WO2018174446A1 - Resin composition for semiconductor package, prepreg using same, and metal foil laminated plate - Google Patents

Resin composition for semiconductor package, prepreg using same, and metal foil laminated plate Download PDF

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Publication number
WO2018174446A1
WO2018174446A1 PCT/KR2018/002779 KR2018002779W WO2018174446A1 WO 2018174446 A1 WO2018174446 A1 WO 2018174446A1 KR 2018002779 W KR2018002779 W KR 2018002779W WO 2018174446 A1 WO2018174446 A1 WO 2018174446A1
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WIPO (PCT)
Prior art keywords
group
carbon atoms
resin
resin composition
semiconductor package
Prior art date
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PCT/KR2018/002779
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French (fr)
Korean (ko)
Inventor
심창보
심희용
민현성
김영찬
송승현
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Priority claimed from KR1020180018018A external-priority patent/KR102049024B1/en
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to JP2019506376A priority Critical patent/JP6756083B2/en
Priority to CN201880003433.9A priority patent/CN109661422B/en
Priority to US16/334,201 priority patent/US11214677B2/en
Priority to EP18770850.8A priority patent/EP3480244B1/en
Publication of WO2018174446A1 publication Critical patent/WO2018174446A1/en

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
    • C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/043—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of metal
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/12—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of paper or cardboard
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    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
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    • B32B5/24—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer
    • B32B5/26—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer another layer next to it also being fibrous or filamentary
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
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    • B32B2260/02—Composition of the impregnated, bonded or embedded layer
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    • B32B2457/00—Electrical equipment
    • B32B2457/08—PCBs, i.e. printed circuit boards
    • C—CHEMISTRY; METALLURGY
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    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C08J2363/02—Polyglycidyl ethers of bis-phenols
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    • C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
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Definitions

  • the present invention relates to a resin composition for a semiconductor package having high fluidity, low thermal expansion characteristics and excellent mechanical properties, and a prepreg and a metal foil laminated plate using the same. More specifically, heat for semiconductor packages that can produce prepregs and metal foil laminates that exhibit excellent physical properties even after reflow of printed circuit boards (PCBs) . It relates to a curable resin composition and a prepreg using the same.
  • PCBs printed circuit boards
  • Copper clad laminates used in conventional printed circuit boards are prepregs when the substrate of glass fiber (Gl ass Fabr ic) is impregnated in the varnish of the thermosetting resin composition and then semi-cured, which is then copper foil. It is prepared by heating and pressing together. The prepreg is used again for the purpose of constructing a circuit pattern on the copper foil laminate and building up on it.
  • Glass fiber Ga ass Fabr ic
  • the semiconductor package is also required to be thin, and at the same time, the necessity of thinning a printed circuit board for a semiconductor package is increasing.
  • the problem of decreasing the rigidity of the printed circuit board during the thinning process is caused by the difference in thermal expansion coefficient between the chip and the printed circuit board . Due to this, warpage problems of semiconductor packages are occurring.
  • the bending phenomenon goes through a high temperature process, such as "reflow is further intensified by the phenomenon that a printed circuit board not wonbok.
  • the present invention is to provide a resin composition for a semiconductor package having high fluidity, low thermal expansion characteristics and excellent mechanical properties.
  • the present invention is to provide a prepreg and a metal foil stacking plate using the resin composition for a semiconductor package.
  • 1 selected from the group consisting of a sulfone group, a carbonyl group, a halogen group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, and an alkylene group having 1 to 20 carbon atoms
  • Amine curing agents comprising at least one functional group; Thermosetting resins; And an inorganic layering agent, wherein the inorganic filler content is 200 parts by weight or more based on 100 parts by weight of the amine curing agent and the thermosetting resin, and the content of the thermosetting resin is 400 parts by weight or less based on 100 parts by weight of the amine curing agent
  • the alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms, the heteroaryl group having 2 to 30 carbon atoms and the alkylene group having 1 to 20 carbon atoms contained in the amine curing agent are each independently
  • This specification also provides the prepreg obtained by impregnating the said resin composition for semiconductor packages in a fiber base material.
  • the prepreg In the present specification, the prepreg; And a metal foil including the prepreg integrated with the prepreg by heating and pressurization.
  • a resin composition for a semiconductor package according to a specific embodiment of the invention
  • a sulfone group, a carbonyl group, a halogen group an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, and an alkylene group having 1 to 20 carbon atoms
  • Amine curing agents comprising at least one functional group selected from the group; Thermosetting resins; And an inorganic layering agent, wherein the inorganic layering agent content is 200 parts by weight or more based on 100 parts by weight of the amine curing agent and the thermosetting resin, and the content of the thermosetting resin is 400 parts by weight or less based on 100 parts by weight of the amine curing agent.
  • C1-C20 alkyl group, C6-C20 aryl group, C2-C30 heteroaryl group and C1-C20 alkylene group contained in the amine curing agent are each independently nitro group, cyano group and halogen
  • a resin composition for a semiconductor package substituted with one or more functional groups selected from the group consisting of groups.
  • the resin composition for a semiconductor package of the above embodiment, a sulfone group, a carbonyl group, a halogen group, a substituted C1-20 alkyl group, a substituted C6-20 aryl group, a substituted C2-30
  • EWG strong electron withdrawing group
  • the thermosetting resin content is included in an amount of 400 parts by weight or less with respect to 100 parts by weight of the amine curing agent, thereby preventing the change of physical properties of the thermosetting resin due to the filler added in a high content.
  • the thermosetting resin can be uniformly cured to a more uniform level without the effect of fillers, and thus the reliability of the final product can be improved, and the mechanical properties such as toughness can also be increased. have.
  • thermosetting resin content to 400 parts by weight or less with respect to 100 parts by weight of the amine curing agent
  • the amine curing agent is relatively When added in excess of the furnace, there was a limit in reducing fluidity and formability due to excessive curing of the thermosetting resin.
  • the electronic drawer functional group to 400 parts by weight or less with respect to 100 parts by weight of the amine curing agent
  • the resin composition for a semiconductor package includes a sulfone group, a carbonyl group, a halogen group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, and 1 to 20 carbon atoms. It may include an amine curing agent containing at least one functional group selected from the group consisting of alkylene groups of.
  • the alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms, the heteroaryl group having 2 to 30 carbon atoms and the alkylene group having 1 to 20 carbon atoms contained in the amine curing agent are each independently a nitro group, It may be substituted with one or more functional groups selected from the group consisting of a no group and a halogen group.
  • the sulfone group, carbonyl group, halogen group, substituted C1-20 alkyl group, substituted C6-C20 aryl group, substituted C2-C30 heteroaryl group and substituted carbon number contained in the amine curing agent At least one functional group selected from the group consisting of alkylene groups of 1 to 20 is a strong electron drag group (EWG), wherein the amine curing agent including the electron drag functional group includes an electron. Compared with the amine curing agent which is not used, the reaction property is reduced, and thus the curing reaction of the resin composition can be easily controlled.
  • EWG electron drag group
  • the amine curing agent may include one or more compounds selected from the group consisting of the following Chemical Formulas 1 to 3.
  • A is a sulfone group, a carbonyl group, or an alkylene group having 1 to 10 carbon atoms
  • Xi to 3 ⁇ 4 are each independently a nitro group, cyano group, hydrogen atom, halogen group, alkyl group having 1 to 6 carbon atoms, and carbon number.
  • to Ys are each independently a nitro group, a cyano group, a hydrogen atom, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms.
  • R 3 , R 3 ', R 4 and' are each independently a hydrogen atom, a halogen group, an alkyl group of 1 to 6 carbon atoms, an aryl group of 6 to 15 carbon atoms, or a heteroaryl group of 2 to 20 carbon atoms, m Is an integer of 1 to 10, wherein the alkyl group of 1 to 6 carbon atoms, the aryl group of 6 to 15 carbon atoms, and the heteroaryl group of 2 to 20 carbon atoms are each independently a nitro group, Cyano group, and said groups being substituted in the halogen group consisting of at least one kinds selected functional group, "
  • ⁇ to Z 4 in Chemical Formula 3 are each independently a nitro group, a cyano group, a hydrogen atom, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms.
  • R 5, R 5 ' , R 6 and R 6 ' are each independently a hydrogen atom, a halogen group, an alkyl group of 1 to 6 carbon atoms, an aryl group of 6 to 15 carbon atoms, or a heteroaryl group of 2 to 20 carbon atoms
  • the alkyl group having 1 to 6 carbon atoms, the aryl group having 6 to 15 carbon atoms, and the heteroaryl group having 2 to 20 carbon atoms are each independently substituted with one or more functional groups selected from the group consisting of nitro, cyano and halogen groups. .
  • the alkyl group is a monovalent functional group derived from alkane, and is, for example, linear, branched or cyclic, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, It may be a nuclear chamber.
  • One or more hydrogen atoms contained in the alkyl group may each be substituted with a substituent.
  • the alkylene group is a divalent functional group derived from alkane, and is, for example, a linear, branched or cyclic group, and is a methylene group, an ethylene group, a propylene group, an isobutylene group, or a sec-butylene group. It may be a tert- butylene group, a pentylene group, a nuclear silane group and the like.
  • One or more hydrogen atoms contained in the alkylene group may be substituted with the same substituents as in the case of the alkyl group, respectively.
  • the aryl group is a monovalent functional group derived from arene rene), for example, may be monocyclic or polycyclic.
  • the monocyclic aryl group may be a phenyl group, biphenyl group, terphenyl group, stilbenyl group and the like, but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthryl group, phenanthryl group, pyrenyl group, perrylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. It is not. At least one hydrogen atom of such an aryl group may be each substituted with the same substituent as in the case of the above alkyl group.
  • the heteroaryl group is a heterocyclic group including 0, N or S as a hetero atom, and the number of carbon atoms is not particularly limited, but may be 2 to 30 carbon atoms.
  • the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group oxazole group, oxadiazole group, triazole group, pyridyl group bipyridyl group, triazine group, acridil group, pyridazine group , Quinolinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group and dibenzo Furan groups and the like, but are not limited thereto. At least one hydrogen atom of such a heteroaryl group may be substituted
  • substituted means that another functional group is bonded instead of a hydrogen atom in the compound, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent may be substituted, and when two or more are substituted, Two or more substituents may be the same or different from each other.
  • Chemical Formula 1 may include a compound represented by Chemical Formula 1-1 below:
  • Xi to 3 ⁇ 4, Ri, Ri ', R 2 and n include the above-mentioned information in the general formula (1).
  • formula 1-1 is 4,4'-diaminodiphenyl sulfone (In Formula 1-1, A is a sulfone group, X 8 , Ri, Ri ', R 2 and R 2 ' are each independently a hydrogen atom.
  • n 1
  • A is a carbonyl group,
  • X 2 , Ri, Ri ', R 2 and' are each independently a hydrogen atom, and
  • ⁇ is 1 4,4 '-(perf luoropropane-2,2-diyl) dianiline
  • A is perfluoropropane-2,2-diyl, Xi to 3 ⁇ 4 3 ⁇ 4 R 2 and' are each independently.
  • Is a hydrogen atom, n is 1.; ) , 4,4 '-(2,2,2-trifluoroethane-l ) l- diyDdiani line (A in Formula 1—1 is 2,2,2— tr if luoroethane — 1, l—diyl, Xi to X 8 , Ri, Ri ' , 3 ⁇ 4 and R 2 ' are each independently a hydrogen atom, n is 1).
  • Chemical Formula 2 may include a compound represented by Chemical Formula 2-1.
  • Chemical Formula 2-1 examples include 2,2 ', 3,3', 5,5 ', 6,6' ⁇ octafluorobiphenyl-4,4'-dlamlne (In Formula 2-1 to Y 8 is halogen fluorine Groups, R 3, and F are each independently a hydrogen atom, m is 1), 2,2'-bis (trifluoromethyl) bipheny 1-4,4 '-diamine (Y 2 and ⁇ 7 are each a tree) Is a fluoromethyl group, ⁇ 1 , ⁇ 3 , ⁇ 4 , ⁇ 5 , ⁇ 6 , ⁇ 8 are hydrogen atoms, R 3 ', 4 and R 4 ' are each independently a hydrogen atom, m is 1 J, etc. Can be mentioned.
  • Chemical Formula 3 may include a compound represented by Chemical Formula 3-1.
  • the contents of ⁇ ⁇ to Z 4 , 5 , R 5 ', Re, and Rs' include the above-described contents in Formula 3 above.
  • Chemical Formula 3-1 may include 2,3,5,6-tetrafluorobenzene-l, 4- and di amines (wherein 1, to Z 4 in Formula 3-1 are halogen, a fluorine group , R 5, R 5 1 , R 6 and 'are each independently a hydrogen atom).
  • thermosetting resin content per 100 parts by weight of the amine curing agent ⁇
  • thermosetting resin mixture content is also 400 parts by weight or less, or 150 parts by weight to 400 parts by weight, based on 100 parts by weight of the amine curing agent mixture, or
  • thermosetting resin content based on 100 parts by weight of the amine curing agent
  • thermosetting resin due to the filler added in a high content
  • fastness may be reduced, and mechanical properties such as toughness may also be reduced.
  • the resin composition for a semiconductor package has an equivalent ratio calculated by Equation 1 below 1.4 or 2.5, or 1.4 to 2.5, or 1.45 to 2.5, or 1.45 to 2. 1, or 1.45 to 1.8, or 1.49 to 1.75 Can be.
  • the total active hydrogen equivalent contained in the amine curing agent refers to the total weight (unit: g) of the amine curing agent divided by the unit hydrogen equivalent (g / eQ) of the amine curing agent.
  • the value obtained by dividing the weight (unit: g) by the unit equivalent of active hydrogen (g / eq) for each compound is obtained, and the sum thereof is contained in the amine curing agent of Equation 1 above.
  • the total equivalent active hydrogen equivalent can be obtained.
  • the active hydrogen contained in the amine curing agent is present in the amine curing agent. It refers to a hydrogen atom contained in the mino group (-N3 ⁇ 4), the active hydrogen can form a cured structure through the reaction with the curable functional group of the thermosetting resin.
  • the total curable work container equivalent contained in the thermosetting resin is a value obtained by dividing the total weight (unit: g) of the thermosetting resin by the unit equivalent (g / eq) of the curable functional group of the thermosetting resin. it means.
  • thermosetting resin When the thermosetting resin is two or more kinds of mixtures, the value obtained by dividing the weight (unit: g) by the unit equivalent weight (g / eq) of the curable functional group for each compound is calculated, and the sum thereof is the thermosetting resin of Equation 1
  • the total curable functional group equivalent contained in can be calculated
  • the curable functional group contained in the thermosetting resin means a functional group that forms a cured structure through reaction with active hydrogen of the amine curing agent, and the type of the curable functional group may also vary according to the thermosetting resin type.
  • the curable functional group contained may be an epoxy group
  • the bismaleimide resin when used as the thermosetting resin, the curable functional group contained in the bismaleimide resin may be a maleimide group.
  • the resin composition for a semiconductor package satisfies that the equivalent ratio calculated by Equation 1 is 1 ⁇ 4 or more, the amine curing agent of a sufficient level so that the curable functional groups contained in all the thermosetting resins can cause a curing reaction. It contains. Therefore, when the equivalent ratio calculated by Equation 1 in the resin composition for semiconductor package is reduced to less than 1.4, a change in physical properties of the thermosetting resin due to the filler added with a high content occurs, the thermosetting resin is more affected by the filler Since it is difficult to uniformly harden to a sufficient level, there is a disadvantage that the reliability of the final product can be reduced, and the mechanical properties can also be reduced.
  • the resin composition for a semiconductor package of the embodiment may include a thermosetting resin.
  • the thermosetting resin may include at least one resin selected from the group consisting of an epoxy resin, a bismaleimide resin, a cyanate ester resin, and a bismaleimide-triazine resin.
