CN106661200B - Epoxy resin composition, resin sheet, prepreg, metal-clad laminate, printed wiring board, and semiconductor device - Google Patents
Epoxy resin composition, resin sheet, prepreg, metal-clad laminate, printed wiring board, and semiconductor device Download PDFInfo
- Publication number
- CN106661200B CN106661200B CN201580037762.1A CN201580037762A CN106661200B CN 106661200 B CN106661200 B CN 106661200B CN 201580037762 A CN201580037762 A CN 201580037762A CN 106661200 B CN106661200 B CN 106661200B
- Authority
- CN
- China
- Prior art keywords
- epoxy resin
- resin composition
- prepreg
- printed wiring
- wiring board
- 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.)
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 92
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 92
- 229920005989 resin Polymers 0.000 title claims abstract description 51
- 239000011347 resin Substances 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 239000004065 semiconductor Substances 0.000 title claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 150000001412 amines Chemical class 0.000 claims abstract description 18
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 claims description 25
- 239000000758 substrate Substances 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 18
- 239000002184 metal Substances 0.000 claims description 18
- 239000011521 glass Substances 0.000 claims description 17
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000011888 foil Substances 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 239000003365 glass fiber Substances 0.000 claims description 7
- 238000010030 laminating Methods 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 3
- 230000001588 bifunctional effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000006068 polycondensation reaction Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 23
- 238000010521 absorption reaction Methods 0.000 abstract description 17
- 239000010410 layer Substances 0.000 description 38
- 238000001723 curing Methods 0.000 description 33
- 238000000034 method Methods 0.000 description 26
- -1 amine compounds Chemical class 0.000 description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 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 16
- 150000001875 compounds Chemical class 0.000 description 15
- 238000000465 moulding Methods 0.000 description 15
- 150000002989 phenols Chemical class 0.000 description 13
- 229910000679 solder Inorganic materials 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 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 12
- 238000010438 heat treatment Methods 0.000 description 12
- 239000004593 Epoxy Substances 0.000 description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 10
- 239000011256 inorganic filler Substances 0.000 description 10
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 10
- 229910019142 PO4 Inorganic materials 0.000 description 9
- 229910003475 inorganic filler Inorganic materials 0.000 description 9
- 239000010452 phosphate Substances 0.000 description 9
- 229910052698 phosphorus Inorganic materials 0.000 description 9
- 239000011574 phosphorus Substances 0.000 description 9
- 239000002966 varnish Substances 0.000 description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000007747 plating Methods 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinyl group Chemical group C1(O)=CC(O)=CC=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 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 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
- 229960004889 salicylic acid Drugs 0.000 description 5
- 229930185605 Bisphenol Natural products 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 238000003825 pressing Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 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 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical class OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- CCDXIADKBDSBJU-UHFFFAOYSA-N phenylmethanetriol Chemical compound OC(O)(O)C1=CC=CC=C1 CCDXIADKBDSBJU-UHFFFAOYSA-N 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 150000003505 terpenes Chemical class 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-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
- 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 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-N 0.000 description 2
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-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
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 description 2
- AMNPXXIGUOKIPP-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]thiourea Chemical compound NC(=S)NC1=CC=C(NC(N)=S)C=C1 AMNPXXIGUOKIPP-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229910002026 crystalline silica Inorganic materials 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 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
- 150000004780 naphthols Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 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
- 229920000728 polyester Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 239000002557 mineral fiber Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 150000004002 naphthaldehydes Chemical class 0.000 description 1
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 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
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical class O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 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
- 230000000704 physical effect Effects 0.000 description 1
- 239000011295 pitch Substances 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-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
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3218—Carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/06—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials
- C08J5/08—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials glass fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
Abstract
The invention aims to provide an epoxy resin composition, and a resin sheet, a metal-clad laminate, a printed wiring board and a semiconductor device using the epoxy resin composition, wherein a cured product of the epoxy resin composition has high heat resistance, water absorption and low dielectric constant. The epoxy resin composition of the present invention comprises, as essential components, an epoxy resin represented by the following general formula (1) and an amine-based curing agent, wherein the ratio of (a) to (b) is (a)/(b) l to 3, G represents a glycidyl group, and n is a repeating number of 0 to 5.
Description
Technical Field
The present invention relates to an epoxy resin composition that provides a cured product having excellent heat resistance and water resistance, and a prepreg, a resin sheet, a metal-clad laminate, a printed wiring board, and a semiconductor device, each obtained by impregnating a fiber base material with the epoxy resin composition.
Background
Epoxy resin compositions are widely used in the fields of electric/electronic parts, structural materials, adhesives, paints, and the like because of their workability and excellent electrical characteristics, heat resistance, adhesiveness, moisture resistance (water resistance), and the like of cured products thereof.
However, in recent years, in the electric and electronic field, further improvement of various properties such as moisture resistance, adhesion, dielectric properties, low viscosity for highly filling a filler (inorganic or organic filler), and improvement of reactivity for shortening a molding cycle has been required, including the increase in purity of a resin composition. In addition, as a structural material, a lightweight material having excellent mechanical properties is required for aerospace materials, leisure/sports equipment applications, and the like. In particular, in the field of semiconductor sealing, a substrate (the substrate itself or a peripheral material thereof) is required to have characteristics which increase year by year, and for example, a high Tg of the peripheral material is required due to an increase in the driving temperature of a semiconductor.
Generally, when the Tg of the epoxy resin is increased, the water absorption rate increases (non-patent document 1). This is the effect of the increased crosslinking density. However, in the demand for higher Tg of semiconductor peripheral materials requiring low moisture absorption, development of resins having these contradictory properties is urgent.
On the other hand, patent document 1 discloses a phenol novolac resin having a biphenyl skeleton and a phenol novolac type epoxy resin obtained by epoxidizing the same, and describes usefulness for semiconductor sealing agent applications.
However, this epoxy resin has both high heat resistance and flame retardancy by combining with a phenol resin, but has a high water absorption rate, and has a problem when used for electronic materials requiring very high reliability.
