KR20140064967A - Circuitry connecting material and connecting method and connecting structure using same - Google Patents
Circuitry connecting material and connecting method and connecting structure using same Download PDFInfo
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- KR20140064967A KR20140064967A KR1020147010110A KR20147010110A KR20140064967A KR 20140064967 A KR20140064967 A KR 20140064967A KR 1020147010110 A KR1020147010110 A KR 1020147010110A KR 20147010110 A KR20147010110 A KR 20147010110A KR 20140064967 A KR20140064967 A KR 20140064967A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
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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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
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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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- 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
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/10—Details of components or other objects attached to or integrated in a printed circuit board
- H05K2201/10007—Types of components
- H05K2201/10128—Display
- H05K2201/10136—Liquid Crystal display [LCD]
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- Adhesives Or Adhesive Processes (AREA)
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Abstract
The present invention provides a circuit connecting material capable of improving the adhesion between the silicon nitride film and the interface and exhibiting excellent connection reliability when subjected to high temperature and high humidity treatment. The circuit connecting material contains (1) a polyfunctional (meth) acrylate monomer, (2) a radical polymerization initiator that generates free radicals by heat or light, and (3) a monofunctional (meth) , The monofunctional (meth) acrylate monomer has a biphenyl group or a naphthalene group, and a bonding position of a biphenyl group or a naphthalene group to an oxygen atom bonding thereto is an ortho, meta or para position.
Description
The present invention relates to a connection method for connecting a pair of circuit members using a circuit connection material and a circuit connection material, and a connection structure obtained by the connection method.
This application is based upon and claims the benefit of priority from Japanese Patent Application No. 2011-206379, filed on September 21, 2011, the entirety of which is incorporated herein by reference.
BACKGROUND ART Conventionally, a circuit connecting member in which conductive particles are dispersed when electrically connecting a pair of circuit members is used. As the circuit connecting member, for example, an anisotropic conductive film (ACF: Anisotropic Conductive Film) may be used. However, anisotropic conductive film may be used as the circuit connecting member. The connecting surface, on which the wiring electrodes of the substrate are formed, As shown in Fig. In the connection method using an anisotropic conductive film, an anisotropic conductive film is attached to the connection surface of the substrate, and the connection surfaces of the anisotropic conductive film and the electronic component are disposed to face each other, so that the electronic components are disposed on the anisotropic conductive film. As a result, the conductive particles in the anisotropic conductive film are sandwiched between the terminal electrodes of the electronic component and the wiring electrodes of the substrate and are crushed. As a result, the terminal electrode of the electronic component and the wiring electrode of the substrate are electrically connected through the conductive particles.
The conductive particles not present between the terminal electrode and the wiring electrode are present in the insulating adhesive composition of the anisotropic conductive film and remain electrically insulated. That is, electrical conduction can be achieved only between the terminal electrode and the wiring electrode.
The adhesive composition constituting such a circuit connecting member may conventionally contain an epoxy resin or the like. The adhesive composition generally contains an epoxy resin, a curing agent such as a phenol resin reacting with the epoxy resin, a latent curing agent for promoting the reaction between the epoxy resin and the curing agent, and the like.
In recent years, in order to shorten the production time, an adhesive composition which performs curing at a low temperature for a short time is required for the anisotropic conductive film. In order to comply with this demand, radical-curable adhesive compositions containing radical polymerization initiators such as (meth) acrylate derivatives and peroxides have attracted attention. The radical curing type circuit connecting material is advantageous for shortening the production time because the curing reaction proceeds in a short time by radicals rich in reactivity (see Patent Documents 1 and 2).
However, the (meth) acrylate derivative has a larger hardening shrinkage upon polymerization than the epoxy resin and the like, and the internal stress tends to be large after curing. Therefore, when a circuit connecting material containing a radical-curing adhesive composition is used, bubbles are generated at the interface between the adhesive layer and a substrate such as an LCD panel, and the connection reliability may be deteriorated. Particularly, in the TFT (Thin Film Transistor) type LCD panel, the occurrence of bubbles becomes remarkable at the interface with the silicon nitride (SiN) film used as the insulating film on the panel wiring, the adhesion is decreased, There is a concern.
