TW201720895A - Adhesive composition and structure - Google Patents

Abstract

This adhesive composition comprises a silane compound having a structure represented by general formula (I). (In the formula, X represents an organic group, R1 and R2 each independently represent an alkyl group, m represents an integer from 0 to 2, and s represents an integer of 6 or greater.)

Description

Substance composition and structure

This invention relates to an adhesive composition and structure.

In the semiconductor element and the liquid crystal display element (display display element), various adhesives have been used for the purpose of combining various members in the element. The properties required for the subsequent agent are in the form of adhesion, and cover various aspects such as heat resistance and reliability in a high-temperature and high-humidity state. Further, as the adherend to be used in the following, a metal (titanium, copper, aluminum, etc.), ITO, IZO, IGZO, or the like, a printed wiring board, an organic substrate (for example, a polyimide substrate), and the like are used. A substrate having various surface states such as SiN _x and SiO ₂ needs to be molecularly designed for an adhesive according to each adherend.

Conventionally, a thermosetting resin (epoxy resin, acrylic resin, or the like) exhibiting high adhesion and high reliability has been used for an adhesive for a semiconductor element or an adhesive for a liquid crystal display device. As a constituent component of an adhesive using an epoxy resin, an epoxy resin and a latent curing agent are generally used, and the latent curing agent generates a cationic species or an anionic species reactive with an epoxy resin by heat or light. The latent hardener is an important factor for determining the hardening temperature and the hardening speed, and various compounds can be used from the viewpoint of storage stability at normal temperature and hardening speed at the time of heating. In the actual step, the desired adhesion is obtained, for example, by hardening under a curing condition at a temperature of from 170 ° C to 250 ° C for 10 seconds to 3 hours.

In addition, in recent years, there has been a concern that the semiconductor element is highly integrated and the liquid crystal display element is highly refined, and the pitch between the elements and the wiring is narrowed, which adversely affects the peripheral member due to heat during curing. Further, in order to reduce the cost, it is necessary to increase the throughput, and it is required to change at a low temperature (90 ° C to 170 ° C) for a short period of time (within 1 hour, preferably within 10 seconds, more preferably within 5 seconds). In other words, it is necessary to cure at a low temperature for a short time (low temperature rapid hardening). It is known that in order to achieve such low-temperature short-time hardening, it is necessary to use a thermal latent catalyst having a low activation energy, but it is extremely difficult to achieve storage stability in the vicinity of normal temperature.

Therefore, in recent years, attention has been paid to the use of a (meth) acrylate derivative and a radical hardening adhesive for a peroxide as a radical polymerization initiator, and an epoxy resin and a cerium salt as a cationic polymerization initiator. A cationic hardening adhesive or the like. Since the radical sclerosis is very reactive as a radical of an active species, it can be hardened for a short period of time, and if it is at least the decomposition temperature of the radical polymerization initiator, the peroxide is stably present, so that the peroxide is stably present. It is a hardening system which combines both low-temperature short-time hardening and storage stability (for example, storage stability near normal temperature). In the cation hardening system, since the onium salt which is a reactive species is highly reactive, it can be hardened in a short time, and if it is at least the decomposition temperature of the onium salt, the cationic species are stably present, and therefore, the low-temperature short-time hardening and storage stability are achieved. Hardening system.

On the other hand, in order to achieve a firm adhesion to the adherend, the adhesive may be adhered to by adhesion using a coupling agent or the like as a hydrophobic interaction due to a covalent bond, a hydrogen bond, or a van der Waals force. The case of low molecular weight additives that interact with body surfaces. As the coupling agent, for example, a decane coupling agent; a compound containing a phosphate group, a carboxyl group or the like can be used. In particular, an organic functional group (for example, an organic functional group represented by an epoxy group, an acrylonitrile group, a vinyl group, or the like) which is incorporated into a matrix of a resin after hardening, and an alkoxydecane which interacts with the surface of the adherend In the case of a coupling agent (for example, a coupling agent having a functional group represented by a phosphate group or the like), the adherend and the adhesive can be adhered more firmly (for example, see Patent Document 1 below). [Prior Art Document] [Patent Literature]

Patent Document 1: Japanese Patent Laid-Open Publication No. 2013-191625. Patent Document 2: International Publication No. 2009/063827

[Problems to be Solved by the Invention] However, an adhesive composition containing a decane compound is required to have excellent adhesion after a reliability test under high temperature and high humidity conditions such as 85 ° C, 85% RH, and 60 ° C, 95% RH. strength.

An object of the present invention is to provide an adhesive composition having excellent adhesion strength after a reliability test, and a structure using the same. [Means for solving the problem]

The adhesive composition of the present invention contains a decane compound having a structure represented by the following formula (I). [Chemical 1] (wherein X represents an organic group, R ¹ and R ² each independently represent an alkyl group, m represents an integer of 0 to 2, and s represents an integer of 6 or more.)

However, there have previously been cases where an adhesive containing a decyl group having an alkoxyalkyl group and an organic group bonded to an alkoxyalkyl group via an alkyl group is used. In this regard, the inventors have found the following findings regarding such decane compounds. That is, in the conventional decane compound, the alkyl group present between the Si and the organic group of the alkoxyalkyl group has a small carbon number (for example, the number of methylene groups (CH ₂ ) is short and is 3 or less). Therefore, when one of the first functional groups of the alkoxyalkyl group and the organic group is reacted with one of the constituents of the adhesive (resin or the like) and the adherend, the alkoxyalkyl group and the organic group are reacted. It is difficult to sufficiently separate, whereby the alkoxyalkyl group and the other second functional group in the organic group have low stereoscopic degrees of freedom, and therefore the constituent components (resin or the like) of the second functional group and the adhesive and the adherend are The other one did not sufficiently react, and the effect as a decane compound could not be sufficiently exhibited. As a result, there is a problem in that sufficient strength is not obtained, and the strength is lowered after the reliability test under high temperature and high humidity conditions such as 85 ° C, 85% RH, and 60 ° C, 95% RH.

On the other hand, the adhesive composition of the present invention has excellent adhesion strength after the reliability test. Further, the adherend composition of the present invention has an excellent adhesion before and after the reliability test for the adherend composed of various materials (for example, inorganic substances (oxides, metals, etc.), organic substances, and composites thereof). strength.

The organic group X preferably contains at least one selected from the group consisting of a (meth) acrylonitrile group, a vinyl group, an epoxy group, a nitrogen atom-containing group, and a sulfur atom-containing group.

The adhesive composition of the present invention may further contain an epoxy resin and a latent curing agent.

The adhesive composition of the present invention may further contain a radically polymerizable compound and a cured product which generates a radical by heat or light.

The adhesive composition of the present invention may further contain conductive particles.

The adhesive composition of the present invention can also be used for circuit connection (electrode composition for circuit connection).

The structure of the present invention comprises the above-described adhesive composition or a cured product thereof.

