JP2015180726A - adhesive composition - Google Patents
adhesive composition Download PDFInfo
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- JP2015180726A JP2015180726A JP2015060454A JP2015060454A JP2015180726A JP 2015180726 A JP2015180726 A JP 2015180726A JP 2015060454 A JP2015060454 A JP 2015060454A JP 2015060454 A JP2015060454 A JP 2015060454A JP 2015180726 A JP2015180726 A JP 2015180726A
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- acrylic resin
- adhesive composition
- epoxy compound
- 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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- 239000000853 adhesive Substances 0.000 title claims abstract description 66
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 66
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 68
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 68
- 239000004593 Epoxy Substances 0.000 claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 36
- -1 alicyclic acid anhydride Chemical class 0.000 claims abstract description 34
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 238000010521 absorption reaction Methods 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims abstract description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract 2
- 230000009477 glass transition Effects 0.000 claims description 10
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical group CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 9
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 9
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 4
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- RIAHASMJDOMQER-UHFFFAOYSA-N 5-ethyl-2-methyl-1h-imidazole Chemical compound CCC1=CN=C(C)N1 RIAHASMJDOMQER-UHFFFAOYSA-N 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims 1
- 238000005260 corrosion Methods 0.000 abstract description 13
- 230000007797 corrosion Effects 0.000 abstract description 13
- 238000004040 coloring Methods 0.000 abstract description 6
- 230000007423 decrease Effects 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 10
- 239000000758 substrate Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- YCIGYTFKOXGYTA-UHFFFAOYSA-N 4-(3-cyanopropyldiazenyl)butanenitrile Chemical compound N#CCCCN=NCCCC#N YCIGYTFKOXGYTA-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 238000007747 plating Methods 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 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 3
- 238000002845 discoloration Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- QARDZRSRMBMAFJ-UHFFFAOYSA-N 1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)-1-[oxiran-2-yl-(oxiran-2-ylmethylamino)methoxy]methanamine Chemical compound C1OC1CNC(C1OC1)OC(C1OC1)NCC1CO1 QARDZRSRMBMAFJ-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000006078 metal deactivator Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- NIDNOXCRFUCAKQ-UMRXKNAASA-N (1s,2r,3s,4r)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@H]2C=C[C@@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-UMRXKNAASA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- GVPODVKBTHCGFU-UHFFFAOYSA-N 2,4,6-tribromoaniline Chemical compound NC1=C(Br)C=C(Br)C=C1Br GVPODVKBTHCGFU-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LJBWJFWNFUKAGS-UHFFFAOYSA-N 2-[bis(2-hydroxyphenyl)methyl]phenol Chemical compound OC1=CC=CC=C1C(C=1C(=CC=CC=1)O)C1=CC=CC=C1O LJBWJFWNFUKAGS-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-M 2-ethylacrylate Chemical compound CCC(=C)C([O-])=O WROUWQQRXUBECT-UHFFFAOYSA-M 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- PUMIRPCJLHGLOT-UHFFFAOYSA-N 3,5-diethyloxane-2,6-dione Chemical compound CCC1CC(CC)C(=O)OC1=O PUMIRPCJLHGLOT-UHFFFAOYSA-N 0.000 description 1
- HCILJBJJZALOAL-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)-n'-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl]propanehydrazide Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 HCILJBJJZALOAL-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- IBFJDBNISOJRCW-UHFFFAOYSA-N 3-methylphthalic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C(O)=O IBFJDBNISOJRCW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- XRBNDLYHPCVYGC-UHFFFAOYSA-N 4-phenylbenzene-1,2,3-triol Chemical group OC1=C(O)C(O)=CC=C1C1=CC=CC=C1 XRBNDLYHPCVYGC-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 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 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
Abstract
Description
本発明は、回路基板にＬＥＤ素子等のチップ部品をフリップチップ実装するための接着剤組成物に関する。 The present invention relates to an adhesive composition for flip-chip mounting a chip component such as an LED element on a circuit board.
発光ダイオード（ＬＥＤ）の光取り出し効率を向上させるために、ＬＥＤチップを基板にフリップチップ実装することが行われている（特許文献１）。この特許文献では、基板にＬＥＤチップを実装する方法の一つとして、導電ペーストが選択的に塗布された配線パターンを有する基板の当該配線パターン側表面に、エポキシ樹脂等の絶縁性樹脂からなるアンダーフィル樹脂を予め塗布しておき、続いてその上からＬＥＤチップをそのバンプ面が基板の配線パターンに対向するように載置し、熱圧着している。この場合、アンダーフィル樹脂は、ＬＥＤチップの正負電極間の絶縁を確保すると共に、ＬＥＤチップを基板に固定する役割を果たしている。 In order to improve the light extraction efficiency of a light emitting diode (LED), an LED chip is flip-chip mounted on a substrate (Patent Document 1). In this patent document, as one method for mounting an LED chip on a substrate, an underlayer made of an insulating resin such as an epoxy resin is formed on the surface of the substrate having a wiring pattern on which a conductive paste is selectively applied. Fill resin is applied in advance, and then the LED chip is placed thereon so that the bump surface faces the wiring pattern of the substrate, and is thermocompression bonded. In this case, the underfill resin serves to secure insulation between the positive and negative electrodes of the LED chip and to fix the LED chip to the substrate.
ところで、ＬＥＤチップを基板にフリップチップ実装する際に用いられるアンダーフィル樹脂であるエポキシ樹脂接着組成物には、硬化したときに無色透明であることが求められており、そのため、一般に、エポキシ成分として、着色の原因となる不飽和結合を持たず且つ速硬化性に優れた脂環式エポキシ化合物やグリシジル水添ビスフェノールＡ化合物を配合し、硬化剤として、硬化物に良好な透明性を付与でき且つ脂環式エポキシ化合物に対し優れた相溶性を示す脂環式酸無水物を配合している。更に、硬化物の弾性率を低下させて耐衝撃性を向上させ、しかも硬化物の耐熱・耐光変色防止性を低下させないという観点から、エポキシ樹脂接着組成物に、密着性が比較的高いという特性を有するアクリル樹脂を配合することが試みられている。 By the way, the epoxy resin adhesive composition which is an underfill resin used when flip-chip mounting an LED chip on a substrate is required to be colorless and transparent when cured. Therefore, in general, as an epoxy component In addition, an alicyclic epoxy compound or a glycidyl hydrogenated bisphenol A compound that does not have an unsaturated bond that causes coloring and is excellent in rapid curing can be blended, and as a curing agent, good transparency can be imparted to the cured product and An alicyclic acid anhydride exhibiting excellent compatibility with the alicyclic epoxy compound is blended. Furthermore, from the viewpoint of reducing the elastic modulus of the cured product to improve impact resistance and not reducing the heat resistance and light-proof discoloration resistance of the cured product, the epoxy resin adhesive composition has a relatively high adhesion property. Attempts have been made to blend acrylic resins having
しかしながら、アクリル樹脂を配合したエポキシ樹脂接着組成物を使用してＬＥＤチップを基板にフリップチップ実装しても、アクリル樹脂の種類により、接着力が低下したり、硬化物が白濁したり、硬化物が着色したり、あるいは実装品の基板に形成された配線が腐食したりするという問題があり、これらの問題を同時に解決したエポキシ樹脂接着組成物は未だ提案されていないというのが現状である。 However, even if the LED chip is flip-chip mounted on the substrate using an epoxy resin adhesive composition containing an acrylic resin, the adhesive strength may be reduced, the cured product may become cloudy, or the cured product may vary depending on the type of acrylic resin. Is colored or the wiring formed on the substrate of the mounted product is corroded, and an epoxy resin adhesive composition that solves these problems at the same time has not yet been proposed.
