CN117882497A - Adhesive film for circuit connection, circuit connection structure, and method for producing same - Google Patents

Adhesive film for circuit connection, circuit connection structure, and method for producing same Download PDF

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Publication number
CN117882497A
CN117882497A CN202280058356.3A CN202280058356A CN117882497A CN 117882497 A CN117882497 A CN 117882497A CN 202280058356 A CN202280058356 A CN 202280058356A CN 117882497 A CN117882497 A CN 117882497A
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CN
China
Prior art keywords
circuit
mass
circuit connection
adhesive film
electrode
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CN202280058356.3A
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Chinese (zh)
Inventor
岩元槙之介
工藤直
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Lishennoco Co ltd
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Lishennoco Co ltd
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Publication of CN117882497A publication Critical patent/CN117882497A/en
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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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/067—Polyurethanes; Polyureas
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • 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
    • H05K1/144—Stacked arrangements of planar printed circuit boards
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
    • H05K3/32—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits
    • H05K3/321—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by conductive adhesives
    • H05K3/323—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by conductive adhesives by applying an anisotropic conductive adhesive layer over an array of pads

Abstract

The adhesive film for circuit connection contains a resin component containing a thermoplastic resin, a radical polymerizable compound, and a radical polymerization initiator, and conductive particles, and the resin component further contains a silane coupling agent having a fluorene skeleton.

Description

Adhesive film for circuit connection, circuit connection structure, and method for producing same
Technical Field
The present invention relates to an adhesive (adhesive) film for circuit connection, a circuit connection structure, and a method for manufacturing the same.
Background
As a circuit connection material for a semiconductor element or a liquid crystal display element, a thermosetting resin using an epoxy resin exhibiting high adhesion (adhesive) and high reliability is known (for example, refer to patent document 1). As a constituent of the resin, a curing agent such as an epoxy resin, a phenol resin reactive with the epoxy resin, or a latent curing agent that promotes a reaction between the epoxy resin and the curing agent is generally used. The latent curing agent is an important factor for determining the curing temperature and curing speed, and various compounds are used from the viewpoints of storage stability at room temperature and curing speed upon heating.
Recently, a radical curable adhesive using both an acrylate derivative and/or a methacrylate derivative (hereinafter, collectively referred to as a "(meth) acrylate derivative") and a peroxide as a radical polymerization initiator has been focused on. Since the radical as a reactive species is highly reactive, radical curing can be cured in a short time (for example, refer to patent documents 2 and 3).
Therefore, a short-time curable adhesive which is advantageous for shortening the production time is currently being popularized. Further, in order to further improve the reactivity of radical curable adhesives, the use of chain transfer agents has been studied (for example, refer to patent documents 4 and 5).
Technical literature of the prior art
Patent literature
Patent document 1: japanese patent laid-open No. 1-113480
Patent document 2: japanese patent laid-open No. 2002-203427
Patent document 3: international publication No. 98/044067 booklet
Patent document 4: japanese patent laid-open No. 2003-221557
Patent document 5: international publication No. 2009/057376 booklet
Disclosure of Invention
Technical problem to be solved by the invention
In connection of circuit members, an adhesive film having anisotropic conductivity in which conductive particles are dispersed in an adhesive is used, but in the case of using a radical curing adhesive as an adhesive, the connection resistance of the obtained circuit connection structure tends to increase after a high-temperature high-humidity test.
Accordingly, an object of the present invention is to provide an adhesive film for circuit connection, which can provide a circuit connection structure having a connection resistance that is less likely to increase even under high temperature and high humidity conditions, and a circuit connection structure using the adhesive film, and a method for producing the same.
Means for solving the technical problems
One side of the present invention provides an adhesive film for circuit connection, comprising: a resin component containing a thermoplastic resin, a radical polymerizable compound, and a radical polymerization initiator; and conductive particles, wherein the resin component further contains a silane coupling agent having a fluorene skeleton.
According to the above-described adhesive film for circuit connection, a circuit connection structure in which the connection resistance is less likely to rise even under high temperature and high humidity conditions (hereinafter also referred to as "high temperature and high humidity connection reliability") can be obtained.
The content of the silane coupling agent having a fluorene skeleton may be 0.3 to 15 mass% based on the total mass of the resin component.
From the viewpoint of further reducing the connection resistance between the connected circuits and obtaining high-temperature high-humidity connection reliability, the content of the silane coupling agent having a fluorene skeleton may be 1 to 30 parts by mass relative to 100 parts by mass of the radical polymerizable compound.
The content of the silane coupling agent having a fluorene skeleton may be 1 to 30 parts by mass relative to 100 parts by mass of the thermoplastic resin from the viewpoint of further reducing the connection resistance between the connected circuits and obtaining high-temperature high-humidity connection reliability.
Another aspect of the present invention provides a circuit connection structure, comprising: a 1 st circuit part having a 1 st electrode; a 2 nd circuit part having a 2 nd electrode; and a connection portion which is disposed between the 1 st circuit member and the 2 nd circuit member and electrically connects the 1 st electrode and the 2 nd electrode to each other, the connection portion including a cured product of the adhesive film for circuit connection.
The circuit connection structure may be one in which the connection resistance is less likely to increase even under high-temperature and high-humidity conditions.
Another aspect of the present invention provides a method for manufacturing a circuit connection structure, including: the 1 st circuit member having the 1 st electrode, the 2 nd circuit member having the 2 nd electrode, and the adhesive film for circuit connection are heated and pressed in a state where the 1 st electrode and the 2 nd electrode are disposed so as to face each other with the adhesive film for circuit connection interposed therebetween, whereby the 1 st electrode and the 2 nd electrode are electrically connected.
According to the above method, a circuit connection structure in which the connection resistance is less likely to rise even under high temperature and high humidity conditions can be obtained.
Effects of the invention
According to the present invention, it is possible to provide an adhesive film for circuit connection, which can provide a circuit connection structure in which the connection resistance is less likely to increase even under high temperature and high humidity conditions, and a circuit connection structure using the adhesive film, and a method for manufacturing the same.
Drawings
Fig. 1 is a schematic cross-sectional view showing an embodiment of a connection structure.
Detailed Description
In the present specification, the numerical ranges shown in "to" are ranges including the numerical values before and after "to" as the minimum value and the maximum value, respectively. In the numerical ranges described in the present specification in stages, the upper limit value or the lower limit value of the numerical range in one stage may be replaced with the upper limit value or the lower limit value of the numerical range in another stage. In addition, within the numerical ranges described in the present specification, the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the embodiment. The upper limit and the lower limit described individually can be arbitrarily combined. In the present specification, "(meth) acrylate" means at least one of an acrylate and a methacrylate corresponding to the acrylate. The same applies to "(meth) acryl", and the like. The "(poly)" means both the case where there is a prefix of "poly" and the case where there is no prefix of "poly". Further, "a or B" may include either or both of a and B. In addition, 1 kind of material may be used alone or 2 or more kinds of material may be used in combination unless otherwise specified. The content of each component in the composition means the total amount of a plurality of substances present in the composition, unless otherwise specified, in the case where the plurality of substances corresponding to each component are present in the composition.
Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings, as the case may be. However, the present invention is not limited to the following embodiments.
Adhesive film for circuit connection
The adhesive film for circuit connection of the present embodiment includes: a resin component containing (a) a thermoplastic resin (hereinafter also referred to as "(a) component"), (B) a radical polymerizable compound (hereinafter also referred to as "(B) component"), (C) a radical polymerization initiator (hereinafter also referred to as "(C) component")) and (D) a silane coupling agent having a fluorene skeleton (hereinafter also referred to as "(D) component"; and (E) conductive particles (hereinafter, also referred to as "(E component").
