JP2007269979A - エポキシ樹脂組成物、その硬化物、半導体封止材料、および半導体装置 - Google Patents
エポキシ樹脂組成物、その硬化物、半導体封止材料、および半導体装置 Download PDFInfo
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- JP2007269979A JP2007269979A JP2006097456A JP2006097456A JP2007269979A JP 2007269979 A JP2007269979 A JP 2007269979A JP 2006097456 A JP2006097456 A JP 2006097456A JP 2006097456 A JP2006097456 A JP 2006097456A JP 2007269979 A JP2007269979 A JP 2007269979A
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- epoxy resin
- resin composition
- epoxy
- mass
- semiconductor
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 173
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 172
- 239000000203 mixture Substances 0.000 title claims abstract description 60
- 239000004065 semiconductor Substances 0.000 title claims abstract description 48
- 239000003566 sealing material Substances 0.000 title claims abstract description 22
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000011256 inorganic filler Substances 0.000 claims abstract description 15
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 15
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 13
- 239000003063 flame retardant Substances 0.000 claims description 32
- 229920005989 resin Polymers 0.000 claims description 31
- 239000011347 resin Substances 0.000 claims description 31
- 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 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 238000011049 filling Methods 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 4
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 abstract description 15
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 description 34
- 238000003786 synthesis reaction Methods 0.000 description 34
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 28
- -1 β-ethylglycidyloxy Chemical group 0.000 description 26
- 238000001723 curing Methods 0.000 description 20
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- 239000004593 Epoxy Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 229920003986 novolac Polymers 0.000 description 15
- 150000002989 phenols Chemical class 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000005011 phenolic resin Substances 0.000 description 13
- 238000005259 measurement Methods 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 150000004780 naphthols Chemical class 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 235000019256 formaldehyde Nutrition 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000000654 additive Substances 0.000 description 5
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 5
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 5
- 239000000347 magnesium hydroxide Substances 0.000 description 5
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920001568 phenolic resin Polymers 0.000 description 5
- 150000008442 polyphenolic compounds Chemical class 0.000 description 5
- 235000013824 polyphenols Nutrition 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000011342 resin composition Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 4
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 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 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- 150000007973 cyanuric acids 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
