WO2012014563A1 - Adhesive composition, connection structure, connection structure manufacturing method and application of adhesive composition - Google Patents
Adhesive composition, connection structure, connection structure manufacturing method and application of adhesive composition Download PDFInfo
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- WO2012014563A1 WO2012014563A1 PCT/JP2011/062418 JP2011062418W WO2012014563A1 WO 2012014563 A1 WO2012014563 A1 WO 2012014563A1 JP 2011062418 W JP2011062418 W JP 2011062418W WO 2012014563 A1 WO2012014563 A1 WO 2012014563A1
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- WIPO (PCT)
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- adhesive composition
- circuit member
- connection terminal
- acrylate
- meth
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- 0 CC(C)(c(cc1)ccc1OC)c(cc1)ccc1OC1=**C1=C Chemical compound CC(C)(c(cc1)ccc1OC)c(cc1)ccc1OC1=**C1=C 0.000 description 2
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- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/06—Polyurethanes from polyesters
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- 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
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
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- C09J11/06—Non-macromolecular additives organic
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- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
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- 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
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- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
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- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
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- 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
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- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
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Definitions
- the present invention relates to an adhesive composition, a connection structure, a manufacturing method of the connection structure, and an application of the adhesive composition.
- adherends used for adhesion include printed wiring boards, organic substrates such as polyimide, polyethylene terephthalate (PET), polycarbonate (PC), polyethylene naphthalate (PEN), metals such as copper and aluminum, Since base materials with various surface states such as ITO (complex oxide of indium and tin), IZO (complex oxide of indium and zinc), SiN, and SiO 2 are used, adhesion suitable for each adherend Molecular design of the agent composition is necessary. In recent years, the thickness of an electronic device on which a semiconductor element and a liquid crystal display element are mounted is required to reduce the thickness of a base material to be an adherend.
- thermosetting resin using an epoxy resin having 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 upon heating, and is an important factor that determines the curing temperature and the curing rate.
- Various compounds have been used from the viewpoints of storage stability at room temperature and curing rate during heating.
- a desired adhesion was obtained by curing at a temperature of 170 to 250 ° C. for 1 to 3 hours.
- a radical curable adhesive using a radical polymerizable compound such as an acrylate derivative or a methacrylate derivative in combination with a peroxide as a radical polymerization initiator has attracted attention.
- the radical curable adhesive can be cured for a short time because radicals that are reactive species are rich in reactivity (see, for example, Patent Document 2).
- the radical curable adhesive has a large cure shrinkage upon heating, it is inferior in adhesive strength as compared with the case of using an epoxy resin.
- Adhesives have been proposed in which flexibility is imparted by ether bonding to improve the adhesive strength against such a decrease in adhesive strength (see Patent Documents 3 and 4).
- an adhesive that improves the adhesive strength by dispersing stress-absorbing particles made of a rubber-based elastic material in the adhesive see Patent Document 5).
- curable adhesive cold, to cure in a short time polyimide, PET, PC, organic substrate and ITO, IZO, SiN, wettability sufficient to give to the inorganic base material such as SiO 2 of PEN, etc. It's hard to be done.
- the methods described in Patent Documents 3 to 5 described above are used, sufficient wettability with respect to the organic substrate and inorganic substrate cannot be obtained, resulting in a problem that adhesive strength is reduced.
- there is a need for more flexible and elongation of the adhesive composition In this method, sufficient flexibility and elongation cannot be obtained with respect to the adhesive composition, resulting in a problem that the adhesive strength is lowered.
- the present invention can obtain excellent adhesive strength even under low-temperature and short-time curing conditions, and stable performance (adhesive strength and connection resistance) even after a long-term reliability test (high-temperature and high-humidity test). It is an object of the present invention to provide an adhesive composition capable of maintaining the above, a connection structure for circuit members using the same, a method for producing the connection structure, and an application of the adhesive composition.
- the present invention connects a first circuit member having a first connection terminal on the main surface and a second circuit member having a second connection terminal on the main surface.
- An adhesive composition for: (a) a thermoplastic resin, (b) a radical polymerizable compound, (c) a radical polymerization initiator, and (d) a vinyl having a phosphate group
- an adhesive composition comprising a compound and (b) a urethane (meth) acrylate having a radically polymerizable compound having a critical surface tension of 20 to 40 mN / m.
- the first adhesive composition contains the above-described components, and (b) the radical polymerizable compound contains a urethane (meth) acrylate having a critical surface tension of 20 to 40 mN / m, whereby polyimide, PET, PC, organic substrate and ITO of PEN, etc., to improve IZO, SiN, wettability to the inorganic base material such as SiO 2 enables bonding at a low temperature curing, to improve the bonding strength between circuit members Can do. In addition, stable performance can be maintained even after a long-term reliability test.
- the radical polymerizable compound contains a urethane (meth) acrylate having a critical surface tension of 20 to 40 mN / m, whereby polyimide, PET, PC, organic substrate and ITO of PEN, etc., to improve IZO, SiN, wettability to the inorganic base material such as SiO 2 enables bonding at a low temperature curing, to improve the bonding strength between circuit members Can do.
- the viscosity of urethane (meth) acrylate at 25 ° C. is preferably 600 to 5000 Pa ⁇ s.
- the viscosity at 25 ° C. of urethane (meth) acrylate is in the above range, appropriate fluidity is obtained, wettability is improved, and adhesive strength between circuit members can be improved.
- the urethane (meth) acrylate preferably has a weight average molecular weight of 10,000 or more and less than 25,000.
- the weight average molecular weight of the urethane (meth) acrylate is in the above range, an appropriate flexibility is imparted to the adhesive composition, the adhesive strength between circuit members is improved, and excellent connection reliability can be obtained. it can.
- the first adhesive composition of the present invention preferably has an elongation at break of 300 to 500%.
- the elongation at break is in the above range, sufficient flexibility is imparted to the adhesive composition, the adhesive strength between the circuit members is improved, and excellent connection reliability can be obtained.
- the present invention is an adhesive composition for connecting a first circuit member having a first connection terminal on a main surface and a second circuit member having a second connection terminal on a main surface.
- the adhesive composition contains (a) a thermoplastic resin, (b) a radically polymerizable compound, and (c) a radical polymerization initiator, and (b) the radically polymerizable compound contains urethane (meth) acrylate.
- An adhesive composition (second adhesive composition) having an elongation at break of 300 to 500% is provided.
- the second adhesive composition contains the above-described components, and (b) the radically polymerizable compound contains urethane (meth) acrylate, and the elongation at break is in the above range, sufficient flexibility. Can be applied to follow the deformation of the adherend (polyimide, PET, PC, PEN, etc.), so that the adhesive strength between the circuit members is improved and excellent connection reliability can be obtained.
- adherend polyimide, PET, PC, PEN, etc.
- the second adhesive composition of the present invention preferably further contains (d) a vinyl compound having a phosphate group.
- a vinyl compound having a phosphate group By containing a vinyl compound having a phosphate group, it is possible to improve the adhesion to a metal substrate. Moreover, the outstanding adhesive strength with respect to the circuit member which has a connection terminal comprised from a metal, ITO, IZO etc. can be obtained.
- the first and / or second adhesive composition of the present invention preferably has a storage elastic modulus at 200 ° C. of 0.5 to 5 MPa.
- a storage elastic modulus at 200 ° C. is in the above range, sufficient flexibility and crosslink density can be achieved, and the stress at the interface between the adherend of the adhesive composition and the adhesive composition is relieved. . Therefore, it is possible to maintain stable performance even after a long-time reliability test while improving the adhesive strength between circuit members.
- the thermoplastic resin is a group consisting of a phenoxy resin, a polyurethane resin, a polyester urethane resin, a butyral resin, an acrylic resin, and a polyimide resin. It is preferable to contain at least one selected from the above.
- the thermoplastic resin By containing the said resin as a thermoplastic resin, the heat resistance of an adhesive composition and adhesiveness improve more.
- first and / or second adhesive composition of the present invention preferably further contains (e) conductive particles.
- conductive particles By containing conductive particles, it is possible to impart good conductivity or anisotropic conductivity to the adhesive composition. Therefore, it is preferably used for bonding applications between circuit members having connection terminals. It becomes possible. Moreover, the connection resistance of the circuit member electrically connected via the said 1st and / or 2nd adhesive composition can be reduced more fully.
- this invention is a circuit member provided with the 1st circuit member which has a 1st connection terminal on a main surface, the 2nd circuit member which has a 2nd connection terminal on a main surface, and a connection member
- the first circuit member and the second circuit member are the first and / or second adhesive compositions so that the first connection terminal and the second connection terminal face each other.
- the first connection terminal and the second connection terminal are electrically connected, and the first circuit member and / or the second circuit member has a glass transition temperature.
- a connection structure for circuit members which is composed of a base material containing a thermoplastic resin at 200 ° C. or lower.
- thermoplastic resin having a glass transition temperature of 200 ° C. or less. It is possible to follow the deformation of the base material including the substrate, the wettability to the base material is improved, and the adhesive strength between the circuit members can be sufficiently increased. In addition, stable performance can be maintained even after a long-term reliability test.
- the thermoplastic resin having a glass transition temperature of 200 ° C. or lower is preferably at least one selected from the group consisting of polyethylene terephthalate, polycarbonate, and polyethylene naphthalate. Since the cured product of the first and / or second adhesive composition of the present invention is used for connecting a pair of circuit members, the connection structure follows the deformation of the base material containing polyethylene terephthalate or the like. Thus, the wettability with respect to the base material is improved, and the adhesive strength between the circuit members can be sufficiently increased. In addition, stable performance can be maintained even after a long-term reliability test.
- one circuit member of the first circuit member or the second circuit member is at least one selected from the group consisting of polyethylene terephthalate, polycarbonate, and polyethylene naphthalate. It is comprised from the base material to contain, and it is preferable that the other circuit member is a polyimide resin among a 1st circuit member or a 2nd circuit member.
- the first circuit member and the second circuit member are composed of the above-described base materials, so that the wettability and adhesive strength with the adhesive composition are further improved, and an excellent connection is achieved. Reliability can be obtained.
- the present invention provides a first circuit member having a first connection terminal on the main surface and a second circuit member having a second connection terminal on the main surface through the adhesive composition.
- the manufacturing method of the connection structure of a circuit member provided with these is provided. According to this manufacturing method, the connection structure of the circuit member which has the outstanding connection reliability can be obtained by connecting the 1st circuit member and the 2nd circuit member with the said adhesive composition.
- the present invention also includes (a) a thermoplastic resin, (b) a radical polymerizable compound, (c) a radical polymerization initiator, and (d) a vinyl compound having a phosphate group, and (b) radical polymerization.
- a first adhesive terminal having a first connection terminal on a main surface of an adhesive composition (first adhesive composition), wherein the adhesive compound includes urethane (meth) acrylate having a critical surface tension of 20 to 40 mN / m
- the application of the adhesive composition for connecting the circuit member and the second circuit member having the second connection terminal on the main surface is provided.
