WO2010087444A1 - 電子部品用接着剤 - Google Patents
電子部品用接着剤 Download PDFInfo
- Publication number
- WO2010087444A1 WO2010087444A1 PCT/JP2010/051253 JP2010051253W WO2010087444A1 WO 2010087444 A1 WO2010087444 A1 WO 2010087444A1 JP 2010051253 W JP2010051253 W JP 2010051253W WO 2010087444 A1 WO2010087444 A1 WO 2010087444A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- adhesive
- electronic components
- epoxy
- weight
- parts
- Prior art date
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 88
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 81
- 239000004593 Epoxy Substances 0.000 claims abstract description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- -1 episulfide compound Chemical class 0.000 claims abstract description 44
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 29
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 26
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 15
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 14
- 229920000570 polyether Polymers 0.000 claims abstract description 14
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002245 particle Substances 0.000 claims description 56
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 40
- 125000006850 spacer group Chemical group 0.000 claims description 24
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 16
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 150000008065 acid anhydrides Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000001723 curing Methods 0.000 description 42
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 26
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 239000000758 substrate Substances 0.000 description 15
- 239000004065 semiconductor Substances 0.000 description 14
- 229920000647 polyepoxide Polymers 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 239000003822 epoxy resin Substances 0.000 description 10
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 5
- 239000012790 adhesive layer Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 150000003553 thiiranes Chemical class 0.000 description 4
- GOYGTBXFJBGGLI-UHFFFAOYSA-N 7a-but-1-enyl-3a-methyl-4,5-dihydro-2-benzofuran-1,3-dione Chemical compound C1=CCCC2(C)C(=O)OC(=O)C21C=CCC GOYGTBXFJBGGLI-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 125000003827 glycol group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910001410 inorganic ion Inorganic materials 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-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
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009775 high-speed stirring Methods 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- BVYPJEBKDLFIDL-UHFFFAOYSA-N 3-(2-phenylimidazol-1-yl)propanenitrile Chemical compound N#CCCN1C=CN=C1C1=CC=CC=C1 BVYPJEBKDLFIDL-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- 239000005997 Calcium carbide Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 102100034343 Integrase Human genes 0.000 description 1
- 108010061833 Integrases Proteins 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011951 cationic catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 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
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- VAUOPRZOGIRSMI-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CNC1=CC=CC=C1 VAUOPRZOGIRSMI-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000007613 slurry method Methods 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CLZWAWBPWVRRGI-UHFFFAOYSA-N tert-butyl 2-[2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-bromophenoxy]ethoxy]-4-methyl-n-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]anilino]acetate Chemical compound CC1=CC=C(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(OCCOC=2C(=CC=C(Br)C=2)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)=C1 CLZWAWBPWVRRGI-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
- C09J171/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
- H01L21/52—Mounting semiconductor bodies in containers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
- H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L24/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
- H01L24/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/062—Copolymers with monomers not covered by C08L33/06
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
- H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
- H01L2924/151—Die mounting substrate
- H01L2924/156—Material
- H01L2924/15786—Material with a principal constituent of the material being a non metallic, non metalloid inorganic material
- H01L2924/15788—Glasses, e.g. amorphous oxides, nitrides or fluorides
Definitions
- the present invention relates to an adhesive for electronic components that can suppress the occurrence of warpage and reflow cracks even when used for bonding thin electronic components.
- the adhesive for electronic parts should be designed so that the elastic modulus of the cured product is low.
- the reflow crack resistance tends to deteriorate. It is difficult to prevent both warpage and reflow cracks.
- Patent Document 1 proposes a resin paste in which a specific imide compound, a liquid rubber compound such as epoxidized polybutadiene, a radical initiator, and a filler are blended for the purpose of preventing the occurrence of warpage and reflow cracks.
- a specific imide compound a liquid rubber compound such as epoxidized polybutadiene, a radical initiator, and a filler are blended for the purpose of preventing the occurrence of warpage and reflow cracks.
- Patent Document 2 describes an epoxy resin composition containing an epoxy resin and an episulfide resin, particularly as an epoxy resin composition with improved reflow crack resistance against copper. Patent Document 2 also describes that a bisphenol A type episulfide resin is preferable as the episulfide resin, and a bisphenol type epoxy resin is preferable as the epoxy resin. However, even when the epoxy resin composition described in Patent Document 2 is used, there is a problem that warpage is increased in a semiconductor chip having a high elastic modulus of a cured resin and a thickness of about several tens of ⁇ m.
- An object of this invention is to provide the adhesive for electronic components which can suppress generation
- the present invention includes an epoxy compound having an aliphatic polyether skeleton and a glycidyl ether group, an epoxy compound containing an epoxy group-containing acrylic polymer, an episulfide compound, and a curing agent, and having the aliphatic polyether skeleton and a glycidyl ether group. It is an adhesive for electronic parts whose content of the said episulfide compound with respect to a weight part is 1 weight part or more and less than 30 weight part.
- the present invention is described in detail below.
- the present inventors have studied in detail the mechanism of occurrence of reflow cracks. As a result, it was found that there are two generation patterns of reflow cracks: interfacial delamination due to insufficient adhesion between substrates or electronic components, and cohesive delamination due to insufficient crosslinking. As a result of further diligent investigation based on this analysis, the occurrence of warpage and reflow cracks in electronic components was achieved by using an epoxy compound having an aliphatic polyether skeleton and a glycidyl ether, an epoxy group-containing acrylic polymer and an episulfide compound in combination. The present invention was completed by finding out that the occurrence of the occurrence can be suppressed at the same time.
- the resulting cured product becomes flexible and can prevent warping.
- the epoxy group-containing acrylic polymer exhibits an effect of increasing the cohesive strength of the adhesive for electronic components, and can prevent the occurrence of reflow cracks due to cohesive peeling.
- the episulfide compound is superior in adhesion to electronic components and substrates compared to epoxy compounds, and can prevent the occurrence of reflow cracks due to interface peeling.
- episulfide compounds are more reactive than epoxy compounds, and have the effect of increasing the degree of cross-linking of the cured product of the adhesive for electronic components to increase the elastic modulus, so that the occurrence of warpage is not induced. It is important to adjust the amount.
