WO2011118157A1 - 半導体封止用エポキシ樹脂組成物およびこれを用いた半導体装置 - Google Patents
半導体封止用エポキシ樹脂組成物およびこれを用いた半導体装置 Download PDFInfo
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- WO2011118157A1 WO2011118157A1 PCT/JP2011/001533 JP2011001533W WO2011118157A1 WO 2011118157 A1 WO2011118157 A1 WO 2011118157A1 JP 2011001533 W JP2011001533 W JP 2011001533W WO 2011118157 A1 WO2011118157 A1 WO 2011118157A1
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- FQYUMYWMJTYZTK-UHFFFAOYSA-N C(C1OC1)Oc1ccccc1 Chemical compound C(C1OC1)Oc1ccccc1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
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Definitions
- the present invention relates to an epoxy resin composition for semiconductor encapsulation and a semiconductor device using the same. More specifically, when a copper lead frame is used, an epoxy resin composition for semiconductor encapsulation excellent in adhesion to copper that has undergone oxidation and releasability from a molding die, and for semiconductor encapsulation
- the present invention relates to a semiconductor device using an epoxy resin composition.
- Improving the adhesion between an insert product such as a lead frame and a cured resin product in order to suppress delamination is contrary to improving the releasability of the cured resin product from the molding die. For this reason, if the adhesiveness with an insert such as a lead frame is improved, the releasability from the molding die will be inferior, and the moldability may be reduced.
- the adhesion to the copper lead frame which has been oxidized is good, and the mold release property and the continuous moldability are also excellent.
- An epoxy resin composition for semiconductor encapsulation and a semiconductor device provided with an element encapsulated thereby are provided.
- the epoxy resin composition for semiconductor sealing containing the hydrocarbon compound which has an ester group is provided.
- the component (D) is an alkene.
- the component (D) is an alkene having 10 or more carbon atoms.
- the component (D) is a 1-alkene having 10 or more carbon atoms.
- the component (D) is a 1-alkene having 28 or more carbon atoms.
- the component (E) includes a compound obtained by half-esterifying a copolymer of 1-alkene and maleic anhydride with an aliphatic alcohol, and montan. It is at least one hydrocarbon compound selected from the group consisting of acid esters.
- the component (E) in the epoxy resin composition for semiconductor encapsulation, is a copolymer of 1-alkene having 5 to 60 carbon atoms and maleic anhydride, and having 10 to 10 carbon atoms. It is a compound half-esterified with 25 long-chain aliphatic alcohols.
- the component (E) is a copolymer of 1-alkene having 28 to 60 carbon atoms and maleic anhydride, It is a compound half-esterified with 20 long-chain aliphatic alcohols.
- the blending ratio of the component (D) and the component (E) is 1: 4 to 1:20 by mass ratio.
- the component (A) in the epoxy resin composition for semiconductor encapsulation, has a biphenyl type epoxy resin represented by the formula (3) and a phenylene skeleton represented by the formula (4). And at least one epoxy resin selected from the group consisting of a phenol aralkyl type epoxy resin and a phenol aralkyl type epoxy resin having a biphenylene skeleton represented by the formula (5).
- R 1 to R 4 are a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms, all of which may be the same or different, and n is 0 to 3 Is an integer.
- R is a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms, all of which may be the same or different, and n is an integer of 0 to 20.
- R 5 to R 13 are a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms, all of which may be the same or different, and n is 0 to 3 Is an integer.
- a semiconductor device including a semiconductor element encapsulated with the above-described epoxy resin composition for encapsulating a semiconductor is provided.
- a semiconductor device having excellent reliability can be obtained by sealing an electronic component such as an IC or LSI using the epoxy resin composition for semiconductor sealing.
- FIG. 3 is a schematic diagram illustrating a cross-sectional structure of a portion A in the vicinity of a medium-sized molded product in FIG. 2.
- the epoxy resin composition for semiconductor encapsulation of the present invention comprises (A) an epoxy resin, (B) a curing agent, (C) an inorganic filler, (D) a hydrocarbon having a structure of formula (1) and formula (2).
- Compound (E) includes a hydrocarbon compound having an ester group.
- epoxy resin (A) used in the epoxy resin composition for semiconductor encapsulation of the present invention those generally used for epoxy resin compositions for semiconductor encapsulation can be used.
- examples of these include, for example, phenols such as phenol novolac type epoxy resins, orthocresol novolac type epoxy resins, phenols such as cresol, xylenol, resorcin, catechol, bisphenol A, bisphenol F and / or ⁇ -naphthol, Epoxylated novolak resin obtained by condensation or co-condensation of naphthols such as ⁇ -naphthol and dihydroxynaphthalene with compounds having aldehyde groups such as formaldehyde, acetaldehyde, propionaldehyde, benzaldehyde, salicylaldehyde in the presence of an acidic catalyst.
- aldehyde groups such as formaldehyde, acetaldehyde, propionaldehyde,
- Diglycidyl ethers such as bisphenol A, bisphenol F, bisphenol S, bisphenol A / D, jigs of alkyl-substituted or unsubstituted biphenol Biphenyl type epoxy resin that is lysidyl ether, epoxidized phenol aralkyl resin synthesized from phenols and / or naphthols and dimethoxyparaxylene or bis (methoxymethyl) biphenyl, stilbene type epoxy resin, hydroquinone type epoxy resin, phthalate Glycidyl ester type epoxy resin obtained by reaction of polybasic acid such as acid and dimer acid and epichlorohydrin, Glycidylamine type epoxy resin obtained by reaction of polyamine such as diaminodiphenylmethane and isocyanuric acid and epichlorohydrin, Dicyclopentadiene and phenol Dicyclopentadiene type epoxy resin, epoxy resin having naphthalene ring, triphenolmethan
- a biphenyl type epoxy resin represented by formula (3) a phenol aralkyl type epoxy resin having a phenylene skeleton represented by formula (4), and formula (5)
- a phenol aralkyl type epoxy resin having a biphenylene skeleton represented by (In the formula (3), R 1 to R 4 are a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms, all of which may be the same or different, and n is 0 to 3 Is an integer.)
- R is a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms, all of which may be the same or different, and n is an integer of 0 to 20.
- R 5 to R 13 are a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms, all of which may be the same or different, and n is 0 to 3 Is an integer.
- R 1 to R 4 in the formula (3) are a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group or the like, an alkyl group having 1 to 10 carbon atoms, a methoxy group, an ethoxy group, C1-C10 alkoxyl groups such as propoxy group and butoxy group, C6-C10 aryl groups such as phenyl group, tolyl group and xylyl group, and C6-C10 such as benzyl group and phenethyl group Although selected from the group consisting of aralkyl groups, among them, a hydrogen atom or a methyl group is preferable.
- Examples of the biphenyl type epoxy resin represented by the formula (3) include 4,4′-bis (2,3-epoxypropoxy) biphenyl or 4,4′-bis (2,3-epoxypropoxy) -3,3 ′, An epoxy resin based on 5,5′-tetramethylbiphenyl, epichlorohydrin, and 4,4′-biphenol or 4,4 ′-(3,3 ′, 5,5′-tetramethyl) biphenol are reacted.
- the resulting epoxy resin examples include epoxy resins mainly composed of 4,4′-bis (2,3-epoxypropoxy) -3,3 ′, 5,5′-tetramethylbiphenyl,
- epoxy resins mainly composed of 4,4′-bis (2,3-epoxypropoxy) -3,3 ′, 5,5′-tetramethylbiphenyl For example, YX-4000K, YX-4000H (trade name of Japan Epoxy Resin Co., Ltd.) and the like are commercially available.
- the blending amount is preferably 20% by mass or more, more preferably 30% by mass or more, and further preferably 50% by mass or more based on the total amount of the epoxy resin used.
