EP1090057A1 - Reworkable thermosetting resin compositions - Google Patents
Reworkable thermosetting resin compositionsInfo
- Publication number
- EP1090057A1 EP1090057A1 EP00916567A EP00916567A EP1090057A1 EP 1090057 A1 EP1090057 A1 EP 1090057A1 EP 00916567 A EP00916567 A EP 00916567A EP 00916567 A EP00916567 A EP 00916567A EP 1090057 A1 EP1090057 A1 EP 1090057A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition according
- composition
- methylimidazole
- bis
- combinations
- 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.)
- Withdrawn
Links
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 45
- 239000011342 resin composition Substances 0.000 title claims abstract description 38
- 239000000203 mixture Substances 0.000 claims abstract description 88
- 239000004065 semiconductor Substances 0.000 claims abstract description 68
- 239000000758 substrate Substances 0.000 claims abstract description 38
- 229920000647 polyepoxide Polymers 0.000 claims description 44
- 239000003822 epoxy resin Substances 0.000 claims description 43
- -1 anhydride compounds Chemical class 0.000 claims description 31
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 31
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 239000004593 Epoxy Substances 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- 239000004643 cyanate ester Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000011256 inorganic filler Substances 0.000 claims description 12
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 238000007789 sealing Methods 0.000 claims description 9
- 150000002460 imidazoles Chemical class 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229920003986 novolac Polymers 0.000 claims description 5
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole Chemical compound CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 claims description 4
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 claims description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 4
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 claims description 4
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 229920001169 thermoplastic Polymers 0.000 claims description 4
- 239000004416 thermosoftening plastic Substances 0.000 claims description 4
- 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 claims description 4
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 235000013849 propane Nutrition 0.000 claims description 3
- 230000003014 reinforcing effect Effects 0.000 claims description 3
- 239000000565 sealant Substances 0.000 claims description 3
- 150000004756 silanes Chemical class 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims description 2
- NOQONXWBCSGVGF-UHFFFAOYSA-N 1,2,4-triphenylimidazole Chemical compound C=1C=CC=CC=1N1C=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 NOQONXWBCSGVGF-UHFFFAOYSA-N 0.000 claims description 2
- KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical compound C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 claims description 2
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 claims description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- XIOGJAPOAUEYJO-UHFFFAOYSA-N 2-(2-methoxyphenyl)-4,5-diphenyl-1h-imidazole Chemical compound COC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 XIOGJAPOAUEYJO-UHFFFAOYSA-N 0.000 claims description 2
- OPHSKKPSEMOQLM-UHFFFAOYSA-N 2-(2-phenylethenyl)-1h-imidazole Chemical compound N=1C=CNC=1C=CC1=CC=CC=C1 OPHSKKPSEMOQLM-UHFFFAOYSA-N 0.000 claims description 2
- YAXVEVGFPVWPKA-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)ethenyl]-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C=CC1=NC=CN1 YAXVEVGFPVWPKA-UHFFFAOYSA-N 0.000 claims description 2
- SLLDUURXGMDOCY-UHFFFAOYSA-N 2-butyl-1h-imidazole Chemical compound CCCCC1=NC=CN1 SLLDUURXGMDOCY-UHFFFAOYSA-N 0.000 claims description 2
- XUZOLVDRTWTQJB-UHFFFAOYSA-N 2-heptadec-1-enyl-5-methyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCC=CC1=NC(C)=CN1 XUZOLVDRTWTQJB-UHFFFAOYSA-N 0.000 claims description 2
- RFWOZDRUDBNGSY-UHFFFAOYSA-N 2-heptadecyl-5-methyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC(C)=CN1 RFWOZDRUDBNGSY-UHFFFAOYSA-N 0.000 claims description 2
- OMBXZTBWATXTMQ-UHFFFAOYSA-N 2-methyl-1-(1-phenyltridecyl)imidazole Chemical compound C1=CN=C(C)N1C(CCCCCCCCCCCC)C1=CC=CC=C1 OMBXZTBWATXTMQ-UHFFFAOYSA-N 0.000 claims description 2
- WBDSXISQIHMTGL-UHFFFAOYSA-N 2-methyl-4,5-diphenyl-1h-imidazole Chemical compound N1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 WBDSXISQIHMTGL-UHFFFAOYSA-N 0.000 claims description 2
- UPOLYUOBDJSLRC-UHFFFAOYSA-N 2-undec-1-enyl-1h-imidazole Chemical compound CCCCCCCCCC=CC1=NC=CN1 UPOLYUOBDJSLRC-UHFFFAOYSA-N 0.000 claims description 2
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 claims description 2
- UIDDPPKZYZTEGS-UHFFFAOYSA-N 3-(2-ethyl-4-methylimidazol-1-yl)propanenitrile Chemical compound CCC1=NC(C)=CN1CCC#N UIDDPPKZYZTEGS-UHFFFAOYSA-N 0.000 claims description 2
- BVYPJEBKDLFIDL-UHFFFAOYSA-N 3-(2-phenylimidazol-1-yl)propanenitrile Chemical compound N#CCCN1C=CN=C1C1=CC=CC=C1 BVYPJEBKDLFIDL-UHFFFAOYSA-N 0.000 claims description 2
- SZUPZARBRLCVCB-UHFFFAOYSA-N 3-(2-undecylimidazol-1-yl)propanenitrile Chemical compound CCCCCCCCCCCC1=NC=CN1CCC#N SZUPZARBRLCVCB-UHFFFAOYSA-N 0.000 claims description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 2
- YGOFNNAZFZYNIX-UHFFFAOYSA-N 3-N-phenylbenzene-1,2,3-triamine Chemical compound NC=1C(=C(C=CC1)NC1=CC=CC=C1)N YGOFNNAZFZYNIX-UHFFFAOYSA-N 0.000 claims description 2
- LTGRDWFVGBZDIR-UHFFFAOYSA-N 4-(4,5-diphenyl-1h-imidazol-2-yl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 LTGRDWFVGBZDIR-UHFFFAOYSA-N 0.000 claims description 2
- MJZYCDYAVCQQEQ-UHFFFAOYSA-N 5-tert-butyl-2-(4,5-diphenyl-1H-imidazol-2-yl)phenol Chemical compound OC1=CC(C(C)(C)C)=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 MJZYCDYAVCQQEQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052582 BN Inorganic materials 0.000 claims description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052581 Si3N4 Inorganic materials 0.000 claims description 2
