WO2020157828A1 - Composition de résine, procédé de fabrication de dispositif à semi-conducteur et dispositif à semi-conducteur - Google Patents

Composition de résine, procédé de fabrication de dispositif à semi-conducteur et dispositif à semi-conducteur Download PDF

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Publication number
WO2020157828A1
WO2020157828A1 PCT/JP2019/002959 JP2019002959W WO2020157828A1 WO 2020157828 A1 WO2020157828 A1 WO 2020157828A1 JP 2019002959 W JP2019002959 W JP 2019002959W WO 2020157828 A1 WO2020157828 A1 WO 2020157828A1
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resin composition
resin
semiconductor device
molecular weight
connection
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PCT/JP2019/002959
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English (en)
Japanese (ja)
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一尊 本田
恵子 上野
望 松原
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日立化成株式会社
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Priority to PCT/JP2019/002959 priority Critical patent/WO2020157828A1/fr
Publication of WO2020157828A1 publication Critical patent/WO2020157828A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/14—Peroxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • 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
    • C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
    • C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • 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

Definitions

  • the present disclosure relates to a resin composition, a method for manufacturing a semiconductor device, and a semiconductor device.
  • Peripheral members such as wiring or bumps that are electrically connected are required to have a small dielectric loss tangent (Df) in order to reduce electric energy loss in the dielectric body.
  • Df dielectric loss tangent
  • connection method FC connection method
  • FC connection method a method of metal-bonding the connection part using solder, tin, gold, silver, copper, etc., a method of metal-bonding the connection part by applying ultrasonic vibration, mechanical contact by contraction force of resin It is known how to hold. From the viewpoint of reliability of the connection portion, a method of metal-bonding the connection portion with solder, tin, gold, silver, copper or the like is generally used.
  • the COB (Chip On Board) type connection method that is actively used in BGA (Ball Grid Array), CSP (Chip Size Package), etc. also corresponds to the FC connection method.
  • the FC connection method is a COC (Chip On Chip) type in which a connection portion (bump or wiring) is formed on a semiconductor chip to connect the semiconductor chips, and a connection portion (bump or wiring) is formed on the semiconductor wafer. Is also widely used for a COW (Chip On Wafer) type connection method for connecting between a semiconductor chip and a semiconductor wafer by forming a (see, for example, Patent Document 1).
  • chip stack type packages in which the above-mentioned connection methods are stacked and multi-staged, POP (Package On Package), TSV (Through-Silicon Via), etc. Is also becoming widespread. Since such a stacking/multi-stage technology arranges the semiconductor chips and the like in three dimensions, the package can be made smaller than the method of arranging in two dimensions. Further, since such a stacking/multi-stage technology is effective for improving the performance of semiconductors, reducing noise, reducing the mounting area, and saving power, it is attracting attention as a next-generation semiconductor wiring technology.
  • the functionality and the degree of integration are advanced.
  • the pitch between the wirings is narrowed along with the functionality and the degree of integration, and the pitch and the fine wiring are advanced. ..
  • An object of the present disclosure is to provide a resin composition capable of forming a cured product having a reduced dielectric loss tangent, a method for manufacturing a semiconductor device using the resin composition, and a semiconductor device.
  • the present disclosure provides (a) a high molecular weight component having a weight average molecular weight of 10,000 or more, (b) a thermosetting resin having a weight average molecular weight of less than 10,000, (c) a curing agent, and (d). And a filler, wherein the filler (d) contains strontium titanate.
  • strontium titanate as the (d) filler, it is possible to form a cured product having a reduced dielectric loss tangent.
  • the filler (d) is usually added to control, for example, the viscosity of the resin composition and the physical properties of the cured product, but strontium titanate not only has the above-mentioned function but also has the effect of reducing the dielectric loss tangent. Can be expressed. Further, strontium titanate does not hinder the conduction of the connecting portion even when the resin composition is used as an adhesive for a semiconductor that seals the periphery of the connecting portion (wiring or bump). Therefore, the resin composition is extremely useful as an adhesive for semiconductors that can achieve a low dielectric loss tangent while ensuring good connectivity of the connection part.
  • the strontium titanate may have an average particle size of 1.0 ⁇ m or less.
  • the average particle diameter is 1.0 ⁇ m or less, biting at the time of flip chip connection can be more sufficiently prevented, visibility (transparency) can be improved, and dielectric loss tangent of a cured product can be further reduced. it can.
  • the high molecular weight component (a) may include a high molecular weight component containing a maleimide skeleton.
  • the high molecular weight component (a) contains the high molecular weight component containing a maleimide skeleton, the curing shrinkage of the resin composition can be reduced and the heat resistance can be improved. Therefore, warpage of the package can be reduced, generation of voids can be suppressed, and insulation reliability can be improved.
  • the glass transition temperature of the high molecular weight component (a) may be 160° C. or lower.
  • the laminating property of the resin composition is improved and the generation of voids is easily suppressed.
  • the thermosetting resin (b) may include an acrylic resin.
  • the thermosetting resin contains an acrylic resin, the resin composition can exhibit good quick-curing properties, and can suppress the occurrence of voids when pressure bonding is performed in a short time. Moreover, when acrylic resin is used, the dielectric loss tangent of the obtained cured product can be more easily reduced.
