JPH06264035A - Adhesive film, its production, and method for adhesion - Google Patents
Adhesive film, its production, and method for adhesionInfo
- Publication number
- JPH06264035A JPH06264035A JP5055601A JP5560193A JPH06264035A JP H06264035 A JPH06264035 A JP H06264035A JP 5055601 A JP5055601 A JP 5055601A JP 5560193 A JP5560193 A JP 5560193A JP H06264035 A JPH06264035 A JP H06264035A
- Authority
- JP
- Japan
- Prior art keywords
- dianhydride
- adhesive film
- bis
- resin
- tetracarboxylic dianhydride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002313 adhesive film Substances 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims abstract description 62
- 229920001721 polyimide Polymers 0.000 claims abstract description 17
- 239000003822 epoxy resin Substances 0.000 claims abstract description 13
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 13
- 150000004985 diamines Chemical class 0.000 claims abstract description 12
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims abstract description 12
- 239000000945 filler Substances 0.000 claims abstract description 10
- 239000009719 polyimide resin Substances 0.000 claims abstract description 10
- 239000005011 phenolic resin Substances 0.000 claims abstract description 8
- -1 Tetracarboxylic acid dianhydride Chemical class 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 15
- 239000004065 semiconductor Substances 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 abstract description 10
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 abstract description 9
- 229910052709 silver Inorganic materials 0.000 abstract description 9
- 239000004332 silver Substances 0.000 abstract description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 125000005591 trimellitate group Chemical group 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
- 229920003986 novolac Polymers 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 7
- 239000004642 Polyimide Substances 0.000 description 7
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229920005992 thermoplastic resin Polymers 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229910015365 Au—Si Inorganic materials 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000006023 eutectic alloy Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000005304 joining Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910000679 solder Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 2
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 2
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical group C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000004377 microelectronic Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920005575 poly(amic acid) Polymers 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OLQWMCSSZKNOLQ-ZXZARUISSA-N (3s)-3-[(3r)-2,5-dioxooxolan-3-yl]oxolane-2,5-dione Chemical compound O=C1OC(=O)C[C@H]1[C@@H]1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-ZXZARUISSA-N 0.000 description 1
- NJPAJFFEXRMGDR-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine;benzo[a]anthracen-7-yloxyboronic acid Chemical compound C1CCC=CN2CCCNC21.C1=CC2=CC=CC=C2C2=C1C(OB(O)O)=C(C=CC=C1)C1=C2 NJPAJFFEXRMGDR-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- GZCGUPFRVQAUEE-UHFFFAOYSA-N 2,3,4,5,6-pentahydroxyhexanal Chemical compound OCC(O)C(O)C(O)C(O)C=O GZCGUPFRVQAUEE-UHFFFAOYSA-N 0.000 description 1
- XMXCPDQUXVZBGQ-UHFFFAOYSA-N 2,3,6,7-tetrachloronaphthalene-1,4,5,8-tetracarboxylic acid Chemical compound ClC1=C(Cl)C(C(O)=O)=C2C(C(=O)O)=C(Cl)C(Cl)=C(C(O)=O)C2=C1C(O)=O XMXCPDQUXVZBGQ-UHFFFAOYSA-N 0.000 description 1
- JZWGLBCZWLGCDT-UHFFFAOYSA-N 2,7-dichloronaphthalene-1,4,5,8-tetracarboxylic acid Chemical compound ClC1=CC(C(O)=O)=C2C(C(=O)O)=CC(Cl)=C(C(O)=O)C2=C1C(O)=O JZWGLBCZWLGCDT-UHFFFAOYSA-N 0.000 description 1
- OJSPYCPPVCMEBS-UHFFFAOYSA-N 2,8-dimethyl-5,5-dioxodibenzothiophene-3,7-diamine Chemical compound C12=CC(C)=C(N)C=C2S(=O)(=O)C2=C1C=C(C)C(N)=C2 OJSPYCPPVCMEBS-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- GWHLJVMSZRKEAQ-UHFFFAOYSA-N 3-(2,3-dicarboxyphenyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O GWHLJVMSZRKEAQ-UHFFFAOYSA-N 0.000 description 1
- LXJLFVRAWOOQDR-UHFFFAOYSA-N 3-(3-aminophenoxy)aniline Chemical compound NC1=CC=CC(OC=2C=C(N)C=CC=2)=C1 LXJLFVRAWOOQDR-UHFFFAOYSA-N 0.000 description 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 1
- ZMPZWXKBGSQATE-UHFFFAOYSA-N 3-(4-aminophenyl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=CC(N)=C1 ZMPZWXKBGSQATE-UHFFFAOYSA-N 0.000 description 1
- TYKLCAKICHXQNE-UHFFFAOYSA-N 3-[(2,3-dicarboxyphenyl)methyl]phthalic acid Chemical compound OC(=O)C1=CC=CC(CC=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O TYKLCAKICHXQNE-UHFFFAOYSA-N 0.000 description 1
- CKOFBUUFHALZGK-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC(CC=2C=C(N)C=CC=2)=C1 CKOFBUUFHALZGK-UHFFFAOYSA-N 0.000 description 1
- FGWQCROGAHMWSU-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC(N)=C1 FGWQCROGAHMWSU-UHFFFAOYSA-N 0.000 description 1
- PAHZZOIHRHCHTH-UHFFFAOYSA-N 3-[2-(2,3-dicarboxyphenyl)propan-2-yl]phthalic acid Chemical compound C=1C=CC(C(O)=O)=C(C(O)=O)C=1C(C)(C)C1=CC=CC(C(O)=O)=C1C(O)=O PAHZZOIHRHCHTH-UHFFFAOYSA-N 0.000 description 1
- UVUCUHVQYAPMEU-UHFFFAOYSA-N 3-[2-(3-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]aniline Chemical compound NC1=CC=CC(C(C=2C=C(N)C=CC=2)(C(F)(F)F)C(F)(F)F)=C1 UVUCUHVQYAPMEU-UHFFFAOYSA-N 0.000 description 1
- DVXYMCJCMDTSQA-UHFFFAOYSA-N 3-[2-(3-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=CC(N)=CC=1C(C)(C)C1=CC=CC(N)=C1 DVXYMCJCMDTSQA-UHFFFAOYSA-N 0.000 description 1
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 description 1
- LBPVOEHZEWAJKQ-UHFFFAOYSA-N 3-[4-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 LBPVOEHZEWAJKQ-UHFFFAOYSA-N 0.000 description 1
- MFTFTIALAXXIMU-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)C(C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MFTFTIALAXXIMU-UHFFFAOYSA-N 0.000 description 1
- NYRFBMFAUFUULG-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=C(N)C=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC(N)=C1 NYRFBMFAUFUULG-UHFFFAOYSA-N 0.000 description 1
- JERFEOKUSPGKGV-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfanylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(SC=3C=CC(OC=4C=C(N)C=CC=4)=CC=3)=CC=2)=C1 JERFEOKUSPGKGV-UHFFFAOYSA-N 0.000 description 1
- WCXGOVYROJJXHA-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 WCXGOVYROJJXHA-UHFFFAOYSA-N 0.000 description 1
- AORTZIIKTZPIQU-UHFFFAOYSA-N 3-butyl-4-methyloxolane-2,5-dione Chemical compound CCCCC1C(C)C(=O)OC1=O AORTZIIKTZPIQU-UHFFFAOYSA-N 0.000 description 1
- JASHGAIOBWYPBI-UHFFFAOYSA-N 3a,4a,7a,7b-tetrahydrodifuro[5,4-a:5',4'-d]furan-1,3,5,7-tetrone Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C1O2 JASHGAIOBWYPBI-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- QGRZMPCVIHBQOE-UHFFFAOYSA-N 4,8-dimethyl-1,2,3,5,6,7-hexahydronaphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)CC(C)=C2C(C(O)=O)C(C(O)=O)CC(C)=C21 QGRZMPCVIHBQOE-UHFFFAOYSA-N 0.000 description 1
