WO2017090659A1 - 回路接続用接着剤組成物及び構造体 - Google Patents

回路接続用接着剤組成物及び構造体 Download PDF

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Publication number
WO2017090659A1
WO2017090659A1 PCT/JP2016/084747 JP2016084747W WO2017090659A1 WO 2017090659 A1 WO2017090659 A1 WO 2017090659A1 JP 2016084747 W JP2016084747 W JP 2016084747W WO 2017090659 A1 WO2017090659 A1 WO 2017090659A1
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WIPO (PCT)
Prior art keywords
circuit
mass
adhesive composition
parts
circuit connection
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PCT/JP2016/084747
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English (en)
French (fr)
Japanese (ja)
Inventor
智樹 森尻
松田　和也
田中　勝
立澤　貴
研吾 篠原
泰典 川端
Original Assignee
日立化成株式会社
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Application filed by 日立化成株式会社 filed Critical 日立化成株式会社
Priority to JP2017552682A priority Critical patent/JP6870618B2/ja
Priority to CN201680068535.XA priority patent/CN108291114A/zh
Priority to KR1020187017184A priority patent/KR102615097B1/ko
Priority to CN202410394464.9A priority patent/CN118291047A/zh
Publication of WO2017090659A1 publication Critical patent/WO2017090659A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C09J9/02—Electrically-conducting adhesives
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/20—Conductive material dispersed in non-conductive organic material
    • H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/14—Structural association of two or more printed circuits
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
    • H05K3/32—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits

Definitions

  • the present invention relates to an adhesive composition for circuit connection and a structure using the same.
  • circuit connection materials include connection between liquid crystal display and TCP, connection between FPC and TCP, connection between FPC and printed wiring board, connection between semiconductor silicon chip and substrate, connection between FPC and touch panel module, FPC An anisotropic conductive adhesive containing conductive particles is used for connection between the FPC and the FPC.
  • thermosetting resins epoxy resin, acrylic resin, etc.
  • a latent curing agent that generates an epoxy resin and a cationic species or anionic species having reactivity with the epoxy resin by heat or light
  • the latent curing agent is an important factor for determining the curing temperature and the curing rate, and various compounds have been used from the viewpoint of storage stability at normal temperature and curing rate during heating. In the actual process, for example, desired adhesiveness was obtained by curing under a curing condition of a temperature of 170 to 250 ° C. for 10 seconds to 3 hours.
  • a radical curing adhesive for example, a radical curing adhesive using a (meth) acrylate derivative and a peroxide as a radical polymerization initiator
  • the radical curing system is capable of curing for a short time because radicals that are reactive species are very reactive, and the adhesive is stable below the decomposition temperature of the radical polymerization initiator. It is a curing system that achieves both short-time curing and storage stability (for example, storage stability near normal temperature).
  • radical curing systems do not use ionic polymerization such as epoxy curing systems such as cation-epoxy curing systems and anion-epoxy curing systems. It is characterized by excellent corrosion resistance when performed.
  • the corrosion may be suppressed by adding a metal hydroxide, a metal oxide or the like (for example, see Patent Documents 1 to 4 below). ).
  • An object of the present invention is to provide an adhesive composition for circuit connection capable of obtaining a structure having excellent salt water resistance, and a structure using the same.
  • the present invention contains (A) a radical polymerizable compound, (B) a radical generator, and (C) particles containing at least one metal compound selected from the group consisting of metal hydroxides and metal oxides.
  • the present invention relates to an adhesive composition for circuit connection, wherein the metal compound contains at least one selected from the group consisting of aluminum, magnesium, zirconium, bismuth, calcium, tin, manganese, antimony, silicon and titanium.
  • the adhesive composition for circuit connection it is possible to obtain a structure having excellent salt water resistance (excellent connection reliability even when exposed to salt water (sweat, seawater, etc.)). it can. Therefore, excellent reliability can be obtained even in severe environments such as wearable applications.
  • a low temperature short time connection can also be achieved. Therefore, it is possible to use an adherend made of a material having low heat resistance such as polyethylene terephthalate (PET) or polycarbonate (PC), so that the options for the adherend can be expanded.
  • PET polyethylene terephthalate
  • PC polycarbonate
  • the radical curing type adhesive composition for circuit connection is low in polarity and the adhesiveness at the interface between the adherend (substrate etc.) and the adhesive composition is low, the ionic component in the salt water is easily present at the interface. It is thought that invasion and adhesion inhibition occur.
  • a polymer of a radical polymerizable compound has a carbon-carbon bond (C—C) as a main skeleton
  • the polarity tends to be low.
  • the adherend has an insulating material portion containing an insulating material such as SiO 2 or SiN x
  • the insulating material portion has a large number of hydroxyl groups on the surface and is easily wetted with water (such as salt water).
  • water such as salt water
  • the present inventors have found that in a radical-curing adhesive composition for circuit connection, by using particles containing a metal hydroxide or metal oxide containing a specific metal element, It has been found that the salt water resistance of can be significantly improved. This is because the metal hydroxide or metal oxide increases the polarity of the adhesive composition itself, and the metal hydroxide or metal oxide captures ionic components that cause adhesion inhibition, thereby suppressing adhesion inhibition. This is considered to be a factor.