  • the acrylic resin may be a solid acrylic resin at 25°C. Solid acrylic resins have better heat resistance than liquid ones, so that it is easier to suppress the occurrence of voids.
  • the curing agent (c) may include a heat radical generator. Further, the curing agent (c) may contain a peroxide. These curing agents are preferable from the viewpoint of handleability and storage stability of the resin composition. Moreover, when these curing agents are used, the dielectric loss tangent of the obtained cured product can be more easily reduced.
  • the above resin composition may be in the form of a film.
  • the handleability of the resin composition can be improved, and the workability and productivity at the time of manufacturing the package can be improved.
  • the resin composition is arranged to electrically connect the connecting portions of the first member having the connecting portion and the second member having the connecting portion to each other, at least a part of the connecting portion is sealed. It may be used as an adhesive for semiconductors that stops.
  • the resin composition of the present disclosure can form a cured product having a small dielectric loss tangent, and thus is suitable as an adhesive for semiconductors.
  • the present disclosure is also a method for manufacturing a semiconductor device, in which connecting portions of a first member having a connecting portion and a second member having a connecting portion are arranged to face each other to electrically connect, and at least the connecting portion is provided.
  • a method for manufacturing a semiconductor device including a step of sealing a part of the resin composition with the above resin composition. According to the above manufacturing method, a semiconductor device with low energy loss can be obtained.
  • the present disclosure further includes a connection structure in which the connecting portions of the first member having the connecting portion and the second member having the connecting portion are arranged facing each other and electrically connected, and at least a part of the connecting portion is sealed. And an adhesive material for forming a semiconductor device, wherein the adhesive material is a cured product of the resin composition.
  • the semiconductor device has a small energy loss.
  • the numerical range indicated by using “to” indicates the range including the numerical values before and after “to” as the minimum value and the maximum value, respectively.
  • the upper limit value or the lower limit value of the numerical range of a certain stage can be arbitrarily combined with the upper limit value or the lower limit value of the numerical range of another stage.
  • the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
  • “A or B” may include either one of A and B, or may include both.
  • the materials exemplified in the present specification can be used alone or in combination of two or more kinds.
  • (meth)acryl means acryl or methacryl corresponding thereto.
  • the resin composition according to the present embodiment has (a) a high molecular weight component having a weight average molecular weight of 10,000 or more (hereinafter, referred to as “(a) component” in some cases), and (b) a thermosetting resin having a weight average molecular weight of less than 10,000.
  • Resin hereinafter sometimes referred to as “(b) component”
  • curing agent hereinafter sometimes referred to as “(c) component”
  • filler hereinafter sometimes referred to as “(d)”.
  • (d) filler contains strontium titanate.
  • the high molecular weight component having a weight average molecular weight of 10,000 or more is not particularly limited, but from the viewpoint of heat resistance and film forming property, for example, bismaleimide resin, epoxy resin, phenoxy resin, polyimide resin, polyamide resin, poly Examples thereof include carbodiimide resin, cyanate ester resin, acrylic resin, polyester resin, polyethylene resin, polyether sulfone resin, polyetherimide resin, polyvinyl acetal resin, urethane resin and acrylic rubber.
  • a bismaleimide resin, an epoxy resin, a phenoxy resin, a polyimide resin, an acrylic resin, and an acrylic rubber are more preferable because they are more excellent in heat resistance and film formability.
  • These high molecular weight components can be used alone or as a mixture or copolymer of two or more kinds.
  • the weight average molecular weight of the component (a) is 10,000 or more. When the weight average molecular weight is 10,000 or more, good film formability is easily obtained.
  • the weight average molecular weight of the component (a) is preferably 1,000,000 or less. When the weight average molecular weight is 1,000,000 or less, it is easy to laminate the resin composition on a semiconductor wafer, a semiconductor chip, a substrate or the like having protrusions such as bumps or pads, and it is easy to suppress the residual voids. Moreover, when the weight average molecular weight is 1,000,000 or less, the viscosity of the resin composition does not become too high at the time of mounting, and the occurrence of connection failure is easily suppressed.
  • the weight average molecular weight of the component (a) is preferably 10,000 to 800,000, and more preferably 10,000 to 600,000.
  • the weight average molecular weight (Mw) means the weight average molecular weight as measured by polystyrene conversion using high performance liquid chromatography (Shimadzu C-R4A).
  • the glass transition temperature (Tg) of the component (a) is preferably 160°C or lower.
  • Tg is 160° C. or less, it is easy to laminate the resin composition on a semiconductor wafer, a semiconductor chip, a substrate, or the like having protrusions such as bumps or pads, and it is easy to suppress the residual voids.
  • Tg is preferably 40° C. or higher from the viewpoint of film formability and film handleability (difficult to handle when film tack is high).
  • Tg means Tg measured using a DSC (DSC-7 manufactured by Perkin Elmer Co., Ltd.) under the conditions of a sample amount of 10 mg, a temperature rising rate of 10° C./min, and a measurement atmosphere of air.
  • the component (a) includes a high molecular weight component having a weight average molecular weight of 10,000 or more and containing a maleimide skeleton from the viewpoint of low shrinkage (warp suppression), high heat resistance (void suppression and high reliability), and low dielectric loss tangent. It is preferable that a high-molecular weight component having a weight average molecular weight of 10,000 or more and containing a bismaleimide skeleton is contained.
