JP5751497B2 - 樹脂組成物及び樹脂組成物を使用して作製した半導体装置 - Google Patents
樹脂組成物及び樹脂組成物を使用して作製した半導体装置 Download PDFInfo
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- JP5751497B2 JP5751497B2 JP2012533009A JP2012533009A JP5751497B2 JP 5751497 B2 JP5751497 B2 JP 5751497B2 JP 2012533009 A JP2012533009 A JP 2012533009A JP 2012533009 A JP2012533009 A JP 2012533009A JP 5751497 B2 JP5751497 B2 JP 5751497B2
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- resin composition
- maleimide
- compound
- meth
- acrylate
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims description 59
- 239000004065 semiconductor Substances 0.000 title claims description 49
- -1 bismaleimide compound Chemical class 0.000 claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000000945 filler Substances 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 11
- 150000003923 2,5-pyrrolediones Chemical class 0.000 claims description 10
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000004185 ester group Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 60
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 14
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
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- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 239000006087 Silane Coupling Agent Substances 0.000 description 9
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- 238000006243 chemical reaction Methods 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- 238000010790 dilution Methods 0.000 description 7
- 239000012895 dilution Substances 0.000 description 7
- 239000010931 gold Substances 0.000 description 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 7
- BSIDXUHWUKTRQL-UHFFFAOYSA-N nickel palladium Chemical compound [Ni].[Pd] BSIDXUHWUKTRQL-UHFFFAOYSA-N 0.000 description 7
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
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- 125000003118 aryl group Chemical group 0.000 description 6
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
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- 239000005077 polysulfide Substances 0.000 description 6
- 229920001021 polysulfide Polymers 0.000 description 6
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- ISSDFLKUSQAECW-UHFFFAOYSA-N acetic acid;pyrrole-2,5-dione Chemical compound CC(O)=O.O=C1NC(=O)C=C1 ISSDFLKUSQAECW-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000007870 radical polymerization initiator Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 description 4
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
