CN107207706A - 鏻化合物、含有其的环氧树脂组成物及使用其制造的半导体装置 - Google Patents
鏻化合物、含有其的环氧树脂组成物及使用其制造的半导体装置 Download PDFInfo
- Publication number
- CN107207706A CN107207706A CN201680007118.4A CN201680007118A CN107207706A CN 107207706 A CN107207706 A CN 107207706A CN 201680007118 A CN201680007118 A CN 201680007118A CN 107207706 A CN107207706 A CN 107207706A
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- China
- Prior art keywords
- epoxy resin
- formula
- resin component
- phenol
- phosphonium compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 173
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 173
- 239000004065 semiconductor Substances 0.000 title claims abstract description 41
- 150000004714 phosphonium salts Chemical class 0.000 title claims abstract description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000005011 phenolic resin Substances 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 27
- -1 trihydroxy methyl Chemical group 0.000 claims description 21
- 238000001721 transfer moulding Methods 0.000 claims description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 15
- 229920003986 novolac Polymers 0.000 claims description 15
- 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 claims description 14
- 239000011256 inorganic filler Substances 0.000 claims description 14
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 14
- 238000003860 storage Methods 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 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 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 229930003836 cresol Natural products 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 229940106691 bisphenol a Drugs 0.000 claims description 5
- 238000005259 measurement Methods 0.000 claims description 5
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 4
- 229930185605 Bisphenol Natural products 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 3
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical class C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 claims description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 claims description 3
- IMHDGJOMLMDPJN-UHFFFAOYSA-N dihydroxybiphenyl Natural products OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 claims description 3
- 150000008442 polyphenolic compounds Polymers 0.000 claims description 3
- 150000003505 terpenes Chemical class 0.000 claims description 3
- 235000007586 terpenes Nutrition 0.000 claims description 3
- 239000004844 aliphatic epoxy resin Substances 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 2
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 claims description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 22
- 239000000470 constituent Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- 239000005350 fused silica glass Substances 0.000 description 12
