KR101819264B1 - Epoxy resin composition and semiconductor sealing material using same - Google Patents
Epoxy resin composition and semiconductor sealing material using same Download PDFInfo
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- KR101819264B1 KR101819264B1 KR1020137019593A KR20137019593A KR101819264B1 KR 101819264 B1 KR101819264 B1 KR 101819264B1 KR 1020137019593 A KR1020137019593 A KR 1020137019593A KR 20137019593 A KR20137019593 A KR 20137019593A KR 101819264 B1 KR101819264 B1 KR 101819264B1
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- 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
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- 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
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
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- 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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/226—Mixtures of di-epoxy compounds
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- 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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
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- 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
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4284—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof together with other curing agents
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- 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
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
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- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
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- 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
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
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- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
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- Health & Medical Sciences (AREA)
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- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
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Abstract
Disclosed is an epoxy resin composition which has a low viscosity and can be cured at a low temperature in a short time and has excellent heat resistance, withstand voltage, electrical insulation, moisture resistance, mechanical strength and adhesiveness, (A) an epoxy resin, (B) 1,4-cyclohexanedimethanol diglycidyl ether, (C) an imidazole-based latent curing agent, and (B) 1,4-cyclohexanedimethanol di (meth) acrylate based on the total mass of the epoxy resin (A) and the 1,4-cyclohexanedimethanol diglycidyl ether (B) Wherein the content of the glycidyl ether is 0.5 to 80 mass%, the content of the (C) imidazole-based latent curing agent relative to the total mass of the total components of the epoxy resin composition is 5 to 25 mass% Phase for total mass (D) the content of the phenolic resin provides an epoxy resin composition, characterized in that 0.5 to 25% by mass.
Description
The present invention relates to an epoxy resin composition suitable for a semiconductor encapsulant and a semiconductor encapsulant using the epoxy resin composition. The semiconductor encapsulant of the present invention can be used either as a primary encapsulating material for semiconductor packaging or as a semiconductor encapsulating material for secondary packaging.
Epoxy resins have been used as electrical insulating materials for electrical and electronic parts such as semiconductor encapsulating materials because of their excellent electrical insulating properties, mechanical strength, heat resistance, moisture resistance and adhesiveness.
As an epoxy resin composition used for this purpose requires excellent voltage resistance and electrical insulation properties, a composition of generally a no-solvent formulation is used, and when used as a semiconductor encapsulating material, Is required.
For the purpose of lowering the viscosity of conventional epoxy resin compositions, monoglycidyl ethers such as butyl glycidyl ether and phenyl glycidyl ether, 1,6-hexanediol diglycidyl ether, neodecanoic acid glycidyl ester and the like Various epoxy resin diluents have been proposed, and the viscosity (25 캜) of the epoxy resin composition obtained by mixing such an epoxy resin diluent is about 350 to 400 cps.
However, although the epoxy resin diluent exhibits a certain effect for reducing the viscosity of the epoxy resin composition, the cured product of the epoxy resin composition is remarkably deteriorated in heat resistance, has sufficient moisture resistance, mechanical strength and electrical characteristics And the like. In addition, since the epoxy resin composition has a low glass transition temperature (Tg) of about 80 to 105 DEG C, there is a problem that solder ball stiffness at the time of sealing is lowered and cracks are generated in a heat cycle test.
In addition, when an epoxy resin diluent is blended, there are problems such as poor storage stability and curability.
In order to solve the above-mentioned problem, in Patent Document 1, a specific epoxy compound (specifically, 1,4-cyclohexanedimethanol diglycidyl ether) is dissolved in a predetermined amount as an epoxy resin diluent (specifically, 100 parts by weight of an epoxy resin It is possible to provide an epoxy resin composition having an excellent heat resistance, withstand voltage, electrical insulation, moisture resistance, mechanical strength, and adhesion without lowering the curability and lowering the curability.
