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WO2012081771A1 - Adhesive composition for a semiconductor, an adhesive film comprising the same and a semiconductor package using the same - Google Patents

Adhesive composition for a semiconductor, an adhesive film comprising the same and a semiconductor package using the same Download PDF

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Publication number
WO2012081771A1
WO2012081771A1 PCT/KR2011/002069 KR2011002069W WO2012081771A1 WO 2012081771 A1 WO2012081771 A1 WO 2012081771A1 KR 2011002069 W KR2011002069 W KR 2011002069W WO 2012081771 A1 WO2012081771 A1 WO 2012081771A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
composition
semiconductor
adhesive composition
adhesive
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2011/002069
Other languages
French (fr)
Korean (ko)
Inventor
편아람
어동선
송기태
조재현
김인환
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cheil Industries Inc
Original Assignee
Cheil Industries Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cheil Industries Inc filed Critical Cheil Industries Inc
Priority to CN201180060456.1A priority Critical patent/CN103261348B/en
Publication of WO2012081771A1 publication Critical patent/WO2012081771A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
    • H01L24/80—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected
    • H01L24/83—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected using a layer connector
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • 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
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • 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
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • 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
    • 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
    • C09J7/35—Heat-activated
    • 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
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C09J9/02—Electrically-conducting adhesives
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
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    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
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Definitions

  • the present invention relates to an adhesive composition for a semiconductor and an adhesive film comprising the same. More specifically, the present invention uses a specific acid anhydride that exhibits flux activity and can simultaneously be cured with an epoxy resin as a flux active curing agent to simultaneously control the flux function and curing of the insulating adhesive layer, while maintaining the stability of the solution and the acid remaining after mounting.
  • the present invention relates to an adhesive composition for semiconductors and an adhesive film including the same.
  • MCP multi-chip package
  • WSP wafer level stack package
  • Both the MCP method and the WSP method as described above are methods for increasing the capacity of a semiconductor device in terms of quantity by bonding and stacking a plurality of chips with an adhesive.
  • a bump is formed on the aluminum electrode of the semiconductor element used for this flip chip mounting, and the bump is electrically connected with wiring on a circuit board.
  • Solder is mainly used as the composition of such bumps, which are formed on exposed aluminum terminals which are connected to the internal wiring of the chip by vapor deposition or plating.
  • gold stud bumps and the like are formed in the wiring joint apparatus.
  • the electrode of the connection part is exposed to air, and the difference in the coefficient of linear expansion between the chip and the substrate is large. A large stress was applied and there was a problem in the reliability of the mounting.
  • a method of fixing the semiconductor element and the substrate by filling and curing the gap between the semiconductor element and the substrate with a resin paste or an adhesive film is adopted. It is.
  • flux activators such as organic acids are conventionally used.
  • acids such as carboxylic acid and sebacic acid have been directly used to develop an insulating adhesive layer that does not perform the flux process separately.
  • the acid is used directly, the solution stability of the insulating adhesive layer itself and the room temperature stability in the form of a film are deteriorated.
  • One object of the present invention is to provide an adhesive composition for a semiconductor, which enables the flux control and curing control of the insulating adhesive layer at the same time while eliminating the stability of the liquid solution and defects due to the acid remaining after mounting, and an adhesive film comprising the same. .
  • Still another object of the present invention is to provide an adhesive composition for a semiconductor, which can be stably applied even in TSV packaging, which is die-bonded at 250 ° C. or higher, and an adhesive film including the same.
  • Still another object of the present invention is to provide an adhesive composition for a semiconductor having excellent electrical connection reliability between bump chips, and an adhesive film including the same.
  • Still another object of the present invention is a high flux semiconductor adhesive composition capable of allowing a flux process to remove oxide films of metal bumps and solders and to allow bumps and solders to be sufficiently connected to each other during chip bonding due to heat and compression, and an adhesive comprising the same. It is for providing a film.
  • Still another object of the present invention is to provide a semiconductor package using the adhesive film.
  • the adhesive composition for a semiconductor includes at least one flux active curing agent represented by the following Chemical Formulas 1 to 3:
  • ring structure containing the acid anhydride of [A] is 0 to 3 Including a double bond, the ring structure is 4 to 8 carbon atoms, [B] is alicyclic, unsaturated alicyclic or aromatic, ring structure is 4 to 8 carbons, R One Is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group and an allyl group, and n is an integer of 0 to 2)
  • ring structure containing the acid anhydride of [C] is 0 to 3 Including a double bond, the ring structure is 4 to 8 carbon atoms, [D] is alicyclic, unsaturated alicyclic or aromatic, ring structure is 4 to 8 carbons, R 2 Is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group and an allyl group, and n is an integer of 1 to 4)
  • ring structure containing the acid anhydride of [E] is 0 to 3 Including a double bond of 4 to 8 carbon atoms in the ring structure, [F] is alicyclic, unsaturated alicyclic or aromatic, the ring structure is 4 to 8 carbon atoms, R 3 Is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group, an allyl group, and R 4 May be selected from the structures of formulas (i) to (viii), and n is an integer of 1 to 4)
  • the flux active hardener may comprise about 0.1 to about 10 weight percent of the total adhesive composition.
  • the flux active curing agent may have a melting point of about 100 to about 300 ° C.
  • the adhesive composition for a semiconductor may have a melt viscosity of about 2 ⁇ 10 4 to about 15 ⁇ 10 4 poise at 260 ° C.
  • the composition may have a contact angle of the solder to the metal bumps after bonding from about 10 to about 80 degrees.
  • the composition may be about 70% or more of the inter-metallic compound layer (Inter-Metallic Compound Layer) between the metal bump and the solder after bonding.
  • Inter-Metallic Compound Layer Inter-Metallic Compound Layer
  • the composition may include about 0.1% to about 5% by weight of an imidazole series curing catalyst.
  • the composition may include a polymer resin, an epoxy resin, at least one of the flux active curing agents of Formulas 1 to 3, a filler, and a curing catalyst.
  • the composition is about 20 to 60% by weight of the polymer resin (based on solids), about 10 to 60% by weight of the epoxy resin, about 0.1 to 10% by weight of the flux active curing agent, about 0.01 to 5% by weight of the curing catalyst, and about the filler It may include 15 to 40% by weight.
  • the polymer resin contains an epoxy group, the glass transition temperature may be about -30 ⁇ 80 °C.
  • composition may further comprise about 0.01 to 10% by weight of a silane coupling agent.
  • Another aspect of the present invention provides an adhesive film for a semiconductor formed from the adhesive composition.
  • the semiconductor package includes a chip mounting substrate; And first and second semiconductor chips stacked on one surface of the house-mounted substrate, wherein the first and second semiconductor chips are bonded with the adhesive film for semiconductor according to claim 11.
  • the present invention enables the flux function and curing control of the insulating adhesive layer at the same time while eliminating crude liquid stability and defects caused by acid remaining after mounting, and lowering the activity of the curing agent by reaction with epoxy and thus the high temperature of the unreacted cured residue. No defects such as decomposition, stable application even in TSV (throung silicon via) packaging that is die-bonded at 250 °C or higher, excellent electrical connection reliability between bump chips, and flux removal of metal bumps and solder oxides.
  • TSV throung silicon via
  • the adhesive composition of the present invention may include a polymer resin, an epoxy resin, at least one of the flux active curing agents of Formulas 1 to 3, a filler, and a curing catalyst.
  • the composition is about 20 to 60% by weight of the polymer resin (based on solids), about 10 to 60% by weight of the epoxy resin, about 0.1 to 10% by weight of the flux active curing agent, about 0.01 to 5% by weight of the curing catalyst, and about the filler It may include 15 to 40% by weight.
  • the polymer resin examples include polyimide resin, polystyrene resin, polyethylene resin, polyester resin, polyamide resin, butadiene rubber, acrylic rubber, (meth) acrylic resin, urethane resin, polyphenylene ether resin, polyether imide Resins, phenoxy resins, polycarbonate resins, polyphenylene ether resins, modified polyphenylene ether resins, mixtures thereof and the like can be used, but is not limited thereto.
  • the polymer resin may contain an epoxy group.
  • an epoxy group-containing (meth) acryl copolymer may be preferably applied.
  • the polymer resin may have a glass transition temperature of about -30 to 80 °C, preferably 0 to 60 °C, more preferably 5 to 35 °C. High flow can be secured in the above range, it is excellent in the ability to remove voids, it is possible to obtain adhesion and reliability.
  • the polymer resin may have a weight average molecular weight of 50,000 to 5,000,000 g / mol.
  • the polymer resin may include about 20 to 60% by weight, preferably 25 to 50% by weight, more preferably 25 to 45% by weight of the total composition (based on solids).
  • the epoxy resin has a curing and adhesive action
  • a liquid epoxy resin, a solid epoxy resin or a mixture thereof may be applied.
  • the liquid epoxy resin is, for example, bisphenol A liquid epoxy resin, bisphenol F liquid epoxy resin, trifunctional or higher polyfunctional liquid epoxy resin, rubber modified liquid epoxy resin, urethane modified liquid epoxy resin, acrylic modified liquid epoxy resin and A photosensitive liquid epoxy resin can be used individually or in mixture, More preferably, it is a bisphenol-A liquid epoxy resin.
  • the liquid epoxy resin (b1) may be used in an epoxy equivalent of about 100 to about 1500g / eq. Preferably from about 150 to about 800 g / eq and from about 150 to about 400 g / eq. It is excellent in the adhesiveness of the cured product in the above range, maintains the glass transition temperature, and may have excellent heat resistance.
  • the weight average molecular weight of the liquid epoxy resin may be used that is about 100 to 1,000 g / mol. There is an excellent flow in the above range.
  • the solid epoxy resin may be an epoxy resin having at least one functional group as a solid at or near solid phase at room temperature, and preferably a softening point Sp of about 30 to 100 ° C.
  • an epoxy resin having at least one functional group as a solid at or near solid phase at room temperature, and preferably a softening point Sp of about 30 to 100 ° C.
  • Products currently available as such solid epoxy resins include bisphenol-based solid epoxy resins of YD-017H, YD-020, YD020-L, YD-014, YD-014ER, YD-013K, YD-019K, and YD- 019, YD-017R, YD-017, YD-012, YD-011H, YD-011S, YD-011, YDF-2004, YDF-2001, and the like.As a phenol novolac-based Yuka Shell Epoxy Co., Ltd. Epicoat 152, Epicoat 154, Nippon Kayaku Co., Ltd.
  • the o-cresol novolac system includes YDCN-500-1P, YDCN-500-2P, YDCN-500-4P, YDCN-500-5P, YDCN-500-7P and YDCN- 500-8P, YDCN-500-10P, YDCN-500-80P, YDCN-500-80PCA60, YDCN-500-80PBC60, YDCN-500-90P, YDCN-500-90PA75, etc.
  • Epiclone N-665-EXP, and bisphenol-based novolac epoxy resins include KBPN-110, KBPN-120, KBPN-115, etc. of Kukdo Chemical, and Yuka Shell Epoxy Co., Ltd. Epon 1031S, Ciba as polyfunctional epoxy resins.
  • Araldito 0163 of Specialty Chemicals Detacol EX-611, Detacol EX-614, Detacol EX-614B, Detacol EX-622, Detacol EX-512, Detacol EX- 521, Detacol EX-421, Detacol EX-411, Detacol EX-321, Kukdo Chemical EP-5200R, KD-1012, EP-5100R, KD-1011, KDT-4400A70, KDT-4400, YH-434L , YH-434, YH-300, and the like.
  • Amine epoxy resins include Yuka Shell Epoxy Epicoat 604, Dokdo Chemical Co., Ltd.
  • heterocyclic epoxy resins include PT-810 of CIBA Specialty Chemical Co., Ltd. L-4234, ERL-4299, ERL-4221, ERL-4206, and naphthol-based epoxy resins include Epiclonal HP-4032, Epiclone HP-4032D, Epiclone HP-4700, and Epiclone 4701 from Japan Ink Chem. These can be used individually or in mixture of 2 or more types.
  • the epoxy resin may be included in about 10 to 60% by weight, preferably about 20 to 50% by weight, more preferably about 25 to 45% by weight of the total composition (based on solids). Excellent reliability and mechanical properties can be obtained in the above range.
  • the content of the epoxy resin b, and the content of the polymer resin a (based on a solid content) it may be a ⁇ b. In this case, better reliability can be obtained.
  • the adhesive composition of the present invention comprises at least one flux active curing agent represented by the following general formulas (1) to (3):
  • ring structure containing the acid anhydride of [A] is 0 to 3 Including a double bond, the ring structure is 4 to 8 carbon atoms, [B] is alicyclic, unsaturated alicyclic or aromatic, ring structure is 4 to 8 carbons, R One Is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group and an allyl group, and n is an integer of 0 to 2)
  • ring structure containing the acid anhydride of [C] is 0 to 3 Including a double bond, the ring structure is 4 to 8 carbon atoms, [D] is alicyclic, unsaturated alicyclic or aromatic, ring structure is 4 to 8 carbons, R 2 Is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group and an allyl group, and n is an integer of 1 to 4)
  • ring structure containing the acid anhydride of [E] is 0 to 3 Including a double bond of 4 to 8 carbon atoms in the ring structure, [F] is alicyclic, unsaturated alicyclic or aromatic, the ring structure is 4 to 8 carbon atoms, R 3 Is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group, an allyl group, and R 4 May be selected from the structures of formulas (i) to (viii), and n is an integer of 1 to 4)
  • the flux active hardener may be cis-5-Norbornene-endo-2,3-dicarboxylic anhydride, diphenic anhydride, bicyclo [2,2,2] oct-7-ene-2,3,5,6- tetracarboxylic dianhydride, phthalic anhydride, benzophenone-3,3'4,4'-tetracarboxylic dianhydride, endo-Bicyclo [2.2.2] oct-5-ene-2,3-dicarboxylic anhydride, Homophthalic anhydride, trans-1,2- Cyclohexanedicarboxylic anhydride, cis-5-Norbornene-exo-2,3-dicarboxylic anhydride, and the like, but are not necessarily limited thereto.
  • the flux active curing agent has a melting point of 100 to 300 ° C, preferably 120 to 250 ° C. It is possible to ensure the stability of the crude liquid even at high speed stirring in the above range.
  • the flux active curing agent may also preferably contain no carboxylic acid.
  • the flux active curing agent is 0.1 to 10% by weight, preferably 1 to 9% by weight of the total adhesive composition (based on solids). More preferably 3 to 8% by weight.
  • the content of the flux-active curing agent is c and the content of the epoxy resin is b
  • b: c may be about 2.5 to 10: 1, preferably about 3 to 8: 1. It has excellent Flux activity and adhesion in the above range.
  • the curing catalyst is a catalyst that shortens the curing time so that the epoxy resin can be completely cured during the semiconductor process.
  • melamine type, imidazole type, triphenylphosphine type catalyst, etc. can be used. Among these, it is preferably an imidazole catalyst.
  • imidazole-based catalyst examples include PN-23, PN-40 of Ajinomoto Precision Technology Co., Ltd., 2P4MZ, 2MA-OK, 2MAOK-PW, 2P4MHZ, etc., and Hoko Chemical Co., Ltd. (HOKKO CHEMICAL INDUSTRY CO., LTD) TPP-K, TPP-MK and the like. These can be used individually or in mixture of 2 or more types.
  • the curing catalyst is about 0.01 to 5% by weight, preferably about 0.05 to 3% by weight, more preferably about 0.1 to 0.8% by weight of the total adhesive composition (based on solids). It is excellent in heat resistance in the said range, a sudden reaction of an epoxy resin does not occur, and it can have the outstanding fluidity and connectivity.
  • the filler may be a metal component gold powder, silver powder, copper powder, nickel, and non-metallic components such as alumina, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, magnesium silicate, calcium oxide, magnesium oxide, aluminum oxide, Aluminum nitride, silica, boron nitride, titanium dioxide, glass, iron oxide, ceramics and the like can be used. Among these, silica is preferable.
  • the shape and size of the filler are not particularly limited, but usually, spherical silica and amorphous silica are mainly used in the filler, and the size thereof is preferably about 5 nm to about 20 ⁇ m.
  • the filler may be included in about 15 to 40% by weight of the total adhesive composition (based on solids). Preferably about 20 to 35% by weight. It may have excellent fluidity and film formability and adhesion in the above range.
  • the coupling agent acts as an adhesion promoter to promote adhesion due to chemical bonding between the surface of the inorganic material such as silica and the organic material when the composition is blended.
  • the coupling agent may be a commonly used silane coupling agent, for example, epoxy-containing 2- (3,4 epoxy cyclohexyl) -ethyltrimethoxysilane, 3-glycidoxytrimethoxysilane, 3-glycidoxypropyltriethoxysilane, N-2 (aminoethyl) 3-amitopropylmethyldimethoxysilane containing amine group, N-2 (aminoethyl) 3-aminopropyltrimethoxysilane, N- 2 (aminoethyl) 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysil-N- (1,3-dimethylbutylidene ) Propylamine, N-phenyl-3-aminopropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxy
  • the coupling agent is about 0.1 to about 10 weight percent, preferably about 0.5 to about 5 weight percent, more preferably about 0.7 to about 3 weight percent of the total adhesive composition (based on solids). Excellent adhesion reliability in the above range and can reduce the bubble generation problem.
  • the adhesive composition may further include an organic solvent.
  • the organic solvent lowers the viscosity of the adhesive composition for a semiconductor to facilitate the manufacture of a film.
  • toluene, xylene, propylene glycol monomethyl ether acetate, benzene, acetone, methyl ethyl ketone, tetrahydrofuran, dimethylformaldehyde, cyclohexanone, and the like may be used, but are not necessarily limited thereto.
  • the adhesive composition for a semiconductor may have a melt viscosity of about 2 ⁇ 10 4 to about 15 ⁇ 10 4 poise at 260 ° C. In the above range, since the metal bump and the smooth contact between the solder can be made well connected. Preferably about 3 ⁇ 10 4 to about 10 ⁇ 10 4 poise.
  • the composition may have a contact angle of the solder to the metal bumps after bonding from about 10 to about 80 degrees.
  • the contact angle when the oxide film of the solder is removed, the surface energy is increased, so that the electrical connection between the metal bump and the solder is well performed with excellent wetting.
  • the composition may be about 70% or more of the inter-metallic compound layer (Inter-Metallic Compound Layer) between the metal bump and the solder after bonding. Preferably at least about 80%, more preferably at least about 90%, most preferably about 95-100%.
  • the adhesive film forms an adhesive layer that satisfies the electrical connection reliability between bump chips, and is capable of a flux process for removing an oxide film of Cu bump and solder.
  • non-flux active hardener phenol hardener (HF-4M, manufacturer: Meiwa Plastic Industry Co., Ltd.)
  • Silane coupling agent Epoxy silane coupling agent (KBM-303, manufacturer: Shin-Etsu Co., Ltd.)
  • Tables 1 and 2 The components shown in Tables 1 and 2 were added to a 1 L cylindrical flask including a high speed stirring rod and dispersed at a low speed at 2000 rpm for 10 minutes and at a high speed at 5000 rpm for 30 minutes to prepare a composition for an adhesive film. Thereafter, each composition was filtered using a 50 ⁇ m capsule filter and then coated with an applicator to a thickness of 20 ⁇ m to prepare an adhesive film. The adhesive film was dried at 90 ° C. for 10 minutes and then dried at 110 ° C. for 5 minutes, and then stored at room temperature for 1 day.
  • Adhesive force [kgf / chip]: A 725 um thick wafer coated with a dioxide film was cut to a size of 5mm x 5mm, and then laminated at 60 degrees with an adhesive film and cut with only the adhesive part remaining. After laminating a piece of adhesive-laminated wafer on a 10 mm x 10 mm wafer with the same thickness of 725 um in order of 100 ° C and 260 ° C with 1.0 kgf for 10 seconds and curing at 175 ° C for 2 hours, PCT conditions (121 ° C) / 100% RH) Shear failure strength in 250 degreeC was measured after performing IR-reflow 3 times for 8 hours.
  • a 80um wafer coated with a dioxide film was cut into 10mm x 10mm in size, and then laminated at 60 degrees with an adhesive film, and cut off leaving only the adhesive part.
  • Adhesive lamination on the 725um 10mm x 10mm size wafer was pressed for 10 seconds at 100 °C and 260 °C in order of 1.0 kgf and irradiated with SAT (Scanning Acoustic Tomograph) to evaluate the good level of foam voids . ⁇ If the surface is satisfactory without foaming,?, If fine foaming occurs partially,?, And if the foaming phenomenon is severe, X is indicated.
  • Solder / Cu Bump connectivity The good level of Bump to Bump connectivity was evaluated according to the adhesive composition using chips manufactured for the evaluation of solder bump and Cu Bump connectivity. ⁇ If the connection is good,? Is partially lost, and?
  • Comparative Example 1 is a composition using trimellictic anhydride exposed to the carboxylic acid, when the acid is present in the composition, the reaction occurs with the epoxy resin due to the heat generated during high-speed stirring of the composition for film formation and the heat received during drying Can be. Therefore, a failure due to a fast curing reaction can be caused.
  • the crude liquid stability is also not good and the curing progresses partially during drying, which results in deterioration of the flow characteristics and disadvantageous characteristics in connection and adhesion between chips.
  • Comparative Examples 2 to 4 can also be seen that the stability of the crude liquid is not secured when the acid is used.

