JP5570453B2 - エポキシ樹脂組成物及び硬化物 - Google Patents
エポキシ樹脂組成物及び硬化物 Download PDFInfo
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- JP5570453B2 JP5570453B2 JP2011026956A JP2011026956A JP5570453B2 JP 5570453 B2 JP5570453 B2 JP 5570453B2 JP 2011026956 A JP2011026956 A JP 2011026956A JP 2011026956 A JP2011026956 A JP 2011026956A JP 5570453 B2 JP5570453 B2 JP 5570453B2
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- Prior art keywords
- epoxy resin
- resin composition
- indene
- phenol
- weight
- Prior art date
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- 239000003822 epoxy resin Substances 0.000 title claims description 97
- 229920000647 polyepoxide Polymers 0.000 title claims description 97
- 239000000203 mixture Substances 0.000 title claims description 60
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 76
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 66
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 229920003986 novolac Polymers 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 13
- 239000011256 inorganic filler Substances 0.000 claims description 12
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 12
- 239000004065 semiconductor Substances 0.000 claims description 12
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000002430 hydrocarbons Chemical group 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims description 6
- 239000003566 sealing material Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- -1 phosphate ester Chemical class 0.000 description 24
- 229920005989 resin Polymers 0.000 description 22
- 239000011347 resin Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 150000002440 hydroxy compounds Chemical class 0.000 description 21
- 150000002989 phenols Chemical class 0.000 description 20
- 150000003440 styrenes Chemical class 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000003063 flame retardant Substances 0.000 description 12
- 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 11
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000004593 Epoxy Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 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 9
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 8
- 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 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 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
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 235000013824 polyphenols Nutrition 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- 239000003377 acid catalyst Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000004780 naphthols Chemical class 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 150000002469 indenes Chemical class 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 229910000000 metal hydroxide Inorganic materials 0.000 description 4