本発明は、回路基板に、ＬＥＤチップなどの光半導体チップをはじめとするチップ部品をフリップチップ実装するための、脂環式エポキシ化合物と脂環式酸無水物とを含有する接着剤組成物にアクリル樹脂を配合した場合に、“接着力の低下”、“硬化物の白濁や着色”、及び“回路基板の配線の腐食”という問題を同時に解決することを目的とする。 The present invention provides an adhesive composition containing an alicyclic epoxy compound and an alicyclic acid anhydride for flip-chip mounting a chip component including an optical semiconductor chip such as an LED chip on a circuit board. When an acrylic resin is blended, the object is to solve simultaneously the problems of “decrease in adhesive strength”, “white turbidity or coloring of a cured product”, and “corrosion of wiring on a circuit board”.
本発明者らは、接着剤組成物を、透明性と耐変色性並びに速硬化性に優れている脂環式エポキシ化合物と脂環式酸無水物系硬化剤とに加えてアクリル樹脂とから構成し、しかも、それらの配合割合を特定し、更に、アクリル樹脂として特定割合のグリシジルメタクリレートとアルキル（メタ）アクリレートとを共重合させたものであって、吸水率が所定割合以下のものを使用することにより、上述の目的を達成できることを見出し、本発明を完成させるに至った。なお、本明細書において、「アルキル（メタ）アクリレート」とは、アルキルアクリレート又はアルキルメタクリレートを意味する。 The present inventors comprise an adhesive composition comprising an acrylic resin in addition to an alicyclic epoxy compound and an alicyclic acid anhydride-based curing agent, which are excellent in transparency, discoloration resistance, and fast curability. In addition, those blending ratios are specified, and further, a specific ratio of glycidyl methacrylate and alkyl (meth) acrylate is copolymerized as an acrylic resin, and the water absorption rate is a predetermined ratio or less. Thus, the inventors have found that the above-described object can be achieved, and have completed the present invention. In the present specification, “alkyl (meth) acrylate” means alkyl acrylate or alkyl methacrylate.
即ち、本発明は、回路基板にチップ部品をフリップチップ実装するための接着剤組成物であって、脂環式エポキシ化合物と脂環式酸無水物系硬化剤とアクリル樹脂とを含有し、
脂環式酸無水物系硬化剤の含有量が、脂環式エポキシ化合物１００質量部に対し８０〜１２０質量部であり、該アクリル樹脂の含有量が、脂肪環式エポキシ化合物と脂環式酸無水物系硬化剤とアクリル樹脂との合計１００質量部中に５〜５０質量部であり、
該アクリル樹脂が、アルキル（メタ）アクリレートと、アルキル（メタ）アクリレート１００質量部に対し２〜１００質量部のグリシジルメタクリレートとを共重合させた吸水率１．２％以下の樹脂であることを特徴とする接着剤組成物を提供する。
That is, the present invention is an adhesive composition for flip-chip mounting chip components on a circuit board, comprising an alicyclic epoxy compound, an alicyclic acid anhydride curing agent, and an acrylic resin,
The content of the alicyclic acid anhydride-based curing agent is 80 to 120 parts by mass with respect to 100 parts by mass of the alicyclic epoxy compound, and the content of the acrylic resin is the alicyclic epoxy compound and the alicyclic acid. 5 to 50 parts by mass in a total of 100 parts by mass of the anhydride-based curing agent and the acrylic resin,
The acrylic resin is a resin having a water absorption of 1.2% or less obtained by copolymerizing alkyl (meth) acrylate and 2 to 100 parts by mass of glycidyl methacrylate with respect to 100 parts by mass of alkyl (meth) acrylate. An adhesive composition is provided.
また、本発明は、回路基板にチップ部品が、上述した異方性導電接着剤を用いてフリップチップ実装された接続構造体を提供する。 The present invention also provides a connection structure in which a chip component is flip-chip mounted on a circuit board using the above-described anisotropic conductive adhesive.
本発明の接着剤組成物は、特定割合の脂環式エポキシ化合物と脂環式酸無水物系硬化剤とアクリル樹脂とから構成され、しかもアクリル樹脂として、特定割合のグリシジルメタクリレートとアルキル（メタ）アクリレートとを重合させたものであって、吸水率が所定割合以下のものを使用する。このため、接着力の低下、硬化物の白濁や着色及び回路基板の配線の腐食という問題の発生を大きく抑制することができる。 The adhesive composition of the present invention is composed of a specific proportion of an alicyclic epoxy compound, an alicyclic acid anhydride-based curing agent, and an acrylic resin, and as the acrylic resin, a specific proportion of glycidyl methacrylate and alkyl (meth). A polymer obtained by polymerizing acrylate and having a water absorption rate of a predetermined ratio or less is used. For this reason, generation | occurrence | production of the problem of the fall of adhesive force, the cloudiness and coloring of hardened | cured material, and the corrosion of the wiring of a circuit board can be suppressed significantly.
本発明は、回路基板にチップ部品をフリップチップ実装するための接着剤組成物であり、組成的には脂環式エポキシ化合物と脂環式酸無水物系硬化剤とアクリル樹脂とを含有する接着剤組成物である。ここで、回路基板としては、ガラスエポキシ基板、ガラス基板、フレキシブル基板などが挙げられる、チップ部品としては、特に限定されないが、本発明の効果を最大限に生かすためには、光半導体チップ、特にＬＥＤチップが挙げられる。 The present invention is an adhesive composition for flip-chip mounting a chip component on a circuit board, and in terms of composition, an adhesive containing an alicyclic epoxy compound, an alicyclic acid anhydride curing agent, and an acrylic resin. Agent composition. Here, examples of the circuit board include a glass epoxy board, a glass board, and a flexible board. The chip component is not particularly limited, but in order to maximize the effects of the present invention, an optical semiconductor chip, particularly An LED chip is mentioned.