  • the bismaleimide skeleton-containing high molecular weight component reacts with the thermosetting resin (b) having a weight average molecular weight of less than 10,000 by the heat radical generator to be an adhesive having more excellent heat resistance.
  • the number of maleimide skeletons in one molecule is preferably 2 to 3 (bis or tri). If the number of maleimide skeletons is larger than this, the number of reaction points increases, curing in a short time does not proceed sufficiently, and the curing reaction rate of the resin composition may decrease. This is because formation of a network due to curing may proceed rapidly and unreacted groups may remain. In addition, when the number of maleimide skeletons is larger than the above, flexibility may be lowered, and a phenomenon such as easy peeling from an adherend or increased warpage may occur.
  • thermosetting resin (b) (b) Thermosetting resin having a weight average molecular weight of less than 10,000)
  • thermosetting resin (b) having a weight average molecular weight of less than 10,000, but it is necessary to react with the curing agent (c). Since a component having a small weight average molecular weight may decompose upon heating and cause voids, the component (b) preferably has heat resistance and further has rapid curing property.
  • the mass ratio of the component (a) and the component (b) is not particularly limited, but it is preferable that the content of the component (b) is 0.01 to 10 parts by mass with respect to 1 part by mass of the component (a).
  • the content of the component (b) with respect to 1 part by mass of the component (a) is more preferably 0.05 to 5 parts by mass, further preferably 0.1 to 5 parts by mass.
  • the component (b) examples include acrylic resin, epoxy resin, bismaleimide resin and the like.
  • an acrylic resin having a fast curing property is preferable from the viewpoint of suppressing voids when pressure bonding is performed in a short time.
  • the acrylic resin is not particularly limited as long as it has at least one acrylic group in the molecule, and examples thereof include bisphenol A type, bisphenol F type, naphthalene type, phenol novolac type, cresol novolac type, phenol aralkyl type, biphenyl. Type, triphenylmethane type, dicyclopentadiene type, fluorene type, adamantane type, various polyfunctional acrylic resins and the like can be used. These can be used alone or as a mixture of two or more kinds.
  • the number of functional groups of the acrylic group in the acrylic resin is preferably 3 functional groups or less. When it is tetrafunctional or more, since the number of functional groups is large, curing in a short time does not proceed sufficiently, and the curing reaction rate of the resin composition may decrease. This is because formation of a network due to curing may proceed rapidly and unreacted groups may remain.
  • the epoxy resin is not particularly limited as long as it has two or more epoxy groups in the molecule, and examples thereof include bisphenol A type, bisphenol F type, naphthalene type, phenol novolac type, cresol novolac type, phenol aralkyl type, and biphenyl.
  • Type, triphenylmethane type, dicyclopentadiene type, various polyfunctional epoxy resins and the like can be used. These can be used alone or as a mixture of two or more kinds.
  • the content of the component (b) is preferably 10 to 50% by mass, more preferably 15 to 40% by mass, based on the total solid content of the resin composition.
  • the content is 10% by mass or more, a sufficient amount of the curing component is present, so that the flow of the resin after curing is easily controlled, and when the content is 50% by mass or less, the cured product does not become too hard. , Easy to reduce the warpage of the package.
  • the component (b) is preferably solid at room temperature (25°C). From the viewpoint of heat resistance, voids are less likely to occur in the solid state than in the liquid state, and the resin composition before curing (B stage) has a low viscosity (tack) and is excellent in handling (easy to form into a film).
  • the curing agent (c) is not particularly limited as long as it functions as a curing agent for the thermosetting resin having a weight average molecular weight of less than 10,000 (b).
  • the curing agent (c) include a thermal radical generator (radical generator by heat) and a photo radical generator (radical generator by light). Of these, the heat radical generator is preferable from the viewpoint of handleability.
  • heat radical generators examples include azo compounds and organic peroxides.
  • Organic peroxides are preferred from the viewpoints of handleability and storage stability.
  • organic peroxides examples include ketone peroxides, peroxyketals, hydroperoxides, dialkyl peroxides, diacyl peroxides, peroxydicarbonates and peroxyesters. From the viewpoint of storage stability, hydroperoxide, dialkyl peroxide and peroxy ester are preferable. Further, from the viewpoint of heat resistance, hydroperoxide and dialkyl peroxide are preferable.
  • azo compound examples include 2,2′-azobisisobutyronitrile, 2,2′-azobis(2-methylbutyronitrile), 1,1′-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile), dimethyl 2,2'-azobis(2-methylpropionate) ), 4,4′-azobis(4-cyanovaleric acid), 2,2′-azobis(2-hydroxymethylpropionitrile), 2,2′-azobis[2-(imidazolin-2-yl)propane ] Etc. are mentioned.
  • the content of the component (c) is preferably 0.5 to 10 parts by mass, preferably 1 to 5 parts by mass, relative to 100 parts by mass of the component (b). More preferable.
  • the content is 0.5 parts by mass or more, the curing is likely to proceed sufficiently, and when the content is 10 parts by weight or less, it is possible to prevent the curing from rapidly progressing and increase the number of reaction points, and to lengthen the molecular chain. At the same time, the remaining unreacted groups tend to be suppressed.
  • the above-mentioned (c) curing agent can be used alone or as a mixture of two or more kinds.
  • the component (b) is an epoxy resin
  • a phenol resin-based curing agent, an acid anhydride-based curing agent, an amine-based curing agent, an imidazole-based curing agent, a phosphine-based curing agent, or the like is used as the (c) curing agent.