- the first adhesive composition contains the above-described components, and (b) the radical polymerizable compound contains a urethane (meth) acrylate having a critical surface tension of 20 to 40 mN / m, whereby polyimide, PET, PC, organic substrate and ITO of PEN, etc., to improve IZO, SiN, wettability to the inorganic base material such as SiO 2 enables bonding at a low temperature curing, to improve the bonding strength between circuit members Can do. In addition, stable performance can be maintained even after a long-term reliability test.
- the radical polymerizable compound contains a urethane (meth) acrylate having a critical surface tension of 20 to 40 mN / m, whereby polyimide, PET, PC, organic substrate and ITO of PEN, etc., to improve IZO, SiN, wettability to the inorganic base material such as SiO 2 enables bonding at a low temperature curing, to improve the bonding strength between circuit members Can do.
- the viscosity of urethane (meth) acrylate at 25 ° C. is preferably 600 to 5000 Pa ⁇ s.
- the viscosity at 25 ° C. of the urethane (meth) acrylate is in the above range, appropriate fluidity is obtained, wettability is improved, and excellent connection reliability can be obtained.
- the weight average molecular weight of urethane (meth) acrylate is preferably 10,000 or more and less than 25,000.
- the weight average molecular weight of the urethane (meth) acrylate is in the above range, an appropriate flexibility is imparted to the adhesive composition, the adhesive strength between circuit members is improved, and excellent connection reliability can be obtained. it can.
- the elongation at break of the adhesive composition is preferably 300 to 500%.
- the elongation at break is in the above range, sufficient flexibility is imparted to the adhesive composition, the adhesive strength between the circuit members is improved, and excellent connection reliability can be obtained.
- the present invention includes (a) a thermoplastic resin, (b) a radical polymerizable compound, and (c) a radical polymerization initiator, (b) the radical polymerizable compound contains urethane (meth) acrylate, A first circuit member having a first connection terminal on a main surface of an adhesive composition (second adhesive composition) having a breaking elongation of 300 to 500%, and a second circuit on a main surface An application of an adhesive composition for connecting a second circuit member having a connection terminal is provided.
- the second adhesive composition contains the above-described components, and (b) the radically polymerizable compound contains urethane (meth) acrylate, and the elongation at break is in the above range, sufficient flexibility. Can be applied to follow the deformation of the adherend (polyimide, PET, PC, PEN, etc.), so that the adhesive strength between the circuit members is improved and excellent connection reliability can be obtained.
- the adhesive composition further contains (d) a vinyl compound having a phosphate group.
- a vinyl compound having a phosphate group By containing a vinyl compound having a phosphate group, it becomes possible to improve the adhesion to a metal substrate, and a circuit member having a connection terminal made of metal, ITO, IZO or the like Excellent adhesion strength can be obtained.
- the storage elastic modulus at 200 ° C. of the adhesive composition is preferably 0.5 to 5 MPa.
- the storage elastic modulus at 200 ° C. is in the above range, sufficient flexibility and crosslink density can be achieved, and the stress at the interface between the adherend of the adhesive composition and the adhesive composition is relieved. . Therefore, it is possible to maintain stable performance even after a long-time reliability test while improving the adhesive strength between circuit members.
- thermoplastic resin contains at least one selected from the group consisting of phenoxy resin, polyurethane resin, polyester urethane resin, butyral resin, acrylic resin, and polyimide resin.
- thermoplastic resin contains at least one selected from the group consisting of phenoxy resin, polyurethane resin, polyester urethane resin, butyral resin, acrylic resin, and polyimide resin.
- the adhesive composition further contains (e) conductive particles.
- conductive particles By containing conductive particles, it is possible to impart good conductivity or anisotropic conductivity to the adhesive composition. Therefore, it is preferably used for bonding applications between circuit members having connection terminals. It becomes possible, and the connection resistance of the circuit member electrically connected via the first and / or second adhesive composition can be more sufficiently reduced.
- adhesive strength and connection resistance can be maintained even after a long-term reliability test (high temperature and high humidity test). It is possible to provide an adhesive composition that can be used, a circuit member connection structure using the same, a method for manufacturing the connection structure, and an application of the adhesive composition.
- (meth) acrylic acid means acrylic acid or methacrylic acid corresponding thereto
- (meth) acrylate means acrylate or corresponding methacrylate
- (meth) acryloyl group means acryloyl group. Or means a methacryloyl group.
- “Critical surface tension ( ⁇ c )” in the present embodiment means that liquid urethane (meth) acrylate or urethane (meth) acrylate is dissolved in a solvent, and the resulting liquid material is applied onto a fluororesin film by a coating apparatus. It was applied and dried with hot air at 70 ° C. for 10 minutes or at a temperature and time that can remove the solvent used, and the resulting film-like urethane (meth) acrylate was mixed with pure water and wet tension test mixed solution No.
- the “storage modulus” in the present embodiment refers to hot air having a temperature and a time at which the adhesive composition is applied onto a fluororesin film by a coating apparatus and the solvent used can be removed at 70 ° C. for 10 minutes. After drying, the obtained film-like adhesive composition was heat-cured at 180 ° C. for 1 hour, and the obtained sample was subjected to viscoelasticity analyzer “RSA-3” (trade name) manufactured by TA Instruments. Is the value of the storage elastic modulus (E ′) at 200 ° C. measured under the conditions of a heating rate of 5 ° C./min, a frequency of 10 Hz, and a measurement temperature of ⁇ 150 to 300 ° C.
- “Elongation at break” in the present embodiment means that the adhesive composition is applied onto a fluororesin film by a coating apparatus, and is dried with hot air at 70 ° C. for 10 minutes or at a temperature and time at which the solvent used can be removed.
- the obtained film-like adhesive composition was heat-cured at 180 ° C. for 1 hour, and the obtained sample was pulled using a material tester “Micro Tester 5548” (trade name) manufactured by Instron Co., Ltd. It is a value obtained by measuring the length L between the gauge points and the original distance L 0 between the gauge points by using the following equation (1) when measured under the conditions of min and measurement temperature of 25 ° C.
- Elongation at break (%) (L ⁇ L 0 ) / L 0 ⁇ 100 (1)
- the “viscosity” in the present embodiment is a value obtained by measuring urethane (meth) acrylate under the conditions of a frequency of 1 Hz and a measurement temperature of 25 ° C. using a rheometer “Physica MCR301” (trade name) manufactured by Anton Paar. Say.
- Glass transition temperature (Tg) in the present embodiment refers to a film-like organic base material using a viscoelasticity analyzer “RSA-3” (trade name) manufactured by TA Instruments, Inc. The value of tan ⁇ peak temperature in the vicinity of Tg, measured under the conditions of 5 ° C./min, frequency 10 Hz, measurement temperature ⁇ 150 to 300 ° C.
- weight average molecular weight and “number average molecular weight” refer to values measured using a standard polystyrene calibration curve from a gel permeation chromatograph (GPC) according to the conditions shown in Table 1.
- the adhesive composition according to the first embodiment of the present invention includes a first circuit member having a first connection terminal on the main surface and a second circuit member having a second connection terminal on the main surface.
- An adhesive composition comprising: (a) a thermoplastic resin, (b) a radical polymerizable compound, (c) a radical polymerization initiator, and (d) phosphoric acid.
- a vinyl compound having a group, and (b) the radically polymerizable compound contains urethane (meth) acrylate having a critical surface tension of 20 to 40 mN / m.
- thermoplastic resin (a) used in this embodiment becomes a highly viscous liquid state by heating and is freely deformed by external force. When cooled and removed, the resin becomes hard while maintaining its shape, and this process is repeated.
- This is a resin (polymer) that has the property of being
- a resin (polymer) having a reactive functional group having the above properties is also included.
- the glass transition temperature (Tg) of the thermoplastic resin is preferably 0 to 190 ° C., more preferably 20 to 170 ° C.
- thermoplastic resin polyimide resin, polyamide resin, phenoxy resin, (meth) acrylic resin, urethane resin, polyester urethane resin, polyvinyl butyral resin 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 weight average molecular weight of the thermoplastic resin is preferably 5,000 to 150,000, and more preferably 10,000 to 80,000. If the weight average molecular weight is less than 5,000, good film formability tends to be difficult to obtain, and if it exceeds 150,000, good compatibility with other components tends to be difficult to obtain.
- the content of the thermoplastic resin (a) in the adhesive composition is preferably 5 to 80% by mass, more preferably 15 to 70% by mass based on the total amount of the adhesive composition.
- this content is less than 5% by mass, particularly when the adhesive composition is used in the form of a film, good film formability tends to be difficult to obtain, and when it exceeds 80% by mass, good adhesion is obtained.
- the fluidity of the agent composition tends to be difficult to obtain.
- the (b) radical polymerizable compound contained in the adhesive composition of the present embodiment refers to a compound that generates radical polymerization by the action of a radical polymerization initiator, but by applying activation energy such as light and heat. It may be a compound that itself generates a radical.
- a compound having a functional group that is polymerized by an active radical such as a vinyl group, a (meth) acryloyl group, an allyl 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, trimethylolpropane tri ( (Meth) acrylate, polyethylene glycol di (meth) acrylate, polyalkylene glycol di (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, neopentyl glycol di (meth) acrylate, di Pentaerythritol hexa (meth) acrylate, isocyanuric acid modified bifunctional (meth) acrylate, isocyanuric acid modified trifunctional (meth) acrylate, bisphenoxyeta (Meth) acrylic acid is added to the glycidyl group of bisphenol fluorene gly
- 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. ]
- the radically polymerizable compound (b) is a solid state having no fluidity such as waxy, waxy, crystalline, glassy or powdery when left alone at 30 ° C.
- the (b) radical polymerizable compound 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, N-octylmaleimide, 4,4'-diphenylmethane Bismaleimide, m-fe Renbismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, 4-methyl-1,3-phenylenebismaleimide, N-methacryloxymaleimide, N-acryloxymaleimide 1,6-bismaleimide- (2,2,2,
- 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 13 represents a hydrogen atom or a methyl group.
- R 14 represents a hydrogen atom or a methyl group.
- N-vinyl compounds selected from the group consisting of N-vinyl compounds and N, N-dialkylvinyl compounds, which are compounds belonging to radically polymerizable compounds, are substituted with other (b) radically polymerizable compounds. Can be used together.
- the N-vinyl compound in combination the crosslinking rate of the adhesive composition can be improved.
- 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.
- (b) radically polymerizable compound in this specification is (d) vinyl which has a phosphate group. It shall mean radically polymerizable compounds other than compounds.
