WO2019044623A1 - Composition adhésive, bande adhésive, et procédé de protection d'un dispositif semi-conducteur - Google Patents

Composition adhésive, bande adhésive, et procédé de protection d'un dispositif semi-conducteur Download PDF

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Publication number
WO2019044623A1
WO2019044623A1 PCT/JP2018/030981 JP2018030981W WO2019044623A1 WO 2019044623 A1 WO2019044623 A1 WO 2019044623A1 JP 2018030981 W JP2018030981 W JP 2018030981W WO 2019044623 A1 WO2019044623 A1 WO 2019044623A1
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Prior art keywords
pressure
sensitive adhesive
adhesive composition
methyl
semiconductor device
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PCT/JP2018/030981
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English (en)
Japanese (ja)
Inventor
亨 利根川
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積水化学工業株式会社
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Priority to CN201880037160.XA priority Critical patent/CN110719944A/zh
Priority to KR1020197030671A priority patent/KR102576890B1/ko
Priority to JP2018546907A priority patent/JP7181087B2/ja
Publication of WO2019044623A1 publication Critical patent/WO2019044623A1/fr

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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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/67—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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature

Definitions

  • the present invention relates to a pressure-sensitive adhesive composition, a pressure-sensitive adhesive tape and a method of protecting a semiconductor device.
  • a pressure-sensitive adhesive tape having a pressure-sensitive adhesive layer made of a pressure-sensitive adhesive composition is applied and protected (for example, , Patent Document 1 etc.).
  • bump connection is used to improve the reliability of electrical connection, and semiconductor devices whose bump height reaches about 100 to 200 ⁇ m are also used.
  • the adhesive composition for sticking and protecting on the surface in which the bump of such a semiconductor device which has a bump was formed is calculated
  • a highly adhesive pressure-sensitive adhesive composition has a problem that it may stick to the surface of a semiconductor device at the time of peeling.
  • a pressure-sensitive adhesive tape having a pressure-sensitive adhesive layer comprising a pressure-sensitive adhesive composition is attached to both sides of a semiconductor device having bumps, the pressure-sensitive adhesive adhered to the surface opposite to the surface on which the bumps are formed is peeled off.
  • the adhesive tape attached to the bump side is also easily peeled off.
  • adhesive residue is generated on the surface of the semiconductor device at the time of peeling.
  • the adhesive composition promotes adhesion by heat, so that adhesive residue is more likely to occur.
  • the adhesive layer made of the adhesive composition bites into the concavo-convex shape of the bumps, so that the occurrence of adhesive residue becomes remarkable.
  • the present invention in view of the above situation, has a high adhesive strength and can be peeled off while suppressing adhesive residue, a pressure-sensitive adhesive tape having a pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition, and the pressure-sensitive adhesive
  • An object of the present invention is to provide a composition or a method of protecting a semiconductor device using the pressure-sensitive adhesive tape.
  • a pressure-sensitive adhesive composition comprising a crosslinked pressure-sensitive adhesive polymer composed of a pressure-sensitive adhesive polymer and a crosslinking agent, having a gel swelling of 500% or more and a gel fraction of 87% or more. Be done.
  • a crosslinked pressure-sensitive adhesive polymer composed of a pressure-sensitive adhesive polymer and a crosslinking agent, having a gel swelling of 500% or more and a gel fraction of 87% or more.
  • the present invention it is possible to achieve both high adhesive strength and excellent releasability in which the adhesive residue at the time of exfoliation is suppressed, when applied to the adherend, particularly the surface of the semiconductor device on which the bumps are formed.
  • the pressure-sensitive adhesive composition which is one embodiment of the present invention comprises a crosslinked pressure-sensitive adhesive polymer composed of a pressure-sensitive adhesive polymer and a crosslinking agent.
  • the pressure-sensitive adhesive composition which is one embodiment of the present invention needs to satisfy the gel swelling rate and the gel fraction described later.
  • the pressure-sensitive adhesive composition which is an embodiment of the present invention has a gel swelling ratio of 500% or more.
  • the lower limit of the gel swelling ratio is preferably 550%, more preferably 580%, still more preferably 600%, particularly preferably 650%, particularly preferably from the viewpoint of achieving both high adhesive strength and reduced adhesive residue reduction.
  • the value is 700%.
  • the upper limit of the gel swelling ratio is not particularly limited, but is preferably 2000% (for example, about 2000%), more preferably 1500% (for example, about 1500%).
  • gel swelling ratio can be measured by the following method. Only 0.1 g of the adhesive composition is peeled off from the adhesive tape, immersed in 50 ml of ethyl acetate, and shaken at a temperature of 23 ° C. and 200 rpm for 24 hours with a shaker. After shaking, ethyl acetate and ethyl acetate are absorbed and the swollen adhesive composition is separated using a metal mesh (mesh size # 200 mesh). Ethyl acetate is absorbed, the weight including the metal mesh of the swollen adhesive composition is measured, and then dried at 110 ° C. for 1 hour.
  • a metal mesh mesh size # 200 mesh
  • the pressure-sensitive adhesive composition which is one embodiment of the present invention has a gel fraction of 87% or more.
