WO2013042203A1 - 接着剤組成物、フィルム状接着剤、接着シート、回路接続体及び回路部材の接続方法 - Google Patents

接着剤組成物、フィルム状接着剤、接着シート、回路接続体及び回路部材の接続方法 Download PDF

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Publication number
WO2013042203A1
WO2013042203A1 PCT/JP2011/071388 JP2011071388W WO2013042203A1 WO 2013042203 A1 WO2013042203 A1 WO 2013042203A1 JP 2011071388 W JP2011071388 W JP 2011071388W WO 2013042203 A1 WO2013042203 A1 WO 2013042203A1
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Prior art keywords
circuit
circuit board
adhesive
adhesive composition
main surface
Prior art date
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PCT/JP2011/071388
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English (en)
French (fr)
Japanese (ja)
Inventor
伊澤　弘行
有福　征宏
加藤木　茂樹
弘 横田
泰三 山村
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日立化成株式会社
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Application filed by 日立化成株式会社 filed Critical 日立化成株式会社
Priority to PCT/JP2011/071388 priority Critical patent/WO2013042203A1/ja
Priority to PCT/JP2012/074051 priority patent/WO2013042724A1/ja
Priority to KR1020147009493A priority patent/KR102193517B1/ko
Priority to CN201280045620.6A priority patent/CN103814100B/zh
Priority to TW101134528A priority patent/TWI587761B/zh
Priority to JP2013534742A priority patent/JP6366936B2/ja
Priority to US13/623,289 priority patent/US20130140083A1/en
Publication of WO2013042203A1 publication Critical patent/WO2013042203A1/ja
Priority to JP2016197363A priority patent/JP6532850B2/ja
Priority to JP2018126916A priority patent/JP2018188646A/ja

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/20—Conductive material dispersed in non-conductive organic material
    • H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
    • H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L24/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L24/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • 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
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/14—Structural association of two or more printed circuits
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/08—Metals
    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/314—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive layer and/or the carrier being conductive
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
    • 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
    • C09J2483/00—Presence of polysiloxane
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29199—Material of the matrix
    • H01L2224/2929—Material of the matrix with a principal constituent of the material being a polymer, e.g. polyester, phenolic based polymer, epoxy
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • H01L2224/29299—Base material
    • H01L2224/2939—Base material with a principal constituent of the material being a polymer, e.g. polyester, phenolic based polymer, epoxy
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
    • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
    • H01L2224/29001—Core members of the layer connector
    • H01L2224/29099—Material
    • H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
    • H01L2224/29298—Fillers
    • H01L2224/29399—Coating material
    • H01L2224/294—Coating material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/80—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected
    • H01L2224/83—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected using a layer connector
    • H01L2224/838—Bonding techniques
    • H01L2224/8385—Bonding techniques using a polymer adhesive, e.g. an adhesive based on silicone, epoxy, polyimide, polyester
    • H01L2224/83851—Bonding techniques using a polymer adhesive, e.g. an adhesive based on silicone, epoxy, polyimide, polyester being an anisotropic conductive adhesive
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/06—Polymers
    • H01L2924/078—Adhesive characteristics other than chemical
    • H01L2924/0781—Adhesive characteristics other than chemical being an ohmic electrical conductor
    • H01L2924/07811—Extrinsic, i.e. with electrical conductive fillers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
    • H01L2924/151—Die mounting substrate
    • H01L2924/156—Material
    • H01L2924/15786—Material with a principal constituent of the material being a non metallic, non metalloid inorganic material
    • H01L2924/15788—Glasses, e.g. amorphous oxides, nitrides or fluorides
    • 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
    • H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
    • H05K2201/0203—Fillers and particles
    • H05K2201/0206—Materials
    • H05K2201/0212—Resin particles
    • 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
    • H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
    • H05K2201/0203—Fillers and particles
    • H05K2201/0206—Materials
    • H05K2201/0221—Insulating particles having an electrically conductive coating

Definitions

  • the present invention relates to an adhesive composition, a film adhesive, an adhesive sheet, a circuit connector, and a circuit member connection method.
  • the adhesive composition includes, for example, a connection between a liquid crystal display element and TCP (Tape Carrier Package) or COF (Chip On Film), a connection between TCP or COF and a printed wiring board, FPC (Flexible Printed Circuit) and printed wiring. It is used for connecting to a board, mounting a semiconductor element on a substrate, and the like.
  • TCP Transmission Carrier Package
  • COF Chip On Film
  • FPC Flexible Printed Circuit
  • adherend examples include printed wiring boards, organic substrates such as polyimide, polyethylene terephthalate (PET), polycarbonate (PC), and polyethylene naphthalate (PEN), metals such as copper and aluminum, and ITO (Indium Tin Oxide).
  • organic substrates such as polyimide, polyethylene terephthalate (PET), polycarbonate (PC), and polyethylene naphthalate (PEN), metals such as copper and aluminum, and ITO (Indium Tin Oxide).
  • a composite oxide of indium and tin), Si 3 N 4 , SiO 2 and other substrates having various surface states are used, and the adhesive composition has a molecular design tailored to each adherend. is necessary.
  • the properties required for such an adhesive composition are diverse, including adhesiveness, heat resistance, reliability in a high temperature and high humidity state, and the like.
  • thermosetting resin containing an epoxy resin exhibiting high adhesiveness and high reliability has been used (for example, see Patent Document 1).
  • a curing agent such as an epoxy resin, a phenol resin having reactivity with the epoxy resin, and a thermal latent catalyst for promoting the reaction between the epoxy resin and the curing agent are generally used.
  • a thermal latent catalyst is a substance that does not react at a storage temperature such as room temperature and exhibits high reactivity when heated. Further, it is an important factor for determining the curing temperature and the curing rate, and various compounds are used from the viewpoint of the storage stability of the adhesive composition at room temperature and the curing rate during heating. In the actual process, desired adhesiveness is obtained by curing conditions for curing at a temperature of 170 ° C. to 250 ° C. for 1 to 3 hours.
  • thermosetting resins including conventional epoxy resins
  • a thermal latent catalyst with low activation energy in order to achieve curing at a low temperature in a short time (low temperature fast curing)
  • the storage stability of the adhesive composition at room temperature decreases.
  • a radical curable adhesive composition using a radical polymerizable compound such as a (meth) acrylate derivative and a peroxide as a radical polymerization initiator as an adhesive composition having a low temperature fast curing property has attracted attention.
  • a radical polymerizable compound such as a (meth) acrylate derivative and a peroxide
  • a radical polymerization initiator as an adhesive composition having a low temperature fast curing property.
  • radical curing radicals that are reactive species are rich in reactivity, so that curing at a low temperature and in a short time is possible.
  • the adhesive composition using radical curing has a large cure shrinkage at the time of curing, it is inferior in adhesive strength compared to the case of using an epoxy resin. There is a tendency to decrease.
  • a method for improving the adhesive strength a method using an adhesion assistant typified by a silane coupling agent (for example, see Patent Document 3), a method for improving the adhesive strength by imparting the flexibility of a cured product by an ether bond.
