WO2012008316A1 - 多層粘着シート及び電子部品の製造方法 - Google Patents
多層粘着シート及び電子部品の製造方法 Download PDFInfo
- Publication number
- WO2012008316A1 WO2012008316A1 PCT/JP2011/065149 JP2011065149W WO2012008316A1 WO 2012008316 A1 WO2012008316 A1 WO 2012008316A1 JP 2011065149 W JP2011065149 W JP 2011065149W WO 2012008316 A1 WO2012008316 A1 WO 2012008316A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- meth
- acrylate
- sensitive adhesive
- adhesive sheet
- pressure
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 59
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 13
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- 239000004065 semiconductor Substances 0.000 claims abstract description 31
- 239000012948 isocyanate Substances 0.000 claims abstract description 30
- 239000012790 adhesive layer Substances 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 24
- 239000003999 initiator Substances 0.000 claims abstract description 18
- 229920005573 silicon-containing polymer Polymers 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 98
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 68
- -1 vinyl compound Chemical class 0.000 claims description 48
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 239000000178 monomer Substances 0.000 claims description 32
- 239000010410 layer Substances 0.000 claims description 20
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- 229920003067 (meth)acrylic acid ester copolymer Polymers 0.000 claims description 13
- 229920002554 vinyl polymer Polymers 0.000 claims description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- 239000010703 silicon Substances 0.000 claims description 10
- 239000013638 trimer Substances 0.000 claims description 7
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
- 230000001678 irradiating effect Effects 0.000 claims description 4
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 10
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- 238000011109 contamination Methods 0.000 description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 6
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 6
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
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- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 4
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- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
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- 238000010438 heat treatment Methods 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
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- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- H01L21/67—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere
- H01L21/683—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L21/6835—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
- H01L21/6836—Wafer tapes, e.g. grinding or dicing support tapes
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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
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/8029—Masked aromatic polyisocyanates
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C—CHEMISTRY; METALLURGY
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
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Definitions
- the present invention relates to a multilayer pressure-sensitive adhesive sheet and a method for producing an electronic component using the multilayer pressure-sensitive adhesive sheet.
- a circuit pattern is formed on a semiconductor wafer such as silicon or gallium arsenide to form an electronic component assembly, and the electronic component assembly is composed of a base film layer and an adhesive layer. This is further fixed to the ring frame, and then cut into individual semiconductor chips (dicing), and the film is stretched (expanded) as necessary. The semiconductor chip is picked up, and the semiconductor chip is glued to the lead frame. The method of fixing to etc. is performed widely.
- a die attach film is laminated and integrated on a pressure sensitive adhesive sheet, thereby providing a multilayer pressure sensitive adhesive sheet (diameter) having both a function as a pressure sensitive adhesive sheet for dicing and a function as an adhesive for fixing a chip to a lead frame or the like.
- a method using a touch film integrated sheet) has been proposed (Patent Document 1 and Patent Document 2).
- the adhesive application step can be omitted, and that the thickness of the adhesive portion can be controlled and the protrusion can be suppressed as compared with the method using the adhesive.
- a general adhesive material such as an acrylic resin, an epoxy resin, or a polyamide resin is used for the die attach film of the multilayer adhesive sheet.
- an acrylate copolymer is used as a material constituting the die attach film, storage stability and film formability can be improved.
- the die attach film containing the acrylate copolymer has an excessively high adhesive strength with the adhesive layer of the adhesive sheet, and the die attach film is difficult to peel from the adhesive layer when picking up the semiconductor chip. In some cases, the chip pick-up property was inferior.
- the present invention has been made in view of the above circumstances, and even when an acrylic ester copolymer is used for the die attach film by making the pressure-sensitive adhesive constituting the pressure-sensitive adhesive layer of the multilayer pressure-sensitive adhesive sheet into a specific composition.
- an acrylic ester copolymer is used for the die attach film by making the pressure-sensitive adhesive constituting the pressure-sensitive adhesive layer of the multilayer pressure-sensitive adhesive sheet into a specific composition.
- the adhesive layer and the die attach film at the time of pick-up can be easily peeled off, and thus the pick-up operation of the semiconductor chip after dicing can be easily performed, and the present invention has been completed.
- stacked on the exposed surface of the adhesion layer is (meth) acrylic acid which comprises an adhesion layer It has an ester copolymer (A), an ultraviolet polymerizable compound (B), a polyfunctional isocyanate curing agent (C), a photopolymerization initiator (D), and a silicone polymer (E), and a (meth) acrylic acid ester
- the copolymer (A) is either a copolymer of a (meth) acrylic acid ester monomer or a copolymer of a (meth) acrylic acid ester monomer and a vinyl compound monomer Both of the (meth) acrylic acid ester monomer and the vinyl compound monomer have no hydroxyl group, and the ultraviolet polymerizable compound (B) is a
- the urethane acrylate oligomer (B1) has 10 or more vinyl groups, a weight average molecular weight Mw of 50000 or more, and a dispersity Mw / Mn which is a ratio of the weight average molecular weight Mw to the number average molecular weight Mn is 5 or more.
- the photopolymerization initiator (D) has a hydroxyl group
- the silicone polymer (E) has a hydroxyl group
- the (meth) acrylic acid ester copolymer (A) is 100.
- the urethane acrylate oligomer (B1) is obtained by reacting a trimer isocyanate of isophorone diisocyanate with a hydroxyl group-containing acrylate containing dipetaerythritol pentaacrylate as a main component, and the polyfunctional (meth) acrylate (B2) is dipentaerythritol.
- the multilayer adhesive sheet according to (1) which is hexaacrylate.
- (3). The multilayer pressure-sensitive adhesive sheet according to (1) or (2), wherein the composition constituting the die attach film has an acrylate copolymer.
- (4). (1) to (3) using the multilayer adhesive sheet according to any one of the above, an adhesive process in which the multilayer adhesive sheet is adhered and fixed to the silicon wafer and the ring frame, and the silicon wafer is diced with a dicing blade to obtain a semiconductor chip
- a method of manufacturing an electronic component comprising: a dicing step of: picking up a chip and a die attach film from an adhesive layer by irradiating at least ultraviolet rays or radiation.
- the multilayer pressure-sensitive adhesive sheet of the present invention even when an acrylic acid ester copolymer is used for the die attach film, peeling between the pressure sensitive adhesive sheet and the die attach film at the time of pickup is easy, and thus dicing is performed. The subsequent chip pick-up operation can be easily performed.
- the multilayer pressure-sensitive adhesive sheet of the present invention has less chip skipping due to dicing (chip retention) and less contamination of the die attach film due to the adhesive layer-derived component (contamination prevention). It can be used suitably for the manufacturing method of an electronic component.
- a monomer unit means a structural unit derived from a monomer. “Parts” and “%” are based on mass.
- (Meth) acrylate is a general term for acrylate and methacrylate.
- a compound containing (meth) such as (meth) acrylic acid is a general term for a compound having “meta” in the name and a compound not having “meta”.
- a multilayer adhesive sheet has a base film, the adhesive layer laminated
- a material in which only the base film and the pressure-sensitive adhesive layer are laminated and integrated is simply referred to as “pressure-sensitive adhesive sheet”, and a material in which a die attach film is further laminated and integrated in the pressure-sensitive adhesive sheet is referred to as “multi-layer pressure-sensitive adhesive sheet”. .
