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WO2013115360A1 - Adhésif conducteur et dispositif électronique utilisant ledit adhésif conducteur - Google Patents

Adhésif conducteur et dispositif électronique utilisant ledit adhésif conducteur Download PDF

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Publication number
WO2013115360A1
WO2013115360A1 PCT/JP2013/052348 JP2013052348W WO2013115360A1 WO 2013115360 A1 WO2013115360 A1 WO 2013115360A1 JP 2013052348 W JP2013052348 W JP 2013052348W WO 2013115360 A1 WO2013115360 A1 WO 2013115360A1
Authority
WO
WIPO (PCT)
Prior art keywords
conductive adhesive
resin
epoxy resin
total
carbon
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2013/052348
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English (en)
Japanese (ja)
Inventor
内田　博
篠崎　研二
圭孝 石橋
克昭 菅沼
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Resonac Holdings Corp
University of Osaka NUC
Original Assignee
Showa Denko KK
Osaka University NUC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Showa Denko KK, Osaka University NUC filed Critical Showa Denko KK
Priority to JP2013556513A priority Critical patent/JP6080776B2/ja
Publication of WO2013115360A1 publication Critical patent/WO2013115360A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/12—Polycondensates containing more than one epoxy group per molecule of polycarboxylic acids with epihalohydrins or precursors thereof
    • 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
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C09J163/10—Epoxy resins modified by unsaturated compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/20—Conductive material dispersed in non-conductive organic material
    • H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
    • 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
    • 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
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0313—Organic insulating material
    • H05K1/032—Organic insulating material consisting of one material
    • H05K1/0326—Organic insulating material consisting of one material containing O
    • 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
    • H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
    • H05K2201/0203—Fillers and particles
    • H05K2201/0206—Materials
    • H05K2201/0215—Metallic fillers

Definitions

  • the present invention relates to a conductive adhesive and an electronic device using the same.
  • conductive adhesives are often used in place of solder for assembling semiconductor elements and various electric / electronic components or bonding them to substrates.
  • Many of such conductive adhesives usually contain an epoxy resin and conductive metal particles.
  • Patent Document 1 listed below discloses a metal filler containing copper as a conductive adhesive having sufficient strength and conductivity, an epoxy compound, a novolac-type phenol resin, and a low-molecular polyhydric phenol compound. And a conductive adhesive containing a curing agent as essential components is described.
  • Patent Document 2 describes a conductive adhesive containing an epoxy resin and a phenol resin that are liquid at room temperature as a conductive adhesive having better adhesive strength.
  • the above conventional technique has a problem that the reliability of the conductive adhesive cannot be ensured due to significant migration or the like caused by halogen such as chlorine contained in the epoxy compound (resin) to be used.
  • An object of the present invention is to provide a conductive adhesive that hardly causes deterioration of a bonded portion due to halogen and an electronic device using the conductive adhesive.
  • the binder resin includes an epoxy resin, and the total chlorine concentration and the total bromine concentration with respect to the total amount of the epoxy resin.
  • the total is 300 ppm by mass or less.
  • the total chlorine concentration and the total bromine concentration with respect to the total amount of the epoxy resin is 50 mass ppm or less.
  • the epoxy resin is obtained by epoxidizing a carbon-carbon double bond of a raw material compound (substrate) having a carbon-carbon double bond with a peroxide as an oxidizing agent.
  • the raw material compound (substrate) is a compound having two or more allyl ether groups.
  • the content of the binder resin in the conductive adhesive is 5 to 99% by volume.
  • the conductive filler is at least one metal selected from the group consisting of gold, silver, copper, nickel, aluminum, palladium, or particles or fibers made of an alloy of the plurality of metals, gold, palladium on the metal surface , Metal particles or fibers plated with any of silver, resin core balls plated with any of nickel, gold, palladium, and silver on resin balls, or particles or fibers of carbon or graphite.
  • One embodiment of the present invention is an electronic device, which joins a semiconductor element, a solar panel, a thermoelectric element, a chip component, a discrete component, or a combination thereof to any of the substrates by any one of the conductive adhesives described above. It is implemented.
