JP2015048403A - ラジカル重合型接着剤組成物、及び電気接続体の製造方法 - Google Patents
ラジカル重合型接着剤組成物、及び電気接続体の製造方法 Download PDFInfo
- Publication number
- JP2015048403A JP2015048403A JP2013180751A JP2013180751A JP2015048403A JP 2015048403 A JP2015048403 A JP 2015048403A JP 2013180751 A JP2013180751 A JP 2013180751A JP 2013180751 A JP2013180751 A JP 2013180751A JP 2015048403 A JP2015048403 A JP 2015048403A
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- Prior art keywords
- radical polymerization
- adhesive layer
- adhesive composition
- photoacid generator
- polymerizable compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000010526 radical polymerization reaction Methods 0.000 title claims abstract description 88
- 239000000203 mixture Substances 0.000 title claims abstract description 87
- 239000000853 adhesive Substances 0.000 title claims abstract description 72
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 72
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 239000012790 adhesive layer Substances 0.000 claims abstract description 49
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 20
- 125000002091 cationic group Chemical group 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 230000001737 promoting effect Effects 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- -1 iron arene Chemical class 0.000 claims description 17
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- 239000000758 substrate Substances 0.000 claims description 9
- 238000003825 pressing Methods 0.000 claims description 6
- 239000012933 diacyl peroxide Substances 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 3
- 125000005409 triarylsulfonium group Chemical group 0.000 claims description 3
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- 238000010538 cationic polymerization reaction Methods 0.000 description 5
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- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
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- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- 229920005992 thermoplastic resin Polymers 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
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
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- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000012663 cationic photopolymerization Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
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- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
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- 230000009257 reactivity Effects 0.000 description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 1
- MCVVDMSWCQUKEV-UHFFFAOYSA-N (2-nitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=CC=C1[N+]([O-])=O MCVVDMSWCQUKEV-UHFFFAOYSA-N 0.000 description 1
- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
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- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000005633 Chrysanthemum balsamita Nutrition 0.000 description 1