  • the epoxy resin can be used without limitation to those usually used in the resin composition for semiconductor packages, the type is not limited, bisphenol A epoxy resin, phenol novolak epoxy resin, phenyl aralkyl epoxy 1 type selected from the group consisting of a resin, a tetraphenyl ethane epoxy resin, a naphthalene epoxy resin, a biphenyl epoxy resin, a dicyclopentadiene epoxy resin, and a mixture of a dicyclopentadiene epoxy resin and a naphthalene epoxy resin It may be abnormal.
  • the epoxy resin is a bisphenol-type epoxy resin represented by the formula (5), a novolak-type epoxy resin represented by the formula (6), a phenyl aralkyl-based epoxy resin represented by the formula (7), represented by the formula (8)
  • a tetraphenylethane type epoxy resin a naphthalene type epoxy resin represented by the following formulas (9) and (10)
  • a dicyclopentadiene type epoxy resin represented by the following formula (12) One or more selected species may be used.
  • n is 0 or an integer from 1 to 50.
  • the epoxy resin of Formula 5 may be a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a bisphenol M type epoxy resin, or a bisphenol S type epoxy resin, respectively, according to the type of R R.
  • R is H or CH 3 ,
  • n is 0 or an integer from 1 to 50.
  • the novolak-type epoxy resin of Formula 6 may be a phenol novolak-type epoxy resin or cresol novolak-type epoxy resin, respectively, depending on the type of R. .
  • n is 0 or an integer from 1 to 50.
  • n is 0 or an integer of 1 to 50.
  • the resin composition for a semiconductor package includes an epoxy resin
  • a curing agent of an epoxy resin may be used together for curing.
  • curing agent of the said epoxy resin what is normally used for the resin composition for semiconductor packages can be used without a restriction
  • a phenol novolak type, an amine type, a thiol type, an acid anhydride type material, etc. are mentioned, These can be used individually or in mixture of 2 or more types.
  • the bismaleimide resin can be used without limitation, which is usually used in the resin composition for semiconductor packages, the type is not limited.
  • the bismaleimide resin is a diphenylmethane type bismaleimide resin represented by the following formula (13), a phenylene type bismaleimide resin represented by the following formula (14), bisphenol A type diphenyl ether bismaleimide represented by the following formula (15) It may be at least one selected from the group consisting of a mid resin, and a bismaleimide resin composed of oligomers of ' diphenylmethane bismaleimide and phenylmethane type maleimide resin represented by the following formula (16).
  • i and 3 ⁇ 4 are each independently H, CH 3 or C 2 3 ⁇ 4.
  • n is 0 or an integer from 1 to 50.
  • cyanate ester resin can be used without limitation, those usually used in the resin composition for semiconductor packages, the type is not limited.
  • the cyanate ester resin is a novolac cyanate resin represented by the following formula (17), a diclopentadiene type cyanate resin represented by the following formula (18), and a bisphenol cyanate resin represented by the following formula (19). And some triazineylated prepolymers thereof, and these may be used alone or in combination of two or more thereof.
  • n is 0 or an integer from 1 to 50.
  • n is 0 or an integer from 1 to 50.
  • the cyanate resin of Formula 19 may be bisphenol A type cyanate resin, bisphenol E type cyanate resin, bisphenol F type cyanate resin, or bisphenol M type cyanate resin, respectively, according to the type of R. .
  • the bismaleimide-triazine resin can be used without limitation, which is usually used in the resin composition for semiconductor packages, the type is not limited.
  • the resin composition for a semiconductor package of the embodiment may include an inorganic filler.
  • the inorganic layer dusting agent may be used without limitation, which is usually used in the resin composition for semiconductor packages, specific examples include silica, aluminum trihydroxide, magnesium hydroxide, molybdenum oxide, zinc molybdate, Zinc borate, zinc stannate, alumina, chlorine), kaolin, talc, calcined kaolin, calcined talc, mica, short glass fiber, glass fine powder, and hollow glass, selected from the group consisting of It may be abnormal.
  • the filler content may be 200 parts by weight or more, or 200 parts by weight to 500 parts by weight, or 250 parts by weight to 400 parts by weight. If the content of the filler is less than about 200 parts by weight, the coefficient of thermal expansion increases, so that the warpage phenomenon in the reflow (ref low) process is intensified, and the rigidity of the printed circuit board is reduced.
  • the inorganic filler may use silica surface-treated with a silane coupling agent in terms of improving moisture resistance and dispersion.
  • a method of dry or wet treatment of silica particles using a silane coupling agent as a surface treatment agent may be used.
  • the silica may be surface treated by a wet method using 0.01 to 1 parts by weight of the silane coupling agent based on the loo parts by weight of the silica particles.
  • the silane coupling agent such as 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, and N—2- (aminoethyl) ⁇ 3-aminopropyl trimethoxysilane
  • epoxy silane coupling group I such as 3-glycidoxypropyltrimeroxysilane
  • vinyl silane coupling agent such as 3-methacryloxypropyl trimethoxysilane
  • N-2- (N-vinylbenzylaminoethyl Cation silane coupling agent and phenyl silane coupling agent such as aminopropyltrimethoxysilane hydrochloride
  • the silane coupling agent may be used alone, or at least two silane coupling agents may be used. Can be used in combination.
  • the silane compound may include an aromatic amino silane or (meth) acrylic silane
  • a preferred example of the inorganic filler is silica, having an average particle diameter of 0.01 to loo, in which a silane compound is bonded to a surface thereof, more preferably. you may use the 100 / silica if the aromatic amino silane treated Hei 1 bacteria "particle diameter 0. 1 / zm to the surface.
  • Specific examples of the silica having an average particle diameter of 0.01 to 100 treated with the aromatic amino silane include SC2050MT0 (Admantechs).
  • the (meth) acryl was used to mean both acryl or methacryl.
  • the resin composition for a semiconductor package of the embodiment is as needed D) It can be used as a solution by adding a solvent.
  • the solvent is not particularly limited as long as it shows good solubility in the resin component, and may be alcohol, ether, ketone, amide, aromatic hydrocarbon, ester bran),
  • group etc. can be used, These can also use the mixed solvent used individually or in combination of 2 or more types.
  • the content of the solvent is not particularly limited as long as the resin composition can be impregnated into the glass fiber during prepreg production.
  • the resin composition of the present invention may further include other thermosetting resins, thermoplastic resins and various high molecular compounds such as oligomers and elastomers, other flame retardant compounds or additives, so long as the properties of the resin composition are not impaired. have. These are not particularly limited as long as they are selected from those commonly used.
  • additives include UV absorbers, antioxidants, photopolymerization initiators, optical brighteners, photosensitizers, pigments, dyes, thickeners, lubricants, antifoaming agents, dispersants, leveling agents, brightening agents, and the like. It is also possible.
  • the resin composition for a semiconductor package of the embodiment has a coefficient of thermal expansion (CTE)
  • the coefficient of thermal expansion is removed by etching the copper foil layer in the copper foil laminated plate state obtained from the resin composition for a semiconductor package, and then made a test piece in the MD direction, by using a TMA (TA Instruments), Q400, Means the measured value in the range of 50 ° C to 150 ° C after measuring at 30 ° C to 260 ° C, temperature rising rate 10 ° C / mi n conditions.
  • TMA TA Instruments
  • the resin composition for the semiconductor package has a low thermal expansion coefficient of the above-described level, minimization of warpage OVarpage of the semiconductor package caused by the difference in thermal expansion coefficient between the chip and the printed circuit board during the metal lamination or build-up process
  • the metal laminate including the prepreg may be usefully used for building up a printed circuit board for a semiconductor package.
  • the resin composition for a semiconductor package of the embodiment is IPC-TM ⁇ 650
  • the resin flowability measured by (2. 3. 17) can be 1-25%, or 153 ⁇ 4> -25%.
  • the resin flowability is IPC-TM—650 using carba press in the prepreg state obtained from the resin composition for the semiconductor package. It can be measured according to (2.3.17).
  • the resin composition for the semiconductor package has the above-described resin flowability, it is possible to make the metal laminated plate or to secure the flowability during the build-up process, so that the fine pattern can be easily filled, and the prepreg is included.
  • the metal laminated tube may be usefully used for building up a printed circuit board for a semiconductor package.
  • the resin composition for a semiconductor package of the embodiment has a minimum viscosity at 140 or more or 145 ° C to 165 ° C, the minimum viscosity is 100 Pa ⁇ s to 500 Pa ⁇ s, or 150 Pa. s to 400 Pa 's, or 200 Pa ⁇ s in not ⁇ s 350 Pa, or 250 Pa ⁇ s to 320 Pa ⁇ s may be.
  • the viscosity can be measured using a Modul ar compact Rheometer (Model MCR 302) of Anton Paar in the prepreg state obtained from the resin composition for semiconductor packages.
  • the resin composition for the semiconductor package exhibits the above-described viscosity, it is possible to secure the flowability during the production of the metal laminate or the build-up process so that the fine pattern can be easily filled, and the metal including the prepreg. Laminates can be useful for building up printed circuit boards for semiconductor packages.
  • the resin composition for a semiconductor package of the embodiment has a tensile elongation of 2.0% or more, or 2.0% to 5.0%, or 2.0% to 3.0%, or 2.3% as measured by IPC-TM-650 (2.4.18.3). To 3.0%.
  • the tensile elongation is 10 minutes in a prepreg state obtained from the resin composition for the semiconductor package, laminated 10 sheets to match the MD and TD direction of the glass fiber, 100 minutes under conditions of 220 ° C and 35 kg / cuf After pressing, in accordance with IPC-TM-650 (2.4.18.3), tensile elongation in the MD direction can be measured using a universal testing machine (Inst ron 3365).
  • the resin composition for semiconductor packages described above By showing the tensile elongation of the level, it is possible to secure the mechanical properties in the process of making a metal laminate or build-up, it can be useful for the build-up of printed circuit board for semiconductor package through excellent durability. Meanwhile, according to another embodiment of the present invention, a prepreg prepared by impregnating the resin composition for a semiconductor package into a fiber substrate may be provided.
  • the prepreg means that the resin composition for the semiconductor package is impregnated into the fiber substrate in a semi-cured state.
  • the kind of the fiber base material is not particularly limited, polyamide-based resin fibers, such as glass fiber base material, polyamide resin fiber, aromatic polyamide resin fiber, polyester resin fiber, aromatic polyester resin fiber, all aromatic polyester Synthetic fiber base, kraft paper, cotton linter paper composed of woven or nonwoven fabric mainly composed of polyester resin fiber such as resin fiber, polyimide resin fiber, polybenzoxazole fiber fluorine resin fiber, etc. Paper substrates mainly composed of grass paper and the like may be used, and glass fiber substrates are preferably used. The glass fiber substrate can improve the strength of the prepreg, lower the absorption rate, and reduce the coefficient of thermal expansion.
  • the glass substrate used in the present invention may be selected from glass substrates used for various printed circuit board materials. Examples thereof include, but are not limited to, glass fibers such as E glass, D glass, S glass, T glass, NE glass and L glass. If necessary, the glass-based material may be selected according to the intended use or performance. Glass-based forms are typically woven, nonwoven, roving, chopped st rand mats, or surface facing mats. The thickness of the glass base material is not particularly limited, but about 0.01 to 0.3 mm can be used. Of these materials, glass fiber materials are more preferred in terms of strength and water absorption ' properties.
  • the method for producing the prepreg in the present invention is not particularly limited and may be prepared by methods well known in the art.
  • the prepreg manufacturing method may be an impregnation method, a coating method using various coaters, spray spraying method and the like.
  • the prepreg after preparing the varnish, may be prepared by impregnating the fiber substrate with the varnish.
  • the solvent for the resin varnish is not particularly limited as long as it is compatible with the resin component and has good solubility.
  • Specific examples thereof include ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclonuxanone, aromatic hydrocarbons such as benzene, toluene and xylene, and amides such as dimethylformamide and dimethylacetamide, Aliphatic alcohols such as methylcellosolve and butyl salosolve.
  • the solvent used is volatilized by 80% by weight or more. Accordingly, also the manufacturing method and drying conditions are limited, the temperature during drying is about 80 ° C to 200 ° C, the time is not particularly limited to the balance with the varnish gelling time.
  • the impregnation amount of the varnish is preferably such that the resin solid content of the varnish is about 30 to 80% by weight relative to the total amount of the resin solid content of the varnish and the base material.
  • the prepreg may have a coefficient of thermal expansion (CTE) of 15 ppm / ° C or less, or 5 ppm / ° C to 15 ppm / t :. 4.
  • the thermal expansion coefficient information includes the above-described contents in the resin composition for a semiconductor package of the embodiment.
  • the prepreg of the other embodiment may have a resin flowability of 10% to 25%, or 15% to 25%, as measured by IPC-TM-650 (2.3.17).
  • the content of the resin flowability includes the above-mentioned content in the resin composition for a semiconductor package of the embodiment.
  • the prepreg of the other embodiment has a minimum viscosity at 140 ° C or more, or 145 ° C to 165 ° C, the minimum viscosity is 100 Pa-s to 500 Pa ⁇ s, or 150 Pa-s to 400 Pa ⁇ s, or 200 Pa ⁇ s to 350 Pa.s, or 250 Pa s to 320 Pa s.
  • the viscosity One embodiment includes the above-described information in the resin composition for a semiconductor package.
  • the prepreg of the other embodiment has a tensile elongation measured by IPC—TM-650 (2.4.18.3) of at least 2. 0%, or from 2. 0% to 5.0%, or from 2.0% to 3%.
  • the prepreg and a metal foil comprising a metal foil integrated with the prepreg by heating and pressurizing.
  • the metal foil is copper foil; Aluminum foil; A composite foil having a three-layer structure including nickel, nickel-phosphorus, nickel-tin alloy, nickel-iron alloy, lead or lead-tin alloy as an intermediate layer, and including copper layers having different thicknesses on both surfaces thereof; Or a composite foil having a two-layer structure in which aluminum and copper foil are combined.
  • the metal foil used in the present invention can be used copper foil or aluminum foil and having a thickness of about 2 to 200, it is preferable that the thickness is about 2 to 35 m.
  • copper foil is used as the metal foil.
  • nickel, nickel-phosphorus, nickel-tin alloy, nickel ferrous alloy, lead, or lead-tin alloy is used as an intermediate layer, and 0.5 to 15 copper layers and 10 to 15 are formed on both surfaces thereof.
  • the three-layered composite foil or the two-layered composite foil obtained by combining aluminum and copper foil may be used.
  • the metal laminate including the prepreg thus prepared can be used for the manufacture of double-sided or multilayer printed circuit boards after laminating in one or more sheets.
  • the present invention can manufacture a double-sided or multilayer printed circuit board by circuit-processing the metal foil laminate, the circuit processing can be applied to a method performed in a general double-sided or multilayer printed circuit board manufacturing process.
  • a resin composition for a semiconductor package having high fluidity, low thermal expansion characteristics and excellent mechanical properties, and a prepreg and a metal lamination plate using the same can be provided.
  • each component was added to methyl ethyl ketone according to the solid content of 65%, followed by mixing, followed by stirring at room temperature at 400 rpm for one day.
  • the resin composition (resin varnish) for packages was prepared.
  • the specific composition of the resin composition prepared in Examples 1 to 5 is as described in Table 1 below
  • the specific composition of the resin composition prepared in Comparative Examples 1 to 6 is as described in Table 2 below.
  • TFB 2,2 -bis (trifl uor omethy 1) benz i d i ne; 2,2'- Bis (tri f luoromethyl) -4,4 '-biphenyldi amine
  • TDA 4,4'-Thiodiani line; 4,4'-diaminodi henyl sulfide
  • Equation 1 the total active hydrogen equivalent weight of DDS is calculated as
  • the total active hydrogen equivalent of TFB is the total weight of TFB (g) divided by the unit equivalent of TFB (80 g / eq) of active hydrogen,
  • the total active hydrogen equivalent of DDM is the total weight of DDM divided by the equivalent weight of the active hydrogen of DDM (49.5 g / eq).
