JPH0224317A - Epoxy resin composition and its use - Google Patents

Abstract

PURPOSE:To obtain a resin composition which can give a cured product excellent in heat resistance, flexibility, humidity resistance and adhesiveness by mixing a polyepoxy compound with a specified fluorinated dicarboxylic acid anhydride compound as a curing agent. CONSTITUTION:The title epoxy resin composition is prepared by mixing a polyepoxy compound with a fluorinated dicarboxylic acid anhydride compound of formula I or II [wherein Rf' and Rf'' are each a group of formula III (wherein m is 1-30), a group of formula IV (wherein R1, R2 and R3 are each CF3, C2F5, C3F7 or C4F9) or a group of formula IV] as a curing agent. The above resin composition can successfully give a cured product containing a large amount of fluorine atoms because the abovementioned compound of formula I or II can act as a crosslinking agent for the epoxy compound. This resin composition is useful as a semiconductor sealing material, a material for laminates or a material for optical discs.

Description

Detailed Description of the Invention [Industrial Application Field] The present invention relates to an epoxy resin composition containing a fluorine-containing dicarboxylic anhydride compound, a semiconductor encapsulation material using the composition, and a laminate. It relates to plate materials and optical disc materials.

[Conventional technology]

In fields such as electronic components and optical components, densification is increasing.

High integration is on the rise. Along with this, the organic materials used in these products have moisture resistance (decreased water absorption and moisture permeability) without sacrificing properties such as heat resistance of molded and cured products.
, imparting flexibility and improving adhesion are required.

Traditionally, in the fields of semiconductor encapsulants and laminates.

Epoxy materials, phenolic materials, and silicone materials are used.

[Problem to be solved by the invention]

Conventional epoxy materials have problems in achieving a balance between imparting flexibility and heat resistance, and with regard to moisture resistance (particularly reducing water absorption and moisture permeability), which is accompanied by a decrease in adhesion. Development of the composition was extremely difficult.

In other words, adding rubber such as polybutadiene to impart flexibility will result in a decrease in heat resistance, and adding a siloxane compound (we are also considering deformed epoxy) to improve moisture resistance will result in poor adhesion. It cannot be said that the epoxy resin composition is necessarily sufficient to cope with future situations, such as a decrease in the epoxy resin composition.

The present invention has been made in view of this situation.

The purpose of the present invention is to produce a cured product with excellent heat resistance, flexibility, moisture resistance (especially reduction in water absorption rate and moisture permeability), and adhesiveness, as well as a cured molded product with excellent transparency and low dielectric constant. The purpose of the present invention is to provide a new epoxy resin composition that can provide various products, and a variety of phase flow applications using the composition.

[Means to solve the problem]

In order to achieve the above object, as a result of various studies on new curing agents for epoxy compounds, the present invention was completed by discovering a fluorine-containing dicarboxylic acid anhydride compound.

The present invention is achieved by performing the following matters.

(1) At least a polyfunctional epoxy compound and a primary formula [I
] and/or the following formula (II) F a [In the above formula, Rt' and R, IT are F+CF-CFz
-〇→, CF-CO- (m is 1 to 30 and is either FδC2, and may be the same or different from each other)] An epoxy resin composition characterized by:

(2) A semiconductor encapsulation material using the epoxy resin composition described in (1).

(3) A laminate material using the epoxy resin composition described in (1).

(4) An optical disc material using the epoxy resin composition described in (1).

(5) The fact that the polyfunctional epoxy compound is a tetrafunctional epoxy compound represented by the following formula (IIIR3) is CF3
1 CzF 31 Cs F 7I C4F! The epoxy resin composition according to (1), characterized by:

It is. Even if they are the same, they are different (6
) At least a polyfunctional epoxy compound, a fluorine-containing dicarboxylic anhydride compound represented by formula (11) and/or formula (II), and an N,N'-substituted unsaturated bisimide compound. This is an epoxy resin composition.

