 12 parts by mass of a phenol resin (trade name "millex XLC-4L" manufactured by Mitsui Chemicals, inc.), 90 parts by mass of spherical silica (average particle diameter 0.01 μm, trade name "YA 010C-SV 1" manufactured by Admatechs corporation), 1 part by mass of a crosslinking agent (trade name "BHS 8515" TOYOCHEM co., manufactured by ltd.), were dissolved or dispersed in methyl ethyl ketone, and stirred at 23 ℃, whereby an adhesive composition having a solid content concentration of 20 mass% was obtained.
The obtained adhesive composition was applied to the release-treated surface of a release film obtained by subjecting one surface of a polyethylene terephthalate film (thickness: 38 μm) to a release treatment by a silicone treatment, and dried at 100 ℃ for 2 minutes to obtain a film-shaped transparent adhesive having a thickness of 20 μm.
[ example 5]
With respect to 100 parts by mass of the acrylic resin (1) (MA/HEA ═ 85/15), 15 parts by mass of an epoxy resin (trade name "CNA-147" Nippon Kayaku co., manufactured by ltd.), 12 parts by mass of a phenol resin (trade name "millex XLC-4L" manufactured by Mitsui Chemicals, inc.), 90 parts by mass of spherical silica (average particle diameter 0.1 μm, trade name "YA 100C-SV 2" manufactured by Admatechs corporation), 1 part by mass of a crosslinking agent (trade name "BHS 8515" TOYOCHEM co., manufactured by ltd.), were dissolved or dispersed in methyl ethyl ketone, and stirred at 23 ℃, whereby an adhesive composition having a solid content concentration of 20 mass% was obtained.
The obtained adhesive composition was applied to the release-treated surface of a release film obtained by subjecting one surface of a polyethylene terephthalate film (thickness: 38 μm) to a release treatment by a silicone treatment, and dried at 100 ℃ for 2 minutes to obtain a film-shaped transparent adhesive having a thickness of 20 μm.
[ example 6]
With respect to 100 parts by mass of the acrylic resin (3) (BA/MA/GMA/HEA ═ 55/15/20/10), 850 parts by mass of a thermosetting resin containing acrylic particles (trade name "Seikaseven SS 02-135" (thermosetting resin containing 6 parts by mass of acrylic fine particles (average particle diameter 0.4 μm) with respect to 100 parts by mass of resin solids), dainiciseika Color & Chemicals mfg.co., manufactured by Lt d.), 150 parts by mass of an energy ray-curable resin (trade name "Seikaseven SS 02-242" dainiciseika Color & Chemicals mfg.co, manufactured by ltd.), 1 part by mass of a crosslinking agent (trade name "BHS 8515" TOYOCHEM co., manufactured by ltd.) were dissolved or dispersed in methyl ethyl ketone, and stirred at 23 ℃, thereby preparing an adhesive composition having a solid content concentration of 40 mass%.
The obtained adhesive composition was applied to the release-treated surface of a release film obtained by subjecting one surface of a polyethylene terephthalate film (thickness: 38 μm) to a release treatment by a silicone treatment, and dried at 100 ℃ for 2 minutes to obtain a film-shaped transparent adhesive having a thickness of 20 μm.
Comparative example 1
With respect to 100 parts by mass of the acrylic resin (3) (BA/MA/GMA/HEA ═ 55/15/20/10), 1000 parts by mass of a thermosetting resin containing a silica filler (trade name "seikaseev en SS 02-193" (a thermosetting resin containing 13 parts by mass of spherical silica (average particle diameter 500 μ M) with respect to 100 parts by mass of resin solids), daiinisesika Color & Chemicals M fg. co., ltd., manufactured), was dissolved or dispersed in methyl ethyl ketone, and stirred at 23 ℃, thereby preparing an adhesive composition having a solid content concentration of 60 mass%.
The obtained adhesive composition was applied to the release-treated surface of a release film obtained by subjecting one surface of a polyethylene terephthalate film (thickness: 38 μm) to a release treatment by a silicone treatment, and dried at 100 ℃ for 2 minutes to obtain a film-shaped transparent adhesive having a thickness of 20 μm.
