Classifications

• • 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
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
  • C08G59/66—Mercaptans
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
  • C08K3/013—Fillers, pigments or reinforcing additives
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/34—Heterocyclic compounds having nitrogen in the ring
  • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
  • C08K5/3472—Five-membered rings
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/34—Heterocyclic compounds having nitrogen in the ring
  • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
  • C08K5/3472—Five-membered rings
  • C08K5/3475—Five-membered rings condensed with carbocyclic rings
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• • 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
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K3/00—Materials not provided for elsewhere
  • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W74/00—Encapsulations, e.g. protective coatings
  • H10W74/10—Encapsulations, e.g. protective coatings characterised by their shape or disposition
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W74/00—Encapsulations, e.g. protective coatings
  • H10W74/40—Encapsulations, e.g. protective coatings characterised by their materials

Definitions

• the present invention relates to an epoxy resin composition, an adhesive containing the same, a sealing material containing the same, a cured product obtained by curing the same, and an electronic component containing the cured product.
• adhesives and sealing materials made of curable resin compositions, especially epoxy resin compositions are used for the purpose of maintaining reliability. Used often.
• the adhesives and sealing materials used are required to exhibit sufficient curability even under low temperature conditions. At the same time, they are also required to cure in a short time from the aspect of production cost.
• Epoxy resin compositions used for adhesives and sealing materials for electronic parts generally contain an epoxy resin and a curing agent.
• epoxy resin compositions those using a thiol-based curing agent as a curing agent are known to cure in a moderately short period of time even under low temperature conditions.
• Thiol-based curing agents include compounds having two or more thiol groups, ie, polyfunctional thiol compounds.
• Examples of such epoxy resin compositions include those disclosed in Patent Document 1.
• fillers such as silica fillers are sometimes added to such epoxy resin compositions for the purpose of improving thermal cycle resistance.
• an epoxy resin composition containing a filler for such purpose the one disclosed in Patent Document 2 can be mentioned.
• an epoxy resin composition that has low viscosity and low thixotropy at the time of injection and has high injectability. If the viscosity of the epoxy resin composition used is not low enough to facilitate injection, heating may reduce the viscosity of the epoxy resin composition and facilitate injection.
• the present invention has been made in view of the above-mentioned problems, and an object of the present invention is to provide an epoxy resin composition that uses a thiol-based curing agent and contains a filler, and has a viscosity reduction to some extent.
• an adhesive containing the same, and a sealing material containing the same which do not accelerate the progress of curing and the accompanying increase in viscosity even when heated.
• Another object of the present invention is to provide a cured product obtained by curing the epoxy resin composition, adhesive or sealing material.
• Still another object of the present invention is to provide an electronic component containing the cured product.
• an epoxy resin composition that uses a thiol-based curing agent and contains a filler does not promote the progress of curing and the accompanying increase in viscosity even when heated to a certain extent.
• Intensive research was conducted in order to develop an epoxy resin composition.
• a specific azole compound to such an epoxy resin composition, under mild heating for the purpose of viscosity reduction, the progress of curing and the accompanying increase in viscosity are suppressed. It was found that the injectability was improved. Based on the above new findings, the present invention has been completed.
• the present invention includes, but is not limited to, the following inventions.
• An adhesive comprising the epoxy resin composition according to any one of 1 to 4 above.
• a sealing material comprising the epoxy resin composition according to any one of 1 to 4 above.
• the epoxy resin composition of the present invention is at least one selected from the group consisting of (A) a polyfunctional thiol compound, (B) a polyfunctional epoxy resin, (C) a benzotriazole compound and a tetrazole compound, an azole compound, (D) a curing catalyst and (E) a filler.