- 238000000465 moulding Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 238000007711 solidification Methods 0.000 description 11
- 230000008023 solidification Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920002545 silicone oil Polymers 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 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 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 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 4
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical class OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000010426 asphalt Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
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- 238000012360 testing method Methods 0.000 description 4
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- 238000010521 absorption reaction Methods 0.000 description 3
- UNRQTHVKJQUDDF-UHFFFAOYSA-N acetylpyruvic acid Chemical compound CC(=O)CC(=O)C(O)=O UNRQTHVKJQUDDF-UHFFFAOYSA-N 0.000 description 3
- 239000002313 adhesive film Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001639 boron compounds Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000002903 organophosphorus compounds Chemical class 0.000 description 3
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 3
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- 239000000047 product Substances 0.000 description 3
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- 239000013589 supplement Substances 0.000 description 3
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 3
- ARWCZKJISXFBGI-UHFFFAOYSA-N (3,4-dihydroxyphenyl)-phenylmethanone Chemical compound C1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 ARWCZKJISXFBGI-UHFFFAOYSA-N 0.000 description 2
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical class OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-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
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 2
- UVTGXFAWNQTDBG-UHFFFAOYSA-N [Fe].[Pb] Chemical compound [Fe].[Pb] UVTGXFAWNQTDBG-UHFFFAOYSA-N 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
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- VEWFZHAHZPVQES-UHFFFAOYSA-N boron;n,n-diethylethanamine Chemical compound [B].CCN(CC)CC VEWFZHAHZPVQES-UHFFFAOYSA-N 0.000 description 1
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
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- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
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- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- QLAGHGSFXJZWKY-UHFFFAOYSA-N triphenylborane;triphenylphosphane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QLAGHGSFXJZWKY-UHFFFAOYSA-N 0.000 description 1