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Abstract

Provided is a high-fluidity adhesive composition for a semiconductor, wherein the composition: contains a flux-action curing agent having a specific structure; allows a flux process which satisfies the requirement for reliability of bump-chip electrical connection and removes any oxide film on the solder and a Cu bump as a bump-chip contact layer; and ensures adequate mutual contact between the solder and bump during chip bonding by thermocompression bonding. Also provided are an adhesive film comprising the composition and a semiconductor package using the composition.

Description

반도체용 접착 조성물, 이를 포함하는 접착 필름 및 이를 이용한 반도체 패키지Adhesive composition for semiconductor, Adhesive film comprising same and Semiconductor package using same

본 발명은 반도체용 접착 조성물 및 이를 포함하는 접착 필름에 관한 것이다. 보다 구체적으로 본 발명은 Flux활성을 나타내면서 에폭시 수지와 경화반응도 동시에 가능한 특정 산무수물을 플럭스 활성 경화제로 사용하여 Flux기능과 절연 접착층의 경화 제어를 동시에 가능하게 하면서 조액 안정성 및 실장 이후 잔류하는 산에 의한 불량이 없는 반도체용 접착 조성물 및 이를 포함하는 접착 필름에 관한 것이다. The present invention relates to an adhesive composition for a semiconductor and an adhesive film comprising the same. More specifically, the present invention uses a specific acid anhydride that exhibits flux activity and can simultaneously be cured with an epoxy resin as a flux active curing agent to simultaneously control the flux function and curing of the insulating adhesive layer, while maintaining the stability of the solution and the acid remaining after mounting. The present invention relates to an adhesive composition for semiconductors and an adhesive film including the same.

반도체 장치의 고용량화를 위해서는 단위면적당 셀의 갯수를 늘리는 질적인 측면의 고집적화 방법과, 여러 개의 칩을 적층하여 용량을 늘리는 양적인 측면의 패키징 기술적인 방법이 있다.In order to increase the capacity of semiconductor devices, there are high quality integration methods for increasing the number of cells per unit area and quantitative packaging technology methods for increasing capacity by stacking multiple chips.

이러한 패키징 방법에 있어서 종래에는 다층 칩 적층 패키지 방법(multi-chip package; 이하 MCP라 함) 방법이 주로 사용되어 왔는데, 이는 여러 개의 칩을 접착제에 의해 적층하고, 상하 칩을 와이어 본딩(wire bonding)을 이용하여 전기적으로 연결해주는 구조로서, 와이어 본딩을 해야하는 공간만큼 전체 패키지 크기가 적층된 칩의 공간보다 크게 되어 불필요한 공간이 존재하였다.In this packaging method, a multi-chip package (hereinafter referred to as MCP) method has been mainly used, which is a method of laminating a plurality of chips by an adhesive and wire bonding the upper and lower chips. It is a structure that is electrically connected by using, and the total package size is larger than the space of the stacked chip as much as the space to be wire bonded, there was an unnecessary space.

이러한 MCP 방법의 미비점을 개선하고자 등장한 것이 웨이퍼 레벨 적층 패키지(wafer level stack package; 이하 WSP라 함)인다. WSP는 회로가 형성된 웨이퍼에 관통전극(TSV, through silicon via)를 형성하고 이를 통전물질로 채워 전기적으로 층간을 직접 연결하는 패키징 방법이다.The wafer level stack package (hereinafter referred to as WSP) has emerged to improve the shortcomings of the MCP method. WSP is a packaging method that forms through-through vias (TSVs) on a wafer on which circuits are formed and fills them with a conductive material to electrically connect the layers directly.

상기와 같은 MCP방법과 WSP 방법은 모두 복수개의 칩을 접착제에 의해 접착하여 적층하는 방식으로 양적인 측면에서 반도체 장치의 용량을 늘리는 방법이다. Both the MCP method and the WSP method as described above are methods for increasing the capacity of a semiconductor device in terms of quantity by bonding and stacking a plurality of chips with an adhesive.