- the content of the (b) radical polymerizable compound in the adhesive composition is preferably 50 to 250 parts by mass, and preferably 60 to 150 parts by mass with respect to 100 parts by mass of the (a) thermoplastic resin. More preferred. When the content is less than 50 parts by mass, sufficient heat resistance tends to be hardly obtained after curing, and when it exceeds 250 parts by mass, good film formability is obtained when used as a film. It tends to be difficult.
- the adhesive composition of this embodiment contains (b) urethane (meth) acrylate having a critical surface tension of 20 to 40 mN / m as a radical polymerizable compound.
- the urethane acrylate having the critical surface tension is more preferably used.
- the urethane (meth) acrylate can be obtained by a condensation reaction of an aliphatic diisocyanate and an aliphatic diol.
- the aliphatic diisocyanate constituting the urethane (meth) acrylate is 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 trimethyl It is selected from xylylene diisocyanate and the like.
- the aliphatic diol constituting the urethane (meth) acrylate is ethylene glycol, propylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, Neopentyl glycol, 1,2-pentanediol, 1,4-pentanediol, 1,5-pentanediol, 2,4-pentanediol, 2-methyl-2,4-pentanediol, 2,4-dimethyl-2 , 4-pentanediol, 2,2,4-trimethyl-1,3-pentanediol, 1,2-hexanediol, 1,5-hexanediol, 1,6-hexanediol, 2,5-hexanediol, 2, -Ethyl-1,3-hexanediol, 2,5-d
- polyester diols obtained from the diols and dicarboxylic acids may be used alone or in combination of two or more polyester diols.
- the critical surface tension of urethane (meth) acrylate can be easily controlled within the range of 20 to 40 mN / m.
- the critical surface tension of the urethane (meth) acrylate is 20 to 40 mN / m, preferably 20 to 35 mN / m, and more preferably 20 to 33 mN / m.
- the critical surface tension of urethane (meth) acrylate is within the above range, it becomes close to the critical surface tension of polyimide, PET, etc., which are adherends, and improves wettability, thereby improving adhesive strength and excellent connection. Reliability can be obtained.
- the critical surface tension of the urethane (meth) acrylate is related to the urethane bond equivalent and can be adjusted by changing the number average molecular weight of the diol. For example, when the number average molecular weight of the diol is increased, the urethane bond equivalent decreases, and the critical surface tension tends to decrease.
- the weight average molecular weight of the urethane (meth) acrylate is within the range of 10,000 or more and less than 25,000 from the viewpoint of improving the adhesive strength to the substrate such as polyimide, PET, PC, PEN. Preferably there is. If the weight average molecular weight of the urethane (meth) acrylate is within the above range, both flexibility and cohesion can be obtained, and the adhesive strength with organic base materials such as polyimide, PET, PC, and PEN can be improved. Excellent connection reliability can be obtained. Further, from the viewpoint of obtaining such effects more sufficiently, the weight average molecular weight of the urethane (meth) acrylate is more preferably 12000 or more and less than 20000. If the weight average molecular weight of the urethane (meth) acrylate is less than 10,000, sufficient flexibility tends not to be obtained, and if it is 25,000 or more, the fluidity of the adhesive composition tends to decrease. .
- the viscosity of the urethane (meth) acrylate at 25 ° C. is preferably 600 to 5000 Pa ⁇ s, and more preferably 600 to 4500 Pa ⁇ s.
- the viscosity at 25 ° C. of the urethane (meth) acrylate is in the above range, sufficient fluidity can be obtained and excellent connection reliability can be obtained. Moreover, an appropriate tack force can be obtained, and the handleability is excellent.
- the pressure is less than 600 Pa ⁇ s, the tack force tends to increase, and the handleability tends to deteriorate. If the pressure exceeds 5000 Pa ⁇ s, sufficient fluidity cannot be obtained, and the wettability to the adherend is reduced, and adhesion Strength and connection reliability tend to deteriorate.
- the content of the urethane (meth) acrylate is preferably 5 to 95% by mass, more preferably 10 to 80% by mass, based on the total amount of the adhesive composition.
- the content is less than 5% by mass, the heat resistance tends to decrease, and when it exceeds 95% by mass, the film formability tends to decrease when used as a film.
- the radical polymerization initiator contained in the adhesive composition of the present embodiment conventionally known organic peroxides, azo compounds, and the like are compounds that generate radicals by applying external energy. Can be used.
- the radical polymerization initiator is preferably an organic peroxide having a one-minute half-life temperature of 90 to 175 ° C. and a molecular weight of 180 to 1000 from the viewpoints of stability, reactivity, and compatibility. When 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, di (2 -Ethylhexyl) peroxydicarbonate, cumylperoxyneodecanoate, 1,1,3,3-tetramethylbutylperoxyneodecanoate, dilauroyl peroxide, 1-cyclohexyl-1-methylethylperoxyneo Decanoate, t-hexylperoxyneodecanoate, t-butylperoxyneodecanoate, t-butylperoxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexa Noate, 2,5-dimethyl-2,5-di (2-ethylhexanoylperoxy) hexane, t Hex
- These compounds may be used alone or in combination of two or more compounds.
- the (c) radical polymerization initiator a compound that generates radicals upon irradiation with light of 150 to 750 nm 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 content of the radical polymerization initiator (c) is preferably 0.1 to 500 parts by weight, more preferably 1 to 300 parts by weight, and more preferably 5 to 50 parts by weight with respect to 100 parts by weight of the (a) thermoplastic resin. More preferred is 10 to 30 parts by mass.
- the content of the radical polymerization initiator is less than 0.1 parts by mass, the adhesive composition tends to be hard to be cured sufficiently, and when it exceeds 500 parts by mass, the storage stability tends to deteriorate.
- the vinyl compound having a phosphate group is not particularly limited as long as it is a compound having a phosphate group and a vinyl group, but the vinyl group has a radical polymerizable property.
- a phosphoric acid (meth) acrylate compound having at least one excellent (meth) acryloyl group in the molecule is more preferred. Examples of such compounds include compounds represented by the following general formulas (M) to (O).
- R 15 represents a (meth) acryloyloxy group
- R 16 represents a hydrogen atom or a methyl group
- k and l each independently represents an integer of 1 to 8.
- R 15 s , R 16 s , k s, and l s may be the same or different.
- R 17 represents a (meth) acryloyloxy group
- m and n each independently represents an integer of 1 to 8.
- R 17 s , m s, and n s may be the same or different.
- R 18 represents a (meth) acryloyloxy group
- R 19 represents a hydrogen atom or a methyl group
- o and p each independently represent an integer of 1 to 8.
- R 19 and o 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, and acid phosphooxypolyoxypropylene glycol.
- examples thereof include monomethacrylate, 2,2′-di (meth) acryloyloxydiethyl phosphate, EO-modified phosphoric acid dimethacrylate, phosphoric acid-modified epoxy acrylate, and vinyl phosphate.
- the content of the (d) phosphate group-containing vinyl compound in the adhesive composition is independent of the content of the (b) radical polymerizable compound other than the phosphate group-containing vinyl compound, and (a) 100 mass of the thermoplastic resin.
- the amount is preferably 0.2 to 300 parts by weight, more preferably 1 to 200 parts by weight, still more preferably 1 to 50 parts by weight, based on 1 part by weight. Is particularly preferred.
- Conductive particles contained in the adhesive composition of the present embodiment may be particles having conductivity on the whole or on the surface, but when used for connection of circuit members having connection terminals, The average particle size is preferably smaller than the distance between the connection terminals.
- the conductive particles include metal particles such as Au, Ag, Ni, Cu, and solder, and carbon. Further, 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 are made of plastic as a core and the core is coated with the above metal, metal particles or carbon, or hot-melt metal particles, they are deformable by heating and pressurization, so that they are in contact with the electrode at the time of connection. This is preferable because the area is increased and the reliability is improved.
- the fine particles obtained by coating the surface of these conductive particles (e) with a polymer resin or the like suppress a short circuit due to contact between particles when the content of the conductive particles is increased. Since insulation can be improved, it may be used alone or in combination with (e) conductive particles.
- the average particle diameter of the conductive particles is preferably 1 to 18 ⁇ m from the viewpoint of dispersibility and conductivity.
- the adhesive composition can be suitably used as an anisotropic conductive adhesive.
- the content of the conductive particles (e) in the adhesive composition is not particularly limited, but is preferably 0.1 to 30% by volume with respect to the total volume of the adhesive composition, preferably 0.1 to 10%. It is more preferable to set it as volume%. If this value is less than 0.1% by volume, the conductivity tends to be low, and if it exceeds 30% by volume, a short circuit tends to occur.
- 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 of the present embodiment in order to control the curing rate and to provide 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 content of the stabilizer is preferably 0.01 to 30 parts by mass, more preferably 0.05 to 10 parts by mass with respect to 100 parts by mass of the adhesive composition.
- the content is less than 0.01 part by mass, it becomes difficult to control the curing rate and storage stability, and when it exceeds 30 parts by mass, the compatibility with other components tends to be adversely affected.
- an adhesive aid such as a coupling agent represented by an alkoxysilane derivative or a silazane derivative, an adhesion improver, and a leveling agent may be appropriately added to the adhesive composition of the present embodiment.
- a compound represented by the following general formula (P) is preferable as the coupling agent.
- the adhesion assistant may be used alone or in admixture of two or more compounds.
- R 20 , R 21 and R 22 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 an alkoxycarbonyl group having 1 to 5 carbon atoms.
- R 23 is 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, a phenylamino group, or a cyclohexylamino group.
- Morpholino group, piperazino group, ureido group or glycidyl group, q represents an integer of 1 to 10.
- a rubber component may be used in combination for the purpose of stress relaxation and adhesion improvement.
- 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.
- Even a compound having a polybutadiene skeleton is classified as (a) a thermoplastic resin if it exhibits thermoplasticity, and (b) as a radically polymerizable compound if it exhibits radical polymerizability.
- 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, acrylonitrile-butadiene rubber containing carboxyl group, hydroxyl group, (meth) acryloyl group or morpholine group at the polymer end, 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 end.
- a liquid acrylonitrile-butadiene rubber specifically includes a carboxyl group, a hydroxyl group, a (meth) acryloyl group or a morpholine group at the polymer end.
- examples thereof include liquid acrylonitrile-butadiene rubber and liquid carboxylated nitrile rubber.
- the content of acrylonitrile, which is a polar group is preferably 10 to 60% by mass.
- These rubber components may be used alone or in combination of two or more compounds.
- organic fine particles may be added to the adhesive composition of the present embodiment for the purpose of stress relaxation and adhesion improvement.
- the average particle size of the organic fine particles is preferably 0.05 to 1.0 ⁇ m.
- organic fine particles consist of the above-mentioned rubber component it classify
- 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
- organic fine particles may be used alone or in combination of two or more compounds.
- the breaking elongation of the adhesive composition of the present embodiment is preferably 300 to 500%, more preferably 300 to 450%.
- the elongation at break is in the above range, sufficient flexibility is imparted, and even if it is an adherend having an organic substrate (polyimide, PET, PC, PEN, etc.), it can follow the deformation.