- MHNHYTDAOYJUEZ-UHFFFAOYSA-N triphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MHNHYTDAOYJUEZ-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- 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
- C08G59/68—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 catalysts used
- C08G59/688—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 catalysts used containing phosphorus
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/08—Dihydroxy benzenes; Alkylated derivatives thereof
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
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- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/235—Metal derivatives of a hydroxy group bound to a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
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- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- 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
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- 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
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K13/04—Ingredients characterised by their shape and organic or inorganic ingredients
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K3/34—Silicon-containing compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/50—Phosphorus bound to carbon only
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- H01L23/3107—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape the device being completely enclosed
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C2603/02—Ortho- or ortho- and peri-condensed systems
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- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
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Abstract
本发明是有关于一种由式1表示的鏻化合物、包含其的环氧树脂组成物及使用其制造的半导体装置。
Description
技术领域
本发明是关于鏻化合物、包含其的环氧树脂组成物以及使用其制造的半导体装置。
背景技术
转移(transfer)模塑由于其低成本及适用于大批量生产的优势而被广泛用作用环氧树脂组成物封装诸如IC(集成电路)及LSI(大规模集成电路)晶片的半导体装置以获得半导体装置的方法。在转移模塑中,作为固化剂的环氧树脂或酚树脂的改性可以改进半导体装置的特性及可靠性。
所述环氧树脂组成物包含环氧树脂、固化剂、固化催化剂等。作为固化催化剂,通常采用咪唑催化剂、胺催化剂以及膦催化剂。
在朝向紧密、轻质并且高效能电子装置的趋势下,半导体装置的高积集度已经逐年加快。随着对半导体装置的表面安装的需求递增,出现了现有环氧树脂组成物未解决的问题。半导体装置的封装材料的其他要求为快速可固化性,以提高生产力及储存稳定性以提高分配及储存期间的处置效能。
韩国专利公开案第2014-0082528号揭示一种使用四价鏻盐的环氧树脂固化催化剂。
发明内容
技术问题
本发明的一个实施例为提供一种用于固化催化剂的化合物,其能够加速固化环氧树脂,具有良好的模塑时流动性及高固化强度,并且甚至可在短固化时间下固化。
本发明的另一实施例为提供一种用于固化催化剂的化合物,其能够在低温下加速固化环氧树脂。
本发明的另一实施例为提供一种用于固化催化剂的化合物,其具有高储存稳定性,仅在所要固化温度下催化固化,但在偏离所要固化温度的温度下不显示任何固化活性。
本发明的另一实施例为提供一种包含所述环氧树脂组成物的半导体装置。
技术解决方案
本发明的一个实施例是关于一种鏻化合物,所述鏻化合物由式1表示:
[式1]
(在式1中,R1、R2、R3、R4、X、Y、1、m以及n如实施方式中所定义)。
在所述鏻化合物中,R1、R2、R3以及R4可以为C6至C30芳基。
当R1、R2、R3以及R4为C6至C30芳基时,R1、R2、R3以及R4中的至少一个可以经羟基取代。
X可以为C6至C30芳基。
所述鏻化合物可以为由式1a至式1f表示的化合物中的任一个:
[式1a]
[式1b]
[式1c]
[式1d]
[式1e]
[式1f]
本发明的另一实施例是关于一种环氧树脂组成物。所述环氧树脂组成物包含环氧树脂、固化剂、无机填充剂以及固化催化剂,其中所述固化催化剂包含充当固化加速剂的鏻化合物。
环氧树脂可以包含以下各个中的至少一个:双酚A型环氧树脂、双酚F型环氧树脂、苯酚酚醛清漆型环氧树脂、第三丁基儿茶酚型环氧树脂、萘型环氧树脂、缩水甘油基胺型环氧树脂、甲酚酚醛清漆型环氧树脂、联苯型环氧树脂、线性脂族环氧树脂、环脂族环氧树脂、杂环环氧树脂、含螺环的环氧树脂、环己烷二甲醇型环氧树脂、三羟甲基型环氧树脂以及卤化环氧树脂。