최근에는 전자기기의 소형화, 고밀도화에 따라 반도체소자를 최소의 면적으로 실장할 수 있는 플립 칩(flip-chip) 실장이 주목받고 있다. 이 플립 칩 실장에 사용되는 반도체소자의 알루미늄 전극 상에는 범프가 형성되어 있고, 범프는 회로기판 상에서 배선과 전기적으로 접합한다. 이러한 범프의 조성으로서는 주로 땜납이 사용되고, 이 땜납범프는 증착이나 도금으로 칩의 내부배선에 연결되는 노출된 알루미늄 단자 상에 형성한다. 그 밖에 배선접합장치에서 형성되는 금 스터드(stud) 범프 등이 있다.Recently, with the miniaturization and densification of electronic devices, a flip-chip mounting that can mount a semiconductor device with a minimum area of attention has attracted attention. A bump is formed on the aluminum electrode of the semiconductor element used for this flip chip mounting, and the bump is electrically connected with wiring on a circuit board. Solder is mainly used as the composition of such bumps, which are formed on exposed aluminum terminals which are connected to the internal wiring of the chip by vapor deposition or plating. In addition, there are gold stud bumps and the like that are formed in the wiring joint apparatus.

이러한 플립 칩에 의해 접속된 반도체장치는 그대로 사용되면 접속부의 전극이 공기중에 노출되어 있고, 칩과 기판의 선팽창계수의 차가 크기 때문에 땜납 리플로우 등의 후속공정의 열 이력에 의해 범프의 접속부분에 큰 응력이 걸려, 실장의 신뢰성에 문제가 있었다. 상기 문제를 해결하기 위해, 범프와 기판을 접속한 후 접합부분의 신뢰성을 향상시키기 위해서, 반도체소자와 기판의 빈틈을 수지 페이스트 또는 접착필름으로 메우고 경화시켜, 반도체소자와 기판을 고정하는 방법이 채택되어 있다. 이 경우 땜납 등의 표면에 존재하는 산화막을 제거하고 금속 접합을 용이하게 하기 위해 종래에는 유기산 등의 플럭스 활성제를 사용하였다. 그러나 플럭스 활성제의 잔사가 남는다면 보이드와 같은 기포가 발생하는 원인이 되거나 산성분에 따라서 배선의 부식이 발생하고 접속 신뢰성이 저하된다. 이에 따라 플럭스 활성제의 잔사를 세척하는 플럭스 공정이 필수적으로 요구된다. 그러나 근래 반도체 칩과 기판과의 사이에 갭이 좁은 경우 플럭스 활성제의 잔사의 세척이 어려운 문제가 있다. 따라서 Flux공정을 별도로 행하지 않게 하는 절연 접착층 개발이 필요한 실정이다. When the semiconductor device connected by the flip chip is used as it is, the electrode of the connection part is exposed to air, and the difference in the coefficient of linear expansion between the chip and the substrate is large. A large stress was applied and there was a problem in the reliability of the mounting. In order to solve the above problem, in order to improve the reliability of the bonded portion after connecting the bump and the substrate, a method of fixing the semiconductor element and the substrate by filling and curing the gap between the semiconductor element and the substrate with a resin paste or an adhesive film is adopted. It is. In this case, in order to remove the oxide film existing on the surface of solder or the like and to facilitate metal bonding, flux activators such as organic acids are conventionally used. However, if the residue of the flux activator remains, it may cause bubbles such as voids or corrosion of the wiring depending on the acid component, resulting in a decrease in connection reliability. Accordingly, a flux process for washing the residue of the flux activator is essential. However, recently, when the gap between the semiconductor chip and the substrate is narrow, it is difficult to wash the residue of the flux activator. Therefore, it is necessary to develop an insulating adhesive layer that does not perform the flux process separately.

Flux공정을 별도로 행하지 않게 하는 절연 접착층 개발을 위해 종래에는 카르복실산, 세바신산과 같은 산류를 직접 사용하였다. 하지만 이렇게 산류를 직접 사용하게 될 경우 절연 접착층 자체의 조액 안정성 및 필름 형태에서의 상온 안정성이 떨어지게 된다. 또한 산에 의해 절연 접착층 자체의 경화를 정확히 제어할 수 없을 뿐만 아니라 제품에 실장이 된 이후 잔류하게 되는 산에 의한 Bump의 부식, ion migration등의 불량이 발생하게 된다. Conventionally, acids such as carboxylic acid and sebacic acid have been directly used to develop an insulating adhesive layer that does not perform the flux process separately. However, if the acid is used directly, the solution stability of the insulating adhesive layer itself and the room temperature stability in the form of a film are deteriorated. In addition, it is impossible to precisely control the curing of the insulating adhesive layer itself by acid, and defects such as corrosion of the bump and ion migration due to the acid remaining after the product is mounted on the product may occur.

본 발명의 하나의 목적은 Flux기능과 절연 접착층의 경화 제어를 동시에 가능하게 하면서 조액 안정성 및 실장 이후 잔류하는 산에 의한 불량을 없앨 수 있는 반도체용 접착 조성물, 이를 포함하는 접착 필름을 제공하기 위한 것이다.One object of the present invention is to provide an adhesive composition for a semiconductor, which enables the flux control and curing control of the insulating adhesive layer at the same time while eliminating the stability of the liquid solution and defects due to the acid remaining after mounting, and an adhesive film comprising the same. .

본 발명의 다른 목적은 플럭스 활성 경화제 자체의 에폭시와의 반응에 의한 경화제 활성 저하와 이에 따른 미반응 경화체 잔류물의 고온 분해와 같은 불량이 발생하지 않는 반도체용 접착 조성물, 이를 포함하는 접착 필름을 제공하기 위한 것이다.It is another object of the present invention to provide an adhesive composition for a semiconductor, in which a defect such as deterioration of the curing agent activity due to the reaction of the flux-active curing agent itself with epoxy and high temperature decomposition of the unreacted curing body residue, does not occur, and an adhesive film comprising the same. It is for.

본 발명의 또 다른 목적은 250℃ 이상의 다이본딩하는 TSV(throung silicon via) 패키징에서도 안정적으로 적용할 수 있는 반도체용 접착 조성물, 이를 포함하는 접착 필름을 제공하기 위한 것이다.Still another object of the present invention is to provide an adhesive composition for a semiconductor, which can be stably applied even in TSV packaging, which is die-bonded at 250 ° C. or higher, and an adhesive film including the same.

본 발명의 또 다른 목적은 범프 Chip간 전기적 접속 신뢰성이 우수한 반도체용 접착 조성물, 이를 포함하는 접착 필름을 제공하기 위한 것이다.Still another object of the present invention is to provide an adhesive composition for a semiconductor having excellent electrical connection reliability between bump chips, and an adhesive film including the same.

본 발명의 또 다른 목적은 금속 Bump와 Solder의 산화막을 제거하는 Flux공정이 가능하고 가열 압착에 따른 Chip Bonding시 Bump와 Solder가 충분히 서로 접속하게 할 수 있는 고유동의 반도체용 접착 조성물, 이를 포함하는 접착 필름을 제공하기 위한 것이다.Still another object of the present invention is a high flux semiconductor adhesive composition capable of allowing a flux process to remove oxide films of metal bumps and solders and to allow bumps and solders to be sufficiently connected to each other during chip bonding due to heat and compression, and an adhesive comprising the same. It is for providing a film.

본 발명의 또 다른 목적은 상기 접착 필름을 이용한 반도체 패키지를 제공하기 위한 것이다.Still another object of the present invention is to provide a semiconductor package using the adhesive film.

본 발명의 하나의 관점은 반도체용 접착 조성물에 관한 것이다. 상기 반도체용 접착 조성물은 하기 화학식 1 내지 3 으로 표시되는 플럭스 활성 경화제를 최소한 1종 포함한다:One aspect of the invention relates to an adhesive composition for a semiconductor. The adhesive composition for a semiconductor includes at least one flux active curing agent represented by the following Chemical Formulas 1 to 3:

[화학식 1][Formula 1]

Figure PCTKR2011002069-appb-I000001
Figure PCTKR2011002069-appb-I000001

(상기에서 [A]의 산무수물이 포함된 환 구조는 0 ~ 3 의 이중결합을 포함하고, 환 구조를 이루는 탄소 수는 4~8 개이고, [B]는 지환족, 불포화 지환족 또는 방향족이며, 환 구조를 이루는 탄소 수는 4~8개이며, R1은 수소원자, 탄소 수 1~6의 알킬기, 탄소 수 6~12의 아릴기, 탄소 수 6~12의 치환 아릴기, 비닐기, 알릴기로 이루어진 군으로부터 선택되며, n은 0~2의 정수임)(In the above-described ring structure containing the acid anhydride of [A] is 0 to 3 Including a double bond, the ring structure is 4 to 8 carbon atoms, [B] is alicyclic, unsaturated alicyclic or aromatic, ring structure is 4 to 8 carbons, ROneIs selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group and an allyl group, and n is an integer of 0 to 2)

[화학식 2][Formula 2]

Figure PCTKR2011002069-appb-I000002
Figure PCTKR2011002069-appb-I000002

(상기에서 [C]의 산무수물이 포함된 환 구조는 0 ~ 3 의 이중결합을 포함하고, 환 구조를 이루는 탄소 수는 4~8 개이고, [D]는 지환족, 불포화 지환족 또는 방향족이며, 환 구조를 이루는 탄소 수는 4~8개이며, R2은 수소원자, 탄소 수 1~6의 알킬기, 탄소 수 6~12의 아릴기, 탄소 수 6~12의 치환 아릴기, 비닐기, 알릴기로 이루어진 군으로부터 선택되며, n은 1~4의 정수임)(In the above-mentioned ring structure containing the acid anhydride of [C] is 0 to 3 Including a double bond, the ring structure is 4 to 8 carbon atoms, [D] is alicyclic, unsaturated alicyclic or aromatic, ring structure is 4 to 8 carbons, R2Is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group and an allyl group, and n is an integer of 1 to 4)

[화학식 3] [Formula 3]

Figure PCTKR2011002069-appb-I000003
Figure PCTKR2011002069-appb-I000003

(상기에서 [E]의 산무수물이 포함된 환 구조는 0 ~ 3 의 이중결합을 포함하고, 환 구조를 이루는 탄소 수는 4~8 개이고, [F]는 지환족, 불포화 지환족 또는 방향족이며, 환 구조를 이루는 탄소 수는 4~8개이며, R3은 수소원자, 탄소 수 1~6의 알킬기, 탄소 수 6~12의 아릴기, 탄소 수 6~12의 치환 아릴기, 비닐기, 알릴기로 이루어진 군으로부터 선택되며, R4는 하기 화학식(i)~(viii)의 구조로부터 선택될 수 있고, n은 1~4의 정수임)(In the above-mentioned ring structure containing the acid anhydride of [E] is 0 to 3 Including a double bond of 4 to 8 carbon atoms in the ring structure, [F] is alicyclic, unsaturated alicyclic or aromatic, the ring structure is 4 to 8 carbon atoms, R3Is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group, an allyl group, and R4May be selected from the structures of formulas (i) to (viii), and n is an integer of 1 to 4)

Figure PCTKR2011002069-appb-I000004
Figure PCTKR2011002069-appb-I000004

구체예에서 상기 플럭스 활성 경화제는 전체 접착 조성물중 약 0.1 내지 약 10 중량% 포함할 수 있다. In embodiments, the flux active hardener may comprise about 0.1 to about 10 weight percent of the total adhesive composition.

상기 플럭스 활성 경화제는 융점이 약 100 내지 약 300 ℃ 일 수 있다. The flux active curing agent may have a melting point of about 100 to about 300 ° C.

상기 반도체용 접착조성물은 260 ℃에서 용융점도가 약 2 ×104 내지 약 15 ×104 poise 일 수 있다. The adhesive composition for a semiconductor may have a melt viscosity of about 2 × 10 4 to about 15 × 10 4 poise at 260 ° C.

상기 조성물은 본딩 후 금속 범프에 대한 Solder의 접촉각이 약 10 내지 약 80 도일 수 있다. The composition may have a contact angle of the solder to the metal bumps after bonding from about 10 to about 80 degrees.

상기 조성물은 본딩 후 금속 범프와 Solder사이의 금속간 화합물층(Inter-Metallic Compound Layer)이 본딩 면적 대비 약 70 % 이상일 수 있다. The composition may be about 70% or more of the inter-metallic compound layer (Inter-Metallic Compound Layer) between the metal bump and the solder after bonding.

상기 조성물은 이미다졸계 경화촉매를 약 0.1 내지 약 5 중량% 포함할 수 있다. The composition may include about 0.1% to about 5% by weight of an imidazole series curing catalyst.

한 구체예에서 상기 조성물은 고분자 수지, 에폭시계 수지, 상기 화학식 1 내지 3의 플럭스 활성 경화제 중 최소한 1종, 충진제 및 경화촉매를 포함할 수 있다. In one embodiment, the composition may include a polymer resin, an epoxy resin, at least one of the flux active curing agents of Formulas 1 to 3, a filler, and a curing catalyst.