The structure of the present invention may be an embodiment including a first circuit member having a first circuit electrode, a second circuit member having a second circuit electrode, and the first circuit member and the first circuit member The circuit connecting member between the two circuit members, the first circuit electrode and the second circuit electrode are electrically connected, and the circuit connecting member comprises the adhesive composition or a cured product thereof. [Effects of the Invention]

According to the present invention, an adhesive composition having excellent adhesion strength after a reliability test and a structure using the same can be provided. Further, according to the present invention, it is possible to provide an adhesive composition having excellent adhesion strength before and after the reliability test for an adherend composed of various materials, and a structure using the same.

The use of an adhesive composition or a cured product thereof in a structure or its manufacture can be provided by the present invention. The use of an adhesive composition or a cured product thereof in circuit connection can be provided by the present invention. The use of an adhesive composition or a cured product thereof in a circuit-connected structure or its manufacture can be provided by the present invention.

Hereinafter, the embodiments of the present invention will be described, but the present invention is not limited to the embodiments.

In the present specification, the "(meth) acrylate" means at least one of an acrylate and a methacrylate corresponding thereto. The same is true for other similar performances such as "(meth)acrylonitrile" and "(meth)acrylic acid". The materials exemplified below may be used singly or in combination of two or more kinds, unless otherwise specified. In the case where the content of each component in the composition is such that a plurality of substances corresponding to the respective components are present in the composition, unless otherwise specified, the total amount of the plurality of substances present in the composition is indicated. The numerical range represented by "~" indicates a range including the numerical values described before and after "~" and each of which is the minimum value and the maximum value. The "A or B" may include either A or B, or both. The "normal temperature" means 25 °C.

In the numerical range recited in the specification, the upper or lower limit of the numerical range of a certain stage may be replaced with the upper or lower limit of the numerical range of the other stage. Further, in the numerical ranges described in the present specification, the upper limit or the lower limit of the numerical range may be replaced with the values shown in the examples.

The adhesive composition of the present embodiment contains a decane compound having a structure represented by the following formula (I) (hereinafter referred to as "decane compound A" as the case may be). According to the adhesive composition of the present embodiment, the alkoxy fluorenyl group is easily separated from the organic group X by substituting a previously extended alkyl group having a small carbon number to a alkyl group having a carbon number of 6 or more, and thus the alkoxy decane After reacting one of the functional groups in the organic group X, the stereoscopic degree of freedom of the other functional group can also be ensured, thereby exhibiting high adhesion strength to various adherends and sufficient adhesion strength after reliability test. . Such an adhesive composition is suitably used as an adhesive composition for circuit connection.

[Chemical 2] (wherein X represents an organic group, R ¹ and R ² each independently represent an alkyl group, m represents an integer of 0 to 2, and s represents an integer of 6 or more. When R ^{1 is} present, each R ¹ may be The same or different from each other. In the case where R ^{2 is} present, each R ² may be the same or different from each other. Each of R ¹ , R ² and C _s H _2s may also be branched)

The alkylene group of the decane compound A may be any of a linear alkyl group and a branched alkyl group. In the case where the carbon number between the alkoxyalkyl group and the organic group X in the linear alkyl group and the branched alkyl group are the same, it is preferably straight from the viewpoint of making it easier to secure the three-dimensional degree of freedom. Chain alkyl. In the case of using a decane compound A having a linear alkylene group, by reacting one of the functional groups of the alkoxyalkyl group and the organic group X by the previous short methylene number of 6 or more, The stereoscopic degree of freedom of the other functional group is ensured, thereby exhibiting high adhesion strength to various adherends and sufficient adhesion strength after reliability test.

Examples of the constituent component of the adhesive composition of the present embodiment include (a) an epoxy resin (hereinafter referred to as "(a) component)"), and (b) a latent curing agent (epoxy resin). The latent curing agent is hereinafter referred to as "(b) component)"), (c) a radically polymerizable compound (hereinafter referred to as "(c) component"), and (d) by heat (heating) A hardener (hereinafter referred to as "(d) component") which generates a radical (free radical) by light (light irradiation). The first embodiment of the adhesive composition of the present embodiment contains the component (a) and the component (b). The second embodiment of the adhesive composition of the present embodiment contains the component (c) and the component (d). The third embodiment of the adhesive composition of the present embodiment contains the component (a), the component (b), the component (c), and the component (d).

Each component will be described below.

(decane compound) The organic group X of the decane compound A having a structure represented by the formula (I) includes an ethylenically unsaturated bond-containing group (a group containing an ethylenically unsaturated bond) and a nitrogen atom-containing group (containing a nitrogen). The atom of the atom, the sulfur atom contains a group (a group containing a sulfur atom), an epoxy group or the like. Examples of the ethylenically unsaturated bond-containing group include a (meth)acrylonitrile group, a vinyl group, and a styryl group. Examples of the nitrogen atom-containing group include an amine group, a monosubstituted amino group, a disubstituted amino group, an isocyanate group, an imidazolyl group, a urea group, and a maleimine group. Examples of the monosubstituted amino group include an alkylamino group (such as a methylamino group), a benzylamino group, a phenylamino group, a cycloalkylamino group (such as a cyclohexylamino group). Examples of the disubstituted amino group include an acyclic disubstituted amino group, a cyclic disubstituted amine group, and the like. Examples of the acyclic disubstituted amine group include a dialkylamino group (such as a dimethylamino group). Examples of the cyclic disubstituted amine group include a morpholinyl group and a piperazinyl group. Examples of the sulfur atom-containing group include a mercapto group and the like. The epoxy group may be contained in an epoxy group-containing group (epoxy group-containing group) such as a glycidyl group or a glycidoxy group. The (meth)acrylonitrile group may also be contained in the (meth) propylene fluorenyloxy group.

The organic group X is preferably reactive with a component of the adhesive composition other than the decane compound. The organic group X preferably contains a (meth)acryloyl group, a vinyl group, an epoxy group, a nitrogen atom-containing group, and the organic group X, from the viewpoint of further improving the reactivity of the component of the adhesive composition other than the decane compound. The sulfur atom contains at least one of the group consisting of groups.

The alkyl group of R ¹ and R ² has a carbon number of, for example, 1 to 20. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, a decyl group, an undecyl group, and a dodecyl group. Tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl and the like. As R ¹ and R ² , each structural isomer of the alkyl group can be used. The carbon number of the alkyl group of R ¹ is preferably from 1 to 10, more preferably 1 from the viewpoint that it is difficult to form a steric hindrance when reacting with the adherend, and further improving the adhesion to the adherend. ~5. The carbon number of the alkyl group of R ² is preferably from 1 to 10, more preferably from 1 to 5, from the viewpoint of further improving the adhesion to the adherend.

m is an integer of 0 to 2. From the viewpoint of further improving the adhesion to the adherend, m is preferably 0 to 1, more preferably 0. s is an integer of 6 or more. From the viewpoint of increasing the physical distance between the organic group X and the alkoxyalkyl group and increasing the reactivity of the functional groups, s is preferably an integer of from 6 to 20, more preferably an integer of from 6 to 10. From the same viewpoint, the carbon number (linear portion) between the organic group X and the alkoxyalkyl group in the formula (I) is preferably from 6 to 20, more preferably from 6 to 10.