  • a method for improving adhesive strength by dispersing stress-absorbing particles made of a rubber-based elastic material in an adhesive composition has been proposed. Yes.
  • the adhesive composition should be used at a lower temperature. It is required to be cured. Moreover, since the surface of PET, PC, PEN or the like is smooth, the adhesion effect due to the physical anchoring effect (anchor effect) is small.
  • organic base materials such as PET, PC, and PEN have a larger coefficient of thermal expansion and different surface energy than glass substrates. Therefore, in order to improve wettability to the adherend and reduce internal stress, it is necessary to impart sufficient flexibility to the adhesive composition.
  • the method described in Patent Document 4 provides sufficient flexibility. It cannot be imparted, and further improvement in adhesive strength is desired.
  • the present invention obtains excellent adhesive strength even when cured at a low temperature on an organic substrate having low heat resistance such as polyethylene terephthalate (PET), polycarbonate (PC), and polyethylene naphthalate (PEN).
  • Adhesive composition that can maintain stable performance (adhesive strength and connection resistance) even after long-term reliability test (high temperature and high humidity test), and film adhesive and adhesive using the same It aims at providing the connection method of a sheet
  • the present inventors have low adhesive strength to semiconductor elements and liquid crystal display elements using organic base materials such as PET, PC and PEN which are thermoplastic resins having low heat resistance. Have found that the relaxation of internal stress is insufficient. As a result of further studies to solve these problems, it was possible to obtain excellent adhesive strength by using silicone fine particles with a specific structure, and stable performance even after a long-term reliability test (high temperature and high humidity test). It was found that (adhesive strength and connection resistance) can be maintained, and the present invention was completed.
  • the present invention includes at least one first circuit member having a first circuit electrode formed on a main surface of a first circuit board, which includes a thermoplastic resin having a glass transition temperature of 200 ° C. or lower; To bond the second circuit member having the second circuit electrode formed on the main surface of the second circuit board so that the first circuit electrode and the second circuit electrode are electrically connected to each other.
  • An adhesive composition comprising a core-shell type silicone fine particle having a core layer and a shell layer provided so as to cover the core layer.
  • the adhesive composition contains the silicone fine particles having the specific structure, the interaction between the silicone fine particles is alleviated and the structural viscosity (non-Newtonian viscosity) is lowered, so that the silicone fine particles are dispersed in the resin. Therefore, it is considered that the internal stress can be sufficiently relaxed effectively.
  • the adhesive strength with respect to the base material for example, PET, PC, PEN etc.
  • a thermoplastic resin whose glass transition temperature (Tg) is 200 degrees C or less can be improved, and the adhesive strength between circuit members can be improved.
  • stable performance (adhesive strength and connection resistance) can be maintained even after a long-term reliability test.
  • the glass transition temperature of the core layer of the silicone fine particles is preferably ⁇ 130 ° C. or higher and ⁇ 20 ° C. or lower, more preferably ⁇ 125 ° C. or higher and ⁇ 40 ° C. or lower, and particularly preferably ⁇ 120 ° C. Above and below -50 ° C. Thereby, since internal stress can fully be relieved, the adhesive strength between circuit members can be improved. In addition, stable performance can be maintained even after a long-term reliability test. When the glass transition temperature is higher than ⁇ 20 ° C., the internal stress cannot be sufficiently relaxed, so that there is a tendency that a sufficient effect of improving the adhesive strength cannot be obtained. When the glass transition temperature is lower than ⁇ 130 ° C., sufficient cohesive force cannot be obtained. There exists a tendency for adhesive strength to fall.
  • the adhesive composition according to the present invention preferably further contains a thermoplastic resin, a radical polymerizable compound, a radical polymerization initiator, and a vinyl compound having a phosphate group.
  • the adhesive composition preferably further contains conductive particles.
  • conductive particles good conductivity or anisotropic conductivity is imparted to the adhesive composition, and therefore, it is more suitably used for bonding applications between circuit members having circuit electrodes (connection terminals). . Further, the connection resistance can be further reduced by electrically connecting the circuit members via the adhesive composition containing conductive particles.
  • the present invention provides a film adhesive obtained by molding the above adhesive composition into a film. Moreover, this invention provides an adhesive sheet provided with a base material and the adhesive bond layer which consists of the said film adhesive formed on this base material.
  • the present invention provides a first circuit member having a first circuit electrode formed on a main surface of a first circuit board, and a second circuit electrode having a second circuit electrode formed on a main surface of a second circuit board. Two circuit members, and interposed between the main surface of the first circuit member and the main surface of the second circuit member, and electrically connecting the first circuit electrode and the second circuit electrode. A connection part to be connected, wherein at least one of the first circuit board and the second circuit board includes a thermoplastic resin having a glass transition temperature of 200 ° C. or lower, and the connection Provided is a circuit connector in which the portion is made of a cured product of the adhesive composition according to the present invention.
  • connection part is made of a cured product of the adhesive composition according to the present invention, so that even when a circuit member containing a thermoplastic resin having a glass transition temperature of 200 ° C. or lower is used, Excellent adhesion strength and stable performance after long-term reliability test (adhesion strength and connection resistance) can be obtained.
  • thermoplastic resin having a glass transition temperature of 200 ° C. or lower preferably contains at least one selected from the group consisting of polyethylene terephthalate, polycarbonate, and polyethylene naphthalate.
  • one of the first circuit board and the second circuit board includes at least one selected from the group consisting of polyethylene terephthalate, polycarbonate, and polyethylene naphthalate, and the other circuit board is It is preferable to contain a polyimide resin and / or polyethylene terephthalate. Thereby, the wettability and adhesive strength of a circuit board and an adhesive composition improve more, and the outstanding connection reliability can be acquired.
  • the present invention provides a first circuit member having a first circuit electrode formed on a main surface of a first circuit board, and a second circuit electrode having a second circuit electrode formed on a main surface of a second circuit board.
  • the first circuit electrode and the second circuit electrode are electrically connected to each other by interposing and curing the adhesive composition according to the present invention between the two circuit members.
  • a circuit member connection method including the thermoplastic resin is provided.
  • circuit member connection method of the present invention even after low temperature curing suitable for a circuit member containing a thermoplastic resin having a glass transition temperature of 200 ° C. or less, after sufficient adhesive strength and long-term reliability test. Thus, a circuit connection body having stable performance (adhesive strength and connection resistance) can be obtained.
  • the present invention is the use of the adhesive composition of the present invention, wherein at least one of the first circuit on the main surface of the first circuit board contains a thermoplastic resin having a glass transition temperature of 200 ° C. or lower.
  • the present invention is the use of the film-like adhesive of the present invention, wherein at least one of the first circuit on the main surface of the first circuit board contains a thermoplastic resin having a glass transition temperature of 200 ° C. or lower.
  • the present invention is the use of the adhesive sheet of the present invention, wherein at least one of the first circuit electrodes includes a thermoplastic resin having a glass transition temperature of 200 ° C. or less on the main surface of the first circuit board.
