WO2008065997A1 - Adhésif et structure de liaison utilisant celui-ci - Google Patents

Adhésif et structure de liaison utilisant celui-ci Download PDF

Info

Publication number
WO2008065997A1
WO2008065997A1 PCT/JP2007/072763 JP2007072763W WO2008065997A1 WO 2008065997 A1 WO2008065997 A1 WO 2008065997A1 JP 2007072763 W JP2007072763 W JP 2007072763W WO 2008065997 A1 WO2008065997 A1 WO 2008065997A1
Authority
WO
WIPO (PCT)
Prior art keywords
adhesive
group
resin
compound
meth
Prior art date
Application number
PCT/JP2007/072763
Other languages
English (en)
Japanese (ja)
Inventor
Shigeki Katogi
Sunao Kudou
Hiroyuki Izawa
Toshiaki Shirasaka
Original Assignee
Hitachi Chemical Company, Ltd.
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 Hitachi Chemical Company, Ltd. filed Critical Hitachi Chemical Company, Ltd.
Priority to CN200780043737.XA priority Critical patent/CN101541903B/zh
Priority to JP2008546976A priority patent/JP5223679B2/ja
Publication of WO2008065997A1 publication Critical patent/WO2008065997A1/fr

Links

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
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C09J9/02—Electrically-conducting adhesives
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
    • H05K3/32—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits
    • H05K3/321—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by conductive adhesives
    • H05K3/323—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by conductive adhesives by applying an anisotropic conductive adhesive layer over an array of pads
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
    • H05K2201/01—Dielectrics
    • H05K2201/0104—Properties and characteristics in general
    • H05K2201/0129—Thermoplastic polymer, e.g. auto-adhesive layer; Shaping of thermoplastic polymer