- the base film is not particularly limited, and a known resin material can be used. Specifically, polyvinyl chloride, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-acrylic acid-acrylic acid ester film, ethylene-ethyl acrylate copolymer, polyethylene, polypropylene, propylene copolymer, ethylene- Examples include acrylic acid copolymers and ionomer resins obtained by crosslinking ethylene- (meth) acrylic acid copolymers, ethylene- (meth) acrylic acid- (meth) acrylic acid ester copolymers, etc. with metal ions. .
- the base film may be a mixture, copolymer or laminate of these resins.
- a propylene copolymer is preferable as the base film.
- a propylene-based copolymer By employing a propylene-based copolymer, chips generated when the semiconductor wafer is cut can be suppressed.
- the propylene-based copolymer include a random copolymer of propylene and other components, a block copolymer of propylene and other components, and an alternating copolymer of propylene and other components.
- other components include ⁇ -olefins such as ethylene, 1-butene, 1-pentene, 1-hexene and 1-heptene, copolymers composed of at least two kinds of ⁇ -olefins, and styrene-diene copolymers. Can be mentioned. Of these, 1-butene is preferred.
- Examples of the method for polymerizing the propylene-based copolymer include a solvent polymerization method, a bulk polymerization method, a gas phase polymerization method, a sequential polymerization method, and the like.
- a homopolymer of ⁇ -olefin or a random copolymer of propylene with a small amount of ethylene and / or ⁇ -olefin is produced in the second and subsequent stages.
- a stepwise sequential polymerization process is preferred.
- the base film is preferably subjected to antistatic treatment.
- antistatic treatment By performing antistatic treatment, it is possible to prevent electrification when the die attach film is peeled off.
- As the antistatic treatment (1) a treatment of adding an antistatic agent to the composition constituting the base film, (2) a treatment of applying the antistatic agent to the surface of the base film on the die attach film lamination side, ( 3) There is a charging process by corona discharge.
- Antistatic agents include quaternary amine salt monomers.
- Examples of the quaternary amine salt monomer include dimethylaminoethyl (meth) acrylate quaternary chloride, diethylaminoethyl (meth) acrylate quaternary chloride, methylethylaminoethyl (meth) acrylate quaternary chloride, p-dimethyl.
- the pressure-sensitive adhesive layer is composed of a pressure-sensitive adhesive, and the pressure-sensitive adhesive comprises a (meth) acrylic acid ester copolymer (A), an ultraviolet polymerizable compound (B), a polyfunctional isocyanate curing agent (C), and a photopolymerization initiator (D). And a silicone polymer (E).
- A acrylic acid ester copolymer
- B ultraviolet polymerizable compound
- C polyfunctional isocyanate curing agent
- D photopolymerization initiator
- E silicone polymer
- the (meth) acrylic acid ester copolymer is a copolymer of only a monomer of (meth) acrylic acid ester, or a copolymer of a monomer of (meth) acrylic acid ester and a vinyl compound monomer. These monomers do not have a hydroxyl group.
- Examples of the (meth) acrylic acid ester monomer include butyl (meth) acrylate, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, pentyl (meth) acrylate, octyl (meth) acrylate, 2- Ethylhexyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, lauryl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, tridecyl (meth) acrylate, myristyl ( (Meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) acryl
- a functional group having one or more functional groups such as a carboxyl group, an epoxy group, an amide group, an amino group, a methylol group, a sulfonic acid group, a sulfamic acid group, or a (phosphite) ester group Contains monomers.
- vinyl compound monomer having a carboxyl group examples include (meth) acrylic acid, crotonic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid, acrylamide N-glycolic acid, and cinnamic acid.
- Examples of the vinyl compound monomer having an epoxy group include allyl glycidyl ether and (meth) acrylic acid glycidyl ether.
- Examples of vinyl compound monomers having an amide group include (meth) acrylamide.
- Examples of the vinyl compound monomer having an amino group include N, N-dimethylaminoethyl (meth) acrylate.
- Examples of the vinyl compound monomer having a methylol group include N-methylolacrylamide.
- Methods for producing the (meth) acrylic acid ester copolymer include emulsion polymerization and solution polymerization). Among these, emulsion polymerization is preferable because the pressure-sensitive adhesive sheet can be easily peeled off from the die attach film after irradiation and high pick-up property of the semiconductor chip can be maintained.
- the ultraviolet polymerizable compound (B) is a mixture of urethane acrylate oligomer (B1) and polyfunctional (meth) acrylate (B2).
- the blending ratio of the urethane acrylate oligomer (B1) and the polyfunctional (meth) acrylate (B2) is preferably such that B1: B2 is 50:50 or more and 95: 5 or less, and is 65:35 or more and 85:15 or less. More preferably.
- the urethane acrylate oligomer (B1) has 10 or more vinyl groups, a weight average molecular weight Mw of 50000 or more, and a dispersity Mw / Mn which is a ratio of the weight average molecular weight Mw to the number average molecular weight Mn is 5 or more. belongs to.
- the urethane acrylate oligomer (B1) was produced by reacting (1) a (meth) acrylate compound containing a hydroxyl group and a plurality of (meth) acrylate groups with a compound having a plurality of isocyanate groups (for example, a diisocyanate compound). (2) A compound having a plurality of isocyanate groups (for example, a diisocyanate compound) is added to and reacted with a polyol oligomer having a plurality of hydroxyl groups to obtain an oligomer having a plurality of isocyanate ends, Some have reacted with a (meth) acrylate compound containing a (meth) acrylate group.
- a compound having a plurality of isocyanate groups for example, a diisocyanate compound
- the number of vinyl groups of the urethane acrylate oligomer (B1) is 10 or more, peeling between the pressure-sensitive adhesive sheet and the die attach film becomes easy after irradiation. Therefore, the pick-up property of the semiconductor chip can be maintained well.
- the adhesive sheet and the die attach the adhesive strength between the films can be reduced, and the die attach film can be easily peeled off from the adhesive sheet after radiation irradiation.
- Examples of the (meth) acrylate compound containing a hydroxyl group and a plurality of (meth) acrylate groups that can form the urethane acrylate oligomer (B1) include hydroxypropylated trimethylolpropane triacrylate, pentaerythritol triacrylate, dipentaerythritol hydroxypenta.
- Examples of the compound having a plurality of isocyanate groups that can constitute the urethane acrylate oligomer (B1) include aromatic isocyanate, alicyclic isocyanate, and aliphatic isocyanate. Of these isocyanates, alicyclic isocyanates and aliphatic isocyanates having a plurality of isocyanate groups are preferred. As the form of the isocyanate component, there are a monomer, a dimer, and a trimer, and among these, a trimer is preferable.
- aromatic diisocyanates examples include tolylene diisocyanate, 4,4-diphenylmethane diisocyanate, and xylylene diisocyanate.
- alicyclic diisocyanate examples include isophorone diisocyanate and methylene bis (4-cyclohexyl isocyanate).
- aliphatic diisocyanate examples include hexamethylene diisocyanate and trimethylhexamethylene diisocyanate.
