KR101970376B1 - Adhesive composition and connection body - Google Patents

Adhesive composition and connection body Download PDF

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KR101970376B1
KR101970376B1 KR1020147008118A KR20147008118A KR101970376B1 KR 101970376 B1 KR101970376 B1 KR 101970376B1 KR 1020147008118 A KR1020147008118 A KR 1020147008118A KR 20147008118 A KR20147008118 A KR 20147008118A KR 101970376 B1 KR101970376 B1 KR 101970376B1
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group
circuit
adhesive
compound
epoxy
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KR1020147008118A
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KR20140059828A (en
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스나오 구도우
가즈야 마츠다
도루 후지나와
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히타치가세이가부시끼가이샤
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C09J9/02—Electrically-conducting adhesives
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
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    • H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
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    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
    • H05K3/32—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits
    • H05K3/321—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by conductive adhesives
    • H05K3/323—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by conductive adhesives by applying an anisotropic conductive adhesive layer over an array of pads
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    • H01L2224/32151—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
    • H01L2224/32221—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
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    • H01L2224/83855—Hardening the adhesive by curing, i.e. thermosetting
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Abstract

An adhesive composition comprising (a) a thermoplastic resin, (b) a radically polymerizable compound, and (c) a radical polymerization initiator, wherein the radically polymerizable compound comprises a compound having an epoxy group.

Description

[0001] ADHESIVE COMPOSITION AND CONNECTION BODY [0002]

The present invention relates to an adhesive composition and a connection member of a circuit member.

BACKGROUND ART In semiconductor devices and liquid crystal display devices, various adhesive compositions have conventionally been used as circuit connecting materials for the purpose of bonding various members in devices. This adhesive composition is required to have various properties such as adhesiveness, heat resistance, reliability at high temperature and high humidity, and the like.

The adherend to be adhered has various surfaces formed of various materials such as an organic material such as a printed wiring board and a polyimide film, a metal such as copper and aluminum, or a metal compound such as ITO, SiN and SiO 2 . Therefore, the adhesive composition needs to be designed for each adherend.

BACKGROUND ART Conventionally, a thermosetting resin composition comprising a thermosetting resin such as an epoxy resin exhibiting high adhesiveness and high reliability has been used as an adhesive composition for a semiconductor element or a liquid crystal display element (see, for example, Patent Document 1) . Such an adhesive composition generally contains an epoxy resin, a curing agent such as a phenol resin which reacts with the epoxy resin, and a thermal latent catalyst for promoting the reaction between the epoxy resin and the curing agent. Among them, the thermal latent catalyst is an important factor for determining the curing temperature and the curing rate. As a result, various compounds have been used as thermal latent catalysts from the viewpoints of storage stability at room temperature and curing rate upon heating. The adhesive composition is generally cured by heating at a temperature of 170 to 250 ° C for 1 to 3 hours to exhibit desired adhesiveness.

Acrylate derivatives, or methacrylate derivatives and peroxides (see, for example, Patent Document 2). Radical polymerization type adhesives are advantageous from the standpoint of short-time curing because the reactive radicals are highly reactive. An example in which a radical polymerization type adhesive and an epoxy resin and an anionic polymerization type curing agent are used together (Patent Document 3).

Japanese Patent Laid-Open No. 1-113480 WO 98/44067 Japanese Patent Application Laid-Open No. 2007-224228

With the recent trend toward higher integration of semiconductor devices and higher definition of liquid crystal devices, the inter-device and inter-wiring pitches have become narrower. Therefore, there is a high possibility that heating during curing for circuit connection adversely affects peripheral members.

Further, in order to lower the cost, there is a need to improve the throughput, and there is a demand for an adhesive composition that is cured at a lower temperature and in a shorter time, in other words, an adhesive composition of " low temperature curing ". In order to achieve the low temperature fast curing of the adhesive composition, for example, a thermal latent catalyst having a low activation energy is sometimes used, but in that case, it is very difficult to maintain the storage stability near room temperature.

The radical curing type adhesive can relatively easily achieve the low temperature curing. However, in the case of the connection member obtained by using the radical-curing adhesive, in many cases, after the connection member is exposed to the high temperature and high humidity environment, the separation bubble is often generated at the interface between the circuit member and the circuit connection material. As one of the causes, it is considered that the radical curing type adhesive tends to cause a large hardening shrinkage as compared with an adhesive containing an epoxy resin.

When the compounding amount of the (meth) acrylate compound is decreased, the peeling of the interface between the circuit member and the circuit connecting material can be suppressed to some extent. However, in this case, there is a tendency that the adhesive strength is lowered or the connection reliability is lowered. Further, when circuit connection is performed under a low-pressure condition such as 1 MPa, for example, the resin between the opposing electrodes is not sufficiently removed, so that satisfactory electrical connection can not be obtained in the conventional circuit connecting material. The circuit connection under a low pressure condition is necessary in order to prevent breakage of the circuit member particularly when a thin circuit member is connected. When an epoxy resin and a radical polymerizable compound are used in combination, radical polymerization is inhibited, so that short-term curing becomes difficult.

The main object of the present invention is to provide a radical curing type adhesive which can maintain sufficient connection reliability even under a low pressure connection condition when used as a circuit connecting material for connecting a circuit member and further can suppress the occurrence of interface delamination under high temperature and high humidity conditions To provide an adhesive composition.

The present invention relates to an adhesive composition comprising (a) a thermoplastic resin, (b) a radically polymerizable compound and (c) a radical polymerization initiator. In one aspect, the radically polymerizable compound in the adhesive composition according to the present invention includes a compound having an epoxy group.

According to such an adhesive composition, when used as a circuit connecting material for connecting a circuit member, sufficient connection reliability can be maintained even under a low-pressure connection condition, and further, occurrence of interface delamination under high temperature and high humidity conditions can be suppressed.

The adhesive composition according to the present invention may further contain (d) a silane coupling agent represented by the following formula (1).

Figure 112014029468592-pct00001

In formula (1), R 1 , R 2 and R 3 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkoxycarbonyl group having 1 to 5 carbon atoms, or an aryl group. At least one of R 1 , R 2 and R 3 is an alkoxy group. R 4 represents a (meth) acryloyl group, a vinyl group, an isocyanate group, an imidazole group, a mercapto group, an amino group, a methylamino group, a dimethylamino group, a benzylamino group, a phenylamino group, a cyclohexylamino group, a morpholino group, Or a glycidyl group. a represents an integer of 1 to 10;

The adhesive composition according to the present invention may further contain (e) conductive particles. Thereby, since the adhesive composition can impart conductivity or anisotropic conductivity, the adhesive composition can be more suitably used as a circuit connecting material. Further, the connection resistance between the circuit electrodes electrically connected through the adhesive composition can be more easily reduced.