  • the lower limit of the gel fraction is preferably 88%, more preferably 88.5%, still more preferably 89%, particularly preferably 90% from the viewpoint of achieving both high adhesive strength and reduced adhesive residue reduction.
  • the upper limit of the gel fraction is not particularly limited, but is preferably about 100%, and more preferably about 99%.
  • a gel fraction may be measured with the following method. It can. Only 0.1 g of the adhesive composition is peeled off from the adhesive tape, immersed in 50 ml of ethyl acetate, and shaken at a temperature of 23 ° C. and 200 rpm for 24 hours with a shaker. After shaking, ethyl acetate and ethyl acetate are absorbed and the swollen adhesive composition is separated using a metal mesh (mesh size # 200 mesh). The separated pressure-sensitive adhesive composition is dried at 110 ° C. for 1 hour.
  • the weight of the pressure-sensitive adhesive composition containing the metal mesh after drying is measured, and the gel fraction is calculated using the following equation.
  • Gel fraction (% by weight) 100 ⁇ (W 1 -W 2 ) / W 0 (W 0 : initial adhesive composition weight, W 1 : adhesive composition weight including the metal mesh after drying, W 2 : initial weight of the metal mesh)
  • W 0 initial adhesive composition weight
  • W 1 adhesive composition weight including the metal mesh after drying
  • W 2 initial weight of the metal mesh
  • the crosslinked pressure-sensitive adhesive polymer preferably has a gel swelling ratio of 500% or more.
  • the lower limit of the gel swelling ratio is preferably 550%, more preferably 580%, particularly preferably 600%, particularly preferably 650%, very preferably, from the viewpoint of achieving both high adhesive strength and reduced adhesive residue reduction.
  • the preferred lower limit is 700%.
  • the upper limit of the gel swelling ratio is not particularly limited, but is preferably 2000% (for example, about 2000%), more preferably 1500% (for example, about 1500%).
  • the adhesive composition which is one embodiment of this invention is used in the form of an adhesive tape, the gel swelling ratio of the said crosslinked adhesive polymer is measured by the method similar to the gel swelling ratio of the said adhesive composition. can do.
  • the cross-linked adhesive polymer preferably has a gel fraction of 87% or more.
  • the lower limit of the gel fraction is more preferably 88%, still more preferably 88.5%, particularly preferably 89%, particularly preferably 90%, from the viewpoint of achieving both high adhesion and reduced adhesive residue. is there.
  • the upper limit of the gel fraction is not particularly limited, but is preferably about 100%, and more preferably about 99%.
  • the adhesive composition which is one embodiment of this invention is used in the form of the adhesive tape which has an adhesive layer which consists of the said adhesive composition
  • the gel fraction of the said crosslinked adhesive polymer is the said adhesive composition. It can be measured by the same method as the gel fraction of a product.
  • the pressure-sensitive adhesive composition which is an embodiment of the present invention, the lower limit is 12N / cm 2 perpendicular peel force measured by tack measuring instrument, it is preferable upper limit is 42N / cm 2.
  • the pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition has a sufficient surface when the pressure-sensitive adhesive composition is attached to the surface of the semiconductor device on which the bumps are formed by adjusting the vertical peeling force within this range. It is compatible with the excellent adhesiveness which can be protected and the outstanding peelability by which the adhesive residue at the time of peeling was controlled.
  • the pressure-sensitive adhesive layer including the pressure-sensitive adhesive composition becomes hard to further peeled from the adherend, when is 42N / cm 2 or less, the pressure-sensitive adhesive composition the adhesive It becomes easy to peel off after the adhesive tape containing the agent layer becomes unnecessary, and the adhesive residue is further suppressed.
  • the lower limit is more preferably 13 N / cm 2 , still more preferably 14 N / cm 2 , still more preferably 15 N / cm 2 .
  • the normal peeling force related to the pressure-sensitive adhesive composition refers to the peeling force when the SUS probe is pressed against the pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition using a tack tester and peeled off in the vertical direction. means.
  • a SUS probe processed to a probe diameter of 5.8 5.8 mm and a tip R 2.9 is applied to a pressure-sensitive adhesive layer (thickness: 40 ⁇ m) made of a pressure-sensitive adhesive composition in a load of 10000 gf / cm 2 for 1 second After pressing, it means the peeling force when peeled off at a speed of 0.8 m / s in the vertical direction.
  • a tack tester for example, a tack tester TA-500 manufactured by UBM can be used.
  • the pressure-sensitive adhesive composition according to one embodiment of the present invention preferably has a lower limit of 600% and an upper limit of 1400% of the elongation at break measured for a sample having a thickness of 350 ⁇ m, a width of 5 mm, and a length of 50 mm.
  • the breaking elongation is 600% or more, the pressure-sensitive adhesive composition does not easily become brittle, breaking of the pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition at the time of peeling is suppressed, and adhesive residue is suppressed.
  • the breaking elongation is 1400% or less, breakage of the pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition which is too stretched at the time of peeling can be suppressed, and adhesive residue can be suppressed.
  • the lower limit is preferably 630%, more preferably 1300%, still more preferably 650%, still more preferably 1250%, particularly preferably 700%.
  • the particularly preferred upper limit is 1200%.