- Examples of the polyol component of a polyol oligomer having a plurality of hydroxyl groups that can constitute the urethane acrylate oligomer (B1) include poly (propylene oxide) diol, poly (propylene oxide) triol, copoly (ethylene oxide-propylene oxide) diol, poly There are (tetramethylene oxide) diol, ethoxylated bisphenol A, ethoxylated bisphenol S spiroglycol, caprolactone modified diol and carbonate diol.
- Multifunctional (meth) acrylate (B2) examples include trimethylolpropane triacrylate, hydroxypropylated trimethylolpropane triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, pentaerythritol ethoxytetraacrylate, diester Pentaerythritol hydroxypentaacrylate, dipentaerythritol hexaacrylate, bis (pentaerythritol) tetraacrylate, tetramethylolmethane-triacrylate, glycidol-diacrylate, and compounds in which some or all of these acrylate groups are methacrylate groups is there.
- the blending amount of the ultraviolet polymerizable compound (B) is preferably 5 parts by mass or more and 200 parts by mass or less with respect to 100 parts by mass of the (meth) acrylic acid ester copolymer (A). If the blending amount of the ultraviolet polymerizable compound (B) is too small, the die attach film is difficult to peel off from the pressure-sensitive adhesive sheet after irradiation, and problems relating to the pick-up property of the semiconductor chip are likely to occur. If the amount of the UV-polymerizable compound (B) is too large, pick-up failure is likely to occur due to the glue being picked up at the time of dicing, and a minute adhesive residue due to a reaction residue will be generated and the die attach film will be contaminated. After bonding the semiconductor chip to which the film is adhered on the lead frame, adhesion failure is likely to occur during heating.
- the polyfunctional isocyanate curing agent (C) has two or more isocyanate groups, and examples thereof include aromatic polyisocyanates, aliphatic polyisocyanates, and alicyclic polyisocyanates.
- Aromatic polyisocyanates include, for example, 1,3-phenylene diisocyanate, 4,4′-diphenyl diisocyanate, 1,4-phenylene diisocyanate, 4,4′-diphenylmethane diisocyanate, 2,4-tolylene diisocyanate, 2,6- Tolylene diisocyanate, 4,4'-toluidine diisocyanate, 2,4,6-triisocyanate toluene, 1,3,5-triisocyanate benzene, dianisidine diisocyanate, 4,4'-diphenyl ether diisocyanate, 4,4 ', 4 ”-Triphenylmethane triisocyanate, ⁇ , ⁇ ′-diisocyanate-1,3-dimethylbenzene, ⁇ , ⁇ ′-diisocyanate-1,4-dimethylbenzene, ⁇ , ⁇ ′-diisocyanate-1,4-diethylbenzene
- aliphatic polyisocyanate examples include trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, 1,2-propylene diisocyanate, 2,3-butylene diisocyanate, 1,3-butylene diisocyanate, dodecamethylene diisocyanate and 2 4,4-trimethylhexamethylene diisocyanate.
- Examples of the alicyclic polyisocyanate include 3-isocyanate methyl-3,5,5-trimethylcyclohexyl isocyanate, 1,3-cyclopentane diisocyanate, 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, methyl-2, There are 4-cyclohexane diisocyanate, methyl-2,6-cyclohexane diisocyanate, 4,4'-methylene bis (cyclohexyl isocyanate), 1,4-bis (isocyanate methyl) cyclohexane and 1,4-bis (isocyanate methyl) cyclohexane.
- the blending ratio of the polyfunctional isocyanate curing agent (C) is preferably 0.5 parts by mass or more and 20 parts by mass or less with respect to 100 parts by mass of the (meth) acrylic acid ester copolymer (A), and the lower limit is 1.0. More than mass part and 10 mass parts or less are more preferable as an upper limit. If the polyfunctional isocyanate curing agent (C) is 0.5 parts by mass or more, since the adhesive strength is not too high, the occurrence of defective pickup can be suppressed. If the polyfunctional isocyanate curing agent (C) is 20 parts by mass or less, the adhesive strength is not too low, so that the retention of the semiconductor chip is maintained during dicing.
- the photopolymerization initiator (D) has at least one hydroxyl group.
- the photopolymerization initiator having one hydroxyl group include 2-hydroxy-methyl-1-phenyl-propan-1-one (manufactured by Ciba Japan, product name Darocur 1173), 1-hydroxy-cyclohexyl-phenyl-ketone ( Ciba Japan Co., Ltd., product name Irgacure 184), and the like.
- Examples of the photopolymerization initiator having two or more hydroxyl groups include 1- [4- (hydroxyethoxy) -phenyl] -2-hydroxy-2methyl- 1-propan-1-one (manufactured by Ciba Japan, product name Irgacure 2959), 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] -phenyl ⁇ -2 -Methyl-propan-1-one (manufactured by Ciba Japan, product name Irgacure 127).
- the number of hydroxyl groups in the photopolymerization initiator (B) having a hydroxyl group is preferably 2 or more.
- the photopolymerization initiator cleaved after irradiation is taken into the reaction system of the acryloyl group of the (meth) acrylate monomer (A), so that migration to the die attach film can be suppressed.
- the upper limit of the number of hydroxyl groups is not particularly limited.
- the blending amount of the photopolymerization initiator (D) is preferably 0.1 parts by mass or more and 20 parts by mass or less with respect to 100 parts by mass of the (meth) acrylic acid ester polymer (A). If the amount is too small, the die attach film cannot be easily peeled off from the pressure-sensitive adhesive sheet after irradiation, and the pick-up property of the semiconductor chip tends to be lowered. If this ratio is too large, contamination will not be suppressed by bleeding out to the surface of the adhesive layer, and after mounting a semiconductor chip with a die attach film on the lead frame, adhesion failure tends to occur during heating. .
- silicone polymer (E) for blending with the pressure-sensitive adhesive has a monomer unit derived from a monomer having a vinyl group at the end of the polydimethylsiloxane bond (hereinafter referred to as “silicone macromonomer”). It is. Specifically, there are homopolymers of silicone macromonomers and vinyl polymers obtained by polymerizing silicone macromonomers and other vinyl compounds.
- the silicone-based macromonomer is preferably a compound in which the terminal of the polydimethylsiloxane bond is a vinyl group such as a (meth) acryloyl group or a styryl group.
- a (meth) acrylic monomer can be used as a vinyl compound other than the silicone-based macromonomer constituting the silicone polymer (E).
- silicone polymer when such a silicone polymer is used, when the adhesive sheet and the die attach film are laminated, the silicone polymer can be prevented from migrating to the die attach film, and when the semiconductor chip is picked up, the particles and It is possible to prevent the occurrence of a minute adhesive residue called.
- the (meth) acrylic monomer include alkyl (meth) acrylate, hydroxyalkyl (meth) acrylate, modified hydroxy (meth) acrylate, and (meth) acrylic acid.
- alkyl (meth) acrylate examples include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, and t-butyl (meth) acrylate.
- hydroxyalkyl (meth) acrylate examples include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, and hydroxybutyl (meth) acrylate.
- modified hydroxy (meth) acrylate examples include ethylene oxide-modified hydroxy (meth) acrylate and lactone-modified hydroxy (meth) acrylate.