Definitions

  • the present invention relates to an adhesive and a connection structure using the adhesive.
  • an adhesive is used for the purpose of bonding various members constituting the element.
  • This adhesive is required to satisfy various properties such as adhesiveness, heat resistance, and reliability in a high temperature and high humidity state.
  • the adherend to which the adhesive is applied is composed of a wide variety of materials such as printed wiring boards and organic substrates such as polyimide, metals such as copper and aluminum, and ITO, SiN, and SiO.
  • a substrate having a surface is used.
  • adhesives it is necessary to design a molecule for each type of adherend.
  • thermosetting resin using an epoxy resin having high adhesiveness and high reliability has been widely used (for example, see Patent Document 1).
  • curing agents such as epoxy resins and phenolic resins that are reactive with epoxy resins
  • thermal latent catalysts that promote the reaction between epoxy resins and curing agents are generally used. It has been.
  • Thermal latent catalysts are important factors that determine the curing temperature and curing rate, and various compounds have been used from the viewpoint of storage stability at room temperature and curing rate during heating. As for the curing conditions in the actual process, heating at a temperature of 170 to 250 ° C. for about 1 to 3 hours is common.
  • radical curable adhesives using a radical polymerizable compound such as an acrylate derivative or a meta acrylate derivative in combination with a peroxide as a radical polymerization initiator have attracted attention.
  • radicals that are reactive species are rich in reactivity, and can be cured in a short time (see, for example, Patent Document 2).
  • the radical curing type adhesive has a large curing shrinkage at the time of curing, the adhesive strength tends to be lower than when an epoxy resin is used.
  • Patent Document 3 a method using a urethane acrylate compound imparted with flexibility and flexibility by an ether bond as a radical polymerizable compound (Patent Document 3, 4) and a method using a radically polymerizable compound, phosphoric acid metatalylate and a melamine resin in combination (see Patent Documents 5 and 6).
  • Patent Document 1 Japanese Patent Laid-Open No. 1 113480
  • Patent Document 2 Japanese Patent Laid-Open No. 2002-203427
  • Patent Document 3 Japanese Patent No. 3522634
  • Patent Document 4 Japanese Patent Laid-Open No. 2002-285128
  • Patent Document 5 Japanese Unexamined Patent Publication No. 2003-89775
  • Patent Document 6 Japanese Patent Laid-Open No. 2003-20464
  • radical curable adhesives using urethane acrylate are good in initial adhesion strength, but have characteristics such as adhesion strength and connection resistance when exposed to high-temperature and high-humidity environments. There was a problem that decreased. Further, according to the study by the present inventors, an adhesive using a metatarylate phosphate and a melamine resin cannot provide sufficient adhesive strength and connection resistance when used after long-term storage, which is insufficient in storage stability. It became clear.
  • the present invention is a radical-curing adhesive that exhibits high adhesive strength, has high resistance to defects in reliability tests under high temperature and high humidity, and also has excellent storage stability. And it aims at providing a connection structure using the same.
  • the adhesive according to the present invention comprises (a) a thermoplastic resin, (b) a radical polymerizable compound, (c) a urea compound represented by the following general formula (10), and (d) a radical. It contains a polymerization initiator and (e) an acid compound.
  • R 1 and R 2 each independently represents an optionally substituted alkyl group or a hydrogen atom, and R 1 and R 2 are bonded to each other to form a ring! /,
  • R 3 and R 4 each independently represent a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 10 carbon atoms.
  • the adhesive according to the present invention employs a combination of the specific components described above, so that it exhibits high adhesive strength and has high resistance to a reliability test under high temperature and high humidity. It also became excellent in storage stability.
  • connection structure includes a first circuit member having a first connection terminal and a second connection terminal, and the second connection terminal faces the first connection terminal.
  • the second circuit member disposed opposite to the first circuit member, and an adhesive layer that is interposed between the first circuit member and the second circuit member and bonds them together.
  • the adhesive layer is formed by the adhesive according to the present invention.
  • connection structure according to the present invention has circuit members bonded to each other with high adhesive strength, and has high and / or resistance to a reliability test under high temperature and high humidity.
  • a radical curable adhesive that exhibits high adhesive strength, has high resistance to a reliability test under high temperature and high humidity, and has excellent storage stability. Is provided.
  • connection structure in which circuit members are bonded to each other with high adhesive strength and has high resistance to a reliability test under high temperature and high humidity.
  • FIG. 1 is a schematic cross-sectional view showing an embodiment of a connection structure. Explanation of symbols
  • connection structure 7 ⁇ ⁇ ⁇ conductive particles, 10 ⁇ ⁇ ⁇ adhesive layer, 11 ⁇ ⁇ ⁇ insulating layer, 20 ⁇ ⁇ ⁇ first circuit member, 21 ⁇ ⁇ ⁇ first Circuit board, 22 ⁇ first connection terminal, 30 ⁇ second circuit member, 31 ⁇ second circuit board, 32 ⁇ second connection terminal.
  • the adhesive according to the present embodiment includes (a) a thermoplastic resin, (b) a radical polymerizable compound, (c) a urea compound, (d) a radical polymerization initiator, and (e) an acidic compound. Containing.
  • the adhesive according to the present invention is suitably used, for example, as an anisotropic conductive adhesive for bonding circuit members having connection terminals to form a connection structure.