- the adhesive for electronic components of the present invention contains an epoxy compound having an aliphatic polyether skeleton and a glycidyl ether group (hereinafter also referred to as “epoxy compound (A1)”).
- epoxy compound (A1) examples include a propylene glycol skeleton and a polytetramethylene glycol skeleton.
- Examples of the epoxy compound (A1) include polytetramethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, polyhexamethylene glycol diglycidyl ether, and the like. Especially, since the softness
- the minimum with a preferable number average molecular weight of the said epoxy compound (A1) is 800, and a preferable upper limit is 10,000.
- a preferable lower limit of the number average molecular weight of the epoxy compound (A1) is 850, the more preferable upper limit is 2000, the still more preferable lower limit is 900, and the more preferable upper limit is 1500.
- the number average molecular weight is a value obtained by using gel permeation chromatography (GPC) with polystyrene as a standard.
- a measuring device manufactured by Waters (column is Shodex GPC LF manufactured by Showa Denko KK). It means a value measured using -804 (length: 300 mm) ⁇ 2, measuring temperature is 40 ° C., flow rate is 1 mL / min, solvent is tetrahydrofuran, and standard material is polystyrene.
- the epoxy compound (A1) preferably has a viscosity of 500 mmPa or less measured at 23 ° C. and 5 rpm using an E-type viscometer.
- paintability of the adhesive agent for electronic components can be improved further as the viscosity of the said epoxy compound (A1) is 500 mmPa or less.
- Examples of the commercially available epoxy compound (A1) include Epogosay PT (Yokkaichi Synthesis, polytetramethylene glycol diglycidyl ether), EX-841 (Nagase ChemteX, polyethylene glycol diglycidyl ether), and the like. .
- the adhesive for electronic components of the present invention contains an epoxy group-containing acrylic polymer.
- the epoxy group reacts with the epoxy compound (A1), and the rupture strength of the cured product of the adhesive for electronic components is increased by the acrylic polymer skeleton, so that reflow due to cohesive peeling Generation of cracks can be effectively prevented.
- the epoxy group-containing acrylic polymer preferably has an acrylic polymer skeleton in the main chain and an epoxy group in the side chain.
- the preferable lower limit of the epoxy equivalent of the epoxy group-containing acrylic polymer is 300, and the preferable upper limit is 1000.
- the epoxy equivalent of the epoxy group-containing acrylic polymer is less than 300, the crosslink density becomes too high, and the elastic modulus of the cured product of the adhesive for electronic parts is increased, and the occurrence of warpage may not be prevented.
- the epoxy equivalent of the epoxy group-containing acrylic polymer exceeds 1000, the number of crosslinking points is small, the crosslinking density is too low, and the occurrence of reflow cracks due to cohesive peeling may not be prevented.
- the more preferable lower limit of the epoxy equivalent of the epoxy group-containing acrylic polymer is 400, and the more preferable upper limit is 800.
- the minimum with a preferable number average molecular weight of the said epoxy group containing acrylic polymer is 5000, and a preferable upper limit is 50000.
- the number average molecular weight of the epoxy group-containing acrylic polymer is less than 5,000, the occurrence of reflow cracks due to cohesive peeling may not be prevented, and when it exceeds 50,000, the compatibility with other components may be reduced.
- the minimum with a more preferable number average molecular weight of the said epoxy group containing acrylic polymer is 7000, and a more preferable upper limit is 20000.
- the content of the epoxy group-containing acrylic polymer is preferably 4 parts by weight and preferably 40 parts by weight with respect to 100 parts by weight of the epoxy compound (A1).
- the amount of the epoxy group-containing acrylic polymer is less than 4 parts by weight, it may not be possible to prevent the occurrence of reflow cracks due to cohesive peeling.
- the amount exceeds 40 parts by weight the viscosity increases and the electronic component is bonded. Workability may be reduced.
- a more preferred lower limit of the amount of the epoxy group-containing acrylic polymer is 10 parts by weight, and a more preferred upper limit is 30 parts by weight.
- the adhesive for electronic components of the present invention contains an episulfide compound.
- Episulfide compounds have higher adhesion to electronic components and substrates than epoxy compounds.
- epoxy compound (A1) By containing a predetermined amount of an episulfide compound with respect to the epoxy compound (A1), it is possible to effectively prevent the occurrence of reflow cracks due to interface peeling with the substrate. Also, the elastic modulus can be optimized and warpage can be prevented.
- the episulfide compound is not particularly limited as long as it has an episulfide group, and examples thereof include those in which the oxygen atom of the epoxy group of the epoxy resin is substituted with a sulfur atom.
- the episulfide compound include a bisphenol type episulfide compound (a compound in which an oxygen atom of an epoxy group of a bisphenol type epoxy resin is substituted with a sulfur atom), a hydrogenated bisphenol type episulfide compound, and the like. Of these, hydrogenated bisphenol type episulfide compounds are preferred because they are liquid and do not increase the viscosity of the adhesive for electronic components more than necessary.
- Examples of commercially available hydrogenated bisphenol episulfide compounds include YL-7007 (manufactured by Japan Epoxy Resin Co., Ltd., hydrogenated bisphenol A episulfide compounds).
- Content of the said episulfide compound is 1 weight part or more and less than 30 weight part with respect to 100 weight part of said epoxy compounds (A1). If the content of the episulfide compound is less than 1 part by weight, the occurrence of reflow cracks due to interfacial peeling cannot be prevented, and if it is 30 parts by weight or more, the elastic modulus of the cured product of the adhesive for electronic components is It becomes high and it cannot prevent warping.
- the minimum with preferable content of the said episulfide compound is 5 weight part, and a preferable upper limit is 20 weight part.
- the adhesive for electronic parts of the present invention preferably contains an epoxy compound (A2) having an aromatic skeleton and a molecular weight of 150 to 500, in addition to the epoxy compound (A1).
- an epoxy compound (A2) By containing an epoxy compound (A2), the elastic modulus at high temperature of the hardened
- the curing speed of the adhesive for electronic components is increased, the occurrence of warpage of the electronic components can be further suppressed.