- 230000000694 effects Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000002484 inorganic compounds Chemical class 0.000 description 4
- 239000012796 inorganic flame retardant Substances 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 238000000199 molecular distillation Methods 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 4
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000005350 fused silica glass Substances 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides Chemical class 0.000 description 3
- 150000002903 organophosphorus compounds Chemical class 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 150000003018 phosphorus compounds Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 3
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 3
- 229940007718 zinc hydroxide Drugs 0.000 description 3
- 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 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- GSKNLOOGBYYDHV-UHFFFAOYSA-N 2-methylphenol;naphthalen-1-ol Chemical compound CC1=CC=CC=C1O.C1=CC=C2C(O)=CC=CC2=C1 GSKNLOOGBYYDHV-UHFFFAOYSA-N 0.000 description 2
- YZEZMSPGIPTEBA-UHFFFAOYSA-N 2-n-(4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2N=C(N)N=C(N)N=2)=N1 YZEZMSPGIPTEBA-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- 238000010521 absorption reaction Methods 0.000 description 2
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- ZRIUUUJAJJNDSS-UHFFFAOYSA-N ammonium phosphates Chemical compound [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O ZRIUUUJAJJNDSS-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000003491 array Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 229910000416 bismuth oxide Inorganic materials 0.000 description 2
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 2
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 description 2
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 2
- 239000008393 encapsulating agent Substances 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910001701 hydrotalcite Inorganic materials 0.000 description 2
- 229960001545 hydrotalcite Drugs 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
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- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000005078 molybdenum compound Substances 0.000 description 2
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- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
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- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 2
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 description 2
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- 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
- WBODDOZXDKQEFS-UHFFFAOYSA-N 1,2,3,4-tetramethyl-5-phenylbenzene Chemical group CC1=C(C)C(C)=CC(C=2C=CC=CC=2)=C1C WBODDOZXDKQEFS-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- IVORCBKUUYGUOL-UHFFFAOYSA-N 1-ethynyl-2,4-dimethoxybenzene Chemical compound COC1=CC=C(C#C)C(OC)=C1 IVORCBKUUYGUOL-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
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Abstract