- 244000260524 Chrysanthemum balsamita Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- AMFGWXWBFGVCKG-UHFFFAOYSA-N Panavia opaque Chemical compound C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 AMFGWXWBFGVCKG-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000006121 base glass Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 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 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
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- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
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- 229920006267 polyester film Polymers 0.000 description 1
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- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- SPVXKVOXSXTJOY-UHFFFAOYSA-O selenonium Chemical class [SeH3+] SPVXKVOXSXTJOY-UHFFFAOYSA-O 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- 125000005490 tosylate group Chemical class 0.000 description 1
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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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F222/10—Esters
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
-
- 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
- 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
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
-
- 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
- C09J2433/00—Presence of (meth)acrylic polymer
-
- 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
- C09J2471/00—Presence of polyether
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/10—Bump connectors; Manufacturing methods related thereto
- H01L2224/15—Structure, shape, material or disposition of the bump connectors after the connecting process
- H01L2224/16—Structure, shape, material or disposition of the bump connectors after the connecting process of an individual bump connector
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- H01L2224/16221—Disposition the bump connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
- H01L2224/16225—Disposition the bump connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation
- H01L2224/16227—Disposition the bump connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation the bump connector connecting to a bond pad of the item
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- H01—ELECTRIC ELEMENTS
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- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
- H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
- H01L2224/29001—Core members of the layer connector
- H01L2224/29099—Material
- H01L2224/2919—Material with a principal constituent of the material being a polymer, e.g. polyester, phenolic based polymer, epoxy
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
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- H01L2224/32—Structure, shape, material or disposition of the layer connectors after the connecting process of an individual layer connector