However, since the epoxy resin composition disclosed in Patent Document 1 uses an acid anhydride-based curing agent as a curing agent, it is impossible to achieve curing at a low temperature in a short time required in a semiconductor encapsulant, particularly, a semiconductor encapsulating material for secondary mounting. In order to prevent thermal damage to the structure on the substrate, the semiconductor encapsulating material, particularly the second encapsulating semiconductor encapsulating material, is used for mounting on a substrate on which other mounted parts such as capacitor chip parts are mounted. Therefore, Specifically, it is required to cure at a temperature of 150 ° C or less for several minutes, but this can not be achieved when an acid anhydride-based curing agent is used as a curing agent.
Further, since an acid anhydride-based curing agent is used as a curing agent, there is a problem that the pot life (pot life) of the semiconductor encapsulating material is short.
The epoxy resin composition containing 1,4-cyclohexanedimethanol diglycidyl ether as an essential component is also disclosed in Patent Document 2, but the epoxy resin composition contains 1,4-cyclohexanedimethanol diglycidyl ether and 1,4- Since the mixture of hydrogenated bisphenol A diglycidyl ether is used as an epoxy resin component, the viscosity is so high that when it is used as a semiconductor encapsulating material, the packing property with respect to the encapsulated part is poor.
Disclosure of Invention Technical Problem [8] In order to solve the problems of the prior art described above, it is an object of the present invention to provide a solder ball reinforcement material which has a low viscosity and can be cured at a low temperature in a short time and has excellent heat resistance, withstand voltage, electrical insulation, moisture resistance, mechanical strength, And an epoxy resin composition having a long pot life, and a semiconductor encapsulating material using the epoxy resin composition.
(B) 1,4-cyclohexanedimethanol diglycidyl ether, (C) an imidazole-based latent curing agent, and (D) a phenolic resin, wherein the epoxy resin (A) ,
The content of 1,4-cyclohexanedimethanol diglycidyl ether (B) relative to the total mass of the epoxy resin (A) and the 1,4-cyclohexanedimethanol diglycidyl ether (B) is 0.5 (D) to the total mass of the total components of the epoxy resin composition, wherein the content of the (C) imidazole-based latent curing agent relative to the total mass of all the components of the epoxy resin composition is 5 to 25 mass% Wherein the content of the phenol resin is 0.5 to 25% by mass.
The epoxy resin composition of the present invention preferably contains a liquid epoxy resin as the (A) epoxy resin.
The epoxy resin composition of the present invention may further contain (E) a boric acid ester compound.
The epoxy resin composition of the present invention may further contain (F) silica filler.
The epoxy resin composition of the present invention may further contain (G) a silane coupling agent.
The present invention also provides a semiconductor sealing material using the epoxy resin composition of the present invention.
The epoxy resin composition of the present invention has a low viscosity at room temperature (25 ° C) of 6000 mPa · s or less, and thus has good workability.
The epoxy resin composition of the present invention is excellent in low-temperature short-time curing property and can be cured by heating for several minutes at a temperature of 150 ° C or lower.
In addition, the epoxy resin composition of the present invention has good storage stability at room temperature (25 DEG C) and has a long pot life.
Further, the epoxy resin composition of the present invention is excellent in solder ball stiffness at the time of sealing, and cracking can be suppressed in the heat cycle test.
By virtue of these properties, the epoxy resin composition of the present invention is suitable as a semiconductor encapsulant of a semiconductor encapsulant for primary mounting or secondary mounting.
Hereinafter, the present invention will be described in detail.
The epoxy resin composition of the present invention contains the following components (A) to (D) as essential components.
(A) Component: Epoxy resin
The epoxy resin as the component (A) is a constituent of the main component of the epoxy resin composition of the present invention.
The epoxy resin as the component (A) is preferably liquid at room temperature, but even if it is solid at room temperature, it may be diluted with another liquid epoxy resin or diluent to form a liquid phase.
Specific examples include bisphenol A type epoxy resins, brominated bisphenol A type epoxy resins, bisphenol F type epoxy resins, biphenyl type epoxy resins, novolak type epoxy resins, alicyclic epoxy resins, naphthalene type epoxy resins, ether type or polyether type Epoxy resin, oxirane ring-containing polybutadiene, silicone epoxy copolymer resin, and the like.