  • the formed first circuit member and the second circuit member in which the second circuit electrode is formed on the main surface of the second circuit board, the first circuit electrode and the second circuit electrode And use of the adhesive sheet for bonding so as to be electrically connected.
  • an excellent adhesive strength is obtained even when cured at low temperature on an organic base material having low heat resistance such as polyethylene terephthalate (PET), polycarbonate (PC), and polyethylene naphthalate (PEN).
  • an organic base material having low heat resistance such as polyethylene terephthalate (PET), polycarbonate (PC), and polyethylene naphthalate (PEN).
  • Adhesive composition that can maintain stable performance (adhesive strength and connection resistance) even after long-term reliability test (high temperature and high humidity test), and film adhesive and adhesive using the same
  • a sheet, a circuit connection body, and a circuit member connection method can be provided.
  • (meth) acrylic acid means acrylic acid or methacrylic acid corresponding to it
  • (meth) acrylate means acrylate or the corresponding methacrylate
  • (meth) acryloyl group Means an acryloyl group or a corresponding methacryloyl group.
  • Glass transition temperature (Tg)” of a thermoplastic resin or circuit board is a temperature rise rate of 5 ° C./min using a viscoelasticity analyzer “RSA-3” (trade name) manufactured by TA Instruments. The value of the tan ⁇ peak temperature measured under conditions of a frequency of 10 Hz and a measurement temperature of ⁇ 150 ° C. to 300 ° C.
  • Glass transition temperature (Tg)” of fine particles refers to a viscoelasticity analyzer “RSA-3” (product of T.A. Instruments) manufactured by dispersing fine particles in a thermoplastic resin having a known Tg. Tan ⁇ peak temperature measured under conditions of a temperature rising rate of 5 ° C./min, a frequency of 10 Hz, and a measurement temperature of ⁇ 150 ° C. to 300 ° C.
  • the “average particle diameter” of the fine particles is an average particle diameter (measured by using Zetasizer Nano-S (trade name, manufactured by Malvern Instruments Ltd.)) after diluting the fine particles to 0.1 wt% (mass%) with methyl ethyl ketone. Z-average value).
  • SALD-2200 trade name, manufactured by Shimadzu Corporation
  • the adhesive composition according to the present invention is characterized by containing silicone fine particles having a core-shell structure.
  • the core-shell type structure include a structure having a core layer and a shell layer provided so as to cover the core layer, and a glass transition temperature higher than the glass transition temperature or elastic modulus of the core material (core layer) surface or Silicone fine particles that have a surface layer (shell layer) having an elastic modulus and those that have a graft layer (shell layer) outside the core material (core layer), and have the same or different composition in the core layer and shell layer Can be used.
  • the core layer constituting the core-shell type silicone fine particles is preferably silicone and silicone rubber from the viewpoint of stress relaxation effect, and the shell layer may be the same kind of polymer of the core layer or other kinds of polymers. It is preferable that the physical properties (glass transition temperature, elastic modulus, etc.) of the shell layer are higher than those of the core layer. Thereby, the structure and shape of a core layer can be stabilized and the performance is exhibited effectively.
  • silicone or silicone rubber is used as the core layer, the silicone or silicone rubber swells with a solvent or a constituent material, thereby preventing the fine particles from adhering to each other to form an aggregate.
  • the glass transition temperature of the core layer of the silicone fine particles is preferably ⁇ 130 ° C. or higher and ⁇ 20 ° C. or lower, more preferably ⁇ 125 ° C. or higher and ⁇ 40 ° C. or lower, and particularly preferably ⁇ 120 ° C. Above and below -50 ° C. Such silicone fine particles can sufficiently relieve the internal stress of the adhesive composition.
  • the molecular weight of the core layer of the silicone fine particles is preferably 1.5 million or less, more preferably 1.5 million or less and 500,000 or more, and particularly preferably 1.4 million or less and 800,000 or more.
  • the shell layer in the core-shell type silicone fine particles preferably has a crosslinked structure in order to achieve stabilization of the core layer structure, maintenance of shape, and high functionality, and a crosslinked structure having a three-dimensional network structure.
  • the structure is more preferable, and the shell layer is particularly preferably a crosslinked structure having a three-dimensional network structure.
  • an organic compound such as a polymethyl methacrylate copolymer or an inorganic compound such as silicone, silica, or silsesquioxane is more preferable. Thereby, relaxation of the internal stress by silicone is exhibited effectively.
  • the cross section of the core-shell type silicone fine particles can be confirmed by surface observation and surface composition analysis.
  • TEM transmission electron microscope
  • Resin casting Epoxy resin (Epomount main agent and curing agent by Refine Tech Co., Ltd.)
  • Heavy metal dyeing A 2% by weight aqueous solution of OsO 4 (osmium tetroxide) is prepared, and the cast sample is bulk dyed therein for 24 hours.
  • Pretreatment While cooling to -120 ° C.
  • atomic force microscope As another method, structural analysis by an atomic force microscope (AFM) can be performed under the following conditions.
  • Resin casting Epoxy resin (Epomount main agent and curing agent by Refine Tech Co., Ltd.)
  • Pretreatment While cooling to -120 ° C. with a cryoultramicrotome, pretreatment is performed with a diamond knife at a blade speed of 0.6 mm / second to form a thin film.
  • Observation A cross section is observed using an atomic force microscope AFM manufactured by SII Nanotechnology, and a shape image and a phase image are measured in a DFM mode, and a core-shell structure is confirmed by the phase image.
  • the average particle size of the silicone fine particles is preferably 0.05 ⁇ m or more and 25 ⁇ m or less, more preferably 0.1 ⁇ m or more and 20 ⁇ m or less, and particularly preferably 0.6 ⁇ m or more and 10 ⁇ m or less.
  • the blending amount of the silicone fine particles is preferably 1% by mass or more and 50% by mass or less, preferably 3% by mass or more and 30% by mass or less based on the mass of the adhesive component (adhesive composition excluding conductive particles). More preferably, it is 5 mass% or more and 30 mass% or less.
  • the core-shell type silicone fine particles may be used alone or in combination of two or more. Furthermore, other silicone fine particles may be used in combination as long as the effects of the present invention are not impaired.
  • the silicone fine particles preferably have a molecular weight of 1.5 million or less, more preferably 1.5 million or less and 500,000 or more, and particularly preferably 1.4 million or less and 800,000 or more.
  • the other silicone fine particles preferably have a three-dimensional crosslinked structure. “Having a three-dimensional crosslinked structure” means that the polymer chain has a three-dimensional network structure. Silicone fine particles having a three-dimensional crosslinked structure have high dispersibility in the resin and are further excellent in stress relaxation after curing.
  • Silicone fine particles having a molecular weight of 1 million or more and / or a three-dimensional crosslinked structure have low solubility in polymers such as thermoplastic resins, monomers, solvents, and the like, so that the dispersibility and the stress relaxation effect can be obtained more remarkably. it can.