• A a polyfunctional thiol compound
• B a polyfunctional epoxy resin
• C a benzotriazole compound and a tetrazole compound
• an azole compound an azole compound
• D a curing catalyst
• E a filler.
• the epoxy resin composition of the present invention contains a polyfunctional thiol compound.
• the polyfunctional thiol compound used in the present invention is a compound containing two or more thiol groups that react with epoxy groups in the polyfunctional epoxy resin described below.
• the polyfunctional thiol compound preferably has 3 or more thiol groups.
• the polyfunctional thiol compound more preferably contains a trifunctional thiol compound and/or a tetrafunctional thiol compound.
• Trifunctional and tetrafunctional thiol compounds are thiol compounds having 3 and 4 thiol groups, respectively.
• the thiol equivalent weight of the polyfunctional thiol compound is preferably 90-150 g/eq, more preferably 90-140 g/eq, even more preferably 90-130 g/eq.
• the polyfunctional thiol compound includes a thiol compound having a hydrolyzable partial structure such as an ester bond in the molecule (i.e. hydrolyzable) and a thiol compound having no such partial structure (i.e. non-hydrolyzable).
• hydrolyzable polyfunctional thiol compounds include trimethylolpropane tris (3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: TMMP), tris-[(3-mercaptopropionyloxy)-ethyl]- Isocyanurate (manufactured by SC Organic Chemical Co., Ltd.: TEMPIC), pentaerythritol tetrakis (3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: PEMP), tetraethylene glycol bis (3-mercaptopropionate) (SC Organic Chemical Co., Ltd.: EGMP-4), dipentaerythritol hexakis (3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: DPMP), pentaerythritol tetrakis (3-mercaptobutyrate) (manufactured by
• non-hydrolyzable polyfunctional thiol compounds include 1,3,4,6-tetrakis (2-mercaptoethyl) glycoluril (manufactured by Shikoku Kasei Co., Ltd.: TS-G), (1,3 , 4,6-tetrakis(3-mercaptopropyl)glycoluril (manufactured by Shikoku Kasei Co., Ltd.: C3 TS-G), 1,3,4,6-tetrakis(mercaptomethyl)glycoluril, 1,3,4, 6-tetrakis(mercaptomethyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(2-mercaptoethyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(3-mercaptopropyl )-3a-methylglycoluril, 1,3,4,6-tetrakis(mercaptomethyl)-3a,6a-d
• the epoxy resin composition of the present invention contains a polyfunctional epoxy resin.
• the polyfunctional epoxy resin used in the present invention is a compound containing two or more epoxy groups that react with the thiol groups in the polyfunctional thiol compound.
• Aliphatic polyfunctional epoxy resins are polyfunctional epoxy resins having structures that do not contain aromatic rings.
• Examples of aliphatic polyfunctional epoxy resins include: - (poly)ethylene glycol diglycidyl ether, (poly)propylene glycol diglycidyl ether, butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, trimethylolpropane diglycidyl ether, poly Tetramethylene ether glycol diglycidyl ether, glycerin diglycidyl ether, neopentyl glycol diglycidyl ether, 1,2-epoxy-4-(2-methyloxiranyl)-1-methylcyclohexane, cyclohexane type diglycidyl ether, dicyclo diep
• aromatic polyfunctional epoxy resin is a polyfunctional epoxy resin having a structure containing an aromatic ring.
• Many conventional epoxy resins such as bisphenol A type epoxy resin, are of this type.
• aromatic polyfunctional epoxy resins include: - bisphenol A type epoxy resin; - branched polyfunctional bisphenol A type epoxy resins such as p-glycidyloxyphenyldimethyltrisbisphenol A diglycidyl ether; - bisphenol F type epoxy resin; - novolac type epoxy resins; - tetrabromobisphenol A type epoxy resin; - a fluorene-type epoxy resin; - biphenyl aralkyl epoxy resins; - diepoxy resins such as 1,4-phenyldimethanol diglycidyl ether; -biphenyl-type epoxy resins such as 3,3',5,5'-tetramethyl-4,4'-diglycidyloxybiphenyl; -glycidylamine type epoxy resins such as dig
• the epoxy resin composition of the present invention - The total number (total amount) of thiol groups contained in the (A) polyfunctional thiol compound, and - The total number (total amount) of epoxy groups contained in the (B) polyfunctional epoxy resin preferably satisfies a predetermined relationship.
• [(B) total number of epoxy groups for polyfunctional epoxy resin]/[(A) total number of thiol groups for polyfunctional thiol compound] is preferably 0.5 to 1.5, more preferably 0.7 to 1.3, still more preferably 0.8 to 1.2.