Particularly, as the liquid epoxy resin, the bisphenol A type epoxy resin has an average molecular weight of about 400 or less; a branched polyfunctional bisphenol A type epoxy resin such as p-glycidyloxyphenyldimethyltris bisphenol A diglycidyl ether; Bisphenol F type epoxy resin; A phenol novolak type epoxy resin having an average molecular weight of about 570 or less; Epoxycyclohexylmethyl (3,4-epoxycyclohexyl) methyl, adipic acid bis (3,4-epoxy-6-methylcyclohexylmethyl) Alicyclic epoxy resins such as 2- (3,4-epoxycyclohexyl) 5,1-spiro (3,4-epoxycyclohexyl) -m-dioxane; Biphenyl-type epoxy resins such as 3,3 ', 5,5'-tetramethyl-4,4'-diglycidyloxybiphenyl; Glycidyl ester type epoxy resins such as diglycidyl hexahydrophthalate, diglycidyl 3-methylhexahydrophthalate and diglycidyl hexahydroterephthalate; Glycidyl amines such as diglycidyl aniline, diglycidyl toluidine, triglycidyl-p-aminophenol, tetraglycidyl-m-xylylenediamine, tetraglycidylbis (aminomethyl) cyclohexane, Type epoxy resin; And 1,3-diglycidyl-5-methyl-5-ethylhydantoin; Naphthalene ring-containing epoxy resins are exemplified. An epoxy resin having a silicon skeleton such as 1,3-bis (3-glycidoxypropyl) -1,1,3,3-tetramethyldisiloxane can also be used. Further, a diepoxide compound such as (poly) ethylene glycol diglycidyl ether, (poly) propylene glycol diglycidyl ether, butanediol glycidyl ether, neopentyl glycol diglycidyl ether; Trimethylolpropane triglycidyl ether, glycerin triglycidyl ether, and the like.
As the epoxy resin, a high molecular weight bisphenol A type epoxy resin, a novolac epoxy resin, a tetrabromo bisphenol A type epoxy resin and the like can be exemplified as the epoxy resin. These may be used in combination with an epoxy resin and / or a diluent which is liquid at room temperature to control the flowability.
In the case of using an epoxy resin which is solid or ultra high at room temperature, an epoxy resin having a low viscosity, for example, (poly) ethylene glycol diglycidyl ether, (poly) propylene glycol diglycidyl ether, butanediol glycidyl ether, Diepoxide compounds such as neopentyl glycol diglycidyl ether; Trimethylol propane triglycidyl ether, glycerin triglycidyl ether, and the like.
When a diluent is used, any of a non-reactive diluent and a reactive diluent may be used, but a reactive diluent is preferred. In the present specification, the reactive diluent refers to a compound having a relatively low viscosity at room temperature having one epoxy group, and may have a polymerizable functional group other than an epoxy group, for example, an alkenyl group such as vinyl or allyl; Or an unsaturated carboxylic acid residue such as acryloyl or methacryloyl. Examples of such a reactive diluent include n-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, phenyl glycidyl ether, cresyl glycidyl ether, ps-butylphenyl glycidyl ether, styrene oxide, Monoepoxide compounds such as oxides; Monoepoxide compounds having other functional groups such as allyl glycidyl ether, glycidyl methacrylate and 1-vinyl-3,4-epoxycyclohexane are exemplified.
The epoxy resin as the component (A) may be used alone or in combination of two or more. It is preferable that the epoxy resin itself is a liquid at room temperature. Among them, preferred are liquid bisphenol type epoxy resins, liquid aminophenol type epoxy resins, silicone modified epoxy resins and naphthalene type epoxy resins. More preferred are liquid bisphenol A type epoxy resins, liquid bisphenol F type epoxy resins, p-aminophenol type liquid epoxy resins, and 1,3-bis (3-glycidoxypropyl) tetramethyldisiloxane.
Component (B): 1,4-cyclohexanedimethanol diglycidyl ether
Cyclohexanedimethanol diglycidyl ether (hereinafter abbreviated as " DME ") as component (B) is obtained by heating 1,4-cyclohexanedimethanol and epichlorohydrin at a temperature of about 50 to 150 ° C Is added as an epoxy resin diluent to an epoxy compound prepared by dehydrochlorination.