SUMMARY OF THE INVENTION The present invention has been proposed in view of such conventional circumstances, and it is an object of the present invention to provide a circuit connecting material capable of improving the adhesion of the interface of a silicon nitride film and exhibiting excellent connection reliability when subjected to high temperature and high humidity treatment, A connection method for connecting a pair of circuit members, and a connection structure obtained by the connection method.
(1) a polyfunctional (meth) acrylate monomer; (2) a radical polymerization initiator that generates a free radical by heat or light; and (Meth) acrylate monomer is represented by the following general formula (1): wherein R is a biphenyl group or a naphthalene group, and R is a bond with an oxygen atom bonding thereto Position is an ortho, meta, or para position, and n is 1 to 10.
In order to solve the above-described problems, the connection structure of the present invention is characterized in that a circuit connecting material is interposed between a pair of circuit members arranged so that circuit electrodes are opposed to each other, and a connection (1) a polyfunctional (meth) acrylate monomer; and (2) a radical polymerization initiator which generates free radicals by heat or light. In the structure, one of the circuit members is covered with a silicon nitride film, (Meth) acrylate monomers are represented by the following general formula (1): wherein R is a biphenyl group or a naphthalene group, and R and a bond And n is an integer of from 1 to 10. The bonding position of the oxygen atom to the oxygen atom is an ortho, meta, or para position.
≪ Formula 1 >
Further, in order to solve the above-mentioned problems, the connection method of the present invention is a method of connecting a circuit connecting material between a pair of circuit members disposed so as to face each other with circuit electrodes, (1) a polyfunctional (meth) acrylate monomer; (2) a free radical is generated by heat or light; and (3) the surface of the circuit member is covered with a silicon nitride film. (Meth) acrylate monomers are represented by the following general formula (1): wherein R is a biphenyl group or a naphthalene group, and R 1 is a biphenyl group or a naphthalene group, The bonding position of R and the oxygen atom bonding thereto is an ortho, meta, or para position, and n is 1 to 10.
≪ Formula 1 >
According to the present invention, it is possible to provide a circuit connecting material capable of improving the adhesion between the silicon nitride film and the interface and exhibiting excellent connection reliability when subjected to a high-temperature and high-humidity treatment, and a circuit connecting material connecting the pair of circuit members And a connecting structure obtained by the connecting method can be provided.
Hereinafter, specific embodiments of the present invention (hereinafter referred to as "present embodiment") will be described in detail in the following order with reference to the drawings.
<1. Circuit connecting material>
<2. Connection method>
<3. Examples>
<1. Circuit connecting material>
The circuit connecting material in this embodiment is interposed between a pair of circuit members disposed so as to face each other with respect to the circuit electrodes, and electrically and mechanically connects the opposing circuit members. The circuit connecting material in this embodiment is applied to an anisotropic conductive film formed by dispersing a plurality of conductive particles in an insulating adhesive composition and formed into a film.
The insulating adhesive composition contains a polyfunctional (meth) acrylate compound, a monofunctional (meth) acrylate monomer, a radical polymerization initiator that generates free radicals by heat or light, and a film forming resin. The (meth) acrylate includes acrylate and methacrylate.
The multifunctional (meth) acrylate compound and the monofunctional (meth) acrylate monomer are all radical polymerizable resins. When the anisotropic conductive film is heated, a cross-linked structure is formed in the insulating adhesive composition, .
The monofunctional (meth) acrylate monomer is represented by the formula (1).
≪ Formula 1 >
In formula (1), R is a biphenyl group or a naphthalene group. The bonding position of R and the oxygen atom O bonded thereto is an ortho, meta or para position. n is from 1 to 10, with 1 to 3 being particularly preferred. When n is too large, the cross-linking structure is loosened and the adhesion (adhesion) of the anisotropic conductive film to the silicon nitride film is lowered.
The monofunctional (meth) acrylate monomer has a structure including such a bulky R, an appropriate length of (CH 2 CH 2 O) n and -COCH = CH 2 performing radical polymerization, The curing shrinkage is reduced and the internal stress after curing is reduced so that the occurrence of bubbles at the interface between the adhesive layer and the silicon nitride film of the substrate at the time of connection is suppressed and the connection can be made with high adhesion. That is, by including such a monofunctional (meth) acrylate monomer in the anisotropic conductive film, high connection reliability can be obtained in the connection structure formed by connecting using the anisotropic conductive film.