구체예에서는 상기 조성물은 고분자 수지 약 20~60 중량% (고형분 기준), 에폭시계 수지 약 10~60 중량%, 플럭스 활성 경화제 약 0.1~10 중량%, 경화촉매 약 0.01~5 중량% 및 충진제 약 15~40 중량% 를 포함할 수 있다. In embodiments, the composition is about 20 to 60% by weight of the polymer resin (based on solids), about 10 to 60% by weight of the epoxy resin, about 0.1 to 10% by weight of the flux active curing agent, about 0.01 to 5% by weight of the curing catalyst, and about the filler It may include 15 to 40% by weight.

상기 고분자 수지는 에폭시기를 함유하며, 유리전이온도가 약 -30 ~ 80℃일 수 있다. The polymer resin contains an epoxy group, the glass transition temperature may be about -30 ~ 80 ℃.

다른 구체예에서는 상기 조성물은 실란커플링제를 약 0.01~10 중량% 더 포함할 수 있다. In another embodiment the composition may further comprise about 0.01 to 10% by weight of a silane coupling agent.

본 발명의 다른 관점은 상기 접착 조성물로 형성된 반도체용 접착 필름을 제공한다. Another aspect of the present invention provides an adhesive film for a semiconductor formed from the adhesive composition.

또한 본 발명의 또 다른 관점은 상기 반도체용 접착필름으로 접착된 반도체 패키지를 제공한다. 상기 반도체 패키지는 칩 탑재 기판; 및 상기 집 탑재 기판의 일면에 적층된 제1 및 제2 반도체 칩을 포함하며, 상기 제1 및 제2 반도체 칩은 제11항에 기재된 반도체용 접착필름으로 접착된 것을 특징으로 한다. In addition, another aspect of the present invention provides a semiconductor package bonded with the adhesive film for the semiconductor. The semiconductor package includes a chip mounting substrate; And first and second semiconductor chips stacked on one surface of the house-mounted substrate, wherein the first and second semiconductor chips are bonded with the adhesive film for semiconductor according to claim 11.

본 발명은 Flux기능과 절연 접착층의 경화 제어를 동시에 가능하게 하면서 조액 안정성 및 실장 이후 잔류하는 산에 의한 불량을 없앨 수 있고, 에폭시와의 반응에 의한 경화제 활성 저하와 이에 따른 미반응 경화체 잔류물의 고온 분해와 같은 불량이 발생하지 않으며, 250℃ 이상의 다이본딩하는 TSV(throung silicon via) 패키징에서도 안정적으로 적용할 수 있고, 범프 Chip간 전기적 접속 신뢰성이 우수며, 금속 Bump와 Solder의 산화막을 제거하는 Flux공정이 가능하고, 가열 압착에 따른 Chip Bonding시 Bump와 Solder가 충분히 서로 접속하게 할 수 있는 고유동의 반도체용 접착 조성물, 이를 포함하는 접착 필름과 상기 접착 필름을 이용한 반도체 패키지를 제공하는 발명의 효과를 갖는다. The present invention enables the flux function and curing control of the insulating adhesive layer at the same time while eliminating crude liquid stability and defects caused by acid remaining after mounting, and lowering the activity of the curing agent by reaction with epoxy and thus the high temperature of the unreacted cured residue. No defects such as decomposition, stable application even in TSV (throung silicon via) packaging that is die-bonded at 250 ℃ or higher, excellent electrical connection reliability between bump chips, and flux removal of metal bumps and solder oxides The process of the present invention, and the high-flow semiconductor adhesive composition that allows the bump and solder to be sufficiently connected to each other during chip bonding due to heat compression, the effect of the invention to provide an adhesive film comprising the same and a semiconductor package using the adhesive film Have

한 구체예에서 본 발명의 접착 조성물은 고분자 수지, 에폭시계 수지, 상기 화학식 1 내지 3의 플럭스 활성 경화제 중 최소한 1종, 충진제 및 경화촉매를 포함할 수 있다. In one embodiment, the adhesive composition of the present invention may include a polymer resin, an epoxy resin, at least one of the flux active curing agents of Formulas 1 to 3, a filler, and a curing catalyst.

구체예에서는 상기 조성물은 고분자 수지 약 20~60 중량% (고형분 기준), 에폭시계 수지 약 10~60 중량%, 플럭스 활성 경화제 약 0.1~10 중량%, 경화촉매 약 0.01~5 중량% 및 충진제 약 15~40 중량% 를 포함할 수 있다. In embodiments, the composition is about 20 to 60% by weight of the polymer resin (based on solids), about 10 to 60% by weight of the epoxy resin, about 0.1 to 10% by weight of the flux active curing agent, about 0.01 to 5% by weight of the curing catalyst, and about the filler It may include 15 to 40% by weight.

고분자 수지Polymer resin

상기 고분자 수지의 종류로는 폴리이미드 수지, 폴리스타이렌 수지, 폴리에틸렌 수지, 폴리에스테르 수지, 폴리아미드 수지, 부타디엔 고무, 아크릴 고무, (메타)아크릴 수지, 우레탄 수지, 폴리페닐렌 에테르 수지, 폴리 에테르 이미드 수지, 페녹시 수지, 폴리카보네이트 수지, 폴리페닐렌 에테르 수지, 변성 폴리페닐렌 에테르 수지 및 이들의 혼합물 등을 사용할 수 있지만, 이에 제한되지 않는다. 바람직하게는 상기 고분자 수지는 에폭시기를 함유할 수 있다. 구체예에서는 에폭시기 함유 (메타)아크릴 공중합체가 바람직하게 적용될 수 있다. Examples of the polymer resin include polyimide resin, polystyrene resin, polyethylene resin, polyester resin, polyamide resin, butadiene rubber, acrylic rubber, (meth) acrylic resin, urethane resin, polyphenylene ether resin, polyether imide Resins, phenoxy resins, polycarbonate resins, polyphenylene ether resins, modified polyphenylene ether resins, mixtures thereof and the like can be used, but is not limited thereto. Preferably, the polymer resin may contain an epoxy group. In an embodiment, an epoxy group-containing (meth) acryl copolymer may be preferably applied.

상기 고분자 수지는 유리전이온도가 약 -30 ~ 80℃, 바람직하게는 0 ~ 60℃, 보다 바람직하게는 5 ~ 35℃일 수 있다. 상기 범위에서 고유동을 확보할 수 있어 보이드 제거 능력이 우수하고, 접착력 및 신뢰성을 얻을 수 있다.  The polymer resin may have a glass transition temperature of about -30 to 80 ℃, preferably 0 to 60 ℃, more preferably 5 to 35 ℃. High flow can be secured in the above range, it is excellent in the ability to remove voids, it is possible to obtain adhesion and reliability.

구체예에서 상기 고분자 수지로는 중량평균분자량이 50,000 내지 5,000,000 g/mol 인 것을 사용될 수 있다. In embodiments, the polymer resin may have a weight average molecular weight of 50,000 to 5,000,000 g / mol.

상기 고분자 수지는 전체 조성물중(고형분 기준) 약 20~60 중량%, 바람직하게는 25~50 중량%, 더욱 바람직하게는 25~45 중량% 포함할 수 있다. The polymer resin may include about 20 to 60% by weight, preferably 25 to 50% by weight, more preferably 25 to 45% by weight of the total composition (based on solids).

에폭시계 수지Epoxy resin

상기 에폭시계 수지는 경화 및 접착 작용을 하는 것으로서, 액상 에폭시 수지, 고상 에폭시 수지 혹은 이들의 혼합이 모두 적용될 수 있다. As the epoxy resin has a curing and adhesive action, a liquid epoxy resin, a solid epoxy resin or a mixture thereof may be applied.

상기 액상 에폭시 수지는 예를 들면 비스페놀A형 액상 에폭시 수지, 비스페놀F형 액상 에폭시 수지, 3관능성 이상의 다관능성 액상 에폭시 수지, 고무변성 액상 에폭시 수지, 우레탄 변성 액상 에폭시 수지, 아크릴 변성 액상 에폭시 수지 및 감광성 액상 에폭시 수지를 단독 또는 혼합하여 이용할 수 있으며, 더욱 바람직하게는 비스페놀A형 액상 에폭시 수지이다. The liquid epoxy resin is, for example, bisphenol A liquid epoxy resin, bisphenol F liquid epoxy resin, trifunctional or higher polyfunctional liquid epoxy resin, rubber modified liquid epoxy resin, urethane modified liquid epoxy resin, acrylic modified liquid epoxy resin and A photosensitive liquid epoxy resin can be used individually or in mixture, More preferably, it is a bisphenol-A liquid epoxy resin.

상기 액상 에폭시 수지(b1)는 에폭시 당량이 약 100 내지 약 1500g/eq 이 사용될 수 있다. 바람직하게는 약 150 내지 약 800g/eq이고, 약 150 내지 약 400g/eq이다. 상기 범위에서 경화물의 접착성이 우수하고, 유리전이온도를 유지하며, 우수한 내열성을 가질 수 있다. The liquid epoxy resin (b1) may be used in an epoxy equivalent of about 100 to about 1500g / eq. Preferably from about 150 to about 800 g / eq and from about 150 to about 400 g / eq. It is excellent in the adhesiveness of the cured product in the above range, maintains the glass transition temperature, and may have excellent heat resistance.

또한 상기 액상 에폭시 수지의 중량평균분자량은 약 100 내지 1,000 g/mol 인 것이 사용될 수 있다. 상기 범위에서 흐름성이 뛰어난 장점이 있다. In addition, the weight average molecular weight of the liquid epoxy resin may be used that is about 100 to 1,000 g / mol. There is an excellent flow in the above range.

상기 고상 에폭시 수지는 상온에서 고상 또는 고상에 근접한 에폭시로서 하나 이상의 관능기를 가지고 있는 에폭시 수지를 사용할 수 있으며, 바람직하게는 연화점(Sp)이 약 30 ~ 100℃인 것을 사용할 수 있다. 예를 들면, 비스페놀계 에폭시, 페놀 노볼락(Phenol novolac)계 에폭시, o-크레졸 노볼락(Cresol novolac)계 에폭시, 다관능 에폭시, 아민계 에폭시, 복소환 함유 에폭시, 치환형 에폭시, 나프톨계 에폭시 및 이들의 유도체를 사용할 수 있다. The solid epoxy resin may be an epoxy resin having at least one functional group as a solid at or near solid phase at room temperature, and preferably a softening point Sp of about 30 to 100 ° C. For example, bisphenol epoxy, phenol novolac epoxy, o-cresol novolac epoxy, polyfunctional epoxy, amine epoxy, heterocyclic containing epoxy, substituted epoxy, naphthol epoxy And derivatives thereof.