Further, there is no description of the properties of the composition containing these epoxy resins and amine-based curing agents, and also there is no description of the usefulness for the use in printed wiring boards.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2013-43958
Non-patent document
Non-patent document 1: xiao large-leaved dogwood Yilang, "relationship between chemical structure and characteristics of epoxy resin", DIC Technical Review No.7, Japan, 2001, p.7
Disclosure of Invention
Problems to be solved by the invention
The present invention has been made to solve the above problems, and an object of the present invention is to provide an epoxy resin composition, a prepreg, a resin sheet, a metal-clad laminate, a printed wiring board, and a semiconductor device using the epoxy resin composition, in which a cured product of the epoxy resin composition has high heat resistance, water absorption, and a low dielectric constant.
Means for solving the problems
The present inventors have conducted extensive studies to solve the above problems, and as a result, the present invention has been completed.
Namely, the present invention provides:
(1)
an epoxy resin composition comprising an epoxy resin represented by the following general formula (1) and an amine-based curing agent as essential components,
(wherein the ratio of (a) to (b) is (a)/(b) 1 to 3, G represents a glycidyl group, and n is a repeating number of 0 to 5);
(2)
a prepreg obtained by impregnating a fibrous base material with the epoxy resin composition according to the above (1);
(3)
the prepreg according to the above (2), wherein the fiber base material is a glass fiber base material;
(4)
the prepreg according to (3), wherein the glass fiber substrate contains at least 1 selected from the group consisting of T glass, S glass, E glass, NE glass, and quartz glass;
(5)
a metal-clad laminate obtained by laminating a metal foil on at least one surface of the prepreg according to the above (2) to (4);
(6)
a resin sheet obtained by forming an insulating layer containing the epoxy resin composition according to the above (1) on a film or a metal foil;
(7)
a printed wiring board obtained by using the metal-clad laminate according to (5) above as an inner layer circuit board;
(8)
a printed wiring board obtained by curing the prepreg according to any one of the above (2) to (4) or the resin sheet according to the above (6);
(9)
a semiconductor device obtained by mounting a semiconductor element on the printed wiring board according to the above (7) or (8).
Effects of the invention
The epoxy resin composition of the present invention provides a cured product that can achieve both high heat resistance and water resistance in a cured product thereof, and is therefore a material extremely useful for producing a laminated board such as a printed wiring board or a build-up board.
According to the present invention, there can be provided an epoxy resin composition, a prepreg, a resin sheet, a metal-clad laminate, a printed wiring board, and a semiconductor device, each using the epoxy resin composition, wherein a cured product of the epoxy resin composition has high heat resistance, water absorption, and a low dielectric constant.
Drawings
FIG. 1 is a graph showing the relationship between heat resistance and water absorption characteristics of a cured product of an epoxy resin composition.
Detailed Description
The epoxy resin composition of the present invention will be described below.
The epoxy resin composition of the present invention contains a compound represented by the following formula (1) (hereinafter, referred to as "epoxy resin of formula (1)") as an epoxy resin and an amine-based curing agent as essential components.
(wherein the ratio of (a) to (b) is 1 to 3, G represents a glycidyl group, and n is a repeating number of 0 to 5).
The epoxy resin of the formula (1) used in the present invention can be synthesized by the methods described in japanese patent application laid-open nos. 2011-252037, 2008-156553, 2013-043958, WO2012/053522 and WO2007/007827, and any epoxy resin synthesized by any method can be used as long as it has the structure of the formula (1).
In the present invention, an epoxy resin is used, in particular, in which the ratio (polyfunctionalization ratio) of the formula (a) to the formula (b) is 1 to 3. (a) When the number of the structures (2) is large, the heat resistance is improved, but the water absorption property is deteriorated and the structure becomes brittle and hard. Therefore, the epoxy resin having a polyfunctionalization ratio within the above range is used.
The softening point (ring and ball method) of the epoxy resin used is preferably 50 to 150 ℃, more preferably 52 to 100 ℃, and particularly preferably 52 to 95 ℃. When the softening point is 50 ℃ or lower, the resulting product may be sticky and difficult to handle, which may cause problems in productivity. When the softening point is 150 ℃ or higher, the temperature is close to the molding temperature, and the fluidity during molding may not be ensured, which is not preferable.
The epoxy equivalent of the epoxy resin used is preferably 180g/eq to 350g/eq. Particularly preferably 190g/eq to 300g/eq. When the epoxy equivalent is less than 180g/eq, the amount of the functional group is too large, and thus the cured product after curing may have a high water absorption rate and may be easily brittle. When the epoxy equivalent exceeds 350g/eq, the softening point is considered to be extremely high, or the epoxidation does not proceed completely, and the chlorine amount is considered to be extremely large in some cases, which is not preferable.
The amount of chlorine in the epoxy resin used in the present invention is preferably 200ppm to 1500ppm, and particularly preferably 200ppm to 900ppm, in terms of total chlorine (hydrolysis method). The chlorine content of the epoxy monomer is also expected to be no more than 900ppm according to the JPCA standard. Further, a large amount of chlorine is not preferable because it may affect the electrical reliability. When the chlorine amount is less than 200ppm, an excessive purification step may be required, which is not preferable because a problem arises in productivity.
The melt viscosity at 150 ℃ of the epoxy resin used in the present invention is preferably 0.05 pas to 5 pas, and particularly preferably 0.05 pas to 2.0 pas. When the melt viscosity is higher than 5 pas, a problem may occur in fluidity and flowability or embeddability under pressure. When the molecular weight is less than 0.05 pas, the molecular weight is too small, and the heat resistance may be insufficient.
The ratio of (a) to (b) in the above formula is (a)/(b) 1 to 3. That is, a form of glycidyl ether characterized by having a resorcinol structure in more than half. This ratio is important for precipitation of crystals and improvement of heat resistance, and (a)/(b) is preferably more than 1. Further, by setting (a)/(b) to 3 or less, the amount of the glycidyl ether form of the resorcinol structure is limited, whereby the water absorption and toughness can be improved.