- R in the formula (4) is a hydrogen atom, methyl group, ethyl group, propyl group, butyl group, isopropyl group, isobutyl group or other alkyl group having 1 to 10 carbon atoms, methoxy group, ethoxy group, propoxy group, butoxy Group consisting of an alkoxyl group having 1 to 10 carbon atoms such as a group, an aryl group having 6 to 10 carbon atoms such as a phenyl group, a tolyl group and a xylyl group, and an aralkyl group having 6 to 10 carbon atoms such as a benzyl group and a phenethyl group.
- a hydrogen atom or a methyl group is preferable.
- NC2000 trade name, manufactured by Nippon Kayaku Co., Ltd.
- the blending amount is preferably 10% by mass or more, more preferably 20% by mass or more, based on the total amount of the epoxy resin used in order to exhibit the performance.
- R 5 to R 13 in the formula (5) are each a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group or other alkyl group having 1 to 10 carbon atoms, a methoxy group, an ethoxy group, C1-C10 alkoxyl groups such as propoxy group and butoxy group, C6-C10 aryl groups such as phenyl group, tolyl group and xylyl group, and C6-C10 such as benzyl group and phenethyl group It is selected from the group consisting of aralkyl groups, and among them, a hydrogen atom or a methyl group is preferable.
- NC-3000L trade name, manufactured by Nippon Kayaku Co., Ltd.
- the blending amount is preferably 10% by mass or more, more preferably 20% by mass or more, based on the total amount of the epoxy resin used in order to exhibit the performance.
- the biphenyl type epoxy resin represented by the formula (3), the phenol aralkyl type epoxy resin having the phenylene skeleton represented by the formula (4), and the phenol aralkyl type epoxy resin having the biphenylene skeleton represented by the formula (5) are each independent. Two or more types may be used in combination. When using 2 or more types together, it is preferable that those compounding quantities shall be 50 mass% or more in total with respect to the epoxy resin used whole quantity, and it is more preferable to set it as 70 mass% or more.
- the blending ratio of the entire epoxy resin as the component (A) is not less than the above lower limit value, there is little possibility of causing a decrease in fluidity.
- the blending ratio of the entire epoxy resin of the component (A) is not more than the above upper limit value, there is little possibility of causing a decrease in solder resistance.
- the curing agent (B) used in the epoxy resin composition for semiconductor encapsulation of the present invention those generally used for epoxy resin compositions for semiconductor encapsulation can be used.
- examples thereof include phenol novolac resins, cresol novolac resins and other phenols, cresol, resorcin, catechol, bisphenol A, bisphenol F, phenylphenol, aminophenol and other phenols and / or ⁇ -naphthol, ⁇ -naphthol, From resins obtained by condensation or cocondensation of naphthols such as dihydroxynaphthalene and compounds having an aldehyde group such as formaldehyde under an acidic catalyst, phenols and / or naphthols and dimethoxyparaxylene or bis (methoxymethyl) biphenyl Examples thereof include synthesized phenol aralkyl resins, and these may be used alone or in combination of two or more.
- a phenol aralkyl resin having a biphenylene skeleton represented by the formula (6) is preferable.
- R 14 to R 22 are a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms, all of which may be the same or different, and n is an integer of 0 to 10) .
- R 14 to R 22 in the formula (6) may all be the same or different and have 1 to 10 carbon atoms such as a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, and an isobutyl group.
- Alkyl groups having 1 to 10 carbon atoms such as alkyl groups, methoxy groups, ethoxy groups, propoxy groups and butoxy groups, aryl groups having 6 to 10 carbon atoms such as phenyl groups, tolyl groups and xylyl groups, and benzyl groups and phenethyl groups.
- the group is selected from the group consisting of a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms such as an aralkyl group having 6 to 10 carbon atoms such as a group, among which a hydrogen atom and a methyl group are preferable.
- a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms such as an aralkyl group having 6 to 10 carbon atoms such as a group, among which a hydrogen atom and a methyl group are preferable.
- MEH-7851SS (trade name, manufactured by Meiwa Kasei Co., Ltd.) is commercially available.
- the blending amount is preferably 50% by mass or more, more preferably 70% by mass or more, based on the total amount of the curing agent used in order to exhibit its performance. preferable.
- curing agent (B) used with the epoxy resin composition for semiconductor sealing of this invention is not specifically limited, 0.5 mass% or more and 12 mass in all the epoxy resin compositions for semiconductor sealing. % Or less, and more preferably 1% by mass or more and 9% by mass or less.
- the blending ratio of the curing agent (B) is not less than the above lower limit, there is little possibility of causing a decrease in fluidity.
- the blending ratio of the curing agent (B) is not more than the above upper limit value, there is little possibility of causing a decrease in solder resistance.
- the equivalent ratio of the (A) component epoxy resin and the (B) component curing agent that is, the ratio of the number of epoxy groups in the epoxy resin (A) / the number of hydroxyl groups in the curing agent (B) is not particularly limited. In order to keep each unreacted component small, it is preferably set in the range of 0.5 to 2, more preferably in the range of 0.6 to 1.5. Further, in order to obtain an epoxy resin composition for semiconductor encapsulation excellent in moldability and reflow resistance, it is more preferably set in the range of 0.8 to 1.2.
- the inorganic filler (C) used in the epoxy resin composition for semiconductor encapsulation of the present invention is used as an epoxy resin composition for semiconductor encapsulation for reducing hygroscopicity, reducing linear expansion coefficient, improving thermal conductivity, and improving strength.
- Blended. Examples include fused silica, crystalline silica, alumina, calcium silicate, calcium carbonate, potassium titanate, silicon carbide, silicon nitride, aluminum nitride, boron nitride, beryllia, zirconia, zircon, fosterite, steatite, spinel, mullite. And powders such as titania, or beads, glass fibers and the like obtained by spheroidizing these.
- examples of the inorganic filler having a flame retardant effect include aluminum hydroxide, magnesium hydroxide, zinc borate, and zinc molybdate. These inorganic fillers may be used alone or in combination of two or more. Among the above inorganic fillers, fused silica is preferable from the viewpoint of reducing the linear expansion coefficient, and alumina is preferable from the viewpoint of high thermal conductivity, and the filler shape is spherical from the viewpoint of fluidity and mold wear during molding. Is preferred.
- the blending amount of the inorganic filler (C) is 80% by mass or more and 96% by mass or less with respect to the epoxy resin composition for semiconductor encapsulation from the viewpoints of moldability, hygroscopicity, reduction of linear expansion coefficient and improvement of strength.
- the range is preferable, the range of 82% by mass to 92% by mass is more preferable, and the range of 86% by mass to 90% by mass is more preferable. If it is less than the lower limit, the reliability tends to decrease, and if it exceeds the upper limit, the moldability tends to decrease.
- the hydrocarbon compound having the structure of the formula (1) and the formula (2) of the component (D) used in the epoxy resin composition for semiconductor encapsulation of the present invention is an epoxy resin for semiconductor encapsulation for improving mold release properties. It is mix
- hydrocarbon compounds include 1-hexene, 2-hexene, 1,3-hexadiene, 1-octene, 2-octene, 3-octene, 1,3-octadiene, 1-decene, 2-decene.
- Branched unsaturated hydrocarbon compounds such as chain unsaturated hydrocarbon compounds, 3-methyl-1-triacontene, 3,4-dimethyl-triacontene, 3-methyl-1-tetracontane, 3,4-dimethyl-tetraconten Hydrogen etc. are mentioned, These may be used independently or may be used in combination of 2 or more type.
- alkenes are preferable from the viewpoints of storage stability and chemical stability, alkenes having 10 or more carbon atoms are more preferable from the viewpoint that voids are not easily formed in molded articles, and from the viewpoint of releasability.
- a 1-alkene having 10 or more carbon atoms is more preferable, a 1-alkene having 28 or more carbon atoms is still more preferable, and a 1-alkene having 28 to 60 carbon atoms is particularly preferable. If the carbon number of the 1-alkene exceeds the upper limit value, the adhesion to the copper lead frame that has been oxidized may be insufficient.