  • thermoplastic resin of component (a) known resins can be used without any particular limitation. For example, heat a phenoxy resin, a polyester resin, a polyurethane resin, a polyester urethane resin, a peticular resin, an acrylic resin, a polyimide resin, a polyamide resin, a poly (meth) phthalate, a polybutyral, or an ethylene butylacetate copolymer. Can be used as a plastic resin.
  • the thermoplastic resin in the adhesive preferably contains at least one selected from the group consisting of phenoxy resin, polyester resin, polyurethane resin, polyester urethane resin, petital resin, acrylic resin and polyimide resin. These can be used alone or in combination of two or more.
  • thermoplastic resin may have a siloxane bond or a substituent containing a fluorine atom. These can be used particularly preferably if they are completely compatible with each other or become micro-turbided due to microphase separation.
  • the weight-average molecular weight of the heatable deciduous tree is preferably 5,000 to 500,000, more preferably 10,000 to 100,000, more preferably force S force S.
  • the weight average molecular weight of less than 5000 will tend to film formability is lowered, and when it exceeds 500,000, the compatibility with other components is prone force s decreases.
  • the radically polymerizable compound of component (b) any known compound can be used as long as it is a compound having a radically polymerizable functional group.
  • a styrene derivative, a maleimide polymer, and a compound having an allyloyl group or a methacryloyl group are used.
  • a radically polymerizable compound contains the polyfunctional (meth) atalylate compound which has a 2 or more (meth) atalyloyl group.
  • polyfunctional (meth) acrylate are epoxy (meth) acrylate oligomer, urethane (meth) acrylate oligomer, polyether (meth) acrylate oligomer, and polyester (meth) acrylate.
  • Oligomers such as oligomers, trimethylol propantry (meth) acrylate, polyethylene glycol di (meth) acrylate, polyalkylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, dipentaerythritol hexa (Meth) acrylate, isocyanuric acid modified bifunctional (meth) acrylate, isocyanuric acid modified trifunctional (meth) acrylate, bisphenol full orange glycidyl ether with (meth) acrylic acid added to glycidyl group Poxy (meth) attalylate, a compound in which ethylene glycol or propylene glycol is added to the glycidyl group of bisphenol fluorenediglycidyl ether, a compound having a (meth) attaroyloxy group, the following general formula (A) or (B ) Is a polyfunctional (meth) acrylate compound.
  • R 21 and R 22 each independently represent a hydrogen atom or a methyl group
  • k and m each independently represent an integer of 1 to 8.
  • R 23 and R 24 represent a hydrogen atom or a methyl group
  • n represents an integer of 1 to 8
  • p represents an integer of 0 to 8.
  • a polyfunctional (meth) acrylate compound and a monofunctional (meth) acrylate compound may be used in combination! /.
  • a monofunctional (meth) acrylate compound By using a monofunctional (meth) acrylate compound, the fluidity of the adhesive is improved.
  • monofunctional (meth) acrylate compounds include pentaerythritol (meth) acrylate, 2-cyanoethyl (meth) acrylate, cyclohexyl (meth) acrylate, dicyclopentyl (meth) acrylate, Dicyclopentenyl diloxychetyl (meth) acrylate, 2- (2-ethoxyethoxy) ethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-ethyl hexyl (meth) acrylate, n-hexyl (meta ) Atarylate, 2-hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, isobornyl (meth) acrylate, isodecyl (meth) acrylate, isooctyl (meth) acrylate, n-lauryl (meta) ) Atarylate,
  • the radical polymerizable compound may include a compound having a radical polymerizable functional group other than the (meth) acrylic group such as a aryl group, a maleimide group and a bur group.
  • a radical polymerizable functional group other than the (meth) acrylic group such as a aryl group, a maleimide group and a bur group.
  • Specific examples thereof include N-Buylimidazole, N-Burpyridine, N-Buylpyrrolidone, N-Vinoleformamide, N-Buhl Force Prolatatam, 4, 4'-Builidenbis (N, N-Dimethinoreaniline), N-Bulacetoamide, N, N-dimethylacrylamide, N-isopropylacrylamide, and N, N-jetylacrylamideacrylamide.
  • the amount of the radical polymerizable compound in the adhesive is preferably 30 to 250 parts by weight with respect to 100 parts by weight of the thermoplastic resin. If the amount of the radically polymerizable compound is less than 30 parts by weight, the heat resistance after curing tends to be lowered, and if it exceeds 250 parts by weight, the adhesive is not cured. When used as an film, film formability tends to decrease. From the same viewpoint, the amount of the radical polymerizable compound is more preferably 50 to 150 parts by weight.
  • the radical polymerizable compound different from component (e) is (b) ) Used as a component.
  • the urea compound as component (c) is a compound represented by the general formula (10).
  • an increase in connection resistance and a decrease in adhesive strength under high temperature and high humidity are suppressed, and storage stability is specifically improved.
  • the initial adhesive strength is relatively good, but the adhesive strength is remarkably lowered after long-term storage. The reason for this is not necessarily clear, but it is thought that the reaction of the melamine resin itself tends to proceed gradually in the presence of an acidic compound during long-term storage.
  • R 1 and R 2 each independently represents an optionally substituted alkyl group or a hydrogen atom, and R 1 and R 2 are bonded to each other to form a ring. May be.
  • R 3 and R 4 each independently represent a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 10 carbon atoms.
  • the alkyl group as R 1 and R 2 is, for example, substituted by a urea group! /, Or may! /.
  • the urea compound is a compound represented by the following general formula (11), (12), (13), (14), (15), (16) or (17): It is preferable to have at least one selected! /.
  • R 3 and R 4 are the same as R 3 and R 4 of formula (10).
  • R 5 and R 6 each independently represent a hydrogen atom, a linear alkyl group having 18 carbon atoms, or a branched alkyl group having 3 to 10 carbon atoms.
  • R 7 and R 8 each independently represent a hydrogen atom, a linear alkyl group having 18 carbon atoms, or a branched alkyl group having 3 to 10 carbon atoms.
  • R 9 represents a hydrogen atom, a linear alkyl group having 18 carbon atoms, or a branched alkyl group having 3 10 carbon atoms.
  • R 1 () and R 11 each independently represent a hydrogen atom, a linear alkyl group having 18 carbon atoms, or a branched alkyl group having 3 to 10 carbon atoms.