  • Total active hydrogen equivalent of DDE is the total weight of DDE (g) divided by the unit equivalent of active hydrogen of DDE (50 g / eq),
  • the total active hydrogen equivalent of TDA is the total weight of TDA (g) divided by the unit equivalent of TDA (54 g / eq),
  • the total epoxy equivalent of the XD-1000 is the total weight ( g ) of XD—1000 divided by XD—1000 and the epoxy unit equivalent (253 g / eq),
  • the total epoxy equivalent of NC—3000H is the total weight (g) of NC—3000H divided by the epoxy unit equivalent (290 g / eq) of NC-3000H.
  • the total epoxy equivalent of HP—6000 is the total weight (g) of HP—6000 divided by the epoxy unit equivalent (250g / eq) of HP-6000,
  • the total maleimide equivalent of BMI-2300 is the total weight (g) of BMI-2300 divided by the maleimide equivalent of BMI-2300 (179 g / eq).
  • TFB 2,2 -bis (trif luoromethyDbenzidine; 2,2'- Bis (tri f luoromethyl) -4, 4 '-b i heny 1 d i am i ne
  • TDA 4,4'-Thiodiani line; 4,4'-diaminodiphenyl sulfide
  • the prepregs obtained in the above examples and comparative examples were placed on both sides of the circuit pattern (pattern height 10um, residual ratio 50%), and copper foil (thickness l / m, manufactured by Mitsui) was placed thereon at 220 ° C. After pressing for 100 minutes under the condition of 35 kg / cm ', the copper foil of both surfaces was etched and the circuit pattern fillability was evaluated on the following reference
  • the resin composition for a semiconductor package of the embodiment and the prepreg, copper foil laminate obtained therefrom has a low thermal expansion coefficient of 9.0 to 10.5 ppm / ° C, low thermal expansion characteristics, minimum viscosity of 158 to It is measured at 260 to 312 Pa 3 s in the range of 163 ° C., and may have a high resin flowability of 15 to 23%, thereby ensuring excellent circuit pattern fillability.
  • the flow rate of resin was decreased by 1 ⁇ 2%, and the storage stability was also excellent.
  • the tensile elongation measurement result was found to have a high toughness (Toughness) of 2.4 to 2.9% to implement excellent mechanical properties.
  • the water for semiconductor packages of Comparative Examples 1 to 4 containing no amine curing agent (DDS or TFB) having an electron drawing (EWG) are significantly higher than those of the examples with a minimum viscosity of 810 to 987 Pa ⁇ s in the range of 119 to 124 ° C., showing very low resin flow of 3.0 to 4.7%. It can be seen that the pattern fill is very poor. .
  • the resin composition for a semiconductor package of Comparative Example 5 and the prepreg and copper foil laminate obtained therefrom were significantly reduced in the amount of the inorganic additive added to 36 parts by weight with respect to 100 parts by weight of the thermosetting resin component and the amine curing agent component in total. It can be seen that there is a limit rising to pp m / ° C.
  • the resin composition for a semiconductor package of Comparative Example 6 and a prepreg and copper foil laminated plate obtained therefrom are 625 parts by weight of a thermosetting resin with respect to 100 parts by weight of an amine curing agent, and the amine curing agent equivalent ratio based on the thermosetting resin equivalent is 0.63. This decrease to 1.7% compared with the embodiment, it can be seen that there is a limit in toughness (Toughness).
  • the equivalent ratio of the thermosetting resin of 400 parts by weight or less with respect to 100 parts by weight of the amine curing agent having an electron drawing (El ectron Withdrawing Group, EWG), and the equivalent amine curing agent equivalent ratio based on the thermosetting resin equivalent is 1.4 or more. While satisfying the above, it was confirmed that when the added amount of the inorganic additive was added in excess of the total content of the resin component and the amine curing agent component, excellent low thermal expansion properties, fluidity, mechanical properties, and storage stability could be ensured.

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Abstract

The present invention relates to a resin composition which is for a semiconductor package and has high flowability, low thermal expansion properties, and excellent mechanical properties, a prepreg using same, and a metal foil laminated plate.

Description

【발명의 명칭】  [Name of invention]
반도체 패키지용 수지 조성물과 이를 이용한 프리프레그 및 금속박 적층판  Resin composition for semiconductor package and prepreg and metal foil laminate using same
【기술분야]  Technical Field
관련 출원 (들)과의 상호 인용 · Cross Citation with Related Application (s)
본 출원은 2017년 3월 22일자 한국 특허 출원 제 10— 2017-0036104호 및 2018년 2월 13일자 한국 특허 출원 제 10-2018-0018018호에 기초한 우선 권의 이익을 주장하며， 해당 한국 특허 출원들의 문헌에 개시된 모든 내용 은 본 명세서의 일부로서 포함된다.  This application claims the benefit of priority based on Korean Patent Application No. 10—2017-0036104 dated March 22, 2017 and Korean Patent Application No. 10-2018-0018018 dated February 13, 2018, and the Korean Patent Application All content disclosed in these documents is included as part of this specification.
' 본 발명은 높은 유동성， 저열팽창 특성 및 우수한 기계적 물성을 갖 는 반도체 패키지용 수지 조성물과 이를 이용한 프리프레그 및 금속박 적층 판에 관한 것이다. 보다 구체적으로, 인쇄 회로 기판 (Pr inted Ci rcui t Board , PCB)의 리플로우 공정을 거쳐도 우수한 물성을 나타내는 프리프레그 와 금속박 적층판을 제조할 수 있는 반도체 패키지용 열.경화성 수지 조성물 과 이를 이용한 프리프레그에 관한 것이다. The present invention relates to a resin composition for a semiconductor package having high fluidity, low thermal expansion characteristics and excellent mechanical properties, and a prepreg and a metal foil laminated plate using the same. More specifically, heat for semiconductor packages that can produce prepregs and metal foil laminates that exhibit excellent physical properties even after reflow of printed circuit boards (PCBs) . It relates to a curable resin composition and a prepreg using the same.
【발명의 배경이 되는 기술】  [Technique to become background of invention]
종래의 인쇄회로기판에 사용되는 동박적층판 (copper cl ad l aminate) 은 유리 섬유 (Gl ass Fabr i c)의 기재를 상기 열경화성 수지 조성물의 바니시 에 함침한 후 반경화시키면 프리프레그가 되고， 이를 다시 동박과 함께 가 열 가압하여 제조한다. 이러한 동박 적층판에 회로 패턴을 구성하고 이 위 에 빌드업 (bui ld-up)을 하는 용도로 프리프레그가 다시 사용되게 된다.  Copper clad laminates used in conventional printed circuit boards are prepregs when the substrate of glass fiber (Gl ass Fabr ic) is impregnated in the varnish of the thermosetting resin composition and then semi-cured, which is then copper foil. It is prepared by heating and pressing together. The prepreg is used again for the purpose of constructing a circuit pattern on the copper foil laminate and building up on it.
최근 전자 기기, 통신기기, 개인용 컴퓨터, 스마트폰 등의 고성능화， 박형화， 경량화가 가속되면서 반도체 패키지 또한 박형화가 요구됨에 따라, 동시에 반도체 패키지용 인쇄회로기판도 박형화의 필요성이 커지고 있다. 그러나, 박형화 과정에서 인쇄회로기판의 강성이 감소하는 문제가 발 생함과 동시에， 칩과 인쇄회로기판간 열팽창률 차이로 .인해 반도체 패키지 의 휨 (Warpage) 문제가 발생하고 있다. 이러한 휨 현상은 '리플로우와 같은 고온 공정을 거치면서 인쇄회로기판이 원복이 되지 않는 현상으로 더 심화 된다. As high-performance, thin, and lightweight electronic devices, communication devices, personal computers, smart phones, and the like are accelerated, the semiconductor package is also required to be thin, and at the same time, the necessity of thinning a printed circuit board for a semiconductor package is increasing. However, the problem of decreasing the rigidity of the printed circuit board during the thinning process is caused by the difference in thermal expansion coefficient between the chip and the printed circuit board . Due to this, warpage problems of semiconductor packages are occurring. The bending phenomenon goes through a high temperature process, such as "reflow is further intensified by the phenomenon that a printed circuit board not wonbok.
이에， 휨 현상을 개선하기 위해 기판의 열팽창률올 낮추는 기술에 대 한 연구가 진행되고 있으며， 예를 들어 프리프레그에 필러를 고함량으로 충 진하는 기술이 제안되고 있으나， 단순히 프리프레그에 필러를 고함량으로 층진하기만 하는 경우 프리프레그의 유동성이 감소하는 한계가 있었다. Therefore, to reduce the thermal expansion coefficient of the substrate in order to improve the warpage phenomenon A research is being conducted, for example, a technique for filling a prepreg with a high content of fillers has been proposed. However, if the filler is simply laminated to the prepreg with a high content, there is a limit to the decrease in fluidity of the prepreg. there was.
따라서， 고온으로 진행하여도 흐름성이 확보되면서도 낮은 열팽창를 및 우수한 기계적 물성을 구현할 수 있는 프리프레그 및 금속박 적층판의 개발이 요구되고 있다.  Therefore, there is a demand for the development of prepreg and metal foil laminates capable of realizing low thermal expansion and excellent mechanical properties while ensuring flowability even at high temperatures.
【발명의 내용】  [Content of invention]
【해결하고자 하는 과제】  Problem to be solved
본 발명은 높은 유동성, 저열팽창 특성 및 우수한 기계적 물성을 갖 는 반도체 패키지용 수지 조성물을 제공하기 위한 것이다.  The present invention is to provide a resin composition for a semiconductor package having high fluidity, low thermal expansion characteristics and excellent mechanical properties.
또한， 본 발명은 상기 반도체 패키지용 수지 조성물을 이용한 프리프 레그 및 금속박 적충판을 제공하기 위한 것이다.  In addition, the present invention is to provide a prepreg and a metal foil stacking plate using the resin composition for a semiconductor package.
【과제의 해결 수단]  [Measures of problem]
본 명세서에서는， 술폰기， 카보닐기， 할로겐기， 탄소수 1 내지 20의 알킬기， 탄소수 6 내지 20의 아릴기， 탄소수 2 내지 30의 헤테로아릴기 및 탄소수 1 내지 20의 알킬렌기로 이루어진 군에서 선택된 1종 이상의 작용기 를 포함한 아민 경화제; 열경화성 수지; 및 무기 층진제를 포함하고， 상기 아민 경화제 및 열경화성 수지 100 중량부에 대하여 상기 무기 충진제 함량 이 200 중량부 이상이며, 상기 아민 경화제 100 중량부에 대하여 상기 열경 화성 수지 함량이 400 중량부 이하이고， 상기 아민 경화제에 포함된 탄소수 1 내지 20의 알킬기, 탄소수 6 내지 20의 아릴기, 탄소수 2 내지 30의 헤테 로아릴기 및 탄소수 1 내지 20의 알킬렌기는 각각 독립적으로 니트로기, 시 아노기 및 할로겐기로 이루어진 군에서 선택된 1종 이상의 작용기로 치환된, 반도체 패키지용 수지 조성물이 제공된다.  In the present specification, 1 selected from the group consisting of a sulfone group, a carbonyl group, a halogen group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, and an alkylene group having 1 to 20 carbon atoms Amine curing agents comprising at least one functional group; Thermosetting resins; And an inorganic layering agent, wherein the inorganic filler content is 200 parts by weight or more based on 100 parts by weight of the amine curing agent and the thermosetting resin, and the content of the thermosetting resin is 400 parts by weight or less based on 100 parts by weight of the amine curing agent, The alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms, the heteroaryl group having 2 to 30 carbon atoms and the alkylene group having 1 to 20 carbon atoms contained in the amine curing agent are each independently a nitro group, a cyano group and a halogen group. Provided is a resin composition for a semiconductor package substituted with one or more functional groups selected from the group consisting of.
본 명세서에서는 또한, 상기 반도체 패키지용 수지 조성물을 섬유 기 재에 함침시켜 얻어진 프리프레그를 제공한다.  This specification also provides the prepreg obtained by impregnating the said resin composition for semiconductor packages in a fiber base material.
본 명세서에서는 또한, 상기 프리프레그; 및 가열 및 가압에 의해 상 기 프리프레그와 일체화돤 포함하는 금속박；을 포함하는 금속박 적층판을 제공한다.  In the present specification, the prepreg; And a metal foil including the prepreg integrated with the prepreg by heating and pressurization.
이하 발명의 구체적인 구현예에 따른 반도체 패키지용 수지 조성물과 이를 이용한 프리프레그 및 금속박 적층판에 대하여 보다 상세하게 설명하 기로 한다. 발명의 일 구현예에 따르면, 술폰기， 카보닐기， 할로겐기， 탄소수 1 내지 20의 알킬기, 탄소수 6 내지 20의 아릴기， 탄소수 2 내지 30의 헤테로 아릴기 및 탄소수 1 내지 20의 알킬렌기로 이루어진 군에서 선택된 1종 이 상의 작용기를 포함한 아민 경화제; 열경화성 수지; 및 무기 층진제를 포함 하고， 상기 아민 경화제 및 열경화성 수지 100 중량부에 대하여 상기 무기 층진제 함량이 200 중량부 이상이며， 상기 아민 경화제 100 중량부에 대하 여 상기 열경화성 수지 함량이 400 중량부 이하이고， 상기 아민 경화제에 포함된 탄소수 1 내지 20의 알킬기， 탄소수 6 내지 20의 아릴기， 탄소수 2 내지 30의 헤테로아릴기 및 탄소수 1 내지 20의 알킬렌기는 각각 독립적으 로 니트로기， 시아노기 및 할로겐기로 이루어진 군에서 선택된 1종 이상의 작용기로 치환된， 반도체 패키지용 수지 조성물이 제공될 수 있다. And a resin composition for a semiconductor package according to a specific embodiment of the invention The prepreg and the metal foil laminate using the same will be described in more detail. According to an embodiment of the present invention, a sulfone group, a carbonyl group, a halogen group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, and an alkylene group having 1 to 20 carbon atoms Amine curing agents comprising at least one functional group selected from the group; Thermosetting resins; And an inorganic layering agent, wherein the inorganic layering agent content is 200 parts by weight or more based on 100 parts by weight of the amine curing agent and the thermosetting resin, and the content of the thermosetting resin is 400 parts by weight or less based on 100 parts by weight of the amine curing agent. ， C1-C20 alkyl group, C6-C20 aryl group, C2-C30 heteroaryl group and C1-C20 alkylene group contained in the amine curing agent are each independently nitro group, cyano group and halogen There may be provided a resin composition for a semiconductor package, substituted with one or more functional groups selected from the group consisting of groups.
본 발명자들은 상기 일 구현예의 반도체 패키지용 수지 조성물을 사 용하면, 술폰기， 카보닐기 , 할로겐기 , 치환된 탄소수 1 내지 20의 알킬기 , 치환된 탄소수 6 내지 20의 아릴기, 치환된 탄소수 2 내지 30의 헤테로아릴 기 및 치환된 탄소수 1 내지 20의 알킬렌기로 이루어진 군에서 선택된 1종 이상의 작용기와 같이 강력한 전자 끌개 작용기 (El ectron Wi thdrawing Group , EWG)를 포함한 아민 경화제를 통해, 아민 경화제의 반응성을 줄여 수지 조성물의 경화 반응을 용이하게 제어할 수 있음을 확인하였다.  When the present inventors use the resin composition for a semiconductor package of the above embodiment, a sulfone group, a carbonyl group, a halogen group, a substituted C1-20 alkyl group, a substituted C6-20 aryl group, a substituted C2-30 The reactivity of the amine curing agent through an amine curing agent including a strong electron withdrawing group (El ectron Withdrawing Group, EWG) such as at least one functional group selected from the group consisting of heteroaryl groups and substituted alkylene groups having 1 to 20 carbon atoms. In short, it was confirmed that the curing reaction of the resin composition can be easily controlled.