  • the electronic device is characterized in that the wiring of the film antenna, the keyboard membrane, the touch panel, and the RFID antenna is formed and connected to the substrate by any one of the above-described conductive adhesives.
  • the present invention it is possible to suppress degradation of the bonded portion derived from halogen during assembly of a semiconductor element and various electric / electronic components or bonding to a substrate.
  • the conductive adhesive according to this embodiment includes a resin that functions as a conductive filler and a binder, the resin includes an epoxy resin, and the total of the total chlorine concentration and the total bromine concentration with respect to the total amount of the epoxy resin is 300 mass ppm or less. It is characterized by being.
  • the total of the total chlorine concentration and the total bromine concentration with respect to the total amount of the epoxy resin is preferably 50 mass ppm or less, and more preferably 10 mass ppm or less.
  • the epoxy resin can be obtained, for example, by epoxidizing a carbon-carbon double bond of a raw material compound (substrate) having a carbon-carbon double bond using peroxide as an oxidizing agent.
  • a compound having a carbon-chlorine bond is not used as a raw material. Therefore, the epoxy resin as the binder resin constituting the conductive adhesive according to the embodiment of the present invention is And substantially free of compounds containing carbon-chlorine bonds in the molecule.
  • substantially free means that a compound containing a carbon-chlorine bond is not used as a raw material used for synthesizing an epoxy resin, that is, such a compound in an epoxy resin and a reaction product thereof. It means that the content of is zero.
  • the oxidizing agent include hydrogen peroxide and peracetic acid, but hydrogen peroxide that is inexpensive and easy to handle is more preferable.
  • epoxy resin refers to a binder component of a conductive adhesive, that is, a compound having an oxirane ring constituting a cured product, and includes any of a monomer, an oligomer, and a polymer.
  • Examples of the raw material compound (substrate) having a carbon-carbon double bond include a cycloalkene having 4 to 12 carbon atoms, an unconjugated cycloalkadiene, cycloalkatriene, or cycloalkatetraene having 6 to 12 carbon atoms, or And compounds having an allyl ether group.
  • raw material compounds include phenyl allyl ethers, cresol monoallyl ethers, cyclohexenes, cyclooctenes, and the like, for example, bisphenol-A diallyl ether, allyl ether compounds of novolac phenolic resins, cyclohexane Dimethanol diallyl ether, trimethylolpropane triallyl ether, pentaerythritol tetraallyl ether, 3,4-epoxycyclohexane-1-carboxylic acid allyl ester, 3,4-cyclohexenylmethyl-3 ′, 4′-cyclohexene carboxylate, etc. Can be illustrated.
  • a compound having two or more allyl ether groups it is preferable to use a compound having two or more allyl ether groups.
  • a glycidyl ether compound obtained by epoxidizing a compound represented by the following general formula (1) with an oxidizing agent such as hydrogen peroxide is used. is there.
  • R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 4 to 6 carbon atoms, an aryl group having 6 to 14 carbon atoms, or R 1 And R 2 together form a cycloalkane having 3 to 12 carbon atoms
  • R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, carbon A cycloalkyl group having 4 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms
  • n represents an integer of 0 or 1.
  • Such compounds include bisphenol-A diallyl ether, bisphenol-F diallyl ether, 2,6,2 ', 6'-tetramethylbisphenol-A diallyl ether, 2,2'-diallyl bisphenol- A diallyl ether, 2,2'-di-t-butylbisphenol-A diallyl ether, 3,3 ', 5,5'-tetramethylbiphenyl-4,4'-diallyl ether, 2,2'-diisopropylbiphenol diallyl Ether, 4,4′-ethylidene bisphenol diallyl ether, 4,4′-cyclohexylidene bisphenol diallyl ether, 4,4 ′-(1- ⁇ -methylbenzylidene) bisphenol diallyl ether, 4,4 ′-(3,3 , 5-Trimethylcyclohexylidene) bisphe Over Luzia Lil ether, 4,4 '- (1-methyl - benzylidene) bisphenol diallyl
  • biphenyl diallyl ether having an aromatic ring and two allyl ether groups examples include 2,2'-biphenyl diallyl ether and tetramethylbiphenyl diallyl ether.
