CN104910584A - Resin composition for sealing semiconductor and semiconductor device - Google Patents
Resin composition for sealing semiconductor and semiconductor device Download PDFInfo
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- CN104910584A CN104910584A CN201510108006.5A CN201510108006A CN104910584A CN 104910584 A CN104910584 A CN 104910584A CN 201510108006 A CN201510108006 A CN 201510108006A CN 104910584 A CN104910584 A CN 104910584A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
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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
- C08G2190/00—Compositions for sealing or packing joints
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Abstract
The invention provides a condensate which has high glass transformation temperature, high mechanical strength and electric insulating performance under high temperature, low moisture absorption performance, and less thermal decomposition and excellent solder reflow-resistant characteristic, and further provides a resin composition with excellent forming performance. The resin composition contains components of A to D, an epoxy compound A indicated by formula 1, a copolymer B obtained through hydrosilylationreaction between an epoxy compound containing alkenyl and organopolysiloxane represented by an average formula 2, a Phenolic compound C represented by formula 3 and inorganic filler D.
Description
Technical field
The present invention relates to resin composition for sealing semiconductor and possess the semiconductor device of the cured article obtained by said composition.
Background technology
At present, the main flow of the semiconductor device such as diode, transistor, IC, LSI is resin packed.Because other thermosetting resin of the formability of epoxy resin, cementability, electrical specification, mechanical characteristics and wet fastness geometric ratio is excellent, so usually composition epoxy resin to be used as the potting resin of semiconductor device.But in recent years in the market of electronics, the miniaturization of semiconductor device, lightweight, high performance and the highly integrated of semiconductor element are in progress day by day.In addition, in the field engineering innovation promoting semiconductor device, increasingly stringent is become to the requirement of the epoxy resin being used as semiconductor sealing material.Due to the high performance, highly integrated of semiconductor device, the thermal value of semiconductor element increases, and junction temperature reaches the high temperature of 150 ~ 175 DEG C.As semiconductor device integral, adopt the structure of easily discharging heat, but also heat-resistant quality is required to potting resin itself.In addition, under the semiconductor device of mobile applications, high withstand voltage purposes is exposed to hot environment, so except thermotolerance more, also require that second-order transition temperature is high, physical strength under high temperature is high.
On the other hand, along with the rising of temperature installed by solder flux, if semiconductor device moisture absorption, then produce encapsulation when mounted and break, or the unfavorable condition such as packaged material and metal frame, organic substrate, semiconductor element interface peel.Therefore, agent of low hygroscopicity and and the high-adhesiveness of metal frame, organic substrate or semiconductor element are also required to potting resin composition.But the moisture uptake of the resin combination that usual second-order transition temperature is high is large, the weight caused by resin decomposition during High temperature storage reduces and becomes large.
Patent documentation 1 describes and makes the epoxy resin containing thiazolinyl carry out addition reaction with the organopolysiloxane with hydrosilyl groups (hydrosilyl) and the multipolymer that obtains, describe by by this multipolymer blending in the composition epoxy resin being main component with curable epoxy resin and solidifying agent, thus the semiconductor component packing material of fracture-resistant excellence can be provided.But thermotolerance, the agent of low hygroscopicity of this resin combination are not enough.
Patent documentation 2 describes the composition epoxy resin containing the phenol novolacs (phenol novolac resin) in crosslinking group with biphenyl support group (biphenylene) structure, epoxy resin and curing catalyst and comprises the semiconductor sealing material of said composition.The second-order transition temperature that patent documentation 2 describes said composition is high.
Patent documentation 3 describes the epoxy resin with the chemical structure 1 valency phenols and divalent phenols being cross-linked and being obtained by biphenylene class.Describe this epoxy resin and there is high second-order transition temperature, the cured article of thermotolerance and excellent in flame retardance can be provided.
In patent documentation 4, describe epoxy resin composition for semiconductor encapsulation, describe and by epoxy resin and phenol resins solidifying agent, there is biphenyl backbone and phenol skeleton respectively and the cured article with the excellent resistance to backflow disruptiveness of agent of low hygroscopicity and excellent toughness, display is provided.Its reason is, because this resin has biphenylene skeleton, so cross-linking set spacing is long, the concentration of epoxy group(ing) is low, and the ratio of phenyl ring is high.
Prior art document
Patent documentation
[patent documentation 1] Japanese Laid-Open Patent Publication 62-212417 publication
[patent documentation 2] Japanese Unexamined Patent Publication 2011-252037 publication
[patent documentation 3] Japanese Unexamined Patent Publication 2013-43958 publication
No. 3388537th, [patent documentation 4] Japanese Patent
[patent documentation 5] WO2012/053522 publication.
Summary of the invention
Invent problem to be solved
But the potting resin composition described in patent documentation 2 and 3 has following problem: agent of low hygroscopicity is not enough; If place for a long time under the condition more at higher temperature than second-order transition temperature, then because of thermolysis, weight reduces; Produce in temperature cycling test and break or peel off.In addition, the potting resin composition described in patent documentation 4 has following problem: second-order transition temperature is low, and physical strength or electric insulating quality reduce under the high temperature conditions.In addition, the potting resin composition described in patent documentation 5 is owing to having high second-order transition temperature, so weight under high temperature reduces little, but has the problem being peeling in temperature cycling test or breaking.Like this, be difficult to obtain that there is high second-order transition temperature and high flame retardant resistance, and there is the resin combination of the storage stability under low water absorbability and high temperature, excellent physical strength and electric insulating quality.
The present invention forms in view of such situation, its object is to, there is provided that a kind of second-order transition temperature is high, physical strength under high temperature and electric insulating quality is excellent and water absorbability is low, thermolysis when at high temperature preserving for a long time is few, the cured article of the excellent of resistance to solder reflow, and provide a kind of resin combination of formability excellence.