- the blending amount of the silicone polymer (E) is preferably 0.1 parts by mass or more and 20 parts by mass or less with respect to 100 parts by mass of the (meth) acrylic acid ester polymer (A). If the amount is too small, the die attach film cannot be easily peeled off from the pressure-sensitive adhesive sheet after irradiation, and the pick-up property of the semiconductor chip tends to be lowered. On the other hand, if the amount is too large, the initial decrease in adhesive strength cannot be suppressed, and the retention of the semiconductor chip tends to be impaired during dicing.
- the ratio of the silicone macromonomer unit in the silicone polymer (E) is preferably 15 parts by mass or more and 50 parts by mass or less in 100 parts by mass of the silicone polymer.
- this ratio decreases, the die attach film can be easily peeled off from the pressure-sensitive adhesive sheet after irradiation, and the pick-up property of the semiconductor chip tends to decrease.
- this ratio increases, contamination due to bleed-out on the pressure-sensitive adhesive surface is not suppressed, and after bonding the semiconductor chip to which the die attach film is adhered on the lead frame, adhesion failure tends to occur during heating.
- Additives such as softeners, anti-aging agents, fillers, ultraviolet absorbers, and light stabilizers can be added to the pressure-sensitive adhesive within a range that does not affect other materials.
- the thickness of the adhesive layer is preferably 3 ⁇ m or more and 100 ⁇ m or less, and particularly preferably 5 ⁇ m or more and 20 ⁇ m or less.
- the die attach film used for the multilayer pressure-sensitive adhesive sheet is obtained by forming an adhesive into a film.
- Specific compositions constituting the die attach film include acrylic ester copolymer, polyamide, polyethylene, polysulfone, epoxy resin, polyimide, polyamic acid, silicone resin, phenol resin, rubber, fluororubber and fluororesin. Alternatively, there are mixtures, copolymers and laminates thereof.
- the composition constituting the die attach film preferably contains an acrylate copolymer from the viewpoint of reliability of adhesion to the chip.
- a photopolymerization initiator, an antistatic agent, a crosslinking agent, a crosslinking accelerator, a filler and the like may be added to the composition.
- the multilayer pressure-sensitive adhesive sheet can be produced by applying a pressure-sensitive adhesive on a base film to create a pressure-sensitive adhesive sheet, and then attaching a die attach film to the pressure-sensitive adhesive-coated surface of the pressure-sensitive adhesive sheet.
- the adhesive is coated on a separator film made of polyethylene terephthalate, etc., and optionally dried, then laminated on the base film to create an adhesive sheet, and then die-attached to the exposed surface from which the separator film has been removed. It can also be manufactured by attaching a film.
- the adhesive strength between the die attach film and the adhesive sheet is too large, pick-up failure tends to occur, and if it is too small, the chip retention tends to decrease, so 0.05 to 1.5 N / 20 mm.
- the pressure-sensitive adhesive constituting the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet is set to the above specific composition, it is possible to maintain a suitable pressure-sensitive adhesive strength even when an acrylate copolymer is used for the die attach film.
- the method of manufacturing an electronic component using the multilayer adhesive sheet described above includes the following steps. (1) Affixing process for adhering and fixing a multilayer adhesive sheet to a silicon wafer and a ring frame; (2) A dicing process in which a silicon wafer is diced together with a die attach film with a dicing blade to form a semiconductor chip, (3) A pick-up step of picking up the semiconductor chip to which the die attach film is attached from at least the adhesive layer by irradiating at least ultraviolet rays or radiation.
- the multi-layer adhesive sheet is excellent in chip retention, pick-up property, and anti-contamination property of semiconductor chips, it is possible to reduce the occurrence of chip jump in the dicing step (2).
- the semiconductor chip with the die attach film attached in step (3) can be easily peeled off and picked up from the adhesive sheet.
- the die attach film is not contaminated after picking up, it has high adhesion to the lead frame and the like. Have power.
- the base film used was a propylene copolymer (product number: X500F) manufactured by Sun Allomer in all of the Examples and Comparative Examples.
- This film has an MFR (melt flow rate) value of 7.5 g / 10 min, a density of 0.89 g / cm 3 , and a thickness of 80 ⁇ m.
- the adhesive layer comprises (meth) acrylic acid ester copolymer (A), ultraviolet polymerizable compound (B), polyfunctional isocyanate curing agent (C), photopolymerization initiator (D) and silicone polymer (described below). It was formed using an adhesive containing E).
- A-1 Acrylic rubber AR53L manufactured by Nippon Zeon Co., Ltd .; a copolymer of 40% ethyl acrylate, 23% butyl acrylate and 37% methoxyethyl acrylate, and is obtained by emulsion polymerization. None of the compounds have hydroxyl groups.
- A-2 In-house polymerized product; a copolymer of 40% ethyl acrylate, 22% butyl acrylate, 37% methoxyethyl acrylate, and 1% acrylic acid, and is obtained by emulsion polymerization. None of the compounds have hydroxyl groups.
- A-3 SK Dyne 1435 manufactured by Soken Chemical Co., Ltd. A copolymer of 67% butyl acrylate, 28% methyl acrylate and 5% 2-hydroxyethyl acrylate, and is obtained by solution polymerization. 2-hydroxyethyl acrylate has hydroxyl groups.
- the urethane acrylate oligomer (B1) is a product obtained by reacting a trimer isocyanate of isophorone diisocyanate with a hydroxyl group-containing acrylate containing dipetaerythritol pentaacrylate as a main component.
- the polyfunctional (meth) acrylate (B2) is mainly composed of dipentaerythritol hexaacrylate. The mixing ratio of both components is 75% for the urethane acrylate oligomer (B1) and 25% for the polyfunctional (meth) acrylate (B2).
- the urethane acrylate oligomer (B1) has a weight average molecular weight of 100,000, a dispersity of 10.7, and 15 vinyl groups.
- B-2 UN-3320HS manufactured by Negami Kogyo Co., Ltd .; B-2 is composed of urethane acrylate oligomer (B1) and polyfunctional (meth) acrylate (B2).
- the urethane acrylate oligomer (B1) is a product obtained by reacting a trimer isocyanate of isophorone diisocyanate with a hydroxyl group-containing acrylate containing dipetaerythritol pentaacrylate as a main component.
- the polyfunctional (meth) acrylate (B2) is mainly composed of dipentaerythritol hexaacrylate.
- the blending ratio of both components is 45% for the urethane acrylate oligomer (B1) and 55% for the polyfunctional (meth) acrylate (B2).
- the urethane acrylate oligomer (B1) has a weight average molecular weight of 11000, a dispersity of 1.2, and 15 vinyl groups.
- B-3 In-house polymerized product A; B-3 comprises urethane acrylate oligomer (B1) and polyfunctional (meth) acrylate (B2).
- the urethane acrylate oligomer (B1) is obtained by reacting a trimethyl isocyanate of hexamethylene diisocyanate with a hydroxyl group-containing acrylate containing dipetaerythritol pentaacrylate as a main component.
- the polyfunctional (meth) acrylate (B2) is mainly composed of dipentaerythritol hexaacrylate. The blending ratio of both components is 45% for the urethane acrylate oligomer (B1) and 55% for the polyfunctional (meth) acrylate (B2).
- the urethane acrylate oligomer (B1) has a weight average molecular weight of 70000, a dispersity of 1.2, and 15 vinyl groups.