  • the elongation at break means a sample when a tensile test is carried out at a speed of 300 mm / min, with a test specimen having a thickness of 350 ⁇ m and a width of 5 mm being 50 mm between chucks of the sample using a tensile tester. It is measured by the elongation at break. For example, when the breaking elongation is 500 mm, the breaking elongation is 1000% when the 50 mm sample is stretched to 500 mm.
  • the adhesive polymer preferably has a molecular weight distribution Mw / Mn of 4.1 or less.
  • Mw / Mn molecular weight distribution
  • the upper limit of the molecular weight distribution is more preferably 3.5, still more preferably 3, and particularly preferably 2.5.
  • the lower limit of the molecular weight distribution is not particularly limited, but is preferably 1.1, more preferably 1.2, and still more preferably about 1.3.
  • the molecular weight distribution (Mw / Mn) is the ratio of weight average molecular weight (Mw) to number average molecular weight (Mn).
  • the weight average molecular weight (Mw) and the number average molecular weight (Mn) are measured by gel permeation chromatography (GPC) as polystyrene equivalent molecular weight. Specifically, weight-average molecular weight (Mw) and number-average molecular weight (Mn) are obtained by filtering the diluted solution obtained by diluting the adhesive polymer 50 times with tetrahydrofuran (THF) with a filter, and using the obtained filtrate It is measured as polystyrene conversion molecular weight by GPC method. In the GPC method, for example, 2690 Separations Model (manufactured by Waters) can be used.
  • the said adhesion polymer is 300,000 or more in weight average molecular weight.
  • the weight average molecular weight of the adhesive polymer is 300,000 or more, an adhesive composition having more excellent adhesion can be obtained.
  • a more preferable lower limit of the above weight average molecular weight is 350,000, a still more preferable lower limit is 400,000, and a particularly preferable lower limit is 450,000.
  • the upper limit of the weight-average molecular weight of the adhesive polymer is not particularly limited, but is, for example, 5,000,000 or less, preferably 3,000,000 or less, more preferably 1,500,000 or less.
  • the manufacturing method of the said adhesion polymer is not specifically limited, For example, it can obtain by various methods, such as living radical polymerization, emulsion polymerization, suspension polymerization, coordination polymerization, UV polymerization.
  • living radical polymerization emulsion polymerization
  • suspension polymerization emulsion polymerization
  • coordination polymerization emulsion polymerization
  • UV polymerization emulsion polymerization
  • by producing the above-mentioned adhesive polymer by combining living radical polymerization and dropping polymerization, the uniformity of each monomer in the adhesive polymer chain can be enhanced, so that cross-linking adhesion is possible.
  • the uniformity of crosslinking in the polymer can be improved, and the gel swelling ratio can be easily controlled within the above range.
  • the above-mentioned adhesive polymer is preferably an acrylic polymer, and is preferably an adhesive polymer obtained by living radical polymerization or a combination of living radical polymerization and dropping polymerization.
  • an acryl-type polymer means the polymer comprised from a (meth) acryl-type monomer.
  • the above-mentioned adhesive polymer preferably has a crosslinkable functional group, and in particular, an acrylic polymer having a crosslinkable functional group obtained by living radical polymerization (in particular, a combination of living radical polymerization and dropping polymerization) It is more preferable to contain (hereinafter, also simply referred to as "living radically polymerized acrylic polymer").
  • the living radical polymerized acrylic polymer is obtained by living radical polymerization, preferably living radical polymerization using an organic tellurium polymerization initiator, using an acrylic monomer such as (meth) acrylic acid ester or (meth) acrylic acid as a raw material.
  • Living radical polymerization is polymerization in which a molecular chain grows without being hindered by side reactions such as termination reaction or chain transfer reaction.
  • a polymer having a more uniform molecular weight and composition can be obtained as compared with free radical polymerization and the like, and generation of low molecular weight components and the like can be suppressed.
  • the pressure-sensitive adhesive layer is further difficult to peel off.
  • living radical polymerization various polymerization methods may be adopted.
  • iron, ruthenium or copper catalysts and a halogen based initiator may be used (ATRP)
  • TEMPO a halogen based initiator
  • an organic tellurium polymerization initiator may be used.
  • living radical polymerization using an organic tellurium polymerization initiator does not protect any radically polymerizable monomer having a polar functional group such as a hydroxyl group or a carboxyl group, and the same initiator Can be polymerized to obtain a polymer having uniform molecular weight and composition. For this reason, the radically polymerizable monomer which has a polar functional group can be copolymerized easily.
  • the organic tellurium polymerization initiator is not particularly limited as long as it is generally used for living radical polymerization, and examples thereof include organic tellurium compounds and organic telluride compounds.
  • Examples of the organic tellurium compound include (methyl-teranyl-methyl) benzene, (1-methyl-teranyl-ethyl) benzene, (2-methyl-teranyl-propyl) benzene, 1-chloro-4- (methyl-teranyl-methyl) benzene, 1-hydroxy- 4- (methyl-teranyl-methyl) benzene, 1-methoxy-4- (methyl-teranyl-methyl) benzene, 1-amino-4- (methyl-teranyl-methyl) benzene, 1-nitro-4- (methyl-teranyl-methyl) benzene, 1- Cyano-4- (methyl-teranyl-methyl) benzene, 1-methylcarbonyl-4- (methyl-teranyl-methyl) benzene, 1-phenylcarbonyl-4- (methyl-ter
  • the methyl teranyl group in these organic tellurium compounds may be ethyl teranyl group, n-propyl teranyl group, isopropyl teranyl group, n-butyl teranyl group, isobutyl teranyl group, t-butyl teranyl group, phenyl teranyl group, etc.
