JP2002275357A - Epoxy-based resin composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an epoxy resin composition which has an ability to withstand the solder reflow at a high temperature. SOLUTION: The epoxy-based resin composition, comprising an epoxy resin (A), a curing agent (B), a filler (C) and a curing accelerator (D), is characterized in that the above epoxy resin (A) contains an epoxy resin expressed by chemical formula (I), and the filler has a content ratio to the whole epoxy-based resin composition of 86-96 wt.% and also the composition contains a polyimide compound (E).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an epoxy resin composition which is excellent in moldability and reliability and is particularly suitable for semiconductor encapsulation.

[0002]

2. Description of the Related Art Epoxy resins are excellent in heat resistance, moisture resistance, electrical properties, adhesiveness, etc., and can be added with various properties by blending and prescription, so that they are used as industrial materials such as paints, adhesives, and electrical insulating materials. Have been.

For example, as a method of sealing an electronic circuit component such as a semiconductor device, a hermetic seal made of metal or ceramic and a resin seal made of phenol resin, silicone resin, epoxy resin or the like have been conventionally proposed. The resin used for such sealing is called a sealing resin. Among them, resin sealing with an epoxy resin is most actively performed in terms of balance between economy, productivity and physical properties. The sealing method using an epoxy resin is generally performed by using a composition in which a curing agent, a filler, and the like are added to an epoxy resin, setting the semiconductor element in a mold, and sealing by a transfer molding method or the like. Have been done.

The properties required of the epoxy resin composition for semiconductor encapsulation include reliability such as solder heat resistance, high temperature reliability, heat resistance and moisture resistance, and moldability such as fluidity and heat resistance. Hardness, burr, etc. are mentioned.

In order to improve the moisture resistance of the sealing resin, it is necessary to reduce impurities contained in components such as an epoxy resin and a curing agent, and to improve the moisture resistance by purifying the sealing resin. No. 57-212224) has been proposed.

Recently, the density and automation of mounting a semiconductor device package on a printed circuit board have been advanced, and the semiconductor device package has been mounted on the surface of the board instead of the conventional "insertion mounting method" in which lead pins are inserted into holes in the board. "Surface mounting method" for soldering has become popular. Along with this, the semiconductor device package has been changed from the conventional DIP (dual in-line package) to a thin FPP (flat plastic package) suitable for high-density mounting and surface mounting.
Package). Among them, recently,
With the advance of fine processing technology, TSO with a thickness of 2mm or less
P, TQFP and LQFP are becoming mainstream. Therefore, it becomes more susceptible to external influences such as humidity and temperature, and reliability such as solder heat resistance, high temperature reliability, and heat resistance becomes more and more important in the future.

In surface mounting, mounting is usually performed by solder reflow. In this method, a semiconductor device package is placed on a substrate, and the semiconductor device package is exposed to a high temperature of 200 ° C. or more, and the solder previously applied to the substrate is melted to adhere the semiconductor device package to the substrate surface. In such a mounting method, since the entire semiconductor device package is exposed to a high temperature, if the sealing resin composition has high water absorption, a phenomenon occurs that the absorbed water explosively expands at the time of solder reflow, and a crack occurs. Therefore, reliability such as solder heat resistance, high-temperature reliability, and heat resistance is very important in the sealing resin composition for semiconductors.

Further, in recent years, lead-free solder containing no lead has been used from the viewpoint of environmental protection. Lead-free solders have a high melting point, which increases the reflow temperature, so that higher solder heat resistance and moisture resistance are required.

In general, it is known that it is effective to increase the ratio of the filler in the sealing resin to improve the solder heat resistance. This is because the moisture resistance is improved and the water absorption is reduced by reducing the resin component in the sealing resin.
However, when the proportion of the filler in the sealing resin increases,
There is a problem that adhesion to members in the package is deteriorated, and there is a problem that separation occurs between members such as a sealing material and a lead frame during reflow.

[0010]

SUMMARY OF THE INVENTION An object of the present invention is to solve the above-mentioned problems of the epoxy resin composition and to provide a resin composition which has improved adhesion to members in a package and excellent reflow resistance. By doing so, a resin-sealed semiconductor corresponding to a higher reflow temperature can be realized.