In another aspect, the present invention relates to a connecting member comprising a pair of circuit members disposed with opposing circuit electrodes, and a connecting member provided between the pair of circuit members, the connecting members being adapted to bond the pair of circuit members to each other. The circuit electrodes of one circuit member and the circuit electrodes of the other circuit member are electrically connected. The connecting member constituting the pair of circuit members is a cured product of the adhesive composition according to the present invention.

In the connector according to the present invention, one circuit member may have a glass substrate and the other circuit member may have a flexible substrate.

The connection member according to the present invention can sufficiently suppress the peeling between the circuit member and the interface of the circuit connecting material after being left in a high temperature and high humidity environment. And sufficient connection reliability can be maintained.

According to the present invention, it is possible to maintain sufficient connection reliability even under a low-pressure connection condition when used as a circuit connecting material for connecting a circuit member while being a radical-curing adhesive, and furthermore, it is possible to suppress the occurrence of interface delamination under high temperature and high humidity conditions An adhesive composition is provided.

1 is a cross-sectional view showing one embodiment of a film-like adhesive.
2 is a cross-sectional view showing an embodiment of a connector.
3 is a cross-sectional view showing an embodiment of a method of manufacturing a connector.
4 is a plan view for explaining the area of compression.

Hereinafter, preferred embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following embodiments. In the drawings, the same or equivalent portions are denoted by the same reference numerals, and duplicate descriptions are appropriately omitted. In the present specification, (meth) acrylic acid refers to acrylic acid or the corresponding methacrylic acid, (meth) acrylate means acrylate or the corresponding methacrylate, and (meth) acryloyloxy group Means an acryloyloxy group or a methacryloyloxy group.

The adhesive composition according to the present embodiment contains (a) a thermoplastic resin, (b) a radically polymerizable compound and (c) a radical polymerization initiator.

The thermoplastic resin contained in the adhesive composition is not particularly limited, and examples thereof include polyimide resin, polyamide resin, phenoxy resin, poly (meth) acrylate resin, polyimide resin, polyester resin, polyurethane resin and polyvinyl And a butyral resin. The thermoplastic resin may contain a siloxane bond and / or a fluorine group. When two or more kinds of thermoplastic resins are used, a combination which is completely compatible with the resin or which is opaque due to micro-phase separation is suitable.

The weight average molecular weight of the thermoplastic resin is not particularly limited, but is preferably 5000 to 20000, and more preferably 10000 to 150000. When the weight average molecular weight of the thermoplastic resin is small, the adhesive strength of the adhesive composition tends to be lowered. If the weight average molecular weight of the thermoplastic resin is large, compatibility with other components of the thermoplastic resin tends to be lowered, or the fluidity of the adhesive tends to be lowered.

The amount of the thermoplastic resin is preferably 20 to 80 mass%, more preferably 30 to 70 mass%, and still more preferably 35 to 65 mass%, based on the total amount of the thermoplastic resin and the radical polymerizable compound . When the amount of the thermoplastic resin is decreased, there is a tendency that the adhesive force is lowered or the film formability of the adhesive composition is lowered. When the amount of the thermoplastic resin is increased, the fluidity of the adhesive tends to be lowered. The upper limit value and the lower limit value of the amount of the thermoplastic resin may be 58 mass%.

As the thermoplastic resin, a rubber component may be used for the purpose of stress relaxation and adhesion improvement. The rubber component includes, for example, an acrylic rubber, a polyisoprene, a polybutadiene, a carboxyl-terminated polybutadiene, a hydroxyl-terminated polybutadiene, a 1,2-polybutadiene, a carboxyl-terminated 1,2-polybutadiene, (Oxypropylene), poly (oxytetramethylene) glycol, polyolefin (polytetrafluoroethylene), polyolefin (polytetrafluoroethylene), and polyolefins such as styrene-butadiene rubber, hydroxyl-terminated styrene-butadiene rubber, carboxyl group, hydroxyl group, carboxylated nitrile rubber, hydroxyl- Glycol and poly-epsilon -caprolactone. From the viewpoint of improving the adhesion, it is preferable that the rubber component has a cyano group or a carboxyl group as a high polar group as a side chain group or a terminal group. These rubber components may be used singly or in combination of two or more.

The adhesive composition according to the present embodiment contains at least one compound having an epoxy group and a radically polymerizable unsaturated group as the radically polymerizable compound (b). The radical polymerizable unsaturated group is preferably a (meth) acryl group (particularly, a (meth) acryloyloxy group).

The radically polymerizable compound having an epoxy group and a radically polymerizable unsaturated group is, for example, a compound having an epoxy group and a (meth) acrylic group produced by the reaction of a polyfunctional epoxy compound having a plurality of epoxy groups with (meth) acrylic acid . In this reaction, the equivalence of the acryloyloxy group of (meth) acrylic acid to the epoxy equivalent of the compound having a plurality of epoxy groups is preferably 0.95 to 1.05, more preferably 1. [

The epoxy equivalent (g / equivalent) of the polyfunctional epoxy compound used to obtain the radically polymerizable compound having an epoxy group is preferably 130 to 250. Since the epoxy equivalent is within this range, the effect of improving the reliability of the connector is particularly remarkable. The upper limit value and the lower limit value of the polyfunctional epoxy compound may be 160, 170, 210, or 220. [

The polyfunctional epoxy compound is not particularly limited, and examples thereof include diglycidyl ether of bisphenol such as bisphenol A, bisphenol F and bisphenol S, polyglycine of polybasic acid such as alicyclic epoxy resin, Diallyl esters, novolak type epoxy resins, and polyglycidyl ethers of aliphatic polyols.

For example, according to the reaction between an epoxy compound having two epoxy groups and an acrylic acid equivalent to an epoxy equivalent of the above epoxy compound, in addition to the compound (i) in which one of two epoxy groups has been converted to an acryloyloxy group, A mixture of a compound (ii) in which an epoxy group is converted into an acryloyloxy group and an unreacted starting material (iii) is often obtained as a product. This mixture can be used as it is for producing an adhesive composition as it is, but it is also possible to purify the product by using a column or the like, if necessary. When the mixture is used as it is, the composition ratio (i) / (ii + iii) (molar ratio) is preferably 0.8 or more, more preferably 1 or more. If (i) / (ii + iii) (molar ratio) is less than 0.8, the effect of suppressing interface peeling of the connector and improving the connection reliability tends to be relatively small. From the same viewpoint, (ii) / (iii) (molar ratio) is preferably 0.95 to 1.05.

The molecular weight of the radically polymerizable compound having an epoxy group is preferably 300 or more and less than 1,000. When the molecular weight is small, the compound tends to volatilize in the process of producing the adhesive composition. When the molecular weight is large, sufficient fluidity tends not to be obtained particularly when a circuit member is connected at a low pressure.