[Effect]

The effects of the present invention are based on the use of the fluorine-containing dicarboxylic anhydride compounds represented by the formulas [I] and (II) as curing agents for polyfunctional epoxy compounds. That is, the water absorption rate of the dicarboxylic acid anhydride represented by formula CI) and formula [II] with a large fluorine content,
This is presumed to be due to the effect of reducing moisture permeability, improving adhesion, and imparting flexibility.

Heat resistance, moisture resistance, flexibility, and adhesive properties of the present invention.

Furthermore, a major factor in achieving a balance between low dielectric constant and imparting transparency is that the new fluorine-containing dicarboxylic acid anhydride compounds represented by formula (1) and formula [II] act as crosslinking agents for epoxy compounds. By becoming, in the cured product,
The success lies in the introduction of a large amount of fluorine-containing functional groups.

In the present invention, the polyfunctional epoxy compound is, for example,
Diglycidyl ether of bisphenol A, butadiene diepoxide, 3,4-epoxycyclohexylmethyl-(3,4-epoxy)cyclohexane carboxylate, vinylcyclohexane dioxide, 4,4'-di(1,2-epoxyethyl)di biphenyl ether, 4
．． 4'-(1,2-epoxyethyl)biphenyl, 2°2-bis(3,4-epoxycyclohexyl)propane, diglycidyl ether of resorcinol, diglycidyl ether of phloroglucin, diglycidyl ether of methylphloroglucin, bis -(2,3-epoxycyclopentyl)ether.

2-(3,4-epoxy)cyclohexane-5゜5-
Spiro(3,4-epoxy)-cyclohexane-m-dioxane, bis-(3,4-epoxy-6-methylcyclohexyl)adipate, N.

N'-m-phenylenebis(4,5-epoxy-1,2
trifunctional epoxy compounds such as -cyclohexane) dicarboximide, triglycidyl ether of para-aminophenol, polyallyl glycidyl ether, 1,3.5-tri(1,2
-Epoxyethyl)benzene, 2°2', 4.4'
- Known trifunctional or higher functional epoxy compounds such as tetraglycidoxytetraphenylethane, polyglycidyl ether of phenol formaldehyde novolac, triglycidyl ether of glycerin, triglycidyl ether of trimethylolpropane, or 4,5-dihydroxyhexane. Epoxy compounds derived from hydrophthalic acid, such as, can be used.

One or more known epoxy compounds including the above-mentioned epoxy compounds may be used in combination.

In the present invention, the fluorine-containing dicarboxylic anhydride compounds represented by formula [I] and formula (11) are, for example, (in the above formula, m is 1 to 30) CFa (the above In the formula, m is 1 to 3o.).

As for the above-format [I] or the general formula synthesis process, for example, (IT) [in the above formula, Rx' and Rx' are F(-CF-C
F2-0-), CF-Co- (m is 1 to 30\CFs, C2F5, CaF7, C
Any one of 4F o. They may be the same or different from each other (manufactured by Shin Nihon Rika Co., Ltd.) gCz and may be the same or different from each other. ] can be obtained from the reaction process as follows.

Incidentally, in the epoxy resin composition of the present invention, the polyfunctional epoxy compound and the fluorine-containing dicarboxylic acid anhydride compounds represented by formula CI] and formula [II] may be suitably combined with each other depending on the purpose and use. The proportion is chosen.

A conventionally known curing agent can also be used in combination with the epoxy resin composition of the present invention. They are written by Hiroshi Nakauchi: Epoxy Resin (published September 1970), pages 109-149, Le
e, by Neville: Epoxy Resins
(Me Gray-Hill Book Company
y Inc: New Work.

Published in 1957) pages 63-141, P, E.

