WO2013035871A1 - 電子装置用シール剤組成物 - Google Patents
電子装置用シール剤組成物 Download PDFInfo
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- WO2013035871A1 WO2013035871A1 PCT/JP2012/072987 JP2012072987W WO2013035871A1 WO 2013035871 A1 WO2013035871 A1 WO 2013035871A1 JP 2012072987 W JP2012072987 W JP 2012072987W WO 2013035871 A1 WO2013035871 A1 WO 2013035871A1
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- compound
- electronic device
- acrylate
- meth
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- 239000000203 mixture Substances 0.000 title claims abstract description 116
- 239000000565 sealant Substances 0.000 title abstract 3
- -1 nitroxide compound Chemical class 0.000 claims abstract description 68
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 11
- 239000003999 initiator Substances 0.000 claims description 12
- 238000007789 sealing Methods 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 3
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 3
- 239000004065 semiconductor Substances 0.000 description 28
- 239000000853 adhesive Substances 0.000 description 24
- 230000001070 adhesive effect Effects 0.000 description 24
- 238000000034 method Methods 0.000 description 21
- 150000003254 radicals Chemical class 0.000 description 20
- 239000006087 Silane Coupling Agent Substances 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- 229920001971 elastomer Polymers 0.000 description 10
- 239000000945 filler Substances 0.000 description 10
- 239000005060 rubber Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
- 239000000758 substrate Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 0 CC(c1ccccc1)ON(C(C(C)(C)C)P(*)=O)C(C)(C)C Chemical compound CC(c1ccccc1)ON(C(C(C)(C)C)P(*)=O)C(C)(C)C 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- 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 5
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
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- 229910003475 inorganic filler Inorganic materials 0.000 description 4
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- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
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- 229910000679 solder Inorganic materials 0.000 description 3
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- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- ZCZFEIZSYJAXKS-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COC(=O)C=C ZCZFEIZSYJAXKS-UHFFFAOYSA-N 0.000 description 2
- NOKSMMGULAYSTD-UHFFFAOYSA-N [SiH4].N=C=O Chemical compound [SiH4].N=C=O NOKSMMGULAYSTD-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
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- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
- RQAGEUFKLGHJPA-UHFFFAOYSA-N prop-2-enoylsilicon Chemical compound [Si]C(=O)C=C RQAGEUFKLGHJPA-UHFFFAOYSA-N 0.000 description 2
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- ZMZHRHTZJDBLEX-UHFFFAOYSA-N (2-phenylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C1=CC=CC=C1 ZMZHRHTZJDBLEX-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- AGKBXKFWMQLFGZ-UHFFFAOYSA-N (4-methylbenzoyl) 4-methylbenzenecarboperoxoate Chemical compound C1=CC(C)=CC=C1C(=O)OOC(=O)C1=CC=C(C)C=C1 AGKBXKFWMQLFGZ-UHFFFAOYSA-N 0.000 description 1
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
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- VBQCFYPTKHCPGI-UHFFFAOYSA-N 1,1-bis(2-methylpentan-2-ylperoxy)cyclohexane Chemical compound CCCC(C)(C)OOC1(OOC(C)(C)CCC)CCCCC1 VBQCFYPTKHCPGI-UHFFFAOYSA-N 0.000 description 1
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- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
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- CMEHZHBJSUHXBC-UHFFFAOYSA-N 10,11-dioctylicosane-1,20-diamine Chemical compound NCCCCCCCCCC(CCCCCCCC)C(CCCCCCCC)CCCCCCCCCN CMEHZHBJSUHXBC-UHFFFAOYSA-N 0.000 description 1
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- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- 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
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- 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
- C09J133/24—Homopolymers or copolymers of amides or imides
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- 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
- C09J135/00—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 a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Adhesives based on derivatives of such polymers
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- 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
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- H01L2224/16—Structure, shape, material or disposition of the bump connectors after the connecting process of an individual bump connector
- H01L2224/161—Disposition
- H01L2224/16151—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
- 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
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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
- 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
- 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
- H01L2224/31—Structure, shape, material or disposition of the layer connectors after the connecting process
- 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
- H01L2224/32225—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 the item being non-metallic, e.g. insulating substrate with or without metallisation
-
- 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
- H01L2224/73—Means for bonding being of different types provided for in two or more of groups H01L2224/10, H01L2224/18, H01L2224/26, H01L2224/34, H01L2224/42, H01L2224/50, H01L2224/63, H01L2224/71
- H01L2224/732—Location after the connecting process
- H01L2224/73201—Location after the connecting process on the same surface
- H01L2224/73203—Bump and layer connectors
- H01L2224/73204—Bump and layer connectors the bump connector being embedded into the layer connector
Definitions
- the present invention relates to a composition that can be used in the manufacture of electronic devices, particularly semiconductor devices, and the use thereof.
- a flip chip technique for directly connecting a semiconductor chip onto a substrate is known.
- the semiconductor chip and the wiring substrate are connected via electrodes (bumps) formed on the element forming surface side of the semiconductor chip.
- an underfill material which is an adhesive composition, between the semiconductor chip and the wiring board.