  • Aliphatic polyallyl ethers having two or more allyl ether groups can also be used. Specifically, 1,5-pentanediol diallyl ether, 1,6-hexanediol diallyl ether, 1,9- Nonanediol diallyl ether, 1,10-decanediol diallyl ether, neopentyl glycol diallyl ether, glycerin triallyl ether, trimethylolpropane triallyl ether, pentaerythritol tetraallyl ether and the like can be mentioned.
  • alicyclic diolefin having two allyl ether groups include 1,4-cyclohexanedimethanol diallyl ether and tricyclo [5.2.1.0 2,6 ] decandimethanol diallyl ether. Can be mentioned.
  • the resin functioning as a binder may include other thermoplastic resins and thermosetting resins in addition to the epoxy resin.
  • the thermoplastic resin include acrylic resin, ethyl cellulose, polyester, polysulfone, phenoxy resin, and polyimide.
  • thermosetting resins include amino resins such as urea resins, melamine resins, and guanamine resins; oxetane resins; phenol resins such as resol types and novolac types; and silicone-modified organic resins such as silicone epoxies and silicone polyesters. Is done.
  • thermoplastic resins and thermosetting resins which function as a binder, preferably have a low chlorine concentration and bromine concentration, and are the sum of the total chlorine concentration and the total bromine concentration relative to the total amount of the resin functioning as the binder. Is preferably 300 ppm by mass or less. More preferably, it is 50 mass ppm or less, More preferably, it is 10 mass ppm or less.
  • epoxy resins bisphenol A type and bisphenol F type epoxy resins are used because excellent adhesiveness and excellent heat resistance can be obtained even if the blending amount of the resin is suppressed to an amount that does not impair the conductivity. preferable. Further, from the same viewpoint, a resol type phenol resin may be mixed.
  • the vehicle When a resin that is liquid at room temperature is used as the resin, the vehicle can be obtained without using an organic solvent, and the drying step can be omitted. For this reason, it is preferable to use a liquid epoxy resin.
  • Liquid epoxy resins include bisphenol A type epoxy resins having an average molecular weight of about 400 or less; branched polyfunctional bisphenol A type epoxy resins such as p-glycidoxyphenyldimethyltolylbisphenol A diglycidyl ether; bisphenol F type Epoxy resin; phenol novolac type epoxy resin having an average molecular weight of about 570 or less; 1,5-pentanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,9-nonanediol diglycidyl ether, 1, 10-decanediol diglycidyl ether, neopentyl glycol diglycidyl ether, glycerin triglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol tetraglycidyl ether Aliphatic polyglycidyl ethers such as vinyl
  • the liquid epoxy resin is compatible within the range in which the mixed system exhibits fluidity, and within a range in which the total chlorine concentration and total bromine concentration with respect to the total amount of the epoxy resin is 300 ppm by mass or less.
  • a resin having a solid or ultra-high viscosity may be mixed and used. Examples of such resins include high molecular weight bisphenol A type epoxy resins, diglycidyl biphenyl, novolac epoxy resins, and epoxy resins such as tetrabromobisphenol A type epoxy resins; novolak phenol resins and the like.
  • a self-curing resin may be used, or a curing agent or a curing accelerator may be used.
  • curing agents usually used for the epoxy resin include acid anhydrides, polyamines, polyphenol compounds, and the like.
