JP5177480B2 - Epoxy resin composition for semiconductor encapsulation and semiconductor device - Google Patents
Epoxy resin composition for semiconductor encapsulation and semiconductor device Download PDFInfo
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- JP5177480B2 JP5177480B2 JP2007158009A JP2007158009A JP5177480B2 JP 5177480 B2 JP5177480 B2 JP 5177480B2 JP 2007158009 A JP2007158009 A JP 2007158009A JP 2007158009 A JP2007158009 A JP 2007158009A JP 5177480 B2 JP5177480 B2 JP 5177480B2
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- Prior art keywords
- epoxy resin
- formula
- resin composition
- semiconductor
- weight
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- 239000003822 epoxy resin Substances 0.000 title claims description 48
- 229920000647 polyepoxide Polymers 0.000 title claims description 48
- 239000004065 semiconductor Substances 0.000 title claims description 29
- 239000000203 mixture Substances 0.000 title claims description 27
- 238000005538 encapsulation Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000011256 inorganic filler Substances 0.000 claims description 14
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000005011 phenolic resin Substances 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000007789 sealing Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 23
- -1 xylylene glycols Chemical class 0.000 description 20
- 150000002989 phenols Chemical class 0.000 description 14
- 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 9
- 229910000077 silane Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical class C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 239000003063 flame retardant Substances 0.000 description 5
- 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 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer 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
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- 150000001463 antimony compounds Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000005350 fused silica glass Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- GVYLCNUFSHDAAW-UHFFFAOYSA-N mirex Chemical compound ClC12C(Cl)(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C4(Cl)C1(Cl)Cl GVYLCNUFSHDAAW-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical class O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 2
- IYSVFZBXZVPIFA-UHFFFAOYSA-N 1-ethenyl-4-(4-ethenylphenyl)benzene Chemical group C1=CC(C=C)=CC=C1C1=CC=C(C=C)C=C1 IYSVFZBXZVPIFA-UHFFFAOYSA-N 0.000 description 2
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- UFERIGCCDYCZLN-UHFFFAOYSA-N 3a,4,7,7a-tetrahydro-1h-indene Chemical compound C1C=CCC2CC=CC21 UFERIGCCDYCZLN-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical class OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-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
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical class O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 150000003935 benzaldehydes Chemical class 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
- 239000012965 benzophenone Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004203 carnauba wax Substances 0.000 description 2
- 235000013869 carnauba wax Nutrition 0.000 description 2
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Chemical class O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 2
- 229940117916 cinnamic aldehyde Drugs 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical class C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Chemical class CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- 229910002026 crystalline silica Inorganic materials 0.000 description 2
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 150000004002 naphthaldehydes Chemical class 0.000 description 2
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 2
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical class O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- 238000001721 transfer moulding Methods 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 description 1
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
- FRWYFWZENXDZMU-UHFFFAOYSA-N 2-iodoquinoline Chemical compound C1=CC=CC2=NC(I)=CC=C21 FRWYFWZENXDZMU-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
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- CXXSQMDHHYTRKY-UHFFFAOYSA-N 4-amino-2,3,5-tris(oxiran-2-ylmethyl)phenol Chemical compound C1=C(O)C(CC2OC2)=C(CC2OC2)C(N)=C1CC1CO1 CXXSQMDHHYTRKY-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N COc1ccccc1 Chemical compound COc1ccccc1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- 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
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical class CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000004643 cyanate ester Chemical class 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical class C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- QLAGHGSFXJZWKY-UHFFFAOYSA-N triphenylborane;triphenylphosphane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QLAGHGSFXJZWKY-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Description
本発明は難燃性、耐湿性に優れた硬化物を与える半導体封止用エポキシ樹脂組成物に関する。 The present invention relates to an epoxy resin composition for semiconductor encapsulation that gives a cured product excellent in flame retardancy and moisture resistance.