- KPSLOKZNJBTGRP-UHFFFAOYSA-N [2-(2-cyanatophenoxy)phenyl] cyanate Chemical class N#COC1=CC=CC=C1OC1=CC=CC=C1OC#N KPSLOKZNJBTGRP-UHFFFAOYSA-N 0.000 claims description 2
- YVXTXJOQTQPNPV-UHFFFAOYSA-N [2-(2-cyanatophenyl)sulfanylphenyl] cyanate Chemical class N#COC1=CC=CC=C1SC1=CC=CC=C1OC#N YVXTXJOQTQPNPV-UHFFFAOYSA-N 0.000 claims description 2
- NTQOTSRMQVHZDE-UHFFFAOYSA-N [2-[(2-cyanatophenyl)methyl]phenyl] cyanate Chemical class N#COC1=CC=CC=C1CC1=CC=CC=C1OC#N NTQOTSRMQVHZDE-UHFFFAOYSA-N 0.000 claims description 2
- LYZFLNSQKAIUHI-UHFFFAOYSA-N [2-[2-(2-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical class C=1C=CC=C(OC#N)C=1C(C)(C)C1=CC=CC=C1OC#N LYZFLNSQKAIUHI-UHFFFAOYSA-N 0.000 claims description 2
- OYQHOGAPGFEZAK-UHFFFAOYSA-N [2-bis(2-cyanatophenoxy)phosphanyloxyphenyl] cyanate Chemical class N#COC1=CC=CC=C1OP(OC=1C(=CC=CC=1)OC#N)OC1=CC=CC=C1OC#N OYQHOGAPGFEZAK-UHFFFAOYSA-N 0.000 claims description 2
- LICDITOZQJQJCC-UHFFFAOYSA-N [2-bis(2-cyanatophenoxy)phosphoryloxyphenyl] cyanate Chemical class C=1C=CC=C(OC#N)C=1OP(OC=1C(=CC=CC=1)OC#N)(=O)OC1=CC=CC=C1OC#N LICDITOZQJQJCC-UHFFFAOYSA-N 0.000 claims description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002318 adhesion promoter Substances 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical group CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 claims description 2
- SEAZOECJMOZWTD-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethyl)silane Chemical compound CO[Si](OC)(OC)CC1CO1 SEAZOECJMOZWTD-UHFFFAOYSA-N 0.000 claims description 2
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 claims 1
- BDHGFCVQWMDIQX-UHFFFAOYSA-N 1-ethenyl-2-methylimidazole Chemical compound CC1=NC=CN1C=C BDHGFCVQWMDIQX-UHFFFAOYSA-N 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 239000004952 Polyamide Substances 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 238000002507 cathodic stripping potentiometry Methods 0.000 abstract description 17
- 238000003491 array Methods 0.000 abstract description 2
- 230000010354 integration Effects 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 13
- 238000001723 curing Methods 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- 150000001913 cyanates Chemical class 0.000 description 10
- 239000000853 adhesive Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 9
- 229910000679 solder Inorganic materials 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 229920003319 Araldite® Polymers 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 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 5
- 230000035939 shock Effects 0.000 description 5
- 238000005382 thermal cycling Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000008439 repair process Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000004036 acetal group Chemical group 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000000712 assembly Effects 0.000 description 2
- 238000000429 assembly Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 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 2
- 238000010586 diagram Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- SOOZEQGBHHIHEF-UHFFFAOYSA-N methyltetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21C SOOZEQGBHHIHEF-UHFFFAOYSA-N 0.000 description 2
- 238000004377 microelectronic Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- UFKLQICEQCIWNE-UHFFFAOYSA-N (3,5-dicyanatophenyl) cyanate Chemical compound N#COC1=CC(OC#N)=CC(OC#N)=C1 UFKLQICEQCIWNE-UHFFFAOYSA-N 0.000 description 1
- YDCUTCGACVVRIQ-UHFFFAOYSA-N (3,6-dicyanatonaphthalen-1-yl) cyanate Chemical compound N#COC1=CC(OC#N)=CC2=CC(OC#N)=CC=C21 YDCUTCGACVVRIQ-UHFFFAOYSA-N 0.000 description 1
- QQZZMAPJAKOSNG-UHFFFAOYSA-N (3-cyanatophenyl) cyanate Chemical compound N#COC1=CC=CC(OC#N)=C1 QQZZMAPJAKOSNG-UHFFFAOYSA-N 0.000 description 1
- GUGZCSAPOLLKNG-UHFFFAOYSA-N (4-cyanatophenyl) cyanate Chemical compound N#COC1=CC=C(OC#N)C=C1 GUGZCSAPOLLKNG-UHFFFAOYSA-N 0.000 description 1
- DEABFUINOSGCMK-UHFFFAOYSA-N (4-ethylphenyl) cyanate Chemical compound CCC1=CC=C(OC#N)C=C1 DEABFUINOSGCMK-UHFFFAOYSA-N 0.000 description 1
- OFIWROJVVHYHLQ-UHFFFAOYSA-N (7-cyanatonaphthalen-2-yl) cyanate Chemical compound C1=CC(OC#N)=CC2=CC(OC#N)=CC=C21 OFIWROJVVHYHLQ-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MKBBSFGKFMQPPC-UHFFFAOYSA-N 2-propyl-1h-imidazole Chemical compound CCCC1=NC=CN1 MKBBSFGKFMQPPC-UHFFFAOYSA-N 0.000 description 1
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/01—Chemical elements
- H01L2924/01067—Holmium [Ho]
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/01—Chemical elements
- H01L2924/01075—Rhenium [Re]
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/01—Chemical elements
- H01L2924/01082—Lead [Pb]
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- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/10—Details of semiconductor or other solid state devices to be connected
- H01L2924/11—Device type
- H01L2924/12—Passive devices, e.g. 2 terminal devices
- H01L2924/1203—Rectifying Diode
- H01L2924/12033—Gunn diode
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- H—ELECTRICITY
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/10—Details of semiconductor or other solid state devices to be connected
- H01L2924/11—Device type
- H01L2924/14—Integrated circuits
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/19—Details of hybrid assemblies other than the semiconductor or other solid state devices to be connected
- H01L2924/1901—Structure
- H01L2924/1904—Component type
- H01L2924/19042—Component type being an inductor
Definitions
- thermosetting resin compositions useful for mounting onto a circuit board semiconductor devices, such as chip size or chip scale packages (“CSPs”), ball grid arrays (“BGAs”), and the like, each of which having a semiconductor chip, such as large scale integration (“LSI”), on a carrier substrate.