本発明の接着剤組成物を構成する脂環式エポキシ化合物としては、分子内に２つ以上のエポキシ基を有するものが好ましく挙げられる。これらは液状であっても、固体状であってもよい。具体的には、グリシジルヘキサヒドロビスフェノールＡ、３，４−エポキシシクロヘキセニルメチル−３′，４′−エポキシシクロヘキセンカルボキシレート、１，３，５−トリス（２，３−エポキシプロピル）−１，３，５−トリアジン−２，４，６（１Ｈ，３Ｈ，５Ｈ）−トリオン等を挙げることができる。中でも、硬化物にＬＥＤ素子の実装等に適した光透過性を確保でき、速硬化性にも優れている点から、グリシジルヘキサヒドロビスフェノールＡ、３，４−エポキシシクロヘキセニルメチル−３′，４′−エポキシシクロヘキセンカルボキシレートを好ましく使用することができる。 As an alicyclic epoxy compound which comprises the adhesive composition of this invention, what has two or more epoxy groups in a molecule | numerator is mentioned preferably. These may be liquid or solid. Specifically, glycidyl hexahydrobisphenol A, 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexene carboxylate, 1,3,5-tris (2,3-epoxypropyl) -1,3 , 5-triazine-2,4,6 (1H, 3H, 5H) -trione and the like. Among them, glycidyl hexahydrobisphenol A, 3,4-epoxycyclohexenylmethyl-3 ′, 4 is preferable because it can ensure light transmission suitable for mounting LED elements on the cured product and is excellent in rapid curing. '-Epoxycyclohexene carboxylate can be preferably used.
本発明において、脂環式エポキシ化合物に加えて、本発明の効果を損なわない限り、他のエポキシ化合物を併用してもよい。例えば、ビスフェノールＡ、ビスフェノールＦ、ビスフェノールＳ、テトラメチルビスフェノールＡ、ジアリールビスフェノールＡ、ハイドロキノン、カテコール、レゾルシン、クレゾール、テトラブロモビスフェノールＡ、トリヒドロキシビフェニル、ベンゾフェノン、ビスレゾルシノール、ビスフェノールヘキサフルオロアセトン、テトラメチルビスフェノールＡ、テトラメチルビスフェノールＦ、トリス（ヒドロキシフェニル）メタン、ビキシレノール、フェノールノボラック、クレゾールノボラックなどの多価フェノールとエピクロルヒドリンとを反応させて得られるグリシジルエーテル、またはグリセリン、ネオペンチルグリコール、エチレングリコール、プロピレングリコール、チレングリコール、ヘキシレングリコール、ポリエチレングリコール、ポリプロピレングリコールなどの脂肪族多価アルコールとエピクロルヒドリンとを反応させて得られるポリグリシジルエーテル； ｐ−オキシ安息香酸、β−オキシナフトエ酸のようなヒドロキシカルボン酸とエピクロルヒドリンとを反応させて得られるグリシジルエーテルエステル、あるいはフタル酸、メチルフタル酸、イソフタル酸、テレフタル酸、テトラハイドロフタル酸、エンドメチレンテトラハイドロフタル酸、エンドメチレンヘキサハイドロフタル酸、トリメリット酸、重合脂肪酸のようなポリカルボン酸から得られるポリグリシジルエステル； アミノフェノール、アミノアルキルフェノールから得られるグリシジルアミノグリシジルエーテル； アミノ安息香酸から得られるグリシジルアミノグリシジルエステル； アニリン、トルイジン、トリブロムアニリン、キシリレンジアミン、ジアミノシクロヘキサン、 ビスアミノメチルシクロヘキサン、４，４’−ジアミノジフェニルメタン、４，４’−ジアミノジフェニルスルホンなどから得られるグリシジルアミン； エポキシ化ポリオレフィン等の公知のエポキシ樹脂類が挙げられる。 In the present invention, in addition to the alicyclic epoxy compound, other epoxy compounds may be used in combination as long as the effects of the present invention are not impaired. For example, bisphenol A, bisphenol F, bisphenol S, tetramethylbisphenol A, diarylbisphenol A, hydroquinone, catechol, resorcin, cresol, tetrabromobisphenol A, trihydroxybiphenyl, benzophenone, bisresorcinol, bisphenol hexafluoroacetone, tetramethylbisphenol G, glycidyl ether obtained by reacting polyphenol such as A, tetramethylbisphenol F, tris (hydroxyphenyl) methane, bixylenol, phenol novolak, cresol novolak and epichlorohydrin, or glycerin, neopentyl glycol, ethylene glycol, propylene Glycol, tylene glycol, hexylene glycol, poly Polyglycidyl ether obtained by reacting an aliphatic polyhydric alcohol such as tylene glycol or polypropylene glycol with epichlorohydrin; obtained by reacting a hydroxycarboxylic acid such as p-oxybenzoic acid or β-oxynaphthoic acid with epichlorohydrin Glycidyl ether esters, or polycarboxylic acids such as phthalic acid, methylphthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, endomethylenetetrahydrophthalic acid, endomethylenehexahydrophthalic acid, trimellitic acid, polymerized fatty acid Polyglycidyl ester obtained; Glycidylaminoglycidyl ether obtained from aminophenol and aminoalkylphenol; Glycidylaminoglycidyl ether obtained from aminobenzoic acid Steal; Glycidylamine obtained from aniline, toluidine, tribromoaniline, xylylenediamine, diaminocyclohexane, bisaminomethylcyclohexane, 4,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylsulfone, epoxidized polyolefin, etc. Known epoxy resins can be mentioned.
脂環式酸無水物系硬化剤としては、具体的には、メチルヘキサヒドロフタル酸無水物、２，４−ジエチル−１，５−ペンタン二酸無水物等を挙げることができる。中でも、硬化物のＬＥＤ素子の実装等に適した光透過性を確保でき、脂環式エポキシ化合物に対して良好な相溶性を示すメチルヘキサヒドロフタル酸無水物を好ましく使用することができる。 Specific examples of the alicyclic acid anhydride-based curing agent include methylhexahydrophthalic anhydride, 2,4-diethyl-1,5-pentanedioic anhydride, and the like. Among them, methylhexahydrophthalic anhydride that can ensure light transmission suitable for mounting of a cured LED element and that exhibits good compatibility with an alicyclic epoxy compound can be preferably used.