• the total number of epoxy groups for a polyfunctional epoxy resin is the quotient obtained by dividing the mass (g) of the polyfunctional epoxy resin by the epoxy equivalent weight of the polyfunctional epoxy resin (when multiple types of epoxy resins are included, each epoxy resin is the sum of such quotients for The epoxy equivalent can be determined by the method described in JIS K7236. If the epoxy equivalent cannot be determined by this method, it may be calculated as a quotient obtained by dividing the molecular weight of the polyfunctional epoxy resin by the number of epoxy groups in one molecule of the polyfunctional epoxy resin.
• the total number of epoxy groups for the monofunctional epoxy resin described below, which may be contained in the epoxy resin composition of the present invention, can also be determined in the same manner as for the polyfunctional epoxy resin.
• the total number of thiol groups for a polyfunctional thiol compound is the quotient obtained by dividing the mass (g) of the polyfunctional thiol compound contained in the polyfunctional thiol compound by the thiol equivalent of the polyfunctional thiol compound (multiple polyfunctional thiol compounds are included. is the sum of such quotients for each polyfunctional thiol compound).
• a thiol equivalent can be determined by an iodometric titration method. This method is widely known and disclosed, for example, in paragraph 0079 of JP-A-2012-153794. If the thiol equivalent cannot be determined by this method, the molecular weight of the polyfunctional thiol compound may be calculated as a quotient divided by the number of thiol groups in one molecule of the polyfunctional thiol compound.
• the epoxy resin composition of the present invention contains an azole compound.
• the azole compound used in the present invention is at least one selected from the group consisting of benzotriazole compounds and tetrazole compounds.
• Azole compounds preferably include benzotriazole compounds.
• the present inventors have found that when an azole compound is added to an epoxy resin composition, curing is less likely to be accelerated when the epoxy resin composition is heated during application by injection, thereby suppressing an increase in viscosity and improving injectability. Furthermore, it has been found that this improvement in injectability becomes even more pronounced when the epoxy resin composition contains a filler, which will be described later.
• the benzotriazole compound as the azole compound used in the present invention is not particularly limited as long as it is a compound having a benzotriazole skeleton, and the benzotriazole compound may be unsubstituted benzotriazole, and has one or more may be a benzotriazole compound having a substituent of The benzotriazole compound preferably has substituents at the 1- and/or 2-positions, more preferably at the 1-position.
• benzotriazole compounds include 1,2,3-benzotriazole, 1-[N,N-bis(2-ethylhexyl)aminomethyl]benzotriazole, carboxybenzotriazole, 1-[N,N-bis(2 -ethylhexyl)aminomethyl]methylbenzotriazole, 2,2'-[[(methyl-1H-benzotriazol-1-yl)methyl]imino]bisethanol, 1,2,3-benzotriazole sodium salt, tolyltriazole , alkoxysilane-substituted benzotriazole, 2-(2′-hydroxy-5′-methylphenyl)benzotriazole, 2-(2′-hydroxy-3′-tert-butyl-5′-methylphenyl)-5-chlorobenzotriazole, 2-(2′-hydroxy-3′,5′-di-tert-amylphenyl)benzo triazole, 2-(2′-hydroxy-5′-tert-oc
• 1,2,3-benzotriazole 1-[N,N-bis(2-ethylhexyl)aminomethyl]benzotriazole, alkoxysilane-substituted benzotriazole, carboxybenzotriazole, 1-[N,N-bis (2-ethylhexyl)aminomethyl]methylbenzotriazole, 2,2′-[[(methyl-1H-benzotriazol-1-yl)methyl]imino]bisethanol, 1,2,3-benzotriazole sodium salt, Tolyltriazole is preferred, 1-[N,N-bis(2-ethylhexyl)aminomethyl]benzotriazole, more preferred is alkoxysilane-substituted benzotriazole, 1-[N,N-bis(2-ethylhexyl)aminomethyl]benzo Triazoles are particularly preferred. These compounds may be used alone or in combination of two or more.
• the tetrazole compound as the azole compound used in the present invention is not particularly limited as long as it is a compound having a tetrazole skeleton. It may be a tetrazole compound having The tetrazole compound is preferably a tetrazole compound having one or more substituents at any position, more preferably a tetrazole compound having a substituent at the 5-position.
• tetrazole compounds include 1H-tetrazole, 5-phenyl-1H-tetrazole, 5-amino-1H-tetrazole, 5-methyl-1H-tetrazole, 1-methyl-5-mercaptotetrazole, 1-methyl-5- Ethyl-tetrazole, 1-(dimethylaminoethyl)-5-mercaptotetrazole, 1H-5 hydroxy-tetrazole, 1-methyl-5-ethyltetrazole, 1-propyl-5-methyl-tetrazole, 1-phenyl-5-hydroxy Tetrazole, 5-mercapto-1-phenyl-1H-tetrazole, 1-(p-ethoxyphenyl)-5-mercaptotetrazole, 1-(4-benzamido)-5-mercaptotetrazole, 5-tolyltetrazole, 5-phenyltetrazole , 5-aminotetrazole, 5-(m-aminophen
• 5-mercapto-1-phenyl-1H-tetrazole 5-mercapto-1-methyltetrazole, 5-phenyl-1H-tetrazole, 5-(ethylthio)-1H-tetrazole are preferred, and 5-mercapto-1 -methyltetrazole, 5-phenyl-1H-tetrazole are particularly preferred.