- the blending ratio of the component (D) used in the epoxy resin composition for semiconductor encapsulation of the present invention is not particularly limited, but is 0.01 parts by mass or more and 100 parts by mass with respect to 100 parts by mass of the epoxy resin of the component (A). 0.1 parts by mass or less is preferable, and 0.02 parts by mass or more and 0.04 parts by mass or less are more preferable.
- the effect which improves mold release property is acquired as a compounding ratio is more than the said lower limit. There is little possibility of causing the adhesive fall etc. that a mixture ratio is below the said upper limit.
- the hydrocarbon compound (E) having an ester group used in the epoxy resin composition for semiconductor encapsulation of the present invention is not particularly limited.
- a copolymer of 1-alkene and maleic anhydride is an aliphatic alcohol.
- examples thereof include semi-esterified compounds and montanic acid esters.
- These hydrocarbon compounds having an ester group may be used alone or in combination of two or more.
- the hydrocarbon compound (E) having an ester group has a high effect of dispersing the component (D) in the epoxy resin (A) or the curing agent (B), and the oxidation progressed when used in combination with the component (D). It is effective in improving the adhesive strength and releasability for copper lead frames.
- the 1-alkene monomer used for the synthesis of a compound obtained by half-esterifying a copolymer of 1-alkene and maleic anhydride with a long-chain aliphatic alcohol is not particularly limited.
- Content 1-Hentria content, 1-Dotria content, 1-Tritria content, 1-Tetratria content, 1-Pentatria content, 1-Hexatria content, 1-Tetra content, 1-Hen tetra content, 1 -Dotetracontane, 1-Tritetracontane, 1-Tetratetracontene, 1-Pentacontene, 1-Henpentacontene, 1-Dopentacontene, 1-Tripentacontengen, 1-Pentapententene, 1-Hexaconteng Linear 1-alkene, 3-methyl-1-triacontene, 3,4-dimethyl, etc.
- Branched-type 1-alkenes such as ru-triacontene, 3-methyl-1-tetracontane, 3,4-dimethyl-tetracontene, etc., which may be used alone or in combination of two or more.
- the number of carbon atoms of the 1-alkene monomer used in the synthesis of a compound obtained by half-esterifying a copolymer of 1-alkene and maleic anhydride with a long-chain aliphatic alcohol is from the viewpoint of adhesion to a copper lead frame that has undergone oxidation. 5 to 60 is preferable, and a carbon number of 28 to 60 is more preferable from the viewpoint of continuous formability (mold release property).
- the long-chain aliphatic alcohol used for the synthesis of a compound obtained by half-esterifying a copolymer of 1-alkene and maleic anhydride with a long-chain aliphatic alcohol is not particularly limited, and examples thereof include decyl alcohol and undecyl alcohol.
- Linear or branched aliphatic saturated alcohols such as lauryl alcohol, tridecyl alcohol, myristyl alcohol, pentadecyl alcohol, cetyl alcohol, heptadecyl alcohol, stearyl alcohol, nonadecyl alcohol, eicosyl alcohol, hexenol, 2- Examples thereof include linear or branched aliphatic unsaturated alcohols such as hexen-1-ol, 1-hexen-3-ol, pentenol, and 2-methyl-1-pentenol.
- More than one species may be used in combinationAmong these, a linear alcohol having 10 to 25 carbon atoms is preferable from the viewpoint of mold release load, and a linear aliphatic saturated alcohol having 15 to 20 carbon atoms is more preferable from the viewpoint of continuous moldability. If the carbon number of the long-chain aliphatic alcohol used in the synthesis of the compound in which the copolymer of 1-alkene and maleic anhydride is half-esterified with a long-chain aliphatic alcohol is less than the lower limit, continuous moldability (release property) If the upper limit is exceeded, the adhesion to a copper lead frame in which oxidation has progressed decreases.
- the copolymer of 1-alkene and maleic anhydride used for the synthesis of the component (E) of the present invention is not particularly limited, but for example, a compound represented by the formula (7), represented by the formula (8)
- Examples of commercially available products include Diacarna (registered trademark) 30 (Mitsubishi Chemical Co., Ltd.) using 1-octacosene, 1-triacontene, 1-tetracontene, 1-pentacontene, 1-hexacontene and the like as raw materials. (Trade name made by Co., Ltd.) is available.
- R represents an aliphatic hydrocarbon group having 3 to 58 carbon atoms, and n is an integer of 1 or more.
- m represents the copolymerization ratio of 1-alkene and maleic anhydride, and is not particularly limited. However, when 1-alkene is X mol and maleic anhydride is Y mol, X / Y, that is, m is 1 / It is preferably 2 to 10/1, more preferably about 1/1 of about equimolar amount.
- the method for producing a copolymer of 1-alkene and maleic anhydride is not particularly limited, and a general copolymerization method such as reaction of raw materials can be used.
- an organic solvent in which 1-alkene and maleic anhydride can be dissolved may be used.
- an organic solvent Toluene is preferable and an aromatic solvent, an ether solvent, a halogen-type solvent etc. can also be used.
- the reaction temperature varies depending on the type of organic solvent used, but is preferably 50 to 200 ° C., more preferably 100 to 150 ° C. from the viewpoint of reactivity and productivity.
- the reaction time is not particularly limited as long as a copolymer can be obtained, but it is preferably 1 to 30 hours, more preferably 2 to 15 hours, and further preferably 4 to 10 hours from the viewpoint of productivity.
- unreacted components, solvents and the like can be removed as necessary under heating and reduced pressure.
- the conditions are as follows: temperature is 100 to 220 ° C., more preferably 120 to 180 ° C., pressure is 13.3 ⁇ 10 3 Pa or less, more preferably 8 ⁇ 10 3 Pa or less, and time is 0.5 to 10 hours. It is preferable.
- a radical polymerization initiator such as azobisisobutyronitrile (AIBN) or benzoyl peroxide (BPO) may be added to the reaction as necessary.
- AIBN azobisisobutyronitrile
- BPO benzoyl peroxide
- the method for esterifying the copolymer of 1-alkene and maleic anhydride with a long-chain aliphatic alcohol is not particularly limited, and includes general methods such as addition reaction of alcohol with the copolymer.
- the reaction molar ratio of the copolymer of 1-alkene and maleic anhydride and the alcohol is not particularly limited and can be arbitrarily set. However, the degree of hydrophilicity is controlled by adjusting the reaction molar ratio. Therefore, it is preferable to set appropriately according to the target epoxy resin composition for sealing.
- an organic solvent in which 1-alkene and maleic anhydride can be dissolved may be used.
- the reaction temperature varies depending on the type of organic solvent used, but is preferably 50 to 200 ° C., more preferably 100 to 150 ° C. from the viewpoint of reactivity and productivity.
- the reaction time is not particularly limited as long as a copolymer can be obtained, but it is preferably 1 to 30 hours, more preferably 2 to 15 hours, and further preferably 4 to 10 hours from the viewpoint of productivity. After completion of the reaction, unreacted components, solvents and the like can be removed as necessary under heating and reduced pressure.
- the conditions are as follows: temperature is 100 to 220 ° C., more preferably 120 to 180 ° C., pressure is 13.3 ⁇ 10 3 Pa or less, more preferably 8 ⁇ 10 3 Pa or less, and time is 0.5 to 10 hours. It is preferable.
- a reaction catalyst such as an amine catalyst such as ethylamine, N, N dimethylaminopyridine, or an acid catalyst such as sulfuric acid or paratoluenesulfonic acid may be added to the reaction as necessary.