In the formula, n is a repeating unit and is 0 to 5. The flowability or fluidity at the time of producing the prepreg or resin sheet is controlled by making n not more than 5. When it exceeds 5, problems arise not only in fluidity but also in solubility in a solvent.
The solubility of the epoxy resin used in the present invention in a solvent is important. For example, when biphenyl aralkyl type epoxy resins having the same skeleton are used in combination, these resins also need to have solubility in a solvent such as methyl ethyl ketone, toluene, and propylene glycol monomethyl ether.
In the present invention, the solubility in methyl ethyl ketone is important, and it is required that crystals are not precipitated under the conditions of 5 ℃ and room temperature for 2 months or more. The ratio of (a)/(b) is also related to the fact that when the value of (a) is large, crystals are likely to precipitate, and therefore it is important that the value of (a)/(b) is 1 or more.
The epoxy resin composition of the present invention contains an amine curing agent as an essential component. Examples of amine-based curing agents that can be used include: diaminodiphenylmethane, diethylenetriamine, triethylenetetramine, diaminodiphenylsulfone, isophoronediamine, naphthalenediamine, aniline resins obtained by polycondensation of aniline with substituted biphenyls (4,4 '-bis (chloromethyl) -1, 1' -biphenyl, 4 '-bis (methoxymethyl) -1, 1' -biphenyl, etc.), substituted phenyls (1, 4-bis (chloromethyl) benzene, 1, 4-bis (methoxymethyl) benzene, 1, 4-bis (hydroxymethyl) benzene, etc.), etc., but the aniline resins are not limited thereto.
Particularly preferred amine-based curing agents are bifunctional or higher amine compounds, and are preferably resins having a structure represented by the following formula.
(wherein n is a repetition number of 1 to 10).
The amine-based curing agents used in the present invention each take the form of crystals or resins.
In the case of crystals, the melting point is preferably from 35 ℃ to 200 ℃, particularly preferably from 40 ℃ to 185 ℃. Since the melting point is different from the softening point and is also related to the solubility in other resins, it is not necessary to set the temperature at or below the molding temperature unlike the resin.
In the case of a resin, the softening point is preferably 50 to 150 ℃ (ring and ball method), and particularly preferably 50 to 100 ℃. In the case of a resin, an amine-based curing agent having a softening point of 50 ℃ or lower is not preferable because it may cause a problem of stickiness, and in the case of a softening point exceeding 150 ℃, a problem may occur such that fluidity is caused during molding, and thus molding cannot be completed, and a solvent cannot be completely removed.
The amine compound preferably has a functional group equivalent of 60g/eq to 600g/eq (as measured by potentiometric titration). When the active hydrogen equivalent is 60 or less, a problem may occur in water absorption and toughness in the cured product. When the amount exceeds 600, it may be difficult to maintain heat resistance.
In the epoxy resin composition of the present invention, the amine curing agent is preferably used in an amount of 0.2 to 0.6 equivalent based on 1 equivalent of the epoxy group of the epoxy resin, in terms of the amine equivalent of the amine compound. Particularly preferably 0.3 equivalent to 0.55 equivalent. When the amount of the epoxy group is less than 0.2 equivalent and when the amount exceeds 0.6 equivalent to 1 equivalent of the epoxy group, curing may be incomplete and favorable cured properties may not be obtained, which is not preferable.
The epoxy resin composition of the present invention may contain a curing accelerator. Specific examples of the curing accelerator that can be used include: acids such as formic acid, acetic acid, lactic acid, glycolic acid, n-butyric acid, isobutyric acid, propionic acid, caproic acid, caprylic acid, n-heptanoic acid, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, thioglycolic acid, phenol, m-cresol, p-chlorophenol, p-nitrophenol, 2, 4-dinitrophenol, o-aminophenol, p-aminophenol, 2,4, 5-trichlorophenol, resorcinol, hydroquinone, catechol, phloroglucinol, benzoic acid, p-toluic acid, p-aminobenzoic acid, p-chlorobenzoic acid, 2, 4-dichlorobenzoic acid, salicylic acid, phthalic acid, isophthalic acid, terephthalic acid, malic acid, oxalic acid, succinic acid, malonic acid, fumaric acid, maleic acid, tartaric acid, citric acid, and the like; amines such as monoethanolamine, diethanolamine, and triethanolamine; thiophenol, 2-mercaptoethanol, sulfur-containing compounds; imidazoles such as 2-methylimidazole, 2-ethylimidazole and 2-ethyl-4-methylimidazole; tertiary amines such as 2- (dimethylaminomethyl) phenol and 1, 8-diazabicyclo [5.4.0] undec-7-ene; phosphines such as triphenylphosphine; and metal compounds such as tin octylate. If necessary, the curing accelerator may be used in an amount of 0.1 to 5.0 parts by weight based on 100 parts by weight of the epoxy resin.
Other epoxy resins may be used in combination with the epoxy resin composition of the present invention. Specific examples of the other epoxy resins that can be used in combination with the epoxy resin of formula (1) include: polycondensates of bisphenols (bisphenol a, bisphenol F, bisphenol S, biphenol, bisphenol AD, etc.) or phenols (phenol, alkyl-substituted phenol, aromatic-substituted phenol, naphthol, alkyl-substituted naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene, dihydroxynaphthalene, etc.) with various aldehydes (formaldehyde, acetaldehyde, alkylaldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde, etc.); polymers of the above phenols with various diene compounds (dicyclopentadiene, terpenes, vinylcyclohexene, norbornadiene, vinylnorbornene, tetrahydroindene, divinylbenzene, divinylbiphenyl, diisopropenylbiphenyl, butadiene, isoprene, etc.); polycondensates of the above phenols with ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone, etc.); polycondensates of the above phenols with aromatic dimethyl alcohols (e.g., benzenedimethanol and biphenyldimethanol); polycondensates of the above phenols with aromatic dichloromethyl groups (a, a' -dichloroxylene, bischloromethylbiphenyl, etc.); polycondensates of the above phenols with aromatic bisalkoxymethyl groups (bismethoxymethyl benzene, bismethoxymethyl biphenyl, bisphenoxymethyl biphenyl, etc.); glycidyl ether-based epoxy resins, alicyclic epoxy resins, glycidyl amine-based epoxy resins, glycidyl ester-based epoxy resins, and the like obtained by glycidylating polycondensates of the above bisphenols with various aldehydes, alcohols, and the like, but the epoxy resins are not limited to those which are generally used. These epoxy resins may be used alone or in combination of 2 or more.