• These compounds may be used alone or in combination of two or more.
• the epoxy resin composition of the present invention contains a curing catalyst.
• a curing catalyst By including a curing catalyst, the epoxy resin composition of the present invention can be cured in a short time even under low temperature conditions.
• the curing catalyst used in the present invention is not particularly limited, and known catalysts can be used.
• the curing catalyst is a basic substance.
• the curing catalyst is a latent curing catalyst.
• a latent curing catalyst is a compound that is inactive at room temperature and is activated by heating to function as a curing catalyst.
• an imidazole compound that is solid at room temperature a solid-dispersed amine adduct-based latent curing catalyst such as a compound (amine-epoxy adduct system); a reaction product of an amine compound and an isocyanate compound or a urea compound (urea adduct system);
• Typical examples of commercially available latent curing catalysts include "Amicure PN-23” (trade name, manufactured by Ajinomoto Fine-Techno Co., Inc.) and “Amicure PN-40” as amine-epoxy adduct system (amine adduct system).
• the curing catalyst may be used alone or in combination of two or more. From the viewpoint of pot life and curability, the curing catalyst is preferably a solid-dispersed amine adduct latent curing catalyst.
• the amount of the curing catalyst is preferably 0.1 to 20% by mass, more preferably 0.5 to 15% by mass, and even more preferably 1 to 10% by mass of the epoxy resin composition.
• Some curing catalysts are provided in the form of a dispersion dispersed in a polyfunctional epoxy resin.
• the amount of polyfunctional epoxy resin in which it is dispersed is also included in the amount of said polyfunctional epoxy resin in the epoxy resin composition of the present invention. be.
• the epoxy resin composition of the present invention contains a filler.
• the present inventors have found that when the epoxy resin composition contains a filler, the viscosity is likely to increase due to heating during injection, and in this case, the epoxy resin composition is hardened by heating during injection. It has been found that the effect of the above azole compound for suppressing is particularly remarkable.
• the filler improves the thermal cycle resistance of the cured product obtained by curing the epoxy resin composition of the present invention. This improvement in thermal cycle resistance is due to a decrease in the coefficient of linear expansion of the cured product, that is, suppression of expansion and contraction of the cured product due to thermal cycles. In addition, shrinkage during curing is also suppressed.
• the filler preferably contains a silica filler and/or an alumina filler, more preferably a silica filler.
• the average particle size of the filler is preferably 0.1 to 5 ⁇ m, more preferably 0.1 to 3 ⁇ m, even more preferably 0.1 to 1 ⁇ m.
• the average particle diameter refers to a volume-based median diameter (d50) measured by a laser diffraction method in accordance with ISO-13320 (2009), unless otherwise specified.
• d50 volume-based median diameter
• the maximum particle size of the filler is preferably 15 ⁇ m or less, more preferably 10 ⁇ m or less, from the viewpoint of preventing sedimentation.
• the content of the filler is preferably 1 to 80% by mass, more preferably 3 to 60% by mass, and further preferably 5 to 50% by mass, relative to the total mass of the epoxy resin composition. It is preferably 5 to 40% by mass, and particularly preferably 5 to 40% by mass.
• the filler may be used alone or in combination of two or more.
• Specific examples of fillers other than silica fillers and alumina fillers include talc fillers, calcium carbonate fillers, polytetrafluoroethylene (PTFE) fillers, silicone fillers, acrylic fillers, styrene fillers, etc., but are limited to these. not.
• the filler may be surface-treated.
• the epoxy resin composition of the present invention may contain optional components other than the above components (A) to (E), such as those described below.
• the epoxy resin composition of the present invention may contain a monofunctional epoxy resin, if desired.
• a monofunctional epoxy resin is an epoxy resin containing one epoxy group.
• the epoxy resin composition of the present invention may contain a monofunctional epoxy resin from the viewpoint of lowering the viscosity.
• Examples of monofunctional epoxy resins include n-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, phenyl glycidyl ether, cresyl glycidyl ether, p-s-butylphenyl glycidyl ether, styrene oxide, ⁇ -pinene oxide, 4-tert.
• the epoxy resin composition of the present invention contains a monofunctional epoxy resin