DME can also be prepared by using epoxidation with hydrogen peroxide using an olefin compound as a raw material without using epichlorohydrin. The DME produced by this procedure has a chlorine concentration as low as 100 ppm or lower and is suitable for use as an epoxy resin diluent.
DME is different from conventional epoxy resin diluents such as monoglycidyl ether such as butyl glycidyl ether and phenyl glycidyl ether, 1,6-hexanediol diglycidyl ether and neodecanoic acid glycidyl ester. , The reactivity is high and the decrease in reactivity due to the addition can be suppressed, so that the viscosity of the epoxy resin composition can be lowered without impairing the cured properties such as heat resistance, moisture resistance, mechanical strength and electrical characteristics.
In the epoxy resin composition of the present invention, the content of DME as the component (B) is 0.5 to 80 mass% with respect to the total mass of the epoxy resin as the component (A) and the DME as the component (B). If the amount is less than 0.5% by mass, the effect of the addition of the epoxy resin diluent becomes insufficient, and the viscosity of the epoxy resin composition at room temperature (25 ° C) can not be lowered to 6000 mPa · s or less.
On the other hand, if it exceeds 80 mass%, the glass transition temperature (Tg) and the adhesiveness are lowered, and the properties of the cured product are adversely affected.
The content of DME as the component (B) is preferably 1 to 70 mass%, more preferably 5 to 62.5 mass% with respect to the total mass of the epoxy resin as the component (A) and the DME as the component (B).
(C): Imidazole-based latent curing agent
The imidazole-based latent curing agent as the component (C) is a curing agent for the epoxy resin. Use of an imidazole-based latent curing agent as a curing agent for an epoxy resin is excellent in low-temperature short-time curing ability and can be cured by heating for several minutes at a temperature of 150 ° C or lower.
Further, by using an imidazole-based latent curing agent, the storage stability at room temperature (25 DEG C) of the epoxy resin composition is improved, and the pot life can be prolonged.
As the imidazole-based latent curing agent, known imidazole-based latent curing agents can be used. Specific examples thereof include PN23, PN40 and PN-H (all trade names, manufactured by Ajinomoto Fine Techno Co., Ltd.). Examples thereof include Nova Cure HX-3088, Nova Cure HX-3941, HX-3742 and HX-3722 (all trade names, all of which are trade names) Manufactured by Asahi Chemical Industry Co., Ltd.) and the like.
Any one of the imidazole-based latent curing agents may be used, or two or more of them may be used in combination.
In the epoxy resin composition of the present invention, the content of the imidazole-based latent curing agent as the component (C) is 5 to 25 mass% with respect to the total mass of the total components of the epoxy resin composition.
If the amount is less than 5% by mass, the curing at low temperature in a short period of time is inferior and the curing can not be performed at a temperature of 150 캜 or less for several minutes while the storage stability at room temperature (25 캜) .
The content of the imidazole-based latent curing agent as the component (C) is preferably 5.6 to 24.3% by mass with respect to the total mass of the entire components of the epoxy resin composition.
(D) Component: phenol resin
The phenol resin as the component (D) is added to achieve uniform curing of the epoxy resin composition. In the case of the epoxy resin composition of the present invention, an imidazole-based latent curing agent is used as a curing agent for an epoxy resin, so that it can be cured by heating for several minutes at a temperature of 150 ° C or lower, There arises a problem that the curing is likely to be non-uniform at the time of curing, the appearance of the cured product is deteriorated, and the adhesion of the cured product is impaired.
As the phenol resin, it is widely used because it is used also as a curing agent of an epoxy resin. Specific examples thereof include allyl acrylphenol resins (for example, MEH8005 (trade name, manufactured by Meiwa Chemical Industry Co., Ltd.)).
In the epoxy resin composition of the present invention, the content of the phenol resin as the component (D) is 0.5 to 25 mass% with respect to the total mass of the total components of the epoxy resin composition.
If it is less than 1% by mass, the curing becomes uneven at the time of low-temperature short-time curing, resulting in deterioration of the appearance of the cured product and impairment of the adhesion of the cured product.
On the other hand, when the amount exceeds 20 mass%, the storage stability of the epoxy resin composition at room temperature (25 캜) is lowered and the pot life is shortened.