  • a phenol resin-based curing agent an acid anhydride-based curing agent, an amine-based curing agent, an imidazole-based curing agent, a phosphine-based curing agent, or the like
  • the phenolic resin-based curing agent is not particularly limited as long as it has two or more phenolic hydroxyl groups in the molecule, and examples thereof include phenol novolac resin, cresol novolac resin, and phenol.
  • Aralkyl resin, cresol naphthol formaldehyde polycondensate, triphenylmethane type polyfunctional phenol resin and various polyfunctional phenol resins can be used. These can be used alone or as a mixture of two or more kinds.
  • the equivalent ratio (phenolic hydroxyl group/epoxy group, molar ratio) of the phenol resin type curing agent to the epoxy resin is preferably 0.3 to 1.5 from the viewpoint of obtaining good curability, adhesiveness and storage stability. , 0.4 to 1.0 are more preferable, and 0.5 to 1.0 are still more preferable.
  • the equivalent ratio is 0.3 or more, the curability and the adhesive strength tend to be improved, and when it is 1.5 or less, the unreacted phenolic hydroxyl group does not remain excessively and the water absorption rate is high. It tends to be kept low and the insulation reliability tends to be improved.
  • Acid Anhydride Curing Agent examples include methylcyclohexanetetracarboxylic dianhydride, trimellitic anhydride, pyromellitic dianhydride, benzophenonetetracarboxylic dianhydride and ethylene. Glycol bisanhydrotrimeritate can be used. These can be used alone or as a mixture of two or more kinds.
  • the equivalent ratio (acid anhydride group/epoxy group, molar ratio) of the acid anhydride type curing agent to the epoxy resin is 0.3 to 1.5 from the viewpoint of obtaining good curability, adhesiveness and storage stability. Is preferred, 0.4 to 1.0 is more preferred, and 0.5 to 1.0 is even more preferred.
  • the equivalent ratio is 0.3 or more, the curability and the adhesive strength tend to be improved, and when it is 1.5 or less, the unreacted acid anhydride does not remain excessively and the water absorption is It tends to be kept low and the insulation reliability tends to be improved.
  • (C-iii) Amine-based curing agent for example, dicyandiamide, various amine compounds and the like can be used. These may be used alone or in combination of two or more.
  • the equivalent ratio (amine/epoxy group, molar ratio) of the amine-based curing agent to the epoxy resin is preferably 0.3 to 1.5, from the viewpoint of obtaining good curability, adhesiveness and storage stability, and is preferably 0. 4-1.0 is more preferable, and 0.5-1.0 is still more preferable. If the equivalent ratio is 0.3 or more, the curability and the adhesive strength tend to be improved, and if it is 1.5 or less, unreacted amine does not remain excessively and the insulation reliability is improved. Tend to do.
  • imidazole-based curing agent examples include 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1-Cyanoethyl-2-undecylimidazole, 1-cyano-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2,4-diamino -6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-ethyl-4'
  • 1-cyanoethyl-2-undecylimidazole 1-cyano-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazoletriazole from the viewpoint of obtaining excellent curability, storage stability and connection reliability.
  • the content of the imidazole-based curing agent is preferably 0.1 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, based on 100 parts by mass of the epoxy resin.
  • the content of the imidazole-based curing agent is 0.1 part by mass or more, the curability tends to be improved, and when it is 20 parts by mass or less, the resin composition does not cure before the metal bond is formed. , Connection failure tends not to occur.
  • (Cv) Phosphine-Based Curing Agent examples include triphenylphosphine, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetra(4-methylphenyl)borate and tetraphenylphosphonium (4-fluorophenyl). Borate is an example. These may be used alone or in combination of two or more.
  • the content of the phosphine-based curing agent is preferably 0.1 to 10 parts by mass, more preferably 0.1 to 5 parts by mass with respect to 100 parts by mass of the epoxy resin.
  • the content of the phosphine-based curing agent is 0.1 part by mass or more, the curability tends to be improved, and when it is 10 parts by mass or less, the resin composition does not cure before the metal bond is formed. , Connection failure tends not to occur.
  • Each of the phenolic resin-based curing agent, the acid anhydride-based curing agent and the amine-based curing agent can be used alone or as a mixture of two or more kinds.
  • the imidazole-based curing agent and the phosphine-based curing agent may be used alone, or may be used together with a phenol resin-based curing agent, an acid anhydride-based curing agent or an amine-based curing agent.
  • the combination of an acrylic resin, a bismaleimide resin, an epoxy resin, and a curing agent is not particularly limited as long as curing proceeds, but as a curing agent to be combined with an epoxy resin, from the viewpoint of handleability, storage stability, and curability, phenol is used. It is preferable to use a resin-based curing agent and an imidazole-based curing agent in combination, an acid anhydride-based curing agent and an imidazole-based curing agent in combination, an amine-based curing agent and an imidazole-based curing agent in combination, and an imidazole-based curing agent alone.
  • the imidazole-based curing agent alone which is excellent in quick-curing property, is more preferable because the productivity is improved when the connection is made in a short time.
  • volatile components such as low-molecular components can be suppressed, so that void generation can be suppressed.
  • an organic peroxide is preferable from the viewpoint of handleability and storage stability.