- the molecular weight of the epoxy compound (A2) is less than 150, it may volatilize during thermal curing, and if it exceeds 500, sufficient high-temperature elastic modulus improvement effect and curing rate acceleration effect cannot be obtained.
- the more preferable lower limit of the molecular weight of the epoxy compound (A2) is 200, and the more preferable upper limit is 300.
- the molecular weight of the said epoxy compound (A2) means the molecular weight which can be calculated from the said structural formula, when the structural formula of the said epoxy compound (A2) can be specified.
- an epoxy compound (A2) is a polymer and a structural formula cannot be specified, it means a number average molecular weight.
- Examples of the epoxy compound (A2) include aniline type epoxy compounds, dicyclopentadiene type epoxy compounds, resorcinol type epoxy compounds, naphthalene type epoxy compounds, biphenyl type epoxy compounds and the like. Among them, aniline type epoxy compounds and resorcinol type epoxy compounds are suitable because the viscosity of the adhesive for electronic parts can be lowered and the coating property can be further improved.
- aniline-type epoxy compound examples include glycidyloxy-N, N-glycidylaniline.
- commercially available products of the above aniline type epoxy compounds include, for example, EP-3900S, EP-3950 (both manufactured by ADEKA) and the like.
- examples of the resorcinol-type epoxy compound include m-resorcinol diglycidyl ether, o-resorcinol diglycidyl ether, and the like.
- examples of commercially available resorcinol-type epoxy compounds include EX-201 and EX-203 (both manufactured by Nagase ChemteX Corporation).
- the preferable minimum with respect to 100 weight part of said epoxy compounds (A1) is 1 weight part, and a preferable upper limit is 20 weight part.
- a preferable upper limit is 20 weight part.
- the content of the epoxy compound (A2) is less than 1 part by weight, an effect such as improvement in elastic modulus at high temperature may not be obtained.
- the content exceeds 20 parts by weight the adhesive for electronic components of the present invention The cured product becomes less flexible and warpage may not be prevented.
- the minimum with more preferable content of the said epoxy compound (A2) is 3 weight part, and a more preferable upper limit is 10 weight part.
- the adhesive for electronic components of the present invention contains a curing agent.
- curing agent is not specifically limited, A conventionally well-known hardening
- acid anhydride curing agents such as trialkyltetrahydrophthalic anhydride and succinic anhydride
- latent curing agents such as phenolic curing agents, amine curing agents, dicyandiamide, and cationic catalyst types Examples thereof include a curing agent.
- These curing agents may be used alone or in combination of two or more.
- an acid anhydride curing agent is preferable because of high adhesion reliability, and an acid anhydride containing a double bond is more preferable.
- the flexibility of the cured product of the adhesive for electronic components can be further increased, and the occurrence of warpage of the electronic component can be reduced.
- the acid anhydride containing the double bond include dodecenyl succinic anhydride, tetrapropenyl succinic anhydride, methylbutenyl tetrahydrophthalic anhydride, and the like.
- the content of the curing agent is a curing agent that reacts in an equal amount, all the curable components (epoxy compound (A1), epoxy group-containing acrylic polymer, episulfide compound, and blended as necessary)
- the preferable lower limit is 30 equivalents and the preferable upper limit is 110 equivalents with respect to 100 parts by weight of the total of the curable functional groups of the epoxy compound (A2)).
- curing agent is a hardening
- a preferable minimum is 1 weight part and a preferable upper limit is 20 weight part with respect to 100 weight part of total of all the sclerosing
- the adhesive for electronic components of the present invention preferably further contains a curing accelerator.
- a curing accelerator By containing a curing accelerator, physical properties such as curing speed and bonding reliability can be further enhanced.
- the curing accelerator examples include imidazole-based curing accelerators and tertiary amine-based curing accelerators. These curing accelerators may be used alone or in combination of two or more. Among these, an imidazole-based curing accelerator is preferable because it is easy to control the reaction system for adjusting the curing speed and the physical properties of the cured product. Of the imidazole curing accelerators, adduct-type imidazole curing accelerators with epoxy are more preferable. When an adduct type imidazole curing accelerator with epoxy is used, curing can be performed at a relatively low temperature in a short time while maintaining storage stability.
- Examples of the imidazole curing accelerator include 1-cyanoethyl-2-phenylimidazole in which the 1-position of imidazole is protected with a cyanoethyl group, and 1-position of imidazole protected with isocyanuric acid (2MA-OK, Shikoku Kasei Kogyo Co., Ltd.). And PN-23J manufactured by Ajinomoto Co., Inc.).
- the content of the curing accelerator is preferably 1 part by weight with respect to 100 parts by weight of the total of all curable components, and 20 parts by weight with respect to the preferable upper limit. If the content of the curing accelerator is less than 1 part by weight, the curing rate and the bonding reliability may not be sufficiently increased. If the content exceeds 20 parts by weight, an unreacted curing accelerator remains after curing. There are things to do.
- the adhesive for electronic components of the present invention preferably further contains silica particles.
- silica particles By containing silica particles, the thermal expansion of the cured product of the adhesive for electronic components can be suppressed, and the occurrence of warpage in the electronic component can be suppressed.
- the silica particles are preferably silica particles that have been surface-treated with a silane coupling agent having a phenyl group. If the silica particles are surface-treated with a silane coupling agent having a phenyl group, the increase in viscosity can be reduced even when added to the epoxy compound (A1), and the applicability of the adhesive for electronic parts can be improved. .
- silane coupling agent having a phenyl group examples include phenyltrimethoxysilane and 3- (N-phenyl) aminopropyltrimethoxysilane.
- the method of surface-treating silica particles with the above-mentioned silane coupling agent having a phenyl group includes, for example, adding silica particles into a mixer capable of high-speed stirring such as a Henschel mixer or a V-type mixer and stirring the silane coupling agent.
- a silica solution is added to a mixer capable of high-speed stirring such as a Henschel mixer or a V-type mixer, and an alcohol aqueous solution, an organic solvent solution or an aqueous solution containing a silane coupling agent is added while stirring.