- B-4 In-house polymerized product B; B-4 is composed of urethane acrylate oligomer (B1) and polyfunctional (meth) acrylate (B2).
- the urethane acrylate oligomer (B1) is obtained by reacting a trimethyl isocyanate of hexamethylene diisocyanate with a hydroxyl group-containing acrylate containing dipetaerythritol pentaacrylate as a main component.
- the polyfunctional (meth) acrylate (B2) is mainly composed of dipentaerythritol hexaacrylate.
- the blending ratio of both components is 45% for the urethane acrylate oligomer (B1) and 55% for the polyfunctional (meth) acrylate (B2).
- the urethane acrylate oligomer (B1) has a weight average molecular weight of 30000, a dispersity of 7.5, and 15 vinyl groups.
- B-5 In-house polymerized product C; B-5 is composed of urethane acrylate oligomer (B1) and polyfunctional (meth) acrylate (B2).
- the urethane acrylate oligomer (B1) is obtained by reacting a hydroxyl group-containing acrylate containing petaerythritol triacrylate as a main component with a hexamethylene diisocyanate trimer isocyanate.
- the polyfunctional (meth) acrylate (B2) is mainly composed of pentaerythritol tetraacrylate. The blending ratio of both components is 45% for the urethane acrylate oligomer (B1) and 55% for the polyfunctional (meth) acrylate (B2).
- the urethane acrylate oligomer (B1) has a weight average molecular weight of 70,000, a degree of dispersion of 8.2, and six vinyl groups.
- C-1 Coronate L-45E manufactured by Nippon Polyurethane; Trimethylolpropane adduct of 2,4-tolylene diisocyanate.
- D-1 Ciba Japan, product name Irgacure 127; 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] -phenyl ⁇ -2-methyl-propane- 1-on. There is a hydroxyl group.
- D-2 Ciba Japan, product name Irgacure 184; 1-hydroxy-cyclohexyl-phenyl-ketone. Has hydroxyl group.
- D-3 Ciba Japan, product name Irgacure 651; benzyl dimethyl ketal. No hydroxyl group.
- E-2 Silicone oil, commercially available product. No hydroxyl group.
- the molecular weight of the urethane acrylate oligomer (B1) contained in the ultraviolet polymerizable compound (B) was measured under the GPC measurement conditions described below.
- Calibration curve prepared using standard polystyrene (PS) (manufactured by Varian), and molecular weight was expressed in terms of PS.
- Die attach film Any of the following was used for the die attach film. 1: Mainly composed of acrylic acid ester copolymer, thickness of 30 ⁇ m. 2: Mainly composed of an epoxy-based adhesive and a thickness of 30 ⁇ m.
- the pressure-sensitive adhesive was coated on a polyethylene terephthalate separator film so that the thickness of the pressure-sensitive adhesive layer after drying was 10 ⁇ m.
- This pressure-sensitive adhesive layer was laminated on a base film and aged at 40 ° C. for 7 days to obtain a pressure-sensitive adhesive sheet with a separator film.
- the separator film was removed, and a die attach film cut into a 8.2 inch diameter circle was laminated on the exposed adhesive layer to obtain a multilayer adhesive sheet.
- Affixing process A silicon wafer having a diameter of 8 inches and a thickness of 0.1 mm on which a dummy circuit pattern was formed and a ring frame were adhered and fixed to the adhesive layer of the multilayer pressure-sensitive adhesive sheet.
- Dicing step Using a dicing blade, the silicon wafer was cut into a semiconductor chip having a size of 9 mm ⁇ 9 mm together with the die attach film of the multilayer adhesive sheet. The dicing process was performed with the following apparatus and conditions.
- Dicing machine DAD341 manufactured by DISCO Dicing blade: NBC-ZH205O-27HEEE made by DISCO Dicing blade shape: outer diameter 55.56 mm, blade width 35 ⁇ m, inner diameter 19.05 mm Dicing blade rotation speed: 40,000 rpm Dicing blade feed rate: 50 mm / sec.
- Cutting depth into adhesive sheet 15 ⁇ m
- Cutting water temperature 25 ° C
- Cutting water amount 1.0 L / min (3)
- Pickup process After reducing the adhesive strength of the adhesive layer by irradiating ultraviolet rays, the semiconductor chip with the die attach film attached was peeled off from the adhesive layer and picked up. The pickup process was performed with the following equipment and conditions.
- Pickup device CAP-300II manufactured by Canon Machinery Needle pin shape: 250 ⁇ mR Needle pin push-up height: 0.5mm Expanding amount: 8mm
- Chip retention was evaluated by the residual ratio of the semiconductor chips held on the adhesive sheet after the dicing process. ⁇ (Excellent): Chip skipping is less than 5%. ⁇ (Good): Chip skipping is 5% or more and less than 10%. X (impossible): Chip jump is 10% or more.
- the anti-contamination property is that the adhesive layer of the adhesive sheet and the die attach film are bonded together and stored for 1 week, then irradiated with 500 mJ / cm 2 of ultraviolet light with a high-pressure mercury lamp, and after 1 week or 4 weeks after irradiation
- the die attach film was peeled from the sheet, and the die attach film was subjected to GC-MS analysis, and a peak derived from the adhesive component was confirmed and evaluated.
- ⁇ No peak derived from the pressure-sensitive adhesive component was observed from the die attach film which was peeled off from the pressure-sensitive adhesive sheet after being stored for 1 week after being irradiated with ultraviolet rays, but peeled off from the pressure-sensitive adhesive sheet after being stored for 4 weeks after being irradiated with ultraviolet light. From the die attach film, a peak derived from the adhesive component was observed.
- X impossible: A peak derived from the pressure-sensitive adhesive component was observed from any die attach film that was peeled off from the pressure-sensitive adhesive sheet after being stored for 1 week and after being stored for 4 weeks.
- Table 1 shows the composition of the adhesive constituting the adhesive layer, the type of die attach film used, and the evaluation results.
- the numerical value representing the composition of the pressure-sensitive adhesive constituting the pressure-sensitive adhesive layer is part by mass.