Examples of the decane compound A include glycidoxyalkyltrial alkoxy decane, glycidoxyalkyl dialkoxy decane, (meth) propylene oxyalkyltrial alkoxy decane, and (methyl group). Ethyl propylene dialkyl dialkoxy decane, alkenyl trialkoxy decane, styryl alkyl trialkoxy decane, N-2-(aminoethyl)-8-aminooctyl Methyldimethoxydecane, N-2-(aminoethyl)-8-aminooctyltrimethoxydecane, 3-aminooctyltrimethoxydecane, 3-aminooctyltriethoxylate Baseline, 3-triethoxydecyl-N-(1,3-dimethylbutylidene)octylamine, N-phenyl-8-aminooctyltrimethoxydecane, 8-ureidooctyl Triethoxy decane, 8-decyloctylmethyldimethoxydecane, 8-decyloctyltrimethoxydecane, 8-isocyanate octyltrimethoxydecane, 8-isocyanate octyltriethoxy Base decane and the like.

Examples of the glycidoxyalkyltrialkoxydecane include 8-glycidoxyoctyltrimethoxydecane, 8-glycidoxyoctyltriethoxydecane, and the like. Examples of the glycidoxyalkyl dialkoxy decane include 8-glycidoxyoctylmethyldimethoxydecane, 8-glycidoxyoctylmethyldiethoxydecane, and the like. Examples of (meth)acryloxyalkyltrimethoxydecane include 8-(methyl)propenyloxyoctyltrimethoxydecane and 8-(methyl)propenyloxyoctyltriethoxylate. Base decane and the like. Examples of the (meth) propylene decyloxy dialkyl dialkoxy decane include 8-(meth) propylene decyl octylmethyl dimethoxy decane and 8-(meth) propylene decyloxy group. Octylmethyldiethoxydecane, and the like. Examples of the alkenyl trialkoxydecane include an octenyl trialkoxydecane, an octenylalkyldialkoxydecane, and the like. Examples of the octenyltrialkoxydecane include 7-octenyltrimethoxynonane, 7-octenyltriethoxydecane, and the like. Examples of the octenylalkyldialkoxydecane include 7-octenylmethyldimethoxydecane and 7-octenylmethyldiethoxydecane. Examples of the styrylalkyltrialkoxydecane include p-styryloctyltrimethoxydecane.

The decane compound A can be synthesized, for example, by a method in which an organochlorosilane is reacted with an alcohol. The decane compound A may be used alone or in combination of two or more. The adhesive composition of the present embodiment may further contain a decane compound having a s of 0 to 5 in the formula (I).

The content of the decane compound A is preferably from the viewpoint of the tendency of the adhesion of the interface between the adherend (circuit member or the like) and the adhesive composition or the cured product (circuit connecting member, etc.) to become stronger. The total mass of the adhesive component (the solid component other than the conductive particles in the adhesive composition, the same applies hereinafter) in the agent composition is in the following range. The content of the decane compound A is preferably 0.1% by mass or more, more preferably 0.25 mass% or more, still more preferably 0.5% by mass or more. The content of the decane compound A is preferably 20% by mass or less, more preferably 10% by mass or less, still more preferably 5% by mass or less. From the viewpoint of the above, the content of the decane compound A is preferably from 0.1% by mass to 20% by mass, more preferably from 0.25 % by mass to 10% by mass, even more preferably from 0.5% by mass to 5% by mass.

((a) component: epoxy resin) Examples of the component (a) include bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, naphthalene epoxy resin, and phenol. Novolak type epoxy resin, cresol novolac type epoxy resin, bisphenol A novolak type epoxy resin, bisphenol F novolak type epoxy resin, alicyclic epoxy resin, glycidyl ester type epoxy Resin, glycidylamine type epoxy resin, intramethylene urea type epoxy resin, isomeric cyanate type epoxy resin, aliphatic chain epoxy resin, and the like. The component (a) may be halogenated or hydrogenated. The component (a) may be used alone or in combination of two or more.

The content of the component (a) is preferably in the range of the following, based on the total mass of the adhesive component of the adhesive composition, from the viewpoint of further improving the adhesion to the adherend. The content of the component (a) is preferably 5% by mass or more, more preferably 10% by mass or more, and still more preferably 15% by mass or more. The content of the component (a) is preferably 90% by mass or less, more preferably 80% by mass or less, still more preferably 70% by mass or less. From the viewpoints of the above, the content of the component (a) is preferably from 5% by mass to 90% by mass, more preferably from 10% by mass to 80% by mass, even more preferably from 15% by mass to 70% by mass.

(Component (b): latent curing agent) The component (b) is not particularly limited as long as it can cure the epoxy resin. Examples of the component (b) include a curing agent capable of generating an anionic species by heat or light (an anionic polymerizable catalyst-type curing agent, etc.), and a curing agent capable of generating a cationic species by heat or light (cationic polymerization) An organic catalyst type hardener, etc.), an addition polymerization type hardener, and the like. The component (b) may be used alone or in combination of two or more. The component (b) is preferably a hardener which can generate an anionic species or a cationic species by heat or light, and is preferably anionic polymerizable or cationically polymerizable, from the viewpoint of excellent rapid hardenability and no need to consider chemical equivalents. Catalytic hardener.

Examples of the anionic polymerizable catalyst-type curing agent include an imidazole-based curing agent, an oxime-based curing agent, a boron trifluoride-amine complex, an amine sulfimine, a tertiary amine, and a diaminobutylene. Disubstituted nitriles, melamine and derivatives thereof, salts of polyamines, dicyandiamide, and the like can also be used. Examples of the cationically polymerizable catalyst-type curing agent include a diazonium salt, a phosphonium salt, and the like, and these may be used. Examples of the addition polymerization type curing agent include polyamines, polythiols, polyphenols, and acid anhydrides.

When a tertiary amine or an imidazole curing agent is used as the anionic polymerizable catalyst-type curing agent, it can be heated at a medium temperature of about 160 to 200 ° C for about 10 seconds to several hours. The epoxy resin is hardened. Therefore, the usable life (pot life) can be made longer.

As the cationically polymerizable catalyst-type curing agent, for example, a photosensitive cerium salt (aromatic diazonium salt, aromatic sulfonium salt, or the like) which can cure the epoxy resin by irradiation with an energy ray is preferable. Further, as an epoxy resin which is activated by heat other than the irradiation energy ray, an aliphatic sulfonium salt or the like can be mentioned. Such a hardener is preferred because of its rapid hardenability.

(b) component is coated with a polymer material (polyurethane type, polyester type, etc.), a metal (nickel, ketone, etc.) film, an inorganic substance (such as calcium citrate), etc., and is microencapsulated. The agent is preferred because it can extend the service life.

From the viewpoint of further improving the adhesion to the adherend, the content of the component (b) is preferably in the following range with respect to 100 parts by mass of the component (a). The content of the component (b) is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, and still more preferably 30 parts by mass or more. The content of the component (b) is preferably 500 parts by mass or less, more preferably 100 parts by mass or less, still more preferably 70 parts by mass or less. From the viewpoints of the above, the content of the component (b) is preferably from 10 parts by mass to 500 parts by mass, more preferably from 20 parts by mass to 100 parts by mass, even more preferably from 30 parts by mass to 70 parts by mass.