  • the component (C) may contain the metal hydroxide.
  • the average primary particle size of the component (C) is preferably 10 ⁇ m or less.
  • the adhesive composition for circuit connection according to the present invention may further contain a silane coupling agent.
  • the adhesive composition for circuit connection according to the present invention may further contain conductive particles.
  • the structure of the present invention includes the adhesive composition or a cured product thereof.
  • the structure of the present invention includes a first circuit member having a first circuit electrode, a second circuit member having a second circuit electrode, and between the first circuit member and the second circuit member. And the first circuit electrode and the second circuit electrode are electrically connected, and the circuit connection member includes the adhesive composition or a cured product thereof. An aspect may be sufficient.
  • an adhesive composition for circuit connection capable of obtaining a structure having excellent salt water resistance, and a structure using the same.
  • an application of an adhesive composition or a cured product thereof to a structure (circuit connection structure or the like) or production thereof can be provided.
  • ADVANTAGE OF THE INVENTION According to this invention, the application of the adhesive composition or its hardened
  • ADVANTAGE OF THE INVENTION According to this invention, the application of the structure to a wearable use can be provided.
  • (meth) acrylate means at least one of acrylate and methacrylate corresponding thereto.
  • the materials exemplified below may be used alone or in combination of two or more unless otherwise specified.
  • the content of each component in the composition means the total amount of the plurality of substances present in the composition unless there is a specific notice when there are a plurality of substances corresponding to each component in the composition.
  • the numerical range indicated by using “to” indicates a range including the numerical values described before and after “to” as the minimum value and the maximum value, respectively. “A or B” only needs to include either A or B, and may include both.
  • Normal temperature means 25 ° C.
  • the upper limit value or lower limit value of a numerical range of a certain step may be replaced with the upper limit value or lower limit value of the numerical range of another step. Further, in the numerical ranges described in this specification, the upper limit value or the lower limit value of the numerical range may be replaced with the values shown in the examples.
  • the adhesive composition of the present embodiment comprises (A) a radical polymerizable compound (radical polymerizable substance, radical reactive component), (B) a radical generator, and (C) a metal hydroxide and a metal oxide.
  • An adhesive composition for circuit connection comprising particles containing at least one metal compound selected from the group consisting of: Hereinafter, each component will be described.
  • the radical polymerizable compound is a compound having a radical polymerizable functional group.
  • examples of such radically polymerizable compounds include (meth) acrylate compounds, maleimide compounds, citraconimide compounds, nadiimide compounds, and the like.
  • “(Meth) acrylate compound” means a compound having a (meth) acryloyl group.
  • a radically polymerizable compound may be used in the state of a monomer or an oligomer, and can also use a monomer and an oligomer together.
  • a radically polymerizable compound may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the (meth) acrylate compound examples include methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, isobutyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, Trimethylolpropane tri (meth) acrylate, tetramethylolmethanetetra (meth) acrylate, 2-hydroxy-1,3-di (meth) acryloxypropane, 2,2-bis [4-((meth) acryloxymethoxy) Phenyl] propane, 2,2-bis [4-((meth) acryloxypolyethoxy) phenyl] propane, dicyclopentenyl (meth) acrylate, tricyclodecanyl (meth) acrylate, tris ((meth) acryloyloxy Chill) isocyanurate, isocyanuric acid EO
  • radically polymerizable compounds other than (meth) acrylate compounds for example, compounds described in Patent Document 5 (International Publication No. 2009/063827) can be preferably used.
  • a (meth) acrylate compound may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the radical polymerizable compound a (meth) acrylate compound is preferable and urethane (meth) acrylate is more preferable from the viewpoint of obtaining further excellent salt water resistance.
  • the (meth) acrylate compound preferably has at least one substituent selected from the group consisting of a dicyclopentenyl group, a tricyclodecanyl group, and a triazine ring.
  • radical polymerizable compound a radical polymerizable compound having a phosphate structure represented by the following general formula (I) is preferably used, and the radical polymerizable compound such as a (meth) acrylate compound and the formula ( It is more preferable to use together with a radically polymerizable compound having a phosphate ester structure represented by I).
  • the adhesive strength with respect to the surface of an inorganic substance (metal etc.) improves, it is suitable for adhesion
  • n represents an integer of 1 to 3, and R represents a hydrogen atom or a methyl group.
  • the radical polymerizable compound having a phosphoric ester structure can be obtained by reacting, for example, phosphoric anhydride with 2-hydroxyethyl (meth) acrylate.
  • Specific examples of the radical polymerizable compound having a phosphoric ester structure include mono (2- (meth) acryloyloxyethyl) acid phosphate, di (2- (meth) acryloyloxyethyl) acid phosphate, and the like.
  • the radically polymerizable compound having a phosphate ester structure represented by the formula (I) may be used alone or in combination of two or more.
  • the content of the radical polymerizable compound having a phosphate ester structure represented by the formula (I) is a radical polymerizable compound (total amount of components corresponding to the radical polymerizable compound. From the viewpoint of obtaining further excellent salt water resistance. Similarly) 20 mass parts or less are preferable with respect to 100 mass parts, and 10 mass parts or less are more preferable.