The radically polymerizable compound having an epoxy group preferably has one glycidyl group and one (meth) acryloyloxy group. By using such a compound, the effect of the present invention is particularly remarkable.

The amount of the radically polymerizable compound having an epoxy group is preferably 2.5 to 15 mass%, more preferably 5 to 12.5 mass%, based on the total amount of the thermoplastic resin and the radical polymerizable compound. When the amount of the radically polymerizable compound having an epoxy group is small, the effect of suppressing the interface separation of the connection member and improving the connection reliability tends to be small. If the amount of the radically polymerizable compound having an epoxy group is large, the effect of suppressing the interface separation after the high temperature and high humidity treatment of the connector tends to be small. The upper limit value and the lower limit value of the amount of the radical polymerizable compound having an epoxy group may be 2.4 mass%, 9.7 mass%, 15 mass%, or 19 mass%.

The adhesive composition according to the present embodiment may contain, as radical polymerizing compound (b), any other compound having a radically polymerizable functional group, in addition to the radical polymerizing compound having an epoxy group. The radically polymerizable compound may be either a monomer or an oligomer, or a combination of both.

As the radically polymerizable compound that can be used in combination with the radically polymerizable compound having an epoxy group, one or more multifunctional (meth) acrylate compounds having two or more (meth) acryloyloxy groups are preferable. Examples of such (meth) acrylate compounds include monomers or oligomers such as epoxy (meth) acrylate, urethane (meth) acrylate, polyether (meth) acrylate and polyester (meth) acrylate, (Meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, neopentyl glycol di (meth) acrylate, dicyclopentenyl (meth) acrylate, Isocyanurate-modified trifunctional (meth) acrylate, dipentaerythritol hexa (meth) acrylate, isocyanuric acid-modified bifunctional (meth) acrylate, isocyanuric acid-modified trifunctional (meth) acrylate, bisphenol fluorene di An epoxy (meth) acrylate produced by adding (meth) acrylic acid to two glycidyl groups of glycidyl ether, and bisphenol fluorene diglycidyl Groups two glycidyl the LE is selected from a compound introduced into the acryloyloxy group in a (meth) acrylate compound in addition to ethylene glycol and / or propylene glycol.

The adhesive composition may contain a monofunctional (meth) acrylate compound as the radically polymerizable compound (b) for the purpose of controlling the flowability and the like. Examples of the monofunctional (meth) acrylate compound include pentaerythritol (meth) acrylate, 2-cyanoethyl (meth) acrylate, cyclohexyl (meth) acrylate, dicyclopentenyl (meth) (Meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, 2- (2-ethoxyethoxy) ethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, n-hexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, isobornyl Acrylate, 2-methoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, 2- (Meth) acryloyloxyethyl phosphate, N, N-dimethylaminoethyl (meth) acrylate Sites, and as N, N- dimethylaminopropyl (meth) acrylate and (meth) acrylate selected from one morpholine. These compounds may be used singly or in combination of two or more.

For the purpose of improving the crosslinking rate or the like, the adhesive composition may contain, as the radical polymerizing compound (b), a compound having a radically polymerizable functional group such as an allyl group, a maleimide group and a vinyl group in addition to the acrylate compound It is possible. Such compounds include, for example, N-vinylimidazole, N-vinylpyridine, N-vinylpyrrolidone, N-vinylformamide, N-vinylcaprolactam, 4,4'- - dimethylaniline), N-vinylacetamide, N, N-dimethylacrylamide, N-isopropylacrylamide and N, N-diethylacrylamide.

The adhesive composition preferably contains a radically polymerizable compound having a phosphoric acid group as the radically polymerizable compound (b) for the purpose of improving the adhesive strength. The radically polymerizable compound having a phosphoric acid group is selected from, for example, a compound represented by the following formula (2), (3) or (4).

Figure 112014029468592-pct00002

In the formula (2), R 5 represents a (meth) acryloyloxy group, R 6 represents a hydrogen atom or a methyl group, and each of w and x independently represents an integer of 1 to 8. A plurality of R 5 , R 6 , w and x in the same molecule may be the same or different.

Figure 112014029468592-pct00003

In the formula (3), R 7 represents (meth) acryloyloxy, and each of y and z independently represents an integer of 1 to 8. A plurality of R 7 , y and z in the same molecule may be the same or different.

Figure 112014029468592-pct00004

In the formula (4), R 8 represents a hydrogen atom or a methyl group, R 9 represents a (meth) acryloyloxy group, and b and c each independently represent an integer of 1 to 8. R 8 in the same molecule may be the same or different.

The radically polymerizable compound having a phosphoric acid group may be, for example, acid phosphoxyethyl methacrylate, acid phosphoxyethyl acrylate, acid phosphoxypropyl methacrylate, acid phosphoxypolyoxyethylene glycol monomethacrylate , Acid phosphoxypolyoxypropylene glycol monomethacrylate, 2,2'-di (meth) acryloyloxydiethyl phosphate, EO-modified phosphoric acid dimethacrylate, phosphoric acid-modified epoxy acrylate, and vinyl phosphate.

The amount of the radical polymerizable compound having a phosphoric acid group is preferably 0.1 to 15 parts by mass, more preferably 0.5 to 10 parts by mass, based on the total amount of the thermoplastic resin and the radical polymerizable compound. If the amount is small, a high adhesive strength tends to be difficult to obtain. If the amount is large, the property of the adhesive composition after curing tends to deteriorate, and the effect of improving the reliability may be reduced.

The total amount of the radically polymerizable compound (b) contained in the adhesive composition is preferably 20 to 80 mass%, more preferably 30 to 70 mass%, based on the total amount of the thermoplastic resin and the radical polymerizable compound , And still more preferably from 35 to 65 mass%. When the amount is small, the heat resistance tends to decrease. When the amount is large, the effect of suppressing peeling after leaving in a high temperature and high humidity environment tends to be small. The upper limit value and the lower limit value of the amount of the radical polymerizable compound may be 42 mass%.

The radical polymerization initiator (c) may be selected from compounds such as peroxides and azo compounds. From the viewpoints of stability, reactivity, and compatibility, a peroxide having a half-life temperature for one minute of 90 to 175 DEG C and a molecular weight of 180 to 1000 is preferable. The "one-minute half-life temperature" refers to a temperature at which the half-life of peroxide is one minute. The "half-life" refers to the time until the concentration of the compound decreases to half of the initial value at a predetermined temperature.