- the adhesion strength between circuit members is improved, and excellent connection reliability can be obtained.
- the elongation at break is less than 300%, sufficient flexibility is not imparted, and there is a tendency that it is difficult to follow the deformation of the adherend, and when it is more than 500%, the flexibility is too large and the adhesive strength between circuit members is increased. Tends to decrease.
- the elongation at break can be adjusted by using urethane (meth) acrylate obtained from an aliphatic or aromatic diisocyanate and an aliphatic diol.
- urethane (meth) acrylate obtained from an aliphatic or aromatic diisocyanate and an aliphatic diol.
- the content of the urethane (meth) acrylate is increased, the elongation at break tends to increase.
- the weight average molecular weight of the said urethane (meth) acrylate becomes large, it exists in the tendency for breaking elongation to also become large.
- the weight average molecular weight of the thermoplastic resin is high and Tg is low, the elongation at break tends to increase.
- the storage elastic modulus at 200 ° C. of the adhesive composition of the present embodiment is preferably 0.5 to 5 MPa, and more preferably 0.5 to 3.5 MPa.
- the storage elastic modulus at 200 ° C. is in the above range, sufficient flexibility and crosslink density can be achieved, and the stress at the interface between the adherend of the adhesive composition and the adhesive composition is relieved. . Therefore, it is possible to maintain stable performance even after a long-time reliability test while improving the adhesive strength between circuit members. If the storage elastic modulus is smaller than 0.5 MPa or larger than 5 MPa, it tends to be difficult to achieve both sufficient connection strength and good connection reliability.
- the adhesive composition of this embodiment can be used in the form of 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 to 150 ° C. at normal pressure. When the boiling point is less than 50 ° C., it tends to volatilize when left at room temperature, and it tends to be difficult to use in an open system. On the other hand, if the boiling point exceeds 150 ° C., it is difficult to volatilize the solvent, and the reliability after adhesion tends to be adversely affected.
- the adhesive composition of the present embodiment can be used in the form of a film.
- 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 placed on a peelable substrate and used as a film after removing the solvent and the like.
- Use of the adhesive composition in the form of a film is more convenient from the viewpoint of handleability and the like.
- the adhesive composition of the present embodiment can be bonded by using both heating and pressing.
- the heating temperature is preferably 100 to 200 ° C.
- the pressure is preferably in a range that does not damage the adherend, and generally 0.1 to 10 MPa. These heating and pressurization are preferably performed in the range of 0.5 seconds to 120 seconds, and can be bonded by heating at 120 to 190 ° C., 3 MPa, and 10 seconds.
- the adhesive composition of the present embodiment can be used as an adhesive for different types of adherends having different thermal expansion coefficients. Specifically, it is used as a semiconductor element adhesive material typified by anisotropic conductive adhesive, silver paste, silver film, etc., circuit connection material, CSP elastomer, CSP underfill material, LOC tape, etc. Can do.
- the adhesive composition which concerns on 2nd Embodiment of this invention is the 1st circuit member which has a 1st connection terminal on a main surface, and the 2nd circuit which has a 2nd connection terminal on a main surface.
- An adhesive composition for connecting a member comprising (a) a thermoplastic resin, (b) a radical polymerizable compound, and (c) a radical polymerization initiator, (b) a radical polymerizable compound Contains urethane (meth) acrylate and has an elongation at break of 300 to 500%.
- the adhesive composition according to the second embodiment contains the above components, the (b) radical polymerizable compound contains urethane (meth) acrylate, and the elongation at break is 300 to 500%.
- Adhesive composition is provided with sufficient flexibility and can follow the deformation of the adherend (polyimide, PET, PC, PEN, etc.), improving the adhesive strength between circuit members and excellent connection reliability Sex can be obtained. More preferably, the breaking elongation of the adhesive composition is 300 to 450%.
- thermoplastic resin and (c) the radical polymerization initiator are the same as those used in the adhesive composition according to the first embodiment.
- the radically polymerizable compound is different in that the critical surface tension of the urethane (meth) acrylate contained is not particularly limited, but in the same manner as the adhesive composition according to the first embodiment, the urethane (The critical surface tension of the (meth) acrylate is preferably 20 to 40 mN / m, more preferably 20 to 35 mN / m, and still more preferably 20 to 33 mN / m.
- the storage elastic modulus at 200 ° C. is preferably 0.5 to 5 MPa, more preferably 0.5 to 3.5 MPa, similarly to the adhesive composition according to the first embodiment. .
- the adhesive composition according to the second embodiment preferably includes (d) a vinyl compound having a phosphate group, like the adhesive composition according to the first embodiment. (D) By including the vinyl compound which has a phosphoric acid group, it becomes possible to improve the adhesiveness to the metal base material of an adhesive composition. Moreover, the outstanding adhesive strength with respect to the circuit member which has a connection terminal comprised from a metal, ITO, IZO etc. can be obtained.
- the adhesive composition according to the second embodiment includes (e) conductive particles, a stabilizer, a coupling agent, an adhesion aid, rubber, as in the adhesive composition according to the first embodiment.
- Components and organic particulates can be added.
- the adhesive composition according to the second embodiment includes (a) a thermoplastic resin, (b) a radical polymerizable compound, and (c) a radical polymerization initiator, and the adhesive composition according to the first embodiment. It is preferable to have a content in a similar range. Further, when (d) a vinyl compound having a phosphate group and (e) conductive particles, a stabilizer, a coupling agent, an adhesion aid, a rubber component, and organic fine particles are contained, these are also the first. It is preferable to have the content in the same range as the adhesive composition according to the embodiment.
- the adhesive composition according to the first embodiment or the second embodiment of the present invention includes a first circuit member having a first connection terminal on the main surface and a second circuit terminal having a second connection terminal on the main surface. It is used as an adhesive composition for connecting two circuit members.
- said 1st circuit member and / or said 2nd circuit member are preferably comprised from the base material containing the thermoplastic resin whose glass transition temperature is 200 degrees C or less, Said 1st connection terminal and / or The second connection terminal is preferably made of ITO and / or IZO.
- a thermoplastic resin whose glass transition temperature is 200 degrees C or less For example, a polyethylene terephthalate, a polycarbonate, a polyethylene naphthalate, etc. are mentioned.
- FIG. 1 is a schematic cross section which shows one Embodiment of the connection structure of a circuit member using the adhesive composition of this embodiment which does not contain (e) electroconductive particle.
- FIG. 2 is a schematic cross-sectional view showing the first circuit member, the second circuit member, and the adhesive composition (containing no conductive particles) before producing the circuit member connection structure shown in FIG. is there.
- a circuit member connection structure 100 shown in FIG. 1 includes a first circuit member 30 having a first connection terminal 32 on a main surface 31 a of a first circuit board 31, and a main surface of a second circuit board 41.
- the main surface 31a of the first circuit board 31 so that the second circuit member 40 having the second connection terminal 42 on 41a and the first connection terminal 32 and the second connection terminal 42 face each other.
- 10C of connection members which connect the main surface 41a of the 2nd circuit board 41.
- the first connection terminal 32 and the second connection terminal 42 are electrically connected by being in contact with each other.
- 10C of connection members consist of hardened
- the circuit member connection structure 100 shown in FIG. 1 can be manufactured, for example, as follows.
- the first circuit member 30, the second circuit member 40, and the adhesive composition 10 formed into a film shape are prepared.
- the adhesive composition 10 is placed on the main surface 41a of the second circuit member 40 on which the second connection terminals 42 are formed, and the first connection terminals are further formed on the adhesive composition 10.
- the first circuit member 30 is placed so that 32 faces the second connection terminal 42.
- the adhesive composition 10 is cured while being heated through the first circuit member 30 and the second circuit member 40, and simultaneously pressurized in a direction perpendicular to the main surfaces 31a and 41a.
- a connection member 10C is formed between the second circuit members 30 and 40 to obtain the circuit member connection structure 100 of FIG.
- FIG. 3 is a schematic cross-sectional view showing an embodiment of a circuit member connection structure using the adhesive composition of this embodiment containing (e) conductive particles.
- 4 is a schematic cross-sectional view showing a first circuit member, a second circuit member, and an adhesive composition (containing conductive particles) before producing the circuit member connection structure shown in FIG. is there.
- a circuit member connection structure 200 shown in FIG. 3 includes a first circuit member 30 having a first connection terminal 32 on a main surface 31 a of a first circuit board 31, and a main surface of a second circuit board 41.
- the main surface 31a of the first circuit board 31 so that the second circuit member 40 having the second connection terminal 42 on 41a and the first connection terminal 32 and the second connection terminal 42 face each other.
- the connecting member 20C is a cured product of the adhesive composition 20 in which the conductive particles 22 are dispersed in the component 21 other than the conductive particles of the adhesive composition (that is, the components other than the conductive particles of the adhesive composition).
- the conductive particles 22 are dispersed in the cured product 21C), and the conductive particles 22 are in contact with both connection terminals between the first connection terminal 32 and the second connection terminal 42 facing each other. Both connection terminals are electrically connected through the conductive particles 22.
- the circuit member connection structure 200 shown in FIG. 3 includes, for example, as shown in FIG. 4, a first circuit member 30, a second circuit member 40, and an adhesive composition 20 formed into a film shape,
- the circuit member connection structure 100 can be manufactured by the same method as described above.
- At least one of the first circuit member 30 and the second circuit member 40 is made of a base material containing a thermoplastic resin having a glass transition temperature of 200 ° C. or lower, such as polyethylene terephthalate, polycarbonate, and polyethylene naphthalate.
- a thermoplastic resin having a glass transition temperature of 200 ° C. or lower such as polyethylene terephthalate, polycarbonate, and polyethylene naphthalate.
- the first circuit board 31 and the second circuit board 41 preferably contains a thermoplastic resin having a glass transition temperature of 200 ° C. or lower, such as polyethylene terephthalate, polycarbonate, and polyethylene naphthalate.
- first circuit member 30 and the second circuit member 40 are made of a base material that does not contain a thermoplastic resin having a glass transition temperature of 200 ° C. or lower, such as polyethylene terephthalate, polycarbonate, and polyethylene naphthalate. It may be configured.
- a base material for forming such a circuit member a base material made of an inorganic material such as a semiconductor, glass or ceramic, a base material made of an organic material such as polyimide, a base material combining an inorganic material such as glass / epoxy and an organic material, etc. Can be used.
- connection terminal 32 and the second connection terminal 42 is composed of at least one selected from the group consisting of ITO and IZO.
- ITO and IZO are suitable as connection terminals because they are easily etched and have excellent pattern processability. And the corrosion of the connection terminal comprised by ITO and / or IZO can fully be suppressed by using the adhesive composition of this embodiment.
- connection terminal 32 and the second connection terminal 42 may be made of a material other than ITO and IZO.