  • These organic tellurium compounds may be used alone or in combination of two or more.
  • organic telluride compound for example, dimethyl ditelluride, diethyl ditelluride, di-n-propyl ditelluride, diisopropyl ditelluride, dicyclopropyl ditelluride, di-n-butyl ditelluride, di-sec-butyl ditelluride , Di-tert-butyl ditelluride, dicyclobutyl ditelluride, diphenyl ditelluride, bis- (p-methoxyphenyl) ditelluride, bis- (p-aminophenyl) ditelluride, bis- (p-nitrophenyl) ditelluride, bis And-(p-cyanophenyl) ditelluride, bis- (p-sulfonylphenyl) ditelluride, dinaphthyl ditelluride, dipyridyl ditelluride and the like.
  • organic telluride compounds may be used alone or in combination of two or more.
  • dimethyl ditelluride, diethyl ditelluride, di-n-propyl ditelluride, di-n-butyl ditelluride and diphenyl ditelluride are preferable.
  • an azo compound may be used as a polymerization initiator for the purpose of accelerating the polymerization rate, as long as the effects of the present invention are not impaired.
  • the azo compound is not particularly limited as long as it is generally used for radical polymerization, and, for example, 2,2'-azobis (isobutyronitrile), 2,2'-azobis (2-methylbutyronitrile) ), 2,2′-azobis (2,4-dimethylvaleronitrile), 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), 1,1-azobis (cyclohexane-1-carbonitrile) ), 1-[(1-cyano-1-methylethyl) azo] formamide, 4,4'-azobis (4-cyanovaleric acid), dimethyl-2,2'-azobis (2-methylpropionate), Dimethyl-1,1'-azobis (1-cyclohexanecarboxylate), 2,2'-azobis
  • the monomer which has a crosslinkable functional group is mix
  • a crosslinkable functional group a hydroxyl group, a carboxyl group, a glycidyl group, an amino group, an amide group, a nitrile group etc. are mentioned, for example.
  • a hydroxyl group or a carboxyl group is preferable, and a hydroxyl group is more preferable.
  • examples of the monomer having a hydroxyl group include (meth) acrylic acid having a hydroxyl group such as 4-hydroxybutyl (meth) acrylate or 2-hydroxyethyl (meth) acrylate. Ester is mentioned.
  • (meth) acrylic acid is mentioned, for example.
  • examples of monomers having a glycidyl group include glycidyl (meth) acrylate.
  • Examples of the monomer having an amide group include hydroxyethyl acrylamide, isopropyl acrylamide, dimethylaminopropyl acrylamide and the like.
  • a monomer which has a nitrile group an acrylonitrile etc. are mentioned, for example.
  • the content thereof is not particularly limited, but a preferable upper limit in the radically polymerizable monomer to be polymerized in the living radical polymerization is 30% by weight.
  • the content is 30% by weight or less, the gel fraction of the pressure-sensitive adhesive composition and the crosslinked pressure-sensitive adhesive polymer does not become too high, and peeling of the pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition is suppressed. It can be improved.
  • the acrylic monomer having a carboxyl group When the acrylic monomer having a carboxyl group is used, its content is not particularly limited, but the preferable lower limit in the radically polymerizable monomer to be polymerized in the above living radical polymerization is 0.1% by weight, and the preferable upper limit is 10% by weight. is there.
  • the content is 0.1% by weight or more, the cross-linked adhesive polymer does not become too soft, and it is possible to suppress a decrease in heat-resistant adhesion.
  • the content When the content is 10% by weight or less, the crosslinked adhesive polymer does not become too hard, and peeling of the adhesive layer formed of the adhesive composition can be suppressed.
  • acrylic monomer to be polymerized in the living radical polymerization a radical polymerizable monomer other than the acrylic monomer having a crosslinkable functional group may be used.
  • other (meth) acrylic acid ester is mentioned, for example.
  • acrylic monomers having other polar functional groups such as amino group, amide group and nitrile group can be used.
  • vinyl compounds may be used as monomers.
  • the above-mentioned other (meth) acrylic acid esters are not particularly limited, and methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, tert-butyl (meth) acrylate, 2 -(Meth) acrylic acid alkyl esters such as ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, isomyristyl (meth) acrylate, stearyl (meth) acrylate, Cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-phenoxyethyl (meth)
  • the vinyl compound is not particularly limited, and examples thereof include (meth) acrylamide compounds such as N, N-dimethyl acrylamide, N, N-diethyl acrylamide, N-isopropyl acrylamide, N-hydroxyethyl acrylamide, acrylamide and the like, N-vinyl pyrrolidone, Examples include N-vinylcaprolactam, N-vinylacetamide, N-acryloyl morpholine, acrylonitrile, styrene, vinyl acetate and the like. These vinyl compounds may be used alone or in combination of two or more.
  • the acrylic monomer to be polymerized in the above living radical polymerization contains (meth) acrylic acid
  • the (meth) acrylic acid in 100 parts by weight of all monomers is from the viewpoint of enhancing the adhesive strength and making the crosslinking point of the crosslinked adhesive polymer uniform.