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- 230000008018 melting Effects 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MEQAXYISVWGLQB-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)O.C(C)C(CC=1C(=O)NC(C1)=O)CC Chemical compound C(C1=CC=CC=C1)(=O)O.C(C)C(CC=1C(=O)NC(C1)=O)CC MEQAXYISVWGLQB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
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- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
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- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical group CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 2
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 2
- CZUQOPAKOZMIPQ-UHFFFAOYSA-N 1-pentylpyrrole-2,5-dione Chemical compound CCCCCN1C(=O)C=CC1=O CZUQOPAKOZMIPQ-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- 229920001342 Bakelite® Polymers 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
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
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- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AVYKQOAMZCAHRG-UHFFFAOYSA-N triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AVYKQOAMZCAHRG-UHFFFAOYSA-N 0.000 description 1
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- FHVAUDREWWXPRW-UHFFFAOYSA-N triethoxy(pentyl)silane Chemical compound CCCCC[Si](OCC)(OCC)OCC FHVAUDREWWXPRW-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- KLFNHRIZTXWZHT-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltrisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSCCC[Si](OCC)(OCC)OCC KLFNHRIZTXWZHT-UHFFFAOYSA-N 0.000 description 1
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- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- NQRACKNXKKOCJY-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSCCC[Si](OC)(OC)OC NQRACKNXKKOCJY-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- LTOKKZDSYQQAHL-UHFFFAOYSA-N trimethoxy-[4-(oxiran-2-yl)butyl]silane Chemical compound CO[Si](OC)(OC)CCCCC1CO1 LTOKKZDSYQQAHL-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
- C08F222/404—Imides, e.g. cyclic imides substituted imides comprising oxygen other than the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
- C08F222/402—Alkyl substituted imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F32/02—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F32/04—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D135/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
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- H—ELECTRICITY
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Description
本願は、2010年9月7日に、日本に出願された特願2010−199889号に基づき優先権を主張し、その内容をここに援用する。
[1]一般式(1)で示されるマレイミド誘導体(A)と、一般式(2)で示されるビスマレイミド化合物(B)とを含む樹脂組成物。