- an adhesive composition containing an epoxy compound and / or a (meth) acrylic compound is known (for example, Patent Document 1).
- the composition using the radical curing reaction of the (meth) acrylic compound has a merit that the reaction rate is higher than that of the composition containing the epoxy compound and the efficiency of electronic device manufacturing can be improved.
- a liquid adhesive composition is applied on a wiring board, a semiconductor chip is mounted, and electrode bonding and sealing are performed simultaneously.
- a method so-called capillary method
- capillary method that applies a liquid adhesive composition to one or more sides of a chip after the connection and seals the gap between the wiring board and the semiconductor chip using a capillary phenomenon. It has been.
- the liquid adhesive composition is uniformly applied on the wiring substrate, and that the gap between the semiconductor chip and the wiring substrate is uniformly filled with the liquid adhesive composition. Therefore, the fluidity
- An object of the present invention is to solve the above problems when a conventional adhesive composition is used, and to provide a composition that improves the productivity of an electronic device. Furthermore, it aims at providing the electronic device and electronic device containing this composition.
- the present invention relates to the following matters.
- a sealing agent composition for electronic devices comprising:
- composition of said 1 containing a radical initiator.
- composition according to 1 or 2 further comprising (b) a maleimide compound.
- composition according to 3 above, wherein the (b) maleimide compound comprises bismaleimide.
- the composition of the present invention does not cause defective electrode bonding in flip chip mounting of a semiconductor chip, and can secure a sufficient working time in the mounting process. Thereby, a higher quality product can be provided without reducing the production efficiency of the electronic device by flip chip mounting.
- the sealing agent composition for electronic devices of the present invention comprises at least (a) a compound having two or more (meth) acryloyl groups, (C) a nitroxide compound and / or a thiocarbonyl thio compound, including.
- a compound having two or more (meth) acryloyl groups (C) a nitroxide compound and / or a thiocarbonyl thio compound, including.
- the composition of the present invention includes a compound having two or more (meth) acryloyl groups (hereinafter also referred to as component (a)) as the (meth) acrylic compound.
- a compound having two (meth) acryloyl groups optionally has a compound having one (meth) acryloyl group and / or three or more (meth) acryloyl groups. It is preferable to use the compound added.
- the (meth) acrylic compound may be a monomer or an oligomer.
- the (meth) acrylic compound that can be used in the present invention is not limited, but examples of the compound having a monofunctional (meth) acryloyl group include phenylphenol acrylate, methoxypolyethylene acrylate, acryloyloxyethyl succinate, Fatty acid acrylate, methacryloyloxyethyl phthalic acid, phenoxyethylene glycol methacrylate, fatty acid methacrylate, ⁇ -carboxyethyl acrylate, isobornyl acrylate, isobutyl acrylate, tertiary butyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, dihydrocyclopentadiethyl acrylate, Cyclohexyl methacrylate, tertiary butyl methacrylate, dimethylaminoethyl Methacrylate, diethylaminoethyl methacrylate, tertiary butyl amino
- These (meth) acrylic compounds may be used alone or in combination of two or more.
- the content of the (meth) acrylic compound can be prepared depending on the use, but it is preferably 10 to 90% by weight, more preferably 20 to 60% by weight based on the total weight of the composition. .
- the content of the (meth) acrylic compound is within this range, the viscosity of the composition before curing is low and the workability is excellent, and the strength after curing is also excellent.
- composition of the present invention contains a nitroxide compound and / or a thiocarbonylthio compound (hereinafter also referred to as component (c)).
- component (c) is a compound that is generally used as a control agent for controlling the growth reaction and termination reaction during living radical polymerization.
- the nitroxide compound means a compound having a nitroxide radical partial structure represented by the formula (II) or a compound capable of generating a nitroxide radical partial structure.
- the nitroxide radical partial structure of the formula (II) is known as a capping agent for capping a radical at a polymer growth end in a nitroxide-mediated living radical polymerization reaction (NMP: Nitroxide-Mediated Radical Polymerization).
- the thiocarbonylthio compound has a structure of the formula (III) and is known as a chain transfer agent in a reversible addition fragmentation chain transfer (RAFT) polymerization reaction, which is a kind of living radical polymerization. ing.
- RAFT reversible addition fragmentation chain transfer
- the composition of the present invention When the composition of the present invention is used for manufacturing a semiconductor device, the composition is applied on, for example, a wiring substrate, as will be described later. In that case, in order to improve the fluidity
- the composition of the present invention contains the component (c), the progress of the curing reaction is sufficiently suppressed, and the efficiency of work in the subsequent mounting process is not reduced. For this reason, the inventors presume that the radical generated in the composition reversibly inactivates the radical species that grow by the radical structure of component (c), thereby suppressing the progress of the curing reaction. ing.
- the composition of the present invention does not inhibit the subsequent curing reaction at a higher temperature, and does not cause any problem in the physical properties of the composition after curing.
- the content of component (c) is preferably 0.001 to 5% by weight, more preferably 0.01 to 1% by weight, based on the total weight of the composition.
