KR20170013644A - Epoxy Resin Composition for Sealing Semiconductor - Google Patents
Epoxy Resin Composition for Sealing Semiconductor Download PDFInfo
- Publication number
- KR20170013644A KR20170013644A KR1020150106584A KR20150106584A KR20170013644A KR 20170013644 A KR20170013644 A KR 20170013644A KR 1020150106584 A KR1020150106584 A KR 1020150106584A KR 20150106584 A KR20150106584 A KR 20150106584A KR 20170013644 A KR20170013644 A KR 20170013644A
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- South Korea
- Prior art keywords
- epoxy resin
- resin composition
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- composition according
- carbon atoms
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Classifications
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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
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- 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
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- C08K3/0033—
-
- 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
-
- 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
-
- 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
- C08G2190/00—Compositions for sealing or packing joints
Abstract
Description
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an epoxy resin composition for semiconductor encapsulation, and more particularly, to an epoxy resin composition for semiconductor encapsulation capable of minimizing warpage in a ball grid array (BGA) package.
BACKGROUND ART Semiconductor encapsulant has a great effect on productivity and reliability of semiconductors as a material that functions to encapsulate semiconductor devices to protect semiconductor circuits from external impacts and contaminants. At present, as a semiconductor encapsulation method, a transfer molding method using an epoxy molding compound (EMC) is mainly used.
In the case of a ball grid array (BGA) package in which a semiconductor package, in particular a semiconductor element, is connected to a substrate by a metal wire, only the one surface of the substrate, that is, one side of the substrate is molded and sealed with the resin composition for sealing. In this case, warpage is likely to occur in the semiconductor package due to mismatch of thermal expansion and heat shrinkage between the substrate and the cured product of the resin composition, or curing shrinkage upon molding and curing of the resin composition.
Korean Patent Publication No. 10-2012-0103896 discloses an epoxy resin composition comprising an epoxy resin, a curing agent, a curing accelerator, and a filler, wherein the epoxy resin contains a sulfur-biphenyl epoxy resin, And to maintain the package bending characteristics and wire warpage to an appropriate level.
However, there is a continuing demand for development of an epoxy resin composition capable of more effectively improving bending properties in a semiconductor package such as a BGA.
The present invention provides an epoxy resin composition for semiconductor encapsulation that minimizes bending phenomenon of a package and imparts excellent moldability.
The present invention also provides a semiconductor device encapsulated using the epoxy resin composition for semiconductor encapsulation.
On the other hand, the present invention provides an epoxy resin composition for semiconductor encapsulation, which comprises an epoxy resin, a curing agent, a curing accelerator and a filler, wherein the epoxy resin comprises a modified naphthalene epoxy resin.
In one embodiment of the present invention, the modified naphthalene epoxy resin may be a compound represented by the following formula (1).
[Chemical Formula 1]
In this formula,
Each R < 1 > is independently hydrogen or a methyl group,
Ar 1 and Ar 2 are each independently a naphthylene group or a phenylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms or a phenyl group,
R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aralkyl group having the following formula (2)
R 3 each independently represents hydrogen, an aralkyl group of the following formula (2) or an epoxy group-containing aromatic hydrocarbon group of the following formula (3)
p and q are each independently an integer of 0 to 4, with the proviso that any of p and q is 1 or more;
(2)
In this formula,
R 4 and R 5 are each independently hydrogen or a methyl group,
Ar 3 is a phenylene group or a naphthylene group, and these groups may be substituted with an alkyl group having 1 to 4 carbon atoms,
r is an integer from 1 to 4;
(3)
In this formula,
R < 6 > is hydrogen or a methyl group,
Ar 4 is an alkyl group having 1 to 4 carbon atoms or a naphthylene group unsubstituted or substituted with a phenyl group,
s is an integer of 1 or 2;
In one embodiment of the present invention, the epoxy resin may further include a biphenyl type epoxy resin.