[0011]

Means for Solving the Problems The present inventors have achieved the above object by including a polyimide compound in an epoxy resin composition, and have obtained an epoxy resin composition meeting the purpose. And arrived at the present invention.

That is, the present invention mainly has the following configuration. That is, in the epoxy resin composition comprising the epoxy resin (A), the curing agent (B), the filler (C), and the curing accelerator (D), the epoxy resin (A)
It contains an epoxy resin represented by the following chemical formula (I), and the proportion of the filler (C) is from 86 to 9 of the entire epoxy resin composition.
An epoxy resin composition, which is 6% by weight and contains a polyimide compound (E).

[0013]

Embedded image (In the formula (I), R _{1 to} R ₈ represent a hydrogen atom, an alkyl group, or a halogen atom, and may be the same or different.)

[0014]

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The configuration of the present invention will be described below in detail.

It is essential that the epoxy resin (A) in the present invention contains a compound represented by the chemical formula (I).

[0016]

Embedded image However, in the chemical formula (I), R _{1 to} R ₈ represent a hydrogen atom, an alkyl group or a halogen atom, and may be the same or different. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, and a butyl group. Examples of the halogen atom include bromine and chlorine. Specific examples of the compound include bisphenol F epoxy resin, tetramethyl bisphenol F epoxy resin, and tetraethyl bisphenol F epoxy resin.

The content of the compound represented by the chemical formula (I) in the epoxy resin (A) is not particularly limited, but is preferably 25 to 100%, more preferably 50 to 100%. If it is less than 25%, sufficient solder heat resistance may not be obtained. Other epoxy resins can be used in combination with these epoxy resins. Examples of other epoxy resins include biphenyl epoxy resin, phenol aralkyl type epoxy resin, 1,5-di (2,3-epoxypropoxy) naphthalene, 1,6-di (2,3-epoxypropoxy) naphthalene, naphthol Naphthalene-type epoxy resins such as aralkyl-type epoxy resins, 3-t-butyl-2,4'-dihydroxy-3 ', 5', 6-glycidyl ether of 6-trimethylstilbene, 3-t-butyl-4,4'- Diglycidyl ether of dihydroxy-3 ', 5,5'-trimethylstilbene, diglycidyl ether of 4,4'-dihydroxy-3,3', 5,5'-tetramethylstilbene, 4,4'-dihydroxy-3 Stilbene-type epoxies such as diglycidyl ether of 3,3'-di-t-butyl-6,6'-dimethylstilbene Resin, epoxy resin having a dicyclopentadiene skeleton, triphenylmethane type epoxy resin, diglycidyl ether of 1,4-bis (3-methyl-4-hydroxycumyl) benzene, diglycidyl ether of 4,4′-dihydroxydiphenyl ether 2 , 2-dimethyl-5,
Bisphenol type epoxy resins such as 5'-di-tert-butyl-4,4'-dihydroxydiphenyl sulfide, bisphenol A type epoxy resins, chain aliphatic epoxy resins, alicyclic epoxy resins, heterocyclic epoxy resins, Examples include spiro ring-containing epoxy resins and halogenated epoxy resins.

In the present invention, the blending amount of the epoxy resin (A) is not particularly limited, but is usually 1.5 to 6.0% by weight based on the whole resin composition.

The curing agent (B) in the present invention is not particularly limited, but contains a curing agent represented by the chemical formulas (II) and (III) so that the adhesion to a member constituting a semiconductor device can be improved. It is preferred in that respect.

[0020]

Embedded image (In the formula (II), n is 0 or an integer of 1 or more.)

[0021]

Embedded image (In the formula (III), n is 0 or an integer of 1 or more.)

Other curing agents can be used. Specific examples thereof include novolak resins such as phenol novolak and cresol novolak, tris (hydroxyphenyl) methane, 1,1,2-tris (hydroxyphenyl). ) Ethane, 1,1,3-tris (hydroxyphenyl) propane, condensation compound of terpene and phenol, phenol resin having dicyclopentadiene skeleton, bisphenol compound such as bisphenol A, maleic anhydride, phthalic anhydride, pyromellitic anhydride Acid anhydrides and aromatic amines such as metaphenylenediamine, diaminodiphenylmethane and diaminodiphenylsulfone. Two or more curing agents can be used in combination.