- the composition of this invention contains the thermal radical initiator mentioned later, and the molar ratio (initiator: component (c)) of an initiator and a component (c) is 1: 0.001 in this case. It is preferably ⁇ 1: 10, more preferably 1: 0.01 to 1: 1. When the content of the component (c) is within this range, there is no problem in the reactivity and physical properties of the composition.
- the compound having a nitroxide radical partial structure is not limited, but 2,2,5-trimethyl-4-phenyl-3-azahexane-3-nitroxide, 2,2,6,6-tetramethyl-1-piperidi Nyloxy radical (TEMPO), 2,2,6,6-tetraethyl-1-piperidinyloxy radical, 2,2,6,6-tetramethyl-4-oxo-1-piperidinyloxy radical, 2, 2,5,5-tetramethyl-1-pyrrolidinyloxy radical, 1,1,3,3-tetramethyl-2-isoindolinyloxy radical, N, N-di-t-butylamineoxy radical, etc. It is done.
- TEMPO 2,2,6,6-tetramethyl-1-piperidi Nyloxy radical
- 2,2,6,6-tetraethyl-1-piperidinyloxy radical 2,2,6,6-tetramethyl-4-oxo-1-piperidinyloxy radical
- R 1 —O—N (R 2 ) (R 3 ) (IV) (Here, R 1 , R 2 and R 3 are organic residues, and R 2 and R 3 may form a cyclic structure.)
- alkoxyamine compound represented by the general formula (IV) examples include the following alkoxyamine compounds described in a paper by Didier Benoit et al. (J. Am. Chem. Soc. 1999, 121, 3904-3920). It is done.
- Examples of the thiocarbonylthio compound include compounds described in JP-T-2004-518773. Specifically, although not particularly limited, for example, 2-cyano-2-propylbenzodithioate, 4-cyano-4- (phenylcarbonothioylthio) pentanoic acid, 2-cyano-2-propyldodecyltrithiocarbo 4-cyano-4-[(dodecylsulfanylthiocarbonyl) sulfanyl] pentanoic acid, 2- (dodecylthiocarbonothioylthio) -2-methylpropionic acid, cyanomethyldodecyltrithiocarbonate, cyanomethylmethyl (phenyl) ) Carbamodithioate, bis (thiobenzoyl) disulfide, bis (dodecylsulfanylthiocarbonyl) disulfide and the like. These are commercially available from, for example, Aldrich
- one type of compound may be used alone, or two or more types of compounds may be used in combination.
- composition of the present invention is further described as (b) maleimide compound (hereinafter referred to as component (b)). In some cases). Although it does not specifically limit as a maleimide compound, The following compounds can be mentioned.
- Maleimide compound has partial structure (I):
- R 1 and R 2 represent H, an alkyl group having 1 to 6 carbon atoms, or R 1 and R 2 together represent an alkylene group having 2 to 6 carbon atoms.
- R 1 and R 2 are both H, or R 1 and R 2 together represent a 1,4-butylene group.
- the maleimide compound is preferably in a liquid state at room temperature, and the group to which the partial structure (I) is bonded is a group that makes the maleimide compound in a liquid state, for example, a length and branch sufficient to make the maleimide compound into a liquid state. It is an organic group containing a branched alkyl, alkylene, alkylene oxide, alkylene carboxyl or alkylene amide structure.
- the maleimide compound can have one or more partial structures (I).
- a compound having two groups is a bismaleimide compound. Even if one maleimide compound is not liquid, it can be used as long as the composition becomes liquid when mixed with other maleimide compounds or when mixed with other components.
- maleimide compounds in which the partial structure (I) is bonded to an alkyl group or an alkylene group include the following compounds. .
- stearyl maleimide particularly preferred are stearyl maleimide, oleyl maleimide, behenyl maleimide, 1,20-bismaleimide derivatives of 10,11-dioctyleicosane, and combinations thereof.
- a 1,20-bismaleimide derivative of 10,11-dioctyleicosane is available from Henkel Corporation under the product name X-BMI, and 1,20-diamino-10,11-dioctyleicosane and / or its cyclic Synthesized from isomeric diamines according to the method described in US Pat. No. 5,973,166 (the disclosure of US Pat. No. 5,973,166 is hereby incorporated by reference).
- X-BMI is 1,20-bismaleimide-10,11-dioctyl-eicosane ⁇ compound represented by the formula (X-1) ⁇ , 1-heptylenemaleimide-2-octylenemaleimide-4-octyl-5 -Heptylcyclohexane ⁇ compound represented by the formula (X-2) ⁇ , 1,2-dioctylenemaleimide-3-octyl-4-hexylcyclohexane ⁇ compound represented by the formula (X-3) ⁇ or the like Includes two or more.
- the bismaleimide compounds represented by the formulas (X-1) to (X-3) are also preferably used alone.
- maleimide compounds in which the partial structure (I) is bonded to a group containing an alkylene oxide structure include the following compounds.
- R is an alkylene group, preferably ethylene or 1,2-propylene
- n is an integer of about 2 to 40, preferably an integer such that this compound is liquid, and distribution of n Is selected.