특히, 상기 일 구현예의 반도체 패키지용 수지 조성물에서는 상기 아 민 경화제 100 중량부에 대하여 상기 열경화성 수지 함량을 400 중량부 이 하로 포함시킴으로서, 고함량으로 투입된 필러에 의한 열경화성 수지의 물 성 변화를 방지하고, 필러의 영향없이 열경화성 수지가 보다 층분한 수준으 로 균일하게 경화가능하도톡 유도하여， 최종 제조되는 제품의 신뢰성이 향 상될 수 있고, 인성 (Toughness)와 같은 기계적 물성 또한 증가시킬 수 있는 장점이 있다.  Particularly, in the resin composition for a semiconductor package of the embodiment, the thermosetting resin content is included in an amount of 400 parts by weight or less with respect to 100 parts by weight of the amine curing agent, thereby preventing the change of physical properties of the thermosetting resin due to the filler added in a high content. In addition, the thermosetting resin can be uniformly cured to a more uniform level without the effect of fillers, and thus the reliability of the final product can be improved, and the mechanical properties such as toughness can also be increased. have.
종래에는 상기 아민 경화제 100 중량부에 대하여 상기 열경화성 수지 함량을 400 중량부 이하로 포함시키는 것과 같이， 아민 경화제를 상대적으 로 과량으로 첨가시 열경화성 수지의 과도한 경화로 인해 유동성 및 성형성 이 감소하는 한계가 있었다. 그러나， 상술한 바와 같이 전자 끌개 작용기Conventionally, as including the thermosetting resin content to 400 parts by weight or less with respect to 100 parts by weight of the amine curing agent, the amine curing agent is relatively When added in excess of the furnace, there was a limit in reducing fluidity and formability due to excessive curing of the thermosetting resin. However, as described above, the electronic drawer functional group
(El ectron Wi thdrawing Group , EWG)를 포함하여 반웅성이 감소한 특정 아민 경화제를 과량으로 첨가하더라도, 경화제의 반웅성 감소로 인해, 열경화성 수지의 경화속도가 급격히 상승하는 것을 억제할 수 있어， 반도체 패키지용 수지 조성물이나 이로부터 얻어지는 프리프레그 상태에서의 장기간 보관시 에도 높은 흐름성을 나타내어 우수한 유동성을 가질 수 있다. Even if an excessive amount of the specific amine curing agent having reduced semicoupling, including (El ectron Withdrawing Group, EWG) is added in excess, it is possible to suppress the rapid increase in the curing rate of the thermosetting resin due to the decrease in the semicoupling of the curing agent. Even when stored for a long time in a prepreg state obtained in the resin composition or a resin therefrom, it has high flowability and can have excellent fluidity.
이를 통해， 프리프레그의 유동성을 층분히 확보하면서도, 필러를 고 함량으로 충진할 수 있어， 낮은 열팽창계수를 구현할 수 있음과 동시에 우 수한 보관안정성까지 달성할 수 있음을 실험을 통하여 확인하고 발명을 완 성하였다.  Through this experiment, it was confirmed that the filler can be filled with high content while securing the fluidity of the prepreg, and the low thermal expansion coefficient can be realized and the excellent storage stability can be achieved through experiments. I did it.
구체적으로， 상기 일 구현예의 반도체 패키지용 수지 조성물은 술폰 기 , 카보닐기， 할로겐기， 탄소수 1 내지 20의 알킬기 , 탄소수 6 내지 20의 아릴기, 탄소수 2 내지 30의 헤테로아릴기 및 탄소수 1 내지 20의 알킬렌기 로 이루어진 군에서 선택된 1종 이상의 작용기를 포함한 아민 경화제를 포 함할 수 있다. 이때， 상기 아민 경화제에 포함된 탄소수 1 내지 20의 알킬 기， 탄소수 6 내지 20의 아릴기, 탄소수 2 .내지 30의 헤테로아릴기 및 탄소 수 1 내지 20의 알킬렌기는 각각 독립적으로 니트로기, 시아노기 및 할로겐 기로 이루어진 군에서 선택된 1종 이상의 작용기로 치환될 수 있다.  Specifically, the resin composition for a semiconductor package according to the embodiment includes a sulfone group, a carbonyl group, a halogen group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, and 1 to 20 carbon atoms. It may include an amine curing agent containing at least one functional group selected from the group consisting of alkylene groups of. In this case, the alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms, the heteroaryl group having 2 to 30 carbon atoms and the alkylene group having 1 to 20 carbon atoms contained in the amine curing agent are each independently a nitro group, It may be substituted with one or more functional groups selected from the group consisting of a no group and a halogen group.
상기 아민 경화제에 포함된 술폰기, 카보닐기， 할로겐기, 치환된 탄 소수 1 내지 20의 알킬기， 치환된 탄소수 6 내지 20의 아릴기， 치환된 탄소 수 2 내지 30의 헤테로아릴기 및 치환된 탄소수 1 내지 20의 알킬렌기로 이 루어진 군에서 선택된 1종 이상의 작용기는 강력한 전자 끌개 작용기 (E l ectron Wi thdrawing Group , EWG)로서, 상기 전자 끌개 작용기를 포함한 아민 경화제는 전자.끌개 작용기를 포함지 않은 아민 경화제에 비해 반웅성 이 감소하여 이로부터 수지 조성물의 경화 반웅을 용이하게 제어할 수 있다. 따라서， 상기 아민 경화제에 의해 조성물의 경화반웅 정도를 조절하 면서 고함량의 무기 충진제를 프리프레그 내에 도입하여 프리프레그의 열팽 창계수를 낮출 수 있으며， 동시에 프리프레그의 유동성을 향상시켜 회로 패 턴 채움성이 향상될 수 있다 . 구체적으로， 상기 아민 경화제는 하기 화학식 1 내지 3으로 이루어진 군에서 선택된 1종 이상의 화합물을 포함할 수 있다. The sulfone group, carbonyl group, halogen group, substituted C1-20 alkyl group, substituted C6-C20 aryl group, substituted C2-C30 heteroaryl group and substituted carbon number contained in the amine curing agent At least one functional group selected from the group consisting of alkylene groups of 1 to 20 is a strong electron drag group (EWG), wherein the amine curing agent including the electron drag functional group includes an electron. Compared with the amine curing agent which is not used, the reaction property is reduced, and thus the curing reaction of the resin composition can be easily controlled. Therefore, while controlling the degree of curing reaction of the composition by the amine curing agent, a high content of inorganic filler can be introduced into the prepreg to lower the coefficient of thermal expansion of the prepreg, and at the same time improve the fluidity of the prepreg to fill the circuit pattern. Sex can be improved. Specifically, the amine curing agent may include one or more compounds selected from the group consisting of the following Chemical Formulas 1 to 3.
[화학식 1]  [Formula 1]
Figure imgf000006_0001
Figure imgf000006_0001
상기 화학식 1에서, A는 술폰기, 카보닐기， 또는 탄소수 1 내지 10의 알킬렌기이며， Xi 내지 ¾는 각각 독립적으로 니트로기， 시아노기， 수소원자, 할로겐기， 탄소수 1 내지 6의 알킬기， 탄소수 6 내지 15의 아릴기 , 또는 탄 소수 2 내지 20의 해테로아릴기이고， ¾ 및 '는 각각 독립적으로 수소원자， 할로겐기, 탄소수 1 내지 6의 알킬기, 탄소수 .6 내지 15의 아릴 기 , 또는 탄소수 2 내지 20의 헤테로아릴기이며， n은 1 내지 10의 정수이고, 상기 탄소수 1 내지 10의 알킬렌기， 탄소수 1 내지 6의 알킬기， 탄소 수 6 내지 15의 아릴기， 및 탄소수 2 내지 20의 헤테로아릴기는 각각 독립 적으로 니트로기， 시아노기 및 할로겐기로 이루어진 군에서 선택된 1종 이 상의 작용기로 치환되며，  In Formula 1, A is a sulfone group, a carbonyl group, or an alkylene group having 1 to 10 carbon atoms, and Xi to ¾ are each independently a nitro group, cyano group, hydrogen atom, halogen group, alkyl group having 1 to 6 carbon atoms, and carbon number. A aryl group of 6 to 15, or a heteroaryl group of 2 to 20 carbon atoms, ¾ and 'are each independently a hydrogen atom, a halogen group, an alkyl group of 1 to 6 carbon atoms, an aryl group of .6 to 15 carbon atoms, or A heteroaryl group having 2 to 20 carbon atoms, n is an integer of 1 to 10, the alkylene group having 1 to 10 carbon atoms, the alkyl group having 1 to 6 carbon atoms, the aryl group having 6 to 15 carbon atoms, and the 2 to 20 carbon atoms Heteroaryl groups are each independently substituted with one or more functional groups selected from the group consisting of nitro, cyano and halogen groups,
[화학식 2]  [Formula 2]
Figure imgf000006_0002
Figure imgf000006_0002
상기 화학식 2에서, 내지 Ys는 각각 독립적으로, 니트로기, 시아노 기, 수소원자， 할로겐기, 탄소수 1 내지 6의 알킬기, 탄소수 6 내지 15의 아릴기., 또는 탄소수 2 내지 20의 헤테로아릴기이고， R3, R3 ' , R4 및 '는 각 각 독립적으로 수소원자, 할로겐기, 탄소수 1 내지 6의 알킬기, 탄소수 6 내지 15의 아릴기， 또는 탄소수 2 내지 20의 헤테로아릴기이며， m은 1 내지 10의 정수이고, 상기 탄소수 1 내지 6의 알킬기， 탄소수 6 내지 15의 아릴 기， 및 탄소수 2 내지 20의 해테로아릴기는 각각 독립적으로 니트로기， 시 아노기 및 할로겐기로 이루어진 군에서 선택된 1종 이상의 작용기로 치환되 며, ' In Formula 2, to Ys are each independently a nitro group, a cyano group, a hydrogen atom, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms. R 3 , R 3 ', R 4 and' are each independently a hydrogen atom, a halogen group, an alkyl group of 1 to 6 carbon atoms, an aryl group of 6 to 15 carbon atoms, or a heteroaryl group of 2 to 20 carbon atoms, m Is an integer of 1 to 10, wherein the alkyl group of 1 to 6 carbon atoms, the aryl group of 6 to 15 carbon atoms, and the heteroaryl group of 2 to 20 carbon atoms are each independently a nitro group, Cyano group, and said groups being substituted in the halogen group consisting of at least one kinds selected functional group, "
[화학식 3]  [Formula 3]
Figure imgf000007_0001
상기 화학식 3에서 ΖΓ내지 Z4는 각각 독립적으로 니트로기， 시아노 기, 수소원자， 할로겐기, 탄소수 1 내지 6의 알킬기， 탄소수 6 내지 15의 아릴기 , 또는 탄소수 2 내지 20의 헤테로아릴기이고， R5 , R5 ' , R6 및 R6 '는 각 각 독립적으로 수소원자, 할로겐기, 탄소수 1 내지 6의 알킬기， 탄소수 6 내지 15의 아릴기， 또는 탄소수 2 내지 20의 헤테로아릴기이며， 상기 탄소 수 1 내지 6의 알킬기， 탄소수 6 내지 15의 아릴기， 및 탄소수 2 내지 20의 헤테로아릴기는 각각 독립적으로 니트로기， 시아노기 및 할로겐기로 이루어 진 군에서 선택된 1종 이상의 작용기로 치환된다.
Figure imgf000007_0001
ΖΓ to Z 4 in Chemical Formula 3 are each independently a nitro group, a cyano group, a hydrogen atom, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms. , R 5, R 5 ' , R 6 and R 6 ' are each independently a hydrogen atom, a halogen group, an alkyl group of 1 to 6 carbon atoms, an aryl group of 6 to 15 carbon atoms, or a heteroaryl group of 2 to 20 carbon atoms The alkyl group having 1 to 6 carbon atoms, the aryl group having 6 to 15 carbon atoms, and the heteroaryl group having 2 to 20 carbon atoms are each independently substituted with one or more functional groups selected from the group consisting of nitro, cyano and halogen groups. .
상기 알킬기는, 알케인 (alkane)으로부터 유래한 1가의 작용기로, 예 를 들어, 직쇄형， 분지형 또는 고리형으로서， 메틸， 에틸, 프로필， 이소부 틸, sec-부틸， tert-부틸, 펜틸, 핵실 등이 될 수 있다. 상기 알킬기에 포 함되어 있는 하나 이상의 수소 원자는 각각 치환기로 치환가능하다.  The alkyl group is a monovalent functional group derived from alkane, and is, for example, linear, branched or cyclic, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, It may be a nuclear chamber. One or more hydrogen atoms contained in the alkyl group may each be substituted with a substituent.
상기 알킬렌기는， 알케인 (alkane)으로부터 유래한 2가의 작용기로ᅳ 예를 들어， 직쇄형, 분지형 또는 고리형으로서, 메틸렌기, 에틸렌기， 프로 필렌기, 이소부틸렌기, sec-부틸렌기， tert-부틸렌기, 펜틸렌기, 핵실렌기 등이 될 수 있다. 상기 알킬렌기에 포함되어 있는 하나 이상의 수소 원자는 각각 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다.  The alkylene group is a divalent functional group derived from alkane, and is, for example, a linear, branched or cyclic group, and is a methylene group, an ethylene group, a propylene group, an isobutylene group, or a sec-butylene group. It may be a tert- butylene group, a pentylene group, a nuclear silane group and the like. One or more hydrogen atoms contained in the alkylene group may be substituted with the same substituents as in the case of the alkyl group, respectively.
상기 아릴기는 아렌 rene)으로부터 유래한 1가의 작용기로， 예를 들 어， 단환식 또는 다환식일 수 있다. 구체적으로， 단환식 아릴기로는 페닐기， 바이페닐기， 터페닐기， 스틸베닐기 등이 될 수 있으나， 이에 한정되는 것은 아니다. 다환식 아릴기로는 나프틸기, 안트릴기， 페난트릴기, 파이레닐기， 페릴레닐기， 크라이세닐기, 플루오레닐기 등이 될 수 있으나， 이에 한정되 는 것은 아니다. 이러한 아릴기 중 하나 이상의 수소 원자는 각각 상기 알 킬기의 경우와 마찬가지의 치환기로 치환가능하다. The aryl group is a monovalent functional group derived from arene rene), for example, may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may be a phenyl group, biphenyl group, terphenyl group, stilbenyl group and the like, but is not limited thereto. The polycyclic aryl group may be naphthyl group, anthryl group, phenanthryl group, pyrenyl group, perrylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. It is not. At least one hydrogen atom of such an aryl group may be each substituted with the same substituent as in the case of the above alkyl group.
상기 헤테로아릴기는 이종원자로 0， N 또는 S를 포함하는 헤테로 고 리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내치 30일 수 있다. 해테로 고리기의 예로는 티오펜기, 퓨란기， 피롤기, 이미다졸기， 티아졸기ᅳ 옥사졸기 , 옥사디아졸기， 트리아졸기 , 피리딜기 비피리딜기， 트리아진기 , 아크리딜기, 피리다진기， 퀴놀리닐기, 이소퀴놀린기， 인돌기, 카바졸기， 벤 조옥사졸기, 벤조이미다졸기, 벤조티아졸기， 벤조카바졸기, 벤조티오펜기， 디벤조티오펜기, 벤조퓨라닐기 및 디벤조퓨란기 등이 있으나， 이들에만 한 정되는 것은 아니다. 이러한 헤테로아릴기 중 하나 이상의 수소 원자는 각 각 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다 .  The heteroaryl group is a heterocyclic group including 0, N or S as a hetero atom, and the number of carbon atoms is not particularly limited, but may be 2 to 30 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group oxazole group, oxadiazole group, triazole group, pyridyl group bipyridyl group, triazine group, acridil group, pyridazine group ， Quinolinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group and dibenzo Furan groups and the like, but are not limited thereto. At least one hydrogen atom of such a heteroaryl group may be substituted with the same substituent as in the case of the alkyl group, respectively.
