Adhesive composition, adhesive film for circuit connection, circuit connection structure, and method for manufacturing the same

Abstract

To provide an adhesive composition and an adhesive film for circuit connection which can provide a circuit connection structure that makes connection resistance between opposing electrodes less likely to increase even under high-temperature and high-humidity conditions, and a circuit connection structure and a method for manufacturing the same.SOLUTION: An 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 contains a cyclopolymerizable monomer as the radical-polymerizable compound.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This disclosure relates to adhesive compositions, adhesive films for circuit connections, circuit connection structures, and methods for manufacturing the same. [Background technology]

[0002] Thermosetting resins using epoxy resins, which exhibit high adhesion and high reliability, are known as circuit connection materials for semiconductor devices and liquid crystal display elements (see, for example, Patent Document 1). The components of the resin generally include epoxy resin, a curing agent such as a phenolic resin that is reactive with the epoxy resin, and a latent curing agent that promotes the reaction between the epoxy resin and the curing agent. The latent curing agent is an important factor in determining the curing temperature and curing rate, and various compounds are used from the viewpoint of storage stability at room temperature and curing rate when heated.

[0003] Recently, radical-curable adhesives that use acrylate derivatives and / or methacrylate derivatives (hereinafter collectively referred to as "(meth)acrylate derivatives") in combination with peroxides, which are radical polymerization initiators, have attracted attention. Radical curing allows for short curing times because the radicals, which are the reactive species, are highly reactive (see, for example, Patent Documents 2 and 3).

[0004] Therefore, short-curing adhesives, which are advantageous for reducing production time, are becoming increasingly popular. In addition, the application of chain transfer agents is being considered to further improve the reactivity of radical-curing adhesives (see, for example, Patent Documents 4 and 5). [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Japanese Patent Application Publication No. 1-113480 [Patent Document 2] Japanese Patent Publication No. 2002-203427 [Patent Document 3] International Publication No. 98 / 044067 Pamphlet [Patent Document 4] Japanese Patent Application Laid-Open No. 2003-221557 [Patent Document 5] International Publication No. WO2009 / 057376 Pamphlet [Summary of the Invention] [Problems to be Solved by the Invention]

[0006] By the way, for the connection of circuit members, an anisotropic conductive adhesive film in which conductive particles are dispersed in an adhesive is used. However, a circuit connection structure obtained by using a radical-curable adhesive as the adhesive tends to have an increase in the connection resistance between opposing electrodes after a high-temperature and high-humidity test.

[0007] Therefore, an object of the present disclosure is to provide an adhesive composition and an adhesive film for circuit connection that can obtain a circuit connection structure in which the connection resistance between opposing electrodes is unlikely to increase even under high-temperature and high-humidity conditions, and a circuit connection structure and a manufacturing method thereof in which the connection resistance between opposing electrodes is unlikely to increase even under high-temperature and high-humidity conditions. [Means for Solving the Problems]

[0008] The gist of the present disclosure is as follows [1] to [8].

[0009] [1] An adhesive composition containing a resin component containing a thermoplastic resin, a radically polymerizable compound, and a radical polymerization initiator, and conductive particles, and containing a cyclization-polymerizable monomer as the radically polymerizable compound.

[0010] According to the above adhesive composition, a circuit connection structure having a property that the connection resistance between opposing electrodes is unlikely to increase even under high-temperature and high-humidity conditions (hereinafter, also referred to as "high-temperature and high-humidity connection reliability") can be obtained.

[0011] [2] The adhesive composition according to [1] above, wherein the content of the cyclization-polymerizable monomer is 3 to 50% by mass based on the total amount of the radically polymerizable compound.

[0012] [3] Further containing a (poly)urethane(meth)acrylate compound as a radically polymerizable compound, the content of the (poly)urethane(meth)acrylate compound being 100 to 1000 parts by mass with respect to 100 parts by mass of the cyclopolymerizable monomer, the adhesive composition according to [1] or [2] above.

[0013] [4] An adhesive film for circuit connection, containing a thermoplastic resin, a radically polymerizable compound, a radical polymerization initiator, and conductive particles, and containing a cyclopolymerizable monomer as the radically polymerizable compound.

[0014] According to the above adhesive film, a circuit connection structure having sufficient high-temperature and high-humidity connection reliability can be obtained.

[0015] [5] The content of the cyclopolymerizable monomer is 3 to 50% by mass based on the total amount of the radically polymerizable compound, the adhesive film for circuit connection according to [4] above.

[0016] [6] Further containing a (poly)urethane(meth)acrylate compound as a radically polymerizable compound, the content of the (poly)urethane(meth)acrylate compound being 100 to 1000 parts by mass with respect to 100 parts by mass of the cyclopolymerizable monomer, the adhesive film for circuit connection according to [4] or [5] above.

[0017] [7] A circuit connection structure including a first circuit member having a first electrode, a second circuit member having a second electrode, and a connection portion disposed between the first circuit member and the second circuit member for electrically connecting the first electrode and the second electrode to each other, the connection portion including a cured product of the adhesive composition according to any one of [1] to [3] above.

[0018] The above circuit connection structure can have sufficient high-temperature and high-humidity connection reliability.

[0019] [8] A method for manufacturing a circuit connection structure, comprising the steps of: heating and pressurizing a first circuit member having a first electrode, a second circuit member having a second electrode, and a circuit connection adhesive film according to any one of [4] to [6] above, with the first electrode and the second electrode facing each other via the circuit connection adhesive film, thereby electrically connecting the first electrode and the second electrode.