- FYYYKXFEKMGYLZ-UHFFFAOYSA-N 4-(1,3-dioxo-2-benzofuran-5-yl)-2-benzofuran-1,3-dione Chemical compound C=1C=C2C(=O)OC(=O)C2=CC=1C1=CC=CC2=C1C(=O)OC2=O FYYYKXFEKMGYLZ-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
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- IWXCYYWDGDDPAC-UHFFFAOYSA-N 4-[(3,4-dicarboxyphenyl)methyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C(C(O)=O)=C1 IWXCYYWDGDDPAC-UHFFFAOYSA-N 0.000 description 1
- NWIVYGKSHSJHEF-UHFFFAOYSA-N 4-[(4-amino-3,5-diethylphenyl)methyl]-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CC=2C=C(CC)C(N)=C(CC)C=2)=C1 NWIVYGKSHSJHEF-UHFFFAOYSA-N 0.000 description 1
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- KZTROCYBPMKGAW-UHFFFAOYSA-N 4-[[4-amino-3,5-di(propan-2-yl)phenyl]methyl]-2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=C(N)C(C(C)C)=CC(CC=2C=C(C(N)=C(C(C)C)C=2)C(C)C)=C1 KZTROCYBPMKGAW-UHFFFAOYSA-N 0.000 description 1
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- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
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- 229930185605 Bisphenol Natural products 0.000 description 1
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- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- GCAIEATUVJFSMC-UHFFFAOYSA-N benzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1C(O)=O GCAIEATUVJFSMC-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical group C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- WOSVXXBNNCUXMT-UHFFFAOYSA-N cyclopentane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)C1C(O)=O WOSVXXBNNCUXMT-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical class NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- GBASTSRAHRGUAB-UHFFFAOYSA-N ethylenetetracarboxylic dianhydride Chemical compound O=C1OC(=O)C2=C1C(=O)OC2=O GBASTSRAHRGUAB-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- JGGWKXMPICYBKC-UHFFFAOYSA-N phenanthrene-1,8,9,10-tetracarboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=C(C(O)=O)C(C(O)=O)=C3C(C(=O)O)=CC=CC3=C21 JGGWKXMPICYBKC-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- RTHVZRHBNXZKKB-UHFFFAOYSA-N pyrazine-2,3,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=NC(C(O)=O)=C(C(O)=O)N=C1C(O)=O RTHVZRHBNXZKKB-UHFFFAOYSA-N 0.000 description 1
- YKWDNEXDHDSTCU-UHFFFAOYSA-N pyrrolidine-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1NC(C(O)=O)C(C(O)=O)C1C(O)=O YKWDNEXDHDSTCU-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
- H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L24/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
- H01L24/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/013—Alloys
- H01L2924/0132—Binary Alloys
- H01L2924/01322—Eutectic Alloys, i.e. obtained by a liquid transforming into two solid phases
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/10—Details of semiconductor or other solid state devices to be connected
- H01L2924/102—Material of the semiconductor or solid state bodies
- H01L2924/1025—Semiconducting materials
- H01L2924/10251—Elemental semiconductors, i.e. Group IV
- H01L2924/10253—Silicon [Si]
Landscapes
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Die Bonding (AREA)
- Dicing (AREA)
- Adhesive Tapes (AREA)
- Epoxy Resins (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は、ICやLSIとリード
フレームの接合材料、すなわちダイボンディング用材料
として用いられる接着フィルム、その製造法及び接着法
に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an adhesive film used as a bonding material for an IC or LSI and a lead frame, that is, a die bonding material, a method for producing the same, and an adhesive method.
【0002】[0002]
【従来の技術】従来、ICやLSIとリードフレームの
接合にはAu−Si共晶合金、半田あるいは銀ペースト
等が用いられている。Au−Si共晶合金は、耐熱性及
び耐湿性は高いが、弾性率が大きいため大型チップへ適
用した場合に割れやすいほか、高価である難点がある。
半田は安価であるものの、耐熱性が劣り、更に弾性率は
Au−Si共晶合金と同様に高く、大型チップへ適用が
困難である。一方、銀ペーストは安価で、耐湿性が高
く、弾性率も上記3者の中では最も低く、350℃の熱
圧着型ワイヤボンダーに適用できる耐熱性も有するの
で、現在のICやLSIとリードフレームの接合用材料
の主流となっている。しかし、近年ICやLSIの高集
積化が進み、それに伴ってチップが大型化しているなか
で、ICやLSIとリードフレームを銀ペーストで接合
しようとする場合、銀ペーストをチップ全面に広げ塗布
するには困難を伴う。2. Description of the Related Art Conventionally, an Au-Si eutectic alloy, solder, silver paste, or the like has been used to bond an IC or LSI to a lead frame. The Au-Si eutectic alloy has high heat resistance and moisture resistance, but has a large elastic modulus and is easily cracked when applied to a large chip, and is expensive.
Although solder is inexpensive, it has poor heat resistance and has a high elastic modulus similar to Au-Si eutectic alloy, making it difficult to apply to large chips. On the other hand, silver paste is inexpensive, has high moisture resistance, has the lowest elastic modulus among the above three, and has heat resistance applicable to a thermocompression bonding wire bonder at 350 ° C. Has become the mainstream of joining materials. However, as ICs and LSIs have become highly integrated in recent years and the chips have become larger in size, when joining the ICs and LSIs with the lead frame with silver paste, the silver paste is spread over the entire surface of the chip and applied. Is difficult.
【0003】マイクロエレクトロニック マニュファク
チャリング アンド テスティング(MICROELECTRONIC
MANUFACTURING AND TESTING 1988年6月,9頁)
に、金属フィラーを熱可塑性樹脂に充填したダイボンド
用の接着フィルムが開示された。これは熱可塑性樹脂の
融点付近まで温度を上げ、加圧接合するものである。Microelectronic Manufacturing and Testing (MICROELECTRONIC
(MANUFACTURING AND TESTING, June 1988, p. 9)
Discloses an adhesive film for die bonding in which a thermoplastic resin is filled with a metal filler. In this method, the temperature is raised to near the melting point of the thermoplastic resin and pressure bonding is performed.
【0004】[0004]
【発明が解決しようとする課題】上記雑誌に開示された
接着フィルムは、融点が低い熱可塑性樹脂を用いると接
合温度が低くなり、リードフレームの酸化等、チップに
与えるダメージは少なくてすむ。しかし、耐熱性が低い
のでダイボンド後の熱処理、例えばワイヤボンド、封止
工程等に耐えられない。そのような熱処理に耐えられる
ように融点の高い熱可塑性樹脂を用いると、接合温度が
高くなり、リードフレームの酸化等のダメージを受ける
問題がある。本発明は、ダイボンド時の熱処理を従来の
銀ペーストと同じように比較的低温で行うことのでき
る、ダイボント用の接着フィルムを提供することを目的
としている。The adhesive film disclosed in the above magazine has a low bonding temperature when a thermoplastic resin having a low melting point is used, and the damage to the chip such as oxidation of the lead frame is small. However, since it has low heat resistance, it cannot withstand heat treatment after die bonding, such as wire bonding and sealing. If a thermoplastic resin having a high melting point is used to withstand such heat treatment, the joining temperature becomes high, and there is a problem that the lead frame is damaged by oxidation or the like. It is an object of the present invention to provide an adhesive film for a die bond, which can be heat-treated at the time of die bonding at a relatively low temperature like a conventional silver paste.
【0005】[0005]
【課題を解決するための手段】本発明は、次の(1)〜
(3)に関する。 (1) (A)次の化2〔式(I)〕The present invention includes the following (1) to (1).