固化剂可以包含酚树脂。
固化剂可以包含以下各个中的至少一个:苯酚芳烷基型酚树脂、苯酚酚醛清漆型酚树脂、扎洛克型酚树脂、甲酚酚醛清漆型酚树脂、萘酚型酚树脂、萜烯型酚树脂、多官能酚树脂、二环戊二烯类酚树脂、从双酚A及间苯二酚合成的酚醛清漆型酚树脂、包含三(羟基苯基)甲烷及二羟基联苯的多羟基酚化合物、包含顺丁烯二酸酐及邻苯二甲酸酐的酸酐、间苯二胺、二胺基二苯基甲烷以及二胺基二苯砜。
固化催化剂可以按约0.01重量%至约5重量%的量存在于环氧树脂组成物中。
鏻化合物可以按约10重量%至约100重量%的量存在于固化催化剂中。
如根据方程式1所计算,环氧树脂组成物可以具有约0.4%或小于0.4%的固化收缩率:
<方程式1>
固化收缩率=|C-D|/C×100,
(在方程式1中,C为通过在175℃下在70公斤力/平方厘米的负载下对环氧树脂组成物进行转移模塑所获得的样本的长度,并且D为在170℃至180℃下后固化所述样本4小时并且冷却之后,所述样本的长度)。
如根据方程式2所计算,环氧树脂组成物可以具有约80%或大于80%的储存稳定性:
<方程式2>
储存稳定性=(F1-F0)/F0×100
(在方程式2中,F1为在25℃/50%相对湿度下储存所述环氧树脂组成物72小时之后,使用转移模塑压床(transfer molding press),在175℃及70公斤力/平方厘米下,根据EMMI-1-66测量的所述环氧树脂组成物的流动长度(寸),并且F0为所述环氧树脂组成物的初始流动长度(寸)。)
本发明的另一实施例是关于一种用所述环氧树脂组成物包覆的半导体装置。
有利效应
本发明可以提供一种能够加速固化环氧树脂及在低温下固化环氧树脂的鏻化合物。
另外,包含本发明的鏻化合物的环氧树脂组成物可甚至在预定范围的时间及温度下使粘度改变降至最低。因此,在高温下固化之后获得的环氧树脂组成物不会由于流动性降低而展现出模塑产物的可模塑性、机械特性、电特性以及化学特性的任何劣化。
附图说明
图1为根据本发明的一个实施例的半导体装置的截面视图。
图2为本发明的另一实施例的半导体装置的截面视图。
图3为本发明的另一实施例的半导体装置的截面视图。
具体实施方式
如本文所用,在“经取代或未经取代”中的术语“经取代”意指对应的官能团中的至少一个氢原子经以下各个取代:羟基、卤素原子、氨基、硝基、氰基、C1至C20烷基、C1至C20卤烷基、C6至C30芳基、C3至C30杂芳基、C3至C10环烷基、C3至C10杂环烷基、C7至C30芳烷基或C1至C30杂烷基。术语“卤基”意指氟、氯、碘或溴。
如本文所用,术语“芳基”是指如下取代基,其中环状取代基中的所有元素具有p轨域并且p轨域形成共轭系统。芳基可以例如为单环或稠合(fused)多环(polycyclic)C6至C30烃基。芳基的特定实例包含苯基、联苯基、萘基、萘酚基以及蒽基,但不限于这些。
如本文所用,术语“杂芳基”意指如下C6至C30芳基,其中环包括碳原子及1至3个由氮、氧、硫以及磷中选出的杂原子。杂芳基的实例包含但不限于吡啶基、吡嗪基、嘧啶基、哒嗪基、三嗪基、喹啉基、异喹啉基、喹喏啉基、吖啶基、喹唑啉基、噌啉基、酞嗪基、噻唑基、苯并噻唑基、异恶唑基、苯并异恶唑基、恶唑基、苯并恶唑基、吡唑基、吲唑基、咪唑基、苯并咪唑基、嘌呤基、噻吩基、苯并噻吩基、呋喃基、苯并呋喃基或异苯并呋喃基。
如本文所用,术语“杂”是指由氮(N)、氧(O)、硫(S)或磷(P)中选出的原子。
鏻化合物
首先,将描述根据本发明的鏻化合物。
根据本发明的鏻化合物由式1表示:
[式1]
在式1中,R1、R2、R3以及R4各自独立地为经取代或未经取代的C1至C30脂族烃基、经取代或未经取代的C6至C30芳族烃基或经取代或未经取代的包含杂原子的C1至C30烃基;
X及Y彼此不同且各自独立地为经取代或未经取代的C1至C30脂族烃基、经取代或未经取代的C6至C30芳族烃基或经取代或未经取代的包含杂原子的C1至C30烃基;1为0至4的整数;m为1至6的整数;且n为1至5的整数。
在式1中,R1、R2、R3以及R4可以为C6至C30芳基。
在式1中,R1、R2、R3以及R4中的至少一个可以经羟基取代。
在式1中,X可以为C6至C30芳基。在此实施例中,包含鏻化合物的组成物可具有相对良好流动性及可模塑性以及良好储存稳定性。
所述鏻化合物可以为例如由式1a到式1f表示的化合物中的任一个:
[式1a]
[式1b]
[式1c]
[式1d]
[式1e]
[式1f]
所述鏻化合物可以添加到包含环氧树脂、固化剂以及无机填充剂中的至少一个的组成物中以便用作潜在固化催化剂。
根据本发明的鏻化合物可以提供如下环氧树脂组成物,所述环氧树脂组成物能够加速固化环氧树脂及固化剂并且能够确保低温可固化性及较高储存稳定性,同时使包含所述化合物以及环氧树脂、固化剂等的混合物的粘度改变降至最低,甚至在所需时间及温度范围内。储存稳定性是指如下活性,其仅在所需固化温度下催化固化,在偏离所需固化温度范围的温度下无任何固化活性。因此,有可能储存环氧树脂组成物较长时间,且不引起粘度变化。一般而言,固化反应的进行在环氧树脂组成物为液体时会导致粘度增加及流动性劣化,并且在环氧树脂组成物为固体时可以展现粘度。
根据本发明的鏻化合物经由在具有酚类-OH基团的不同化合物之间生成簇而形成单价阴离子。在所述化合物中,阳离子及阴离子的位置经适当安排,从而允许两个分子之间的离子键相对较强。由于所述簇利用相对较弱氢键形成,故施加足够热能将快速断裂氢键以破坏阴离子簇,从而使阳离子及阴离子解离,此将引起快速固化反应。因此,鏻化合物可展现相对较长流动性同时在固化持续相同的固化时间之后维持相同的固化强度。
环氧树脂组成物
接下来,将描述根据本发明的环氧树脂组成物。
根据本发明的环氧树脂组成物可包含环氧树脂、固化剂、无机填充剂以及固化催化剂中的至少一个。在下文中,将更详细地描述本发明的环氧树脂组成物的每一组分。
(1)环氧树脂
环氧树脂可以每分子具有两个或超过两个环氧基。环氧树脂的实例包含双酚A型环氧树脂、双酚F型环氧树脂、苯酚酚醛清漆型环氧树脂、第三丁基儿茶酚型环氧树脂、萘型环氧树脂、缩水甘油基胺型环氧树脂、甲酚酚醛清漆型环氧树脂、联苯型环氧树脂、线性脂族环氧树脂、环脂族环氧树脂、杂环环氧树脂、含螺环的环氧树脂、环己烷二甲醇型环氧树脂、三羟甲基型环氧树脂以及卤化环氧树脂,但不限于这些。这些环氧树脂可单独使用或以其两个以上的组合形式使用。举例而言,环氧树脂可以每分子具有两个或超过两个环氧基及一个或多个羟基。环氧树脂可以包含固相环氧树脂及液相环氧树脂中的至少一个。较佳地使用固相环氧树脂。
在一个实施例中,环氧树脂可以为由式2表示的联苯型环氧树脂、由式3表示的苯酚芳烷基型环氧树脂或其组合:
[式2]