- Examples of the compound obtained by esterifying a copolymer of 1-alkene and maleic anhydride with a long-chain aliphatic alcohol include, for example, diesters represented by the following formula (a) or (b), and formulas (c) to (c) Examples thereof include compounds containing one or more selected from the monoesters represented by f) as repeating units. Such a compound may further contain a non-ester represented by the formula (g) or (h). As such a compound, the main chain skeleton includes any one of (1) (a) to (f), and (2) any two or more of (a) to (f) are randomly selected.
- any one or more of (a) to (f) and (g) and / or (h) at random Including regularly or in blocks.
- Such compounds may be used alone or in combination of two or more.
- the compound comprised may be included.
- the esterification rate of a compound obtained by esterifying a copolymer of 1-alkene and maleic anhydride with a long-chain aliphatic alcohol is preferably 20 mol% or more from the viewpoint of releasability and adhesiveness.
- R 1 represents an aliphatic hydrocarbon group having 3 to 58 carbon atoms
- R 2 represents a hydrocarbon group having 10 to 25 carbon atoms
- m represents a copolymerization molar ratio X / Y of 1-alkene (X) and maleic anhydride (Y), preferably 1/2 to 10/1, more preferably about 1/1.
- the number average molecular weight of a compound obtained by esterifying a copolymer of 1-alkene and maleic anhydride with a long-chain aliphatic alcohol is not particularly limited as long as the repeating unit is 1 or more, and in any molecular weight region, the component (D) Can be used to achieve both adhesion and releasability to a copper lead frame that has been oxidized, but preferably has a number average molecular weight of 2,000 to 10,000.
- the compounding amount of the compound obtained by esterifying a copolymer of 1-alkene and maleic anhydride with a long-chain aliphatic alcohol is not particularly limited, but is 0.5 mass with respect to 100 parts by mass of the (A) component epoxy resin. Part or more and 10 parts by mass or less are preferable, and 1 part by mass or more and 5 parts by mass or less are more preferable. If the blending amount is less than the above lower limit value, the releasability tends to decrease, and if it exceeds the above upper limit value, the adhesion to the copper lead frame in which oxidation has progressed tends to be insufficient.
- montanic acid ester examples include montanic acid ester wax and a partially saponified product of montanic acid ester wax.
- montanic acid ester is a montanic acid ester obtained by dehydrating condensation reaction of montanic acid with a diol compound such as ethylene glycol or butylene glycol, or a triol compound such as glycerin, and further with calcium and the like. Mixtures with saponified products are commercially available.
- ethylene glycol dimontanate and glycerin trimontanate are preferable from the viewpoint of adhesion to copper oxide.
- Rico Wax (registered trademark) E and Ricorub (registered trademark) WE4 both trade names manufactured by Clariant Japan KK are available as commercial products.
- the total compounding amount of the component (D) and the component (E) in the epoxy resin composition for semiconductor encapsulation of the present invention is not particularly limited, it is 0.00% with respect to 100 parts by mass of the component (A) epoxy resin. 5 mass parts or more and 10 mass parts or less are preferable, and 1 mass part or more and 5 mass parts or less are more preferable. If the blending amount is less than the lower limit value, the releasability tends to decrease, and if the blending amount exceeds the upper limit value, the adhesion to the copper lead frame in which oxidation has progressed tends to be insufficient.
- the mixing ratio of the (D) component and the (E) component is preferably 1: 4 to 1:20. If the amount of component (D) is greater than the above range, component (D) will not be dispersed in the epoxy resin composition, the surface of the package will be heavily soiled, and the adhesion to copper lead frames that have undergone oxidation will also tend to decrease. It is in. If the blending amount of component (D) is less than the above range, the continuous moldability tends to deteriorate.
- the epoxy resin composition for semiconductor encapsulation of the present invention may further contain a curing accelerator.
- the curing accelerator is generally used in an epoxy resin composition for semiconductor encapsulation and is not particularly limited.
- 1,8-diaza-bicyclo (5,4,0) undecene-7 1,5 A cycloamidine compound such as diaza-bicyclo (4,3,0) nonene, 5,6-dibutylamino-1,8-diaza-bicyclo (5,4,0) undecene-7, and benzyldimethylamine, triethanol Tertiary amine compounds such as amine, dimethylaminoethanol, tris (dimethylaminomethyl) phenol and their derivatives, imidazole compounds such as 2-methylimidazole, 2-phenylimidazole and 2-phenyl-4-methylimidazole and their derivatives , Tributylphosphine, methyldiphenylphosphine, triphenylphosphine, Organic phosphines such
- an organic phosphorus compound is preferable, an organic phosphine and an adduct of an organic phosphine and a quinone compound are more preferable, and triphenylphosphine, triphenylphosphine, tris (4-methylphenyl) phosphine, tris ( More preferred are adducts of tertiary phosphines such as 4-methoxyphenyl) phosphine and quinone compounds such as p-benzoquinone and 1,4-naphthoquinone.
- the compounding quantity of a hardening accelerator will not be restrict
- a siloxane addition polymer can be added to the epoxy resin composition for semiconductor encapsulation of the present invention for the purpose of obtaining an epoxy resin composition having good solder stress resistance and good fluidity.
- the siloxane addition polymer is not particularly limited, and a conventionally known polymer can be used.
- a part of the methyl substituent of dimethylsiloxane may be an alkyl group, an epoxy group, a carboxyl group, an amino group, or the like. Examples thereof include modified silicone oil substituted with a substituent.
- the siloxane addition polymer-modified product can be used singly or in combination of two or more and used in a proportion of 0.1% by mass or more and 2% by mass or less based on the entire epoxy resin composition. If the blending amount exceeds the upper limit value, surface contamination is likely to occur and the resin bleed may be lengthened. If the blending amount is less than the lower limit value, sufficient low elastic modulus and dispersibility of the release agent There may be a problem that it becomes impossible to obtain.
- An anion exchanger can also be added to the epoxy resin composition for semiconductor encapsulation of the present invention from the viewpoint of improving the moisture resistance and high temperature storage characteristics of a semiconductor element such as an IC.
- the anion exchanger is not particularly limited and conventionally known anion exchangers can be used.
- hydrotalcite, hydrous oxide of an element selected from antimony, bismuth, zirconium, titanium, tin, magnesium, and aluminum can be used, and these can be used alone or in combination of two or more.
- hydrotalcite and bismuth hydrous oxide represented by the following general formula (9) are preferable.
- Mg 1-X Al X (OH) 2 (CO 3 ) X / 2 ⁇ mH 2 O (9) In General Formula (9), 0 ⁇ X ⁇ 0.5, m is a positive integer.
- the amount of the anion exchanger is not particularly limited as long as it is a sufficient amount capable of capturing ionic impurities such as halogen ions, but is 0.1 parts by mass or more and 30 parts by mass with respect to 100 parts by mass of the epoxy resin (A). 1 part by mass or more, 10 parts by mass or less are more preferable, and 2 parts by mass or more and 5 parts by mass or less are more preferable. If the blending amount is less than the lower limit value, the trapping of ionic impurities tends to be insufficient, and if the blending amount exceeds the upper limit value, it is economically disadvantageous because there is no large difference in effect compared to the lower limit value.
- epoxy silane In the epoxy resin composition for semiconductor encapsulation of the present invention, epoxy silane, mercapto silane, amino silane, alkyl silane, ureido silane, vinyl silane, etc., if necessary, in order to enhance the adhesion between the resin component and the inorganic filler.
- Various known coupling agents such as various silane compounds, titanium compounds, aluminum chelates, and aluminum / zirconium compounds can be added.