  • it is 0.1 parts by weight or more, more preferably 0.5 parts by weight or more.
  • (meth) acrylic acid in 100 parts by weight of total monomers is preferably 15 parts by weight or less, more preferably 10 parts by weight or less.
  • a dispersion stabilizer may be used.
  • the dispersion stabilizer include polyvinyl pyrrolidone, polyvinyl alcohol, methyl cellulose, ethyl cellulose, poly (meth) acrylic acid, poly (meth) acrylic acid ester, polyethylene glycol and the like.
  • the method of the living radical polymerization conventionally known methods are used, and for example, solution polymerization (boiling point polymerization or constant temperature polymerization), emulsion polymerization, suspension polymerization, bulk polymerization and the like can be mentioned.
  • the polymerization solvent is not particularly limited.
  • polymerization solvent examples include nonpolar solvents such as hexane, cyclohexane, octane, toluene and xylene, water, methanol, ethanol, propanol, butanol, acetone, methyl ethyl ketone, methyl isobutyl ketone, tetrahydrofuran, dioxane, N, N- Highly polar solvents such as dimethylformamide can be used. These polymerization solvents may be used alone or in combination of two or more.
  • the polymerization temperature is preferably 0 to 110 ° C. from the viewpoint of the polymerization rate.
  • the crosslinking agent is not particularly limited, and a crosslinking agent capable of crosslinking these is appropriately selected depending on the crosslinking group.
  • the crosslinking agent include isocyanate crosslinking agents, aziridine crosslinking agents, epoxy crosslinking agents, metal chelate crosslinking agents, and the like. Especially, since it is excellent in the adhesion
  • the above crosslinking agents may be used alone or in combination of two or more.
  • (meth) acrylic acid when used as the monomer constituting the adhesive polymer, it is easy to form a uniform network of the crosslinked adhesive polymer and from the viewpoint of facilitating control of the gel swelling rate.
  • epoxy based crosslinking agents are preferred.
  • isocyanate type crosslinking agent Coronate HX (made by Nippon Polyurethane Industry Co., Ltd.), Coronate L (made by Nippon Polyurethane Industry Co., Ltd.), Mytec NY260A (made by Mitsubishi Chemical Corporation) etc. are mentioned, for example.
  • examples of the epoxy-based crosslinking agent include E-5XM (manufactured by Soken Chemical Co., Ltd.), E-AX (manufactured by Soken Chemical Co., Ltd.), and the like.
  • a preferable lower limit is 0.01 parts by weight and a preferable upper limit is 5 parts by weight with respect to 100 parts by weight of the pressure-sensitive adhesive polymer (for example, living radically polymerized acrylic polymer).
  • the gel swelling ratio and the gel fraction of the pressure-sensitive adhesive composition and the crosslinked pressure-sensitive adhesive polymer can be adjusted by appropriately adjusting the type or amount of the crosslinking agent.
  • the pressure-sensitive adhesive composition which is an embodiment of the present invention preferably contains a bleeding agent.
  • the bleeding agent can bleed out on the surface of the pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition, and the peeling from the semiconductor device can be facilitated.
  • the above-mentioned bleeding agent is not particularly limited, and a known bleeding agent used for an adhesive can be used. Among them, silicone-based bleeding agents are preferable because of their high heat resistance.
  • the pressure-sensitive adhesive polymer is the living radical-polymerized acrylic polymer, it is preferable to use a bleeding agent having an acrylic moiety, because the compatibility with the crosslinked pressure-sensitive adhesive polymer is high.
  • the content of the bleed agent is 100 parts by weight of the above-mentioned adhesive polymer (for example, living radical polymerization acrylic polymer) from the viewpoint of adhesion control.
  • the lower limit is 0 parts by weight and the upper limit is 10 parts by weight.
  • the lower limit of the content of the bleeding agent is preferably 0.1 parts by weight, more preferably 5 parts by weight, particularly preferably 0.3 parts by weight, and more preferably 2 parts by weight.
  • the pressure-sensitive adhesive composition which is an embodiment of the present invention may contain an inorganic filler.
  • the inorganic filler include hydroxides and oxides of metals such as aluminum hydroxide, magnesium hydroxide, calcium oxide, magnesium oxide, aluminum oxide, zinc oxide, titanium oxide and antimony oxide, metal powders such as zinc, and the like.
  • Carbonates of metals such as calcium carbonate, magnesium carbonate, barium carbonate and zinc carbonate, alkali metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate, and alkaline earth metal carbonates such as calcium hydrogencarbonate and magnesium hydrogencarbonate Hydrogen salts, calcium sulfate, barium sulfate, calcium silicate, mica, talc, bentonite, zeolite, silica gel and the like can be mentioned.
  • a strong acid as an acid catalyst it is necessary to add metal powder and carbonate in the range which does not influence adjustment of pot life.
  • These inorganic fillers may be used alone or in combination of two or more.
  • the content of the inorganic filler is 100 parts by weight of the pressure-sensitive adhesive polymer (for example, living radical polymerization acrylic polymer) from the viewpoint of elastic modulus control.