The adhesive film for circuit connection of the present embodiment can be preferably used as an adhesive film for circuit connection for connecting a 1 st circuit component having a 1 st electrode (for example, a 1 st circuit component having a 1 st circuit electrode formed on a main surface of a 1 st substrate) and a 2 nd circuit component having a 2 nd electrode (for example, a 2 nd circuit component having a 2 nd circuit electrode formed on a main surface of a 2 nd substrate) in a state in which the 1 st electrode and the 2 nd electrode (the 1 st circuit electrode and the 2 nd circuit electrode) are arranged to face each other.
[ (A) component: thermoplastic resin ]
As the component a, a polyvinyl butyral resin, a polyvinyl formal resin, a polyamide resin, a polyester resin, a phenol resin, an epoxy resin, a phenoxy resin, a polystyrene resin, a xylene resin, a polyurethane resin, a polyester urethane resin, or the like can be used. These can be used singly or in combination of 2 or more.
The weight average molecular weight of the thermoplastic resin may be 1.0X10 from the viewpoint of film forming property and the like 4 From the viewpoint of the miscibility, the ratio may be 1.0X10 4 The above and less than 1.0X10 6 。
The weight average molecular weight of the thermoplastic resin is a value measured by gel permeation chromatography (GP C) using a calibration curve based on standard polystyrene under the following conditions.
GPC conditions ]
The using device comprises: hitachi L-6000 type [ Hitachi, ltd. ], column: gelpackg GL-R420+Gelpackg GL-R430+Gelpackg GL-R440 (3 total) [ Hitachi Chemical C o., manufactured by Ltd.) eluent: tetrahydrofuran, determination temperature: 40 ℃, flow rate: 1.75ml/min, detector: l-3300RI (Hitachi, ltd.)
As the component (A), a component having a Tg (glass transition temperature) of 40℃or higher and a weight average molecular weight of 1.0X10 can be used 4 The above hydroxyl group-containing resin (e.g., phenoxy resin). The hydroxyl-containing resin may be modified by an epoxy-containing elastomer.
In the present specification, the thermoplastic resin having a radical polymerizable functional group is formulated as the radical polymerizable compound (B).
The phenoxy resin can be obtained by reacting a difunctional phenol with an epihalohydrin to a high molecular weight or by polymerizing a difunctional epoxy resin with a difunctional phenol.
As the component (a), a polyester urethane resin can be used.
From the viewpoint of further improving the peeling-inhibiting effect, the content of the component (a) in the adhesive film for circuit connection may be 5% by mass or more or 30% by mass or less, 80% by mass or less or 60% by mass or 5 to 80% by mass or 30 to 60% by mass based on the resin component (for example, component other than the conductive particles and the filler) of the adhesive film for circuit connection.
[ (B) component: radical polymerizable Compound
(B) As the component (a), a compound having a radical polymerizable functional group can be used. The radical polymerizable functional group is preferably a vinyl group, an acryl group, a methacryl group, or the like. Of these, compounds having an acryl group and/or a methacryl group are more preferable. (B) The components can be used singly or in combination of 1 or more than 2.
As the component (B), a compound described below can be used even in any of a monomer and an oligomer, and a monomer and an oligomer can be used at the same time.
Examples of the component (B) include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, tetramethylolmethane tetra (meth) acrylate, 2-hydroxy-1, 3-di (meth) acryloxypropane, 2-bis [4- ((meth) acryloxymethoxy) phenyl ] propane, 2-bis [4- ((meth) acryloxypolyethoxy) phenyl ] propane, dicyclopentenyl (meth) acrylate, tricyclodecyl (meth) acrylate, tris ((meth) acryloxyethyl) isocyanurate, urethane (meth) acrylate, dimethyloltricyclodecane di (meth) acrylate, EO (ethylene oxide) modified diacrylate, and 2-methacryloxyethyl phosphate.
As the component (B), a compound having at least one partial structure selected from the group consisting of a dicyclopentane skeleton, a tricyclodecane skeleton, and a triazine ring can be used. By using a radical polymerizable substance having such a partial structure, the heat resistance of the cured product of the adhesive film becomes excellent.
The component (B) may contain a (meth) acrylate compound having a tricyclodecane skeleton from the viewpoint of taking a balance of the crosslinking density and the curing shrinkage and further reducing the connection resistance. The content of the (meth) acrylate compound having a tricyclodecane skeleton may be, for example, 0 to 90 mass%, 5 to 60 mass% or 10 to 30 mass% based on the total mass of the component (B) from the viewpoint of balance between the crosslinking density and the curing shrinkage.
As the component (B), a polymer such as polyurethane, polystyrene, polyethylene, polyvinyl butyral, polyvinyl formal, polyimide, polyamide, polyester, polyvinyl chloride, polyphenyl oxide, urea resin, melamine resin, phenol resin, xylene resin, epoxy resin, polyisocyanate resin, or phenoxy resin can be used. The polymer used as the component (B) has at least one radical polymerizable functional group in the molecule.
When the polymer is contained as the component (B), the handling property is also good, and the stress relaxation at the time of curing is also excellent, so that it is preferable that the adhesion is improved when the polymer has a functional group such as a hydroxyl group, and it is more preferable. More preferably, the compound is obtained by modifying each polymer with a radical polymerizable functional group.
The weight average molecular weight of these polymers may be 1.0X10 4 From the viewpoint of the miscibility, the ratio may be 1.0X10 4 Above and 1.0X10 6 The following is given. The weight average molecular weight herein was determined by Gel Permeation Chromatography (GPC) using a calibration curve based on standard polystyrene, according to the conditions described in the examples.
The component (B) may contain a (poly) urethane (meth) acrylate compound from the viewpoint of balancing the crosslinking density with the curing shrinkage and further reducing the connection resistance to improve the high temperature and high humidity resistance connection reliability. From the viewpoint of balance of crosslinking density and curing shrinkage, the content of the (poly) urethane (meth) acrylate compound may be, for example, 0 to 100 mass%, 20 to 90 mass%, or 40 to 80 mass% based on the total mass of the component (B).
(B) The component (c) may contain a (meth) acrylate compound represented by the following formula (1) (a (meth) acrylate compound having a phosphate structure). In this case, since the adhesive strength to the surface of the inorganic substance (metal or the like) is improved, the adhesive is suitable for adhesion between electrodes (for example, between circuit electrodes).
In the formula (1), n represents an integer of 1 to 3, and R represents a hydrogen atom or a methyl group.
The (meth) acrylate compound represented by the formula (1) is obtained, for example, by reacting phosphoric anhydride with 2-hydroxyethyl (meth) acrylate. Specific examples of the (meth) acrylate compound represented by the formula (1) include mono (2- (meth) acryloyloxyethyl) phosphate and the like, di (2- (meth) acryloyloxyethyl) phosphate and the like.
The content of the (meth) acrylate compound represented by the formula (1) may be, for example, 0 to 20 mass%, 1 to 10 mass%, or 2 to 5 mass% based on the total mass of the component (B) in view of easy availability of a crosslinking density required for improving connection reliability in order to reduce connection resistance.
The content of the component (B) in the adhesive film for circuit connection may be 5 mass% or more, 20 mass% or more, or 40 mass% or more, 90 mass% or less, 75 mass% or less, or 60 mass% or less, or 5 to 90 mass%, 20 to 75 mass%, or 40 to 60 mass% based on the total mass of the resin components (e.g., components other than the conductive particles and the filler) of the adhesive film for circuit connection, in order to easily obtain a crosslinking density required for improving the connection reliability against high temperature and high humidity in order to reduce the connection resistance.
[ (C) component: radical polymerization initiator ]
As the component (C), a compound that generates a free radical can be used, and examples thereof include a peroxide compound, an azo compound, and the like, which generate a free radical by thermal decomposition. The radical polymerization initiator is appropriately selected according to the target joining temperature, joining time, and the like. (C) The components can be used singly or in combination of 1 or more than 2.