本発明の接着剤組成物中の脂環式エポキシ化合物と脂環式酸無水物系硬化剤のそれぞれの使用量は、脂環式酸無水物系硬化剤が少なすぎると接着力が低下し、多すぎると耐腐食性が低下する傾向があるので、脂環式エポキシ化合物１００質量部に対し脂環式酸無水物系硬化剤を好ましくは８０〜１２０質量部、より好ましくは９０〜１１０質量部の割合で使用する。 Each use amount of the alicyclic epoxy compound and the alicyclic acid anhydride-based curing agent in the adhesive composition of the present invention decreases the adhesive strength when the alicyclic acid anhydride-based curing agent is too small, If the amount is too large, the corrosion resistance tends to decrease. Therefore, the alicyclic acid anhydride curing agent is preferably 80 to 120 parts by weight, more preferably 90 to 110 parts by weight with respect to 100 parts by weight of the alicyclic epoxy compound. Use at a rate of.
本発明の接着剤組成物は、硬化物の弾性率を低下させ、耐衝撃性を向上させる等の目的でアクリル樹脂を含有する。このアクリル樹脂は、アルキル（メタ）アクリレート１００質量部に対し、グリシジルメタアクリレートを２〜１００質量部、好ましくは５〜７０質量部を共重合させた樹脂である。ここで、好ましいアルキル（メタ）アクリレートとしては、エチルアクリレート、ブチルアクリレート、２−エチルアクリレート等を挙げることができる。 The adhesive composition of the present invention contains an acrylic resin for the purpose of reducing the elastic modulus of the cured product and improving impact resistance. This acrylic resin is a resin obtained by copolymerizing 2 to 100 parts by mass, preferably 5 to 70 parts by mass of glycidyl methacrylate with respect to 100 parts by mass of alkyl (meth) acrylate. Here, as preferable alkyl (meth) acrylate, ethyl acrylate, butyl acrylate, 2-ethyl acrylate, and the like can be given.
また、アクリル樹脂は、その吸水率が１．２％以下、好ましくは１．０％以下のものである。これは、吸水率が１．２％を超えると金属製の電極を腐食する危険性が増大するからである。ここで、吸水率は、ＪＩＳ Ｋ７２０９に準拠して求められたものであり、具体的には、１．０ｍｍ厚のアクリル樹脂シートを１ｃｍ幅で１ｃｍ長さにカットして試料とし、得られた試料を８０℃の真空オーブンで２０時間乾燥させ、重量（Ｗ０）を測定する。その後、８５℃、８５％ＲＨの環境下に２４時間放置し、重量（Ｗ１）を測定し、以下の式に従って吸水率を算出する。 The acrylic resin has a water absorption of 1.2% or less, preferably 1.0% or less. This is because when the water absorption rate exceeds 1.2%, the risk of corroding the metal electrode increases. Here, the water absorption rate was obtained in accordance with JIS K7209. Specifically, a 1.0 mm thick acrylic resin sheet was cut into a 1 cm width and a 1 cm length to obtain a sample. The sample is dried in a vacuum oven at 80 ° C. for 20 hours, and the weight (W 0 ) is measured. Then, it is left in an environment of 85 ° C. and 85% RH for 24 hours, the weight (W 1 ) is measured, and the water absorption is calculated according to the following formula.
また、アクリル樹脂の重量平均分子量は、それが小さすぎると接着力が低下し、大きすぎると脂環式エポキシ化合物と混和し難くなるので、好ましくは５０００〜２０００００、より好ましくは１００００〜１０００００である。加えて、アクリル樹脂のガラス転移温度は、その温度が高すぎると接着力が低下するので、好ましくは５０℃以下、より好ましくは２０℃以下である。 Further, the weight average molecular weight of the acrylic resin is preferably 5000 to 200,000, more preferably 10,000 to 100,000, since the adhesive strength is lowered if it is too small, and it becomes difficult to mix with the alicyclic epoxy compound if it is too large. . In addition, the glass transition temperature of the acrylic resin is preferably 50 ° C. or less, more preferably 20 ° C. or less, because the adhesive strength is lowered when the temperature is too high.
このようなアクリル樹脂の使用量は、少なすぎると接着力が低下し、多すぎると光学特性が低下する傾向があるので、脂環式エポキシ化合物と脂環式酸無水物系硬化剤とアクリル樹脂の合計１００質量部中に、好ましくは５〜５０質量部、より好ましくは１０〜４０質量部の割合で使用する。 If the amount of the acrylic resin used is too small, the adhesive strength is lowered, and if it is too much, the optical properties tend to be lowered. Therefore, the alicyclic epoxy compound, the alicyclic acid anhydride curing agent, and the acrylic resin are used. Is preferably used in a proportion of 5 to 50 parts by mass, more preferably 10 to 40 parts by mass.
本発明の接着剤組成物には、更に、必要に応じて硬化促進剤としてイミダゾール化合物を配合することができる。イミダゾール化合物の具体例としては２−メチル−４−エチルイミダゾールを挙げることができる。このようなイミダゾール化合物の使用量は、少なすぎると硬化が不十分となり、多すぎると光学特性が低下するので、脂環式エポキシ化合物と脂環式酸無水物系硬化剤とアクリル樹脂の合計１００質量部に対し、好ましくは０．０１〜１０質量部、より好ましくは０．１〜５質量部である。 The adhesive composition of the present invention may further contain an imidazole compound as a curing accelerator as necessary. Specific examples of the imidazole compound include 2-methyl-4-ethylimidazole. If the amount of such an imidazole compound is too small, curing will be insufficient, and if it is too large, the optical properties will deteriorate, so a total of 100 cycloaliphatic epoxy compounds, cycloaliphatic anhydride-based curing agents and acrylic resins. Preferably it is 0.01-10 mass parts with respect to a mass part, More preferably, it is 0.1-5 mass parts.