  • the preferable lower limit is 0 parts by weight
  • the preferable upper limit is 20 parts by weight
  • the more preferable lower limit is 3 parts by weight
  • the more preferable upper limit is 15 parts by weight.
  • the application of the pressure-sensitive adhesive composition according to one embodiment of the present invention is not particularly limited, it is excellent in adhesive performance and adhesive residue suppression performance, and is used for application to protect the surface of a semiconductor device on which bumps are formed. It can use especially suitably.
  • An adhesive tape can be manufactured using the adhesive composition which is one embodiment of this invention.
  • the adhesive tape which has an adhesive layer which consists of an adhesive composition which is one embodiment of such this invention is also one of this invention.
  • the pressure-sensitive adhesive tape may be a support tape having a pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition on one side or both sides of a substrate, or may be a non-support tape having no substrate.
  • the substrate is, for example, transparent such as acrylic, olefin, polycarbonate, vinyl chloride, ABS, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), nylon, urethane, polyimide, etc.
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • nylon urethane
  • polyimide etc.
  • a sheet made of resin, a sheet having a reticulated structure, a sheet with holes, etc. may be mentioned.
  • the thickness of the substrate is not particularly limited, but the preferred lower limit is 25 ⁇ m, the more preferred lower limit is 50 ⁇ m, the preferred upper limit is 250 ⁇ m, and the more preferred upper limit is 125 ⁇ m. While being excellent in handleability because the said base material layer is this range, it can be made easy to process an adhesive tape in roll shape.
  • the above-mentioned base material may contain additives such as an antistatic agent, a mold release agent, an antioxidant, a weathering agent, a crystal nucleating agent, and a resin modifier such as polyolefin, polyester, polyamide and elastomer.
  • additives such as an antistatic agent, a mold release agent, an antioxidant, a weathering agent, a crystal nucleating agent, and a resin modifier such as polyolefin, polyester, polyamide and elastomer.
  • the pressure-sensitive adhesive tape preferably has a vertical peeling force of 12 to 42 N / cm 2 as measured by a tack measuring machine.
  • the vertical peeling force of the above-mentioned pressure-sensitive adhesive tape means the peeling force when the SUS probe is pressed against the pressure-sensitive adhesive layer of the pressure-sensitive adhesive tape using a tack tester and peeled off in the vertical direction.
  • a SUS probe processed to a probe diameter of 5.8 5.8 mm and a tip R 2.9 is pressed against the adhesive layer of the adhesive tape from the vertical direction with a load of 10000 gf / cm 2 for 1 second, and then 0 in the vertical direction .Peeling force when peeled off at a speed of 8 m / s.
  • a tack tester for example, a tack tester TA-500 manufactured by UBM can be used.
  • the vertical peel strength of the pressure-sensitive adhesive composition is measured by forming the pressure-sensitive adhesive composition into a 40 ⁇ m-thick pressure-sensitive adhesive layer, but the vertical peel force of the pressure-sensitive adhesive tape is the thickness of the pressure-sensitive adhesive layer of the pressure-sensitive adhesive tape. Regardless of the measurement.
  • the thickness of the pressure-sensitive adhesive layer is preferably 5 ⁇ m or more, more preferably 10 ⁇ m or more, still more preferably 15 ⁇ m or more, and particularly preferably 20 ⁇ m or more from the viewpoint of sufficiently protecting the bumps of the semiconductor device.
  • the thickness of the pressure-sensitive adhesive layer is preferably 500 ⁇ m or less, more preferably 300 ⁇ m or less, still more preferably 200 ⁇ m or less, particularly preferably 150 ⁇ m or less, particularly preferably from the viewpoint of suppressing blocking in roll form of the pressure-sensitive adhesive tape. It is 100 ⁇ m or less, very preferably 75 ⁇ m or less.
  • the method for producing the pressure-sensitive adhesive tape is not particularly limited.
  • a pressure-sensitive adhesive solution containing a pressure-sensitive adhesive composition is applied to a release-treated PET film and then dried to form a pressure-sensitive adhesive layer.
  • the method of making it dry is mentioned.
  • the pressure-sensitive adhesive solution is applied to a release-treated PET film, the pressure-sensitive adhesive layer formed by drying may be used as a non-support type double-sided pressure-sensitive adhesive tape as it is without a substrate.
  • Pre-UV treatment may be performed on the adhesive tape.
  • the pre-UV treatment means a treatment of irradiating the pressure-sensitive adhesive layer of the above-mentioned pressure-sensitive adhesive tape with ultraviolet light before or after applying to an adherend.
  • pre-UV treatment various physical properties of the pressure-sensitive adhesive tape can be adjusted, and for example, the breaking elongation can be controlled.
  • the pre-UV treatment specifically, for example, the adhesive layer of the adhesive tape, using a UV lamp, the ultraviolet rays having a wavelength of 300 ⁇ 450 nm, integrated irradiation dose illuminance 10 ⁇ 100mW / cm 2 3000mJ / cm 2 It can be carried out by irradiation under the conditions of As the UV lamp, for example, a high pressure mercury lamp can be used.
  • the pressure-sensitive adhesive composition and the pressure-sensitive adhesive tape can be used to apply and protect the surface on which a bump of a semiconductor device is formed.