近年、半導体素子の高性能化ならびに使用分野・環境の多様化に伴い、半導体パッケージには小型化、軽量化、薄型化などの形状の要求や、高温や高湿条件化での耐久性の要求が益々高まっている。また、昨今の環境問題に対する意識の高まりにより、半田の鉛フリー化、パッケージのノンハロゲン・ノンアンチモン難燃化が要求されている。特許文献１にはエポキシ樹脂と硬化剤が共にフェノールアラルキル構造を有するエポキシ樹脂組成物の硬化物がノンハロゲン・ノンアンチモンで難燃性を発現出来る事が記載されている。一方同文献ではジシクロペンタジエン・フェノール重合体の構造は比較例において難燃性が著しく劣ることが記載されている。また、特許文献２においてはジシクロペンタジエン・フェノール重合体のエポキシ樹脂と硬化剤としてフェノールアラルキル樹脂の組み合わせが記載されており、ノンハロゲン・ノンアンチモンの系では無機充填剤が８９％以上でＶ−０を達成していることが記載されている。しかしながら、特許文献１の系の場合コストが下がりにくいため、高い製品すなわち市場に出回る絶対量の少ない製品ほど環境対応に優れるというジレンマを解決できないという問題がある。また、特許文献２の系では無機充填剤の高充填でＶ−０を達成しているため、現在主流である銅系リードフレームの半導体装置の場合には封止材との線膨張が合わなくなるという問題が発生する。 In recent years, as semiconductor devices have become more sophisticated and their fields of use and environments have diversified, semiconductor packages have been required to be smaller, lighter, thinner, and more durable at high temperatures and high humidity. Is growing more and more. In addition, due to the recent increase in awareness of environmental problems, solder-free soldering and non-halogen / non-antimony flame retardant packaging are required. Patent Document 1 describes that a cured product of an epoxy resin composition in which both an epoxy resin and a curing agent have a phenol aralkyl structure can exhibit flame retardancy with non-halogen / non-antimony. On the other hand, this document describes that the structure of dicyclopentadiene / phenol polymer is significantly inferior in flame retardancy in the comparative example. Patent Document 2 describes a combination of an epoxy resin of dicyclopentadiene / phenol polymer and a phenol aralkyl resin as a curing agent. In a non-halogen / non-antimony system, the inorganic filler is 89% or more and V-0. It is described that the above is achieved. However, in the case of the system of Patent Document 1, since the cost is unlikely to decrease, there is a problem that a dilemma that a higher product, that is, a product with a smaller absolute quantity on the market, is better in environmental response cannot be solved. Further, in the system of Patent Document 2, V-0 is achieved by high filling with an inorganic filler, and therefore, in the case of a semiconductor device of a copper-based lead frame which is currently mainstream, the linear expansion with the sealing material is not suitable. The problem occurs.
本発明はハロゲン化合物やアンチモン化合物などの難燃剤を使用することなく、その硬化物において難燃性を付与し、且つ優れた耐湿性を有する半導体封止用エポキシ樹脂組成物および半導体装置を提供することを目的とする。 The present invention provides an epoxy resin composition for semiconductor encapsulation and a semiconductor device that imparts flame retardancy to the cured product and has excellent moisture resistance without using a flame retardant such as a halogen compound or an antimony compound. For the purpose.
本発明者らは前記課題を解決するために鋭意研究した結果、本発明を完成させるに到った。 As a result of intensive studies to solve the above problems, the present inventors have completed the present invention.
すなわち本発明は
（１）式（１）
で表される成分の含有割合が１０重量％以上であるフェノール樹脂、無機充填剤および必要により硬化促進剤を含有する半導体封止用エポキシ樹脂組成物。
（２）無機充填剤の含有割合が７５〜８５重量％である上記（１）記載の半導体封止用エポキシ樹脂組成物。
（３）上記（１）または（２）記載の半導体封止用エポキシ樹脂組成物で半導体素子を封止した半導体装置。
（４）半導体素子が銅系のリードフレームに搭載されている、上記（３）記載の半導体装置。
を、提供するものである。
That is, the present invention relates to (1) formula (1)
An epoxy resin composition for encapsulating a semiconductor containing a phenol resin having a content ratio of 10% by weight or more, an inorganic filler, and, if necessary, a curing accelerator.
(2) The epoxy resin composition for semiconductor encapsulation according to the above (1), wherein the content of the inorganic filler is 75 to 85% by weight.
(3) A semiconductor device in which a semiconductor element is sealed with the epoxy resin composition for sealing a semiconductor according to (1) or (2).
(4) The semiconductor device according to (3), wherein the semiconductor element is mounted on a copper-based lead frame.
Is provided.
本発明の半導体封止用エポキシ樹脂組成物はハロゲン化合物やアンチモン化合物などの難燃剤を用いることなく、その硬化物において難燃性を有し、且つ高湿下での高信頼性を有するため、半導体素子を保護するのにきわめて有用である。 Since the epoxy resin composition for semiconductor encapsulation of the present invention has flame retardancy in the cured product without using a flame retardant such as a halogen compound or an antimony compound, and has high reliability under high humidity, It is extremely useful for protecting semiconductor devices.