Examples of the radical polymerization initiator include 1,1,3,3-tetramethylbutyl peroxyneodecanoate, di (4-t-butylcyclohexyl) peroxydicarbonate, di (2-ethylhexyl) Oxydicarbonate, cumyl peroxyneodecanoate, 1,1,3,3-tetramethylbutyl peroxyneodecanoate, dilauryl peroxide, 1-cyclohexyl-1-methylethyl peroxyneo Decanoate, t-hexyl peroxyneodecanoate, t-butyl peroxyneodecanoate, t-butyl peroxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexa (2-ethylhexanoylperoxy) hexane, t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate , t-butylperoxyneoheptanoate, t-amylperoxy-2-ethylhexanoate, di-t-butylperoxyhexahydroterephthalate, t-amylperoxy-3,5,5-trimethylhexa Nonoate, 3-hydroxy-1,1-dimethylbutyl Peroxyneodecanoate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, t-amylperoxineodecanoate, t-amylperoxy-2-ethylhexanoate (3-methylbenzoyl) peroxide, dibenzoyl peroxide, di (4-methylbenzoyl) peroxide, 2,2'-azobis-2, Azobis (1-acetoxy-1-phenylethane), 2,2'-azobisisobutyronitrile, 2,2'-azobis 2-azobisisobutyronitrile, 4,4'-azobis (4-cyanovaleric acid), 1,1'-azobis (1-cyclohexanecarbonitrile) t-butyl peroxyisopropyl monocarbonate, t-butyl peroxymaleic acid, t-butyl peroxy-3,5,5-trimethyl hexanoate, t-butyl peroxy laurate, 2,5- -2,5-di (3-methylbenzoylperoxy) hexane, t-butylperoxy-2-ethylhexyl monocarbonate, t- 2,5-dimethyl-2,5-di (benzoyl peroxy) hexane, t-butyl peroxybenzoate, dibutyl peroxytrimethyl adipate, t- amyl peroxynormal octoate, t-amyl Peroxyisononanoate, and t-amylperoxybenzoate.

As the radical polymerization initiator, a compound capable of generating a radical by light irradiation at a wavelength of 150 to 750 nm may be used. Such a compound is not particularly limited, but is described in, for example, Photoinitiation, Photopolymerization, and Photocuring, J.-P. Acetaminophenone derivatives and phosphine oxide derivatives described in Fouassier, Hanser Publishers (1995), p17 to p35] are more preferred because of their high sensitivity to light irradiation. These compounds may be used singly or in combination of two or more. These compounds and the peroxide and the azo compound may be combined. Alternatively, the adhesive composition may include a radical polymerization initiator that generates radicals by ultrasonic waves, electromagnetic waves, or the like.

In order to suppress the corrosion of the connection terminals (circuit electrodes) of the circuit member, the amount of chlorine ions and organic acid contained in the radical polymerization initiator is preferably 5000 ppm or less. From the same viewpoint, a radically polymerizable compound having a small amount of organic acid generated after decomposition is preferable. From the standpoint of improving the stability of the circuit connecting material, a radical polymerization initiator having a mass retention ratio of 20 mass% or more after being left at room temperature under atmospheric pressure for 24 hours is preferable.

The amount of the radical polymerization initiator is preferably from 1 to 15 mass%, more preferably from 2.0 to 10 mass%, based on the total amount of the thermoplastic resin and the radical polymerizable compound.

The adhesive composition according to the present embodiment may contain a silane coupling agent. The silane coupling agent is preferably a compound represented by the following formula (1).

Figure 112014029468592-pct00005

In formula (1), R 1 , R 2 and R 3 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkoxycarbonyl group having 1 to 5 carbon atoms, or an aryl group. At least one of R 1 , R 2 and R 3 is an alkoxy group. R 4 represents a (meth) acryloyl group, a vinyl group, an isocyanate group, an imidazole group, a mercapto group, an amino group, a methylamino group, a dimethylamino group, a benzylamino group, a phenylamino group, a cyclohexylamino group, a morpholino group, Or a glycidyl group. a represents an integer of 1 to 10;

The silane coupling agent of the formula (1) is, for example, vinyltrimethoxysilane, vinyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3- Acryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, , N-2 (aminoethyl) 3-aminopropylmethyldimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane and 3-isocyanatopropyltriethoxysilane.

The amount of the silane coupling agent is preferably 0.1 to 10 mass%, more preferably 0.25 to 5 mass%, based on the total amount of the thermoplastic resin and the radical polymerizable compound. When the amount of the silane coupling agent is small, there is a tendency that the effect of suppressing the occurrence of separation bubbles at the interface between the circuit member and the circuit connecting material tends to be small. When the amount of the silane coupling agent is large, the solubility time of the adhesive composition tends to be shortened.

The adhesive composition according to the present embodiment may further contain conductive particles. The adhesive composition containing conductive particles can be particularly suitably used as an anisotropic conductive adhesive.

The conductive particles include core particles containing non-conductive materials such as metal particles including Au, Ag, Pd, Ni, Cu and solder, carbon particles, glass, ceramics and plastic, Metal particles, metal particles, carbon particles, and the like. The metal particles may be copper particles and particles having a silver layer covering the copper particles. The core particle of the composite particle is preferably a plastic particle.

Since the composite particles have deformability that is deformed by heating and pressing, when the circuit members are bonded to each other, the contact area between the circuit electrodes and the conductive particles of the circuit member can be increased. Therefore, according to the adhesive composition containing these composite particles as the conductive particles, a connecting material having a better connection reliability can be obtained.

The adhesive composition may contain an insulating coating conductive particle having an insulating layer or insulating particles covering the conductive particles and at least a part of the surface of the conductive particles. The insulating layer can be provided by a method such as hybridization. The insulating layer or insulating particles are formed of an insulating material such as a polymer resin. By using such insulating coated conductive particles, short circuit due to contact between adjacent conductive particles is less likely to occur.

The average particle diameter of the conductive particles is preferably 1 to 18 mu m from the viewpoint of obtaining good dispersibility and conductivity.

The amount of the conductive particles is not particularly limited, but is preferably 0.1 to 30% by volume, more preferably 0.1 to 10% by volume, and still more preferably 0.5 to 7.5% by volume based on the total volume of the adhesive composition. When the amount is small, the conductivity tends to deteriorate. If this amount is large, a short circuit tends to occur between the circuit electrodes. The amount (volume%) of the conductive particles is determined based on the volume at 23 캜 of each component constituting the adhesive composition before curing. The volume of each component can be obtained by converting mass to volume using specific gravity. A suitable solvent (water, alcohol, or the like) capable of sufficiently wetting the component is put into a measuring cylinder without dissolving or swelling the component whose volume is to be measured and the component to be measured is added thereto, As the volume of the water.

The adhesive composition may contain insulating organic fine particles and / or inorganic fine particles in addition to the conductive particles. The inorganic fine particles are selected from metal oxide fine particles represented by, for example, silica fine particles, alumina fine particles, silica-alumina fine particles, titania fine particles and zirconia fine particles, and nitride fine particles. The organic fine particles are selected from, for example, silicon fine particles, methacrylate-butadiene-styrene fine particles, acrylic-silicon fine particles, polyamide fine particles and polyimide fine particles. These fine particles may have a uniform structure or may have a core-shell type structure.