Written by Brunis: Epoxy Re5ins Tec
hnology(Interscience Publ.
ishers, New York, 1968)
Compounds described on pages 45 to 111, such as aliphatic polyamines, aromatic polyamines, amines including secondary and tertiary amines, carboxylic acids, carboxylic acid anhydrides, aliphatic and aromatic polyamide oligomers, and Polymers, boron trifluoride-amine complexes, synthetic resin initial condensates such as phenol resins, melamine resins, urea resins, and urethane resins, as well as dicyandiamide, carboxylic acid hydrazides, and monomaleimides.

Examples include polyaminomaleimides.

One or more types of these curing agents can be used depending on the use and purpose.

A catalyst that promotes the curing reaction between the epoxy compound and the fluorine-containing dicarboxylic anhydride compound can be used in the resin composition of the present invention.

Such catalysts include, for example, tertiary amines such as triethanolamine, tetramethylbutanediamine, tetramethylbutanediamine, tetramethylhexanediamine, triethylenediamine, dimethylaniline, oxyalkyl amines such as dimethylaminoethanol, dimethylaminopetanol, etc. There are amines such as amine, tris(dimethylaminomethyl)phenol, N-methylmorpholine, and N-ethylmorpholine.

Also, cetyltrimethylammonium bromide, cetyltrimethylammonium chloride, dodecyltrimethylammonium iodide, trimethyldodecylammonium chloride, benzyldimethyltetradecylammonium chloride, benzylmethylpalmitylammonium chloride, allyldodecyltrimethylammonium bromide, benzyldimethylstearylammonium bromide, stearyl There are quaternary ammonium salts such as trimethylammonium chloride and benzyldimethyltetradecylammonium acetate.

Also, 2-ethylimidazole, 2-undecylimidazole, 2-heptadecyl imidazole, 2-methyl-
4-ethylimidazole, 1-butylimidazole, 1
-Propyl-2-methylimidazole, 1-benzyl-
2-Methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-azine-2-methylimidazole, 1-azine-2-undecyl Imidazole such as imidazole, triphenylphosphine tetraphenylborate, tetraphenylphosphonium tetraphenylborate, triethylaminete-1-raphenylborate, N-methylmorpholinetetraphenylborate, 2-ethyl-4-
Examples include tetraphenylborate such as methylimidazoletetraphenylborate and 2-ethyl-1,4-dimethylimidazoletetraphenylborate.

Also, 1,5-diaza-bicyclo(4,2,O)octene-5,1,8-diaza-bicyclo(7°2.0)undecene-8,1,4-diaza-bicyclo(3,3, O)
octene-4,3-methyl-1,4-diazabicyclo(
3,3,O)octene-4,3,6,7,7-tetramethyl-1,4-diazadicyclo(3,3,O)octene-4,1,5-diaza-bicyclo(3,4,O ) Nonene-5,1,8-diaza-bicyclo(7,3,O) Dodecene-8,1,7-diazabicyclo(4,3゜0) Nonene-6,1,5-diazabicyclo(4゜4.0 )decene-5,1,8-diazabicyclo(7,4,0))-lysocene-8,1,8-diazabicyclo(5,3,O)decene-7,9-methyl-1,8-diazabicyclo(5 ,3
, O) Decene-7,1,8-diazabicyclo(5,4,
O) undecene-7,1,6-diazabicyclo(5,5
゜0) Dodecene-6,1,7-diazabicyclo (6゜5
．． O) Tridecene-7,1,8-diazabicyclo(
7,5,O) Tetradecene-8,'l,10-diazabicyclo(7,3,O) Dodecene-9,1゜10-diazabicyclo(7,4,O) Tridecene-9,1,
14-diazabicyclo(11,3,O)hexadecene-
Also useful are diazabicyclo-alkenes such as 13,1,14-diazabicyclo(11,4,0)butadecene-13. One or more of these compounds can be used in combination depending on the purpose and use.