  • the urea compound is represented by the formula (11), R 3 and R 4 are hydrogen atoms, N, N′-dimethylolurea, represented by the formula (12), R 3 And 1,3-dimethoxymethylethyleneurea in which R 4 is a methyl group, and R 3 R 4 R 1 () and R 11 are methyl groups represented by the formula (17) -Tetrakis (methoxymethyl) glycoluril.
  • the amount of the urea compound in the adhesive is preferably 1 with respect to 100 parts by weight of the thermoplastic resin.
  • the amount of urea compound is less than 1 part by weight, The effect of improving the resistance tends to be small, and when it exceeds 50 parts by weight, the film formability tends to decrease when the adhesive is used as a film. From the same viewpoint, the amount of the urea compound is more preferably 5 to 30 parts by weight.
  • radical polymerization initiator of component (d) known compounds such as conventionally known peroxides and azo compounds can be used. From the viewpoints of stability, reactivity, and compatibility, peroxides having a 1 minute half-life temperature of 90 to 175 ° C and a molecular weight of 180 to 1000 are preferred.
  • radical polymerization initiators include 1,1,3,3 tetramethylbutyl carboxyneodecanoate, di (4 t butylcyclohexenole) peroxy dicarbonate, Di (2-ethylhexyl) peroxydicarbonate, Tamylperoxyneodecanoate, 1,1,3,3-Tetramethylbutylperoxyneodecanoate, Dilauroyl peroxide, 1-Cyclohexinole 1-Metinoreethinolevoxinoedecanoate, t-hexenoreperoxyneodecanoate, t-butinoreperoxyneodecanoate, t-butinoreperoxybivalate, 1, 1, 3, 3—Tetramethinolebutinolevoxy 2— Ethenolehexanoate, 2, 5 Dimethenole 2,5 Di (2 Ethenolehexanoreperoxy) hexane
  • radical polymerization initiator a radical photopolymerization initiator that generates a radical upon irradiation with light (typically 150 to 750 nm) is also preferable.
  • photo radical polymerization initiators include ⁇ -acetoaminophenone derivatives and phosphines described in ⁇ _ ⁇ , Photoinitiation, Photopolymerization, and Photocuring, J. —P. F assiassier, Hanser Publishers (1995), ⁇ 17 to ⁇ 35 ⁇ . Oxide derivatives are more preferred because of their high sensitivity to light irradiation.
  • These radical photopolymerization initiators may be used alone or in combination with a peroxide or a azo compound.
  • the amount of the radical polymerization initiator in the adhesive is preferably 0.1 to 30 parts by weight with respect to 100 parts by weight of the thermoplastic resin. If the amount of the radical polymerization initiator is less than 0.1 part by weight, the possibility of insufficient curing tends to increase, and if it exceeds 30 parts by weight, the effect of improving storage stability tends to be reduced. From the same viewpoint, the amount of the radical polymerization initiator is more preferably 2 to 20 parts by weight.
  • the acidic compound of component (e) is a compound having one or more acidic groups such as a phosphate group.
  • an acidic compound having a phosphate group and a bur group is preferable.
  • an acidic compound having a phosphate group and a bur group it is possible to maintain a higher adhesive force.
  • the acidic compound having a phosphoric acid group and a bur group include compounds represented by the following general formula (21), (22) or (23).
  • R 3 ° and R 31 each independently represent a hydrogen atom or a methyl group, and w and X each independently represent an integer of 1 to 8.
  • R 3 ° represents a hydrogen atom or a methyl group, and x, y and z each independently represents an integer of 1 to 8.
  • R 3 ° and R 31 each independently represent a hydrogen atom or a methyl group, and a and b each independently represent an integer of 1 to 8.
  • the acidic compound may be acid phosphoxoxyl metatalylate, acid.
  • the amount of the acidic compound in the adhesive is preferably 0.05 to 30 parts by weight with respect to 100 parts by weight of the thermoplastic resin. If the amount of the acidic compound is less than 0.05 parts by weight, high adhesive strength tends to be obtained, and if it exceeds 30 parts by weight, the physical properties of the adhesive after curing will decrease, and reliability will be improved. The effect tends to be small. From the same viewpoint, the amount of the acidic compound is more preferably 0.;!-20 parts by weight.
  • the adhesive according to the present embodiment may further contain conductive particles as the component (f).
  • Adhesives containing conductive particles are particularly useful as anisotropic conductive adhesives.
  • conductive particles include metal particles such as Au, Ag, Ni, Cu, and solder, and carbon.
  • Coated particles having a nonconductive core made of glass, ceramic, plastic, etc. and a coating layer made of metal or carbon covering the core may be used as the conductive particles. If the conductive particles are coated particles having a core made of plastic and a coating layer made of a metal or carbon covering the core, or heat-melted metal particles, the conductive particles are deformable by heating and pressing. Therefore, it is preferable because the contact area with the electrode is increased at the time of connection and the reliability is improved.
  • fine particles with the surface of these conductive particles coated with a polymer resin or the like suppress short circuit due to contact between the particles when the amount of the conductive particles is increased, and the insulation between the electrode circuits is reduced. Because it can be improved, it can be used alone or mixed with conductive particles.
  • the average particle diameter of the conductive particles is preferably 1 to 18 m from the viewpoint of dispersibility and conductivity.
  • the amount of the conductive particles in the adhesive is preferably 0.;! To 30% by volume with respect to the total volume of the adhesive including the conductive particles. If the amount of the conductive particles is less than 0.1% by volume, sufficient conductivity tends to be obtained, and if it exceeds 30% by volume, a short circuit tends to occur. From the same viewpoint, the amount of the conductive particles is more preferably 0.
  • the volume% of the conductive particles is determined based on the volume at 23 ° C of each component before curing. The volume of each component can be converted from weight to volume using specific gravity. Alternatively, do not dissolve or swell each component, put an appropriate solvent (water, alcohol, etc.) that wets each component well into a graduated cylinder, and add each component to it and determine the increased volume as that volume. You can also.