- CSPs chip size or chip scale packages
- BGAs ball grid arrays
- LSI large scale integration
- the compositions of this invention are reworkable when subjected to appropriate conditions.
- the CSP/BGA assembly is connected to electrical conductors on a circuit board by use of a solder connection or the like.
- a solder connection or the like.
- the reliability of the solder connection between the circuit board and the CSP/BGA often becomes suspect .
- the space between the CSP/BGA assembly and the circuit board is often now filled with a sealing resin (often referred to as underfill sealing) in order to relieve stresses caused by thermal cycling, thereby improving heat shock properties and enhancing the reliability of the structure.
- thermosetting resins are typically used as the underfill sealing material, in the event of a failure after the CSP/BGA assembly is mounted on the circuit board, it is very difficult to replace the CSP/BGA assembly without destroying or scrapping the structure in its entirety.
- Japanese Laid-Open Patent Publication No. 77264/94 it is conventional to use a solvent to remove residual resin from a circuit board.
- swelling the resin with a solvent is a time consuming process and the corrosive organic acid ordinarily used as the solvent may reduce the reliability of the circuit board.
- that disclosure speaks to a method for removing residual resin by irradiation with electromagnetic radiation.
- 251516/93 also discloses a mounting process using bisphenol A type epoxy resin (CV5183 or CV5183S; manufactured by Matsushita Electric Industrial Co., Ltd.).
- CV5183 or CV5183S manufactured by Matsushita Electric Industrial Co., Ltd.
- the removal process so disclosed does not consistently permit easy removal of the chip, the curing step is lengthy at elevated temperatures, and the process generally results in poor productivity.
- thermoplastic underfill resins are known for use in semiconductor chip attachment. See U.S. Patent No. 5,783,867 (Belke, Jr.).
- thermoplastic resins tend to leak under relatively modest temperature conditions.
- thermosetting resins cure into a matrix which ordinarily have greater thermal stability under end use operating temperatures .
- 5,512,613 (Afzali-Ardakani) and 5,560,934 (Afzali-Ardakani) , each refer to a reworkable thermoset composition based on a diepoxide component in which the organic linking moiety connecting the two epoxy groups of the diepoxide includes an acid cleavable acyclic acetal group.
- acid cleavable acyclic acetal groups forming the bases of the reworkable composition, a cured thermoset need only be introduced to an acidic environment in order to achieve softening and a loss of much of its adhesiveness.
- U.S. Patent No. 5,872,158 (Kuczynski) refers to thermosetting compositions capable of curing upon exposure to actinic radiation, which are based on acetal diacrylates, and reaction products of which are reported to be soluble in dilute acid.
- U.S. Patent No. 5,760,337 refers to thermally reworkable crosslinked resins to fill the gap created between a semiconductor device and a substrate to which it is attached. These resins are produced by reacting a dienophile (with a functionality greater than 1) with a 2.5-dialkyl substituted furan-containing polymer.
- thermosetting resin composition capable of sealing underfilling between a semiconductor device including a semiconductor chip mounted on a carrier substrate and a circuit board to which said semiconductor device is electrically connected.
- the composition includes about 100 parts by weight of an epoxy resin, about 3 to about 60 parts by weight of a curing agent, and about 1 to about 90 parts by weight of a plasticizer.
- the area around the cured thermoset is to be heated at a temperature of about 190 to about 260°C for a period of time ranging from about 10 seconds to about 1 minute in order to achieve softening and a loss of much of its adhesiveness.
- an underfilling sealing material to provide good productivity and thermal shock properties, while allowing the substrates with which it is to be used to be readily processed and easily separated from a semiconductor device without application of acidic media or elevated temperature conditions that may compromise the integrity of the semiconductor devices remaining on the substrate or the substrate itself.
- thermosetting resin composition which is used as an underfill sealant between a semiconductor device and a circuit board to which the semiconductor device is electrically connected, includes broadly a curable resin component an epoxy resin component, a portion of which is an epoxy compound having at least one thermally cleavable linkage; an optional inorganic filler component; and a curing agent component including an anhydride component, a nitrogen-containing component, such as an amine compound, an amide compound, and/or an imidazole compound, and combinations thereof.
- Reaction products of these compositions are capable of softening under exposure to elevated temperature conditions, such as in excess of the tempertures used to cure the composition.
- elevated temperature conditions such as in excess of the tempertures used to cure the composition.
- Such temperature exposure combined with the epoxy compound having at least one thermally cleavable linkage provides the reworkable aspect of this invention.
- the remaining components, discussed below, provide the physical properties and characteristics for the compositions and reaction products to render the compositions attractive for commercial use, particularly in the microelectronics industry.