Regarding (3). (1) (A) The following chemical formula 2 [Formula (I)]
【化2】 (ただし、n=2〜20の整数を示す。)で表されるテ
トラカルボン酸二無水物が全酸二無水物に対し70モル
%以上含まれるテトラカルボン酸二無水物に、ジアミン
を反応させて得られるポリイミド系樹脂; (B)エポキシ樹脂; (C)フェノール樹脂; (D)硬化促進剤;及び (E)無機物質フィラー、を含有してなる接着フィル
ム。 (2)(A)式(I)で表されるテトラカルボン酸二無
水物が、全酸二無水物に対し70モル%以上含まれるテ
トラカルボン酸二無水物に、ジアミンを反応させて得ら
れるポリイミド系樹脂、(B)エポキシ樹脂;及び
(C)フェノール樹脂;を有機溶媒に溶解し、これに
(D)硬化促進剤;及び(E)無機物質フィラー、を加
え、混合し、ベースフィルム上に塗布したのち、加熱す
ることを特徴とする接着フィルムの製造法。 (3)半導体素子と支持部材の間に上記(1)の接着フ
ィルムを挾み、加熱圧着する、半導体素子と支持部材と
の接着法。 本発明で用いるポリイミド樹脂は、[Chemical 2] (However, n is an integer of 2 to 20.) Tetracarboxylic acid dianhydride represented by 70 mol% or more based on the total acid dianhydride is reacted with diamine. An adhesive film comprising a polyimide resin obtained by the above; (B) an epoxy resin; (C) a phenol resin; (D) a curing accelerator; and (E) an inorganic substance filler. (2) The tetracarboxylic dianhydride represented by formula (I) (A) is obtained by reacting a tetracarboxylic dianhydride containing 70 mol% or more with respect to the total acid dianhydride with a diamine. Polyimide resin, (B) epoxy resin; and (C) phenol resin; are dissolved in an organic solvent, and (D) a curing accelerator; and (E) an inorganic substance filler are added to and mixed with the base film. A method for producing an adhesive film, which comprises heating the composition after applying it to the. (3) A method of adhering a semiconductor element and a supporting member, in which the adhesive film of (1) above is sandwiched between the semiconductor element and the supporting member and thermocompression bonding is performed. The polyimide resin used in the present invention is
【化3】 (ただし、n=2〜20の整数を示す。)で表されるテ
トラカルボン酸二無水物が全酸二無水物に対し70モル
%以上含まれるテトラカルボン酸二無水物に、ジアミン
を反応させて得られるポリイミド系樹脂、が用いられ
る。[Chemical 3] (However, n is an integer of 2 to 20.) Tetracarboxylic acid dianhydride represented by 70 mol% or more based on the total acid dianhydride is reacted with diamine. The polyimide-based resin obtained by the above is used.
【0006】本発明で用いるエポキシ樹脂(B)は、分
子内に少なくとも2個のエポキシ基を含むもので、硬化
性や硬化物特性の点からフェノールのグリシジルエーテ
ル型のエポキシ樹脂が好ましく用いられる。このような
樹脂としては、ビスフェノールA、ビスフェノールA
D、ビスフェノールS、ビスフェノールFもしくはハロ
ゲン化ビスフェノールAとエピクロルヒドリンの縮合
物、フェノールノボラック樹脂のグリシジルエーテル、
クレゾールノボラック樹脂のグリシジルエーテル、ビス
フェノールAノボラック樹脂のグリシジルエーテル等が
挙げられる。エポキシ樹脂の量は、ポリイミド樹脂10
0重量部に対して1〜200重量部、好ましくは5〜1
00重量部の範囲でこれより少ないと接着性が悪くな
り、多いとフィルム形成性が劣る。The epoxy resin (B) used in the present invention contains at least two epoxy groups in the molecule, and a phenol glycidyl ether type epoxy resin is preferably used from the viewpoint of curability and cured product characteristics. Examples of such resins include bisphenol A and bisphenol A.
D, bisphenol S, bisphenol F or a condensate of halogenated bisphenol A and epichlorohydrin, glycidyl ether of phenol novolac resin,
Examples thereof include glycidyl ether of cresol novolac resin and glycidyl ether of bisphenol A novolac resin. The amount of epoxy resin is polyimide resin 10
1 to 200 parts by weight, preferably 5-1 to 0 parts by weight
If the amount is less than 100 parts by weight, the adhesiveness will be poor, and if the amount is too large, the film formability will be poor.
【0007】本発明で用いるフェノール樹脂(C)は、
分子中に少なくとも2個のフェノール性水酸基を有する
もので、このような樹脂としては例えば、フェノールノ
ボラック樹脂、クレゾールノボラック樹脂、ビスフェノ
ールAノボラック樹脂、ポリ−p−ビニルフェノール、
フェノールアラルキル樹脂等が挙げられる。フェノール
樹脂の量は、エポキシ樹脂100重量部に対して2〜1
50重量部、好ましくは50〜120重量部の範囲で、
これより多くても少なくても硬化性が不充分となる。The phenolic resin (C) used in the present invention is
It has at least two phenolic hydroxyl groups in the molecule, and examples of such a resin include phenol novolac resin, cresol novolac resin, bisphenol A novolac resin, poly-p-vinylphenol,
Examples thereof include phenol aralkyl resin. The amount of the phenol resin is 2-1 with respect to 100 parts by weight of the epoxy resin.
50 parts by weight, preferably in the range of 50 to 120 parts by weight,
If it is more or less than this, the curability becomes insufficient.
【0008】本発明で用いる硬化促進剤(D)は、エポ
キシ樹脂を硬化させるために用いられるものであれば特
に制限はない。このようなものとしては例えば、イミダ
ゾール類、ジシアンジアミド誘導体、ジカルボン酸ジヒ
ドラジド、トリフェニルホスフィン、テトラフェニルホ
スホニウムテトラフェニルボレート、2−エチル−4−
メチルイミダゾール−テトラフェニルボレート、1,8
−ジアザビシクロ(5,4,0)ウンデセン−7−テト
ラフェニルボレート等が用いられる。これらは、2種以
上を併用してもよい。硬化促進剤の量はエポキシ樹脂1
00重量部に対し、0.01〜50重量部、好ましくは
0.1〜20重量部の範囲で、これより少ないと硬化性
が不充分となり、多いと保存安定性が悪くなる。The curing accelerator (D) used in the present invention is not particularly limited as long as it is used for curing the epoxy resin. Examples of such compounds include imidazoles, dicyandiamide derivatives, dicarboxylic acid dihydrazides, triphenylphosphine, tetraphenylphosphonium tetraphenylborate, and 2-ethyl-4-.
Methylimidazole-tetraphenylborate, 1,8
-Diazabicyclo (5,4,0) undecene-7-tetraphenylborate and the like are used. These may be used in combination of two or more. The amount of curing accelerator is epoxy resin 1
The amount is in the range of 0.01 to 50 parts by weight, preferably 0.1 to 20 parts by weight, relative to 00 parts by weight.
【0009】本発明で用いる無機物質フィラー(E)
は、接着剤に低熱膨張性、低吸湿率を付与する目的で添
加されるものであり、シリカ、アルミナ、チタニア、ガ
ラス、酸化鉄、セラミック等の無機絶縁体を単独又は2
種以上混合して用いる。無機物質フィラーの量は、ポリ
イミド樹脂100重量部に対し1〜8000重量部、好
ましくは50〜4000重量部の範囲である。これより
も少ないと充分な低熱膨張性、低吸湿性が得られず、こ
れよりも多いと接着性が低下する。Inorganic substance filler (E) used in the present invention
Is added for the purpose of imparting low thermal expansion and low moisture absorption to the adhesive, and an inorganic insulating material such as silica, alumina, titania, glass, iron oxide or ceramic is used alone or 2
Used as a mixture of two or more species. The amount of the inorganic substance filler is in the range of 1 to 8000 parts by weight, preferably 50 to 4000 parts by weight, based on 100 parts by weight of the polyimide resin. If it is less than this, sufficient low thermal expansion and low hygroscopicity cannot be obtained, and if it is more than this, the adhesiveness decreases.
【0010】本発明で用いる、式(I)で表されるテト
ラカルボン酸二無水物としては、エチレンビストリメリ
テート二無水物、トリメチレンビストリメリテート二無
水物、テトラメチレンビストリメリテート二無水物、ペ
ンタメチレンビストリメリテート二無水物、ヘキサメチ
レンビストリメリテート二無水物、ヘプタメチレンビス
トリメリテート二無水物、オクタメチレンビストリメリ
テート二無水物、ノナメチレンビストリメリテート二無
水物、デカメチレンビストリメリテート二無水物、ドデ
カメチレンビストリメリテート二無水物、ヘキサデカメ
チレンビストリメリテート二無水物、オクタデカメチレ
ンビストリメリテート二無水物等があり、2種以上を併
用してもよい。The tetracarboxylic dianhydride represented by the formula (I) used in the present invention is ethylene bis trimellitate dianhydride, trimethylene bis trimellitate dianhydride, tetramethylene bis trimellitate dianhydride. , Pentamethylene bis trimellitate dianhydride, hexamethylene bis trimellitate dianhydride, heptamethylene bis trimellitate dianhydride, octamethylene bis trimellitate dianhydride, nonamethylene bis trimellitate dianhydride, decamethylene bis trimellitate dianhydride There are tate dianhydride, dodecamethylene bis trimellitate dianhydride, hexadecamethylene bis trimellitate dianhydride, octadecamethylene bis trimellitate dianhydride and the like, and two or more kinds may be used in combination.