- Direct processing methods such as a dry method to be added to the mixer, a slurry method to add an organosilane coupling agent to the silica particle slurry, and a spray method to spray the silane coupling agent after the silica particles have been dried And when preparing adhesives for electronic components, mixing silica particles with other components Integrase barrel blending method of adding the coupling agent directly, and the like.
- a preferable minimum is 0.1 weight part with respect to 100 weight part of silica particles, and a preferable upper limit is 15 Parts by weight.
- the amount of the silane coupling agent having a phenyl group is less than 0.1 parts by weight, the silica particles may not be sufficiently surface treated.
- the amount exceeds 15 parts by weight an unreacted silane coupling agent is formed. It may remain, and the heat resistance of the cured product of the adhesive for electronic components may decrease.
- silica particles surface-treated with the phenyl group-containing silane coupling agent may be used as the silica particles surface-treated with the phenyl group-containing silane coupling agent.
- the content of the silica particles is preferably 50 parts by weight and preferably 400 parts by weight with respect to 100 parts by weight of the epoxy compound (A1).
- the content of the silica particles is less than 50 parts by weight, the effect of suppressing the thermal expansion of the cured product may not be sufficiently obtained.
- the content exceeds 400 parts by weight the viscosity increases and the coating stability is poor. There is a case.
- the minimum with more preferable content of the said silica particle is 100 weight part, and a more preferable upper limit is 200 weight part.
- the preferable lower limit of the average particle diameter of the silica particles is 500 nm, and the preferable upper limit is 20 ⁇ m.
- the average particle diameter of the silica particles is less than 500 nm, the increase in viscosity due to the addition of silica may be remarkable.
- the average particle size of the silica particles exceeds 20 ⁇ m, the maximum particle size also increases, and the thickness of the bonding material when bonding electronic components may be unnecessarily large.
- the adhesive for electronic parts of the present invention preferably further contains spacer particles.
- spacer particles By containing the spacer particles, when the plurality of electronic components are laminated and bonded using the adhesive for electronic components of the present invention, the interval between the electronic components can be kept constant.
- the spacer particles are preferably spherical.
- the spacer particles preferably have an aspect ratio of 1.1.
- the aspect ratio means the ratio of the length of the major axis of the particle to the length of the minor axis of the particle (length of major axis / length of minor axis). The closer the aspect ratio value is to 1, the closer the shape of the spacer particle is to a true sphere.
- the average particle size of the spacer particles may be appropriately selected so that the distance between the electronic components is within a desired range, but the preferable lower limit is 5 ⁇ m and the preferable upper limit is 200 ⁇ m. If the average particle size of the spacer particles is less than 5 ⁇ m, it may be difficult to reduce the distance between the electronic components to the particle size of the spacer particles. If the average particle size exceeds 200 ⁇ m, the interval between the electronic components is more than necessary. May become large. The more preferable lower limit of the average particle diameter of the spacer particles is 9 ⁇ m, and the more preferable upper limit is 50 ⁇ m.
- the spacer particles preferably have a particle diameter CV value of 10% or less.
- the CV value of the particle diameter of the spacer particles is more preferably 6% or less, still more preferably 4% or less.
- the said CV value is a numerical value calculated
- required by a following formula. CV value (%) ( ⁇ 2 / Dn 2 ) ⁇ 100 In the above formula, ⁇ 2 represents the standard deviation of the particle diameter, and Dn 2 represents the number average particle diameter.
- the spacer particles are preferably resin particles made of resin or organic-inorganic hybrid particles.
- the resin constituting the resin particles include polyethylene, polypropylene, polymethylpentene, polyvinyl chloride, polytetrafluoroethylene, polystyrene, polymethyl methacrylate, polyethylene terephthalate, polybutylene terephthalate, polyamide, polyimide, polysulfone, Non-crosslinked resins such as polyphenylene oxide and polyacetal, epoxy resins, phenol resins, melamine resins, unsaturated polyester resins, divinylbenzene polymers, divinylbenzene-styrene copolymers, divinylbenzene-acrylate copolymers, diallyl phthalates
- cross-linked resins such as polymers, triallyl isocyanurate polymers, and benzoguanamine polymers. Especially, since it is easy to adjust the hardness and compression recovery rate of spacer particle
- the spacer particles may be surface-treated as necessary. By subjecting the spacer particles to a surface treatment, the viscosity of the adhesive for electronic components can be easily adjusted to a desired range.
- Examples of the method for surface-treating the spacer particles include a method of imparting a hydrophilic group to the surface of the spacer particles when the adhesive for electronic components exhibits hydrophobicity as a whole.
- Examples of the method of imparting a hydrophilic group to the surface of the spacer particle include a method of treating the surface of the resin particle with a coupling agent having a hydrophilic group when the resin particle is used as the spacer particle.
- the content of the spacer particles is preferably 0.01 parts by weight and preferably 1 part by weight with respect to 100 parts by weight of the epoxy compound (A1).
- the content of the spacer particles is less than 0.01 parts by weight, the distance between the electronic parts may not be stably maintained.
- the content exceeds 1 part by weight, the distance between the electronic parts is stabilized. As a result, it may not be possible to maintain a constant ratio, or the proportion of other components may be relatively reduced, which may reduce the applicability of the adhesive for electronic components and the flexibility of the cured product.
- the adhesive for electronic components of the present invention may contain an inorganic ion exchanger.
- an inorganic ion exchanger By containing an inorganic ion exchanger, it is possible to trap ionic impurities in the adhesive for electronic parts and prevent corrosion of the electrodes of the electronic parts.
- examples of commercially available inorganic ion exchangers include the IXE series (manufactured by Toagosei Co., Ltd.).
- the adhesive for electronic parts of the present invention may contain a thickener for the purpose of adjusting the viscosity.
- the thickener include silica particles, ethyl cellulose, calcium carbide and the like.
- the minimum with the preferable average particle diameter of a silica particle is 5 nm, and a preferable upper limit is 50 nm.