- the epoxy compounds with at least one thermally cleavable linkage may be chosen from those within the following formula:
- each R is independently selected from hydrogen, methyl, ethyl, propyl , isopropyl, butyl, isobutyl, t-butyl, C j ⁇ . 4 alkoxy, halogen, cyano and nitro
- each R 3 is independently selected from hydrogen, methyl, ethyl, propyl, and isopropyl
- R x and R 2 are each independently selected from hydrogen, methyl, ethyl, propyl, phenyl , tolyl, and benzyl, provided that both R x and R 2 cannot be hydrogen and m is 0 or 1.
- Particularly desirable epoxy compounds within formula I are given in the section entitled "Detailed Description of the Invention", which follows hereinafter.
- the inventive thermosetting resin composition is useful as an underfilling sealing resin, and enables a semiconductor device, such as a CSP/BGA assembly which includes a semiconductor chip mounted on a carrier substrate, to be securely connected to a circuit board by short-time heat curing and with good productivity.
- Reaction products of the inventive compositions demonstrate excellent heat shock properties (or thermal cycle properties) , and permit the semiconductor device to be easily removed from the circuit board by localized heating in the event of semiconductor device or connection failure. This makes it possible to reuse the circuit board (with the remaining functioning semiconductor devices still electrically attached) and thereby achieve an improvement in the yield of the production process and a reduction in production cost.
- compositions of this invention may also be used for microelectronic applications beyond sealing underfill, such as with glob top, die attachment and other applications for thermosetting compositions in which rapid cure time and an extended useful working life are desirable.
- FIG. 1 depicts a cross-sectional view showing an example of the mounting structure in which the thermosetting resin composition of the present invention is used.
- FIG. 2 depicts a flow diagram of a procedure useful to rework a cured thermosetting resin composition in accordance with the present invention, so as to remove a semiconductor device from a circuit board to which it had been attached.
- the composition includes about 10 to about 60 weight percent of the epoxy resin component by weight of the total composition, of which about 25 to about 75 weight percent thereof is comprised of an epoxy compound having at least one thermally cleavable linkage; about 0 to about 60 weight percent of the inorganic filler component; and 0.01 to about 60 weight percent of the curing agent component, of which about 0 to about 60 weight percent thereof is comprised of an anhydride compound, 0 to about 5 weight percent thereof is comprised of an amide compound, such as a cyano-functionalized amide, like dicyandamide, and 0 to about 2 weight percent thereof is comprised of an imidazole compound.
- these values may vary somewhat. Such variation may be achieved without undue experimentation by those persons skilled in the art, and accordingly are contemplated within the scope of the present invention.
- the epoxy resin component of the present invention may include any common epoxy resin, such as a multifunctional epoxy resin.
- the multifunctional epoxy resin should be included in an amount within the range of about 15 weight percent to about 75 weight percent of the total of the epoxy resin component .
- the amount thereof should be in the range of from about 35 to about 65 weight percent, such as about 40 to about 50 weight percent of the total of the epoxy resin component.
- multifunctional epoxy resin examples include bisphenol-A-type epoxy resin, bisphenol-F-type epoxy resin (such as RE-404-S from Nippon Kayaku, Japan) , phenol novolac-type epoxy resin, and cresol novolac-type epoxy from resin (such as "ARALDITE” ECN 1871 from Ciba Specialty Chemicals, Hawthorne, New York) .
- epoxy resins include polyepoxy compounds based on aromatic amines and epichlorohydrin, such as N,N,N' ,N' -tetraglycidyl-4 , 4 ' -diaminodiphenyl methane; N- diglycidyl-4-aminophenyl glycidyl ether; and N,N,N',N'- tetraglycidyl-1, 3-propylene bis-4-aminobenzoate .
- polyepoxy compounds based on aromatic amines and epichlorohydrin such as N,N,N' ,N' -tetraglycidyl-4 , 4 ' -diaminodiphenyl methane; N- diglycidyl-4-aminophenyl glycidyl ether; and N,N,N',N'- tetraglycidyl-1, 3-propylene bis-4-aminobenzoate .
- epoxy resins suitable for use herein also include polyglycidyl derivatives of phenolic compounds, such as those available commercially under the tradename "EPON”, such as “EPON” 828, “EPON” 1001, “EPON” 1009, and “EPON” 1031 from Shell Chemical Co.; "DER” 331, “DER” 332, “DER” 334, and “DER” 542 from Dow Chemical Co.; and BREN-S from Nippon Kayaku.
- EPON polyglycidyl derivatives of phenolic compounds
- Suitable epoxy resins include polyepoxides prepared from polyols and the like and polyglycidyl derivatives of phenol-formaldehyde novolacs, the latter of which are available commercially under the tradename "DEN”, such as "DEN” 431, "DEN” 438, and "DEN” 439 from Dow Chemical. Cresol analogs are also available commercially under the tradename "ARALDITE”, such as
- ARALDITE ECN 1235, “ARALDITE” ECN 1273, and “ARALDITE” ECN 1299 from Ciba Specialty Chemicals Corporation.
- SU-8 is a bisphenol-A-type epoxy novolac available from Interez, Inc. Polyglycidyl adducts of amines, aminoalcohols and polycarboxylic acids are also useful in this invention, commercially available resins of which include “GLYAMINE” 135, “GLYAMINE” 125, and “GLYAMINE” 115 from F.I.C. Corporation; "ARALDITE” MY-720, “ARALDITE” 0500, and "ARALDITE” 0510 from Ciba Specialty Chemicals and PGA-X and PGA-C from the Sherwin-Williams Co.