Solve the means of problem
Present inventor has performed further investigation, found that, by as follows, can reach above-mentioned problem: there is the epoxy compounds of biphenylene skeleton and phenolic compound have divalent respectively phenol skeleton with specified proportion, and composition contains hydrosilylation reactions by the epoxy compounds containing thiazolinyl and organopolysiloxane and the multipolymer obtained.
That is, the invention provides a kind of composition containing following (A) ~ (D) composition.
(A) with the epoxy compounds that following general formula (1) represents
[changing 1]
(1)
(in formula (1), R
1, R
2and R
3be alkyl, the aryl or aralkyl of hydrogen atom or substituted or unsubstituted carbonatoms 1 ~ 10 independently of each other, m
1, m
2and m
3be the integer of 1 or 2 independently of each other, relative to m
1, m
2and m
3the summation of number, be the m of integer 2
1, m
2and m
3the summation of number be 20 ~ 100%, l
1=5-m
1, l
3=5-m
3, l
2=4-m
2, n is the integer of 0 ~ 15)
(B) hydrosilylation reactions of the organopolysiloxane represented by epoxy compounds and the following column average formula (2) containing thiazolinyl and the multipolymer that obtains are 2 ~ 20 mass parts relative to (A) composition of total 100 mass parts, (B) composition with (C) composition
[changing 2]
(2)
(in formula (2), R is 1 valency alkyl of substituted or unsubstituted carbonatoms 1 ~ 10 independently of each other, and a is the positive number of 0.01≤a≤1, and b is the positive number of 1≤b≤3,1.01≤a+b < 4)
(C) phenolic compound represented with following general formula (3) is 20 ~ 50 mass parts relative to (A) composition of total 100 mass parts, (B) composition and (C) composition
[changing 3]
(3)
(in formula (3), R
4, R
5and R
6be alkyl, the aryl or aralkyl of hydrogen atom or substituted or unsubstituted carbonatoms 1 ~ 10 independently of each other, p
1, p
2and p
3be the integer of 1 or 2 independently of each other, relative to p
1, p
2and p
3the summation of number, be the p of integer 2
1, p
2and p
3the summation of number be 20 ~ 100%, q
1=5-p
1, q
3=5-p
3, q
2=4-p
2, n ' is the integer of 0 ~ 15), and
(D) inorganic filler is 150 ~ 1500 mass parts relative to (A) composition of total 100 mass parts, (B) composition and (C) composition.
In addition, the invention provides a kind of semiconductor device possessing the cured article solidified by above-mentioned composition.
The effect of invention
Composition of the present invention provides that second-order transition temperature is high, the cured article of excellent heat resistance, at high temperature physical strength and electric insulating quality excellence.Even if preserve for a long time under the high temperature of this cured article more than second-order transition temperature, the weight caused by thermolysis reduces also few, and water absorbability is low in addition, and resistance to solder reflow is also excellent.Therefore, composition of the present invention is particularly suitable as the potting resin of the semiconductor device of surface installing type.
Embodiment
Below, the present invention will be described in more detail.
(A) composition is the epoxy compounds represented with following general formula (1).
[changing 4]
(1)
(in formula (1), R
1, R
2and R
3be alkyl, the aryl or aralkyl of hydrogen atom or substituted or unsubstituted carbonatoms 1 ~ 10, preferably carbonatoms 1 ~ 6 independently of each other, m
1, m
2and m
3be the integer of 1 or 2 independently of each other, relative to m
1, m
2and m
3the summation of number, be the m of integer 2
1, m
2and m
3the summation of number be 30 ~ 100%, l
1=5-m
1, l
3=5-m
3, l
2=4-m
2, n is the integer of 0 ~ 15)
Above-mentioned (A) epoxy compounds is by obtaining following phenolic compound epoxidation, and described phenolic compound has the structure 1 valency phenol skeleton of specified proportion and divalent phenol skeleton being linked and obtained by biphenylene skeleton.This epoxy compounds has divalent phenol skeleton with following ratio: in above-mentioned formula (1), at m
1, m
2and m
3total number in, be the m of integer 2
1, m
2and m
3ratio (ratio of divalent phenol skeleton) be 20 ~ 100%, preferably 30 ~ 100%.If the ratio of divalent phenol skeleton in above-mentioned scope, then becomes second-order transition temperature high, the composition of High temperature storage characteristic, water absorbability excellence.
The present inventor finds: because epoxy compounds and following phenolic compound have the divalent phenol skeleton of above-mentioned specified quantitative, ortho-cresol phenolic aldehyde (o-cresol novolac) the type epoxy resin known with the epoxy compounds high as the effect improving second-order transition temperature, tris-phenol type epoxy resin, naphthalene type epoxy resin are compared with dicyclopentadiene type epoxy resin etc., can provide that second-order transition temperature is high, excellent heat resistance, the cured article of not thermolysis and then water absorbability excellence when High temperature storage.
As R
1, R
2and R
3hydrogen atom can be listed, the alkyl such as methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, amyl group, neo-pentyl, hexyl, octyl group, nonyl, decyl, the aryl such as phenyl, tolyl, xylyl, naphthyl, the aralkyl such as benzyl, phenylethyl, phenyl propyl, and by part or all group obtained with displacements such as halogen atom, cyano group such as fluorine, bromine, chlorine of the hydrogen atom of these groups.Be preferably hydrogen atom, methyl, ethyl, phenyl.
Together can use with above-mentioned epoxy compounds: be the m of integer 1
1, m
2and m
3ratio (ratio of 1 valency phenol skeleton) be 100% epoxy compounds.In addition, the epoxy compounds (such as phenol aralkyl type epoxy resin, biphenyl type epoxy resin, dihydroxyphenyl propane (bis A) type epoxy resin, Bisphenol F (bis F) type epoxy resin, naphthalene type epoxy resin, ortho-cresol phenol aldehyde type epoxy resin, trisphenol alkane type epoxy resin, dicyclopentadiene type epoxy resin etc.) of the structure beyond the structure having and represent with above-mentioned formula (1) can also be used.Relative to the summation of the epoxy compounds with above-mentioned formula (1), the amount of these epoxy compoundss is advisable with below 50 quality %, preferably below 30 quality %.