- the content of the thickener is preferably 1 part by weight with respect to 100 parts by weight of the total of all curable components, and 20 parts by weight with a preferred upper limit.
- the adhesive for electronic components of the present invention may contain conventionally known additives such as an anti-bleeding agent and an adhesion-imparting agent, if necessary.
- the adhesive for electronic components of the present invention has a preferred lower limit of 5 Pa ⁇ s and a preferred upper limit of 30 Pa ⁇ s, measured using an E-type viscometer at 25 ° C. and 10 rpm.
- the viscosity of the adhesive for electronic components of the present invention is less than 5 Pa ⁇ s, when the adhesive for electronic components is applied on the electronic component, the applied shape may not be maintained and cast. If it exceeds 30 Pa ⁇ s, the adhesive for electronic components may not be applied uniformly or in a desired shape on the electronic component.
- the more preferable lower limit of the viscosity of the adhesive for electronic components is 8 Pa ⁇ s, and the more preferable upper limit is 20 Pa ⁇ s.
- the viscosity of the adhesive for electronic components of the present invention exceeds 30 Pa ⁇ s, after bonding the electronic components using the adhesive for electronic components, an unfilled portion of the adhesive for electronic components is interposed between the electronic components. In some cases, it may be difficult for the electronic component adhesive to spread to the unfilled portion due to the surface tension of the electronic component or the electronic component adhesive at room temperature.
- the adhesive for electronic parts of the present invention is a value obtained by dividing the viscosity measured under the conditions of 25 ° C. and 5 rpm using an E-type viscometer by the viscosity measured under the conditions of 25 ° C. and 0.5 rpm (thixo value). ) Is preferably 2 or more and 5 or less. When the thixo value is 2 or more, even when moisture remains on the substrate, the migration of moisture can be suppressed, and no void is generated.
- the thixo value exceeds 5, after bonding electronic components using an adhesive for electronic components, if there is an unfilled portion of the adhesive for electronic components between electronic components, the electronic component or electronic component at room temperature It may be difficult for the adhesive for electronic components to spread to the unfilled portion due to the surface tension of the adhesive for use.
- the preferable lower limit of the elastic modulus at the reflow temperature of the cured product is 6 MPa, and the preferable upper limit is 35 MPa. If the elastic modulus at the reflow temperature is less than 6 MPa, reflow cracks may not be sufficiently prevented, and if it exceeds 35 MPa, warpage of the electronic component may not be sufficiently prevented.
- the upper limit of the elastic modulus at the reflow temperature is more preferably 25 MPa, the more preferable lower limit is 7 MPa, and the further preferable upper limit is 20 MPa.
- the preferable lower limit of the glass transition temperature (Tg) of the cured product is ⁇ 20 ° C., and the preferable upper limit is 25 ° C. If the glass transition temperature is less than ⁇ 20 ° C., sufficient heat resistance may not be exhibited in the adhesive for electronic components, and if it exceeds 25 ° C., warpage of the electronic components may not be sufficiently prevented. .
- the adhesive for electronic parts of the present invention has a more preferred lower limit of glass transition temperature of ⁇ 10 ° C., a more preferred upper limit of 20 ° C., a still more preferred lower limit of ⁇ 5 ° C., a still more preferred upper limit of 15 ° C., and even more.
- a preferred lower limit is 0 ° C. and an even more preferred upper limit is 12 ° C.
- the adhesive for electronic parts according to the present invention includes, for example, the silica compound after mixing the epoxy compound (A1), the epoxy group-containing acrylic polymer, the episulfide compound, and a curing agent with other components blended as necessary. It can manufacture by the method of mix
- the adhesive for electronic components of the present invention can be suitably used for bonding electronic components such as semiconductor chips or bonding an electronic component and a substrate. If the adhesive for electronic components of this invention is used, even when it is used for adhesion of thin electronic components, it is possible to suppress the occurrence of warpage of the electronic components and the occurrence of reflow cracks.
- the adhesive agent for electronic components which can suppress generation
- Example 1 to 18 and Comparative Examples 1 to 4 Each component shown in Table 1, Table 2 and Table 3 was blended in each blending ratio, and an electronic component adhesive was prepared by stirring and mixing using a homodisper. Each component used is as follows.
- Epoxy compound (A1) Epogosay PT (polytetramethylene glycol diglycidyl ether, manufactured by Yokkaichi Gosei Co., Ltd., number average molecular weight 900)
- EXA-4850-150 polypropylene glycol skeleton-containing epoxy, manufactured by Dainippon Ink, Inc., number average molecular weight 900
- EXA-4850-1000 polypropylene glycol skeleton-containing epoxy, manufactured by Dainippon Ink Co., Ltd., number average molecular weight 700
- EP-931 propylene glycol diglycidyl ether, manufactured by Nagase ChemteX Corporation, number average molecular weight 770
- Epoxy group-containing acrylic polymer CP-15 (manufactured by NOF Corporation, number average molecular weight 11000, epoxy equivalent 1000)
- CP-30 manufactured by NOF Corporation, number average molecular weight 9000, epoxy equivalent 530
- CP-50M manufactured by NOF Corporation, number average molecular weight 10,000, epoxy equivalent 310
- CP-50S manufactured by NOF Corporation, number average molecular weight 20000, epoxy equivalent 310)
- CP-20SAP manufactured by NOF Corporation, number average molecular weight 8000, epoxy equivalent 750
- Epoxy compound (A2) EX-201 resorcinol type epoxy compound, manufactured by Nagase ChemteX Corporation, molecular weight 222
- Silica particles (filler) SE-4050-SPE sica particles surface-treated with a silane coupling agent having a phenyl group, average particle size 1 ⁇ m, manufactured by Admatechs
- SE-4050-SEE sica particles surface-treated with a silane coupling agent having an epoxy group, average particle size 1 ⁇ m, manufactured by Admatechs
- Curing agent DDSA dodecenyl succinic anhydride, manufactured by Shin Nippon Rika Co., Ltd.
- YH-306 Metalbutenyltetrahydrophthalic anhydride, manufactured by Japan Epoxy Resin
- Curing accelerator 2MZ-A imidazole compound, manufactured by Shikoku Kasei Kogyo Co., Ltd.