- This compound is available as LUMICURE (registered trademark) MIA200 manufactured by Dainippon Ink and Chemicals, Inc.
- the maleimide compounds can be used alone or in combination of two or more.
- the content of the maleimide compound is preferably 0 to 50% by weight, more preferably 0.1 to 50% by weight, and more preferably 1 to 20% by weight with respect to the total weight of the composition. More preferably it is. When the content of the maleimide compound is within this range, the curing rate is excellent.
- the composition when the composition contains a maleimide compound, the (meth) acrylic compound and the maleimide compound in the composition undergo radical polymerization by heating to a predetermined temperature.
- a homopolymer can be formed by polymerizing only with a compound, or a copolymer can be formed by polymerizing two or more compounds.
- the composition of the present invention may contain a filler.
- a filler By blending a filler, it is possible to obtain an electronic device composition having a low coefficient of linear expansion, excellent dimensional stability, and improved flame retardancy.
- the filler either an insulating inorganic filler or a conductive inorganic filler can be selected depending on the application.
- the insulating inorganic filler include silica, calcium silicate, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, aluminum nitride, and boron nitride. Silica is particularly preferable.
- the conductive inorganic filler include metals and carbon black.
- the filler that has been subjected to surface modification as necessary may be used.
- Commercially available products include, for example, Mitsubishi Chemical's “Mitsubishi Carbon Black” lineup, Asahi Carbon's “Asahi” series, Kawai Lime Industry's calcium silicate “PCM Light” series, aluminum hydroxide “ALH” series, and alumina-based “Sera” Sur, Titanium Chemical's titanium oxide “STR series”, Silica “Scicus series”, Zinc oxide “FINEEX series”, Magnesium oxide “SMO series”, Zirconium oxide “STR series”, Admattex silica, Alumina oxide “Adma” Examples include the “Fine” series, the “Snowtex” series of silica from Nissan Chemical Industries, and the “Nanotech” series of metal oxides containing silica and aluminum oxide.
- the average particle size of the filler is preferably smaller than the gap size between the semiconductor chip element formation surface and the wiring board. If the average particle size of the filler is too large, when the semiconductor device is manufactured, the filler may be trapped between the metal connections, and good electrical reliability may not be obtained, or the chip may be destroyed.
- the blending amount of the filler can be adjusted according to the use, but for example, it is preferably 1 to 99% by weight and more preferably 10 to 80% by weight with respect to the total weight of the adhesive composition. Within the above range, it is possible to obtain a composition having a viscosity that has a sufficient effect due to the addition of the filler and has no problem in handling properties.
- the composition of the present invention preferably contains a radical initiator, and more preferably contains a thermal radical initiator.
- a thermal radical initiator an organic peroxide is preferable, and one that generates radicals at an appropriate temperature is selected.
- the radical initiator is not particularly limited, and examples thereof include diisobutyl peroxide, cumyl peroxyneodecanate, di-n-propyl peroxycarbonate, diisopropyl peroxycarbonate, and di-sec-butyl peroxycarbonate.
- 1,1,3,3-tetramethylbutylperoxyneodecane di (4-t-butylcyclohexyl) peroxydicarbonate, di (2-ethylhexyl) peroxydicarbonate, t-hexylperoxyneodecane Nate, t-butyl peroxyneodecanate, t-butyl peroxyneoheptanate, t-hexyl peroxypivalate, t-butyl peroxypivalate, di (3,5,5-trimethylhexanoyl) peroxide Dilauroyl peroxide 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanate, disuccinic acid peroxide, 2,5-dimethyl-2,5-di (2-ethylhexanoylperoxy) hexane, t-hexylper Oxy-2-ethylhexanate, di (4-methylbenz
- the blending amount of the radical initiator is preferably 0.01 to 10% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition.
- the blending amount of the thermal radical initiator is within the above range, there is no problem in stability when the composition is applied, and there is no problem that a long curing time is required.
- the composition of the present invention can contain additives such as a silane coupling agent, a rubber component, an antioxidant, a light-resistant stabilizer, a radical stabilizer, and a surfactant, if necessary. Adhesiveness of the composition is improved by the silane coupling agent and the rubber component, and further, there are advantages such that stress is relieved and warpage of the reaction cured product is reduced. Antioxidants and radical stabilizers can be used when it is desired to further increase the pot life.
- the surfactant can also be added in the case of improving defoaming at the time of coating, wettability to the coating target, and leveling properties.
- the adhesiveness of the adhesive can be improved by blending the silane coupling agent into the composition.
- silane coupling agent for example, an aminosilane coupling agent, an epoxy silane coupling agent, a ureido silane coupling agent, an isocyanate silane coupling agent, a vinyl silane coupling agent, a (meth) acryl silane coupling agent And ketimine silane coupling agents, among which isocyanate silane coupling agents, (meth) acryl silane coupling agents, and epoxy silane coupling agents are preferred.
- silane coupling agents can be purchased from Toray Dow Corning, Shin-Etsu Silicone, Matsumoto Fine Chemical, Tokyo Chemical Industry Co., etc.