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Abstract
Description
(1).基材フィルムと、基材フィルムの一方の面に積層された粘着層と、粘着層の露出面に積層されたダイアタッチフィルムとを有し、粘着層を構成する粘着剤が(メタ)アクリル酸エステル共重合体(A)と紫外線重合性化合物(B)と多官能イソシアネート硬化剤(C)と光重合開始剤(D)とシリコーン重合体(E)とを有し、(メタ)アクリル酸エステル共重合体(A)が、(メタ)アクリル酸エステル単量体の共重合体、又は、(メタ)アクリル酸エステル単量体とビニル化合物単量体との共重合体のいずれか一方であり、(メタ)アクリル酸エステル単量体とビニル化合物単量体のいずれもが水酸基を有さないものであり、紫外線重合性化合物(B)がウレタンアクリレートオリゴマ(B1)と多官能(メタ)アクリレート(B2)からなり、ウレタンアクリレートオリゴマ(B1)はビニル基を10個以上有し、重量平均分子量Mwが50000以上、かつ、前記重量平均分子量Mwと数平均分子量Mnの比である分散度Mw/Mnが5以上であり、光重合開始剤(D)が水酸基を有し、シリコーン重合体(E)が水酸基を有し、粘着層を構成する粘着剤において(メタ)アクリル酸エステル共重合体(A)が100質量部、紫外線重合性化合物(B)が5~200質量部、多官能イソシアネート硬化剤(C)が0.5~20質量部、光重合開始剤(D)が0.1~20質量部並びにシリコーン重合体(E)が0.1~20質量部である多層粘着シート。
(2).ウレタンアクリレートオリゴマ(B1)がイソホロンジイソシアネートの三量体のイソシアネートにジペタエリスリトールペンタアクリレートを主成分とする水酸基含有アクリレートを反応させたものであり、多官能(メタ)アクリレート(B2)がジペンタエリスリトールヘキサアクリレートである(1)記載の多層粘着シート。
(3).ダイアタッチフィルムを構成する組成物がアクリル酸エステル共重合体を有する(1)又は(2)記載の多層粘着シート。
(4).(1)乃至(3)のいずれか一項記載の多層粘着シートを用いて、多層粘着シートをシリコンウエハとリングフレームに貼り付けて固定する貼付工程、ダイシングブレードでシリコンウエハをダイシングして半導体チップにするダイシング工程、少なくとも紫外線又は放射線を照射し、チップとダイアタッチフィルムを粘着層からピックアップするピックアップ工程、を含む、電子部品の製造方法。
単量体単位とは単量体に由来する構造単位を意味する。「部」及び「%」は質量基準である。(メタ)アクリレートとはアクリレート及びメタアクリレートの総称である。(メタ)アクリル酸等の(メタ)を含む化合物等も同様に、名称中に「メタ」を有する化合物と「メタ」を有さない化合物の総称である。
多層粘着シートは、基材フィルムと、基材フィルムの一方の面に積層された粘着層と、粘着層の露出面に積層されたダイアタッチフィルムとを有する。すなわち、多層粘着シートは、基材フィルム、粘着層、ダイアタッチフィルムがこの順に積層された多層構造体である。本明細書中、基材フィルムと粘着層のみを積層一体化させたものを単に「粘着シート」と称し、粘着シートにダイアタッチフィルムをさらに積層一体化させたものを「多層粘着シート」と称する。
基材フィルムは、特に限定されるものではなく公知の樹脂材料を用いることができる。具体的には、ポリ塩化ビニル、ポリエチレンテレフタレート、エチレン-酢酸ビニル共重合体、エチレン-アクリル酸-アクリル酸エステルフィルム、エチレン-エチルアクリレート共重合体、ポリエチレン、ポリプロピレン、プロピレン系共重合体、エチレン-アクリル酸共重合体、及び、エチレン-(メタ)アクリル酸共重合体やエチレン-(メタ)アクリル酸-(メタ)アクリル酸エステル共重合体等を金属イオンで架橋したアイオノマ樹脂を挙げることができる。基材フィルムは、これら樹脂の混合物、共重合体又はこれらの積層物であっても良い。
粘着層は粘着剤から構成され、粘着剤は、(メタ)アクリル酸エステル共重合体(A)と紫外線重合性化合物(B)と多官能イソシアネート硬化剤(C)と光重合開始剤(D)とシリコーン重合体(E)とを有する。
(メタ)アクリル酸エステル共重合体は、(メタ)アクリル酸エステルの単量体のみの共重合体、又は、(メタ)アクリル酸エステルの単量体とビニル化合物単量体との共重合体であり、これらの単量体が水酸基を持たないものである。
紫外線重合性化合物(B)は、ウレタンアクリレートオリゴマ(B1)と多官能(メタ)アクリレート(B2)との混合物である。ウレタンアクリレートオリゴマ(B1)と多官能(メタ)アクリレート(B2)との配合比は、B1:B2が50:50以上95:5以下であることが好ましく、65:35以上85:15以下であることがさらに好ましい。
ウレタンアクリレートオリゴマ(B1)は、ビニル基を10個以上有し、重量平均分子量Mwが50000以上であり、且つ前記重量平均分子量Mwと数平均分子量Mnの比である分散度Mw/Mnが5以上のものである。
多官能(メタ)アクリレート(B2)としては、例えばトリメチロールプロパントリアクリレート、ヒドロキシプロピル化トリメチロールプロパントリアクリレート、ペンタエリスリトールトリアクリレート、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トリアクリレート、ペンタエリスリトールエトキシテトラアクリレート、ジペンタエリスリトールヒドロキシペンタアクリレート、ジペンタエリスリトールヘキサアクリレート、ビス(ペンタエリスリトール)テトラアクリレート、テトラメチロールメタン-トリアクリレート、グリシドール-ジアクリレートや、これらのアクリレート基の一部又は全部をメタアクリレート基とした化合物がある。
多官能イソシアネート硬化剤(C)は、イソシアネート基を2個以上有するものであり、例えば芳香族ポリイソシアネート、脂肪族ポリイソシアネート、脂環族ポリイソシアネートがある。
光重合開始剤(D)は、少なくとも1個の水酸基を有するものである。1個の水酸基を有する光重合開始剤としては、2-ヒドロキシ-メチル-1-フェニル-プロパン-1-オン(チバ・ジャパン社製、製品名Darocur1173)、1-ヒドロキシ-シクロヘキシル-フェニル-ケトン(チバ・ジャパン社製、製品名Irgacure184)、等が挙げられ、2個以上の水酸基を有する光重合開始剤としては、1-[4-(ヒドロキシエトキシ)-フェニル]-2-ヒドロキシ-2メチル-1-プロパン-1-オン(チバ・ジャパン社製、製品名Irgacure2959)、2-ヒドロキシ-1-{4-[4-(2-ヒドロキシ-2-メチル-プロピオニル)-ベンジル]-フェニル}-2-メチル-プロパン-1-オン(チバ・ジャパン社製、製品名Irgacure127)等が挙げられる。水酸基を有する光重合開始剤(B)の水酸基の数は、2個以上が好ましい。2個以上有することで、放射線照射後に開裂した光重合開始剤が(メタ)アクリル酸エステル単量体(A)のアクリロイル基の反応系に取り込まれるため、ダイアタッチフィルムへのマイグレーションを抑制できる。なお、水酸基の数の上限については特に限定するものではない。
粘着剤に配合するのに好ましいシリコーン重合体(E)は、ポリジメチルシロキサン結合の末端にビニル基を有する単量体(以下、「シリコーン系マクロモノマ」という)に由来する単量体単位を有するものである。具体的には、シリコーン系マクロモノマのホモポリマー、シリコーン系マクロモノマと他のビニル化合物とを重合したビニル重合体がある。シリコーン系マクロモノマは、ポリジメチルシロキサン結合の末端が(メタ)アクリロイル基又はスチリル基等のビニル基である化合物が好ましい。