  • the content of the radically polymerizable compound having a phosphate ester structure represented by the formula (I) is such that the radically polymerizable compound and the film-forming material (components used as necessary) are from the viewpoint of obtaining excellent salt water resistance. 20 mass parts or less are preferable with respect to a total of 100 mass parts, and 10 mass parts or less are more preferable.
  • the radical polymerizable compound may contain allyl (meth) acrylate.
  • the content of allyl (meth) acrylate is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass in total of the radical polymerizable compound and the film forming material (components used as necessary). 5 to 5 parts by mass is more preferable.
  • the content of the radical polymerizable compound is based on the total mass of the adhesive component of the adhesive composition (solid content other than the conductive particles in the adhesive composition; the same applies hereinafter) from the viewpoint of obtaining further excellent salt water resistance.
  • the following ranges are preferred.
  • the content of the radical polymerizable compound is preferably 10% by mass or more, more preferably 20% by mass or more, and further preferably 30% by mass or more.
  • the content of the radical polymerizable compound is preferably 90% by mass or less, more preferably 80% by mass or less, and further preferably 70% by mass or less. From these viewpoints, the content of the radical polymerizable compound is preferably 10 to 90% by mass, more preferably 20 to 80% by mass, and still more preferably 30 to 70% by mass.
  • the radical generator is a curing agent (radical polymerization initiator or the like) that generates free radicals by being decomposed by heat, light (UV, etc.), ultrasonic waves, electromagnetic waves, or the like.
  • the radical generator examples include peroxides (such as organic peroxides) and azo compounds.
  • the radical generator is appropriately selected depending on the intended connection temperature, connection time, pot life, and the like.
  • the 10 minute half-life temperature of the radical generator is preferably 40 ° C. or higher, more preferably 60 ° C. or higher, from the viewpoint of high reactivity and pot life improvement.
  • the 1 minute half-life temperature of the radical generator is preferably 180 ° C. or lower, more preferably 170 ° C. or lower, from the viewpoint of high reactivity and improvement of pot life.
  • the radical generator is preferably an organic peroxide having a 10-minute half-life temperature of 40 ° C. or higher and a 1-minute half-life temperature of 180 ° C. or lower from the viewpoint of high reactivity and pot life, and a 10-minute half-life.
  • An organic peroxide having a temperature of 60 ° C. or higher and a 1 minute half-life temperature of 170 ° C. or lower is more prefer
  • a curing agent having a concentration of contained chlorine ions and organic acids of 5000 ppm or less is preferable, and a curing agent that generates less organic acids after thermal decomposition. Is more preferable.
  • Specific examples of such curing agents include diacyl peroxides, peroxydicarbonates, peroxyesters, dialkyl peroxides, hydroperoxides, silyl peroxides, and the like from the viewpoint of obtaining high reactivity. At least one selected from the group consisting of peroxide, peroxydicarbonate and peroxyester is preferred. Curing agents that generate free radicals by heat may be used singly or in combination of two or more.
  • Peroxyesters include cumylperoxyneodecanoate, 1,1,3,3-tetramethylbutylperoxyneodecanoate, 1-cyclohexyl-1-methylethylperoxyneodecanoate, and t-hexyl.
  • Peroxyneodecanoate t-butylperoxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 2,5-dimethyl-2,5-di (2- Ethylhexanoylperoxy) hexane, 1-cyclohexyl-1-methylethylperoxy-2-ethylhexanoate, t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate Ate, t-butylperoxyisobutyrate, 1,1-bis (t-butylperoxy) cyclohexane t-hexylperoxyisopropyl monocarbonate, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxylaurate, 2,5-dimethyl-2,5-di (m-tolu
  • a peroxy ester may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the curing agent that generates free radicals by heat other than the peroxyester for example, the compounds described in Patent Document 5 (International Publication No. 2009/063827) can be suitably used.
  • azo compounds which are curing agents that generate free radicals by heat include 2,2′-azobisisobutyronitrile, 2,2′-azobis (2-methylbutyronitrile), 1,1′-azobis. (Cyclohexane-1-carbonitrile), 2,2′-azobis (2,4-dimethylvaleronitrile), 2,2′-azobis (2,4-dimethyl-4-methoxyvaleronitrile), dimethyl 2,2 ′ -Azobis (2-methylpropionate), 4,4'-azobis (4-cyanovaleric acid), 2,2'-azobis (2-hydroxymethylpropionitrile), 2,2'-azobis [2 -(Imidazolin-2-yl) propane] and the like.
  • a compound that generates radicals by light having a wavelength of 150 to 750 nm can be used.
  • Photoinitiation, Photopolymerization, and Photocuring, J.A. -P. ⁇ -Acetaminophenone derivatives and phosphine oxide derivatives described in Fouassier, Hanser Publishers (1995), p17 to p35 are preferred.
  • Curing agents that generate free radicals by light may be used singly or in combination of two or more.
  • the radical generator may be used alone or in combination of two or more.
  • a curing agent that generates free radicals by heat peroxide, azo compound, etc.
  • a curing agent that generates free radicals by light may be used in combination.
  • the radical generator may be microencapsulated by coating with a polyurethane-based or polyester-based polymer substance or the like. A microencapsulated curing agent is preferred because the pot life is extended.
  • the content of the radical generator is preferably in the following range from the viewpoint that a sufficient reaction rate can be easily obtained when the connection time is 25 seconds or less.