Also, at least one metal selected from aluminum, titanium, tin, zinc, lead and zirconium,
A metal chelate-1-compound consisting of a ligand selected from β-diketones and β-keto acid esters is used. For example, tris(2,4-pentanedioner-1.)
Aluminum, (2,4-pentanedionate) bis(
ethyl acetoacetate) aluminum, tris(ethylacetoacetate) aluminum, bis(ethylacetoacetate) titanium, te 1 herakis (2,4-pentanedionate) titanium, dibutyl bis(2,4-pentanedionate) tin , dimethylbis(ethylacetoacetate)tin, bis(2,4-pentanedionato)zinc, bis(ethylacetoacetate)lead, tetrakis(ethylacetoacetate)zirconium, and the like.

Furthermore, an alcoholate compound of at least one metal selected from aluminum, titanium, tin, zinc, lead, and zirconium is used as a component. Such alcoholate compounds include, for example, aluminum methylate, aluminum methylate, aluminum propylate, aluminum n-butyrate, mono-5ec-butoxyaluminum, aluminum propylate, ethylaluminum, diethyl-1 -, ethylaluminum, Jimmy propylate-1-, titanium, tetra-1-propylate, tin, tetra-1-propylate, zinc, Jimmy propylate, lead, Jimmy propylate, zirconium, tetra-1- There are propylate and the like, and one or more of them can be used, and some or all of them may be used as a prepolymer obtained by polycondensation.

In the present invention, the N,N'-substituted unsaturated bisimide compound is of the form (IV) [wherein D is a dicarboxylic acid residue having an ethylenically unsaturated double bond]. Also, or alkylene group.

Indicates an arylene group or a divalent organic group substituted therewith. ], such as N,N'-ethylene bismaleimide, N,N'-
Hexamethylene bismaleimide, N,N'-dodecamethylene bismaleimide, N.

N'-m-phenylene bismaleimide, N, N'-P-
Phenylene bismaleimide, N,N'-I'-phenylenebiscitraconimide, N,N'P-phenylenebisitaconimide, N,N'P-phenylenebispirociconimide, N,N'-P-phenylene-endo Methylenetetrahydrophthalimide, N,N'-4,4'-
diphenylmethane bismaleimide, N,N'-4,4'
-dicyclohexylmethane bismaleimito, N, N'
-m-xylene bismaleimide, N,N'-diphenylcyclohexane bismaleimide, 4,4'-bismaleimideminnamanilide, 6,6'bismaleimide-2
, 2'-bipyridine, or.

and so on.

In the epoxy resin composition of the present invention, N.

When blending the N'-substituted unsaturated bisimide compound, various additives having polymerizable reactive groups can be used in combination. For example, styrene, vinyltoluene, α-methylstyrene, vinylbenzene, diallylphthalate,
Diallyl phthalate prepolymer, chlorstyrene, dichlorostyrene, bromstyrene, dibromstyrene, diallylbenzene phosphonate, diallyl arylphosphylate, acrylic ester, methacrylic ester, triallyl cyanurate, triallyl cyanurate prepolymer and Tribromophenol allyl ether and the like are used. In addition, it is possible to add various modifications and modifiers, and furthermore, the unsaturated polyester resin is not limited to one type, but a mixture of two or more of them is also possible.
It is possible.

It is represented by general formula [I] in the present invention.

The blending ratio of the imide compound and the unsaturated polyester resin is not particularly limited, but in order to impart heat resistance, the former
It is appropriate that the latter be in the range of 10 to 100 parts by weight.

It is desirable to add a polymerization initiator to the resin composition of the present invention in order to complete its curing by heating for a short time. Such polymerization initiators include benzoyl peroxide, p-chlorobenzoyl peroxide, 2,4-dichlorobenzoyl peroxide, cabrylyl peroxide, lauroyl peroxide, acetyl peroxide, methyl ethyl ketone peroxide, cyclohexanone peroxide, bis (1-hydroxycyclohexyl peroxide), hydroxyhebutyl peroxide, tertiary butyl hydroperoxide, p-menthane hydroperoxide, tertiary butyl perbenzoate, tertiary butyl peracetate, tertiary butyl peroct Organic peroxides such as ester, tertiary butylperoxyisobutylene-1 to di-tertiary butylshiba phthalate are useful, and one or more of them can be used.