In one embodiment of the present invention, the curing agent may comprise a phenolic resin.
In one embodiment of the present invention, the filler may include molten or synthetic silica having an average degree of sphericity of 0.92 or more and an average particle diameter of 1 to 30 mu m.
On the other hand, the present invention provides a semiconductor device encapsulated using the epoxy resin composition for semiconductor encapsulation.
INDUSTRIAL APPLICABILITY The epoxy resin composition for semiconductor encapsulation of the present invention can overcome the package warpage phenomenon caused by the difference in coefficient of linear expansion between the epoxy resin composition, the substrate and the semiconductor chip, including the modified naphthalene epoxy resin. In addition, stable flowability can be ensured even when a large amount of filler is used, and reliability can be improved by improving mechanical strength and low moisture absorption.
Hereinafter, the present invention will be described in more detail.
An epoxy resin composition for semiconductor encapsulation according to an embodiment of the present invention comprises an epoxy resin, a curing agent, a curing accelerator and a filler, and the epoxy resin includes a modified naphthalene epoxy resin.
In one embodiment of the present invention, the modified naphthalene epoxy resin may be a compound represented by the following formula (1).
[Chemical Formula 1]
In this formula,
Each R < 1 > is independently hydrogen or a methyl group,
Ar 1 and Ar 2 are each independently a naphthylene group or a phenylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms or a phenyl group,
R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aralkyl group having the following formula (2)
R 3 each independently represents hydrogen, an aralkyl group of the following formula (2) or an epoxy group-containing aromatic hydrocarbon group of the following formula (3)
p and q are each independently an integer of 0 to 4, with the proviso that any of p and q is 1 or more;
(2)
In this formula,
R 4 and R 5 are each independently hydrogen or a methyl group,
Ar 3 is a phenylene group or a naphthylene group, and these groups may be substituted with an alkyl group having 1 to 4 carbon atoms,
r is an integer from 1 to 4;
(3)
In this formula,
R < 6 > is hydrogen or a methyl group,
Ar 4 is an alkyl group having 1 to 4 carbon atoms or a naphthylene group unsubstituted or substituted with a phenyl group,
s is an integer of 1 or 2;
In one embodiment of the present invention, the compound of Formula 1 is a compound wherein R 1 is each independently hydrogen or a methyl group, Ar 1 and Ar 2 are each independently a naphthylene group or a phenylene group, An alkyl group or a phenyl group, each of R 2 is independently hydrogen or an alkyl group having 1 to 4 carbon atoms, R 3 is hydrogen, and p and q are 1.
Commercially available examples of the modified naphthalene epoxy resin of Formula 1 include HP-6000, EXA-7310, EXA-7311, EXA-7311-L, EXA-7311-G3 and EXA- But is not limited thereto.
Such a modified naphthalene epoxy resin may be used in an amount of 10 to 70% by weight based on the total weight of the epoxy resin. When the content of the modified naphthalene epoxy resin is less than 10% by weight, the linear expansion coefficient of the epoxy resin composition may be increased to increase the tensile strength. When the content exceeds 70% by weight, the rigidity and hydrophobicity due to the naphthalene structure become strong, It can be disadvantageous in terms of sex.
The epoxy resin may also include a biphenyl type epoxy resin. Examples of the biphenyl type epoxy resin include 4,4'-dihydroxybiphenyl, 4,4'-bis (2,3-epoxypropoxy) -3,3 ', 5,5'-tetramethylbis Phenyl, 4,4'-dihydroxy-3,3'-ditertiarybutyl-6,6'-dimethylbiphenyl, 2,2'-dihydroxy-3,3'- '-Dimethylbiphenyl, 4,4'-dihydroxy-3,3'-ditertiarybutyl-5,5'-dimethylbiphenyl, 4,4'-dihydroxy-3,3''-Tetra-tert-butylbiphenyl, and the like. As an example, 4,4'-bis (2,3-epoxypropoxy) -3,3 ', 5,5'-tetramethylbiphenyl may be used in terms of flow (low viscosity).