When the epoxy resin composition of the present invention is blended, a conventionally known curing agent can be used in combination. Examples of other curing agents that can be used in combination include: acid anhydride compounds, amide compounds, phenol compounds, carboxylic acid compounds, and the like. Specific examples of the curing agent that can be used include: amide compounds such as dicyandiamide, polyamide resins synthesized from a dimer of linolenic acid and ethylenediamine; acid anhydride compounds such as phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylnadic anhydride, hexahydrophthalic anhydride, and methylhexahydrophthalic anhydride; bisphenol a, bisphenol F, bisphenol S, bisphenol fluorene, terpene diphenol, 4 '-biphenol, 2, 2' -biphenol, 3 ', 5, 5' -tetramethyl- [1,1 '-biphenyl ] -4, 4' -diol, hydroquinone, resorcinol, naphthalenediol, tris (4-hydroxyphenyl) methane, 1,2, 2-tetrakis (4-hydroxyphenyl) ethane; novolac resins that are polycondensates of phenols (phenol, alkyl-substituted phenol, naphthol, alkyl-substituted naphthol, dihydroxybenzene, dihydroxynaphthalene, etc.) with formaldehyde, acetaldehyde, benzaldehyde, p-hydroxybenzaldehyde, o-hydroxybenzaldehyde, p-hydroxyacetophenone, o-hydroxyacetophenone, furfural; phenol aralkyl resins and modified products thereof as a reaction product of phenol or cresol with bis (hydroxymethyl) benzene, bis (methoxymethyl) benzene or bis (halomethyl) benzene, or a reaction product of phenol or cresol with bischloromethylbiphenyl, dimethoxymethylbiphenyl or dihydroxymethylbiphenyl, or a reaction product of phenol with diisopropylbenzene, diisopropylbenzene dimethyl ether or phenylbis (chloroisopropyl); halogenated bisphenols such as tetrabromobisphenol A; phenolic compounds such as condensates of terpenes and phenols, imidazoles, trifluoroborane-amine complexes, guanidine derivatives, and the like, but are not limited thereto. These curing agents may be used alone or in combination of two or more.
The epoxy resin composition of the present invention may contain a phosphorus-containing compound as a flame retardant component. The phosphorus-containing compound may be a reactive phosphorus-containing compound or an additive phosphorus-containing compound. Specific examples of the phosphorus-containing compound include: phosphoric acid ester compounds such as trimethyl phosphate, triethyl phosphate, tricresyl phosphate, trixylyl phosphate, cresyldiphenyl-2, 6-dixylyl phosphate, 1, 3-phenylenebis (dixylyl phosphate), 1, 4-phenylenebis (dixylyl phosphate), and 4, 4' -biphenyl (dixylyl phosphate); phosphines such as 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide and 10- (2, 5-dihydroxyphenyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide; phosphorus-containing epoxy compounds and red phosphorus obtained by reacting an epoxy resin with active hydrogen of the phosphine are preferably phosphoric acid esters, phosphines or phosphorus-containing epoxy compounds, and particularly preferably 1, 3-phenylenebis (dixylyl phosphate), 1, 4-phenylenebis (dixylyl phosphate), 4' -biphenyl (dixylyl phosphate) or phosphorus-containing epoxy compounds.
However, the amount of the phosphate ester compound used is preferably 0.1 or less (weight ratio) to the epoxy resin, because of environmental problems and concerns about electrical characteristics. More preferably 0.05 or less. It is particularly preferable that the phosphorus-containing compound is not added except for the addition as a curing accelerator.
The epoxy resin composition of the present invention may contain an inorganic filler. Examples of the inorganic filler include: fused silica, crystalline silica, alumina, calcium carbonate, calcium silicate, barium sulfate, talc, clay, magnesium oxide, alumina, beryllium oxide, iron oxide, titanium oxide, aluminum nitride, silicon nitride, boron nitride, mica, glass, quartz, mica, and the like. In addition, in order to impart a flame retardant effect, a metal hydroxide such as magnesium hydroxide or aluminum hydroxide is also preferably used. But is not limited thereto. In addition, more than 2 kinds may be used in combination. Among these inorganic fillers, fused silica, crystalline silica and other silica-based fillers are preferred because they are inexpensive and have good electrical reliability.
In the epoxy resin composition of the present invention, the amount of the inorganic filler used is usually in the range of 5 to 70% by weight, preferably 10 to 60% by weight, and more preferably 15 to 60% by weight in terms of the internal proportion. If the amount is too small, the linear expansion increases and warpage becomes a problem, or the substrate becomes thinner and does not have rigidity, which may cause a problem in the process. In addition, if the amount is too large, there is a possibility that the homogeneity is lost due to sedimentation of the filler or the like, or there is a possibility that the insertion property of the substrate is deteriorated or the adhesion to the metal is deteriorated, and therefore, there is a high possibility that the substrate is molded to have an adverse effect on the electrical characteristics such as peeling or breakdown voltage.
The shape, particle size and the like of the inorganic filler are not particularly limited, and the inorganic filler usually has a particle size of 0.01 to 50 μm, preferably 0.1 to 15 μm.
The epoxy resin composition of the present invention may contain a release agent in order to improve the release from a mold during molding. As the release agent, any of conventionally known release agents can be used, and examples thereof include: ester waxes such as carnauba wax and montan wax; fatty acids such as stearic acid and palmitic acid, and metal salts thereof; polyolefin waxes such as oxidized polyethylene and non-oxidized polyethylene. These release agents may be used alone, or 2 or more of them may be used in combination. The amount of the release agent is preferably 0.5 to 3% by weight based on the total organic components. If the amount is too small, the mold may be released from the mold to be poor, and if the amount is too large, the adhesion to a substrate or the like may be poor.