As the monofunctional (meth) acrylate monomer, for example, ethoxylated o-phenylphenol acrylate represented by the general formula (2) can be given.
The bonding position of the biphenyl group and the oxygen atom bonding to the biphenyl group is not limited to the ortho position as shown in the general formula (2) but may be a meta position (ethoxylated m-phenylphenol acrylate) or a para position (ethoxylated p-phenylphenol acrylate ).
Further, even when R is a naphthalene group, the bonding position of the naphthalene group and the oxygen atom bonding to the naphthalene group may be an ortho, meta, or para position.
The blending amount of the monofunctional (meth) acrylate monomer in the insulating adhesive composition is preferably 3 to 20 mass% (3 to 20 mass parts with respect to 100 mass parts of the insulating adhesive composition). If it is less than 3% by mass, the effect of the monofunctional (meth) acrylate monomer becomes difficult to obtain and the bonding strength becomes weak. On the other hand, if it exceeds 20% by mass, the cured product becomes poor in heat resistance, and the conduction resistance value becomes high.
By including such a monofunctional (meth) acrylic monomer, the adhesion of the interface of the silicon nitride film can be improved while suppressing the fluctuation of the resistance value between the circuit electrodes when subjected to the high temperature and high humidity treatment, and to exhibit excellent connection reliability.
Examples of the polyfunctional (meth) acrylate compound include polyfunctional (meth) acrylate monomers, polyfunctional (meth) acrylate oligomers and polyfunctional (meth) acrylate polymers.
Examples of the bifunctional (meth) acrylate include bisphenol F-EO modified di (meth) acrylate, bisphenol A-EO modified di (meth) acrylate, polypropylene glycol di (meth) acrylate, polyethylene glycol (Meth) acrylate, dicyclopentadiene (meth) acrylate, and the like.
Examples of the trifunctional (meth) acrylate include trimethylolpropane tri (meth) acrylate, trimethylolpropane PO-modified (meth) acrylate, and isocyanuric acid EO-modified tri (meth) acrylate.
Examples of the tetrafunctional or higher (meth) acrylate include dipentaerythritol penta (meth) acrylate, pentaerythritol hexa (meth) acrylate, pentaerythritol tetra (meth) acrylate, ditrimethylol propane tetraacrylate, . Other polyfunctional urethane (meth) acrylates may also be used.
The radical polymerization initiator may be a known radical polymerization initiator as a curing agent which decomposes by heat or light to generate free radicals. Examples thereof include peroxide-based polymerization initiators such as diacyl peroxide, peroxydicarbonate, peroxy ester, peroxyketal, dialkyl peroxide and hydroperoxide, azo-based polymerization initiators such as azobisbutyronitrile, Redox polymerization initiators, and the like.
Too small an amount of the radical polymerization initiator in the insulating adhesive composition causes insufficient curing, while if too large, the cohesive force of the anisotropic conductive film lowers. Therefore, the amount is preferably 1 to 10 parts by mass per 100 parts by mass of the (meth) Mass part, and more preferably 3 to 7 mass parts.
As the film-forming resin, for example, a thermoplastic elastomer such as an epoxy resin, a polyester resin, a polyurethane resin, a phenoxy resin, a polyamide, EVA or the like can be used. Among them, a polyester resin, a polyurethane resin, a phenoxy resin, particularly a phenoxy resin, for example, a bis A type epoxy resin and a phenoxy resin having a fluorene skeleton can be mentioned for heat resistance and adhesiveness.
If the amount of the film-forming resin is too small, the film is not formed. If the film-forming resin is too much, the exclusion of the resin for obtaining electrical connection tends to be lowered. Therefore, when 100 mass% of resin solids (an adhesive composition comprising a polymerizable acrylic compound and a film- Is preferably 80 to 30 parts by mass, more preferably 70 to 40 parts by mass.