상기 "치환''이라는 용어는 화합물 내의 수소 원자 대신 다른 작용기 가 결합하는 것을 의미하며， 치환되는 위치는 수소 원자가 치환되는 위치 즉， 치환기가 치환 가능한 위치라면 한정되지 않으며， 2 이상 치환되는 경 우， 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.  The term "substituted" means that another functional group is bonded instead of a hydrogen atom in the compound, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent may be substituted, and when two or more are substituted, Two or more substituents may be the same or different from each other.
보다 구체적으로， 상기 화학식 1은 하기 화학식 1-1로 표시되는 화합물 을 포함할 수 있다ᅳ  More specifically, Chemical Formula 1 may include a compound represented by Chemical Formula 1-1 below:
[화학식 1-1]  [Formula 1-1]
Figure imgf000008_0001
Figure imgf000008_0001
상기 화학식 1-1에서， , Xi 내지 ¾， Ri, Ri', R2 및 n에 대한 내 용은 상기 화학식 1에서 상술한 내용을 포함한다. In Chemical Formula 1-1, Xi to ¾, Ri, Ri ', R 2 and n include the above-mentioned information in the general formula (1).
상기 화학식 1-1의 구체적인 예로는 4,4'-diaminodiphenyl sulfone (화 학식 1—1에서 A는 술폰기, 내지 X8, Ri, Ri', R2 및 R2'는 각각 독립적으로 수소원자이며, n은 1 이다. )， bis(4-aminophenyl)methanone (화학식 1-1에서 A는 카보닐기， ， X2, Ri, Ri', R2 및 '는 각각 독립적으로 수소원자이며 , η 은 1 이다.) , 4,4'-(perf luoropropane-2,2-diyl)dianiline (화학식 1-1에서 A 는 perfluoropropane-2,2-diyl, Xi 내지 ¾ ¾ R2 및 '는 각각 독립적 으로 수소원자이며， n은 1 이다.；)， 4,4'-(2,2,2-trifluoroethane-l)l- diyDdiani line (화학식 1—1에서 A는 2,2,2— tr if luoroethane—1, l—diyl， Xi 내 지 X8, Ri, Ri', ¾ 및 R2'는 각각 독립적으로 수소원자이며， n은 1 이다.) 등 을 들 수 있다. Specific examples of the formula 1-1 is 4,4'-diaminodiphenyl sulfone (In Formula 1-1, A is a sulfone group, X 8 , Ri, Ri ', R 2 and R 2 ' are each independently a hydrogen atom. , n is 1.), bis (4-aminophenyl) methanone (In Formula 1-1, A is a carbonyl group,, X 2 , Ri, Ri ', R 2 and' are each independently a hydrogen atom, and η is 1 4,4 '-(perf luoropropane-2,2-diyl) dianiline (In Formula 1-1, A is perfluoropropane-2,2-diyl, Xi to ¾ ¾ R 2 and' are each independently. Is a hydrogen atom, n is 1.; ) , 4,4 '-(2,2,2-trifluoroethane-l ) l- diyDdiani line (A in Formula 1—1 is 2,2,2— tr if luoroethane — 1, l—diyl, Xi to X 8 , Ri, Ri ' , ¾ and R 2 ' are each independently a hydrogen atom, n is 1).
또한, 상기 화학식 2는 하기 화학식 2-1로 표시되는 화합물을 포함할 수 있다.  In addition, Chemical Formula 2 may include a compound represented by Chemical Formula 2-1.
[화학식 2-1]  [Formula 2-1]
Figure imgf000009_0001
Figure imgf000009_0001
상기 화학식 2—1에서， Yi 내지 Y8, 및 IV , m에 대한 내용은 상기 화학식 2에서 상술한 내용을 포함한다. In Chemical Formula 2-1, Yi to Y 8 , and IV, m include the above-mentioned information in Chemical Formula 2.
상기 화학식 2—1의 구체적인 예로는 2，2' ,3，3'，5，5' ,6,6'ᅳ octafluorobiphenyl-4，4'-dlamlne (화학식 2-1에서 내지 Y8은 할로겐으로 플루오르기, R3, 및 F 는 각각 독립적으로 수소원자이며, m은 1 이 다 .), 2 ,2'-bis(trifluoromethyl)bipheny 1-4,4' -diamine (Y2 및 Υ7은 각각 트리플루오로메틸기이며， Υ1; Υ3, Υ4, Υ5, Υ6, Υ8은 수소원자, , R3', 4 및 R4'는 각각 독립적으로 수소원자이며 , m은 1 이다 J 등을 들 수 있다. Specific examples of Chemical Formula 2-1 include 2,2 ', 3,3', 5,5 ', 6,6' ᅳ octafluorobiphenyl-4,4'-dlamlne (In Formula 2-1 to Y 8 is halogen fluorine Groups, R 3, and F are each independently a hydrogen atom, m is 1), 2,2'-bis (trifluoromethyl) bipheny 1-4,4 '-diamine (Y 2 and Υ 7 are each a tree) Is a fluoromethyl group, Υ 1 , Υ 3 , Υ 4 , Υ 5 , Υ 6 , Υ 8 are hydrogen atoms, R 3 ', 4 and R 4 ' are each independently a hydrogen atom, m is 1 J, etc. Can be mentioned.
또한, 상기 화학식 3는 하기 화학식 3-1로 표시되는 화합물을 포함할 수 있다.  In addition, Chemical Formula 3 may include a compound represented by Chemical Formula 3-1.
[화학식 3一1]  [Formula 3 一 1]
Figure imgf000009_0002
상기 화학식 3—1에서, τλ 내지 Z4, 5, R5', Re 및 Rs'에 대한 내용은 상 기 화학식 3에서 상술한 내용을 포함한다.
Figure imgf000009_0002
In Formula 3-1, the contents of τ λ to Z 4 , 5 , R 5 ', Re, and Rs' include the above-described contents in Formula 3 above.
상기 화학식 3—1의 구체적인 예로는 2,3,5,6-tetrafluorobenzene-l,4- di amine (화학식 3-1에서 1、 내지 Z4는 할로겐으로 플루오르기, R5 , R5 1 , R6 및 '는 각각 독립적으로 수소원자이다. )등을 들 수 있다. Specific examples of Chemical Formula 3-1 may include 2,3,5,6-tetrafluorobenzene-l, 4- and di amines (wherein 1, to Z 4 in Formula 3-1 are halogen, a fluorine group , R 5, R 5 1 , R 6 and 'are each independently a hydrogen atom).
상기 아민 경화제 100 중량부에 대하여 상기 열경화성 수지 함량^ The thermosetting resin content per 100 parts by weight of the amine curing agent ^
400 중량부 이하， 또는 150 중량부 내지 400 중량부, 또는 180 중량부 내지 300 충량부， 또는 180 중량부 내지 290 중량부， 또는 190 중량부 내지 290 중량부일 수 있다ᅳ 상기 아민 경화제 또는 열경화성 수지가 2종 이상의 흔 합물인 경우, 아민 경화제 혼합물 100 중량부에 대하여 열경화성 수지 흔합 물 함량 또한 400 중량부 이하， 또는 150 중량부 내지 400 중량부， 또는400 parts by weight or less, or 150 parts by weight to 400 parts by weight, or 180 parts by weight to 300 parts by weight, or 180 parts by weight to 290 parts by weight, or 190 parts by weight to 290 parts by weight. In the case of two or more mixtures, the thermosetting resin mixture content is also 400 parts by weight or less, or 150 parts by weight to 400 parts by weight, based on 100 parts by weight of the amine curing agent mixture, or
180 중량부 내지 300 중량부, 또는 180 중량부 내지 290 중량부， 또는 190 중량부 내지 290 중량부일 수 있다. 180 parts by weight to 300 parts by weight, or 180 parts by weight to 290 parts by weight, or 190 parts by weight to 290 parts by weight.
상기 아민 경화제 100 중량부에 대하여 상기 열경화성 수지 함량을 The thermosetting resin content based on 100 parts by weight of the amine curing agent
400 중량부 초과로 지나치게 증가할 경우, 고함량으로 투입된 필러에 의한 열경화성 수지의 물성 변화가 발생하고, 필러의 영향으로 열경화성 수지가 보다 층분한 수준까지 균일하게 경화되기 어려워， 최종 제조되는 제품의 신 뢰성이 감소할 수 있고, 인성 (Toughness)와 같은 기계적 물성 또한 감소될 수 있는 단점이 있다. If it is excessively increased to more than 400 parts by weight, the change of physical properties of the thermosetting resin due to the filler added in a high content occurs, it is difficult to uniformly harden the thermosetting resin to a more granular level under the influence of the filler, There is a disadvantage that the fastness may be reduced, and mechanical properties such as toughness may also be reduced.
이때， 상기 반도체 패키지용 수지 조성물은 하기 수학식 1로 계산되는 당량비가 1 .4 이상, 또는 1.4 내지 2.5， 또는 1.45 내지 2.5 , 또는 1.45 내 지 2. 1， 또는 1.45 내지 1.8， 또는 1.49 내지 1.75일 수 있다.  At this time, the resin composition for a semiconductor package has an equivalent ratio calculated by Equation 1 below 1.4 or 2.5, or 1.4 to 2.5, or 1.45 to 2.5, or 1.45 to 2. 1, or 1.45 to 1.8, or 1.49 to 1.75 Can be.
[수학식 1 ]  Equation 1
당량비 = 상기 아민 경화제에 함유된 총 활성수소 당량 I 상기 열경 화성 수지에 함유된 총 경화성 작용기 당량  Equivalence ratio = total active hydrogen equivalent in the amine curing agent I total curable functional group equivalent in the thermosetting resin
보다 구체적으로， 상기 수학식 1에서. 상기 아민 경화제에 함유된 총 활성수소 당량은， 상기 아민 경화제의 총 중량 (단위: g)을 상기 아민 경화 제의 활성수소 단위당량 (g/eQ)로 나눈 값을 의미한다.  More specifically, in Equation 1 above. The total active hydrogen equivalent contained in the amine curing agent refers to the total weight (unit: g) of the amine curing agent divided by the unit hydrogen equivalent (g / eQ) of the amine curing agent.
상기 아민 경화제가 2종 이상의 흔합물인 경우， 각각의 화합물 별로 중량 (단위: g)을 활성수소 단위당량 (g/eq)로 나눈 값을 구하고， 이를 합한 값으로 상기 수학식 1의 아민 경화제에 함유된 총 활성수소 당량을 구할 수 있다.  When the amine curing agent is a mixture of two or more kinds, the value obtained by dividing the weight (unit: g) by the unit equivalent of active hydrogen (g / eq) for each compound is obtained, and the sum thereof is contained in the amine curing agent of Equation 1 above. The total equivalent active hydrogen equivalent can be obtained.
상기 아민 경화제에 함유된 활성수소는， 아민 경화제에 존재하는 아 미노기 (-N¾)에 포함된 수소원자를 의미하며 , 상기 활성수소가 열경화성 수 지의 경화성 작용기와의 반웅을 통해 경화구조를 형성할 수 있다. The active hydrogen contained in the amine curing agent is present in the amine curing agent. It refers to a hydrogen atom contained in the mino group (-N¾), the active hydrogen can form a cured structure through the reaction with the curable functional group of the thermosetting resin.
또한， 상기 수학식 1에서， 상기 열경화성 수지에 함유된 총 경화성 작 용기 당량 은， 상기 열경화성 수지의 총 중량 (단위: g)을 상기 열경화성 수 지의 경화성 작용기 단위당량 (g/eq)로 나눈 값을 의미한다.  In addition, in Equation 1, the total curable work container equivalent contained in the thermosetting resin is a value obtained by dividing the total weight (unit: g) of the thermosetting resin by the unit equivalent (g / eq) of the curable functional group of the thermosetting resin. it means.
상기 열경화성 수지가 2종 이상의 흔합물인 경우, 각각의 화합물 별 로 중량 (단위: g)을 경화성 작용기 단위당량 (g/eq)로 나눈 값을 구하고， 이 를 합한 값으로 상기 수학식 1의 열경화성 수지에 함유된 총 경화성 작용기 당량을 구할 수 있다.  When the thermosetting resin is two or more kinds of mixtures, the value obtained by dividing the weight (unit: g) by the unit equivalent weight (g / eq) of the curable functional group for each compound is calculated, and the sum thereof is the thermosetting resin of Equation 1 The total curable functional group equivalent contained in can be calculated | required.
상기 열경화성 수지에 함유된 경화성 작용기는， 상기 아민 경화제의 활성수소와의 반응을 통해 경화구조를 형성하는 작용기를 의미하며， 상기 열경화성 수지 종류에 따라 경화성 작용기의 종류 또한 달라질 수 있다.  The curable functional group contained in the thermosetting resin means a functional group that forms a cured structure through reaction with active hydrogen of the amine curing agent, and the type of the curable functional group may also vary according to the thermosetting resin type.
예를 들어， 상기 열경화성 수지로 에폭시 수지를 사용할 경우， 상기 에폭시 수지에. 함유된 경화성 작용기는 에폭시기가 될 수 있고， 상기 열경 화성 수지로 비스말레이미드수지를 사용할 경우， 상기 비스말레이미드 수지 에 함유된 경화성 작용기는 말레이미드기가 될 수 있다.  For example, when using an epoxy resin as the thermosetting resin, to the epoxy resin. The curable functional group contained may be an epoxy group, and when the bismaleimide resin is used as the thermosetting resin, the curable functional group contained in the bismaleimide resin may be a maleimide group.
즉， 상기 반도체 패키지용 수지 조성물이 상기 수학식 1로 계산되는 당량비가 1ᅳ4 이상을 만족한다는 것은， 모든 열경화성 수지에 함유된 경화 성 작용기가 경화반응을 일으킬 수 있을 정도로 충분한 수준의 아민 경화제 가 함유되어있음을 의미한다. 따라서， 상기 반도체 패키지용 수지 조성물에 서 상기 수학식 1로 계산되는 당량비가 1.4 미만으로 감소하는 경우， 고함량 으로 투입된 필러에 의한 열경화성 수지의 물성 변화가 발생하고, 필러의 영향으로 열경화성 수지가 보다 충분한 수준까지 균일하게 경화되기 어려워, 최종 제조되는 제품의 신뢰성이 감소할 수 있고， 기계적 물성 또한 감소할 수 있는 단점이 있다. That is, the resin composition for a semiconductor package satisfies that the equivalent ratio calculated by Equation 1 is 1 ᅳ 4 or more, the amine curing agent of a sufficient level so that the curable functional groups contained in all the thermosetting resins can cause a curing reaction. It contains. Therefore, when the equivalent ratio calculated by Equation 1 in the resin composition for semiconductor package is reduced to less than 1.4, a change in physical properties of the thermosetting resin due to the filler added with a high content occurs, the thermosetting resin is more affected by the filler Since it is difficult to uniformly harden to a sufficient level, there is a disadvantage that the reliability of the final product can be reduced, and the mechanical properties can also be reduced.
또한, 상기 일 구현예의 반도체 패키지용 수지 조성물은 열경화성 수 지를 포함할 수 있다.  In addition, the resin composition for a semiconductor package of the embodiment may include a thermosetting resin.
상기 열경화성 수지는 에폭시 수지 , 비스말레이미드 수지 , 시아네이 트 에스터 수지 및 비스말레이미드-트리아진 수지로 이루어진 군으로부터 선택되는 1종 이상의 수지를 포함할 수 있다. 이 때， 상기 에폭시 수지로는 통상 반도체 패키지용 수지 조성물에 사용되는 것을 제한 없이 사용 할 수 있으며, 그 종류가 한정되지는 않으며， 비스페놀 A 형 에폭시 수지， 페놀 노볼락 에폭시 수지， 페닐 아랄킬계 에폭 시 수지 , 테트라페닐 에탄 에폭시 수지 , 나프탈렌계 에폭시 수지， 바이페닐 계 에폭시 수지， 디시클로펜타디엔 에폭시 수지 , 및 디시클로펜타디엔계 에 폭시 수지와 나프탈렌계 에폭시 수지의 흔합물로 이루어진 군에서 선택된 1 종 이상일 수 있다. The thermosetting resin may include at least one resin selected from the group consisting of an epoxy resin, a bismaleimide resin, a cyanate ester resin, and a bismaleimide-triazine resin. At this time, as the epoxy resin can be used without limitation to those usually used in the resin composition for semiconductor packages, the type is not limited, bisphenol A epoxy resin, phenol novolak epoxy resin, phenyl aralkyl epoxy 1 type selected from the group consisting of a resin, a tetraphenyl ethane epoxy resin, a naphthalene epoxy resin, a biphenyl epoxy resin, a dicyclopentadiene epoxy resin, and a mixture of a dicyclopentadiene epoxy resin and a naphthalene epoxy resin It may be abnormal.