In order to improve the adhesiveness between the inorganic filler and the resin component, a coupling agent may be blended in the epoxy resin composition of the present invention. Any conventionally known coupling agent can be used as the coupling agent, and examples thereof include: various alkoxysilane compounds such as vinylalkoxysilane, epoxyalkoxysilane, styrylalkoxysilane, methacryloyloxyalkoxysilane, acryloxyalkoxysilane, aminoalkoxysilane, mercaptoalkoxysilane, and isocyanatoalkoxysilane, alkoxytitanium compounds, and aluminum chelate compounds. These coupling agents may be used alone, or 2 or more kinds may be used in combination. The surface of the inorganic filler may be treated with the coupling agent in advance and then kneaded with the resin, or the coupling agent may be mixed with the resin and then the inorganic filler may be kneaded.
The epoxy resin composition of the present invention may be prepared as a varnish composition (hereinafter, simply referred to as varnish) by adding an organic solvent thereto. Examples of the solvent used include: amide solvents such as γ -butyrolactone, N-methylpyrrolidone, N-dimethylformamide, N-dimethylacetamide, and N, N-dimethylimidazolidinone; sulfones such as sulfolane; ether solvents such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, propylene glycol monomethyl ether monoacetate, and propylene glycol monobutyl ether; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone; aromatic solvents such as toluene and xylene. The solvent is used in a range of usually 10 to 80% by weight, preferably 20 to 70% by weight, of the solid content concentration of the varnish other than the solvent.
In addition, a known additive may be blended as necessary in the epoxy resin composition of the present invention. Specific examples of additives that can be used include: polybutadiene and modified products thereof, modified products of acrylonitrile copolymers, polyphenylene oxide, polystyrene, polyethylene, polyimide, fluorine-containing resins, maleimide compounds, cyanate ester compounds, silicone gel, silicone oil, and colorants such as carbon black, phthalocyanine blue, and phthalocyanine green.
The resin sheet of the present invention will be explained.
A resin sheet using the epoxy resin composition of the present invention is obtained by: the varnish is obtained by applying the varnish onto a planar support by various coating methods known per se, such as gravure coating, screen printing, metal mask method, and spin coating, so that the thickness after drying becomes a predetermined thickness, for example, 5 to 100 μm, and then drying the resultant; which coating method is used may be appropriately selected depending on the kind, shape, size, thickness of coating, heat resistance of the support, and the like of the support.
Examples of the planar support include: films made of various polymers and/or copolymers thereof such as polyamide, polyamideimide, polyarylate, polyethylene terephthalate, polybutylene terephthalate, polyether ketone, polyetherimide, polyether ether ketone, polyketone, polyethylene, polypropylene, teflon (registered trademark), and metal foils such as copper foils.
The sheet-like composition (resin sheet of the present invention) can be obtained by drying after coating, but a sheet-like cured product can also be obtained by further heating the sheet. Further, the solvent drying and curing step may be performed by one heating.
The epoxy resin composition of the present invention can be applied to both surfaces or one surface of the support by the above-mentioned method and heated to form a layer of a cured product on both surfaces or one surface of the support. Alternatively, an adherend may be bonded and cured before curing to produce a laminate.
The resin sheet of the present invention may be used as an adhesive sheet by being peeled from a support, or may be adhered while being cured by bringing the resin sheet into contact with an adherend and applying pressure and heat as necessary.
The prepreg of the present invention will be explained.
The prepreg of the present invention is obtained by impregnating a fiber base material with the epoxy resin composition of the present invention. Thus, a prepreg having excellent heat resistance, low expansibility, and flame retardancy can be obtained. Examples of the fiber base material include: glass fiber base materials such as glass woven cloth, glass nonwoven cloth, and glass paper; woven or nonwoven fabrics comprising synthetic fibers such as paper, aramid, polyester, aromatic polyester, fluorine-containing resin, and the like; woven fabrics, nonwoven fabrics, mats, and the like comprising metal fibers, carbon fibers, mineral fibers, and the like. These substrates may be used alone or in combination. Among them, glass fiber substrates are preferred. This can further improve the rigidity and dimensional stability of the prepreg.
The glass fiber substrate preferably contains at least one selected from the group consisting of T glass, S glass, E glass, NE glass, and quartz glass.
Examples of the method for impregnating the fiber base material with the epoxy resin composition of the present invention include: a method of immersing the base material in the resin varnish, a method of coating with various coating machines, a method of blowing with a spraying device, and the like. Among these methods, a method of impregnating the base material with the resin varnish is preferable. This can improve the impregnation of the resin composition into the base material. When the base material is impregnated with the resin varnish, a common impregnation coating apparatus may be used.
For example, the epoxy resin composition of the present invention is impregnated as it is or in the form of a varnish obtained by dissolving or dispersing it in a solvent into a substrate such as a glass cloth, and then dried in a drying oven at a temperature of usually 80 to 200 ℃ (wherein the temperature is set to be not less than the temperature at which the solvent can volatilize when the solvent is used) for 2 to 30 minutes, preferably 2 to 15 minutes, to obtain a prepreg.
The metal-clad laminate of the present invention will be explained.
The laminate used in the present invention is a laminate obtained by heating and pressing the prepreg of the present invention described above. Thus, a metal-clad laminate excellent in heat resistance, low expansion properties and flame retardancy can be obtained. In the case of 1 prepreg, a metal foil is stacked on both upper and lower surfaces or one surface thereof. In addition, 2 or more prepregs may be laminated. When 2 or more prepregs are laminated, a metal foil or a film is laminated on both upper and lower surfaces or one surface of the outermost prepreg after lamination. Next, a metal-clad laminate can be obtained by heating and pressing a material obtained by stacking a prepreg and a metal foil. The heating temperature is not particularly limited, but is preferably 120 to 220 ℃, and more preferably 150 to 200 ℃. The pressure for the pressurization is not particularly limited, but is preferably 1.5MPa to 5MPa, and particularly preferably 2MPa to 4 MPa. If necessary, the post-curing may be carried out at a temperature of 150 to 300 ℃ in a high-temperature bath or the like.