Examples of the radical polymerization initiator include diacyl peroxides, peroxydicarbonates, peroxyesters, peroxyketals, dialkyl peroxides, and hydroperoxides.
Examples of diacyl peroxides include 2, 4-dichlorobenzoyl peroxide, 3, 5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, distearyl peroxide, succinyl peroxide, benzoyl peroxide toluene peroxide, benzoyl peroxide, and the like.
Examples of the peroxydicarbonates include di-n-propyl peroxydicarbonate, diisopropyl peroxydicarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, di-2-ethoxymethoxy peroxydicarbonate, di (2-ethylhexyl peroxy) dicarbonate, dimethoxybutyl peroxydicarbonate, and di (3-methyl-3-methoxybutyl peroxy) dicarbonate.
As the peroxyesters, there are used, examples thereof include 1, 3-tetramethylbutyl peroxyneodecanoate, 1-cyclohexyl-1-methylethyl peroxyneodecanoate, t-hexyl peroxyneodecanoate, t-butyl peroxypivalate, 1, 3-tetramethylbutyl peroxy2-ethylhexanoate, 2, 5-dimethyl-2, 5-di (2-ethylhexyl peroxyhexane, 1-cyclohexyl-1-methylethyl peroxy2-ethylhexanoate, t-hexyl peroxy2-ethylhexanoate, t-butyl peroxy2-ethylhexanoate tert-butyl peroxyisobutyrate, 1-bis (tert-butyl peroxy) cyclohexane, tert-hexyl peroxyisopropyl monocarbonate, tert-butyl peroxy-3, 5-trimethylethylhexanoic acid, tert-butyl peroxylaurate, 2, 5-dimethyl-2, 5-di (m-toluene peroxy) hexane, tert-butyl peroxyisopropyl monocarbonate, tert-butyl peroxy-2-ethylhexyl monocarbonate, tert-hexyl peroxybenzoate, tert-butyl peroxyacetate, and the like.
Examples of the peroxyketal include 1, 1-bis (t-hexylperoxy) -3, 5-trimethylcyclohexane, 1-bis (t-hexylperoxy) cyclohexane, 1-bis (t-butylperoxy) -3, 5-trimethylcyclohexane, 1- (t-butylperoxy) cyclododecane, and 2, 2-bis (t-butylperoxy) decane.
Examples of the dialkyl peroxides include α, α' -bis (t-butylperoxy) diisopropylbenzene, diisopropylbenzene peroxide, 2, 5-dimethyl-2, 5-di (t-butylperoxy) hexane, t-butylperoxycumene, and the like.
Examples of the hydrogen peroxide include diisopropylbenzene hydroperoxide and isopropylbenzene hydroperoxide.
These radical polymerization initiators may be used in combination with decomposition accelerators, inhibitors, and the like. Further, a material in which these radical polymerization initiators are coated with a polyurethane-based or polyester-based polymer material or the like and subjected to microencapsulation is preferable because the preservability can be prolonged.
From the viewpoint of pot life, the content of the component (C) in the adhesive film for circuit connection may be 0.1 mass% or more, 0.5 mass% or more, or 1 mass% or more, 20 mass% or less, 10 mass% or less, or 5 mass% or less, or 0.1 to 20 mass%, 0.5 to 10 mass%, or 1 to 5 mass% based on the total mass of the resin components (e.g., components other than the conductive particles and the filler) of the adhesive film for circuit connection.
[ (D) component: silane coupling agent having fluorene skeleton ]
As the component (D), an alkoxysilane compound having a fluorene skeleton can be used.
Examples of the alkoxysilane compound having a fluorene skeleton include compounds represented by the following general formula (2).
In the general formula (2), R 1 R is R 2 Each independently represents an alkyl group having 1 to 4 carbon atoms, X 1 X is X 2 Each independently represents a metal represented by-Si (OR) 3 ) a (R 4 ) 3-a A group represented by Y 1 Y and Y 2 Each independently represents a 2-valent linking group. Wherein a represents an integer of 1 to 3, R 3 Represents an alkyl group having 1 to 4 carbon atoms or an alkoxyalkyl group having 2 to 8 carbon atoms, R 4 Represents a hydrogen atom, a hydroxyl group, a halogen atom or a hydrocarbon group. However, where there are multiple R' s 3 R is R 4 In the above case, they may be the same or different.
And, in the case where a is 2 or 3, a plurality of R 3 May be the same or different. And, when a is 1, a plurality of R 4 May be the same or different. m1 and m2 each independently represent an integer of 1 to 5, and n1 and n2 each independently represent an integer of 0 to 4. However, the total of m1 and n1 and the total of m2 and n2 are integers of 5 or less, respectively.
As R 1 R is R 2 Examples of the alkyl group having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and tert-butyl.
In the general formula (2), n1 and n2 may be integers of 0 to 2, or may be 0 or 1. m1 and m2 may be an integer of 1 to 3, may be 1 or 2, or may be 1.
As R 3 Examples of the alkyl group having 1 to 4 carbon atoms include methyl, ethyl, propyl and butyl. As R 3 Examples of the alkoxyalkyl group having 2 to 8 carbon atoms include an alkyl group having 1 to 4 carbon atoms having an alkoxy group having 1 to 4 carbon atoms such as a methoxymethyl group, a methoxyethyl group, a methoxypropyl group, a methoxybutyl group, an ethoxymethyl group, an ethoxyethyl group, an ethoxypropyl group, an ethoxybutyl group, a propoxymethyl group, a propoxyethyl group, a propoxypropyl group, a propoxybutyl group, a butoxymethyl group, a butoxyethyl group, a butoxypropyl group, and a butoxybutyl group.
As R 4 Examples of the halogen atom include a fluorine atom, a chlorine atom and a bromine atom. As R 4 Examples of the hydrocarbon group(s) include alkyl groups having 1 to 10 carbon atoms such as methyl, ethyl and propyl; aryl groups having 6 to 10 carbon atoms such as phenyl and tolyl.
As Y 1 Y and Y 2 A 2-valent linking group of (2)Examples thereof include a thioether group represented by the following general formula (3-1) or general formula (3-2). In general formulae (3-1) and (3-2), R 6 And X in the general formula (2) 1 Or X 2 Si bond of (c).
—O—R 5 —S—R 6 — (3-1)
In the general formula (3-1), R 5 An alkylene group having 2 to 6 carbon atoms. Examples of the alkylene group having 2 to 6 carbon atoms include ethylene, propylene, butylene, pentylene and hexylene. And R is 6 Represents a methylene group or an alkylene group having 2 to 6 carbon atoms. Examples of the alkylene group having 2 to 6 carbon atoms include ethylene, trimethylene, propylene, 1, 2-butylene and hexylene.
In the general formula (3-2), R 6 And R in the general formula (3-1) 6 The meaning is the same. N represents an integer of 2 to 6, and may be 2 or 3, or may be 2. M3 represents an integer of 1 to 6. R is R 7 Represents a hydrogen atom or a methyl group.
Specific examples of the compound represented by the general formula (2) include a compound represented by the following general formula (2-1) and a compound represented by the general formula (2-2). In addition, me represents a methyl group.
The compounds represented by the general formula (2) may be commercially available products such as OGSOL SC-001 and OGSOL SC-003 (above, osaka Gas Chemicals Co., ltd., product name).
The compound represented by the general formula (2) can be synthesized by reacting a compound represented by the general formula (4-1) below or a compound represented by the general formula (4-2) below with a compound represented by the general formula (5-1) below and a compound represented by the general formula (5-2) below.