- 150000004692 metal hydroxides Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 229960001755 resorcinol Drugs 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- IXCOKTMGCRJMDR-UHFFFAOYSA-N 9h-fluorene;phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 IXCOKTMGCRJMDR-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 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
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 238000010538 cationic polymerization reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000748 compression moulding Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 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
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
- 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
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- HDPBBNNDDQOWPJ-UHFFFAOYSA-N 4-[1,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HDPBBNNDDQOWPJ-UHFFFAOYSA-N 0.000 description 2
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- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
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- 229930185605 Bisphenol Natural products 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
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- 229910019142 PO4 Inorganic materials 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
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- 239000002253 acid Substances 0.000 description 2
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- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 239000010941 cobalt Substances 0.000 description 2
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
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- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
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- DAJPMKAQEUGECW-UHFFFAOYSA-N 1,4-bis(methoxymethyl)benzene Chemical compound COCC1=CC=C(COC)C=C1 DAJPMKAQEUGECW-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Description
別の観点からは、本発明に使用するStPNEは、1分子あたりのα‐メチルベンジル基の置換数(数平均)は、1以上であることが好ましく、より好ましくは2以上、更に好ましくは2.6〜4である。
StPNの製造方法は、一般式(4)で表される多価ヒドロキシ化合物のヒドロキシ基1モルに対し、スチレン類0.1〜2.5モルを、酸触媒の存在下に反応させることにより行う。一般式(4)で表わされる多価ヒドロキシ化合物としては、フェノールノボラック又はクレゾールノボラックが代表的である。スチレン類の使用量は、ヒドロキシ基1モルに対し、0.1〜2.5であるが、0.1〜1.0が好ましく、0.3〜0.8がより好ましい。
(ここで、M1およびM2は互いに異なる金属元素を示し、a、b、c、d、m、n及びlは正の数を示す。)
上記組成式(I)中のM1及びM2は互いに異なる金属元素であれば特に制限はないが、難燃性の観点からは、M1とM2が同一とならないようにM1が第3周期の金属元素、IIA族のアルカリ土類元素、IVB族、IIB族、VII族、IB族、IIIA族及びIVA族に属する金属元素から選ばれ、M2がIIIB〜IIB族の遷移金属元素から選ばれることが好ましい。そして、M1がマグネシウム、カルシウム、アルミニウム、スズ、チタン、鉄、コバルト、ニッケル、銅及び亜鉛から選ばれ、M2が鉄、コバルト、ニッケル、銅及び亜鉛から選ばれることが好ましい。流動性の観点からは、M1がマグネシウムでM2が亜鉛であることが好ましい。m及びnのモル比は本発明の効果が得られれば特に制限はないが、m/nが99/1〜50/50であることが好ましい。金属水酸化物系難燃剤をエポキシ樹脂組成物に配合する場合の含有率は、1〜10重量%の範囲がよい。好ましくは2〜9重量%であり、より好ましくは5〜9重量%である。これより小さいと有機成分の含有率が高くなり難燃性が十分に発揮されない。また反対にこれより大きくなると、成形物の体積固有抵抗値が悪くなることで、絶縁信頼性が低下するとともに流動性が悪化する。金属水酸化物系難燃剤は無機充填材としても作用するので、前記無機充填剤の配合量の計算においては、無機充填剤に含めて計算する。