本発明のエポキシ樹脂組成物は、前記式（１）で表されるエポキシ樹脂を含有する。式（１）のエポキシ樹脂は、フェノールとジシクロペンタジエンを酸触媒によって重合させることにより得られるフェノール樹脂を原料とし、エピクロロヒドリンと脱塩酸反応させることにより得られる。この時のフェノール仕込み割合を多くすると、低分子量物の含有割合が多くなり、結果として得られるエポキシ樹脂の軟化点が低くなる。本発明においては、通常式（１）のエポキシ樹脂として、軟化点が５０℃〜８０℃のものを用いる。軟化点が低い方が流動性及び難燃性は向上するが、耐熱性を上げるには軟化点が高いものを使用することが好ましい。 The epoxy resin composition of the present invention contains an epoxy resin represented by the formula (1). The epoxy resin of the formula (1) can be obtained by using a phenol resin obtained by polymerizing phenol and dicyclopentadiene with an acid catalyst as a raw material, and causing a dehydrochlorination reaction with epichlorohydrin. If the proportion of phenol charged at this time is increased, the content ratio of low molecular weight substances is increased, and the resulting epoxy resin has a lower softening point. In the present invention, an epoxy resin having a softening point of 50 to 80 ° C. is usually used as the epoxy resin of the formula (1). The lower the softening point, the better the fluidity and flame retardancy, but it is preferable to use a higher softening point in order to increase the heat resistance.
本発明のエポキシ樹脂組成物は、前記式（２）で表されるフェノール樹脂を含有する。式（２）のフェノール樹脂は必要により酸性触媒の存在下、フェノールとビスハロゲノメチルベンゼン類、ビスアルコキシメチルベンゼン類、キシリレングリコール類またはジビニルベンゼン類などとを反応させることにより得られる。
本発明においては、フェノールとビスハロゲノメチルベンゼン類、ビスアルコキシメチルベンゼン類、キシリレングリコール類またはジビニルベンゼン類の仕込み比をモル比で、前者：後者＝１：０．６５〜０．１０で反応を行うことにより、下記式（ａ）
で表される成分の含有割合が通常１０重量％以上１００重量％以下、好ましくは１５重量％以上５０重量％以下の範囲である式（２）の化合物を使用する。式（ａ）の化合物の含有割合は、通常ゲルパーミエーションクロマトグラフィー（ＧＰＣ）で測定することができる。また式（２）の化合物において、低分量物の含有割合が多いとその軟化点が低くなる傾向にあり、本発明においては通常、その軟化点が５０〜８０℃のものを用いる。軟化点が低い方が流動性及び難燃性は向上するが、耐熱性を上げるには軟化点が高いもの使用することが好ましい。
The epoxy resin composition of the present invention contains a phenol resin represented by the formula (2). The phenol resin of the formula (2) can be obtained by reacting phenol with bishalogenomethylbenzenes, bisalkoxymethylbenzenes, xylylene glycols or divinylbenzenes in the presence of an acidic catalyst if necessary.
In the present invention, the reaction ratio of phenol and bishalogenomethylbenzenes, bisalkoxymethylbenzenes, xylylene glycols or divinylbenzenes in molar ratio is the former: latter = 1: 0.65 to 0.10. By performing the following formula (a)
The compound represented by formula (2) is used in which the content of the component is usually in the range of 10 wt% to 100 wt%, preferably 15 wt% to 50 wt%. The content ratio of the compound of the formula (a) can be usually measured by gel permeation chromatography (GPC). Further, in the compound of the formula (2), when the content of the low fraction is large, the softening point tends to be low. In the present invention, those having a softening point of 50 to 80 ° C. are usually used. The lower the softening point, the better the fluidity and flame retardancy, but in order to increase the heat resistance, it is preferable to use a material with a higher softening point.
本発明のエポキシ樹脂組成物は無機充填剤を含有する。無機充填剤としては溶融シリカ、結晶性シリカ、アルミナ、炭酸カルシウム、ケイ酸カルシウム、硫酸バリウム、タルク、クレー、酸化マグネシウム、酸化アルミニウム、酸化ベリリウム、酸化鉄、酸化チタン、窒化アルミニウム、窒化ケイ素、窒化ホウ素、マイカ、ガラス、石英、雲母などが上げられるがこれらに限定されない。また２種以上を混合して使用しても良い。これら無機充填剤のうち、溶融シリカや結晶性シリカなどのシリカ類はコストが安く、電気信頼性も良好なため好ましい。無機充填剤の使用量は内割りで通常５０重量％〜９０重量％、好ましくは７５重量％〜８５重量％の範囲である。少なすぎると難燃性の効果が得られず、多すぎると封止する半導体素子が銅系リードフレームに搭載されている場合に封止樹脂とフレームの線膨張率が合わなくて、ヒートショックなどの熱応力による不具合が発生する可能性がある。 The epoxy resin composition of the present invention contains an inorganic filler. Inorganic fillers include fused silica, crystalline silica, alumina, calcium carbonate, calcium silicate, barium sulfate, talc, clay, magnesium oxide, aluminum oxide, beryllium oxide, iron oxide, titanium oxide, aluminum nitride, silicon nitride, and nitride Examples include, but are not limited to, boron, mica, glass, quartz, and mica. Two or more kinds may be mixed and used. Of these inorganic fillers, silicas such as fused silica and crystalline silica are preferred because of low cost and good electrical reliability. The amount of the inorganic filler used is usually in the range of 50% to 90% by weight, preferably 75% to 85% by weight. If the amount is too small, the flame retardant effect cannot be obtained. If the amount is too large, when the semiconductor element to be sealed is mounted on a copper lead frame, the linear expansion coefficient of the sealing resin and the frame does not match, and heat shock, etc. There is a possibility that a problem due to thermal stress will occur.