  • a curing agent specifically in the case of an acid anhydride, hexahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 3-methyl-1,2,3,6-tetrahydrophthalic anhydride, 4-methyl-1,2,3,6-tetrahydrophthalic anhydride, 3-methyl-hexahydrophthalic anhydride, 4-methyl-hexahydrophthalic anhydride Acid, 5-norbornene-2,3-dicarboxylic acid anhydride, norbornane-2,3-dicarboxylic acid anhydride, methyl-3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride, methyl- In addition to 3,6-endomethylenehexahydrophthalic anhydride, dodecenyl succinic anhydride and alicyclic compounds having conjugated double bonds such as ⁇ -terpinene and allooci
  • Polyamines include aliphatic amines such as diethylenetriamine, triethylenetetramine, tetraethylenepentamine, dipropylenediamine, diethylaminopropylamine, N-aminoethylpiperazine, isophoronediamine, m-xylylenediamine, p-xylylenediamine, hydrogenated
  • aromatic amine examples include m-phenylenediamine, diaminodiphenylmethane, and diaminodiphenylsulfone.
  • phenol resin such as a phenol novolak resin or a cresol novolak resin, polyvinyl phenol, or the like is used.
  • a curing accelerator such as imidazole or dicyandiamide can be used in combination. Needless to say, it is preferable that the content of chlorine and bromine is low in these curing agents and curing accelerators.
  • the conductive filler used in the conductive adhesive of this embodiment is made of at least one metal selected from the group consisting of gold, silver, copper, nickel, aluminum, and palladium, or an alloy of the plurality of metals.
  • Particles or fibers, metal particles or fibers plated with gold, palladium or silver on the metal surface, resin core balls plated with nickel, gold, palladium or silver on resin balls, carbon or graphite It is preferably a particle or fiber, but is not limited thereto, and may be used as long as it can exhibit electrical conductivity and does not significantly deteriorate the adhesiveness (to the extent that it cannot be used as an adhesive). it can.
  • the shape of the conductive filler is not particularly limited, and in the case of particles, various shapes such as a spherical shape, a flat plate shape (flat shape), and a rod shape can be used.
  • a preferable particle diameter is 5 nm to 20 ⁇ m.
  • the particle diameter here is a number-based D50 (median diameter) particle measured by a laser diffraction / scattering method when the particle diameter is 500 nm or more, and by a dynamic light scattering method when it is less than 500 nm. Means diameter.
  • fibers those having a diameter of 0.1 to 3 ⁇ m, a length of 1 to 10 ⁇ m, and an aspect ratio of 5 to 100 are preferable.
  • the compounding amount of the resin in the conductive adhesive is preferably 5 to 99% by volume with respect to the total of the resin and the conductive filler, from the printability and the conductivity of the conductive layer obtained by curing.
  • the content is more preferably 40 to 85% by volume, and still more preferably 60 to 75% by volume.
  • the binder resin content is preferably 95 to 99% by volume.
  • the anisotropic conductive connection refers to a connection that is conductive between opposing electrodes (vertical direction) and insulative between adjacent electrodes (horizontal direction). An anisotropic conductive adhesive is used by being sandwiched between electrodes electrically connected by anisotropic conductive connection.
  • the conductive adhesive of the present embodiment is selected from the type and amount of the binder resin including the conductive filler and the epoxy resin, and if necessary, by using a diluent, a printing method or application to an element, a substrate, etc. Depending on the method, it can be adjusted to an appropriate viscosity.
  • a diluent for example, in the case of screen printing, an organic solvent having a boiling point of 200 ° C. or higher is preferably used as a diluent. Examples of such an organic solvent include diethylene glycol monomethyl ether acetate, diethylene glycol monobutyl ether acetate, and diethylene glycol monobutyl ether. Can be mentioned.
  • the preferred viscosity of the conductive adhesive is 20 Pa ⁇ s to 500 Pa ⁇ s as measured at 25 ° C. with a rheometer.
  • the conductive adhesive of the present embodiment includes an aluminum chelate compound such as diisopropoxy (ethylacetoacetate) aluminum as a dispersion aid, if necessary, such as isopropyltriisostearoyl titanate.
  • An aliphatic polycarboxylic acid ester; an unsaturated fatty acid amine salt; a surfactant such as sorbitan monooleate; or a polymer compound such as a polyesteramine salt or polyamide may be used.