In the present invention, the amount of the curing agent (B) is not particularly limited, but it is usually 1.5 to the total resin composition.
~ 6.0% by weight. Furthermore, epoxy resin (A)
The mixing ratio of (B) to the curing agent (B) is such that the chemical equivalent ratio of (B) to (A) is 0.5 to 0.5 in view of mechanical properties and moisture resistance.
It is preferably in the range of 1.3, especially 0.6 to 1.1.

In the present invention, a curing accelerator (D) is used to accelerate the curing reaction between the epoxy resin (A) and the curing agent (B). The curing accelerator (D) is not particularly limited as long as it accelerates the curing reaction. Examples thereof include 2-methylimidazole, 2,4-dimethylimidazole,
Ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2-
Imidazole compounds such as heptadecyl imidazole,
Triethylamine, benzyldimethylamine, α-methylbenzylmethylamine, 2- (dimethylaminomethyl) phenol, 2,4,6-tris (dimethylaminomethyl) phenol, 1,8-diazabicyclo (5,
Tertiary amine compounds such as (4,0) undecene-7 and salts thereof; organometallic compounds such as zirconium tetramethoxide, zirconium tetrapropoxide, tetrakis (acetylacetonato) zirconium, and tri (acetylacetonato) aluminum; Organic phosphine compounds such as phenylphosphine, trimethylphosphine, triethylphosphine, tributylphosphine, tri (p-methylphenyl) phosphine, tri (nonylphenyl) phosphine, and salts thereof. Preferably, a curing accelerator represented by the chemical formula (IV) is preferable from the viewpoint of improving adhesion to a member constituting the semiconductor device.

[0025]

Embedded image However, in the formula (IV), R _{9 to} R ₁₈ represent a hydrogen atom or a monovalent organic group, and may be the same or different. 1
Specific examples of the valent organic group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, an alkyl group such as a hexyl group, a vinyl group, an allyl group, a propenyl group,
Examples thereof include alkenyl groups such as a butenyl group, and aralkyls such as a phenyl group, a tolyl group, and a naphthyl group.

These curing accelerators (D) may be used in combination of two or more depending on the use. The amount of the curing accelerator (D) is 0.1 to 10 parts by weight per 100 parts by weight of the epoxy resin (A). Is desirable.

As the filler (C) in the present invention, an inorganic filler is preferable. Specifically, fused silica, crystalline silica, calcium carbonate, magnesium carbonate, alumina, magnesia, clay, talc, calcium silicate,
And titanium oxide. Among these, it is preferable to use silica. The particle size is not particularly limited, but it is preferable to use a filler having an average particle size of 3 to 40 μm from the viewpoint of fluidity and moldability. More preferably, the average particle size is 5 to 25 μm. Here, the average particle size refers to a median size obtained by a particle size distribution measurement. When two or more fillers having different average particle diameters are used, the average particle diameter after mixing is indicated. As for the shape of the filler, it is desirable to use a spherical filler from the viewpoint of fluidity. Depending on the application,
It is also possible to add a crushed one.

In the present invention, the proportion of the filler (C) needs to be 86 to 96% by weight based on the whole resin composition. Here, the ratio of the filler (C) is the ratio of the residual weight after burning the resin composition in air at 600 ° C. for 24 hours based on the total weight of the resin composition. Here, the state of the resin composition is the powder and tablet before molding and curing,
Any of the cured moldings.

If the content of the filler (C) is less than 86% by weight, the water absorption of the sealing resin tends to increase, and good solder heat resistance cannot be obtained. On the other hand, if it exceeds 96% by weight, the adhesiveness and the package filling property are reduced. More preferably, the proportion of the filler (C) is 89 to 96% by weight.

The epoxy resin composition of the present invention contains a coloring agent such as carbon black and iron oxide, silicone rubber,
Styrene block copolymers, olefin polymers, modified nitrile rubber, modified polybutadiene rubber and other elastomers, thermoplastic resins such as polystyrene, coupling agents such as titanate coupling agents, long chain fatty acids, metal salts of long chain fatty acids A releasing agent such as an ester of a long-chain fatty acid, an amide of a long-chain fatty acid, or paraffin wax, and a crosslinking agent such as an organic peroxide can be optionally added.