In the present invention, it is also possible to use known accelerators such as mercaptans, sulfides, β-diketones, metal chelates, and metal soaps in combination with the above-mentioned polymerization catalyst. In order to improve the storage stability of the resin composition at room temperature, for example, quinones such as p-benzoquinone, naphthoquinone, and phenanthraquinone, hydroquinone,
Known polymerization inhibitors such as phenols and nitro compounds and metal salts such as p-tert-butylcatechol and 2,5-di-tert-butylhydroquinone can be used if desired.

Furthermore, various materials may be added to the resin composition of the present invention depending on its use. That is, for example, for use as a molding material, zircon oxide, silica, alumina, aluminum hydroxide, titania, subsalt flower, calcium carbonate,
Templates such as magnesite, clay kaolin, talc, silica sand, glass, fused silica glass, asbestos, mica, various whiskers, inorganic fillers such as carbon black, graphite and molybdenum disulfide, higher fatty acids and waxes, etc. Coupling agents such as agents, epoxysilanes, vinylsilanes, borane, alkoxytitanate compounds, etc. are blended. Further, flame retardant imparting agents such as halogen-containing compounds, antimony oxide, and phosphorus compounds can be used as necessary.

Also, various polymers, such as polystyrene, polyethylene, polybutadiene, polymethyl methacrylate, polyacrylic ester, acrylic ester-methacrylic ester copolymer, phenol resin, siloxane resin, and melamine resin.

Alternatively, known resin modifiers such as urea resins can be used.

It can also be used as a solution, such as a varnish. The solvents used in this case are N-methyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide, N,N-diethylformamide, N-
Methylformamide, dimethylsulfoxide, N, N
-diethylacetamide, N,N-dimethylmethoxyacetamide, hexamethylphosphoramide, pyridine, dimethylsulfone, tetramethylsulfone, and dimethylteheramethylenesulfone, and the phenolic solvent group includes phenol, Examples include cresol and xylenol.

The above substances may be used alone or in combination of two or more.

The composition of the present invention can be applied to heat, ultraviolet rays, visible light, 'W
The cross-linking reaction progresses due to actinic rays such as single rays and X-rays,
It becomes a hardened molded product.

That is, when the purpose is to enhance the polymerization effect by actinic rays, conventionally known sensitizers and photopolymerization initiators can be added to the composition of the present invention.

The sensitizer and photoinitiator are Michler's ketone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, 2-ter
t-Butylanthraquinone, 1゜2-benzo-9,10
-Anthraquinone, 4゜4'-bis(diethylamino)
Benzophenone, acetophenone, benzophenone, thioxanthone, 1,5-acenaphthene, N-acetyl-
Examples include 4-nitro-1-naphthylamine.

The amount added is preferably 0.1 to 10 parts by weight based on 100 parts by weight of the polyfunctional epoxy compound of the composition of the present invention.

It is desirable to apply the solution containing the compound represented by the general formula (1) and/or the general formula [11] of the present invention to the surface of a semiconductor element, etc., and examples of the solvent include benzene, toluene, xylene, etc. In addition to aromatic hydrocarbons, alcohols such as methanol, ethanol, and 2-puquipanol, ketones such as methyl ethyl ketone and acetone, cellosolve acetates such as ethyl cellosolve, chlorinated hydrocarbons, or dimethylacetamide, dimethylformamide, N -methyl-2-
Examples include polar solvents such as pyrrolidone.

Solutions of these compounds are applied to the surfaces of semiconductor elements, lead wires, and the like. The coating is carried out by dipping the element and lead wires into the solution, dropping the solution onto the element and lead wires, spraying, spinner coating, or the like.