  • silicone fine particles include fine particles of polyorganosilsesquioxane resin having rubber elasticity, and spherical and amorphous silicone fine particles are used. Specifically, silicone fine particles obtained by the reaction of an organopolysiloxane containing at least two vinyl groups, an organohydropolyene polysiloxane having at least two hydrogen atoms bonded to silicon atoms, and a platinum-based catalyst (for example, special No.
  • organopolysiloxane having an alkenyl group organopolysiloxane having a hydrosilyl group
  • silicone fine particles obtained using a platinum-based catalyst see, for example, JP-A-63-77742
  • di Silicone fine particles obtained using organosiloxane, monoorganosilsesquioxane, triorganosiloxane and platinum-based catalyst for example, see JP-A-62-270660
  • water of methylsilane triol and / or partial condensate thereof / Alcohol soluble The silicone particles obtained by performing the dropped polycondensation reaction in an aqueous alkaline solution (for example, see Patent JP No.
  • silicone fine particles to which an epoxy compound is added or copolymerized (for example, see JP-A-3-167228) or an acrylate compound is added or copolymerized. Silicone fine particles can also be used.
  • thermoplastic resin contained in the adhesive composition becomes a high-viscosity liquid state by heating and deforms freely by external force, and when cooled and removed, the shape becomes hard while maintaining its shape, and this process is repeated.
  • Resins (polymer) having properties that can be used can be suitably used.
  • a resin (polymer) having a reactive functional group having the above properties is also included.
  • the Tg of the thermoplastic resin is preferably ⁇ 30 ° C. or higher and 190 ° C. or lower, more preferably ⁇ 25 ° C. or higher and 170 ° C. or lower, and particularly preferably ⁇ 20 ° C. or higher and 150 ° C. or lower.
  • thermoplastic resin polyimide resin, polyamide resin, phenoxy resin, (meth) acrylic resin, urethane resin, polyester urethane resin, polyvinyl butyral resin, vinyl acetate copolymer and the like can be used. These can be used alone or in admixture of two or more. Further, these thermoplastic resins may contain a siloxane bond or a fluorine substituent. These can be suitably used as long as the resins to be mixed are completely compatible with each other or microphase separation occurs and becomes cloudy.
  • the higher the molecular weight of the thermoplastic resin the easier it is to obtain good film formability and the fluidity as a film adhesive.
  • the melt viscosity that affects the viscosity can be set in a wide range.
  • the weight average molecular weight of the thermoplastic resin is preferably from 5,000 to 150,000, more preferably from 7,000 to 100,000, and particularly preferably from 10,000 to 80,000. When the weight average molecular weight of the thermoplastic resin is within the above range, it becomes easy to achieve both good film formability and good compatibility with other components.
  • the content of the thermoplastic resin is preferably 5% by mass or more and 80% by mass or less, and preferably 15% by mass or more and 70% by mass or less, based on the mass of the adhesive component (adhesive composition excluding conductive particles). More preferably.
  • the content of the thermoplastic resin is within the above range, when the adhesive composition is used in the form of a film, it is possible to achieve both good film formability and good fluidity of the film adhesive. It becomes easy.
  • the radically polymerizable compound contained in the adhesive composition is a compound that generates radical polymerization by the action of a radical polymerization initiator, and is a compound that itself generates radicals by applying activation energy such as light and heat. There may be.
  • a compound having a functional group that is polymerized by an active radical such as a vinyl group, a (meth) acryloyl group, an aryl group, or a maleimide group can be preferably used.
  • radical polymerizable compound examples include epoxy (meth) acrylate oligomers, urethane (meth) acrylate oligomers, polyether (meth) acrylate oligomers, polyester (meth) acrylate oligomers, and trimethylolpropane tri (meth) acrylate.
  • Epoxy (meth) acrylate a compound in which ethylene glycol or propylene glycol is added to a glycidyl group of bisphenol fluorenediglycidyl ether, a compound in which a (meth) acryloyloxy group is introduced, represented by the following general formula (A) or (B) And the like.
  • R 1 and R 2 each independently represent a hydrogen atom or a methyl group, and a and b each independently represent an integer of 1 to 8.
  • R 3 and R 4 each independently represent a hydrogen atom or a methyl group, and c and d each independently represents an integer of 0 to 8.
  • radically polymerizable compounds include N, N′-methylenebisacrylamide, diacetone acrylamide, N-methylolacrylamide, N-phenylmethacrylamide, 2-acrylamido-2-methylpropanesulfonic acid, tris ( 2-acryloyloxyethyl) isocyanurate, N-phenylmaleimide, N- (o-methylphenyl) maleimide, N- (m-methylphenyl) maleimide, N- (p-methylphenyl) -maleimide, N- (o- Methoxyphenyl) maleimide, N- (m-methoxyphenyl) maleimide, N- (p-methoxyphenyl) -maleimide, N-methylmaleimide, N-ethylmaleimide
  • e represents an integer of 1 to 10.
  • R 5 and R 6 each independently represent a hydrogen atom or a methyl group, and f represents an integer of 15 to 30.
  • R 7 and R 8 each independently represent a hydrogen atom or a methyl group, and g represents an integer of 15 to 30.
  • R 9 represents a hydrogen atom or a methyl group.
  • R 10 represents a hydrogen atom or a methyl group
  • h represents an integer of 1 to 10.
  • R 11 represents a hydrogen atom or an organic group represented by the following general formula (i) or (ii), and i represents an integer of 1 to 10.
  • R 12 represents a hydrogen atom or an organic group represented by the following general formula (iii) or (iv), and j represents an integer of 1 to 10.
  • R 12 may be the same or different.
  • R 13 represents a hydrogen atom or a methyl group.
  • R 14 represents a hydrogen atom or a methyl group.
  • urethane acrylate can be used alone or in combination with other radical polymerizable compounds as the radical polymerizable compound.
  • flexibility is improved and adhesion strength to organic base materials such as PET, PC, and PEN can be improved.
  • the urethane acrylate represented by the following general formula (M) is an aliphatic or alicyclic diisocyanate and at least one aliphatic or alicyclic ester diol or aliphatic or alicyclic carbonate type. It can be obtained by a condensation reaction with a diol.
  • R 15 and R 16 each independently represent a hydrogen atom or a methyl group
  • R 17 represents an ethylene group or a propylene group
  • R 18 represents a saturated aliphatic group or a saturated alicyclic group
  • R 19 represents a saturated aliphatic group or saturated alicyclic group containing an ester group, a saturated aliphatic group or saturated alicyclic group containing a carbonate group
  • k represents an integer of 1 to 40.
  • R 17 s , R 18 s , and R 19 s may be the same or different.
  • the aliphatic diisocyanates constituting the urethane acrylate are tetramethylene diisocyanate, hexamethylene diisocyanate, lysine diisocyanate, 2-methylpentane-1,5-diisocyanate, 3-methylpentane-1,5-diisocyanate, 2,2,4 Trimethylhexamethylene-1,6-diisocyanate, 2,4,4-trimethylhexamethylene-1,6-diisocyanate, isophorone diisocyanate, cyclohexyl diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated trimethylxylylene diisocyanate Selected from etc.