(在式2中,R为C1至C4烷基且a平均为0至7的数字。)
[式3]
(在式3中,b平均为1至7的数字)。
就固体含量而言,所述组成物所包含的环氧树脂的量可以为约2重量%至约17重量%,例如约3重量%至约15重量%,例如约3重量%至约12重量%。在此范围内,所述组成物可以确保可固化性。
(2)固化剂
固化剂可以包含苯酚芳烷基型酚树脂、苯酚酚醛清漆型酚树脂、扎洛克型酚树脂、甲酚酚醛清漆型酚树脂、萘酚型酚树脂、萜烯型酚树脂、多官能酚树脂、二环戊二烯类酚树脂、自双酚A及甲阶酚醛树脂合成的酚醛清漆型酚树脂、包含三(羟基苯基)甲烷及二羟基联苯的多羟基酚化合物、包含顺丁烯二酸酐及邻苯二甲酸酐的酸酐以及包含间苯二胺、二胺基二苯基甲烷、二胺基二苯砜的芳族胺等。较佳地,固化剂可以为具有一个或多个羟基的酚树脂。
在一个实施例中,固化剂可以为由式4表示的扎洛克型酚树脂及由式5表示的苯酚芳烷基型酚树脂。
[式4]
(在式4中,c平均为0至7的数字。)
[式5]
(在式5中,d平均为1至7的数字。)
就固体含量而言,环氧树脂组成物所包含的固化剂的量可以为约0.5重量%至约13重量%,例如约1重量%至约10重量%,例如约2重量%至约8重量%。在此范围内,所述组成物可以确保可固化性。
(3)无机填充剂
环氧树脂组成物可还包含无机填充剂。无机填充剂用于改进环氧树脂组成物的机械特性,同时降低其应力。无机填充剂的实例包含以下各个中的至少一个:熔融硅石、结晶硅石、碳酸钙、碳酸镁、氧化铝、氧化镁、粘土(clay)、滑石(talc)、硅酸钙、氧化钛、氧化锑以及玻璃纤维。
就降低应力而言,具有低线性膨胀系数的熔融硅石为较佳的。熔融硅石是指比重为2.3或小于2.3的非结晶硅石。熔融硅石可以通过熔融结晶硅石制备或可以包含由各种原材料合成的非结晶硅石产物。熔融硅石的形状及粒子直径不受特定限制。无机填充剂可以包含以无机填充剂的总重量计40重量%至100重量%的熔融硅石混合物,其中熔融硅石混合物包含约50重量%至约99重量%的平均粒子直径为约5微米至约30微米的球形熔融硅石及约1重量%至约50重量%的平均粒子直径为约0.001微米至约1微米的球形熔融硅石。取决于环氧树脂组成物的应用,无机填充剂也可以调整至约45微米、约55微米或约75微米的最大粒子直径。球形熔融硅石可以在硅石表面上包含导电碳作为外来物质。球形熔融硅石必须并有较少量的极性外来物质。
取决于环氧树脂组成物的所需物理特性,例如可模塑性、低应力特性以及高温强度,无机填充剂可以按恰当量存在。具体而言,无机填充剂可以按以环氧树脂组成物的总重量计约60重量%至约95重量%、较佳地约75%至约92重量%的量存在。在此范围内,环氧树脂组成物可以确保良好的阻燃性、流动性以及可靠性。
固化催化剂
环氧树脂组成物可以包含固化催化剂,所述固化催化剂包含由式1表示的鏻化合物。鏻化合物可以按约0.01重量%至约5重量%、例如约0.02重量%至约1.5重量%、例如约0.05重量%至约1.5重量%的量存在于环氧树脂组成物中。在此范围内,环氧树脂组成物可以确保流动性,但不延长固化反应时间。
环氧树脂组成物可以还包含不含鏻的非鏻固化催化剂。非鏻固化催化剂的实例可以包含三级胺、有机金属化合物、有机磷化合物、咪唑、硼化合物等。三级胺的实例可以包含苯甲基二甲胺、三乙醇胺、三亚乙基二胺、二乙基胺基乙醇、三(二甲基胺基甲基)苯酚、2-2-(二甲基胺基甲基)苯酚、2,4,6-三(二胺基甲基)苯酚、己酸三-2-乙酯等。有机金属化合物的实例包含乙酰丙酮酸铬、乙酰丙酮酸锌、乙酰丙酮酸镍等。有机磷化合物的实例可以包含三-4-甲氧基膦、三苯基膦、三苯基膦三苯基硼烷、三苯基膦-1,4-苯醌加合物等。咪唑的实例可以包含2-甲基咪唑、2-苯基咪唑、2-胺基咪唑、2-甲基-1-乙烯基咪唑、2-乙基-4-甲基咪唑、2-十七烷基咪唑及类似物。硼化合物的实例可以包含硼酸三苯基膦四苯酯、硼酸四苯酯、三氟硼烷正己胺、三氟硼烷单乙胺、四氟硼烷三乙胺、四氟硼烷胺等。另外,有可能使用1,5-二氮杂双环[4.3.0]壬-5-烯(1,5-diazabicyclo[43.0]non-5-ene:DBN)、1,8-二氮杂双环[5.4.0]十一-7-烯(1,8-diazabicyclo[5.4.0]undec-7-ene:DBU)、苯酚酚醛清漆树脂盐等。确切而言,有机磷化合物、硼化合物以及胺或咪唑固化促进剂可以单独使用或以组合形式使用。通过使环氧树脂或固化剂预反应获得的加合物可以用作固化催化剂。
根据本发明的鏻化合物可以按以固化催化剂的总重量计约10重量%至约100重量%、例如约60重量%至约100重量%的量存在。在此范围内,环氧树脂组成物可以确保流动性,但不延长固化反应时间。
固化催化剂可以按约0.01重量%至约5重量%、例如约0.02重量%至约1.5重量%、例如约0.05重量%至约1.5重量%的量存在于环氧树脂组成物中。在此范围内,环氧树脂组成物可以确保流动性,但不延长固化反应时间。
根据本发明的组成物可以还包含典型的添加剂。在一个实施例中,所述添加剂可以包含以下各个中的至少一个:偶合剂、脱模剂、应力松弛剂、交联强化剂、流平剂以及着色剂。
偶合剂可以包含由环氧硅烷、胺基硅烷、巯基硅烷、烷基硅烷以及烷氧基硅烷中选出的至少一个,但不限于这些。偶合剂可以按约0.1重量%至约1重量%的量存在于环氧树脂组成物中。
脱模剂可以包含由石蜡、酯蜡、高级脂肪酸、高级脂肪酸的金属盐、天然脂肪酸以及天然脂肪酸金属盐中选出的至少一个。脱模剂可以按约0.1重量%至约1重量%的量存在于环氧树脂组成物中。
应力释放剂可以包含由改性硅酮油、硅酮弹性体、硅酮粉末以及硅酮树脂中选出的至少一个,但不限于这些。应力释放剂可以视情况按约0重量%至约6.5重量%、例如约0重量%至约1重量%、例如约0.1重量%至约1重量%的量存在于环氧树脂组成物中。关于改性硅酮油,可以使用具有良好耐热性的任何硅酮聚合物。改性硅酮油可以包含以环氧树脂组成物的总重量计约0.05重量%至约1.5重量%的硅酮油混合物,其中所述混合物包含由以下各个所组成的群组中的至少一个或两个:具有环氧基官能团的硅酮油、具有胺官能团的硅酮油、具有羧基官能团的硅酮油以及其组合。然而,若硅酮油的量大于1.5重量%,则容易发生表面污染并且会遭遇过长树脂溢出(bleed)。若硅酮油的量小于0.05重量%,则会存在如下问题:无法获得足够低的弹性模量。另外,平均粒子直径为15微米的硅酮粉末为尤其较佳的,因为所述粉末不会降低可模塑性。硅酮粉末可以视情况按以环氧树脂组成物的总重量计0重量%至5重量%、例如0.1重量%至5重量%的量存在。
添加剂可以按0.1重量%至10重量%、例如0.1重量%至3重量%的量存在于环氧树脂组成物中。