By such a method, the semiconductor elements and lead wires coated with the compound solution are then heat-baked at a temperature of at least 100°C or higher, particularly preferably 120 to 250°C. Through this treatment, the compound has a higher molecular weight and is crosslinked to form a protective coating layer. The thickness of the coating layer is not particularly limited. Depending on the purpose and use, chinus with excellent effects are used as appropriate.

For example, the interlayer insulating film (Figure 2) of a multilayer wiring type LSI is
A film thickness of 500 to several μm, and a film thickness of 10 to 200 μm for the δ-ray shielding film (FIG. 1), are effective in achieving the desired effect.

The epoxy resin composition of the present invention has excellent heat resistance, low water absorption and moisture permeability, and good adhesion to metals, so it is useful as a sealant for semiconductor devices, and is useful for devices and devices. Used to cover and seal lead wires.

When the composition of the present invention is used to seal a semiconductor device, the method is not particularly limited, and known methods such as casting and transfer molding can be applied.

Furthermore, since the epoxy resin composition of the present invention has excellent heat resistance and moisture resistance, it is also useful as a material for laminated boards.

The epoxy resin composition of the present invention is also effective in imparting transparency and is useful as a material for optical fibers and optical discs.

<Examples 1 to 8> Five types of fluorine-containing dicarboxylic acid anhydride compounds were selected. In addition to these, bisphenol A type epoxy DER332 (manufactured by Dow Chemical Company), orthodiallyl bisphenol F, 2゜2-bis(4-(4-maleimidophenoxy)phenyl)hexafluoropropane (
DAPP-FMI) and triallylisocyanurate (TAIC) were separately blended in predetermined amounts (parts by weight) shown in Table 1 to prepare the following formulations. These formulations each contain, as a curing accelerator,
Dicyandiamide, benzoguanamine, and dicumyl peroxide (OCPO) were added in predetermined amounts as well as epoxysilane KBM403 (manufactured by Shin-Etsu Chemical Co., Ltd.) as a coupling agent.

These formulations were then dissolved in an isostatic mixture of N-methyl-2-pyrrolidone (NMP) and methyl ethyl ketone (MEK) to form a varnish containing 45-48% solids by weight.

Using this varnish solution, apply a glass cloth (WE-made by Nittobo Co., Ltd.)
116P BY-54), resin impregnated and coated, 160
'C1 It was dried for 15 minutes to prepare a coated cloth having a resin content of 45 to 48% by weight.

Next, apply a sheet to the coated cloth, and apply a 35 μm thick T layer above and below it.
Layer AI-treated copper foil (manufactured by Furukawa Denki CFC) and
Lamination and adhesion were carried out for 80 minutes under conditions of ~185° C. and 40 kg-f/cJ to create a double-sided copper-clad laminate having a thickness of about 1.6 nl11.

This copper-clad laminate was further post-cured at 200° C. for 4 hours. Table 1 shows the properties of the obtained copper-clad laminate material.

In addition, the constant force method for each characteristic is as follows.

(a) Copper foil peel strength After cutting a test piece into a size of 25+nm x 100 mm from a copper-clad laminate, a copper foil with a width of 10 nyn was left in the center, and the other copper foils were removed by etching. Next, the copper foil in the center was peeled off in the vertical direction at a speed of 5+a/min, and its strength was measured.

(b) A test piece was cut into a 25ffn square from a solder heat-resistant copper-clad laminate. This test piece was floated in a solder bath heated to 300'C, and the time required for abnormalities such as blistering to occur was measured.

(c) Anti-inflammatory properties were measured according to the UL-94 vertical method. A test piece was cut from the above copper-clad laminate to a width of 12 nm and a length of 125 mm, and a copper foil was etched thereon.

Each test piece was measured in detail and expressed as an average extinguishing time.

In addition, an average flame-out time of 5 seconds or less and a maximum flame-out time of 10 seconds or less is UL-94, V-0, and an average flame-out time of 25 seconds or less and a maximum flame-out time of 30 seconds or less is UL-94, V-1.