이러한 고상 에폭시계 수지로서 현재 시판되고 있는 제품에는 비스페놀계 고상 에폭시로 국도화학의 YD-017H, YD-020, YD020-L, YD-014, YD-014ER, YD-013K, YD-019K, YD-019, YD-017R, YD-017, YD-012, YD-011H, YD-011S, YD-011, YDF-2004, YDF-2001 등이 있고, 페놀 노볼락(Phenol novolac)계로서는 유카 쉘 에폭시 주식회사의 체피코트 152, 에피코트 154, 일본화약주식회사의 EPPN-201, 다우케미컬의 DN-483, 국도화학의 YDPN-641, YDPN-638A80, YDPN-638, YDPN-637, YDPN-644, YDPN-631 등이 있고, o-크레졸 노볼락(Cresol novolac)계로서는 국도화학의 YDCN-500-1P, YDCN-500-2P, YDCN-500-4P, YDCN-500-5P, YDCN-500-7P, YDCN-500-8P, YDCN-500-10P, YDCN-500-80P, YDCN-500-80PCA60, YDCN-500-80PBC60, YDCN-500-90P, YDCN-500-90PA75 등이 있고 일본화약주식회사의 EOCN-102S, EOCN-103S, EOCN-104S, EOCN-1012, EOCN-1025, EOCN-1027, 독도화학주식회사의 YDCN-701, YDCN-702, YDCN-703, YDCN-704, 대일본 잉크화학의 에피클론 N-665-EXP 등이 있고, 비스페놀계 노볼락 에폭시로는 국도화학의 KBPN-110, KBPN-120, KBPN-115 등이 있고, 다관능 에폭시 수지로서는 유카 쉘 에폭시 주식회사 Epon 1031S, 시바스페샬리티케미칼주식회사의 아랄디이토 0163, 나가섭씨온도화성 주식회사의 데타콜 EX-611, 데타콜 EX-614, 데타콜 EX-614B, 데타콜 EX-622, 데타콜 EX-512, 데타콜 EX-521, 데타콜 EX-421, 데타콜 EX-411, 데타콜 EX-321, 국도화학의 EP-5200R, KD-1012, EP-5100R, KD-1011, KDT-4400A70, KDT-4400, YH-434L, YH-434, YH-300 등이 있으며, 아민계 에폭시 수지로서는 유카 쉘 에폭시 주식회사 에피코트 604, 독도화학주식회사의 YH-434, 미쓰비시가스화학 주식회사의 TETRAD-X, TETRAD-C, 스미토모화학주식회사의 ELM-120 등이 있고, 복소환 함유 에폭시 수지로는 시바스페샬리티케미칼주식회사의 PT-810, 치환형 에폭시 수지로는 UCC사의 ERL-4234, ERL-4299, ERL-4221, ERL-4206, 나프톨계 에폭시로는 대일본 잉크화학의 에피클론 HP-4032, 에피클론 HP-4032D, 에피클론 HP-4700, 에피클론 4701 등이 있고, 이것들은 단독으로 또는 2종류 이상을 혼합하여 사용할 수 있다.Products currently available as such solid epoxy resins include bisphenol-based solid epoxy resins of YD-017H, YD-020, YD020-L, YD-014, YD-014ER, YD-013K, YD-019K, and YD- 019, YD-017R, YD-017, YD-012, YD-011H, YD-011S, YD-011, YDF-2004, YDF-2001, and the like.As a phenol novolac-based Yuka Shell Epoxy Co., Ltd. Epicoat 152, Epicoat 154, Nippon Kayaku Co., Ltd. EPPN-201, Dow Chemical's DN-483, Kukdo Chemical's YDPN-641, YDPN-638A80, YDPN-638, YDPN-637, YDPN-644, YDPN-631 The o-cresol novolac system includes YDCN-500-1P, YDCN-500-2P, YDCN-500-4P, YDCN-500-5P, YDCN-500-7P and YDCN- 500-8P, YDCN-500-10P, YDCN-500-80P, YDCN-500-80PCA60, YDCN-500-80PBC60, YDCN-500-90P, YDCN-500-90PA75, etc. EOCN-103S, EOCN-104S, EOCN-1012, EOCN-1025, EOCN-1027, YDCN-701, YDCN-702, YDCN-703, YDCN-704 from Japan Dokdo Chemical Co., Ltd. Epiclone N-665-EXP, and bisphenol-based novolac epoxy resins include KBPN-110, KBPN-120, KBPN-115, etc. of Kukdo Chemical, and Yuka Shell Epoxy Co., Ltd. Epon 1031S, Ciba as polyfunctional epoxy resins. Araldito 0163 of Specialty Chemicals, Detacol EX-611, Detacol EX-614, Detacol EX-614B, Detacol EX-622, Detacol EX-512, Detacol EX- 521, Detacol EX-421, Detacol EX-411, Detacol EX-321, Kukdo Chemical EP-5200R, KD-1012, EP-5100R, KD-1011, KDT-4400A70, KDT-4400, YH-434L , YH-434, YH-300, and the like.Amine epoxy resins include Yuka Shell Epoxy Epicoat 604, Dokdo Chemical Co., Ltd. YH-434, Mitsubishi Gas Chemical Co., Ltd., TETRAD-X, TETRAD-C, and Sumitomo Chemical Co., Ltd. ELM-120 and the like, and heterocyclic epoxy resins include PT-810 of CIBA Specialty Chemical Co., Ltd. L-4234, ERL-4299, ERL-4221, ERL-4206, and naphthol-based epoxy resins include Epiclonal HP-4032, Epiclone HP-4032D, Epiclone HP-4700, and Epiclone 4701 from Japan Ink Chem. These can be used individually or in mixture of 2 or more types.

상기 에폭시계 수지는 전체 조성물(고형분 기준)중 약 10~60 중량%, 바람직하게는 약 20~50 중량%, 더욱 바람직하게는 약 25~45 중량%로 포함될 수 있다. 상기 범위에서 우수한 신뢰성 및 기계적 물성을 얻을 수 있다. 구체예에서는 상기 에폭시계 수지의 함량을 b, 상기 고분자 수지의 함량을 a (고형분 기준) 라고 할 때, a < b 일 수 있다. 이 경우 보다 우수한 신뢰성을 얻을 수 있다. The epoxy resin may be included in about 10 to 60% by weight, preferably about 20 to 50% by weight, more preferably about 25 to 45% by weight of the total composition (based on solids). Excellent reliability and mechanical properties can be obtained in the above range. In embodiments, when the content of the epoxy resin b, and the content of the polymer resin a (based on a solid content), it may be a <b. In this case, better reliability can be obtained.

플럭스 활성 경화제Flux active hardener

본 발명의 접착 조성물은 하기 화학식 1 내지 3 으로 표시되는 플럭스 활성 경화제를 최소한 1종 포함한다:The adhesive composition of the present invention comprises at least one flux active curing agent represented by the following general formulas (1) to (3):

[화학식 1][Formula 1]

Figure PCTKR2011002069-appb-I000005
Figure PCTKR2011002069-appb-I000005

(상기에서 [A]의 산무수물이 포함된 환 구조는 0 ~ 3 의 이중결합을 포함하고, 환 구조를 이루는 탄소 수는 4~8 개이고, [B]는 지환족, 불포화 지환족 또는 방향족이며, 환 구조를 이루는 탄소 수는 4~8개이며, R1은 수소원자, 탄소 수 1~6의 알킬기, 탄소 수 6~12의 아릴기, 탄소 수 6~12의 치환 아릴기, 비닐기, 알릴기로 이루어진 군으로부터 선택되며, n은 0~2의 정수임)(In the above-described ring structure containing the acid anhydride of [A] is 0 to 3 Including a double bond, the ring structure is 4 to 8 carbon atoms, [B] is alicyclic, unsaturated alicyclic or aromatic, ring structure is 4 to 8 carbons, ROneIs selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group and an allyl group, and n is an integer of 0 to 2)

[화학식 2][Formula 2]

Figure PCTKR2011002069-appb-I000006
Figure PCTKR2011002069-appb-I000006

(상기에서 [C]의 산무수물이 포함된 환 구조는 0 ~ 3 의 이중결합을 포함하고, 환 구조를 이루는 탄소 수는 4~8 개이고, [D]는 지환족, 불포화 지환족 또는 방향족이며, 환 구조를 이루는 탄소 수는 4~8개이며, R2은 수소원자, 탄소 수 1~6의 알킬기, 탄소 수 6~12의 아릴기, 탄소 수 6~12의 치환 아릴기, 비닐기, 알릴기로 이루어진 군으로부터 선택되며, n은 1~4의 정수임)(In the above-mentioned ring structure containing the acid anhydride of [C] is 0 to 3 Including a double bond, the ring structure is 4 to 8 carbon atoms, [D] is alicyclic, unsaturated alicyclic or aromatic, ring structure is 4 to 8 carbons, R2Is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group and an allyl group, and n is an integer of 1 to 4)

[화학식 3] [Formula 3]

Figure PCTKR2011002069-appb-I000007
Figure PCTKR2011002069-appb-I000007

(상기에서 [E]의 산무수물이 포함된 환 구조는 0 ~ 3 의 이중결합을 포함하고, 환 구조를 이루는 탄소 수는 4~8 개이고, [F]는 지환족, 불포화 지환족 또는 방향족이며, 환 구조를 이루는 탄소 수는 4~8개이며, R3은 수소원자, 탄소 수 1~6의 알킬기, 탄소 수 6~12의 아릴기, 탄소 수 6~12의 치환 아릴기, 비닐기, 알릴기로 이루어진 군으로부터 선택되며, R4는 하기 화학식(i)~(viii)의 구조로부터 선택될 수 있고, n은 1~4의 정수임)(In the above-mentioned ring structure containing the acid anhydride of [E] is 0 to 3 Including a double bond of 4 to 8 carbon atoms in the ring structure, [F] is alicyclic, unsaturated alicyclic or aromatic, the ring structure is 4 to 8 carbon atoms, R3Is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group, an allyl group, and R4May be selected from the structures of formulas (i) to (viii), and n is an integer of 1 to 4)

Figure PCTKR2011002069-appb-I000008
Figure PCTKR2011002069-appb-I000008

예를 들면, 상기 플럭스 활성 경화제로는 cis-5-Norbornene-endo-2,3-dicarboxylic anhydride, diphenic anhydride, bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, phthalic anhydride, benzophenone-3,3'4,4'-tetracarboxylic dianhydride, endo-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride , Homophthalic anhydride , trans-1,2-Cyclohexanedicarboxylic anhydride , cis-5-Norbornene-exo-2,3-dicarboxylic anhydride 등이 있으며, 반드시 이에 제한되는 것은 아니다. For example, the flux active hardener may be cis-5-Norbornene-endo-2,3-dicarboxylic anhydride, diphenic anhydride, bicyclo [2,2,2] oct-7-ene-2,3,5,6- tetracarboxylic dianhydride, phthalic anhydride, benzophenone-3,3'4,4'-tetracarboxylic dianhydride, endo-Bicyclo [2.2.2] oct-5-ene-2,3-dicarboxylic anhydride, Homophthalic anhydride, trans-1,2- Cyclohexanedicarboxylic anhydride, cis-5-Norbornene-exo-2,3-dicarboxylic anhydride, and the like, but are not necessarily limited thereto.

구체예에서는 상기 플럭스 활성 경화제는 융점이 100 내지 300 ℃, 바람직하게는 120 내지 250 ℃이다. 상기 범위에서 고속 교반시에도 조액 안정성을 확보할 수 있다. In specific embodiments, the flux active curing agent has a melting point of 100 to 300 ° C, preferably 120 to 250 ° C. It is possible to ensure the stability of the crude liquid even at high speed stirring in the above range.

또한 상기 플럭스 활성 경화제는 바람직하게는 카르복실산을 함유하지 않을 수 있다. The flux active curing agent may also preferably contain no carboxylic acid.

구체예에서 상기 플럭스 활성 경화제는 전체 접착 조성물(고형분 기준)중 0.1 내지 10 중량%, 바람직하게는 1 내지 9 중량%. 더욱 바람직하게는 3 내지 8 중량% 포함할 수 있다. 상기 범위에서 Flux활성도 나타내면서 접속이 용이할 정도로 에폭시 수지와 반응성을 조절할 수 있다, 또한 고유동을 확보할 수 있어 Bump간 접속성이 우수하다. 구체예에서는 상기 플럭스 활성 경화제의 함량이 c 이고, 상기 상기 에폭시계 수지의 함량을 b 라고 할 때, b: c = 약 2.5~10: 1, 바람직하게는 약 3~8 :1 일 수 있다. 상기 범위에서 우수한 Flux활성과 접착력을 갖는다. In embodiments the flux active curing agent is 0.1 to 10% by weight, preferably 1 to 9% by weight of the total adhesive composition (based on solids). More preferably 3 to 8% by weight. In the above range, it is possible to control the reactivity with the epoxy resin to the extent that it is easy to connect while showing Flux activity, and also it is possible to secure a high flow and excellent connection between the bumps. In an embodiment, when the content of the flux-active curing agent is c and the content of the epoxy resin is b, b: c may be about 2.5 to 10: 1, preferably about 3 to 8: 1. It has excellent Flux activity and adhesion in the above range.

경화촉매Curing catalyst

상기 경화촉매는 반도체 공정 동안에 에폭시 수지가 완전히 경화될 수 있도록 경화시간을 단축시키는 촉매이다. 구체예에서는 멜라민계, 이미다졸계, 트리페닐포스핀계 촉매 등을 사용할 수 있다. 이중 바람직하게는 이미다졸계 촉매이다. The curing catalyst is a catalyst that shortens the curing time so that the epoxy resin can be completely cured during the semiconductor process. In a specific example, melamine type, imidazole type, triphenylphosphine type catalyst, etc. can be used. Among these, it is preferably an imidazole catalyst.

상기 이미다졸계 촉매의 예로는 아지노모토 정밀기술주식회사의 PN-23, PN-40, 사국화학주식회사의 2P4MZ, 2MA-OK, 2MAOK-PW, 2P4MHZ 등이 있고, 호코케미칼사(HOKKO CHEMICAL INDUSTRY CO., LTD)의 TPP-K, TPP-MK 등이 있다. 이들은 단독 또는 2종 이상을 혼합하여 사용할 수 있다.Examples of the imidazole-based catalyst include PN-23, PN-40 of Ajinomoto Precision Technology Co., Ltd., 2P4MZ, 2MA-OK, 2MAOK-PW, 2P4MHZ, etc., and Hoko Chemical Co., Ltd. (HOKKO CHEMICAL INDUSTRY CO., LTD) TPP-K, TPP-MK and the like. These can be used individually or in mixture of 2 or more types.

상기 경화촉매는 전체 접착 조성물(고형분 기준)중 약 0.01~5 중량%, 바람직하게는 약 0.05~3 중량%, 더욱 바람직하게는 약 0.1~0.8 중량% 이다. 상기 범위에서 내열성이 우수하고, 에폭시 수지의 급격한 반응이 일어나지 않으며, 우수한 유동성 및 접속성을 가질 수 있다. The curing catalyst is about 0.01 to 5% by weight, preferably about 0.05 to 3% by weight, more preferably about 0.1 to 0.8% by weight of the total adhesive composition (based on solids). It is excellent in heat resistance in the said range, a sudden reaction of an epoxy resin does not occur, and it can have the outstanding fluidity and connectivity.