环氧树脂组成物可在低温下固化。举例而言,固化引发温度可以介于90℃至120℃范围内。在此范围内,环氧树脂组成物可以在低温下固化,从而确保在低温下固化。
环氧树脂组成物可具有使用转移模塑压床在175℃及70公斤力/平方厘米下根据EMMI-1-66测量的59寸至75寸、较佳地65寸至85寸的流动长度。在此范围内,环氧树脂组成物可用于广泛应用中,用于包覆半导体装置、粘性膜、诸如预浸材料等的绝缘树脂片、电路板、阻焊剂、底层填料、晶粒接合材料、组分补充树脂等。
如根据方程式1所计算,环氧树脂组成物可以具有0.40%或小于0.40%、例如0.01%至0.39%的固化收缩率。在此范围内,环氧树脂组成物可用于需要此类环氧树脂组成物的广泛应用中,用于包覆半导体装置、粘性膜、诸如预浸材料等的绝缘树脂片、电路板、阻焊剂、底层填料、晶粒接合材料、组分补充树脂等。
<方程式1>
固化收缩率=|C-D|/C×100
(在方程式1中,C为通过在175℃下,在70公斤力/平方厘米的负载下对环氧树脂组成物进行转移模塑获得的样本的长度,并且D为在170℃至180℃下后固化所述样本4小时并且冷却之后,所述样本的长度)。
如根据方程式2所计算,环氧树脂组成物可以具有约80%或大于80%、较佳约90%或大于90%的储存稳定性:
<方程式2>
储存稳定性=(F1-F0)/F0×100
(在方程式2中,F1为在25℃/50%RH下储存所述组成物72小时之后,使用转移模塑压床(transfer molding press),在175℃及70公斤力/平方厘米下,根据EMMI-1-66测量的所述环氧树脂组成物的流动长度(寸),并且F0为所述环氧树脂组成物的初始流动长度(寸))。
在环氧树脂组成物中,环氧树脂可以单独使用或以加合物形式使用,所述加合物诸如熔融母料(melt master bach),通过环氧树脂与诸如固化剂、固化催化剂、脱模剂、偶合剂以及应力松弛剂的添加剂的预反应获得。虽然关于根据本发明的环氧树脂组成物的制备方法不存在特定限制,但是环氧树脂组成物可以通过如下制备:使用合适的混合器均匀地混合树脂组成物的所有组分,紧接着在辊筒研磨机或捏合机中,在90℃至120℃下熔融捏合,冷却并且研磨。
根据本发明的环氧树脂组成物可以用于需要此类环氧树脂组成物的广泛应用中,用于包覆半导体装置、粘性膜、诸如预浸材料等的绝缘树脂片、电路基板、阻焊剂、底层填料、晶片接合材料以及组分补充树脂,但不限于这些。
半导体装置的包覆
接下来,将描述根据本发明的半导体装置。
根据本发明的半导体装置可以用环氧树脂组成物包覆。
图1为根据本发明的一个实施例的半导体装置的截面视图。参看图1,根据一个实施例的半导体装置(100)包含接线板(10)、形成于接线板(10)上的凸块(30)以及形成于凸块(30)上的半导体晶片(20),其中接线板(10)与半导体晶片(20)之间的间隙用环氧树脂组成物(40)包覆,并且环氧树脂组成物可以为根据本发明实施例的环氧树脂组成物。
图2为根据本发明的另一实施例的半导体装置的截面视图。参看图2,根据另一实施例的半导体装置(200)包含接线板(10)、形成于接线板(10)上的凸块(30)以及形成于凸块(30)上的半导体晶片(20),其中接线板(10)与半导体晶片(20)之间的间隙及半导体晶片(30)的整个顶表面用环氧树脂组成物(40)包覆,并且环氧树脂组成物可以为根据本发明实施例的环氧树脂组成物。
图3为根据本发明的另一实施例的半导体装置的截面视图。参看图3,根据另一实施例的半导体装置(300)包含接线板(10)、形成于接线板(10)上的凸块(30)以及形成于凸块(30)上的半导体晶片(20),其中接线板(10)与半导体晶片(20)之间的间隙及半导体晶片(30)中除了半导体晶片(30)顶表面的整个侧表面用环氧树脂组成物(40)包覆,并且环氧树脂组成物可以为根据本发明实施例的环氧树脂组成物。
在图1至图3中,接线板、凸块以及半导体晶片各自的大小以及凸块的数量为视情况的并且可以修改。
半导体装置可以最常用环氧树脂组成物通过低压转移模塑来包覆。然而,半导体装置也可以通过注塑(injection)、浇铸(casting)等模塑。可以利用此类模塑制程制造的半导体装置可以包含铜引线框架、铁引线框架、预镀覆至少一种由镍、铜以及钯中选出的金属的铁引线框架或有机层压框架。
本发明的模式
接下来,将参考一些实例更详细描述本发明。应了解,这些实例只是为了说明而提供的,并且不应以任何方式理解为限制本发明。
实例
制备实例1:制备由式1a表示的鏻化合物
向50克MeOH中添加13.5克3,4-二羟基苯甲腈(3,4-Dihydroxybenzonitrile)及17.0克2-苯基苯酚(2-phenylphenol),紧接着添加21.6克25%甲醇钠溶液(sodiummethoxide solution),其继而完全溶解同时在室温下反应30分钟。向所述溶液中缓慢添加41.9克预先溶解于50克甲醇中的四苯基溴化鏻(tetraphenylphosphonium bromide)的溶液,且允许混合物进一步反应1小时,接着引入300克蒸馏水。过滤所得白色固体,获得54克化合物。所述化合物基于NMR资料鉴别为由式1a表示的化合物。
[式1a]
1H NMR δ8.00-7.94(4H,dt),7.85-7.70(16H,m),7.44-7.38(6H,m),6.88-6.83(6H,m)
制备实例2:制备由式1b表示的鏻化合物
向50克MeOH中添加21.4克3,4-二羟基二苯甲酮(3,4-Dihydroxybenzophenone)及12.4克4-甲基儿茶酚(4-methylcatechol),紧接着添加21.6克25%甲醇钠溶液(sodiummethoxide solution),其继而完全溶解同时在室温下反应30分钟。向所述溶液中缓慢添加41.9克预先溶解于50克甲醇中的四苯基溴化鏻(tetraphenylphosphonium bromide)的溶液,且允许混合物进一步反应1小时,接着引入300克蒸馏水。过滤所得棕色固体,获得60克化合物。所述化合物基于NMR资料鉴别为由式1b表示的化合物。
[式1b]
1H NMRδ8.00-7.94(4H,dt),7.85-7.70(16H,m),7.60(2H,d),7.43-7.38(3H,m),7.09(1H,d),6.97(1H,s),6.75-6.71(3H,m),6.51(1H,d),2.21(3H,s)
制备实例3:制备由式1c表示的鏻化合物