As the conductive particles, conductive particles used in conventional anisotropic conductive films can be used. For example, metal particles such as gold particles, silver particles, and nickel particles, and metal particles such as benzoguanamine resin and styrene resin, , Metal coated resin particles coated with a metal such as nickel or zinc, and the like. The average particle diameter of the conductive particles is preferably 1 to 20 占 퐉, more preferably 2 to 10 占 퐉, from the viewpoint of connection reliability.
The average particle density of the conductive particles in the insulating adhesive composition is preferably 500 to 50,000 / mm 2 , more preferably 1000 to 30,000 / mm 2 in terms of connection reliability and insulation reliability.
The insulating adhesive composition may contain phosphoric acid acrylate in order to improve the adhesion to the metal.
The insulating adhesive composition may contain other additives such as diluting monomers such as various acrylic monomers, fillers, softening agents, coloring agents, flame retarding agents, thixotropic agents, silane coupling agents, and silica fine particles.
By including the silane coupling agent, the adhesion at the interface between the organic material and the inorganic material is improved. By containing silica fine particles, it is possible to improve the connection reliability by adjusting the storage elastic modulus and the linear expansion coefficient.
The anisotropic conductive film of the present embodiment comprises a multifunctional (meth) acrylate compound as a radical polymerizable resin, a monofunctional (meth) acrylate monomer represented by the general formula (1), a (meth) acrylate compound, , The conductive particles are uniformly dispersed and mixed in an insulating adhesive composition containing a film-forming resin by a known dispersing method, and the resulting mixture is applied to a release film such as a silicone-peeled polyester film by a known coating method such as a bar coater To a dry thickness of 10 to 50 占 퐉, and the mixture is put in a constant temperature bath at 50 to 90 占 폚 and dried, for example. When the insulating adhesive film is laminated on the anisotropic conductive film, it can be obtained by applying an insulating adhesive composition on the anisotropic conductive film and drying the insulating adhesive film.
As the release film, for example, a release agent such as silicone is applied to PET (Poly Ethylene Terephthalate), OPP (Oriented Polypropylene), PMP (Poly-4-methylpentene-1), PTFE (Polytetrafluoroethylene) And keeps the shape of the anisotropic conductive film.
According to the anisotropic conductive film of the present embodiment, by containing the monofunctional (meth) acrylic monomer having the structure represented by the formula (1), it is possible to suppress the fluctuation of the resistance value between the circuit electrodes when subjected to the high- So that it is possible to exhibit excellent connection reliability.
<2. Connection method>
Provided is a connection method for connecting a glass substrate constituting an LCD (Liquid Crystal Display) panel and a COF (Chip On Film) as a wiring material through the anisotropic conductive film of the present embodiment. On the glass substrate, wiring electrodes are formed at a fine pitch. In the COF, a terminal electrode is formed in accordance with the wiring pattern of the wiring electrode. By this connection method, the wiring structure of the glass substrate and the terminal electrode of the COF are anisotropically electrically connected to each other to obtain a connection structure.
Hereinafter, a connection method for press-connecting the glass substrate and the COF through the anisotropic conductive film will be described in detail. First, the surface on which the wiring electrodes are formed on the glass substrate and the anisotropic conductive film are attached to the glass substrate (adhesion step). In this attachment, the pressing surface of the head portion heated to a low temperature of the pressure bonder is lightly pressed on the upper surface of the conductive particle-containing layer to pressurize it with a low pressure. The heating temperature is a low temperature (for example, a predetermined value of 60 to 80 캜) at which the insulating adhesive composition flows but does not harden. The pressing pressure in the adhesion step is a predetermined value, for example, 0.5 MPa to 2 MPa. The heat pressing time in the adhesion step is, for example, a predetermined time in 1 to 3 seconds (sec).
The anisotropic conductive film is peeled off after the peeling step, and the anisotropic conductive film is peeled off from the anisotropic conductive film after the peeling step. And a repairing process is carried out to attach it from the correct position (repairing step).
Subsequently, the bumps and the wiring electrodes are opposed to each other, and the COF is arranged on the anisotropic conductive film (arrangement step).
Then, the pressurized surface (not shown) of the heated head portion of the pressure bonder is pressed against the upper surface of the COF to press-connect the glass substrate and the COF (connection step).