R in the general formula (4-1) 1 、R 2 N1, n2 and R in the general formula (2) 1 、R 2 N1 and n2 have the same meaning. R in the general formula (4-1) 8 R is R 9 Each independently represents an alkenyl group having 2 to 6 carbon atoms. Examples of the alkenyl group having 2 to 6 carbon atoms include vinyl, allyl, 1-butynyl, 1-pentynyl and 1-hexynyl.
R in the general formula (4-2) 1 、R 2 N1, n2 and R in the general formula (2) 1 、R 2 N1 and n2 have the same meaning. And n, m3, R in the general formula (4-2) 7 And n, m3, R in the general formula (3-2) 7 The meaning is the same.
X 1 —R 6 —SH (5-1)
X 2 —R 6 —SH (5-2)
X in the general formula (5-1) 1 And X in the general formula (2) 1 The meaning is the same. R in the general formula (5-1) 6 And R in the general formula (3-2) 6 (R in the general formula (3-1)) 6 ) The meaning is the same. And X in the general formula (5-2) 2 And X in the general formula (2) 2 The meaning is the same. R in the general formula (5-2) 6 And R in the general formula (3-2) 6 (R in the general formula (3-1)) 6 ) The meaning is the same.
The compound represented by the general formula (4-1) can be synthesized by a conventionally known method, for example, by an addition reaction of a compound represented by the following general formula (6) by a method such as allylation. Further, the compounds represented by the general formula (4-1) may be commercially available ones.
In the general formula (6), R 1 、R 2 R in the general formula (2), m1, m2, n1 and n2 1 、R 2 M1, m2, n1 and n2 have the same meaning.
The compound represented by the general formula (4-2) may be synthesized by a conventionally known method. For example, the compound represented by the general formula (6) can be synthesized by reacting the compound with an alkylene oxide or an alkylene carbonate, and then reacting the compound with (meth) acrylic acid or a derivative thereof. In the reaction, an acid catalyst or a basic catalyst may be used.
The reaction of the compound represented by the general formula (4-1) or the compound represented by the general formula (4-2) with the compound represented by the general formula (5-1) and the compound represented by the general formula (5-2) can be carried out by a radical reaction. As the radical reaction initiator, a thermal radical initiator or a photo radical initiator can be used.
Examples of the photo radical initiator include benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; acetophenones such as acetophenone, p-dimethyl acetophenone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-diethoxy acetophenone, 2-dimethoxy-2-phenylacetophenone, 2-diethoxy-2-phenylacetophenone, 2-phenyl-2-hydroxy-acetophenone, 1-dichloro acetophenone, and 1-hydroxycyclohexyl phenyl ketone; propyl benzene ketones such as p-dimethylaminopropyl benzene ketone, 2-hydroxy-2-methyl-propyl benzene ketone, and 2, 2-dimethoxy-1, 2-diphenylethane-1-one; butyryl phenones such as 1- [4- (2-hydroxyethoxy) phenyl ] -2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methyl-propan-1-one, and the like; 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2-dimethylamino-2-methyl-1-phenylpropane-1-one, 2-diethylamino-2-methyl-1-phenylpropane-1-one, 2-methyl-2-morpholino-1-phenylpropane-1-one, 2-dimethylamino-2-methyl-1- (4-methylphenyl) propan-1-one, 1- (4-butylphenyl) -2-dimethylamino-2-methylpropan-1-one, 2-dimethylamino-1- (4-methoxyphenyl) -2-methylpropan-1-one, 2-dimethylamino-2-methyl-1- (4-methylthiophenyl) propan-1-one, 2-benzyl-2-dimethylamino-1- (4-methylphenyl) -butan-1-one, and the like, benzophenones such as benzyl, N '-bis (dimethylamino) benzophenone (Michler's ketone) and 3, 3-dimethyl-4-methoxybenzophenone; ketals such as acetophenone dimethyl ketal and benzil dimethyl ketal; thioxanthenes such as thioxanthene, 2-chlorothioxanthene, and 2, 4-diethylthioxanthene; anthraquinones such as 2-ethylanthraquinone, 1-chloroanthraquinone, 1, 2-benzanthraquinone, and 2, 3-diphenylanthraquinone; (thioxanthones such as thioxanthone, 2, 4-dimethylthioxanthone, 2, 4-diethylthioxanthone, 2-chlorothioxanthone, and 2, 4-diisopropylthioxanthone; acridines such as 1, 3-bis- (9-acridinyl) propane, 1, 7-bis- (9-acridinyl) heptane, and 1, 5-bis- (9-acridinyl) pentane; triazines such as 2,4, 6-tris (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4, 6-bis (trichloromethyl) -s-triazine, and 2, 4-bis-trichloromethyl-6- (3-bromo-4-methoxy) styrylbenzene-s-triazine; thio ethers such as benzyl diphenyl sulfide; acyl phosphine oxides such as 2,4, 6-trimethylbenzoyl diphenyl phosphorus oxide; cyclopentadienyl titanium light free radical initiator; oxime esters, and the like. The photo radical initiator may be used alone or in combination of 1 or more than 2.
Examples of the thermal radical initiator include dialkyl peroxides such as di-t-butyl peroxide and dicumyl peroxide; diacyl peroxides such as lauroyl peroxide, benzoyl toluene peroxide and toluene peroxide; peroxyesters such as t-butyl peroxyacetate, t-butyl peroxyisooctanoate, and t-butyl peroxybenzoate; ketone peroxides; peroxydicarbonates; peroxy ketals; azoamide compounds such as azonitrile compounds such as 2,2' -azobis (2, 4-dimethylvaleronitrile), 2' -azobis (isobutyronitrile), 2' -azobis (2-methylbutyronitrile), 2' -azobis (4-methoxy-2, 4-dimethylvaleronitrile), and 2,2' -azobis { 2-methyl-N- [1, 1-bis (hydroxymethyl) -2-hydroxyethyl ] propionamide }; azoamidine compounds such as 2,2 '-azobis (2-amidinopropane) dihydrochloride and 2,2' -azobis [2- (2-imidazolin-2-yl) propane ] dihydrochloride; azoalkane compounds such as 2,2 '-azobis (2, 4-trimethylpentane) and 4,4' -azobis (4-cyanovaleric acid); azo compounds having an oxime skeleton such as 2,2' -azobis (2-methylpropionamide oxime). The thermal radical initiator may be used alone or in combination of 1 or more than 2.
The amount of the radical initiator to be blended may be 0.1 to 15 parts by mass, may be 0.3 to 10 parts by mass, or may be 0.7 to 5 parts by mass based on 100 parts by mass of the compound represented by the general formula (4-1) or the compound represented by the general formula (4-2) and the total amount of the compound represented by the general formula (5-1) and the compound represented by the general formula (5-2).
The photo radical initiator may be combined with a photosensitizer. Examples of the photosensitizer include tertiary amines such as trialkylamine and triethanolamine; dialkyl aminobenzoic acid alkyl esters such as ethyl N, N-dimethyl aminobenzoate and amyl N, N-dimethyl aminobenzoate; bis (dialkylamino) benzophenones such as 4, 4-bis (dimethylamino) benzophenone and 4,4' -diethylamino benzophenone; phosphines such as triphenylphosphine; toluidines such as N, N-dimethyl toluidine; anthracene such as 9, 10-dimethoxy anthracene, 2-ethyl-9, 10-dimethoxy anthracene, and 2-ethyl-9, 10-diethoxy anthracene. The photosensitizers may be used alone or in combination of 1 or more than 2.
The amount of the photosensitizer to be blended may be 0.1 to 150 parts by mass or 5 to 75 parts by mass based on 100 parts by mass of the photo-radical initiator.