The printed wiring board of the present invention will be explained.
The printed wiring board of the present invention uses the metal-clad laminate of the present invention as an inner layer circuit board. A circuit is formed on one surface or both surfaces of the metal-clad laminate. In some cases, the through-hole may be formed by drilling or laser processing, and the electrical connection may be obtained on both sides by plating or the like.
A commercially available resin sheet according to the present invention or a prepreg according to the present invention may be laminated on the inner circuit board and subjected to heat and pressure molding to obtain a multilayer printed wiring board.
Specifically, the resin sheet can be obtained by bonding the insulating layer side of the resin sheet to the inner circuit board, vacuum-heating and pressure-molding the resin sheet using a vacuum pressure type laminating apparatus or the like, and then heating and curing the insulating layer using a hot air drying apparatus or the like.
The conditions for the hot press molding are not particularly limited, and may be, for example, at a temperature of 60 ℃ to 160 ℃ and a pressure of 0.2MPa to 3 MPa. The conditions for heat curing are not particularly limited, and may be, for example, 140 to 240 ℃ for 30 to 120 minutes.
Alternatively, the prepreg of the present invention may be obtained by laminating the prepreg on an inner layer circuit board and molding the laminate by heating and pressing the laminate using a flat press or the like. The conditions for the hot press molding are not particularly limited, and may be, for example, 140 to 240 ℃ and 1 to 4 MPa. In such heat and pressure molding by a flat press apparatus or the like, the heat and pressure molding is performed while the insulating layer is heated and cured.
In addition, the method for manufacturing a multilayer printed wiring board according to the present invention includes: the method for manufacturing a multilayer printed circuit board includes a step of continuously laminating the resin sheet or the prepreg of the present invention on the surface of the inner layer circuit board on which the inner layer circuit pattern is formed, and a step of forming a conductor circuit layer by a semi-additive method.
In curing the insulating layer formed of the resin sheet or the prepreg of the present invention, the insulating layer may be preliminarily set in a semi-cured state in order to facilitate the subsequent laser irradiation and removal of resin residue and to improve the desmear property. Further, the first insulating layer is heated at a temperature lower than the normal heating temperature to partially cure (semi-cure) the insulating layer, and one or more insulating layers are further formed on the insulating layer, and the semi-cured insulating layer is re-heated and cured to such an extent that there is no problem in practical use, whereby the adhesion between the insulating layers and the circuit can be improved. The temperature for semi-curing in this case is preferably 80 to 200 ℃, more preferably 100 to 180 ℃. In the subsequent step, the insulating layer is irradiated with laser light to form an opening, but the substrate needs to be peeled off before that. The peeling of the substrate is not particularly problematic at any point of time after the insulating layer is formed, before the heating and curing, or after the heating and curing.
As the inner layer circuit board used for obtaining the multilayer printed wiring board, for example, an inner layer circuit board obtained by forming predetermined conductor circuits on both surfaces of a copper-clad laminate by etching or the like and blackening the conductor circuit portions can be preferably used.
Resin residues and the like after laser irradiation are preferably removed by an oxidizing agent such as permanganate and dichromate. In addition, the surface of the smooth insulating layer can be roughened at the same time, so that the adhesion of the conductive wiring circuit formed by the subsequent metal plating can be improved.
Next, an outer layer circuit is formed. The outer layer circuit is formed by the following method: the connection between the insulating resin layers is achieved by metal plating, and the outer layer circuit pattern is formed by etching. A multilayer printed wiring board can be obtained in the same manner as when a resin sheet or prepreg is used.
When a resin sheet or prepreg having a metal foil is used, circuit formation can be performed by etching so as to be used as a conductor circuit without peeling the metal foil. In this case, when an insulating resin sheet with a base material using a thick copper foil is used, since it is difficult to form fine pitches in the subsequent circuit pattern formation, an extra thin copper foil of 1 μm to 5 μm is used, or half etching is sometimes performed to reduce a copper foil of 12 μm to 18 μm to 1 μm to 5 μm by etching.
In the design of the multilayer printed wiring board, after the circuit is formed on the outermost layer, a solder resist layer may be formed. The method for forming the solder resist layer is not particularly limited, and is accomplished, for example, by the following method: a method of forming by laminating (laminating), exposing and developing a dry film type solder resist layer; or a method of forming a solder resist layer by exposing and developing the printed liquid resist. When the obtained multilayer printed wiring board is used in a semiconductor device, a connecting electrode portion is provided for mounting a semiconductor element. The connecting electrode portion can be appropriately coated with a metal coating such as a gold plating layer, a nickel plating layer, or a solder plating layer. A multilayer printed wiring board can be produced by such a method.
Next, a semiconductor device of the present invention will be explained.
A semiconductor element having solder bumps is mounted on the multilayer printed wiring board obtained as described above, and connection to the multilayer printed wiring board is achieved via the solder bumps. Then, a liquid sealing resin is filled between the multilayer printed wiring board and the semiconductor element, thereby forming a semiconductor device. The solder bump is preferably composed of an alloy containing tin, lead, silver, copper, bismuth, or the like.
The method for connecting the semiconductor element and the multilayer printed wiring board is as follows: the connection electrode portion on the substrate and the solder bump of the semiconductor element are aligned by using a flip chip bonding machine or the like, and then the solder bump is heated to a melting point or higher by using an infrared reflow apparatus (IR reflow apparatus), a hot plate, or another heating apparatus, and the multilayer printed wiring substrate and the solder bump are fusion-bonded to each other, thereby performing connection. In order to improve connection reliability, a metal layer having a low melting point such as solder paste may be formed in advance on the connection electrode portion on the multilayer printed wiring board. Before the bonding step, a flux may be applied to the solder bump and/or the surface layer of the connecting electrode portion on the multilayer printed wiring board, thereby improving the connection reliability.