(多価ヒドロキシ樹脂の合成)
1Lの4口フラスコに、多価ヒドロキシ化合物成分としてフェノールノボラック(昭和高分子製;BRG−555、水酸基当量105g/eq.、軟化点67℃、150℃での溶融粘度0.08Pa・s)を105g、トルエン5.3g、酸触媒としてp−トルエンスルホン酸0.055g(300ppm)を仕込み100℃に昇温した。次に、100℃にて攪拌しながら、スチレン73g(0.7モル)を3時間かけて滴下し反応させた。さらに、100℃にて2時間反応後、30%Na2CO30.049gを添加し中和を行った。次に、MIBK330gに溶解させ、80℃にて5回水洗を行った。続いて、MIBKを減圧留去した後、多価ヒドロキシ樹脂170gを得た。その水酸基当量は178g/eq.、軟化点は78℃、150℃での溶融粘度は0.13Pa・sであった。水酸基当量からこの多価ヒドロキシ樹脂のpは0.7と計算された。この樹脂をStPN−Aという。
(エポキシ樹脂の合成)
四つ口セパラブルフラスコに合成例1で得たStPN−A150g、エピクロルヒドリン468g、ジエチレングリコールジメチルエーテル70gを入れ撹拌溶解させた。均一に溶解後、130mmHgの減圧下65℃に保ち、48%水酸化ナトリウム水溶液70.3gを4時間かけて滴下し、この滴下中に還流留出した水とエピクロルヒドリンを分離槽で分離しエピクロルヒドリンは反応容器に戻し、水は系外に除いて反応した。反応終了後、濾過により生成した塩を除き、更に水洗したのちエピクロルヒドリンを留去し、エポキシ樹脂185gを得た(StPNE−A)。得られた樹脂のエポキシ当量は246g/eq.、軟化点は56℃、150℃における溶融粘度は0.10Pa・sであった。
上記の合成例2で得られたエポキシ樹脂(StPNE−A)、硬化剤、無機充填剤及びインデン系オリゴマーと硬化促進剤としてのトリフェニルホスフィンと、その他の添加剤を表1〜2に示す配合割合で混練してエポキシ樹脂組成物を調製した。表中の数値は配合における重量部を示す。
エポキシ樹脂A:o-クレゾールノボラック型エポキシ樹脂(エポキシ当量200、軟化点65℃、新日鐵化学製)、
エポキシ樹脂B:フェノールアラルキル型エポキシ樹脂(エポキシ当量238、軟化点51℃、150℃での溶融粘度0.12Pa・s)を用いた。
硬化剤成分として、
PA:フェノールアラルキル樹脂(MEH−7800SS(明和化成製)、OH当量175、軟化点67℃)、
PN:フェノールノボラック(PSM−4261(群栄化学製)、OH当量103、軟化点 82℃)を用いた。
無機充填剤として、電気化学工業製の球状溶融シリカFB−60(平均粒径21μm)を使用した。
インデン系オリゴマー成分として、
I−100(新日鐵化学製;インデン、スチレン及びフェノールの共重合物、軟化点100℃)、
IP−100(新日鐵化学製;インデンの重合物、軟化点98℃)、
IS−100BT(新日鐵化学製;インデン、ベンゾチオフェンの共重合物、軟化点92℃)を用いた。
電位差滴定装置を用い、溶媒としてメチルエチルケトンを使用し、臭素化テトラエチルアンモニウム酢酸溶液を加え、電位差滴定装置にて0.1mol/L過塩素酸−酢酸溶液を用いて測定した。
自動軟化点装置(明峰社製作所(株)製、ASP−M4SP)を用い、JIS−K−2207に従い環球法にて測定した。
BROOKFIELD製、CAP2000H型回転粘度計を用いて、150℃にて測定した。
セイコーインスツル製TMA120C型熱機械測定装置により、昇温速度10℃/分の条件でTgを求めた。
25℃、相対湿度50%の条件を標準状態とし、85℃、相対湿度85%の条件で100時間吸湿させた後の重量変化率とした。
密着性は、194アロイ板2枚の間に25mm×12.5mm×0.5mmの成形物を圧縮成型機により175℃で成形し、175℃、12時間ポストキュアを行った後、引張剪断強度を求めることにより評価した。
厚さ1/16インチの試験片を成形し、UL94V-0規格によって評価し、5本の試験片での合計の燃焼時間で表した。
8)耐リフロー性
体積固8mm×10mm×0.4mmのシリコンチップを搭載した外形寸法20mm×14mm×2mmの80ピンフラットパッケージ(QFP)を、エポキシ樹脂組成物を用いて175℃で成形し、更に175℃にて12時間ポストキュアを行い、85℃、85%RH、168時間の条件で加湿させた後、235℃で10秒の条件でリフロー処理を行い、クラックの有無を観察し、試験パッケージ数(5個)に対するクラック発生パッケージ数で評価した。
Claims (6)
- エポキシ樹脂、フェノール系硬化剤、無機充填剤及びインデン系オリゴマーを含有するエポキシ樹脂組成物において、エポキシ樹脂成分が、下記一般式(1)で示されるエポキシ樹脂を60重量%以上含有すること、フェノール系硬化剤成分が、アラルキル型フェノール系硬化剤及びノボラック型フェノール系硬化剤から選ばれる少なくとも1種を含有するものであること、エポキシ樹脂とフェノール系硬化剤の配合比率が、エポキシ基と硬化剤中のフェノール性OH基の当量比で0.8〜1.5の範囲であること、エポキシ樹脂組成物中の請無機充填剤の含有率が、60〜94重量%であること、及びインデン系オリゴマーの含有量がエポキシ樹脂100重量部に対し、5〜30重量部であることを特徴とするエポキシ樹脂組成物。
- インデン系オリゴマーが、インデン類、スチレン類及びフェノール類を含有するモノマーを共重合させることにより得られるオリゴマーであることを特徴とする請求項1に記載のエポキシ樹脂組成物。
- インデン系オリゴマーが、インデン類及びベンゾチオフェン類を含有するモノマーを共重合させることにより得られるオリゴマーであることを特徴とする請求項1又は2に記載のエポキシ樹脂組成物。
- 半導体封止材用のエポキシ樹脂組成物であることを特徴とする請求項1〜3のいずれかに記載のエポキシ樹脂組成物。
- 請求項1〜4のいずれかに記載のエポキシ樹脂組成物を硬化してなるエポキシ樹脂硬化物。
- 請求項4に記載のエポキシ樹脂組成物で、半導体素子を封止した半導体装置。
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