- the epoxy compounds with at least one thermally cleavable linkage may be chosen from those within the following formula:
- each R is independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert butyl, Ci- 4 alkoxy, halogen, cyano and nitro
- each R 3 is independently selected from hydrogen, methyl, ethyl, propyl, and isopropyl
- Ri and R 2 are each independently selected from hydrogen, methyl, ethyl, propyl, phenyl, tolyl and benzyl, provided that both Rx and R 2 cannot be hydrogen and m is 0 or 1.
- Particularly desirable epoxy compounds within formula I include:
- epoxy resin component of the epoxy compound (s) with at least one thermally cleavable linkage allows for repair, replacement, recovery and/or recycling of operative electronic components from assemblies that have become at least in part inoperative.
- epoxy compounds can be prepared from cycloaliphatic diene esters having the following formula
- R, Ri, R 2 , R 3 and m are as given above, which themselves are the condensation product of an alcohol within formula A below:
- the condensation reaction is ordinarily performed in an anhydrous polar solvent at a temperature ranging from 0 to 20°C for a time period ranging from 6 to 18 hours.
- a peracid such as peracetic acid, perbenzoic acid, meta-chloroperbenzoic acid, and the like
- the reaction carried out until epoxidization of diene ester occurs, typically within a period of time of from 2 to 18 hours.
- the inorganic filler component may often include reinforcing silicas, such as fused silicas, and may be untreated or treated so as to alter the chemical nature of their surface. Virtually any reinforcing fused silica may be used.
- Particularly desirable ones have a low ion concentration and are relatively small in particle size
- the inorganic filler component should include materials capable of catalyzing the polymerization of the epoxy resin component of the inventive compositions.
- Desirable curing agents for use with the present invention include an anhydride component, a nitrogen-containing component, such as an amine compound, an amide compound, and an imidazole compound, and combinations thereof.
- Appropriate anhydride compounds for use herein include mono- and poly-anhydrides, such as hexahydrophthalic anhydride (“HHPA”) and methyl hexahydrophthalic anhydride (“MHHPA”) (commercially available from Lindau Chemicals, Inc., Columbia, South Carolina, used individually or as a combination, which combination is available under the trade designation "LINDRIDE” 62C) and 5- (2 , 5-dioxotetrahydrol) -3- methyl-3 -cyclohexene-1, 2-dicarboxylic anhydride (commercially available from ChrisKev Co., Leewood, Kansas under the trade designation B-4400) .
- HHPA hexahydrophthalic anhydride
- MHHPA methyl hexahydrophthalic anhydride
- amine compounds examples include aliphatic polyamines, such as diethylenetriamine, triethylenetetramine and diethylaminopropylamine; aromatic polyamines, such as m- xylenediamine and diaminodiphenylamine; and alicyclic polyamines, such as isophoronediamine and menthenediamine .
- amide compounds include cyano- functionalized amides, such as dicyandiamide .
- the imidazole compounds may be chosen from imidazole, isoimidazole, and substituted imidazoles -- such as alkyl-substituted imidazoles (e.g. , 2-methyl imidazole, 2-ethyl-4-methylimidazole, 2 , 4-dimethylimidazole, butylimidazole, 2-heptadecenyl-4-methylimidazole, 2- methylimidazole, 2-undecenylimidazole, l-vinyl-2- methylimidazole, 2-n-heptadecylimidazole, 2- undecylimidazole, 2-heptadecylimidazole, 2-ethyl 4- methylimidazole, l-benzyl-2-methylimidazole, l-propyl-2- methylimidazole, 1-cyanoethyl-2-methylimidazole, 1- cyanoethyl-2-ethyl-4
- Examples of commercial imidazole compounds are available from Air Products, Allentown, Pennsylvania under the trade designation “CUREZOL” 1B2MZ and from Synthron, Inc., Morganton, North Carolina under the trade designation “ACTIRON” NXJ-60.
- the curing agent component may be used in an amount of from about 5 to about 40 parts by weight, per 100 parts of the epoxy resin, such as from about 5 to about 40 parts by weight, per 100 parts of the epoxy resin.
- composition may also include a flowability agent, such as a silane and/or titanate.
- a flowability agent such as a silane and/or titanate.
- silanes for use herein include octyl trimethoxy silane (commercially available from OSI Specialties Co., Danbury, Connecticut under the trade designation A-137) , and methacryloxy propyl trimethoxy silane (commercially available from OSI under the trade designation A-174) .
- titanates for use herein include titanium IV tetrakis [2, 2-bis [ (2-propenyloxy) methyl] -1- butanolato-0] [bis (ditridecylphosphito-0) , dihydrogen] 2 (commercially available from Kenrich Petrochemical Inc., Bayonne, New Jersey under the trade designation KR-55) .
- the flowability agent When used, the flowability agent may be used in an amount of 0 to about 2 parts by weight, per 100 parts of the epoxy resin.
- adhesion promoters such as the silanes, glycidyl trimethoxysilane (commercially available from OSI under the trade designation A-187) or gamma-amino propyl triethoxysilane (commercially available from OSI under the trade designation A-1100) , may be used.
- Cyanate esters may also be used in the inventive compositions.
- the cyanate esters useful as a component in the inventive compositions may be chosen from dicyanatobenzenes, tricyanatobenzenes, dicyanatonaphthalenes, tricyanatonaphthalenes, dicyanato- biphenyl, bis (cyanatophenyl) methanes and alkyl derivatives thereof, bis (dihalocyanatophenyl) propanes, bis (cyanatophenyl) ethers, bis (cyanatophenyl) sulfides, bis (cyanatophenyl) propanes, tris (cyanatophenyl) phosphites, tris (cyanatophenyl) phosphates, bis (halocyanatophenyl) methanes, cyanated novolac, bis [cyanatophenyl (methylethylidene) ] benzene, cyanated bisphenol-terminated thermoplastic oligomers / and combinations thereof.
- aryl compounds having at least one cyanate ester group on each molecule may be generally represented by the formula Ar(OCN) m , where Ar is an aromatic radical and m is an integer from 2 to 5.