向50克MeOH中添加21.4克2,4-二羟基二苯甲酮(2,4-Dihydroxybenzophenone)及35.0克9,9-双(4-羟苯基)茀(9,9-Bis(4-hydroxyphenyl)fluorine),紧接着添加21.6克25%甲醇钠溶液(sodium methoxide solution),其继而完全溶解同时在室温下反应30分钟。向所述溶液中缓慢添加41.9克预先溶解于50克甲醇中的四苯基溴化鏻(tetraphenylphosphonium bromide)的溶液,且允许混合物进一步反应1小时,接着引入300克蒸馏水。过滤所得白色固体,获得66克化合物。所述化合物基于NMR资料鉴别为由式1c表示的化合物。
[式1c]
1H NMRδ8.00-7.94(4H,dt),7.85-7.70(18H,m),7.60(2H,d),7.47(2H,d),7.30-7.24(8H,m),6.88(4H,d),6.61(4H,d),6.34(1H,d),6.21(1H,s)
制备实例4:制备由式1d表示的鏻化合物
向50克MeOH中添加23.0克2,3,4-三羟基二苯甲酮(2,3,4-trihydroxybenzophenone)及12.4克连苯三酚(pyrogallol),紧接着添加21.6克25%甲醇钠溶液(sodium methoxide solution),其继而完全溶解同时在室温下反应30分钟。向所述溶液中缓慢添加41.9克预先溶解于50克甲醇中的四苯基溴化鏻(tetraphenylphosphoniumbromide)的溶液,且允许混合物进一步反应1小时,接着引入300克蒸馏水。过滤所得棕色固体,获得61克化合物。所述化合物基于NMR资料鉴别为由式1d表示的化合物。
[式1d]
1H NMRδ8.00-7.94(4H,dt),7.85-7.70(16H,m),7.60(2H,d),7.32-7.27(3H,m),6.96(1H,d),6.55-6.50(2H,m),6.06(2H,d)
制备实例5:制备由式1e表示的鏻化合物
向1升圆底烧瓶中引入100克三苯基膦(triphenylphosphine)、60克4-溴苯酚(4-Bromophenol)以及3.7克NiBr2,紧接着添加130克乙二醇(ethylene glycol),并且接着在180℃下反应6小时,从而获得由式1e′表示的具有经取代的苯酚的溴化鏻。
[式1e′]
向50克MeOH中添加21.4克2,4-二羟基二苯甲酮(2,4-dihydroxybenzophenone)及18.4克2,2-联苯酚(2,2-Biphenol),紧接着添加21.6克25%甲醇钠溶液(sodiummethoxide solution),其继而完全溶解同时在室温下反应30分钟。向所述溶液中缓慢添加43.5克预先溶解于50克甲醇中的由式1e′表示的溴化鏻的溶液,且允许混合物进一步反应1小时,接着引入300克蒸馏水。过滤所得白色固体,获得68克化合物。所述化合物基于NMR资料鉴别为由式1e表示的化合物。
[式1e]
1H NMRδ7.87(3H,t),7.77-7.73(6H,m),7.69-7.65(6H,m),7.60(2H,d),7.39(1H,dd),7.32(2H,d),7.28-7.24(3H,m),7.08-7.02(4H,m),6.88(2H,dd),6.79(2H,d),6.55(2H,dd),6.34(1H,d),6.21(1H,s)
制备实例6:制备由式1f表示的鏻化合物
向50克MeOH中添加21.4克3,4-二羟基二苯甲酮(3,4-dihydroxybenzophenone)及12.4克间苯三酚(phloroglucinol),紧接着添加21.6克25%甲醇钠溶液(sodiummethoxide solution),其继而完全溶解同时在室温下反应30分钟。向所述溶液中缓慢添加43.5克预先溶解于50克甲醇中的由式1e′表示的溴化鏻的溶液,且允许混合物进一步反应1小时,接着引入300克蒸馏水。过滤所得白色固体,获得61克化合物。所述化合物基于NMR资料鉴别为由式1f表示的化合物。
[式1f]
1H NMRδ7.87(3H,t),7.77-7.73(6H,m),7.69-7.65(6H,m),7.60(2H,d),7.42-7.37(3H,m),7.09(1H,d),6.97(1H,s),6.88(2H,dd),6.55(2H,dd),6.51(1H,d),5.83(3H,s)
实例及比较例中所用的组分详情如下。
(A)环氧树脂
NC-3000(日本化药)用作联苯型环氧树脂。
(B)固化剂
HE100C-10(爰沃特)用作扎洛克型酚树脂。
(C)固化催化剂
在制备实例1至制备实例6中制备的鏻化合物用作(C1)至(C6)。
(C7)
三苯基膦(Triphenyl phosphine)
(C8)
三苯基膦及1,4-苯醌的加合物
(D)无机填充剂
使用平均粒子直径为18微米的球形熔融硅石及平均粒子直径为0.5微米的球形熔融硅石9∶1(重量比)的混合物。
(E)偶合剂
使用(e1)巯基丙基三甲氧基硅烷KBM-803(信越)及(e2)甲基三甲氧基硅烷SZ-6070(道康宁化学公司)的混合物。
(F)添加剂
使用(f1)巴西棕榈蜡作为脱模剂并且使用(f2)碳黑MA-600(松下化学)作为着色剂。
实例及比较例
对组分进行称重,如表1中所列(单位:重量份)并且使用亨舍尔混合器均匀地混合,从而制备第一粉末组成物。接着,利用连续式捏合机,在95℃下,熔融捏合所述组成物中的每一个,将其冷却并且研磨,从而制备用于包覆半导体装置的环氧树脂组成物。
表1
借助于以下测量方法评估实例及比较例中制造的环氧树脂组合物及其中使用相应环氧树脂组成物的封装的表2中列出的物理特性。
(1)流动性(寸):使用转移模塑压床(transfer molding press),在试验模具中,在175℃及70公斤力/平方厘米下,根据EMMI-1-66测量环氧树脂组成物中的每一个的流动长度。所测得的值越高,表示流动性越好。
(2)固化收缩率(%):使用转移模塑压床(transfer molding press),在用于挠曲强度样本构造的ASTM模具中,在175℃及70公斤力/平方厘米下,模塑环氧树脂组成物中的每一个,从而获得模塑样本(125×12.6×6.4毫米)。使所述样本在烘箱中,在170℃至180℃下,经历模塑后固化(PMC:post-molding cure)4小时。在冷却之后,使用卡尺测量样本长度。根据方程式1计算环氧树脂组成物的固化收缩率:
<方程式1>
固化收缩率=|C-D|/C×100
(在方程式1中,C为通过在175℃下在70公斤力/平方厘米的负载下对环氧树脂组成物进行转移模塑所获得的样本的长度,并且D为在170℃至180℃下后固化所述样本4小时并且冷却之后,所述样本的长度)。
(3)玻璃转化温度(℃):使用热机械分析仪(Thermomechanical Analyzer,TMA),在以10℃/分钟的速率从25℃加热至300℃的同时以TMA测量玻璃转化温度。