  • an organic peroxide is preferable from the viewpoint of handleability and storage stability.
  • Radical polymerization (acrylic curing system) is preferable as the curing system.
  • the anion-polymerized epoxy resin or the like is contained, it is difficult for the curing reaction rate of the resin composition to be 50% or more. Therefore, the content of the epoxy resin is preferably 20 parts by mass or less relative to 80 parts by mass of the acrylic resin, More preferably, it is not added.
  • the filler contains strontium titanate.
  • the filler is used for controlling the viscosity and the physical properties of the cured product, and for suppressing the generation of voids and suppressing the moisture absorption rate when the semiconductor chip and the substrate are connected (compressed) at a high temperature.
  • Strontium titanate not only exhibits sufficient performance for the above-mentioned applications, but also has an effect of reducing the dielectric loss tangent (Df).
  • the shape of the strontium titanate filler is not particularly limited, but a spherical shape is preferable from the viewpoint of ease of viscosity control and improvement of handleability.
  • the average particle size of the strontium titanate filler is preferably 1.0 ⁇ m or less, and 0.5 ⁇ m or less from the viewpoint of preventing biting during flip chip connection and improving visibility (transparency). Is more preferable.
  • the lower limit of the average particle size is not particularly limited, but may be 0.01 ⁇ m or more, for example.
  • the average particle diameter of the filler is the median diameter (D50) and can be measured by a laser diffraction type particle size distribution measuring device.
  • the strontium titanate filler may be subjected to a glycidyl-based, phenylamino-based, acrylic-based, or methacrylic-based surface treatment from the viewpoint of dispersibility, fluidity, and adhesive strength. From the viewpoint of storage stability, phenyl-based, acrylic-based, and methacrylic-based surface treatments are more preferable.
  • the content of the strontium titanate filler is preferably 30 to 90% by mass, and more preferably 40 to 80% by mass, based on the total solid content of the resin composition.
  • the content is 30% by mass or more, heat dissipation is more excellent, the dielectric loss tangent (Df) can be further reduced, and the adhesive force tends to be improved.
  • the content is 90% by mass or less, it is possible to prevent the fluidity of the resin composition from decreasing due to an increase in viscosity, to prevent the filler from being trapped (trapping) in the connection portion, and improving the connection reliability. Tends to be able to.
  • the resin composition contains a strontium titanate filler other than the strontium titanate filler for controlling the viscosity and the physical properties of the cured product, and for suppressing the occurrence of voids and suppressing the moisture absorption rate when connecting the semiconductor chip and the substrate.
  • a strontium titanate filler other than the strontium titanate filler for controlling the viscosity and the physical properties of the cured product, and for suppressing the occurrence of voids and suppressing the moisture absorption rate when connecting the semiconductor chip and the substrate.
  • You may mix
  • other fillers include insulating inorganic fillers, whiskers, resin fillers and the like.
  • the material of the insulating inorganic filler include glass, silica, alumina, titanium oxide, carbon black, mica, boron nitride and the like.
  • silica, alumina, titanium oxide, boron nitride and the like are preferable, and silica, alumina and boron nitride are more preferable.
  • the material of the whiskers include aluminum borate, aluminum titanate, zinc oxide, calcium silicate, magnesium sulfate, boron nitride and the like.
  • the material of the resin filler include polyurethane and polyimide. These other fillers can be used alone or as a mixture of two or more kinds. The shape, particle size, and blending amount of other fillers are not particularly limited.
  • the shape, particle size, and amount of other fillers are not particularly limited. Further, the physical properties may be appropriately adjusted by surface treatment.
  • the average particle size is preferably 1.0 ⁇ m or less, and 0.5 ⁇ m or less from the viewpoint of preventing biting and improving visibility (transparency) during flip chip connection. Is more preferable.
  • fillers are preferably surface-treated fillers from the viewpoint of improving dispersibility and adhesive strength.
  • examples of the surface treatment include glycidyl (epoxy), amine, phenyl, phenylamino, acryl, vinyl and the like.
  • a silane treatment with a silane compound such as an epoxysilane type, an aminosilane type, an acrylsilane type is preferable because of the ease of surface treatment.
  • a glycidyl-based compound, a phenylamino-based compound, or a (meth)acrylic compound is preferable from the viewpoint of excellent dispersibility and fluidity and further improving the adhesive force.
  • resin fillers can impart flexibility at high temperatures such as 260°C, so they are suitable for improving reflow resistance. Further, since it imparts flexibility, it is also effective in improving the film forming property.
  • the (d) filler is insulative.
  • the resin composition preferably does not contain a conductive metal filler such as a silver filler or a solder filler.
  • the compounding amount of the (d) filler is preferably 30 to 90% by mass, and 40 to 80% by mass, based on the total solid content of the resin composition, including the strontium titanate filler and other additive fillers. More preferably. When the content is 30% by mass or more, the heat dissipation is more excellent and the adhesive strength tends to be improved. When the content is 90% by mass or less, it is possible to suppress a decrease in fluidity of the resin composition due to an increase in viscosity, it is possible to suppress the trapping (trapping) of the filler into the connection portion, and it is possible to improve the connection reliability. Tend.
  • the resin composition may contain, in addition to the above-mentioned components, a flux component, that is, a flux activator that is a compound exhibiting flux activity (activity for removing oxides and impurities).
  • a flux component that is, a flux activator that is a compound exhibiting flux activity (activity for removing oxides and impurities).