The substrate is used as a motherboard, a network substrate (ネ ッ ト ワ ー ク substrate), a package substrate, or the like. In particular, the present invention is useful as a thin substrate for a single-sided sealing material as a package substrate. In the case of using as a semiconductor encapsulating material, examples of semiconductor devices obtained by blending the semiconductor encapsulating material include: DIP (Dual in-line Package), QFP (Quad Flat Package), BGA (Ball grid array), CSP (Chip Scale Package), SOP (Small Outline Package), TSOP (Thin Small Outline Package), TQFP (Thin Quad Flat Package), and the like.
Examples
The features of the present invention will be described in further detail below with reference to synthesis examples and examples. The materials, processing contents, processing steps, and the like described below can be modified as appropriate within a range not departing from the gist of the present invention. Therefore, the scope of the present invention should not be construed as being limited to the specific examples shown below.
The conditions for measuring the physical property values are as follows.
Epoxy equivalent weight
Measured by the method described in JIS K-7236, and the unit is g/eq.
Softening point
Measured by the method according to JIS K-7234 in terms of ℃ C.
Modulus of elasticity (DMA)
Dynamic viscoelasticity measuring apparatus: TA-instruments, DMA-2980
Measurement temperature range: -30 ℃ to 280 DEG C
Temperature rise rate: 2 ℃ per minute
Test piece size: using a test piece cut into 5mm x 50mm
Tg: the peak point of Tan-delta in the DMA measurement was taken as Tg.
Water absorption
Weight gain (%)
Synthesis example 1
In a flask equipped with a stirrer, a reflux condenser and a stirrer, 134 parts of a phenol resin represented by the following formula ((a)/(b) 1.3, n 1.5, hydroxyl equivalent 134g/eq., softening point 93 ℃) prepared according to W02007/007827, was added while purging with nitrogen, 450 parts of epichlorohydrin and 54 parts of methanol were dissolved with stirring, and the temperature was raised to 70 ℃. Subsequently, 42.5 parts of flaky sodium hydroxide was added stepwise over 90 minutes, and then the reaction was further carried out at 70 ℃ for 1 hour. After the reaction, the organic layer was washed with water to remove the salt, and then excess solvent such as epichlorohydrin was distilled off under reduced pressure using a rotary evaporator. To the residue was added 500 parts of methyl isobutyl ketone and dissolved, 17 parts of a 30 wt% aqueous sodium hydroxide solution was added under stirring to perform a reaction for 1 hour, and then water washing was performed until the washing water of the oil layer became neutral, and methyl isobutyl ketone and the like were distilled off under reduced pressure from the resulting solution using a rotary evaporator, whereby 195 parts of the epoxy resin of formula (1) (EP1) was obtained. The epoxy equivalent of the obtained epoxy resin was 211g/eq, the softening point was 71 ℃, and the melt viscosity at 150 ℃ (ICI melt viscosity, cone #1) was 0.34Pa · s.
Example 1
The epoxy resin (EP1) obtained in Synthesis example 1 was uniformly mixed and kneaded using a kneader, in which A-1 (amine equivalent 198g/eq, active hydrogen equivalent 97.5g/eq, softening point 55 ℃ C.) was added as a curing agent in an amount of 0.5 equivalent to 1 molar equivalent of the epoxy equivalent, and salicylic acid was added as a catalyst in an amount of 1 part by weight per 100 parts by weight of the epoxy resin, to obtain an epoxy resin composition. The epoxy resin composition was pulverized with a stirrer and then tableted with a tablet machine. The epoxy resin composition after the press-molding was subjected to transfer molding (175 ℃ C.. times.60 seconds), and then cured under conditions of 160 ℃ C.. times.2 hours +180 ℃ C.. times.6 hours after the mold release, to obtain a test piece for evaluation. The evaluation results are shown in table 1.
The details of the epoxy resins used for the evaluation are shown in table 2 below.
Comparative examples 1 to 7
Using the epoxy resin (EP1) obtained in Synthesis example 1 and various epoxy resins, phenol Novolac was prepared using an equivalent amount of A-1 or HA-1 (Minghuazai Kasei Co., Ltd.)
Lacquer resin) as curing agent and Triphenylphosphine (TPP) or salicylic acid as catalyst, with
A comparative test piece for evaluation was obtained in the same manner as in example 1. Will evaluate the knot
The results are shown in Table 1.
TABLE 1
Epoxy resin | Epoxide equivalent weight | Curing agent | Active hydrogen equivalent | Catalyst and process for preparing same | Tg(℃) | Water absorption (%) | |
Comparative example 1 | EPPN-502H | 170 | HA-1 | 106 | TPP 1phr | 220 | 1.98 |
Comparative example 2 | EPPN-501H | 166 | HA-1 | 106 | TPP lphr | 220 | 1.91 |
Comparative example 3 | EP1 | 211 | HA-1 | 106 | TPP 1phr | 209 | 1.58 |
Example 1 | EP1 | 211 | A-1 | 97.5 | Salicylic acid 1phr | 256 | 1.44 |
Comparative example 4 | NC-3000 | 277 | A-1 | 97.5 | Salicylic acid 1phr | 172 | 1.06 |
Comparative example 5 | RE-310S | 182 | A-1 | 97.5 | Without catalyst | 155 | 1.19 |
Comparative example 6 | EOCN-1020-55 | 195 | HA-1 | 106 | TPP 1phr | 185 | 1.15 |
Comparative example 7 | FAE-2500 | 217 | HA-1 | 106 | TPP 1phr | 215 | 1.73 |
TABLE 2
Name of product | Manufacturer(s) | Structure of the product |
EPPN-502H | Japanese chemical (Kyoho) | Trihydroxyphenyl methane type epoxy resin |
EPPN-501H | Japanese chemical (Kyoho) | Trihydroxyphenyl methane type epoxy resin |
NC-3000 | Japanese chemical (Kyoho) | Biphenyl phenol aralkyl resin |
RE-310S | Japanese chemical (Kyoho) | Bisphenol A epoxy resin |
EOCN-1020-55 | Japanese chemical (Kyoho) | Cresol novolac type epoxy resin |
FAE-2500 | Japanese chemical (Kyoho) | Trihydroxyphenyl methane type epoxy resin |
From table 1, when example 1 and comparative example 3 were compared, it was confirmed that a cured product having excellent heat resistance and water absorption properties was specifically formed by using an amine-based curing agent, as compared with using a phenol resin as a curing agent.