<Example 9> Two types of fluorine-containing dicarboxylic acid anhydride compounds were selected. In addition, O-cresol novolak type epoxy ○CEN-102 (epoxy manufactured by Nippon Kayaku Co., Ltd.)
i195), novolac type phenolic resin HP607N
(Manufactured by Hitachi Chemical), Tetrahydrophthalic anhydride T
HP A, as a catalyst, triethylamine tetraphenylborate TEA-K (manufactured by Hokko Chemical Co., Ltd.), 2.2-bis[4-(4-maleimidophenoxy)phenyl]hexafluoropropane (BAPPF-MI), a filler,
Predetermined amounts of spherical quartz glass powder having an average particle diameter of 10 to 16 μm as shown in Table 2 were blended. Each of these formulations separately contained 2 parts by weight of epoxysilane KBH403 (manufactured by Shin-Etsu Chemical Co., Ltd.) as a coupling agent, and 3 parts by weight of Hoechst wax E (manufactured by Hoechst Japan Co., Ltd.) as a mold release agent.
．． 0 parts by weight, polyimide coated red phosphorus 4 as a flame retardant material
Parts by weight, and 2.0 parts by weight of carbon black (manufactured by Cabot) as a coloring agent were added.

The mixture was heated and kneaded for 8 minutes at 75 to 85° C. with two rolls of 8 inch diameter, cooled, and coarsely ground to obtain a molding material for semiconductor encapsulation.

Next, using a molding material for semiconductor encapsulation, IM bit D
-RAMLSI, 180℃, 70kg-f/cd1
．． Transfer molding was performed for 5 minutes to obtain resin-sealed memory LSIs (DIL-P type LSIs) on each side.

The above DIL-p type LSI was left in a supersaturated steam oven (PCT oven) at 121° C. and 2 atm for a predetermined period of time, and then taken out and checked to see if the wiring on the element was disconnected due to corrosion.

In addition, the DIL-p type LSI was heated at -196℃ for 3 minutes and 2 hours.
A thermal cycle test was conducted in which one cycle was immersion in 00'C silicone oil for 3 minutes.

The presence or absence of cracks in the appearance of the molded product was checked under the load of the cooling and heating cycles, and the presence or absence of abnormality in electrical operation was checked.

〔Effect of the invention〕

A molded article obtained by curing the epoxy resin composition of the present invention has excellent heat resistance, cold/heat cycle resistance, and adhesiveness. Furthermore, the effects of lower dielectric constant and lower water absorption are remarkable.

[Brief explanation of the drawing]

FIG. 1 is a cross-sectional view of a semiconductor device according to an embodiment of the present invention, and FIGS. 2 and 3 are partial cross-sectional views of an element portion of a semiconductor device according to the present invention.

Claims (1)

[Claims] 1. At least a polyfunctional epoxy compound and the following formula [I
] and/or the following formula [II] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [ I ] or/and [II] [In the above formula, R_f' and R_f'' are ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ CF_2-O-)_mCF-CO-
(m is 1 to 30.), ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (R_1, R_2, R_3 are CF_3, C_2
It is either F_5, C_3F_7, or C_4F_9. They may be the same or different. ) ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and they can be the same or different. ] An epoxy resin composition characterized by containing a fluorine-containing dicarboxylic acid anhydride compound represented by the following. 2. A semiconductor encapsulation material using the epoxy resin composition according to claim 1. 3. A laminate material using the epoxy resin composition according to claim 1. 4. An optical disc material using the epoxy resin composition according to claim 1. 5. The polyfunctional epoxy compound according to claim 1, wherein the polyfunctional epoxy compound is a tetrafunctional epoxy compound represented by the following formula [III] ▼ Numerical formula, chemical formula, table, etc. ▼ [III] Epoxy resin composition. 6. In claim 1, furthermore, N, N'
- An epoxy resin composition comprising a substituted unsaturated bisimide compound.