- the aromatic radical Ar should contain at least 6 carbon atoms, and may be derived, for example, from aromatic hydrocarbons, such as benzene, biphenyl, naphthalene, anthracene, pyrene or the like.
- the aromatic radical Ar may also be derived from a polynuclear aromatic hydrocarbon in which at least two aromatic rings are attached to each other through a bridging group.
- the aromatic radical Ar may also contain further ring-attached, non-reactive substituents .
- cyanate esters include, for instance, 1, 3-dicyanatobenzene; 1, 4-dicyanatobenzene; 1,3,5- tricyanatobenzene; 1,3-, 1,4-, 1,6-, 1,8-, 2,6- or 2,7- dicyanatonaphthalene; 1, 3 , 6-tricyanatonaphthalene; 4,4'- dicyanato-biphenyl; bis (4-cyanatophenyl) methane and 3 , 3 ' , 5, 5 ' -tetramethyl bis (4-cyanatophenyl) methane; 2,2- bis (3, 5-dichloro-4-cyanatophenyl)propane; 2,2-bis(3,5- dibromo-4-dicyanatophenyl
- the cyanate esters When used, the cyanate esters may be used in an amount of about 1 to about 20 weight percent based on the total amount of the epoxy resin component .
- compositions of the present invention may also be used in the compositions of the present invention to achieve certain desired physical properties of the composition, the cured reaction product, or both.
- a reactive co-monomer component for the epoxy resin component such as a reactive diluent.
- Appropriate reactive diluents for use herein may include monofunctional or certain multifunctional epoxy resins .
- the reactive diluent should have a viscosity which is lower than that of the epoxy resin component . Ordinarily, the reactive diluent should have a viscosity less than about 250 cps .
- such resin should be employed in an amount of up to about 50 parts based on the total of the epoxy resin component.
- the monofunctional epoxy resin should have an epoxy group with an alkyl group of about 6 to about 28 carbon atoms, examples of which include C 6 _ 28 alkyl glycidyl ethers, C 6 . 28 fatty acid glycidyl esters and C 6 . 28 alkylphenol glycidyl ethers.
- monofunctional epoxy resin reactive diluents include those from Pacific Epoxy Polymers, Richmond, Michigan, under the trade designations PEP-6770 (glycidyl ester of neodecandoic acid) , PEP-6740 (phenyl glycidyl ether) and PEP-6741 (butyl glycidyl ether) .
- compositions of the present invention may further contain other additives, such as defoaming agents, leveling agents, dyes, and pigments.
- photopolymerization initiators may also be incorporated therein, provided that such initiators do not adversely affect the properties of the composition or reaction products formed therefrom.
- thermosetting resin compositions of the present invention may be of the one-pack type, in which all the ingredients are mixed together, or of the two-pack type in which the curable component (s) , is (are) included in one part and the curing agent is stored separately in a second part, and mixed together only prior to use.
- thermosetting resin compositions according to the present invention penetrate and flow readily into the space between the semiconductor chip and the circuit board, or at least show a reduction in viscosity under heated or use conditions thus penetrating and flowing easily.
- thermosetting resin compositions of this invention by selecting the types and proportions of various components to reach a viscosity at a temperature of 25°C in the range of 500 to 70,000 cps, such as 800 to 3,000 cps, depending on the amount present (if any) of an inorganic filler component, so as to improve its ability to penetrate into the space (e.g. , of 10 to 200 ⁇ m) between the circuit board and the semiconductor device.
- the gel times of the compositions will also be tailored to a specified period of time (such as 15 seconds, or 1 or 2 minutes) at a temperature of about 150°C.
- the inventive compositions should show no or substantially no increase of viscosity after a period of time of about six hours. With such a gel time, the compositions penetrate into the space (e.g. , of 10 to 200 ⁇ m) between the circuit board and the semiconductor device relatively rapidly, and allow for a greater number of assemblies to be filled without observing a viscosity increase in the composition thereby rendering it less effective for application.
- Reference to FIG. 1 shows a mounted structure
- thermosetting resin composition of the present invention in which a thermosetting resin composition of the present invention has been applied and cured.
- the FC package 4 is formed by connecting a semiconductor chip (a bare chip) 2 to a carrier substrate 1 (e.g. , a circuit board) and sealing the space therebetween suitably with a thermosetting resin composition 3.
- the semiconductor chip 2 may be passed over a substrate bearing a conductive adhesive paste (such as a metal-filled epoxy) to form a layer thereof on the semiconductor chip 2.
- a conductive adhesive paste such as a metal-filled epoxy
- the layer is ordinarily formed by a printing mechanism.
- the conductive adhesive paste may be applied on either the carrier substrate or the semiconductor chip.
- This connection may also be made by an anisotropically conductive adhesive. See International Patent Publication No. PCT/US97/13677.
- the semiconductor chip 2 is positioned over the carrier substrate 1 in such a manner so that the semiconductor chip 2 is in alignment with the electrodes 5 and 6 on the carrier substrate 1, now coated with a patterned layer of conductive adhesive paste or solder, 7 and 8.
- the conductive adhesive paste may be cured by a variety of ways, though ordinarily a heat cure mechanism is employed.
- the space between the semiconductor chip 2 and the carrier substrate 1 is sealed with a thermosetting resin composition 3.
- the cured product of the thermosetting resin composition should completely fill that space.
- the semiconductor ship ordinarily may be coated with a polyimide-, benzocyclobutane- or silicone nitride- based material to passivate environmental corrosion.
- Carrier substrates may be constructed from ceramic substrates of A1 2 0 3 , SiN 3 and mullite (Al 2 0 3 -Si0 2 ) ; substrates or tapes of heat-resistant resins, such as polyimides; glass-reinforced epoxy; ABS and phenolic substrates which are also used commonly as circuit boards; and the like. Any electrical connection of the semiconductor chip to the carrier substrate may be used, such as connection by a high- melting solder or electrically (or anisotropically) conductive adhesive and the like. In order to facilitate connections, particularly in SBB technology, the electrodes may be formed as wire bond bumps .