- the amount of the silane coupling agent can be adjusted as appropriate, but for example, it is preferably 0 to 10% by weight, more preferably 0 to 5% by weight, based on the total weight of the composition.
- a void will generate
- the rubber is not particularly limited, and examples thereof include rubber products such as acrylic rubber, nitrile rubber, butadiene rubber, and nitrile butadiene rubber, and low molecular weight rubber crosslinking agents.
- Commercially available rubber products include, for example, “Paraklon RP” series manufactured by Negami Kogyo Co., “Staffyroid IM” series and “Staffyroid AC” series manufactured by Ganz Kasei Co., “Zeon” series manufactured by ZEON Kasei Co., Ltd., and Mitsubishi Rayon “Metabrene C / E / W / S / SX / SRX” manufactured by the company is mentioned.
- Low molecular weight rubber crosslinking agents include, for example, “Ricon” series manufactured by SARTOMER, “poly bd”, “poly ip” series, “Epol” series, “KRASOL”, manufactured by Nippon Soda Co., Ltd. “NISSO-PB” and the like. These may be used alone or in combination of two or more.
- the blending amount of rubber can be adjusted as appropriate, but is preferably 0 to 30% by weight, and more preferably 0 to 20% by weight with respect to the total weight of the adhesive composition. If the rubber content is too high, the viscosity of the adhesive composition will increase excessively, resulting in poor handling, miscibility with other components, and poor adhesive adhesion. There is.
- antioxidants and radical stabilizers include hydroquinones, benzoquinones, hindered phenols, and examples of light-resistant stabilizers include benzotriazole, triazine, benzophenone, benzoate, and hindered amine ultraviolet absorbers. It is done.
- the surfactant can be selected from a commercially available catalog according to the purpose.
- the composition of the present invention can be obtained by uniformly mixing the above-described components and, if necessary, a solvent.
- the composition should just be adjusted to the viscosity which can be apply
- the composition of the present invention is not particularly limited.
- various known kneaders such as a homodisperser, a universal mixer, a Banbury mixer, a kneader, a two-roll, a three-roll, and an extruder are used alone or in combination. And it can manufacture by kneading
- the composition for an electronic device of the present invention is not particularly limited, but is preferably used for a sealing agent for an electronic device.
- a sealing agent an underfill material (sealing material) of an electronic device including a semiconductor chip, an insulating varnish, an insulating material for a printed wiring board, an impregnating resin for a printed wiring board, a coating agent for an electronic device, an electronic device Potting agents, adhesives for electronic devices, and the like, and the present invention is particularly preferably used as an underfill material.
- the manufacturing method of the electronic device is not particularly limited, but it is preferable to use a flip chip method.
- the composition of the present invention is particularly preferably applied on the circuit surface of the wiring board.
- an electronic device manufacturing method for example, (1) A coating process for coating the composition of the present invention on the circuit surface of the wiring board; (2) a bonding / sealing step in which a semiconductor chip is disposed on a composition coated on a wiring board, and electrical connection between the semiconductor chip and the wiring board and sealing of a gap between the semiconductor chip and the wiring board; including. Each step will be described below.
- the composition of the present invention is coated on the circuit surface of the wiring board.
- the composition may be applied to the entire surface of the wiring substrate, or may be applied only to the portion where the semiconductor chip is mounted.
- Examples of the coating method include a method of coating with a spin coater, a dispenser, a roller, etc., screen printing, and the like.
- ⁇ (2) Joining / sealing process> an electrical connection between the semiconductor element and the wiring board is performed, and at the same time, the gap between the semiconductor element and the circuit board is sealed with the composition of the present invention to manufacture an electronic device.
- a semiconductor chip is placed on a portion of the wiring board where the adhesive composition has been applied.
- alignment is performed so that the circuit surface of the wiring board (that is, the surface coated with the composition in the coating step) and the element formation surface of the semiconductor chip face each other.
- thermocompression bonding is performed. After thermocompression bonding, heating may be further performed for the purpose of curing the adhesive composition.
- thermocompression bonding generally, a method of aligning using a flip chip bonder and then performing thermocompression bonding as it is, or a method of heat-connecting an object after alignment and temporary mounting in a reflow furnace or the like is used. At that time, a thermal profile suitable for the package and the sealing method is used. In addition, not only flip chip bonder but also die bonder or the like that can be aligned can be used for chip mounting.
- the temperature at which the thermocompression bonding is performed is not particularly limited, but when the electrode is a solder bump or a solder mounting bump, the temperature is preferably 10 to 100 ° C. higher than its melting point, and preferably 200 ° C. or higher. It is preferably 210 to 300 ° C.
- the time for performing thermocompression bonding is preferably 1 to 20 seconds, and the pressure is preferably 0.1 to 7 MPa. Further, when further heating is performed in order to complete the curing of the adhesive composition after the thermocompression bonding, for example, it is preferably 30 to 180 minutes at 150 to 220 ° C.
- the electronic device obtained as described above can be used in many electronic devices that use semiconductor chips such as mobile phones, personal computers, and televisions.
- the devices used in the following examples and comparative examples are as follows.