The structure of the polyimide compound (E) in the present invention is not particularly limited, and any compound having an imide structure can be used. Among them, an aromatic polyimide having an aromatic group in the skeleton is preferable from the viewpoint of heat resistance. Further, among them, a polyimide compound having a biphenyl skeleton is preferable. In addition, it is preferable to use a polyimide compound containing a carbonyl group in addition to an ether group or an imide group from the viewpoint that flexibility can be given to the skeleton.

Specific examples of the polyimide compound (E) in the present invention include pyromellitic dianhydride and 4,4 ′
-Diaminodiphenyl ether, 3,3 ', 4,4'-
Benzophenonetetracarboxylic dianhydride and 4,4'-
Diaminodiphenyl ether, 3,3 ', 4,4'-biphenyltetracarboxylic dianhydride and 4,4'-diaminodiphenyl ether, pyromellitic dianhydride and 3,
3 '(or 4,4')-diaminodiphenyl sulfone, pyromellitic dianhydride and 3,3 ', 4,4'
-Benzophenonetetracarboxylic dianhydride and 3,3 '
(Or 4,4 ′)-diaminodiphenyl sulfone,
3,3 ', 4,4'-benzophenonetetracarboxylic dianhydride and 3,3' (or 4,4 ')-diaminodiphenyl sulfone, 3,3', 4,4'-biphenyltetracarboxylic dianhydride Object and 3,3 '(or 4,4')-
Diaminodiphenyl sulfone, pyromellitic dianhydride and 4,4'-diaminodiphenyl sulfide, 3,3
', 4,4'-benzophenonetetracarboxylic dianhydride and 4,4'-diaminodiphenyl sulfide, 3,3
', 4,4'-biphenyltetracarboxylic dianhydride and 4,4'-diaminodiphenyl sulfide, 3,3',
4,4'-benzophenonetetracarboxylic dianhydride and paraphenylenediamine, 3,3 ', 4,4'-biphenyltetracarboxylic dianhydride and paraphenylenediamine, pyromellitic dianhydride and 3,3' , 4,4 '
-Benzophenonetetracarboxylic dianhydride and paraphenylenediamine, pyromellitic dianhydride and 3,3
', 4,4'-biphenyltetracarboxylic dianhydride and paraphenylenediamine, 3,3', 4,4'-diphenylethertetracarboxylic dianhydride and 4,4'-diaminodiphenyl ether, 3,3 ', 4,4'-diphenylethertetracarboxylic dianhydride and paraphenylenediamine, butanetetracarboxylic dianhydride and 1,
3-bis (3-aminophenoxy) benzene, cyclopentanetetracarboxylic dianhydride and 4,4'-diaminodiphenylmethane, pyromellitic dianhydride and 4,4 '
And polyimide obtained by dehydrating polyamic acid synthesized from diaminodiphenyl ether and bis (3-aminopropyl) tetramethyldisiloxane.

The content of the polyimide compound is not particularly limited, but is preferably 0.05 to 6%, more preferably
0.1 to 3%. If it is less than 0.05%, sufficient solder heat resistance may not be obtained, and if it exceeds 6%, it is not preferable in terms of strength reduction.

The method for producing the polyimide compound (E) in the present invention is not particularly limited, but an example of a method for producing the polyimide compound will be described below. First, a diamine compound and an acid dianhydride are reacted in a solvent to obtain a polyamic acid solution. The solution is then poured into water or alcohol to precipitate the polyamic acid. After the polyamic acid is taken out by filtration and dried with a drier, the polyamic acid is pulverized into powder or small pieces. The obtained powdery or small piece polyamic acid is heat-treated in an oven at 350 to 400 ° C. for 4 to 6 hours to obtain a powdery or small piece polyimide compound. As the solvent used in the above production method, a polar solvent is preferably used in view of the solubility of the polymer, and an aprotic polar solvent is particularly preferable. Examples of aprotic polar solvents include N-methyl-2-pyrrolidone, N, N-dimethylformamide,
N, N-dimethylacetamide, dimethylsulfoxide, hexamethylphosphorotriamide, γ-butyrolactone and the like are preferably used.