  • the aliphatic ester diol constituting the urethane acrylate is ethylene glycol, propylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol.
  • the polycarbonate diol constituting the urethane acrylate is selected from polycarbonate diols obtained by a reaction of at least one kind of the glycols with phosgene.
  • the polycarbonate diols obtained by the reaction of the glycols and phosgene may be used alone or in combination of two or more polycarbonate diols.
  • the weight-average molecular weight of the urethane acrylate can be freely adjusted and suitably used within the range of 5000 or more and less than 30000 from the viewpoint of improving the adhesive strength to a substrate such as PET, PC, PEN and the like. If the weight average molecular weight of the urethane acrylate is within the above range, both flexibility and cohesion can be obtained, and the adhesive strength with organic substrates such as PET, PC, PEN and the like is improved, and excellent connection reliability is achieved. Sex can be obtained. Furthermore, when the weight average molecular weight of the urethane acrylate is within the above range, it becomes easy to achieve both sufficient flexibility and fluidity of the adhesive composition. Further, from the viewpoint of obtaining such effects more sufficiently, the weight average molecular weight of the urethane acrylate is more preferably 80000 or more and less than 25000, and particularly preferably 10,000 or more and less than 20000.
  • the blending amount of the urethane acrylate is preferably 5% by mass or more and 95% by mass or less, preferably 10% by mass or more and 80% by mass or less, based on the mass of the adhesive component (adhesive composition excluding conductive particles). More preferably, it is more preferably 15% by mass or more and 70% by mass or less.
  • the blending amount of the urethane acrylate is within the above range, sufficient heat resistance is obtained after curing, and it is easy to obtain good film formability when used as a film adhesive.
  • a vinyl compound having a phosphate group (phosphate group-containing vinyl compound), an N-vinyl selected from the group consisting of an N-vinyl compound and an N, N-dialkylvinyl compound, which is a compound belonging to a radical polymerizable compound.
  • System compounds can be used in combination with radically polymerizable compounds other than these.
  • the combined use of the phosphoric acid group-containing vinyl compound makes it possible to improve the adhesion of the adhesive composition to the metal substrate.
  • the combined use of the N-vinyl compound can improve the crosslinking rate of the adhesive composition.
  • the phosphate group-containing vinyl compound is not particularly limited as long as it is a compound having a phosphate group and a vinyl group, but compounds represented by the following general formulas (N) to (P) are preferable.
  • R 20 represents a (meth) acryloyloxy group
  • R 21 represents a hydrogen atom or a methyl group
  • l and m each independently represents an integer of 1 to 8.
  • R 20 s , R 21 s , l s, and m s may be the same or different.
  • R 22 represents a (meth) acryloyloxy group
  • n, o and p each independently represent an integer of 1 to 8.
  • R 22 s , n s, o s, and p s may be the same or different.
  • R 23 represents a (meth) acryloyloxy group
  • R 24 represents a hydrogen atom or a methyl group
  • q and r each independently represents an integer of 1 to 8.
  • R 23 s , R 24 s , q s, and r s may be the same or different.
  • the phosphoric acid group-containing vinyl compound examples include acid phosphooxyethyl methacrylate, acid phosphooxyethyl acrylate, acid phosphooxypropyl methacrylate, acid phosphooxypolyoxyethylene glycol monomethacrylate, acid phosphooxypolyoxypropylene glycol monomethacrylate, Examples include 2,2′-di (meth) acryloyloxydiethyl phosphate, EO-modified phosphate dimethacrylate, phosphate-modified epoxy acrylate, and vinyl phosphate.
  • N-vinyl compounds include N-vinylimidazole, N-vinylpyridine, N-vinylpyrrolidone, N-vinylformamide, N-vinylcaprolactam, 4,4′-vinylidenebis (N, N -Dimethylaniline), N-vinylacetamide, N, N-dimethylacrylamide, N, N-diethylacrylamide and the like.
  • the compounding amount of the phosphoric acid group-containing vinyl compound and the N-vinyl compound is independent of the compounding amount of the radical polymerizable compound other than the phosphoric acid group-containing vinyl compound.
  • Adhesive component adheresive composition excluding conductive particles
  • the blending amount of the phosphate group-containing vinyl compound and the N-vinyl compound is within the above range, it becomes easy to achieve both high adhesive strength of the adhesive composition and physical properties after curing of the adhesive composition. , Making it easier to ensure reliability.
  • the blending amount of the radical polymerizable compound excluding the phosphate group-containing vinyl compound and the N-vinyl compound is 5% by mass or more and 95% by mass based on the mass of the adhesive component (adhesive composition excluding conductive particles). It is preferably 10% by mass or more and 80% by mass or less, more preferably 15% by mass or more and 70% by mass or less.
  • the blending amount of the radical polymerizable compound is within the above range, sufficient heat resistance is obtained after curing, and it is easy to obtain good film formability when used as a film adhesive.
  • the radical polymerization initiator contained in the adhesive composition conventionally known compounds such as organic peroxides and azo compounds that generate radicals by external energy application can be used.
  • the radical polymerization initiator is preferably an organic peroxide having a 1 minute half-life temperature of 90 ° C. or more and 175 ° C. or less and a molecular weight of 180 or more and 1000 or less from the viewpoints of stability, reactivity, and compatibility.
  • the 1-minute half-life temperature is within this range, the storage stability is excellent, the radical polymerizability is sufficiently high, and the composition can be cured in a short time.
  • radical polymerization initiator examples include 1,1,3,3-tetramethylbutylperoxyneodecanoate, di (4-t-butylcyclohexyl) peroxydicarbonate, and di (2-ethylhexyl).
  • Peroxydicarbonate cumylperoxyneodecanoate, 1,1,3,3-tetramethylbutylperoxyneodecanoate, dilauroyl peroxide, 1-cyclohexyl-1-methylethylperoxyneodecanoate T-hexylperoxyneodecanoate, t-butylperoxyneodecanoate, t-butylperoxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 2,5-dimethyl-2,5-di (2-ethylhexanoylperoxy) hexane, t-hexane Luperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t-butylperoxyneoheptanoate, t-amylperoxy-2-ethylhexano
  • radical polymerization initiator a compound that generates radicals by light irradiation of 150 nm or more and 750 nm or less can be used.
  • Such compounds include, for example, Photoinitiation, Photopolymerization, and Photocuring, J. MoI. -P. ⁇ -acetaminophenone derivatives and phosphine oxide derivatives described in Fouassier, Hanser Publishers (1995, p17 to p35) are more preferred because of their high sensitivity to light irradiation. These compounds may be used alone or in combination with the above organic peroxides or azo compounds.