また本発明のエポキシ樹脂組成物においては必要により硬化促進剤を使用する。使用できる硬化促進剤の例としては２−メチルイミダゾール、２−エチルイミダゾール、２−エチル−４−メチルイミダゾールなどのイミダゾール類、２−（ジメチルアミノメチル）フェノール、１，８−ジアザ−ビシクロ（５，４，０）ウンデセン−７等の第３級アミン類、トリフェニルホスフィン、トリシクロヘキシルホスフィン、トリフェニルホスフィントリフェニルボランなどのホスフィン類、オクチル酸スズ等の金属化合物が挙げられる。硬化促進剤はエポキシ樹脂１００重量部に対して０．０２〜５．０重量部が必要に応じ用いられる。 Moreover, in the epoxy resin composition of this invention, a hardening accelerator is used if necessary. Examples of curing accelerators that can be used include imidazoles such as 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2- (dimethylaminomethyl) phenol, 1,8-diaza-bicyclo (5 , 4, 0) tertiary amines such as undecene-7, phosphines such as triphenylphosphine, tricyclohexylphosphine, triphenylphosphine triphenylborane, and metal compounds such as tin octylate. If necessary, the curing accelerator is used in an amount of 0.02 to 5.0 parts by weight based on 100 parts by weight of the epoxy resin.
本発明のエポキシ樹脂組成物においては式（１）のエポキシ樹脂以外のエポキシ樹脂を併用しても良い。併用できる他のエポキシ樹脂の具体例としては、フェノール類（フェノール、アルキル置換フェノール、芳香族置換フェノール、ナフトール、アルキル置換ナフトール、ジヒドロキシベンゼン、アルキル置換ジヒドロキシベンゼン、ジヒドロキシナフタレン等）と各種アルデヒド（ホルムアルデヒド、アセトアルデヒド、アルキルアルデヒド、ベンズアルデヒド、アルキル置換ベンズアルデヒド、ヒドロキシベンズアルデヒド、ナフトアルデヒド、グルタルアルデヒド、フタルアルデヒド、クロトンアルデヒド、シンナムアルデヒド等）との重縮合物；フェノール類と各種ジエン化合物（テルペン類、ビニルシクロヘキセン、ノルボルナジエン、ビニルノルボルネン、テトラヒドロインデン、ジビニルベンゼン、ジビニルビフェニル、ジイソプロペニルビフェニル、ブタジエン、イソプレン等）との重合物、フェノール類とケトン類（アセトン、メチルエチルケトン、メチルイソブチルケトン、アセトフェノン、ベンゾフェノン等）との重縮合物；フェノール類とビスクロロメチルビフェニルとの重縮合物；フェノール類とビスクロロメチルベンゼンとの重縮合物；ビスフェノール類と各種アルデヒドの重縮合物またはアルコール類等をグリシジル化したグリシジルエーテル系エポキシ樹脂；４−ビニル−１−シクロヘキセンジエポキシドや３，４−エポキシシクロヘキシルメチル−３，４´−エポキシシクロヘキサンカルボキシラートなどを代表とする脂環式エポキシ樹脂；テトラグリシジルジアミノジフェニルメタン（ＴＧＤＤＭ）やトリグリシジル−ｐ−アミノフェノールなどを代表とするグリシジルアミン系エポキシ樹脂；グリシジルエステル系エポキシ樹脂等が挙げられるが、通常用いられるエポキシ樹脂であればこれらに限定されるものではない。これらは単独で用いてもよく、２種以上を用いてもよい。これらのエポキシ樹脂の全エポキシ樹脂中に占める割合は３０重量％以下が好ましく、特に２０重量％以下が好ましい。 In the epoxy resin composition of this invention, you may use together epoxy resins other than the epoxy resin of Formula (1). Specific examples of other epoxy resins that can be used in combination include phenols (phenol, alkyl-substituted phenol, aromatic-substituted phenol, naphthol, alkyl-substituted naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene, dihydroxynaphthalene, etc.) and various aldehydes (formaldehyde, Polycondensates of acetaldehyde, alkyl aldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde, etc .; phenols and various diene compounds (terpenes, vinylcyclohexene, norbornadiene) , Vinyl norbornene, tetrahydroindene, divinylbenzene, divinylbiphenyl, diiso Polymers with lopenyl biphenyl, butadiene, isoprene, etc.), polycondensates of phenols with ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone, etc.); polycondensation of phenols with bischloromethyl biphenyl Polycondensates of phenols and bischloromethylbenzene; glycidyl ether epoxy resins obtained by glycidylation of polycondensates of bisphenols and various aldehydes or alcohols; 4-vinyl-1-cyclohexene diepoxide and 3, Alicyclic epoxy resins such as 4-epoxycyclohexylmethyl-3,4'-epoxycyclohexanecarboxylate; tetraglycidyldiaminodiphenylmethane (TGDDM), triglycidyl-p-aminophenol, etc. Glycidylamine-based epoxy resins; glycidyl ester-based epoxy resins and the like, but are not limited thereto as long as they are usually used epoxy resins. These may be used alone or in combination of two or more. The proportion of these epoxy resins in the total epoxy resin is preferably 30% by weight or less, particularly preferably 20% by weight or less.