구체적으로， 상기 애폭시 수지는 하기 화학식 5로 표시되는 비스페놀 형 에폭시 수지 , 하기 화학식 6로 표시되는 노볼락형 에폭시 수지， 하기 화 학식 7로 표시되는 페닐 아랄킬계 에폭시 수지, 하기 화학식 8로 표시되는 테트라페닐에탄형 에폭시 수지， 하기 화학식 9과 10으로 표시되는 나프탈렌 형 에폭시 수지, 하기 화학식 11로 표시되는 바이페닐형 에폭시 수지， 및 하기 화학식 12로 표시되는 디시클로펜타디엔형 에폭시 수지로 이루어진 군 에서 선택된 1종 이상을 사용할 수 있다.  Specifically, the epoxy resin is a bisphenol-type epoxy resin represented by the formula (5), a novolak-type epoxy resin represented by the formula (6), a phenyl aralkyl-based epoxy resin represented by the formula (7), represented by the formula (8) In the group consisting of a tetraphenylethane type epoxy resin, a naphthalene type epoxy resin represented by the following formulas (9) and (10), a biphenyl type epoxy resin represented by the following formula (11), and a dicyclopentadiene type epoxy resin represented by the following formula (12) One or more selected species may be used.
[화학식 5]  [Formula 5]
Figure imgf000012_0001
Figure imgf000012_0001
n은 0 또는 1 내지 50의 정수이다.  n is 0 or an integer from 1 to 50.
보다 구체적으로， 상기 화학식 5의 에폭시 수지는 R의 종류에 따라， 각각 비스페놀 A형 에폭시 수지, 비스페놀 F형 에폭시 수지, 비스페놀 M형 에폭시 수지 또는 비스페놀 S형 에폭시 수지일 수 있다ᅳ  More specifically, the epoxy resin of Formula 5 may be a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a bisphenol M type epoxy resin, or a bisphenol S type epoxy resin, respectively, according to the type of R R.
[  [
Figure imgf000012_0002
상기 화학식 6에서,
Figure imgf000012_0002
In Chemical Formula 6,
R은 H 또는 CH3이고， R is H or CH 3 ，
n은 0 또는 1 내지 50의 정수이다.  n is 0 or an integer from 1 to 50.
보다 구체적으로， 상기 화학식 6의 노볼락형 에폭시 수지는 R의 종류 에 따라, 각각 페놀 노볼락형 에폭시 수지 또는 크레졸 노볼락형 에폭시 수 지일 수 있다. .  More specifically, the novolak-type epoxy resin of Formula 6 may be a phenol novolak-type epoxy resin or cresol novolak-type epoxy resin, respectively, depending on the type of R. .
[화학식 7]  [Formula 7]
Figure imgf000013_0001
Figure imgf000013_0001
[화학식 8]  [Formula 8]
Figure imgf000013_0002
Figure imgf000013_0002
[화학식 11]
Figure imgf000013_0003
상기 화학식 11에서, [Formula 11]
Figure imgf000013_0003
In Chemical Formula 11,
n은 0 또는 1 내지 50의 정수이다. [화학식 12] n is 0 or an integer from 1 to 50. [Formula 12]
Figure imgf000014_0001
Figure imgf000014_0001
상기 화학식 12에서， n은 0 또는 1 내지 50의 정수이다.  In Formula 12, n is 0 or an integer of 1 to 50.
그리고， 상기 반도체 패키지용 수지 조성물이 에폭시 수지를 포함하 는 경우에는 경화를 위하여 에폭시 수지의 경화제를 함께 사용할 수 있다. 상기 에폭시 수지의 경화제로는 통상 반도체 패키지용 수지 조성물에 사용되는 것을 제한 없아 사용 할 수 있으며， 그 종류가 한정되지는 않는다. 예를 들어, 페놀 노볼락 형， 아민 형, 사이올 ( thi ol ) 형, 산무수물화 형 물 질 등을 들 수 있고， 이들을 단독 또는 2종 이상 흔합하여 사용할 수 있다. 그리고, 상기 비스말레이미드 수지는 통상 반도체 패키지용 수지 조 성물에 사용되는 것을 제한 없이 사용 할 수 있으며, 그 종류가 한정되지는 않는다.  In addition, when the resin composition for a semiconductor package includes an epoxy resin, a curing agent of an epoxy resin may be used together for curing. As a hardening | curing agent of the said epoxy resin, what is normally used for the resin composition for semiconductor packages can be used without a restriction | limiting, The kind is not limited. For example, a phenol novolak type, an amine type, a thiol type, an acid anhydride type material, etc. are mentioned, These can be used individually or in mixture of 2 or more types. In addition, the bismaleimide resin can be used without limitation, which is usually used in the resin composition for semiconductor packages, the type is not limited.
바람직한 일례를 들면.， 상기 비스말레이미드 수지는 하기 화학식 13 으로 표시되는 디페닐메탄형 비스말레이미^ 수지, 하기 화학식 14로 표시 되는 페닐렌형 비스말레이미드 수지， 하기 화학식 15로 표시되는 비스페놀 A형 디페닐 에테르 비스말레이미드 수지, 및 하기 화학식 16으로 표시되는' 디페닐메탄형 비스말레이미드 및 페닐메탄형 말레이미드 수지의 올리고머로 구성된 비스말레이미드 수지로 이루어진 군에서 선택된 1종 이상일 수 있다. G. The preferred embodiment. , The bismaleimide resin is a diphenylmethane type bismaleimide resin represented by the following formula (13), a phenylene type bismaleimide resin represented by the following formula (14), bisphenol A type diphenyl ether bismaleimide represented by the following formula (15) It may be at least one selected from the group consisting of a mid resin, and a bismaleimide resin composed of oligomers of ' diphenylmethane bismaleimide and phenylmethane type maleimide resin represented by the following formula (16).
Figure imgf000014_0002
Figure imgf000014_0002
상기 화학식 13에서， In Chemical Formula 13,
i 및 ¾는 각각 독립적으로 H , CH3 또는 C2¾이다. i and ¾ are each independently H, CH 3 or C 2 ¾.
[화학식 14] [Formula 14]
Figure imgf000015_0001
Figure imgf000015_0002
Figure imgf000015_0003
Figure imgf000015_0001
Figure imgf000015_0002
Figure imgf000015_0003
상기 화학식 16에서,  In Chemical Formula 16,
n은 0 또는 1 내지 50의 정수이다.  n is 0 or an integer from 1 to 50.
또한， 상기 시아네이트 에스터 수지는 통상 반도체 패키지용 수지 조 성물에 사용되는 것을 제한 없이 사용 할 수 있으며, 그 종류가 한정되지는 않는다.  In addition, the cyanate ester resin can be used without limitation, those usually used in the resin composition for semiconductor packages, the type is not limited.
바람직한 일례를 들면， 상기 시아네이트 에스터 수지는 하기 화학식 17로 표시되는 노볼락형 시아네이트 수지， 하기 화학식 18로 표시되는 디시 클로펜타디엔형 시아네이트 수지， 하기 화학식 19로 표시되는 비스페놀형 시아네이트 수지 및 이들의 일부 트리아진화된 프리폴리머를 들 수 있고, 이들은 단독 혹은 2종 이상 흔합하여 사용할 수 있다.  As a preferred example, the cyanate ester resin is a novolac cyanate resin represented by the following formula (17), a diclopentadiene type cyanate resin represented by the following formula (18), and a bisphenol cyanate resin represented by the following formula (19). And some triazineylated prepolymers thereof, and these may be used alone or in combination of two or more thereof.
[화학식 17]  [Formula 17]
Figure imgf000015_0004
Figure imgf000015_0004
상기 화학식 17에서,  In Chemical Formula 17,
n은 0 또는 1 내지 50의 정수이다. [화학식 18] n is 0 or an integer from 1 to 50. [Formula 18]
Figure imgf000016_0001
Figure imgf000016_0001
상기 화학식 18에서,  In Chemical Formula 18,
n은 0 또는 1 내지 50의 정수이다.  n is 0 or an integer from 1 to 50.
[화학식 19]
Figure imgf000016_0002
[Formula 19]
Figure imgf000016_0002
상기 화학식 19에  In Chemical Formula 19
R은
Figure imgf000016_0003
또는 이다. 보다 구체적으로， 상기 화학식 19의 시아네이트 수지는 R의 종류에 따라, 각각 비스페놀 A형 시아네이트 수지 , 비스페놀 E형 시아네이트 수지， 비스페놀 F형 시아네이트 수지， 또는 비스페놀 M형 시아네이트 수지일 수 있다. R is
Figure imgf000016_0003
Or is More specifically, the cyanate resin of Formula 19 may be bisphenol A type cyanate resin, bisphenol E type cyanate resin, bisphenol F type cyanate resin, or bisphenol M type cyanate resin, respectively, according to the type of R. .
그리고, 상기 비스말레이미드-트리아진 수지는 통상 반도체 패키지용 수지 조성물에 사용되는 것을 제한 없이 사용 할 수 있으며, 그 종류가 한 정되지는 않는다.  In addition, the bismaleimide-triazine resin can be used without limitation, which is usually used in the resin composition for semiconductor packages, the type is not limited.
또한， 상기 일 구현예의 반도체 패키지용 수지 조성물은 무기 충진제 를 포함할 수 있다. 상기 무기 층진제는 통상 반도체 패키지용 수지 조성물 에 사용되는 것을 제한 없이 사용 할 수 있으며, 구체적인 예로는 실리카, 알루미늄 트리하이드록사이드, 마그네슴 하이드록사이드, 몰리브데늄 옥사 이드， 징크 몰리브데이트, 징크 보레이트， 징크 스타네이트, 알루미나， 클 러)이 , 카올린 , 탈크， 소성 카올린， 소성 탈크 , 마이카， 유리 단섬유, 글라 스 미세 파우더 및 중공 글라스를 들 수 있으며 이들로 이루어진 군에서 선 택된 1종 이상일 수 있다.  In addition, the resin composition for a semiconductor package of the embodiment may include an inorganic filler. The inorganic layer dusting agent may be used without limitation, which is usually used in the resin composition for semiconductor packages, specific examples include silica, aluminum trihydroxide, magnesium hydroxide, molybdenum oxide, zinc molybdate, Zinc borate, zinc stannate, alumina, chlorine), kaolin, talc, calcined kaolin, calcined talc, mica, short glass fiber, glass fine powder, and hollow glass, selected from the group consisting of It may be abnormal.
상기 아민 경화제 및 열경화성 수지 100 중량부에 대하여 상기 무기 충진제 함량이 200 중량부 이상, 또는 200 중량부 내지 500 중량부， 또는 250 중량부 내지 400 중량부일 수 있다. 상기 충진제의 함량이 약 200 중량 부 미만이면 열팽창계수가 증가하여 리플로우 (ref l ow) 공정시 휨 현상이 심 화되며, 인쇄회로기판의 강성이 감소하는 문제가 있다. The inorganic based on 100 parts by weight of the amine curing agent and the thermosetting resin The filler content may be 200 parts by weight or more, or 200 parts by weight to 500 parts by weight, or 250 parts by weight to 400 parts by weight. If the content of the filler is less than about 200 parts by weight, the coefficient of thermal expansion increases, so that the warpage phenomenon in the reflow (ref low) process is intensified, and the rigidity of the printed circuit board is reduced.
본 발명의 바람직한 구현예에 따라, 상기 무기 충진제는 내습성， 분 산성을 향상시키는 관점에서 실란 커플링제로 표면처리된 실리카를 사용할 수 있다.  According to a preferred embodiment of the present invention, the inorganic filler may use silica surface-treated with a silane coupling agent in terms of improving moisture resistance and dispersion.
상기 무기 충진제를 표면 처리하는 방법은, 실란 커플링제를 표면 처 리제로 이용하여 실리카 입자를 건식 또는 습식으로 처리하는 방법이 사용 될 수 있다. 예를 들어, 실리카 입자 loo 중량부를 기준으로 0.01 내지 1 중량부의 실란 커플링제를 사용하여 습식방법으로 실리카를 표면처리하여 사용할 수 있다.  As the method for surface treatment of the inorganic filler, a method of dry or wet treatment of silica particles using a silane coupling agent as a surface treatment agent may be used. For example, the silica may be surface treated by a wet method using 0.01 to 1 parts by weight of the silane coupling agent based on the loo parts by weight of the silica particles.
구체적으로, 상기 실란커플링제로는 3-아미노프로필트리에톡시실란, N-페닐 -3-아미노프로필트리메록시실란 및 N— 2- (아미노에틸)ᅳ 3-아미노프로필 트리메록시실란과 같은 아미노실란 커플링제， 3-글리시독시프로필트리메록 시실란과 같은 에폭시 실란커플링겨 I , 3-메타크릴옥시프로필 트리메톡시실란 과 같은 비닐 실란커플링제, N-2-(N-비닐벤질아미노에틸 )— 3—아미노프로필트 리메톡시실란 하이드로클로라이드와 같은 양이온 실란커플링제 및 페닐 실 란커플링제를 들 수 있으며, 실란 커플링제는 단독으로 사용될 수 있으며, 또는 필요에 따라 적어도 두 개의 실란 커플링제를 조합하여 사용할 수 있 다.  Specifically, the silane coupling agent, such as 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, and N—2- (aminoethyl) ᅳ 3-aminopropyl trimethoxysilane Aminosilane coupling agent, epoxy silane coupling group I such as 3-glycidoxypropyltrimeroxysilane, vinyl silane coupling agent such as 3-methacryloxypropyl trimethoxysilane, N-2- (N-vinylbenzylaminoethyl Cation silane coupling agent and phenyl silane coupling agent such as aminopropyltrimethoxysilane hydrochloride, and the silane coupling agent may be used alone, or at least two silane coupling agents may be used. Can be used in combination.
보다 구체적으로， 상기 실란 화합물은 방향족 아미노 실란 또는 (메 트)아크릴실란을 포함할 수 있으며, 상기 무기 충진제의 바람직한 예로는 표면에 실란 화합물이 결합한 평균 입경 0. 1 내지 loo 인 실리카, 보 다 바람직하게는 표면에 방향족 아미노 실란이 처리된 평 1균 '입경 0. 1 /zm 내 지 100 / 인 실리카를 사용할 수 있다. 상기 방향족 아미노 실란이 처리된 평균 입경 0. 1 내지 100 인 실리카의 구체적인 예로는 SC2050MT0(Admantechs사)를 들 수 있다. 상기 (메트)아크릴은 아크릴 또는 메타크릴을 모두 포함하는 의미로 사용되었다. More specifically, the silane compound may include an aromatic amino silane or (meth) acrylic silane, and a preferred example of the inorganic filler is silica, having an average particle diameter of 0.01 to loo, in which a silane compound is bonded to a surface thereof, more preferably. you may use the 100 / silica if the aromatic amino silane treated Hei 1 bacteria "particle diameter 0. 1 / zm to the surface. Specific examples of the silica having an average particle diameter of 0.01 to 100 treated with the aromatic amino silane include SC2050MT0 (Admantechs). The (meth) acryl was used to mean both acryl or methacryl.