  • the blending amount of the radical polymerization initiator is preferably 0.5% by mass or more and 40% by mass or less, preferably 1% by mass or more and 30% by mass based on the mass of the adhesive component (adhesive composition excluding conductive particles). % Or less is more preferable, and 2% by mass or more and 20% by mass or less is particularly preferable. When the blending amount of the radical polymerization initiator is within the above range, it becomes easy to achieve both curability and storage stability of the adhesive composition.
  • the conductive particles contained in the adhesive composition may be particles having conductivity on the whole or on the surface, but when used for connection of circuit members having connection terminals (circuit electrodes), the distance between the connection terminals. It is preferable that the average particle size is smaller.
  • the conductive particles include metal particles such as Au, Ag, Ni, Cu, Pd, and solder, and carbon.
  • non-conductive glass, ceramic, plastic or the like may be used as a core, and the core may be coated with the metal, metal particles, or carbon.
  • the conductive particles may be, for example, particles obtained by coating silver on copper metal particles.
  • a metal powder having a shape in which a large number of fine metal particles are connected in a chain shape as described in JP-A-2005-116291 can be used.
  • this since short-circuiting due to contact between particles when the amount of conductive particles is increased can be suppressed and insulation between the electrode circuits can be improved, this may be used alone or mixed with other conductive particles as appropriate. .
  • the average particle diameter of the conductive particles is preferably 1 ⁇ m or more and 18 ⁇ m or less from the viewpoint of dispersibility and conductivity.
  • the adhesive composition can be suitably used as an anisotropic conductive adhesive.
  • the amount of conductive particles used is not particularly limited, but is preferably 0.1% by volume or more and 30% by volume or less, and 0.1% by volume or more and 10% by volume or less with respect to the total volume of the adhesive composition. More preferably. When the amount of the conductive particles used is within the above range, a short circuit can be sufficiently suppressed while sufficient conductivity is obtained.
  • volume% is determined based on the volume of each component before 23 degreeC hardening, the volume of each component can be converted into a volume from a weight using specific gravity. In addition, do not dissolve or swell the component in a graduated cylinder, etc., and put the component in a suitable solvent (water, alcohol, etc.) that wets the component well. It can also be determined as a volume.
  • a stabilizer can be added to the adhesive composition in order to control the curing rate and impart storage stability.
  • known compounds can be used without particular limitation, but quinone derivatives such as benzoquinone and hydroquinone; phenol derivatives such as 4-methoxyphenol and 4-t-butylcatechol; , 6,6-tetramethylpiperidine-1-oxyl, 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl, and the like; hindered amine derivatives such as tetramethylpiperidyl methacrylate;
  • the blending amount of the stabilizer is preferably 0.005% by mass or more and 10% by mass or less based on the mass of the adhesive component (adhesive composition excluding the conductive particles), and 0.01% by mass or more and 8% by mass or less. More preferably, it is 0.02 mass% or less and 5 mass% or less is especially preferable.
  • the curing rate can be controlled and storage stability can be imparted without adversely affecting the compatibility with other components.
  • adhesion aids such as coupling agents represented by alkoxysilane derivatives and silazane derivatives, adhesion improvers, and leveling agents may be appropriately added to the adhesive composition.
  • the compound represented by the following general formula (Q) is preferable as the coupling agent, and two or more compounds may be mixed and used in addition to the compound used alone.
  • R 25 , R 26 and R 27 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or 1 to 5 carbon atoms.
  • R 28 represents a (meth) acryloyl group, a vinyl group, an isocyanate group, an imidazole group, a mercapto group, an amino group, a methylamino group, a dimethylamino group, a benzylamino group, or a phenylamino group. Cyclohexylamino group, morpholino group, piperazino group, ureido group or glycidyl group, and s represents an integer of 1 to 10.
  • the adhesive composition may be used in combination with a rubber component for the purpose of improving adhesiveness.
  • the rubber component refers to a component that exhibits rubber elasticity (JIS K6200) as it is or a component that exhibits rubber elasticity by reaction.
  • the rubber component may be solid or liquid at room temperature (25 ° C.), but is preferably liquid from the viewpoint of improving fluidity.
  • a compound having a polybutadiene skeleton is preferable.
  • the rubber component may have a cyano group, a carboxyl group, a hydroxyl group, a (meth) acryloyl group, or a morpholine group.
  • a rubber component containing a cyano group or a carboxyl group, which is a highly polar group, in the side chain or terminal is preferable.
  • a rubber component containing a cyano group or a carboxyl group, which is a highly polar group, in the side chain or terminal is preferable.
  • thermoplasticity if it has a polybutadiene skeleton, if it exhibits thermoplasticity, it is classified as a thermoplastic resin, and if it exhibits radical polymerizability, it is classified as a radical polymerizable compound.
  • rubber components 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-butadiene rubber, carboxyl group, hydroxyl group, (meth) acryloyl group or morpholine group-containing acrylonitrile-butadiene rubber, carboxylated nitrile rubber, hydroxyl-terminated poly (oxypropylene) ), Alkoxysilyl group-terminated poly (oxypropylene), poly (oxytetramethylene) glycol, polyolefin glycol, and the like.
  • the rubber component having a high polar group and being liquid at room temperature specifically includes a liquid acrylonitrile-butadiene rubber, a carboxyl group, a hydroxyl group, a (meth) acryloyl group or a morpholine group at the polymer terminal.
  • a liquid acrylonitrile-butadiene rubber specifically includes a carboxyl group, a hydroxyl group, a (meth) acryloyl group or a morpholine group at the polymer terminal.
  • examples thereof include liquid acrylonitrile-butadiene rubber and liquid carboxylated nitrile rubber.
  • the content of acrylonitrile as a polar group is preferably 10% by mass or more and 60% by mass or less.
  • These compounds may be used alone or in combination of two or more compounds.
  • the adhesive composition may contain organic fine particles other than the core-shell type silicone fine particles according to the present invention for the purpose of stress relaxation and adhesion improvement.
  • the average particle size of the organic fine particles is preferably 0.05 ⁇ m or more and 1.0 ⁇ m or less.
  • organic fine particles consist of the above-mentioned rubber component it classifies into a rubber component instead of organic fine particles
  • organic fine particles consist of the above-mentioned thermoplastic resin it classifies into a thermoplastic resin instead of organic fine particles.
  • organic fine particles include polyisoprene, polybutadiene, carboxyl-terminated polybutadiene, hydroxyl-terminated polybutadiene, 1,2-polybutadiene, carboxyl-terminated 1,2-polybutadiene, acrylic rubber, styrene-butadiene rubber, acrylonitrile-butadiene rubber, Acrylonitrile-butadiene rubber, carboxylated nitrile rubber, hydroxyl-terminated poly (oxypropylene), alkoxysilyl-terminated poly (oxypropylene), poly (oxypropylene) containing carboxyl group, hydroxyl group, (meth) acryloyl group or morpholine group at the polymer end Tetramethylene) glycol, polyolefin glycol (meth) acrylic acid alkyl-butadiene-styrene copolymer, (meth) acrylic acid alkyl-silicone copolymer or Recone (meth) - include organic
  • the adhesive composition can be used as a paste when it is liquid at room temperature. In the case of a solid at room temperature, it may be used by heating, or may be pasted using a solvent.