The radical reaction may be carried out in a reaction liquid containing a solvent. Examples of the solvent include alcohols such as ethanol, propanol, isopropanol, ethylene glycol, and propylene glycol; hydrocarbons such as hexane, cyclohexane, toluene, and xylene; halogenated hydrocarbons such as methylene chloride and chloroform; ethers such as dimethyl ether, diethyl ether, dioxane, and tetrahydrofuran; esters such as methyl acetate, ethyl acetate, butyl acetate, ethyl lactate, and ethyl butyrate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and N-methyl-2-pyrrolidone; fibrinolytic substances such as methyl fibrinolytic substance, ethyl fibrinolytic substance, butyl fibrinolytic substance, and the like; carbitols such as methyl carbitol, ethyl carbitol, butyl carbitol, and the like; propylene glycol monoalkyl ethers such as propylene glycol monomethyl ether, propylene glycol monoethyl ether, and propylene glycol mono-n-butyl ether; glycol ether esters such as ethylene glycol monomethyl ether acetate and propylene glycol monomethyl ether acetate; amides such as N, N-dimethylformamide and N, N-dimethylacetamide; sulfoxides such as dimethyl sulfoxide; organic solvents such as nitriles including acetonitrile and benzonitrile. The solvent may be used alone or in combination of 1 or more than 2.
The total concentration of the compound represented by the general formula (4-1) or the compound represented by the general formula (4-2) and the compound represented by the general formula (5-1) and the compound represented by the general formula (5-2) in the reaction solution may be 1 to 90% by mass, may be 5 to 80% by mass, or may be 10 to 50% by mass.
The radical reaction can be performed by imparting active energy to a reaction system including the compound represented by the general formula (4-1) or the compound represented by the general formula (4-2), and the compound represented by the general formula (5-1) and the compound represented by the general formula (5-2).
As the activation energy, at least one of thermal energy and optical energy can be utilized according to the kind of radical initiator or the like.
When heat energy is applied, the heating temperature may be 50 to 250 ℃, 60 to 200 ℃, or 80 to 180 ℃.
When the light energy is applied, radiation (gamma rays, X rays, etc.), ultraviolet rays, visible rays, etc. can be used as the light.
As the light source, for example, in the case of ultraviolet rays, a Deep ultraviolet lamp, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a halogen lamp, a laser light source (a light source such as helium-cadmium laser or excimer laser), or the like can be used. The wavelength of light may be 150 to 800nm, 150 to 600nm or 200 to 400nm. The irradiation light amount (irradiation energy) may be 1 to 10000mW, 5 to 5000mW, or 10 to 1000mW. The irradiation time may be 5 seconds to 60 minutes, 10 seconds to 30 minutes, or 30 seconds to 10 minutes.
The separation and purification of the compound represented by the general formula (2) from the reaction mixture can be carried out by a conventionally known method such as recrystallization and chromatography.
As the alkoxysilane compound having a fluorene skeleton, japanese patent laid-open No. 2020-1 can be usedExamples of fluorene compounds disclosed in Japanese patent application laid-open No. 80063 include 9, 9-bis [3- (tric) C 1-4 Alkoxysilyl groups C 2-4 Alkylthio) propoxynaphthyl]Fluorene, and the like.
The content of the component (D) in the adhesive film for circuit connection may be 0.3 to 15% by mass, or 0.5 to 6% by mass, or 1 to 3% by mass, based on the total mass of the resin components.
The content of the component (D) may be 0.1 to 300 parts by mass, or 0.5 to 100 parts by mass, or 1 to 50 parts by mass, or 1 to 30 parts by mass, based on 100 parts by mass of the total mass of the component (a), from the viewpoint of further reducing the connection resistance between the connected circuits and obtaining high-temperature high-humidity connection reliability.
The content of the component (D) may be 0.1 to 300 parts by mass, or 0.5 to 100 parts by mass, or 1 to 50 parts by mass, or 1 to 30 parts by mass, relative to 100 parts by mass of the total of the component (B), from the viewpoint of further reducing the connection resistance between the connected circuits and obtaining high-temperature high-humidity connection reliability.
[ (E) component: conductive particles ]
The component (E) may be Au, ag, ni, cu, metal particles such as solder, conductive carbon particles composed of conductive carbon, or the like. The component (E) may be a component in which the surface of a transition metal such as Ni is coated with a noble metal such as Au. From the viewpoint of obtaining a sufficient pot life, the surface layer may be made of Au, ag, or a platinum group noble metal, or may be made of Au. The component (E) may be coated conductive particles comprising a noble metal, in which a conductive layer is formed on the surface of nonconductive particles such as glass, ceramic, or plastic by coating the surface of the nonconductive particles with the conductive material. In the case of using such particles or hot-melt metal particles, since the particles are deformable by heating and pressurizing, the contact area with the electrode at the time of connection can be increased to improve the reliability.
(E) The component may be the metal particles, conductive carbon particles, or insulating coated conductive particles including insulating layers which coat the conductive particles and the surfaces of the particles and which contain an insulating material such as a resin. If the component (E) is an insulating coated conductive particle, even when the content of the component (E) is large, the surface of the particle is coated with the resin, so that it is possible to suppress occurrence of a short circuit due to contact between the components (E) and to improve the insulation between adjacent electrode circuits.
(E) The component (c) may be used alone or in combination of 1 or more than 2 of the above-mentioned various conductive particles.
(E) The maximum particle size of the component needs to be smaller than the minimum spacing of the electrodes (shortest distance between adjacent electrodes). The maximum particle diameter of the component (E) may be 1.0 μm or more, or may be 2.0 μm or more, or may be 2.5 μm or more, from the viewpoint of excellent dispersibility and conductivity. The maximum particle diameter of the component (E) may be 50 μm or less, 30 μm or less, or 20 μm or less from the viewpoint of excellent dispersibility and electrical conductivity. From these viewpoints, the maximum particle diameter of the component (E) may be 1.0 to 50. Mu.m, 2.0 to 30. Mu.m, or 2.5 to 20. Mu.m. In the present specification, the particle size was measured by observation using a Scanning Electron Microscope (SEM) for any 300 (pcs) of conductive particles, and the obtained maximum value was taken as the maximum particle size of the component (E). In addition, when the component (E) has a protrusion or the like that is not spherical, the particle diameter of the component (E) is set to be a diameter of a circle circumscribed with the conductive particles in the SEM image.
The average particle diameter of the component (E) may be 1.0 μm or more, may be 2.0 μm or more, or may be 2.5 μm or more from the viewpoint of excellent dispersibility and conductivity. The average particle diameter of the component (E) may be 50 μm or less, 30 μm or less, or 20 μm or less from the viewpoint of excellent dispersibility and electrical conductivity. From these viewpoints, the average particle diameter of the component (E) may be 1.0 to 50. Mu.m, may be 2.0 to 30. Mu.m, or may be 2.5 to 20. Mu.m. In this specification, the particle size was measured for any 300 (pcs) of conductive particles by observation using a Scanning Electron Microscope (SEM), and the average value of the obtained particle sizes was taken as the average particle size.
The content of the component (E) in the adhesive film for circuit connection may be in the range of 0.1 to 30 parts by volume with respect to 100 parts by volume of the resin component (for example, component other than the conductive particles and the filler) of the adhesive film for circuit connection, in view of easy obtaining of stable connection resistance. The content of the component (E) may be 0.1 to 10 parts by volume from the viewpoint of preventing short-circuiting of adjacent circuits or the like due to excessive conductive particles.
The content of the component (E) may be 0.5 to 60 mass%, 3 to 45 mass%, or 6 to 30 mass% based on the total mass of the component (a), the component (B), the component (C), and the component (D) in view of easy obtaining of stable connection resistance.
[ other Components ]
The adhesive film for circuit connection of the present embodiment may further contain other components than the above components. Examples of the other components include a thiol compound (hereinafter, also referred to as component (F)), a coupling agent other than component (D) (hereinafter, also referred to as component (H)), and a filler. These components can be used singly or in combination of 1 or more than 2.