- H01L2224/321—Disposition
- H01L2224/32151—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
- H01L2224/32221—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
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Abstract
Description
前記接着剤層に、他方の電気部品の端子を配置する工程と、
対向配置された二つの電気部品の一方を他方に向かって押圧しながら、接着剤層に対し加熱と光照射とを行うことにより接着剤層を硬化させて対向配置された二つの電気部品同士を電気的に接続する工程と
を有する電気接続体の製造方法において、
当該接着剤層が、上述のラジカル重合型接着剤組成物から形成されたものであって、
接着剤層の硬化の際、光照射により光酸発生剤から酸を発生させ、それによりラジカル重合型接着剤組成物の熱ラジカル重合反応を促進させて接着剤層の硬化を行う製造方法を提供する。
前記接着剤層に、他方の電気部品の端子を配置する工程と、
対向配置された二つの電気部品の一方を他方に向かって押圧しながら、接着剤層に対し加熱と光照射とを行うことにより接着剤層を硬化させて対向配置された二つの電気部品同士を電気的に接続する工程と
を有する電気接続体の製造方法において、
当該接着剤層が、上述のラジカル重合型接着剤組成物から形成されたものであって、
接着剤層に対する加熱を、当該ラジカル重合型接着剤組成物から光酸発生剤が取り除かれているものに相当するラジカル重合型対照組成物の熱ラジカル重合反応温度よりも低い温度で行う製造方法を提供する。
本発明のラジカル重合型接着剤組成物は、ラジカル重合性化合物と、熱ラジカル重合開始剤と、光酸発生剤とを含有し、該光酸発生剤が発生する酸によりカチオン重合するカチオン重合性化合物、具体的にはエポキシ化合物、オキセタン化合物、ビニルエーテル化合物を含有しないものである。
本発明のラジカル重合型接着剤組成物を構成するラジカル重合性化合物は、熱ラジカル重合開始剤の熱分解により生ずる活性ラジカルによりラジカル重合反応し得る化合物であり、好ましくは分子内に1個以上の炭素不飽和結合を有するものであり、いわゆる単官能ラジカル重合性化合物、多官能ラジカル重合性化合物を包含する。ラジカル重合性化合物が、多官能ラジカル重合性化合物を含有した場合には、ラジカル重合型接着剤組成物の硬化物のダイシェア強度をより向上させることが可能となる。従って、ラジカル重合性化合物は、多官能ラジカル重合性化合物を好ましくは少なくとも30質量%以上、より好ましくは少なくとも50質量%以上含有する。
本発明のラジカル重合型接着剤組成物を構成する熱ラジカル重合開始剤は、熱分解により、ラジカル重合性化合物をラジカル重合するための活性ラジカルを発生するものであり、公知の熱ラジカル重合開始剤、例えば、有機過酸化物やアゾ系化合物等を好ましく使用することができる。中でも、優れた保存安定性と低温速硬化性とを実現可能である点から、有機過酸化物を好ましく使用することができる。
本発明のラジカル重合型接着剤組成物を構成する光酸発生剤は、紫外線などの光の照射を受けると酸を発生し、熱ラジカル重合開始剤の分解を促進するものである。換言すれば、光酸発生剤は、ラジカル重合型接着剤組成物の熱ラジカル重合反応を促進させる性質を有するものである。より具体的には、ラジカル重合型接着剤組成物の熱ラジカル重合反応を、当該ラジカル重合型接着剤組成物から更に光酸発生剤が取り除かれているものに相当するラジカル重合型対照組成物の熱ラジカル重合反応よりも促進させることが可能となる。
本発明のラジカル重合型接着剤組成物は、更に、フェノキシ樹脂等の熱可塑性樹脂を成膜用樹脂として含有することができる。このような熱可塑性樹脂の配合量は、ラジカル重合性化合物100質量部に対し、好ましくは10〜70質量部、より好ましくは20〜60質量部である。
本発明のラジカル重合型接着剤組成物は、ラジカル重合性化合物と、熱ラジカル重合開始剤と、光酸発生剤と、必要に応じて配合される熱可塑性樹脂等の他の成分とを、公知の混合手段により均一に混合することにより調製することができる。
本発明の電気接続体の製造方法(その1)は、以下の工程(イ)〜(ハ)を有する。以下に工程毎に説明する。
対向配置されるべき二つの電気部品の一方の電気部品の端子上に、公知の手法に従って接着剤層を配置する。ここで、対向配置されるべき二つの電気部品の一方としては、リジッド回路基板、フレキシブル配線基板等が挙げられる。それらの端子としては、銅、アルミニウム、銀、金、ITO等の電極材料から形成されたパッド電極、ライン電極、バンプ電極等が挙げられる。また、接着層は、前述した本発明のラジカル重合型接着剤組成物から形成されたものである。かかる接着層の形成は、公知の手法、例えば、各種塗布法や印刷法、更にはフォトリソグラフ技術などを利用して行うことができる。
次に、工程(イ)で形成された接着剤層に、他方の電気部品の端子を公知の手法に従って配置する。他方の電気部品としては、ICチップ、液晶パネル、有機ELパネル、ICモジュール、太陽電池モジュール等が挙げられる。それらの端子としては、銅、アルミニウム、銀、金、ITO等の電極材料から形成されたパッド電極、ライン電極、バンプ電極等が挙げられる。
工程(ロ)において対向配置された二つの電気部品の一方を他方に向かって、公知の加熱加圧ツールを用いて押圧しながら、接着剤層に対し加熱を行う。この加熱と同時に若しくは組成物の軟化若しくは溶融を待って、加熱開始後、加熱を継続しながら好ましくは2、3秒後から接着剤層に対し紫外線等の光、好ましくはLED光源のI線を用いて光照射を行い、接着剤層を硬化させる。ここで、少なくとも一方の電気部品が透明基板の片面に遮光部となり得る金属端子が形成されたものである場合、接着剤層への光照射を、電気部品の透明基板の他面側から行うことが好ましい。このように硬化させることにより電気接続体が得られる。この際、光照射により光酸発生剤から酸を発生させ、それによりラジカル重合型接着剤組成物の熱ラジカル重合を、当該ラジカル重合型接着剤組成物から光酸発生剤を取り除いたものに相当するラジカル重合型対照組成物の熱ラジカル重合よりも促進させて接着剤層の硬化を行う。これにより、遮光部が存在したとしても接着剤層を十分に硬化させることができ、対向配置された二つの電気部品同士を低い導電抵抗値で接続することができる。しかも、良好なダイシェア強度を実現することができ、また、電気接続体に反りが発生することを抑制することができる。