本発明のエポキシ樹脂組成物においては式（２）のフェノール樹脂以外のエポキシ樹脂用硬化剤を併用しても良い。併用し得る硬化剤としてはアミン系化合物、酸無水物系化合物、アミド系化合物、フェノ−ル系化合物などが使用できる。使用できる硬化剤の具体例としては、ジアミノジフェニルメタン、ジエチレントリアミン、トリエチレンテトラミン、ジアミノジフェニルスルホン、イソホロンジアミン、ジシアンジアミド、リノレン酸の２量体とエチレンジアミンとより合成されるポリアミド樹脂等のアミン系化合物；無水フタル酸、無水トリメリット酸、無水ピロメリット酸、無水マレイン酸、テトラヒドロ無水フタル酸、メチルテトラヒドロ無水フタル酸、無水メチルナジック酸、ヘキサヒドロ無水フタル酸、メチルヘキサヒドロ無水フタル酸等の酸無水物系化合物；ビスフェノール類、フェノール類（フェノール、アルキル置換フェノール、芳香族置換フェノール、ナフトール、アルキル置換ナフトール、ジヒドロキシベンゼン、アルキル置換ジヒドロキシベンゼン、ジヒドロキシナフタレン等）と各種アルデヒド（ホルムアルデヒド、アセトアルデヒド、アルキルアルデヒド、ベンズアルデヒド、アルキル置換ベンズアルデヒド、ヒドロキシベンズアルデヒド、ナフトアルデヒド、グルタルアルデヒド、フタルアルデヒド、クロトンアルデヒド、シンナムアルデヒド等）との重縮合物、フェノール類と各種ジエン化合物（ジシクロペンタジエン、テルペン類、ビニルシクロヘキセン、ノルボルナジエン、ビニルノルボルネン、テトラヒドロインデン、ジビニルベンゼン、ジビニルビフェニル、ジイソプロペニルビフェニル、ブタジエン、イソプレン等）との重合物、フェノール類とケトン類（アセトン、メチルエチルケトン、メチルイソブチルケトン、アセトフェノン、ベンゾフェノン等）との重縮合物、フェノール類とビスクロロメチルビフェニルとの重縮合物、ビスフェノール類と各種アルデヒドの重縮合物、ビフェノール類及びこれらの変性物等のフェノ−ル系化合物；イミダゾ−ル、グアニジン誘導体等のアミド系化合物、ＢＦ3 −アミン錯体などが挙げられる。これらは単独で用いてもよく、２種以上を用いてもよい。これらの硬化剤の全硬化剤中に占める割合は３０重量％以下が好ましく、特に２０重量％以下が好ましい。 In the epoxy resin composition of this invention, you may use together the hardening | curing agent for epoxy resins other than the phenol resin of Formula (2). As the curing agent that can be used in combination, an amine compound, an acid anhydride compound, an amide compound, a phenol compound, and the like can be used. Specific examples of curing agents that can be used include amine compounds such as diaminodiphenylmethane, diethylenetriamine, triethylenetetramine, diaminodiphenylsulfone, isophoronediamine, dicyandiamide, and a linolenic acid dimer and a polyamide resin synthesized from ethylenediamine; Acid anhydrides such as phthalic acid, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methyl nadic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride Compounds: bisphenols, phenols (phenol, alkyl-substituted phenol, aromatic-substituted phenol, naphthol, alkyl-substituted naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene Polycondensates of dihydroxynaphthalene, etc.) with various aldehydes (formaldehyde, acetaldehyde, alkylaldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde, etc.), phenols and various Polymers with diene compounds (dicyclopentadiene, terpenes, vinylcyclohexene, norbornadiene, vinylnorbornene, tetrahydroindene, divinylbenzene, divinylbiphenyl, diisopropenylbiphenyl, butadiene, isoprene, etc.), phenols and ketones (acetone, Polycondensates with methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone, etc.) Phenolic compounds such as polycondensates of phenols and bischloromethylbiphenyl, polycondensates of bisphenols and various aldehydes, biphenols and modified products thereof; amides such as imidazole and guanidine derivatives; Examples thereof include BF 3 -amine complex. These may be used alone or in combination of two or more. The proportion of these curing agents in the total curing agent is preferably 30% by weight or less, particularly preferably 20% by weight or less.
