WO2010076990A2 - Compositions pour un film conducteur anisotrope, et film conducteur anisotrope les utilisant - Google Patents

Compositions pour un film conducteur anisotrope, et film conducteur anisotrope les utilisant Download PDF

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Publication number
WO2010076990A2
WO2010076990A2 PCT/KR2009/007519 KR2009007519W WO2010076990A2 WO 2010076990 A2 WO2010076990 A2 WO 2010076990A2 KR 2009007519 W KR2009007519 W KR 2009007519W WO 2010076990 A2 WO2010076990 A2 WO 2010076990A2
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meth
acrylate
weight
conductive film
anisotropic conductive
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PCT/KR2009/007519
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English (en)
Korean (ko)
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WO2010076990A3 (fr
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황자영
어동선
박진성
강정구
이태현
김현영
배상식
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제일모직 주식회사
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Publication of WO2010076990A2 publication Critical patent/WO2010076990A2/fr
Publication of WO2010076990A3 publication Critical patent/WO2010076990A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • 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
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/16—Solid spheres
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2333/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • 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
    • H05K2201/0137—Materials
    • H05K2201/0145—Polyester, e.g. polyethylene terephthalate [PET], polyethylene naphthalate [PEN]
    • 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
    • H05K2201/0137—Materials
    • H05K2201/0162—Silicon containing polymer, e.g. silicone

Definitions

  • the present invention relates to an anisotropic conductive film composition. More specifically, the present invention provides an anisotropic conductive film composition and an anisotropic conductive film formed of the composition by introducing a polyester-polysiloxane copolymer, having excellent adhesion and high reliability even when driving for a long time under high temperature / high humidity and thermal shock conditions It is about.
  • An anisotropic conductive film generally means the film-form adhesive which disperse
  • the anisotropic conductive film is generally used for LCD panel and tape carrier package (hereinafter referred to as TCP) or electrical connection such as printed circuit board and TCP, and is also used as a connection material such as COG mounting or COF mounting. It is getting a lot of attention.
  • the anisotropic conductive film is generally composed of a binder resin portion, a curing portion and conductive particles, and depending on the curing portion, (i) an epoxy type using a curing portion composed of an epoxy or phenolic resin and a curing agent or (ii) ((meth) It is divided into the (meth) acrylate type using the hardening part which consists of an acryl-type oligomer, a monomer, and a radical initiator.
  • the double epoxy type anisotropic conductive film has a strong network structure after curing due to the aromatic benzene rings contained in the epoxy resin, and thus can express good reliability.
  • it is not easy to control the flow characteristics at high temperature and high pressure because a plurality of aromatic benzene rings are essentially included, and a large amount of bubbles are generated when the connection is made, and thus there is a problem of low adhesive strength.
  • the conductive particles are not sufficiently mounted between the circuit to be connected.
  • due to the very high reaction temperature and long reaction time maintenance of the process control and the connecting device has been difficult.
  • the acrylic type (ii) can achieve rapid curing within a few seconds by using a rapid reaction rate of the radical curing reaction, it has the advantage that can significantly reduce the take time (Take Time), the product production rate is greatly improved.
  • the low glass transition temperature of the polymer resin mainly used for film formation and flow control purposes there is a problem in that long-term reliability is weak in terms of connection and adhesion due to repeated shrinkage and expansion in the state connected between circuits.
  • the polymer resin of high glass transition temperature is used, there may be a problem that initial properties such as poor connection and low adhesion due to poor flowability may occur.
  • An object of the present invention is to introduce a polyester-polysiloxane copolymer as a binder component, it is excellent in fluidity, not only the initial adhesive force, but also prevents the lifting phenomenon for a variety of adhesives during long time operation under high temperature / high humidity and thermal shock conditions, the initial appearance And an anisotropic conductive film composition having high reliability for connection resistance.
  • the anisotropic conductive film composition comprises a binder resin, a curable component and conductive particles, the binder resin is characterized in that it comprises a polyester-polysiloxane copolymer (a1) represented by the following formula (1):
  • a is an integer of 1 or more
  • (A) is a polyester unit having a structure of H- [O- (CR 1 2 ) n -CO-] m -XR 2-
  • B is (R 3 2 SiO 2/2 ) p (R 3 3 SiO 1/2 ) q [O 1/2 H] r [O 1/2 SiR 4 2 ] t
  • Polysiloxane units having a structure
  • X is oxygen or NR x And (double, R x Is a monovalent, substituted or unsubstituted hydrocarbon radical, hydrogen or -SiR ', having from 1 to 20 carbon atoms and wherein individual carbon atoms can be substituted with oxygen atoms.