  • the adhesive according to the present embodiment may contain a stabilizer.
  • a stabilizer By using a stabilizer, the effect of improving storage stability can be made more remarkable while appropriately controlling the curing rate.
  • Stabilizers include quinone derivatives such as benzoquinone and neodroquinone, phenol derivatives such as 4-methoxyphenol and 4-t-butylcatechol, 2, 2, 6, 6 tetramethylbiperidine 1-oxyl and 4-hydroxy-2, 2 , 6, 6-tetramethylpiperidine 1-oxyl and the like, and hindered amine derivatives such as tetramethylpiperidyl methacrylate are preferably selected.
  • the amount of the stabilizer in the adhesive is preferably 0.01 to 30 parts by weight with respect to 100 parts by weight of the thermoplastic resin. If the amount of stabilizer is less than 0.01 parts by weight, the effect is reduced. When the amount exceeds 30 parts by weight, the compatibility with other components tends to decrease. From the same viewpoint, the amount of the stabilizer is more preferably 0.05 to 10 parts by weight.
  • the adhesive according to this embodiment may contain a coupling agent typified by an alkoxysilane derivative and a silazane derivative, and an adhesion aid such as an adhesion improver and a leveling agent.
  • the adhesive may contain a silane compound represented by the following general formula (30). Such silane compounds may be used alone or in combination of two or more.
  • R 32 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkoxycarbonyl group having 1 to 5 carbon atoms, or an aryl group. Multiple R 32s in the same molecule may be the same or different.
  • R 33 is a (meth) atalylooxy group, a bur group, an isocyanate group, an imidazole group, a mercapto group, an amino group, a methylamino group, a dimethyl group.
  • a luminamino group, a benzylamino group, a phenylamino group, a cyclohexylamino group, a morpholino group, a piperazino group, a ureido group or a glycidyl group, c represents an integer of 1 to 10;
  • R 33 is a (meth) ataryloxy group
  • a silane compound is used as the component (b).
  • the radically polymerizable compound of the component (b) may include a silane compound represented by the formula (30), wherein R 33 is a (meth) ataryloxy group.
  • the adhesive according to the present embodiment may contain rubber.
  • rubber By using rubber, the effects of stress relaxation and improved adhesion can be obtained.
  • Specific examples of rubber include polyisoprene, polybutadiene, carboxyl-terminated polybutadiene, hydroxyl-terminated polybutadiene, 1,2-polybutadiene, carboxyl-terminated 1,2-polybutadiene, hydroxyl-terminated 1,2-polybutadiene, acrylic rubber, styrene butadiene rubber , Hydroxyl-terminated styrene-butadiene rubber, acrylonitrile monobutadiene rubber, carboxyl group, hydroxyl group, acrylonitrile butadiene rubber containing a (meth) acryloyl group or morpholine group at the polymer end, carboxylated nitrile rubber, hydroxyl-terminated poly (oxypropylene), alkoxy Sirinole Examples include base terminal poly (oxypropylene), poly (oxyte
  • a rubber having a highly polar group, a cyano group or a carboxyl group, in the side chain or terminal is preferred.
  • liquid rubber is more preferable.
  • Specific examples include liquid acrylonitrile monobutadiene rubber, liquid acrylonitrile butadiene rubber containing a carboxyl group, a hydroxyl group, a (meth) atalyloyl group or a morpholine group at the polymer end, and a liquid carboxylated nitrile rubber. These rubber is preferably acrylonitrile containing 10 to 60 wt 0/0. These rubbers may be used alone or in combination of two or more.
  • the adhesive according to the present embodiment may be liquid (preferably pasty) at normal temperature (0 to 30 ° C), or may be solid.
  • the solid adhesive may be used by heating, or may be made into a paste using a solvent.
  • Solvents that can be used are not particularly limited as long as they are not reactive with each component of the adhesive and exhibit sufficient solubility, but have a boiling point of 50 to 150 ° C at normal pressure. Is preferred. If the boiling point is less than 50 ° C, it may volatilize if left at room temperature (0 to 30 ° C), which limits the use in open systems. Also, if the boiling point exceeds 150 ° C, the reliability after adhesion, which makes it difficult to volatilize the solvent, may be adversely affected.
  • the adhesive according to the present embodiment may be in the form of a film.
  • Use in the form of a film is more convenient in terms of handling.
  • a film-like adhesive is prepared by applying a solution obtained by dissolving an adhesive in a solvent onto a peelable substrate such as a fluororesin film, a polyethylene terephthalate film, or a release paper, or impregnating a substrate such as a nonwoven fabric. It can be obtained by a method of placing on a peelable substrate and then removing the solvent.
  • the adhesive according to this embodiment can be used as an adhesive for adhering a combination of different types of adherends having different thermal expansion coefficients. Specifically, it is suitably used as a circuit connecting material represented by anisotropic conductive adhesive, silver paste, silver film and the like. Alternatively, the adhesive according to this embodiment may be used as a semiconductor element adhesive material typified by an elastomer for CSP, an underfill material for CSP, a LOC tape, a die attach film, and the like.
  • FIG. 1 is a schematic cross-sectional view showing an embodiment of a connection structure. The connection structure 1 shown in FIG.
  • first circuit member 21 having a first circuit board 21 and a first connection terminal 22 formed on the main surface 21a thereof, a second circuit board 31 and The second circuit member 30 having the second circuit electrode 32 formed on the main surface 31a thereof, and the first circuit member 20 and the second circuit member 30 are interposed and bonded together.
  • the adhesive layer 10 is provided.
  • the second circuit member 30 is disposed opposite to the first circuit member 20 such that the second connection terminal 32 faces the first connection terminal 22.
  • the adhesive layer 10 is formed of the above-described adhesive containing conductive particles, and includes an insulating layer 11 and conductive particles 7 dispersed in the insulating layer 11.