충진제Filler

상기 충진제는 금속성분인 금분, 은분, 동분, 니켈을 사용할 수 있고, 비금속성분인 알루미나, 수산화알루미늄, 수산화마그네슘, 탄산칼슘, 탄산마그네슘, 규산칼슘, 규산마그네슘, 산화칼슘, 산화마그네슘, 산화알루미늄, 질화알루미늄, 실리카, 질화붕소, 이산화티타늄, 유리, 산화철, 세라믹 등을 사용할 수 있다. 이중 바람직하게는 실리카이다. The filler may be a metal component gold powder, silver powder, copper powder, nickel, and non-metallic components such as alumina, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, magnesium silicate, calcium oxide, magnesium oxide, aluminum oxide, Aluminum nitride, silica, boron nitride, titanium dioxide, glass, iron oxide, ceramics and the like can be used. Among these, silica is preferable.

상기 충진제의 형상과 크기는 특별히 제한되지 않으나, 통상적으로 충진제 중에서는 구형 실리카와 무정형 실리카가 주로 사용되고, 그 크기는 약 5㎚ 내지 약 20㎛인 것이 바람직하다.The shape and size of the filler are not particularly limited, but usually, spherical silica and amorphous silica are mainly used in the filler, and the size thereof is preferably about 5 nm to about 20 μm.

상기 충진제는 전체 접착 조성물(고형분 기준)중 약 15~40 중량%로 포함될 수 있다. 바람직하게는 약 20~35 중량%이다. 상기 범위에서 우수한 유동성과 필름형성성 및 접착성을 가질 수 있다. The filler may be included in about 15 to 40% by weight of the total adhesive composition (based on solids). Preferably about 20 to 35% by weight. It may have excellent fluidity and film formability and adhesion in the above range.

커플링제Coupling agent

상기 커플링제는 조성물 배합시 실리카와 같은 무기물질의 표면과 유기물질간의 화학적 결합으로 인한 접착력을 증진시키기 위한 접착증진제의 작용을 한다.The coupling agent acts as an adhesion promoter to promote adhesion due to chemical bonding between the surface of the inorganic material such as silica and the organic material when the composition is blended.

상기 커플링제는 통상적으로 사용되는 실란 커플링제를 사용할 수 있으며, 예를 들어 에폭시가 함유된 2-(3,4 에폭시 사이클로 헥실)-에틸트리메톡시실란, 3-글리시독시트리메톡시실란, 3-글리시독시프로필트리에톡시실란, 아민기가 함유된 N-2(아미노에틸)3-아미토프로필메틸디메톡시실란, N-2(아미노에틸)3-아미노프로필트리메톡시실란, N-2(아미노에틸)3-아미노프로필트리에톡시실란, 3-아미노프로필트리메톡시실란, 3-아미노프로필트리에톡시실란, 3-트리에톡시실리-N-(1,3-디메틸뷰틸리덴)프로필아민, N-페닐-3-아미노프로필트리메톡시실란, 머캅토가 함유된 3-머캅토프로필메틸디메톡시실란, 3-머캅토프로필트리에톡시실란, 이소시아네이트가 함유된 3-이소시아네이트프로필트리에톡시실란 등이 있으며, 이들을 단독 또는 2종 이상을 혼합하여 사용할 수 있다.The coupling agent may be a commonly used silane coupling agent, for example, epoxy-containing 2- (3,4 epoxy cyclohexyl) -ethyltrimethoxysilane, 3-glycidoxytrimethoxysilane, 3-glycidoxypropyltriethoxysilane, N-2 (aminoethyl) 3-amitopropylmethyldimethoxysilane containing amine group, N-2 (aminoethyl) 3-aminopropyltrimethoxysilane, N- 2 (aminoethyl) 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysil-N- (1,3-dimethylbutylidene ) Propylamine, N-phenyl-3-aminopropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane with mercapto, 3-mercaptopropyltriethoxysilane, 3-isocyanatepropyl with isocyanate Triethoxysilane and the like, and these may be used alone or in combination of two or more thereof. have.

상기 커플링제는 전체 접착 조성물(고형분 기준)중 약 0.1 내지 약 10 중량%, 바람직하게는 약 0.5 내지 약 5 중량%, 더욱 바람직하게는 약 0.7 내지 약 3 중량%이다. 상기 범위에서 접착신뢰성이 우수하고 기포발생 문제를 줄일 수 있다. The coupling agent is about 0.1 to about 10 weight percent, preferably about 0.5 to about 5 weight percent, more preferably about 0.7 to about 3 weight percent of the total adhesive composition (based on solids). Excellent adhesion reliability in the above range and can reduce the bubble generation problem.

유기용매Organic solvent

상기 접착 조성물은 유기용매를 추가로 포함할 수 있다. 상기 유기용매는 반도체용 접착 조성물의 점도를 낮게 하여 필름의 제조가 용이하도록 한다. 구체적으로 톨루엔, 자일렌, 프로필렌 글리콜 모노메틸 에테르 아세테이트, 벤젠, 아세톤, 메틸에틸케톤, 테트라히드로 퓨란, 디메틸포름알데히드, 시클로헥사논 등을 사용할 수 있으며, 반드시 이에 제한되지 않는다. The adhesive composition may further include an organic solvent. The organic solvent lowers the viscosity of the adhesive composition for a semiconductor to facilitate the manufacture of a film. Specifically, toluene, xylene, propylene glycol monomethyl ether acetate, benzene, acetone, methyl ethyl ketone, tetrahydrofuran, dimethylformaldehyde, cyclohexanone, and the like may be used, but are not necessarily limited thereto.

상기 반도체용 접착조성물은 260 ℃에서 용융점도가 약 2 ×104 내지 약 15 ×104 poise 일 수 있다. 상기 범위일 경우, 금속 범프와 solder간의 원활한 접촉을 가지므로 전기 접속이 잘 이루어 질 수 있다. 바람직하게는 약 3 ×104 내지 약 10 ×104 poise 일 수 있다. The adhesive composition for a semiconductor may have a melt viscosity of about 2 × 10 4 to about 15 × 10 4 poise at 260 ° C. In the above range, since the metal bump and the smooth contact between the solder can be made well connected. Preferably about 3 × 10 4 to about 10 × 10 4 poise.

상기 조성물은 본딩 후 금속 범프에 대한 Solder의 접촉각이 약 10 내지 약 80 도일 수 있다. 상기 접촉각일 경우, solder의 산화막이 제거 되면 표면에너지가 높아져서 우수한 wetting을 가지고 금속 범프와 solder의 전기 접속이 잘 이루어진다.The composition may have a contact angle of the solder to the metal bumps after bonding from about 10 to about 80 degrees. In the case of the contact angle, when the oxide film of the solder is removed, the surface energy is increased, so that the electrical connection between the metal bump and the solder is well performed with excellent wetting.

상기 조성물은 본딩 후 금속 범프와 Solder사이의 금속간 화합물층(Inter-Metallic Compound Layer)이 본딩 면적 대비 약 70 % 이상일 수 있다. 바람직하게는 약 80 % 이상, 더욱 바람직하게는 약 90 % 이상, 가장 바람직하게는 약 95~100 % 일 수 있다. The composition may be about 70% or more of the inter-metallic compound layer (Inter-Metallic Compound Layer) between the metal bump and the solder after bonding. Preferably at least about 80%, more preferably at least about 90%, most preferably about 95-100%.

본 발명의 다른 관점은 상기 접착 조성물로 형성된 반도체용 접착 필름에 관한 것이다. 상기 접착 필름은 범프 Chip간 전기적 접속 신뢰성을 만족하는 접착층을 형성하며, Cu Bump와 Solder의 산화막을 제거하는 Flux공정이 가능하다. 또한 가열 압착에 따른 Chip Bonding시 Bump와 Solder가 충분히 서로 접속하게 할 수 있다. 또한 접착력이 우수할 뿐만 아니라, 발포성 보이드가 발생하지 않고 Bump와 Solder간 imc 층을 충분한 면적으로 형성할 수 있다. Another aspect of the present invention relates to an adhesive film for a semiconductor formed from the adhesive composition. The adhesive film forms an adhesive layer that satisfies the electrical connection reliability between bump chips, and is capable of a flux process for removing an oxide film of Cu bump and solder. In addition, it is possible to make the bump and the solder fully connected to each other during chip bonding due to heat and compression. In addition to excellent adhesion, it is possible to form a sufficient area of the imc layer between the bump and the solder without foaming voids.

본 발명은 하기의 실시예에 의하여 보다 더 잘 이해 될 수 있으며, 하기의 실시예는 본 발명의 예시목적을 위한 것이며 첨부된 특허청구범위에 의하여 한정되는 보호범위를 제한하고자 하는 것은 아니다.The invention can be better understood by the following examples, which are intended to illustrate the invention and are not intended to limit the scope of protection defined by the appended claims.

실시예Example

하기 실시예 및 비교예에서 사용된 각 성분의 사양은 다음과 같다: The specifications of each component used in the following Examples and Comparative Examples are as follows:

(A) 고분자 수지(A) polymer resin

(a1) 에폭시기 함유 고분자 수지 (SG-P3TEA, Tg=15℃, 고형분 15%, 제조원: 나가세켐텍스) (a1) epoxy group-containing polymer resin (SG-P3TEA, Tg = 15 ℃, solid content 15%, manufacturer: Nagase Chemtex)

(a2) 에폭시기 함유 고분자 수지 (KLS-1062DR, Tg=19℃, 고형분 20%, 제조원: 후지쿠라화학) (a2) Epoxy group-containing polymer resin (KLS-1062DR, Tg = 19 ° C., solid content 20%, manufacturer: Fujikura Chemical)

(B) 에폭시계 수지(B) epoxy resin

(b1)크레졸 노볼락계 에폭시 수지 (YDCN-500-10P, 제조원: 국도화학)(b1) Cresol novolac epoxy resin (YDCN-500-10P, manufactured by Kukdo Chemical)

(b2)나프탈렌계 에폭시 수지 (NC-3000H, 제조원: 일본화약)(b2) Naphthalene epoxy resin (NC-3000H, manufacturer: Nippon Gunpowder)

(b3)비스페놀 A형 에폭시 수지 (YD-011, 제조원: 국도화학)(b3) Bisphenol A epoxy resin (YD-011, manufactured by Kukdo Chemical)

(C) 플럭스 활성 경화제(C) flux active hardener

(c1)Benzophenone-3,3'4,4'-tetracarboxylic dianhydride, 제조원: Sigma-Aldrich, mp 220℃(c1) Benzophenone-3,3'4,4'-tetracarboxylic dianhydride, manufactured by Sigma-Aldrich, mp 220

(c2)Diphenic anhydride, 제조원: Sigma-Aldrich, mp 226℃(c2) Diphenic anhydride, manufactured by Sigma-Aldrich, mp 226 ℃

(c3)cis-5-Norbornene-endo-2,3-dicarboxylic anhydride, 제조원: Sigma-Aldrich, mp 166℃(c3) cis-5-Norbornene-endo-2,3-dicarboxylic anhydride manufactured by Sigma-Aldrich, mp 166 ° C

(c4)Phthalic anhydride, 제조원: Sigma-Aldrich, mp 130℃(c4) Phthalic anhydride, manufactured by Sigma-Aldrich, mp 130 ° C

(c5)Bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, 제조원: Sigma-Aldrich, mp 300℃ (c5) Bicyclo [2,2,2] oct-7-ene-2,3,5,6-tetracarboxylic dianhydride from Sigma-Aldrich, mp 300 ° C

(c6)Trimellitic anhydride, 제조원: Sigma-Aldrich), mp 226℃(c6) Trimellitic anhydride, manufactured by Sigma-Aldrich), mp 226 ° C

(c7)Citric Acid, 제조원: Sigma-Aldrich, mp 156℃(c7) Citric Acid, manufactured by Sigma-Aldrich, mp 156 ° C

(c8)Iminodiacetic acid, 제조원: Sigma-Aldrich, mp 243℃(c8) Iminodiacetic acid, manufactured by Sigma-Aldrich, mp 243 ° C

(c9)Ethylenediaminetetraacetic acid, 제조원: Sigma-Aldrich, mp 250℃(c9) Ethylenediaminetetraacetic acid, manufactured by Sigma-Aldrich, mp 250 ° C

(C') 비플럭스 활성 경화제: 페놀 경화제 (HF-4M, 제조원: 메이와 플라스틱산업주식회사)(C ') non-flux active hardener: phenol hardener (HF-4M, manufacturer: Meiwa Plastic Industry Co., Ltd.)

(D) 경화촉매: 이미다졸계 경화촉매 (2P4MHZ-PW, 제조원: 사국화학)(D) Curing catalyst: imidazole series curing catalyst (2P4MHZ-PW, manufactured by Saguk Chemical)

(E) 충진제: 구형 실리카 (SC-2500SQ, 제조원: 아드마텍스(Admatechs)(E) Filler: Spherical Silica (SC-2500SQ, manufacturer: Admatechs)

(F) 실란커플링제: 에폭시 실란 커플링제 (KBM-303, 제조원: 신에쯔주식회사)(F) Silane coupling agent: Epoxy silane coupling agent (KBM-303, manufacturer: Shin-Etsu Co., Ltd.)