  • a method of protecting a semiconductor device comprising the steps of applying an adhesive composition to the surface of the semiconductor device on which the bumps are formed or attaching an adhesive tape to the surface of the semiconductor devices on which the bumps are formed,
  • the pressure-sensitive adhesive tape has a pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition, and the pressure-sensitive adhesive composition contains a crosslinked pressure-sensitive adhesive polymer composed of an adhesive polymer and a crosslinking agent, and has a gel swelling of 500% or more.
  • the method whose fraction is 87% or more is also one of the present invention. According to this method of use, the pressure-sensitive adhesive tape can have high adhesive strength and can suppress adhesive residue at the time of peeling.
  • the said semiconductor device will not be specifically limited if it is a semiconductor device which has a bump.
  • the pressure-sensitive adhesive composition and the pressure-sensitive adhesive tape according to the present invention are particularly high in the protection of semiconductor devices having high bumps which reach about 100 to 200 ⁇ m because the adhesive strength and adhesive residue suppressing performance are excellent. Exert an effect.
  • a pressure-sensitive adhesive composition according to an embodiment of the present invention is directly coated on the surface of the semiconductor device on which the bumps are formed to form a pressure-sensitive adhesive layer, or the pressure-sensitive adhesive composition And a support tape having a pressure-sensitive adhesive layer comprising the above-mentioned pressure-sensitive adhesive composition on one surface of a substrate.
  • the above-mentioned application includes the act of directly applying the above-mentioned pressure-sensitive adhesive composition to form a pressure-sensitive adhesive layer.
  • the thickness of the pressure-sensitive adhesive layer can further suppress adhesive residue. Therefore, the height is preferably 70% or less with respect to the height of the bump of the semiconductor device.
  • the thickness of the pressure-sensitive adhesive layer is usually higher than 0% with respect to the height of the bump of the semiconductor device.
  • FIG. 1 A cross-sectional view schematically showing a state in which the surface of the semiconductor device on which the bumps are formed is protected by a pressure-sensitive adhesive tape having a pressure-sensitive adhesive layer comprising a pressure-sensitive adhesive composition according to an embodiment of the present invention is shown in FIG. .
  • a support tape in which a bump 12 is formed on one surface of a semiconductor device 1 and an adhesive layer 2 made of the above adhesive composition is laminated on one surface of a substrate 3 on the surface on the bump 12 side. It is protected by pasting.
  • the support plate 5 is attached to the surface of the semiconductor device 1 on which the bumps 12 are not formed via the layer 4 made of the temporary fixing pressure-sensitive adhesive composition, and the surface is protected.
  • a pressure-sensitive adhesive composition having high adhesive strength and capable of peeling while suppressing adhesive residue a pressure-sensitive adhesive tape having a pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition, or the pressure-sensitive adhesive composition or It is possible to provide a method for protecting a semiconductor device using the adhesive tape.
  • a reaction vessel in an argon-exchanged glove box, obtained is obtained the obtained ethyl 2-methyl-2-n-butylteranyl-propionate 0.026 mL, V-60 (2,2'-azobisisobutyronitrile, sum After charging 0.007 g of Optical Pure Chemical Industries, Ltd. and 1 mL of ethyl acetate, the reaction vessel was sealed, and the reaction vessel was taken out of the glove box. Subsequently, while flowing argon gas into the reaction vessel, 50 g of ethyl acetate as a polymerization solvent was charged into the reaction vessel, and the temperature was adjusted to 60.degree.
  • the resulting diluted solution is filtered with a filter, the filtrate is supplied to a gel permeation chromatography, and GPC measurement is performed under the conditions of a sample flow rate of 1 ml / min and a column temperature of 40 ° C. to measure the polystyrene equivalent molecular weight of the polymer.
  • the weight average molecular weight (Mw) and the molecular weight distribution (Mw / Mn) were determined.
  • Mw weight average molecular weight
  • Mw / Mn molecular weight distribution
  • Mw weight average molecular weight
  • Mw / Mn molecular weight distribution
  • Example 1 Production of adhesive composition and adhesive tape Ethyl acetate is added to the obtained resin A-containing solution with respect to 100 parts by weight of the non-volatile content, and the mixture is stirred. And an epoxy crosslinking agent were added and stirred to obtain an ethyl acetate solution of a pressure-sensitive adhesive composition (hereinafter simply referred to as a pressure-sensitive adhesive composition) containing a crosslinked pressure-sensitive adhesive polymer having a nonvolatile content of 30% by weight.
  • a pressure-sensitive adhesive composition a pressure-sensitive adhesive composition
  • a solution of the obtained pressure-sensitive adhesive composition in ethyl acetate is used as a doctor knife so that the thickness of the dry film becomes 40 ⁇ m. And the coating solution was dried by heating at 110.degree. C. for 5 minutes. Thereafter, stationary curing was carried out at 40 ° C. for 3 days to obtain an adhesive tape.
  • E-5XM manufactured by Soken Chemical & Engineering Co., Ltd. was used as the epoxy crosslinking agent.
  • EBECRYL 350 manufactured by Daicel Ornex was used.
  • As an inorganic filler MT-10 manufactured by Tokuyama Corp. was used.