  • Solvents that can be used are preferably those that are not reactive with the adhesive composition and additives and that exhibit sufficient solubility, and those having a boiling point of 50 ° C. or higher and 150 ° C. or lower at normal pressure. When the boiling point of the solvent is within the above range, it is difficult to volatilize even if it is left at room temperature, it is easy to use in an open system, and the solvent can be sufficiently volatilized to ensure sufficient reliability after bonding. .
  • the adhesive composition of the present invention can be formed into a film and used as a film adhesive.
  • a solution in which a solvent or the like is added to the adhesive composition as necessary is applied onto a peelable substrate such as a fluororesin film, a polyethylene terephthalate film or a release paper, or a substrate such as a nonwoven fabric is impregnated with the above solution. It can be used as a film adhesive by placing on a peelable substrate and removing the solvent. Use in the form of a film is more convenient from the viewpoint of handleability.
  • the adhesive composition of the present invention can be bonded using heating and pressurization together.
  • the heating temperature is preferably 100 ° C. or higher and 200 ° C. or lower.
  • the pressure is preferably in a range that does not damage the adherend, and is generally from 0.1 MPa to 10 MPa. These heating and pressurization are preferably performed in the range of 0.5 second or more and 120 seconds or less, and can be adhered by heating at 110 ° C. or more and 190 ° C. or less, 3 MPa, or 10 seconds.
  • the adhesive composition of the present invention can be used as an adhesive composition for different types of adherends having different thermal expansion coefficients. Specifically, it can be used as a circuit connection material typified by anisotropic conductive adhesive, silver paste, silver film and the like.
  • circuit members for example, a first circuit member having a first circuit electrode formed on the main surface of the first circuit board, and a second circuit member
  • the first circuit electrode and the second circuit member are cured.
  • At least one of the first circuit board and the second circuit board includes at least one selected from the group consisting of polyethylene terephthalate, polycarbonate, and polyethylene naphthalate as a thermoplastic resin having a glass transition temperature of 200 ° C. or lower. It is preferable to include. By including such a thermoplastic resin, wettability with the adhesive composition of the present invention is improved, and adhesive strength and connection reliability are improved.
  • one of the first circuit board and the second circuit board includes at least one selected from the group consisting of polyethylene terephthalate, polycarbonate, and polyethylene naphthalate, and the other circuit board is polyimide. It is preferable to contain resin and / or polyethylene terephthalate.
  • an inorganic substrate such as a semiconductor, glass or ceramic, or an organic substrate such as polyimide or polycarbonate can be used in combination.
  • the adhesive composition of the present invention does not need to reach full curing (the highest degree of curing that can be achieved under predetermined curing conditions), and may be in a partially cured state as long as the above characteristics are produced.
  • a nickel layer having a thickness of 0.2 ⁇ m is provided on the surface of particles having polystyrene as a core, and a gold layer having a thickness of 0.02 ⁇ m is provided outside the nickel layer, and conductive particles having an average particle diameter of 10 ⁇ m and a specific gravity of 2.5 are provided. Produced.
  • polyester urethane resin A Using terephthalic acid (manufactured by Aldrich) for digalbonic acid, isophthalic acid (manufactured by Aldrich), neopentyl glycol (manufactured by Aldrich) for diol, and 4,4'-diphenylmethane diisocyanate (manufactured by Aldrich) for isocyanate, terephthalic acid Polyester urethane resin A having a molar ratio of / isolutaric acid / neopentyl glycol / 4,4′-diphenylmethane diisocyanate of 0.34 / 0.66 / 1.1 / 0.33 was prepared.
  • the number average molecular weight of the obtained polyester urethane resin A was 25000.
  • the obtained polyester urethane resin A (PEU-A) was dissolved in 1: 1 of methyl ethyl ketone and toluene so as to have a solid content of 40% by mass.
  • YP-50 Phenoxy resin
  • YP-50 Phenoxy resin
  • EV40W ethylene-vinyl acetate copolymer
  • a toluene-dissolved product of ethylene-vinyl acetate copolymer (solid content 30% by mass) (EV40W (trade name) manufactured by Mitsui DuPont Polychemical Co., Ltd.) was used.
  • ⁇ Radically polymerizable compound> (UA1: urethane acrylate resin 1) Poly (1,6-hexanediol carbonate) with a number average molecular weight of 1000 (trade name: DURANOL T5652, Asahi Kasei Co., Ltd.) in a reaction vessel equipped with a stirrer, thermometer, reflux condenser with calcium chloride drying tube, and nitrogen gas introduction tube Chemicals Co., Ltd.) 2500 parts by mass (2.50 mol) and isophorone diisocyanate (Sigma Aldrich) 666 parts by mass (3.00 mol) are uniformly added dropwise over 3 hours, and nitrogen gas is sufficiently added. After the introduction, the reaction was conducted by heating to 70 to 75 ° C.
  • BR crosslinked polybutadiene fine particles
  • Pure water was put into a stainless steel autoclave, and polyvinyl alcohol (manufactured by Kanto Chemical Co., Inc.) was added and dissolved as a suspending agent.
  • Butadiene manufactured by Sigma Aldrich
  • benzoyl peroxide (trade name: Cadox CH-50L, manufactured by Kayaku Akzo Co., Ltd.) was dissolved and stirred as a radical polymerization initiator.
  • the autoclave was then heated to 60-65 ° C. and polymerized for 45 minutes with stirring.
  • crosslinked polybutadiene particles After releasing the unreacted monomer, the produced crosslinked polybutadiene particles were filtered, washed with water, and washed with ethanol, and the obtained crosslinked polybutadiene particles were dried under vacuum to obtain crosslinked polybutadiene fine particles (BR).
  • the obtained crosslinked polybutadiene fine particles were dispersed in methyl ethyl ketone, and the average particle size of the particles was measured using Zetasizer Nano-S (manufactured by Malvern Instruments Ltd.). The average particle size was 0.5 ⁇ m.
  • Silicone rubber fine particles (trade name: KMP594, average particle size of 5 ⁇ m, glass transition temperature: ⁇ 70 ° C.) manufactured by Shin-Etsu Chemical Co., Ltd. were used.
  • BTA-712 Core-shell alkyl acrylate-butadiene-styrene copolymer fine particles (trade name: Paraloid BTA-712) manufactured by Rohm & Haas Co. were used.
  • connection resistance and adhesive strength [Measurement of connection resistance and adhesive strength] (Reference Examples 1-9)
  • the film adhesives of Examples 1, 2, 5 and Comparative Examples 3, 5-7, 9, 10 have 500 copper circuits having a line width of 25 ⁇ m, a pitch of 50 ⁇ m and a thickness of 18 ⁇ m on a polyimide film (Tg 350 ° C.). It was interposed between a flexible circuit board (FPC) and glass (thickness 1.1 mm, surface resistance 20 ⁇ / ⁇ ) on which a thin layer of 0.2 ⁇ m ITO was formed. This was heat-pressed at 150 ° C. and 2 MPa for 10 seconds using a thermocompression bonding apparatus (heating method: constant heat type, manufactured by Toray Engineering Co., Ltd.) and bonded over a width of 2 mm to produce a circuit connection body.