(G) 용매: 메틸에틸케톤 (제조원: 삼전화학)(G) Solvent: Methyl ethyl ketone (Samjeon Chemical)

표 1 실시예 1 2 3 4 5 (A) (a1) - - 100 42.4 - (a2) 133.3 145.1 - 80 133.3 (B) (b1) 29.4 16 - 12 8 (b2) 4.0 16 24 - 8 (b3) - - 10.7 20 16.8 (C) (c1) - - - - 6.2 (c2) - 5.2 - - - (c3) 5.6 - - - - (c4) - - - 6.5 - (c5) - - 4.2 - - (c6) - - - - - (c7) - - - - - (c8) - - - - - (c9) - - - - - (C') - - - - - (D) 0.2 0.2 0.2 0.2 0.2 (E) 20 20 20 20 20 (F) 0.8 0.8 0.8 0.8 0.8 (G) 80 80 80 80 80 Table 1 Example One 2 3 4 5 (A) (a1) - - 100 42.4 - (a2) 133.3 145.1 - 80 133.3 (B) (b1) 29.4 16 - 12 8 (b2) 4.0 16 24 - 8 (b3) - - 10.7 20 16.8 (C) (c1) - - - - 6.2 (c2) - 5.2 - - - (c3) 5.6 - - - - (c4) - - - 6.5 - (c5) - - 4.2 - - (c6) - - - - - (c7) - - - - - (c8) - - - - - (c9) - - - - - (C ') - - - - - (D) 0.2 0.2 0.2 0.2 0.2 (E) 20 20 20 20 20 (F) 0.8 0.8 0.8 0.8 0.8 (G) 80 80 80 80 80

표 2 비교예 1 2 3 4 5 (A) (a1) 100 120 48 - 73.6 (a2) - - 66.7 115.2 53.3 (B) (b1) - 14.6 10.4 12 12 (b2) 10.2 - 24 - 11.4 (b3) 24 16 - 22.2 4 (C) (c1) - - - - - (c2) - - - - - (c3) - - - - - (c4) - - - - - (c5) - - - - - (c6) 4.8 - - - - (c7) - - 5 - - (c8) - - - 7.5 - (c9) - 4.4 - - - (C') - - - - 8.8 (D) 0.2 0.2 0.2 0.2 0.2 (E) 20 20 20 20 20 (F) 0.8 0.8 0.8 0.8 0.8 (G) 80 80 80 80 80 TABLE 2 Comparative example One 2 3 4 5 (A) (a1) 100 120 48 - 73.6 (a2) - - 66.7 115.2 53.3 (B) (b1) - 14.6 10.4 12 12 (b2) 10.2 - 24 - 11.4 (b3) 24 16 - 22.2 4 (C) (c1) - - - - - (c2) - - - - - (c3) - - - - - (c4) - - - - - (c5) - - - - - (c6) 4.8 - - - - (c7) - - 5 - - (c8) - - - 7.5 - (c9) - 4.4 - - - (C ') - - - - 8.8 (D) 0.2 0.2 0.2 0.2 0.2 (E) 20 20 20 20 20 (F) 0.8 0.8 0.8 0.8 0.8 (G) 80 80 80 80 80

접착 필름 제조Adhesive film manufacturers

고속 교반봉을 포함하는 1L 원통형 플라스크에 상기 표 1 및 2에 기재된 성분을 첨가하고 10분간 2000 rpm에서 저속으로, 그리고 30분간 5000rpm에서 고속으로 분산하여 접착 필름용 조성물을 제조하였다. 이후, 각 조성물을 50㎛ 캡슐 필터를 이용하여 여과한 뒤 어플리케이터로 20㎛ 두께로 코팅하여 접착 필름을 제조하였으며, 90℃에서 10분 건조한 뒤 110 ℃에서 5분간 건조한 후 실온에서 1일간 보관하였다.The components shown in Tables 1 and 2 were added to a 1 L cylindrical flask including a high speed stirring rod and dispersed at a low speed at 2000 rpm for 10 minutes and at a high speed at 5000 rpm for 30 minutes to prepare a composition for an adhesive film. Thereafter, each composition was filtered using a 50 μm capsule filter and then coated with an applicator to a thickness of 20 μm to prepare an adhesive film. The adhesive film was dried at 90 ° C. for 10 minutes and then dried at 110 ° C. for 5 minutes, and then stored at room temperature for 1 day.

상기 실시예1 ~ 5 및 비교예1 ~ 5에서 제조된 접착 필름을 이용하여 하기와 같은 방법으로 실험하고, 그 결과를 하기 표 3에 나타내었다.Experiment using the adhesive film prepared in Examples 1 to 5 and Comparative Examples 1 to 5 in the following manner, the results are shown in Table 3 below.

(1) 고속 분산 후 조액 안정성 : 조성 성분 투입 후 고속 교반봉을 이용하여 10분간 2000rpm, 30분간 5000rpm으로 고속 분산을 실시, 50um캡슐 필터를 사용하여 여과시킨 후 필름 형성을 하게 된다. 이때 고속 분산에 따른 열이 발생하여 조성 성분끼리 반응성이 빠르거나 안정성이 떨어지게 된다면 겔(gel)화 되어 필름 형성 작업이 용이하지 않게 된다. 고속 분산 후 겔화 되는 정도를 판단하여 이상이 없을 시에 ○, 약간 겔화되었으면 △, 전부 겔화되었을 때에는 ×로 표시하였다.(1) Crude liquid stability after high-speed dispersion: After the composition component is added, high-speed dispersion is performed at 2000 rpm for 10 minutes and 5000 rpm for 30 minutes using a high-speed stirring rod, and then filtered using a 50um capsule filter to form a film. At this time, if heat is generated due to high-speed dispersion, and the reactivity between components is fast or inferior in stability, gelation becomes a gel and thus the film forming operation is not easy. The degree of gelation after high-speed dispersion was judged, and when there was no abnormality,?

(2) 용융점도 at 260℃ (× 10^4[P]) : 필름의 점도를 측정하기 위하여 각각의 필름을 여러 겹 60℃에서 합지하고 지름이 8mm로 원형 컷팅하였다. 이때 두께는 400 ~ 450um정도이다. 점도측정범위는 30℃에서 300℃까지 측정하였고 승온조건은 5℃/분이다. 표에는 칩간 접착이 행해지는 온도인 260℃에서의 흐름성을 가늠하는 260℃에서의 에타(Eta) 값을 제시하였다.(2) Melt Viscosity at 260 ° C. (× 10 4 [P]): In order to measure the viscosity of the films, each film was laminated at several layers at 60 ° C. and circular cut to a diameter of 8 mm. At this time, the thickness is about 400 ~ 450um. Viscosity measurement range was measured from 30 ℃ to 300 ℃ and the temperature rise condition is 5 ℃ / min. The table shows the Eta value at 260 ° C., which measures the flowability at 260 ° C., which is the temperature at which the chip-to-chip adhesion is performed.

(3) 접착력 [kgf/chip] : 이산화 막으로 코팅되어있는 두께 725um 웨이퍼를 5mm x 5mm 크기로 자른 뒤 접착 필름과 함께 60도 조건에서 라미네이션(Lamination)하고 접착부분만 남기고 절단하였다. 동일한 두께 725um인 10mm x 10mm 크기 웨이퍼 위에 접착제가 라미네이션된 웨이퍼 조각을 10초 동안 1.0 kgf의 힘으로 100℃, 260℃ 각각 순서대로 압착하고 175℃에서 2시간을 경화한 후, PCT조건 (121℃／100％RH) 8시간, IR-reflow 3회 실시 후 250℃에서의 전단 파괴 강도를 측정했다.(3) Adhesive force [kgf / chip]: A 725 um thick wafer coated with a dioxide film was cut to a size of 5mm x 5mm, and then laminated at 60 degrees with an adhesive film and cut with only the adhesive part remaining. After laminating a piece of adhesive-laminated wafer on a 10 mm x 10 mm wafer with the same thickness of 725 um in order of 100 ° C and 260 ° C with 1.0 kgf for 10 seconds and curing at 175 ° C for 2 hours, PCT conditions (121 ° C) / 100% RH) Shear failure strength in 250 degreeC was measured after performing IR-reflow 3 times for 8 hours.

(4) 발포성 void : 이산화 막으로 코팅되어있는 두께 80um 웨이퍼를 10mm x 10mm 크기로 자른 뒤 접착 필름과 함께 60도 조건에서 라미네이션(Lamination)하고 접착부분만 남기고 절단하였다. 725um인 10mm x 10mm 크기 웨이퍼 위에 접착제가 라미네이션된 웨이퍼 조각을 10초 동안 1.0 kgf의 힘으로 100℃, 260℃ 각각 순서대로 압착하고 SAT(Scanning Acoustic Tomograph)로 조사하여 발포성 void의 양호수준을 평가하였다. 발포 없이 면상 양호하면 ○, 부분적으로 미세 발포가 발생하면 △, 발포 현상이 심하면 ×로 표시하였다.(4) Foamed void: A 80um wafer coated with a dioxide film was cut into 10mm x 10mm in size, and then laminated at 60 degrees with an adhesive film, and cut off leaving only the adhesive part. Adhesive lamination on the 725um 10mm x 10mm size wafer was pressed for 10 seconds at 100 ℃ and 260 ℃ in order of 1.0 kgf and irradiated with SAT (Scanning Acoustic Tomograph) to evaluate the good level of foam voids . ○ If the surface is satisfactory without foaming,?, If fine foaming occurs partially,?, And if the foaming phenomenon is severe, X is indicated.

(5) Solder/Cu Bump 접속성 : Solder Bump와 Cu Bump의 접속성 평가를 위해 제작된 칩을 사용하여 접착제 조성에 따른 Bump to Bump의 접속성 양호수준을 평가하였다. 접속이 양호하면 ○, 부분적으로 접속이 안되면 △, 모든 부분에서 접속이 안되면 ×로 표시하였다.(5) Solder / Cu Bump connectivity: The good level of Bump to Bump connectivity was evaluated according to the adhesive composition using chips manufactured for the evaluation of solder bump and Cu Bump connectivity. ○ If the connection is good,? Is partially lost, and?

(6) Solder/Cu間 IMC Layer유무 : Solder Bump와 Cu Bump접속 시 Flux활성에 따른 산화막 제거가 발현된다면 Solder/Cu間 IMC(Intermetallic Compound) Layer가 생성된다. (ref. Journal of Alloys and Compounds 381 (2004) 151 　157) 산화막 제거능에 대한 평가를 위해 Cu foil에 접착 필름과 Solder Ball (Sn96.8Ag3.0Cu0.2, 760um)을 올려 놓고 260℃로 압착하여 몰딩한 후 측면을 polishing하여 Cu foil과 Solder ball 사이의 IMC layer를 SEM을 이용하여 관찰하였다. IMC layer가 있으면 ○, 없으면 ×로 표시하였다.(6) Presence of Solder / Cu 間 IMC Layer: Solder / Cu 間 IMC (Intermetallic Compound) layer is formed if oxide film removal due to Flux activity is expressed when Solder Bump and Cu Bump are connected. (ref.Journal of Alloys and Compounds 381 (2004) 151 157) To evaluate the oxide removal ability, the adhesive film and solder ball (Sn96.8Ag3.0Cu0.2, 760um) were placed on Cu foil and pressed to 260 ℃ for molding. After polishing the side, the IMC layer between Cu foil and solder ball was observed by SEM. If there is an IMC layer, it is indicated by ○ and without ×.

(7) 접촉각: Cu foil에 접착 필름과 솔더 Ball (Sn96.8Ag3.0Cu0.2, 760um)을 올려 놓고 260℃로 압착하여 몰딩한 후 측면을 polishing하여 Cu foil과 솔더 ball 사이의 접촉 부분을 SEM을 이용하여 관찰하였다. 이때 Flux활성에 따른 산화막 제거가 발현된다면 Cu foil면에 솔더 ball이 wetting하게 되고 접촉 부분에서 접촉각 측정이 가능하게 된다. 측정된 접촉각을 표시하였다. (7) Contact angle: Put the adhesive film and solder ball (Sn96.8Ag3.0Cu0.2, 760um) on the Cu foil, compress it by molding at 260 ℃, and polish the side to make a SEM contact point between the Cu foil and the solder ball. It was observed using. At this time, if the oxide film is removed due to the flux activity, the solder ball is wetting on the Cu foil surface and the contact angle can be measured at the contact portion. The measured contact angle is indicated.