The pressing pressure in the connecting process is a predetermined value, for example, from 1 MPa to 5 MPa. The heating temperature in the connection step is a temperature (for example, a predetermined value of 160 to 210 캜) at which the insulating particles are melted and the insulating adhesive composition is cured. The heat pressing time in the connecting step is, for example, a predetermined time of 3 to 10 seconds.
In this manner, the conductive particles are sandwiched between the wiring electrodes and the bumps, and the adhesive composition is cured. Thus, the glass substrate and the COF are electrically and mechanically connected. Then, a connection structure in which the glass substrate and the COF are anisotropically electrically connected is obtained. The resulting connection structure can exhibit excellent connection reliability and conduction reliability while maintaining good insulation reliability as described above.
Although the present invention has been described above, it is needless to say that the present invention is not limited to the above-described embodiments, and various modifications are possible without departing from the gist of the present invention.
In the above-described embodiment, an anisotropic conductive film is used as the anisotropic conductive adhesive member. However, the structure of the anisotropic conductive adhesive member is not limited to this. For example, an anisotropic conductive film having a two-layer structure in which an insulating adhesive layer is further laminated may be used. It is also possible to form a two-layer adhesive layer by, for example, including a conductive adhesive paste in which conductive particles are contained in an insulating adhesive composition and an insulating adhesive paste containing an insulating adhesive composition.
In the above-described embodiment, a glass substrate constituting an LCD (Liquid Crystal Display) panel is used as the glass substrate. However, the glass substrate is not limited to this. For example, a PDP substrate (PDP panel) , An organic EL substrate (organic EL panel), or the like.
In the above-described embodiment, the case where a glass substrate is used as the substrate has been described, but it may be another substrate such as a rigid substrate, a flexible substrate, or the like. In the above-described embodiment, the case where the COF is used as the electronic component has been described, but it may be another electronic component such as an IC chip or a TAB.
Although the present invention is applied to FOG (Film On Glass) in the above-described embodiments, the present invention can be applied to other mounting methods such as COG (Chip On Glass) and FOB .
[Example]
Hereinafter, specific examples of the present invention will be described based on experimental results.
≪ Example 1 >
As a film-forming resin, 60 parts by mass of a polyester urethane resin (trade name: UR8200, manufactured by Toyobo Chemical Co., Ltd., dissolved in a mixed solvent of methyl ethyl ketone / toluene = 50: 50 in 20 mass% , 33 parts by mass (33 mass%) of a radical polymerizable resin (trade name: EB-600, manufactured by Daicel-Cytech Kabushiki Kaisha) and ethoxylated o-phenylphenol acrylate (trade name: 1 part by mass (1% by mass), a silane coupling agent (trade name: KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd.) (trade name: A-LEN-10, Shinnakamura Kagaku Kagaku Kagaku Co., 1 part by mass), 1 part by mass (1 mass%) of phosphoric acid acrylate (trade name: P-1M, manufactured by Kyowa Chemical Co., Ltd.), a radical polymerization initiator (trade name: Perhexa C, manufactured by Nippon Yushi Kikai Co., And 4 parts by mass (4% by mass) of an insulating adhesive composition , Conductive particles (trade name: AUL704, manufactured by Sekisui Chemical Co., Ltd.) were uniformly dispersed so as to have a particle density of 10,000 / mm 2 , and the conductive particle-containing composition was applied on a peeling film by a bar coater and dried, A circuit connecting material having a thickness of 15 mu m was produced.
Then, a process of connecting a glass substrate and a COF (50 탆 P, Cu 8 탆 t-Sn plating, 38 탆 t-S'perflex substrate) was performed through the produced anisotropic conductive film. As the glass substrate, an IZO-coated glass substrate (entire surface IZO coating, glass thickness: 0.7 mm) and a SiN-coated glass substrate (entire surface SiN coating) were used for measuring the continuity resistance value. First, the anisotropic conductive film was slit with a width of 1.5 mm on the surface on which the wiring electrode was formed on the glass substrate, and was attached on the glass substrate (adhesion step). In this attachment, the pressing surface of the head portion heated by the low temperature of the pressure bonder was lightly pressed on the upper surface of the conductive particle-containing layer to pressurize it with a low pressure. The heating temperature was set at 70 캜, which is a low temperature at which the insulating particles do not dissolve and the insulating adhesive composition flows but does not cure. Further, the pressing pressure in the adhesion step was set to 1 MPa. In addition, the heat pressing time in the adhesion step was 2 seconds.