The content of the phenol resin as the component (D) is preferably 1 to 20.1% by mass with respect to the total mass of the entire components of the epoxy resin composition.
The epoxy resin composition of the present invention may contain the components described below in addition to the above components (A) to (D), if necessary.
Component (E): boric acid ester compound
The epoxy resin composition of the present invention may contain a boric acid ester compound as the component (E) in order to improve the storage stability at room temperature (25 캜) to prolong the pot life.
Examples of the boric ester compound of the component (E) include 2,2'-oxybis (5,5'-dimethyl-1,3,2-oxaborinane), trimethylborate, triethylborate, But are not limited to, borate, triisopropyl borate, tri-n-butyl borate, tripentyl borate, triallyl borate, trihexyl borate, tricyclohexyl borate, trioctyl borate, trinonyl borate, tridecyl borate, Decyl borate, trioctadecyl borate, tris (2-ethylhexyloxy) borane, bis (1,4,7,10-tetraoxydecyl) (1,4,7,10,13-pentaoxatetradecyl) (1,4,7-trioxandecyl) borane, tribenzylborate, triphenylborate, tri-o-tolylborate, tri-m-tolylborate and triethanolamine borate.
When the boric acid ester compound is contained as the component (E), it is preferably 0.05 to 5 mass%, more preferably 0.1 to 3 mass%, and still more preferably 0.5 to 1.5 mass%, based on the total mass of all components of the epoxy resin composition Do.
(F) Component: silica filler
The epoxy resin composition of the present invention may contain a silica filler as the component (F) in order to control the viscosity of the resin composition and to improve the heat resistance and humidity resistance of the cured product of the resin composition.
When the silica filler is contained as the component (F), the content is preferably 5 to 80 mass%, more preferably 15 to 70 mass%, and still more preferably 20 to 65 mass%, based on the total mass of all components of the epoxy resin composition .
The shape of the silica filler as the component (F) is not particularly limited, and may be any of a granular form, a powder form, a scaly form and the like.
The silica filler as the component (F) may be subjected to surface treatment if necessary. For example, an oxide film may be formed on the surface of the particles.
The average particle diameter of the silica filler as the component (F) (the average maximum diameter when it is not a granular phase) is not particularly limited, but it is preferably from 0.01 to 30 탆, because the filling property with respect to the sealing portion becomes good, , More preferably 0.1 to 10 mu m.
(G) Component: Silane coupling agent
The epoxy resin composition of the present invention may contain a silane coupling agent as the component (G) in order to improve the adhesion of the cured product.
When the silane coupling agent is contained as the component (G), the amount is preferably 0.01 to 10% by mass, more preferably 0.05 to 5% by mass, still more preferably 0.1 to 3% by mass based on the total mass of all components of the epoxy resin composition Do.
The epoxy resin composition of the present invention may contain components other than the above (A) to (G), if necessary. Specific examples of such components include a filler, a leveling agent, a colorant, an ion trap agent, a defoaming agent, an antioxidant, a flame retardant, and the like. The kind and blending amount of each compounding agent are in a usual manner.
(Preparation of epoxy resin composition)
The epoxy resin composition of the present invention is prepared by mixing the above components (A) to (D), and optionally mixing the components (E) to (G) Mixing and stirring may be performed using a roll mill, but the present invention is not limited thereto. When the epoxy resin as the component (A) is solid, it is preferably liquefied or fluidized by heating or the like and mixed.
Each component may be mixed at the same time, and some components may be mixed first, and the remaining components may be mixed later.
Hereinafter, the characteristics of the epoxy resin composition of the present invention will be described.
The epoxy resin composition of the present invention has a viscosity as low as 6000 mPa · s or less at room temperature (25 ° C), and thus has good workability when used in applications such as semiconductor encapsulation materials.
The epoxy resin composition of the present invention preferably has a viscosity at room temperature (25 ° C) of not more than 5500 mPa · s, more preferably not more than 4000 mPa · s, and still more preferably not more than 3000 mPa · s.
The epoxy resin composition of the present invention is excellent in low-temperature short-time curing property and can be cured at a temperature of 150 ° C or lower for several minutes (for example, heating at 120 ° C for 3 minutes).