From the viewpoint of further improving the adhesion to the adherend, the content of the component (b) is preferably the following in terms of 100 parts by mass of the total of the component (a) and the film-forming material (component to be blended as necessary). The scope. The content of the component (b) is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, and still more preferably 30 parts by mass or more. The content of the component (b) is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, still more preferably 70 parts by mass or less. From the viewpoints of the above, the content of the component (b) is preferably from 10 parts by mass to 90 parts by mass, more preferably from 20 parts by mass to 80 parts by mass, even more preferably from 30 parts by mass to 90 parts by mass.

(Component (c): Radical Polymerizable Compound) The component (c) is a compound having a radical polymerizable functional group. Examples of the component (c) include a (meth) acrylate compound, a maleimide compound, a citraconazole resin, and a nadic ylide resin. The "(meth) acrylate compound" means a compound having a (meth) acryl fluorenyl group. The component (c) may be used in the form of a monomer or an oligomer, or may be used in combination with an oligomer. The component (c) may be used alone or in combination of two or more.

Specific examples of the (meth) acrylate compound include methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, isobutyl (meth) acrylate, and ethylene. Alcohol di(meth)acrylate, diethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, tetramethylolmethanetetra(meth)acrylate, 2-hydroxyl -1,3-bis(meth)acryloxypropane, 2,2-bis[4-((meth)acryloxymethoxy)phenyl]propane, 2,2-bis[4- ((Meth)acryloxypolyethoxy)phenyl]propane, dicyclopentenyl (meth)acrylate, tricyclodecyl (meth)acrylate, iso-cyanuric acid (( Methyl)propenyloxyethyl)ester, octa-ocyanuric acid EO-modified di(meth)acrylate, (meth)acrylic acid urethane or the like. For example, a compound described in Patent Document 2 (International Publication No. 2009/063827) can be suitably used as the radically polymerizable compound other than the (meth) acrylate compound. The (meth) acrylate compound may be used alone or in combination of two or more.

The component (c) is preferably a (meth) acrylate compound, more preferably a (meth) acrylate urethane, from the viewpoint of excellent reactivity and stress relaxation property. From the viewpoint of improving heat resistance, it is preferred that the (meth) acrylate compound has at least one substituent selected from the group consisting of a dicyclopentenyl group, a tricyclodecanyl group, and a triazine ring.

Further, as the component (c), a radical polymerizable compound having a phosphate structure represented by the following formula (II) is preferably used, and more preferably, the radical polymerization is carried out by a (meth) acrylate compound or the like. The compound is used in combination with a radically polymerizable compound having a phosphate structure represented by the formula (II). In such cases, the adhesion strength to the surface of the inorganic material (metal or the like) is improved, and thus it is suitable for, for example, the subsequent connection of the circuit electrodes.

[Chemical 3] [wherein, p represents an integer of 1 to 3, and R represents a hydrogen atom or a methyl group]

The radically polymerizable compound having a phosphate structure can be obtained, for example, by reacting anhydrous phosphoric acid with 2-hydroxyethyl (meth)acrylate. Specific examples of the radically polymerizable compound having a phosphate structure include mono(2-(methyl)propenyloxyethyl) phosphate and di(2-(methyl)propenyloxy phosphate. Ethyl) ester and the like. The radically polymerizable compound having a phosphate structure represented by the formula (II) may be used alone or in combination of two or more.

The content of the radically polymerizable compound having a phosphate structure represented by the formula (II) is preferably a ratio with respect to the radical polymerizable compound (corresponding to radical polymerization property) from the viewpoint of further improving the adhesion to the adherend. The total amount of the components of the compound is from 0.1 part by mass to 1000 parts by mass, more preferably from 1 part by mass to 100 parts by mass, per 100 parts by mass. From the viewpoint of further improving the adhesion to the adherend, the content of the radically polymerizable compound having a phosphate structure represented by the formula (II) is preferably a ratio of the radical polymerizable compound and the film forming material. The total amount of 100 parts by mass of the component to be used is from 0.01 part by mass to 50 parts by mass, more preferably from 0.5 part by mass to 10 parts by mass.

The radically polymerizable compound may also contain allyl (meth)acrylate. In this case, the content of the allyl (meth) acrylate is preferably 0.1 part by mass based on 100 parts by mass of the total of the radically polymerizable compound and the film-forming material (components to be used as needed). 10 parts by mass, more preferably 0.5 parts by mass to 5 parts by mass.

From the viewpoint of further improving the adhesion to the adherend, the content of the component (c) is preferably in the range of the following based on the total mass of the adhesive component of the adhesive composition. The content of the component (c) is preferably 10% by mass or more, more preferably 20% by mass or more, and still more preferably 30% by mass or more. The content of the component (c) is preferably 90% by mass or less, more preferably 80% by mass or less, still more preferably 70% by mass or less. From the viewpoints of the above, the content of the component (c) is preferably from 10% by mass to 90% by mass, more preferably from 20% by mass to 80% by mass, even more preferably from 30% by mass to 70% by mass.

(Component (d): a curing agent that generates a radical by light or heat) As the component (d), (d1) a curing agent that generates free radicals by heat (hereinafter referred to as "(d1)" "Component") or (d2) a curing agent that generates free radicals by light (hereinafter referred to as "(d2) component"). The component (d1) is a hardener which decomposes by heat to generate free radicals. Examples of the component (d1) include a peroxide (such as an organic peroxide) and an azo compound. The (d1) component is preferably an organic peroxide having a 10-hour half-life temperature of 40 ° C or higher and a 1-minute half-life temperature of 180 ° C or less, more preferably a 10-hour half-life, from the viewpoint of high reactivity and a long life. The organic peroxide having a temperature of 60 ° C or higher and a one-minute half-life temperature of 170 ° C or lower.

Specific examples of the component (d1) include dinonyl peroxide (such as benzoyl peroxide), peroxydicarbonate, peroxyester, peroxyketal, dialkyl peroxide, and hydrogen peroxide. , decyl peroxide and the like.

From the viewpoint of corrosion of the suppression electrode (circuit electrode or the like), the component (d1) is preferably a hardener containing a chloride ion or an organic acid having a concentration of 5000 ppm or less, more preferably an organic substance produced after thermal decomposition. A hardener with less acid. Specific examples of the component (d1) include a peroxyester, a dialkyl peroxide, hydrogen peroxide, a decyl peroxide, and the like, and more preferably a peroxyester from the viewpoint of obtaining high reactivity.