The cured properties obtained in table 1 were plotted with the heat resistance (Tg) on the horizontal axis and the water absorption (%) on the vertical axis, and the obtained graph is shown in fig. 1.
As can be seen from FIG. 1, the cured products of comparative examples 1 to 3 and comparative examples 4 to 7 have a correlation in which the water absorption rate increases as Tg increases. On the other hand, it was confirmed that the cured product using the epoxy resin of formula (1) and the amine-based curing agent had high heat resistance, but had low water absorption and was a specific combination different from the above-mentioned correlation.
The present invention has been described in detail with reference to the specific embodiments, but it is apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the present invention.
It should be noted that the present application is based on japanese patent application (japanese patent application 2014-157629) proposed on 8/1 in 2014, which is incorporated by reference in its entirety. Additionally, all references cited herein are incorporated herein by reference in their entirety.
Industrial applicability
The epoxy resin composition of the present invention provides a cured product that can achieve both high heat resistance and water resistance in a cured product thereof, and is therefore a material extremely useful for producing a laminated board such as a printed wiring board or a build-up board.
Claims (9)
1. An epoxy resin composition comprising, as essential components, an epoxy resin represented by the following general formula (1) and an amine-based curing agent, wherein the amine-based curing agent is a bifunctional or higher aniline resin obtained by polycondensation of aniline and a substituted biphenyl or a substituted phenyl, and the amine-based curing agent has a functional group equivalent of 60g/eq to 600g/eq,
wherein the ratio of (a) to (b) is (a)/(b) 1 to 3, G represents a glycidyl group, and n is a repeating number of 0 to 5.
2. A prepreg obtained by impregnating a fibrous base material with the epoxy resin composition according to claim 1.
3. A prepreg according to claim 2 wherein the fibrous substrate is a glass fibre substrate.
4. The prepreg according to claim 3, wherein the glass fiber substrate contains at least 1 selected from the group consisting of T glass, S glass, E glass, NE glass, and quartz glass.
5. A metal-clad laminate obtained by laminating a metal foil on at least one side of the prepreg according to any one of claims 2 to 4.
6. A resin sheet obtained by forming an insulating layer comprising the epoxy resin composition according to claim 1 on a film or a metal foil.
7. A printed wiring board obtained by using the metal-clad laminate according to claim 5 for an inner layer circuit board.
8. A printed wiring board obtained by curing the prepreg according to any one of claims 2 to 4 or the resin sheet according to claim 6.
9. A semiconductor device obtained by mounting a semiconductor element on the printed wiring board according to claim 7 or claim 8.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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JP2014157629A JP2016034996A (en) | 2014-08-01 | 2014-08-01 | Epoxy resin composition, prepreg, metal-clad laminate and printed wiring board |
JP2014-157629 | 2014-08-01 | ||
PCT/JP2015/071632 WO2016017751A1 (en) | 2014-08-01 | 2015-07-30 | Epoxy resin composition, resin sheet, and prepreg, and metal-clad laminate board, printed circuit board, and semiconductor device |
Publications (2)
Publication Number | Publication Date |
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CN106661200A CN106661200A (en) | 2017-05-10 |
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WO2018174447A1 (en) * | 2017-03-22 | 2018-09-27 | 주식회사 엘지화학 | Resin composition for semiconductor package, prepreg using same, and metal foil laminated plate |
KR102057255B1 (en) | 2017-03-22 | 2019-12-18 | 주식회사 엘지화학 | Resin composition for semiconductor package, prepreg and metal clad laminate using the same |
WO2018174446A1 (en) * | 2017-03-22 | 2018-09-27 | 주식회사 엘지화학 | Resin composition for semiconductor package, prepreg using same, and metal foil laminated plate |
KR102049024B1 (en) * | 2017-03-22 | 2019-11-26 | 주식회사 엘지화학 | Resin composition for semiconductor package, prepreg and metal clad laminate using the same |
KR102246974B1 (en) * | 2018-04-10 | 2021-04-30 | 주식회사 엘지화학 | Resin composition for semiconductor package, prepreg and metal clad laminate using the same |
KR102257926B1 (en) | 2018-09-20 | 2021-05-28 | 주식회사 엘지화학 | Multilayered printed circuit board, method for manufacturing the same, and semiconductor device using the same |
JP6636599B2 (en) * | 2018-11-30 | 2020-01-29 | 日本化薬株式会社 | Epoxy resin composition, prepreg and metal-clad laminate, printed wiring board |
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JPH05170874A (en) * | 1991-12-19 | 1993-07-09 | Mitsui Toatsu Chem Inc | Epoxy resin composition |
JP3476027B2 (en) * | 1994-04-28 | 2003-12-10 | 日本化薬株式会社 | Manufacturing method of epoxy resin |
JP3525152B2 (en) * | 1996-09-30 | 2004-05-10 | 独立行政法人 科学技術振興機構 | Epoxy resin curable composition |
JP2004189811A (en) * | 2002-12-10 | 2004-07-08 | Toho Tenax Co Ltd | Woven fabric prepreg |
JP5195582B2 (en) * | 2009-03-30 | 2013-05-08 | 日立化成株式会社 | Thermosetting insulating resin composition, and insulating film with support, prepreg, laminate and multilayer printed wiring board using the same |
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JP5754731B2 (en) * | 2011-08-25 | 2015-07-29 | 明和化成株式会社 | Epoxy resin, method for producing epoxy resin, and use thereof |
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JP6410405B2 (en) * | 2012-08-01 | 2018-10-24 | 住友ベークライト株式会社 | Resin substrate, prepreg, printed wiring board, semiconductor device |
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