(B) composition is the copolymerization that the hydrosilylation reactions of the hydrogen organopolysiloxane (hydrogen organopolysiloxane) represented by the epoxy compounds containing thiazolinyl and following column average formula (2) is obtained.Composition of the present invention is by guaranteeing high thermotolerance and water absorbability containing this multipolymer.
[changing 5]
(2)
(in formula, R is 1 valency alkyl of substituted or unsubstituted carbonatoms 1 ~ 10, preferably carbonatoms 1 ~ 6, and a is 0.01≤a≤1, and b is 1≤b≤3,1.01≤a+b < 4)
Epoxy compounds containing thiazolinyl such as by with Epicholorohydrin by the phenol resins epoxidation containing thiazolinyl or make 2-chavicol and current known epoxy compounds carry out partial reaction and obtain.This epoxy compounds such as can following average formula (4) or (5) expression.
[changing 6]
(4)
(R
2 'for there is the aliphatic monovalent hydrocarbon of carbonatoms 3 ~ 15, the preferably carbonatoms 3 ~ 5 of thiazolinyl, R
3 'for glycidyl oxygen base or with-OCH
2cH (OH) CH
2the group that OR ' represents, R ' for having the monovalent hydrocarbon of carbonatoms 3 ~ 10, the preferably carbonatoms 3 ~ 5 of thiazolinyl, k to be 1, k ' be 0 or 1, x be the positive number of 1 ~ 30, y is the positive number of 1 ~ 3)
[changing 7]
(5)
(R
2 ', R
3 ', k and k ' be described above, x ' is the positive number of 1 ~ 30, and y ' is the positive number of 1 ~ 3)
As the epoxy compounds represented with above-mentioned average formula, include, for example out following compounds.
[changing 8]
[changing 9]
[changing 10]
(in above-mentioned formula, x and y is the positive number represented with 1 < x < 10,1 < y < 3)
The hydrogen organopolysiloxane represented with above-mentioned average formula (2) at least has 1 SiH base in 1 molecule.In formula (2), R can list methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, amyl group, neo-pentyl, hexyl, octyl group, nonyl, the alkyl such as decyl, vinyl, allyl group, propenyl, pseudoallyl, butenyl, hexenyl, cyclohexenyl, the thiazolinyls such as octenyl, phenyl, tolyl, xylyl, the aryl such as naphthyl, benzyl, phenylethyl, the aralkyl such as phenyl propyl, with part or all of the hydrogen atom by these groups with fluorine, bromine, the halogen atoms such as chlorine, the group that cyano group etc. are replaced and obtained, such as chloromethyl, chloropropyl, bromotrifluoromethane, the halogen-substituted alkyls such as trifluoro propyl, with cyano ethyl etc.Be preferably methyl, ethyl, phenyl.
The organopolysiloxane represented with above-mentioned average formula (2) can be straight-chain, ring-type and branched in any one.Such as can represent by following formula (a) ~ (c).
[changing 11]
(a)
In above-mentioned formula, R is substituted or unsubstituted, carbonatoms 1 ~ 10, preferably carbonatoms 1 ~ 6 monovalent hydrocarbon independently of each other, R
9for hydrogen atom or the group of option being selected from R, R
8for group as follows.N
1be the integer of 5 ~ 200, n
2be the integer of 0 ~ 2, n
3be the integer of 0 ~ 10, n
4be 1 or 0.
[changing 12]
R and R
9as mentioned above, n
5it is the integer of 1 ~ 10.But the compound of above-mentioned formula (a) at least has the hydrogen atom that 1 is bonded to Siliciumatom in 1 molecule.
[changing 13]
(b)
In formula (b), R is described above, n
6be the integer of 1 ~ 10, n
7be 1 or 2.
[changing 14]
(c)
In formula (c), R and R
9as mentioned above, r is the integer of 0 ~ 3, R
10maybe can have the monovalent hydrocarbon of the carbonatoms 1 ~ 10 of Sauerstoffatom for hydrogen atom, the compound of above-mentioned formula (c) at least has the hydrogen atom that 1 is bonded to Siliciumatom in 1 molecule.
As above-mentioned hydrogen organopolysiloxane, two end hydrogen methyl polysiloxane, two end hydrogen methyl phenyl silicones etc. are applicable.Such as preferred following compound.
[changing 15]
(in formula, n is the integer of 20 ~ 100)
[changing 16]
(in formula, m is the integer of 1 ~ 10, and n is the integer of 10 ~ 100)
(B) composition is the multipolymer making above-mentioned epoxy compounds containing thiazolinyl and hydrogen organopolysiloxane carry out hydrosilylation reactions to obtain.As long as hydrosilylation reactions is according to current known method.Such as obtain by carrying out reacting by heating under existing at the platinum class catalyzer of such as Platinic chloride and so on.This hydrosilylation reactions is particularly advisable to be heated to 60 ~ 120 DEG C in the inert solvents such as benzene, toluene, methyl iso-butyl ketone (MIBK).About the mixing proportion of epoxy compounds and siloxanes, the number of the thiazolinyl 1 that the SiH base had by siloxanes has relative to epoxy compounds is set to more than 1.0, preferably 1.5 ~ 5.0 and is advisable.
Relative to (A) composition of total 100 mass parts, (B) composition and (C) composition, the amount of (B) composition in composition is 2 ~ 20 mass parts, is preferably 2 ~ 8 mass parts.
(C) composition is the phenolic compound represented with following general formula (3).