本発明の電気接続体の製造方法(その2)は、製造方法(その1)の工程(イ)〜(ハ)と同様の工程を有するが、工程(ハ)において、接着剤層に対する加熱を、当該ラジカル重合型接着剤組成物から更に光酸発生剤が取り除かれているものに相当するラジカル重合型対照組成物の熱ラジカル重合反応温度よりも低い温度で行うという具体的な加熱条件を明示している点で異なる。熱ラジカル重合反応温度T0よりも低い温度で加熱硬化を行うので、電気接合体の反りの発生を抑制でき、しかも光酸発生剤が発生する酸により、ラジカル重合型接着剤組成物の熱ラジカル重合反応温度T1がT0よりも低くなっているので、十分に硬化させることが可能となり、対向配置された二つの電気部品同士を低い導電抵抗値で接続することができる。しかも、良好なダイシェア強度を実現することができ、また、電気接続体に反りが発生することを抑制することができる。
表1に示す配合組成の成分を常法にて混合して得た混合物(接着剤組成物)を剥離ポリエステルフィルムに塗布し、70℃で乾燥することにより、20μm厚の接着シートを得た。
得られた接着シートを、評価基材としてのIC(外寸:1.8mm×20mm、バンプ高さ15μm)と、裏面に200μm巾の500nm厚のアルミニウムライン電極(遮光部)を200μmピッチで設けたベースガラス基板としてのITOコーティングガラス(ガラス厚0.5mm、ITO厚200nm)との間に挟み、表1の加熱温度、80MPaの圧力、5秒間という条件でICを加熱加圧し、加熱開始後2秒後に表1のUV照射条件(UV光源:UV照射器ZUV−C30H(オムロン(株))でUV照射を、ガラス基板の裏面側(アルミニウムライン電極形成面側)から3秒間行うことにより、試験評価用の電気接続体を作成した。
作成した電気接続体に2mAの電流を流した際の当該電気接続体の導通抵抗値を、抵抗測定機(デジタルマルチメータ7555、横河電機社製)を用いて4端子法にて測定した。得られた結果を表1に示す。実用上、1.0Ω以下であることが望まれる。
作成した電気接続体のダイシェア強度を、ダイシェアテスター(万能型ボンドテスターシリーズ4000、デイジ・ジャパン社製)を用いて、ツール速度100μm/秒という条件で測定した。得られた結果を表1に示す。実用上、100kgf以上であることが望まれる。
作成した電気接続体のガラス基板のアルミニウムライン電極形成面を、触針式表面粗度計(SE−3H、(株)小坂研究所)のプローブで走査し、反り量(μm)を測定した。得られた結果を表1に示す。実用上、10μm以下であることが望まれる。
ラジカル重合性化合物を含有する比較例1のラジカル重合性接着剤組成物は、光酸発生剤を含有するものの、有機過酸化物(熱ラジカル重合開始剤)を含有していない。このため、ラジカル反応(硬化反応)が進行しないために、導通抵抗値も非常に高く、またダイシェア強度も非常に低いものであった。
Claims (10)
- ラジカル重合性化合物と、熱ラジカル重合開始剤と、光酸発生剤とを含有し、該光酸発生剤が発生する酸によりカチオン重合するカチオン重合性化合物を含有しないラジカル重合型接着剤組成物。
- 光酸発生剤は、ラジカル重合型接着剤組成物の熱ラジカル重合反応を促進させる性質を有している請求項1記載のラジカル重合型接着剤組成物。
- 熱ラジカル重合開始剤が有機過酸化物であり、光酸発生剤がスルホニウム塩、ヨードニウム塩又は鉄アレーン錯体である請求項1又は2記載のラジカル重合型接着剤組成物。
- 熱ラジカル重合開始剤である有機過酸化物が1分間半減期温度80〜170℃且つ分子量180〜1000のパーオキシエステル又はジアシルパーオキサイドであり、光酸発生剤がトリアリールスルホニウム塩である請求項4記載のラジカル重合型接着剤組成物。
- 対向配置されるべき二つの電気部品の一方の電気部品の端子上に、接着剤層を配置する工程と、
前記接着剤層に、他方の電気部品の端子を配置する工程と、
対向配置された二つの電気部品の一方を他方に向かって押圧しながら、接着剤層に対し加熱と光照射とを行うことにより接着剤層を硬化させて対向配置された二つの電気部品同士を電気的に接続する工程と
を有する電気接続体の製造方法において、
当該接着剤層が、請求項1〜4のいずれかに記載のラジカル重合型接着剤組成物から形成されたものであって、
接着剤層の硬化の際、光照射により光酸発生剤から酸を発生させ、それによりラジカル重合型接着剤組成物の熱ラジカル重合反応を促進させて接着剤層の硬化を行う製造方法。 - 対向配置されるべき二つの電気部品の一方の電気部品の端子上に、接着剤層を配置する工程と、
前記接着剤層に、他方の電気部品の端子を配置する工程と、
対向配置された二つの電気部品の一方を他方に向かって押圧しながら、接着剤層に対し加熱と光照射とを行うことにより接着剤層を硬化させて対向配置された二つの電気部品同士を電気的に接続する工程と
を有する電気接続体の製造方法において、
当該接着剤層が、請求項1〜4のいずれかに記載のラジカル重合型接着剤組成物から形成されたものであって、
接着剤層に対する加熱を、当該ラジカル重合型接着剤組成物から光酸発生剤が取り除かれているものに相当するラジカル重合型対照組成物の熱ラジカル重合反応温度よりも低い温度で行う製造方法。 - 少なくとも一方の電気部品が透明基板の片面に金属端子が形成されたものであり、接着剤層への光照射を、該電気部品の透明基板の他面側から行う請求項5又は6記載の製造方法。
- 接着剤層に対する加熱を行った後に、光照射を行う請求項5〜7のいずれかに記載の製造方法。
- 熱ラジカル重合開始剤が有機過酸化物であり、光酸発生剤がスルホニウム塩、ヨードニウム塩又は鉄アレーン錯体である請求項5〜8のいずれかに記載の製造方法。
- 熱ラジカル重合開始剤である有機過酸化物が1分間半減期温度80〜170℃且つ分子量180〜1000のパーオキシエステル又はジアシルパーオキサイドであり、光酸発生剤がトリアリールスルホニウム塩である請求項9記載の製造方法。
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KR102148639B1 (ko) | 2020-08-27 |
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TWI651384B (zh) | 2019-02-21 |
CN110591570A (zh) | 2019-12-20 |
JP6232855B2 (ja) | 2017-11-22 |
CN110591570B (zh) | 2022-03-11 |
US20160115354A1 (en) | 2016-04-28 |
KR20160048032A (ko) | 2016-05-03 |
WO2015029622A1 (ja) | 2015-03-05 |
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