  • FPC flexible circuit board
  • glass thickness 1.1 mm, surface resistance 20 ⁇ / ⁇
  • the resistance value between adjacent circuits of the circuit connection body 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 240 hours (after the test). The resistance value was shown as an average of 37 resistances between adjacent circuits.
  • connection body was measured by a 90-degree peeling method according to JIS-Z0237 and evaluated.
  • a measuring device for the adhesive strength “Tensilon UTM-4” (trade name) manufactured by Toyo Baldwin Co., Ltd. (peeling speed 50 mm / min, 25 ° C.) was used. The measurement results are shown in Table 2.
  • the circuit connections of Reference Examples 1 to 9 had a good connection resistance of 4.0 ⁇ or less and 560 N / m immediately after bonding and after the test under the condition of a heating temperature of 150 ° C.
  • the above good adhesive strength was exhibited. That is, it was confirmed that the difference in the type of organic fine particles does not significantly affect the connection resistance and the adhesive strength in the adhesion between the flexible circuit board made of polyimide film and the glass on which the ITO thin film is formed.
  • Examples 1 to 5 and Comparative Examples 1 to 14 A flexible circuit board (FPC) having 80 copper circuits having a line width of 150 ⁇ m, a pitch of 300 ⁇ m, and a thickness of 8 ⁇ m on a polyimide film (Tg 350 ° C.) with the film adhesives of Examples 1 to 5 and Comparative Examples 1 to 14; It was interposed between a PET substrate (thickness 0.1 ⁇ m) on which a thin layer of 5 ⁇ m thick Ag paste was formed. Subsequently, using a thermocompression bonding apparatus (heating method: constant heat type, manufactured by Toray Engineering Co., Ltd.), the film was bonded by heating and pressing at 150 ° C. and 2 MPa for 20 seconds over a width of 2 mm to prepare a circuit connection body.
  • FPC flexible circuit board
  • the resistance value between adjacent circuits of the circuit connection body 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 240 hours (after the test). The resistance value was shown as an average of 37 resistances between adjacent circuits. Table 3 shows the measurement results.
  • the adhesive strength of the circuit connection body was measured by a 90 ° peeling method according to JIS-Z0237 and evaluated.
  • As a measuring device for the adhesive strength “Tensilon UTM-4” (trade name) manufactured by Toyo Baldwin Co., Ltd. (peeling speed 50 mm / min, 25 ° C.) was used. Table 3 shows the measurement results.
  • circuit connectors produced using the film adhesives of Examples 1 to 5 had a good connection resistance of about 2.6 ⁇ or less immediately after bonding and after the test under the condition of a heating temperature of 150 ° C. Good adhesive strength of about 600 N / m or more was exhibited.
  • circuit connection bodies prepared using the film adhesives of Comparative Examples 1 to 14 (excluding Comparative Examples 4, 8, and 12) containing no silicone fine particles exhibit good connection resistance, Immediately after, the adhesive strength was as low as 590 N / m or less, and the adhesive strength after the test was as low as 510 N / m or less.
  • the adhesive composition containing the silicone fine particles according to the present invention is used. It is clear that excellent adhesive strength can be obtained even under low temperature curing conditions, and that stable performance (adhesive strength and connection resistance) can be maintained even after a long-term reliability test (high temperature and high humidity test). It became.
  • the adhesive composition according to the present invention can obtain excellent adhesive strength even when cured at a low temperature for a circuit board containing a thermoplastic resin having a glass transition temperature of 200 ° C. or lower. It is suitably used for bonding a semiconductor element and an FPC using an organic base material having low heat resistance such as PEN.
  • Adhesive sheet 6 ... Base material, 8 ... Adhesive layer (adhesive composition), 9 ... Adhesive component, 10 ... Silicone fine particle, 10a ... Core-shell type silicone fine particle, 11 ... Core layer, 12 ... Share layer, 20 ... conductive particles, 30 ... first circuit member, 31 ... first circuit board, 31a ... main surface of the first circuit board, 32 ... first circuit electrode, 40 ... second circuit member, 41 ... 2nd circuit board, 41a ... main surface of 2nd circuit board, 42 ... 2nd circuit electrode, 50 ... connection part, 100 ... circuit connection body.
PCT/JP2011/071388 2011-09-20 2011-09-20 接着剤組成物、フィルム状接着剤、接着シート、回路接続体及び回路部材の接続方法 WO2013042203A1 (ja)

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PCT/JP2011/071388 WO2013042203A1 (ja) 2011-09-20 2011-09-20 接着剤組成物、フィルム状接着剤、接着シート、回路接続体及び回路部材の接続方法
PCT/JP2012/074051 WO2013042724A1 (ja) 2011-09-20 2012-09-20 接着剤組成物、フィルム状接着剤、接着シート、回路接続体、回路部材の接続方法、接着剤組成物の使用、フィルム状接着剤の使用及び接着シートの使用
KR1020147009493A KR102193517B1 (ko) 2011-09-20 2012-09-20 접착제 조성물, 필름상 접착제, 접착 시트, 회로 접속체, 회로 부재의 접속 방법, 접착제 조성물의 용도, 필름상 접착제의 용도 및 접착 시트의 용도
CN201280045620.6A CN103814100B (zh) 2011-09-20 2012-09-20 粘接剂组合物、膜状粘接剂、粘接片材、电路连接体、电路构件的连接方法、粘接剂组合物的使用、膜状粘接剂的使用以及粘接片材的使用
TW101134528A TWI587761B (zh) 2011-09-20 2012-09-20 接著劑組成物、膜狀接著劑、接著片、電路連接體、電路構件的連接方法、接著劑組成物的使用、膜狀接著劑的使用及接著片的使用
JP2013534742A JP6366936B2 (ja) 2011-09-20 2012-09-20 接着剤組成物、フィルム状接着剤、接着シート、回路接続体、回路部材の接続方法、接着剤組成物の使用、フィルム状接着剤の使用及び接着シートの使用
US13/623,289 US20130140083A1 (en) 2011-09-20 2012-09-20 Adhesive composition, film-like adhesive, adhesive sheet, circuit connection structure, method for connecting circuit members, use of adhesive composition, use of film-like adhesive and use of adhesive sheet
JP2016197363A JP6532850B2 (ja) 2011-09-20 2016-10-05 接着剤組成物、フィルム状接着剤、接着シート、回路接続体、回路部材の接続方法、接着剤組成物の使用、フィルム状接着剤の使用及び接着シートの使用
JP2018126916A JP2018188646A (ja) 2011-09-20 2018-07-03 接着剤組成物、フィルム状接着剤、接着シート、回路接続体、回路部材の接続方法、接着剤組成物の使用、フィルム状接着剤の使用及び接着シートの使用

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