- the circuit board and (2) the semiconductor chip constitute a daisy chain by connecting the two, and can conduct when all the bumps in the chip are connected. That is, 544 pieces. If even one of the bumps cannot be connected, insulation will be shown in the continuity test.
- Example 1> (Preparation of composition) The compounds shown in Table 2 were collected so as to have the respective compounding amounts, and were uniformly kneaded with three rolls. This was deaerated in a vacuum to prepare an adhesive composition A.
- the composition A was applied onto the circuit board using an auto dispenser to obtain a circuit board B coated with the adhesive composition A.
- circuit board B (Electronic device mounting) Flip chip bonder with pulse heat function immediately after obtaining circuit board B (leaving time 0 minutes) or after leaving on a hot plate at 80 ° C. for 15, 30, 45, 60 or 90 minutes
- the semiconductor chip and the circuit board B were aligned and pressure-welded with each other, followed by thermocompression bonding at 240 ° C. by pulse heat. Thereafter, the composition A was cured by a dryer at 150 ° C. for 1 hour to obtain an electronic device C.
- Examples 2 to 13 An electronic device was manufactured by the same method as in Example 1 except that each component blended in the composition was changed as shown in Table 2. Also in Examples 2 to 13, the circuit board coated with the composition was allowed to stand at 80 ° C. for 0 minutes, 15 minutes, 30 minutes, 45 minutes, 60 minutes, and 90 minutes, and then an electronic device was manufactured to provide conductivity. I investigated. As a result, good conductivity was obtained in all cases. Therefore, it was shown that the compositions of Examples 2 to 13 also maintained liquid properties that could be worked even when left on a hot plate at 80 ° C.
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Abstract
Description
(c)ニトロキシド化合物および/またはチオカルボニルチオ化合物と、
を含む、電子装置用シール剤組成物。
(a)2以上の(メタ)アクリロイル基を有する化合物と、
(c)ニトロキシド化合物および/またはチオカルボルニルチオ化合物と、
を含む。以下、各成分について説明する。
本発明の組成物は、(メタ)アクリル化合物として、2以上の(メタ)アクリロイル基を有する化合物(以下、成分(a)と記載することもある)を含む。通常、2つの(メタ)アクリロイル基を有している化合物に、必要により、1つの(メタ)アクリロイル基を有している化合物および/または3つ以上の(メタ)アクリロイル基を有している化合物を加えて使用することが好ましい。また、(メタ)アクリル化合物は、モノマーであってもオリゴマーであってもよい。
2以上の(メタ)アクリロイル基を有する化合物としては、ヘキサンジオールジメタクリレート、ヒドロキシアクリロイロキシプロピルメタクリレート、ヘキサンジオールジアクリレート、ウレタンアクリレート、エポキシアクリレート、ビスフェノールA型エポキシアクリレート、変性エポキシアクリレート、脂肪酸変性エポキシアクリレート、アミン変性ビスフェノールAタイプエポキシアクリレート、アリルメタクリレート、エチレングリコールジメタクリレート、ジエチレングリコールジメタクリレート、エトキシ化ビスフェノールAジメタクリレート、トリシクロデカンジメタノールジメタクリレート、グリセリンジメタクリレート、ポリプロピレングリコールジアクリレート、プロポキシ化エトキシ化ビスフェノールAジアクリレート、9,9-ビス(4-(2-アクリロイルオキシエトキシ)フェニル)フルオレン、トリシクロデカンジアクリレート、ジプロピレングリコールジアクリレート、ポリプロピレングリコールジアクリレート、プロポキシ化ネオペンチルグリコールジアクリレート、トリシクロデカンジメタノールジアクリレート、1,12-ドデカンジオールジメタクリレート、トリメチロールプロパントリメタクリレート、ジペンタエリストールポリアクリレート、ジペンタエリストールヘキサアクリレート、トリメチロールプロパントリアクリレート、トリメチロールプロパンエトキシトリアクリレート、ポリエーテルトリアクリレート、グリセリンプロポキシトリアクリレート、ペンタエリスリトールテトラアクリレート、ペンタエリスリトールエトキシテトラアクリレート、ジトリメチロールプロパンテトラアクリレート、モノペンタエリスリトールアクリレート、ジペンタエリスリトールアクリレート、トリペンタエリスリトールアクリレート、ポリペンタエリスリトールアクリレート、ペンタエリスリトールトリアクリレートが挙げられる。