  • the insulating layer 11 is a cured body derived from components other than the conductive particles in the adhesive and formed by radical polymerization of a radical polymerizable compound.
  • Opposing first connection terminal 22 and second connection terminal 32 are electrically connected via conductive particles 7.
  • the first connection terminals 22 and the second connection terminals 32 formed on the same circuit board are insulated.
  • the first circuit board 31 and the second circuit board 21 for example, a substrate of an inorganic material such as a semiconductor, glass and ceramic, a plastic substrate, or a glass / epoxy substrate is used.
  • the plastic substrate include a polyimide film, a polycarbonate film, and a polyester film.
  • the first connection terminal and the second connection terminal are formed from a metal such as copper.
  • one of the first circuit member 20 and the second circuit member 30 has a glass substrate or a plastic substrate as a circuit substrate, and a liquid crystal having a connection terminal formed of ITO or the like. It may be a display panel.
  • one of the first circuit member 20 and the second circuit member 30 is a flexible printed wiring board (FPC), a tape carrier package (TCP) or a chip-on-film (COF) having a polyimide film as a circuit board, Alternatively, it may be a semiconductor silicon chip having a semiconductor substrate as a circuit substrate.
  • FPC flexible printed wiring board
  • TCP tape carrier package
  • COF chip-on-film
  • the connection structure 1 includes, for example, the first circuit member 20, the film adhesive, and the second circuit.
  • the road member 30 is formed by a method in which the first connection terminal 22 and the second connection terminal 32 are overlapped in this order so that the first connection terminal 22 and the second connection terminal 32 face each other, and in this state, the adhesive is cured by heating and pressing.
  • the heating temperature is not particularly limited but is preferably 100 to 250 ° C.
  • the pressure is not particularly limited as long as it does not damage the adherend, but it is generally preferably 0.1 to 10 MPa. These heating and pressurization are performed in the range of 0.5 second to 120 seconds, preferably S, and can be bonded even by heating at 140 to 200 ° C., 3 MPa, and 10 seconds.
  • Example 1 Example
  • Phenoxy resin PKHM-30 (trade name), manufactured by InChem
  • Petitral resin Denkabutyral 3000-1 (trade name), manufactured by Denki Kagaku Kogyo Co., Ltd.
  • Polyester urethane resin UR-3500 (trade name), manufactured by Toyobo
  • Urethane resin 450 parts by weight of polybutylene adipate diol having an average molecular weight of 2000, 450 parts by weight of polyoxytetramethylene glycol having an average molecular weight of 2000 and 100 parts by weight of 1,4-butylene glycol are uniformly distributed in 4000 parts by weight of methyl ethyl ketone. The mixture was mixed, and 390 parts by weight of diphenylmethane diisocyanate was added and reacted at 50 ° C. (weight average molecular weight 100,000).
  • urea compound 3 • 1,3-Dimethoxymethylethyleneurea (urea compound 3): 2-Imidazolidone (manufactured by Aldrich) 43 parts by weight and 122% by weight 37% formaldehyde (manufactured by Kanto Chemical) under basic conditions was allowed to react at 100 ° C for 1 hour, cooled to room temperature (25 ° C), 2 parts by weight of methanol (manufactured by Kanto Chemical) 3 was added, and the mixture was stirred for 30 minutes under acidic conditions. (Yield 72%).
  • Lataton-modified phosphoric acid metatalylate KAMAR PM-21 (trade name), manufactured by Nippon Kayaku Co., Ltd.
  • a particle size of 4 ⁇ m and a specific gravity of 2.5) were prepared.
  • thermoplastic resin a radical polymerizable compound, a urea compound, a radical polymerization initiator, and an acidic compound are mixed in the composition shown in Table 1 (solid weight ratio), and the conductive particles are added in an amount of 1.5% by volume. This was added in proportion and dispersed to prepare the adhesive solutions of the examples and comparative examples.
  • the obtained adhesive solution was applied to a fluororesin film having a thickness of 80 am using a coating apparatus, and a film-like adhesive having a thickness of 18 m was obtained by drying with hot air at 70 ° C for 10 minutes.
  • a flexible circuit board having 500 copper circuits with a line width of 25 m, a pitch of 50 m, and a thickness of 12 mm 111, and 0.2 m of indium oxide (ITO)
  • a glass substrate with a thin layer is used at a temperature of 160 ° C using a hot-pressing device (heating method: constant heat type, manufactured by Toray Engineering Co., Ltd.).
  • a connection structure was prepared by connecting and connecting over a width of 2 mm by heating and pressing at 3 MPa for 10 seconds.
  • the resistance value between adjacent circuits of the obtained connection structure was measured with a multimeter immediately after bonding and after being held in a high-temperature and high-humidity tank at 85 ° C. and 85% RH for 168 hours.
  • the resistance value is shown as an average of 37 points of resistance between adjacent circuits.
  • connection structure was measured by a 90-degree peeling method according to JIS-Z0237.
  • the adhesive strength measuring device uses Tensilon UTM-4 (peeling speed 50mm / min, 2o C) manufactured by Toyo Baldwin Co., Ltd.
  • connection resistance and adhesion strength were performed immediately after adhesion and after being subjected to a reliability test in which the connection structure was held in a high-temperature and high-humidity tank at 85 ° C and 85% RH for 168 hours. Table 2 shows the measurement results.
  • Example 1 1.3 2.7 640 530 Example 2 1.2 2.5 740 650 Example 3 1.4 2.9 660 550 Example 4 1.4 2.7 765 630 Example 5 1.6 2.8 720 580 Example 6 1.8 3.5 71 0 605 Example 7 1.7 1.7 740 625 Comparative Example 1 1.8 4.8 580 280 Comparative Example 2 2.3 7.2 550 300 Comparative Example 3 1.5 3.5 650 380 Comparative Example 4 3.5 Open 80 Peel
  • the film adhesives obtained in Examples 3 and 6 were vacuum packaged and left at 40 ° C. for 3 days. Thereafter, a connection structure was prepared in the same manner as in “(1) Adhesive strength and connection resistance”, and the adhesive strength and connection resistance were measured. The measurement results are shown in Table 3 together with the values before standing (immediately after bonding).