The thiol compound of the component (F) may be a thiol compound having 1 thiol group (monofunctional thiol compound), or may be a thiol compound having a plurality of thiol groups (multifunctional thiol compound).
(F) The thiol group of the component may be a primary thiol group, a secondary thiol group, or a tertiary thiol group.
Examples of the monofunctional thiol compound include 2-mercaptobenzothiazole, 2-methyl-4, 5-dihydrofuran-3-thiol, 3-mercapto-1-hexanol, mercaptomethylbutanol, 3-mercapto-2-methylpentanol, 3-mercapto-3-methylbutanol, 4-ethoxy-2-methyl-2-butanethiol, hexanethiol, isobutylthiol, 1-dimethylheptanethiol, 2-ethylhexyl-3-mercaptopropionate, n-octyl-3-mercaptopropionate, methoxybutyl-3-mercaptopropionate, and stearyl-3-mercaptopropionate.
Examples of the polyfunctional thiol compound include pentaerythritol tetrakis (3-mercaptobutyrate), ethanedithiol, 1, 3-propanethiol, 1, 4-butanethiol, trimethylolpropane tris (3-mercaptopropionate), tris- [ (3-mercaptopropionyloxy) -ethyl ] -isocyanurate, and tetraethyleneglycol bis (3-mercaptopropionate).
The content of the component (F) may be 0.05 mass% or more, 0.5 mass% or more, 1.0 mass% or more, or 1.5 mass% or more based on the mass of the resin component from the viewpoint of suppressing peeling at the interface of the cured adhesive film and the circuit member and suppressing an increase in the connection resistance of the circuit connection structure. The content of the component (F) may be 5.0 mass% or less, 3.0 mass% or less, 2.5 mass% or less, or 2.0 mass% or less from the viewpoint of suppressing peeling at the interface between the cured adhesive film and the circuit member and suppressing an increase in connection resistance of the circuit connection structure.
As the coupling agent of the component (H), a compound having at least one of a vinyl group, an acrylic group (acryl group), an amino group, an epoxy group, or an isocyanate group can be used from the viewpoint of improving the adhesion.
Examples of the filler include nonconductive fillers (e.g., nonconductive particles). The filler may be any of an inorganic filler and an organic filler. Examples of the inorganic filler include metal oxide particles such as silica particles, alumina particles, silica-alumina particles, titania particles, and zirconia particles; inorganic particles such as nitride particles. Examples of the organic filler include organic particles such as silicone particles, methacrylate-butadiene-styrene particles, acrylic-silicone particles, polyamide particles, and polyimide particles. These particles may have a uniform structure or may have a core-shell structure. The maximum diameter of the filler material may be smaller than the minimum particle diameter of the conductive particles.
The filler may be contained in an amount of 4 to 60% by volume, 5 to 50% by volume, or 6 to 30% by volume based on the total volume of the adhesive film for circuit connection. From the viewpoint of improving connection reliability, the content of the filler may be 3 to 60 mass%, 4 to 40 mass%, or 5 to 20 mass% based on the total mass of the (a), (B), (C), and (D) components.
The adhesive film for circuit connection of the present embodiment may contain other additives such as a softener, an accelerator, an anti-aging agent, a colorant, a flame retardant, a thixotropic agent, and a polymerization inhibitor. Examples of the polymerization inhibitor include hydroquinone and methyl ether hydroquinone.
The adhesive film of the present embodiment has been described above, but the present invention is not limited to the above embodiment.
For example, the adhesive film for circuit connection may have a multilayer structure of 2 or more layers in view of easy obtaining of stable connection resistance.
The adhesive film for circuit connection of the above embodiment may be an adhesive film for circuit connection containing no conductive particles.
The adhesive film for circuit connection of the present embodiment can be produced by the following method. Specifically, first, the component (a), the component (B), the component (C), the component (D), and the component (E), and other components added as needed, are added to a solvent (organic solvent), and dissolved or dispersed by stirring, mixing, kneading, or the like, to prepare a varnish composition (varnish-like adhesive composition). Thereafter, the varnish composition is applied to the substrate subjected to the release treatment using a blade coater, roll coater, applicator, comma coater, die coater, or the like, and then the solvent is volatilized by heating, whereby an adhesive film for circuit connection can be formed on the substrate.
As the solvent used for preparing the varnish composition, a solvent having a property of being able to uniformly dissolve or disperse each component can be used. Examples of such solvents include toluene, acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, propyl acetate, butyl acetate, and the like. These solvents can be used singly or in combination of 2 or more. The stirring and mixing in the preparation of the varnish composition and the mixing can be performed by using, for example, a stirrer, a grinder, a three-roll, a ball mill, a bead mill, and a homogenizing and dispersing machine.
The substrate is not particularly limited as long as it has heat resistance capable of withstanding the heating conditions at the time of volatilizing the solvent, and for example, a substrate (e.g., film) made of stretched polypropylene (OPP), polyethylene terephthalate (PET), polyethylene naphthalate, polyethylene isophthalate, polybutylene terephthalate, polyolefin, polyacetate, polycarbonate, polyphenylene sulfide, polyamide, polyimide, cellulose, ethylene/vinyl acetate copolymer, polyvinyl chloride, polyvinylidene chloride, synthetic rubber, liquid crystal polymer, or the like can be used.
The heating conditions for evaporating the solvent from the varnish composition applied to the substrate may be conditions sufficient to evaporate the solvent. The heating condition may be, for example, 40 ℃ to 120 ℃ and 0.1 to 10 minutes.
In the adhesive film for circuit connection of the present embodiment, a part of the solvent may remain without being removed. The content of the solvent in the adhesive film for circuit connection of the present embodiment may be, for example, 10 mass% or less or 5 mass% or less based on the total mass of the adhesive film.
Circuit connection structure and method for manufacturing the same
Next, a circuit connection structure and a method for manufacturing the same will be described.
The circuit connection structure of the present embodiment includes: a 1 st circuit part having a 1 st electrode; a 2 nd circuit part having a 2 nd electrode; and a connection portion which is disposed between the 1 st circuit member and the 2 nd circuit member and electrically connects the 1 st electrode and the 2 nd electrode to each other, the connection portion including a cured product of the adhesive film for circuit connection of the present embodiment.
The method for manufacturing the circuit connection structure of the present embodiment includes the steps of: the 1 st circuit member having the 1 st electrode, the 2 nd circuit member having the 2 nd electrode, and the adhesive film for circuit connection of the present embodiment are heated and pressed in a state where the 1 st electrode and the 2 nd electrode are disposed so as to face each other with the adhesive film for circuit connection interposed therebetween, whereby the 1 st electrode and the 2 nd electrode are electrically connected.
Fig. 1 is a schematic cross-sectional view showing an embodiment of a circuit connection structure. The circuit connection structure 1 shown in fig. 1 includes: a 1 st circuit member 20 having a 1 st circuit substrate 21 and a 1 st circuit electrode (1 st connection terminal) 22 formed on a main surface 21a thereof; a 2 nd circuit member 30 having a 2 nd circuit substrate 31 and a 2 nd circuit electrode (2 nd connection terminal) 32 formed on a main surface 31a thereof; and a connection portion 10 interposed between and bonding the 1 st circuit part 20 and the 2 nd circuit part 30. The 2 nd circuit member 30 is disposed to face the 1 st circuit member 20 so that the 2 nd circuit electrode 32 faces the 1 st circuit electrode 22.