Subsequently, COF was placed on the anisotropic conductive film so as to face the terminal electrodes of the COF and the wiring electrodes of the glass substrate (arrangement step).
Then, the pressing surface (1.5 mm width) of the heated head portion of the pressure bonder was pressed onto the upper surface of the COF through a cushioning material (100 μm Teflon (registered trademark)) to press-connect the glass substrate and the COF (connection step).
The pressing pressure in the connection step was 4 MPa. The heating temperature in the connecting step was 190 占 폚. The heat pressing time in the connecting step was 5 seconds.
In this manner, the conductive particles were sandwiched between the wiring electrode and the bump, and the adhesive composition was cured to electrically and mechanically connect the glass substrate and the COF to obtain a connection structure.
≪ Example 2 >
32 parts by mass of a radical polymerizable resin (trade name: EB-600, manufactured by Daicel-Cytec Co., Ltd.), 30 parts by mass of ethoxylated o-phenylphenol acrylate (trade name: A-LEN-10, manufactured by Shinnakamura Kagaku Kogyo Kabushiki Kaisha) ) Was changed to 2 parts by mass, a circuit connecting material was produced under the same conditions as in Example 1. [
≪ Example 3 >
31 parts by mass of a radical polymerizable resin (trade name: EB-600, manufactured by Daicel-Cytech Kabushiki Kaisha), 10 parts by mass of ethoxylated o-phenylphenol acrylate (trade name: A-LEN-10, manufactured by Shin Namakura Kagaku Kogyo K.K.) ) Was changed to 3 parts by mass, a circuit connecting material was produced under the same conditions as in Example 1. [
<Example 4>
30 parts by mass of a radical polymerizable resin (trade name: EB-600, manufactured by Daicel Scientific Co., Ltd.), 30 parts by mass of ethoxylated o-phenylphenol acrylate (trade name: A-LEN-10, manufactured by Shinnakamura Kagaku Kogyo K.K. ) Was changed to 4 parts by mass, a circuit connecting material was produced under the same conditions as in Example 1. [
≪ Example 5 >
, 29 parts by mass of a radical polymerizable resin (trade name: EB-600, manufactured by Daicel-Cytech Kabushiki Kaisha Ltd.), 10 parts by mass of ethoxylated o-phenylphenol acrylate (trade name: A-LEN-10, manufactured by Shinnakamura Kagaku Kogyo Kabushiki Kaisha) ) Was changed to 5 parts by mass, a circuit connecting material was prepared under the same conditions as in Example 1. [
≪ Example 6 >
19 parts by mass of a radical polymerizable resin (trade name: EB-600, manufactured by Daicel-Cytech Kabushiki Kaisha) and 50 parts by mass of ethoxylated o-phenylphenol acrylate (trade name: A-LEN-10, manufactured by Shin Nakatama Kagaku Kogyo K.K.) ) Was changed to 15 parts by mass, a circuit connecting material was produced under the same conditions as in Example 1. [
≪ Example 7 >
, 14 parts by mass of a radical polymerizable resin (trade name: EB-600, manufactured by Daicel-Cytech Kabushiki Kaisha), 10 parts by mass of ethoxylated o-phenylphenol acrylate (trade name: A-LEN-10, manufactured by Shinnakamura Kagaku Kogyo Kabushiki Kaisha) ) Was changed to 20 parts by mass, a circuit connecting material was produced under the same conditions as in Example 1. [
≪ Example 8 >
9 parts by mass of a radical polymerizable resin (trade name: EB-600, manufactured by Daicel Scientific Co., Ltd.), 10 parts by mass of ethoxylated o-phenylphenol acrylate (trade name: A-LEN-10, manufactured by Shin Nakamura Kagaku Kogyo Kabushiki Kaisha) ) Was changed to 25 parts by mass, a circuit connecting material was prepared under the same conditions as in Example 1. [
≪ Comparative Example 1 &
Except that 34 parts by mass of a radical polymerizable resin (trade name: EB-600, manufactured by Daicel Scientific Co., Ltd.) was contained and no ethoxylated o-phenylphenol acrylate was contained Circuit connecting material.