- PN-23J epoxy adduct type imidazole compound, manufactured by Ajinomoto Co., Inc.
- Spacer particles SP-210 (average particle size 10 ⁇ m, manufactured by Sekisui Chemical Co., Ltd.)
- Silane coupling agent KBM-573 Phenylaminopropyltrimethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.
- the coating stability was evaluated using an air dispenser (SHOT MASTER300, manufactured by Musashi Engineering Co., Ltd.).
- the parts used were a precision nozzle (made by Musashi Engineering, inner diameter 0.3 mm), and a 10 mL syringe (made by Musashi Engineering).
- the discharge pressure was 0.4 MPa
- the gap between the semiconductor chip and the needle was 200 ⁇ m
- the dispensing was performed 40 times with the aim of a discharge amount of 5 mg.
- the difference between the maximum value and the minimum value of 40 times is less than 0.3 mg is “ ⁇ ”, and the difference between the maximum value and the minimum value of 40 times is 0.3 mg or more and less than 0.5 mg “ ⁇ ”, when the difference between the maximum value and the minimum value of 40 times is 0.5 mg or more and less than 1.0 mg, “ ⁇ ”, when the difference between the maximum value of 40 times and the minimum value is 1.0 mg or more was evaluated as “ ⁇ ”.
- a flip chip bonder (DB-100, manufactured by Shibuya Kogyo Co., Ltd.)
- a semiconductor chip was placed on an organic substrate (manufactured by Daisho Electronics Co., Ltd., thickness 180 um) on which an adhesive layer was formed, at a normal pressure of 0.1 MPa.
- Lamination was performed by pressing for 2 seconds. Thereafter, heating was performed at 110 ° C. for 40 minutes and 170 ° C. for 15 minutes to cure the adhesive layer, thereby producing an electronic component joined body.
- the height position of the upper surface of the semiconductor chip is measured using a laser displacement meter (LT9010M, KS-1100, manufactured by KEYENCE), and the maximum difference in height position on the diagonal line of the semiconductor chip is measured. The amount of warpage was calculated.
- ⁇ indicates that the number of occurrences of reflow cracks was 0
- ⁇ indicates that the number of occurrences of reflow cracks was 1
- the adhesive agent for electronic components which can suppress generation
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Abstract
Description
以下に本発明を詳述する。
上記脂肪族ポリエーテル骨格は、例えば、プロピレングリコール骨格、ポリテトラメチレングリコール骨格等が挙げられる。このような脂肪族ポリエーテル骨格を有するエポキシ化合物(A1)を含有することにより、本発明の電子部品用接着剤の硬化物の柔軟性が高くなり、反りの発生を防止することができる。
なお、本明細書において数平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)を用いてポリスチレンをスタンダードとして求めた値であり、例えば、Waters社製の測定装置(カラムを昭和電工社製Shodex GPC LF-804(長さ300mm)×2本、測定温度を40℃、流速を1mL/min、溶媒をテトラヒドロフラン、標準物質をポリスチレンとする条件)を用いて測定した値を意味する。
上記エピスルフィド化合物は、例えば、ビスフェノール型エピスルフィド化合物(ビスフェノール型エポキシ樹脂のエポキシ基の酸素原子が硫黄原子に置換されたもの)、水添ビスフェノール型エピスルフィド化合物等が挙げられる。なかでも、液状であり、電子部品用接着剤の粘度を必要以上に上げないことから、水添ビスフェノール型エピスルフィド化合物が好適である。
エポキシ化合物(A2)を含有することにより、得られる電子部品用接着剤の硬化物の高温での弾性率を高めることができ、接着信頼性を高めることができる。また、電子部品用接着剤の硬化速度も速くなることから、電子部品の反りの発生をより一層抑制することができる。
なお、上記エポキシ化合物(A2)の分子量は、上記エポキシ化合物(A2)の構造式が特定できる場合には、当該構造式から算出できる分子量を意味する。また、エポキシ化合物(A2)が重合体であって構造式が特定できない場合には、数平均分子量を意味する。
上記レゾルシノール型エポキシ化合物は、例えば、m-レゾルシノールジグリシジルエーテル、o-レゾルシノールジグリシジルエーテル等が挙げられる。