The connection portion 10 is a connection portion formed by interposing the adhesive film for circuit connection of the present embodiment between the 1 st circuit member 20 and the 2 nd circuit member 30 and pressurizing the same, and includes a cured product of the adhesive film for circuit connection (for example, a cured product of an adhesive composition including (a), (B), (C), and (D)). In the present embodiment, an example of the case where the connection portion 10 is formed using an adhesive film for circuit connection containing conductive particles is shown, and the connection portion 10 is composed of the insulating layer 11 and the conductive particles 7 dispersed in the insulating layer 11. The insulating layer 11 contains a cured body formed by radical polymerization of a radical polymerizable compound derived from components other than the conductive particles in the adhesive film.
The 1 st circuit electrode 22 and the 2 nd circuit electrode 32 which are opposed to each other are electrically connected via the conductive particles 7. On the other hand, the 1 st circuit electrode 22 and the 2 nd circuit electrode 32 formed on the same circuit substrate are insulated from each other.
The 1 st circuit board 21 and the 2 nd circuit board 31 include chip components such as semiconductor chips, resistor chips, and capacitor chips, and substrates such as printed boards. In general, a large number of connection terminals are provided on the circuit part, but the connection terminals may be single according to circumstances.
More specifically, a substrate of an inorganic material such as a semiconductor, glass, or ceramic, a plastic substrate, or a glass/epoxy substrate is used. Examples of the plastic substrate include polyimide films, polycarbonate films, and polyester films. The 1 st circuit electrode and the 2 nd circuit electrode are formed of a metal such as copper. In order to obtain a better electrical connection, the surface of at least one of the 1 st circuit electrode and the 2 nd circuit electrode is preferably made of a metal selected from gold, silver, tin, and platinum groups. The surface layer is selected from any one of gold, silver, platinum group or tin, and they may be used in combination. Also, a plurality of metals may be combined to form a multilayer structure, such as copper/nickel/gold.
One of the 1 st circuit member 20 and the 2 nd circuit member 30 may be a liquid crystal display panel having a glass substrate or a plastic substrate as a circuit substrate and having connection terminals made of ITO or the like. One of the 1 st circuit member 20 and the 2 nd circuit member 30 may be a flexible printed circuit board (FPC) having a polyimide film as a circuit substrate, a Tape Carrier Package (TCP) or a Chip On Film (COF), or a semiconductor silicon chip having a semiconductor substrate as a circuit substrate. These various circuit components are appropriately combined as necessary to construct a circuit connection structure.
In order to eliminate the influence of the volatile components on the connection due to the heating during the connection, it is preferable to perform a preliminary heating treatment on the substrate provided with the circuit electrode before the connection step by the adhesive film for circuit connection.
The circuit connection structure 1 is formed, for example, by: the 1 st circuit member 20, the adhesive film for circuit connection, and the 2 nd circuit member 30 are sequentially stacked so that the 1 st connection terminal 22 and the 2 nd connection terminal 32 face each other, and pressurized or heated further in this state. The pressure is not particularly limited as long as it is within a range that does not damage the adherend, but is usually preferably 0.1 to 10MPa. The heating temperature is not particularly limited, but is preferably 100 to 200 ℃. These pressing and heating are preferably performed in the range of 0.5 seconds to 100 seconds, and can be bonded even under heating at 130 to 180 ℃, 3MPa, and 10 seconds.
The present invention can provide the inventions described in the following [1] to [6 ].
[1] An adhesive film for circuit connection, comprising: a resin component containing a thermoplastic resin, a radical polymerizable compound, and a radical polymerization initiator; the conductive particles are formed of a material having a specific shape,
the resin component further contains a silane coupling agent having a fluorene skeleton.
[2] The adhesive film for circuit connection according to the above [1], wherein,
the content of the silane coupling agent having a fluorene skeleton is 0.3 to 15 mass% based on the total mass of the resin component.
[3] The adhesive film for circuit connection according to the above [1] or [2], wherein,
the content of the silane coupling agent having a fluorene skeleton is 1 to 30 parts by mass per 100 parts by mass of the radical polymerizable compound.
[4] The adhesive film for circuit connection according to any one of the above [1] to [3], wherein,
the content of the silane coupling agent having a fluorene skeleton is 1 to 30 parts by mass relative to 100 parts by mass of the thermoplastic resin.
[5] A circuit connection structure is provided with: a 1 st circuit part having a 1 st electrode; a 2 nd circuit part having a 2 nd electrode; and a connection portion disposed between the 1 st circuit member and the 2 nd circuit member to electrically connect the 1 st electrode and the 2 nd electrode to each other, the connection portion comprising a cured product of the adhesive film for circuit connection described in any one of the above [1] to [4 ].
[6] A method for manufacturing a circuit connection structure includes the steps of: the 1 st circuit member having the 1 st electrode, the 2 nd circuit member having the 2 nd electrode, and the adhesive film for circuit connection described in any one of [1] to [4] above, are heated and pressurized in a state where the 1 st electrode and the 2 nd electrode are disposed so as to face each other with the adhesive film for circuit connection interposed therebetween, whereby the 1 st electrode and the 2 nd electrode are electrically connected.
Examples
The present invention will be described more specifically with reference to examples, but the present invention is not limited to the examples.
< Synthesis of urethane acrylate (UA 1) >)
2500 parts by mass (2.50 mol) of poly (1, 6-hexanediol carbonate) (trade name: duran ol T5652, manufactured by Asahi Kasei corporation, number average molecular weight 1000) and 666 parts by mass (3.00 mol) of isophorone diisocyanate (manufactured by Sigma-Aldrich Co.LLC) were uniformly dropped over 3 hours into a reaction vessel equipped with a stirrer, a thermometer, a reflux cooling tube having a calcium chloride drying tube, and a nitrogen gas inlet tube. Then, after sufficiently introducing nitrogen gas into the reaction vessel, the reaction vessel was heated to 70 to 75℃to react the nitrogen gas. Subsequently, 0.53 parts by mass (4.3 mmol) of hydroquinone monomethyl ether (manufactured by Sigma-Aldrich Co.LLC) and 5.53 parts by mass (8.8 mmol) of dibutyltin dilaurate (manufactured by Sigma-Aldrich Co.LLC) were added to the reaction vessel, and 238 parts by mass (2.05 mol) of 2-hydroxyethyl acrylate (manufactured by Sigma-Aldrich Co.LLC) was added thereto, followed by reaction at 70℃for 6 hours in an air atmosphere. Thus, urethane acrylate (UA 1) was obtained. The weight average molecular weight of the urethane acrylate (UA 1) was 15000. In addition, the weight average molecular weight was determined by Gel Permeation Chromatography (GPC) and using a calibration curve based on standard polystyrene according to the following conditions.
(measurement conditions)
The device comprises: GPC-8020 manufactured by TOSOH CORPORATION
A detector: RI-8020 manufactured by TOSOH CORPORATION
Chromatographic column: hitachi Chemical Company Gelpack GLA160S+GLA150S manufactured by Ltd
Sample concentration: 120mg/3mL
Solvent: tetrahydrofuran (THF)
Injection amount: 60 mu L
Pressure: 2.94×10 6 Pa(30kgf/cm 2 )
Flow rate: 1.00mL/min
< preparation of conductive particles >)
On the surface of the polystyrene particles, a layer formed of nickel was formed so that the thickness of the layer became 0.2 μm. Thus, conductive particles having an average particle diameter of 4 μm, a maximum particle diameter of 4.5 μm and a specific gravity of 2.5 were obtained.
(examples 1 to 14, comparative examples 1 to 8)
[ production of adhesive film ]
The following components were mixed in the amounts (parts by mass) shown in tables 1 to 3 to prepare varnish compositions.