- a connection terminal made of a metal such as copper, silver, aluminum, gold, palladium, nickel, or an alloy thereof can be used.
- connection member does not need to be completely cured (the highest degree of curing that can be achieved under predetermined curing conditions) and is in a partially cured state as long as the above characteristics are produced. May be.
- polyester urethane resin Preparation of polyester urethane
- UR-8200 trade name
- a 1: 1 mixed solvent solution of methyl ethyl ketone and toluene having a resin content of 30% by mass was used.
- Phenoxy resin manufactured by Toto Kasei Co., Ltd., YP-50 (trade name) was prepared by dissolving 40 parts by mass of resin in 60 parts by mass of methyl ethyl ketone to obtain a solution having a solid content of 40% by mass.
- urethane acrylate had a critical surface tension of 27 mN / m, a weight average molecular weight of 13,800, and a viscosity of 650 Pa ⁇ s.
- the urethane acrylate (UA4) obtained had a critical surface tension of 43 mN / m, a weight average molecular weight of 18500, and a viscosity of 4800 Pa ⁇ s.
- the urethane acrylate (UA5) obtained had a critical surface tension of 17 mN / m, a weight average molecular weight of 14500, and a viscosity of 2900 Pa ⁇ s.
- the urethane acrylate (UA6) obtained had a critical surface tension of 41 mN / m, a weight average molecular weight of 23500, and a viscosity of 6800 Pa ⁇ s.
- urethane acrylate had a critical surface tension of 16 mN / m, a weight average molecular weight of 20400, and a viscosity of 3500 Pa ⁇ s.
- Isocyanuric acid-modified bifunctional acrylate (manufactured by Toagosei Co., Ltd., M-215 (trade name)) was prepared.
- Dibenzoyl peroxide (trade name: Nyper BW, manufactured by NOF Corporation) was prepared as a radical polymerization initiator.
- 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. Was made.
- Examples 1 to 12 and Comparative Examples 1 to 5 As shown in Table 2 in terms of solid mass ratio, a thermoplastic resin, a radical polymerizable compound, and a radical polymerization initiator were blended, and 1.5% by volume of conductive particles were blended and dispersed to obtain an adhesive composition.
- the obtained adhesive composition was applied on a fluororesin film having a thickness of 80 ⁇ m using a coating apparatus, and a film-like adhesive composition having an adhesive layer thickness of 20 ⁇ m was dried by hot air at 70 ° C. for 10 minutes. Obtained.
- a flexible circuit board having 500 copper circuits having a line width of 25 ⁇ m, a pitch of 50 ⁇ m, and a thickness of 8 ⁇ m on the polyimide film, the film-like adhesive compositions of Examples 1 to 12 and Comparative Examples 1 to 5; It was interposed between the glass (thickness 1.1 mm, surface resistance 20 ⁇ / ⁇ ) on which a thin layer of 2 ⁇ m ITO was formed. Using a thermocompression bonding apparatus (heating method: constant heat type, manufactured by Toray Engineering Co., Ltd.), this was heated and pressurized at 160 ° C.
- connection body was measured with a multimeter immediately after bonding and after being held in a high-temperature and high-humidity bath 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.
- Tensilon UTM-4 peeleling speed 50 mm / min, 25 ° C.
- Toyo Baldwin Co., Ltd. was used as an adhesive strength measuring apparatus.
- the elongation at break of the film-like adhesive composition was determined by heating and curing the film-like adhesive composition at 180 ° C. for 1 hour, and subjecting the obtained sample to a material tester “Micro Tester 5548” (Instrument speed) 50 mm / min, 25 ° C.).
- the storage elastic modulus of the film-like adhesive composition was determined by heating and curing the film-like adhesive composition at 180 ° C. for 1 hour, and subjecting the obtained sample to a viscoelasticity analyzer “RSA” manufactured by TA Instruments. -3 "(heating rate 5 ° C / min, frequency 10Hz, measurement temperature -150 to 300 ° C). Table 3 below shows the results of measurement of the elongation at break, storage elastic modulus, connection resistance, and adhesive strength of the film adhesive composition performed as described above.
- the adhesive compositions obtained in Examples 1 to 7 contain components (a), (b), (c) and (d), and urethane (having a specific range of critical surface tension as component (b))
- a heating temperature of 160 ° C. was higher than in Examples 8 to 12 and Comparative Examples 1 to 5 using an adhesive composition containing a critical surface tension outside a specific range.
- the adhesive compositions obtained in Comparative Examples 1 to 5 exhibited low adhesive strength immediately after bonding and after being held in a high-temperature and high-humidity bath at 85 ° C. and 85% RH for 240 hours (after the test).
- the adhesive compositions obtained in Comparative Examples 4 and 5 have high connection resistance and low adhesive strength after being held in a high-temperature and high-humidity bath at 85 ° C. and 85% RH for 240 hours (after the test). It was.
- Comparative Examples 2 and 3 were smaller than the range in which the elongation at break was good, and Comparative Examples 4 and 5 were The elongation at break was larger than the good range. Furthermore, Comparative Examples 2 and 3 also showed values larger than the good range for the storage elastic modulus.
- the adhesive compositions obtained in Examples 8 to 12 contain the components (a), (b) and (c), and include urethane (meth) acrylate as the component (b).
- the balance between connection resistance and adhesive strength was better than those of Comparative Examples 2 to 5 where the elongation at break was out of the range. From this, by setting the elongation at break of the adhesive composition to a specific range, even if a urethane (meth) acrylate having a critical surface tension in a specific range is not used, flexibility is imparted to the adhesive composition. It is thought that a well-balanced characteristic could be obtained.
- the film-like adhesive compositions of Examples 1, 2, 4, 5 and 10 and Comparative Example 5 were prepared by using FPC having 80 copper circuits having a line width of 150 ⁇ m, a pitch of 300 ⁇ m and a thickness of 18 ⁇ m on a polyimide film, and PET.
- a thermocompression bonding apparatus 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 pressure-bonded over a width of 2 mm to prepare a connected body.
- Example 13 to 16 The adhesive compositions obtained in Examples 13 to 16 were heated at 150 ° C. for any substrate immediately after bonding and after being kept in a high-temperature and high-humidity tank at 85 ° C. and 85% RH for 240 hours. (After the test) showed a good adhesive strength of 560 N / m or more. On the other hand, in Comparative Example 6, the adhesive strength was low 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). In Example 17, although not as large as Examples 13 to 16, the adhesive strength was improved as compared with Comparative Example 6.
- adhesive strength and connection resistance can be maintained even after a long-term reliability test (high temperature and high humidity test). It is possible to provide an adhesive composition that can be used, a circuit member connection structure using the same, a method for manufacturing the connection structure, and an application of the adhesive composition.
- Adhesive composition 10C, 20C ... Connection member, 21 ... Adhesive composition which does not contain electroconductive particle, 22 ... Conductive particle, 21C ... Hardened
Abstract
Description
破断伸び(%)=(L-L0)/L0×100 …(1) “Elongation at break” in the present embodiment means that the adhesive composition is applied onto a fluororesin film by a coating apparatus, and is dried with hot air at 70 ° C. for 10 minutes or at a temperature and time at which the solvent used can be removed. The obtained film-like adhesive composition was heat-cured at 180 ° C. for 1 hour, and the obtained sample was pulled using a material tester “Micro Tester 5548” (trade name) manufactured by Instron Co., Ltd. It is a value obtained by measuring the length L between the gauge points and the original distance L 0 between the gauge points by using the following equation (1) when measured under the conditions of min and measurement temperature of 25 ° C.
Elongation at break (%) = (L−L 0 ) / L 0 × 100 (1)
本発明の第1の実施形態に係る接着剤組成物は、主面上に第一の接続端子を有する第一の回路部材と、主面上に第二の接続端子を有する第二の回路部材とを接続するための接着剤組成物であって、接着剤組成物は、(a)熱可塑性樹脂、(b)ラジカル重合性化合物、(c)ラジカル重合開始剤、及び、(d)リン酸基を有するビニル化合物を含有し、(b)ラジカル重合性化合物が20~40mN/mの臨界表面張力を有するウレタン(メタ)アクリレートを含むことを特徴とするものである。 (First embodiment)
The adhesive composition according to the first embodiment of the present invention includes a first circuit member having a first connection terminal on the main surface and a second circuit member having a second connection terminal on the main surface. An adhesive composition comprising: (a) a thermoplastic resin, (b) a radical polymerizable compound, (c) a radical polymerization initiator, and (d) phosphoric acid. A vinyl compound having a group, and (b) the radically polymerizable compound contains urethane (meth) acrylate having a critical surface tension of 20 to 40 mN / m.
また、本発明の第2実施形態に係る接着剤組成物は、主面上に第一の接続端子を有する第一の回路部材と、主面上に第二の接続端子を有する第二の回路部材とを接続するための接着剤組成物であって、(a)熱可塑性樹脂、(b)ラジカル重合性化合物、及び、(c)ラジカル重合開始剤を含有し、(b)ラジカル重合性化合物がウレタン(メタ)アクリレートを含有し、破断伸びが300~500%であることを特徴とするものである。 (Second Embodiment)
Moreover, the adhesive composition which concerns on 2nd Embodiment of this invention is the 1st circuit member which has a 1st connection terminal on a main surface, and the 2nd circuit which has a 2nd connection terminal on a main surface. An adhesive composition for connecting a member, comprising (a) a thermoplastic resin, (b) a radical polymerizable compound, and (c) a radical polymerization initiator, (b) a radical polymerizable compound Contains urethane (meth) acrylate and has an elongation at break of 300 to 500%.
(ポリエステルウレタンの準備)
ポリエステルウレタン樹脂(東洋紡株式会社製、UR-8200(商品名))は、樹脂分30質量%のメチルエチルケトンとトルエンの1:1混合溶媒溶解品を用いた。 <Thermoplastic resin>
(Preparation of polyester urethane)
As the polyester urethane resin (Toyobo Co., Ltd., UR-8200 (trade name)), a 1: 1 mixed solvent solution of methyl ethyl ketone and toluene having a resin content of 30% by mass was used.
フェノキシ樹脂(東都化成株式会社製、YP-50(商品名))は樹脂40質量部を、メチルエチルケトン60質量部に溶解して、固形分40質量%の溶液とした。 (Preparation of phenoxy resin)
Phenoxy resin (manufactured by Toto Kasei Co., Ltd., YP-50 (trade name)) was prepared by dissolving 40 parts by mass of resin in 60 parts by mass of methyl ethyl ketone to obtain a solution having a solid content of 40% by mass.
エチレン-酢酸ビニル共重合体(三井デュポンポリケミカルズ製、EV40W(商品名))は樹脂分30質量%のトルエン溶解品を用いた。 (Preparation of ethylene-vinyl acetate copolymer)
As the ethylene-vinyl acetate copolymer (manufactured by Mitsui DuPont Polychemicals, EV40W (trade name)), a toluene-dissolved product having a resin content of 30% by mass was used.