The epoxy resin composition of the present invention preferably has a gel time of 180 seconds or less, more preferably 90 seconds or less and more preferably 60 seconds or less, as measured by the procedure described in the following Examples.
In addition, the epoxy resin composition of the present invention has good storage stability at room temperature (25 DEG C) and has a long pot life. Concretely, the viscosity after storage for 48 hours in an environment of 25 DEG C and 50% humidity is 1.2 times lower than the viscosity before storage, preferably, the viscosity after 168 hours is 1.2 times lower than the viscosity before storage.
Further, the epoxy resin composition of the present invention is excellent in adhesiveness and has a peel strength of 10 kg or more, preferably 15 kg or more, and more preferably 17 kg or more as measured by the procedure described in Examples described later.
Further, since the epoxy resin composition of the present invention has a glass transition temperature (Tg) of 120 ° C or higher, the epoxy resin composition of the present invention is excellent in solder ball stiffness at the time of sealing and can be subjected to a heat cycle test (for example, repeating a heat cycle from -40 ° C to 125 ° C Cracking is suppressed in the test of durability). The epoxy resin composition of the present invention preferably has a glass transition temperature (Tg) of 125 캜 or higher, and more preferably 130 캜 or higher.
With these properties, the epoxy resin composition of the present invention is suitable as a semiconductor encapsulating material for primary mounting or secondary mounting.
The epoxy resin composition of the present invention is also suitable for adhesives and die bonding agents.
Example
Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited thereto.
(Examples 1 to 14 and Comparative Examples 1 to 4)
The raw materials were kneaded using a roll mill so that the blending ratios shown in the following Table were prepared to prepare the epoxy resin compositions of Examples 1 to 14 and Comparative Examples 1 to 4. Further, numerical values relating to each composition in the table indicate mass parts.
The symbols in the table indicate below.
Epoxy resin: bisphenol A type epoxy resin, product name EXA850CRP, manufactured by DIC Co., Ltd.)
DME: 1,4-cyclohexanedimethanol diglycidyl ether, product name ZX1658GS, manufactured by Shin-Nittsu Chemical Co., Ltd.
(Imidazole type latent curing agent): Microcapsule type imidazole (containing imidazole component and bisphenol A type epoxy resin), product name HX3742, manufactured by Asahi Kasei Emergeries Co., Ltd.
Phenol resin: allyl acrylphenol resin, product name MEH8005, manufactured by Meiwa Chemical Industry Co., Ltd.
Acid anhydride-based curing agent: (product name: HN-5500, manufactured by Hitachi Chemical Co., Ltd.)
The following evaluation was made on the epoxy resin composition thus prepared.
(Exterior of hardened cargo)
A test piece coated with 10 mg of a test sample to be in contact with the long side of a silicon chip (2 x 20 x 0.75 mm) adhered on a polyimide film was placed in an oven and heated at 120 캜 for 3 minutes to cure the epoxy resin composition. The exterior appearance of the cured product after heating was visually observed. A case where appearance defects such as wrinkles and orange peel or color irregularities were not observed on the cured product was evaluated as & cir &, and a case where appearance defects such as wrinkles, orange peel,
(Viscosity, port life)
The viscosity (initial viscosity) of the test sample immediately after preparation at a liquid temperature of 25 캜 and at 1 rpm was measured using an EMD-type viscometer (manufactured by TOKYO CORP., Equipment name: TV-22).
Thereafter, the sample for evaluation was placed in a closed container, and the viscosity was measured at the time when it was stored at 25 ° C and 50% humidity for 48 hours. A case where the viscosity after storage for 48 hours was less than 1.2 times of the initial viscosity was evaluated as & cir &, and a case where the viscosity was 1.2 times or more was evaluated as x.
The sample for evaluation was placed in a closed container, and the viscosity was measured at 168 ° C for 168 hours in an environment of 25 ° C and a humidity of 50%. A case where the viscosity after storage for 168 hours was less than 1.2 times of the initial viscosity was rated "? &Quot;, and a case where the viscosity was 1.2 times or more was evaluated as x.