  • the conductive adhesive of the present embodiment can be prepared by uniformly mixing the blended components by a mixing means such as a reika machine, a propeller stirrer, a kneader, a roll, and a pot mill.
  • a mixing means such as a reika machine, a propeller stirrer, a kneader, a roll, and a pot mill.
  • Preparation temperature is not specifically limited, For example, it can prepare at normal temperature.
  • the conductive adhesive of the present embodiment can be printed or applied to the substrate by any method such as screen printing, gravure printing, dispensing, or the like.
  • an organic solvent is used as a diluent, the organic solvent is volatilized after printing or coating at room temperature or by heating.
  • the resin is usually heated at 70 to 250 ° C., for example, in the case of an epoxy resin using a phenol resin as a curing agent, for 2 to 30 minutes depending on the type of the resin and the curing agent or curing accelerator.
  • a conductive pattern can be formed on a necessary portion of the substrate surface.
  • an electronic device in which a semiconductor element, a solar panel, a thermoelectric element, a chip part, a discrete part, or a combination thereof is mounted on a substrate can be formed.
  • the conductive adhesive of the present embodiment it is also possible to form an electronic device in which a film antenna, a keyboard membrane, a touch panel, and an RFID antenna are formed and connected to a substrate.
  • the conductive filler used in the examples is the following two types of silver particles.
  • N300 Toxen Industries Co., Ltd. silver particle (flat plate)
  • D50 470 nm
  • EHD Silver particles (spherical) manufactured by Mitsui Mining & Smelting Co., Ltd.
  • D50 620 nm
  • D50 is a number-based median diameter measured by N300 using a dynamic light scattering method and EHD using a laser diffraction / scattering method.
  • N300 had a number average value of 30 nm obtained by observing 10 points by SEM while changing the observation location at a magnification of 30,000 times.
  • the epoxy equivalent, number average molecular weight, total chlorine concentration and total bromine concentration were determined by the following methods, respectively.
  • the epoxy equivalent was determined according to JIS-K7236. Weigh 0.1 to 0.2 g of the sample, put it in an Erlenmeyer flask, and add 10 mL of chloroform to dissolve. Next, 20 mL of acetic acid is added, followed by 10 mL of tetraethylammonium bromide solution (100 g of tetraethylammonium bromide dissolved in 400 mL of acetic acid). 4 to 6 drops of crystal violet indicator was added to this solution, and titrated with a 0.1 mol / L perchloric acid acetic acid solution. Based on the titration result, the epoxy equivalent was determined according to the following formula.
  • Epoxy equivalent (g / eq) (1000 ⁇ m) / ⁇ (V1 ⁇ V0) ⁇ c ⁇ m: weight of the sample (g)
  • V0 Amount of perchloric acid acetic acid solution consumed for titration to the end point in the blank test (mL)
  • V1 Amount of perchloric acid acetic acid solution consumed for titration to the end point (mL)
  • c Concentration of perchloric acid acetic acid solution (0.1 mol / L)
  • GPC gel permeation chromatography
  • Total chlorine concentration and total bromine concentration were measured by burning and decomposing the epoxy compound at a high temperature of 800 ° C. or higher, absorbing the decomposed gas in ultrapure water, etc., and quantifying it by ion chromatography (pretreatment combustion apparatus) AGF-100 (manufactured by Mitsubishi Chemical Analytic Co., Ltd.), gas adsorption device GA-100 (manufactured by Mitsubishi Chemical Analytic Co., Ltd.), ion chromatograph ICS-100 (manufactured by Dionex Corporation)).
  • Synthesis example 2 Synthesis of 3,3 ′, 5,5′-tetramethylbiphenyl-4,4′-glycidyl ether 3,3 ′, 5,5′-tetramethyl-4,4′-biphenyl was added to a 2000 ml eggplant type flask. Diol (China: Gansu Chemical Research Institute) 150g (0.619mol), 50% water content 5% -Pd / C (Pd / C with 5% by mass of Pd with respect to the total mass of Pd and C was impregnated with water. The mass of water is 50% by mass with respect to the total mass of Pd / C and water) -STD type (manufactured by N.E.