Examples of the peroxyester ester include cumyl peroxy neodecanoate, peroxy neodecanoic acid-1,1,3,3-tetramethylbutyl ester, and peroxy neodecanoic acid-1-cyclohexyl-1-yl Ethyl ethyl ester, third hexyl peroxy neodecanoate, tert-butyl peroxypivalate, 2-ethylhexanoic acid-1,1,3,3-tetramethylbutyl ester, 2,5 -Dimethyl-2,5-bis(2-ethylhexylperoxy)hexane, 2-ethylhexanoic acid-1-cyclohexyl-1-methylethyl ester, 2-oxide Tertylhexyl ethylhexanoate, tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxyisobutyrate, 1,1-bis(t-butylperoxy)cyclohexane, Third hexyl isopropyl peroxycarbonate, tert-butyl peroxy 3,5,5-trimethylhexanoate, tert-butyl peroxy laurate, 2,5-dimethyl-2,5 - bis(m-tolylhydrazolyloxy)hexane, butyl peroxy methoxycarbonate, tert-butyl peroxy 2-ethylhexyl monocarbonate, and third hexyl peroxybenzoate , third butyl peroxyacetate, and the like. For the component (d1) other than the peroxy ester, for example, a compound described in Patent Document 2 (International Publication No. 2009/063827) can be suitably used. The peroxy esters may be used alone or in combination of two or more.

The component (d2) is a hardener which is decomposed by light to generate a free radical. As the component (d2), a compound which generates free radicals by irradiating light having a wavelength of from 150 nm to 750 nm can be used. As such a compound, for example, from the viewpoint of high sensitivity to light irradiation, photoinitiation, photopolymerization, and photocuring, and J.-P. Fouassier, are preferable. α-Acetylbenzophenone derivatives and phosphine oxide derivatives described in Hanser Publishers (1995), pages 17 to 35. The component (d2) may be used alone or in combination of two or more. The component (d2) may be used in combination with the component (d1) (the peroxide, an azo compound, or the like). The component (d1) or the component (d2) may be used in combination with a curing agent that generates free radicals by ultrasonic waves, electromagnetic waves, or the like.

The component (d) can be appropriately selected depending on the connection temperature, the connection time, the use period, and the like of the target. The component (d) may be used alone or in combination of two or more. Further, the component (d) may be used in combination with a decomposition accelerator, a decomposition inhibitor, or the like. Further, the component (d) may be coated with a macromolecular substance such as a polyurethane or a polyester to be microencapsulated. Microencapsulated hardeners are preferred because they extend the useful life.

When the connection time is 25 seconds or less, the content of the component (d) is preferably in the following range from the viewpoint of easily obtaining a sufficient reaction rate. The content of the component (d) is preferably 0.1 part by mass or more, and more preferably 1 part by mass or more based on 100 parts by mass of the component (c). The content of the component (d) is preferably 40 parts by mass or less, and more preferably 20 parts by mass or less based on 100 parts by mass of the component (c). From the viewpoint of the above, the content of the component (d) is preferably from 0.1 part by mass to 40 parts by mass, more preferably from 1 part by mass to 20 parts by mass, per 100 parts by mass of the component (c).

When the connection time is 25 seconds or less, the content of the component (d) is preferably in the following range from the viewpoint of easily obtaining a sufficient reaction rate. The content of the component (d) is preferably 0.1 parts by mass or more, and more preferably 1 part by mass or more, based on 100 parts by mass of the total of the component (c) and the film-forming material (components to be used as needed). The content of the component (d) is preferably 40 parts by mass or less, more preferably 20 parts by mass or less, based on 100 parts by mass of the total of the component (c) and the film-forming material (components to be used as needed). In view of the above, the content of the component (d) is preferably from 0.1 part by mass to 40 parts by mass, more preferably, based on 100 parts by mass of the total of the component (c) and the film-forming material (component to be used). It is 1 part by mass to 20 parts by mass.

From the viewpoint of easily obtaining a sufficient reaction rate, the content of the component (d) in the case where the connection time is not limited is preferably in the following range. The content of the component (d) is preferably 0.01 parts by mass or more, and more preferably 0.1 parts by mass or more based on 100 parts by mass of the component (c). The content of the component (d) is preferably 30 parts by mass or less, and more preferably 15 parts by mass or less based on 100 parts by mass of the component (c). From the viewpoint of the above, the content of the component (d) is preferably from 0.01 part by mass to 30 parts by mass, more preferably from 0.1 part by mass to 15 parts by mass, per 100 parts by mass of the component (c).

From the viewpoint of easily obtaining a sufficient reaction rate, the content of the component (d) in the case where the connection time is not limited is preferably in the following range. The content of the component (d) is preferably 0.01 parts by mass or more, and more preferably 0.1 parts by mass or more, based on 100 parts by mass of the total of the component (c) and the film-forming material (components to be used as needed). The content of the component (d) is preferably 30 parts by mass or less, and more preferably 15 parts by mass or less, based on 100 parts by mass of the total of the component (c) and the film-forming material (components to be used as needed). In view of the above, the content of the component (d) is preferably from 0.01 part by mass to 30 parts by mass, more preferably 100 parts by mass based on the total of the component (c) and the film-forming material (component to be used). It is from 0.1 part by mass to 15 parts by mass.

(Film Forming Material) The adhesive composition of the present embodiment may contain a film forming material as needed. When the liquid-form adhesive composition is solidified into a film shape, the film forming material can improve the workability of the film in a normal state (normal temperature and normal pressure), and it is difficult to crack the film, which is difficult to be broken, and is difficult to be sticky. And other characteristics. Examples of the film forming material include phenoxy resin, polyethylene formaldehyde, polystyrene, polyvinyl butyral, polyester, polyamide, xylene resin, and polyurethane. From the viewpoints of excellent adhesion, compatibility, heat resistance and mechanical strength, phenoxy resins are preferred among these. The film forming materials may be used alone or in combination of two or more.

Examples of the phenoxy resin include a resin obtained by addition polymerization of a bifunctional epoxy resin and a bifunctional phenol, and a reaction obtained by reacting a bifunctional phenol with an epihalohydrin until macromolecularization. Resin. The phenoxy resin can be, for example, a 1 mol 2 functional phenol and 0.985 mol to 1.015 molohalool in the presence of a catalyst such as an alkali metal hydroxide in a non-reactive solvent at 40 ° C to 120 ° C. Obtained by carrying out the reaction at the temperature. From the viewpoint of excellent mechanical properties and thermal properties of the resin, it is particularly preferable that the phenoxy resin has a compounding equivalent ratio of the bifunctional epoxy resin to the bifunctional phenol to be an epoxy group/phenolic hydroxyl group=1/0.9. ~1/1.1, in the presence of a catalyst such as an alkali metal compound, an organophosphorus compound or a cyclic amine compound, an organic solvent having a boiling point of 120 ° C or higher (an amine, an ether, a ketone or a lactone) In the case of an alcohol or the like, it is obtained by heating to 50 to 200 ° C under the conditions of a reaction solid content of 50% by mass or less to carry out an addition polymerization reaction. The phenoxy resin may be used alone or in combination of two or more.

Examples of the bifunctional epoxy resin include bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol AD epoxy resin, bisphenol S epoxy resin, biphenyl diglycidyl ether, and armor. A substituted biphenyl diglycidyl ether or the like. The bifunctional phenol is a compound having two phenolic hydroxyl groups. Examples of the bifunctional phenols include hydroquinones, bisphenol A, bisphenol F, bisphenol AD, bisphenol S, and bisphenol oxime (4,4'-(9-fluorenylene)diphenol). a bisphenol such as a bisphenol hydrazide substituted with a methyl group, a dihydroxybiphenyl group, or a dihydroxybiphenyl group substituted with a methyl group. The phenoxy resin may also be modified with a free radically polymerizable functional group, or other reactive compound (e.g., epoxy modified).