  • the flux activator include nitrogen-containing compounds having an unshared electron pair such as imidazoles and amines, carboxylic acids, phenols and alcohols. It should be noted that, compared with alcohols, carboxylic acids more strongly develop flux activity and are easier to improve connectivity.
  • the content of the flux activator is preferably 0.2 to 3% by mass, and is 0.4 to 1.8% by mass, based on the total solid content of the resin composition. Is more preferable.
  • the resin composition may further contain an ion trapper, an antioxidant, a silane coupling agent, a titanium coupling agent, a leveling agent and the like. These may be used alone or in combination of two or more. The blending amount of these may be appropriately adjusted so that the effect of each additive is exhibited.
  • the curing reaction rate of the resin composition when kept at 200° C. for 5 seconds is preferably 50% or more, more preferably 80% or more.
  • the curing reaction rate is 50% or more, it is possible to prevent the solder from scattering or flowing at the time of connection (above the solder melting temperature), and it is possible to suppress the occurrence of poor connection and poor insulation reliability.
  • the resin composition according to this embodiment can be pressure-bonded at a high temperature of 200° C. or higher.
  • the resin composition according to the present embodiment is suitable as an adhesive for semiconductors, and exerts an effect more when used in a flip chip package in which a metal such as solder is melted to form a connection.
  • the resin composition according to this embodiment is preferably in the form of a film (film adhesive) from the viewpoint of improving productivity.
  • the method for producing the film adhesive will be described below.
  • component, component, (b) component, (c) component, (d) component and, if necessary, other components are added to an organic solvent and then dissolved or dispersed by stirring and mixing, kneading and the like.
  • prepare resin varnish After that, on the base film that has been subjected to a mold release treatment, after applying a resin varnish using a knife coater, roll coater, applicator, die coater, comma coater, etc., the organic solvent is reduced by heating, and the base film Form a film adhesive on top. Further, before the organic solvent is reduced by heating, a resin adhesive varnish may be spin-coated on a wafer or the like to form a film, and then the film adhesive may be formed on the wafer by a solvent drying method.
  • organic solvent used for preparing the resin varnish those having a property capable of uniformly dissolving or dispersing each component are preferable, and examples thereof include dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, diethylene glycol dimethyl ether, Examples include toluene, benzene, xylene, methyl ethyl ketone, tetrahydrofuran, ethyl cellosolve, ethyl cellosolve acetate, butyl cellosolve, dioxane, cyclohexanone, and ethyl acetate. These organic solvents can be used alone or in combination of two or more kinds.
  • Stirring and mixing and kneading at the time of preparing the resin varnish can be performed using, for example, a stirrer, a raker, a three-roll, a ball mill, a bead mill or a homodisper.
  • the substrate film is not particularly limited as long as it has heat resistance to withstand the heating conditions when volatilizing the organic solvent, polyester film, polypropylene film, polyethylene terephthalate film, polyimide film, polyetherimide film, poly Examples thereof include ether naphthalate film and methylpentene film.
  • the base film is not limited to a single layer made of one of these films, and may be a multilayer film made of two or more types of films.
  • the conditions for volatilizing the organic solvent from the applied resin varnish specifically, heating at 50 to 200° C. for 0.1 to 90 minutes is preferable. It is preferable that the organic solvent be volatilized up to 1.5% by mass or less if it does not affect the voids and the viscosity adjustment after mounting.
  • the thickness of the film in the film adhesive according to the present embodiment is preferably 10 to 100 ⁇ m, more preferably 20 to 50 ⁇ m from the viewpoint of visibility, fluidity and filling property.
  • the resin composition according to the present embodiment is preferably used for a semiconductor device, and is a semiconductor in which the connecting portions of the first member having the connecting portion and the second member having the connecting portion are arranged to face each other and electrically connect to each other.
  • it is preferably used as an adhesive for semiconductors that seals at least a part of the connection portion.
  • the first member includes a semiconductor chip and a semiconductor wafer
  • the second member includes a printed circuit board, a semiconductor chip, and a semiconductor wafer.
  • the electrodes of the connection portion in the semiconductor device may be either metal-bonded between the bump and the wiring or metal-bonded between the bump and the bump.
  • flip-chip connection that obtains electrical connection via a semiconductor adhesive may be used.
  • FIG. 1 is a schematic cross-sectional view showing an embodiment (a COB type connection mode of a semiconductor chip and a substrate) of a semiconductor device.
  • the first semiconductor device 100 is arranged on the semiconductor chip 10 and the substrate (wiring circuit board) 20 facing each other, and on the surfaces of the semiconductor chip 10 and the substrate 20 facing each other.
  • the wiring 15, the connection bumps 30 that connect the wirings 15 of the semiconductor chip 10 and the substrate 20 to each other, and the adhesive material 40 that fills the space between the semiconductor chip 10 and the substrate 20 without any gap.
  • the semiconductor chip 10 and the substrate 20 are flip-chip connected by the wiring 15 and the connection bumps 30.
  • the wiring 15 and the connection bumps 30 are sealed with an adhesive material 40 and are shielded from the external environment.
  • the adhesive material 40 is a cured product of the semiconductor adhesive of the present embodiment.
  • FIG. 2 is a schematic cross-sectional view showing another embodiment of a semiconductor device (COC type connection mode between semiconductor chips).