  • the content of the radical generator is preferably 0.1 parts by mass or more, more preferably 0.5 parts by mass or more with respect to 100 parts by mass of the radical polymerizable compound, and 1 part by mass or more. More preferably.
  • the content of the radical generator is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and still more preferably 20 parts by mass or less with respect to 100 parts by mass of the radical polymerizable compound. . From these viewpoints, the content of the radical generator is preferably 0.1 to 40 parts by mass, more preferably 0.5 to 30 parts by mass with respect to 100 parts by mass of the radical polymerizable compound. More preferably, it is 1 to 30 parts by mass.
  • the content of the radical generator is preferably in the following range from the viewpoint that a sufficient reaction rate can be easily obtained when the connection time is 25 seconds or less.
  • the content of the radical generator is preferably 0.1 parts by mass or more with respect to 100 parts by mass in total of the radical polymerizable compound and the film forming material (components used as necessary), and 0.5 parts by mass. More preferably, it is more preferably 1 part by mass or more.
  • the content of the radical generator is preferably 40 parts by mass or less, and 30 parts by mass or less, with respect to 100 parts by mass in total of the radical polymerizable compound and the film forming material (components used as necessary). Is more preferable, and it is still more preferable that it is 20 mass parts or less.
  • the content of the radical generator is preferably 0.1 to 40 parts by mass with respect to 100 parts by mass in total of the radical polymerizable compound and the film forming material (components used as necessary). 0.5 to 30 parts by mass is more preferable, and 1 to 20 parts by mass is even more preferable.
  • the content of the radical generator in the case where the connection time is not limited is preferably in the following range from the viewpoint that a sufficient reaction rate can be easily obtained.
  • the content of the radical generator is preferably 0.1 parts by mass or more, more preferably 0.5 parts by mass or more with respect to 100 parts by mass of the radical polymerizable compound, and 1 part by mass or more. More preferably.
  • the content of the radical generator is preferably 30 parts by mass or less, more preferably 20 parts by mass or less, and further preferably 15 parts by mass or less with respect to 100 parts by mass of the radical polymerizable compound. . From these viewpoints, the content of the radical generator is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the radical polymerizable compound. More preferably, it is 1 to 15 parts by mass.
  • the content of the radical generator in the case where the connection time is not limited is preferably in the following range from the viewpoint that a sufficient reaction rate can be easily obtained.
  • the content of the radical generator is preferably 0.1 parts by mass or more with respect to 100 parts by mass in total of the radical polymerizable compound and the film forming material (components used as necessary), and 0.5 parts by mass. More preferably, it is more preferably 1 part by mass or more.
  • the content of the radical generator is preferably 30 parts by mass or less, and 20 parts by mass or less, with respect to 100 parts by mass in total of the radical polymerizable compound and the film-forming material (components used as necessary). Is more preferably 15 parts by mass or less.
  • the content of the radical generator is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass in total of the radical polymerizable compound and the film forming material (components used as necessary). 0.5 to 20 parts by mass is more preferable, and 1 to 15 parts by mass is even more preferable.
  • the adhesive composition of this embodiment contains particles (hereinafter sometimes referred to as “component (C)”) containing at least one metal compound selected from the group consisting of metal hydroxides and metal oxides.
  • the component (C) may contain a metal hydroxide or a metal oxide.
  • the metal compound includes at least one selected from the group consisting of aluminum, magnesium, zirconium, bismuth, calcium, tin, manganese, antimony, silicon, and titanium as a metal hydroxide or a metal element constituting the metal oxide.
  • the metal hydroxide is preferably at least one selected from the group consisting of aluminum hydroxide, magnesium hydroxide and calcium hydroxide from the viewpoint of obtaining further excellent salt water resistance.
  • the oxide is preferably at least one selected from the group consisting of silicon oxide, aluminum oxide, magnesium oxide, antimony oxide, tin oxide, titanium oxide, manganese oxide, and zirconium oxide, from the viewpoint of obtaining superior salt water resistance. . (C)
  • a component may be used individually by 1 type and may be used in combination of 2 or more type. You may use together the particle
  • the average primary particle size of the component (C) is the viewpoint of obtaining excellent dispersibility in the adhesive composition and high adhesion to the adherend, the viewpoint of preventing the adherend from being corroded, and the capture of the ionic component. From the viewpoint of obtaining performance, and from the viewpoint of suppressing short circuit due to large particles (short circuit when the component (C) becomes a foreign substance), it is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, and 1 ⁇ m or less. More preferably it is.
  • the effect of obtaining high adhesion to the adherend due to the increase in the specific surface area of the entire component (C) in the adhesive composition by reducing the average primary particle size of the component (C), corrosion of the adherend It is considered that the effect of preventing the ionic component and the effect of obtaining the ion component capturing ability can be obtained.
  • the average primary particle size of the component (C) may be 0.5 ⁇ m or more, or 1 ⁇ m or more.
  • the average primary particle size of the component (C) can be measured by, for example, a scanning electron microscope.
  • the content of the component (C) is preferably in the following range based on the total mass of the adhesive component of the adhesive composition.