(4)吸湿率(%);在170℃至180℃的模具温度、70公斤/平方厘米的夹持压力、1,000psi的转移压力以及0.5厘米/秒至1厘米/秒的转移速度下,对在实例及比较例中制备的树脂组成物中的每一个进行模塑,持续120秒固化时间,从而获得呈直径为50毫米并且厚度为1.0毫米的圆盘形式的固化样本。使所述样本在烘箱中,在170℃至180℃下,经历模塑后固化(PMC:post molding cure)4小时,并且在85℃及85%RH下静置168小时。测量样本在吸湿之前及之后的重量。根据方程式3计算树脂组成物的吸湿率:
<方程式3>
吸湿率=(样本在吸湿之后的重量-样本在吸湿之前的重量)×(样本在吸湿之前的重量)×100
(5)粘合强度(kgf):以试验片形式制备大小适应模具的铜金属装置用于粘合强度测量。在试验片上,在170℃至180℃的模具温度、70公斤力/平方厘米的夹持压力、1,000psi时的转移压力以及0.5厘米/秒至1厘米/秒的转移速度下,对在实例及比较例中制备的树脂组成物中的每一个进行模塑,持续120秒固化时间,从而获得固化样本。使所述样本在烘箱中,在170℃至180℃下,经历模塑后固化(PMC:post molding cure)4小时。与所述样本接触的环氧树脂组成物的面积为40±1平方毫米。使用UTV(万能试验机)测量环氧树脂组成物的粘合强度。每个组成物产生12个样本。在重复测量程序之后,对所测得的粘合强度值取平均。
(6)固化度(肖氏D):使用配备有模具的MPS(多活塞系统),在175℃下固化环氧树脂组成物中的每一个,持续40秒、50秒、60秒、70秒以及80秒,从而构造出eTQFP(暴露的薄型四面扁平封装),各自包含宽度为24毫米、长度为24毫米并且厚度为1毫米的铜金属装置。使用肖氏D硬度计直接测量根据固化时间在模具上的封装中的经固化产物的硬度值。硬度值越高,表示固化度越好。
(7)储存稳定性:在将环氧树脂组成物在设定成在25℃/50%RH下的恒温恒湿器中储存一周的同时,以24小时的时间间隔,根据(1)中所述的方法测量所述组成物中的每一个的流动长度(寸)。计算储存后的流动长度相比于紧接在组成物制备后的流动长度的百分比(%)。值越高,表示储存稳定性越好。
表2
在表2中显示实例1至实例6以及比较例1及比较例2的实验结果,可以看出,鉴于每个固化时间段的可固化性,甚至在较短固化时间段中,在实例1至实例6中制备的环氧树脂组成物都具有比比较例1及比较例2的环氧树脂组成物高的流动性及比其高的固化度。关于储存稳定性,显而易见,实例1至实例6的环氧树脂组成物显示,在72小时储存后流动性改变更小。
相反地,在比较例1及比较例2中制备的不包含本发明鏻化合物的组成物具有低储存稳定性、高固化收缩率以及低流动性。因此,可以看出,呈封装形式的比较例的组成物不能确保本发明的作用。
尽管本文中已经描述了一些实施例,但所属领域中相关技术人员将显而易知,这些实施例仅以说明方式给出,并且在不脱离本发明的精神及范畴的情况下,可以进行各种修改、改变、更改以及等效实施例。本发明的范畴应仅受所附权利要求书及其等效物限制。
Claims (14)
1.一种鏻化合物,由式1表示:
[式1]
(在式1中,R1、R2、R3以及R4各自独立地为经取代或未经取代的C1至C30脂族烃基、经取代或未经取代的C6至C30芳族烃基或经取代或未经取代的包含杂原子的C1至C30烃基;X及Y彼此不同且各自独立地为经取代或未经取代的C1至C30脂族烃基、经取代或未经取代的C6至C30芳族烃基或经取代或未经取代的包含杂原子的C1至C30烃基;1为0至4的整数;m为1至6的整数;且n为1至5的整数。)
2.根据权利要求1所述的鏻化合物,其中R1、R2、R3以及R4为C6至C30芳基。
3.根据权利要求2所述的鏻化合物,其中R1、R2、R3以及R4中的至少一个经羟基取代。
4.根据权利要求1所述的鏻化合物,其中X为C6至C30芳基。
5.根据权利要求1所述的鏻化合物,其中所述鏻化合物为由式1a至式1f表示的化合物中的任一个:
[式1a]
[式1b]
[式1c]
[式1d]
[式1e]
[式1f]
6.一种环氧树脂组成物,包括:
环氧树脂、固化剂、无机填充剂以及固化催化剂,
其中所述固化催化剂包括权利要求1至5中任一项所述的鏻化合物。
7.根据权利要求6所述的环氧树脂组成物,其中所述环氧树脂包括以下各个中的至少一个:双酚A型环氧树脂、双酚F型环氧树脂、苯酚酚醛清漆型环氧树脂、第三丁基儿茶酚型环氧树脂、萘型环氧树脂、缩水甘油基胺型环氧树脂、甲酚酚醛清漆型环氧树脂、联苯型环氧树脂、线性脂族环氧树脂、环脂族环氧树脂、杂环环氧树脂、含螺环的环氧树脂、环己烷二甲醇型环氧树脂、三羟甲基型环氧树脂以及卤化环氧树脂。
8.根据权利要求6所述的环氧树脂组成物,其中所述固化剂包括酚树脂。
9.根据权利要求6所述的环氧树脂组成物,其中所述固化剂包括以下各个中的至少一个:苯酚芳烷基型酚树脂;苯酚酚醛清漆型酚树脂;扎洛克型酚树脂;甲酚酚醛清漆型酚树脂;萘酚型酚树脂;萜烯型酚树脂;多官能酚树脂;二环戊二烯类酚树脂;自双酚A及甲阶酚醛树脂合成的酚醛清漆型酚树脂;多羟基酚化合物,包含三(羟基苯基)甲烷及二羟基联苯;酸酐,包含顺丁烯二酸酐及邻苯二甲酸酐;以及芳族胺,包含间苯二胺、二胺基二苯基甲烷以及二胺基二苯砜。
10.根据权利要求6所述的环氧树脂组成物,其中所述固化催化剂以0.01重量%至5重量%的量存在于所述环氧树脂组成物中。
11.根据权利要求6所述的环氧树脂组成物,其中所述鏻化合物以10重量%至100重量%的量存在于所述固化催化剂中。
12.根据权利要求6所述的环氧树脂组成物,其中根据方程式1所计算,所述环氧树脂组成物具有不超过0.4%的固化收缩率:
<方程式1>
固化收缩率=|C-D|/C×100
(在方程式1中,C为通过在175℃及70公斤力/平方厘米下对所述环氧树脂组成物进行转移模塑所获得的样本的长度,并且D为在170℃至180℃下后固化所述样本4小时并且冷却之后所述样本的长度)。
13.根据权利要求6所述的环氧树脂组成物,其中根据方程式2所计算,所述环氧树脂组成物具有80%或大于80%的储存稳定性:
<方程式2>
储存稳定性=(F1-F0)/F0×100
(在方程式2中,F1为在25℃/50%相对湿度下储存所述环氧树脂组成物72小时之后,使用转移模塑压床(transfer molding press),在175℃及70公斤力/平方厘米下,根据EMMI-1-66测量的所述环氧树脂组成物的流动长度(寸),并且F0为所述环氧树脂组成物的初始流动长度(寸))。
14.一种半导体装置,用权利要求6所述的环氧树脂组成物包覆。
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