  • R x is the same or different monovalent substituted or unsubstituted hydrocarbon radical
  • R is 2 Is a divalent substituted or unsubstituted hydrocarbon radical having 1 to 40 carbon atoms and wherein individual carbon atoms can be substituted with oxygen atoms
  • R 1 means a monovalent substituted or unsubstituted hydrocarbon radical or hydrogen, R 1 is the same as or different from each other,
  • R 2 is a divalent substituted or hydrocarbon radical having 1 to 40 carbon atoms and wherein individual carbon atoms can be substituted with oxygen atoms,
  • n is an integer from about 3 to about 10 and m is an integer from about 1 to about 1000;
  • R 3 Is the same or different, substituted or unsubstituted, aliphatic saturated or unsaturated, linear, cyclic, or branched hydrocarbon or hydrocarbon-oxy radical having 1 to 20 carbon atoms, or substituted or unsubstituted 6 to 20 Aromatics with carbon atoms Hydrocarbon or aromatic Means a hydrocarbon-oxy radical,
  • R 4 is the same or different, substituted or unsubstituted, aliphatic saturated, linear, cyclic, or branched hydrocarbon or hydrocarbon-oxy radical having 1 to 20 carbon atoms, or substituted or unsubstituted 6 to 20 An aromatic hydrocarbon or aromatic hydrocarbon-oxy radical having a carbon atom,
  • p is an integer from about 0 to about 3000
  • q is an integer from about 0 to about 50
  • r is an integer of at least about 1
  • t is an integer of at least about 1.
  • the binder resin may be (a1) polyester-polysiloxane copolymer and (a2) acrylonitrile-based resin, styrene-acrylonitrile-based resin, methyl methacrylate-butadiene-styrene-based resin, butadiene-based resin, or acrylic-based resin.
  • Resin, urethane resin, epoxy resin, phenoxy resin, polyamide resin, olefin resin, silicone resin, polyvinyl butyral resin, polyvinyl formal resin and polyester At least one matrix resin selected from the group consisting of resins.
  • the matrix resin (a2) may have a weight average molecular weight in the range of about 1,000 to about 1,000,000.
  • the curable component may be a (meth) acrylate radical curable material or an epoxy resin.
  • the conductive particles may include metal particles including Au, Ag, Ni, Cu, Pb; Carbon particles; Particles coated with a metal on the polymer resin; And at least one particle selected from the group consisting of particles insulated on a surface of a particle coated with a metal on the polymer resin.
  • the composition may further include additives such as coupling agents, fillers, tackifiers, polymerization inhibitors, antioxidants, heat stabilizers, curing accelerators.
  • additives such as coupling agents, fillers, tackifiers, polymerization inhibitors, antioxidants, heat stabilizers, curing accelerators.
  • the anisotropic conductive film composition comprises a) a binder resin, b1) a (meth) acrylate radical curable material, c1) a radical initiator, and d) conductive particles.
  • the a) binder resin includes about 5 wt% to about 75 wt% of the polyester-polysiloxane copolymer (a1) based on 100 wt% of the binder resin (based on solids).
  • the anisotropic conductive film composition comprises a) 100 parts by weight of a binder resin, b1) about 100 to about 300 parts by weight of a (meth) acrylate radical curable material, c1) about 5 to about 15 parts by weight of a radical initiator and d) About 10 to about 40 parts by weight of the conductive particles may be included.
  • the (meth) acrylate radical curable material is a (meth) acrylate monomer, a (meth) acrylate oligomer or a mixture thereof.
  • the (meth) acrylate monomers include hydroxy group-containing (meth) acrylates, C 1-20 linear alkyl (meth) acrylates, C 1-20 branched alkyl (meth) acrylates, C 6-20 aryl (meth) ) Acrylate, C 6-20 arylalkyl (meth) acrylate, C 6-20 cycloalkyl-containing (meth) acrylate, polycyclic (meth) acrylate, heterocyclic (meth) acrylate, ether group containing Alkyl (meth) acrylate, epoxy group-containing (meth) acrylate, aryloxy group-containing (meth) acrylate, alkylene glycol (meth) acrylate, bisphenol-A di (meth) acrylate, fluorene-based (meth) Acrylates and the like.
  • the (meth) acrylate oligomers include urethane-based (meth) acrylates, epoxy-based (meth) acrylates, polyester-based (meth) acrylates, fluorine-based (meth) acrylates, fluorene-based (meth) acrylates, and silicone-based ( Meth) acrylate, phosphate (meth) acrylate, maleimide modified (meth) acrylate, acrylate (methacrylate) and the like.
  • the (meth) acrylate oligomer may have a weight average molecular weight in the range of about 1,000 to about 100,000.
  • the radical initiator may be at least one selected from the group consisting of a photopolymerization initiator and a thermosetting initiator.
  • the anisotropic conductive film composition may further include a coupling agent in an amount of about 3 to about 8 parts by weight based on 100 parts by weight (based on solids) of the binder resin.
  • the anisotropic conductive film composition comprises a) binder resin, b2) epoxy resin, c2) curing agent, d) conductive particles, e) coupling agent and f) filler, wherein a) binder resin is polyester-
  • the polysiloxane copolymer (a1) is included in an amount of about 3 wt% to about 60 wt% based on 100 wt% (based on solids) of the binder resin.