- vinyltriethoxysilane vinyltris ( ⁇ -methoxyethoxy) silane, ⁇ -methacryloxypropyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ -glycidoxypropyltri Methoxysilane, ⁇ -glycidoxypropylmethyldimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, vinyltriacetoxysilane, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -mercaptopropylmethyldimethoxysilane, ⁇ -mercaptopropyltriethoxy Silane, ⁇ -aminopropyltrimethoxysilane, ⁇ -aminopropylmethyldimethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ -anilinopropyltri
- the blending amount of the coupling agent is preferably 0.05 parts by mass or more and 5 parts by mass or less, and 0.1 parts by mass or more and 2.5 parts by mass or less with respect to 100 parts by mass of the inorganic filler (C). It is more preferable that If it is less than the lower limit, the moisture resistance tends to decrease, and if it exceeds the upper limit, the moldability of the package tends to decrease.
- the epoxy resin composition for semiconductor encapsulation of the present invention includes, as other additives, halogen atoms such as brominated epoxy resin, antimony trioxide, antimony tetroxide, and antimony pentoxide, antimony atoms, nitrogen atoms, or phosphorus.
- halogen atoms such as brominated epoxy resin, antimony trioxide, antimony tetroxide, and antimony pentoxide, antimony atoms, nitrogen atoms, or phosphorus.
- halogen atoms such as brominated epoxy resin, antimony trioxide, antimony tetroxide, and antimony pentoxide, antimony atoms, nitrogen atoms, or phosphorus.
- halogen atoms such as brominated epoxy resin, antimony trioxide, antimony tetroxide, and antimony pentoxide, antimony atoms, nitrogen atoms, or phosphorus.
- Known organic or inorganic compounds containing atoms, flame retardants
- adhesion promoters such as these derivatives, anthranilic acid, gallic acid, malonic acid, malic acid, maleic acid, aminophenol, quinoline, etc. and their derivatives, aliphatic acid amide compounds, dithiocarbamate, thiadiazole derivatives, etc. It can be blended accordingly.
- the epoxy resin composition for semiconductor encapsulation of the present invention can be prepared by any method as long as various raw materials can be uniformly dispersed and mixed.
- a raw material having a predetermined blending amount is mixed with a raw material.
- a method of cooling and pulverizing after melt-kneading with a mixing roll, kneader, extruder or the like It is easy to use if it is tableted with dimensions and mass that match the molding conditions.
- the epoxy resin composition for semiconductor encapsulation of the present invention can be dissolved in various organic solvents and used as an epoxy resin composition for liquid semiconductor encapsulation. It can also be used as a sheet or film-like epoxy resin composition for semiconductor encapsulation obtained by coating thinly on a film and dispersing an organic solvent under conditions that do not allow the resin curing reaction to proceed so much.
- the semiconductor device of this invention is obtained by sealing a semiconductor element with the epoxy resin composition for semiconductor sealing of this invention.
- a semiconductor device an element such as a semiconductor chip, an active element such as a transistor, a diode, or a thyristor, or a passive element such as a capacitor, a resistor, or a coil is mounted on a support member of a copper lead frame, and a necessary part is mounted.
- the semiconductor device etc. which were sealed with the epoxy resin composition for semiconductor sealing of this invention are mentioned.
- a semiconductor element is fixed on a copper lead frame, and a terminal portion and a lead portion of an element such as a bonding pad are connected by wire bonding or bump, and then the semiconductor sealing of the present invention is performed.
- DIP Dual Inline Package
- PLCC Plastic Leaded Chip Package
- QFP Quad Flat Package
- SOP Small Outline Package
- SOJ Small Line Package
- Outline J-lead package TSOP (Thin Small Outline Package), TQFP (Thin Quad Flat Package)
- the general resin sealing type IC such.
- a semiconductor package in which semiconductor chips such as MCP (Multi Chip Stacked Package) are stacked in multiple stages is also exemplified.
- FIG. 1 is a view showing a cross-sectional structure of an example of a semiconductor device using the epoxy resin composition for semiconductor encapsulation according to the present invention.
- a semiconductor element 1 is stacked and fixed in two stages on a die pad 3 via a die bond material cured body 2.
- the electrode pad of the semiconductor element 1 and the lead frame 5 are connected by a gold wire 4.
- the semiconductor element 1 is sealed with a cured body 6 of a sealing resin composition.
- a low-pressure transfer molding method is most common, but an injection molding method, a compression molding method, or the like may be used.
- the epoxy resin composition for semiconductor encapsulation is liquid or pasty at normal temperature, a dispensing method, a casting method, a printing method, and the like can be given.
- an epoxy resin composition for semiconductor sealing is not in direct contact with the element. It can be suitably used as an epoxy resin composition.
- Synthesis Example 1 Synthesis of a compound (E) obtained by esterification of a copolymer of a 1-alkene having 28 to 60 carbon atoms and maleic anhydride with an alcohol having 18 carbon atoms 1-octacosene, 1-triacontene, 1-tetra Copolymer of a mixture of content, 1-pentacontene, 1-hexacontene and the like and maleic anhydride (trade name Diacarna (registered trademark) 30 manufactured by Mitsubishi Chemical Corporation), 300 g and stearyl alcohol, 140 g of toluene, 500 ml And then reacting at 110 ° C.
- Synthesis Example 2 Synthesis of compound (E) obtained by esterifying a copolymer of 1-alkene having 28 to 60 carbon atoms and maleic anhydride with alcohol having 10 carbon atoms, instead of stearyl alcohol, 1-decanol (manufactured by Tokyo Chemical Industry Co., Ltd.) )
- Compound 2 378 g having a monoesterification rate of 100 mol% was obtained by the method described in Synthesis Example 1 except that 82 g was used.
- the molecular weight was measured by polystyrene permeation chromatography using tetrahydrofuran as an eluent.
- the number average molecular weight (Mn) was 3700 and the molecular weight distribution (Mw / Mn) was 3.71, and unreacted 1-decanol.
- the residual amount was 1% or less of the entire compound 2.
- Synthesis Example 4 Synthesis of a compound (E) obtained by esterifying a copolymer of a 1-alkene having 28 to 60 carbon atoms and maleic anhydride with an alcohol having 8 carbon atoms, instead of stearyl alcohol, 1-octanol (manufactured by Tokyo Chemical Industry Co., Ltd.) )
- Compound 4 and 340 g having a monoesterification rate of 100 mol% were obtained by the method described in Synthesis Example 1 except that 68 g was used.
- the molecular weight was measured by polystyrene-permeated gel permeation chromatography using tetrahydrofuran as an eluent.
- the residual amount was 1% or less of the entire compound 4.
- Synthesis Example 6 Synthesis of a compound obtained by esterifying a copolymer of a 1-alkene having 20 to 24 carbon atoms and maleic anhydride with an alcohol having 18 carbon atoms.
- Epoxy resin 2 Phenol aralkyl type epoxy resin having a phenylene skeleton having an epoxy equivalent of 237 and a softening point of 52 ° C. (trade name NC2000, manufactured by Nippon Kayaku Co., Ltd.)
- Epoxy resin 3 phenol aralkyl type epoxy resin having a biphenylene skeleton having an epoxy equivalent of 273 and a softening point of 52 ° C.