The content of the film forming material is preferably from 10 parts by mass to 90 parts by mass, more preferably from 20 parts by mass to 60 parts by mass, per 100 parts by mass of the adhesive component of the adhesive composition.

(Electrically Conductive Particles) The adhesive composition of the present embodiment may further contain conductive particles. Examples of the constituent material of the conductive particles include metals such as gold (Au), silver (Ag), nickel (Ni), copper (Cu), and solder, and carbon. Further, a non-conductive resin, glass, ceramic, plastic, or the like may be used as a core, and the core may be coated with the metal (metal particles or the like) or carbon coated conductive particles. Since the coated conductive particles or the hot-melt metal particles are deformed by heating and pressurization, the height of the circuit electrodes is not uniform at the time of connection, and the contact area with the electrodes at the time of connection increases, so that reliability is improved.

The average particle diameter of the conductive particles is preferably from 1 μm to 30 μm from the viewpoint of excellent dispersibility and conductivity. The average particle diameter of the conductive particles can be measured, for example, by machine analysis such as a laser diffraction method. The content of the conductive particles is preferably 0.1 parts by mass or more, and more preferably 1 part by mass or more, based on 100 parts by mass of the adhesive component of the adhesive composition. The content of the conductive particles is preferably 100 parts by mass or less, more preferably 50 parts by mass or less, based on 100 parts by mass of the adhesive component of the adhesive composition, from the viewpoint of easily suppressing the short circuit of the electrode (circuit electrode or the like).

(Other components) The adhesive composition of the present embodiment may optionally contain a polymerization inhibitor such as hydroquinone or hydroquinone methyl ether.

The adhesive composition of the present embodiment may further contain a homopolymer obtained by polymerizing at least one monomer component selected from the group consisting of (meth)acrylic acid, (meth)acrylic acid ester, and acrylonitrile. Copolymer. From the viewpoint of excellent stress relaxation, it is preferred that the adhesive composition of the present embodiment contains an acrylic rubber or the like which is obtained by polymerizing glycidyl (meth)acrylate having a glycidyl ether group. Things. The weight average molecular weight of the acrylic rubber is preferably 200,000 or more from the viewpoint of enhancing the cohesive force of the adhesive composition.

The adhesive composition of the present embodiment may further include coated fine particles in which the surface of the conductive particles is coated with a polymer resin or the like. In the case where such coated fine particles are used in combination with the conductive particles, even in the case where the content of the conductive particles is increased, it is easy to suppress a short circuit caused by the contact of the conductive particles with each other, thereby insulating the adjacent circuit electrodes. Sexual improvement. The coated fine particles may be used alone without using conductive particles, and the coated fine particles may be used in combination with the conductive particles.

The adhesive composition of the present embodiment may further contain rubber fine particles, a filler, a softener, an accelerator, an anti-aging agent, a colorant, a flame retardant, a thixotropic agent, a coupling agent, a phenol resin, a melamine resin, an isocyanate. Wait. The adhesive composition of the present embodiment may suitably contain an additive such as an adhesion improving agent (excluding a coupling agent), a tackifier, a leveling agent, a coloring agent, and a weather resistance improving agent.

The rubber fine particles preferably have an average particle diameter of twice or less the average particle diameter of the conductive particles, and the storage elastic modulus at normal temperature is 1/2 of the storage elastic modulus of the conductive particles and the adhesive composition at normal temperature. The following particles. In particular, the material of the rubber microparticles is an anthrone, an acrylic emulsion, a Styrene Butadiene Rubber (SBR), a Nitrile-Butadiene Rubber (NBR) or a polybutadiene. In the case of rubber, the rubber fine particles are preferably used singly or in combination of two or more. The three-dimensionally crosslinked rubber fine particles are excellent in solvent resistance and are easily dispersed in the adhesive composition.

The filler can improve the electrical characteristics (connection reliability, etc.) between the circuit electrodes. As the filler, for example, particles having an average particle diameter of 1/2 or less of the average particle diameter of the conductive particles can be suitably used. When particles having no conductivity and a filler are used in combination, particles having an average particle diameter or less of particles having no conductivity can be used as a filler. The content of the filler is preferably 5 parts by mass to 60 parts by mass based on 100 parts by mass of the adhesive component of the adhesive composition. When the content is 60 parts by mass or less, the effect of improving the connection reliability tends to be more sufficiently obtained. When the content is 5 parts by mass or more, the effect of adding the filler tends to be sufficiently obtained.

When the adhesive composition of the present embodiment is liquid at normal temperature, it can be used in a paste form. In the case of being a solid at normal temperature, it may be gelatinized using a solvent in addition to heating. The solvent to be used is not particularly limited as long as it is not reactive with the adhesive composition and the additive, and exhibits sufficient solubility. It is preferably a boiling point of 50 ° C at normal pressure. ~150 ° C solvent. When the boiling point is 50 ° C or more, the volatility of the solvent is poor at normal temperature, so that it can be used even in an open system. When the boiling point is 150 ° C or less, the solvent is easily volatilized, so that good reliability can be obtained after that.

The adhesive composition of the present embodiment may also be in the form of a film. A solution obtained by adding a solvent or the like to the adhesive composition or the like may be applied to a fluororesin film, a polyethylene terephthalate film, a release substrate (release paper, etc.), and then a solvent or the like. Removal, thereby obtaining a film. Further, after the solution is impregnated on a substrate such as a nonwoven fabric and placed on a release substrate, a solvent or the like is removed to obtain a film. When it is used in the form of a film, it is more convenient from the viewpoint of excellent workability and the like.

The adhesive composition of the present embodiment can be followed by pressurization together with heating or light irradiation. By using heat and light irradiation in combination, it is possible to carry out the subsequent step at a low temperature for a short time. The light irradiation is preferably irradiated with light in a wavelength region of 150 nm to 750 nm. The low-pressure mercury lamp, the medium-pressure mercury lamp, the high-pressure mercury lamp (ultra-high pressure mercury lamp, etc.), a xenon lamp, a metal halide lamp, etc. can be hardened by the irradiation amount of 0.1 J/cm<^2> to 10 J/cm<^2> . The heating temperature is not particularly limited, but is preferably a temperature of from 50 ° C to 170 ° C. The pressure is not particularly limited as long as it does not cause damage to the adherend, and is preferably 0.1 MPa to 10 MPa. It is preferred to carry out heating and pressurization in the range of 0.5 second to 3 hours.

The adhesive composition of the present embodiment can be used as an adhesive for different kinds of adherends having different thermal expansion coefficients. Specifically, it can be used as a circuit connecting material represented by an anisotropic conductive adhesive, a silver paste, a silver film, or the like; an elastomer for a chip size package (CSP), an underfill material for a CSP, and a lead on a wafer (Lead) On Chip, LOC) A semiconductor element represented by a tape or the like is used in the form of a material or the like. The adherend composition of the present embodiment has excellent adhesion strength before and after the reliability test for the adherend composed of various materials (for example, inorganic materials (oxides, metals, etc.), organic materials, and composites thereof) .