In addition, the above-mentioned epoxy resin may be used in combination with other epoxy resins commonly used in semiconductor encapsulants such as bisphenol A, alicyclic, linear aliphatic, ortho cresol novolac, naphthol novolak, multifilament, dicyclopenta Diene-type epoxy resin, and the like.
In an embodiment of the present invention, the epoxy resin may be contained in an amount of 3 to 6% by weight based on the total weight of the epoxy resin composition. When the content of the epoxy resin satisfies the above range, the flexural characteristic of the semiconductor package can be maintained at a satisfactory level, and sufficient adhesiveness, insulation, flowability and moldability can be secured.
In one embodiment of the present invention, the curing agent may be a phenol resin having excellent physical properties such as moisture resistance, heat resistance and storage stability, but is not limited thereto, as a component that reacts with the epoxy resin to advance the curing of the composition.
In one embodiment of the present invention, the curing agent may be at least one selected from a xylock type phenol resin, a novolak type phenol resin, a multi-aromatic type phenol resin, and a polyfunctional phenol resin. As an example, a mixture of a xylock-type phenolic resin and a polyfunctional phenolic resin may be used in view of minimizing warping of the package and excellent moldability.
In one embodiment of the present invention, the curing agent may be contained in an amount of 3 to 6% by weight based on the total weight of the epoxy resin composition. When the content of the curing agent satisfies the above range, the flexural characteristics of the semiconductor package can be maintained at a satisfactory level, and sufficient adhesiveness, insulation, flowability and moldability can be secured.
In one embodiment of the present invention, the curing accelerator is a component for promoting the curing reaction between the epoxy resin and the curing agent, and is not particularly limited as long as it is commonly used in the art. For example, there may be mentioned 2-methylimidazole, 2,4-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, Imidazole compound, triethylamine, benzyldimethylamine, methylbenzyldimethylamine, 2- (dimethylaminomethyl) phenol, 2,4,6-tris (dimethylaminomethyl) phenol, 1,8-diazabicyclo 4,0) undecene-7, and a tertiary amine compound such as triphenylphosphine, trimethylphosphine, triethylphosphine, tributylphosphine, tri (p-methylphenyl) An organic phosphine compound such as a pin can be used, and organic phosphine having excellent moisture resistance and heat hardness can be used. These curing accelerators may be used alone or in combination of two or more.
In one embodiment of the present invention, the curing accelerator may be contained in an amount of 0.01 to 5% by weight based on the total weight of the epoxy resin composition. When the range is satisfied, adequate curability can be secured.
In one embodiment of the present invention, the filler is a component for improving the strength of the encapsulant and lowering the moisture absorption amount. For example, an inorganic filler such as silica, silica nitride, alumina, aluminum nitride or boron nitride may be used alone Or two or more of them may be used in combination. For example, when the molten or synthetic silica having an average degree of sphericity of 0.92 or more and an average particle diameter of 1 to 30 탆 is used as the filler, the mechanical strength can be improved and the reliability by low moisture absorption can be improved.
In one embodiment of the present invention, the filler may be contained in an amount of 88 to 91% by weight based on the total weight of the epoxy resin composition. When the content of the filler is less than 88 wt%, the strength is lowered due to an increase in the moisture absorption amount, and the adhesiveness after the reflow soldering process may deteriorate. When the content of the filler exceeds 91 wt%, the viscosity increases, This can be bad.
The epoxy resin composition according to an embodiment of the present invention may further include an additive generally used in a semiconductor encapsulant to the extent that the epoxy resin composition does not deviate from the object. (Silane) coupling agents which give a bonding force between the resin components to be used and inorganic fillers, coloring agents such as carbon black, iron oxide, and spinach, hydrotalcite ion capturing agents, long chain fatty acids, metal salts of long chain fatty acids, paraffin wax At least one additive selected from the group consisting of a release agent such as carnauba wax and silicone oil, a modifier such as silicone powder, and a low-stress agent such as a modified silicone resin and a modified polybutadiene in an amount of 0.1 to 5 wt% based on the total weight of the epoxy resin composition, As shown in FIG.