  • the content of the component (C) is preferably 0.1% by mass or more, more preferably 1% by mass or more, and more preferably 2% by mass or more from the viewpoint of obtaining further excellent saltwater resistance. More preferably, it is 3% by mass or more, particularly preferably 4% by mass or more.
  • the content of the component (C) is preferably 50% by mass or less, and preferably 10% by mass or less from the viewpoint that short circuiting caused by aggregated particles is easily suppressed by obtaining excellent dispersibility. More preferred is 5% by mass or less.
  • the content of the component (C) is preferably 0.1 to 50% by mass, more preferably 1 to 50% by mass, and still more preferably 2 to 10% by mass. It is particularly preferably 3 to 10% by mass, and very preferably 4 to 5% by mass.
  • the content of the component (C) is preferably in the following range with respect to 100 parts by mass of the radical polymerizable compound.
  • the content of the component (C) is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and more preferably 2 parts by mass or more from the viewpoint of obtaining further excellent salt water resistance. More preferably, it is 3 parts by mass or more, particularly preferably 4 parts by mass or more, very preferably 5 parts by mass or more, and even more preferably 7 parts by mass or more.
  • the content of the component (C) is preferably 200 parts by mass or less and preferably 100 parts by mass or less from the viewpoint of easily suppressing short circuit due to the aggregated particles by obtaining excellent dispersibility.
  • component (C) is preferably 0.1 to 200 parts by mass, more preferably 1 to 200 parts by mass, and even more preferably 2 to 100 parts by mass. It is particularly preferably 3 to 50 parts by weight, very preferably 4 to 30 parts by weight, very preferably 5 to 20 parts by weight, and even more preferably 7 to 10 parts by weight. .
  • the adhesive composition of this embodiment may contain a silane coupling agent.
  • a silane coupling agent By using a silane coupling agent, the adhesive force of the adhesive composition (adhesive force to glass, etc.) can be increased.
  • the silane coupling agent include vinyltrimethoxysilane, vinyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3- (meth) acryloxypropylmethyldimethoxy.
  • Silane 3- (meth) acryloxypropyltrimethoxysilane, 3- (meth) acryloxypropylmethyldiethoxysilane, 3- (meth) acryloxypropyltriethoxysilane, N-2- (aminoethyl) -3- Aminopropylmethyldimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, and condensates thereof And the like.
  • the content of the silane coupling agent is preferably 0.1 to 10% by mass, more preferably 0.25 to 5% by mass, based on the total mass of the adhesive component of the adhesive composition. If content of a silane coupling agent is 0.1 mass% or more, there exists a tendency for the effect which suppresses generation
  • the adhesive composition of the present embodiment may contain a film forming material as necessary.
  • Film-forming material improves the handling of the film under normal conditions (normal temperature and normal pressure) when the liquid adhesive composition is solidified into a film, and is difficult to tear, hard to break, and sticky Can be imparted to the film.
  • the film forming material include phenoxy resin, polyvinyl formal, polystyrene, polyvinyl butyral, polyester, polyamide, xylene resin, and polyurethane.
  • a phenoxy resin is preferable from the viewpoint of excellent adhesiveness, compatibility, heat resistance, and mechanical strength.
  • a film forming material may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the phenoxy resin examples include a resin obtained by polyaddition of a bifunctional epoxy resin and a bifunctional phenol, and a resin obtained by reacting the bifunctional phenol and epihalohydrin until they are polymerized.
  • the phenoxy resin contains 1 mol of a bifunctional phenol and 0.985 to 1.015 mol of epihalohydrin in the presence of a catalyst such as an alkali metal hydroxide at a temperature of 40 to 120 ° C. in a non-reactive solvent. It can be obtained by reacting.
  • An organic solvent amide type, ether type, ketone type, lactone type, alcohol type
  • a catalyst such as an alkali metal compound, an organic phosphorus type compound, a cyclic amine type compound, etc. Etc.
  • a phenoxy resin may be used individually by 1 type, and may be used in combination of 2 or more type.
  • bifunctional epoxy resin examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AD type epoxy resin, bisphenol S type epoxy resin, biphenyl diglycidyl ether, methyl substituted biphenyl diglycidyl ether, and the like.
  • Bifunctional phenols are compounds having two phenolic hydroxyl groups. Examples of the bifunctional phenols include hydroquinones, bisphenol A, bisphenol F, bisphenol AD, bisphenol S, bisphenol fluorene, methyl substituted bisphenol fluorene, dihydroxy biphenyl, and methyl substituted dihydroxy biphenyl.
  • the phenoxy resin may be modified (for example, epoxy-modified) with a radical polymerizable functional group or other reactive compound.
  • the content of the film-forming material is preferably 10 to 90% by mass, more preferably 20 to 60% by mass, based on the total mass of the adhesive component of the adhesive composition.
  • the adhesive composition of this embodiment may further contain conductive particles.
  • conductive particles examples include gold (Au), silver (Ag), nickel (Ni), copper (Cu), metals such as solder, carbon, and the like.
  • coated conductive particles in which a nonconductive resin, glass, ceramic, plastic, or the like is used as a core and the metal (metal particles or the like) or carbon is coated on the core may be used. Covered conductive particles (for example, conductive particles with plastic as the core) or hot-melt metal particles are deformable by heating and pressurization, so the circuit electrode height variation is eliminated during connection, and the contact area with the electrode during connection Since the reliability increases, it is preferable.