Landscapes

  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Electric Connection Of Electric Components To Printed Circuits (AREA)
  • Combinations Of Printed Boards (AREA)
  • Wire Bonding (AREA)
  • Conductive Materials (AREA)

Abstract

L'invention concerne un adhésif contenant une résine thermoplastique (a), un composé polymérisable par voie radicalaire (b), un composé urée (c) représenté par la formule générale (10) ci-après, un amorceur de polymérisation radicalaire (d), et un composé acide (e).
PCT/JP2007/072763 2006-12-01 2007-11-26 Adhésif et structure de liaison utilisant celui-ci WO2008065997A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN200780043737.XA CN101541903B (zh) 2006-12-01 2007-11-26 粘接剂和使用该粘接剂的连接结构体
JP2008546976A JP5223679B2 (ja) 2006-12-01 2007-11-26 接着剤及びこれを用いた接続構造体

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2006325559 2006-12-01
JP2006-325559 2006-12-01
JP2007-234590 2007-09-10
JP2007234590 2007-09-10

Publications (1)

Publication Number Publication Date
WO2008065997A1 true WO2008065997A1 (fr) 2008-06-05

Family

ID=39467789

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2007/072763 WO2008065997A1 (fr) 2006-12-01 2007-11-26 Adhésif et structure de liaison utilisant celui-ci

Country Status (5)

Country Link
JP (1) JP5223679B2 (fr)
KR (1) KR101090577B1 (fr)
CN (1) CN101541903B (fr)
TW (1) TW200846435A (fr)
WO (1) WO2008065997A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008239863A (ja) * 2007-03-28 2008-10-09 Yokohama Rubber Co Ltd:The 硬化性樹脂組成物
WO2009031472A1 (fr) * 2007-09-05 2009-03-12 Hitachi Chemical Company, Ltd. Adhésif et structure de liaison l'utilisant
JP2009108226A (ja) * 2007-10-31 2009-05-21 Yokohama Rubber Co Ltd:The 硬化性樹脂組成物
JP2009299011A (ja) * 2008-06-16 2009-12-24 Fujikura Kasei Co Ltd 接着剤組成物、およびこれを含有する異方導電性接着剤
JP2010106261A (ja) * 2008-09-30 2010-05-13 Sony Chemical & Information Device Corp 異方性導電接着剤及びそれを用いた接続構造体の製造方法
JP2010111846A (ja) * 2008-10-09 2010-05-20 Hitachi Chem Co Ltd 接着剤組成物、回路接続用接着剤及び回路接続体
US20150014819A1 (en) * 2012-03-29 2015-01-15 Fujifilm Corporation Underlying film composition for imprints and pattern forming method using the same
JP2015025028A (ja) * 2013-07-24 2015-02-05 日立化成株式会社 接続材料、これを用いた接続構造体及びその製造方法
JP2015025029A (ja) * 2013-07-24 2015-02-05 日立化成株式会社 接続材料、接続構造体及びその製造方法
GB2518363A (en) * 2013-09-18 2015-03-25 Novalia Ltd Circuit board assembly

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011118719A1 (fr) * 2010-03-25 2011-09-29 日立化成工業株式会社 Composition adhésive, son utilisation, structure de connexion pour éléments de circuit, et procédé de production
CN102984610A (zh) * 2012-12-08 2013-03-20 张情情 一种音响

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6024826B2 (ja) * 1979-01-12 1985-06-14 田岡化学工業株式会社 接着方法
JP2003089775A (ja) * 2001-07-05 2003-03-28 Bridgestone Corp 異方性導電フィルム
JP2005054140A (ja) * 2003-08-07 2005-03-03 Hitachi Chem Co Ltd 接着剤組成物、回路接続用接着剤組成物、接続体及び半導体装置
JP2005123025A (ja) * 2003-10-16 2005-05-12 Bridgestone Corp 異方性導電フィルム
WO2007083623A1 (fr) * 2006-01-17 2007-07-26 Asahi Kasei Kabushiki Kaisha Composition de resine polyimide et stratifie polyimide metal

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100675412B1 (ko) * 2003-09-09 2007-01-29 다이니폰 인사츠 가부시키가이샤 광학용 시트 및 그 제조방법