  • the anisotropic conductive film composition may comprise a) 100 parts by weight of a binder resin, b2) about 25 to about 60 parts by weight of an epoxy resin, c2) about 5 to about 20 parts by weight of a curing agent, and d) about 5 to about 25 parts by weight of conductive particles. Parts, e) about 1 to about 8 parts by weight coupling agent and f) about 10 to about 50 parts by weight filler.
  • the epoxy resin may include one or more epoxy monomers, epoxy oligomers and epoxy polymers selected from the group consisting of bisphenol, novolac, glycidyl, aliphatic and cycloaliphatic.
  • the curing agent may be at least one selected from the group consisting of acid anhydrides, amines, imidazoles and hydrazides and cationics.
  • Another aspect of the invention relates to an anisotropic conductive film formed of the anisotropic conductive film composition.
  • the present invention is an anisotropic conductive film excellent in fluidity, and maintains the initial appearance by preventing the lifting phenomenon for a variety of adhesives for a long time under high temperature / high humidity and thermal shock conditions, as well as the initial adhesive strength, high reliability of connection resistance It has the effect of providing the composition and the anisotropic conductive film formed of the anisotropic conductive film composition.
  • the anisotropic conductive film composition includes a binder resin, a curable component, and conductive particles, and the binder resin includes a polyester-polysiloxane copolymer.
  • a (meth) acrylate radical curable material is used as a curable component as a radical curable anisotropic conductive anisotropic conductive film composition.
  • an epoxy resin is used as the curable component as the epoxy type anisotropic conductive film composition.
  • the binder resin includes (a1) polyester-polysiloxane copolymer and (a2) matrix resin.
  • the binder resin when (meth) acrylate-based radical curable materials are used as the curable component, the binder resin may comprise about 5 to about 75 weight percent of (a1) polyester-polysiloxane copolymer and (a2) about 25 to about 95 matrix resin. Contains weight percent. It has excellent initial adhesiveness and reliability in the above range, it can also maintain the initial appearance by preventing the lifting phenomenon even when driving for a long time under high temperature / high humidity and thermal shock conditions, and has a high reliability for connection resistance.
  • the binder resin comprises about 3 to about 60 weight percent of (a1) polyester-polysiloxane copolymer and about 40 to about 97 weight percent of (a2) matrix resin . It has excellent initial adhesiveness and reliability in the above range, it can also maintain the initial appearance by preventing the lifting phenomenon even when driving for a long time under high temperature / high humidity and thermal shock conditions, and has a high reliability for connection resistance.
  • polyester-polysiloxane copolymer (a1) used in the present invention is represented by the following Chemical Formula 1:
  • a is an integer of 1 or more
  • (A) is a polyester unit having a structure of H- [O- (CR 1 2 ) n -CO-] m -XR 2-
  • B is (R 3 2 SiO 2/2 ) p (R 3 3 SiO 1/2 ) q [O 1/2 H] r [O 1/2 SiR 4 2 ] t
  • Polysiloxane units having a structure
  • X is oxygen or NR x And (double, R x Is a monovalent, substituted or unsubstituted hydrocarbon radical, hydrogen or -SiR ', having from 1 to 20 carbon atoms and wherein individual carbon atoms can be substituted with oxygen atoms.
  • R x is the same or different monovalent substituted or unsubstituted hydrocarbon radical
  • R is 2 Is a divalent substituted or unsubstituted hydrocarbon radical having 1 to 40 carbon atoms and wherein individual carbon atoms can be substituted with oxygen atoms
  • R 1 means a monovalent substituted or unsubstituted hydrocarbon radical or hydrogen, R 1 is the same as or different from each other,
  • R 2 is a divalent substituted or unsubstituted hydrocarbon radical having 1 to 40 carbon atoms and wherein individual carbon atoms can be substituted with oxygen atoms,
  • n is an integer from about 3 to about 10 and m is an integer from about 1 to about 1000;
  • R 3 is the same or different, substituted or unsubstituted, aliphatic saturated or unsaturated, linear, cyclic, or branched hydrocarbon or hydrocarbon-oxy radical having 1 to 20 carbon atoms, or substituted or An aromatic hydrocarbon or aromatic hydrocarbon-oxy radical having 6 to 20 carbon atoms unsubstituted,
  • R 4 is the same or different, substituted or unsubstituted, aliphatic saturated, linear, cyclic, or branched hydrocarbon or hydrocarbon-oxy radical having 1 to 20 carbon atoms, or substituted or unsubstituted 6 to 20 An aromatic hydrocarbon or aromatic hydrocarbon-oxy radical having a carbon atom,
  • p is an integer from about 0 to about 3000
  • q is an integer from about 0 to about 50
  • r is an integer of at least about 1
  • t is an integer of at least about 1.
  • the polyester-polysiloxane copolymer (a1) of the present invention exhibits several excellent properties by controlling the degree of polymerization and the ratio of polysiloxane component to polyester content.
  • the polyester-polysiloxane copolymers (a1) of the present invention show superior improved physical properties compared to simple mixtures. There is also a characteristic that does not exhibit any bleeding effect.