(ウレタンアクリレート(UA1)の合成)
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に2-ヒドロキシエチルアクリレート(Aldrich株式会社製)238質量部(2.05モル)、ハイドロキノンモノメチルエーテル(Aldrich株式会社製)0.53質量部、数平均分子量1000のポリ(1,6-ヘキサンジオールカーボネート)(商品名:デュラノール T5652、旭化成ケミカルズ株式会社製)2000質量部(2.00モル)、ジブチルスズジラウレート(Aldrich株式会社製)5.53質量部を投入した。充分に窒素ガスを導入した後、70~75℃に加熱し、水素添加ジフェルメタンジイソシアネート(商品名:VESTANAT H12MD、Degussa社製)787質量部(3.00モル)を3時間で均一に滴下し、反応させた。滴下完了後11時間反応させ、IR測定によりイソシアネートが消失したことを確認して反応を終了し、ウレタンアクリレートを得た。得られたウレタンアクリレート(UA1)の臨界表面張力は24mN/m、重量平均分子量が13500、粘度2500Pa・sであった。 <Radically polymerizable compound>
(Synthesis of urethane acrylate (UA1))
238 parts by mass (2.05 mol) of 2-hydroxyethyl acrylate (manufactured by Aldrich) in a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser equipped with a calcium chloride drying tube, and a nitrogen gas introduction tube, hydroquinone monomethyl ether 0.53 parts by mass (manufactured by Aldrich Co., Ltd.), poly (1,6-hexanediol carbonate) having a number average molecular weight of 1000 (trade name: DURANOL T5652, manufactured by Asahi Kasei Chemicals Co., Ltd.) 2000 parts by mass (2.00 mol), Dibutyltin dilaurate (Aldrich Co., Ltd.) 5.53 parts by mass was added. After sufficiently introducing nitrogen gas, the mixture is heated to 70 to 75 ° C., and 787 parts by mass (3.00 mol) of hydrogenated difermethane diisocyanate (trade name: VESTATAN H 12 MD, manufactured by Degussa) is uniformly added in 3 hours. It was dripped at and reacted. It was made to react for 11 hours after completion | finish of dripping, it confirmed that the isocyanate lose | disappeared by IR measurement, reaction was complete | finished, and urethane acrylate was obtained. The urethane acrylate (UA1) obtained had a critical surface tension of 24 mN / m, a weight average molecular weight of 13500, and a viscosity of 2500 Pa · s.
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に2-ヒドロキシエチルアクリレート(Aldrich株式会社製)238質量部(2.05モル)、ハイドロキノンモノメチルエーテル(Aldrich株式会社製)0.53質量部、数平均分子量1000のポリ(1,6-ヘキサンジオールカーボネート)(商品名:デュラノール T5652、旭化成ケミカルズ株式会社製)1000質量部(2.00モル)、ジブチルスズジラウレート(Aldrich株式会社製)5.53質量部を投入した。充分に窒素ガスを導入した後、70~75℃に加熱し、水素添加ジフェルメタンジイソシアネート(商品名:VESTANAT H12MD、Degussa社製)787質量部(3.00モル)を3時間で均一に滴下し、反応させた。滴下完了後13時間反応させ、IR測定によりイソシアネートが消失したことを確認して反応を終了し、ウレタンアクリレートを得た。得られたウレタンアクリレート(UA2)の臨界表面張力は23mN/m、重量平均分子量が15500、粘度4100Pa・sであった。 (Synthesis of urethane acrylate (UA2))
238 parts by mass (2.05 mol) of 2-hydroxyethyl acrylate (manufactured by Aldrich) in a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser equipped with a calcium chloride drying tube, and a nitrogen gas introduction tube, hydroquinone monomethyl ether (Aldrich Co., Ltd.) 0.53 parts by mass, number average molecular weight 1000 poly (1,6-hexanediol carbonate) (trade name: DURANOL T5652, manufactured by Asahi Kasei Chemicals Co., Ltd.) 1000 parts by mass (2.00 mol), Dibutyltin dilaurate (Aldrich Co., Ltd.) 5.53 parts by mass was added. After sufficiently introducing nitrogen gas, the mixture is heated to 70 to 75 ° C., and 787 parts by mass (3.00 mol) of hydrogenated difermethane diisocyanate (trade name: VESTATAN H 12 MD, manufactured by Degussa) is uniformly added in 3 hours. It was dripped at and reacted. It was made to react for 13 hours after completion | finish of dripping, it confirmed that the isocyanate lose | disappeared by IR measurement, reaction was complete | finished, and urethane acrylate was obtained. The urethane acrylate (UA2) obtained had a critical surface tension of 23 mN / m, a weight average molecular weight of 15500, and a viscosity of 4100 Pa · s.
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に2-ヒドロキシエチルアクリレート(Aldrich株式会社製)238質量部(2.05モル)、ハイドロキノンモノメチルエーテル(Aldrich株式会社製)0.53質量部、数平均分子量2000のポリカプロラクトンジオール(商品名:プラクセル220、ダイセル化学工業株式会社製)4000質量部(2.00モル)、ジブチルスズジラウレート(Aldrich株式会社製)5.53質量部を投入した。充分に窒素ガスを導入した後、70~75℃に加熱し、イソホロンジイソシアネート(Aldrich株式会社製)666質量部(3.00モル)を3時間で均一に滴下し、反応させた。滴下完了後12時間反応させ、IR測定によりイソシアネートが消失したことを確認して反応を終了し、ウレタンアクリレートを得た。得られたウレタンアクリレート(UA3)の臨界表面張力は27mN/m、重量平均分子量は13800、粘度650Pa・sであった。 (Synthesis of urethane acrylate (UA3))
238 parts by mass (2.05 mol) of 2-hydroxyethyl acrylate (manufactured by Aldrich) in a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser equipped with a calcium chloride drying tube, and a nitrogen gas introduction tube, hydroquinone monomethyl ether (Aldrich Co., Ltd.) 0.53 parts by mass, number-average molecular weight 2000 polycaprolactone diol (trade name: Plaxel 220, Daicel Chemical Industries, Ltd.) 4000 parts by mass (2.00 mol), dibutyltin dilaurate (Aldrich Co., Ltd.) (Made) 5.53 mass parts was thrown in. After sufficiently introducing nitrogen gas, the mixture was heated to 70 to 75 ° C., and 666 parts by mass (3.00 mol) of isophorone diisocyanate (manufactured by Aldrich Co., Ltd.) was uniformly added dropwise over 3 hours to be reacted. It was made to react for 12 hours after completion | finish of dripping, it confirmed that the isocyanate lose | disappeared by IR measurement, reaction was complete | finished, and urethane acrylate was obtained. The obtained urethane acrylate (UA3) had a critical surface tension of 27 mN / m, a weight average molecular weight of 13,800, and a viscosity of 650 Pa · s.
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に、3-メチル-1,5-ペンタンジオール1650質量部(14モル)とセバシン酸2023質量部(10モル)を反応器に仕込み、常圧下、充分に窒素ガスを導入した後、約170℃で生成する水を系外に留去しながらエステル化反応を行った。ポリエステルの酸価が0.3mgKOH/g以下になった時点で真空ポンプにより徐々に真空度を上げ、反応を完結させた。このようにして得られたポリエステルジオールは数平均分子量1000を有していた。 (Synthesis of urethane acrylate (UA4))
In a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser equipped with a calcium chloride drying tube, and a nitrogen gas introduction tube, 1650 parts by mass (14 mol) of 3-methyl-1,5-pentanediol and 2023 parts by mass of sebacic acid (10 mol) was charged into the reactor, and nitrogen gas was sufficiently introduced under normal pressure. Then, the esterification reaction was carried out while distilling off the water produced at about 170 ° C. out of the system. When the acid value of the polyester became 0.3 mgKOH / g or less, the degree of vacuum was gradually increased by a vacuum pump to complete the reaction. The polyester diol thus obtained had a number average molecular weight of 1000.
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に2-ヒドロキシエチルアクリレート(Aldrich株式会社製)238質量部(2.05モル)、ハイドロキノンモノメチルエーテル(Aldrich株式会社製)0.53質量部、数平均分子量1000のポリテトラメチレンエーテルグリコール(商品名:保土谷化学工業株式会社製、TG1000)2000質量部(2.00モル)、ジブチルスズジラウレート(Aldrich株式会社製)5.53質量部を投入した。充分に窒素ガスを導入した後、70~75℃に加熱し、イソホロンジイソシアネート(Aldrich株式会社製)666質量部(3.00モル)を3時間で均一に滴下し、反応させた。滴下完了後13時間反応させた。IR測定によりイソシアネートが消失したことを確認して反応を終了し、ウレタンアクリレートを得た。得られたウレタンアクリレート(UA5)の臨界表面張力は17mN/m、重量平均分子量が14500、粘度2900Pa・sであった。 (Synthesis of urethane acrylate (UA5))
238 parts by mass (2.05 mol) of 2-hydroxyethyl acrylate (manufactured by Aldrich) in a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser equipped with a calcium chloride drying tube, and a nitrogen gas introduction tube, hydroquinone monomethyl ether (Aldrich Co., Ltd.) 0.53 parts by mass, number average molecular weight 1000 polytetramethylene ether glycol (trade name: Hodogaya Chemical Co., Ltd., TG1000) 2000 parts by mass (2.00 mol), dibutyltin dilaurate (Aldrich) 5.53 parts by mass). After sufficiently introducing nitrogen gas, the mixture was heated to 70 to 75 ° C., and 666 parts by mass (3.00 mol) of isophorone diisocyanate (manufactured by Aldrich Co., Ltd.) was uniformly added dropwise over 3 hours to be reacted. It was made to react for 13 hours after completion of dripping. The reaction was terminated after confirming that the isocyanate had disappeared by IR measurement, and urethane acrylate was obtained. The urethane acrylate (UA5) obtained had a critical surface tension of 17 mN / m, a weight average molecular weight of 14500, and a viscosity of 2900 Pa · s.
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に、3-メチル-1,5-ペンタンジオール1650質量部(14モル)とセバシン酸2023質量部(10モル)を反応器に仕込み、常圧下、充分に窒素ガスを導入した後、約170℃で生成する水を系外に留去しながらエステル化反応を行った。ポリエステルの酸価が0.3mgKOH/g以下になった時点で真空ポンプにより徐々に真空度を上げ、反応を完結させた。このようにして得られたポリエステルジオールは数平均分子量1000を有していた。 (Synthesis of urethane acrylate (UA6))
In a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser equipped with a calcium chloride drying tube, and a nitrogen gas introduction tube, 1650 parts by mass (14 mol) of 3-methyl-1,5-pentanediol and 2023 parts by mass of sebacic acid (10 mol) was charged into the reactor, and nitrogen gas was sufficiently introduced under normal pressure. Then, the esterification reaction was carried out while distilling off the water produced at about 170 ° C. out of the system. When the acid value of the polyester became 0.3 mgKOH / g or less, the degree of vacuum was gradually increased by a vacuum pump to complete the reaction. The polyester diol thus obtained had a number average molecular weight of 1000.