本発明の組成物は、ニトロキシド化合物および/またはチオカルボニルチオ化合物(以下、成分(c)と記載することもある。)を含む。成分(c)は、一般にリビングラジカル重合の際、成長反応や停止反応を制御する制御剤として用いられる化合物である。
R1-O-N(R2)(R3) (IV)
(ここでR1、R2、R3は有機残基であり、R2とR3とが環状構造を形成しても良い。)
本発明の組成物は、上記(a)(メタ)アクリル化合物と、(c)ニトロキシド化合物および/またはチオカルボニルチオ化合物に加え、さらに(b)マレイミド化合物(以下、成分(b)と記載することもある。)を含むことが好ましい。マレイミド化合物としては、特に限定されないが、以下の化合物を挙げることができる。
本発明の組成物はフィラーを含んでもよい。フィラーを配合することにより、線膨張係数が低くて寸法安定性に優れ、かつ、難燃性が改善された電子装置用組成物を得ることができる。フィラーは、用途に応じて絶縁性無機フィラーまたは導電性無機フィラーのいずれかを選択することができる。絶縁性無機フィラーとしては、シリカ、ケイ酸カルシウム、水酸化アルミニウム、水酸化マグネシウム、炭酸カルシウム、炭酸マグネシウム、酸化マグネシウム、窒化アルミニウム、窒化ホウ素等が挙げられ、特にシリカが好ましい。導電性無機フィラーとしては、金属やカーボンブラックが挙げられる。
本発明の組成物は、ラジカル開始剤を含むことが好ましく、熱ラジカル開始剤を含むことがより好ましい。熱ラジカル開始剤としては、有機過酸化物が好ましく、適当な温度でラジカルを発生するものを選択する。
本発明の組成物は、上述の各成分と、必要により溶剤を加えて均一に混合して得ることができる。組成物は使用時にディスペンサー等の塗布装置で塗布できる粘度に調整されていればよく、無溶剤であってもよい。また、組成物中の化合物の選択および配合量を調整して粘度を調整することも可能である。本発明の組成物は、特に限定されないが、例えば、ホモディスパーサー、万能ミキサー、バンバリーミキサー、ニーダー、2本ロール、3本ロール、押出機等の公知の各種混練機を単独で用いるか又は併用して、所定量の各成分を均一に混練することにより製造できる。該混練は、常温下若しくは加熱下で、常圧下、減圧下、加圧下若しくは不活性ガス気流下等の条件下で行われる。
次に、本発明の組成物を含む電子装置の製造方法について説明する。電子装置の製造方法としては、特に限定はされないが、フリップチップ工法を用いることが好ましい。フリップチップ工法において、本発明の組成物は、配線基板の回路面上に塗布されることが特に好ましい。電子装置の製造方法としては、例えば、
(1)本発明の組成物を配線基板の回路面上に塗布する塗布工程と、
(2)配線基板上に塗布された組成物の上に半導体チップを配置し、半導体チップと配線基板との電気的接続と、その間隙の封止とを行う接合・封止工程と、
を含む。以下各工程について説明する。
塗布工程では、本発明の組成物を配線基板の回路面上に塗布する。該組成物は、配線基板の表面上全体に塗布されてもよいし、半導体チップが搭載される部分のみに塗布されてもよい。塗布方法としては、スピンコーター、ディスペンサー、ローラ等で塗布する方法や、スクリーン印刷等が挙げられる。また、組成物の流動性を向上させるために、必要に応じて塗布工程に用いるシリンジや、基板等を室温以上の温度に加温してもよい。
接合・封止工程においては、半導体素子と配線基板との電気的接続を行うと同時に、半導体素子と回路基板との間隙を本発明の組成物で封止して、電子装置を製造する。まず、配線基板上の接着剤組成物が塗布された部分に半導体チップを配置する。その際、配線基板の回路面(すなわち、上記塗布工程において組成物が塗布された面)と半導体チップの素子形成面が対向するように位置合わせを行う。続いて加熱圧着接合する。加熱圧着接合後に、接着剤組成物を硬化させる目的で、更に加熱してもよい。加熱圧着接合する方法としては、一般的には、フリップチップボンダーを用いて位置合わせをした後、そのまま加熱圧着する方法、または位置合わせ、仮搭載が終わったものをリフロー炉などで加熱接続させる方法が用いられる。その際、パッケージや封止法に適した熱プロファイルが用いられる。また、チップ搭載にはフリップチップボンダーのみならず、ダイボンダーなど位置合わせが可能なもので代替することもできる。
(1)回路基板:株式会社ウォルツ社製のWALTS-KIT MB50-0102JY_CR、パッドはCuOSP仕様。
(2)半導体チップ:株式会社ウォルツ社製のWALTS-TEG MB50-0101JY、Cuピラーとはんだからなるバンプを544個搭載している。
(上記(1)回路基板と(2)半導体チップとは両者の接続によりデイジーチェーンを構成し、チップ内の全てのバンプが接続されたときに導通可能となるものである。すなわち、544個のバンプの内1個でも接続できなければ導通試験で絶縁性を示す。)
以下の方法により、各成分を混合し、接着剤組成物を調製した。各実施例および比較例において配合した化合物とその配合量(重量%)は表2に示したとおりである。
(組成物の調製)
表2に示した化合物を各配合量となるように採取し、3本ロールで均一に混練した。これを真空で脱気して、接着剤組成物Aを調製した。