The amount of the organic fine particles and the inorganic fine particles is preferably 2.5 to 30 mass%, more preferably 5 to 20 mass%, based on the total amount of the thermoplastic resin and the radical polymerizable compound. If the amount of the inorganic fine particles is small, it tends to be relatively difficult to maintain the electrical connection between the opposing electrodes. If the amount of the inorganic fine particles is increased, the fluidity of the adhesive composition tends to be lowered.

The adhesive composition may contain a stabilizer in order to control the curing rate or to impart storage stability. These stabilizers are not particularly limited, but preferred are quinone derivatives such as benzoquinone and hydroquinone, phenol derivatives such as 4-methoxyphenol and 4-t-butylcatechol, 2,2,6,6-tetramethylpiperazine 1-oxyl and 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl, and hindered amine derivatives such as tetramethylpiperidyl methacrylate .

The amount of the stabilizer is preferably 0.01 to 30 parts by mass, more preferably 0.05 to 10 parts by mass, based on the total amount of the thermoplastic resin and the radical polymerizable compound. If this amount is small, the effect of the stabilizer tends to be small. If the amount is large, compatibility with other components may be deteriorated.

The adhesive composition according to the present embodiment can be used as a paste-like adhesive when it is liquid at room temperature (25 캜). When the adhesive composition is a solid at room temperature (25 캜), it may be heated and used. Alternatively, a paste may be used by adding a solvent. The solvent used for paste-making is not particularly limited as long as it has substantially no reactivity with the adhesive composition (including additives) and can sufficiently dissolve the adhesive composition. The boiling point of the solvent at normal pressure is preferably 50 to 150 ° C. If the boiling point of the solvent is less than 50 캜, there is a possibility of volatilization if left at room temperature (25 캜), so that the use in an open system may be restricted. If the boiling point of the solvent exceeds 150 ° C, it is difficult to volatilize the solvent, which may cause the effect of improving the reliability after adhesion to become small.

The adhesive composition according to the present embodiment may be molded into a film and used as a film-like adhesive. The film-like adhesive can be obtained by, for example, applying a solution obtained by adding a solvent or the like to the adhesive composition, if necessary, on a releasable support such as a fluororesin film, a polyethylene terephthalate film, a release paper or the like, Impregnating the solution with the solution, placing the solution on a releasable substrate, and removing the solvent or the like. The film-like adhesive is more convenient in terms of handleability and the like.

1 is a cross-sectional view showing one embodiment of a laminated film having a film-like adhesive. The laminated film 100 shown in Fig. 1 has a support 8 and a film-like adhesive 40 provided on the support 8. The film-like adhesive 40 is the above-described adhesive composition molded into a film and is composed of an insulating adhesive layer 5 and conductive particles 7 dispersed in the insulating adhesive layer 5. [ The insulating adhesive layer 5 is composed of components other than the conductive particles in the above-mentioned adhesive composition. This film-like adhesive can be easily handled, can be easily installed on an adherend, and can be easily connected. The film-like adhesive may have a multi-layer structure including two or more layers. When the film-like adhesive contains conductive particles, a film-like adhesive may be suitably used as the anisotropic conductive film.

According to the adhesive composition and the film-like adhesive according to the present embodiment, adherends can be adhered to each other by using heating and pressurization in combination. The heating temperature is not particularly limited, but is preferably 100 to 250 ° C. The pressure is not particularly limited as long as it does not cause damage to the adherend, but it is generally preferably 0.1 to 10 MPa. The heating and the pressurization are preferably performed in the range of 0.5 to 120 seconds. According to the adhesive composition and the film-like adhesive according to the present embodiment, adherends can be sufficiently adhered even under short-term heating and pressurization for 10 seconds at a low pressure of, for example, 150 to 200 DEG C and 1 MPa or so.

The adhesive composition and the film-like adhesive according to the present embodiment can be used as an adhesive for a different adherend having a different thermal expansion coefficient. Concretely, an adhesive composition may be used as a circuit connecting material represented by an anisotropic conductive adhesive, a silver paste and a silver film, or a semiconductor element bonding material typified by an elastomer for CSP, an underfill material for CSP and an LOC tape.

Hereinafter, as an example of a method for connecting circuit members having circuit electrodes and circuit electrodes formed on the main surface of a circuit board with an adhesive composition according to the present embodiment, a film-like adhesive according to this embodiment is used as an anisotropic conductive film A method of manufacturing a connector according to an embodiment of the present invention will be described.

2 is a cross-sectional view showing an embodiment of a connecting member of a circuit member. The connector 1 shown in Fig. 2 is provided with a first circuit member 20 and a second circuit member 30 which are disposed to face each other. Between the first circuit member 20 and the second circuit member 30, a connecting member 10 for bonding and connecting them is provided.

The first circuit member 20 includes a first circuit substrate 21 and a first circuit electrode 22 formed on the main surface 21a of the circuit board 21. The first circuit member 21 has a first circuit electrode 22 formed thereon. An insulating layer may be formed on the main surface 21a of the circuit board 21. [

The second circuit member 30 has a second circuit board 31 and a second circuit electrode 32 formed on the main surface 31a of the circuit board 31. [ An insulating layer may also be formed on the main surface 31a of the circuit board 31. [

The first and second circuit members 20 and 30 are not particularly limited as long as they have circuit electrodes requiring electrical connection. The circuit boards 21 and 31 are formed of a substrate made of an inorganic material such as semiconductor, glass and ceramics, a substrate made of an organic material such as polyimide and polycarbonate, a substrate containing an inorganic material such as glass / . The first circuit substrate 21 may be a glass substrate and the second circuit substrate 31 may be a flexible substrate (preferably, a resin film such as a polyimide film).

Specific examples of the circuit member to be connected include a glass or plastic substrate on which an electrode such as an ITO film is formed, a printed wiring board, a ceramic wiring board, a flexible wiring board, and a semiconductor silicon chip used in a liquid crystal display. These are used in combination as needed. Thus, according to the adhesive composition according to the present embodiment, the printed wiring board and a polyimide film or the like of, in addition to a member having a surface formed from an organic material, copper, and metal such as aluminum, (indium tin oxide) ITO, silicon nitride (SiN x ) and as a member having a surface formed of an inorganic material such as silicon dioxide (SiO 2), may be used to bond the circuit members having a wide variety of surface conditions.

For example, when one of the circuit members is a solar cell having an electrode such as a finger electrode and a bus bar electrode, and the other circuit member is a tap line, the connecting member obtained by connecting them is a solar cell, (A cured product of an adhesive composition) to be adhered to each other.