The epoxy resin composition for semiconductor encapsulation according to the present invention can be produced by a conventional method in the art, preferably a melt kneading method using a Banbury mixer, a kneader, a roll, a single or twin screw extruder, and a cone. For example, the above-mentioned components are uniformly mixed and then melted and mixed at a temperature of 100 to 130 ° C using a heat kneader, cooled to room temperature, pulverized into a powder state, Whereby an epoxy resin composition can be obtained.
An embodiment of the present invention provides a semiconductor device encapsulated using the epoxy resin composition for semiconductor encapsulation.
The method of encapsulating a semiconductor element using the epoxy resin composition of the present invention can be carried out according to a conventional method in the art, for example, a molding method such as a transfer mold, a compression mold, and an injection mold.
In one embodiment of the present invention, the semiconductor device may be a transistor, a diode, a microprocessor, a semiconductor memory, or the like.
Hereinafter, the present invention will be described more specifically with reference to Examples, Comparative Examples and Experimental Examples. It should be apparent to those skilled in the art that these examples, comparative examples and experimental examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.
Example 1 to 3 and Comparative Example 1 to 2: Manufacture of epoxy resin composition for semiconductor encapsulation
Each component was mixed in the composition shown in the following Table 1 (unit: wt%), and melt-mixed, cooled, pulverized and blended to obtain an epoxy resin composition for semiconductor encapsulation.
1) 4,4'-bis (2,3-epoxypropoxy) -3,3 ', 5,5'-tetramethyl (1,1'-biphenyl) (YX-4000K, Mitsubishi Chemical Corporation) Equivalent: 192, melting point: 107 占 폚, viscosity: 0.2 poise)
2) EXA-7311-G4 (DIC) (epoxy equivalent: 250, melting point: 57 캜, viscosity: 50 mPa.s)
3) A phenol polymer (MEH-7800-4S, Meiwa Chemicla) (OH equivalent: 169, softening point: 65 캜, viscosity: 0.65 poise) having 1,4-bis (methoxymethyl)
4) Phenol polymer having hydroxybenzaldehyde (MEH-7500-3S, Meiwa Chemicla) (OH equivalent: 97, softening point: 84 캜, viscosity: 1.3 poise)
5) FB-975FD (specific surface area: 3.4 m 2 / g, average particle diameter: 15.5 탆, average sphericity: 0.92)
6) Y-9669 (Momentive Performance Material INC)
7) KMP-594 (Shin-Etsu Chemical)
8) KF-1002 (Shin-Etsu Chemical)
9) CAR-WAX (KAHL GMBH)
10) MA-600 (Mitsubishi Chemical)
11) TPP (HOKKO Chemical)
Experimental Example One:
The physical properties of the epoxy resin compositions prepared in Examples 1 to 3 and Comparative Examples 1 and 2 were measured by the following methods, and the results are shown in Table 2 below.
(1) spiral flow
The prepared epoxy resin composition was molded using a spiral flow mold in a heat transfer molding machine (pressure = 70 kg / cm 2, temperature = 175 ° C, curing time = 120 sec), and the flowability of the product was measured.
(2) Gelation time
The prepared epoxy resin composition was spread over a gel timer in a small and uniform manner to measure the time required for gelation of the product.
(3) Glass transition temperature (T g)
The epoxy resin composition thus prepared was molded in a heat transfer molding machine, and then the glass transition temperature was measured using a TMA (Thermomechanical Analyzer) (temperature raising rate 10 ° C / min, temperature change range 20 to 270 ° C).