  • the average particle diameter of the conductive particles is preferably 1 to 30 ⁇ m from the viewpoint of excellent dispersibility and conductivity.
  • the average particle diameter of the conductive particles can be measured using instrumental analysis such as laser diffraction.
  • the content of the conductive particles is preferably 0.1 parts by mass or more and more preferably 1 part by mass or more with respect to 100 parts by mass of the adhesive component of the adhesive composition from the viewpoint of excellent conductivity.
  • the content of the conductive particles is preferably 100 parts by mass or less, more preferably 50 parts by mass or less, with respect to 100 parts by mass of the adhesive component of the adhesive composition, from the viewpoint of easily suppressing the short circuit of the electrode (circuit electrode or the like). preferable. From these viewpoints, the content of the conductive particles is preferably 0.1 to 100 parts by mass, and more preferably 1 to 50 parts by mass.
  • the adhesive composition of this embodiment may contain a polymerization inhibitor such as hydroquinone and methyl ether hydroquinone as needed.
  • the adhesive composition of this embodiment is a homopolymer or copolymer obtained by polymerizing at least one monomer component selected from the group consisting of (meth) acrylic acid, (meth) acrylic acid ester and acrylonitrile. Furthermore, you may contain.
  • the adhesive composition of the present embodiment preferably contains acrylic rubber or the like, which is a copolymer obtained by polymerizing glycidyl (meth) acrylate having a glycidyl ether group, from the viewpoint of excellent stress relaxation.
  • the weight average molecular weight of the acrylic rubber is preferably 200,000 or more from the viewpoint of increasing the cohesive force of the adhesive composition.
  • the adhesive composition of the present embodiment may contain coated fine particles obtained by coating the surfaces of the conductive particles with a polymer resin or the like.
  • coated fine particles obtained by coating the surfaces of the conductive particles with a polymer resin or the like.
  • the coated fine particles may be used alone without using conductive particles, or the coated fine particles and conductive particles may be used in combination.
  • the adhesive composition of the present embodiment comprises rubber fine particles, a filler (excluding the component (C)), a softener, an accelerator, an anti-aging agent, a colorant, a flame retardant, a thixotropic agent, a coupling agent, A phenol resin, a melamine resin, isocyanates, etc. can also be contained.
  • the adhesive composition of the present embodiment may appropriately contain additives such as an adhesion improver (excluding a coupling agent), a thickener, a leveling agent, a colorant, and a weather resistance improver.
  • the rubber fine particles have an average particle size not more than twice the average particle size of the conductive particles, and the storage elastic modulus at normal temperature is 1/2 of the storage elastic modulus at normal temperature of the conductive particles and the adhesive composition.
  • the following particles are preferred.
  • the material of the rubber fine particles is silicone, acrylic emulsion, SBR, NBR or polybutadiene rubber, the rubber fine particles are preferably used alone or in admixture of two or more.
  • the three-dimensionally cross-linked rubber fine particles have excellent solvent resistance and are easily dispersed in the adhesive composition.
  • the filler can improve the electrical characteristics (connection reliability, etc.) between the circuit electrodes.
  • the filler for example, particles having an average particle size of 1/2 or less of the average particle size of the conductive particles can be suitably used.
  • particles having no conductivity are used in combination with a filler, particles having an average particle size not more than the particles having no conductivity can be used as the filler.
  • the content of the filler is preferably 5 to 60% by mass based on the total mass of the adhesive component of the adhesive composition. When the content is 60% by mass or less, the effect of improving connection reliability tends to be obtained more sufficiently. When the content is 5% by mass or more, the effect of adding the filler tends to be sufficiently obtained.
  • the adhesive composition of this embodiment can be used in the form of a paste when it is liquid at room temperature.
  • the adhesive composition When the adhesive composition is solid at room temperature, it may be heated and used, or may be made into a paste using a solvent.
  • the solvent that can be used is not particularly limited as long as it is not reactive with the components in the adhesive composition and exhibits sufficient solubility.
  • the solvent is preferably a solvent having a boiling point of 50 to 150 ° C. at normal pressure. When the boiling point is 50 ° C. or higher, the solvent is poorly volatile at room temperature, and can be used even in an open system. When the boiling point is 150 ° C. or lower, it is easy to volatilize the solvent, and thus good reliability can be obtained after bonding.
  • the adhesive composition of the present embodiment may be in the form of a film. If necessary, a solution of an adhesive composition containing a solvent or the like is applied onto a fluororesin film, a polyethylene terephthalate film, a peelable substrate (release paper, etc.), and then the solvent is removed to remove the solvent. An adhesive composition can be obtained. Moreover, after making a base material, such as a nonwoven fabric, impregnate the above solution and placing it on a peelable base material, a film-like adhesive composition can be obtained by removing the solvent and the like. Use of the adhesive composition in the form of a film is more convenient from the viewpoint of excellent handleability.
  • the thickness of the film adhesive composition may be 1 to 100 ⁇ m or 5 to 50 ⁇ m.
  • the adhesive composition of the present embodiment can be adhered by, for example, applying pressure together with heating or light irradiation. By using heating and light irradiation in combination, it can be bonded at a lower temperature in a shorter time.