回路基板Bを得た直後(放置時間0分)、または、80℃のホットプレート上で15分、30分、45分、60分もしくは90分放置した後、パルスヒート機能を具備したフリップチップボンダーを用いて、半導体チップと回路基板Bとの位置合わせを行って圧接し、続いてパルスヒートにて240℃で熱圧着を行った。その後、乾燥機にて150℃、1時間、組成物Aを硬化させ、電子装置Cを得た。
上記で得た電子装置Cの導通性を調べたところ、80℃のホットプレート上での放置時間がいずれの場合であっても導通性は良好であった(表3)。すなわち、半導体チップ上の544個のすべてのバンプが接続された。したがって、実施例1の組成物は、80℃のホットプレート上に放置されても作業可能な液状性を保っていることが示された。
組成物に配合する各成分を表2のように変えた以外は、実施例1と同様の方法により電子装置を製造した。実施例2~13においても、組成物が塗布された回路基板を、80℃に0分、15分、30分、45分、60分、90分放置した後、電子装置を製造して導通性を調べた。その結果、すべての場合において良好な導通性が得られた。したがって、実施例2~13の組成物も、80℃のホットプレート上に放置されても作業可能な液状性を保っていることが示された。
組成物に配合する各成分を表2のように変え、マレイミド化合物と成分(c)を配合せずに、実施例1と同様の方法により電子装置を製造した。比較例1においても、組成物が塗布された回路基板を、80℃で、0分、15分、30分、45分、60分、90分放置した後、電子装置を製造して導通性を調べた。その結果、80℃に放置せずに(放置時間0分で)製造した電子装置の導通性は良好であったが、それ以外の場合はすべて、導通性が得られなかった(表4)。したがって、比較例1の組成物は、80℃に放置することにより組成物の硬化が進行してしまい、良好な導通性が得られないことが示された。
組成物に配合する各成分を表2のように変え、成分(c)を配合せずに、実施例1と同様の方法により電子装置を製造した。比較例2においても、実施例1と同様にして導通性を調べた。その結果、80℃に放置せずに(放置時間0分で)製造した電子装置の導通性は良好であったが、それ以外の場合(80℃に放置した場合)はすべて、導通性が得られなかった。比較例2の組成物も、80℃に放置することにより組成物の硬化が進行してしまい、良好な導通性が得られないことを確認した。
組成物に配合する各成分を表2のように変え、成分(c)に代えて重合禁止剤であるベンゾキノンを用いて、実施例1と同様の方法により電子装置を製造した。比較例3においても、実施例1と同様にして導通性を調べた。その結果、80℃に放置せずに(放置時間0分で)製造した電子装置の導通性は良好であったが、それ以外の場合(80℃に放置した場合)はすべて、導通性が得られなかった。比較例3の組成物も、80℃に放置することにより組成物の硬化が進行してしまい、良好な導通性が得られないことを確認した。
組成物に配合する各成分を表2のように変え、成分(c)に代えて重合禁止剤であるヒドロキノンを用いて、実施例1と同様の方法により電子装置を製造した。比較例4においても、実施例1と同様にして導通性を調べた。その結果、80℃に放置せずに(放置時間0分で)製造した電子装置の導通性は良好であったが、それ以外の場合(80℃に放置した場合)はすべて、導通性が得られなかった。比較例4の組成物も、80℃に放置することにより組成物の硬化が進行してしまい、良好な導通性が得られないことを確認した。
Claims (8)
- (a)2以上の(メタ)アクリロイル基を有する化合物と、
(c)ニトロキシド化合物および/またはチオカルボニルチオ化合物と、
を含む、電子装置用シール剤組成物。 - さらに、ラジカル開始剤を含む、請求項1に記載の組成物。
- さらに(b)マレイミド化合物を含む、請求項1または2に記載の組成物。
- 前記(b)マレイミド化合物が、ビスマレイミドを含む、請求項3に記載の組成物。
- アンダーフィル材として使用される請求項1~4のいずれか1項に記載の組成物。
- フリップチップ実装において使用される請求項1~5のいずれか1項に記載の組成物。
- 請求項1~6のいずれか1項に記載の組成物の硬化物を含む電子装置。
- 請求項7に記載の電子装置を含む電子機器。
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CN113366041A (zh) * | 2019-01-31 | 2021-09-07 | 松下知识产权经营株式会社 | 热固性树脂组合物、树脂片、层压体和印刷线路板 |
JP7450224B2 (ja) | 2019-01-31 | 2024-03-15 | パナソニックIpマネジメント株式会社 | 熱硬化性樹脂組成物、樹脂シート、積層板及びプリント配線板 |
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Also Published As
Publication number | Publication date |
---|---|
PT2755232T (pt) | 2017-04-12 |
EP2755232A4 (en) | 2015-09-30 |
EP2755232A1 (en) | 2014-07-16 |
US20160177148A1 (en) | 2016-06-23 |
SG11201400489QA (en) | 2014-05-29 |
TWI618790B (zh) | 2018-03-21 |
WO2013035206A1 (ja) | 2013-03-14 |
KR101900130B1 (ko) | 2018-09-18 |
CN103858217A (zh) | 2014-06-11 |
US9771500B2 (en) | 2017-09-26 |
TW201321488A (zh) | 2013-06-01 |
JPWO2013035871A1 (ja) | 2015-03-23 |
EP2755232B1 (en) | 2017-02-08 |
KR20140068928A (ko) | 2014-06-09 |
US20140187714A1 (en) | 2014-07-03 |
JP6084567B2 (ja) | 2017-02-22 |
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