[changing 17]
(3)
(in formula (3), R
4, R
5and R
6be hydrogen atom or substituted or unsubstituted, carbonatoms 1 ~ 10, preferably carbonatoms 1 ~ 6 alkyl, aryl or aralkyl independently of each other, p
1, p
2and p
3be the integer of 1 or 2 independently of each other, relative to p
1, p
2and p
3the summation of number, be the p of integer 2
1, p
2and p
3the summation of number be 20 ~ 100%, be preferably 30 ~ 100%, q
1=5-p
1, q
3=5-p
3, q
2=4-p
2, n ' is the integer of 0 ~ 15)
The compound of above-mentioned formula (3) is for becoming the compound of the precursor of above-mentioned (A) epoxy compounds.As mentioned above, composition of the present invention has the divalent phenol skeleton of specified quantitative in the structure by (C) phenolic compound, and the cured article obtained is that second-order transition temperature is high, and the cured article of thermotolerance, water absorbability excellence.
As R
4, R
5and R
6hydrogen atom can be listed, the alkyl such as methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, amyl group, neo-pentyl, hexyl, octyl group, nonyl, decyl, the aryl such as phenyl, tolyl, xylyl, naphthyl, the aralkyl such as benzyl, phenylethyl, phenyl propyl, and by part or all group obtained with displacements such as halogen atom, cyano group such as fluorine, bromine, chlorine of the hydrogen atom of these groups.Be preferably hydrogen atom, methyl, ethyl, phenyl.
Together can use with above-mentioned phenolic compound: be the p of integer 1
1, p
2and p
3ratio (ratio of 1 valency phenol skeleton) be 100% phenolic compound.In addition, also the phenolic compound of the structure beyond the structure that has and represent with above-mentioned formula (3) can be used, such as phenol novolacs, the phenol resins containing naphthalene nucleus, aralkyl type phenol resin, trisphenol alkane type phenol resins, biphenyl type phenol resin, ester ring type phenol resins, heterocyclic type phenol resins, phenol resins containing naphthalene nucleus, the bisphenol type such as bisphenol A type resin, bisphenol F type resin phenol resins etc.Relative to the summation of the phenolic compound with above-mentioned formula (3), the amount of these phenolic compound is advisable with below 50 quality %, preferably below 30 quality %.
Relative to (A) composition of total 100 mass parts, (B) composition and (C) composition, the amount of (C) composition in composition can be 20 ~ 50 mass parts, preferably 30 ~ 45 mass parts.
(D) composition is inorganic filler.As this inorganic filler, fused silica, crystallinity silicon-dioxide, cristobalite etc. can be listed silica-based, aluminum oxide, silicon nitride, aluminium nitride, boron nitride, titanium oxide, glass fibre, magnesium oxide, zinc oxide.The median size of these inorganic fillers, shape, without particular restriction, are selected according to purposes.Usual median size is 1 ~ 50 μm, especially 4 ~ 20 μm.This median size is for by Cirrus Laser (シ ー ラ ス レ ー ザ ー) etc. laser diffraction granularity measure of spread and the value obtained.
In these inorganic fillers, as under 120 DEG C, 2.1 normal atmosphere with the extraction conditions of 5g sample/50g water extract impurity, chlorion is below 10ppm and sodium ion is below 10ppm is suitable, and chlorion is below 5ppm and sodium ion is that below 5ppm is more suitable.If more than 10ppm, then the resistance to moisture performance of the semiconductor device that encapsulates of useful composition situation about reducing.
Relative to (A) composition of total 100 mass parts, (B) composition and (C) composition, the blending amount of inorganic filler is 150 ~ 1,500 mass parts, is preferably 250 ~ 1,200 mass parts.Particularly can be 60 ~ 94 quality % of composition in its entirety, preferably 70 ~ 92 quality %, further preferred 75 ~ 90 quality %.
About inorganic filler, in order to strengthen the bonding strength of resin and inorganic filler, preferred blending has carried out surface-treated weighting agent with the coupling agent such as silane coupling agent, titanate coupling agent in advance.As such coupling agent, preferred use γ-glycidoxypropyltrimewasxysilane, γ-glycidoxypropyl diethoxy silane, β-(3, 4-epoxycyclohexyl) epoxy silane such as ethyl trimethoxy silane, N-β (amino-ethyl)-gamma-amino propyl trimethoxy silicane, the reactant of imidazoles and γ-glycidoxypropyltrimewasxysilane, γ aminopropyltriethoxy silane, the aminosilanes such as N-phenyl-gamma-amino propyl trimethoxy silicane, γ-hydrosulphonyl silane, the silane coupling agents such as hydrosulphonyl silane such as γ-thiirane oxygen base propyl trimethoxy silicane (γ-エ ピ ス Le Off ィ De キ シ プ ロ ピ Le ト リ メ ト キ シ シ ラ Application: γ-episulfidoxypropyltrimethoxysilane).The blending amount of the coupling agent that surface treatment uses and surface treatment method without particular restriction, as long as according to current known method.
In the present compositions, can the various additive such as blending releasing agent, fire retardant, ion-trapping agent, antioxidant, cementability imparting agent as required further.
As releasing agent, without particular restriction, known releasing agent can be used.Include, for example out carnauba wax, rice bran wax (rice wax), polyethylene, oxidic polyethylene, montanic acid, the wax such as ester cpds of montanic acid and saturated alcohol, 2-(2-Hydroxy-ethylamino)-ethanol, ethylene glycol, glycerine etc.; The multipolymer etc. of stearic acid, stearate, stearylamide, ethylene bis stearamide, ethene and vinyl acetate, they can be used alone a kind or combinationally use two or more.Relative to (A) composition of total 100 mass parts, (B) composition and (C) composition, the blending amount of releasing agent is 0.5 ~ 5 mass parts, is preferably 1 ~ 3 mass parts.
As fire retardant, without particular restriction, known fire retardant can be used.Include, for example out phosphazene compound, silicone compounds, load has the talcum of zinc molybdate, load has zinc molybdate zinc oxide, aluminium hydroxide, magnesium hydroxide, molybdenum oxide, ANTIMONY TRIOXIDE SB 203 99.8 PCT etc., they can be used alone a kind or combinationally use two or more.Relative to (A) composition of total 100 mass parts, (B) composition and (C) composition, the blending amount of fire retardant is 2 ~ 20 mass parts, is preferably 3 ~ 10 mass parts.