Comparative example 2
With respect to 100 parts by mass of the acrylic resin (3) (BA/MA/GMA/HEA ═ 55/15/20/10), 850 parts by mass of a thermosetting resin containing acrylic particles (trade name "Seikaseven SS 02-135" (thermosetting resin containing 6 parts by mass of acrylic fine particles (average particle diameter 0.4 μm) with respect to 100 parts by mass of the resin solid content), dainiciseika Color & Chemicals mfg.co., manufactured by ltd.), 1200 parts by mass of an energy ray-curable resin (trade name "Seikaseven SS 02-242" dainiciseika Color & Chemicals mfg.co., manufactured by ltd.), 1 part by mass of a crosslinking agent (trade name "BHS 8515" TOYOCHEM co., manufactured by ltd.) were dissolved or dispersed in methyl ethyl ketone, and stirred at 23 ℃, thereby preparing an adhesive composition having a solid content concentration of 40% by mass.
The obtained adhesive composition was applied to the release-treated surface of a release film obtained by subjecting one surface of a polyethylene terephthalate film (thickness: 38 μm) to a release treatment by a silicone treatment, and dried at 100 ℃ for 2 minutes to obtain a film-shaped transparent adhesive having a thickness of 20 μm.
Comparative example 3
With respect to 100 parts by mass of the acrylic resin (1) (MA/HEA ═ 85/15), 15 parts by mass of an epoxy resin (trade name "CNA-147" Nippon Kayaku co., manufactured by ltd.), 12 parts by mass of a phenol resin (trade name "millex XLC-4L" manufactured by Mitsui Chemicals, inc.), 90 parts by mass of spherical silica (average particle diameter 500nm, trade name "SC 2050-MA" manufactured by admatech), 1 part by mass of a crosslinking agent (trade name "BHS 8515" TOYOCHEM co., manufactured by ltd.) were dissolved or dispersed in methyl ethyl ketone, and stirred at 23 ℃, thereby obtaining an adhesive composition having a solid content concentration of 20 mass%.
The obtained adhesive composition was applied to the release-treated surface of a release film obtained by subjecting one surface of a polyethylene terephthalate film (thickness: 38 μm) to a release treatment by a silicone treatment, and dried at 100 ℃ for 2 minutes to obtain a film-shaped transparent adhesive having a thickness of 20 μm.
Table 1 summarizes the compositions of the film-like transparent binders of examples 1 to 6 and comparative examples 1 to 3.
The film-like transparent adhesive with the release film obtained above was bonded to a glass wafer having a thickness of 100 μm at 70 ℃ (D263T eco, manufactured by SCHOTTAG), the release film was removed to prepare a laminate of the glass wafer and the film-like transparent adhesive, and the film-like transparent adhesive was cured at 175 ℃ for 5 hours in an oven.
However, since the film-shaped transparent adhesives of examples 3 and 6 and comparative example 2 contain an energy ray curable resin, a laminate of a glass wafer and the film-shaped transparent adhesive was irradiated with ultraviolet rays (illuminance 220 mW/cm) using an ultraviolet irradiation apparatus (RAD-2000m/12 linetec corporation, dominant wavelength 365nm)2Light quantity of 120mJ/cm2) Then, the film-like transparent adhesive was cured at 175 ℃ for 5 hours in an oven.
The following items were evaluated for each of the glass wafer and the laminate of the film-like transparent adhesive after thermal curing.
(light transmittance)
The light transmittance at a wavelength of 850nm was determined by measuring the light transmittance (%) at a wavelength of 800 to 2000nm of a thermally cured laminate using a direct light-receiving unit without using an integrating sphere and a glass wafer having a thickness of 150 μm as a reference (reference) using a spectrophotometer (UV-VIS-NIR SPECTROPHOTOMETER UV-3600, manufactured by SHIMADZU CORPORATION).
In the wavelength range of 800-2000 nm, the light transmittance is always 80% or more for good evaluation, other than the evaluation as x.
(shear Strength)
One side of the film-like transparent adhesive of an adhesive tape in which a film-like transparent adhesive was laminated on a low-density polyethylene base material (thickness 100 μm) was attached to a ground surface (dry polishing) of a silicon wafer (diameter 200mm, thickness 350 μm) at 60 ℃ and fixed to a ring frame at the same time. Next, using a dicing apparatus (manufactured by DISCO Corporation, DFD6361), the wafer was diced into a chip size of 5mm × 5 mm. The amount of the cut was set so that the base material was cut into 20 μm.