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6024826B2 (ja) * 1979-01-12 1985-06-14 田岡化学工業株式会社 接着方法
JP2003089775A (ja) * 2001-07-05 2003-03-28 Bridgestone Corp 異方性導電フィルム
JP2005054140A (ja) * 2003-08-07 2005-03-03 Hitachi Chem Co Ltd 接着剤組成物、回路接続用接着剤組成物、接続体及び半導体装置
JP2005123025A (ja) * 2003-10-16 2005-05-12 Bridgestone Corp 異方性導電フィルム
WO2007083623A1 (fr) * 2006-01-17 2007-07-26 Asahi Kasei Kabushiki Kaisha Composition de resine polyimide et stratifie polyimide metal

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008239863A (ja) * 2007-03-28 2008-10-09 Yokohama Rubber Co Ltd:The 硬化性樹脂組成物
WO2009031472A1 (fr) * 2007-09-05 2009-03-12 Hitachi Chemical Company, Ltd. Adhésif et structure de liaison l'utilisant
JP2009108226A (ja) * 2007-10-31 2009-05-21 Yokohama Rubber Co Ltd:The 硬化性樹脂組成物
JP2009299011A (ja) * 2008-06-16 2009-12-24 Fujikura Kasei Co Ltd 接着剤組成物、およびこれを含有する異方導電性接着剤
KR20110063500A (ko) * 2008-09-30 2011-06-10 소니 케미카루 앤드 인포메이션 디바이스 가부시키가이샤 이방성 도전 접착제 및 그것을 사용한 접속 구조체의 제조 방법
JP2010106261A (ja) * 2008-09-30 2010-05-13 Sony Chemical & Information Device Corp 異方性導電接着剤及びそれを用いた接続構造体の製造方法
KR101683312B1 (ko) * 2008-09-30 2016-12-06 데쿠세리아루즈 가부시키가이샤 이방성 도전 접착제 및 그것을 사용한 접속 구조체의 제조 방법
JP2010111846A (ja) * 2008-10-09 2010-05-20 Hitachi Chem Co Ltd 接着剤組成物、回路接続用接着剤及び回路接続体
US20150014819A1 (en) * 2012-03-29 2015-01-15 Fujifilm Corporation Underlying film composition for imprints and pattern forming method using the same
JP2015025028A (ja) * 2013-07-24 2015-02-05 日立化成株式会社 接続材料、これを用いた接続構造体及びその製造方法
JP2015025029A (ja) * 2013-07-24 2015-02-05 日立化成株式会社 接続材料、接続構造体及びその製造方法
GB2518363A (en) * 2013-09-18 2015-03-25 Novalia Ltd Circuit board assembly
WO2015040397A1 (fr) 2013-09-18 2015-03-26 Novalia Ltd Ensemble carte à circuit imprimé

Also Published As

Publication number Publication date
CN101541903B (zh) 2013-04-17
CN101541903A (zh) 2009-09-23
TWI359851B (fr) 2012-03-11
JP5223679B2 (ja) 2013-06-26
TW200846435A (en) 2008-12-01
KR101090577B1 (ko) 2011-12-08
KR20090096489A (ko) 2009-09-10
JPWO2008065997A1 (ja) 2010-03-04

Similar Documents

Publication Publication Date Title
WO2008065997A1 (fr) Adhésif et structure de liaison utilisant celui-ci
JP4998468B2 (ja) 接着剤組成物及び回路部材の接続構造
KR100780135B1 (ko) 회로접속용 접착제조성물
KR102329065B1 (ko) 회로 접속 재료, 회로 접속 구조체, 접착 필름 및 권중체
JP5251393B2 (ja) 接着剤組成物、回路接続用接着剤及びそれを用いた接続体
JP6173928B2 (ja) 接着剤組成物、回路接続用接着剤及び接続体
JP2006257208A (ja) 接着剤、回路接続用接着剤、接続体及び半導体装置
KR102478959B1 (ko) 접착제 조성물 및 접속체
JP5292838B2 (ja) 接着剤、及び回路部材の接続構造体
JP6045918B2 (ja) 回路接続材料、回路接続部材の接続構造及び半導体装置
JP5577635B2 (ja) 接着剤組成物、回路接続用接着剤及び回路接続体
JP2009256581A (ja) 接着剤組成物、回路接続用接着剤及びそれを用いた接続体
JP2011037953A (ja) 接着剤組成物、回路接続構造体及び半導体装置
JP5298977B2 (ja) 接着剤組成物、回路接続用接着剤、接続体及び半導体装置
JP5236144B2 (ja) 接着剤組成物、回路接続構造体及び半導体装置
JP5034494B2 (ja) 接着剤組成物、回路接続用接着剤、接続体及び半導体装置
JP2013227420A (ja) 回路接続材料、回路接続構造体、接着フィルム及び巻重体。
JP2003277694A (ja) 回路接続用接着剤組成物及びそれを用いた回路接続構造体
TWI570208B (zh) 電路連接材料及連接體
TW202239933A (zh) 電路連接用接著膜及連接體

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200780043737.X

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07832488

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2008546976

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 1020097013674

Country of ref document: KR

122 Ep: pct application non-entry in european phase

Ref document number: 07832488

Country of ref document: EP

Kind code of ref document: A1