<Structure and Method of Producing the Same> The structure of the present embodiment includes the adhesive composition of the present embodiment or a cured product thereof. The structure of the present embodiment is, for example, a semiconductor device such as a circuit connection structure. In one embodiment of the structure of the present embodiment, the circuit connection structure includes a first circuit member having a first circuit electrode, a second circuit member having a second circuit electrode, and a first circuit member and a second circuit A circuit connection member between the members. The first circuit member includes, for example, a first substrate and a first circuit electrode disposed on the first substrate. The second circuit member includes, for example, a second substrate and a second circuit electrode disposed on the second substrate. The first circuit electrode and the second circuit electrode are oppositely and electrically connected. The circuit connecting member includes the adhesive composition of the present embodiment or a cured product thereof. The structure of the present embodiment may include the adhesive composition of the present embodiment or a cured product thereof, and a member (such as a substrate) that does not have a circuit electrode may be used instead of the circuit member of the circuit connection structure.

The method for producing a structure of the present embodiment includes a step of curing the adhesive composition of the present embodiment. In one embodiment of the method for manufacturing a structure of the present embodiment, the method of manufacturing a circuit-connecting structure includes a step of disposing a first circuit member having a first circuit electrode and a second circuit member having a second circuit electrode The adhesive composition of the present embodiment is disposed, and a heating and pressurizing step is performed to pressurize the first circuit member and the second circuit member to electrically connect the first circuit electrode and the second circuit electrode, and to the adhesive composition It is heated to harden it. In the configuring step, the first circuit electrode and the second circuit electrode may be arranged to face each other. In the heating and pressurizing step, the direction in which the first circuit member and the second circuit member oppose may be pressurized.

Hereinafter, a circuit connection structure and a method of manufacturing the same will be described as an embodiment of the present embodiment with reference to the drawings. Fig. 1 is a schematic cross-sectional view showing an embodiment of a structure. The circuit connection structure 100a shown in FIG. 1 includes a facing circuit member (first circuit member) 20 and a circuit member (second circuit member) 30, and a connection between the circuit member 20 and the circuit member 30 is disposed. The circuit connection member 10 of the member. The circuit connecting member 10 includes a cured product of the adhesive composition of the present embodiment.

The circuit member 20 includes a substrate (first substrate) 21 and a circuit electrode (first circuit electrode) 22 disposed on the main surface 21a of the substrate 21. An insulating layer (not shown) may be disposed on the main surface 21a of the substrate 21 as the case may be.

The circuit member 30 includes a substrate (second substrate) 31 and a circuit electrode (second circuit electrode) 32 disposed on the main surface 31a of the substrate 31. An insulating layer (not shown) may be disposed on the main surface 31a of the substrate 31 as the case may be.

The circuit connecting member 10 includes an insulating material (a cured product of components other than the conductive particles) 10a and conductive particles 10b. The conductive particles 10b are disposed at least between the opposing circuit electrodes 22 and the circuit electrodes 32. In the circuit connection structure 100a, the circuit electrode 22 and the circuit electrode 32 are electrically connected via the conductive particles 10b.

The circuit member 20 and the circuit member 30 have single or a plurality of circuit electrodes (connection terminals). As the circuit member 20 and the circuit member 30, for example, a member including an electrode that requires electrical connection can be used. As the circuit member, a wafer component such as a semiconductor wafer (IC wafer), a resistor wafer, or a capacitor wafer, a substrate such as a printed substrate or a semiconductor mounting substrate, or the like can be used. As a combination of the circuit member 20 and the circuit member 30, for example, a semiconductor wafer and a semiconductor mounting substrate can be used. Examples of the material of the substrate include inorganic materials such as semiconductors, glass, and ceramics; organic substances such as polyimide, polyethylene terephthalate, polycarbonate, (meth)acrylic resin, and cyclic olefin resin; and glass/ a composite such as epoxy or the like. The substrate can also be a plastic substrate.

Fig. 2 is a schematic cross-sectional view showing another embodiment of the structure. The circuit connection structure 100b shown in FIG. 2 has the same configuration as the circuit connection structure 100a except that the circuit connection member 10 does not contain the conductive particles 10b. In the circuit connection structure 100b shown in FIG. 2, the circuit electrode 22 and the circuit electrode 32 are not in direct contact with each other via the conductive particles, and are electrically connected.

The circuit connection structure 100a and the circuit connection structure 100b can be manufactured, for example, by the following method. First, when the adhesive composition is in the form of a paste, the adhesive composition is applied and dried, whereby the resin layer containing the adhesive composition is placed on the circuit member 20. When the adhesive composition is in the form of a film, the film-like adhesive composition is attached to the circuit member 20, whereby the resin layer containing the adhesive composition is placed on the circuit member 20. Then, the circuit member 30 is placed on the resin layer disposed on the circuit member 20 such that the circuit electrode 22 and the circuit electrode 32 face each other. Next, the resin layer containing the adhesive composition is subjected to heat treatment or light irradiation, whereby the adhesive composition is cured to obtain a cured product (circuit connecting member 10). The circuit connection structure 100a and the circuit connection structure 100b are obtained by the above. [Examples]

Hereinafter, the present invention will be specifically described based on examples, but the present invention is not limited to the following examples.

<Preparation of film-like adhesive composition> [Example 1] A bisphenol A type epoxy resin and a phenol compound having an anthracene ring structure in a molecule (4,4'-(9-fluorenylene)-di Phenol) to synthesize phenoxy resin. This phenoxy resin was dissolved in a mixed solution of toluene/ethyl acetate=50/50 (mass ratio) to prepare a solution having a solid content of 40% by mass. Next, as the rubber component, an acrylic rubber (40 parts by mass of butyl acrylate - 30 parts by mass of ethyl acrylate - 30 parts by mass of acrylonitrile - 3 parts by mass of glycidyl methacrylate, and a weight average molecular weight of 800,000) was prepared. This acrylic rubber was dissolved in a mixed solution of toluene/ethyl acetate = 50/50 (mass ratio) to prepare a solution having a solid content of 15% by mass. Further, a liquid capsule containing a microcapsule latent curing agent (a microencapsulated amine curing agent), a bisphenol F type epoxy resin, and a naphthalene type epoxy resin is prepared at a mass ratio of 34:49:17. Hardener epoxy resin (epoxy equivalent: 202). Further, as the decane compound, 8-glycidoxyoctyltrimethoxydecane (product name: KBM4803, manufactured by Shin-Etsu Chemical Co., Ltd.) was prepared.

The varnish A1 is prepared by blending the materials with a mass ratio (solid content) of a phenoxy resin, an acrylic rubber, a hardener-containing epoxy resin, and a decane compound of 20:30:47:3 (adhesive composition containing liquid) ). Further, conductive particles A having a nickel layer having a thickness of 0.2 μm were formed on the surface of particles having polystyrene as a core. The conductive particles had an average particle diameter of 5 μm and a specific gravity of 2.5. To the 100 parts by mass of the solid component of the varnish A1, 5 parts by mass of the conductive particles A were blended to prepare a varnish B1 (circuit connecting material-containing liquid). On a polyethylene terephthalate (PET) film having a thickness of 50 μm which was surface-treated on one side, varnish B1 was applied using a coating tool, and then hot air dried at 70 ° C for 3 minutes. A film-like adhesive composition having a thickness of 20 μm was formed on the PET film.