  • Examples 2 to 14, Comparative Examples 1 to 4 A pressure-sensitive adhesive composition and a pressure-sensitive adhesive tape were obtained in the same manner as in Example 1 except that the type of resin, the blending amount of the bleeding agent and the inorganic filler, and the type and blending amount of the crosslinking agent were as shown in Tables 2 and 3. .
  • the gel swelling ratio, gel fraction, vertical peel strength and breaking elongation were measured in the same manner as in Example 1. The results are shown in Tables 2 and 3.
  • As the isocyanate crosslinking agent Coronate L-45 manufactured by Nippon Polyurethane Industry Co., Ltd. was used.
  • the heat resistance evaluation is performed by placing a bumped chip (WALTS-TEG FC150SCJY LF (PI) Type A) in the center of the jig 420 made of SUS420 shown in FIG. 2 and using a 2 kg roller at a speed of 10 mm / sec.
  • the adhesive tape cut into the size of 40 mm long and 40 mm wide was stuck, and it aged at normal temperature for 15 minutes. Thereafter, a heat treatment process was performed at 180 ° C. for 6 hours in an oven and at 250 ° C. for 10 minutes on a hot plate. It observed visually and performed the heat resistance evaluation by the following references
  • C Although peeling did not occur in the process, adhesive residue was observed at the time of peeling. The adhesive residue could not be removed even by washing.
  • a pressure-sensitive adhesive composition having high adhesion and capable of peeling while suppressing adhesive residue a pressure-sensitive adhesive tape having a pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition, and the pressure-sensitive adhesive composition or It is possible to provide a method for protecting a semiconductor device using an adhesive tape.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention a pour objet de fournir : une composition adhésive présentant une force d'adhérence élevée et pouvant être séparée en même temps que le résidu adhésif est réduit; une bande adhésive dont une couche adhésive comprend la composition adhésive; et un procédé de protection d'un dispositif semi-conducteur au moyen de la composition adhésive ou de la bande adhésive. L'invention concerne une composition adhésive comprenant un polymère adhésif de réticulation constitué d'un polymère adhésif et d'un agent de réticulation, la composition adhésive présentant un taux de gonflement de gel d'au moins 500% et une fraction de gel d'au moins 87%.
PCT/JP2018/030981 2017-08-29 2018-08-22 Composition adhésive, bande adhésive, et procédé de protection d'un dispositif semi-conducteur WO2019044623A1 (fr)

Priority Applications (3)

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CN201880037160.XA CN110719944A (zh) 2017-08-29 2018-08-22 粘合剂组合物、粘合带和半导体设备的保护方法
KR1020197030671A KR102576890B1 (ko) 2017-08-29 2018-08-22 점착제 조성물, 점착 테이프 및 반도체 디바이스의 보호 방법
JP2018546907A JP7181087B2 (ja) 2017-08-29 2018-08-22 粘着剤組成物、粘着テープ及び半導体デバイスの保護方法

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WO2023053912A1 (fr) * 2021-09-30 2023-04-06 日東電工株式会社 Stratifié, élément optique, et dispositif optique

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WO2007119884A1 (fr) * 2006-04-14 2007-10-25 Otsuka Chemical Co., Ltd. Composition de resine et adhesif thermoresistant
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JP2011074380A (ja) * 2009-09-07 2011-04-14 Lintec Corp 保護フィルム及び保護フィルムの製造方法
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JPWO2009037990A1 (ja) * 2007-09-21 2011-01-06 積水化学工業株式会社 表面保護粘着シート
CN102439769B (zh) * 2009-04-03 2014-10-08 东洋油墨Sc控股株式会社 非水系二次电池电极用粘结剂组合物
JP6347657B2 (ja) * 2014-04-22 2018-06-27 デクセリアルズ株式会社 保護テープ、及びこれを用いた半導体装置の製造方法

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JPH04227673A (ja) * 1990-04-20 1992-08-17 Minnesota Mining & Mfg Co <3M> 低電圧電子線硬化性エラストマーベース感圧接着テープ
WO2007119884A1 (fr) * 2006-04-14 2007-10-25 Otsuka Chemical Co., Ltd. Composition de resine et adhesif thermoresistant
JP2007314584A (ja) * 2006-05-23 2007-12-06 Sekisui Chem Co Ltd 粘着テープ
JP2011074380A (ja) * 2009-09-07 2011-04-14 Lintec Corp 保護フィルム及び保護フィルムの製造方法
WO2012036209A1 (fr) * 2010-09-16 2012-03-22 積水化学工業株式会社 Composé adhésif autocollant, bande adhésive autocollante, et procédé de traitement de tranche
JP2013077435A (ja) * 2011-09-30 2013-04-25 Oji Holdings Corp 導電性転写シートおよび導電性積層体
JP2016141749A (ja) * 2015-02-03 2016-08-08 リンテック株式会社 保護膜形成用シート、及び保護膜形成用複合シート

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Publication number Priority date Publication date Assignee Title
WO2023053912A1 (fr) * 2021-09-30 2023-04-06 日東電工株式会社 Stratifié, élément optique, et dispositif optique

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TW201917189A (zh) 2019-05-01
KR20200044722A (ko) 2020-04-29
JP7181087B2 (ja) 2022-11-30
JPWO2019044623A1 (ja) 2020-08-13
KR102576890B1 (ko) 2023-09-08
CN110719944A (zh) 2020-01-21

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