上記レゾルシノール型エポキシ化合物の市販品は、例えば、EX-201、EX-203(いずれもナガセケムテックス社製)等が挙げられる。
上記硬化剤は特に限定されず、従来公知の硬化剤を用いることができる。具体的には、例えば、トリアルキルテトラヒドロ無水フタル酸、コハク酸無水物等の酸無水物硬化剤や、フェノール系硬化剤、アミン系硬化剤、ジシアンジアミド等の潜在性硬化剤や、カチオン系触媒型硬化剤等が挙げられる。これらの硬化剤は単独で用いてもよく、2種以上を併用してもよい。なかでも、接着信頼性が高いことから、酸無水物硬化剤が好適であり、二重結合を含有する酸無水物がより好適である。二重結合を含有する酸無水物を用いると、電子部品用接着剤の硬化物の柔軟性をより一層高めることができ、電子部品の反りの発生を低減することができる。
上記二重結合を含有する酸無水物は、例えば、ドデセニル無水コハク酸、テトラプロペニル無水コハク酸、メチルブテニルテトラヒドロ無水フタル酸等が挙げられる。
上記スペーサー粒子は、アスペクト比の好ましい上限が1.1である。上記スペーサー粒子のアスペクト比が1.1以下であると、電子部品を積層する際に、電子部品同士の間隔を安定して一定に保つことができる。
なお、本明細書においてアスペクト比とは、粒子の短径の長さに対する粒子の長径の長さの比(長径の長さ/短径の長さ)を意味する。アスペクト比の値が1に近いほどスペーサー粒子の形状は真球に近くなる。
なお、本明細書において、上記CV値とは、下記式により求められる数値のことである。
CV値(%)=(σ2/Dn2)×100
上記式中、σ2は、粒子径の標準偏差を表し、Dn2は、数平均粒子径を表す。
上記樹脂粒子を構成する樹脂は、例えば、ポリエチレン、ポリプロピレン、ポリメチルペンテン、ポリ塩化ビニル、ポリテトラフルオロエチレン、ポリスチレン、ポリメチルメタクリレート、ポリエチレンテレフタラート、ポリブチレンテレフタラート、ポリアミド、ポリイミド、ポリスルフォン、ポリフェニレンオキサイド、ポリアセタール等の非架橋樹脂や、エポキシ樹脂、フェノール樹脂、メラミン樹脂、不飽和ポリエステル樹脂、ジビニルベンゼン重合体、ジビニルベンゼン-スチレン共重合体、ジビニルベンゼン-アクリル酸エステル共重合体、ジアリルフタレート重合体、トリアリルイソシアヌレート重合体、ベンゾグアナミン重合体等の架橋樹脂が挙げられる。なかでも、スペーサー粒子の硬さと圧縮回復率とを調整しやすく、電子部品用接着剤の硬化物の耐熱性を向上させることができることから、架橋樹脂が好ましい。
上記スペーサー粒子を表面処理する方法は、例えば、電子部品用接着剤が全体として疎水性を示す場合には、スペーサー粒子の表面に親水基を付与する方法が挙げられる。スペーサー粒子の表面に親水基を付与する方法は、例えば、スペーサー粒子として上記樹脂粒子を用いる場合には、樹脂粒子の表面を親水基を有するカップリング剤で処理する方法等が挙げられる。
上記無機イオン交換体の市販品は、例えば、IXEシリーズ(東亞合成社製)等が挙げられる。
上記増粘剤は、例えば、シリカ粒子、エチルセルロース、炭化カルシウム等が挙げられる。
なお、増粘剤としてシリカ粒子を用いる場合、シリカ粒子の平均粒子径の好ましい下限は5nm、好ましい上限は50nmである。
上記増粘剤の含有量は、全ての硬化性成分の総和100重量部に対して、好ましい下限が1重量部、好ましい上限が20重量部である。
上記成分の混合方法は、例えば、ホモディスパー、万能ミキサー、バンバリーミキサー、又はニーダー等を用いる方法等が挙げられる。
表1、表2及び表3に示した各成分を各配合割合にて配合し、ホモディスパーを用いて攪拌混合することにより電子部品用接着剤を調製した。
用いた各成分は、以下のようである。
エポゴーセーPT(ポリテトラメチレングリコールジグリシジルエーテル、四日市合成社製、数平均分子量900)
EXA-4850-150(ポリプロピレングリコール骨格含有エポキシ、大日本インキ社製、数平均分子量900)
EXA-4850-1000(ポリプロピレングリコール骨格含有エポキシ、大日本インキ社製、数平均分子量700)
EP-931(プロピレングリコールジグリシジルエーテル、ナガセケムテックス社製、数平均分子量770)
CP-15(日油社製、数平均分子量11000、エポキシ当量1000)
CP-30(日油社製、数平均分子量9000、エポキシ当量530)
CP-50M(日油社製、数平均分子量10000、エポキシ当量310)
CP-50S(日油社製、数平均分子量20000、エポキシ当量310)
CP-20SAP(日油社製、数平均分子量8000、エポキシ当量750)
YL-7007(水添ビスフェノールA型エピスルフィド化合物、ジャパンエポキシレジン社製)
EX-201(レゾルシノール型エポキシ化合物、ナガセケムテックス社製、分子量222)
SE-4050―SPE(フェニル基を有するシランカップリング剤により表面処理されたシリカ粒子、平均粒子径1μm、アドマテックス社製)
SE-4050―SEE(エポキシ基を有するシランカップリング剤により表面処理されたシリカ粒子、平均粒子径1μm、アドマテックス社製)
DDSA(ドデセニル無水コハク酸、新日本理化社製)
YH-306(メチルブテニルテトラヒドロ無水フタル酸、ジャパンエポキシレジン社製)
2MZ-A(イミダゾール化合物、四国化成工業社製)
PN-23J(エポキシアダクト型イミダゾール化合物、味の素社製)
SP-210(平均粒子径10μm、積水化学工業社製)
KBM-573(フェニルアミノプロピルトリメトキシシラン、信越化学工業社製)
PM-20L(表面シリコーンオイル処理ヒュームドシリカ、トクヤマ社製)
実施例及び比較例で製造した電子部品用接着剤について、以下の方法により評価を行った。
結果を表1、表2及び表3に示した。
(1-1)粘度の測定
E型粘度測定装置(VISCOMETER TV-22、東海産業社製、φ15mmローターを使用)を用いて、25℃、10rpmの条件で粘度を測定した。
エアーディスペンサー(SHOT MASTER300、武蔵エンジニアリング社製)を用いて、塗布安定性を評価した。使用した部品は、精密ノズル(武蔵エンジニアリング社製、内径0.3mm)、10mLシリンジ(武蔵エンジニアリング社製)である。吐出条件は、吐出圧0.4MPa、半導体チップとニードルとのギャップ200μmで、吐出量5mg狙いで40回ディスペンスを行った。
塗布安定性について、40回の最大値と最小値の差が0.3mg未満である場合を「◎」、40回の最大値と最小値の差が0.3mg以上0.5mg未満である場合を「○」、40回の最大値と最小値の差が0.5mg以上1.0mg未満である場合を「△」、40回の最大値と最小値の差が1.0mg以上である場合を「×」と評価した。
(2-1)リフロー温度での弾性率の測定
電子部品用接着剤からなる接着剤層の硬化物について、粘弾性測定機(型式「DVA-200」、アイティー計測制御社製)を用いて、昇温速度5℃/分、引っ張り、つかみ幅24mm、10Hzで-60℃から300℃まで昇温して弾性率(MPa)を測定した。このとき、tanδのピーク温度をガラス転移温度(Tg)(℃)とした。
(3-1)半導体チップの反りの評価