【0011】これらのテトラカルボン酸二無水物は、無
水トリメリット酸モノクロライド及び対応するジオール
から合成することができる。上記テトラカルボン酸二無
水物は、全テトラカルボン酸二無水物に対し70モル%
以上を含むものである。70モル%未満であると、接着
フィルムの接合時の温度が高くなり好ましくない。These tetracarboxylic dianhydrides can be synthesized from trimellitic anhydride monochloride and the corresponding diols. The above-mentioned tetracarboxylic dianhydride is 70 mol% with respect to the total tetracarboxylic dianhydride.
It includes the above. When it is less than 70 mol%, the temperature at the time of joining the adhesive film becomes high, which is not preferable.
【0012】式(I)のテトラカルボン酸二無水物と共
に使用できるテトラカルボン酸無水物としては、例え
ば、ピロメリット酸二無水物、3,3′,4,4′−ジ
フェニルテトラカルボン酸二無水物、2,2′,3,
3′−ジフェニルテトラカルボン酸二無水物、2,2−
ビス(3,4−ジカルボキシフェニル)プロパン二無水
物、2,2−ビス(2,3−ジカルボキシフェニル)プ
ロパン二無水物、1,1−ビス(2,3−ジカルボキシ
フェニル)エタン二無水物、1,1−ビス(3,4−ジ
カルボキシフェニル)エタン二無水物、ビス(2,3−
ジカルボキシフェニル)メタン二無水物、ビス(3,4
−ジカルボキシフェニル)メタン二無水物、ビス(3,
4−ジカルボキシフェニル)スルホン二無水物、3,
4,9,10−ペリレンテトラカルボン酸二無水物、ビ
ス(3,4−ジカルボキシフェニル)エーテル二無水
物、ベンゼン−1,2,3,4−テトラカルボン酸二無
水物、3,4,3′,4′−ベンゾフェノンテトラカル
ボン酸二無水物、2,3,2′,3−ベンゾフェノンテ
トラカルボン酸二無水物、2,3,3′,4′−ベンゾ
フェノンテトラカルボン酸二無水物、1,2,5,6−
ナフタレンテトラカルボン酸二無水物、2,3,6,7
−ナフタレンテトラカルボン酸二無水物、1,2,4,
5−ナフタレン−テトラカルボン酸二無水物、1,4,
5,8−ナフタレン−テトラカルボン酸二無水物、Tetracarboxylic acid anhydrides which can be used with the tetracarboxylic acid dianhydride of formula (I) include, for example, pyromellitic dianhydride and 3,3 ', 4,4'-diphenyltetracarboxylic dianhydride. Things, 2, 2 ', 3,
3'-diphenyltetracarboxylic dianhydride, 2,2-
Bis (3,4-dicarboxyphenyl) propane dianhydride, 2,2-bis (2,3-dicarboxyphenyl) propane dianhydride, 1,1-bis (2,3-dicarboxyphenyl) ethane dianhydride Anhydride, 1,1-bis (3,4-dicarboxyphenyl) ethane dianhydride, bis (2,3-
Dicarboxyphenyl) methane dianhydride, bis (3,4
-Dicarboxyphenyl) methane dianhydride, bis (3,3
4-dicarboxyphenyl) sulfone dianhydride, 3,
4,9,10-Perylenetetracarboxylic dianhydride, bis (3,4-dicarboxyphenyl) ether dianhydride, benzene-1,2,3,4-tetracarboxylic dianhydride, 3,4 3 ', 4'-benzophenone tetracarboxylic dianhydride, 2,3,2', 3-benzophenone tetracarboxylic dianhydride, 2,3,3 ', 4'-benzophenone tetracarboxylic dianhydride, 1 , 2, 5, 6-
Naphthalenetetracarboxylic dianhydride, 2,3,6,7
-Naphthalene tetracarboxylic dianhydride, 1,2,4
5-naphthalene-tetracarboxylic dianhydride, 1,4
5,8-naphthalene-tetracarboxylic dianhydride,
【0013】2,6−ジクロルナフタレン−1,4,
5,8−テトラカルボン酸二無水物、2,7−ジクロル
ナフタレン−1,4,5,8−テトラカルボン酸二無水
物、2,3,6,7−テトラクロルナフタレン−1,
4,5,8−テトラカルボン酸二無水物、フエナンスレ
ン−1,8,9,10−テトラカルボン酸二無水物、ピ
ラジン−2,3,5,6−テトラカルボン酸二無水物、
チオフエン−2,3,4,5−テトラカルボン酸二無水
物、2,3,3′,4′−ビフェニルテトラカルボン酸
二無水物、3,4,3′,4′−ビフェニルテトラカル
ボン酸二無水物、2,3,2′,3′−ビフェニルテト
ラカルボン酸二無水物、ビス(3,4−ジカルボキシフ
ェニル)ジメチルシラン二無水物、ビス(3,4−ジカ
ルボキシフェニル)メチルフェニルシラン二無水物、ビ
ス(3,4−ジカルボキシフェニル)ジフェニルシラン
二無水物、1,4−ビス(3,4−ジカルボキシフェニ
ルジメチルシリル)ベンゼン二無水物、1,3−ビス
(3,4−ジカルボキシフェニル)−1,1,3,3−
テトラメチルジシクロヘキサン二無水物、p−フェニル
ビス(トリメリット酸モノエステル酸無水物)、2,6-dichloronaphthalene-1,4
5,8-tetracarboxylic dianhydride, 2,7-dichloronaphthalene-1,4,5,8-tetracarboxylic dianhydride, 2,3,6,7-tetrachloronaphthalene-1,
4,5,8-tetracarboxylic dianhydride, phenanthrene-1,8,9,10-tetracarboxylic dianhydride, pyrazine-2,3,5,6-tetracarboxylic dianhydride,
Thiofene-2,3,4,5-tetracarboxylic dianhydride, 2,3,3 ', 4'-biphenyltetracarboxylic dianhydride, 3,4,3', 4'-biphenyltetracarboxylic dianhydride Anhydride, 2,3,2 ', 3'-biphenyltetracarboxylic dianhydride, bis (3,4-dicarboxyphenyl) dimethylsilane dianhydride, bis (3,4-dicarboxyphenyl) methylphenylsilane Dianhydride, bis (3,4-dicarboxyphenyl) diphenylsilane dianhydride, 1,4-bis (3,4-dicarboxyphenyldimethylsilyl) benzene dianhydride, 1,3-bis (3,4) -Dicarboxyphenyl) -1,1,3,3-
Tetramethyldicyclohexane dianhydride, p-phenylbis (trimellitic acid monoester acid anhydride),
【0014】エチレンテトラカルボン酸二無水物、1,
2,3,4−ブタンテトラカルボン酸二無水物、デカヒ
ドロナフタレン−1,4,5,8−テトラカルボン酸二
無水物、4,8−ジメチル−1,2,3,5,6,7−
ヘキサヒドロナフタレン−1,2,5,6−テトラカル
ボン酸二無水物、シクロペンタン−1,2,3,4−テ
トラカルボン酸二無水物、ピロリジン−2,3,4,5
−テトラカルボン酸二無水物、1,2,3,4−シクロ
ブタンテトラカルボン酸二無水物、ビス(エキソ−ビシ
クロ〔2,2,1〕ヘプタン−2,3−ジカルボン酸無
水物)スルホン、ビシクロ−(2,2,2)−オクト
(7)−エン2,3,5,6−テトラカルボン酸二無水
物、2,2−ビス(3,4−ジカルボキシフェニル)ヘ
キサフルオロプロパン二無水物、2,2−ビス〔4−
(3,4−ジカルボキシフェノキシ)フェニル〕ヘキサ
フルオロプロパン二無水物、4,4′−ビス(3,4−
ジカルボキシフェノキシ)ジフェニルスルフイド二無水
物、1,4−ビス(2−ヒドロキシヘキサフルオロイソ
プロピル)ベンゼンビス(トリメリット酸無水物)、
1,3−ビス(2−ヒドロキシヘキサフルオロイソプロ
ピル)ベンゼンビス(トリメリット酸無水物)、5−
(2,5−ジオキソテトラヒドロフリル)−3−メチル
−3−シクロヘキセン−1,2−ジカルボン酸無水物、
テトラヒドロフラン−2,3,4,5−テトラカルボン
酸二無水物等があり、2種類以上を混合して用いてもよ
い。Ethylene tetracarboxylic dianhydride, 1,
2,3,4-butanetetracarboxylic dianhydride, decahydronaphthalene-1,4,5,8-tetracarboxylic dianhydride, 4,8-dimethyl-1,2,3,5,6,7 −
Hexahydronaphthalene-1,2,5,6-tetracarboxylic dianhydride, cyclopentane-1,2,3,4-tetracarboxylic dianhydride, pyrrolidine-2,3,4,5
-Tetracarboxylic acid dianhydride, 1,2,3,4-cyclobutanetetracarboxylic acid dianhydride, bis (exo-bicyclo [2,2,1] heptane-2,3-dicarboxylic acid anhydride) sulfone, bicyclo -(2,2,2) -Octo (7) -ene 2,3,5,6-tetracarboxylic dianhydride, 2,2-bis (3,4-dicarboxyphenyl) hexafluoropropane dianhydride , 2,2-bis [4-
(3,4-Dicarboxyphenoxy) phenyl] hexafluoropropane dianhydride, 4,4'-bis (3,4-
Dicarboxyphenoxy) diphenyl sulfide dianhydride, 1,4-bis (2-hydroxyhexafluoroisopropyl) benzenebis (trimellitic anhydride),
1,3-bis (2-hydroxyhexafluoroisopropyl) benzenebis (trimellitic anhydride), 5-
(2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2-dicarboxylic acid anhydride,
There are tetrahydrofuran-2,3,4,5-tetracarboxylic dianhydride and the like, and two or more kinds may be mixed and used.