  • the light irradiation is preferably performed in the wavelength region of 150 to 750 nm.
  • As the light source a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp (extra-high-pressure mercury lamp, etc.), a xenon lamp, a metal halide lamp, or the like can be used.
  • the irradiation dose may be 0.1-10 J / cm 2 .
  • the heating temperature is not particularly limited, but a temperature of 50 to 170 ° C. is preferable.
  • the pressure is not particularly limited as long as it does not damage the adherend, but is preferably 0.1 to 10 MPa. Heating and pressurization are preferably performed in the range of 0.5 seconds to 3 hours.
  • the adhesive composition of the present embodiment may be used as an adhesive for the same type of adherend, or as an adhesive for different types of adherends having different thermal expansion coefficients. Specifically, it is used as a circuit connecting material represented by anisotropic conductive adhesive, silver paste, silver film, etc .; semiconductor device adhesive material represented by CSP elastomer, CSP underfill material, LOC tape, etc. be able to.
  • the structure (circuit connection body) of the present embodiment includes the adhesive composition of the present embodiment or a cured product thereof.
  • the structure of this embodiment is a semiconductor device such as a circuit connection structure.
  • the circuit connection structure includes a first circuit member having a first circuit electrode, a second circuit member having a second circuit electrode, and a first circuit member. And a circuit connecting member disposed between the second circuit members.
  • the first circuit member includes, for example, a first substrate and a first circuit electrode disposed on the first substrate.
  • the second circuit member includes, for example, a second substrate and a second circuit electrode disposed on the second substrate. The first circuit electrode and the second circuit electrode face each other and are electrically connected.
  • the circuit connection member includes the adhesive composition of the present embodiment or a cured product thereof.
  • the structure of the present embodiment only needs to include the adhesive composition of the present embodiment or a cured product thereof, and a member that does not have a circuit electrode (such as a substrate) instead of the circuit member of the circuit connection structure. ) May be used.
  • the structure manufacturing method of the present embodiment includes a step of curing the adhesive composition of the present embodiment.
  • the circuit connection structure manufacturing method includes a first circuit member having a first circuit electrode, and a second circuit member having a second circuit electrode. Between the step of arranging the adhesive composition of the present embodiment, and pressurizing the first circuit member and the second circuit member to electrically connect the first circuit electrode and the second circuit electrode. And a heating and pressing step of heating and curing the adhesive composition. In the arranging step, the first circuit electrode and the second circuit electrode can be arranged to face each other. In the heating and pressurizing step, the first circuit member and the second circuit member can be pressurized in the opposite directions.
  • the adhesive composition of the present embodiment is interposed between the circuit electrodes of the semiconductor elements facing each other and the circuit electrodes of the semiconductor mounting substrate, and the circuit electrodes facing each other are added.
  • a mode in which the electrodes in the pressurizing direction are electrically connected by pressing is also possible.
  • FIG. 1 is a schematic cross-sectional view showing an embodiment of a structure.
  • a circuit connection structure 100 a shown in FIG. 1 includes a circuit member (first circuit member) 20 and a circuit member (second circuit member) 30 that are opposed to each other, and between the circuit member 20 and the circuit member 30.
  • the circuit connection member 10 which connects these is arrange
  • the circuit connection member 10 includes a cured product of the adhesive composition of the present embodiment.
  • the circuit member 20 includes a substrate (first substrate) 21 and a circuit electrode (first circuit electrode) 22 disposed on the main surface 21 a of the substrate 21.
  • An insulating layer (not shown) may be disposed on the main surface 21a of the substrate 21 as the case may be.
  • the circuit member 30 includes a substrate (second substrate) 31 and a circuit electrode (second circuit electrode) 32 disposed on the main surface 31 a of the substrate 31.
  • An insulating layer (not shown) may be disposed on the main surface 31a of the substrate 31 in some cases.
  • the circuit connecting member 10 contains an insulating substance (cured product of components excluding conductive particles) 10a and conductive particles 10b.
  • the conductive particles 10b are disposed at least between the circuit electrode 22 and the circuit electrode 32 facing each other. In the circuit connection structure 100a, the circuit electrode 22 and the circuit electrode 32 are electrically connected via the conductive particles 10b.
  • the circuit members 20 and 30 have one or a plurality of circuit electrodes (connection terminals).
  • a chip component such as a semiconductor chip (IC chip), a resistor chip, or a capacitor chip; a substrate such as a printed board or a semiconductor mounting board can be used.
  • Examples of the combination of the circuit members 20 and 30 include a semiconductor chip and a semiconductor mounting substrate.
  • the material of the substrate include inorganic substances such as semiconductor, glass, and ceramic; organic substances such as polyimide, polyethylene terephthalate, polycarbonate, (meth) acrylic resin, and cyclic olefin resin; and composites of glass and epoxy.
  • the substrate may be a plastic substrate.
  • FIG. 2 is a schematic cross-sectional view showing another embodiment of the structure.
  • the circuit connection structure 100b shown in FIG. 2 has the same configuration as the circuit connection structure 100a except that the circuit connection member 10 does not contain the conductive particles 10b.
  • the circuit electrode 22 and the circuit electrode 32 are in direct contact and are electrically connected without interposing conductive particles.