また、本発明の接着剤組成物には、耐熱性及び耐熱光性の向上を目的として、ＩＲＧＡＮＯＸ １０１０（チバ・スペシャリティー・ケミカルズ（株））等の熱酸化防止剤、ＩＲＧＡＮＯＸ ＭＤ １０２４（チバ・スペシャリティー・ケミカルズ（株））等の金属不活性剤、Ｃｈｉｍａｓｏｒｂ ８１（チバ・スペシャリティー・ケミカルズ（株））等の紫外線防止剤を同時に含有させることが好ましい。これらの含有量は、脂環式エポキシ化合物と脂環式酸無水物系硬化剤とアクリル樹脂の合計１００質量部に対し、熱酸化防止剤を好ましくは０．０１〜１０質量部、より好ましくは０．１〜５質量部、金属不活性剤を好ましくは０．０１〜１０質量部、より好ましくは０．１〜５質量部、紫外線吸収剤を好ましくは０．０１〜１０質量部、より好ましくは０．１〜５質量部である。 In addition, the adhesive composition of the present invention includes thermal antioxidants such as IRGANOX 1010 (Ciba Specialty Chemicals Co., Ltd.), IRGANOX MD 1024 (Ciba It is preferable to simultaneously contain a metal deactivator such as Specialty Chemicals Co., Ltd. and an ultraviolet light inhibitor such as Chimasorb 81 (Ciba Specialty Chemicals Co., Ltd.). These contents are preferably 0.01 to 10 parts by mass, more preferably a thermal antioxidant for 100 parts by mass in total of the alicyclic epoxy compound, the alicyclic acid anhydride curing agent and the acrylic resin. 0.1 to 5 parts by mass, preferably 0.01 to 10 parts by mass of metal deactivator, more preferably 0.1 to 5 parts by mass, and preferably 0.01 to 10 parts by mass of UV absorber. Is 0.1 to 5 parts by mass.
本発明の接着剤組成物には、必要に応じ、従来の接着剤組成物でも用いられている種々の添加剤を配合することができる。例えば、シランカップリング剤、フィラー等を配合することができる。 In the adhesive composition of the present invention, various additives that are also used in conventional adhesive compositions can be blended as necessary. For example, a silane coupling agent, a filler, etc. can be mix | blended.
本発明の接着剤組成物は、常法に従って脂環式エポキシ化合物と、脂環式酸無水物系硬化剤と、アクリル樹脂と、必要に応じて他の添加剤とを均一に混合することにより製造することができる。その際、常法に従ってペースト形態、フィルム形態、高粘性液体形態等の形態に加工することができる。また、この接着剤組成物は、熱硬化型であり、通常１５０〜２５０℃に加熱することにより硬化させることができる。 The adhesive composition of the present invention is obtained by uniformly mixing an alicyclic epoxy compound, an alicyclic acid anhydride curing agent, an acrylic resin, and other additives as required according to a conventional method. Can be manufactured. In that case, it can process into forms, such as a paste form, a film form, and a highly viscous liquid form, according to a conventional method. Moreover, this adhesive composition is a thermosetting type | mold, and can be hardened normally by heating to 150-250 degreeC.
本発明の接着剤組成物は、回路基板に光半導体チップ、特にＬＥＤチップ等のチップ部品をフリップチップ実装するために使用するものである。従って、本発明の接着剤組成物を使用して回路基板に光半導体チップ、特にＬＥＤチップ等のチップ部品をフリップチップ実装した接続構造体は、接着力の低下、硬化物の白濁や着色及び回路基板の配線の腐食という問題の発生が大きく抑制されたものとなる。 The adhesive composition of the present invention is used for flip-chip mounting a chip component such as an optical semiconductor chip, particularly an LED chip, on a circuit board. Therefore, a connection structure in which a chip component such as an optical semiconductor chip, particularly an LED chip, is flip-chip mounted on a circuit board using the adhesive composition of the present invention has a reduced adhesive force, white turbidity or coloring of a cured product, and circuit. The occurrence of the problem of corrosion of the wiring on the board is greatly suppressed.
以下、本発明を実施例により具体的に説明する。 Hereinafter, the present invention will be specifically described by way of examples.
参考例１（アクリル樹脂Ａの製造）
攪拌機、冷却管を備えた四つ口フラスコに、エチルアクリレート（ＥＡ）５０ｇ、ブチルアクリレート（ＢＡ）５０ｇ、グリシジルメタクリレート（ＧＭＡ）１０ｇ、アゾビスブチロニトリル０．２ｇ、酢酸エチル３００ｇ、及びアセトン５ｇを仕込み、撹拌しながら７０℃で８時間重合反応させた。沈殿した粒子を濾取し、エタノールで洗浄し乾燥することによりアクリル樹脂Ａを得た。得られたアクリル樹脂Ａ（EA50:BA50:GMA10）の重量平均分子量は８００００であり、ガラス転移温度は−５６℃であった。また、吸水率は１．０％であった。
Reference Example 1 (Production of acrylic resin A)
In a four-necked flask equipped with a stirrer and a condenser tube, 50 g of ethyl acrylate (EA), 50 g of butyl acrylate (BA), 10 g of glycidyl methacrylate (GMA), 0.2 g of azobisbutyronitrile, 300 g of ethyl acetate, and 5 g of acetone The polymerization reaction was carried out at 70 ° C. for 8 hours with stirring. The precipitated particles were collected by filtration, washed with ethanol, and dried to obtain acrylic resin A. The resulting acrylic resin A (EA50: BA50: GMA10) had a weight average molecular weight of 80000 and a glass transition temperature of −56 ° C. Further, the water absorption was 1.0%.
参考例２（アクリル樹脂Ｂの製造）
攪拌機、冷却管を備えた四つ口フラスコに、ブチルアクリレート（ＢＡ）７０ｇ、グリシジルメタクリレート（ＧＭＡ）３０ｇ、アゾビスブチロニトリル０．２ｇ、酢酸エチル３００ｇ、及びアセトン５ｇを仕込み、撹拌しながら７０℃で８時間重合反応させた。沈殿した粒子を濾取し、エタノールで洗浄し乾燥することによりアクリル樹脂Ｂを得た。得られたアクリル樹脂Ｂ(BA70:GMA30)の重量平均分子量は１１００００であり、ガラス転移温度は−３４℃であった。また、吸水率は０．５％であった。
Reference Example 2 (Production of acrylic resin B)
A four-necked flask equipped with a stirrer and a condenser is charged with 70 g of butyl acrylate (BA), 30 g of glycidyl methacrylate (GMA), 0.2 g of azobisbutyronitrile, 300 g of ethyl acetate, and 5 g of acetone while stirring. The polymerization reaction was carried out at 0 ° C. for 8 hours. The precipitated particles were collected by filtration, washed with ethanol and dried to obtain acrylic resin B. The resulting acrylic resin B (BA70: GMA30) had a weight average molecular weight of 110,000 and a glass transition temperature of -34 ° C. Further, the water absorption was 0.5%.