本発明のエポキシ樹脂組成物は成形時の金型との離型を良くするために離型剤を配合することができる。離型剤としては従来公知のものいずれも使用できるが、例えばカルナバワックス、モンタンワックスなどのエステル系ワックス、ステアリン酸、パルチミン酸などの脂肪酸およびこれらの金属塩、酸化ポリエチレン、非酸化ポリエチレンなどのポリオレフィン系ワックスなどが挙げられる。これらは単独で使用しても２種以上併用しても良い。これら離型剤の配合量は全有機成分に対して０．５〜３重量％が好ましい。これより少なすぎると金型からの離型が悪く、多すぎるとリードフレームなどとの接着が悪くなる。 The epoxy resin composition of the present invention can contain a release agent in order to improve the release from the mold during molding. Any conventionally known release agent can be used, for example, ester waxes such as carnauba wax and montan wax, fatty acids such as stearic acid and palmitic acid, and metal salts thereof, polyolefins such as polyethylene oxide and non-oxidized polyethylene And waxes. These may be used alone or in combination of two or more. The compounding amount of these release agents is preferably 0.5 to 3% by weight with respect to the total organic components. If the amount is too small, release from the mold is poor, and if the amount is too large, adhesion to the lead frame and the like is poor.
本発明のエポキシ樹脂組成物は無機充填剤と樹脂成分との接着性を高めるためにカップリング剤を配合することができる。カップリング剤としては従来公知のものをいずれも使用できるが、例えばビニルアルコキシシラン、エポキアルコキシシラン、スチリルアルコキシシラン、メタクリロキシアルコキシシラン、アクリロキシアルコキシシラン、アミノアルコキシシラン、メルカプトアルコキシシラン、イソシアナートアルコキシシランなどの各種アルコキシシラン化合物、アルコキシチタン化合物、アルミニウムキレート類などが挙げられる。これらは単独で使用しても２種以上併用しても良い。カップリング剤の添加方法は、カップリング剤であらかじめ無機充填剤表面を処理した後、樹脂と混練しても良いし、樹脂にカップリング剤を混合してから無機充填剤と混練しても良い。 The epoxy resin composition of the present invention can contain a coupling agent in order to enhance the adhesion between the inorganic filler and the resin component. Any conventionally known coupling agent can be used. For example, vinyl alkoxy silane, epoxy alkoxy silane, styryl alkoxy silane, methacryloxy alkoxy silane, acryloxy alkoxy silane, amino alkoxy silane, mercapto alkoxy silane, isocyanate alkoxy Examples include various alkoxysilane compounds such as silane, alkoxytitanium compounds, and aluminum chelates. These may be used alone or in combination of two or more. The coupling agent may be added by treating the surface of the inorganic filler with the coupling agent in advance and then kneading with the resin, or mixing the coupling agent with the resin and then kneading with the inorganic filler. .
更に本発明のエポキシ樹脂組成物には、必要に応じて公知の添加剤を配合することが出来る。用いうる添加剤の具体例としては、ポリブタジエン及びこの変性物、アクリロニトリル共重合体の変性物、ポリフェニレンエーテル、ポリスチレン、ポリエチレン、ポリイミド、フッ素樹脂、マレイミド系化合物、シアネートエステル系化合物、シリコーンゲル、シリコーンオイル、並びにカーボンブラック、フタロシアニンブルー、フタロシアニングリーン等の着色剤などが挙げられる。 Furthermore, a known additive can be blended in the epoxy resin composition of the present invention as necessary. Specific examples of additives that can be used include polybutadiene and modified products thereof, modified products of acrylonitrile copolymer, polyphenylene ether, polystyrene, polyethylene, polyimide, fluororesin, maleimide compounds, cyanate ester compounds, silicone gel, and silicone oil. And colorants such as carbon black, phthalocyanine blue, and phthalocyanine green.
本発明のエポキシ樹脂組成物は、各成分を均一に分散混合できる従来公知のいかなる手法を用いても製造することができる。例えば各成分を全て粉砕して粉砕化しヘンシェルミキサーなどで混合後、加熱ロールによる溶融混練、ニーダーによる溶融混練、特殊混合機による混合、あるいはこれら各方法の適切な組み合わせを用いることで調製される。また、本発明の半導体装置はリードフレームなどに搭載された半導体素子を、本発明のエポキシ樹脂組成物を用いてトランスファー成形などにより樹脂封止することで製造することができる。 The epoxy resin composition of the present invention can be produced by any conventionally known technique capable of uniformly dispersing and mixing each component. For example, all the components are pulverized and pulverized, mixed with a Henschel mixer, etc., then melt kneaded with a heating roll, melt kneaded with a kneader, mixed with a special mixer, or an appropriate combination of these methods. The semiconductor device of the present invention can be manufactured by resin-sealing a semiconductor element mounted on a lead frame or the like by transfer molding or the like using the epoxy resin composition of the present invention.