그리고， 상기 일 구현예의 반도체 패키지용 수지 조성물은 필요에 따 라 용제를 첨가하여 용액으로 사용할 수 있다. 상기 용제로는 수지 성분에 대해 양호한 용해성을 나타내는 것이면 그 종류가 특별히 한정되지 않으며， 알코올계， 에테르계, 케톤계, 아미드계， 방향족 탄화수소계， 에스테르겨) ,And, the resin composition for a semiconductor package of the embodiment is as needed D) It can be used as a solution by adding a solvent. The solvent is not particularly limited as long as it shows good solubility in the resin component, and may be alcohol, ether, ketone, amide, aromatic hydrocarbon, ester bran),
■ 니트릴계 등을 사용할 수 있고, 이들은 단독 또는 2종 이상 병용한 흔합 용 제를 이용할 수도 있다. 또한 상기 용매의 함량은 프리프레그 제조시 유리 섬유에 수지 조성물을 함침할 수 있는 정도면 특별히 한정되지 않는다. ■ Nitrile type | system | group etc. can be used, These can also use the mixed solvent used individually or in combination of 2 or more types. In addition, the content of the solvent is not particularly limited as long as the resin composition can be impregnated into the glass fiber during prepreg production.
또한 본 발명의 수지 조성물은 , 수지 조성물 고유의 특성을 손상시키 지 않는 한, 기타 열경화성 수지， 열가소성 수지 및 이들의 올리고머 및 엘 라스토머와 같은 다양한 고분자 화합물， 기타 난연성 화합물 또는 첨가제를 더 포함할 수도 있다. 이들은 통상적으로 사용되는 것으로부터 선택되는 것 이라면 특별히 한정하지 않는다. 예를 들어 첨가제로는 자외선흡수제, 산화 방지제， 광중합개시제， 형광증백제， 광증감제, 안료, 염료， 증점제, 활제, 소포제， 분산제, 레벨링제， 광택제 등이 있고， 목적에 부합되도록 흔합하여 사용하는 것도 가능하다.  In addition, the resin composition of the present invention may further include other thermosetting resins, thermoplastic resins and various high molecular compounds such as oligomers and elastomers, other flame retardant compounds or additives, so long as the properties of the resin composition are not impaired. have. These are not particularly limited as long as they are selected from those commonly used. For example, additives include UV absorbers, antioxidants, photopolymerization initiators, optical brighteners, photosensitizers, pigments, dyes, thickeners, lubricants, antifoaming agents, dispersants, leveling agents, brightening agents, and the like. It is also possible.
상기 일 구현예의 반도체 패키지용 수지 조성물은 열팽창계수 (CTE)가 The resin composition for a semiconductor package of the embodiment has a coefficient of thermal expansion (CTE)
15 ppm/ 0C 이하, 또는 5 ppm/ °C 내지 15 ppm/ °C일 수 있다. 구체적으로, 상 기 열팽창계수는 상기 반도체 패키지용 수지 조성물로부터 얻어진 동박적층 판 상태에서 동박층을 에칭하여 제거한 후, MD방향으로 시험편을 제작하여， TMA(TA Inst rument s , Q400)를 이용하여 , 30 °C에서 260 °C까지， 승온 속도 10 °C /mi n 조건으로 측정한 후, 50 °C 에서 150 °C 범위의 측정값을 의미한 다. 15 ppm / 0 C or less, or 5 ppm / ° C. to 15 ppm / ° C. Specifically, the coefficient of thermal expansion is removed by etching the copper foil layer in the copper foil laminated plate state obtained from the resin composition for a semiconductor package, and then made a test piece in the MD direction, by using a TMA (TA Instruments), Q400, Means the measured value in the range of 50 ° C to 150 ° C after measuring at 30 ° C to 260 ° C, temperature rising rate 10 ° C / mi n conditions.
상기 반도체 패키지용 수지 조성물이 상술한 수준의 낮은 열팽창계수 를 가짐에 따라, 금속적층판을 만들거나 빌드업 과정에서 칩과 인쇄회로기 판간 열팽창률 차이로 인해 발생하는 반도체 패키지의 휨 OVarpage) 발생을 최소화할 수 있어， 상기 프리프레그를 포함하는 금속 적층판은 반도체 패키 지용 인쇄회로기판의 빌드업 용도로 유용하게 사용될 수 있다.  As the resin composition for the semiconductor package has a low thermal expansion coefficient of the above-described level, minimization of warpage OVarpage of the semiconductor package caused by the difference in thermal expansion coefficient between the chip and the printed circuit board during the metal lamination or build-up process As such, the metal laminate including the prepreg may be usefully used for building up a printed circuit board for a semiconductor package.
상기 일 구현예의 반도체 패키지용 수지 조성물은 IPC-TMᅳ 650 The resin composition for a semiconductor package of the embodiment is IPC-TM ᅳ 650
(2. 3. 17)에 의해 측정한 수지 흐름성이 1 내지 25% , 또는 15¾> 내지 25%일 수 있다. 구체적으로， 상기 수지 흐름성은 상기 반도체 패키지용 수지 조성 물로부터 얻어진 프리프레그 상태에서 카바프레스를 이용하여 IPC-TM— 650 (2.3. 17)에 따라 측정할 수 있다. 상기 반도체 패키지용 수지 조성물이 상 술한 수준의 수지 흐름성을 가짐에 따라 금속적층판을 만들거나 빌드업 과 정에서 흐름성을 확보할 수 있어 미세 패턴을 용이하게 채울 수 있어, 상기 프리프레그를 포함하는 금속 적층관은 반도체 패키지용 인쇄회로기판의 빌 드업 용도로 유용하게 사용될 수 있다. The resin flowability measured by (2. 3. 17) can be 1-25%, or 15¾> -25%. Specifically, the resin flowability is IPC-TM—650 using carba press in the prepreg state obtained from the resin composition for the semiconductor package. It can be measured according to (2.3.17). As the resin composition for the semiconductor package has the above-described resin flowability, it is possible to make the metal laminated plate or to secure the flowability during the build-up process, so that the fine pattern can be easily filled, and the prepreg is included. The metal laminated tube may be usefully used for building up a printed circuit board for a semiconductor package.
상기 반도체 패키지용 수지 조성물의 수지 흐름성이 지나치게 감소하 게 되면， 금속 적층 및 빌드업 공정에서 미세 패턴 채움성이 감소함에 따라 적층 보이드 (Void) 발생 및 공정 수율 및 효율성이 감소할 수 있다. 또한, 상기 반도체 패키지용 수지 조성물의 수지 흐름성이 지나치게 증가하게 되 면, 적층 공정 시, 수지 흐름의 과다로 인해 인쇄회로기판의 두께 불균일 문제가 발생하거나， 설계된 두께보다 얇아져 강성이 감소할 수 있다.  When the resin flowability of the resin composition for the semiconductor package is excessively reduced, as the fine pattern fillability decreases in the metal lamination and buildup process, the generation of laminated voids and the process yield and efficiency may be reduced. In addition, when the resin flowability of the resin composition for the semiconductor package is excessively increased, a problem of thickness unevenness of the printed circuit board may occur due to the excessive flow of resin during the lamination process, or may become thinner than the designed thickness, thereby reducing the rigidity. .
또한， 상기 일 구현예의 반도체 패키지용 수지 조성물은 140 이상 또는 145 °C 내지 165 °C에서 최소점도를 가지며， 상기 최소점도가 100 Pa · s 내지 500 Paᅳ s , 또는 150 Pa . s 내지 400 Pa ' s , 또는 200 Pa · s 내 지 350 Pa ■ s , 또는 250 Pa · s 내지 320 Pa · s 일 수 있다. 구체적으로， 상 기 점도는 상기 반도체 패키지용 수지 조성물로부터 얻어진 프리프레그 상 태에서 Anton Paar사의 Modul ar compact Rheometer (모델 MCR 302)를 이용하 여 측정할 수 있다. 상기 반도체 패키지용 수지 조성물이 상술한 수준의 점 도를 나타냄에 따라, 금속적층판을 만들거나 빌드업 과정에서 흐름성을 확 보할 수 있어 미세 패턴을 용이하게 채울 수 있어, 상기 프리프레그를 포함 하는 금속 적층판은 반도체 패키지용 인쇄회로기판의 빌드업 용도로 유용하 게 사용될 수 있다. In addition, the resin composition for a semiconductor package of the embodiment has a minimum viscosity at 140 or more or 145 ° C to 165 ° C, the minimum viscosity is 100 Pa · s to 500 Pa ᅳ s, or 150 Pa. s to 400 Pa 's, or 200 Pa · s in not ■ s 350 Pa, or 250 Pa · s to 320 Pa · s may be. Specifically, the viscosity can be measured using a Modul ar compact Rheometer (Model MCR 302) of Anton Paar in the prepreg state obtained from the resin composition for semiconductor packages. As the resin composition for the semiconductor package exhibits the above-described viscosity, it is possible to secure the flowability during the production of the metal laminate or the build-up process so that the fine pattern can be easily filled, and the metal including the prepreg. Laminates can be useful for building up printed circuit boards for semiconductor packages.
또한， 상기 일 구현예의 반도체 패키지용 수지 조성물은 IPC-TM— 650 (2.4. 18.3)에 의해 측정한 인장신율이 2.0 % 이상, 또는 2.0 % 내지 5.0%, 또는 2.0 % 내지 3.0% , 또는 2.3 % 내지 3.0%일 수 있다. 구체적으로， 상기 인장신율은 상기 반도체 패키지용 수지 조성물로부터 얻어진 프리프레그 상 태에서， 유리섬유의 MD 및 TD방향이 일치하도록 10매를 적층하여， 220 °C 및 35 kg/cuf의 조건으로 100분간 프레스 한 후， IPC-TM-650 (2.4. 18.3)에 따라， Universal Test ing Machine( Inst ron 3365)장비를 이용하여 MD방향의 인장신율을 측정할 수 있다. 상기 반도체 패키지용 수지 조성물이 상술한 수준의 인장신율을 나타냄에 따라, 금속적층판을 만들거나 빌드업 과정에서 기계적 물성을 확보할 수 있어 우수한 내구성을 통해 반도체 패키지용 인쇄 회로기판의 빌드업 용도로 유용하게 사용될 수 있다. 한편， 발명의 다른 구현예에 따르면 , 상기 반도체 패키지용 수지 조 성물을 섬유 기재에 함침시켜 제조된 프리프레그가 제공될 수 있다. In addition, the resin composition for a semiconductor package of the embodiment has a tensile elongation of 2.0% or more, or 2.0% to 5.0%, or 2.0% to 3.0%, or 2.3% as measured by IPC-TM-650 (2.4.18.3). To 3.0%. Specifically, the tensile elongation is 10 minutes in a prepreg state obtained from the resin composition for the semiconductor package, laminated 10 sheets to match the MD and TD direction of the glass fiber, 100 minutes under conditions of 220 ° C and 35 kg / cuf After pressing, in accordance with IPC-TM-650 (2.4.18.3), tensile elongation in the MD direction can be measured using a universal testing machine (Inst ron 3365). The resin composition for semiconductor packages described above By showing the tensile elongation of the level, it is possible to secure the mechanical properties in the process of making a metal laminate or build-up, it can be useful for the build-up of printed circuit board for semiconductor package through excellent durability. Meanwhile, according to another embodiment of the present invention, a prepreg prepared by impregnating the resin composition for a semiconductor package into a fiber substrate may be provided.
상기 프리프레그는 상기 반도체 패키지용 수지 조성물이 반경화 상태 로 섬유 기재에 함침되어 있는 것을 의미한다.  The prepreg means that the resin composition for the semiconductor package is impregnated into the fiber substrate in a semi-cured state.
상기 섬유 기재는 그 종류가 특별히 한정되지는 않으나， 유리 섬유 기재， 폴리아미드 수지 섬유, 방향족 폴리아미드 수지 섬유 등의 폴리아미 드계 수지 섬유, 폴리에스테르 수지 섬유， 방향족 폴리에스테르 수지 섬유, 전 방향족 폴리에스테르 수지 섬유 등의 폴리에스테르계 수지 섬유， 폴리이 미드 수지 섬유， 폴리벤족사졸 섬유 불소 수지 섬유 등을 주성분으로 하는 직포 또는 부직포로 구성되는 합성 섬유 기재, 크래프트지, 코튼 린터지ᅵ , 린터와 크래프트 필프의 흔초지 등을 주성분으로 하는 종이 기재 등이 사용 될 수 있으며 , 바람직하게 유리 섬유 기재를 사용한다. 상기 유리 섬유 기 재는 프리프레그의 강도가 향상되고 흡수율을 내릴 수 있으며， 또 열팽창 계수를 작게 할 수 있다.  Although the kind of the fiber base material is not particularly limited, polyamide-based resin fibers, such as glass fiber base material, polyamide resin fiber, aromatic polyamide resin fiber, polyester resin fiber, aromatic polyester resin fiber, all aromatic polyester Synthetic fiber base, kraft paper, cotton linter paper composed of woven or nonwoven fabric mainly composed of polyester resin fiber such as resin fiber, polyimide resin fiber, polybenzoxazole fiber fluorine resin fiber, etc. Paper substrates mainly composed of grass paper and the like may be used, and glass fiber substrates are preferably used. The glass fiber substrate can improve the strength of the prepreg, lower the absorption rate, and reduce the coefficient of thermal expansion.
본 발명에서 사용되는 유리기재는 다양한 인쇄회로기판 물질용으로 사용되는 유리기재로부터 선택될 수 있다. 이들의 예로서는, E 글라스, D 글라스， S 글라스， T 글라스， NE 글라스 및 L 글라스와 같은 유리 섬유를 포함하나 이에 한정되는 것은 아니다. 필요에 따라서 의도된 용도 또는 성 능에 따라， 상기 유리기재 물질을 선택할 수 있다. 유리기재 형태는 전형적 으로 직포, 부직포, 로빙 ( roving) , 잘개 다진 스트랜드 매트 (chopped st rand mat ) 또는 서페이싱 매트 (sur facing mat )이다. 상기 유리기재 기재 의 두께는 특별히 한정되지 않지만, 약 0. 01 내지 0.3mm 등을 사용할 수 있 다. 상기 물질 중, 유리 섬유 물질이 강도 및 수분 흡수'특성 면에서 더욱 바람직하다. The glass substrate used in the present invention may be selected from glass substrates used for various printed circuit board materials. Examples thereof include, but are not limited to, glass fibers such as E glass, D glass, S glass, T glass, NE glass and L glass. If necessary, the glass-based material may be selected according to the intended use or performance. Glass-based forms are typically woven, nonwoven, roving, chopped st rand mats, or surface facing mats. The thickness of the glass base material is not particularly limited, but about 0.01 to 0.3 mm can be used. Of these materials, glass fiber materials are more preferred in terms of strength and water absorption ' properties.
■ 또한 본 발명에서 상기 프리프레그를 제조하는 방법은 특별히 한정되 지 않으며 , 이 분야에 잘 알려진 방법에 의해 제조될 수 있다. 예를 들면， 상기 프리프레그의 제조방법은 함침법， 각종 코터를 이용하는 코팅법, 스프 레이 분사법 등을 이용할 수 있다. In addition, the method for producing the prepreg in the present invention is not particularly limited and may be prepared by methods well known in the art. For example, The prepreg manufacturing method may be an impregnation method, a coating method using various coaters, spray spraying method and the like.
상기 함침법의 경우 바니시를 제조한 후， 상기 섬유 기재를 바니시에 함침하는 방법으로 프리프레그를 제조할 수 있다.  In the case of the impregnation method, after preparing the varnish, the prepreg may be prepared by impregnating the fiber substrate with the varnish.