The connecting member 10 includes a cured product of the adhesive composition according to the present embodiment. The connecting member 10 contains the insulating layer 11 and the conductive particles 7 dispersed in the insulating layer 11. The conductive particles 7 are arranged not only between the opposing circuit electrodes 22 and the circuit electrodes 32 but also between the main surfaces 21a and 31a. The circuit electrodes 22 and 32 are electrically connected through the conductive particles 7. The conductive particles 7 are in direct contact with both the circuit electrodes 22 and 32. As a result, the connection resistance between the circuit electrodes 22 and 32 is sufficiently reduced. Therefore, the flow of current between the circuit electrodes 22 and 32 can be smoothly performed, and the function of the circuit can be sufficiently exhibited. When the connecting member does not contain conductive particles, the circuit electrode 22 and the circuit electrode 32 are in direct contact with each other and are electrically connected.

The bonding strength of the connecting member 10 to the circuit member 20 or 30 is sufficiently high in that the connecting member 10 is formed of the cured product of the adhesive composition according to the present embodiment. Therefore, even after the reliability test (high-temperature and high-humidity test), the decrease of the bonding strength and the increase of the connection resistance can be sufficiently suppressed.

The connection member 1 includes, for example, a step of arranging a pair of circuit members having opposite circuit electrodes, with a film-like adhesive containing an adhesive composition therebetween, a pair of circuit members and a film- (A connecting step) of adhering a pair of circuit members through a cured product of an adhesive composition by heating while pressing in the thickness direction of the film-like adhesive in the direction of the thickness of the adhesive.

Fig. 3 is a cross-sectional view showing an embodiment of a method of manufacturing the connector 1. Fig. 3 (a), a film-like adhesive 40 is stacked on the main surface of the first circuit member 20 on the circuit electrode 22 side. When a film-like adhesive 40 is provided on the above-mentioned support, a laminate of a film-like adhesive and a support is stacked on the circuit member in the direction in which the film-like adhesive 40 is positioned on the first circuit member 20 side do. The film-like adhesive 40 is easy to handle in that it is a film. The film adhesive 40 can be easily interposed between the first circuit member 20 and the second circuit member 30 and the first circuit member 20 and the second circuit member 30 can be easily interposed between the first circuit member 20 and the second circuit member 30. [ The connection operation can be easily performed.

The film-like adhesive 40 is the above-mentioned adhesive composition (circuit connection material) formed into a film, and has the conductive particles 7 and the insulating adhesive layer 5. The adhesive composition can be used as a circuit connecting material for anisotropically conductive bonding, even when it does not contain conductive particles. A circuit connecting material not containing conductive particles may be referred to as NCP (Non-Conductive Paste). When the adhesive composition contains conductive particles, the circuit connecting material using the adhesive composition may be referred to as ACP (Anisotropic Conductive Paste).

The thickness of the film-like adhesive 40 is preferably 10 to 50 mu m. If the thickness of the film-like adhesive 40 is small, the space between the circuit electrodes 22 and 32 tends to be hard to be filled with the adhesive. If the thickness of the film-like adhesive is large, the adhesive composition between the circuit electrodes 22 and 32 can not be entirely removed sufficiently, and it becomes difficult to secure the conduction between the circuit electrodes 22 and 32.

The film adhesive 40 is temporarily connected to the first circuit member 20 by applying the pressure A and B in the thickness direction of the film adhesive 40 as shown in Fig. At this time, it may be pressurized while heating. However, the heating temperature is set at a temperature at which the adhesive composition in the film-like adhesive 40 does not cure, that is, a temperature sufficiently lower than a temperature at which the radical polymerization initiator abruptly generates radicals.

3 (c), the second circuit member 30 is placed on the film-like adhesive 40 in the direction in which the second circuit electrode is positioned on the first circuit member 20 side do. When the film-like adhesive 40 is provided on the support, the second circuit member 30 is placed on the film-like adhesive 40 after the support is peeled off.

The film adhesive 40 is heated while being pressed in the thickness directions A and B thereof. The heating temperature at this time is set to a temperature at which the radical polymerization initiator sufficiently generates radicals. As a result, radicals are generated from the radical polymerization initiator and polymerization of the radical polymerizable compound is initiated. The insulating adhesive 11 is formed by heating the adhesive agent 40 on the film so that the distance between the circuit electrode 22 and the circuit electrode 32 is sufficiently small. As a result, the first circuit member 20 and the second circuit member 30 are firmly connected through the connecting member 10 including the insulating layer 11. By this connection, the connection member shown in Fig. 2 is obtained.

The connection is preferably performed under the conditions of a heating temperature of 100 to 250 DEG C, a pressure of 0.1 to 10 MPa, and a pressing time of 0.5 to 120 seconds. These conditions are appropriately selected depending on the application to be used, the adhesive composition, and the circuit member. According to the adhesive composition according to the present embodiment, it is possible to obtain a connector having sufficient reliability under low-pressure conditions such as 1.0 to 1.5 MPa. After the connection, if necessary, post-curing may be performed.

The pressure of this connection is calculated from the load and the area to be compressed by the formula: load / compression area. The compressed area is the area of the portion to be pressed out of the smallest rectangular area surrounding the entire portion where the first circuit electrode and the second circuit electrode overlap when viewed in the thickness direction of the adhesive agent (adhesive composition) on the film.

Referring to the plan view of FIG. 4, a method for obtaining the area of the pressed area will be described in more detail. 4 (a) is a plan view showing a film-like adhesive laminated (temporarily connected) on the circuit member 20 and the circuit member 20. Fig. A plurality of rectangular first circuit electrodes 22 having a length y are juxtaposed over the width x on the main surface 21a of the first circuit substrate 21 such that the respective ends of the first circuit electrodes 22 are arranged substantially in a straight line. The film-like adhesive 40 is stacked so as to cover the entire first circuit electrodes 22.

The second circuit board 31 is mounted on the film-like adhesive 40 so that the second circuit electrode provided on the main surface thereof faces the first circuit electrode 22 as shown in Fig. 4 (b) . (Hereinafter referred to as " electrode facing area ") of the rectangular area surrounding the entire area where the first circuit electrode and the second circuit electrode overlap, when viewed from the thickness direction of the film-like adhesive 40 A pressure is applied to the region 50a containing the liquid. 4B, the electrode facing region is a rectangular region having a width x and a length y 1 (= y). When the whole of the electrode facing region is thus pressed, the area of the pressed area is the product of the width x of the electrode facing region and the length y 1 .

As shown in FIG. 4 (c), when pressure is applied to the region 50b including a part of the electrode facing region, the pressing area is the width x of the electrode facing region and the width x of the portion It is the product of the length y 2 .