(4) Coefficient of linear expansion
The epoxy resin composition thus prepared was molded in a heat transfer molding machine, and then the coefficient of linear expansion? 1 before the glass transition temperature and the coefficient of linear expansion? 2 after the glass transition temperature were measured using a TMA (Thermomechanical Analyzer).
(5) Warpage
The FBGA (Fine pitch Ball Grid Array) package was encapsulated in a transfer molding method (175 ° C, 70 kgf / cm 2 , 100 sec) using the epoxy resin composition prepared. The positional deviation of the upper and lower parts of the package was measured using a mechanical measuring device (AXP, Akrometrix, Inc.).
As can be seen from the above Table 2, the epoxy resin compositions of Examples 1 to 3 containing the modified naphthalene epoxy resin had a lower linear expansion coefficient than those of Comparative Examples 1 and 2 which did not use the modified naphthalene epoxy resin, Much less.
It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the invention. Do. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.
Accordingly, the actual scope of the invention is defined by the appended claims and their equivalents.
Claims (12)
[Chemical Formula 1]
In this formula,
Each R < 1 > is independently hydrogen or a methyl group,
Ar 1 and Ar 2 are each independently a naphthylene group or a phenylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms or a phenyl group,
R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aralkyl group having the following formula (2)
R 3 each independently represents hydrogen, an aralkyl group of the following formula (2) or an epoxy group-containing aromatic hydrocarbon group of the following formula (3)
p and q are each independently an integer of 0 to 4, with the proviso that any of p and q is 1 or more;
(2)
In this formula,
R 4 and R 5 are each independently hydrogen or a methyl group,
Ar 3 is a phenylene group or a naphthylene group, and these groups may be substituted with an alkyl group having 1 to 4 carbon atoms,
r is an integer from 1 to 4;
(3)
In this formula,
R < 6 > is hydrogen or a methyl group,
Ar 4 is an alkyl group having 1 to 4 carbon atoms or a naphthylene group unsubstituted or substituted with a phenyl group,
s is an integer of 1 or 2;
Each R < 1 > is independently hydrogen or a methyl group,
Ar 1 and Ar 2 are each independently a naphthylene group or a phenylene group which may be substituted with an alkyl group having 1 to 4 carbon atoms or a phenyl group,
R 2 is independently hydrogen or an alkyl group having 1 to 4 carbon atoms,
R < 3 > is hydrogen,
and p and q are 1.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020150106584A KR20170013644A (en) | 2015-07-28 | 2015-07-28 | Epoxy Resin Composition for Sealing Semiconductor |
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| Application Number | Priority Date | Filing Date | Title |
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| KR1020150106584A KR20170013644A (en) | 2015-07-28 | 2015-07-28 | Epoxy Resin Composition for Sealing Semiconductor |
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| KR20170013644A true KR20170013644A (en) | 2017-02-07 |
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| KR1020150106584A KR20170013644A (en) | 2015-07-28 | 2015-07-28 | Epoxy Resin Composition for Sealing Semiconductor |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190061832A (en) * | 2017-11-28 | 2019-06-05 | 주식회사 케이씨씨 | Epoxy resin composition |
| KR102274197B1 (en) | 2020-01-14 | 2021-07-06 | 강주현 | size converting shoe |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120103896A (en) | 2011-03-11 | 2012-09-20 | 주식회사 케이씨씨 | Epoxy resin composition for sealing semiconductor and semiconductor device sealed using the same |
-
2015
- 2015-07-28 KR KR1020150106584A patent/KR20170013644A/en not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120103896A (en) | 2011-03-11 | 2012-09-20 | 주식회사 케이씨씨 | Epoxy resin composition for sealing semiconductor and semiconductor device sealed using the same |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190061832A (en) * | 2017-11-28 | 2019-06-05 | 주식회사 케이씨씨 | Epoxy resin composition |
| KR102274197B1 (en) | 2020-01-14 | 2021-07-06 | 강주현 | size converting shoe |
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