  • Polysiloxanes tend to show a high affinity for basic substances, and also have a lower compatibility with other organic compounds. However, when the polyester is copolymerized with the polysiloxane, overall physical properties such as solubility, flowability, adhesion to various substrates, heat resistance, impact resistance, weather resistance, and coating properties are improved compared to the polysiloxane.
  • the polyester-polysiloxane copolymer can realize various physical properties according to the main component.
  • the main component of the copolymer is polyester, the properties such as moisture / water resistance, weather resistance, anti-wear effect, antiblock, and slip prevention can be improved.
  • the polysiloxane when the polysiloxane is the main component, the electrical and mechanical properties are improved, so that it can be used not only for anisotropic conductive films, but also for electrical and electronic components, laminated circuit boards, composite materials, paints, adhesives, structural materials, and anticorrosive materials. have.
  • polyester-polysiloxane copolymer (a1) of the present invention can improve the properties of various thermosetting / thermoplastic resins included in the binder.
  • thermosetting resins to which the polyester-polysiloxane copolymer may be added include epoxy resins, polyurethanes, polyureas, polyamides, epoxy resins, unsaturated polyester resins, polyester-polyether copolymers, polyimides, melamine resins, Phenolic resins, diallyl phthalate resins and derivatives thereof.
  • thermoplastic resins to which the polyester-polysiloxane copolymer may be added include polyacrylonitrile, polymethacrylonitrile, polymethyl acrylate, polyacrylamide, polymethacrylate, polymethacrylate esters, and other acrylic based Resins, polystyrenes, polyesters, polyamides, polyesteramides, thermoplastic polyurethanes, polyvinyl chloride, polycarbonate, polyacetal, polyvinylidene chloride, polyvinyl alcohol and cellulose derivatives.
  • the polyester-polysiloxane copolymer (a1) is used in an amount of about 5 wt% to about 75 wt% based on 100 wt% of the binder resin. There is an effect of improving reliability within the above range, the appearance characteristics are not impaired.
  • the polyester-polysiloxane copolymer (a1) is used in an amount of about 3 wt% to about 60 wt% based on 100 wt% of the binder resin. There is an effect of improving reliability within the above range, the appearance characteristics are not impaired.
  • the matrix resin (a2) forms a binder portion that serves as a matrix required to form a film, and may be used by selecting one or more from the group consisting of ordinary thermosetting / thermoplastic resins.
  • acrylonitrile resin styrene acrylonitrile resin, methyl methacrylate-butadiene-styrene resin, butadiene resin, acrylic resin, urethane resin, epoxy resin, phenoxy resin, polyamide type A resin, an olefin resin, a silicone resin, a polyvinyl butyral resin, a polyvinyl formal resin, a polyester resin, or the like may be used, but is not necessarily limited thereto. These can be used individually or in mixture of 2 or more types.
  • polyvinyl butyral, polyvinyl formal, polyester, phenol resin, epoxy resin, phenoxy resin, acrylic polymerizable resin, or the like can be used.
  • the matrix resin (a2) may be acrylonitrile-based resin, styrene-acrylonitrile-based resin, methyl methacrylate-butadiene-styrene-based resin, butadiene-based resin.
  • Resin, acrylic resin, urethane resin, polyamide resin, olefin resin, silicone resin, polyvinyl butyral resin, polyvinyl formal resin, polyester resin and the like can be used. have.
  • the matrix resin (a2) may be an epoxy resin, a phenoxy resin, a methyl methacrylate-butadiene-styrene resin, or the like.
  • the matrix resin preferably has a weight average molecular weight in the range of about 1,000 to about 1,000,000.
  • a resin having a weight average molecular weight of less than 1,000 film properties may be poor due to excessive tack characteristics, which are disadvantageous for film molding.
  • a resin having a weight average molecular weight of more than 1,000,000 is used, the compatibility with (meth) acrylate oligomers and monomers participating in the curing reaction may be deteriorated, and phase separation may occur when preparing the composition mixture.
  • styrene-acrylonitrile copolymer resin shows particularly excellent reliability.
  • a styrene-acrylonitrile (SAN) copolymer, a styrene-acrylonitrile-styrene (ASA) copolymer, or the like may be used.
  • thermoplastic resin having a high glass transition temperature for the purpose of improving reliability has a hard structure that is hard and brittle after curing. Therefore, when continuous stress is applied from the outside, it may cause cracking or deterioration of physical properties as the stress cannot be released from the inside.
  • the above problem can be solved by adding a resin having a low glass transition temperature and rubber characteristics.
  • Polymers such as acrylonitrile, methyl methacrylate-butadiene-styrene, butadiene, acryl, and urethane may be used as the resin having such low glass transition temperature and rubber properties.
  • the use of the resin may be minimized because it may cause a problem of deterioration of reliability by causing expansion of the anisotropic conductive film under high temperature / high humidity conditions.
  • a core of a polymer resin having a low glass transition temperature such as butadiene is used as a core, and a polymer resin having a relatively high glass transition temperature such as acrylic or styrene is used as a shell.