【解決手段】 2,7−ジヒドロキシナフタレン等のジヒドロキシナフタレン類とβ−アルキルエピハロヒドリンとを反応させて得られるエポキシ樹脂であって、かつ、前記エポキシ樹脂中の全エポキシ基に占めるβ−アルキルグリシジル基の割合が95%以上であるエポキシ樹脂(A)、及び硬化剤(B)を必須成分とする。
【選択図】 なし。
Description
この際、ジヒドロキシナフタレン類の水酸基に対するβ−アルキルエピハロヒドリンの過剰率を調節することにより、得られるエポキシ樹脂(A)中のジ(β−アルキルグリシジルオキシ)ナフタレン構造を有する化合物の含有率、特に前記式1で表されるエポキシ樹脂の場合においてはn=0成分の含有率を調節することができる。具体的には、ジヒドロキシナフタレン類の水酸基に対するβ−メチルエピクロルヒドリンのモル数を10倍以上に高めることが望ましい。
ポリナフトール樹脂類とホルムアルデヒド類との反応生成物である脂環式水素含有ポリフェノールノボラック樹脂類又はポリナフトールノボラック樹脂類のポリグリシジルエーテル;フェノール類やナフトール類と芳香族カルボニル化合物との縮合反応により得られる多価フェノールや多価ナフトール類のグリシジルエーテル化合物類;フロログリシン、トリス(4−ヒドロキシフェニル)メタン、1,1,2,2−テトラキス(4−ヒドロキシフェニル)エタン、1,3−ビス[(4−ヒドロキシフェニル)メチル]ベンゼン、1,4−ビス[(4−ヒドロキシフェニル)メチル]ベンゼン等を基本骨格とする三価以上のフェノール類のポリグリシジルエーテル;カリクサレン等の環状フェノール類から誘導されるグリシジルエーテル化合物等;
p−アミノフェノール、m−アミノフェノール、4−アミノメタクレゾール、6−アミノメタクレゾール、4,4’−ジアミノジフェニルメタン、3,3’−ジアミノジフェニルメタン、4,4’−ジアミノジフェニルエーテル、3,4’−ジアミノジフェニルエーテル、1,4−ビス(4−アミノフェノキシ)ベンゼン、1,4−ビス(3−アミノフェノキシ)ベンゼン、1,3−ビス(4−アミノフェノキシ)ベンゼン、1,3−ビス(3−アミノフェノキシ)ベンゼン、2,2−ビス(4−アミノフェノキシフェニル)プロパン、P−フェニレンジアミン、m−フェニレンジアミン、2,4−トルエンジアミン、2,6−トルエンジアミン、p−キシリレンジアミン、m−キシリレンジアミン、1,4−シクロヘキサンビス(メチルアミン)、1,3−シクロヘキサンビス(メチルアミン)、N、N−ジグリシジルアニリン等から誘導されるアミン系エポキシ樹脂;p−オキシ安息香酸、m−オキシ安息香酸、テレフタル酸、イソフタル酸等の芳香族カルボン酸から誘導されるグリシジルエステル系化合物;5,5−ジメチルヒダントイン等から誘導されるヒダントイン系エポキシ化合物;2、2−ビス(3、4−エポキシ シクロヘキシル)プロパン、2,2−ビス[4−(2,3−エポキシ プロピル)シクロヘキシル]プロパン、ビニルシクロヘキセンジオキサイド、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レート等の脂環式エポキシ樹脂;ポリブタジエン等の不飽和炭化水素化合物中の二重結合を酸化して得られる脂肪族エポキシ樹脂等が挙げられる。これらのエポキシ樹脂の一種または二種以上使用しても良い。
攪拌機、温度計、ディーンスタークトラップ、コンデンサーが装着された4つ口フラスコに2,7−ジヒドロキシナフタレン320g(2モル)にβ-メチルエピクロルヒドリン1598g(15モル)とn-ブタノール300gを添加して、50℃で49%NaOH359g(4.4モル)を3時間要して滴下した。その後、50℃で1時間攪拌を続けてエポキシ化反応を完結して、攪拌を停止して下層を棄却した。次いで、過剰のβ-メチルエピクロルヒドリンを蒸留回収した後に、MIBK1000gとn-ブタノール100gを加えて粗樹脂を溶解した。それに10%NaOH30gを添加して、80℃で3時間攪拌して、攪拌を停止して下層を棄却した。それに水300gを加えて2回水洗して、脱水−濾過−脱溶媒を経てエポキシ樹脂540gを得た。このエポキシ樹脂はエポキシ当量が187g/eq、前記の式(1)中のn=0成分を70質量%含有していた。さらに、このエポキシ樹脂をトルエン500gに溶解させ、メタノール100gを徐々に加え、再結晶させ、析出した結晶を濾別し、メタノールで洗浄した後乾燥させてエポキシ樹脂(A)270gを得た。このエポキシ樹脂はエポキシ当量が163g/eq、前記の式(1)中のn=0成分を90質量%含有しており、DSC測定融点は115℃、溶融粘度(150℃、ICI粘度計)は2mPa・sであった。
再結晶を分子蒸留(260℃、1KPa以下)に変更した以外は合成例1と同様にして、目的のエポキシ樹脂(B)300gを得た。このエポキシ樹脂はエポキシ当量が169g/eq、前記の式(1)中のn=0成分を80質量含有しており、DSC測定融点は103℃、溶融粘度(150℃、ICI粘度計)は2mPa・sであった。
再結晶を実施しなかった以外は合成例1と同様にして、目的のエポキシ樹脂(C)540gを得た。このエポキシ樹脂はエポキシ当量が187g/eq、前記の式(1)中のn=0成分を70質量含有しており、半固形状で、溶融粘度(150℃、ICI粘度計)は10mPa・sであった。
2,7−ジヒドロキシナフタレンを同量の1、6−ジヒドロキシナフタレンに変更した以外は合成例1と同様にして、目的のエポキシ樹脂(D)275gを得た。このエポキシ樹脂はエポキシ当量が163g/eq、前記の式(1)中のn=0成分を90質量含有しており、DSC測定融点は80℃、溶融粘度(150℃、ICI粘度計)は2mPa・sであった。
2,7−ジヒドロキシナフタレンを同量の1、4−ジヒドロキシナフタレンに変更した以外は合成例1と同様にして、目的のエポキシ樹脂(E)265gを得た。このエポキシ樹脂はエポキシ当量が163g/eq、前記の式(1)中のn=0成分を90質量含有しており、DSC測定融点は135℃、溶融粘度(150℃、ICI粘度計)は2mPa・sであった。
2,7−ジヒドロキシナフタレンを同量の1、5−ジヒドロキシナフタレンに変更した以外は合成例1と同様にして、目的のエポキシ樹脂(F)267gを得た。このエポキシ樹脂はエポキシ当量が163g/eq、前記の式(1)中のn=0成分を90質量含有しており、DSC測定融点は185℃、溶融粘度(150℃、ICI粘度計)は測定不可であった。
β-メチルエピクロルヒドリンをエピクロロヒドリン1388g(15モル)に変更した以外は合成例1と同様にして、目的のエポキシ樹脂(G)245gを得た。このエポキシ樹脂はエポキシ当量が141g/eq、前記の式(1)中のn=0成分を95質量含有しており、DSC測定融点は93℃、溶融粘度(150℃、ICI粘度計)は1mPa・sであった。
2,7−ジヒドロキシナフタレンを同量の1、6−ジヒドロキシナフタレンに変更、β-メチルエピクロルヒドリンをエピクロロヒドリン1388g(15モル)に変更した以外は合成例1と同様にして、目的のエポキシ樹脂(H)240gを得た。このエポキシ樹脂はエポキシ当量が142g/eq、前記の式(1)中のn=0成分を96質量含有しており、DSC測定融点は60℃、溶融粘度(150℃、ICI粘度計)は1mPa・sであった。