  • the distillate is a solid having a melting point of 51.7 ° C., and the viscosity at 60 ° C. measured by a rheometer (Phisica MCR301 manufactured by Anton Paar Co., Ltd .: CP25-2, 25 mm diameter, angle 2 °) is 29 mPa ⁇ s. Met.
  • Synthesis example 3 Synthesis of bisphenol-A-glycidyl ether In a 2000 ml eggplant-shaped flask, 148.4 g (0.650 mol) of bisphenol-A (manufactured by Mitsui Chemicals), 50% water content 5% -Pd / C-STD type (N.
  • 45% aqueous hydrogen peroxide (53.92 g, 713.5 mmol) was added dropwise over 4 hours using a 100 mL dropping funnel (the pH was adjusted to 10 to 10 hours so that the reaction temperature did not exceed 30 ° C. for 4 hours during this period). Then, the mixture was stirred for 4 hours while controlling the pH to 10.5 (acetonitrile concentration at the end of the reaction was 3.5 mol%).
  • the reaction solution was diluted with pure water (100 g), and the solvent was distilled off under reduced pressure. The residue was extracted with ethyl acetate (100 g), pure water (100 g) was added again, and a liquid separation operation was performed.
  • Ethyl acetate was distilled off with an evaporator to obtain the desired epoxidation product.
  • the chlorine concentration measured in the same manner as in Synthesis Example 1 was 6 ppm by mass, the total bromine concentration was less than 1 ppm by mass, and the epoxy equivalent was 178 g / eq. there were.
  • connection resistance (m ⁇ ) of the circuit sample is measured by a tester (manufactured by SANWA, model: PC500a RS-232C).
  • connection resistance was almost the same value in the example and the comparative example, and the connection strength was a little lower in the example 1, but the other examples were almost the same value as the comparative example.
  • the migration time was more than 10 minutes in all the examples, compared with 0.1 minutes in the comparative example.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Dispersion Chemistry (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Physics & Mathematics (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
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Abstract

Le problème décrit par la présente invention est de fournir : un adhésif conducteur qui n'est pas sensible à la détérioration dans une partie liée provoquée par un halogène ; et un dispositif électronique utilisant l'adhésif conducteur. La solution selon l'invention porte sur un adhésif conducteur qui contient une charge conductrice et une résine liante, la résine liante contenant une résine époxy dans laquelle la somme de la concentration totale en chlore et de la concentration totale en brome est inférieure ou égale à 300 ppm en masse par rapport à la quantité totale de la résine époxy contenue dans la résine liante. Dans ladite résine époxy, la somme de la concentration totale en chlore et de la concentration totale en brome est de préférence inférieure ou égale à 50 ppm en masse, et ladite résine époxy est de préférence obtenue par époxydation d'une double liaison carbone-carbone d'un composé de départ (un matériau de base) comprenant une double liaison carbone-carbone, tout en utilisant le peroxyde d'hydrogène comme oxydant.
PCT/JP2013/052348 2012-02-03 2013-02-01 Adhésif conducteur et dispositif électronique utilisant ledit adhésif conducteur Ceased WO2013115360A1 (fr)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015160932A (ja) * 2014-02-28 2015-09-07 昭和電工株式会社 導電性接着剤及びそれらを使用した電子機器
KR101593088B1 (ko) * 2015-05-14 2016-02-11 한화케미칼 주식회사 카본계 접착제 조성물 및 이를 이용하는 폴리실리콘의 제조방법
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WO2016063957A1 (fr) * 2014-10-22 2016-04-28 スガイ化学工業株式会社 Dérivé de décaline et procédé de production associé
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WO2023199925A1 (fr) * 2022-04-15 2023-10-19 株式会社スリーボンド Composition de résine électroconductrice et produit durci de celle-ci
CN119241475A (zh) * 2024-10-15 2025-01-03 中国科学院长春应用化学研究所 一种环氧树脂的制备方法和电子电器用材料

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