- the resulting structure is ordinarily subjected to a continuity test or the like. After passing such test, the semiconductor chip may be fixed thereto with a thermosetting resin composition, as described below. In this way, in the event of a failure, the semiconductor chip may be removed before it is fixed to the carrier substrate with the thermosetting resin composition.
- thermosetting resin composition in accordance with this invention is applied to the periphery of the electronically-connected semiconductor chip.
- the composition penetrates by capillary action into the space between the carrier substrate and the semiconductor chip.
- thermosetting resin composition is then thermally cured by the application of heat.
- the thermosetting resin composition shows a significant reduction in viscosity and hence an increase in fluidity, so that it more easily penetrates into the space between the carrier substrate and the semiconductor chip.
- the thermosetting resin composition is allowed to penetrate fully into the entire space between the carrier substrate and the semiconductor chip.
- Thermosetting resin compositions of the present invention may ordinarily be cured by heating to a temperature in the range of about 120 to about 180°C for a period of time of about 0.5 to 30 minutes. However, generally after application of the composition, an initial cure time of about 1 minute sets up the composition, and complete cure is observed after about 5 to about 15 minutes at 165°C. Thus, the composition of the present invention can be used at relatively moderate temperatures and short- time curing conditions, and hence achieve very good productivity.
- the amount of thermosetting resin composition applied should be suitably adjusted so as to fill almost completely the space between the carrier substrate and the semiconductor chip, which amount of course may vary depending on application. Cured reaction products of the thermosetting resin compositions of the present invention demonstrate excellent adhesive force, heat resistance and electric properties, and acceptable mechanical properties, such as flex-cracking resistance, chemical resistance, moisture resistance and the like, for the applications for which they are used herein.
- thermosetting resin composition of the present invention In the mounting process by using the thermosetting resin composition of the present invention, after the semiconductor device is mounted on the circuit board as described above, the resulting structure is tested with respect to characteristics of the semiconductor device, connection between the semiconductor device and the circuit board, other electrical characteristics, and the state of sealing. In the event a failure is found, repair can be made in the following manner and as shown in the flow diagram depicted in FIG. 2.
- the area around the semiconductor device which has failed is heated at a temperature of about 190 to about 260 °C for a period of time ranging from about 10 seconds to about 1 minute. (See FIG. 2, step 1.) Desirably, the temperature should be maintained in the range of about 210 to about 220°C and the period of time should be within the 30 seconds to 1 minute range. Although no particular limitation is placed on the way in which heating occurs, localized heating is particularly desirable, such as the application of hot air to the failure site by a heating gun.
- the semiconductor device may be pulled apart and removed from the substrate, such as with tweezers or pliers .
- a residue of the cured reaction product of the thermosetting resin composition and a residue of the solder are left on the circuit board 5.
- the residue of the cured product of the thermosetting resin composition can be removed, for example, by scraping it off after the residue has been softened by heating it to a predetermined temperature.
- the residue of the solder can be removed, for example, by use of a solder-absorbing braided wire. (See FIG. 2, step 2.)
- a new semiconductor chip may be mounted again onto the circuit board (which has been cleaned as described above) in the manner as described above.
- thermosetting resin composition in accordance with this invention may be dispensed in the area between the semiconductor device and the circuit board. (See FIG. 2, step 4.) Repair of the failure site is thus completed.
- the semiconductor device can be reused by removing the residue of the cured reaction product of the thermosetting resin composition and the residue of the - -
- compositions in accordance with the present invention were prepared and evaluated for performance .
- thermosetting resin composition in accordance with this invention was prepared by mixing together in accordance with this invention for a period of time of about 10 minutes at room temperature in an open vessel the following components in the order noted:
- an epoxy resin component including
- a curing agent component including 0.2 grams of an imidazole component
- anhydride component comprised of 42.42 grams of a mixture in an 50:50 ratio of "HHPA” and “MHHPA” anhydrides (commercially available from Lindau under the trade designation “LINDRIDE” 62C) , and 7.48 grams of a cycloaliphatic dianhydride (commercially available from
- Example Nos. 2-28 Seven other formulations (Sample Nos. 2-8) were prepared having the following components in the amounts noted below in Table 1. Table 1
- compositions were used upon formation (see below) , they may be stored for a period of time of up to about 3 to about 6 months at a temperature of about -40°C without experiencing viscosity increase.
- composition was transferred to a 10 ml syringe made of non-reactive plastic.
- compositions of this invention may be dispensed through a 12G needle connected to the syringe into the junction between the carrier substrate and semiconductor device an assembly previously formed as above.
- the assembly was transferred to an oven while the temperature was maintained at about 165°C.
- the composition cured initially after about 1 minute, and thereafter cured completely after about 15 minutes at that temperature.
- compositions have a variety of properties in both the uncured and cured state which are measurable and useful parameters for the end user in choosing a particular formulation for a desired need.
- the flow rate is of interest; in reaching the cured state, the adhesion and reworkability are of interest .
- the flow time allows the end user to determine the rapidity with which the adhesive may be applied during a fabrication process, such as a circuit assembly operation. It may be measured by passing the composition through a 25 ⁇ m gap between glass slides aligned perpendicular to one another, using metal shims as spacers. The time required for the composition to flow between the slides is then measured at a length of about one inch, at 0.25 inch intervals. Values in seconds for the flow times of the compositions set forth above are presented as an average of three measurements below in Table 2.
- the cure schedule refers to the time required for the onset of cure to occur at a certain temperatrue, in a specified period of time. This may be seen in more detail with regard to certain of the samples prepared in accordance with the present invention below in Table 2.
- the adhesion provides information on the strength of the bond formed by the cured composition.