  • a polymer type polymer having a specific structure of the shell type it is possible to simultaneously solve the stress relaxation problem and the expansion problem related to reliability in the cured anisotropic conductive film.
  • Such core-shell polymer copolymer resins include Ganz's AC series and Resinous Kasei's RKB series, and Regina's RKB series is an epoxy resin. It is a product which disperse
  • the matrix resin (a2) may comprise about 5 to about 50% by weight relative to 100% by weight of the total composition. The problem that the film characteristic becomes weak does not arise within the said range, and external appearance characteristic and connection resistance are not impaired.
  • b1) (meth) acrylate radical curable material or b2) epoxy resin may be used as the curable component.
  • a (meth) acrylate oligomer, a (meth) acrylate monomer or a mixture thereof can be used as the radically curable material.
  • the radically curable material (b1) preferably includes about 100 to about 300 parts by weight based on 100 parts by weight (based on solids) of the binder. It is excellent in appearance and hardening characteristic within the said range, and is excellent in adhesiveness, reliability, and film characteristic with a base material.
  • one or more oligomers selected from the group of known (meth) acrylate oligomers can be used without limitation, and preferably a urethane-based (meth) acryl having a weight average molecular weight in the range of about 1,000 to about 100,000.
  • epoxy type (meth) acrylate polyester type (meth) acrylate, fluorine type (meth) acrylate, fluorene type (meth) acrylate, silicone type (meth) acrylate, phosphoric acid type (meth) acrylate, Oligomers, such as maleimide modified (meth) acrylate and an acrylate (methacrylate), can be used individually or in combination of 2 or more types, respectively.
  • the intermediate molecular structure is bisphenol, such as 2-bromohydroquinone, resorcinol, catechol, bisphenol A, bisphenol F, bisphenol AD, bisphenol S, 4,4'- dihydride It may contain a skeleton such as oxybiphenyl, bis (4-hydroxyphenyl) ether, and one substituent of an alkyl group, aryl group, methylol group, allyl group, cyclic aliphatic group, halogen (such as tetrabromobisphenol A) It can contain more.
  • bisphenol such as 2-bromohydroquinone, resorcinol, catechol, bisphenol A, bisphenol F, bisphenol AD, bisphenol S, 4,4'- dihydride It may contain a skeleton such as oxybiphenyl, bis (4-hydroxyphenyl) ether, and one substituent of an alkyl group, aryl group, methylol group, allyl group, cyclic aliphatic
  • the (meth) acrylate oligomer of this invention contains at least 2 or more maleimide groups in a molecule
  • numerator for example, 1-methyl- 2, 4-bismaleimide benzene, N, N'-m-phenylene Bismaleimide, N, N'-p-phenylenebismaleimide, N, N'-m-toylene bismaleimide, N, N'-4,4-biphenylene bismaleimide, N, N ' -4,4- (3,3'-dimethylbiphenylene) bismaleimide, N, N'-4,4- (3,3'-dimethyl diphenyl methane) bismaleimide, N, N'-4 , 4- (3,3'-diethyl diphenyl methane) bismaleimide, N, N'-4,4-diphenylmethanebismaleimide, N, N'-4,4-diphenylpropanebismaleimide , N, N'-4,4-
  • one or more fluorene-based (meth) acrylate oligomers obtained from fluorene derivatives represented by the following formula (2) may be included and used.
  • R is each independently an alkyl group, an alkoxy group, an aryl group or a cycloalkyl group
  • m is each independently an integer of 0 to 4
  • n is each independently an integer of 2 to 5).
  • fluorene-based (meth) acrylates examples include fluorene-based epoxy (meth) acrylate oligomers and fluorene-based urethane (meth) acrylate oligomers.
  • the fluorene-based epoxy (meth) acrylate oligomer may be obtained by reacting (meth) acrylic acid glycidyl with a fluorene compound in a temperature range at 50 to 120 ° C. for 5 to 30 hours using a solvent.
  • the fluorene-based urethane (meth) acrylate oligomer may be obtained by reacting fluorene derivative diol with (meth) acrylate having a hydroxyl group on diisocyanate and ester.
  • the solvent examples include alkylene monoalkyl ether acetates such as methyl cellosolve acetate, propylene glycol monomethyl ether acetate, and 3-methoxy butyl-1-acetate; Methyl ethyl ketone, methyl amyl ketone and the like.
  • the (meth) acrylate monomer serves as a reactive diluent.
  • (meth) acrylate one or more monomers selected from conventionally known (meth) acrylate monomer groups can be used without limitation.