Cutting knife: 27HECC
Cutting speed: 50mm/s
Cutting rotating speed: 30000rpm
Then, the chips cut into 10mm × 10mm were bonded at 150 ℃ and 300gf for 1 second, and further heated at 175 ℃ for 5 hours to cure the resin, and then the shear strength (N/5mm □) was measured on a plate heated to 250 ℃ in a state where the stacked body of chips was heated at a shear rate of 0.2mm/s, using a Nordson DAGE 4000HS weld Strength tester (manufactured by Nordson Corporation).
The evaluation results of the film-shaped transparent adhesives of examples 1 to 6 and comparative examples 1 to 3 are summarized in Table 2.
From the above results, it is clear that the film-like adhesives after heat curing in examples 1 to 6 have a transmittance at a wavelength of 850nm of 90% or more, preferably 90% or more, and a transmittance at a wavelength of 800 to 2000nm of 80% or more, preferably 80% or more.
In contrast, the film-like adhesives of comparative examples 1 to 3, which were thermally cured, had a transmittance of 5 to 42% for infrared rays at a wavelength of 850nm and a transmittance of less than 80% for wavelengths of 800 to 2000nm, and were not usable for bonding an infrared receiving element and a glass wafer because of low infrared transmittance.
Industrial applicability
The film-like transparent adhesive of the present invention can be suitably used for bonding an infrared ray receiving element having an infrared ray receiving portion of an infrared ray sensor module to a glass wafer.
Claims (5)
1. An infrared sensor module in which an infrared receiving element having an infrared receiving portion provided so as to receive infrared rays transmitted through a glass wafer and a cured film-like transparent adhesive is cured and bonded to the glass wafer by the thermosetting film-like transparent adhesive,
the thermosetting film-like transparent adhesive contains a polymer component (a) comprising an acrylic resin,
the light transmittance of the thermosetting film-like transparent adhesive at a wavelength of 800nm after curing is 80% or more.
2. The infrared sensor module according to claim 1, wherein the light transmittance of the thermosetting film-like transparent adhesive at a wavelength of 800 to 2000nm after curing is 80% or more.
3. The infrared sensor module according to claim 1 or 2, wherein the light transmittance at a wavelength of 850nm after curing of the thermosetting film-like transparent adhesive is 90% or more.
4. The infrared sensor module according to claim 1 or 2, wherein the thermosetting film-like transparent adhesive contains a filler, and an average particle diameter of the filler is 450nm or less.
5. The infrared sensor module as set forth in claim 3, wherein the thermosetting film-like transparent adhesive contains a filler, and an average particle diameter of the filler is 450nm or less.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2017-163632 | 2017-08-28 | ||
| JP2017163632 | 2017-08-28 | ||
| PCT/JP2018/018093 WO2019044046A1 (en) | 2017-08-28 | 2018-05-10 | Film-like transparent adhesive and infrared sensor module |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111051455A CN111051455A (en) | 2020-04-21 |
| CN111051455B true CN111051455B (en) | 2022-05-03 |
Family
ID=65527580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201880055290.6A Active CN111051455B (en) | 2017-08-28 | 2018-05-10 | Film-like transparent adhesive and infrared sensor module |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP7107946B2 (en) |
| CN (1) | CN111051455B (en) |
| SG (1) | SG11202001719RA (en) |
| TW (1) | TWI758479B (en) |
| WO (1) | WO2019044046A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020164792A (en) * | 2019-03-26 | 2020-10-08 | 日東電工株式会社 | Transparent adhesive sheet and transparent adhesive sheet having release material |
| JP2020164564A (en) * | 2019-03-28 | 2020-10-08 | リンテック株式会社 | Coating liquid and method for producing adhesive tape using the same |
| JP7520497B2 (en) * | 2019-11-08 | 2024-07-23 | リンテック株式会社 | Adhesive films and composite adhesive sheets |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104903385A (en) * | 2012-12-21 | 2015-09-09 | 日本山村硝子株式会社 | Organic-inorganic hybrid prepolymer, organic-inorganic hybrid material, and element sealing structure |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4180253B2 (en) * | 2001-06-29 | 2008-11-12 | 大日本塗料株式会社 | Sealant for infrared light receiving element |