参考例３（アクリル樹脂Ｃの製造）
攪拌機、冷却管を備えた四つ口フラスコに、２−エチルヘキシルアクリレート（２−ＥＨＡ）７０ｇ、グリシジルメタクリレート（ＧＭＡ）３０ｇ、アゾビスブチロニトリル０．２ｇ、酢酸エチル３００ｇ、及びアセトン５ｇを仕込み、撹拌しながら７０℃で８時間重合反応させた。沈殿した粒子を濾取し、エタノールで洗浄し乾燥することによりアクリル樹脂Ｃを得た。得られたアクリル樹脂Ｃ(2-EHA70:GMA30)の重量平均分子量は１１００００であり、ガラス転移温度は−３３℃であった。また、吸水率は０．５％であった。
Reference Example 3 (Production of acrylic resin C)
A four-necked flask equipped with a stirrer and a condenser is charged with 70 g of 2-ethylhexyl acrylate (2-EHA), 30 g of glycidyl methacrylate (GMA), 0.2 g of azobisbutyronitrile, 300 g of ethyl acetate, and 5 g of acetone. The polymerization reaction was carried out at 70 ° C. for 8 hours with stirring. The precipitated particles were collected by filtration, washed with ethanol and dried to obtain acrylic resin C. The resulting acrylic resin C (2-EHA70: GMA30) had a weight average molecular weight of 110,000 and a glass transition temperature of −33 ° C. Further, the water absorption was 0.5%.
参考例４（アクリル樹脂Ｄの製造）
攪拌機、冷却管を備えた四つ口フラスコに、ブチルアクリレート（ＢＡ）３０ｇ、ブチルメタクリレート（ＢＭＡ）５０ｇ、グリシジルメタクリレート（ＧＭＡ）２０ｇ、アゾビスブチロニトリル０．２ｇ、酢酸エチル３００ｇ、及びアセトン５ｇを仕込み、撹拌しながら７０℃で８時間重合反応させた。沈殿した粒子を濾取し、エタノールで洗浄し乾燥することによりアクリル樹脂Ｄを得た。得られたアクリル樹脂Ｄ（BA30:BMA50:GMA20）の重量平均分子量は８００００であり、ガラス転移温度は−４．２℃であった。また、吸水率は０．５％であった。
Reference Example 4 (Production of acrylic resin D)
In a four-necked flask equipped with a stirrer and a condenser, butyl acrylate (BA) 30 g, butyl methacrylate (BMA) 50 g, glycidyl methacrylate (GMA) 20 g, azobisbutyronitrile 0.2 g, ethyl acetate 300 g, and acetone 5 g The polymerization reaction was carried out at 70 ° C. for 8 hours with stirring. The precipitated particles were collected by filtration, washed with ethanol and dried to obtain acrylic resin D. The resulting acrylic resin D (BA30: BMA50: GMA20) had a weight average molecular weight of 80000 and a glass transition temperature of −4.2 ° C. Further, the water absorption was 0.5%.
参考例５（アクリル樹脂ａの製造）
攪拌機、冷却管を備えた四つ口フラスコに、エチルアクリレート（ＥＡ）１００ｇ、アクリル酸１０ｇ、アゾビスブチロニトリル０．２ｇ、酢酸エチル３００ｇ、及びアセトン５ｇを仕込み、撹拌しながら７０℃で８時間重合反応させた。沈殿した粒子を濾取し、エタノールで洗浄し乾燥することによりアクリル樹脂ａを得た。得られたアクリル樹脂ａ(EA100:Aac10)の重量平均分子量は９５０００であり、ガラス転移温度は−３３℃であった。また、吸水率は１．５％であった。
Reference Example 5 (Production of acrylic resin a)
A four-necked flask equipped with a stirrer and a condenser tube was charged with 100 g of ethyl acrylate (EA), 10 g of acrylic acid, 0.2 g of azobisbutyronitrile, 300 g of ethyl acetate, and 5 g of acetone. The polymerization reaction was performed for a time. The precipitated particles were collected by filtration, washed with ethanol and dried to obtain acrylic resin a. The resulting acrylic resin a (EA100: Aac10) had a weight average molecular weight of 95,000 and a glass transition temperature of −33 ° C. Further, the water absorption was 1.5%.
参考例６（アクリル樹脂ｂの製造）
攪拌機、冷却管を備えた四つ口フラスコに、メチルアクリレート（ＭＡ）７０ｇ、グリシジルメタクリレート（ＧＭＡ）３０ｇ、アゾビスブチロニトリル０．２ｇ、酢酸エチル３００ｇ、及びアセトン５ｇを仕込み、撹拌しながら７０℃で８時間重合反応させた。沈殿した粒子を濾取し、エタノールで洗浄し乾燥することによりアクリル樹脂ｂを得た。得られたアクリル樹脂ｂ(MA70:GMA30)の重量平均分子量は１１００００であり、ガラス転移温度は１７℃であった。また、吸水率は１．７％であった。
Reference Example 6 (Production of acrylic resin b)
A four-necked flask equipped with a stirrer and a condenser is charged with 70 g of methyl acrylate (MA), 30 g of glycidyl methacrylate (GMA), 0.2 g of azobisbutyronitrile, 300 g of ethyl acetate, and 5 g of acetone while stirring. The polymerization reaction was carried out at 0 ° C. for 8 hours. The precipitated particles were collected by filtration, washed with ethanol and dried to obtain acrylic resin b. The resulting acrylic resin b (MA70: GMA30) had a weight average molecular weight of 110,000 and a glass transition temperature of 17 ° C. Further, the water absorption was 1.7%.
参考例７（アクリル樹脂ｃの製造）
攪拌機、冷却管を備えた四つ口フラスコに、エチルアクリレート７０ｇ、グリシジルメタクリレート（ＧＭＡ）３０ｇ、アゾビスブチロニトリル０．２ｇ、酢酸エチル３００ｇ、及びアセトン５ｇを仕込み、撹拌しながら７０℃で８時間重合反応させた。沈殿した粒子を濾取し、エタノールで洗浄し乾燥することによりアクリル樹脂ｃを得た。得られたアクリル樹脂ｃ(EA70:GMA30)の重量平均分子量は１０００００であり、ガラス転移温度は−６℃であった。また、吸水率は１．５％であった。
Reference Example 7 (Production of acrylic resin c)
A four-necked flask equipped with a stirrer and a condenser tube was charged with 70 g of ethyl acrylate, 30 g of glycidyl methacrylate (GMA), 0.2 g of azobisbutyronitrile, 300 g of ethyl acetate, and 5 g of acetone, and stirred at 70 ° C. for 8 g. The polymerization reaction was performed for a time. The precipitated particles were collected by filtration, washed with ethanol and dried to obtain acrylic resin c. The resulting acrylic resin c (EA70: GMA30) had a weight average molecular weight of 100,000 and a glass transition temperature of −6 ° C. Further, the water absorption was 1.5%.