As ion-trapping agent, without particular restriction, known ion-trapping agent can be used.Such as can use hydrotalcite, bismuth hydroxide compound, rare-earth oxide etc., they can be used alone a kind or combinationally use two or more.Relative to (A) composition of total 100 mass parts, (B) composition and (C) composition, the blending amount of ion-trapping agent is 0.5 ~ 10 mass parts, is preferably 1.5 ~ 5 mass parts.
As cementability imparting agent, without particular restriction, known cementability imparting agent can be used.Include, for example out above-mentioned coupling agent.They can be used alone a kind or combinationally use two or more.Relative to (A) composition of total 100 mass parts, (B) composition and (C) composition, the blending amount of cementability imparting agent is 0.2 ~ 5 mass parts, is preferably 0.5 ~ 3 mass parts.
The preparation method of composition of the present invention is without particular restriction.As long as such as (A) ~ (D) composition and other composition are as required carried out blending with the ratio of components of regulation, after being mixed sufficiently uniformly by mixing machine etc., carry out the melting mixing process using hot roll, kneader, forcing machine etc., then carry out cooling curing and be ground into suitable size.The composition obtained can serve as shaped material.
Composition of the present invention is effective especially as the potting resin of the semiconductor devices such as transistor-type, modular type, DIP type, SO type, Flat Package, ball grid array type.Utilize the method for packing of the semiconductor device of the present composition without particular restriction, as long as utilize the current method of forming (such as transfer molding, injection molding, injection molding etc.).Be particularly preferably transfer molding.
Shaping (solidification) condition of composition of the present invention is without particular restriction, but preferred 45 ~ 180 seconds at 160 ~ 190 DEG C.In addition, the after fixing carrying out 2 ~ 16 hours at 170 ~ 250 DEG C is wished.
The weight caused by thermolysis that composition of the present invention at high temperature, particularly carries out when preserving for a long time at 200 DEG C ~ 250 DEG C reduces little, and long term high temperature is excellent in reliability.In addition, excellent with the adhesivity of copper lead frame or silver coating, there is high insulativity.In addition, with the wet fastness of the semiconductor device packaged by the cured article of said composition or resistance to solder reflow also excellent.In addition, can use the device identical with the composition epoxy resin being typically used as transfer molding material, condition of molding, throughput is also excellent.
Embodiment
Below, illustrate that embodiment and comparative example are to illustrate in greater detail the present invention, but do not limit the invention to the following example.
[A composition]
Epoxy compounds 1
Epoxy compounds so that following formula (6) represents: NC-3500 (Japanese chemical drug system)
[changing 18]
(6)
In above-mentioned formula, R
1~ R
3for hydrogen atom, the ratio of the phenol of 1 valency and the phenol of divalent is=36/64 (number ratio (%)), and n=1.4 (mean value), epoxy equivalent (weight) is 208.
Epoxy compounds 2
In the glass reaction vessel possessing whipping appts, condenser and nitrogen ingress pipe, add the following SH-005-04 (bright and change into system, the phenol resins of ratio=71/29 of 1 valency phenol and divalent phenol) of 55.0g (0.33 mole), the Epicholorohydrin of 365.6g (4.0 moles), the methyl alcohol of 50g also dissolves equably.Drop into 96% sodium hydroxide of the solid state of 13.7g (0.3 mole) with gradation in 90 minutes in 50 DEG C.Then, in 50 DEG C of reactions 2 hours, after being warming up to 70 DEG C, reaction 2 hours is continued further.After the completion of reaction, excessive Epicholorohydrin is under reduced pressure removed.
In reactor residue, drop into the methyl iso-butyl ketone (MIBK) of 85g and make it dissolve.Add 25% aqueous sodium hydroxide solution of 5.3g (0.03 mole) and react 1 hour in 70 DEG C.After the completion of reaction, repeat 7 washing process and become neutrality to water layer.By removing methyl iso-butyl ketone (MIBK) at heating evaporated under reduced pressure, thus obtain representing and R with above-mentioned formula (6) of 75g
1~ R
3the value of=H, n is the epoxy compounds 2 of 1.3.The epoxy equivalent (weight) of the epoxy compounds obtained is 224.
Epoxy compounds 3
In the glass reactor possessing whipping appts, condenser and nitrogen ingress pipe, the Resorcinol of 220g (2.0 moles) is dissolved in the water of 150g, add 4 of 125.5g (0.5 mole), 4 '-two (chloromethyl) biphenyl, in 100 DEG C of reactions 3 hours.Then, be warming up to 160 DEG C, make 4,4 '-two (chloromethyl) biphenyl complete reaction.Therebetween, distillation removes the HCl and water that generate.After the completion of reaction, remove unreacted Resorcinol by underpressure distillation, obtain the phenol resins of the 1 valency phenol of 180g and ratio=0/100 (number ratio (%)) of divalent phenol thus.The hydroxyl equivalent of this phenol resins is 115g/eq.
Then, add the above-mentioned phenol novolacs of 50.0g (0.41 mole), the Epicholorohydrin of 451.2g (4.9 moles), 50g methyl alcohol and dissolve equably.Drop into 96% sodium hydroxide of the solid state of 16.9g (0.4 mole) with gradation in 90 minutes in 50 DEG C.Then, in 50 DEG C of reactions 2 hours, after being warming up to 70 DEG C, reaction 2 hours is continued further.After the completion of reaction, excessive Epicholorohydrin is under reduced pressure removed.In reactor residue, drop into the methyl iso-butyl ketone (MIBK) of 85g and make it dissolve.Add 25% aqueous sodium hydroxide solution of 6.5g (0.04 mole) and react 1 hour in 70 DEG C.After the completion of reaction, repeat 7 washing process and become neutrality to water layer.By removing methyl iso-butyl ketone (MIBK) at heating evaporated under reduced pressure, thus obtain representing and R with above-mentioned formula (6) of 67g
1~ R
3the value of=H, n is the epoxy compounds 3 of 1.2.The epoxy equivalent (weight) of the epoxy compounds obtained is 176.
Epoxy compounds 4
Biphenyl aralkyl-type epoxy resin: NC-3000 (Japanese chemical drug system), ratio=100/0 (number ratio (%)) of 1 valency phenol and divalent phenol, epoxy equivalent (weight): 272.
Epoxy compounds 5
Triphenylalkane type epoxy resin: EPPN-501H (Japanese chemical drug system), ratio=100/0 (number ratio (%)) of 1 valency phenol and divalent phenol, epoxy equivalent (weight): 165.
[B component]
By the reaction of the epoxy compounds containing thiazolinyl and organopolysiloxane and the copolymerization obtained
To the internal volume possessing reflux exchanger, thermometer, agitator and dropping funnel be add respectively in the four neck flasks of 1 liter 200g with the phenol novolacs of glycidyl allyl ether modification, (phenol equivalent is for 125, allyl group equivalent is 1100), the chloromethyl oxirane of 800g, the cetyl trimethylammonium bromide of 0.6g heat, at the temperature of 110 DEG C, be uniformly mixed 3 hours.Cooled to make temperature be 70 DEG C, after being decompressed to 160mmHg, while carrying out azeotropic dehydration, dripped 50% aqueous solution of the sodium hydroxide of 128g wherein with 3 hours.The content decompression obtained is distilled except desolventizing, then after dissolving with the mixed solvent of the methyl iso-butyl ketone (MIBK) of 300g and the acetone of 300g, wash, it is under reduced pressure distilled except desolventizing thus obtains containing allylic epoxy resin (allyl group equivalent is 1590, and epoxy equivalent (weight) is 190).Add the methyl iso-butyl ketone (MIBK) of this epoxy resin and 170g, the toluene of 330g, the platinum concentration of 0.07g be 2% 2-Ethylhexyl Alcohol modification platinum acid chloride solution, carry out the azeotropic dehydration of 1 hour, drip the organopolysiloxane represented with following formula (7) of 133g at a reflux temperature with the time for adding of 30 minutes.And then stir 4 hours at the same temperature with after reacting, washed by the content obtained, under reduced pressure distillation is except the multipolymer obtaining white yellow opaque solid during desolventizing.Epoxy equivalent (weight) is the ICI melt viscosity at 280,150 DEG C is 800cP, and silicone content is 31%.
[changing 19]
(7)
[C composition]
Phenolic compound 1
Compound so that following formula (8) represents: SH-005-02 (bright and change into system)
[changing 20]
(8)
In above-mentioned formula (8), R
4~ R
6for hydrogen atom, ratio=36/64 (number ratio (%)) of 1 valency phenol and divalent phenol, n '=1.4 (mean value), hydroxyl equivalent is 135.
Phenolic compound 2
SH-005-04 (bright and change into system): represent and R with above-mentioned formula (8)
4~ R
6ratio=71/29 (number ratio (%)) of=H, 1 valency phenol and divalent phenol, hydroxyl equivalent are the compound of 169
Phenolic compound 3
MEHC-7851SS (bright and change into system): to represent with following formula (9) and ratio=100/0 of 1 valency phenol and divalent phenol (number ratio (%)), hydroxyl equivalent are the compound of 203
[changing 21]
(9)
Phenolic compound 4
TD-2131 (DIC system): to represent with following formula (10) and ratio=100/0 of 1 valency phenol and divalent phenol (number ratio (%)), hydroxyl equivalent are the compound of 110
[changing 22]
(10)
[D composition]
Inorganic filler: melting spherical silicon dioxide (median size is 15 μm, imperial gloomy system)
[other composition]
Carnauba wax (TOWAX-131, East Asia changes into system)
Silane coupling agent:
3-mercaptopropyi Trimethoxy silane (KBM-803, SHIN-ETSU HANTOTAI's chemistry system)
3-glycidoxypropyltrimewasxysilane (KBM-403, SHIN-ETSU HANTOTAI's chemistry system)
Curing catalyst: triphenyl phosphine (northern Xinghua length of schooling)
Fire retardant material: load has the zinc oxide (KEMGARD-911B, Sherwin Williams system) of molybdenum
Ion-trapping agent: hydrotalcite compound (DHT-4A-2, consonance chemistry system).
According to the composition described in lower list 1 and table 2, mentioned component is carried out blending, by the two roll melting mixing equably of heat, cooling, pulverizes thus obtains composition.According to method as follows, each composition obtained is evaluated.Result is recorded in table 1 and table 2.
(i) helical flow
Use the mould meeting EMMI standard, with 175 DEG C, 6.9N/mm
2, molding time is that the condition of 180 seconds measures.
(ii) second-order transition temperature
With the condition that 175 DEG C × 120 seconds, forming pressure are 6.9MPa, each composition is carried out transfer molding, then carry out the after fixing of 4 hours in 250 DEG C, obtain the test film of 5 × 5 × 15mm thus.The dimensional change of determination test sheet under the heat-up rate of 5 DEG C/min (Rigaku TMA8310), the intersection point according to the tangent line of the tangent lines of 50 ~ 100 DEG C and 270 ~ 290 DEG C tries to achieve glass transition point.
(iii) changes in weight when high temperature is placed
With the condition that 175 DEG C × 120 seconds, forming pressure are 6.9MPa, each composition is carried out transfer molding, then carry out the after fixing of 4 hours in 180 DEG C, obtain the test film of 10 × 100 × 4mm thus.Test film is preserved 336 hours in 250 DEG C of baking ovens.Measure the weight of the test film before based on preservation, because preserving the ratio (%) of the weight minimizing caused.
(iv) HTSL characteristic confirms
Cu alloy (Olin C7025) the 100pin QFP lead frame processed utilizing each composition the chip of 6mm × 6mm, DA agent (Ablestick 84-1LMI-SR4), die pads portion (8mm × 8mm) and wire bonds portion to be coated with Ag encapsulates by the following method: carry out transfer molding with the condition that 175 DEG C × 120 seconds, forming pressure are 6.9MPa, then carry out the after fixing of 4 hours in 180 DEG C.With lead frame cutting unit, connecting rod (tie bar) is cut off, obtain the QFP encapsulation of 20mm × 14mm × 2.7mm.This is encapsulated in 200 DEG C of baking ovens and preserves 500 hours, carry out encapsulating the confirmation of breaking after being saved and observe internal rupture, stripping with lead frame (LF) by reflectoscope.
V () temperature cycle characteristic confirms
Utilize each composition, Cu alloy (Olin C7025) the 100pin QFP lead frame processed chip of 6mm × 6mm, DA agent (Ablestick 84-1LMI-SR4), die pads portion (8mm × 8mm) and wire bonds portion being coated with Ag encapsulates by the following method: carry out transfer molding with the condition that 175 DEG C × 120 seconds, forming pressure are 6.9MPa, then carry out the after fixing of 4 hours in 180 DEG C.With lead frame cutting unit, connecting rod is cut off, obtain the QFP encapsulation of 20mm × 14mm × 2.7mm.For this encapsulation, with-65 DEG C × 30 minutes
temperature cycling test is carried out 1000 circulations by the condition of 175 DEG C × 30 minutes, carries out encapsulating the confirmation of breaking and observes internal rupture, stripping with lead frame by reflectoscope.
(vi) moisture absorption solder reflow test
Utilize each composition, Cu alloy (Olin C7025) the 100pin QFP lead frame processed chip of 6mm × 6mm, DA agent (Ablestick 84-1LMI-SR4), die pads portion (8mm × 8mm) and wire bonds portion being coated with Ag encapsulates by the following method: carry out transfer molding with the condition that 175 DEG C × 120 seconds, forming pressure are 6.9MPa, then carry out the after fixing of 4 hours in 180 DEG C.With lead frame cutting unit, connecting rod is cut off, obtain the QFP encapsulation of 20mm × 14mm × 2.7mm.After making this encapsulation moisture absorption with the condition of 30 DEG C/60%RH × 192h, by 3 times in IR reflow ovens (top temperature is 265 DEG C), carry out encapsulating the confirmation of breaking and observe internal rupture, stripping with lead frame by reflectoscope.
(vii) 260 DEG C of flexural strengths
According to JIS K6911, with the condition that 175 DEG C × 120 seconds, forming pressure are 6.9MPa, each composition is carried out transfer molding, then carry out the after fixing of 4 hours in 180 DEG C, obtain the test film of 100 × 100 × 4mm thus.After test film is placed 3 minutes in 250 DEG C of baking ovens, use Shimadzu Seisakusho Ltd.'s autoplotter (autograph) to carry out 3 pliability tests, try to achieve flexural strength.
(viii) 175 DEG C of volume specific resistances
According to JIS K6911, with the condition that 175 DEG C × 120 seconds, forming pressure are 6.9MPa, each composition is carried out transfer molding, then carry out the after fixing of 4 hours in 180 DEG C, obtain that diameter is 90mm, thickness is the test film of 2mm thus.This test film is used to measure volume specific resistance at 175 DEG C.
Utilizability in industry
Resin combination of the present invention provides that second-order transition temperature is high, the cured article of excellent heat resistance.Therefore, the thermolysis (weight minimizing) at high temperature, particularly at 200 DEG C ~ 250 DEG C during long-term preservation is few.In addition, the water absorbability of the cured article obtained by resin combination of the present invention is low, and resistance to solder reflow is also excellent.In addition, this cured article physical strength at high temperature and electric insulating quality excellent.In addition, the good forming ability of composition of the present invention.Therefore, composition of the present invention is particularly suitable as the potting resin of the semiconductor device of surface installing type.
Claims (4)
1. a composition, it contains following (A) composition ~ (D) composition:
(A) with the epoxy compounds that following general formula (1) represents,
[changing 1]
(1)
In formula (1), R
1, R
2and R
3be alkyl, the aryl or aralkyl of hydrogen atom or substituted or unsubstituted carbonatoms 1 ~ 10 independently of each other, m
1, m
2and m
3be the integer of 1 or 2 independently of each other, relative to m
1, m
2and m
3the summation of number, be the m of integer 2
1, m
2and m
3the summation of number be 20 ~ 100%, l
1=5-m
1, l
3=5-m
3, l
2=4-m
2, n is the integer of 0 ~ 15;
(B) multipolymer obtained by the hydrosilylation reactions of organopolysiloxane represented containing the epoxy compounds of thiazolinyl and following column average formula (2), be 2 ~ 20 mass parts relative to (A) composition of total 100 mass parts, (B) composition and (C) composition
[changing 2]
(2)
In formula (2), R is 1 valency alkyl of substituted or unsubstituted carbonatoms 1 ~ 10 independently of each other, and a is the positive number of 0.01≤a≤1, and b is the positive number of 1≤b≤3,1.01≤a+b < 4;
(C) with the phenolic compound that following general formula (3) represents, be 20 ~ 50 mass parts relative to (A) composition of total 100 mass parts, (B) composition and (C) composition,
[changing 3]
(3)
In formula (3), R
4, R
5and R
6be alkyl, the aryl or aralkyl of hydrogen atom or substituted or unsubstituted carbonatoms 1 ~ 10 independently of each other, p
1, p
2and p
3be the integer of 1 or 2 independently of each other, relative to p
1, p
2and p
3the summation of number, be the p of integer 2
1, p
2and p
3the summation of number be 20 ~ 100%, q
1=5-p
1, q
3=5-p
3, q
2=4-p
2, n ' is the integer of 0 ~ 15; With
(D) inorganic filler is 150 ~ 1500 mass parts relative to (A) composition of total 100 mass parts, (B) composition and (C) composition.
2. composition according to claim 1, wherein, the described epoxy compounds containing thiazolinyl in (B) composition is at least a kind of compound of being selected from following column average formula (4) or (5) and representing:
[changing 4]
(4)
R
2 'for there is the aliphatic monovalent hydrocarbon of the carbonatoms 3 ~ 15 of thiazolinyl, R
3 'for glycidyl oxygen base or with-OCH
2cH (OH) CH
2the group that OR ' represents, R ' for having the monovalent hydrocarbon of the carbonatoms 3 ~ 10 of thiazolinyl, k to be 1, k ' be 0 or 1, x be the positive number of 1 ~ 30, y is the positive number of 1 ~ 3;
[changing 6]
(5)
R
2 ', R
3 ', k and k ' be described above, x ' is the positive number of 1 ~ 30, and y ' is the positive number of 1 ~ 3.
3. the composition described in claim 1 or 2, wherein, the described organopolysiloxane in (B) composition is for being selected from least a kind of the compound represented with following formula (a) ~ (c):
[changing 7]
(a)
In formula (a), R is the monovalent hydrocarbon of substituted or unsubstituted carbonatoms 1 ~ 10 independently of each other, R
9for hydrogen atom or the group of option being selected from R, R
8for group as follows,
[changing 8]
Herein, R and R
9as mentioned above, n
5be the integer of 1 ~ 10,
N
1be the integer of 5 ~ 200, n
2be the integer of 0 ~ 2, n
3be the integer of 0 ~ 10, n
4be 1 or 0, but the compound of above-mentioned formula (a) at least have the hydrogen atom that 1 is bonded to Siliciumatom in 1 molecule;
[changing 9]
(b)
In formula (b), R is described above, n
6be the integer of 1 ~ 10, n
7be 1 or 2;
[changing 10]
(c)
In formula (c), R and R
9as mentioned above, r is the integer of 0 ~ 3, R
10maybe can have the monovalent hydrocarbon of the carbonatoms 1 ~ 10 of Sauerstoffatom for hydrogen atom, the compound of above-mentioned formula (c) at least has the hydrogen atom that 1 is bonded to Siliciumatom in 1 molecule.
4. a semiconductor device, it possesses the cured article of the composition solidification according to any one of claim 1 ~ 3.
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| JP2014-050160 | 2014-03-13 | ||
| JP2014050160A JP2015174874A (en) | 2014-03-13 | 2014-03-13 | Resin composition for encapsulating semiconductor and semiconductor device |
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|---|---|
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| KR (1) | KR20150107624A (en) |
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| CN109467942A (en) * | 2017-09-07 | 2019-03-15 | 信越化学工业株式会社 | Resin combination, resin film, semiconductor layer stack, the manufacturing method of the manufacturing method of semiconductor layer stack and semiconductor device |
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| JP6275620B2 (en) * | 2014-10-17 | 2018-02-07 | 日本化薬株式会社 | Photosensitive resin composition and cured product thereof |
| JP2018104603A (en) * | 2016-12-27 | 2018-07-05 | 日立化成株式会社 | Curable resin composition and electronic component device |
| US20200325292A1 (en) | 2017-12-27 | 2020-10-15 | Mitsubishi Gas Chemical Company, Inc. | Resin composition, prepreg, laminate, metal foil-clad laminate, printed wiring board, and multilayer printed wiring board |
| JP6848950B2 (en) * | 2018-10-30 | 2021-03-24 | 味の素株式会社 | Resin composition |
| JP6636599B2 (en) * | 2018-11-30 | 2020-01-29 | 日本化薬株式会社 | Epoxy resin composition, prepreg and metal-clad laminate, printed wiring board |
| JP7375406B2 (en) * | 2019-09-20 | 2023-11-08 | 住友ベークライト株式会社 | Photosensitive resin composition, electronic device manufacturing method, and electronic device |
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| JP2006233149A (en) * | 2005-02-28 | 2006-09-07 | Shin Etsu Chem Co Ltd | Resin composition for sealing low-dielectric film forming element and semiconductor apparatus |
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| JP3476027B2 (en) * | 1994-04-28 | 2003-12-10 | 日本化薬株式会社 | Manufacturing method of epoxy resin |
| JP3672011B2 (en) * | 1998-09-25 | 2005-07-13 | 信越化学工業株式会社 | Epoxy resin composition and laminated film and semiconductor device using this epoxy resin composition |
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2014
- 2014-03-13 JP JP2014050160A patent/JP2015174874A/en active Pending
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- 2015-03-10 KR KR1020150032924A patent/KR20150107624A/en unknown
- 2015-03-12 CN CN201510108006.5A patent/CN104910584A/en active Pending
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| JP2006233149A (en) * | 2005-02-28 | 2006-09-07 | Shin Etsu Chem Co Ltd | Resin composition for sealing low-dielectric film forming element and semiconductor apparatus |
| CN1962802A (en) * | 2005-11-07 | 2007-05-16 | 信越化学工业株式会社 | Semiconductor encapsulating epoxy resin composition and semiconductor device |
| CN103168061A (en) * | 2010-10-19 | 2013-06-19 | 住友电木株式会社 | Sealing resin composition and electronic component device |
| WO2013136685A1 (en) * | 2012-03-16 | 2013-09-19 | 住友ベークライト株式会社 | Sealing resin composition and electronic device using same |
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| CN109467942A (en) * | 2017-09-07 | 2019-03-15 | 信越化学工业株式会社 | Resin combination, resin film, semiconductor layer stack, the manufacturing method of the manufacturing method of semiconductor layer stack and semiconductor device |
| CN109467942B (en) * | 2017-09-07 | 2022-02-11 | 信越化学工业株式会社 | Resin composition, resin film, semiconductor laminate, method for producing semiconductor laminate, and method for producing semiconductor device |
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| KR20150107624A (en) | 2015-09-23 |
| JP2015174874A (en) | 2015-10-05 |
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