  • the third semiconductor device 300 is similar to the first semiconductor device 100 except that the two semiconductor chips 10 are flip-chip connected by the wiring 15 and the connection bumps 30. Is.
  • the fourth semiconductor device 400 is similar to the second semiconductor device 200, except that the two semiconductor chips 10 are flip-chip connected by the bumps 32.
  • the semiconductor chip 10 is not particularly limited, and various semiconductors such as elemental semiconductors composed of the same type of element such as silicon and germanium and compound semiconductors such as gallium/arsenic and indium/phosphorus can be used.
  • the substrate 20 is not particularly limited as long as it is a wired circuit board, and is formed on the surface of an insulating substrate containing glass epoxy resin, polyimide resin, polyester resin, ceramics, epoxy resin, bismaleimide triazine resin, etc. as main components.
  • a circuit board on which wiring (wiring pattern) is formed by etching away unnecessary portions of the metal layer, a circuit board on which wiring (wiring pattern) is formed on the surface of the insulating substrate by metal plating, etc., a surface of the insulating substrate It is possible to use a circuit board or the like on which wiring (wiring pattern) is formed by printing a conductive substance on.
  • connection parts such as the wiring 15 and the bumps 32 are mainly composed of gold, silver, copper, solder (main components are, for example, tin-silver, tin-lead, tin-bismuth, tin-copper), nickel, tin, lead, etc. And may contain a plurality of metals.
  • the surface of the wiring contains gold, silver, copper, solder (main components are, for example, tin-silver, tin-lead, tin-bismuth, tin-copper), tin, nickel, etc. as main components.
  • a metal layer may be formed. This metal layer may be composed of only a single component, or may be composed of a plurality of components. Further, it may have a structure in which a plurality of metal layers are laminated. Copper and solder are commonly used because they are inexpensive. Since copper and solder contain oxides, impurities, etc., it is preferable that the semiconductor adhesive has flux activity.
  • the main components are gold, silver, copper, solder (main components are, for example, tin-silver, tin-lead, tin-bismuth, tin-copper), tin, nickel, etc. Is used and may be composed of only a single component or may be composed of a plurality of components. Further, it may be formed to have a structure in which these metals are laminated.
  • the bump may be formed on the semiconductor chip or the substrate. Copper and solder are commonly used because they are inexpensive. Since copper and solder contain oxides, impurities, etc., it is preferable that the semiconductor adhesive has flux activity.
  • an adhesive may be flip-chip connected or laminated via semiconductor chips to form a hole penetrating the semiconductor chip and connected to an electrode on the pattern surface.
  • FIG. 3 is a schematic cross-sectional view showing another embodiment of the semiconductor device (semiconductor chip stacked type (TSV)).
  • TSV semiconductor chip stacked type
  • the wiring 15 formed on the interposer 50 is connected to the wiring 15 of the semiconductor chip 10 via the connection bumps 30, so that the semiconductor chip 10 and the interposer 50 are connected. And are flip-chip connected.
  • the gap between the semiconductor chip 10 and the interposer 50 is filled with the adhesive material 40 without any gap.
  • the semiconductor chip 10 is repeatedly laminated via the wiring 15, the connection bumps 30, and the adhesive material 40.
  • the wirings 15 on the pattern surfaces on the front and back of the semiconductor chip 10 are connected to each other by the through electrodes 34 filled in the holes penetrating the inside of the semiconductor chip 10.
  • the through electrode 34 copper, aluminum or the like can be used.
  • the through electrode 34 is vertically passed through the semiconductor chip 10, the distance between the semiconductor chips 10 facing each other or the distance between the semiconductor chip 10 and the interposer 50 can be shortened to enable flexible connection.
  • the semiconductor adhesive according to the present embodiment is suitably used as a sealing material between the semiconductor chips 10 facing each other or between the semiconductor chips 10 and the interposer 50 in such a TSV technique.
  • the semiconductor device manufacturing method uses the semiconductor adhesive according to the present embodiment to dispose the connecting portions of the first member having the connecting portion and the second member having the connecting portion so as to face each other. Connect electrically.
  • the method for manufacturing a semiconductor device according to the present embodiment is, for example, connecting the first member and the second member to each other via an adhesive for a semiconductor and connecting the respective connecting portions of the first member and the second member to each other. And a step of electrically connecting to each other to obtain a semiconductor device. Further, in this step, at least a part of the connecting portion is sealed with the semiconductor adhesive.
  • the respective connection portions of the first member and the second member can be connected to each other by metal bonding.
  • a substrate for example, a glass epoxy substrate
  • the wiring 15 of the semiconductor chip 10 and the wiring 15 of the substrate 60 are electrically connected by connection bumps (solder bumps) 30.
  • a solder resist 70 is arranged on the surface of the substrate 60 on which the wiring 15 is formed except for the positions where the connection bumps 30 are formed.
  • a semiconductor adhesive film adhesive or the like
  • the sticking can be performed by hot pressing, roll laminating, vacuum laminating, or the like.
  • the supply area and thickness of the semiconductor adhesive are appropriately set depending on the size of the semiconductor chip 10 or the substrate 60, the bump height, and the like.
  • the semiconductor adhesive may be attached to the semiconductor chip 10.
  • the semiconductor adhesive is attached to the semiconductor wafer 10 by applying the semiconductor adhesive to a semiconductor wafer and then dicing the semiconductor wafer into individual pieces. May be produced.