(Gel time)
5 mg 占 1 mg of the epoxy resin composition was supplied onto a hot plate at 120 占 폚 and stirred while being circled by a stirring rod. When the stirring rod was lifted while being stirred from the time of feeding, the thread drag was 5 mm or less Was measured.
(Adhesion)
An evaluation sample is printed on a glass epoxy substrate and a 2 mm x 2 mm silicon chip is placed on the sample. This is heat cured in a hot air dryer at 150 ± 2 ° C for 5 minutes. Using this as a test piece, a load is applied to a silicon chip using a versatile bond tester " DAGE4000 " manufactured by Dage to measure the strength (peel strength) when the chip is peeled off. n = 10, and the evaluation value is set as an inspection value.
Glass Transition Temperature (Tg): Glass transition temperature was measured by the TMA method using TM3000 manufactured by Vacuum Corporation for a cured product cured by heating at 120 ° C for 3 minutes.
Example One
(B) 31.1 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 5.6 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 5 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Example 2
(B) Component 31.2 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 11.2 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 5 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Example 3
(B) Component 31.2 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 15.0 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 5 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Example 4
(B) 31.3 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 18.8 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 5 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Example 5
(B) Component 31.2 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 24.3 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 5 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Example 6
(B) Component 31.2 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 15 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 1.0% by mass Component
(Relative to the total mass of all components of the epoxy resin composition)
Example 7
(B) Component 31.2 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 15 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) Component 3.1 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Example 8
(B) Component 31.2 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 15 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) Component 9.4 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Example 9
(B) 31.1 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 15 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) Component 14.7 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Example 10
(B) component 31.0 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 15 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 20.1 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Example 11
Component (B) 5.0 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 15 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 5 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Example 12
Component (B) 10.0 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 15 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 5 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Example 13
Component (B) 50.0 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 15 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 5 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Example 14
Component (B) 62.5 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 15 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 5 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Comparative Example One
(B) 31.1 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 3.0 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 5 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Comparative Example 2
(B) Component 31.2 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 15 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 0 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Comparative Example 3
(B) 0 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 15 mass%
(Relative to the total mass of all components of the epoxy resin composition)
(D) 5 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Comparative Example 4
(B) Component 29.1 mass%
(With respect to the total mass of the component (A) (including the epoxy resin component of (C)) and the component (B)
(C) component (imidazole component) 5 mass%
(Relative to the total mass of all components of the epoxy resin composition)
Comparative Example 4 contains a conventional amount of microcapsule imidazole used as a curing accelerator. As the curing agent, 0.6 equivalent of an acid anhydride curing agent is contained in an equivalent ratio to the epoxy resin component in the composition.
(D) 0 mass%
(Relative to the total mass of all components of the epoxy resin composition)
It was confirmed that the epoxy resin compositions of Examples 1 to 14 had good cured appearance and uniform curing. The viscosity at 25 占 폚 was 6000 mPa 占 퐏 or less. Also, it was confirmed that the gel time was 120 s or less and excellent low temperature short time curing property was obtained. Also, the adhesion was good and the glass transition temperature (Tg) was 120 DEG C or more. Also, the port life after 48 hours storage was good.
Examples 1 to 4, 6 to 9, and 11 to 14 in which the content of the component (C) was 5.6 to 24.3 mass% and the content of the component (D) was 1 to 20.1 mass% were good in the port life after 168 hours of storage.
On the other hand, the epoxy resin composition of Comparative Example 1 in which the content of the component (C) is less than 5% by mass was not cured even after 180 seconds elapsed in the gel time evaluation, and it was confirmed that the low temperature short-time curability was poor. For this reason, the appearance of the cured product and the adhesion property were not evaluated. It was confirmed that Comparative Example 2, which did not contain the component (D), was inferior in appearance of the cured product and could not be uniformly cured. Therefore, the evaluation of the adhesion and the measurement of the glass transition temperature were not carried out. And Comparative Example 3 containing no component (B) had a viscosity as high as 6000 mPa · s at 20 ° C. Comparative Example 4 in which the acid anhydride-based curing agent was not used and the microcapsule-type imidazole was used as the curing accelerator was not cured even after 180 seconds elapsed in the gel time evaluation, and the low-temperature short- It was confirmed that this was lagging behind. The reason for this is believed to be that the curing action by imidazole is delayed by the presence of the acid anhydride-based curing agent. Also, since it was confirmed that the low-temperature short-time curing property was poor, the adhesion evaluation was not carried out. In addition, the port life after 48 hours was lagging behind. For this reason, the Port Life evaluation after 168 hours of storage was not conducted.