• its content is 0.01 to 30 parts by mass with respect to 100 parts by mass of the total amount of components (A) to (E). It is preferably from 0.05 to 25 parts by mass, and even more preferably from 0.1 to 20 parts by mass.
• the epoxy resin composition of the present invention may contain a stabilizer, if desired.
• the epoxy resin composition of the present invention may contain a stabilizer in order to improve its storage stability and prolong its pot life.
• Various stabilizers known in the art can be used as stabilizers for one-component adhesives based on epoxy resins. At least one selected from the group consisting of acids is preferred, and at least one selected from the group consisting of liquid boric acid ester compounds and aluminum chelates is more preferred.
• borate ester compounds include 2,2′-oxybis(5,5′-dimethyl-1,3,2-oxaborinane), trimethylborate, triethylborate, tri-n-propylborate, triisopropylborate, tri - n-butylborate, tripentylborate, triallylborate, trihexylborate, tricyclohexylborate, trioctylborate, trinonylborate, tridecylborate, tridodecylborate, trihexadecylborate, trioctadecylborate, tris(2 -ethylhexyloxy)borane, bis(1,4,7,10-tetraoxaundecyl)(1,4,7,10,13-pentoxatetradecyl)(1,4,7-trioxaundecyl) Borane, tribenzylborate, triphenylborate,
• liquid borate ester compound is liquid at room temperature (25° C.), it is preferable because the viscosity of the formulation can be kept low.
• aluminum chelate for example, aluminum chelate A (manufactured by Kawaken Fine Chemicals Co., Ltd.) can be used.
• organic acid for example, barbituric acid can be used.
• the content thereof is preferably 0.01 to 30 parts by mass with respect to 100 parts by mass of the total amount of components (A) to (E). It is more preferably 0.05 to 25 parts by mass, even more preferably 0.1 to 20 parts by mass.
• the epoxy resin composition of the present invention may contain a coupling agent, if desired. Addition of a coupling agent, particularly a silane coupling agent, is preferable from the viewpoint of improving adhesive strength.
• a coupling agent various silane coupling agents such as epoxy-based, amino-based, vinyl-based, methacrylic-based, acryl-based, and mercapto-based coupling agents can be used. Specific examples of silane coupling agents include 3-glycidoxypropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, vinyltrimethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene).
• silane coupling agents may be used alone or in combination of two or more.
• the content thereof is from 0.01 part by mass to 100 parts by mass of the total amount of components (A) to (E) from the viewpoint of improving adhesive strength. It is preferably 50 parts by mass, more preferably 0.1 to 30 parts by mass.
• the epoxy resin composition of the present invention may contain other additives, such as carbon black, titanium black, ion trapping agents, leveling agents, antioxidants, if desired, within the scope of the present invention. agents, antifoaming agents, thixotropic agents, viscosity modifiers, flame retardants, colorants, solvents, and the like. The kind and content of each additive are as usual.
• the method for producing the epoxy resin composition of the present invention is not particularly limited.
• components (A) to (E) and, if desired, other additives are simultaneously or separately introduced into a suitable mixer and mixed by stirring while melting by heating if necessary, By forming a uniform composition, the epoxy resin composition of the present invention can be obtained.
• the mixer is not particularly limited, but a Raikai machine equipped with a stirring device and a heating device, a Henschel mixer, a three-roll mill, a ball mill, a planetary mixer, a bead mill, or the like can be used. Also, these devices may be used in combination as appropriate.
• the epoxy resin composition obtained in this way is thermosetting, and at a temperature of 80°C, it preferably cures within 5 hours, more preferably within 1 hour. Curing at a high temperature and in a very short time such as several seconds at a temperature of 150° C. is also possible.
• the curable composition of the present invention is used in the manufacture of image sensor modules containing parts that degrade under high temperature conditions, the composition is heat cured at a temperature of 60-90° C. for 30-120 minutes, or 120 Heat curing is preferably performed at a temperature of up to 200° C. for 1 to 300 seconds.
• the epoxy resin composition may be slightly heated in order to lower the viscosity and facilitate the injection. In the case of conventional epoxy resin compositions, such heating may actually make injection difficult due to the increase in viscosity that accompanies the progress of curing.