  • the adhesive for semiconductors has a high light transmittance, the visibility is ensured even when the alignment mark is covered, so that the range to be applied not only on the semiconductor wafer (semiconductor chip) but also on the substrate It is not limited and is easy to handle.
  • connection bumps 30 on the wirings 15 of the semiconductor chip 10 and the wirings 15 of the substrate 60 are aligned using a connection device such as a flip chip bonder. .. Then, the semiconductor chip 10 and the substrate 60 are pressed while being heated at a temperature equal to or higher than the melting point of the connection bump 30 (when solder is used for the connection portion, it is preferable that the solder portion has a temperature of 240° C. or higher), and the semiconductor chip 10 and the substrate. 60 is connected, the adhesive for semiconductor is cured, and the gap between the semiconductor chip 10 and the substrate 60 is sealed and filled with the adhesive material 40 made of a cured product of the adhesive for semiconductor.
  • connection load depends on the number of bumps, but is set in consideration of bump height variation absorption, control of bump deformation amount, and the like.
  • the connection time is preferably short from the viewpoint of improving productivity. It is preferable to melt the solder, remove the oxide film, surface impurities, and the like, and form a metal joint at the connection portion.
  • Short-time connection time means that the time required for the connection to be 240°C or higher during connection formation (main crimping) (for example, the time when solder is used) is 10 seconds or less.
  • the connection time is preferably 5 seconds or less, more preferably 3 seconds or less.
  • the semiconductor chip and the substrate are temporarily fixed (in a state where the semiconductor adhesive is used) and heat-treated in a reflow furnace to melt the solder bumps.
  • Temporary fixing does not require the need to form metal joints remarkably, so compared to the above-described main pressure bonding, a lower load, shorter time, and lower temperature may be used, and there are advantages such as improved productivity and prevention of deterioration of the connection part. ..
  • heat treatment may be performed in an oven or the like to further cure the semiconductor adhesive.
  • the heating temperature is a temperature at which the adhesive for semiconductors is cured, and is preferably almost completely cured. The heating temperature and the heating time may be set appropriately.
  • the present disclosure is not limited to the above embodiments.
  • the semiconductor chip and the semiconductor chip can be connected by the same method. After connecting the semiconductor chips, the voids may be eliminated by a pressure oven or pressure reflow.
  • thermosetting resin (b) having a weight average molecular weight of less than 10,000, the inorganic filler (d-1), and the resin filler (d-2) having the compounding amounts (units: parts by mass) shown in Table 1 were mixed with NV values ([ It was added to the organic solvent (cyclohexanone) so that the amount of the coating material after drying]/[the weight of coating material before drying] ⁇ 100) was 60% by mass.
  • the obtained coating varnish was coated on a base film (manufactured by Teijin DuPont Films Co., Ltd., product name: Purex A55) with a small precision coating device (manufactured by Renui Seiki Co., Ltd.), and a clean oven ( By drying (100° C./10 min) by ESPEC, a film adhesive having a film thickness of 20 ⁇ m was obtained.
  • a plurality of the obtained film adhesives are laminated at 80° C. with a roll laminator (manufactured by LAMI CORPORATION INC., product name: GK-13DX) to produce film adhesives with a predetermined thickness (40 ⁇ m and 200 ⁇ m). did.
  • the produced film adhesive was cut into a predetermined size (length 7.3 mm ⁇ width 7.3 mm ⁇ thickness 0.04 mm (40 ⁇ m)), and a semiconductor chip with solder bumps (chip size: length 7.3 mm ⁇ width 7. 3mm x thickness 0.05mm, bump height (total height of copper pillar + solder): about 45 ⁇ m, number of bumps: 1048 pins, pitch: 80 ⁇ m, product name: WALTS-TEG CC80, manufactured by WALTS) Lamination was performed under the conditions of 80° C./0.5 MPa/60 seconds. Lamination was performed using a vacuum laminator V130 (manufactured by Nikko Materials Co., Ltd.).
  • a semiconductor chip with a solder bump laminated with a film adhesive is used as a semiconductor chip (vertical 10 mm ⁇ horizontal 10 mm ⁇ thickness 0.1 mm, connection metal: Ni/Au, product name: WALTS-TEG IP80, manufactured by WALTS) )
  • a flip chip mounting device FCB3 manufactured by Panasonic Corporation.
  • the pressure bonding conditions were 80° C./0.5 seconds+260° C./3 seconds and 75N.
  • the stage temperature was 80°C. Thereafter, curing was performed at 175° C./2 hours to obtain a semiconductor device.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Wire Bonding (AREA)

Abstract

L'invention concerne une composition de résine qui comprend : (a) un composant de poids moléculaire élevé ayant un poids moléculaire moyen en poids de 10 000 ou plus, (b) une résine thermodurcissable ayant un poids moléculaire moyen en poids inférieur à 10 000, (c) un agent de durcissement et (d) une charge, la charge (d) comprenant du titanate de strontium.
PCT/JP2019/002959 2019-01-29 2019-01-29 Composition de résine, procédé de fabrication de dispositif à semi-conducteur et dispositif à semi-conducteur WO2020157828A1 (fr)

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JPH1060138A (ja) * 1996-08-27 1998-03-03 Matsushita Electric Works Ltd 配線基板材料
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