(thermoplastic resin)
A1: a40 mass% solution prepared by dissolving 40g of bisphenol A type phenoxy resin (trade name: PKHC, UNIONCARBIDEJAPA NLIMITED. Manufactured) in 60g of methyl ethyl ketone was used (the blending amount in the table indicates the blending amount of bisphenol A type phenoxy resin)
(radical polymerizable Compound)
B1: polyurethane acrylate (UA 1) synthesized as described above
B2: diacrylates having a tricyclodecane skeleton (dicyclopentadiene type diacrylates) (trade name: manufactured by DCP-A, KYOEISHACHEMICALCO., LTD.)
B3: 2-methacryloyloxyethyl acid phosphate (trade name: LIGHT ESTER P-2M,KY OEISHA CHEMICAL Co, manufactured by LTD.)
(radical polymerization initiator)
C1: benzoyl peroxide (product name: NYPER BMT-K40, manufactured by NOF CORPORATION)
(coupling agent)
D1: silane coupling agent having fluorene skeleton (trade name: OGSOLSC-001,Osaka Gas Che micals Co, manufactured by ltd.)
D2: silane coupling agent having fluorene skeleton (trade name: OGSOLSC-003,Osaka Gas Che micals Co, manufactured by ltd.)
H1: 3-methacryloxypropyl trimethoxysilane (trade name: KBM503, shin-Etsu Chemical Co., ltd.)
(conductive particles)
E1: conductive particles produced as described above
(thiol Compound ]
F1: pentaerythritol tetrakis (3-mercaptobutyrate) (trade name: CURRANTS MT PE-1 ("CURRANTS MT" is a registered trademark), manufactured by SHOWA DENKO K.K.), viscosity (@ 25 ℃): 1P a s, molecular weight: 544.8
(filling Material)
G1: silica fine particles (trade name: R104, NIPPON AEROSIL CO., LTD. Manufactured, average particle diameter (primary particle diameter): 12 nm)
The varnish composition obtained in the above was coated on a PET film having a thickness of 50 μm using a coating apparatus. Subsequently, hot air drying was performed at 70℃for 3 minutes, and an adhesive film having a thickness (thickness after drying) of 10 μm was formed on the PET film.
[ production of Circuit connection Structure ]
The prepared adhesive film for circuit connection was provided on a glass substrate with a film electrode (height:) Is manufactured by GEOMATEC co., L td.) using a thermocompression bonding apparatus (heating method: a circuit connection structure (connection structure) was produced by heating and pressurizing with contact heat (manufactured by TA IYO KIKAI ltd.) so as to connect the circuit connection structure over the entire width of 1 mm.
[ evaluation of Circuit connection Structure ]
The obtained circuit connection structure was evaluated as follows.
(connection resistance)
The connection resistance between the counter electrodes immediately after connection and after high-temperature and high-humidity test was measured by a universal meter for the obtained circuit connection structure. The high temperature and high humidity test was performed by placing the test piece in a constant temperature and humidity tank at 85 ℃ and 85% R H for 100 hours. The connection resistance value was obtained as an average value of resistances between the opposing electrodes at 16.
(bond force)
The obtained circuit connection structure was measured for adhesion at room temperature immediately after connection and after high temperature and high humidity test (100 hours in a constant temperature and humidity tank at 85 ℃ and 85% RH) using Tensilon UTM-4 (Toyo Baldwin Co., ltd., peel strength 50 mm/min).
(stripping)
The appearance of the circuit connection structure immediately after connection and the appearance of the connection after high-temperature and high-humidity test were observed by using an optical microscope, and the peeled area was evaluated. Specifically, whether or not peeling occurred at the interface between the glass substrate and the circuit connection portion from the glass substrate side with the thin film electrode was visually checked, and when peeling occurred, the peeling area was calculated and evaluated as 4 stages according to the following criteria.
A: the ratio of the peeling area is less than 10%
B: the ratio of the peeling area is 10% or more and less than 30%
C: the peeling area ratio is 30% or more and less than 60%
D: the ratio of the peeling area is 60% or more
TABLE 1
TABLE 2
TABLE 3
As shown in tables 1 and 2, in examples 1 to 14 using an adhesive film containing a silane coupling agent having a fluorene skeleton, a circuit connection structure capable of sufficiently maintaining a small connection resistance was obtained even after a high-temperature high-humidity test.
On the other hand, in comparative examples 1 to 9 in which the adhesive film did not contain the silane coupling agent having a fluorene skeleton, the connection resistance increased in the circuit connection structure after the high temperature and high humidity test.
In comparative examples 2 to 4, although the adhesion force showed a high value immediately after the connection and after the high temperature and high humidity test, the connection resistance increased in the circuit connection structure after the high temperature and high humidity test. On the other hand, in the circuit connection structure in which the connection resistance increases, since peeling of the connection portion from the circuit member occurs in large amounts, it is assumed that the following is the reason why the above-described effects of the embodiment can be obtained: by blending the silane coupling agent having a fluorene skeleton, (i) adhesion between the adhesive film and the circuit member is improved (adhesion area between the adhesive film and the circuit member is increased) by the chemical reaction of the silane coupling agent at the time of circuit connection, and peeling at the interface between the circuit member and the cured adhesive film can be prevented, and besides, (ii) the adhesive film cured after connection contains a fluorene skeleton, low moisture permeability can be maintained even under high temperature and high humidity conditions, and peeling at the interface with the circuit member is difficult to occur.
Symbol description
1-circuit connection structure, 7-conductive particles, 10-connection portion, 11-insulating layer, 20-1 st circuit component, 21-1 st circuit substrate, 22-1 st circuit electrode (1 st connection terminal), 30-2 nd circuit component, 31-2 nd circuit substrate, 32-2 nd circuit electrode (2 nd connection terminal).

Claims (6)

1. An adhesive film for circuit connection, comprising: a resin component containing a thermoplastic resin, a radical polymerizable compound, and a radical polymerization initiator; the conductive particles are formed of a material having a specific shape,
the resin component further contains a silane coupling agent having a fluorene skeleton.
2. The adhesive film for circuit connection according to claim 1, wherein,
the content of the silane coupling agent having a fluorene skeleton is 0.3 to 15 mass% based on the total mass of the resin component.
3. The adhesive film for circuit connection according to claim 1, wherein,
the content of the silane coupling agent having a fluorene skeleton is 1 to 30 parts by mass relative to 100 parts by mass of the radical polymerizable compound.
4. The adhesive film for circuit connection according to claim 1, wherein,
the content of the silane coupling agent having a fluorene skeleton is 1 to 30 parts by mass relative to 100 parts by mass of the thermoplastic resin.
5. A circuit connection structure is provided with:
a 1 st circuit part having a 1 st electrode;
a 2 nd circuit part having a 2 nd electrode; and
A connection portion disposed between the 1 st circuit member and the 2 nd circuit member and electrically connecting the 1 st electrode and the 2 nd electrode to each other,
the connecting portion comprises a cured product of the adhesive film for circuit connection according to any one of claims 1 to 4.
6. A method for manufacturing a circuit connection structure includes the steps of:
the 1 st circuit member having the 1 st electrode, the 2 nd circuit member having the 2 nd electrode, and the adhesive film for circuit connection according to any one of claims 1 to 4 are heated and pressurized in a state in which the 1 st electrode and the 2 nd electrode are disposed so as to face each other with the adhesive film for circuit connection interposed therebetween, thereby electrically connecting the 1 st electrode and the 2 nd electrode.
CN202280058356.3A 2021-07-01 2022-06-24 Adhesive film for circuit connection, circuit connection structure, and method for producing same Pending CN117882497A (en)

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JP2610900B2 (en) 1987-10-27 1997-05-14 ソニーケミカル 株式会社 Thermosetting anisotropic conductive adhesive sheet and method for producing the same
EP0979854B1 (en) 1997-03-31 2006-10-04 Hitachi Chemical Company, Ltd. Circuit connecting material, and structure and method of connecting circuit terminal
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