The form of the polyimide compound used in the present invention is not particularly limited, and any form such as a powder, a film, and a small piece can be used. Among them, a powdery form is preferred for inclusion in the epoxy resin composition.

The chlorine ion content of the polyimide compound in the present invention is not particularly limited, but is preferably less than 10 ppm from the viewpoint of reliability, more preferably 5 ppm.
pm or less.

The epoxy resin composition of the present invention is preferably produced by mixing each raw material with a mixer or the like and then melt-kneading. For example, it is manufactured by melt-kneading using a known kneading method such as a Banbury mixer, a kneader, a roll, a single-screw or twin-screw extruder and a co-kneader. Thereafter, the mixture is cooled and pulverized to obtain a powdery resin composition. However, it is also preferable to form these powders into tablets and pellets for easy molding. After melt-kneading, it can be directly made into tablets.

In the present invention, the term "semiconductor device" refers to an electronic circuit (integrated circuit) formed by integrating and wiring transistors, diodes, resistors, capacitors, and the like on a semiconductor chip or substrate. Refers to an electronic component sealed with an epoxy resin composition. Then, a semiconductor device can be obtained by sealing a semiconductor element formed of a semiconductor chip using the epoxy resin composition of the present invention.

As a method of manufacturing a semiconductor device, for example,
With the semiconductor element fixed to the lead frame, the epoxy resin composition of the present invention is molded at a temperature of, for example, 120 to 250 ° C., preferably 150 to 200 ° C. by a method such as transfer molding, injection molding, or casting. Thereby, a semiconductor device sealed with a cured product of the epoxy resin composition is manufactured. If necessary, additional heat treatment (post-curing: for example, 150 to 200 ° C., 2 to 16
Time) can be done.

[0040]

The present invention will be described below in detail with reference to examples.

Examples 1 to 16 and Comparative Examples 1 to 13 Raw materials used in the present invention are shown below. In addition, the compounding quantity was shown by the weight ratio in the table | surface (Table 2-Table 4) of an Example and a comparative example. <Epoxy resin I> 150 represented by the following chemical formula (V)
Epoxy resin with an ICI viscosity of 0.07 Ps at ° C.

Embedded image

<Epoxy resin II> An epoxy resin represented by the following chemical formula (VI) and having an ICI viscosity at 150 ° C. of 0.09 Ps.

Embedded image

<Epoxy resin III> I at 150 ° C.
Cresol novolak epoxy with an epoxy equivalent of 199 with a CI viscosity of 2.0 Ps. <Curing agent I> hydroxyl equivalent 2 represented by the following chemical formula (II)
03, a phenol aralkyl resin having a biphenyl skeleton having an ICI viscosity of 0.8 Ps at 150 ° C.

Embedded image (However, n is an integer of 0 or more)

<Curing Agent II> Hydroxyl equivalent represented by the following chemical formula (III): 175, ICI viscosity at 150 ° C.
An 8Ps phenyl skeleton-containing phenol aralkyl resin.

Embedded image (However, n is an integer of 0 or more)

<Curing Agent III> A phenol novolak resin having an ICI viscosity of 2.2 Ps at 150 ° C. and a hydroxyl equivalent of 107. <Inorganic filler> Amorphous spherical fused silica having an average particle size of about 23 μm. <Silane coupling agent> N-phenylaminopropyltrimethoxysilane. <Curing accelerator I> Triphenylphosphine. <Curing accelerator II> Tetraphenylphosphonium tetraphenylborate. <Colorant> Carbon black. <Release agent> Carnauba wax. <Polyimide compound I> See Table 1. <Polyimide compound II> See Table 1.

[0046]

【table 1】

Each component is represented by the composition ratio shown in Tables 2 to 4,
Dry blending was performed with a mixer. However, the form of the polyimide compound I and the polyimide compound II to be added is a powder. When the polyimide compound is added, 0.1% is added to the total weight of the resin composition. This was heated and kneaded for 6 minutes using a mixing roll having a roll surface temperature of 92 ° C., and then cooled and pulverized to produce an epoxy resin composition for semiconductor encapsulation.