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に、2-ヒドロキシエチルアクリレート(Aldrich株式会社製)238質量部(2.05モル)、ハイドロキノンモノメチルエーテル(Aldrich株式会社製)0.53質量部、数平均分子量1000のポリテトラメチレンエーテルグリコール(商品名:保土谷化学工業株式会社製、TG1000)2500質量部(2.50モル)、ジブチルスズジラウレート(Aldrich株式会社製)5.53質量部を投入した。充分に窒素ガスを導入した後、70~75℃に加熱し、イソホロンジイソシアネート(Aldrich株式会社製)666質量部(3.00モル)を3時間で均一に滴下し、反応させた。滴下完了後15時間反応させた。IR測定によりイソシアネートが消失したことを確認して反応を終了し、ウレタンアクリレートを得た。得られたウレタンアクリレート(UA7)の臨界表面張力は16mN/m、重量平均分子量が20400、粘度3500Pa・sであった。 (Synthesis of urethane acrylate (UA7))
In a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser equipped with a calcium chloride drying tube, and a nitrogen gas introduction tube, 238 parts by mass (2.05 mol) of 2-hydroxyethyl acrylate (manufactured by Aldrich), hydroquinone monomethyl Ether (manufactured by Aldrich) 0.53 parts by mass, polytetramethylene ether glycol having a number average molecular weight of 1000 (trade name: Hodogaya Chemical Co., Ltd., TG1000) 2500 parts by mass (2.50 mol), dibutyltin dilaurate ( (Aldrich Co., Ltd.) 5.53 parts by mass were charged. After sufficiently introducing nitrogen gas, the mixture was heated to 70 to 75 ° C., and 666 parts by mass (3.00 mol) of isophorone diisocyanate (manufactured by Aldrich Co., Ltd.) was uniformly added dropwise over 3 hours to be reacted. It was made to react for 15 hours after completion of dripping. The reaction was terminated after confirming that the isocyanate had disappeared by IR measurement, and urethane acrylate was obtained. The obtained urethane acrylate (UA7) had a critical surface tension of 16 mN / m, a weight average molecular weight of 20400, and a viscosity of 3500 Pa · s.
イソシアヌル酸変性2官能アクリレート(東亞合成株式会社製、M-215(商品名)を準備した。 (Preparation of isocyanuric acid-modified bifunctional acrylate (M-215))
Isocyanuric acid-modified bifunctional acrylate (manufactured by Toagosei Co., Ltd., M-215 (trade name)) was prepared.
2-(メタ)アクリロイロキシエチルホスフェート(商品名:ライトエステルP-2M、共栄社化学株式会社製)を準備した。 (Preparation of a vinyl compound having a phosphate group (P-2M))
2- (Meth) acryloyloxyethyl phosphate (trade name: Light Ester P-2M, manufactured by Kyoeisha Chemical Co., Ltd.) was prepared.
ラジカル重合開始剤としてジベンゾイルパーオキサイド(商品名:ナイパーBW、日油株式会社製)を準備した。 <Radical polymerization initiator>
Dibenzoyl peroxide (trade name: Nyper BW, manufactured by NOF Corporation) was prepared as a radical polymerization initiator.
(導電性粒子の作製)
ポリスチレンを核とする粒子の表面に、厚み0.2μmのニッケル層を設け、このニッケル層の外側に、厚み0.02μmの金層を設け、平均粒径10μm、比重2.5の導電性粒子を作製した。 <Conductive particles>
(Preparation of conductive particles)
A nickel layer having a thickness of 0.2 μm is provided on the surface of particles having polystyrene as a core, and a gold layer having a thickness of 0.02 μm is provided outside the nickel layer, and conductive particles having an average particle diameter of 10 μm and a specific gravity of 2.5. Was made.
固形質量比で表2に示すように熱可塑性樹脂、ラジカル重合性化合物及びラジカル重合開始剤を配合し、さらに導電性粒子を1.5体積%配合分散させ、接着剤組成物を得た。得られた接着剤組成物を、塗工装置を用いて厚み80μmのフッ素樹脂フィルム上に塗布し、70℃、10分の熱風乾燥によって接着剤層の厚みが20μmのフィルム状接着剤組成物を得た。 [Examples 1 to 12 and Comparative Examples 1 to 5]
As shown in Table 2 in terms of solid mass ratio, a thermoplastic resin, a radical polymerizable compound, and a radical polymerization initiator were blended, and 1.5% by volume of conductive particles were blended and dispersed to obtain an adhesive composition. The obtained adhesive composition was applied on a fluororesin film having a thickness of 80 μm using a coating apparatus, and a film-like adhesive composition having an adhesive layer thickness of 20 μm was dried by hot air at 70 ° C. for 10 minutes. Obtained.
実施例1~12及び比較例1~5のフィルム状接着剤組成物を、ポリイミドフィルム上にライン幅25μm、ピッチ50μm、厚み8μmの銅回路を500本有するフレキシブル回路板(FPC)と、0.2μmのITOの薄層を形成したガラス(厚み1.1mm、表面抵抗20Ω/□)との間に介在させた。これを、熱圧着装置(加熱方式:コンスタントヒート型、東レエンジニアリング社製)を用いて、160℃、3MPaで10秒間加熱加圧して幅2mmにわたり接続し、接続体を作製した。この接続体の隣接回路間の抵抗値を、接着直後と、85℃、85%RHの高温高湿槽中に240時間保持した後(試験後)にマルチメータで測定した。抵抗値は隣接回路間の抵抗37点の平均で示した。 (Measurement of elongation at break, storage elastic modulus, connection resistance, adhesive strength)
A flexible circuit board (FPC) having 500 copper circuits having a line width of 25 μm, a pitch of 50 μm, and a thickness of 8 μm on the polyimide film, the film-like adhesive compositions of Examples 1 to 12 and Comparative Examples 1 to 5; It was interposed between the glass (thickness 1.1 mm, surface resistance 20Ω / □) on which a thin layer of 2 μm ITO was formed. Using a thermocompression bonding apparatus (heating method: constant heat type, manufactured by Toray Engineering Co., Ltd.), this was heated and pressurized at 160 ° C. and 3 MPa for 10 seconds to be connected over a width of 2 mm to produce a connected body. The resistance value between adjacent circuits of this connection body was measured with a multimeter immediately after bonding and after being held in a high-temperature and high-humidity bath 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.
Claims (22)
- 主面上に第一の接続端子を有する第一の回路部材と、主面上に第二の接続端子を有する第二の回路部材とを接続するための接着剤組成物であって、
前記接着剤組成物は、(a)熱可塑性樹脂、(b)ラジカル重合性化合物、(c)ラジカル重合開始剤、及び、(d)リン酸基を有するビニル化合物を含有し、
前記(b)ラジカル重合性化合物が20~40mN/mの臨界表面張力を有するウレタン(メタ)アクリレートを含む、接着剤組成物。 An adhesive composition for connecting a first circuit member having a first connection terminal on the main surface and a second circuit member having a second connection terminal on the main surface,
The adhesive composition contains (a) a thermoplastic resin, (b) a radical polymerizable compound, (c) a radical polymerization initiator, and (d) a vinyl compound having a phosphate group,
The adhesive composition comprising (b) a urethane (meth) acrylate having a radical surface tension of 20 to 40 mN / m. - 前記ウレタン(メタ)アクリレートの25℃での粘度が600~5000Pa・sである、請求項1記載の接着剤組成物。 The adhesive composition according to claim 1, wherein the viscosity of the urethane (meth) acrylate at 25 ° C is 600 to 5000 Pa · s.
- 前記ウレタン(メタ)アクリレートの重量平均分子量が10000以上25000未満である、請求項1又は2記載の接着剤組成物。 The adhesive composition according to claim 1 or 2, wherein the urethane (meth) acrylate has a weight average molecular weight of 10,000 or more and less than 25,000.
- 破断伸びが300~500%である、請求項1~3のいずれか一項に記載の接着剤組成物。 The adhesive composition according to any one of claims 1 to 3, wherein the elongation at break is 300 to 500%.
- 主面上に第一の接続端子を有する第一の回路部材と、主面上に第二の接続端子を有する第二の回路部材とを接続するための接着剤組成物であって、
前記接着剤組成物は、(a)熱可塑性樹脂、(b)ラジカル重合性化合物、及び、(c)ラジカル重合開始剤を含有し、
前記(b)ラジカル重合性化合物がウレタン(メタ)アクリレートを含み、
破断伸びが300~500%である、接着剤組成物。 An adhesive composition for connecting a first circuit member having a first connection terminal on the main surface and a second circuit member having a second connection terminal on the main surface,
The adhesive composition contains (a) a thermoplastic resin, (b) a radical polymerizable compound, and (c) a radical polymerization initiator,
The (b) radical polymerizable compound contains urethane (meth) acrylate,
An adhesive composition having an elongation at break of 300 to 500%. - (d)リン酸基を有するビニル化合物をさらに含有する、請求項5記載の接着剤組成物。 (D) The adhesive composition according to claim 5, further comprising a vinyl compound having a phosphate group.
- 200℃における貯蔵弾性率が0.5~5MPaである、請求項1~6のいずれか一項に記載の接着剤組成物。 The adhesive composition according to any one of claims 1 to 6, wherein the storage elastic modulus at 200 ° C is 0.5 to 5 MPa.
- 前記(a)熱可塑性樹脂が、フェノキシ樹脂、ポリウレタン樹脂、ポリエステルウレタン樹脂、ブチラール樹脂、アクリル樹脂、及び、ポリイミド樹脂からなる群より選ばれる少なくとも1種を含有する、請求項1~7のいずれか一項に記載の接着剤組成物。 The thermoplastic resin (a) contains at least one selected from the group consisting of a phenoxy resin, a polyurethane resin, a polyester urethane resin, a butyral resin, an acrylic resin, and a polyimide resin. The adhesive composition according to one item.
- (e)導電性粒子をさらに含有する、請求項1~8のいずれか一項に記載の接着剤組成物。 (E) The adhesive composition according to any one of claims 1 to 8, further comprising conductive particles.
- 主面上に第一の接続端子を有する第一の回路部材と、主面上に第二の接続端子を有する第二の回路部材と、接続部材と、を備える回路部材の接続構造体であって、
前記第一の接続端子及び前記第二の接続端子が対向するように、前記第一の回路部材及び前記第二の回路部材が請求項1~9のいずれか一項に記載の接着剤組成物からなる前記接続部材を介して配置されるとともに、前記第一の接続端子及び前記第二の接続端子が電気的に接続されており、
前記第一の回路部材及び/又は前記第二の回路部材が、ガラス転移温度が200℃以下の熱可塑性樹脂を含む基材から構成されている、回路部材の接続構造体。 A circuit member connection structure comprising: a first circuit member having a first connection terminal on a main surface; a second circuit member having a second connection terminal on a main surface; and a connection member. And
The adhesive composition according to any one of claims 1 to 9, wherein the first circuit member and the second circuit member are arranged so that the first connection terminal and the second connection terminal face each other. And the first connection terminal and the second connection terminal are electrically connected with each other through the connection member.