【0015】本発明で使用されるジアミンとしては、
1,2−ジアミノエタン、1,3−ジアミノプロパン、
1,4−ジアミノブタン、1,5−ジアミノペンタン、
1,6−ジアミノヘキサン、1,7−ジアミノヘプタ
ン、1,8−ジアミノオクタン、1,9−ジアミノノナ
ン、1,10−ジアミノデカン、1,11−ジアミノウ
ンデカン、1,12−ジアミノドデカン等の脂肪族ジア
ミン、o−フェニレンジアミン、m−フェニレンジアミ
ン、p−フェニレンジアミン、3,3′−ジアミノジフ
ェニルエーテル、3,4′−ジアミノジフェニルエーテ
ル、4,4′−ジアミノジフェニルエーテル、3,3′
−ジアミノジフェニルメタン、3,4′−ジアミノジフ
ェニルメタン、4,4′−ジアミノジフェニルメタン、
3,3′−ジアミノジフェニルジフルオロメタン、3,
4′−ジアミノジフェニルジフルオロメタン、4,4′
−ジアミノジフェニルジフルオロメタン、3,3′−ジ
アミノジフェニルスルホン、3,4′−ジアミノジフェ
ニルスルホン、4,4′−ジアミノジフェニルスルホ
ン、3,3′−ジアミノジフェニルスルフイド、3,
4′−ジアミノジフェニルスルフイド、4,4′−ジア
ミノジフェニルスルフイド、As the diamine used in the present invention,
1,2-diaminoethane, 1,3-diaminopropane,
1,4-diaminobutane, 1,5-diaminopentane,
Fats such as 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, 1,11-diaminoundecane and 1,12-diaminododecane Group diamine, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,3 '
-Diaminodiphenylmethane, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane,
3,3'-diaminodiphenyldifluoromethane, 3,
4'-diaminodiphenyldifluoromethane, 4,4 '
-Diaminodiphenyldifluoromethane, 3,3'-diaminodiphenylsulfone, 3,4'-diaminodiphenylsulfone, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, 3,
4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide,
【0016】3,3′−ジアミノジフェニルケトン、
3,4′−ジアミノジフェニルケトン、4,4′−ジア
ミノジフェニルケトン、2,2−ビス(3−アミノフェ
ニル)プロパン、2,2′−(3,4′−ジアミノジフ
ェニル)プロパン、2,2−ビス(4−アミノフェニ
ル)プロパン、2,2−ビス(3−アミノフェニル)ヘ
キサフルオロプロパン、2,2−(3,4′−ジアミノ
ジフェニル)ヘキサフルオロプロパン、2,2−ビス
(4−アミノフェニル)ヘキサフルオロプロパン、1,
3−ビス(3−アミノフェノキシ)ベンゼン、1,4−
ビス(3−アミノフェノキシ)ベンゼン、1,4−ビス
(4−アミノフェノキシ)ベンゼン、3,3′−(1,
4−フェニレンビス(1−メチルエチリデン))ビスア
ニリン、3,4′−(1,4−フェニレンビス(1−メ
チルエチリデン))ビスアニリン、4,4′−(1,4
−フェニレンビス(1−メチルエチリデン))ビスアニ
リン、2,2−ビス(4−(3−アミノフェノキシ)フ
ェニル)プロパン、2,2−ビス(4−(4−アミノフ
ェノキシ)フェニル)プロパン、2,2−ビス(4−
(3−アミノフェノキシ)フェニル)ヘキサフルオロプ
ロパン、2,2−ビス(4−(4−アミノフエノキシ)
フエニル)ヘキサフルオロプロパン、ビス(4−(3−
アミノフェノキシ)フェニル)スルフイド、ビス(4−
(4−アミノフェノキシ)フェニル)スルフイド、ビス
(4−(3−アミノフェノキシ)フェニル)スルホン、
ビス(4−(4−アミノフェノキシ)フェニル)スルホ
ン、3,3’−ジメトキシ−4,4’−ジアミノビフェ
ニル、4,4’−メチレン−ビス(2,6−ジエチルア
ニリン)、o−トリジンスルホン、1,4−ビス(4−
アミノフェノキシ)ベンゼン、4,4−メチレン−ビス
(2,6−ジイソプロピルアニリン)、4,4’−ビス
(4−アミノフェノキシ)ビフェニル、1,1−ビス
(4−(4−アミノフェノキシ)フェニル)シクロヘキ
サン、1,3−ビス(3−アミノプロピル)テトラメチ
ルジシロキサン等の芳香族ジアミンを挙げることができ
る。3,3'-diaminodiphenyl ketone,
3,4'-diaminodiphenyl ketone, 4,4'-diaminodiphenyl ketone, 2,2-bis (3-aminophenyl) propane, 2,2 '-(3,4'-diaminodiphenyl) propane, 2,2 -Bis (4-aminophenyl) propane, 2,2-bis (3-aminophenyl) hexafluoropropane, 2,2- (3,4'-diaminodiphenyl) hexafluoropropane, 2,2-bis (4- Aminophenyl) hexafluoropropane, 1,
3-bis (3-aminophenoxy) benzene, 1,4-
Bis (3-aminophenoxy) benzene, 1,4-bis (4-aminophenoxy) benzene, 3,3 ′-(1,
4-phenylenebis (1-methylethylidene)) bisaniline, 3,4 '-(1,4-phenylenebis (1-methylethylidene)) bisaniline, 4,4'-(1,4
-Phenylene bis (1-methylethylidene)) bisaniline, 2,2-bis (4- (3-aminophenoxy) phenyl) propane, 2,2-bis (4- (4-aminophenoxy) phenyl) propane, 2, 2-bis (4-
(3-Aminophenoxy) phenyl) hexafluoropropane, 2,2-bis (4- (4-aminophenoxy))
Phenyl) hexafluoropropane, bis (4- (3-
Aminophenoxy) phenyl) sulfide, bis (4-
(4-aminophenoxy) phenyl) sulfide, bis (4- (3-aminophenoxy) phenyl) sulfone,
Bis (4- (4-aminophenoxy) phenyl) sulfone, 3,3′-dimethoxy-4,4′-diaminobiphenyl, 4,4′-methylene-bis (2,6-diethylaniline), o-tolidine sulfone , 1,4-bis (4-
Aminophenoxy) benzene, 4,4-methylene-bis (2,6-diisopropylaniline), 4,4'-bis (4-aminophenoxy) biphenyl, 1,1-bis (4- (4-aminophenoxy) phenyl ) Aromatic diamines such as cyclohexane and 1,3-bis (3-aminopropyl) tetramethyldisiloxane can be mentioned.