[2]更にアリルエステル基を有する化合物(C)を含む[1]に記載の樹脂組成物。
[3]前記アリルエステル基を有する化合物(C)が脂肪族環を有するものである[2]に記載の樹脂組成物。
[4]上記化合物Cが、一般式(3)の官能基を有する[3]に記載の樹脂組成物。
[5]更に充填剤を含む[1]乃至[4]のいずれか1つに記載の樹脂組成物。
[6][1]乃至[5]のいずれか1つに記載の樹脂組成物を用いて作製した半導体装置。
なお、「(メタ)アクリレート」とは、α位に水素原子が結合したアクリレートと、α位にメチル基が結合したメタクリレートの一方あるいは両方を意味する。
マレイミド誘導体(A)(A1〜A6)の合成例を下記に示す。合成方法は以下の方法に限定されるものではなく、種々公知の方法を用いることができる。
(化合物A1:マレイミド酢酸n−ペンチルの合成)
ディーンスタークトラップを備えたセパラブルフラスコに、マレイミド酢酸(試薬)31.0(0.2mol)、p−トルエンスルホン酸(試薬)5.2g(0.03mol)、トルエン(試薬)300mlを仕込んだ後、n−ペンタノール(試薬)17.6g(0.2mol)を滴下しながら減圧下80℃で1時間、攪拌しながら反応させた。滴下後、更に4時間攪拌をし、反応を続けた。その間、生成した水はディーンスタークトラップにて除去した。反応後、トルエン300mlを加え、イオン交換水100mlで3回洗浄後、得られた有機相を採取し、エバポレータ及び真空乾燥機を用いてトルエンを留去し、マレイミド酢酸n−ペンチル43.5gを得た。(収率約91%。GPC測定にてマレイミド酢酸、n−ペンタノールが残存していないことを確認した。DMSO−d6を用いた1H−NMRの測定によりマレイミド酢酸n−ペンチルの存在を確認した。以下化合物A1という。)
なお、化合物A1においては、R1は炭素原子数1のアルキレン基であり、R2は炭素原子数5の直鎖アルキル基であり、R1とR2の炭素原子数の和は6である。
1H−NMR(400MHz,DMSO−d6):6.9ppm(2H,−CH=CH−)、4.0ppm(2H,−CH2−COO−)、3.8ppm(2H,−O−CH2−)
(化合物A2:マレイミド酢酸2−エチルブチルの合成)
合成例2において、n−ペンタノール17.6gの代わりに2−エチルブタノール(試薬)20.0gを用いた以外は、合成例1と同様にして、マレイミド酢酸2−エチルブチル47.3gを得た。(収率約88%。GPC測定にてマレイミド酢酸、2−エチルブタノールが残存していないことを確認した。DMSO−d6を用いた1H−NMRの測定によりマレイミド酢酸2−エチルブチルの存在を確認した。以下化合物A2という。)
なお、化合物A2においては、R1は炭素原子数1のアルキレン基であり、R2は炭素原子数6の分枝アルキル基であり、R1とR2の炭素原子数の和は7である。
1H−NMR(400MHz,DMSO−d6):6.9ppm(2H,−CH=CH−)、4.0ppm(2H,−CH2−COO−)、3.8ppm(2H,−O−CH2−)
(化合物A3:マレイミドカプロン酸n−ペンチルの合成)
合成例1において、マレイミド酢酸31.0gの代わりにマレイミドカプロン酸(試薬)38.6gを用いた以外は、合成例1と同様にして、マレイミドカプロン酸n−ペンチル45.2gを得た。(収率約86%。GPC測定にてマレイミド酢酸、n−ペンタノールが残存していないことを確認した。DMSO−d6を用いた1H−NMRの測定によりマレイミドカプロン酸n−ペンチルの存在を確認した。以下化合物A3という。)
なお、化合物A3においては、R1は炭素原子数5の直鎖アルキレン基であり、R2は炭素原子数5の直鎖アルキル基であり、R1とR2の炭素原子数の和は10である。
1H−NMR(400MHz,DMSO−d6):6.9ppm(2H,−CH=CH−)、2.3ppm(2H,−CH2−COO−)、3.7ppm(2H,−O−CH2−)
(化合物A4:マレイミド酢酸エチルの合成)
セパラブルフラスコで、無水酢酸(試薬)800mlにグリシンエチル塩酸塩(試薬)279g(2mol)を混合させた後、室温で撹拌しながら無水酢酸600mlに無水マレイン酸(試薬)196g(2mol)を溶解させたものを3時間かけて滴下した。滴下後、更に1時間撹拌して生じた沈殿を吸引ろ過により採取し、イオン交換水で洗浄、乾燥させた。この得られた生成物382g、トリエチルアミン(試薬)404g(4mol)、トルエン1200mlを、ディーンスタークトラップを備えたセパラブルフラスコに仕込んだ後、120℃で2時間、撹拌しながら反応させた。その間、生成した水はディーンスタークトラップにて除去した。反応後、トルエン300mlを加え、イオン交換水で3回洗浄後、得られた有機相を採取し、エバポレータ及び真空乾燥機を用いてトルエンを留去し、マレイミド酢酸エチル165gを得た。(収率約38%。GPC測定にてマレイミド酢酸エチルの生成を確認した。DMSO−d6を用いた1H−NMRの測定によりマレイミド酢酸エチルの存在を確認した。以下化合物A4という。)
なお、化合物A4においては、R1は炭素原子数1のアルキレン基であり、R2は炭素原子数2の直鎖アルキル基であり、R1とR2の炭素原子数の和は3である。
1H−NMR(400MHz,DMSO−d6):6.9ppm(2H,−CH=CH−)、4.0ppm(2H,−CH2−COO−)、3.8ppm(2H,−O−CH2−)
(化合物A5:マレイミド酢酸tert−ブチルの合成)
合成例1において、n−ペンタノール17.6gの代わりにtert−ブタノール(試薬)3.7gを用いた以外は、合成例1と同様にして、マレイミド酢酸tert−ブチル35.0gを得た。(収率約83%。GPC測定にてマレイミド酢酸、tert−ブタノールが残存していないことを確認した。DMSO−d6を用いた1H−NMRの測定によりマレイミド酢酸tert−ブチルの存在を確認した。以下化合物A5という。)
なお、化合物A5においては、R1は炭素原子数1のアルキレン基であり、R2は炭素原子数4の分枝アルキル基であり、R1とR2の炭素原子数の和は5である。