電子部品用接着剤を10mLシリンジ(武蔵エンジニアリング社製)に充填し、シリンジの先端に精密ノズル(武蔵エンジニアリング社製、ノズル先端径0.3mm)を取り付け、ディスペンサ装置(SHOT MASTER300、武蔵エンジニアリング社製)を用いて、吐出圧0.4MPa、半導体チップとニードルとのギャップ200μm及び塗布量5mgの条件で、電子部品用接着剤をガラス基板上に塗布し、接着剤層を形成した。塗布に際しては、接合部分の中央領域の塗布量に対する接合部分の中央領域を囲む外周縁領域の塗布量の比が4となるように塗布した。
得られた電子部品接合体を、85℃及び相対湿度85%の恒温恒湿オーブンに48時間放置した。その後、電子部品接合体を、180℃以上が20秒以上でかつ最高温度が260℃となるIRリフロー炉に3回投入した。リフロー処理後、電子部品接合体30個中におけるリフロークラックの発生個数を、超音波探傷装置(SAT)を用いて観察した。
耐リフロー性について、リフロークラック発生数が0個であった場合を「◎」、リフロークラック発生数が1個であった場合を「○」、リフロークラック発生数が2個であった場合を「△」、リフロークラック発生数が3個以上であった場合を「×」と評価した。
得られた電子部品接合体についてサンプルを10個作製し、各電子部品接合体の積層状態をレーザー変位計(KS-1100、KEYENCE社製)を用いて測定した。具体的には、チップと基板上面との段差を測定し、測定値からチップ厚みを引くことで、チップと基板との間の距離を求めた。チップ-基板間距離が10個のサンプルすべてで5~15μmの範囲にある場合を「○」、一つでも5~15μmの範囲から外れた場合は「×」と評価した。
Claims (10)
- 脂肪族ポリエーテル骨格とグリシジルエーテル基とを有するエポキシ化合物、エポキシ基含有アクリルポリマー、エピスルフィド化合物及び硬化剤を含有し、
前記脂肪族ポリエーテル骨格とグリシジルエーテル基とを有するエポキシ化合物100重量部に対する前記エピスルフィド化合物の含有量が1重量部以上、30重量部未満である
ことを特徴とする電子部品用接着剤。 - 脂肪族ポリエーテル骨格とグリシジルエーテル基とを有するエポキシ化合物は、数平均分子量が800~10000であることを特徴とする請求項1記載の電子部品用接着剤。
- エポキシ基含有アクリルポリマーは、エポキシ当量が300~1000であることを特徴とする請求項1又は2記載の電子部品用接着剤。
- エポキシ基含有アクリルポリマーは、数平均分子量が5000~50000であることを特徴とする請求項1、2又は3記載の電子部品用接着剤。
- エピスルフィド化合物は、水添ビスフェノール型エピスルフィド化合物であることを特徴とする請求項1、2、3又は4記載の電子部品用接着剤。
- 硬化剤は、酸無水物硬化剤であることを特徴とする請求項1、2、3、4又は5記載の電子部品用接着剤。
- 更に、芳香族骨格を有し、かつ、数平均分子量が150~500であるエポキシ化合物を、脂肪族ポリエーテル骨格とグリシジルエーテル基とを有するエポキシ化合物100重量部に対して1~20重量部含有することを特徴とする請求項1、2、3、4、5又は6記載の電子部品用接着剤。
- 更に、シリカ粒子を、脂肪族ポリエーテル骨格とグリシジルエーテル基とを有するエポキシ化合物100重量部に対して50~400重量部含有することを特徴とする請求項1、2、3、4、5、6又は7記載の電子部品用接着剤。
- シリカ粒子は、フェニル基を有するシランカップリング剤で表面処理されたシリカ粒子であることを特徴とする請求項8記載の電子部品用接着剤。
- 更に、スペーサー粒子を含有することを特徴とする請求項1、2、3、4、5、6、7、8又は9記載の電子部品用接着剤。
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JP2013110422A (ja) * | 2011-03-09 | 2013-06-06 | Sekisui Chem Co Ltd | 電子部品用接着剤及び半導体チップ実装体の製造方法 |
JP2014130808A (ja) * | 2012-11-30 | 2014-07-10 | Sekisui Chem Co Ltd | 導電材料及び接続構造体 |
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JP6009751B2 (ja) * | 2011-10-04 | 2016-10-19 | 積水化学工業株式会社 | フリップチップ実装用封止剤及び半導体チップ実装体の製造方法 |
JP6223155B2 (ja) * | 2013-11-29 | 2017-11-01 | サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. | 接着剤層用塗布組成物、半導体用接着フィルムおよびその製造方法、ならびに、これを用いた半導体装置の製造方法 |
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JP2006117824A (ja) * | 2004-10-22 | 2006-05-11 | Toray Ind Inc | 半導体装置用接着剤組成物およびそれを用いた半導体装置用接着剤シート |
WO2009011383A1 (ja) * | 2007-07-19 | 2009-01-22 | Sekisui Chemical Co., Ltd. | 電子部品用接着剤 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2012126762A (ja) * | 2010-12-13 | 2012-07-05 | Sekisui Chem Co Ltd | 熱伝導性接着剤 |
JP2013110422A (ja) * | 2011-03-09 | 2013-06-06 | Sekisui Chem Co Ltd | 電子部品用接着剤及び半導体チップ実装体の製造方法 |
JP2013079316A (ja) * | 2011-10-03 | 2013-05-02 | Sekisui Chem Co Ltd | 電子部品用接着剤 |
JP2014130808A (ja) * | 2012-11-30 | 2014-07-10 | Sekisui Chem Co Ltd | 導電材料及び接続構造体 |
Also Published As
Publication number | Publication date |
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JP4729130B2 (ja) | 2011-07-20 |
TWI481685B (zh) | 2015-04-21 |
US20120016057A1 (en) | 2012-01-19 |
CN102292407B (zh) | 2014-01-01 |
TW201031726A (en) | 2010-09-01 |
KR20110123731A (ko) | 2011-11-15 |
JP2011116996A (ja) | 2011-06-16 |
JPWO2010087444A1 (ja) | 2012-08-02 |
CN102292407A (zh) | 2011-12-21 |
US8901207B2 (en) | 2014-12-02 |
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