【0017】テトラカルボン酸二無水物とジアミンの縮
合反応は、有機溶媒中で行う。この場合、テトラカルボ
ン酸二無水物とジアミンは等モル又はほぼ等モルで用い
るのが好ましく、各成分の添加順序は任意である。用い
る有機溶媒としては、ジメチルアセトアミド、ジメチル
ホルムアミド、N−メチル−2−ピロリドン、ジメチル
スルホキシド、ヘキサメチルホスホリルアミド、m−ク
レゾール、o−クロルフェノール等がある。The condensation reaction of tetracarboxylic dianhydride and diamine is carried out in an organic solvent. In this case, the tetracarboxylic dianhydride and the diamine are preferably used in equimolar or almost equimolar amounts, and the addition order of each component is arbitrary. Examples of the organic solvent used include dimethylacetamide, dimethylformamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, hexamethylphosphorylamide, m-cresol, and o-chlorophenol.
【0018】反応温度は80℃以下、好ましくは0〜5
0℃である。反応が進行するにつれ反応液の粘度が徐々
に上昇する。この場合、ポリイミドの前駆体であるポリ
アミド酸が生成する。The reaction temperature is 80 ° C. or lower, preferably 0-5.
It is 0 ° C. As the reaction proceeds, the viscosity of the reaction solution gradually increases. In this case, polyamic acid that is a precursor of polyimide is generated.
【0019】ポリイミド樹脂は、前記反応物(ポリアミ
ド酸)を脱水閉環させて得ることができる。脱水閉環は
120℃〜250℃で熱処理する方法や化学的方法を用
いて行うことができる。120℃〜250℃で熱処理す
る方法の場合、脱水反応で生じる水を系外に除去しなが
ら行うことが好ましい。この際、ベンゼン、トルエン、
キシレン等を用いて水を共沸除去してもよい。The polyimide resin can be obtained by dehydrating and ring-closing the reaction product (polyamic acid). The dehydration ring closure can be performed by a method of heat treatment at 120 ° C to 250 ° C or a chemical method. In the case of the method of heat treatment at 120 ° C. to 250 ° C., it is preferable to perform it while removing water generated by the dehydration reaction outside the system. At this time, benzene, toluene,
Water may be removed azeotropically using xylene or the like.
【0020】化学的方法で脱水閉環させる場合は、閉環
剤として無水酢酸、無水プロピオン酸、無水安息香酸の
酸無水物、ジシクロヘキシルカルボジイミド等のカルボ
ジイミド化合物等を用いる。このとき必要に応じてピリ
ジン、イソキノリン、トリメチルアミン、アミノピリジ
ン、イミダゾール等の閉環触媒を用いてもよい。閉環剤
又は閉環触媒は、テトラカルボン酸二無水物1モルに対
し、それぞれ1〜8モルの範囲で使用するのが好まし
い。In the case of performing dehydration ring closure by a chemical method, acetic anhydride, propionic anhydride, acid anhydride of benzoic anhydride, carbodiimide compound such as dicyclohexylcarbodiimide, etc. are used as a ring-closing agent. At this time, a ring-closing catalyst such as pyridine, isoquinoline, trimethylamine, aminopyridine, or imidazole may be used if necessary. The ring-closing agent or ring-closing catalyst is preferably used in the range of 1 to 8 mol per 1 mol of tetracarboxylic dianhydride.
【0021】また、本発明の接着フィルムに、必要に応
じてシランカップリング剤、チタン系カップリング剤、
ノニオン系界面活性剤、フッ素系界面活性剤、シリコー
ン系添加剤等を適宜加えてもよい。If necessary, the adhesive film of the present invention may further contain a silane coupling agent, a titanium coupling agent,
Nonionic surfactants, fluorochemical surfactants, silicone additives, etc. may be added as appropriate.
【0022】本発明の接着フィルムの製造は、以下のよ
うにする。まずエポキシ樹脂、フェノール樹脂、ポリイ
ミド系樹脂を有機溶媒に溶解する。ここで用いられる有
機溶媒は、上記材料を均一に溶解又は混練できるもので
あれば特に制限はなく、そのようなものとしては例え
ば、ジメチルホルムアミド、ジメチルアセトアミド、N
−メチルピロリドン、ジメチルスルホキシド、ジエチレ
ングリコールジメチルエーテル、トルエン、ベンゼン、
キシレン、メチルエチルケトン、テトラヒドロフラン、
エチルセロソルブ、エチルセロソルブアセテート、ブチ
ルセロソルブ、ジオキサン等が挙げられる。The adhesive film of the present invention is manufactured as follows. First, an epoxy resin, a phenol resin, and a polyimide resin are dissolved in an organic solvent. The organic solvent used here is not particularly limited as long as it can uniformly dissolve or knead the above materials, and examples thereof include dimethylformamide, dimethylacetamide, and N.
-Methylpyrrolidone, dimethyl sulfoxide, diethylene glycol dimethyl ether, toluene, benzene,
Xylene, methyl ethyl ketone, tetrahydrofuran,
Examples thereof include ethyl cellosolve, ethyl cellosolve acetate, butyl cellosolve and dioxane.
【0023】次いで、硬化促進剤、無機物質フィラー及
び必要に応じ添加剤を加え、混合する。この場合、通常
の攪拌機、らいかい機、三本ロール、ボールミルなどの
分散機を適宜組み合せて、混練を行ってもよい。Next, a hardening accelerator, an inorganic substance filler and, if necessary, additives are added and mixed. In this case, the kneading may be carried out by appropriately combining an ordinary stirrer, a raker, a three-roller, a ball mill and other dispersing machines.
【0024】こうして得たペースト状混合物を、例えば
プロピレン製シート等のベースフィルム上に均一に塗布
し、使用した溶媒が充分に揮散する条件、すなわち、お
おむね60〜200℃の温度で、0.1〜30分間加熱
し、接着フィルムを得る。The paste mixture thus obtained is evenly applied onto a base film such as a propylene sheet, and the solvent used is sufficiently volatilized, that is, at a temperature of about 60 to 200 ° C. Heat for ~ 30 minutes to obtain an adhesive film.
【0025】本発明で得られた接着フィルムは、IC、
LSI等の半導体素子のリードフレーム、セラミックス
配線板、ガラスエポキシ配線板、ガラスポリイミド配線
板の支持部材の接着に用いられる。The adhesive film obtained in the present invention is an IC,
It is used for bonding lead frames of semiconductor elements such as LSIs, ceramic wiring boards, glass epoxy wiring boards, and glass polyimide wiring board support members.
【0026】本発明の接着フィルムは、例えば、ICや
LSI等の半導体素子とリードフレームとを接着する場
合、次の様な方法で接着することができる。The adhesive film of the present invention can be adhered by the following method, for example, when adhering a semiconductor element such as IC or LSI to a lead frame.
【0027】第一に、接着フィルムをテープリボン状に
形成し、これを半導体素子の大きさに合わせて切断し、
リードフレームと半導体素子の間に挟み込んで、加熱接
着させる方法がある。この方法で接着する場合には、例
えば半田リボン用のダイボンディング装置等を応用した
装置で接着させることができる。First, an adhesive film is formed into a tape ribbon shape, which is cut according to the size of a semiconductor element,
There is a method in which it is sandwiched between a lead frame and a semiconductor element and heat-bonded. When the bonding is performed by this method, the bonding can be performed by a device to which a die bonding device for a solder ribbon or the like is applied.
【0028】第二に、接着フィルムをまずリードフレー
ムに形成しておき、次に半導体素子を加熱接着させる方
法がある。リードフレームに接着フィルムを形成するに
は、接着フィルムを半導体素子の大きさに合わせて切断
し、加熱して貼り付ける方法あるいは溶媒を塗布して貼
り付ける方法等がある。また、接着フィルムのワニスを
リードフレーム上に印刷塗布する方法で形成させること
もできる。リードフレームに接着フィルムを形成した
後、半導体素子を接着するには、例えば、従来、銀ペー
ストで用いられていたダイボンディング装置等を応用し
た装置で接着させることができる。Second, there is a method in which an adhesive film is first formed on the lead frame and then the semiconductor element is heated and adhered. In order to form the adhesive film on the lead frame, there are a method of cutting the adhesive film according to the size of the semiconductor element, heating and pasting, a method of applying a solvent and pasting. Alternatively, the varnish of the adhesive film may be formed by printing on the lead frame. After the adhesive film is formed on the lead frame, the semiconductor element can be adhered by, for example, an apparatus to which a die bonding apparatus or the like conventionally used for silver paste is applied.