参考例８（アクリル樹脂ｄの製造）
攪拌機、冷却管を備えた四つ口フラスコに、エチルアクリレート（ＥＡ）７０ｇ、グリシジルメタクリレート（ＧＭＡ）２５ｇ、ヒドロキシエチルメタクリレレート５ｇ、アゾビスブチロニトリル０．２ｇ、酢酸エチル３００ｇ、及びアセトン５ｇを仕込み、撹拌しながら７０℃で８時間重合反応させた。沈殿した粒子を濾取し、エタノールで洗浄し乾燥することによりアクリル樹脂ｄを得た。得られたアクリル樹脂ｄ(EA70:GMA25:HEMA5)の重量平均分子量は１２００００であり、ガラス転移温度は−５℃であった。また、吸水率は１．５％であった。
Reference Example 8 (Production of acrylic resin d)
In a four-necked flask equipped with a stirrer and a condenser, 70 g of ethyl acrylate (EA), 25 g of glycidyl methacrylate (GMA), 5 g of hydroxyethyl methacrylate, 0.2 g of azobisbutyronitrile, 300 g of ethyl acetate, and 5 g of acetone The polymerization reaction was carried out at 70 ° C. for 8 hours with stirring. The precipitated particles were collected by filtration, washed with ethanol and dried to obtain acrylic resin d. The obtained acrylic resin d (EA70: GMA25: HEMA5) had a weight average molecular weight of 120,000 and a glass transition temperature of −5 ° C. Further, the water absorption was 1.5%.
実施例１〜４、比較例１〜８
表１に示す配合の成分を遊星型撹拌器で均一に混合することにより接着剤組成物を調製した。
Examples 1-4, Comparative Examples 1-8
An adhesive composition was prepared by uniformly mixing the components shown in Table 1 with a planetary stirrer.
評価試験
実施例１〜４及び比較例１〜８で得られたペースト状の接着剤組成物について、以下に説明する様に、接着力、光学特性（フィルム外観、色差）、耐腐食性を評価した。
Evaluation Test As described below, the adhesive strength, optical characteristics (film appearance, color difference), and corrosion resistance of the paste-like adhesive compositions obtained in Examples 1 to 4 and Comparative Examples 1 to 8 were evaluated. did.
＜接着力試験＞
Ｃｕ配線部分にＡｕフラッシュメッキが施されたガラスエポキシ回路基板に、ペースト状の接着剤組成物を２５μｍ厚となるように塗布し、その上に１．５ｍｍ角のＩＣチップを載置し、フリップチップボンダーを使用し２００℃で６０秒間加熱することにより熱圧着して接続構造体を得た。得られた直後（初期）、リフロー後（２６０℃）、１５０℃で１００時間放置後の接続構造体のＩＣチップについて、ダイシェアーテスター（ＲＴＲ−１１００、レスカ社）を用いて接着強度（Ｎ／Ｃｈｉｐ）を測定した。得られた結果を表１に示す。本接着力試験の条件を前提にした場合には、実用上、接着力は５Ｎ／ｃｈｉｐ以上であることが望ましい。
<Adhesion test>
A paste adhesive composition is applied to a glass epoxy circuit board with an Au flash plating applied to a Cu wiring portion so as to have a thickness of 25 μm, and a 1.5 mm square IC chip is placed thereon and flipped. A connection structure was obtained by thermocompression bonding by heating at 200 ° C. for 60 seconds using a chip bonder. Immediately after being obtained (initial stage), after reflowing (260 ° C.), and the IC chip of the connection structure after being left at 150 ° C. for 100 hours, using a die shear tester (RTR-1100, Resca), the adhesive strength (N / (Chip) was measured. The obtained results are shown in Table 1. When the conditions for this adhesion strength test are assumed, it is practically desirable that the adhesion strength be 5 N / chip or more.
＜光学特性試験＞
接着剤組成物を熱プレス機で加熱加圧して硬化させ、７５μｍ厚のフィルムを作成し、試料とした。得られた試料のフィルム外観を目視観察した。その後、ピーク温度２６０℃の鉛フリーハンダ対応リフロー炉を通し、ＪＩＳ Ｋ７１０５に従って色差（ΔＥ＊ａｂ）を求めた。その後、熱エージング試験（１５０℃オーブン中に３００時間投入）及び光エージング試験（３０Ｗ／ｍ２、３８０ｎｍピーク波長光源、６０℃、１００時間（フェードメーター、スガ試験器（株）））を行い、試験前後の色差（ΔＥ＊ａｂ）を求めた。
得られた結果を表１に示す。
<Optical characteristics test>
The adhesive composition was cured by heating and pressing with a hot press to prepare a 75 μm thick film as a sample. The film appearance of the obtained sample was visually observed. Then, the color difference ((DELTA) E * ab) was calculated | required according to JISK7105 through the reflow furnace corresponding to lead-free solder with a peak temperature of 260 degreeC. Thereafter, a thermal aging test (300 hours in a 150 ° C. oven) and a light aging test (30 W / m 2 , 380 nm peak wavelength light source, 60 ° C., 100 hours (Fade Meter, Suga Test Instruments Co., Ltd.)) The color difference (ΔE * ab) before and after the test was determined.
The obtained results are shown in Table 1.
＜耐腐食性試験＞
銅パターンにＡｇメッキが施されたＡｇメッキ配線を有する２ｃｍ四方のガラスエポキシ基板の表面に、０．０５ｇの接着剤組成物を塗布し、１５０℃のオーブンに１時間投入し、接着剤組成物を硬化させた。配線の端部の配線パッドに無鉛ハンダで配線を接続した。これを、８５℃、８５％ＲＨの恒温恒湿チャンバーに投入し、５０時間、電極間に２０Ｖを印加し、その後、Ａｇメッキ部分を目視観察し、以下の評価基準に従って接着剤組成物の耐腐食性を評価した。得られた結果を表１に示す。
<Corrosion resistance test>
An adhesive composition is applied to the surface of a 2 cm square glass epoxy substrate having an Ag plating wiring in which an Ag plating is applied to a copper pattern, and is placed in an oven at 150 ° C. for 1 hour. Was cured. Wiring was connected to the wiring pad at the end of the wiring with lead-free solder. This was put into a constant temperature and humidity chamber at 85 ° C. and 85% RH, 20 V was applied between the electrodes for 50 hours, and then the Ag plating portion was visually observed, and the resistance of the adhesive composition was evaluated according to the following evaluation criteria. Corrosivity was evaluated. The obtained results are shown in Table 1.