Claims (7)
The content of 1,4-cyclohexanedimethanol diglycidyl ether (B) relative to the total mass of the epoxy resin (A) and the 1,4-cyclohexanedimethanol diglycidyl ether (B) is 0.5 (C) the content of the imidazole-based latent curing agent relative to the total mass of all components of the epoxy resin composition is 5 to 25 mass%, and (D) the total mass of the total components of the epoxy resin composition, Wherein the content of the phenol resin is 1 to 20.1% by mass.
(A) an epoxy resin composition containing a liquid epoxy resin as an epoxy resin.
(E) a boric acid ester compound.
(F) an epoxy resin composition containing a silica filler.
(G) a silane coupling agent.
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| PCT/JP2011/067640 WO2012105072A1 (en) | 2011-02-03 | 2011-08-02 | Epoxy resin composition and semiconductor sealing material using same |
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| JP6013906B2 (en) * | 2012-12-27 | 2016-10-25 | ナミックス株式会社 | Liquid epoxy resin composition |
| JP5681327B2 (en) * | 2013-01-17 | 2015-03-04 | 積水化学工業株式会社 | Curable anisotropic conductive material for electronic parts, connection structure, and method of manufacturing connection structure |
| JP5758463B2 (en) * | 2013-03-26 | 2015-08-05 | 太陽インキ製造株式会社 | Epoxy resin composition, hole filling composition, and printed wiring board using the same |
| JP6340174B2 (en) * | 2013-07-30 | 2018-06-06 | ハリマ化成株式会社 | Conductive paste |
| CN104513455B (en) * | 2013-09-26 | 2017-01-11 | 常州市迪波电子材料有限公司 | Waterproof encapsulating material used in temperature sensors |
| JP2015209516A (en) * | 2014-04-28 | 2015-11-24 | 株式会社クラレ | Curable composition, and cured product |
| WO2015173906A1 (en) | 2014-05-14 | 2015-11-19 | 三菱電機株式会社 | Method for manufacturing semiconductor device |
| US10696840B2 (en) * | 2014-11-26 | 2020-06-30 | Kyocera Corporation | Resin composition for semiconductor encapsulation and semiconductor device |
| JP6754741B2 (en) | 2017-09-07 | 2020-09-16 | 信越化学工業株式会社 | Semiconductor laminates, methods for manufacturing semiconductor laminates, and methods for manufacturing semiconductor devices |
| JP6800115B2 (en) | 2017-09-07 | 2020-12-16 | 信越化学工業株式会社 | Resin composition, resin film, semiconductor laminate, semiconductor laminate manufacturing method and semiconductor device manufacturing method |
| CN107739598B (en) * | 2017-10-31 | 2021-01-26 | 南昌航空大学 | Permanent epoxy resin cementing agent |
| CN113045864A (en) * | 2021-04-26 | 2021-06-29 | 上海方乾科技有限公司 | Halogen-free flame-retardant epoxy resin containing naphthalene ring structure and preparation method thereof |
| CN113265211A (en) * | 2021-05-13 | 2021-08-17 | 苏州震坤科技有限公司 | Encapsulation resin for reducing encapsulation delamination and encapsulation method thereof |
| JP2022175617A (en) * | 2021-05-14 | 2022-11-25 | 住友化学株式会社 | Epoxy resin composition and cured material thereof |
| TW202330702A (en) | 2021-11-19 | 2023-08-01 | 日商納美仕有限公司 | Curable resin composition |
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| JP3454437B2 (en) * | 1992-10-02 | 2003-10-06 | ナショナル スターチ アンド ケミカル インベストメント ホールディング コーポレイション | One-part epoxy resin adhesive composition with low viscosity and no solvent |
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