[Comparative Example 1] 3-Glycidoxypropyltrimethoxydecane (product name: KBM403, manufactured by Shin-Etsu Chemical Co., Ltd.) was used as a decane compound instead of 8-glycidoxyoctyltrimethoxydecane. A film-like adhesive composition was produced in the same manner as in Example 1 except that it was carried out.

[Example 2] 50 g of phenoxy resin (product name: PKHC, Union Carbide Co., Ltd., weight average molecular weight 45000) was dissolved in toluene / ethyl acetate = 50 / 50 (mass ratio) A phenoxy resin solution having a solid content of 40% by mass was prepared by mixing the solutions. As the radical polymerizable compound, EO-modified diacrylate of isocyanuric acid (product name: M-215, manufactured by Toagosei Co., Ltd.), and 2-(methyl) propylene methoxyethyl phosphate ( Product name: P-2M, manufactured by Kyoeisha Chemical Co., Ltd.) and urethane acrylate (product name: U-2PPA, manufactured by Shin-Nakamura Chemical Co., Ltd.). As a decane compound, 7-octenyltrimethoxydecane (product name: KBM1083, manufactured by Shin-Etsu Chemical Co., Ltd.) was prepared. As a radical generator, a benzammonium peroxide group (product name: NYPER-BMT-K40, manufactured by Nippon Oil Co., Ltd.) was prepared.

Mass ratio of phenoxy resin, EO-modified diacrylate of isocyanuric acid, 2-(meth) propylene methoxyethyl phosphate, urethane acrylate, decane compound, and radical generator ( The solid content was adjusted to 50:19:3:20:3:5 to prepare varnish B1 (adhesive composition-containing liquid). Furthermore, 5 parts by mass of the conductive particles A were blended with respect to 100 parts by mass of the solid content of the varnish B1 to prepare a varnish B2 (circuit connecting material-containing liquid). On a polyethylene terephthalate (PET) film having a thickness of 50 μm which was surface-treated on one side, varnish B2 was applied using a coating tool, and then dried at 70 ° C for 3 minutes by hot air drying. A film-like adhesive having a thickness of 20 μm was formed on the PET film.

[Comparative Example 2] The same procedure as in Example 2 was carried out except that vinyl trimethoxy decane (product name: KBM103, manufactured by Shin-Etsu Chemical Co., Ltd.) was used as the decane compound instead of 7-octenyltrimethoxydecane. A film-like adhesive composition was produced.

[Example 3] In addition to 7-octenyltrimethoxydecane, 8-methylpropenyloxyoctyltrimethoxydecane (product name: KBM5803, manufactured by Shin-Etsu Chemical Co., Ltd.) was used as a decane compound. A film-like adhesive composition was produced in the same manner as in Example 2.

[Comparative Example 3] In place of 7-octenyltrimethoxydecane, 3-methylpropenyloxypropyltrimethoxydecane (product name: KBM503, manufactured by Shin-Etsu Chemical Co., Ltd.) was used as a decane compound. A film-like adhesive composition was produced in the same manner as in Example 2.

<Evaluation of Strength Next> As a first circuit member, a flexible printed circuit (FPC) having 500 copper circuits having a line width of 75 μm, a pitch of 150 μm, and a thickness of 18 μm was prepared. As the second circuit member, glass (thickness: 0.7 mm) glass having a thin layer of 0.5 μm of tantalum nitride (SiN _x ) was prepared. In the state in which the film-like adhesive composition of Examples 1 to 3 or Comparative Examples 1 to 3 is interposed between the first circuit member and the second circuit member, a thermocompression bonding apparatus is used (heating method: constant temperature) The model, manufactured by Toray Engineering Co., Ltd., was heated and pressurized at 170 ° C and 3 MPa for 20 seconds, and connected at a width of 2 mm to fabricate a circuit-connected structure (connector).

The circuit-connecting structure was measured by a 90-degree peeling method according to Japanese Industrial Standards (JIS) Z0237, and then followed by (after heating and pressurizing for 20 seconds at 170 ° C and 3 MPa). The strength of the bond after standing for 100 hours in a constant temperature and humidity chamber at 85 ° C and 85% RH. At this time, the strength measuring device was Tensilon UTM-4 manufactured by Toyo Baldwin Co., Ltd. (peeling speed: 50 mm/min, 25° C.).

The results of the measurement as described above are shown in Table 1.

[Table 1]

From the above, it was confirmed that each of Examples 1 to 3 was higher in the subsequent strength than Comparative Examples 1 to 3, and also after the reliability test (high temperature and high humidity treatment). The adhesion to the surface of the substrate (inorganic substrate) can be well maintained.

10‧‧‧Circuit connection components
10a‧‧‧Insulating substances
10b‧‧‧ conductive particles
20‧‧‧First circuit component
21‧‧‧First substrate
21a, 31a‧‧‧ main surface
22‧‧‧First circuit electrode
30‧‧‧Second circuit components
31‧‧‧second substrate
32‧‧‧Second circuit electrode
100a, 100b‧‧‧ circuit connection structure

Fig. 1 is a schematic cross-sectional view showing an embodiment of a structure of the present invention. Fig. 2 is a schematic cross-sectional view showing another embodiment of the structure of the present invention.

10‧‧‧Circuit connection components

10a‧‧‧Insulating substances

10b‧‧‧ conductive particles

20‧‧‧First circuit component

21‧‧‧First substrate

21a, 31a‧‧‧ main surface

22‧‧‧First circuit electrode

30‧‧‧Second circuit components

31‧‧‧second substrate

32‧‧‧Second circuit electrode

100a‧‧‧Circuit connection structure

Claims (8)

An adhesive composition containing a decane compound having a structure represented by the following formula (I), In the formula, X represents an organic group, R ¹ and R ² each independently represent an alkyl group, m represents an integer of 0 to 2, and s represents an integer of 6 or more. The adhesive composition according to claim 1, wherein the organic group X is selected from the group consisting of a (meth) acryl fluorenyl group, a vinyl group, an epoxy group, a nitrogen atom-containing group, and a sulfur atom-containing group. At least one of the group consisting of. The adhesive composition according to claim 1 or 2, further comprising an epoxy resin and a latent curing agent. The adhesive composition according to any one of claims 1 to 3, further comprising a radical polymerizable compound and a curing agent which generates a radical by heat or light. The adhesive composition according to any one of claims 1 to 4, further comprising conductive particles. The adhesive composition according to any one of claims 1 to 5, which is used for circuit connection. A structure comprising the adhesive composition according to any one of claims 1 to 6 or a cured product thereof. A structure including a first circuit member having a first circuit electrode, a second circuit member having a second circuit electrode, and a circuit connection member disposed between the first circuit member and the second circuit member The first circuit electrode and the second circuit electrode are electrically connected, and the circuit connecting member includes the adhesive composition or the cured product thereof according to any one of claims 1 to 6. .