耐腐食性評価基準
Ａ： Ａｇメッキ配線の外観に変化が認められない場合
Ｂ： Ａｇメッキ配線の外観に茶変色が認められる場合
Ｃ： Ａｇメッキ配線にＡｇマイグレーションが発生した場合
Corrosion Resistance Evaluation Criteria A: No change in the appearance of the Ag plating wiring B: Brown discoloration in the appearance of the Ag plating wiring C: When Ag migration occurs in the Ag plating wiring
表１からわかるように、実施例１〜４の接着剤組成物は、脂環式エポキシ化合物１００質量部に対し８１．２質量部の脂環式酸無水物系硬化剤と、脂肪環式エポキシ化合物と脂環式酸無水物系硬化剤との合計１００質量部に対し３０〜４０質量部のアクリル樹脂を含有し、そのアクリル樹脂が、グリシジルメタクリレートと、グリシジルメタクリレート１００質量部に対し２３０〜１０００質量部のアルキルアクリレートとを共重合させた吸水率０．５％以下のものであるので、接着力、光学特性、耐腐食性のいずれも良好な結果を示した。 As can be seen from Table 1, the adhesive compositions of Examples 1 to 4 were 81.2 parts by mass of an alicyclic acid anhydride curing agent and an alicyclic epoxy with respect to 100 parts by mass of the alicyclic epoxy compound. 30 to 40 parts by mass of acrylic resin is contained with respect to 100 parts by mass in total of the compound and the alicyclic acid anhydride curing agent, and the acrylic resin is 230 to 1000 with respect to 100 parts by mass of glycidyl methacrylate and glycidyl methacrylate. Since the water absorption was 0.5% or less obtained by copolymerization with a part by mass of alkyl acrylate, good results were exhibited in all of adhesive strength, optical characteristics, and corrosion resistance.
それに対し、比較例１の接着剤組成物の場合、アクリル樹脂が脂環式エポキシ化合物に溶解しないので、フィルム外観に白濁が生じた。 On the other hand, in the case of the adhesive composition of Comparative Example 1, since the acrylic resin was not dissolved in the alicyclic epoxy compound, the film appearance was clouded.
比較例２の接着剤組成物の場合、ＳＥＢＳゴムが脂環式エポキシ化合物に溶解しないので、フィルム外観に白濁が生じた。 In the case of the adhesive composition of Comparative Example 2, the SEBS rubber was not dissolved in the alicyclic epoxy compound, so that the film appearance was clouded.
比較例３の接着剤組成物の場合、ＳＩＳゴムが脂環式エポキシ化合物に溶解しないので、フィルム外観に白濁が生じた。 In the case of the adhesive composition of Comparative Example 3, since the SIS rubber was not dissolved in the alicyclic epoxy compound, the film appearance was clouded.
比較例４の接着剤組成物の場合、その硬化物が固く脆いため、接着強度が低くかった。 In the case of the adhesive composition of Comparative Example 4, since the cured product was hard and brittle, the adhesive strength was low.
比較例５の接着剤組成物の場合、アクリル樹脂の吸水率が高いため、Ａｇメッキ配線に著しい腐食が生じた。 In the case of the adhesive composition of Comparative Example 5, since the water absorption rate of the acrylic resin was high, significant corrosion occurred in the Ag-plated wiring.
比較例６の接着剤組成物の場合、アクリル樹脂が多くのグリシジル基を含有し、吸水率が高いため、Ａｇメッキ配線に著しい腐食が生じた。 In the case of the adhesive composition of Comparative Example 6, since the acrylic resin contains many glycidyl groups and has a high water absorption, significant corrosion occurred in the Ag-plated wiring.
比較例７の接着剤組成物の場合、アクリル樹脂が多くのＯＨ基を含有し、吸水率が高いため、Ａｇメッキ配線に著しい腐食が生じた。 In the case of the adhesive composition of Comparative Example 7, since the acrylic resin contains many OH groups and has a high water absorption rate, significant corrosion occurred in the Ag-plated wiring.
比較例８の接着剤組成物の場合、エポキシ化合物の含有量が多いため、エポキシ化合物の一部が未硬化のままとなり、接着強度が低くなった。 In the case of the adhesive composition of Comparative Example 8, since the content of the epoxy compound was large, a part of the epoxy compound remained uncured and the adhesive strength was lowered.
本発明の接着剤組成物は、特定割合の脂環式エポキシ化合物と脂環式酸無水物系硬化剤とアクリル樹脂とから構成され、しかもアクリル樹脂として、特定割合のグリシジルメタクリレートとアルキルアクリレートとを重合させたものであって、吸水率が所定割合以下のものを使用する。このため、接着力の低下、硬化物の白濁や着色及び回路基板の配線の腐食という問題の発生を大きく抑制することができる。よって、ＬＥＤチップなどの光半導体チップを回路基板にフリップチップ実装する際に有用である。 The adhesive composition of the present invention is composed of a specific proportion of an alicyclic epoxy compound, an alicyclic acid anhydride-based curing agent, and an acrylic resin, and as the acrylic resin, a specific proportion of glycidyl methacrylate and alkyl acrylate. A polymerized product having a water absorption rate of a predetermined ratio or less is used. For this reason, generation | occurrence | production of the problem of the fall of adhesive force, the cloudiness and coloring of hardened | cured material, and the corrosion of the wiring of a circuit board can be suppressed significantly. Therefore, it is useful when flip-chip mounting an optical semiconductor chip such as an LED chip on a circuit board.
Claims (8)
脂環式酸無水物系硬化剤の含有量が、脂環式エポキシ化合物１００質量部に対し８０〜１２０質量部であり、該アクリル樹脂の含有量が、脂肪環式エポキシ化合物と脂環式酸無水物系硬化剤とアクリル樹脂との合計１００質量部中に５〜５０質量部であり、
該アクリル樹脂が、アルキル（メタ）アクリレートと、アルキル（メタ）アクリレート１００質量部に対し２〜１００質量部のグリシジルメタクリレートとを共重合させた吸水率１．２％以下の樹脂であることを特徴とする接着剤組成物。 An adhesive composition for flip-chip mounting chip components on a circuit board, comprising an alicyclic epoxy compound, an alicyclic acid anhydride curing agent, and an acrylic resin,
The content of the alicyclic acid anhydride-based curing agent is 80 to 120 parts by mass with respect to 100 parts by mass of the alicyclic epoxy compound, and the content of the acrylic resin is the alicyclic epoxy compound and the alicyclic acid. 5 to 50 parts by mass in a total of 100 parts by mass of the anhydride-based curing agent and the acrylic resin,
The acrylic resin is a resin having a water absorption of 1.2% or less obtained by copolymerizing alkyl (meth) acrylate and 2 to 100 parts by mass of glycidyl methacrylate with respect to 100 parts by mass of alkyl (meth) acrylate. An adhesive composition.
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