  • the (meth) acrylate monomers include hydroxy group-containing (meth) acrylates, C 1-20 linear alkyl (meth) acrylates, C 1-20 branched alkyl (meth) acrylates, C 6-20 aryl (meth) ) Acrylate, C 6-20 arylalkyl (meth) acrylate, C 6-20 cycloalkyl-containing (meth) acrylate, polycyclic (meth) acrylate, heterocyclic (meth) acrylate, ether group containing Alkyl (meth) acrylate, epoxy group-containing (meth) acrylate, aryloxy group-containing (meth) acrylate, alkylene glycol (meth) acrylate, bisphenol-A di (meth) acrylate, fluorene-based (meth) Acrylate and acid phosphoxy ethyl (meth) acrylate and the like can be used, but are not necessarily limited thereto. These can be used individually or in mixture of
  • the (meth) acrylate monomers are 1,6-hexanediol mono (meth) acrylate, 2-hydroxy ethyl (meth) acrylate, 2-hydroxy propyl (meth) acrylate, 2-hydroxy Butyl (meth) acrylate, 2-hydroxy-3-phenyl oxypropyl (meth) acrylate, 1,4-butanediol (meth) acrylate, 2-hydroxyalkyl (meth) acryloyl phosphate, 4-hydroxy Roxy cyclohexyl (meth) acrylate, neopentylglycol mono (meth) acrylate, trimethylol-epan di (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, di Pentaerythritol penta (meth) acrylate, pentaerythritol hexa (
  • the (meth) acrylate monomer is also preferably used a fluorene-based (meth) acrylate monomer having a fluorene-based skeleton represented by the formula (2), as such a fluorene-based (meth) acrylate monomer
  • a fluorene-based (meth) acrylate monomer having a fluorene-based skeleton represented by the formula (2) as such a fluorene-based (meth) acrylate monomer
  • Conventionally known conventional fluorene-based epoxy (meth) acrylate monomers, fluorene-based urethane (meth) acrylate monomers, and the like can be used.
  • commercially available examples of the fluorene-based (meth) acrylate monomers include BPEF-A (Osaka Gas).
  • the epoxy resin may include one or more epoxy monomers, epoxy oligomers and epoxy polymers selected from the group consisting of bisphenol, novolac, glycidyl, aliphatic and cycloaliphatic.
  • epoxy resin any material containing at least one bond structure that can be selected from among the known epoxy-based molecular structures such as bisphenol type, novolak type, glycidyl type, aliphatic, alicyclic, etc. is not limited. Can be used
  • the epoxy resin which is solid at normal temperature and the epoxy resin which is liquid at normal temperature can be used together, and a flexible epoxy resin can be used together further here.
  • the solid epoxy resin include a phenol novolac epoxy resin, a cresol novolac epoxy resin, and an epoxy resin mainly composed of dicyclo pentadiene and bisphenol A. Or an F-type polymer or a modified epoxy resin, but is not necessarily limited thereto.
  • the liquid epoxy resin at room temperature may include bisphenol A type or F type or mixed epoxy resin, but is not necessarily limited thereto.
  • Non-limiting examples of the flexible epoxy resins include dimer acid-modified epoxy resins, epoxy resins based on propylene glycol, urethane (urethane) modified epoxy resins, and the like.
  • the excellent insulation properties inherent in the molecular structure can reduce the possibility of short circuits, especially between circuits, and ensure low initial connection resistance and excellent reliability, thereby improving productivity and reliability of the final product.
  • a fluorene-based epoxy resin may be used, and the fluorene base structure is as shown in Chemical Formula 2 above.
  • the epoxy resin (b2) is preferably used in the range of about 25 to about 60 parts by weight based on 100 parts by weight (based on solids) of the binder resin. It is excellent in appearance and connection characteristics in the above range, and excellent in film characteristics and reliability.
  • Examples of commercially available epoxy resins (b2) include DER-331 (DOW Chemical), YDCN-500-80P (Kukdo Chemical), YDCN-500-90P (Kukdo Chemical), YP-50 (Kukdo Chemical)
  • Examples of common resins such as PKFE (INCHEMREZ) and fluorene-based epoxy resins include BPFG and BPEGF (Osaka Gas), but are not necessarily limited to the products described.
  • the radical initiator (c1) is used when the curable component is a radical curable material.
  • the radical initiator (c1) may be a photopolymerization initiator, a thermosetting initiator or a mixture thereof.
  • peroxide-based and azo-based may be used as the radical initiator (c1).
  • the peroxide-based initiator include t-butyl peroxylaurate, 1,1,3,3-t-methylbutylperoxy-2. -Ethyl hexanonate, 2,5-dimethyl-2,5-di (2-ethylhexanoyl peroxy) hexane, 1-cyclohexyl-1-methylethyl peroxy-2-ethyl hexanonate, 2,5 -Dimethyl-2,5-di (m-toluoyl peroxy) hexane, t-butyl peroxy isopropyl monocarbonate, t-butyl peroxy-2-ethylhexyl monocarbonate, t-hexyl peroxy benzoate, t -Butyl peroxy acetate, dicumyl peroxide, 2,5, -dimethyl-2,5-di (t
  • the radical initiator preferably contains about 5 to about 15 parts by weight based on 100 parts by weight (based on solids) of the binder resin of the present invention. If the content is less than 5 parts by weight, the curing reaction may not be sufficiently performed, the appearance characteristics and reliability characteristics may be inhibited. If the content exceeds 15 parts by weight, corrosion and deterioration of reliability due to residual radicals may occur.