When the film-like adhesive contains a radical polymerization initiator that generates radicals by light irradiation, light irradiation can be performed instead of heating when the film-like adhesive is cured for this connection. Instead of the film-like adhesive prepared in advance, for example, an adhesive composition in a paste state may be used as a circuit connecting material. For example, by a method including a step of coating the first circuit member 20 or the second circuit member 30 with a coating liquid prepared by dissolving the adhesive composition in a solvent as required, and drying the coating film A film-like adhesive can be formed.

Example

Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. However, the present invention is not limited to the following examples.

(Review I)

1. Synthesis of polyurethane resin

1000 parts by mass of polypropylene glycol (Mn = 2000), which is a diol having an ester bond, and 4000 parts by weight of methyl ethyl ketone as a solvent were added to a separable flask equipped with a reflux condenser, a thermometer and a stirrer, and the mixture was stirred at 40 DEG C for 30 minutes . After the solution was heated to 70 캜, 12.7 mg of dimethyl tin laurate as a catalyst was added. Subsequently, a solution prepared by dissolving 125 parts by weight of 4,4-diphenylmethane-diisocyanate in 125 parts by weight of methyl ethyl ketone was added dropwise to this solution over one hour. Thereafter, stirring was continued at this temperature until the absorption peak of NCO could not be seen with an infrared spectrophotometer to obtain a methyl ethyl ketone solution of a polyurethane resin. The solution was adjusted so that the solid concentration (concentration of the polyurethane resin) was 30 mass%. The weight average molecular weight of the obtained polyurethane resin was 320000 (in terms of standard polystyrene) as a result of measurement by GPC. The analysis conditions of GPC are described below.

Figure 112014029468592-pct00006

2. Synthesis of urethane acrylate

4000 parts by mass of a polycarbonate diol (manufactured by Aldrich Chemical Co., Ltd., number average molecular weight: 2000) and 2 parts by mass of 2-hydroxyethyl acrylate , 0.49 parts by mass of hydroquinone monomethyl ether, and 4.9 parts by mass of a tin catalyst were added to the reaction mixture. 666 parts by mass of isophorone diisocyanate (IPDI) was uniformly added dropwise to the reaction solution heated to 70 占 폚 over 3 hours and reacted. The reaction was continued for 15 hours after completion of the dropwise addition, and when the NCO% became 0.2% or less, the reaction was regarded as the completion of the reaction to obtain urethane acrylate. As a result of analysis by GPC, the weight average molecular weight of the urethane acrylate was 8500 (in terms of standard polystyrene).

3. Synthesis of acrylate compound having epoxy group

(Acrylate Compound A)

330 parts by mass of a bisphenol F type epoxy resin (diglycidyl ether of bisphenol F, JER806 (product name, manufactured by Mitsubishi Chemical Corporation, epoxy equivalent: 160 to 170) was added to a reactor equipped with a stirrer, a reflux condenser and a thermometer , 1 part by mass of benzyltriethylammonium chloride, and 0.1 part by mass of t-butylcatechol were added to 72 parts by mass of acrylic acid (ratio of 1 mole of acrylic acid to 2 moles of epoxy group in epoxy resin). The reaction solution was stirred at 100 占 폚 for 3 hours while allowing the reaction between the epoxy group and acrylic acid to proceed. After completion of the reaction, the reaction solution was returned to room temperature, and 300 parts by mass of benzene was added thereto to dissolve the product therein. Subsequently, an aqueous solution of sodium carbonate and distilled water were added in this order, and the solution was washed three times. Thereafter, the benzene was sufficiently distilled off to obtain a crude product. The crude product was analyzed by liquid chromatography. As a result, it was found that, in addition to the acrylate compound having one epoxy group as the target compound, a bifunctional acrylate compound having no epoxy group and a raw bisphenol F type epoxy resin were included in the crude product I could. Thereupon, the crude product was purified to obtain an acrylate compound A having one epoxy group and one acryloyloxy group and having a bisphenol F skeleton.

(Acrylate compound B)

Except that 430 parts by mass of diglycidyl ether of hydrogenated bisphenol A (HBE-100 (product name), Shin-Nippon Rikagaku Co., Ltd., epoxy equivalent: 210 to 220) was used in place of bisphenol F type epoxy resin. By the same procedure, an acrylate compound B having one epoxy group and one acryloyloxy group and having a hydrogenated bisphenol A skeleton was obtained.

4. Fabrication of conductive particles

A nickel layer having a thickness of 0.2 mu m was formed on the surface of the polystyrene particles, and then a gold layer having a thickness of 0.04 mu m was formed outside the nickel layer. Thus, conductive particles having an average particle diameter of 4 탆 were produced.

5. Production of adhesive on film

The raw materials shown in Table 2 were mixed at a mass ratio shown in Table 2. The conductive particles were dispersed in a proportion of 1.5% by volume to obtain a coating solution for forming a film-like adhesive agent. This coating solution was applied to a polyethylene terephthalate (PET) film having a thickness of 50 탆 by using a coating and spreading apparatus. The coated film was hot-air dried at 70 DEG C for 10 minutes to form a film-like adhesive having a thickness of 18 mu m.

The polyurethane resin, urethane acrylate, acrylate compound A and acrylate compound B shown in Table 2 were synthesized as described above. The phenoxy resin was used in the form of a 40 mass% solution prepared by dissolving 40 g of PKHC (trade name, manufactured by Union Carbide, average molecular weight 45000) in 60 g of methyl ethyl ketone. The acrylate compound C is a monofunctional acrylate compound (CHA, trade name, manufactured by Toagosei Co., Ltd.). Acrylate Compound D is a bifunctional acrylate compound (ABE-300, trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.). 2-methacryloyloxyethyl acid phosphate (Lightestester P-2M, trade name, manufactured by Kyowa Chemical Co., Ltd.) was used as the phosphoric acid ester. As the silane coupling agent, 3-methacryloxypropyltrimethoxysilane (KBM-503, trade name, manufactured by Shin-Etsu Chemical Co., Ltd.) was used. T-hexylperoxy-2-ethylhexanoate (perhexyl O, trade name, manufactured by Nichichi Co., Ltd.) was used as a radical polymerization initiator. 10 g of silica particles (R104, trade name, manufactured by Nippon Aerosil Co., Ltd.) as inorganic particles were dispersed in a mixed solvent of 45 g of toluene and 45 g of ethyl acetate to prepare a 10 mass% dispersion, which was then compounded in the coating solution. The mixing ratio of the silica particles was 20 parts by mass based on 100 parts by mass of the total amount of the phenoxy resin, the polyurethane resin, the urethane acrylate and the acrylate compounds A to D.