[Measurement of continuity resistance value]
Initial resistance and resistance after a TH test (Thermal Humidity Test) at a temperature of 85 캜 and a humidity of 85% RH for 500 hours were measured for the connection structures produced in Examples 1 to 8 and Comparative Example 1. The connection resistance was measured when a current of 1 mA was passed through a 4-terminal method using a digital multimeter (digital multimeter 7561, manufactured by Yokogawa Denshiki Co., Ltd.).
[Measurement of Adhesive Strength]
The connection structures of Examples 1 to 8 and Comparative Example 1 were pulled up at 90 degrees (Y-axis direction) at a peeling speed of 50 mm / min using a tensile tester (Tensilon, Orientech) cm) was measured.
The results of the measurement of the conditions, the conduction resistance and the connection strength of Examples 1 to 8 and Comparative Example 1 are shown in Table 1 below.
Since the anisotropic conductive films of Examples 1 to 8 contain ethoxylated o-phenylphenol acrylate, the anisotropic conductive films of Examples 1 to 8 can be produced by mixing a bulky biphenyl group, (CH 2 CH 2 O) n (n = 1) It is considered that the structure including -COCH = CH 2 reduces the curing shrinkage upon polymerization and also reduces the internal stress after curing. Accordingly, it is considered that bubbles are prevented from being generated at the interface between the adhesive layer and the silicon nitride film of the substrate during connection, and high adhesion strength (connection reliability) can be obtained by excellent adhesion.
In particular, in Examples 3 to 7 containing ethoxylated o-phenylphenol acrylate in an amount of 3 to 20% by weight, good values of conduction resistance and adhesion strength were obtained.
On the other hand, in Comparative Example 1, since the ethoxylated o-phenylphenol acrylate is not contained, the curing shrinkage during polymerization is increased and the internal stress after curing is also increased. As a result, at the time of connection, the interface between the adhesive layer and the silicon nitride film It is thought that bubbles are generated in the adhesive layer, resulting in lowered adhesive strength.
Claims (5)
(2) a radical polymerization initiator which generates free radicals by heat or light,
(3) a monomer containing a monofunctional (meth) acrylate monomer,
The monofunctional (meth) acrylate monomer is represented by the general formula (1)
≪ Formula 1 >
In the formula (1), R is a biphenyl group or a naphthalene group, a bonding position of R and an oxygen atom bonding thereto is an ortho, meta or para position, and n is 1 to 10.
The circuit connecting material
(1) a polyfunctional (meth) acrylate monomer,
(2) a radical polymerization initiator which generates free radicals by heat or light,
(3) a monomer containing a monofunctional (meth) acrylate monomer,
The monofunctional (meth) acrylate monomer is represented by the following general formula (1)
≪ Formula 1 >
Wherein R is a biphenyl group or a naphthalene group, a bonding position of R and an oxygen atom bonding thereto is an ortho, meta, or para position, and n is 1 to 10.
Wherein one of the circuit members has a surface covered with a silicon nitride film,
The circuit connecting material
(1) a polyfunctional (meth) acrylate monomer,
(2) a radical polymerization initiator which generates free radicals by heat or light,
(3) a monomer containing a monofunctional (meth) acrylate monomer,
The monofunctional (meth) acrylate monomer is represented by the following general formula (1)
≪ Formula 1 >
Wherein R is a biphenyl group or a naphthalene group, the bonding position of R and an oxygen atom bonding thereto is an ortho, meta, or para position, and n is 1 to 10.