• the epoxy resin composition of the present invention contains an azole compound in combination with a filler, its curing is not accelerated even by heating to a certain extent, and therefore the viscosity does not increase with the progress of curing. Therefore, the epoxy resin composition of the present invention can be heated to lower its viscosity and can be easily injected into the application site.
• the epoxy resin composition of the present invention can be sufficiently cured by heating under conventionally used conditions. The deterioration of the properties of the cured product obtainable by curing the epoxy resin composition of the present invention, associated with the presence of azole compounds and fillers, is also substantially unnoticeable.
• the epoxy resin composition of the present invention is, for example, a semiconductor device containing various electronic parts, an adhesive for fixing, joining or protecting parts constituting electronic parts, a sealing material, a damming agent, or a raw material thereof. can be used as
• the present invention also provides an adhesive comprising the epoxy resin composition of the present invention.
• the adhesive of the present invention is useful, for example, in manufacturing and fixing modules and electronic components.
• the present invention also provides a sealing material containing the epoxy resin composition of the present invention.
• the sealing material of the present invention is suitable, for example, as a filling material for protecting and fixing modules, electronic components, and the like.
• the present invention also provides a cured product obtainable by curing the epoxy resin composition, adhesive or sealing material of the present invention.
• the present invention further provides an electronic component containing the cured product of the present invention.
• Examples 1-11, Comparative Example 1, Reference Examples 1-2 Epoxy resin compositions were prepared according to the formulations shown in Table 1 by mixing predetermined amounts of each component using a three-roll mill. In Table 1, the amount of each component is expressed in parts by mass (unit: g).
• (A) Polyfunctional Thiol Compounds Compounds used as polyfunctional thiol compounds in Examples and Comparative Examples are as follows.
• (A-2): Pentaerythritol tetrakis(3-mercaptopropionate) (trade name: PEMP, manufactured by SC Organic Chemical, thiol equivalent: 122)
• Table 1 the total number (mol) of thiol groups for (A) the polyfunctional thiol compound corresponding to each compounding amount of these compounds is shown in parentheses.
• (B) Polyfunctional Epoxy Resin Compounds used as polyfunctional epoxy resins in Examples and Comparative Examples are as follows.
• Table 1 the total number (mol) of epoxy groups for (B) the polyfunctional epoxy resin corresponding to each compounding amount of these compounds is shown in parentheses.
• (C) Azole Compounds Compounds used as azole compounds in Examples and Comparative Examples are as follows.
• (D) Curing Catalyst Compounds used as curing catalysts in Examples and Comparative Examples are as follows.
• E Filler Compounds used as fillers in Examples and Comparative Examples are as follows.
• any epoxy resin composition containing (A) a polyfunctional thiol compound, (B) a polyfunctional epoxy resin, (C) an azole compound, (D) a curing catalyst, and (E) a filler no significant increase in viscosity is observed even when heated to a certain extent (Examples 1 to 11).
• Such an epoxy resin composition can be easily injected into the application site by lowering its viscosity by heating.
• the cured product has excellent thermal cycle resistance.
• the epoxy resin composition of the present invention contains an azole compound in combination with a filler, even if it is heated to some extent for the purpose of reducing viscosity, the progress of curing and the associated increase in viscosity are not accelerated. Therefore, the epoxy resin composition of the present invention can be heated to lower its viscosity and can be easily injected into the application site. Moreover, the cured product of the epoxy resin composition of the present invention has excellent thermal cycle resistance. Since such an epoxy resin composition can improve the efficiency of bonding work, it is extremely useful in the manufacture of various electronic components such as camera modules.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Epoxy Resins (AREA)
• Sealing Material Composition (AREA)

Priority Applications (1)

Applications Claiming Priority (2)

Publications (1)

Family

ID=85240599

Family Applications (1)

Country Status (3)

Citations (3)

• 2022
  • 2022-08-16 TW TW111130796A patent/TW202319431A/zh unknown
  • 2022-08-16 JP JP2023542408A patent/JPWO2023022148A1/ja active Pending
  • 2022-08-16 WO PCT/JP2022/030949 patent/WO2023022148A1/ja not_active Ceased

Patent Citations (3)

Also Published As

Similar Documents

Legal Events