1H−NMR(400MHz,DMSO−d6):6.9ppm(2H,−CH=CH−)、4.1ppm(2H,−CH2−COO−)、1.5ppm(9H,−O−C(CH3)3)
(化合物A6:マレイミド安息香酸2−エチルブチルの合成)
合成例3において、マレイミド酢酸31.0gの代わりにマレイミド安息香酸43.4gを用いた以外は、合成例1と同様にして、マレイミド安息香酸2−エチルブチル50.4gを得た。(収率約80%。GPC測定にてマレイミド安息香酸、2−エチルブタノールが残存していないことを確認した。DMSO−d6を用いた1H−NMRの測定によりマレイミド安息香酸2−エチルブチルの存在を確認した。以下化合物A6という。)
なお、化合物A6においては、R1は炭素原子数6の芳香族環を有するフェニレン基であり、R2は炭素原子数6の分枝アルキル基であり、R1とR2の炭素原子数の和は12である。
1H−NMR(400MHz,DMSO−d6):7.5〜8.0ppm(4H,−C6H4−)、7.0ppm(2H,−CH=CH−)、3.8ppm(2H,−O−CH2−)
化合物B:ポリテトラメチレングリコールとマレイミド化酢酸の反応により得られたポリアルキレンマレイミド酢酸エステル(DIC(株)製、ルミキュアMIA−200、分子量580、以下化合物Bという。)
化合物C:シクロヘキサンジカルボン酸のジアリルエステルとプロピレングリコールとの反応により得られたジアリルエステル化合物(昭和電工(株)製、DA101、分子量1000、以下化合物Cという。)
化合物D:ポリエチレングリコールジ(メタ)アクリレート(共栄社化学(株)製、ライトエステル4EG、以下化合物Dという。)
反応性希釈剤:2−メタクリロイルオキシエチルコハク酸(共栄社化学(株)製、ライトエステルHOMS、以下単に反応性希釈剤という。)
ラジカル重合開始剤:1,1−ジ(tert−ブチルパーオキシ)シクロヘキサン(日本油脂(株)製、パーヘキサCS、以下単に開始剤という。)
充填材:平均粒径3μm、最大粒径20μmのフレーク状銀粉(全ての実施例及び比較例において、充填剤の含有量を22体積%に設定した。)
上記化合物、充填材の他に下記添加剤を用いた。
カップリング剤1:γ−グリシジルプロピルトリメトキシシラン(信越化学工業(株)製、KBM−403E、以下カップリング剤1という。)
カップリング剤2:ビス(トリメトキシシリルプロピル)テトラスルフィド(ダイソー(株)製、カブラス4、以下カップリング剤2という。)
上記より得られた実施例および比較例の樹脂組成物及び半導体装置について以下の評価試験を行った。評価結果を表1に示す。
(半導体装置の製造)
支持体として、封止樹脂のにじみ防止のために裏面にカプトンテープを貼り付けた、ニッケル−パラジウムメッキされた銅フレーム(ダイパッドサイズ:8×8mm、厚み220μm、1パネルあたりダイパッドが4列×4段)を用い、この支持体と、表面にSiN層を持つ半導体素子(5×5mm、厚さ350μm)とを上述した実施例及び比較例の樹脂組成物で接着し、175℃、30分間オーブン内で硬化して接着した。次に、半導体封止用エポキシ樹脂組成物(住友ベークライト社製、EME−G620)を用いて、1パネル50mm×50mm、リードフレームを含めた1パネルの厚みが750μmに封止し、175℃、4時間ポストモールドキュアを行い、その後ダイシングソーなどで個片化し、試験用半導体装置(84LQFN、サイズ10×10mm、封止樹脂厚み750μm)を得た。この試験用半導体装置の260℃加熱後の反りを反り量とした。
前記の通り定義した反り量は以下の方法で測定、算出した。
反り量:温度可変レーザー三次元測定機(日立エンジニアリングアンドサービス社製、LSI−150)を用いて上述の試験用半導体装置端部の四隅の高さ平均HEおよび試験用半導体装置中央部の高さHCを測定し、前記HEと前記HCの差すなわち下記式1により得られる数値を反り量とした。
式1:反り量=HE−HC
上述した実施例及び比較例の樹脂組成物を用いて、5×5mmシリコンチップ(厚み525μm)を支持体ニッケル−パラジウムメッキされた銅フレーム上にマウントし、オーブンを用いて175℃15分(25℃から175℃まで昇温速度5℃/分)の硬化温度プロファイルにて硬化した後、260℃環境下における熱時ダイシェア強度を測定した。得られた強度を密着強度とした(単位:N/チップ)。通常30N以上の密着強度が出れば、ワイヤーボンディング時や封止時に剥がれてしまうことはないため、30Nを超えるかどうかを判断基準とした。
E型粘度計(3°コーン)を用い25℃、2.5rpmでの値を実施例及び比較例の樹脂組成物作製直後に測定した。粘度が15〜30Pa・sの場合を合格とした。粘度の単位はPa・sである。
上述した実施例及び比較例の樹脂組成物を用いて、Al−1%Si−0.5%Cuの組成の電極を有するシリコンチップを、Agメッキを施した42アロイ製リードフレームに接着し、Auワイヤーをボンディングした。このボンディングしたワイヤーにフックをかけて引張り試験を行った。その際、ワイヤーの密着強度が十分な場合はワイヤー部分で破断するが、密着強度が不十分な場合はワイヤーとボンディングパッドの接合部で剥離する。表1における各符号は、以下の通りである。
○:接合部での剥離が全体の10%未満(合格)。
×:接合部での剥離が全体の10%以上(不良)。
支持体として、封止樹脂のにじみ防止のために裏面にカプトンテープを貼り付けた、ニッケル−パラジウムメッキされた銅フレーム(ダイパッドサイズ:8×8mm、厚み220μm、1パネルあたりダイパッドが4列×4段)を用い、この支持体と、表面にSiN層を持つ半導体素子(5×5mm、厚さ350μm)とを上述した実施例及び比較例の樹脂組成物で接着し、175℃、30分間オーブン内で硬化して接着した。次に、半導体封止用エポキシ樹脂組成物(住友ベークライト社製、EME−G620)を用いて、1パネル50mm×50mm、リードフレームを含めた1パネルの厚みが750μmに封止し、175℃、4時間ポストモールドキュアを行い、その後ダイシングソーなどで個片化し、試験用半導体装置(84LQFN、サイズ10×10mm、封止樹脂厚み750μm)を得た。この試験用半導体装置を60℃、相対湿度60%の条件下で120時間吸湿処理した後、IRリフロー処理(260℃、10秒、3回リフロー)を行い、処理後のパッケージを超音波深傷装置(透過型)により剥離面積の割合を測定し、10%未満の場合を合格とした。