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| JP2011206379A JP5844589B2 (en) | 2011-09-21 | 2011-09-21 | Anisotropic conductive film, connection method using the same, and connection structure |
| JPJP-P-2011-206379 | 2011-09-21 | ||
| PCT/JP2012/073696 WO2013042633A1 (en) | 2011-09-21 | 2012-09-14 | Circuitry connecting material and connecting method and connecting structure using same |
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| JP6065407B2 (en) * | 2012-04-27 | 2017-01-25 | 日立化成株式会社 | Circuit connection material, film-like circuit connection material, circuit connection sheet, circuit connection body and circuit member connection method |
| JP2017103303A (en) * | 2015-11-30 | 2017-06-08 | 日立化成株式会社 | Adhesive for semiconductor, semiconductor device, and method for manufacturing the same |
| JP7413024B2 (en) * | 2020-01-07 | 2024-01-15 | 日本化学工業株式会社 | Conductive adhesive, bonded structures and electronic components using the same |
| JP2022019451A (en) * | 2020-07-17 | 2022-01-27 | 京都エレックス株式会社 | Conductive adhesive composition |
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| JPH11172205A (en) * | 1997-12-11 | 1999-06-29 | Sumitomo Bakelite Co Ltd | Preparation of die attach paste |
| JP2005054140A (en) * | 2003-08-07 | 2005-03-03 | Hitachi Chem Co Ltd | Adhesive composition, adhesive composition for connecting circuit, connected body and semiconductor device |
| JP2008291199A (en) | 2007-04-23 | 2008-12-04 | Hitachi Chem Co Ltd | Circuit connecting material, and connected structure using the same |
| JP2011037953A (en) | 2009-08-07 | 2011-02-24 | Hitachi Chem Co Ltd | Adhesive agent composition, circuit-connecting structure and semiconductor device |
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| JPS62244143A (en) * | 1986-04-16 | 1987-10-24 | Matsushita Electric Ind Co Ltd | Electrical connection for semiconductor element |
| JP3313054B2 (en) * | 1997-12-16 | 2002-08-12 | 住友ベークライト株式会社 | Die attach paste |
| JP3209954B2 (en) * | 1997-12-19 | 2001-09-17 | 住友ベークライト株式会社 | Die attach paste |
| JP2000008021A (en) * | 1998-06-18 | 2000-01-11 | Nichiban Co Ltd | Thermosetting adhesive composition and sheet made of the same |
| JP4900553B2 (en) * | 2005-03-30 | 2012-03-21 | ソニーケミカル＆インフォメーションデバイス株式会社 | Thermosetting anisotropic conductive adhesive |
| JP2009164500A (en) * | 2008-01-10 | 2009-07-23 | Sumitomo Bakelite Co Ltd | Adhesive, and semiconductor package |
| CN102695731B (en) * | 2010-01-07 | 2015-01-21 | 日本合成化学工业株式会社 | Actinic-radiation curable composition and uses thereof |
| TWI494403B (en) * | 2010-01-21 | 2015-08-01 | Nippon Synthetic Chem Ind | Adhesive, adhesive for optical component, optical component with adhesive layer, image display, active energy ray and/or heat hardening adhesive composite, adhesive composite |
| JP2010245546A (en) * | 2010-06-10 | 2010-10-28 | Nitto Denko Corp | Adhesive sheet |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11172205A (en) * | 1997-12-11 | 1999-06-29 | Sumitomo Bakelite Co Ltd | Preparation of die attach paste |
| JP2005054140A (en) * | 2003-08-07 | 2005-03-03 | Hitachi Chem Co Ltd | Adhesive composition, adhesive composition for connecting circuit, connected body and semiconductor device |
| JP2008291199A (en) | 2007-04-23 | 2008-12-04 | Hitachi Chem Co Ltd | Circuit connecting material, and connected structure using the same |
| JP2011037953A (en) | 2009-08-07 | 2011-02-24 | Hitachi Chem Co Ltd | Adhesive agent composition, circuit-connecting structure and semiconductor device |
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| JP2012041541A (en) | 2012-03-01 |
| CN103797078A (en) | 2014-05-14 |
| CN103797078B (en) | 2016-08-31 |
| TWI540195B (en) | 2016-07-01 |
| KR101872562B1 (en) | 2018-06-28 |
| JP5844589B2 (en) | 2016-01-20 |
| WO2013042633A1 (en) | 2013-03-28 |
| TW201336956A (en) | 2013-09-16 |
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