- Epoxy resin 4 Orthocresol novolak type epoxy resin having an epoxy equivalent of 220 and a softening point of 52 ° C. (trade name EOCN-104S manufactured by Nippon Kayaku)
- Hydrocarbon compound (D) having the structure of formula (1) and formula (2): 1-alkene (C28-60): trade name Alpha Olefin C30 + manufactured by Chevron Phillips Chemical Company 1-alkene (C20-24): Idemitsu Kosan brand name Linearlen 2024 1-Alkene (C10): Tokyo Kasei brand name 1-Decene
- Hydrocarbon compound having an ester group (E) Compound 1 obtained in Synthesis Example 1
- Compound 2 obtained in Synthesis Example 2
- Compound 3 obtained in Synthesis Example 3
- Compound 4 obtained in Synthesis Example 4
- Compound 5 obtained in Synthesis Example 5
- Compound 6 obtained in Synthesis Example 6
- Montanic acid-based wax Product name Rico Wax E manufactured by Clariant
- Oxidized polyethylene wax Brand name PED191 manufactured by Clariant
- Curing accelerator 1 Adduct of triphenylphosphine and p-benzoquinone
- Colorant 1 Carbon black (trade name carbon # 5 manufactured by Mitsubishi Chemical Corporation)
- Adhesive strength with copper oxide A copper oxide base material and a tableted epoxy resin composition are integrally molded under conditions of 175 ° C., 6.9 MPa, 2 minutes, and a truncated cone on a copper oxide base material (diameter 3.6 mm, thickness 0.5 mm) After obtaining a molded product (upper diameter 3 mm ⁇ lower diameter 3.6 mm ⁇ thickness 3 mm, contact area 10 mm 2 between the copper oxide base material and the cured resin), the base material of each obtained molded product was fixed. The cured portion of the epoxy resin composition was pushed from the lateral direction, and its torque (N) was measured. This evaluation has a certain degree of correlation with the solder reflow resistance in the semiconductor. As a result of the determination, 14N or more was evaluated as ⁇ , 12N or more and less than 14N as ⁇ , and less than 12N as ⁇ .
- FIG. 2 shows a schematic plan view of the middle mold after molding.
- the shape of the molded product that adheres to the middle mold after molding is 14.0 mm in diameter and 1.5 mm in height.
- 11 indicates a medium size
- 12 indicates a cal
- 13 indicates a runner.
- Reference numeral 14 denotes a molded product
- 15 denotes an air vent.
- Reference numeral 16 denotes a handle.
- FIG. 3 shows a cross-sectional structure of the A portion of the medium-sized molded product of FIG.
- Reference numeral 17 denotes a push-pull gauge insertion hole.
- the evaluation material was transfer molded at a mold temperature of 175 ° C., an injection pressure of 6.9 MPa, and a curing time of 1 minute.
- a push bull gauge was applied from the upper hole 17 of the middle mold (see FIG. 3), and the load applied when the molded product was protruded was measured.
- measurement was performed on a 10-shot molded product in the latter half of the evaluation material formed by 20 shots, and the average value was shown as a release load.
- the evaluation has a certain degree of correlation with the stable productivity in mass production molding. As a result of the determination, 12N or less was evaluated as ⁇ , 12N or less, 15N or less as ⁇ , and 15N or less as ⁇ .
- a preferable order is the order of A, B, C...
- B: The spread of dirt is 20 area% or less of the cavity surface
- a preferable order is the order of A, B, C...
- the air vent block was also evaluated.
- the air vent block is evaluated by visually observing the mold every 50 shots, so that the air vent block (the air vent (width 0.5 mm, thickness 50 ⁇ m) is fixed to the air vent and the air vent is blocked) is observed. The presence or absence was confirmed and evaluated in the following four stages.
- a preferable order is the order of A, B, C...
- the evaluation results are shown below.
- C Air vent block generated up to 200 shots
- D Air vent block generated up to 100 shots
- Evaluation results were ranked A: Examples 1, 2, 10 Evaluation results were ranked B: Examples 3, 6, 7, 8, 9, 12
- the evaluation result was C rank: Examples 4, 5, 11, 13, 14 Evaluation result was D rank: None
- a lead frame mounted with a semiconductor element is 180 degrees. After setting on a mold at °C, preheat for 2 minutes, and inject the epoxy resin composition and mount the semiconductor element (silicon chip) under the conditions of mold temperature of 180 °C, injection pressure of 7.4MPa and curing time of 120 seconds 80pQFP (Cu lead frame, size is 14x20mm x thickness 2.00mm, semiconductor element is 7x7mm x thickness 0.35mm, inner part of semiconductor element and lead frame) The lead portion is bonded with a 25 ⁇ m diameter gold wire.
- GP-ELF low-pressure transfer molding machine
- Examples 1 to 14 are (A) an epoxy resin, (B) a curing agent, (C) an inorganic filler, (D) a hydrocarbon compound having a structure of formula (1) and formula (2), and (E) an ester. It contains a hydrocarbon compound having a group, and includes (A) the blending amount of component, (D) component type and blending amount, and (E) component type and blending amount changed. As a result, it was possible to obtain excellent solder resistance by IR reflow treatment after humidification treatment using a lead frame having high adhesion strength with copper oxide and advanced oxidation. In each of Examples 1 to 14, the release load is low, and the continuous moldability (mold dirt, package dirt, and air vent block) when a semiconductor element or the like is sealed is obtained. It was.
- an epoxy resin 1 which is a biphenyl type epoxy resin represented by the general formula (3)
- an epoxy resin 2 which is a phenol aralkyl type epoxy resin having a phenylene skeleton represented by the general formula (4)
- 50% by mass or more of epoxy resin 3 which is a phenol aralkyl type epoxy resin having a biphenylene skeleton represented by the general formula (5) is used in an amount of 50% by mass or more
- (D) component is a 1-alkene having 28 to 60 carbon atoms.
- Example 8 in which 54.4% by mass of the epoxy resin 4 which is an ortho-cresol novolac type epoxy resin was used as the component (A) was releasability (mold release load), continuous moldability (mold dirt, package dirt and air vent block) ) was good, but the adhesive strength to copper oxide tended to be slightly lower, and the solder resistance was slightly inferior.
- Example 11 using Compound 4 obtained by esterifying a copolymer of a 1-alkene having 28 to 60 carbon atoms and maleic anhydride with an alcohol having 8 carbon atoms as the component (E) has an adhesive strength and resistance to copper oxide. Solderability, moldability of continuous formability, and package dirt were good, but the release load tended to be slightly higher, resulting in slightly inferior continuous formable air vent blocks.
- the continuous formability of the air vent block was good, but the adhesive strength to copper oxide tended to be slightly lower, and the solder resistance was slightly inferior.
- the moldability of the continuous formability and the package contamination were somewhat inferior.
- Example 14 using montanic acid ester wax as the component (E), the adhesion strength to copper oxide, the solder resistance, the mold stain and the package stain of continuous formability were good, but the release load was slightly There was a tendency to be higher, and the air mold block with continuous formability was slightly inferior.
- Comparative Examples 1 to 3 which do not contain the component (E), have extremely low adhesion strength to copper oxide, and the solder resistance by IR reflow treatment after humidification using a lead frame that has undergone oxidation is extremely poor. It became. In addition, the moldability and package contamination of the continuous moldability were remarkably inferior.
- Comparative Example 4 using an oxidized polyethylene wax instead of the component (D) resulted in low adhesive strength to copper oxide and poor solder resistance. In addition, the moldability and package stains of continuous formability were inferior.
- Comparative Examples 5 to 8 using the compounds 2 and 4 to 6 as the component (E) without using the component (D) are only in that 1-alkene having 28 to 60 carbon atoms was used as the component (D). Compared with the different Examples 9 and 11 to 13, the release load was remarkably high. Further, Comparative Examples 5 to 8 were inferior to molds 9 and 11 to 13 in terms of continuous form mold stains and package stains.
- an epoxy resin composition for semiconductor encapsulation excellent in adhesion to a copper lead frame in which oxidation has progressed, releasability, continuous moldability, etc.
- oxidation of copper lead frames proceeds, such as MCP (Multi Chip Stacked Package) in which electronic components such as ICs and LSIs, in particular, semiconductor chips are stacked in multiple stages. It can be suitably used for an easy semiconductor package.