- the glass transition temperature (“Tg”) which is measured by differential scanning calerimetry (“DSC”) or by thermal mechanical analysis (“TMA”), provides information on the hardness and strength of the cured reaction product (or, network) , and its behavior with respect to changes in temperature -- that is, a higher Tg should afford a material that is better able to withstand elevated temperatures.
- the area around the CSP, fixed to the circuit board with the compositions of Sample Nos. 1-2 and 4-5, should be heated by applying hot air at a temperature of about 215°C for a period of time of 1 minute. Then, the CSP may be easily removed by pulling or twisting the semiconductor chip from the circuit board using tweezers .
- thermosetting resin composition of this invention may be applied around the periphary of the newly-replaced semiconductor chip and cured by heating to a temperature of about 165°C for a period of 7 minutes.
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- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Computer Hardware Design (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US27494399A | 1999-03-23 | 1999-03-23 | |
US274943 | 1999-03-23 | ||
PCT/US2000/007452 WO2000056799A1 (en) | 1999-03-23 | 2000-03-22 | Reworkable thermosetting resin compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1090057A1 true EP1090057A1 (en) | 2001-04-11 |
Family
ID=23050240
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00916567A Withdrawn EP1090057A1 (en) | 1999-03-23 | 2000-03-22 | Reworkable thermosetting resin compositions |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP1090057A1 (en) |
JP (1) | JP2002540235A (en) |
KR (1) | KR20010043524A (en) |
CN (1) | CN1300301A (en) |
AU (1) | AU3765600A (en) |
CA (1) | CA2331790A1 (en) |
MX (1) | MXPA00011554A (en) |
WO (1) | WO2000056799A1 (en) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1232515C (en) * | 2000-03-31 | 2005-12-21 | 亨凯尔公司 | Reworkable composition of oxirane (S) or thiirane (S)-containing resin and curing agent |
US7012120B2 (en) | 2000-03-31 | 2006-03-14 | Henkel Corporation | Reworkable compositions of oxirane(s) or thirane(s)-containing resin and curing agent |
WO2001083607A1 (en) * | 2000-04-21 | 2001-11-08 | Henkel Loctite Corporation | Rheology-controlled epoxy-based compositions |
WO2002058108A2 (en) | 2000-11-14 | 2002-07-25 | Henkel Loctite Corporation | Wafer applied fluxing and underfill material, and layered electronic assemblies manufactured therewith |
US20090137777A1 (en) * | 2004-10-20 | 2009-05-28 | Kansai Paint Co., Ltd. | Polyepoxy compound, method for producing same, thermosetting resin composition containing same, cured product of such composition, and method for removing such cured product |
JP2006303192A (en) * | 2005-04-20 | 2006-11-02 | Sumitomo Bakelite Co Ltd | Semiconductor device and method for reproducing chip |
KR101132920B1 (en) * | 2006-01-12 | 2012-04-04 | 에스케이 텔레콤주식회사 | System for monitoring reverse call information using mobile network |
WO2008087972A1 (en) * | 2007-01-16 | 2008-07-24 | Sumitomo Bakelite Co., Ltd. | Insulating resin sheet multilayer body, multilayer printed wiring board obtained by laminating the insulating resin sheet multilayer bodies |
JP6596412B2 (en) | 2013-03-22 | 2019-10-23 | ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング | Thermosetting resin composition having diene / dienophile pair and repairability |
CN108219367B (en) * | 2016-12-22 | 2022-05-13 | 广东生益科技股份有限公司 | Halogen-free thermosetting resin composition, prepreg containing same, laminated board and printed circuit board |
CN113046007A (en) * | 2021-03-22 | 2021-06-29 | 东莞澳中新材料科技股份有限公司 | Thermal de-bonding composition, thermal de-bonding protective film comprising same and preparation method |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU566647B2 (en) * | 1982-09-30 | 1987-10-29 | Union Carbide Corporation | Curable epoxy resin molding composition |
US5106947A (en) * | 1989-04-17 | 1992-04-21 | Ciba-Geigy Corporation | Curable composition based on cycloaliphatic epoxy resins |
US5821456A (en) * | 1996-05-01 | 1998-10-13 | Motorola, Inc. | Microelectronic assembly including a decomposable encapsulant, and method for forming and reworking same |
US6008266A (en) * | 1996-08-14 | 1999-12-28 | International Business Machines Corporation | Photosensitive reworkable encapsulant |
US5948922A (en) * | 1997-02-20 | 1999-09-07 | Cornell Research Foundation, Inc. | Compounds with substituted cyclic hydrocarbon moieties linked by secondary or tertiary oxycarbonyl containing moiety providing reworkable cured thermosets |
-
2000
- 2000-03-22 JP JP2000606659A patent/JP2002540235A/en active Pending
- 2000-03-22 CN CN00800298A patent/CN1300301A/en active Pending
- 2000-03-22 CA CA002331790A patent/CA2331790A1/en not_active Abandoned
- 2000-03-22 EP EP00916567A patent/EP1090057A1/en not_active Withdrawn
- 2000-03-22 AU AU37656/00A patent/AU3765600A/en not_active Abandoned
- 2000-03-22 KR KR1020007012625A patent/KR20010043524A/en not_active Application Discontinuation
- 2000-03-22 WO PCT/US2000/007452 patent/WO2000056799A1/en not_active Application Discontinuation
- 2000-11-23 MX MXPA00011554 patent/MXPA00011554A/en unknown
Non-Patent Citations (1)
Title |
---|
See references of WO0056799A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO2000056799A1 (en) | 2000-09-28 |
KR20010043524A (en) | 2001-05-25 |
AU3765600A (en) | 2000-10-09 |
CA2331790A1 (en) | 2000-09-28 |
MXPA00011554A (en) | 2001-12-02 |
JP2002540235A (en) | 2002-11-26 |
CN1300301A (en) | 2001-06-20 |
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