本発明の半導体装置は前記の本発明のエポキシ樹脂組成物で封止されたもの等の本発明のエポキシ樹脂組成物の硬化物を有する。半導体装置としては、例えばＤＩＰ（デュアルインラインパッケージ）、ＱＦＰ（クワッドフラットパッケージ）、ＢＧＡ（ボールグリッドアレイ）、ＣＳＰ（チップサイズパッケージ）、ＳＯＰ（スモールアウトラインパッケージ）、ＴＳＯＰ（シンスモールアウトラインパッケージ）、ＴＱＦＰ（シンクワッドフラットパッケージ）等が挙げられる。
また、熱放散性や高速電気特性の問題から銅系リードフレームを用いるのが好ましい。銅系のリードフレームとは、銅合金を素材とし、各種メッキ化工を施したリードフレームである。
The semiconductor device of the present invention has a cured product of the epoxy resin composition of the present invention such as the one sealed with the epoxy resin composition of the present invention. As semiconductor devices, for example, DIP (Dual Inline Package), QFP (Quad Flat Package), BGA (Ball Grid Array), CSP (Chip Size Package), SOP (Small Outline Package), TSOP (Thin Small Outline Package), TQFP (Sink Quad Flat Package).
Moreover, it is preferable to use a copper-based lead frame because of heat dissipation and high-speed electrical characteristics. The copper-based lead frame is a lead frame made of a copper alloy and subjected to various plating processes.
以下、実施例、比較例により本発明を具体的に説明する。尚、実施例１及び実施例２は、各々参考例１及び参考例２と読み替えるものとする。 Hereinafter, the present invention will be specifically described with reference to Examples and Comparative Examples. In addition, Example 1 and Example 2 shall be read as Reference Example 1 and Reference Example 2, respectively.
実施例１〜６および比較例１〜３
各種成分を表１の割合（重量部）で配合し、ミキシングロールで混練、タブレット化後、トランスファー成形で樹脂成形体を調製し、１６０℃で２時間、更に１８０℃で８時間硬化させ、硬化物の物性を測定した。結果を表１に示す。
なお、硬化物の物性は以下の要領で測定した。
・吸湿率：１２１℃で湿度１００％の条件下で２４時間保存後の重量増加率。試験片は直径５０ｍｍ×厚み４ｍｍの円盤。
・難燃性：ＵＬ９４に準拠して行った。ただし、サンプルサイズは幅１２．５ｍｍ×長さ１５０ｍｍとし、厚さは０．８ｍｍと１．６ｍｍの２種類で試験を行った。
・残炎時間：５個１組のサンプルに１０回接炎したあとの残炎時間の合計
Examples 1-6 and Comparative Examples 1-3
Various components are blended in the proportions (parts by weight) shown in Table 1, kneaded with a mixing roll, converted into a tablet, a resin molded product is prepared by transfer molding, cured at 160 ° C. for 2 hours, and further cured at 180 ° C. for 8 hours and cured The physical properties of the material were measured. The results are shown in Table 1.
In addition, the physical property of hardened | cured material was measured in the following ways.
Hygroscopicity: Weight increase rate after storage for 24 hours under the conditions of 121 ° C. and 100% humidity. The test piece is a disk having a diameter of 50 mm and a thickness of 4 mm.
Flame retardance: Performed according to UL94. However, the sample size was 12.5 mm wide × 150 mm long, and the thickness was 0.8 mm and 1.6 mm.
・ Afterflame time: Total afterflame time after 10 times contact with 5 samples
注）
（Ｅ１）：式（１）の化合物（商品名：ＸＤ−１０００ 日本化薬製 エポキシ当量２５４ｇ／ｅｑ 軟化点７４℃）
（Ｅ２）：式（１）の化合物（商品名：ＸＤ−１０００−Ｌ 日本化薬製 エポキシ当量２４５ｇ／ｅｑ 軟化点６６℃）
（Ｅ３）：式（１）の化合物（商品名：ＸＤ−１０００−２Ｌ 日本化薬製 エポキシ当量２４１ｇ／ｅｑ 軟化点５７℃）
（Ｅ４）下記式（３）の化合物
note)
(E1): Compound of formula (1) (trade name: XD-1000, Nippon Kayaku Epoxy equivalent 254 g / eq, softening point 74 ° C.)
(E2): Compound of formula (1) (trade name: XD-1000-L, Nippon Kayaku Epoxy equivalent 245 g / eq, softening point 66 ° C.)
(E3): Compound of formula (1) (trade name: XD-1000-2L, Nippon Kayaku Epoxy equivalent 241 g / eq, softening point 57 ° C.)