[0020] According to the above method, a circuit connection structure with sufficient high-temperature and high-humidity connection reliability can be obtained. [Effects of the Invention]

[0021] According to this disclosure, it is possible to provide an adhesive composition and an adhesive film for circuit connections that can obtain a circuit connection structure in which the connection resistance between opposing electrodes does not easily increase even under high temperature and high humidity conditions, as well as a circuit connection structure in which the connection resistance between opposing electrodes does not easily increase even under high temperature and high humidity conditions, and a method for manufacturing the same. [Brief explanation of the drawing]

[0022] [Figure 1] Figure 1 is a schematic cross-sectional view showing one embodiment of the connection structure. [Modes for carrying out the invention]

[0023] In this specification, numerical ranges indicated using "~" represent a range that includes the numbers before and after "~" as the minimum and maximum values, respectively. In numerical ranges described stepwise in this specification, the upper or lower limit of one step in the numerical range may be replaced with the upper or lower limit of another step in the numerical range. Also, in numerical ranges described in this specification, the upper or lower limit of that numerical range may be replaced with the values ​​shown in the examples. Furthermore, the upper and lower limits described individually can be combined in any way. In this specification, "(meth)acrylate" means at least one of acrylate and its corresponding methacrylate. The same applies to other similar expressions such as "(meth)acryloyl". Furthermore, "(poly)" means both with and without the prefix "poly". Furthermore, "A or B" means that either A or B is included, or both are included. Furthermore, unless otherwise specified, the materials exemplified below may be used individually or in combination of two or more. The content of each component in a composition refers to the total amount of any multiple substances present in the composition, unless otherwise specified, if multiple substances corresponding to each component exist in the composition.

[0024] The embodiments of this disclosure will be described in detail below, with reference to the drawings as appropriate. However, this disclosure is not limited to the embodiments described below.

[0025] <Adhesive composition> The adhesive composition of this embodiment may include a resin component containing (A) a thermoplastic resin (hereinafter also referred to as "component (A)"), (B) a radical polymerizable compound (hereinafter also referred to as "component (B)"), and (C) a radical polymerization initiator (hereinafter also referred to as "component (C)"), and (G) conductive particles (hereinafter also referred to as "component (G)").

[0026] [(A) Component: Thermoplastic resin] (A) The following can be used as components: polyvinyl butyral resin, polyvinyl formal resin, polyamide resin, polyester resin, phenolic resin, epoxy resin, phenoxy resin, polystyrene resin, xylene resin, polyurethane resin, polyester urethane resin, etc. These can be used individually or in combination of two or more.

[0027] The weight-average molecular weight of the above thermoplastic resin is 1.0 × 10⁻⁶, from the perspective of film-forming properties and other factors. 4 The above is also acceptable, and from the viewpoint of mixability, 1.0 × 10 4 The above 1.0 × 10 6 It is acceptable to be less than [a certain value].

[0028] The weight-average molecular weight of a thermoplastic resin is determined by gel permeation chromatography (GPC) using a calibration curve based on standard polystyrene, according to the following conditions. [GPC conditions] Equipment used: Hitachi L-6000 model [Hitachi, Ltd.], Column: Gelpack GL-R420 + Gelpack GL-R430 + Gelpack GL-R440 (3 in total) [Hitachi Chemical Co., Ltd.], Eluent: Tetrahydrofuran, Measurement temperature: 40℃, Flow rate: 1.75 ml / min, Detector: L-3300RI [Hitachi, Ltd.]

[0029] Furthermore, component (A) has a Tg (glass transition temperature) of 40°C or higher and a weight-average molecular weight of 1.0 × 10⁻⁶. 4 A hydroxyl group-containing resin (e.g., phenoxy resin) meeting the above criteria can be used. The hydroxyl group-containing resin may be modified with an epoxy group-containing elastomer.

[0030] In this specification, thermoplastic resins having radically polymerizable functional groups are to be formulated as (B) radically polymerizable compounds.

[0031] Phenoxy resins can be obtained by reacting difunctional phenols with epihalohydrins to a high molecular weight, or by polyaddition reaction between difunctional epoxy resins and difunctional phenols.

[0032] Alternatively, polyester urethane resin may be used as component (A).

[0033] From the viewpoint of further improving the peel-inhibiting effect, the content of component (A) in the adhesive composition may be 5% by mass or more or 30% by mass or more, 80% by mass or less or 60% by mass or less, 5 to 80% by mass or 30 to 60% by mass, based on the resin components of the adhesive composition (for example, components other than conductive particles and fillers).

[0034] [(B) Component: Radical polymerizable compound] (B) Component can be a compound having a radically polymerizable functional group. Examples of radically polymerizable functional groups include vinyl groups, acryloyl groups, and methacryloyl groups. Of these, compounds having an acryloyl group and / or a methacryloyl group are more preferred. Component (B) can be used alone or in combination of two or more.

[0035] The adhesive composition of this embodiment may contain a cyclopolymerizable monomer (hereinafter also referred to as "component (B1)") as component (B).

[0036] (B1) A diene structure-containing monomer can be used as component (B1). Examples of diene structure-containing monomers include 1,5-diene structure-containing monomers which may contain heteroatoms, and 1,6-diene structure-containing monomers which may contain heteroatoms. Component (B1) can be used alone or in combination of two or more.

[0037] As component (B1), an acrylic diene structure-containing monomer represented by the following general formula (1) can be used. [ka] [In formula (1), R 1 represents a hydrogen atom or an organic group having 1 to 30 carbon atoms, and R 2 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a phenyl group, a carboxyl group, an ester group or a cyano group. X and Y each independently represent a methylene group, an imino group, a carbonyl group, an oxygen atom or a sulfur atom which may have an alkyl group having 1 to 4 carbon atoms. Z represents a direct bond, a methylene group which may have an alkyl group having 1 to 4 carbon atoms, an imino group, a carbonyl group, an oxygen atom or a sulfur atom. At least one of the groups X, Y and Z is an oxygen atom, a sulfur atom or an imino group (however, in X - Y - Z, heteroatoms are not adjacent to each other).]

[0038] R 1 When is an organic group having 1 to 30 carbon atoms, examples of such an organic group include a linear saturated hydrocarbon group having 1 to 30 carbon atoms, a linear unsaturated hydrocarbon group having 2 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 3 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, a cyclic ether group having 2 to 30 carbon atoms, and the like. In these organic groups, part or all of the hydrogen atoms may be substituted with at least one substituent selected from the group consisting of an alkoxy group having 1 to 30 carbon atoms, a hydroxyl group and a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like. R 1 may be a methyl group, an ethyl group, an isopropyl group, a phenoxyethyl group, a cyclohexyl group, an isobornyl group, a benzyl group or a tetrahydrofurfuryl group, and may also be a methyl group or a cyclohexyl group.

[0039] R 2 When is an ester group, examples of such an ester group include -COOR 3 (wherein R 3 represents an organic group having 1 to 30 carbon atoms), and the like. R 3 may be the same group as R 1 described above.

[0040] The adhesive composition of this embodiment contains the above-mentioned acrylic diene structure-containing monomer as component (B), making it easy to obtain a circuit connection structure that has the characteristic of not easily increasing the connection resistance between opposing electrodes even under high temperature and high humidity conditions. The inventors speculate as follows on why such an effect can be obtained. In the radical polymerization reaction system containing the above-mentioned acrylic diene structure-containing monomer, it is thought that decyclization and cyclization reactions proceed when heating is performed when connecting circuit members. These reactions form polymers with high crosslink density, polymers with a ring structure in the main chain of the polymer, and polymers with both a crosslink structure and a ring structure, which makes it possible to suppress interfacial delamination by reducing shrinkage stress during connection and to impart heat resistance and moisture resistance to the cured product constituting the connection part, and as a result, the above effect can be obtained.

[0041] Component (B1) can be a monomer containing a 1,6-diene structure represented by the following general formulas (1a) to (1c). In this case, the shrinkage stress generated during connection can be reduced, further suppressing interfacial delamination, thereby further improving the reliability of high-temperature and high-humidity connection.

[0042] [ka] [In formula (1a), R 1 This is synonymous with the above.

[0043] [ka] [In formula (1b), R 1 This is synonymous with the above.

[0044] [ka] [In formula (1c), R 1 This is synonymous with the above, and the two R 1They may be the same or they may be different.

[0045] When the adhesive composition of this embodiment contains the above-mentioned 1,6-diene structure-containing monomer, it becomes even easier to obtain a circuit connection structure with excellent high-temperature and high-humidity connection reliability. This effect is thought to be due to the formation of a THF ring structure in the polymer, which further reduces shrinkage stress during connection.

[0046] Examples of monomers containing a 1,6-diene structure represented by general formula (1a) include allyloxymethylacrylic acid esters such as α-allyloxymethylacrylic acid, methyl α-allyloxymethylacrylate, ethyl α-allyloxymethylacrylate, propyl α-allyloxymethylacrylate, isopropyl α-allyloxymethylacrylate, butyl α-allyloxymethylacrylate, tert-butyl α-allyloxymethylacrylate, phenoxyethyl α-allyloxymethylacrylate, cyclohexyl α-allyloxymethylacrylate, dicyclopentadienyl α-allyloxymethylacrylate, isobornyl α-allyloxymethylacrylate, adamantyl α-allyloxymethylacrylate, benzyl α-allyloxymethylacrylate, and tetrahydrofurfuryl α-allyloxymethylacrylate.

[0047] Examples of monomers containing a 1,6-diene structure represented by general formula (1b) include methallyloxymethylacrylic acid esters such as α-methallyloxymethylacrylic acid, α-methallyloxymethylacrylate methyl, α-methallyloxymethylacrylate ethyl, α-methallyloxymethylacrylate propyl, α-methallyloxymethylacrylate isopropyl, α-methallyloxymethylacrylate butyl, α-methallyloxymethylacrylate tert-butyl, α-methallyloxymethylacrylate phenoxyethyl, α-methallyloxymethylacrylate cyclohexyl, α-methallyloxymethylacrylate dicyclopentadienyl, α-methallyloxymethylacrylate isobornyl, α-methallyloxymethylacrylate adamantyl, α-methallyloxymethylacrylate benzyl, and α-methallyloxymethylacrylate tetrahydrofurfuryl.

[0048] Examples of monomers containing a 1,6-diene structure represented by general formula (1c) include ethers of α-hydroxymethylacrylic acid monomers such as bis(α-hydroxymethylacrylate) ether, bis(α-hydroxymethylacrylate) ether, bis(α-hydroxymethylacrylate) ethyl ether, bis(α-hydroxymethylacrylate) propyl ether, bis(α-hydroxymethylacrylate) isopropyl ether, bis(α-hydroxymethylacrylate) butyl ether, bis(α-hydroxymethylacrylate) tert-butyl ether, bis(α-hydroxymethylacrylate) ether, bis(α-hydroxymethylacrylate) phenoxyethyl ether, bis(α-hydroxymethylacrylate) cyclohexyl ether, bis(α-hydroxymethylacrylate) dicyclopentadienyl ether, bis(α-hydroxymethylacrylate) isobornyl ether, bis(α-hydroxymethylacrylate) adamantyl ether, bis(α-hydroxymethylacrylate) benzyl ether, and bis(α-hydroxymethylacrylate) tetrahydrofurfuryl ether.

[0049] The above monomers can be prepared, for example, by the methods described in Japanese Patent Publication No. 10-226669 and Japanese Patent Publication No. 2012-184402. Alternatively, commercially available products such as "FX-AO-MA" (manufactured by Nippon Shokubai Co., Ltd., trade name) can be used.

[0050] As a 1,5-diene structure-containing monomer that may contain heteroatoms, for example, a 1,5-diene structure-containing monomer represented by the following general formulas (1d) to (1e) can be used.

[0051] [ka] [In formula (1d), R 1 This is synonymous with the above.

[0052] [ka] [In formula (1e), R 1 This is synonymous with the above.

[0053] The content of component (B1) in the adhesive composition may be 3% by mass or more, 7% by mass or more, 50% by mass or less, 45% by mass or less, 3 to 50% by mass, 7 to 45% by mass, 10 to 40% by mass, or 13 to 37% by mass, based on the total mass of component (B), from the viewpoint of reducing the shrinkage stress generated during connection and further suppressing interfacial delamination.

[0054] Furthermore, the content of component (B1) in the adhesive composition may be 1% by mass or more or 4% by mass or more, 35% by mass or less or 30% by mass or less, 1 to 35% by mass, 4 to 30% by mass, 7 to 25% by mass, or 10 to 20% by mass, based on the total mass of the resin components (e.g., components other than conductive particles and fillers) of the adhesive composition, from the viewpoint of reducing shrinkage stress generated during connection and further suppressing interfacial delamination.

[0055] The adhesive composition of this embodiment may contain component (B1) and a radical polymerizable compound other than (B1) (hereinafter also referred to as "component (B2)").

[0056] (B2) Component may also be a polymer such as polyurethane, polystyrene, polyethylene, polyvinyl butyral, polyvinyl formal, polyimide, polyamide, polyester, polyvinyl chloride, polyphenylene oxide, urea resin, melamine resin, phenol resin, xylene resin, epoxy resin, polyisocyanate resin, or phenoxy resin. The polymer used as component (B2) has at least one radically polymerizable functional group in its molecule.

[0057] (B2) It is preferable to include a polymer as component because it is easy to handle and has excellent stress relaxation during curing, and it is even more preferable if the polymer has functional groups such as hydroxyl groups because it improves adhesion.

[0058] The weight-average molecular weight of the above polymer is 1.0 × 10⁻⁶. 4 It may be greater than or equal to 1.0 × 10 in terms of mixability. 4 The above 1.0 × 10 6 The following may also apply. The weight-average molecular weight here is measured using a calibration curve with standard polystyrene by gel permeation chromatography (GPC) according to the conditions described in the examples.

[0059] (B2) Component (B2) can be a (poly)urethane (meth)acrylate compound, which balances the crosslinking density and curing shrinkage when used in combination with component (B1), further reduces connection resistance, and improves high-temperature, high-humidity connection reliability.

[0060] The content of the (poly)urethane (meth)acrylate compound may be 40-95% by mass, 50-90% by mass, or 55-85% by mass, based on the total mass of component (B), in terms of the balance between crosslinking density and curing shrinkage.

[0061] Furthermore, the content of the (poly)urethane (meth)acrylate compound may be 100 to 1000 parts by mass, 130 to 800 parts by mass, or 150 to 650 parts by mass per 100 parts by mass of component (B1), from the viewpoint of balancing crosslink density and curing shrinkage and further reducing connection resistance.

[0062] The component (B2) can be 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, 2,2-bis[4-((meth)acryloxymethoxy)phenyl]propane, 2,2-bis[4-((meth)acryloxypolyethoxy)phenyl]propane, dicyclopentenyl(meth)acrylate, tricyclodecanyl(meth)acrylate, tris((meth)acryloyloxyethyl) isocyanurate, urethane(meth)acrylate, dimethyloltricyclodecane di(meth)acrylate, isocyanurate EO (ethylene oxide) modified diacrylate, 2-methacryloyloxyethyl acid phosphate, etc.

[0063] Furthermore, as component (B2), a substructure having at least one selected from the group consisting of a dicyclopentane skeleton, a tricyclodecane skeleton, and a triazine ring can be used.

[0064] Component (B2) may contain a (meth)acrylate compound represented by the following formula (2) (a (meth)acrylate compound having a phosphate ester structure). In this case, the adhesive strength to the surface of inorganic materials (metals, etc.) is improved, making it suitable for bonding electrodes to each other (for example, circuit electrodes to each other). [ka] In formula (2), n represents an integer from 1 to 3, and R represents a hydrogen atom or a methyl group.

[0065] The (meth)acrylate compound represented by formula (2) can be obtained, for example, by reacting phosphoric anhydride with 2-hydroxyethyl (meth)acrylate. Specific examples of the (meth)acrylate compound represented by formula (1) include mono(2-(meth)acryloyloxyethyl) acid phosphate and di(2-(meth)acryloyloxyethyl) acid phosphate.

[0066] The content of the (meth)acrylate compound represented by formula (2) may be, for example, 1 to 10% by mass, 2 to 5% by mass, or 2.5 to 4% by mass, based on the total mass of component (B), in that it is easier to obtain the crosslink density necessary to reduce connection resistance and improve connection reliability.

[0067] The content of component (B) in the adhesive film for circuit connections may be 5% by mass or more, 20% by mass or more, or 40% by mass or more, based on the total mass of the resin components of the adhesive composition (e.g., components other than conductive particles and fillers), or 5 to 90% by mass, 20 to 75% by mass or 40 to 60% by mass, in order to reduce connection resistance and make it easier to obtain the crosslinking density necessary to improve high temperature and high humidity connection reliability.

[0068] [(C) Component: Radical polymerization initiator] (C) Component can be a compound that generates free radicals, for example, peroxide compounds, azo compounds, and other compounds that decompose upon heating to generate free radicals. The radical polymerization initiator is selected as appropriate depending on the desired connection temperature, connection time, etc. Component (C) can be used alone or in combination of two or more.

[0069] Examples of radical polymerization initiators include diacyl peroxides, peroxydicarbonates, peroxyesters, peroxyketals, dialkyl peroxides, and hydroperoxides.

[0070] Examples of diacyl peroxides include 2,4-dichlorobenzoyl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, stearoyl peroxide, succinic peroxide, benzoyl peroxytoluene, and benzoyl peroxide.

[0071] Examples of peroxydicarbonates include di-n-propyl peroxydicarbonate, diisopropyl peroxydicarbonate, bis(4-t-butylcyclohexyl)peroxydicarbonate, di-2-ethoxymethoxyperoxydicarbonate, di(2-ethylhexylperoxy)dicarbonate, dimethoxybutyl peroxydicarbonate, and di(3-methyl-3-methoxybutylperoxy)dicarbonate.

[0072] Peroxyesters include 1,1,3,3-tetramethylbutyl peroxyneodecanoate, 1-cyclohexyl-1-methylethyl peroxyneodecanoate, t-hexyl peroxyneodecanoate, t-butyl peroxypivalate, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanonate, 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane, 1-cyclohexyl-1-methylethyl peroxy-2-ethylhexanonate, t-hexyl peroxy-2-ethylhexanonate, and t-butyl peroxy Examples include c-2-ethylhexanonate, t-butyl peroxyisobutyrate, 1,1-bis(t-butylperoxy)cyclohexane, t-hexylperoxyisopropyl monocarbonate, t-butylperoxy-3,5,5-trimethylhexanonate, t-butylperoxylaurate, 2,5-dimethyl-2,5-di(m-toluylperoxy)hexane, t-butylperoxyisopropyl monocarbonate, t-butylperoxy-2-ethylhexyl monocarbonate, t-hexylperoxybenzoate, and t-butylperoxyacetate.

[0073] Examples of peroxyketals include 1,1-bis(t-hexylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(t-hexylperoxy)cyclohexane, 1,1-bis(t-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-(t-butylperoxy)cyclododecane, and 2,2-bis(t-butylperoxy)decane.

[0074] Examples of dialkylperoxides include α,α'-bis(t-butylperoxy)diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, and t-butylcumyl peroxide.

[0075] Examples of hydroperoxides include diisopropylbenzene hydroperoxide and cumene hydroperoxide.

[0076] These radical polymerization initiators may be used in combination with decomposition accelerators, inhibitors, etc. Furthermore, those radical polymerization initiators coated with polyurethane-based or polyester-based polymers and microencapsulated are preferred because they extend their shelf life.

[0077] The content of component (C) in the adhesive composition may be 0.1% by mass or more, 0.5% by mass or more, or 1% by mass or more, or 20% by mass or less, 10% by mass or less, or 5% by mass or less, or 0.1 to 20% by mass, 0.5 to 10% by mass, or 1 to 5% by mass, based on the total mass of the resin components of the adhesive composition (e.g., components other than conductive particles and fillers), from the viewpoint of pot life.

[0078] [(G) Component: Conductive particles] Component (G) may be metal particles such as Au, Ag, Ni, Cu, or solder, or conductive carbon particles composed of conductive carbon. Component (G) may also be a transition metal such as Ni coated with a noble metal such as Au. From the viewpoint of obtaining sufficient pot life, the surface layer can be Au, Ag, or platinum group noble metals, and may be Au. Furthermore, component (G) may be a coated conductive particle in which a conductive layer is formed on the surface of a non-conductive particle by coating the surface of a non-conductive particle such as glass, ceramic, or plastic with the aforementioned conductive material, and the outermost layer is composed of a noble metal. When using such particles or molten metal particles, their deformability under heating and pressurization increases the contact area with the electrode during connection, improving reliability.

[0079] Component (G) may be insulating coated conductive particles comprising the above-mentioned metal particles, conductive carbon particles, or coated conductive particles, and an insulating layer that covers the surface of the particles and contains an insulating material such as resin. When component (G) is insulating coated conductive particles, even if the content of component (G) is high, the surface of the particles is covered with resin, so the occurrence of short circuits due to contact between components (G) can be suppressed, and the insulation between adjacent electrode circuits can also be improved.

[0080] Component (G) is used by using one of the various conductive particles described above, either alone or in combination of two or more.

[0081] The maximum particle size of component (G) must be smaller than the minimum electrode spacing (the shortest distance between adjacent electrodes). From the viewpoint of excellent dispersibility and conductivity, the maximum particle size of component (G) may be 1.0 μm or larger, 2.0 μm or larger, or 2.5 μm or larger. From the viewpoint of excellent dispersibility and conductivity, the maximum particle size of component (G) may be 50 μm or smaller, 30 μm or smaller, or 20 μm or smaller. From these viewpoints, the maximum particle size of component (G) may be 1.0 to 50 μm, 2.0 to 30 μm, or 2.5 to 20 μm. In this specification, the particle size of any 300 conductive particles (pcs) is measured by observation using a scanning electron microscope (SEM), and the largest value obtained is taken as the maximum particle size of component (G). If component (G) is not spherical, such as having protrusions, the particle size of component (G) is taken as the diameter of the circle circumscribing the conductive particle in the SEM image.

[0082] The average particle size of component (G) may be 1.0 μm or larger, 2.0 μm or larger, or 2.5 μm or larger, from the viewpoint of excellent dispersibility and conductivity. The average particle size of component (G) may be 50 μm or smaller, 30 μm or smaller, or 20 μm or smaller, from the viewpoint of excellent dispersibility and conductivity. From these viewpoints, the average particle size of component (G) may be between 1.0 and 50 μm, between 2.0 and 30 μm, or between 2.5 and 20 μm. In this specification, the particle size of 300 arbitrary conductive particles (pcs) is measured by observation using a scanning electron microscope (SEM), and the average value of the obtained particle sizes is defined as the average particle size.

[0083] The content of component (G) in the adhesive composition may be in the range of 0.1 to 30 parts by volume per 100 parts by volume of the resin component (e.g., components other than conductive particles and fillers) of the adhesive composition, in order to easily obtain stable connection resistance. The content of component (G) may also be 0.1 to 10 parts by volume, from the viewpoint of preventing short circuits of adjacent circuits due to excessive conductive particles.

[0084] Furthermore, the content of component (G) may be 0.5 to 60% by mass, 3 to 45% by mass, or 6 to 30% by mass, based on the total mass of the resin components (e.g., components other than conductive particles and fillers) of the adhesive composition, in order to easily obtain a stable connection resistance.

[0085] [Other ingredients] The adhesive composition of this embodiment may further contain other components in addition to those described above. Examples of other components include thiol compounds (hereinafter also referred to as component (D)), coupling agents (hereinafter also referred to as component (E)), fillers (hereinafter also referred to as component (F)), and so on. These components can be used individually or in combination of two or more.

[0086] The thiol compound that is component (D) may be a thiol compound having one thiol group (monofunctional thiol compound), or it may be a thiol compound having multiple thiol groups (polyfunctional thiol compound).

[0087] The thiol group in component (D) may be a primary thiol group, a secondary thiol group, or a tertiary thiol group.

[0088] Examples of monofunctional thiol compounds 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, 1,1-dimethylheptanethiol, 2-ethylhexyl-3-mercaptopropionate, n-octyl-3-mercaptopropionate, methoxybutyl-3-mercaptopropionate, and stearyl-3-mercaptopropionate.

[0089] Examples of polyfunctional thiol compounds include pentaerythritol tetrakis(3-mercaptobutyrate), ethanedithiol, 1,3-propanethiol, 1,4-butanethiol, trimethylolpropanetris(3-mercaptopropionate), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate, and tetraethylene glycol bis(3-mercaptopropionate).

[0090] The content of component (D) may be 0.05% by mass or more, 0.5% by mass or more, 1.0% by mass or more, or 1.5% by mass or more, based on the total mass of the resin components of the adhesive composition (e.g., components other than conductive particles and fillers), from the viewpoint of suppressing peeling at the interface between the cured adhesive composition and the circuit member, and suppressing an increase in the connection resistance of the circuit connection structure. Furthermore, the content of component (D) may be 5.0% by mass or less, 3.0% by mass or less, 2.5% by mass or less, or 2.0% by mass or less, based on the total mass of the resin components of the adhesive composition (e.g., components other than conductive particles and fillers), from the viewpoint of suppressing peeling at the interface between the cured adhesive composition and the circuit member, and suppressing an increase in the connection resistance of the circuit connection structure.

[0091] As the coupling agent for component (E), a compound having at least one of a vinyl group, an acrylic group (acryloyl group), an amino group, an epoxy group, or an isocyanate group can be used from the viewpoint of improving adhesion. The coupling agent may be a silane coupling agent, and examples include vinyltrimethoxysilane, vinyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-(meth)acryloxypropylmethyldimethoxysilane, 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropylmethyldiethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatetopropyltriethoxysilane, and condensates thereof. These may be used individually or in combination of two or more.

[0092] The content of component (E) may be 0.5% by mass or more, 1% by mass or more, or 2% by mass or more, and may be 15% by mass or less, 10% by mass or less, or 5% by mass or less, based on the total mass of the resin components of the adhesive composition (for example, components other than conductive particles and fillers).

[0093] (F) The filler material may be, for example, a non-conductive filler (e.g., non-conductive particles). The filler material may be either an inorganic filler or an organic filler. Examples of inorganic fillers include metal oxide nanoparticles such as silica nanoparticles, alumina nanoparticles, silica-alumina nanoparticles, titania nanoparticles, and zirconia nanoparticles; and inorganic nanoparticles such as nitride nanoparticles. Examples of organic fillers include organic nanoparticles such as silicone nanoparticles, methacrylate-butadiene-styrene nanoparticles, acrylic-silicone nanoparticles, polyamide nanoparticles, and polyimide nanoparticles. These nanoparticles may have a uniform structure or a core-shell structure. The maximum diameter of the filler material may be less than the minimum particle size of the conductive particles.

[0094] The content of component (F) may be 4 to 60% by volume, 5 to 50% by volume, or 6 to 30% by volume, based on the total volume of the adhesive composition. Furthermore, the content of the filler may be 3 to 60% by mass, 4 to 40% by mass, or 5 to 20% by mass, based on the total mass of the resin components of the adhesive composition (e.g., components other than conductive particles and fillers), from the viewpoint of improving connection reliability.

[0095] Furthermore, the adhesive composition of this embodiment may contain other additives such as softeners, accelerators, antioxidants, colorants, flame retardants, thixotropic agents, and polymerization inhibitors. Examples of polymerization inhibitors include hydroquinone and methyl ether hydroquinones.

[0096] <Adhesive film for circuit connections> The adhesive film for circuit connection of this embodiment may contain a resin component containing (A) a thermoplastic resin, (B) a radical polymerizable compound, and (C) a radical polymerization initiator, and (G) conductive particles, and may have the same configuration as the adhesive composition of this embodiment described above.

[0097] Furthermore, regarding the content of each component, "based on the total amount of the adhesive composition" shall be read as "based on the total amount of the adhesive film," and "based on the total mass of the resin components of the adhesive composition (e.g., components other than conductive particles and fillers)" shall be read as "based on the total mass of the resin components of the adhesive film (e.g., components other than conductive particles and fillers)."

[0098] When the adhesive film of this embodiment contains conductive particles, the particle density of the conductive particles in the adhesive film for circuit connection is 100 particles / mm² from the viewpoint of obtaining stable connection resistance. 2 More than 1000 pieces / mm 2 or more, or 3000 pieces / mm 2 The above is acceptable. The particle density of conductive particles in the adhesive film for circuit connections should be 100,000 particles / mm² from the viewpoint of ensuring insulation between adjacent electrodes. 2 Below, 50000 pieces / mm 2 The following, or 30,000 pieces / mm 2 The following may apply. From these perspectives, the particle density of conductive particles in the adhesive film for circuit connections is 100 to 100,000 particles / mm². 2 , 1000~50000 pieces / mm 2 , or 3000-30000 pieces / mm 2 That's fine.

[0099] The thickness of the adhesive film for circuit connection may be, for example, 3 μm or more or 10 μm or more, and 30 μm or less or 20 μm or less.

[0100] The circuit connection adhesive film of this embodiment can be suitably used as a circuit connection adhesive film for connecting a first circuit member having a first electrode (for example, a first circuit member having a first circuit electrode formed on the main surface of a first substrate) and a second circuit member having a second electrode (for example, a second circuit member having a second circuit electrode formed on the main surface of a second substrate) with the first electrode and the second electrode (the first circuit electrode and the second circuit electrode) facing each other.

[0101] The adhesive film for circuit connections may have a multilayer structure of two or more layers, as this makes it easier to obtain stable connection resistance.

[0102] The adhesive film for circuit connections may also be an adhesive film for circuit connections that does not contain conductive particles.

[0103] The adhesive film for circuit connection according to this embodiment can be manufactured by the following method. Specifically, first, components (A), (B), and (C), as well as other components added as needed, are added to a solvent (organic solvent) and dissolved or dispersed by stirring, mixing, kneading, etc., to prepare a varnish composition (varnish-like adhesive composition). Then, the varnish composition is applied to a substrate that has been treated with a release agent using a knife coater, roll coater, applicator, comma coater, die coater, etc., and the solvent is evaporated by heating to form an adhesive film for circuit connection on the substrate.

[0104] The solvent used in preparing the varnish composition may be one that has the property of uniformly dissolving or dispersing each component. Examples of such solvents include toluene, acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, propyl acetate, and butyl acetate. These solvents can be used individually or in combination of two or more. The stirring, mixing, and kneading during the preparation of the varnish composition can be carried out using, for example, a stirrer, a 3-roll mill, a ball mill, a bead mill, or a homodisper.

[0105] As for the base material, there are no particular restrictions as long as it has heat resistance that can withstand the heating conditions when the solvent is evaporated. For example, base materials (e.g., films) 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, etc. can be used.

[0106] The heating conditions for volatilizing the solvent from the varnish composition applied to the substrate may be such that the solvent volatilizes sufficiently. For example, the heating conditions may be 40°C to 120°C for 0.1 minutes to 10 minutes.

[0107] The adhesive film for circuit connections in this embodiment may have some solvent remaining without being removed. The solvent content in the adhesive film for circuit connections in this embodiment may be, for example, 10% by mass or less, or 5% by mass or less, based on the total mass of the adhesive film.

[0108] <Circuit connection structure and method for manufacturing the same> Next, a circuit connection structure and its manufacturing method will be described.

[0109] The circuit connection structure of this embodiment comprises a first circuit member having a first electrode, a second circuit member having a second electrode, and a connecting portion disposed between the first circuit member and the second circuit member and electrically connecting the first electrode and the second electrode to each other, wherein the connecting portion includes the adhesive composition of this embodiment or a cured product of the circuit connection adhesive film of this embodiment.

[0110] The manufacturing method of the circuit connection structure of this embodiment comprises the step of electrically connecting the first electrode and the second electrode by heating and pressurizing a first circuit member having a first electrode, a second circuit member having a second electrode, and the circuit connection adhesive film of this embodiment, while the first electrode and the second electrode are arranged facing each other via the circuit connection adhesive film.

[0111] Figure 1 is a schematic cross-sectional view showing one embodiment of a circuit connection structure. The circuit connection structure 1 shown in Figure 1 comprises a first circuit member 20 having a first circuit board 21 and a first circuit electrode (first connection terminal) 22 formed on its main surface 21a, a second circuit member 30 having a second circuit electrode (second connection terminal) 32 formed on a second circuit board 31 and its main surface 31a, and a connection portion 10 interposed between the first circuit member 20 and the second circuit member 30 to bond them together. The second circuit member 30 is positioned opposite the first circuit member 20 such that the second circuit electrode 32 faces the first circuit electrode 22.

[0112] The connection portion 10 is formed by interposing the circuit connection adhesive film of this embodiment between the first circuit member 20 and the second circuit member 30 and applying pressure in that state, and includes a cured product of the circuit connection adhesive film. In this embodiment, an example is shown in which the connection portion 10 is formed using a circuit connection adhesive film containing conductive particles, and the connection portion 10 consists of an insulating layer 11 and conductive particles 7 dispersed within the insulating layer 11. The insulating layer 11 is derived from components of the adhesive film other than the conductive particles and includes a cured product formed by radical polymerization of a radically polymerizable compound.

[0113] The opposing first circuit electrode 22 and second circuit electrode 32 are electrically connected via conductive particles 7. On the other hand, the first circuit electrodes 22 and the second circuit electrodes 32 formed on the same circuit board are insulated from each other.

[0114] Examples of the first circuit board 21 and the second circuit board 31 include chip components such as semiconductor chips, resistor chips, and capacitor chips, and substrates such as printed circuit boards. Typically, circuit components are provided with numerous connection terminals, but in some cases, there may be only one connection terminal.

[0115] More specifically, substrates made of inorganic materials such as semiconductors, glass, and ceramics, plastic substrates, or glass / epoxy substrates are used. Examples of plastic substrates include polyimide film, polycarbonate film, and polyester film. The first and second circuit electrodes are formed from a metal such as copper. To obtain better electrical connections, it is preferable that at least one surface of the first and second circuit electrodes be made of a metal selected from gold, silver, tin, and platinum group metals. The surface layer may be selected from gold, silver, platinum group metals, or tin, or a combination of these may be used. Alternatively, a multilayer structure may be formed by combining multiple metals, such as copper / nickel / gold.

[0116] Furthermore, one of the first circuit member 20 and the second circuit member 30 may be a liquid crystal display panel having a glass substrate or a plastic substrate as a circuit board and connection terminals formed from ITO or the like. Alternatively, one of the first circuit member 20 and the second circuit member 30 may be a flexible printed circuit board (FPC), tape curia package (TCP), or chip-on-film (COF) having a polyimide film as a circuit board, or a semiconductor silicon chip having a semiconductor substrate as a circuit board. These various circuit members can be combined as needed to form a circuit connection structure.

[0117] Furthermore, it is preferable to preheat the substrate equipped with circuit electrodes before the connection process using the circuit connection adhesive film in order to eliminate the influence of volatile components caused by heating during connection on the connection.

[0118] The circuit connection structure 1 is formed, for example, by overlapping a first circuit member 20, a circuit connection adhesive film, and a second circuit member 30 in this order, such that the first connection terminal 22 and the second connection terminal 32 face each other, and then applying pressure or further heating in that state. The pressure is not particularly limited as long as it does not damage the adherend, but generally 0.1 to 10 MPa is preferred. The heating temperature is not particularly limited, but 100 to 200°C is preferred. These pressurizing and heating processes are preferably carried out in the range of 0.5 to 100 seconds, and bonding is also possible with heating at 130 to 180°C, 3 MPa, and 10 seconds. [Examples]

[0119] The present invention will be described more specifically below with reference to examples, but the present invention is not limited to these examples.

[0120] <Synthesis of Polyurethane Acrylate (UA1)> In a reaction vessel equipped with a stirrer, thermometer, reflux condenser with calcium chloride drying tube, and nitrogen gas inlet tube, 2500 parts by mass (2.50 mol) of poly(1,6-hexanediol carbonate) (trade name: Duranol T5652, manufactured by Asahi Kasei Chemicals Corporation, number average molecular weight 1000) and 666 parts by mass (3.00 mol) of isophorone diisocyanate (manufactured by Sigma-Aldrich) were uniformly added dropwise over 3 hours. Then, after sufficiently introducing nitrogen gas into the reaction vessel, the reaction was carried out by heating the inside of the reaction vessel to 70-75°C. Next, 0.53 parts by mass (4.3 mmol) of hydroquinone monomethyl ether (Sigma-Aldrich) and 5.53 parts by mass (8.8 mmol) of dibutyltin dilaurate (Sigma-Aldrich) were added to the reaction vessel. Then, 238 parts by mass (2.05 mol) of 2-hydroxyethyl acrylate (Sigma-Aldrich) were added, and the reaction was carried out at 70°C for 6 hours under an air atmosphere. This yielded polyurethane acrylate (UA1). The weight-average molecular weight of polyurethane acrylate (UA1) was 15,000. The weight-average molecular weight was measured using a calibration curve with standard polystyrene by gel permeation chromatography (GPC) according to the following conditions. (Measurement conditions) Equipment: GPC-8020 manufactured by Tosoh Corporation Detector: RI-8020 manufactured by Tosoh Corporation Column: Hitachi Chemical Co., Ltd. Gelpack GLA160S + GLA150S Sample concentration: 120mg / 3mL Solvent: tetrahydrofuran Injection volume: 60μL Pressure: 2.94 × 10 6 Pa(30kgf / cm 2 ) Flow rate: 1.00mL / min

[0121] <Preparation of conductive particles> By forming a nickel layer with a thickness of 0.2 μm on the surface of polystyrene particles, conductive particles with an average particle size of 4 μm, a maximum particle size of 4.5 μm, and a specific gravity of 2.5 were obtained.

[0122] (Examples 1-4, Comparative Examples 1-4) [Fabrication of adhesive film] The following components were mixed in the amounts (parts by mass) shown in Table 1 to prepare the respective varnish compositions.

[0123] (thermoplastic resin) A1: A 40% by mass solution prepared by dissolving 40g of bisphenol A type phenoxy resin (trade name: PKHC, manufactured by Union Carbide) in 60g of methyl ethyl ketone was used (the amounts in the table indicate the amount of bisphenol A type phenoxy resin).

[0124] (Radical polymerizable compounds) B1-1: Cyclopolymerizable monomer (Product name: FX-AO-MA, manufactured by Nippon Shokubai Co., Ltd.) B2-1: Polyurethane acrylate (UA1) synthesized as described above. B2-2:2-Methacryloyloxyethyl acid phosphate (Product name: Light Ester P-2M, manufactured by Kyoeisha Chemical Co., Ltd.) B2-3: Diacrylate with a tricyclodecane skeleton (dicyclopentadiene type diacrylate) (Trade name: DCP-A, manufactured by Kyoeisha Chemical Co., Ltd.) B2-4: Isobornyl acrylate (product name: IBXA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) (Radical polymerization initiator) C1: Benzoyl peroxide (Product name: Niper BMT-K40, manufactured by NOF Corporation) (Thiol compounds) D1: Pentaerythritol tetrakis(3-mercaptobutyrate) (Product name: Karenz MT PE-1 ("Karenz MT" is a registered trademark), manufactured by Showa Denko K.K.), Viscosity (@25℃): 1 Pa·s, Molecular weight: 544.8 (Coupling agent) E1:3-Methacryloxypropyltrimethoxysilane (Trade name: KBM503, manufactured by Shin-Etsu Chemical Co., Ltd.) (filling material) F1: Silica microparticles (Product name: R104, manufactured by Nippon Aerosil Co., Ltd., average particle size (primary particle size): 12 nm) (Conductive particles) G1: Conductive particles prepared as described above

[0125] The varnish composition obtained above was applied to a 50 μm thick PET film using a coating apparatus. Then, hot air drying was performed at 70°C for 3 minutes to form an adhesive film with a thickness (after drying) of 10 μm on the PET film.

[0126] [Fabrication of circuit connection structures] A circuit connection structure (connection structure) was fabricated by connecting a COF (FLEXSEED) with a pitch of 25 μm and a glass substrate with a thin-film electrode (Geomatec), which has a thin-film electrode made of silicon nitride (SiNx) on a glass substrate (height: 1200 Å), over a width of 1 mm using a thermocompression bonding device (heating method: constant heat type, manufactured by Taiyo Kikai Seisakusho Co., Ltd.) under the conditions of 180°C and 4.5 MPa for 4 seconds.

[0127] [Evaluation of circuit connection structures] The following evaluations were performed on the obtained circuit connection structure.

[0128] (Connection resistance) The connection resistance between opposing electrodes of the obtained circuit connection structure was measured using a multimeter immediately after connection and after the high-temperature, high-humidity test. The high-temperature, high-humidity test was performed by leaving the structure in a constant temperature and humidity chamber at 85°C and 85%RH for 100 hours. The connection resistance was determined as the average value of 16 resistance points between opposing electrodes.

[0129] [Table 1]

[0130] As shown in Table 1, in Examples 1 to 4, which used adhesive films containing cyclopolymerizable monomers, we were able to obtain circuit connection structures that could maintain a sufficiently low connection resistance between opposing electrodes even after high-temperature and high-humidity testing. [Explanation of Symbols]

[0131] 1...Circuit connection structure, 7...Conductive particles, 10...Connection part, 11...Insulating layer, 20...First circuit member, 21...First circuit board, 22...First circuit electrode (first connection terminal), 30...Second circuit member, 31...Second circuit board, 32...Second circuit electrode (second connection terminal).

Claims

1. The material comprises a thermoplastic resin, a radical polymerizable compound, a radical polymerization initiator, and conductive particles. An adhesive composition containing a cyclizable monomer as the radical polymerizable compound.

2. The adhesive composition according to claim 1, wherein the content of the cyclizable monomer is 3 to 50% by mass based on the total amount of the radical polymerizable compound.

3. The radical polymerizable compound further contains a (poly)urethane (meth)acrylate compound, The adhesive composition according to claim 1 or 2, wherein the content of the (poly)urethane (meth)acrylate compound is 100 to 1000 parts by mass per 100 parts by mass of the cyclizable monomer.

4. The material comprises a thermoplastic resin, a radical polymerizable compound, a radical polymerization initiator, and conductive particles. A circuit connection adhesive film containing a cyclizable monomer as the radical polymerizable compound.

5. The circuit connection adhesive film according to claim 4, wherein the content of the cyclizable monomer is 3 to 50% by mass based on the total amount of the radical polymerizable compound.

6. The radical polymerizable compound further contains a (poly)urethane (meth)acrylate compound, The circuit connection adhesive film according to claim 4 or 5, wherein the content of the (poly)urethane (meth)acrylate compound is 100 to 1000 parts by mass per 100 parts by mass of the cyclizable monomer.

7. A first circuit member having a first electrode, A second circuit member having a second electrode, A connecting portion is disposed between the first circuit member and the second circuit member and electrically connects the first electrode and the second electrode to each other, Equipped with, A circuit connection structure wherein the connection portion includes a cured product of the adhesive composition described in claim 1 or 2.

8. A first circuit member having a first electrode, A second circuit member having a second electrode, The circuit connection adhesive film according to claim 4 or 5, A method for manufacturing a circuit connection structure, comprising the step of heating and pressurizing the first electrode and the second electrode while they are arranged facing each other via the circuit connection adhesive film, thereby electrically connecting the first electrode and the second electrode.

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