  • the circuit connection structures 100a and 100b can be manufactured, for example, by the following method. First, when the adhesive composition is in a paste form, the resin layer containing the adhesive composition is disposed on the circuit member 20 by applying and drying the adhesive composition. When the adhesive composition is in the form of a film, the resin layer containing the adhesive composition is disposed on the circuit member 20 by sticking the film-like adhesive composition to the circuit member 20. Subsequently, the circuit member 30 is placed on the resin layer disposed on the circuit member 20 so that the circuit electrode 22 and the circuit electrode 32 are opposed to each other. And a heat treatment or light irradiation is performed to the resin layer containing an adhesive composition, an adhesive composition hardens
  • Example 1 50 g of phenoxy resin (trade name: PKHC, manufactured by Union Carbide Co., Ltd., weight average molecular weight 45000) is dissolved in a mixed solvent of toluene / ethyl acetate (mass ratio: 50/50) to obtain a phenoxy resin having a solid content of 40% by mass. A solution was prepared.
  • PKHC manufactured by Union Carbide Co., Ltd., weight average molecular weight 45000
  • radical polymerizable compounds isocyanuric acid EO-modified diacrylate (trade name: M-215, manufactured by Toa Gosei Co., Ltd.), 2-methacryloyloxyethyl acid phosphate (phosphate ester, trade name: light ester P-2M, Kyoeisha) Chemical Co., Ltd.) and urethane acrylate (trade name: U-2PPA, Shin-Nakamura Chemical Co., Ltd.) were used.
  • silane coupling agent 3-methacryloxypropyltrimethoxysilane (trade name: KBM503, manufactured by Shin-Etsu Chemical Co., Ltd.) was prepared.
  • Benzoyl peroxide (trade name: Nyper BMT-K40, manufactured by NOF Corporation, 1 minute half-life temperature: 131.1 ° C., 10 minute half-life temperature: 73 ° C.) was prepared as a radical generator.
  • component (C) aluminum hydroxide (Al (OH) 3 ) particles having an average primary particle size of 1 ⁇ m were prepared.
  • the circuit connection material-containing liquid is applied on a PET film having a thickness of 50 ⁇ m, which is surface-treated on one side, and then dried with hot air at 70 ° C. for 3 minutes, thereby forming a film having a thickness of 20 ⁇ m on the PET film.
  • the circuit connection material was obtained.
  • Example 2 A film-like circuit connection material was produced in the same manner as in Example 1 except that the component (C) was changed to magnesium hydroxide (Mg (OH) 3 ) particles having an average primary particle size of 1 ⁇ m.
  • component (C) was changed to magnesium hydroxide (Mg (OH) 3 ) particles having an average primary particle size of 1 ⁇ m.
  • Example 3 A film-like circuit connection material was produced in the same manner as in Example 1 except that the component (C) was changed to magnesium oxide (Mg 2 O 3 ) particles having an average primary particle size of 1 ⁇ m.
  • Example 4 A film-like circuit connection material was produced in the same manner as in Example 1 except that the component (C) was changed to zirconium oxide (ZrO 2 ) particles having an average primary particle size of 1 ⁇ m.
  • a flexible circuit board having 500 copper circuits having a line width of 75 ⁇ m, a pitch of 150 ⁇ m, and a thickness of 18 ⁇ m, and a silicon nitride (SiN x ) having a thickness of 0.5 ⁇ m through the film-like circuit connecting material obtained by the above-described manufacturing method
  • a glass plate (thickness 0.7 mm) on which a thin layer was formed was heated and pressurized at 170 ° C. and 3 MPa for 20 seconds using a thermocompression bonding apparatus (heating method: constant heat type, manufactured by Toray Engineering Co., Ltd.). And connected over a width of 2 mm to produce a circuit connection structure.
  • the adhesiveness (salt water resistance) to the surface of the adherend (inorganic substrate) can be favorably maintained even after spraying with salt water in the example in comparison with the comparative example. Moreover, in an Example, it is confirmed that adhesiveness (salt water tolerance) can be maintained favorable, achieving a low-temperature short-time connection.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Manufacturing & Machinery (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Dispersion Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Conductive Materials (AREA)
  • Parts Printed On Printed Circuit Boards (AREA)
  • Combinations Of Printed Boards (AREA)
PCT/JP2016/084747 2015-11-25 2016-11-24 回路接続用接着剤組成物及び構造体 WO2017090659A1 (ja)

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CN201680068535.XA CN108291114A (zh) 2015-11-25 2016-11-24 电路连接用粘接剂组合物和结构体
KR1020187017184A KR102615097B1 (ko) 2015-11-25 2016-11-24 회로 접속용 접착제 조성물 및 구조체
CN202410394464.9A CN118291047A (zh) 2015-11-25 2016-11-24 电路连接用粘接剂组合物和结构体

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WO2022158594A1 (ja) * 2021-01-25 2022-07-28 昭和電工マテリアルズ株式会社 フィルム状接着剤及び接続構造体の製造方法
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JPWO2020184583A1 (zh) * 2019-03-13 2020-09-17

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CN118291047A (zh) 2024-07-05
JP6870618B2 (ja) 2021-05-12
TW202402994A (zh) 2024-01-16
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JPWO2017090659A1 (ja) 2018-09-13
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