표 3 실시예 비교예 1 2 3 4 5 1 2 3 4 5 고속분산후조액안정성 ○ ○ ○ ○ ○ △ × × × ○ 용융점도(at 250℃)×104[P] 5.3 4.2 4.7 5.5 6.1 31 - - - 5.9 접착력[kgf/chip] 12 12 13 11 13 3 - - - 10 발포성void ○ ○ ○ ○ ○ ○ - - - △ solder/Cu bump 접속성 ○ ○ ○ ○ ○ × - - - ○ solder/Cu 간 IMC layer 유무 ○ ○ ○ ○ ○ ○ - - - × 접촉각(도) 41 45 38 45 50 35 - - - - TABLE 3 Example Comparative example One 2 3 4 5 One 2 3 4 5 High speed dispersion liquid after dispersion ○ ○ ○ ○ ○ △ × × × ○ Melt viscosity (at 250 ℃) × 10 4 [P] 5.3 4.2 4.7 5.5 6.1 31 - - - 5.9 Adhesive force [kgf / chip] 12 12 13 11 13 3 - - - 10 Effervescent ○ ○ ○ ○ ○ ○ - - - △ solder / Cu bump connectivity ○ ○ ○ ○ ○ × - - - ○ IMC layer between solder / Cu ○ ○ ○ ○ ○ ○ - - - × Contact angle (degrees) 41 45 38 45 50 35 - - - -

상기 표 3에 나타난 바와 같이 실시예 1-5는 모든 측정 항목에서 양호한 것을 알 수 있다. 반면, 비교예 1의 경우 carboxylic acid가 노출된 trimellictic anhydride를 사용한 조성인데, 산류가 조성물에 존재할 경우 필름 형성을 위한 조성물의 고속 교반시 발생하는 열 및 건조 시 받게 되는 열에 의해 에폭시 수지와 반응이 발생할 수 있다. 따라서 빠른 경화 반응에 의한 불량이 야기될 수 있다. 고속 분산 후 조액 안정성도 양호하지 않으며 건조 시 경화가 일부 진행되어 유동특성이 저하되고 칩간 접속 및 접착에 불리한 특성을 보이게 된다. 비교예 2~4 역시 마찬가지로 산류를 사용하였을 때 조액 안정성이 확보되지 않음을 알 수 있다. 비교예 5의 경우 Flux활성 경화제 대산 페놀 경화제를 사용한 경우인데, Flux활성에 따른 Solder, Cu의 산화막 제거가 발생하지 않기 때문에 IMC layer형성이 안되어 칩간 접속이 원활히 이루어지지 않음을 알 수 있다. As shown in Table 3, it can be seen that Example 1-5 is good in all measurement items. On the other hand, Comparative Example 1 is a composition using trimellictic anhydride exposed to the carboxylic acid, when the acid is present in the composition, the reaction occurs with the epoxy resin due to the heat generated during high-speed stirring of the composition for film formation and the heat received during drying Can be. Therefore, a failure due to a fast curing reaction can be caused. After the high-speed dispersion, the crude liquid stability is also not good and the curing progresses partially during drying, which results in deterioration of the flow characteristics and disadvantageous characteristics in connection and adhesion between chips. Comparative Examples 2 to 4 can also be seen that the stability of the crude liquid is not secured when the acid is used. In the case of Comparative Example 5 Flux active curing agent Daesan phenol curing agent is used, since the removal of the oxide film of the solder, Cu according to the Flux activity does not occur, it can be seen that the connection between the chip is not made smoothly because the IMC layer is not formed.

본 발명은 상기 실시예들에 한정되는 것이 아니라 서로 다른 다양한 형태로 제조될 수 있으며, 본 발명이 속하는 기술분야에서 통상의 지식을 가진 자는 본 발명의 기술적 사상이나 필수적인 특징을 변경하지 않고서 다른 구체적인 형태로 실시될 수 있다는 것을 이해할 수 있을 것이다. 그러므로 이상에서 기술한 실시예들은 모든 면에서 예시적인 것이며 한정적이 아닌 것으로 이해해야 한다.The present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

Claims (15)

하기 화학식 1 내지 3 으로 표시되는 플럭스 활성 경화제를 최소한 1종 포함하는 반도체용 접착 조성물:An adhesive composition for a semiconductor comprising at least one flux active curing agent represented by the following Chemical Formulas 1 to 3: [화학식 1][Formula 1]
Figure PCTKR2011002069-appb-I000009
Figure PCTKR2011002069-appb-I000009
 (상기에서 [A]의 산무수물이 포함된 환 구조는 0 ~ 3 의 이중결합을 포함하고, 환 구조를 이루는 탄소 수는 4~8 개이고, [B]는 지환족, 불포화 지환족 또는 방향족이며, 환 구조를 이루는 탄소 수는 4~8개이며, R1은 수소원자, 탄소 수 1~6의 알킬기, 탄소 수 6~12의 아릴기, 탄소 수 6~12의 치환 아릴기, 비닐기, 알릴기로 이루어진 군으로부터 선택되며, n은 0~2의 정수임)(In the above-mentioned ring structure containing the acid anhydride of [A] contains a double bond of 0 to 3, the ring structure is 4 to 8 carbon atoms, [B] is alicyclic, unsaturated alicyclic or aromatic , The ring structure has 4 to 8 carbon atoms, R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group, Is selected from the group consisting of allyl groups, n is an integer of 0 to 2) [화학식 2][Formula 2]
Figure PCTKR2011002069-appb-I000010
Figure PCTKR2011002069-appb-I000010
 (상기에서 [C]의 산무수물이 포함된 환 구조는 0 ~ 3 의 이중결합을 포함하고, 환 구조를 이루는 탄소 수는 4~8 개이고, [D]는 지환족, 불포화 지환족 또는 방향족이며, 환 구조를 이루는 탄소 수는 4~8개이며, R2은 수소원자, 탄소 수 1~6의 알킬기, 탄소 수 6~12의 아릴기, 탄소 수 6~12의 치환 아릴기, 비닐기, 알릴기로 이루어진 군으로부터 선택되며, n은 1~4의 정수임)(In the above-mentioned ring structure containing the acid anhydride of [C] comprises a double bond of 0 to 3, the ring structure is 4 to 8 carbon atoms, [D] is alicyclic, unsaturated alicyclic or aromatic , Ring carbon number is 4-8, R 2 is a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, an aryl group of 6 to 12 carbon atoms, a substituted aryl group of 6 to 12 carbon atoms, a vinyl group, Selected from the group consisting of allyl groups, n is an integer from 1 to 4) [화학식 3] [Formula 3]
Figure PCTKR2011002069-appb-I000011
Figure PCTKR2011002069-appb-I000011
 (상기에서 [E]의 산무수물이 포함된 환 구조는 0 ~ 3 의 이중결합을 포함하고, 환 구조를 이루는 탄소 수는 4~8 개이고, [F]는 지환족, 불포화 지환족 또는 방향족이며, 환 구조를 이루는 탄소 수는 4~8개이며, R3은 수소원자, 탄소 수 1~6의 알킬기, 탄소 수 6~12의 아릴기, 탄소 수 6~12의 치환 아릴기, 비닐기, 알릴기로 이루어진 군으로부터 선택되며, R4는 하기 화학식(i)~(viii)의 구조로부터 선택될 수 있고, n은 1~4의 정수임)(In the above-mentioned ring structure containing the acid anhydride of [E] includes a double bond of 0 to 3, the ring structure is 4 to 8 carbon atoms, [F] is alicyclic, unsaturated alicyclic or aromatic , The ring structure has 4 to 8 carbon atoms, R 3 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a substituted aryl group having 6 to 12 carbon atoms, a vinyl group, Selected from the group consisting of allyl groups, R 4 may be selected from the structures of formulas (i) to (viii), and n is an integer of 1 to 4)
Figure PCTKR2011002069-appb-I000012
Figure PCTKR2011002069-appb-I000012
 제1항에 있어서, 상기 플럭스 활성 경화제는 전체 접착 조성물중 약 0.1 내지 약 10 중량%로 포함되는 것을 특징으로 하는 반도체용 접착 조성물.The adhesive composition of claim 1, wherein the flux active curing agent comprises from about 0.1 to about 10 weight percent of the total adhesive composition. 제1항에 있어서, 상기 플럭스 활성 경화제는 융점이 약 100 내지 약 300 ℃ 인 것을 특징으로 하는 반도체용 접착 조성물.The adhesive composition of claim 1, wherein the flux active curing agent has a melting point of about 100 to about 300 ° C. 제1항에 있어서, 상기 조성물은 260 ℃에서 용융점도가 약 2 ×104 내지 약 15 ×104 poise 인 접착 조성물.The adhesive composition of claim 1, wherein the composition has a melt viscosity at 260 ° C. of about 2 × 10 4 to about 15 × 10 4 poise. 제1항에 있어서, 상기 조성물은 본딩 후 금속 범프에 대한 Solder의 접촉각이 약 10 내지 약 80 도인 반도체용 접착 조성물.The adhesive composition of claim 1 wherein the composition has a contact angle of the solder relative to the metal bump after bonding from about 10 to about 80 degrees. 제1항에 있어서, 상기 조성물은 이미다졸계 경화촉매를 약 0.1 내지 약 5 중량% 포함하는 것을 특징으로 하는 반도체용 접착 조성물.The adhesive composition of claim 1, wherein the composition comprises about 0.1 to about 5 wt% of an imidazole series curing catalyst. 제1항에 있어서, 상기 조성물은 고분자 수지, 에폭시계 수지, 상기 화학식 1 내지 3의 플럭스 활성 경화제 중 최소한 1종, 충진제 및 경화촉매를 포함하는 반도체용 접착 조성물.The adhesive composition of claim 1, wherein the composition comprises a polymer resin, an epoxy resin, at least one of a flux active curing agent of Formulas 1 to 3, a filler, and a curing catalyst. 제7항에 있어서, 상기 조성물은 고분자 수지 약 20~60 중량% (고형분 기준), 에폭시계 수지 약 10~60 중량%, 플럭스 활성 경화제 약 0.1~10 중량%, 경화촉매 약 0.01~5 중량% 및 충진제 약 15~40 중량% 를 포함하는 반도체용 접착 조성물.According to claim 7, wherein the composition is about 20 to 60% by weight of the polymer resin (based on solids), about 10 to 60% by weight of the epoxy resin, about 0.1 to 10% by weight of the flux active curing agent, about 0.01 to 5% by weight of the curing catalyst. And about 15-40% by weight of a filler. 제8항에 있어서, 상기 고분자 수지는 에폭시기를 함유하며, 유리전이온도가 약 -30 ~ 80℃인 것을 특징으로 하는 반도체용 접착 조성물.The adhesive composition according to claim 8, wherein the polymer resin contains an epoxy group and has a glass transition temperature of about -30 to 80 ° C. 제8항에 있어서, 상기 조성물은 실란커플링제를 약 0.01~10 중량% 더 포함하는 것을 특징으로 하는 반도체용 접착 조성물.The adhesive composition of claim 8, wherein the composition further comprises about 0.01 to 10 wt% of a silane coupling agent. 제1항 내지 제10항 중 어느 한 항의 접착 조성물로 형성된 반도체용 접착 필름.The adhesive film for semiconductors formed from the adhesive composition of any one of Claims 1-10. 제11항에 있어서, 상기 반도체용 접착 필름은 본딩 후 금속 범프와 Solder사이의 금속간 화합물층(Inter-Metallic Compound Layer)이 본딩 면적 대비 약 70 % 이상인 것을 특징으로 하는 반도체용 접착필름.The adhesive film for semiconductor according to claim 11, wherein the adhesive film for semiconductor has an inter-metal compound layer between the metal bumps and the solder after bonding to about 70% of the bonding area. 제11항에 있어서, 상기 반도체용 접착 필름은 본딩 후 Cu와 Solder사이의 금속간 화합물층(Inter-Metallic Compound Layer)이 본딩 면적 대비 약 70 % 이상인 것을 특징으로 하는 반도체용 접착필름.The adhesive film for semiconductor according to claim 11, wherein the adhesive film for semiconductor is about 70% or more of the inter-metallic compound layer between the Cu and the solder after the bonding. 범프된 제1 및 제2 반도체 칩 사이를 제1항 내지 제10항 중 어느 한 항의 접착 조성물로 형성된 접착필름으로 접착하는 방법.11. A method of bonding between bumped first and second semiconductor chips with an adhesive film formed from the adhesive composition of any one of claims 1 to 10. 칩 탑재 기판; 및Chip mounted substrate; And 상기 칩 탑재 기판의 일면에 적층된 제1 및 제2 반도체 칩을 포함하며, 상기 제1 및 제2 반도체 칩은 제11항에 기재된 반도체용 접착필름으로 접착된 반도체 패키지.A semiconductor package comprising first and second semiconductor chips laminated on one surface of the chip mounting substrate, wherein the first and second semiconductor chips are bonded with the adhesive film for semiconductor according to claim 11.
PCT/KR2011/002069 2010-12-15 2011-03-25 Adhesive composition for a semiconductor, an adhesive film comprising the same and a semiconductor package using the same Ceased WO2012081771A1 (en)

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