多層粘着シートに用いられるダイアタッチフィルムは、接着剤をフィルム状に成形したものである。ダイアタッチフィルムを構成する具体的な組成物としては、アクリル酸エステル共重合体、ポリアミド、ポリエチレン、ポリスルホン、エポキシ樹脂、ポリイミド、ポリアミド酸、シリコーン樹脂、フェノール樹脂、ゴム、フッ素ゴム及びフッ素樹脂の単体又はこれらの混合物、共重合体及び積層体がある。ダイアタッチフィルムを構成する組成物は、チップとの接着信頼性の面からアクリル酸エステル共重合体を含むことが好ましい。この組成物には、光重合開始剤、帯電防止剤、架橋剤、架橋促進剤、フィラーなどを添加してもよい。
多層粘着シートは、基材フィルム上に粘着剤を塗布して粘着シートを作成した後、粘着シートの粘着剤塗布面にダイアタッチフィルムを貼り付けることによって製造できる。また、粘着剤を、ポリエチレンテレフタレート等からなるセパレータフィルム上に塗工し、任意に乾燥させた後に、基材フィルムに積層して粘着シートを作成し、次いでセパレータフィルムを取り外した露出面にダイアタッチフィルムを貼り付けることによっても製造できる。
上述の多層粘着シートを用いて電子部品を製造する方法は、次の工程を含む。
(1)多層粘着シートをシリコンウエハとリングフレームに貼り付けて固定する貼付工程、
(2)ダイシングブレードでシリコンウエハをダイアタッチフィルムごとダイシングして半導体チップにするダイシング工程、
(3)少なくとも紫外線又は放射線を照射し、ダイアタッチフィルムが付着した半導体チップを粘着層からピックアップするピックアップ工程。
基材フィルムは、実施例及び比較例の全てにおいて、サンアロマー社製プロピレン系共重合体(品番:X500F)を用いた。このフィルムのMFR(メルトフローレート)値は7.5g/10分、密度は0.89g/cm3、厚さは80μmである。
粘着層は、以下に記載する(メタ)アクリル酸エステル共重合体(A)、紫外線重合性化合物(B)、多官能イソシアネート硬化剤(C)、光重合開始剤(D)及びシリコーン重合体(E)を含有する粘着剤を用いて形成した。
〔(メタ)アクリル酸エステル共重合体(A)〕
A-1:日本ゼオン社製アクリルゴムAR53L;エチルアクリレート40%、ブチルアクリレート23%、メトキシエチルアクリレート37%の共重合体であり、乳化重合により得られる。いずれの化合物にも水酸基なし。
A-2:自社重合品;エチルアクリレート40%、ブチルアクリレート22%、メトキシエチルアクリレート37%、アクリル酸1%の共重合体であり、乳化重合により得られる。いずれの化合物にも水酸基なし。
A-3:綜研化学社製SKダイン1435;ブチルアクリレート67%、メチルアクリレート28%、2-ヒドロキシエチルアクリレート5%の共重合体であり、溶液重合により得られる。2-ヒドロキシエチルアクリレートに水酸基あり。
〔紫外線重合性化合物(B)〕
B-1:根上工業社製UN-905;B-1は、ウレタンアクリレートオリゴマ(B1)と多官能(メタ)アクリレート(B2)からなる。ウレタンアクリレートオリゴマ(B1)は、イソホロンジイソシアネートの三量体のイソシアネートに、ジペタエリスリトールペンタアクリレートを主成分とする水酸基含有アクリレートを反応させたものである。多官能(メタ)アクリレート(B2)は、ジペンタエリスリトールヘキサアクリレートを主成分とするものである。両成分の配合比は、ウレタンアクリレートオリゴマ(B1)が75%、多官能(メタ)アクリレート(B2)が25%である。ウレタンアクリレートオリゴマ(B1)は、重量平均分子量100000、分散度10.7でビニル基の数が15個である。
B-2:根上工業社製UN-3320HS;B-2は、ウレタンアクリレートオリゴマ(B1)と多官能(メタ)アクリレート(B2)からなる。ウレタンアクリレートオリゴマ(B1)は、イソホロンジイソシアネートの三量体のイソシアネートに、ジペタエリスリトールペンタアクリレートを主成分とする水酸基含有アクリレートを反応させたものである。多官能(メタ)アクリレート(B2)は、ジペンタエリスリトールヘキサアクリレートを主成分とするものである。両成分の配合比は、ウレタンアクリレートオリゴマ(B1)が45%、多官能(メタ)アクリレート(B2)が55%である。ウレタンアクリレートオリゴマ(B1)は、重量平均分子量11000、分散度1.2でビニル基の数が15個である。
B-3:自社重合品A;B-3は、ウレタンアクリレートオリゴマ(B1)と多官能(メタ)アクリレート(B2)からなる。ウレタンアクリレートオリゴマ(B1)は、ヘキサメチレンジイソシアネートの三量体のイソシアネートに、ジペタエリスリトールペンタアクリレートを主成分とする水酸基含有アクリレートを反応させたものである。多官能(メタ)アクリレート(B2)は、ジペンタエリスリトールヘキサアクリレートを主成分とするものである。両成分の配合比は、ウレタンアクリレートオリゴマ(B1)が45%、多官能(メタ)アクリレート(B2)が55%である。ウレタンアクリレートオリゴマ(B1)は、重量平均分子量70000、分散度1.2でビニル基の数が15個である。
B-4:自社重合品B;B-4は、ウレタンアクリレートオリゴマ(B1)と多官能(メタ)アクリレート(B2)からなる。ウレタンアクリレートオリゴマ(B1)は、ヘキサメチレンジイソシアネートの三量体のイソシアネートに、ジペタエリスリトールペンタアクリレートを主成分とする水酸基含有アクリレートを反応させたものである。多官能(メタ)アクリレート(B2)は、ジペンタエリスリトールヘキサアクリレートを主成分とするものである。両成分の配合比は、ウレタンアクリレートオリゴマ(B1)が45%、多官能(メタ)アクリレート(B2)が55%である。ウレタンアクリレートオリゴマ(B1)は、重量平均分子量30000、分散度7.5でビニル基の数が15個である。
B-5:自社重合品C;B-5は、ウレタンアクリレートオリゴマ(B1)と多官能(メタ)アクリレート(B2)からなる。ウレタンアクリレートオリゴマ(B1)は、ヘキサメチレンジイソシアネートの三量体のイソシアネートに、ペタエリスリトールトリアクリレートを主成分とする水酸基含有アクリレートを反応させたものである。多官能(メタ)アクリレート(B2)は、ペンタエリスリトールテトラアクリレートを主成分とするものである。両成分の配合比は、ウレタンアクリレートオリゴマ(B1)が45%、多官能(メタ)アクリレート(B2)が55%である。ウレタンアクリレートオリゴマ(B1)は、重量平均分子量70000、分散度8.2でビニル基の数が6個である。
〔多官能イソシアネート硬化剤(C)〕
C-1:日本ポリウレタン社製コロネートL-45E;2,4-トリレンジイソシアネートのトリメチロールプロパンアダクト体。
〔光重合開始剤(D)〕
D-1:チバ・ジャパン社製、製品名Irgacure127;2-ヒドロキシ-1-{4-[4-(2-ヒドロキシ-2-メチル-プロピオニル)-ベンジル]-フェニル}-2-メチル-プロパン-1-オン。水酸基あり。
D-2:チバ・ジャパン社製、製品名Irgacure184;1-ヒドロキシ-シクロヘキシル-フェニル-ケトン。水酸基あり。
D-3:チバ・ジャパン社製、製品名Irgacure651;ベンジルジメチルケタール。水酸基なし。
〔シリコーン重合体(E)〕