| JP2006321832A (en) * | 2005-05-17 | 2006-11-30 | Konishi Kagaku Ind Co Ltd | Resin composition for sealing optical semiconductor and optical semiconductor device using the same |
| JP2009215520A (en) * | 2008-03-13 | 2009-09-24 | Kyocera Chemical Corp | Epoxy resin composition for sealing optical semiconductor and optical semiconductor device |
| KR101442442B1 (en) * | 2010-10-01 | 2014-09-22 | 쇼와 덴코 가부시키가이샤 | Photocurable composition for transparent adhesive sheet |
| DE102010062823A1 (en) * | 2010-12-10 | 2012-06-21 | Tesa Se | Adhesive composition and method for encapsulating an electronic device |
| JP2012136022A (en) * | 2012-01-04 | 2012-07-19 | Jnc Corp | Heat dissipating member, electronic device and battery |
| WO2014021450A1 (en) * | 2012-08-02 | 2014-02-06 | リンテック株式会社 | Film-like adhesive, adhesive sheet for semiconductor junction, and method for producing semiconductor device |
| KR20160114049A (en) * | 2014-01-29 | 2016-10-04 | 히타치가세이가부시끼가이샤 | Adhesive composition, resin cured product obtained from adhesive composition, method for manufacturing semiconductor device using adhesive composition, and solid-state imaging element |
| WO2016027883A1 (en) * | 2014-08-22 | 2016-02-25 | リンテック株式会社 | Protective-coating-forming sheet and method for manufacturing semiconductor chip provided with protective coating |
| TWI553410B (en) * | 2015-10-08 | 2016-10-11 | 新應材股份有限公司 | Composition, infrared ray transmitting filter and fabricating method thereof, and infrared ray sensor |
-
2018
- 2018-05-10 CN CN201880055290.6A patent/CN111051455B/en active Active
- 2018-05-10 SG SG11202001719RA patent/SG11202001719RA/en unknown
- 2018-05-10 JP JP2019538963A patent/JP7107946B2/en active Active
- 2018-05-10 WO PCT/JP2018/018093 patent/WO2019044046A1/en active Application Filing
- 2018-05-14 TW TW107116256A patent/TWI758479B/en active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104903385A (en) * | 2012-12-21 | 2015-09-09 | 日本山村硝子株式会社 | Organic-inorganic hybrid prepolymer, organic-inorganic hybrid material, and element sealing structure |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2019044046A1 (en) | 2020-08-13 |
| SG11202001719RA (en) | 2020-03-30 |
| TW201913982A (en) | 2019-04-01 |
| CN111051455A (en) | 2020-04-21 |
| JP7107946B2 (en) | 2022-07-27 |
| WO2019044046A1 (en) | 2019-03-07 |
| TWI758479B (en) | 2022-03-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110249414B (en) | Curable resin film and first protective film-forming sheet | |
| CN108138012B (en) | Sheet for forming No. 1 protective film, method for forming No. 1 protective film, and method for manufacturing semiconductor chip | |
| US20190330465A1 (en) | Curable resin film and first protective film forming sheet | |
| CN111670231B (en) | Film-like adhesive and sheet for semiconductor processing | |
| JP6344811B1 (en) | First protective film forming sheet | |
| CN108140585B (en) | No. 1 protective film-forming sheet | |
| JP6659308B2 (en) | Sheet for forming first protective film | |
| CN110622302B (en) | Semiconductor device and method for manufacturing the same | |
| CN111051455B (en) | Film-like transparent adhesive and infrared sensor module | |
| CN114728508A (en) | Resin film, composite sheet, and method for manufacturing semiconductor device | |
| CN108243614B (en) | Curable resin film and 1 st protective film-forming sheet | |
| CN108140622B (en) | Kit of thermosetting resin film and 2 nd protective film forming film, and method for forming same | |
| KR102538766B1 (en) | Curable resin film and sheet for forming the first protective film | |
| CN108260356B (en) | Curable resin film and 1 st protective film-forming sheet | |
| KR102534927B1 (en) | Thermosetting resin film, sheet for forming the first protective film, and method for forming the first protective film | |
| CN108352365B (en) | Protective film forming sheet | |
| JP6821580B2 (en) | Thermosetting resin film and first protective film forming sheet | |
| CN111279468A (en) | Film for forming protective film, composite sheet for forming protective film, and method for producing semiconductor chip | |
| TWI750140B (en) | Wafer protecting method | |
| WO2021182554A1 (en) | Protective film-forming sheet | |
| CN112778917A (en) | Adhesive film and adhesive composite sheet | |
| CN111344850A (en) | Semiconductor chip with first protective film, method for manufacturing same, and method for evaluating semiconductor chip-first protective film laminate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |