adhesive composition

Abstract

To provide an adhesive composition which has excellent storage stability and can be cured at a relatively low temperature in a short time.SOLUTION: There is provided an adhesive composition which comprises an onium salt represented by the following formula (1) and a cationic polymerizable material. [In formula (1), R1, R2, R3 and R4 each independently represents a hydrogen atom, an alkyl group, an aryl group, an alkenyl group, a heterocycle group, an alkoxyl group, an aryloxy group or a heterocyclic oxy group, R1, R2, R3 and R4 may be bonded together to form a ring structure and X- represents SbF6-, PF6-, B(C6F5)4-, Ga(C6F5)4-, Ga(C6F5)2F2-, Ga(C6F5)F3- or C(CF3SO2)3-.]SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an adhesive composition and a film-like adhesive composition. [Background technology]

[0002] In recent years, various adhesives have been used in fields such as semiconductors and liquid crystal displays for fixing electronic components, connecting circuits, etc. In these applications, the density and definition are becoming increasingly higher, and adhesives are also required to have high adhesive strength and reliability.

[0003] In particular, anisotropic conductive adhesives, which have conductive particles dispersed in the adhesive, are used as circuit connection materials for connecting liquid crystal displays and TCPs (Tape Carrier Packages), FPCs (Flexible Printed Circuits) and TCPs, or FPCs and printed wiring boards. Recently, even when mounting semiconductor silicon chips on substrates, a method known as COG (Chip On Glass) has been adopted, in which semiconductor silicon chips are directly mounted on substrates rather than the conventional wire bonding method, and anisotropic conductive adhesives are also used here.

[0004] In recent years, in the field of precision electronic devices, the density of circuits has increased, resulting in extremely narrow electrode widths and electrode spacing. Therefore, under the connection conditions of conventional circuit connection adhesives using epoxy resins, there are problems such as circuit (wiring) detachment, peeling, and misalignment, and COG has a problem of warping due to the difference in thermal expansion between the chip and the substrate. Furthermore, to reduce costs, it is necessary to improve throughput, and there is a demand for adhesives that can be cured at relatively low temperatures (e.g., 150 to 170°C) and in a short time (e.g., within 10 seconds) (low-temperature fast-curing adhesives).

[0005] In response to such demands, it is known that an onium salt containing a sulfonium cation having a predetermined structure is used as a polymerization initiator in an adhesive (see Patent Documents 1 and 2 below). [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Patent No. 2706833 [Patent Document 2] Japanese Patent Application Publication No. 6-345726 Summary of the Invention [Problem to be solved by the invention]

[0007] However, when the polymerization initiators described in Patent Documents 1 and 2 are used, polymerization may begin even at temperatures of about 40 to 60°C, and curing of the adhesive may proceed during storage. On the other hand, when a polymerization initiator (e.g., an iodonium salt compound) with lower reactivity than the polymerization initiators described in Patent Documents 1 and 2 is used, storage stability is ensured, but it is difficult to cure the adhesive at a relatively low temperature (e.g., 150 to 170°C) in a short time (e.g., within 10 seconds).

[0008] Therefore, an object of the present invention is to provide an adhesive composition and a film-like adhesive composition that have excellent storage stability and can be cured at a relatively low temperature (for example, 150 to 170°C) in a short time (for example, within 10 seconds). [Means for solving the problem]

[0009] In order to achieve the above object, the present inventors have conducted various studies and discovered that by using an onium salt containing a specific nitrogen onium cation and a counter anion, it is possible to achieve both storage stability and curability at a relatively low temperature in a short time, and have completed the present invention.

[0010] That is, the present invention provides an adhesive composition containing an onium salt represented by the following general formula (1) and a cationically polymerizable substance. [ka] [In formula (1), R 1 , R 2 , R 3 and R 4 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic oxy group; R 1 , R 2 , R 3 and R 4 may be bonded to each other to form a ring structure, and X - is SbF6 - , PF6 - , B(C6F5)4 - , Ga(C6F5)4 - , Ga(C6F5)2F2 - , Ga(C6F5)F3 - or C(CF3SO2)3 - represents.]

[0011] The adhesive composition according to the present invention has excellent storage stability and can be cured at a relatively low temperature (e.g., 150 to 170°C) in a short time (e.g., within 10 seconds). Such an adhesive composition can be suitably used as an adhesive composition for circuit connection.

[0012] The onium salt is preferably at least one selected from the group consisting of anilinium salts and pyridinium salts.

[0013] R in general formula (1) 1 , R 2 , R 3 and R 4 Preferably, any one of the groups is a substituted or unsubstituted benzyl group, a substituted or unsubstituted naphthylmethyl group, or a substituted or unsubstituted cinnamyl group.

[0014] The cationically polymerizable substance may be at least one selected from the group consisting of epoxy compounds, oxetane compounds, and vinyl ether compounds.

[0015] The adhesive composition may further contain a film property-imparting polymer.The adhesive composition may further contain conductive particles.

[0016] The adhesive composition may have anisotropic conductivity. The adhesive composition may be for circuit connection.

[0017] The present invention also provides a film-like adhesive composition obtained by forming the adhesive composition into a film. [Effects of the Invention]

[0018] According to the present invention, it is possible to provide an adhesive composition and a film-like adhesive composition that have excellent storage stability and can be cured at a relatively low temperature (for example, 150 to 170° C.) in a short time (for example, within 10 seconds). [Brief explanation of the drawings]

[0019] [Figure 1] 1 is a schematic cross-sectional view showing one embodiment of a film-like adhesive composition having anisotropic conductivity. [Figure 2] FIG. 1 is a schematic cross-sectional view showing one embodiment of a structure. [Figure 3] 3A to 3C are schematic cross-sectional views showing a method for manufacturing the structure of FIG. 2. DETAILED DESCRIPTION OF THE INVENTION

[0020]

[0023] In the present specification, the content of each component in a composition means the total amount of each component in the composition unless otherwise specified, when the composition contains multiple substances corresponding to each component.

[0021] The adhesive composition according to the present embodiment contains (A) an onium salt (onium salt compound; hereinafter also referred to as "component (A)") represented by the following general formula (1), and (B) a cationically polymerizable substance (hereinafter also referred to as "component (B)").

[0022] [ka] [In formula (1), R 1 , R 2 , R 3 and R 4 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic oxy group; R 1 , R 2 , R 3 and R 4 may be bonded to each other to form a ring structure, and X - is SbF6 - , PF6 - , B(C6F5)4 - , Ga(C6F5)4 - , Ga(C6F5)2F2 - , Ga(C6F5)F3 - or C(CF3SO2)3 - represents.]

[0023] Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an aralkyl group. Examples of the aralkyl group include a benzyl group, a naphthylmethyl group, and a cinnamyl group. These alkyl groups may have a substituent.

[0024] Examples of the aryl group include a phenyl group, a naphthyl group, a biphenyl group, etc. These aryl groups may have a substituent.

[0025] Examples of the alkenyl group include a propenyl group, a 2-butenyl group, a 2-pentanyl group, and a 2-hexanyl group. Examples of the heterocyclic group include a pyridinyl group. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group. Examples of the aryloxy group include a 4-phenylmethoxy group, a 4-phenylethoxy group, and a 4-phenyloxycarbonylmethyl group. Examples of the heterocyclic oxy group include a 4-cyclohexaneoxide group. These groups may have a substituent.

[0026] Examples of substituents in the alkyl, aryl, and other groups include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, and hexyl; aryl groups such as phenyl and naphthyl; alkoxy groups such as methoxy, ethoxy, propoxy, and butoxy; alkoxycarbonyl groups such as acetoxy, propionyloxy, decylcarbonyloxy, and dodecylcarbonyloxy; ester groups such as methoxycarbonyl, ethoxycarbonyl, and benzoyloxy; phenylthio; halogen atoms such as fluorine, chlorine, bromine, and iodine; cyano; nitro; and hydroxy. The substitution positions of these substituents are not particularly limited and may be any positions.

[0027] X in equation (1) - represents a counter anion of the nitrogen onium cation. - For example, SbF6 - , PF6 - , B(C6F5)4 - , Ga(C6F5)4 - , Ga(C6F5)2F2 - , Ga(C6F5)F3 - and C(CF3SO2)3 - When the nucleophilicity of the anion is low, better curing properties can be obtained, so SbF6 - , (C6F5)4B - , (CF3SO2)3C - is preferred.

[0028] R 1 , R 2 , R 3 and R 4 One of the following (R 1 , R 2 , R 3 and R 4 From the viewpoint of lowering the decomposition temperature of the initiator and further improving the curability, it is preferable that the alkyl group (only one of the above) is a substituted or unsubstituted benzyl group, a substituted or unsubstituted naphthylmethyl group, or a substituted or unsubstituted cinnamyl group.

[0029] R 1 , R 2 , R 3 and R 4 may be bonded to each other to form a ring structure, for example, R 1 , R 2 , R 3 and R 4 Adjacent groups among these bond to each other to form a ring structure. Examples of nitrogen onium cations having a ring structure include cations represented by the following general formula (2). Examples of the ring structure Q include heterocycles, aromatic rings, heteroaromatic rings (such as pyridinium rings), and alicyclic rings. The ring structure Q is, for example, a multi-membered ring such as a four-membered ring, a five-membered ring, a six-membered ring, or a seven-membered ring. The ring structure Q may be unsubstituted or may have a substituent. Examples of the substituent include the substituents described above for each group such as an alkyl group or an aryl group. m represents 1 or 2. R 5 is R 1 , R 2 , R 3 and R 4 is a group equivalent to

[0030] [ka]

[0031] From the viewpoint of achieving even better storage stability, the component (A) is preferably a compound that exhibits activity at temperatures of 80 to 250°C, and specifically, at least one selected from the group consisting of anilinium salts (anilinium salt compounds) and pyridinium salts (pyridinium salt compounds) is more preferred.

[0032] As the anilinium salt, from the viewpoint of lowering the decomposition temperature and further improving the curability, N-alkylanilinium salts, N,N-dialkylanilinium salts and N,N,N-trialkylanilinium salts are preferred. Specific examples of anilinium salts include N-benzyl-N,N-dimethylanilinium antimony hexafluoride, N-(4-nitrobenzyl)-N,N-dimethylanilinium antimony hexafluoride, N-(4-methoxybenzyl)-N,N-dimethylanilinium antimony hexafluoride, N-(α-phenylbenzyl)-N,N-dimethylanilinium antimony hexafluoride, N-(α-methylbenzyl)-N,N-dimethylanilinium antimony hexafluoride, N-(1-naphthylmethyl)-N,N-dimethylanilinium antimony hexafluoride, N-cinnamyl-N,N-dimethylanilinium antimony hexafluoride, and onium salts having a substituted benzylanilinium cation (e.g., K-PURE CXC-1612 (KING Industries, counter anion: SbF6), K-PURE CXC-1738 (KING Industries, counter anion: SbF6)). Examples of anilinium salts include KING Industries, K-PURE CXC-1740 (KING Industries, K-PURE CXC-1741 (KING Industries, K-PURE CXC-1741, counter anion: SbF6), and K-PURE CXC-1821 (KING Industries, K-PURE CXC-1821, counter anion: B(C6F5)4). In these compounds, the aromatic ring bonded to the nitrogen atom may be unsubstituted or may have a substituent. Examples of anilinium salts having a substituent on the aromatic ring include N-(1-naphthylmethyl)-N,N-dimethyl(4-bromophenyl)anilinium antimony hexafluoride.

[0033] As the anilinium salt, from the viewpoint of lowering the decomposition temperature and further improving the curability, N-benzyl-N,N-dialkylanilinium salt and N-naphthylmethyl-N,N-dialkylanilinium salt are preferred, and N-benzyl-N,N-dimethylanilinium salt and N-naphthylmethyl-N,N-dimethylanilinium salt are more preferred. As the counter anion of these anilinium salts, from the viewpoint of improving the reaction rate of the cationic polymerization reaction and further improving the curability, SbF6 - is preferred.

[0034] As the pyridinium salt, N-benzylpyridinium salt, N-naphthylmethylpyridinium salt, and N-cinnamylpyridinium salt are preferred from the viewpoint of lowering the decomposition temperature and further improving the curability. As the counter anion of these pyridinium salts, SbF6 is preferred from the viewpoint of improving the reaction rate of the cationic polymerization reaction and further improving the curability. - is preferred. Specific examples of pyridinium salts include N-benzylpyridinium antimony hexafluoride, N-(4-nitrobenzyl)pyridinium antimony hexafluoride, N-(4-methoxybenzyl)pyridinium antimony hexafluoride, N-(α-phenylbenzyl)pyridinium antimony hexafluoride, N-(α-methylbenzyl)pyridinium antimony hexafluoride, N-(1-naphthylmethyl)pyridinium antimony hexafluoride, and N-cinnamylpyridinium antimony hexafluoride. The pyridinium ring in these compounds may be unsubstituted or may have a substituent. Examples of pyridinium salts having a substituted pyridinium ring include N-(α-phenylbenzyl)-4-cyanopyridinium antimony hexafluoride, naphthylmethyl-2-cyanopyridinium antimony hexafluoride, and cinnamyl-2-cyanopyridinium antimony hexafluoride.

[0035] The content of component (A) is preferably 0.05 parts by mass or more, and more preferably 0.1 parts by mass or more, per 100 parts by mass of component (B), since the adhesive composition tends to be sufficiently cured easily. The content of component (A) is preferably 30 parts by mass or less, and more preferably 15 parts by mass or less, per 100 parts by mass of component (B), since the compatibility tends to be improved.

[0036] The component (A) may be used alone or in combination with multiple types. Furthermore, in order to increase the cation generation efficiency of the component (A) and the reaction rate of the component (B), a chain transfer agent may be used as appropriate in addition to the components (A) and (B). The chain transfer agent is not particularly limited as long as it is a protic compound, and known compounds can be used. Examples of the chain transfer agent that can be used include alcohols such as cyclohexene diol, 2,3-butane diol, ethylene glycol, diethylene glycol, and triethylene glycol, as well as derivatives thereof.

[0037] The (B) cationically polymerizable substance is a substance having a cationically polymerizable substituent. Examples of the cationically polymerizable substituent include an epoxy group, an oxetanyl group, and a vinyl ether group. Examples of the (B) component include an epoxy compound, an oxetane compound, and a vinyl ether compound. Examples of the epoxy compound include a glycidyl ether type epoxy compound and an alicyclic epoxy compound. The (B) component may be used alone or in combination of two or more types.

[0038] The glycidyl ether-type epoxy compound of component (B) may be any known compound that has a glycidyl ether group in the molecule and that cures upon exposure to actinic rays or heat in the presence or absence of a curing agent. Among these, glycidyl ether-type epoxy compounds having two or more epoxy groups per molecule are preferred because they increase the crosslink density upon curing. Examples of glycidyl ether-type epoxy compounds include bisphenol-type epoxy resins derived from epichlorohydrin and bisphenol compounds (such as bisphenol A and bisphenol F); polyglycidyl ethers; novolac-type epoxy compounds such as cresol novolac-type epoxy resins and phenol novolac-type epoxy resins; biphenyl diglycidyl ether, glycidyl alkyl isocyanurate, polyglycidyl methacrylate, and copolymers of glycidyl methacrylate and a vinyl monomer copolymerizable therewith. The glycidyl ether-type epoxy compounds may be used alone or in combination.

[0039] The alicyclic epoxy compound (B) may be any known compound having an epoxy group in the molecule that can be cured by irradiation with actinic rays or heating in the presence or absence of a curing agent. Among these, alicyclic epoxy compounds having two or more epoxy groups in one molecule are preferred because they increase the crosslink density upon curing. Examples of alicyclic epoxy compounds that can be used include cyclohexene oxide- or cyclopentene oxide-containing compounds obtained by oxidizing a cyclohexene ring-containing compound or a cyclopentene ring-containing compound. Examples of the alicyclic epoxy compounds include 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane-metadioxane, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, 3, Examples of the alicyclic epoxy compounds include 4-epoxy-6-methylcyclohexylcarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, ethylene bis(3,4-epoxycyclohexanecarboxylate), dicyclopentadiene diepoxide, bis(3,4-epoxycyclohexylmethyl)adipate, and methylene bis(3,4-epoxycyclohexane). The alicyclic epoxy compounds may be used alone or in combination of two or more.

[0040] The oxetane compound of component (B) may be any oxetane compound having an oxetanyl group in the molecule that is cured by irradiation with actinic rays or heating in the presence or absence of a curing agent. Among these, oxetane compounds having two or more oxetanyl groups are preferred because they increase the crosslink density when cured. From the viewpoint of achieving even better curability, aliphatic or alicyclic compounds having 2 to 6 oxetanyl groups and 1 to 6 hydroxyl groups in the molecule are particularly preferred. The oxetane compounds may be used alone or in combination.

[0041] Specific examples of the oxetane compound include compounds represented by the following general formula (3). [ka]

[0042] In formula (3), R 11 represents a hydrogen atom, a fluorine atom, or a monovalent hydrocarbon group, and R 12 represents a hydrogen atom or an n-valent hydrocarbon group, where n is an integer of 1 or more. 12 When R represents a monovalent hydrocarbon group, examples of the hydrocarbon group include an alkyl group and an aryl group. 12 When is a hydrogen atom, n is 1. When n is an integer of 2 or more, R 12 The oxygen atoms bonded to each other are R 12 may be bonded to the same carbon atom of R 12 In addition, n is, for example, an integer of 4 or less.

[0043] Examples of the oxetane compound include 1,4-di[(3-oxetanyl-n-butoxy)methyl]benzene, 4,4'-bis[(3-oxetanyl-n-butoxy)methyl]biphenyl, 3-ethyl-3{[(3-ethyloxetan-3-yl)methoxy]methyl}oxetane, 3-ethyl-3-hydroxymethyloxetane, and 2-ethylhexyloxetane.

[0044] The vinyl ether compound of component (B) may be any compound having a vinyl ether group in the molecule that can be cured by irradiation with actinic rays or heating in the presence or absence of a curing agent. Among these, vinyl ether compounds having two or more vinyl ether groups in one molecule are preferred because they increase the crosslink density when cured. The vinyl ether compounds may be used alone or in combination.

[0045] Specific examples of the vinyl ether compound include compounds represented by the following general formula (4). [ka]

[0046] In formula (4), R 13 represents a p-valent hydrocarbon group, where p is an integer of 1 or more. 13 When R represents a monovalent hydrocarbon group, examples of the hydrocarbon group include an alkyl group and an aryl group. When p is an integer of 2 or more, R 13 The oxygen atoms bonded to each other are R 13 may be bonded to the same carbon atom of R 13 In addition, p is, for example, an integer of 4 or less.

[0047] Examples of the vinyl ether compound include 1,4-butanediol divinyl ether, cyclohexanedimethanol divinyl ether, diethylene glycol divinyl ether, and triethylene glycol divinyl ether.

[0048] The cationic polymerizable substituent equivalent of component (B) is preferably 43 to 1000 g / mol, more preferably 50 to 800 g / mol, and even more preferably 73 to 600 g / mol. If the cationic polymerizable substituent equivalent is 43 g / mol or more or 1000 g / mol or less, sufficient adhesive strength can be ensured when connecting electrodes, as described below.

[0049] The (B) component contains impurity ions (Na+ , Cl - From the viewpoint of corrosion prevention, it is preferable to use a high-purity product in which the content of hydrolyzable chlorine, etc. is reduced to 300 ppm or less.

[0050] The content of component (B) is preferably 10% by mass or more, and more preferably 25% by mass or more, based on the total amount of the adhesive composition, from the viewpoint of obtaining even better physical properties (glass transition temperature, elastic modulus, etc.) of the cured product of the adhesive composition. The content of component (B) is preferably 90% by mass or less, and more preferably 75% by mass or less, based on the total amount of the adhesive composition, from the viewpoint of suppressing shrinkage of the adhesive composition during curing and maintaining adhesive strength.

[0051] The adhesive composition according to this embodiment may further contain a film-forming polymer (C) (hereinafter also referred to as "component (C)") as a component different from components (A) and (B) for the purpose of thickening or improving film-forming properties. Any known polymer can be used as component (C) without limitation, as long as it does not inhibit the curing of component (B). Examples of such polymers include polyimide, polyamide, phenoxy resin, polymethacrylate, polyacrylate, polyurethane, polyester, polyesterurethane, polyvinyl butyral, SBS (styrene-butadiene-styrene copolymer) and its epoxy-modified derivatives, SEBS (styrene-ethylene-butylene-styrene copolymer) and its modified derivatives, and NBR (acrylonitrile-butadiene copolymer) and its hydrogenated derivatives. Component (C) may be used alone or in combination. These polymers may contain siloxane bonds or fluorine substituents. Such polymers are suitable for use in adhesive compositions when the resins to be mixed are completely compatible with each other or when microphase separation occurs, resulting in a cloudy appearance.

[0052] The weight-average molecular weight of component (C) is not particularly limited, but is preferably in the following range. From the viewpoints of easily improving film-forming properties and enabling the melt viscosity, which affects the flowability of the adhesive composition, to be set over a wide range, the weight-average molecular weight of component (C) is preferably 5,000 or more, more preferably 10,000 or more. From the viewpoint of ensuring sufficient compatibility between component (C) and other components, the weight-average molecular weight of component (C) is preferably 150,000 or less, more preferably 80,000 or less. The weight-average molecular weight of component (C) can be calculated using gel permeation chromatography (GPC) by conversion from a calibration curve using standard polystyrene. Measurement conditions that can be used include, for example, the following conditions. (Measurement conditions) Equipment: Tosoh GPC-8020 Detector: Tosoh Corporation RI-8020 Column: Hitachi Chemical Co., Ltd. Gelpack GL-A-160-S + GL-A150 Sample concentration: 120mg / 3ml Solvent: tetrahydrofuran Injection volume: 60μl Pressure: 30kgf / cm 2 Flow rate: 1.00ml / min

[0053] The content of component (C) is preferably 20 to 320 parts by mass per 100 parts by mass of component (B). When the content is within this range, the adhesive composition tends to have sufficient fluidity and adhesiveness.

[0054] The adhesive composition according to this embodiment may further contain (D) conductive particles. Examples of the (D) conductive particles include particles of metals such as Au, Ag, Ni, Cu, solder, and carbon. The (D) conductive particles may be particles in which a non-conductive core of glass, ceramic, plastic, or the like is coated with the above metal or carbon. Conductive particles in which a plastic core is coated with the above metal or carbon, or heat-fusible metal particles, are preferred because they deform under heat and pressure, increasing the contact area between the conductive particles and electrodes during connection and improving connection reliability. The (D) conductive particles may also be coated particles in which the surfaces of the above conductive particles are further coated with a polymer resin or the like. The coated particles can suppress short circuits caused by contact between particles when the particle content is increased and improve insulation between electrode circuits. The coated particles may be used alone or in combination with conductive particles that are not coated with a polymer resin or the like. The (D) conductive particles may be used alone or in combination.

[0055] The average particle size of the (D) conductive particles is preferably 1 to 18 μm from the viewpoint of excellent dispersibility and conductivity. The content of the (D) conductive particles is not particularly limited, but is preferably 0.1 to 30 vol%, and more preferably 0.1 to 10 vol%, based on the total amount of the adhesive composition. A content of 0.1 vol% or more tends to improve conductivity, while a content of 30 vol% or less tends to sufficiently suppress short circuits. The above content (vol%) is determined based on the volume of each component of the adhesive composition at 23°C before curing. The volume of each component can be converted from mass to volume using specific gravity. The volume of each component can also be determined as the increase in volume when the component is placed in a measuring cylinder or the like containing a solvent (water, alcohol, etc.) that thoroughly wets the component without dissolving or swelling it.

[0056] The adhesive composition according to this embodiment may further contain at least one selected from the group consisting of metal hydroxides and metal oxides for the purpose of preventing corrosion of the adherend. Specifically, the metal hydroxide is preferably at least one selected from the group consisting of aluminum hydroxide, magnesium hydroxide, and calcium hydroxide. Specifically, the metal oxide is preferably at least one selected from the group consisting of silicon oxide, aluminum oxide, magnesium oxide, antimony oxide, tin oxide, titanium oxide, manganese oxide, and zirconium oxide. From the viewpoints of excellent dispersibility in the adhesive composition, adhesive strength to the adherend, and corrosion prevention ability for the adherend, these metal hydroxides or metal oxides are preferably in the form of particles with a particle size of 10 μm or less.

[0057] The total content of the metal hydroxide and metal oxide is preferably 0.1 to 60 parts by mass, and more preferably 1 to 30 parts by mass, per 100 parts by mass of component (B). When the content is 0.1 part by mass or more, a sufficient corrosion prevention effect is obtained, and when the content is 60 parts by mass or less, sufficient dispersibility in the adhesive composition can be ensured.

[0058] The adhesive composition according to the present embodiment may further contain at least one compound selected from the group consisting of a chain ether compound and a cyclic ether compound as a component different from components (A) to (C) for the purpose of controlling the curing behavior of component (B). The chain ether compound or cyclic ether compound is not particularly limited as long as it has two or more ether groups per molecule, and known compounds can be used. Examples of chain ether compounds include polyethylene glycols such as diethylene glycol, triethylene glycol, and tetraethylene glycol; derivatives of these polyethylene glycols in which the terminal hydroxyl groups are functionalized with an ether bond or an ester bond; monofunctional epoxy polymers such as ethylene oxide, propylene oxide, and cyclohexene oxide; crosslinked polyfunctional epoxy polymers; monofunctional or polyfunctional oxetane polymers; and monofunctional or polyfunctional tetrahydrofuran polymers. Examples of cyclic ether compounds include cyclic ether compounds such as 12-crown-4-ether, 14-crown-4-ether, 15-crown-5-ether, 18-crown-6-ether, 21-crown-7-ether, 24-crown-8-ether, 30-crown-7-ether, benzo-18-crown-6-ether, dibenzo-18-crown-6-ether, and tribenzo-18-crown-6-ether; cyclized polyethylene glycol; and cyclized monofunctional epoxy polymers such as ethylene oxide, propylene oxide, and cyclohexene oxide. The chain ether compounds and cyclic ether compounds may each be used alone or in combination.

[0059] Among the chain ether compounds and cyclic ether compounds, cyclic ether compounds are preferred from the viewpoint of excellent reaction controllability, and 12-crown-4-ether, 14-crown-4-ether, 15-crown-5-ether, 18-crown-6-ether, 21-crown-7-ether, 24-crown-8-ether, 30-crown-7-ether, benzo-18-crown-6-ether, dibenzo-18-crown-6-ether and tribenzo-18-crown-6-ether are more preferred.

[0060] The total content of the chain ether compound and cyclic ether compound relative to component (A) is preferably 0.05 to 20 chemical equivalents, more preferably 0.1 to 10. When the content is 0.05 chemical equivalents or more, high adhesive strength is easily obtained, and when the content is 20 chemical equivalents or less, curing is easily performed favorably, and as a result, high crosslink density is easily obtained.

[0061] The adhesive composition according to the present embodiment may further contain various known additives within a range that does not impair the effects of the invention. Examples of additives include inorganic fillers, reinforcing agents, colorants, stabilizers (thermal stabilizers, weather resistance improvers, etc.), extenders, viscosity modifiers, tackifiers such as terpene-phenol copolymers, terpene resins, rosin derivatives, and alicyclic hydrocarbon resins, flame retardants, ultraviolet absorbers, antioxidants, anti-discoloration agents, antibacterial agents, antifungal agents, antioxidants, antistatic agents, plasticizers, lubricants, foaming agents, and mold release agents.

[0062] Examples of colorants include dyes such as direct dyes, acid dyes, basic dyes, and metal complex dyes; inorganic pigments such as carbon black and mica; and organic pigments such as coupling azo pigments, condensed azo pigments, anthraquinone pigments, thioindigo pigments, dioxazone pigments, and phthalocyanine pigments. Examples of stabilizers include hindered phenol pigments, hydrazine pigments, phosphorus pigments, benzophenone pigments, benzotriazole pigments, and oxalic acid anilide pigments. Examples of inorganic fillers include inorganic fibers such as glass fibers, asbestos fibers, carbon fibers, silica fibers, alumina fibers, zirconia fibers, boron nitride fibers, silicon nitride fibers, basic magnesium sulfate fibers, boron fibers, stainless steel fibers, aluminum fibers, titanium fibers, copper fibers, brass fibers, and magnesium fibers; metal powders such as copper, iron, nickel, zinc, tin, lead, stainless steel, aluminum, gold, and silver; wood flour; salts such as aluminum silicate, carbonates, sulfates, phosphates, borates, borosilicates, aluminosilicates, and titanates; basic salts such as basic sulfates and basic carbonates; glass materials such as hollow glass spheres and glass flakes; silicon carbide; aluminum nitride; and minerals such as talc, clay, mullite, and cordierite.

[0063] If the adhesive composition according to this embodiment is liquid at room temperature (25°C; the same applies below), it can be used in a paste form. If the adhesive composition according to this embodiment is solid at room temperature, it may be used in a paste form by heating or by using a solvent. There are no particular restrictions on the solvent as long as it is non-reactive with the adhesive composition and exhibits sufficient solubility, but solvents with a boiling point of 50 to 150°C at normal pressure are preferred. If the boiling point is 50°C or higher, evaporation at room temperature can be suppressed, making it suitable for use in an open system. If the boiling point is 150°C or lower, the solvent can be easily evaporated, ensuring sufficient reliability after adhesion.

[0064] The adhesive composition according to this embodiment can be suitably used as a film-like adhesive composition. The film-like adhesive composition is obtained by forming the adhesive composition according to this embodiment into a film. The film-like adhesive composition can be obtained, for example, by applying a paste-like adhesive composition onto a resin film such as a PET (polyethylene terephthalate) film and drying it.

[0065] The adhesive composition according to this embodiment can be cured, for example, by heat treatment. The heating temperature is preferably 40°C to 250°C, more preferably 40°C to 180°C, and even more preferably 50°C to 150°C. A heating temperature of 40°C or higher makes it easy to ensure a sufficient curing rate, and a heating temperature of 250°C or lower can suppress undesired side reactions. The heating time is preferably 0.1 seconds to 10 hours, and more preferably 1 second to 1 hour. A heating time of 0.1 seconds or longer allows the curing reaction to proceed favorably, and a heating time of 10 hours or shorter can improve the productivity of the cured product and suppress undesired side reactions.

[0066] The adhesive composition according to this embodiment can be bonded to an adherend by applying heat and pressure in combination. The heating temperature is not particularly limited, but is preferably 50 to 190°C. The pressure is not particularly limited as long as it does not damage the adherend, but is generally preferably 0.1 to 30 MPa. The heating and pressure are preferably applied for 0.5 to 120 seconds.

[0067] The adhesive composition according to the present embodiment can be used as an adhesive for bonding adherends of the same kind together, and can also be used as an adhesive for bonding adherends of different kinds (for example, adherends with different thermal expansion coefficients) together. Specifically, the adhesive composition according to the present embodiment can be used as an anisotropic conductive adhesive; an adhesive for circuit connection typified by silver paste, silver film, etc.; an elastomer for CSP, an underfill material for CSP, an adhesive for semiconductor elements typified by LOC tape, etc.

[0068] The adhesive composition according to the present embodiment may have anisotropic conductivity. The adhesive composition having anisotropic conductivity (anisotropic conductive adhesive) contains, for example, (D) conductive particles. The adhesive composition having anisotropic conductivity may be an anisotropic conductive adhesive film (a film-like adhesive composition having anisotropic conductivity).

[0069] Fig. 1 is a schematic cross-sectional view showing one embodiment of an anisotropically conductive adhesive film. As shown in Fig. 1, the anisotropically conductive adhesive film 1 comprises a film-like adhesive component 2 and a plurality of conductive particles 3 disposed in the adhesive component 2.

[0070] The thickness of the anisotropic conductive adhesive film 1 is preferably 10 to 50 μm. If the thickness of the anisotropic conductive adhesive film 1 is 10 μm or more, when used as a circuit connecting material, the circuit connecting material will be sufficiently filled between the circuit electrodes. If the thickness of the anisotropic conductive adhesive film 1 is 50 μm or less, when used as a circuit connecting material, the circuit connecting material can be prevented from leaking out from between the circuit electrodes.

[0071] The adhesive composition according to this embodiment is suitable for use in circuit connection (circuit connection material). Hereinafter, an example of a structure (connection body, circuit connection structure, etc.) using an anisotropic conductive adhesive film 1 containing conductive particles 3, and a method for producing the structure will be described.

[0072] Fig. 2 is a schematic cross-sectional view showing one embodiment of a structure 10. As shown in Fig. 2, a structure 10 includes a first circuit member 4 and a second circuit member 5 facing each other, and a circuit connecting member 6 that connects the first circuit member 4 and the second circuit member 5 between the first circuit member 4 and the second circuit member 5.

[0073] The first circuit member 4 includes a first circuit board 41 and first circuit electrodes 42 formed on a main surface 41a of the first circuit board 41. Note that an insulating layer (not shown) may be formed on the main surface 41a of the first circuit board 41, if necessary.

[0074] The second circuit member 5 includes a second circuit board 51 and second circuit electrodes 52 formed on a main surface 51a of the second circuit board 51. In addition, an insulating layer (not shown) may be formed on the main surface 51a of the second circuit board 51, as the case may be.

[0075] There are no particular limitations on the first circuit member 4 and the second circuit member 5, as long as they are members on which electrodes that require electrical connection are formed. Examples of members on which electrodes are formed (circuit members, etc.) include inorganic substrates such as semiconductors, glass, and ceramics; polyimide substrates such as TCP, FPC, and COF; substrates on which electrodes are formed on films such as polycarbonate, polyester, and polyethersulfone; printed wiring boards, and combinations of two or more of these may also be used.

[0076] The circuit connection member 6 is formed from a cured product of the anisotropic conductive adhesive film 1, and contains an insulating material 7, which is a cured product of the adhesive component 2, and conductive particles 3. The conductive particles 3 may be disposed not only between the opposing first circuit electrode 42 and second circuit electrode 52, but also between the main surface 41 a of the first circuit board 41 and the main surface 51 a of the second circuit board 51. In the structure 10, the first circuit electrode 42 and the second circuit electrode 52 are electrically connected via the conductive particles 3. That is, the conductive particles 3 are in contact with both the first circuit electrode 42 and the second circuit electrode 52.

[0077] In the structure 10, as described above, the opposing first circuit electrode 42 and second circuit electrode 52 are electrically connected via the conductive particles 3. This sufficiently reduces the connection resistance between the first circuit electrode 42 and the second circuit electrode 52. This allows the current to flow smoothly between the first circuit electrode 42 and the second circuit electrode 52, allowing the first circuit member 4 and the second circuit member 5 to fully exhibit their functions.

[0078] A method for manufacturing a structure according to this embodiment includes, for example, a step of placing the electrodes of two substrates, each having an electrode formed thereon, opposite each other, and a compression step of applying heat and pressure to an anisotropically conductive adhesive film disposed between the opposing electrodes of the two substrates. In the compression step, the anisotropically conductive adhesive film is connected to the electrodes, thereby electrically connecting the electrodes via the conductive particles of the anisotropically conductive adhesive film and bonding the substrates together with the anisotropically conductive adhesive film.

[0079] Next, a method for manufacturing a structure will be specifically described with reference to Fig. 3. Fig. 3 is a schematic cross-sectional view showing one embodiment of a method for manufacturing a structure.

[0080] First, a first circuit member 4 and an anisotropic conductive adhesive film 1 are prepared (see FIG. 3(a)).

[0081] Next, the anisotropically conductive adhesive film 1 is placed on the main surface 41a of the first circuit member 4. When the anisotropically conductive adhesive film 1 is laminated on a support (not shown), the laminate is placed on the first circuit member 4 with the anisotropically conductive adhesive film 1 side of the laminate facing the first circuit member 4.

[0082] Then, the anisotropically conductive adhesive film 1 is pressed in the directions of arrows A and B in Figure 3(a) to temporarily connect the anisotropically conductive adhesive film 1 to the first circuit member 4 (see Figure 3(b)). At this time, heating may be performed together with the pressing.

[0083] 3(c), a second circuit member 5 is further placed on the anisotropically conductive adhesive film 1 placed on the first circuit member 4 so that the second circuit electrodes 52 face the first circuit member 4 (i.e., so that the first circuit electrodes 42 and the second circuit electrodes 52 face each other). If the anisotropically conductive adhesive film 1 is laminated on a support (not shown), the support is peeled off and then the second circuit member 5 is placed on the anisotropically conductive adhesive film 1.

[0084] Then, while heating the anisotropically conductive adhesive film 1, pressure is applied in the directions of arrows A and B in Figure 3(c). This hardens the anisotropically conductive adhesive film 1, completing the permanent connection. As a result, a structure 10 as shown in Figure 2 is obtained.

[0085] In the structure 10 obtained as described above, it is possible to bring the conductive particles 3 into contact with both the opposing first circuit electrode 42 and second circuit electrode 52, and the connection resistance between the first circuit electrode 42 and the second circuit electrode 52 can be sufficiently reduced.

[0086] Furthermore, by applying pressure to the anisotropic conductive adhesive film 1 while heating, the adhesive component 2 hardens to form an insulating material 7 while the distance between the first circuit electrode 42 and the second circuit electrode 52 is kept sufficiently small, and the first circuit member 4 and the second circuit member 5 are firmly connected via the circuit connecting member 6. That is, in the structure 10, the circuit connecting member 6 is composed of a cured product of the circuit connecting material, which is the adhesive composition, and therefore the adhesive strength of the circuit connecting member 6 to the first circuit member 4 and the second circuit member 5 is sufficiently high, particularly under high-temperature and high-humidity conditions. Furthermore, in the structure 10, the sufficiently high adhesive strength is maintained for a long period of time. Therefore, in the structure 10, changes over time in the distance between the first circuit electrode 42 and the second circuit electrode 52 are sufficiently suppressed, and the long-term reliability of the electrical properties between the first circuit electrode 42 and the second circuit electrode 52 is excellent.

[0087] In the above embodiment, the structure 10 is manufactured using the anisotropically conductive adhesive film 1, which is easy to handle. Therefore, the anisotropically conductive adhesive film 1 can be easily interposed between the first circuit member 4 and the second circuit member 5, and the first circuit member 4 and the second circuit member 5 can be easily connected. However, an adhesive composition that is not in a film form may be used instead of the anisotropically conductive adhesive film 1. Even in this case, the adhesive composition can be interposed between the first circuit member 4 and the second circuit member 5 by applying a solution obtained by dissolving the adhesive composition in a solvent to either the first circuit member 4 or the second circuit member 5 and drying it.

[0088] According to the present embodiment, there is provided an application of the adhesive composition to circuit connection. According to the present embodiment, there is provided an application of the adhesive composition for producing an adhesive for circuit connection. According to the present embodiment, there is provided an application of the adhesive composition for producing a structure. [Example]

[0089] The present invention will be described in more detail below based on examples, but the present invention is not limited to these examples.

[0090] [Preparation of film-like adhesive composition] Example 1 N-(α-phenylbenzyl)-4-cyanopyridinium antimony hexafluoride was mixed as component (A), an alicyclic epoxy compound (product name GT401, manufactured by Daicel Corporation) as component (B), and a phenoxy resin (product name YP-70, manufactured by Tohto Kasei Co., Ltd.) as component (C). The mixing ratios of each component are shown in Table 1. Furthermore, conductive particles were dispersed at 8 volume % to obtain an adhesive composition. The conductive particles used were polystyrene core particles with an average particle size of 3 μm and a specific gravity of 2.5, each having a 0.2 μm-thick nickel layer on the surface and a 0.02 μm-thick metal layer on the outside of this nickel layer. The adhesive composition was then applied to a 40 μm-thick PET (polyethylene terephthalate) film using a coating device, and dried with hot air at 70°C for 5 minutes to obtain a film-like adhesive composition with an adhesive layer thickness of 20 μm.

[0091] Example 2 A film-like adhesive composition was obtained in the same manner as in Example 1, except that naphthylmethyl-2-cyanopyridinium antimony hexafluoride was used as component (A). The mixing ratio of each component is shown in Table 1.

[0092] Example 3 A film-like adhesive composition was obtained in the same manner as in Example 1, except that cinnamyl-2-cyanopyridinium hexafluoride was used as component (A). The mixing ratio of each component is shown in Table 1.

[0093] Example 4 A film-like adhesive composition was obtained in the same manner as in Example 1, except that naphthylmethyldimethyl(4-bromophenyl)anilinium antimony hexafluoride was used as component (A). The mixing ratio of each component is shown in Table 1.

[0094] Example 5 A film-like adhesive composition was obtained in the same manner as in Example 1, except that benzyldimethylphenylammonium antimony hexafluoride synthesized according to the method described below was used as component (A). The mixing ratios of the components are shown in Table 1. <Synthesis of benzyldimethylphenylammonium antimony hexafluoride> A 10% aqueous solution of benzyldimethylphenylammonium chloride (6.19 g (25 mmol), manufactured by Tokyo Chemical Industry Co., Ltd.) and sodium hexafluoroantimonate (7.11 g (27.5 mmol), manufactured by Wako Pure Chemical Industries, Ltd.) was mixed and stirred for 1 hour. The solvent was removed under reduced pressure to obtain a precipitate. A small amount of water was added to the precipitate, and the mixture was filtered under reduced pressure. The collected residue was dried to obtain a solid. The obtained solid was confirmed to be benzyldimethylphenylammonium antimony hexafluoride. 1 H-NMR spectrum and 19 This was confirmed by F-NMR spectroscopy.

[0095] Example 6 A film-like adhesive composition was obtained in the same manner as in Example 1, except that benzyldimethylphenylammonium tetrakis(pentafluorophenyl)borate (BABF), synthesized according to the method described below, was used as component (A). The mixing ratios of the components are shown in Table 1. <Synthesis of benzyldimethylphenylammonium tetrakis(pentafluorophenyl)borate (BABF)> Benzyldimethylphenylammonium chloride (6.19 g (25 mmol), manufactured by Tokyo Chemical Industry Co., Ltd.) and a 10% aqueous solution of sodium tetrakis(pentafluorophenyl)borate (193.19 g (27.5 mmol), manufactured by Nippon Shokubai Co., Ltd.) were mixed and stirred for 1 hour. The solvent was removed under reduced pressure to obtain a precipitate. A small amount of water was added to the precipitate, and the mixture was filtered under reduced pressure. The collected residue was dried to obtain a solid. The obtained solid was confirmed to be benzyldimethylphenylammonium tetrakis(pentafluorophenyl)borate (BABF). 1 H-NMR spectrum and 19 This was confirmed by F-NMR spectroscopy.

[0096] Example 7 A film-like adhesive composition was obtained in the same manner as in Example 6, except that an oxetane compound (product name OXT-121, manufactured by Toagosei Co., Ltd.) was used as component (B). The mixing ratios of the components are shown in Table 1.

[0097] Example 8 A film-like adhesive composition was obtained in the same manner as in Example 6, except that an alicyclic epoxy compound (product name GT401, manufactured by Daicel Corporation) and an oxetane compound (product name OXT-121, manufactured by Toagosei Co., Ltd.) were used as component (B). The mixing ratios of each component are shown in Table 1.

[0098] (Comparative Example 1) A film-like adhesive composition was obtained in the same manner as in Example 1, except that a sulfonium salt compound (product name: San-Aid SI-60, manufactured by Sanshin Chemical Industry Co., Ltd.) was used as component (A'). The mixing ratios of each component are shown in Table 2.

[0099] (Comparative Example 2) A film-like adhesive composition was obtained in the same manner as in Comparative Example 1, except that an oxetane compound (product name OXT-121, manufactured by Toagosei Co., Ltd.) was used as component (B). The mixing ratios of the components are shown in Table 2.

[0100] (Comparative Example 3) A film-like adhesive composition was obtained in the same manner as in Comparative Example 1, except that an alicyclic epoxy compound (product name GT401, manufactured by Daicel Corporation) and an oxetane compound (product name OXT-121, manufactured by Toagosei Co., Ltd.) were used as component (B). The mixing ratios of each component are shown in Table 2.

[0101] Comparative Example 4 A film-like adhesive composition was obtained in the same manner as in Comparative Example 1, except that a sulfonium salt compound (product name: San-Aid SI-80, manufactured by Sanshin Chemical Industry Co., Ltd.) was used as component (A'). The mixing ratios of each component are shown in Table 2.

[0102] (Comparative Example 5) A film-like adhesive composition was obtained in the same manner as in Comparative Example 2, except that a sulfonium salt compound (product name: San-Aid SI-80, manufactured by Sanshin Chemical Industry Co., Ltd.) was used as component (A'). The mixing ratios of each component are shown in Table 2.

[0103] (Comparative Example 6) A film-like adhesive composition was obtained in the same manner as in Comparative Example 3, except that a sulfonium salt compound (product name: San-Aid SI-80, manufactured by Sanshin Chemical Industry Co., Ltd.) was used as component (A'). The mixing ratios of each component are shown in Table 2.

[0104] [DSC measurement] Using an electronic balance (product name HR202, manufactured by A&D Co., Ltd.), 3.0±0.2 mg of the film-like adhesive composition obtained in each Example and Comparative Example was weighed out as a measurement sample. Using a differential scanning calorimetry (DSC) device (product name DSC7, manufactured by Perkin-Elmer), measurements were performed under a nitrogen gas flow at a temperature range of 30°C to 250°C and a heating rate of 10°C / min, and the exothermic peak temperature (cure temperature) was calculated. The results are shown in Tables 1 and 2.

[0105] The above DSC measurement results show that in all of Examples 1 to 8 and Comparative Examples 1 to 6, the exothermic peak was 150°C or less, indicating that the adhesive composition cures at a relatively low temperature. In particular, in Examples 5, 6, and 8, which used CXC-1612 or CXC1821 as component (A) and the alicyclic epoxy compound GT401 as component (B), the exothermic peak was approximately 100°C, indicating that the adhesive composition cures at a relatively low temperature. Furthermore, it was found that the exothermic peaks in Examples 5, 6, and 8 were equivalent to those in Comparative Examples 1, 3, 4, and 6, which used a sulfonium salt compound as component (A') and the alicyclic epoxy compound GT401 as component (B).

[0106] [Evaluation of storage stability] The infrared absorption spectrum of the film-like adhesive composition obtained in each Example and Comparative Example was measured, and the functional group of component (B) (epoxy group (789 cm -1 ) and oxetanyl group (979cm -1 )) and the sum of the peak areas of aromatic groups (1610 cm -1) was calculated as the ratio R0 (functional group of component (B) / aromatic group) of the total peak area derived from the film-like adhesive composition obtained in each Example and Comparative Example. The film-like adhesive compositions obtained in each Example and Comparative Example were left in a thermostatic chamber at 40°C for one day. After leaving the film-like adhesive compositions at 40°C, the peak area ratio Rx (functional group of component (B) / aromatic group) in the infrared absorption spectrum was calculated in the same manner as above. The cure rate of the film-like adhesive composition was calculated using the following formula (I). The results are shown in Tables 1 and 2. Curing rate (%)=(1-Rx / R0)×100…(I)

[0107] From the above evaluation of storage stability, it can be seen that in Examples 1 to 8, which used component (A), curing hardly progressed and storage stability was good. On the other hand, when SI-60 or SI-80 was used as the sulfonium salt compound as in Comparative Examples 1 to 6, curing progressed rapidly and storage stability was poor in all cases.

[0108] [Table 1]

[0109] [Table 2]

[0110] [Creating a connector] The film-like adhesive compositions obtained in each Example and Comparative Example were transferred from a PET film to a glass substrate (Corning #1737, outer dimensions 38 mm x 28 mm, thickness 0.5 mm, with an ITO (indium tin oxide) wiring pattern (pattern width 50 μm, pitch 50 μm) on the surface) in a size of 2 × 20 mm. Under the mounting conditions (temperature and time) shown in Tables 3 and 4, a load of 80 MPa (equivalent to the bump area) was applied and the substrate was heated and pressurized to mount an IC chip (outer dimensions 1.7 mm x 17.2 mm, thickness 0.55 mm, bump size 50 μm x 50 μm, bump pitch 50 μm). Furthermore, similar mounting was performed using the film-like adhesive compositions after evaluation of storage stability.

[0111] [Connection resistance measurement] The resistance between adjacent circuits of the resulting connection body (the maximum value among the 14 terminals measured) was measured. The results are shown in Tables 3 and 4.

[0112] For all of Examples 1 to 8, measurement of connection resistance after connection at 150°C for 5 seconds showed good values ​​of 10Ω or less both before and after the storage stability evaluation. Furthermore, for Examples 5, 6, and 8, measurement of connection resistance after connection at 130°C for 5 seconds also showed good values ​​of 10Ω or less both before and after the storage stability evaluation. On the other hand, for Comparative Examples 1 to 6, which used a sulfonium salt compound, no connection was possible after the storage stability evaluation.

[0113] [Table 3]

[0114] [Table 4] [Explanation of symbols]

[0115] 1...anisotropic conductive adhesive film, 2...adhesive component, 3...conductive particles, 4...first circuit member, 5...second circuit member, 6...circuit connecting member, 7...insulating material, 10...structure, 41...first circuit board, 42...first circuit electrode, 51...second circuit board, 52...second circuit electrode.

Claims

1. The composition contains an onium salt represented by the following general formula (1) and a cationically polymerizable substance, the cationically polymerizable material comprises an alicyclic epoxy compound; The adhesive composition, wherein the cationically polymerizable substance does not contain an oxetane compound. 【Chemical 1】 [In formula (1), R １ , R ２ , R ３ and R ４ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic oxy group; R １ , R ２ , R ３ and R ４ do not bond to each other to form a ring structure, and X － is PF ６ － , B(C ６ F ５ ) ４ － , Ga(C ６ F ５ ) ４ － , Ga(C ６ F ５ ) ２ F ２ － , Ga(C ６ F ５ ) F ３ － or C(CF ３ SO ２ ) ３ － represents.]

2. The adhesive composition of claim 1 , wherein the onium salt is an anilinium salt.

3. R in general formula (1) １ , R ２ , R ３ and R ４ 3. The adhesive composition according to claim 1, wherein any one of the following is a substituted or unsubstituted benzyl group, a substituted or unsubstituted naphthylmethyl group, or a substituted or unsubstituted cinnamyl group.

4. The adhesive composition according to any one of claims 1 to 3, further comprising a film-imparting polymer.

5. The adhesive composition according to any one of claims 1 to 4, further comprising conductive particles.

6. The adhesive composition according to any one of claims 1 to 5, which has anisotropic conductivity.

7. The adhesive composition according to any one of claims 1 to 6, which is used for circuit connection.

8. The adhesive composition according to any one of claims 1 to 6, which is used as an adhesive for semiconductor elements.

9. The adhesive composition according to any one of claims 1 to 8, which is in a paste form.

10. A film-like adhesive composition obtained by forming the adhesive composition according to any one of claims 1 to 9 into a film.

11. A method for bonding adherends together using the adhesive composition according to any one of claims 1 to 9 or the film-like adhesive composition according to claim 10.

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