  • the curing agent (c2) is used when the curable component is an epoxy resin.
  • the curing agent (c2) can be used without limitation any of the thermosetting agent of the epoxy curing type known in the art. Specific examples thereof include acid anhydride, amine, imidazole, hydrazide, and cationic, but are not limited thereto. These can be used individually or in mixture of 2 or more types.
  • Preferred of these is cationic, and specific examples include ammonium / antimony hexafluoride and the like.
  • Such epoxy curing agent (c2) is preferably included in the range of about 5 to about 20 parts by weight based on 100 parts by weight of the binder resin solid content. If the content is less than about 5 parts by weight, the curing reaction may not be sufficiently performed, which may hinder the appearance and reliability characteristics. If the content is more than about 20 parts by weight, the stability and reliability may be reduced by the residual curing agent. .
  • the electroconductive particle used by this invention is applied as a filler for giving electroconductive performance.
  • conductive particles conventionally known conductive particles can be used without limitation. Specific examples include metal particles including Au, Ag, Ni, Cu, Pb; Carbon particles; Particles coated with a metal on the polymer resin; And particles insulated on the surface of the metal coated with the polymer resin, but are not necessarily limited thereto. These may be used alone or in combination of two or more thereof.
  • the carbon particles include carbon black, graphite, activated carbon, carbon whiskers, fullerene, carbon nanotubes, and the like.
  • the polymer resin may include polyethylene, polypropylene, polyester, polystyrene, polyvinyl alcohol, and the like, but is not limited thereto.
  • Examples of the metal coating the polymer resin include Au, Ag, and Ni, but are not necessarily limited thereto.
  • the size of the electroconductive particle can be selected and used according to a use in the range of about 2 to about 30 micrometers by the pitch of the circuit to which it is applied.
  • the conductive particles may include about 10 to about 40 parts by weight based on 100 parts by weight (based on solids) of the binder resin in the case of radical curing. If the content is less than about 10 parts by weight, it is easy to cause a poor connection due to the reduction of the connection area when Mis-Align occurs between the terminals during the connection process, and when the content exceeds about 40 parts by weight, it is easy to cause poor insulation.
  • the epoxy curable adhesive may include about 5 parts by weight to about 25 parts by weight based on 100 parts by weight of the binder resin (based on solids). Connection and insulation failures do not occur within the above range.
  • the coupling agent includes vinyl trichloro silane, vinyl trimethoxy silane, 3-glycidoxy propyl trimethoxy silane, 3-methacryloxy propyl trimethoxy silane, 2-aminoethyl-3-aminopropyl methyldimethoxy Silane, 3-ureidopropyl triethoxy silane, and the like, and various kinds of such silane coupling agents may be used.
  • the coupling agent (e) may include about 10 parts by weight or less, preferably about 3 to about 8 parts by weight, based on 100 parts by weight (based on solids) of the binder resin in the case of a radical curing type.
  • the content of the coupling agent (e) for the epoxy curable adhesive may include about 1 to about 8 parts by weight based on 100 parts by weight (based on solids) of the binder resin.
  • the filler (f) may be preferably included in the epoxy curable composition.
  • the filler (f) may be included in about 20 to about 50 parts by weight based on 100 parts by weight (based on solids) of the binder.
  • hydrophobic nano silica particles having a size of about 5 to 20 nanometers (nm) may be used.
  • the hydrophobic nano silica particles may be surface treated with an organic silane.
  • Commercialized products include Aerosil R-972, Aerosil R-202, Aerosil R-805, Aerosil R-812, Aerosil R-8200 (above Degussa), and may be used in any kind. It is not limited
  • the filler (f) functions to provide excellent initial adhesion and low connection resistance by suppressing thermal expansion at high temperature by providing proper flow and solid curing structure in the bonding and curing process.
  • the anisotropic conductive film composition of the present invention may further include other additives such as tackifiers, polymerization inhibitors, antioxidants, heat stabilizers, curing accelerators, and the like to add additional physical properties without inhibiting basic physical properties.
  • the additives may be used alone or in combination of two or more.
  • the additive may include about 0.1 to about 5 parts by weight based on 100 parts by weight (based on solids) of the binder resin.
  • polymerization inhibitor one or more selected from the group consisting of hydroquinone, hydroquinone monomethyl ether, p-benzoquinone, phenothiazine and mixtures thereof can be used.
  • antioxidant a branched phenolic or hydroxy cinnamate-based substance may be added.
  • Examples include tetrakis- (methylene- (3,5-di-t-butyl-4-hydro cinnamate) methane, 3,5-bis (1,1-dimethylethyl) -4-hydroxy benzene propanoic liquid Seed thiol di-2,1-ethanediyl ester, octadecyl 3,5-di-t-butyl-4-hydroxy hydrocinnamate (above manufactured by Ciba), 2,6-di-tertiary-p-methyl Phenols and the like.