- MCP Multi Chip Stacked Package
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Abstract
Description
(E)エステル基を有する炭化水素化合物を含む、半導体封止用エポキシ樹脂組成物が提供される。
(式(3)において、R1~R4は、水素原子、あるいは炭素数1~10の置換または非置換の炭化水素基であり、全てが同一でも異なっていてもよく、nは0~3の整数である。)
(式(4)において、Rは、水素原子、あるいは炭素数1~10の置換または非置換の炭化水素基であり、全てが同一でも異なっていてもよく、nは0~20の整数である。)
(式(5)において、R5~R13は、水素原子、あるいは炭素数1~10の置換または非置換の炭化水素基であり、全てが同一でも異なっていてもよく、nは0~3の整数である。)
(式(3)において、R1~R4は、水素原子、あるいは炭素数1~10の置換または非置換の炭化水素基であり、全てが同一でも異なっていてもよく、nは0~3の整数である。)
(式(4)において、Rは、水素原子、あるいは炭素数1~10の置換または非置換の炭化水素基であり、全てが同一でも異なっていてもよく、nは0~20の整数である。)
(式(5)において、R5~R13は、水素原子、あるいは炭素数1~10の置換または非置換の炭化水素基であり、全てが同一でも異なっていてもよく、nは0~3の整数である。)
(ここで、R14~R22は水素原子、あるいは炭素数1~10の置換または非置換の炭化水素基であり、全てが同一でも異なっていてもよく、nは0~10の整数である。)
Mg1-XAlX(OH)2(CO3)X/2・mH2O (9)
(一般式(9)において、0<X≦0.5、mは正の整数。)
1-オクタコセン、1-トリアコンテン、1-テトラコンテン、1-ペンタコンテン、1-ヘキサコンテン等の混合物と無水マレイン酸との共重合物(三菱化学株式会社製商品名ダイヤカルナ(登録商標)30)、300gおよびステアリルアルコール、140gをトルエン、500mlに溶解して110℃で8時間反応させた後、160℃まで段階的に昇温しながらトルエンを除去し、減圧下160℃で6時間反応を行うことにより未反応成分を除去し、目的のモノエステル化率100モル%の化合物1、489gを得た。分子量は、テトラヒドロフランを溶離液として、ポリスチレン換算のゲル浸透クロマトグラフィーにより測定したところ、数平均分子量(Mn)=4100、分子量分布(Mw/Mn)=3.52であり、未反応のステアリルアルコール残留量は化合物1全体の1%以下であった。
ステアリルアルコールの代わりに1-デカノール(東京化成製)82gを用いたことを除いては合成例1に記載の方法によって、モノエステル化率100モル%の化合物2、378gを得た。分子量は、テトラヒドロフランを溶離液として、ポリスチレン換算のゲル浸透クロマトグラフィーにより測定したところ、数平均分子量(Mn)=3700、分子量分布(Mw/Mn)=3.71であり、未反応の1-デカノール残留量は化合物2全体の1%以下であった。
ステアリルアルコールの代わりにベヘニルアルコール(花王株式会社製商品名カルコール220-80)170gを用いたことを除いては合成例1に記載の方法によって、モノエステル化率100モル%の化合物3、458gを得た。分子量は、テトラヒドロフランを溶離液として、ポリスチレン換算のゲル浸透クロマトグラフィーにより測定したところ、数平均分子量(Mn)=4400、分子量分布(Mw/Mn)=3.55であり、未反応のベヘニルアルコール残留量は化合物3全体の1%以下であった。
ステアリルアルコールの代わりに1-オクタノール(東京化成製)68gを用いたことを除いては合成例1に記載の方法によって、モノエステル化率100モル%の化合物4、340gを得た。分子量は、テトラヒドロフランを溶離液として、ポリスチレン換算のゲル浸透クロマトグラフィーにより測定したところ、数平均分子量(Mn)=3700、分子量分布(Mw/Mn)=3.80であり、未反応の1-オクタノール残留量は化合物4全体の1%以下であった。
ステアリルアルコールの代わりにオクタコサノール(株式会社素材機能研究所製商品名ポリコサノール(米糠由来))、214gを添加したことを除いては合成例1に記載の方法によって、モノエステル化率100モル%の化合物5、506gを得た。分子量は、テトラヒドロフランを溶離液として、ポリスチレン換算のゲル浸透クロマトグラフィーにより測定したところ、数平均分子量(Mn)=4800、分子量分布(Mw/Mn)=3.91であり、未反応のオクタコサノール残留量は化合物5全体の1%以下であった。
1-エイコセン、1-ドコセン、1-テトラコセンの混合物(出光興産株式会社製商品名リニアレン2024)、180gと無水マレイン酸、58gをトルエン、500mlに溶解し、110℃で加熱しながら20分毎にBPO、0.16gを3回に分けて添加した。BPOを添加終了後、反応溶液をさらに7時間110℃で加熱した。この共重合物のトルエン溶液にステアリルアルコール162gを添加して110℃で8時間反応させた後、160℃まで段階的に昇温しながらトルエンを除去し、減圧下160℃で6時間反応を行うことにより未反応成分を除去し、目的のモノエステル化率100モル%の化合物6、380gを得た。分子量は、テトラヒドロフランを溶離液として、ポリスチレン換算のゲル浸透クロマトグラフィーにより測定したところ、数平均分子量(Mn)=9800、分子量分布(Mw/Mn)=2.63であり、未反応のステアリルアルコール残留量は化合物6全体の1%以下であった。
エポキシ樹脂(A):
エポキシ樹脂1:エポキシ当量185、融点108℃のビフェニル型エポキシ樹脂(ジャパンエポキシ株式会社製商品名エピコートYX‐4000K)
エポキシ樹脂2:エポキシ当量237、軟化点52℃のフェニレン骨格を有するフェノールアラルキル型エポキシ樹脂(日本化薬製商品名NC2000)
エポキシ樹脂3:エポキシ当量273、軟化点52℃のビフェニレン骨格を有するフェノールアラルキル型エポキシ樹脂(日本化薬製商品名NC-3000L)
エポキシ樹脂4:エポキシ当量220、軟化点52℃のオルソクレゾールノボラック型エポキシ樹脂(日本化薬製商品名EOCN-104S)
フェノール樹脂1:水酸基当量199、軟化点64℃のビフェニレン骨格を有するフェノールアラルキル型フェノール樹脂(明和化成株式会社製商品名MEH-7851SS)
無機充填材1:平均粒径10.8μm、比表面積5.1m2/gの球状溶融シリカ
1-アルケン(C28~60):Chevron Phillips Chemical Company製商品名Alpha Olefin C30+
1-アルケン(C20~24):出光興産製商品名リニアレン2024
1-アルケン(C10):東京化成製商品名1-デセン
合成例1で得られた化合物1
合成例2で得られた化合物2
合成例3で得られた化合物3
合成例4で得られた化合物4
合成例5で得られた化合物5
合成例6で得られた化合物6
モンタン酸系ワックス:クラリアント社製商品名リコワックスE
酸化ポリエチレンワックス:クラリアント社製商品名PED191
硬化促進剤1:トリフェニルホスフィンとp-ベンゾキノンとの付加物
カップリング剤1:γ-グリシドキシプロピルトリメトキシシラン(チッソ製商品名S510=GPS‐M)
着色剤1:カーボンブラック(三菱化学株式会社製商品名カーボン#5)
酸化銅基材とタブレット化したエポキシ樹脂組成物を175℃、6.9MPa、2分の条件で一体成形して、酸化銅基材(直径3.6mm、厚さ0.5mm)上に円錐台状の成形品(上径3mm×下径3.6mm×厚さ3mm、酸化銅基材と樹脂硬化物の接触面積10mm2)を得た後、得られた各成形品の基材を固定し、エポキシ樹脂組成物の硬化部位を横方向から押し、そのトルク(N)を測定した。本評価は、半導体における耐半田リフロー性とある程度の相関を有するものであり、判定結果として、14N以上を◎、12N以上14N未満を○、12N未満を×とした。
離型時荷重評価用金型は、トランスファー成形型として上型、中型、下型からなる。図2に成形後の中型の平面概略図を示した。成形後に中型に付着する成形品の形状は、直径14.0mm、高さ1.5mm厚である。図2において、11は中型を示し、12はカルを示し、13はランナーを示す。14は成形品を示し、15はエアベントを示す。16は、取っ手を示す。また図2の中型の成形品のA部の断面構造を図3に示す。17はプッシュプルゲージ挿入用の穴を示す。
低圧トランスファー自動成形機(第一精工(株)製、GP-ELF)を用いて、金型温度175℃、注入圧力9.8MPa、硬化時間70秒で、80ピンクワッドフラットパッケージ(80pQFP;Cu製リードフレーム、パッケージ外寸:14mm×20mm×2mm厚、パッドサイズ:6.5mm×6.5mm、チップサイズ6.0mm×6.0mm×0.35mm厚)を、連続で400ショットまで封止成形した。
A:汚れなし
B:汚れの広がりがキャビティ表面の20面積%以下