(E4) Compound of the following formula (3)
（Ｈ１）：式（２）の化合物（商品名：ミレックス ＸＬＣ−ＬＬ 三井化学製 軟化点７７℃ 水酸基当量１７６ｇ／ｅｑ 式（ａ）の成分の含有割合は１７重量％）
（Ｈ２）：式（２）の化合物（商品名：ミレックス ＸＬＣ−３Ｌ 三井化学製 軟化点７１℃ 水酸基当量１７２ｇ／ｅｑ 式（ａ）の成分の含有割合は２１重量％）
（Ｈ３）：式（２）の化合物（商品名：ミレックス ＸＬＣ−４Ｌ 三井化学製 軟化点６３℃ 水酸基当量１７０ｇ／ｅｑ 式（ａ）の成分の含有割合は２７重量％）
（Ｈ４）：式（２）の化合物（商品名：ミレックス ＸＬ−２２５ 三井化学製 軟化点９１℃ 式（ａ）の成分の含有割合は８重量％）
＊式（ａ）の成分の含有割合は下記のＧＰＣ条件で測定した。
カラム：Shodex KF-803＋KF-802＋KF-801
カラム温度：４０℃
溶剤：テトラヒドロフラン
流量：１ｍｌ／ｍｉｎ
検出：ＲＩ
(H1): Compound of formula (2) (trade name: Mirex XLC-LL, made by Mitsui Chemicals, softening point 77 ° C., hydroxyl equivalent 176 g / eq, content of component of formula (a) is 17% by weight)
(H2): Compound of formula (2) (trade name: Mirex XLC-3L, manufactured by Mitsui Chemicals, softening point 71 ° C., hydroxyl equivalent 172 g / eq, content of component of formula (a) is 21% by weight)
(H3): Compound of formula (2) (trade name: Mirex XLC-4L, manufactured by Mitsui Chemicals, softening point 63 ° C., hydroxyl equivalent 170 g / eq, content of component of formula (a) is 27% by weight)
(H4): Compound of formula (2) (trade name: Millex XL-225, manufactured by Mitsui Chemicals, softening point: 91 ° C. The content of the component of formula (a) is 8% by weight)
* The content ratio of the component of the formula (a) was measured under the following GPC conditions.
Column: Shodex KF-803 + KF-802 + KF-801
Column temperature: 40 ° C
Solvent: Tetrahydrofuran Flow rate: 1 ml / min
Detection: RI
硬化促進剤：トリフェニルホスフィン（北興化学工業製）
無機充填剤：溶融シリカ（商品名：ＭＳＲ−２２１２、龍森製）
離型剤：カルナバワックス１号（セラリカ野田製）
カップリング剤：ＫＢＭ−３０３（信越化学製）
Curing accelerator: Triphenylphosphine (manufactured by Hokuko Chemical)
Inorganic filler: fused silica (trade name: MSR-2212, manufactured by Tatsumori)
Mold release agent: Carnauba wax No. 1 (manufactured by Celerica Noda)
Coupling agent: KBM-303 (manufactured by Shin-Etsu Chemical)
表１から、本発明のエポキシ樹脂組成物は、ハロゲンやアンチモン化合物等の難燃剤を用いることなく、難燃性に優れた硬化物を与える。特に、式（２）のフェノール樹脂であって式（ａ）の化合物の含有割合が多いもの、すなわち分子量が低くて軟化点が低いものの方が、消炎時間が短く難燃性が良好である。 From Table 1, the epoxy resin composition of this invention gives the hardened | cured material excellent in the flame retardance, without using flame retardants, such as a halogen and an antimony compound. In particular, the phenol resin of the formula (2) having a higher content of the compound of the formula (a), that is, the one having a lower molecular weight and a lower softening point has a shorter flame extinguishing time and better flame retardancy.
Claims (4)
で表される成分の含有割合が１０重量％以上である水酸基当量が１７２ｇ／ｅｑ．以下のフェノール樹脂、無機充填剤および必要により硬化促進剤を含有する半導体封止用エポキシ樹脂組成物。ただし、（Ａ）エポキシ樹脂、（Ｂ）硬化剤、（Ｃ）下記一般式（Ｉ）で示される化合物を含有し、（Ｃ）下記一般式（Ｉ）で示される化合物が組成物全体の０．４〜２．０重量％である封止用エポキシ樹脂組成物を除く。
The hydroxyl group equivalent in which the content ratio of the component represented by the formula is 10% by weight or more is 172 g / eq. The epoxy resin composition for semiconductor sealing containing the following phenol resins, an inorganic filler, and a hardening accelerator as needed. However, it contains (A) an epoxy resin, (B) a curing agent, (C) a compound represented by the following general formula (I), and (C) a compound represented by the following general formula (I) is 0% of the total composition. Excluding the epoxy resin composition for sealing, which is 4 to 2.0% by weight.
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