  • tetrakis- (methylene- (3,5-di-t-butyl-4-hydro cinnamate) methane 3,5-bis (1,1-dimethylethyl) -4-hydroxy benzene propanoic liquid Seed thiol di-2,1-ethanediyl ester, octadecyl 3,5-di-t-butyl-4-hydroxy
  • the curing accelerator at least one of a solid imidazole-based accelerator, a solid phase and a liquid amine curing accelerator, and the like may be used.
  • the various additives are not limited to the types described.
  • Another aspect of the present invention relates to an anisotropic conductive film formed of the anisotropic conductive film composition according to.
  • the manufacturing method of the said anisotropic conductive film is not specifically limited.
  • one or more selected resins of the matrix resin constituting the binder part are dissolved in an organic solvent to be liquefied, and then, the polyester-polysiloxane copolymer, the curable component, and the conductive particles are mixed and stirred for a predetermined time within a range not to be crushed.
  • it is applied to a thickness of about 10 to about 50 ⁇ m on a release film and then dried for a certain time to obtain an anisotropic conductive film having a single layer structure by volatilizing the organic solvent.
  • a conventional organic solvent can be used as the organic solvent without limitation, and in the present invention, an anisotropic conductive film having a multilayer structure of two or more layers may be obtained by repeating the above procedure two or more times.
  • Phenoxy resins dissolved in toluene at 30% by weight PKHH, Inchemrez, USA
  • Coupling agent ⁇ -glycidoxy propyl trimethoxy silane (KBM-403, ShinEtsu)
  • composition which mixed the component of following Table 1 was stirred at 300 rpm at the normal temperature (25 degreeC) for 60 minutes.
  • the composition was formed into a silicon base surface-treated polyethylene base film with a thickness of 20 ⁇ m, using a casting knife to form a film, the drying time of the film was 10 minutes at 50 °C. .
  • Example 1-6 shows excellent results in both the initial adhesive strength and the adhesive strength after the reliability evaluation compared to Comparative Example 1-4.
  • Example 1-6 have low resistance values in both the initial connection resistance and the connection resistance after the reliability evaluation.
  • the present invention has been described as the preferred embodiment mentioned above, it is possible to make various modifications or variations without departing from the spirit and scope of the invention.
  • the present invention includes all of the polyester-polysiloxane copolymer represented by the general formula (1), and is not limited to the kind described in the above general formula in the claims, the appended claims belong to the gist of the present invention. Includes modifications and variations.

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  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Non-Insulated Conductors (AREA)
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Abstract

L'invention concerne des compositions pour un film conducteur anisotrope qui comprend des résines formant liant, des ingrédients thermodurcissables et des particules conductrices, dans lesquelles les résines formant liant contiennent des copolymères polyester-polysiloxane. Les compositions de film conducteur anisotrope possèdent une fluidité et une adhérence initiale supérieures, et empêchent le film d'être détaché de divers d'objets, ce qui maintient l'apparence extérieure initiale même lorsque le film est utilisé sur une longue période de temps dans des conditions d'impact thermique et de température élevée/d'humidité élevée. Les compositions de la présente invention possèdent une fiabilité élevée contre la résistance de connexion. Par conséquent, les compositions selon la présente invention améliorent la fiabilité de toute une gamme de dispositifs d'affichage, et peuvent être largement utilisées en tant que compositions pour divers adhésifs.
PCT/KR2009/007519 2008-12-29 2009-12-16 Compositions pour un film conducteur anisotrope, et film conducteur anisotrope les utilisant WO2010076990A2 (fr)

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CN114149264A (zh) * 2021-12-14 2022-03-08 福建臻璟新材料科技有限公司 一种原位聚合成型氮化硅陶瓷薄片的制备工艺

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KR101351617B1 (ko) * 2010-12-23 2014-01-15 제일모직주식회사 이방 도전성 필름
KR101397690B1 (ko) * 2010-12-31 2014-05-22 제일모직주식회사 이방 전도성 필름
US20140193985A1 (en) * 2013-01-10 2014-07-10 Pioneer Material Precision Tech Co., Ltd. Electrically conductive connecting member, method of forming and using the same
KR20150082099A (ko) * 2014-01-06 2015-07-15 주식회사 동진쎄미켐 전도성 필름 형성용 조성물 및 전도성 필름
CN114271040A (zh) * 2019-08-21 2022-04-01 阿莫绿色技术有限公司 散热塑料

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WO2000060614A1 (fr) * 1999-04-01 2000-10-12 Mitsui Chemicals, Inc. Pate a conduction anisotrope
JP2001291431A (ja) * 2000-04-10 2001-10-19 Jsr Corp 異方導電性シート用組成物、異方導電性シート、その製造方法および異方導電性シートを用いた接点構造
JP2005126569A (ja) * 2003-10-23 2005-05-19 Sumitomo Bakelite Co Ltd 異方導電性接着剤、異方導電性接着フィルムおよび表示装置
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KR20100077793A (ko) 2010-07-08

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