C:汚れの広がりがキャビティ表面の20面積%超~40面積%以下
D:汚れの広がりがキャビティ表面の40面積%超~60面積%以下
E:汚れの広がりがキャビティ表面の60面積%超
A:汚れなし
B:汚れの広がりがパッケージ表面の20面積%以下
C:汚れの広がりがパッケージ表面の20面積%超~40面積%以下
D:汚れの広がりがパッケージ表面の40面積%超~60面積%以下
E:汚れの広がりがパッケージ表面の60面積%超
A:400ショットまで問題なし
B:300ショットまでにエアベントブロック発生
C:200ショットまでにエアベントブロック発生
D:100ショットまでにエアベントブロック発生
評価結果がAランクだったもの:実施例1、2、10
評価結果がBランクだったもの:実施例3、6、7、8、9、12
評価結果がCランクだったもの:実施例4、5、11、13、14
評価結果がDランクだったもの:なし
低圧トランスファー成形機(第一精工(株)製、GP-ELF)を用いて、酸化状態を再現するため、半導体素子(シリコンチップ)が搭載されたリードフレーム等を180℃の金型上にセット後、2分間予熱し、金型温度180℃、注入圧力7.4MPa、硬化時間120秒間の条件で、エポキシ樹脂組成物を注入して半導体素子(シリコンチップ)が搭載されたリードフレーム等を封止成形し、80pQFP(Cu製リードフレーム、サイズは14×20mm×厚さ2.00mm、半導体素子は7×7mm×厚さ0.35mm、半導体素子とリードフレームのインナーリード部とは25μm径の金線でボンディングされている。)なる半導体装置を作製した。ポストキュアとして175℃で4時間加熱処理した半導体装置6個を、60℃、相対湿度60%で120時間加湿処理した後、IRリフロー処理(260℃、JEDEC・Level3条件に従う)を行った。これらの半導体装置内部の剥離およびクラックの有無を超音波探傷装置(日立建機ファインテック製、mi-scope10)で観察し、剥離またはクラックのいずれか一方でも発生したものを不良とした。n=6中の不良半導体装置の個数を表示した。不良個数が1以下であれば実用可能範囲である。
Claims (11)
- 前記(D)成分がアルケンである、請求項1に記載の半導体封止用エポキシ樹脂組成物。
- 前記(D)成分が炭素数10以上のアルケンである、請求項1に記載の半導体封止用エポキシ樹脂組成物。
- 前記(D)成分が炭素数10以上の1-アルケンである、請求項1に記載の半導体封止用エポキシ樹脂組成物。
- 前記(D)成分が炭素数28以上の1-アルケンである、請求項1に記載の半導体封止用エポキシ樹脂組成物。
- 前記(E)成分が、1-アルケンと無水マレイン酸の共重合体を脂肪族アルコールで半エステル化した化合物およびモンタン酸エステルからなる群から選ばれる少なくとも1つの炭化水素化合物である、請求項1に記載の半導体封止用エポキシ樹脂組成物。
- 前記(E)成分が、炭素数5~60の1-アルケンと無水マレイン酸の共重合体を、炭素数10~25の長鎖脂肪族アルコールで半エステル化した化合物である、請求項1に記載の半導体封止用エポキシ樹脂組成物。
- 前記(E)成分が、炭素数28~60の1-アルケンと無水マレイン酸の共重合体を、炭素数15~20の長鎖脂肪族アルコールで半エステル化した化合物である、請求項1に記載の半導体封止用エポキシ樹脂組成物。
- 前記(D)成分と前記(E)成分の配合比率が、質量比で1:4~1:20である、請求項1に記載の半導体封止用エポキシ樹脂組成物。
- 前記(A)成分が、式(3)で示されるビフェニル型エポキシ樹脂、式(4)で示されるフェニレン骨格を有するフェノールアラルキル型エポキシ樹脂、および式(5)で示されるビフェニレン骨格を有するフェノールアラルキル型エポキシ樹脂からなる群から選ばれる少なくとも1つのエポキシ樹脂を含む、請求項1に記載の半導体封止用エポキシ樹脂組成物。
(式(3)において、R1~R4は、水素原子、あるいは炭素数1~10の置換または非置換の炭化水素基であり、全てが同一でも異なっていてもよく、nは0~3の整数である。)
(式(4)において、Rは、水素原子、あるいは炭素数1~10の置換または非置換の炭化水素基であり、全てが同一でも異なっていてもよく、nは0~20の整数である。)
(式(5)において、R5~R13は、水素原子、あるいは炭素数1~10の置換または非置換の炭化水素基であり、全てが同一でも異なっていてもよく、nは0~3の整数である。) - 請求項1に記載の半導体封止用エポキシ樹脂組成物で封止された半導体素子を含む、半導体装置。
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CN201180015608.6A CN102822271B (zh) | 2010-03-25 | 2011-03-16 | 半导体封装用环氧树脂组合物和使用其的半导体装置 |
SG2012063160A SG183815A1 (en) | 2010-03-25 | 2011-03-16 | Epoxy resin composition for semiconductor encapsulation, and semiconductor device using the same |
US13/581,637 US9048187B2 (en) | 2010-03-25 | 2011-03-16 | Epoxy resin composition for semiconductor encapsulation, and semiconductor device using the same |
KR1020127027621A KR101789349B1 (ko) | 2010-03-25 | 2011-03-16 | 반도체 밀봉용 에폭시 수지 조성물 및 이것을 사용한 반도체 장치 |
JP2012506802A JP5725016B2 (ja) | 2010-03-25 | 2011-03-16 | 半導体封止用エポキシ樹脂組成物およびこれを用いた半導体装置 |
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JP (1) | JP5725016B2 (ja) |
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CN (1) | CN102822271B (ja) |
MY (1) | MY156340A (ja) |
SG (1) | SG183815A1 (ja) |
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JPWO2020195883A1 (ja) * | 2019-03-27 | 2021-04-08 | 住友ベークライト株式会社 | 封止用樹脂組成物および半導体装置 |
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JP6267261B2 (ja) * | 2016-03-30 | 2018-01-24 | 旭化成株式会社 | 熱硬化性樹脂組成物 |
TWI752222B (zh) * | 2017-04-28 | 2022-01-11 | 日商昭和電工材料股份有限公司 | 密封用薄膜、密封結構體、及密封結構體的製造方法 |
NL2021145B1 (en) * | 2018-06-18 | 2020-01-06 | Besi Netherlands Bv | Mould for encapsulating electronic components, insert for such a mould, method for producing an insert and method for encapsulating electronic components |
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JPWO2011118157A1 (ja) | 2013-07-04 |
TW201141937A (en) | 2011-12-01 |
TWI488912B (zh) | 2015-06-21 |
US20120319306A1 (en) | 2012-12-20 |
CN102822271B (zh) | 2014-12-31 |
US9048187B2 (en) | 2015-06-02 |
KR101789349B1 (ko) | 2017-10-23 |
MY156340A (en) | 2016-02-15 |
KR20130018788A (ko) | 2013-02-25 |
JP5725016B2 (ja) | 2015-05-27 |
CN102822271A (zh) | 2012-12-12 |
SG183815A1 (en) | 2012-10-30 |
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