Claims (6)
- 更にアリルエステル基を有する化合物(C)を含む請求項1に記載の樹脂組成物。
- 前記アリルエステル基を有する化合物(C)が脂肪族環を有するものである請求項2記載の樹脂組成物。
- 更に充填剤を含む請求項1に記載の樹脂組成物。
- 請求項1に記載の樹脂組成物を用いて作製した半導体装置。
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JPH0855940A (ja) * | 1994-08-12 | 1996-02-27 | Sumitomo Chem Co Ltd | 熱硬化性樹脂組成物 |
WO2000010974A2 (en) * | 1998-08-20 | 2000-03-02 | Dsm N.V. | Process for the preparation of a maleimide compound, maleimide compound, radiation-curable compositions comprising said compound and coated products |
JP2001322976A (ja) * | 2000-03-07 | 2001-11-20 | Dainippon Ink & Chem Inc | マレイミド誘導体の製造方法 |
WO2005090510A1 (ja) * | 2004-03-19 | 2005-09-29 | Sumitomo Bakelite Company, Ltd. | 樹脂組成物及び該樹脂組成物を使用して作製した半導体装置 |
JP2007238680A (ja) * | 2006-03-06 | 2007-09-20 | Sumitomo Bakelite Co Ltd | 樹脂組成物及び樹脂組成物を使用して作製した半導体装置 |
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JPS59213687A (ja) | 1983-05-18 | 1984-12-03 | 積水ハウス株式会社 | 軽量気泡コンクリ−ト製建築用パネルの製造法 |
JPH09157333A (ja) * | 1995-10-03 | 1997-06-17 | Sumitomo Bakelite Co Ltd | 熱硬化性樹脂組成物 |
JP2000072851A (ja) | 1998-08-31 | 2000-03-07 | Hitachi Chem Co Ltd | 樹脂ペースト組成物及びこれを用いた半導体装置 |
JP2000216299A (ja) | 1999-01-21 | 2000-08-04 | Toshiba Corp | 半導体パッケ―ジ、半導体装置、及び半導体パッケ―ジの製造方法 |
JP3007632B1 (ja) | 1999-04-01 | 2000-02-07 | 松下電子工業株式会社 | 樹脂封止型半導体装置およびその製造方法 |
JP4202632B2 (ja) | 2001-09-28 | 2008-12-24 | 株式会社東芝 | 一括封止型半導体パッケージの樹脂封止構造およびその製造装置 |
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2011
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JPH0855940A (ja) * | 1994-08-12 | 1996-02-27 | Sumitomo Chem Co Ltd | 熱硬化性樹脂組成物 |
WO2000010974A2 (en) * | 1998-08-20 | 2000-03-02 | Dsm N.V. | Process for the preparation of a maleimide compound, maleimide compound, radiation-curable compositions comprising said compound and coated products |
JP2001322976A (ja) * | 2000-03-07 | 2001-11-20 | Dainippon Ink & Chem Inc | マレイミド誘導体の製造方法 |
WO2005090510A1 (ja) * | 2004-03-19 | 2005-09-29 | Sumitomo Bakelite Company, Ltd. | 樹脂組成物及び該樹脂組成物を使用して作製した半導体装置 |
JP2007238680A (ja) * | 2006-03-06 | 2007-09-20 | Sumitomo Bakelite Co Ltd | 樹脂組成物及び樹脂組成物を使用して作製した半導体装置 |
Also Published As
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US8754178B2 (en) | 2014-06-17 |
CN103080160A (zh) | 2013-05-01 |
KR20130102046A (ko) | 2013-09-16 |
EP2615122A4 (en) | 2015-02-25 |
EP2615122A1 (en) | 2013-07-17 |
SG188309A1 (en) | 2013-04-30 |
JPWO2012033135A1 (ja) | 2014-01-20 |
CN103080160B (zh) | 2014-12-17 |
US20130158188A1 (en) | 2013-06-20 |
WO2012033135A1 (ja) | 2012-03-15 |
TW201217449A (en) | 2012-05-01 |
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