Figure 112014029468592-pct00007

6. Connecting body

(FPC) having 2200 copper circuits each having a line width of 75 mu m, a pitch of 150 mu m, and a thickness of 18 mu m using the film-like adhesive as a circuit connecting material, and a flexible circuit board An ITO substrate (thickness: 1.1 mm, surface resistance: 20? /?) Having a thin layer of indium oxide (ITO) was connected. The connection was performed by heating and pressing at 180 DEG C, 3 MPa, or 1 MPa for 5 seconds using a thermocompression bonding apparatus (heating method: Constant heat type, manufactured by Toray Engineering Co., Ltd.). As a result, a connection body in which an FPC and an ITO substrate were connected by a cured product of a film-like adhesive agent over a width of 1.5 mm was manufactured. The pressure of the pressurization was calculated as 4.95 cm 2. In place of the ITO substrate, an SiN substrate (thickness: 0.7 mm) having a thin layer of silicon nitride (SiN) having a thickness of 0.2 占 퐉 formed on a glass substrate and a glass substrate was heated at 180 占 폚 and 3 MPa for 5 seconds and pressurized Thereby manufacturing a connection body between the FPC and the SiN substrate.

(Measurement of connection resistance and adhesive strength)

The resistance value (connection resistance) between adjacent circuits of the obtained connecting member was measured by a multimeter. The resistance value was expressed as an average of 37 points of resistance between adjacent circuits. Further, the adhesive force of the connector was measured by a 90 degree peel method according to JIS-Z0237. Tensilon UTM-4 (peeling speed: 50 mm / min, 25 占 폚) manufactured by Toyo Baldwin Co., Ltd. was used as the adhesive strength measuring apparatus. The connection resistance and the adhesive strength were measured immediately after the connection and after the high temperature and high humidity test in which the connection was maintained for 250 hours in a high-temperature and high-humidity bath at 85 ° C and 85% RH.

(Observation of external appearance of connection body)

The presence or absence of peeling of the interface between the cured product of the circuit connecting material and the FPC and the glass after the high temperature and high humidity test was examined with respect to the ITO substrate and the SiN substrate connecting member using a microscope (trade name: ECLIPSE L200, manufactured by Nikon Corporation) Respectively. Quot; A ", " C ", " C ", " C ", " Respectively.

Figure 112014029468592-pct00008

The evaluation results of the connector are shown in Table 3. According to the film-like adhesive of each of the examples, it was found that any of the cases immediately after the connection and after the high temperature and high humidity test showed good connection resistance (5 Ω or less) and adhesive strength (8 N / cm or more) . On the other hand, in the case of the film-like adhesive of the comparative example which contained no acrylate compound having an epoxy group at all, especially at a low pressure of 1 MPa, the connection resistance was high or peeling was observed after the high temperature and high humidity test.

(Review II)

As described below, the same circuit connecting material as that of the embodiment described in JP-A-2007-224228 was prepared, and a connector manufactured using the circuit connecting material was evaluated.

, 44 parts by mass of an imidazole-based microcapsule mixed type epoxy resin (HX-3941HP, manufactured by Asahi Kasei Chemicals Co., Ltd.) and 10 parts by mass of a radical polymerizing compound, ethylene glycol diacrylate (A-600, Shinnakamura Kagaku Kogyo Co., ) And 16 parts by mass of 3 parts by mass of a radical polymerization initiator 2,5-dimethyl-2,5-di (2-ethylhexanoyl) hexane (manufactured by Nippon Oil Co., Hexa 25O is a 50% solution, the mixing amount of perhexa 25O is 6 parts by mass), and 100 parts by mass of a toluene / ethyl acetate solution having a concentration of PKHC of 40% by mass are mixed and polystyrene spheres And 4 parts by mass of conductive particles having a Ni layer and an Au layer of 0.1 mu m provided on the surface thereof were blended. Further, 1 part by mass of? -Glycidoxypropyltrimethoxysilane (SH6040, manufactured by Dow Corning Silicone Co., Ltd.) was added to obtain a mixed solution for forming a film-like adhesive. This solution was applied to a PET film using an applicator, and the coated film was dried by hot air drying at 70 DEG C for 10 minutes to form a film-like adhesive of 20 mu m in thickness.

Using the obtained film-like adhesive, the connection between the FPC and the ITO substrate was made by the same operation as in Examination 1, by heating and pressing at 180 deg. C, 3 MPa for 5 seconds. The connection resistance immediately after the connection of the connector was 5.8? And the adhesive force was 3.6 N / cm, which was clearly poor as compared with the connector of the example of Examination 1.

One… 5, Insulating adhesive layer, 7 ... Conductive particles, 8 ... The support, 10 ... Connecting member, 11 ... Insulation layer, 20 ... The first circuit member, 21 ... The first circuit board, 21a ... If you give, 22 ... The first circuit electrode, 30 ... A second circuit member 31, The second circuit board, 31a ... If you give, 32 ... The second circuit electrode, 40 ... Film adhesive, 100 ... Laminated film.

Claims (5)

A circuit connecting material comprising (a) a thermoplastic resin, (b) a radically polymerizable compound, (c) a radical polymerization initiator, and (e)
Wherein the thermoplastic resin is contained in an insulating adhesive agent which is composed of components other than the conductive particles and disperses the conductive particles in the circuit connecting material and is a polyimide resin, a polyamide resin, a phenoxy resin, a polyester resin, a polyurethane resin And a polyvinyl butyral resin.
Wherein the radically polymerizable compound comprises a compound having an epoxy group,
Wherein the compound having an epoxy group is a compound having an epoxy group and a (meth) acrylic group produced by a reaction between a polyfunctional epoxy compound having a plurality of epoxy groups and (meth) acrylic acid, wherein the epoxy equivalent of the polyfunctional epoxy compound is , 130 to 250 g / equivalent,
Wherein the amount of the epoxy group-containing compound is 5 to 15% by mass based on the total amount of the thermoplastic resin and the radical polymerizable compound. The circuit connecting material according to claim 1, further comprising (d) a silane coupling agent represented by the following formula (1).
Figure 112017130497691-pct00014

R 1 , R 2 and R 3 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkoxycarbonyl group having 1 to 5 carbon atoms or an aryl group, R 1, R 2 and R at least one of the three is the alkoxy group having 1 to 5, R 4 is a (meth) acryloyloxy group with an acrylic, a vinyl group, an isocyanate group, an imidazole group, a mercapto group, an amino group, a methylamino group, A methylamino group, a dimethylamino group, a benzylamino group, a phenylamino group, a cyclohexylamino group, a morpholino group, a piperazino group, an ureido group or a glycidyl group, and a represents an integer of 1 to 10, A pair of circuit members disposed opposite to each other with circuit electrodes,
And a connection member which is provided between the pair of circuit members and which bonds the pair of circuit members to each other,
And,
The circuit electrodes of one circuit member and the circuit electrodes of the other circuit member are electrically connected,
Wherein the connecting member is a cured product of the circuit connecting material according to any one of claims 1 and 2. The connector according to claim 3, wherein one circuit member has a glass substrate and the other circuit member has a flexible substrate. delete
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