The connection structure of a circuit member, wherein the first circuit member and / or the second circuit member is composed of a base material containing a thermoplastic resin having a glass transition temperature of 200 ° C. or lower. - 前記ガラス転移温度が200℃以下の熱可塑性樹脂は、ポリエチレンテレフタレート、ポリカーボネート及びポリエチレンナフタレートからなる群より選ばれる少なくとも1種である、請求項10記載の回路部材の接続構造体。 The circuit member connection structure according to claim 10, wherein the thermoplastic resin having a glass transition temperature of 200 ° C or lower is at least one selected from the group consisting of polyethylene terephthalate, polycarbonate, and polyethylene naphthalate.
- 前記第一の回路部材又は前記第二の回路部材のうち一方の回路部材が、ポリエチレンテレフタレート、ポリカーボネート及びポリエチレンナフタレートからなる群より選ばれる少なくとも1種を含有する基材から構成され、
前記第一の回路部材又は第二の回路部材のうちもう一方の回路部材が、ポリイミド樹脂である、請求項10又は11記載の回路部材の接続構造体。 One of the first circuit member or the second circuit member is composed of a base material containing at least one selected from the group consisting of polyethylene terephthalate, polycarbonate and polyethylene naphthalate,
The circuit member connection structure according to claim 10 or 11, wherein the other circuit member of the first circuit member or the second circuit member is a polyimide resin. - 主面上に第一の接続端子を有する第一の回路部材と、主面上に第二の接続端子を有する第二の回路部材とを、請求項1~9のいずれか一項に記載の接着剤組成物を介して前記第一の接続端子及び前記第二の接続端子が対向するように、配置する工程と、
前記接着剤組成物を加熱し、硬化させて、前記第一の回路部材と前記第二の回路部材とを接続する工程と、
を備える、回路部材の接続構造体の製造方法。 The first circuit member having a first connection terminal on the main surface and the second circuit member having a second connection terminal on the main surface are described in any one of claims 1 to 9. A step of arranging the first connection terminal and the second connection terminal to face each other through an adhesive composition;
Heating and curing the adhesive composition to connect the first circuit member and the second circuit member;
The manufacturing method of the connection structure of a circuit member provided with this. - (a)熱可塑性樹脂、(b)ラジカル重合性化合物、(c)ラジカル重合開始剤、及び、(d)リン酸基を有するビニル化合物を含有し、前記(b)ラジカル重合性化合物が20~40mN/mの臨界表面張力を有するウレタン(メタ)アクリレートを含む、接着剤組成物の、
主面上に第一の接続端子を有する第一の回路部材と、主面上に第二の接続端子を有する第二の回路部材とを接続するための接着剤組成物の応用。 (A) a thermoplastic resin, (b) a radically polymerizable compound, (c) a radical polymerization initiator, and (d) a vinyl compound having a phosphoric acid group. An adhesive composition comprising a urethane (meth) acrylate having a critical surface tension of 40 mN / m,
Application of an adhesive composition for connecting a first circuit member having a first connection terminal on the main surface and a second circuit member having a second connection terminal on the main surface. - 前記ウレタン(メタ)アクリレートの25℃での粘度が600~5000Pa・sである、請求項14記載の応用。 The application according to claim 14, wherein the urethane (meth) acrylate has a viscosity at 25 ° C of 600 to 5000 Pa · s.
- 前記ウレタン(メタ)アクリレートの重量平均分子量が10000以上25000未満である、請求項14又は15記載の応用。 The application according to claim 14 or 15, wherein the urethane (meth) acrylate has a weight average molecular weight of 10,000 or more and less than 25,000.
- 前記接着剤組成物の破断伸びが300~500%である、請求項14~16のいずれか一項に記載の応用。 The application according to any one of claims 14 to 16, wherein the elongation at break of the adhesive composition is 300 to 500%.
- (a)熱可塑性樹脂、(b)ラジカル重合性化合物、及び、(c)ラジカル重合開始剤を含有し、
前記(b)ラジカル重合性化合物がウレタン(メタ)アクリレートを含み、
破断伸びが300~500%である、接着剤組成物の、
主面上に第一の接続端子を有する第一の回路部材と、主面上に第二の接続端子を有する第二の回路部材とを接続するための接着剤組成物の応用。 (A) a thermoplastic resin, (b) a radical polymerizable compound, and (c) a radical polymerization initiator,
The (b) radical polymerizable compound contains urethane (meth) acrylate,
The adhesive composition having an elongation at break of 300 to 500%,
Application of an adhesive composition for connecting a first circuit member having a first connection terminal on the main surface and a second circuit member having a second connection terminal on the main surface. - 前記接着剤組成物が(d)リン酸基を有するビニル化合物をさらに含有する、請求項18記載の応用。 The application according to claim 18, wherein the adhesive composition further contains (d) a vinyl compound having a phosphate group.
- 前記接着剤組成物の200℃における貯蔵弾性率が0.5~5MPaである、請求項14~19のいずれか一項に記載の応用。 The application according to any one of claims 14 to 19, wherein the storage elastic modulus of the adhesive composition at 200 ° C is 0.5 to 5 MPa.
- 前記(a)熱可塑性樹脂が、フェノキシ樹脂、ポリウレタン樹脂、ポリエステルウレタン樹脂、ブチラール樹脂、アクリル樹脂、及び、ポリイミド樹脂からなる群より選ばれる少なくとも1種を含有する、請求項14~20のいずれか一項に記載の応用。 The thermoplastic resin (a) contains at least one selected from the group consisting of a phenoxy resin, a polyurethane resin, a polyester urethane resin, a butyral resin, an acrylic resin, and a polyimide resin. Application according to one paragraph.
- 前記接着剤組成物が(e)導電性粒子をさらに含有する、請求項14~21のいずれか一項に記載の応用。 The application according to any one of claims 14 to 21, wherein the adhesive composition further contains (e) conductive particles.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020137006456A KR101385422B1 (en) | 2010-07-26 | 2011-05-30 | Adhesive composition, connection structure, and method for producing connection structure |
JP2011525059A JP5454578B2 (en) | 2010-07-26 | 2011-05-30 | Adhesive composition, connection structure, method for producing connection structure, and application of adhesive composition |
KR1020137030959A KR20130143673A (en) | 2010-07-26 | 2011-05-30 | Adhesive composition, connection structure, and method for producing connection structure |
CN201180001017.3A CN102449095B (en) | 2010-07-26 | 2011-05-30 | The application of adhesive composite, connection structural bodies, the manufacture method of connection structural bodies and adhesive composite |
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JP2010-167264 | 2010-07-26 | ||
JP2010167264 | 2010-07-26 | ||
JP2010188574 | 2010-08-25 | ||
JP2010-188574 | 2010-08-25 |
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PCT/JP2011/062418 WO2012014563A1 (en) | 2010-07-26 | 2011-05-30 | Adhesive composition, connection structure, connection structure manufacturing method and application of adhesive composition |
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JP (1) | JP5454578B2 (en) |
KR (3) | KR101385422B1 (en) |
CN (3) | CN105860910A (en) |
TW (1) | TWI445789B (en) |
WO (1) | WO2012014563A1 (en) |
Cited By (2)
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WO2014156882A1 (en) * | 2013-03-26 | 2014-10-02 | 日東電工株式会社 | Underfill material, sealing sheet, and method for producing semiconductor device |
JP2015503220A (en) * | 2011-11-02 | 2015-01-29 | ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング | Adhesive for electronic parts |
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KR101535600B1 (en) * | 2012-11-06 | 2015-07-09 | 제일모직주식회사 | Anisotropic conductive film and semiconductor device |
JP6123547B2 (en) * | 2013-07-26 | 2017-05-10 | 日立化成株式会社 | Circuit connection material, circuit connection structure, method for manufacturing circuit connection structure, adhesive composition, and adhesive sheet |
CN103525355B (en) * | 2013-10-16 | 2015-02-18 | 烟台德邦科技有限公司 | Ultraviolet curing adhesive for liquid crystal display television side frame and preparation method of ultraviolet curing adhesive |
JP6374192B2 (en) * | 2014-03-25 | 2018-08-15 | デクセリアルズ株式会社 | Anisotropic conductive film, connection method, and joined body |
TWI754073B (en) * | 2017-06-26 | 2022-02-01 | 日商東亞合成股份有限公司 | Adhesive composition and heat-adhesive member using the same |
JP7140289B2 (en) * | 2019-08-30 | 2022-09-21 | Dic株式会社 | Adhesive tape |
KR102515779B1 (en) * | 2021-05-27 | 2023-03-31 | 유한회사 대구특수금속 | Mehtod for manufacturing in-mold electrronics having terminal connector with stiffness and airtightness |
KR102528889B1 (en) * | 2021-05-27 | 2023-05-04 | 유한회사 대구특수금속 | In-mold electrronics having terminal connector with stiffness and airtightness |
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- 2011-05-30 KR KR1020137006456A patent/KR101385422B1/en active IP Right Grant
- 2011-05-30 WO PCT/JP2011/062418 patent/WO2012014563A1/en active Application Filing
- 2011-05-30 KR KR1020117018210A patent/KR20120068751A/en not_active Application Discontinuation
- 2011-05-30 CN CN201610239583.2A patent/CN105860910A/en active Pending
- 2011-05-30 JP JP2011525059A patent/JP5454578B2/en not_active Expired - Fee Related
- 2011-05-30 CN CN201180001017.3A patent/CN102449095B/en not_active Expired - Fee Related
- 2011-05-30 KR KR1020137030959A patent/KR20130143673A/en not_active Application Discontinuation
- 2011-05-30 CN CN2013102289914A patent/CN103351838A/en active Pending
- 2011-05-31 TW TW100119004A patent/TWI445789B/en active
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Also Published As
Publication number | Publication date |
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TW201204797A (en) | 2012-02-01 |
TWI445789B (en) | 2014-07-21 |
KR20130042018A (en) | 2013-04-25 |
CN102449095B (en) | 2016-06-01 |
KR101385422B1 (en) | 2014-04-14 |
CN102449095A (en) | 2012-05-09 |
CN103351838A (en) | 2013-10-16 |
KR20130143673A (en) | 2013-12-31 |
CN105860910A (en) | 2016-08-17 |
JP5454578B2 (en) | 2014-03-26 |
KR20120068751A (en) | 2012-06-27 |
JPWO2012014563A1 (en) | 2013-09-12 |
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