【0029】第三に、接着フィルムをウェハ裏面に形成
しておき、次にダイシング工程でウェハ及び接着フィル
ムを切断し、リードフレームに接着する方法がある。ウ
ェハ裏面に接着フィルムを形成するには、接着フィルム
を加熱して貼り付ける方法あるいは溶媒を塗布して貼り
付ける方法等がある。また、接着フィルムのワニスをウ
ェハ裏面に印刷塗布あるいはスピンコートする方法で形
成させることもできる。ウェハ裏面に接着フィルムを形
成した後、半導体素子を接着するには、例えば、従来、
銀ペーストで用いられていたダイボンディング装置等を
応用した装置で接着させることができる。Thirdly, there is a method in which an adhesive film is formed on the back surface of the wafer, and then the wafer and the adhesive film are cut in a dicing step and adhered to the lead frame. To form the adhesive film on the back surface of the wafer, there are a method of heating and attaching the adhesive film, a method of applying a solvent and attaching. Alternatively, the varnish of the adhesive film may be formed on the back surface of the wafer by printing or spin coating. After the adhesive film is formed on the back surface of the wafer, for bonding the semiconductor element, for example, conventionally,
Bonding can be performed with a device to which a die bonding device or the like used for silver paste is applied.
【0030】上記の方法の他に、ダイシング工程で用い
られる粘着性のダイシングフィルムの上に、接着フィル
ムを形成させておき、これにウェハを貼り付けた後、ダ
イシング工程で半導体素子と接着フィルムを切断し、リ
ードフレームに貼り付ける方法等があるが、本発明の接
着フィルムは、上記に例示したいずれの方法に限定され
るものではない。In addition to the above method, an adhesive film is formed on an adhesive dicing film used in the dicing process, a wafer is attached to the adhesive film, and then the semiconductor element and the adhesive film are bonded in the dicing process. There are methods such as cutting and attaching to a lead frame, but the adhesive film of the present invention is not limited to any of the methods exemplified above.
【0031】[0031]
【実施例】以下、本発明を実施例を用いて説明する。 合成例1 温度計、攪拌機及び塩化カルシウム管を備えた500m
lの四つ口フラスコに、2,2−ビス(4−(4−アミ
ノフェノキシ)フェニル)プロパン41g(0.1モ
ル)及びジメチルアセトアミド150gをとり、攪拌し
た。ジアミンの溶解後、フラスコを氷浴中で冷却しなが
ら、エチレンビストリメリテート二無水物41g(0.
1モル)を少量ずつ添加した。室温で3時間反応させた
のち、キシレン30gを加え、N2 ガスを吹き込みなが
ら150℃で加熱し、水と共にキシレンを共沸除去し
た。その反応液を水中に注ぎ、沈澱したポリマーを濾過
により採り、乾燥してポリイミドAを得た。EXAMPLES The present invention will be described below with reference to examples. Synthesis Example 1 500 m equipped with a thermometer, stirrer and calcium chloride tube
41 g (0.1 mol) of 2,2-bis (4- (4-aminophenoxy) phenyl) propane and 150 g of dimethylacetamide were placed in a 1-liter four-necked flask and stirred. After dissolution of the diamine, 41 g of ethylenebis trimellitate dianhydride (0.
1 mol) was added in small portions. After reacting for 3 hours at room temperature, 30 g of xylene was added, and the mixture was heated at 150 ° C. while blowing N 2 gas to remove xylene azeotropically with water. The reaction solution was poured into water, and the precipitated polymer was collected by filtration and dried to obtain polyimide A.
【0032】合成例2 温度計、攪拌機及び塩化カルシウム管を備えた500m
lの四つ口フラスコに、4,4’−メチレン−ビス
(2,6−ジイソプロピルアニリン)32.94g
(0.09モル)、1,3−ビス(3−アミノプロピ
ル)テトラメチルジシロキサン2.48g(0.01モ
ル)及びN−メチル−2−ピロリドン150gをとり、
攪拌した。ジアミンの溶解後、室温で、テトラメチレン
ビストリメリテート二無水物43.8g(0.1モル)
を加えた。5℃以下で5時間反応させ、無水酢酸20.
4g(0.2モル)及びピリジン15.8g(0.2モ
ル)を加え、1時間室温で攪拌した。この反応液を水中
に注ぎ、沈澱したポリマーを濾過により採り、乾燥して
ポリイミドBを得た。Synthesis Example 2 500 m equipped with a thermometer, stirrer and calcium chloride tube
32.94 g of 4,4′-methylene-bis (2,6-diisopropylaniline) was placed in a 4-necked flask having a volume of 1 l.
(0.09 mol), 1,3-bis (3-aminopropyl) tetramethyldisiloxane 2.48 g (0.01 mol) and N-methyl-2-pyrrolidone 150 g are taken,
It was stirred. After dissolution of the diamine, at room temperature, 43.8 g (0.1 mol) of tetramethylene bis trimellitate dianhydride.
Was added. The reaction was carried out at 5 ° C or lower for 5 hours, and acetic anhydride 20.
4 g (0.2 mol) and 15.8 g (0.2 mol) of pyridine were added and stirred for 1 hour at room temperature. The reaction solution was poured into water, and the precipitated polymer was collected by filtration and dried to obtain polyimide B.
【0033】合成例3 温度計、攪拌機、塩化カルシウム管を備えた500ml
の四つ口フラスコに、2,2−ビス(4−アミノフェノ
キシフェニル)プロパン32.8g(0.08モル)、
3,3′,5,5′−テトラメチル−4,4′−ジアミ
ノジフェニルメタン5.08g(0.02モル)及びジ
メチルアセトアミド100gをとり、攪拌した。ジアミ
ンの溶解後、フラスコを氷浴中で冷却しながら、デカメ
チレンビストリメリテート二無水物41.8g(0.0
8モル)及びベンゾフェノンテトラカルボン酸二無水物
6.44g(0.02モル)を少量ずつ添加した。添加
終了後、氷浴中で3時間、更に室温で4時間反応させた
後、無水酢酸25.5g(0.25モル)及びピリジン
19.8g(0.25モル)を添加し、2時間室温で攪
拌した。その反応液を水中に注ぎ、沈澱したポリマーを
濾過により採り、乾燥してポリイミドCを得た。Synthesis Example 3 500 ml equipped with a thermometer, stirrer and calcium chloride tube
In a four-necked flask of No. 2,2-bis (4-aminophenoxyphenyl) propane 32.8 g (0.08 mol),
5.08 g (0.02 mol) of 3,3 ', 5,5'-tetramethyl-4,4'-diaminodiphenylmethane and 100 g of dimethylacetamide were taken and stirred. After dissolution of the diamine, while cooling the flask in an ice bath, decamethylene bis trimellitate dianhydride 41.8 g (0.0
8 mol) and 6.44 g (0.02 mol) of benzophenone tetracarboxylic dianhydride were added in small portions. After completion of the addition, the mixture was reacted in an ice bath for 3 hours and further at room temperature for 4 hours, then, 25.5 g (0.25 mol) of acetic anhydride and 19.8 g (0.25 mol) of pyridine were added, and the mixture was kept at room temperature for 2 hours. It was stirred at. The reaction solution was poured into water, and the precipitated polymer was collected by filtration and dried to obtain polyimide C.