2,7−ジヒドロキシナフタレンを同量の1、4−ジヒドロキシナフタレンに変更、β-メチルエピクロルヒドリンをエピクロロヒドリン1388g(15モル)に変更した以外は合成例1と同様にして、目的のエポキシ樹脂(I)250gを得た。このエポキシ樹脂はエポキシ当量が142g/eq、前記の式(1)中のn=0成分を95質量含有しており、DSC測定融点は110℃、溶融粘度(150℃、ICI粘度計)は1mPa・sであった。
2,7−ジヒドロキシナフタレンを同量の1、5−ジヒドロキシナフタレンに変更、β-メチルエピクロルヒドリンをエピクロロヒドリン1388g(15モル)に変更した以外は合成例1と同様にして、目的のエポキシ樹脂(J)248gを得た。このエポキシ樹脂はエポキシ当量が141g/eq、前記の式(1)中のn=0成分を95質量含有しており、DSC測定融点は165℃、溶融粘度(150℃、ICI粘度計)は測定不可であった。
2,7−ジヒドロキシナフタレンを同量の1、5−ジヒドロキシナフタレンに変更、β-メチルエピクロルヒドリン1598g(15モル)をβ-メチルエピクロルヒドリン479g(4.5モル)とエピクロロヒドリン1064g(11.5モル)との混合物に変更、また再結晶を実施しなかった以外は合成例1と同様にして、目的のエポキシ樹脂(J)490gを得た。このエポキシ樹脂はエポキシ当量が164g/eq、前記の式(1)中のn=0成分を81質量含有しており、DSC測定融点は128℃、溶融粘度(150℃、ICI粘度計)は5mPa・sであった。また、C−NMRのピーク強度比率から算出したβ−メチル置換/非置換の比率は47/53であった。
エポキシ樹脂として合成例1〜11で得られたエポキシ樹脂(A)〜(K)とYX−4000Hを用い、硬化剤として「フェノライト TD−2131」(フェノールノボラック樹脂、大日本インキ化学工業(株)製、水酸基当量104g/eq、軟化点80℃)を用い、促進剤としてトリフェニルフォスフィン(TPP)を用いて、表2中の配合比に従って調整しエポキシ組成物を得た。次いで150℃で20分間の条件でプレス成形し、その後175℃でさらに5時間の条件で後硬化(アフターキュア)して、硬化物を得た。得られた硬化物を各評価に必要な試験サイズに切り出し、以下の方法で評価試験を行った。
(1)吸湿率
東京理化(株)製恒温恒湿装置「KCL−2000A」を用いて、85℃/85%RHの条件下、硬化物試験片を300時間処理した前後の質量変化率(wt%)を吸湿率として測定した(試験片のサイズ75×25×2mm)。
(2)線膨張係数
セイコー電子工業(株)製熱機械分析装置「TMA/SS6100」を用いて、昇温速度3℃/分により測定し、40〜60℃までに変化させた際の線膨張係数(α1:ガラス領域での線膨張係数)を測定した。
(3)誘電特性(誘電率、誘電正接)
JIS−C−6481に準拠した方法により、アジレント・テクノロジー(株)製インピーダンス・マテリアル・アナライザ「HP4291B」により、絶乾後、23℃、湿度50%の室内に24時間保管した後の硬化物の100MHzの周波数における誘電率と誘電正接を測定した(試験片のサイズ75×25×2mm)。
Claims (10)
- ジヒドロキシナフタレン類とβ−アルキルエピハロヒドリンとを必須の単量体成分として反応させて得られるエポキシ樹脂であって、かつ、前記エポキシ樹脂中の全エポキシ基に占めるβ−アルキルグリシジル基の割合がモル基準で95%以上であるエポキシ樹脂(A)、及び硬化剤(B)を必須成分とすることを特徴とするエポキシ樹脂組成物。
- 前記エポキシ樹脂(A)がジ(β−アルキルグリシジルオキシ)ナフタレン構造を有する化合物を該エポキシ樹脂(A)中、75質量%以上となる割合で含有するものである請求項1記載のエポキシ樹脂組成物。
- 前記エポキシ樹脂(A)が、結晶性エポキシ樹脂である請求項1又は2記載のエポキシ樹脂組成物。
- 前記エポキシ樹脂(A)及び硬化剤(B)に加え、無機充填材(C)を必須成分として含有する請求項1〜4の何れか1つに記載のエポキシ樹脂組成物。
- 無機充填材(C)の充填率が90質量%以上であることを特徴とする請求項5に記載のエポキシ樹脂組成物。
- 非ハロゲン系難燃剤(D)を含有することを特徴とする請求項1〜6の何れか1つに記載のエポキシ樹脂組成物。
- 請求項6又は請求項7に記載のエポキシ樹脂組成物からなることを特徴とする半導体封止材料。
- 半導体チップと樹脂パッケージ及び電極通電部を必須の構成要素とする半導体装置であって、請求項8記載の半導体封止材料から構成されるものであることを特徴とする半導体装置。
- 請求項1〜7の何れか1つに記載のエポキシ樹脂組成物を硬化させて得られることを特徴とする硬化物。
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JP2008094896A (ja) * | 2006-10-06 | 2008-04-24 | Sumitomo Bakelite Co Ltd | 半導体封止用樹脂組成物及び半導体装置 |
JP2010083952A (ja) * | 2008-09-30 | 2010-04-15 | Mitsubishi Materials Corp | 導電性インク組成物及び該組成物を用いて形成された太陽電池モジュール |
JP2010083953A (ja) * | 2008-09-30 | 2010-04-15 | Mitsubishi Materials Corp | 導電性インク組成物及び該組成物を用いて形成された太陽電池モジュール |
WO2012141027A1 (ja) * | 2011-04-14 | 2012-10-18 | ソニーケミカル&インフォメーションデバイス株式会社 | 異方性導電フィルム |
KR101202028B1 (ko) | 2010-03-17 | 2012-11-16 | 한국생산기술연구원 | 새로운 에폭시 수지 및 이를 포함하는 반도체 봉지용 에폭시 수지 복합체 |
JP2013219389A (ja) * | 2013-07-04 | 2013-10-24 | Mitsubishi Materials Corp | 太陽電池セル及び該太陽電池セルを備えた太陽電池モジュール |
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JPWO2018139112A1 (ja) * | 2017-01-24 | 2019-04-18 | Dic株式会社 | エポキシ樹脂およびこれを含むエポキシ樹脂組成物、並びに前記エポキシ樹脂組成物を用いた硬化物 |
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JP2008094896A (ja) * | 2006-10-06 | 2008-04-24 | Sumitomo Bakelite Co Ltd | 半導体封止用樹脂組成物及び半導体装置 |
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JPWO2018139112A1 (ja) * | 2017-01-24 | 2019-04-18 | Dic株式会社 | エポキシ樹脂およびこれを含むエポキシ樹脂組成物、並びに前記エポキシ樹脂組成物を用いた硬化物 |
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