Using this resin composition, a simulated element having a surface treated with a nitride film was mounted by low-pressure transfer molding under the conditions of 180 ° C. and a cure time of 150 seconds.
176pinLQFP with chip size 10 × 10mm
(Outer dimensions: 23 x 23 x 1.4 mm, frame material: copper)
Was molded and post-cured at 175 ° C. for 8 hours, and the physical properties of each resin composition were evaluated by the following physical property measuring methods.

Solder heat resistance: 176 pin LQFP is 20
After individual molding and humidification at 85 ° C./70% RH for 200 hours, heat treatment was performed for 15 seconds in an IR reflow furnace at a maximum temperature of 245 ° C., and the number of packages having external cracks was determined. High temperature solder heat resistance: The same test as the above solder heat resistance, but the maximum temperature of the IR reflow furnace was 275 ° C.

Adhesion: 20 pieces of 176 pin LQFP were molded, humidified at 85 ° C./70% RH for 200 hours, heat-treated in an IR reflow furnace at a maximum temperature of 275 ° C. for 15 seconds, and then peeled off the silver plating portion of the lead frame. With an ultrasonic flaw detector (“mi-scope1” manufactured by Hitachi Construction Machinery Co., Ltd.)
0 "), and the number of packages where peeling occurred was examined. In addition, about Examples 1-16 and Comparative Examples 1-17,
The proportion of the filler in the present invention, that is, the proportion of the residual weight after burning the resin composition in air at 600 ° C. for 24 hours with respect to the weight of the resin composition was measured. The composition ratio was consistent with the composition ratio of the inorganic filler shown in FIG.

Tables 2 to 4 show the evaluation results. As seen from the examples, the epoxy resin composition of the present invention is excellent in solder heat resistance, high-temperature solder heat resistance, and adhesion.

[0052]

[Table 2]

[0053]

[Table 3]

[0054]

[Table 4]

On the other hand, in the comparative example, high-temperature solder heat resistance,
It can be seen that the adhesion is inferior. Thus, it can be seen that sufficient performance is exhibited only when the polyimide compound is blended and the proportion of the filler is satisfied.

[0056]

According to the present invention, the proportion of the filler is 86 to 96% by weight of the whole epoxy resin composition, and by containing the polyimide compound, an epoxy resin composition having high high-temperature solder heat resistance can be obtained.

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Claims (9)

[Claims] 1. An epoxy resin composition comprising an epoxy resin (A), a curing agent (B), a filler (C), and a curing accelerator (D), wherein the epoxy resin (A) has the following chemical formula:
An epoxy resin containing the epoxy resin represented by (I), wherein the proportion of the filler (C) is 86 to 96% by weight of the whole epoxy resin composition, and which contains the polyimide compound (E). Resin composition. Embedded image (In the formula (I), R _{1 to} R ₈ represent a hydrogen atom, an alkyl group, or a halogen atom, and may be the same or different.) 2. The epoxy resin composition according to claim 1, wherein the polyimide compound (E) contains an aromatic polyimide compound. 3. The epoxy resin composition according to claim 1, wherein the polyimide compound (E) contains a polyimide compound having an ether group. 4. The epoxy resin composition according to claim 1, wherein the polyimide compound (E) contains a polyimide compound having a carbonyl group in addition to the imide group. 5. The epoxy resin composition according to claim 1, wherein the polyimide compound (E) contains a polyimide compound having a biphenyl group. 6. The epoxy resin composition according to claim 1, wherein the curing agent (B) contains a curing agent represented by the following chemical formula (II) or (III). 2] (In the formula (II), n is 0 or an integer of 1 or more.) (In the formula (III), n is 0 or an integer of 1 or more.) 7. The epoxy resin composition according to claim 1, wherein the proportion of the filler (C) is 89 to 96% by weight of the whole epoxy resin composition. 8. The epoxy resin composition according to claim 1, wherein the curing accelerator (D) contains a curing accelerator represented by the formula (IV). Embedded image (In the formula (IV), R _{9 to} R ₁₈ represent a hydrogen atom or a monovalent organic group, and may be the same or different.) 9. A semiconductor device sealed with the epoxy resin composition according to claim 1.