【0034】実施例1〜5 表1の配合表に示す通り、No.1〜7(本発明の実施
例:No.1〜5、比較例:No.6〜7)のワニスを
調合した。なお、表1において、種々の記号は下記のも
のを意味する。 YDCH-702:東都化成、クレゾールノボラック型エポキシ
(エポキシ当量220 ) N-865 :大日本インキ製、ビスフェノールノボラック型
エポキシ(エポキシ当量208 ) ESCN-195:住友化学、クレゾールノボラック型エポキシ
(エポキシ当量200 ) H-1 :明和化成、フェノールノボラック( OH 当量106
) VH-4170 :大日本インキ、ビスフェノールAノボラック
( OH 当量118 )Examples 1 to 5 As shown in the formulation table of Table 1, Nos. Varnishes 1 to 7 (Examples of the present invention: No. 1 to 5, Comparative Examples: No. 6 to 7) were prepared. In Table 1, various symbols mean the following. YDCH-702: Tohto Kasei, Cresol novolac type epoxy (epoxy equivalent 220) N-865: Dainippon Ink, bisphenol novolac type epoxy (epoxy equivalent 208) ESCN-195: Sumitomo Chemical, cresol novolac epoxy (epoxy equivalent 200) H-1: Meiwa Kasei, phenol novolac (OH equivalent 106
) VH-4170: Dainippon Ink, Bisphenol A Novolac (OH equivalent 118)
【0035】[0035]
【表1】 表1 配合表 (単位:重量部) ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ No. 1 2 3 4 5 6 7 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ ポリイミド A B C A A − A 100 100 100 100 100 100 ──────────────────────────────────── エポキシ樹脂 YDCN-702 N-865 ESCN-195 N-865 N-865 YDCN-702 − 50部 20部 10部 10部 100部 100部 − ──────────────────────────────────── フェノー H-1 H-1 VH-4170 VH-4170 VH-4170 H-1 − ル樹脂 24 10 5.9 5.6 70 48 − ──────────────────────────────────── 硬化促進 2P4MHZ TPPK 2MA-0K TPPK TPPK 2P4MHZ − 剤 0.5 0.4 0.1 0.5 10 1 − ──────────────────────────────────── 無機物質 シリカ シリカ シリカ アルミナ アルミナ シリカ シリカ フィラー 80 45 18 100 190 180 180 ──────────────────────────────────── 溶 媒 DMAC NMP DMF DMF DMF DMAC DMAC 400 200 100 100 1000 1000 500 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ ただし、表1中の記号は、下記の意味である。 DMAC:ジメチルアセトアミド NMP :N−メチルピロリドン DMF :ジメチルホルムアミド このワニスを30〜50μmの厚さにポリプロピレンフ
ィルム上に塗布し、80℃で10分、つづいて120℃
で30分加熱し、接着フィルムを得た。[Table 1] Table 1 Recipe (Unit: parts by weight) ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ No. 1 2 3 4 5 6 7 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Polyimide A B C A A-A 100 100 100 100 100 100 100 ──────────────────────────────────── Epoxy resin YDCN-702 N-865 ESCN-195 N-865 N-865 YDCN-702 − 50 parts 20 parts 10 parts 10 parts 100 parts 100 parts − ────────────────────── ─────────────── pheno H-1 H-1 VH-4170 VH-4170 VH-4170 H-1 − resin 24 10 5.9 5.6 70 48 − ─────── ────────────────────────────── Curing acceleration 2P4MHZ TPPK 2MA-0K TPPK TPPK 2P4MHZ − Agent 0.5 0.4 0.1 0.5 10 1 − ─ ────── ───────────────────────────── Inorganic substance Silica Silica Silica Alumina Alumina Silica Silica Filler 80 45 18 100 190 180 180 ──── ──────────────────────────────── SOLVENT DMAC NMP DMF DMF DMF DMAC DMAC 400 200 100 100 1000 1000 500 ━━ ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ However, the symbols in Table 1 have the following meanings. DMAC: dimethylacetamide NMP: N-methylpyrrolidone DMF: dimethylformamide This varnish was applied on a polypropylene film to a thickness of 30 to 50 μm, and the temperature was 80 ° C. for 10 minutes, followed by 120 ° C.
And heated for 30 minutes to obtain an adhesive film.
【0036】次に、得られた接着フィルムの接着力を試
験した。接着フィルムを4×4mmの大きさに切断し、
これを4×4mmのシリコンチップと銀メッキ付42ア
ロイリードフレームの間に挟み、1000gの荷重をか
けて、260℃、3秒間圧着させたのち、剪断接着力を
プッシュプルゲージを用いて、室温時及び350℃加熱
20秒後の熱時に、接着力を測定した(表2)。Next, the adhesive strength of the obtained adhesive film was tested. Cut the adhesive film into a size of 4 x 4 mm,
This is sandwiched between a 4 × 4 mm silicon chip and a 42-plated alloy lead frame with silver plating, a load of 1000 g is applied and pressure is applied at 260 ° C. for 3 seconds, and then shear adhesive force is applied at room temperature using a push-pull gauge. At the time of heating and after heating for 20 seconds at 350 ° C., the adhesive force was measured (Table 2).
【0037】[0037]
【表2】 表2 ペーストのフィルム成型性及び接着フィルムの接着力 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ *1 No.1 2 3 4 5 6(比較)7(比較) ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 接着力 室温 10.7 11.0 11.5 10.3 14.0 − 11.0 (kg/ chip)───────────────────────────── 350 ℃ 2.2 2.4 3.2 2.0 2.3 − 0.4 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ *1 胞いためフィルム状にならず、接着力を測定できなかった。[Table 2] Table 2 Paste film formability and adhesive film adhesive strength ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ ━━ * 1 No. 1 2 3 4 5 6 (Comparison) 7 (Comparison) ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Room temperature 10.7 11.0 11.5 10.3 14.0 − 11.0 (kg / chip) ───────────────────────────── 350 ℃ 2.2 2.4 3.2 2.0 2.3 − 0.4 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━lop could not.
【0038】[0038]
【発明の効果】本発明の接着フィルムは、熱硬化性であ
るため熱時の接着性に優れている。本発明の接着フィル
ムを用いれば、ICやLSIの大型チップに均一に接着
剤層を設けることが可能である。Since the adhesive film of the present invention is thermosetting, it has excellent adhesiveness when heated. By using the adhesive film of the present invention, it is possible to uniformly provide an adhesive layer on a large chip of IC or LSI.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 FI 技術表示箇所 C09J 163/00 JFP 8830−4J // H01L 21/52 E 7376−4M (72)発明者 宮寺 康夫 茨城県つくば市和台48番 日立化成工業株 式会社筑波開発研究所内─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification number Reference number within the agency FI Technical display location C09J 163/00 JFP 8830-4J // H01L 21/52 E 7376-4M (72) Inventor Yasuo Miyadera 48, Wadai, Tsukuba-shi, Ibaraki Tsukuba Development Laboratory, Hitachi Chemical Co., Ltd.
Claims (3)
トラカルボン酸二無水物が、全酸二無水物に対し70モ
ル%以上含まれるテトラカルボン酸二無水物に、ジアミ
ンを反応させて得られるポリイミド系樹脂; (B)エポキシ樹脂; (C)フェノール樹脂; (D)硬化促進剤;及び (E)無機物質フィラー、 を含有してなる接着フィルム。1. (A) The following chemical formula 1 [Formula (I)] (However, n is an integer of 2 to 20.) Tetracarboxylic acid dianhydride is reacted with diamine to tetracarboxylic acid dianhydride contained in 70 mol% or more based on the total acid dianhydride. An adhesive film comprising: a polyimide resin obtained by the above; (B) an epoxy resin; (C) a phenol resin; (D) a curing accelerator; and (E) an inorganic substance filler.
酸二無水物が、全酸二無水物に対し70モル%以上含ま
れるテトラカルボン酸二無水物に、ジアミンを反応させ
て得られるポリイミド系樹脂 (B)エポキシ樹脂;及び (C)フェノール樹脂;を有機溶媒に溶解し、これに (D)硬化促進剤;及び (E)無機物質フィラー、を加え、混合し、ベースフィ
ルム上に塗布したのち、加熱することを特徴とする請求
項1の接着フィルムの製造法。2. A tetracarboxylic dianhydride represented by formula (A) (I) is contained in an amount of 70 mol% or more based on the total acid dianhydride by reacting a diamine with the tetracarboxylic dianhydride. The resulting polyimide resin (B) epoxy resin; and (C) phenol resin; are dissolved in an organic solvent, and (D) a curing accelerator; and (E) an inorganic substance filler are added to and mixed with the base film. The method for producing an adhesive film according to claim 1, wherein the coating film is applied and then heated.
着フィルムを挾み、加熱圧着することを特徴とする半導
体素子と支持部材との接着法。3. A method for adhering a semiconductor element and a supporting member, wherein the adhesive film according to claim 1 is sandwiched between the semiconductor element and the supporting member and thermocompression bonding is performed.
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JP5055601A JP2964823B2 (en) | 1993-03-16 | 1993-03-16 | Adhesive film, manufacturing method thereof, adhesion method, support member with adhesive film, and semiconductor device |
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JP2964823B2 JP2964823B2 (en) | 1999-10-18 |
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