E-1:綜研化学社製UTMM-LS2;シリコーン分子鎖の末端に(メタ)アクリロイル基を有するシリコーン系オリゴマ系単位を含有し、メチルメタアクリレート等からなるアクリルビニル単位を重合したシリコーン系グラフト共重合体。水酸基あり。
E-2:シリコーン油、市販品。水酸基なし。
装置名:HLC-81・BR>Q0GPC(東ソー社製)
カラム:TSK Guard HZ-L1本とHZM-N3本を直列
温度:40℃
検出:示差屈折率
溶媒:テトラヒドロフラン
濃度:0.2質量/体積%
検量線:標準ポリスチレン(PS)(Varian社製)を用いて作成し、分子量はPS換算値で表した。
ダイアタッチフィルムは、以下のいずれかを用いた。
1:アクリル酸エステル共重合体を主体とし、厚さ30μm。
2:エポキシ系接着剤を主体とし、厚さ30μm。
粘着剤を、ポリエチレンテレフタレート製のセパレータフィルム上に、乾燥後の粘着層の厚みが10μmとなるように塗工した。この粘着層を基材フィルムに積層し、40℃で7日間熟成させ、セパレータフィルム付き粘着シートを得た。次いでセパレータフィルムを取り外し、露出した粘着層上に直径8.2インチの円形に切断したダイアタッチフィルムをラミネートして、多層粘着シートを得た。
得られた多層粘着シートを用いて、以下の工程(1)~(3)により、シリコンウエハを固定し、ダイシングし、半導体チップをピックアップして、チップ保持性、ピックアップ性及び汚染防止性について評価を行った。
(2)ダイシング工程:ダイシングブレードを用いて、シリコンウエハを多層粘着シートのダイアタッチフィルムごと9mm×9mmのサイズの半導体チップに切断した。ダイシング工程は以下の装置及び条件で行った。
ダイシング装置:DISCO社製DAD341
ダイシングブレード:DISCO社製NBC-ZH205O-27HEEE
ダイシングブレード形状:外径55.56mm、刃幅35μm、内径19.05mm
ダイシングブレード回転数:40,000rpm
ダイシングブレード送り速度:50mm/秒
粘着シートへの切り込み量:15μm
切削水温度:25℃
切削水量 :1.0L/分
(3)ピックアップ工程:紫外線を照射して粘着層の粘着力を低下させた後に、ダイアタッチフィルムが付着した半導体チップを接着層から剥離させてピックアップした。ピックアップ工程は以下の装置及び条件で行った。
ピックアップ装置:キヤノンマシナリー社製CAP-300II
ニードルピン形状:250μmR
ニードルピン突き上げ高さ:0.5mm
エキスパンド量:8mm
チップ保持性は、ダイシング工程後において、粘着シートに保持されている半導体チップの残存率で評価した。
◎(優):チップ飛びが5%未満。
○(良):チップ飛びが5%以上10%未満。
×(不可):チップ飛びが10%以上。
ピックアップ性は、ピックアップ工程においてピックアップできたチップの比率で評価した。
◎(優):95%以上のチップがピックアップできた。
○(良):80%以上95%未満のチップがピックアップできた。
×(不可):80%未満のチップがピックアップできた。
汚染防止性は、粘着シートの粘着層とダイアタッチフィルムとを貼り合わせて、1週間保管した後に高圧水銀灯で紫外線を500mJ/cm2照射し、照射からさらに1週間保管後又は4週間保管後に粘着シートからダイアタッチフィルムを剥離し、ダイアタッチフィルムについてGC-MS分析を行い、粘着剤成分由来のピークを確認して評価した。
◎(優):紫外線を照射して1週間保管後及び4週間保管後に粘着シートから剥離したいずれのダイアタッチフィルムからも粘着剤成分由来のピークは認められなかった。
○(良):紫外線を照射して1週間保管後に粘着シートから剥離したダイアタッチフィルムからは粘着剤成分由来のピークは認められなかったが、紫外線を照射して4週間保管後に粘着シートから剥離したダイアタッチフィルムからは粘着剤成分由来のピークが認められた。
×(不可):紫外線を照射して1週間保管後及び4週間保管後に粘着シートから剥離したいずれのダイアタッチフィルムからも粘着剤成分由来のピークが認められた。
Claims (4)
- 基材フィルムと、基材フィルムの一方の面に積層された粘着層と、粘着層の露出面に積層されたダイアタッチフィルムとを有し、
粘着層を構成する粘着剤が(メタ)アクリル酸エステル共重合体(A)と紫外線重合性化合物(B)と多官能イソシアネート硬化剤(C)と光重合開始剤(D)とシリコーン重合体(E)とを有し、
(メタ)アクリル酸エステル共重合体(A)が、(メタ)アクリル酸エステル単量体の共重合体、又は、(メタ)アクリル酸エステル単量体とビニル化合物単量体との共重合体のいずれか一方であり、(メタ)アクリル酸エステル単量体とビニル化合物単量体のいずれもが水酸基を有さないものであり、
紫外線重合性化合物(B)がウレタンアクリレートオリゴマ(B1)と多官能(メタ)アクリレート(B2)からなり、ウレタンアクリレートオリゴマ(B1)はビニル基を10個以上有し、重量平均分子量Mwが50000以上、かつ、前記重量平均分子量Mwと数平均分子量Mnの比である分散度Mw/Mnが5以上であり、
光重合開始剤(D)が水酸基を有し、
シリコーン重合体(E)が水酸基を有し、
粘着層を構成する粘着剤において(メタ)アクリル酸エステル共重合体(A)が100質量部、紫外線重合性化合物(B)が5~200質量部、多官能イソシアネート硬化剤(C)が0.5~20質量部、光重合開始剤(D)が0.1~20質量部並びにシリコーン重合体(E)が0.1~20質量部である多層粘着シート。 - ウレタンアクリレートオリゴマ(B1)がイソホロンジイソシアネートの三量体のイソシアネートにジペタエリスリトールペンタアクリレートを主成分とする水酸基含有アクリレートを反応させたものであり、多官能(メタ)アクリレート(B2)がジペンタエリスリトールヘキサアクリレートである請求項1記載の多層粘着シート。
- ダイアタッチフィルムを構成する組成物がアクリル酸エステル共重合体を有する請求項1又は2記載の多層粘着シート。
- 請求項1乃至3のいずれか一項記載の多層粘着シートを用いて、多層粘着シートをシリコンウエハとリングフレームに貼り付けて固定する貼付工程、ダイシングブレードでシリコンウエハをダイシングして半導体チップにするダイシング工程、少なくとも紫外線又は放射線を照射し、チップとダイアタッチフィルムを粘着層からピックアップするピックアップ工程、を含む、電子部品の製造方法。
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SG2012092219A SG186726A1 (en) | 2010-07-14 | 2011-07-01 | Multilayer adhesive sheet and method for manufacturing electronic component |
US13/805,749 US9028638B2 (en) | 2010-07-14 | 2011-07-01 | Multilayer adhesive sheet and method for manufacturing electronic component |
CN201180031760.3A CN102971839B (zh) | 2010-07-14 | 2011-07-01 | 多层粘合片及电子元件的制造方法 |
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US20130092318A1 (en) | 2013-04-18 |
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