즉, 상기 프리프레그의 제조 조건 등은 특별히 제한하는 것은 아니지 만， 상기 반도체 패키지용 수지 조성물에 용제를 첨가한 바니시 상태로 사 용하는 것이 바람직하다 . 상기 수지 바니시용 용제는 상기 수지 성분과 흔 합 가능하고 양호한 용해성을 갖는 것이라면 특별히 한정하지 않는다. 이들 의 구체적인 예로는, 아세톤, 메틸 에틸 케톤, 메틸이소부틸 케톤 및 시클 로핵사논과 같은 케톤， 벤젠, 를루엔 및 자일렌과 같은 방향족 하이드로카 본, 및 디메틸포름아미드 및 디메틸아세트아미드와 같은 아미드, 메틸셀로 솔브, 부틸샐로솔브 같은 알리파틱 알코올 등이 있다.  That is, although the manufacturing conditions, etc. of the said prepreg are not specifically limited, It is preferable to use it in the varnish state which added the solvent to the said resin composition for semiconductor packages. The solvent for the resin varnish is not particularly limited as long as it is compatible with the resin component and has good solubility. Specific examples thereof include ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclonuxanone, aromatic hydrocarbons such as benzene, toluene and xylene, and amides such as dimethylformamide and dimethylacetamide, Aliphatic alcohols such as methylcellosolve and butyl salosolve.
또한, 상기 프리프레그로 제조시, 사용된 용제가 80 중량 % 이상 휘 발하는 것이 바람직하다. 이 때문에， 제조 방법이나 건조 조건 등도 제한은 없고, 건조시의 온도는 약 80 °C 내지 200 °C , 시간은 바니시의 겔화 시간 과의 균형으로 특별히 제한은 없다. 또한， 바니시의 함침량은 바니시의 수 지 고형분과 기재의 총량에 대하여 바니시의 수지 고형분이 약 30 내지 80 중량%가 되도록 하는 것이 바람직하다. In addition, when preparing the prepreg, it is preferable that the solvent used is volatilized by 80% by weight or more. Accordingly, also the manufacturing method and drying conditions are limited, the temperature during drying is about 80 ° C to 200 ° C, the time is not particularly limited to the balance with the varnish gelling time. In addition, the impregnation amount of the varnish is preferably such that the resin solid content of the varnish is about 30 to 80% by weight relative to the total amount of the resin solid content of the varnish and the base material.
상기 다른 구현예의 ,프리프레그는 열팽창계수 (CTE)가 15 ppm/ °C 이하， 또는 5 ppm/ °C 내지 15 ppm/ t:일 수 있다. 상기 열팽창계수에 대한 내용은 상기 일 구현예의 반도체 패키지용 수지 조성물에서 상술한 내용을 포함한 4. . - 상기 다른 구현예의 프리프레그는 IPC— TM-650 (2 .3. 17)에 의해 측정 한 수지 흐름성이 10% 내지 25% , 또는 15% 내지 25%일 수 있다. 상기 수지 흐름성에 대한 내용은 상기 일 구현예의 반도체 패키지용 수지 조성물에서 상술한 내용을 포함한다. In another embodiment , the prepreg may have a coefficient of thermal expansion (CTE) of 15 ppm / ° C or less, or 5 ppm / ° C to 15 ppm / t :. 4. The thermal expansion coefficient information includes the above-described contents in the resin composition for a semiconductor package of the embodiment. The prepreg of the other embodiment may have a resin flowability of 10% to 25%, or 15% to 25%, as measured by IPC-TM-650 (2.3.17). The content of the resin flowability includes the above-mentioned content in the resin composition for a semiconductor package of the embodiment.
또한, 상기 다른 구현예의 프리프레그는 140 °C 이상, 또는 145 °C 내지 165 °C에서 최소점도를 가지며， 상기 최소점도가 100 Pa - s 내지 500 Pa ■ s , 또는 150 Pa - s 내지 400 Pa ■ s , 또는 200 Pa ■ s 내지 350 Pa · s , 또는 250 Pa s 내지 320 Pa s 일 수 있다. 상기 점도에 대한 내용은 상기 일 구현예의 반도체 패키지용 수지 조성물에서 상술한 내용을 포함한다. 또한， 상기 다른 구현예의 프리프레그는 IPC— TM-650 (2.4. 18.3)에 의 해 측정한 인장신율이 2. 0 % 이상, 또는 2. 0 % 내지 5. 0%, 또는 2.0 % 내지 3 .0% , 또는 2.3 % 내지 3 .0%일 수 있다. 상기 인장신율에 대한 내용은 상기 일 구현예의 반도체 패키지용 수지 조성물에서 상술한 내용을 포함한다. 또한, 발명의 또 다른 구현예에 따르면， 상기 프리프레그; 및 가열 및 가압에 의해 상기 프리프레그와 일체화된 포함하는 금속박；을 포함하는 금속박 적층판이 제공될 수 있다. In addition, the prepreg of the other embodiment has a minimum viscosity at 140 ° C or more, or 145 ° C to 165 ° C, the minimum viscosity is 100 Pa-s to 500 Pa ■ s, or 150 Pa-s to 400 Pa ■ s, or 200 Pa ■ s to 350 Pa.s, or 250 Pa s to 320 Pa s. For information on the viscosity One embodiment includes the above-described information in the resin composition for a semiconductor package. In addition, the prepreg of the other embodiment has a tensile elongation measured by IPC—TM-650 (2.4.18.3) of at least 2. 0%, or from 2. 0% to 5.0%, or from 2.0% to 3%. 0%, or 2.3% to 3.0%. Details of the tensile elongation include those described above in the resin composition for a semiconductor package of the embodiment. Further, according to another embodiment of the invention, the prepreg; And a metal foil comprising a metal foil integrated with the prepreg by heating and pressurizing.
상기 금속박은 동박; 알루미늄박; 니켈, 니켈 -인， 니켈 -주석 합금, 니켈-철 합금， 납 또는 납 -주석 합금을 중간층으로 하고 , 이 양면에 서로 다른 두께의 구리층을 포함하는 3층 구조의 복합박; 또는 알루미늄과 동박 을 복합한 2층 구조의 복합박을 포함한다.  The metal foil is copper foil; Aluminum foil; A composite foil having a three-layer structure including nickel, nickel-phosphorus, nickel-tin alloy, nickel-iron alloy, lead or lead-tin alloy as an intermediate layer, and including copper layers having different thicknesses on both surfaces thereof; Or a composite foil having a two-layer structure in which aluminum and copper foil are combined.
바람직한 일 구현예에 따르면 , 본 발명에 이용되는 금속박은 동박이 나 알루미늄박이 이용되고 약 2 내지 200 의 두께를 갖는 것을 사용할 수 있지만, 그 두께가 약 2 내지 35 m인 것이 바람직하다. 바람직하게, 상 기 금속박으로는 동박을 사용한다. 또한 본 발명에 따르면 금속박으로서 니켈, 니켈 -인， 니켈 -주석 합금, 니켈ᅳ철 합금, 납, 또는 납 -주석 합금 등 을 중간층으로 하고， 이의 양면에 0 .5 내지 15 의 구리층과 10 내지 300 의 구리층을 설치한, 3층 구조의 복합박 또는 알루미늄과 동박올 복합한 2층 구조 복합박을 사용할 수도 있다.  According to a preferred embodiment, the metal foil used in the present invention can be used copper foil or aluminum foil and having a thickness of about 2 to 200, it is preferable that the thickness is about 2 to 35 m. Preferably, copper foil is used as the metal foil. According to the present invention, as the metal foil, nickel, nickel-phosphorus, nickel-tin alloy, nickel ferrous alloy, lead, or lead-tin alloy is used as an intermediate layer, and 0.5 to 15 copper layers and 10 to 15 are formed on both surfaces thereof. The three-layered composite foil or the two-layered composite foil obtained by combining aluminum and copper foil may be used.
이렇게 제조된 프리프레그를 포함하는 금속 적층판은 1매 이상으로 적층한 후， 양면 또는 다층 인쇄 회로 기판의 제조에 사용할 수 있다 . .본 발명은 상기 금속박 적층판을 회로 가공하여 양면 또는 다층 인쇄회로기판 을 제조할 수 있으며， 상기 회로 가공은 일반적인 양면 또는 다층 인쇄 회 로 기판 제조 공정에서 행해지는 방법을 적용할 수 있다. The metal laminate including the prepreg thus prepared can be used for the manufacture of double-sided or multilayer printed circuit boards after laminating in one or more sheets. . The present invention can manufacture a double-sided or multilayer printed circuit board by circuit-processing the metal foil laminate, the circuit processing can be applied to a method performed in a general double-sided or multilayer printed circuit board manufacturing process.
【발명의 효과】  【Effects of the Invention】
본 발명에 따르면, 높은 유동성， 저열팽창 특성 및 우수한 기계적 물 성을 갖는 반도체 패키지용 수지 조성물과 이를 이용한 프리프레그 및 금속 박 적충판이 제공될 수 있다 . 【발명을 실시하기 위한 구체적인 내용】 According to the present invention, a resin composition for a semiconductor package having high fluidity, low thermal expansion characteristics and excellent mechanical properties, and a prepreg and a metal lamination plate using the same can be provided. [Specific contents to carry out invention]
발명을 하기의 실시예에서 보다 상세하게 설명한다. 단， 하기의 실시 예는 본 발명을 예시하는 것일 뿐， 본 발명의 내용이 하기의 실시예에 의하 여 한정되는 것은 아니다.  The invention is explained in more detail in the following examples. However, the following examples are merely to illustrate the present invention, the content of the present invention is not limited by the following examples.
<실시예 및 비교예: 반도체 패키지용 수지 조성물， 프리프레그 및 동 박 적층판 > <Examples and Comparative Examples: Resin Compositions, Prepregs, and Copper Foil Laminates for Semiconductor Packages>
(1) 반도체 패키지용 수지 조성물의 제조  (1) Preparation of Resin Composition for Semiconductor Package
하기 표 1 및 표 2의 조성에 따라 각 성분을 메틸에틸케톤에 고형분 65%에 맞추어 투입하여 흔합한 후, 400 rpm 속도로 하루동안 상온 교반하여 실시예 1 내지 5, 비교예 1 내지 6의 반도체 패키지용 수지 조성물 (수지 바 니시)를 제조하였다. 구체적으로 상기 실시예 1 내지 5에서 제조된 수지 조 성물의 구체적인 조성은 하기 표 1에 기재된 바와 같고, 상기 비교예 1 내지 6에서 제조된 수지 조성물의 구체적인 조성은 하기 표 2에 기재된 바와 같다.  According to the composition of Table 1 and Table 2, each component was added to methyl ethyl ketone according to the solid content of 65%, followed by mixing, followed by stirring at room temperature at 400 rpm for one day. The resin composition (resin varnish) for packages was prepared. Specifically, the specific composition of the resin composition prepared in Examples 1 to 5 is as described in Table 1 below, and the specific composition of the resin composition prepared in Comparative Examples 1 to 6 is as described in Table 2 below.
(2) 프리프레그 및 동박 적층판의 제조  (2) Preparation of prepreg and copper foil laminate
상기 제조된 반도체 패키지용 수지 조성물 (수지 바니시)을 두께 15 의 유리 섬유 (Nittobo사 제조， T— glass #1017)에 함침시킨 후， 170 °C의 온 도에서 2~5분간 열풍 건조하여 25 의 프리프레그를 제조하였다.  After impregnating the resin composition (resin varnish) for the semiconductor package prepared above into glass fiber having a thickness of 15 (manufactured by Nittobo, T—glass # 1017), it was dried by hot air for 2 to 5 minutes at a temperature of 170 ° C. Prepregs were prepared.
상기에서 제조된 프리프레그 2매를 적층한 후, 그 양면에 동박 (두께 I2im, Mitsui사 제조)을 위치시켜 적층하고， 220 t 및 35 kg/c '의 조건으 로 100분간 경화시켜 동박 적층판을 제조하였다.  After the two prepregs prepared above were laminated, copper foil (thickness I2im, manufactured by Mitsui) was placed on both sides of the prepreg, and the copper foil laminated plates were cured for 100 minutes under conditions of 220 t and 35 kg / c '. Prepared.
【표 1】 Table 1
반도체 패키지용 수지 조성물의 조성  Composition of Resin Composition for Semiconductor Package
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000025_0001
* DDS- 4, 4 '-di ami nodi phenyl sulfone  * DDS-4, 4'-di ami nodi phenyl sulfone
* TFB: 2,2 -bis(trifl uor omethy 1 ) benz i d i ne； 2,2'- Bis(tri f luoromethyl )-4,4' -biphenyldi amine  * TFB: 2,2 -bis (trifl uor omethy 1) benz i d i ne; 2,2'- Bis (tri f luoromethyl) -4,4 '-biphenyldi amine
* DDM: 4 , 4 ' -d i am i nod i heny 1 methane  * DDM: 4, 4 '-d i am i nod i heny 1 methane
* DDE: 4,4' -diaminodi henyl ether  * DDE: 4,4 '-diaminodi henyl ether
* TDA: 4,4' -Thiodiani line; 4, 4 '-diaminodi henyl sulfide  TDA: 4,4'-Thiodiani line; 4,4'-diaminodi henyl sulfide
* XD-1000: 에폭시 수지 (Nippon kayaku사)  * XD-1000: epoxy resin (Nippon kayaku)
* NC-3000H: 에폭시 수지 (Nippon kayaku사)  * NC-3000H: epoxy resin (Nippon kayaku)
* HP-6000: 나프탈렌계 에폭시 수지 (DIC사)  * HP-6000: Naphthalene epoxy resin (DIC)
* BMI— 2300: 비스말레이미드 수지 (DAIWA KASEI사)  * BMI-2300: Bismaleimide Resin (DAIWA KASEI Co., Ltd.)
* SC2050MTO: 페닐아미노실란 처리된 슬러리 타입의 마이크로 실리카， 평균입경 0.5 m (Admantechs사)  * SC2050MTO: Slurry type micro silica with phenylaminosilane treatment, average particle size 0.5 m (Admantechs)
* 당량비 ： 하기 수학식 1을 통해 계산됨  * Equivalence Ratio ： calculated by Equation 1 below
[수학식 1]  [Equation 1]
열경화성 수지 대비 아민 경화제 당량비 = (DDS 의 총 활성수소 당량 Amine curing agent equivalent ratio to thermosetting resin = (total active hydrogen equivalent of DDS
+ TFB의 총 활성수소 당량 + DDM의 ^ 활성수소 당량 + DDE의 총 활성수소 당량 + TDA의 총 활성수소 당량) I {(XD-1000의 총 에폭시 당량 + NC-3000H 의 총 에폭시 당량 + HP-6000의 총 에폭시 당량) + (BMI-2300의 총 말레이 미드 당량) } + Total active hydrogen equivalent of TFB + ^ Active hydrogen equivalent of DDM + Total active hydrogen equivalent of DDE + Total active hydrogen equivalent of TDA) I {(Total epoxy equivalent of XD-1000 + Total epoxy equivalent of NC-3000H + HP- 6000 total epoxy equivalents) + (total maleimide equivalents of BMI-2300)}
상기 수학식 1에서， DDS의 총 활성수소 당량은 DDS의 총 증량 (g)을 In Equation 1, the total active hydrogen equivalent weight of DDS is calculated as
DDS의 활성수소 단위당량 (62g/eq)으로 나눈 값이고， TFB의 총 활성수소 당량은 TFB의 총 중량 (g)을 TFB의 활성수소 단위 당량 (80g/eq)으로 나눈 값이고， Divided by the unit equivalent of DDS (62 g / eq) of active hydrogen, The total active hydrogen equivalent of TFB is the total weight of TFB (g) divided by the unit equivalent of TFB (80 g / eq) of active hydrogen,
DDM의 총 활성수소 당량은 DDM의 총 중량 (g)을 DDM의 활성수소 단위 당량 (49.5g/eq)으로 나눈 값이고  The total active hydrogen equivalent of DDM is the total weight of DDM divided by the equivalent weight of the active hydrogen of DDM (49.5 g / eq).
DDE의 총 활성수소 당량은 DDE의 총 중량 (g)을 DDE의 활성수소 단위 당량 (50g/eq)으로 나눈 값이고,  Total active hydrogen equivalent of DDE is the total weight of DDE (g) divided by the unit equivalent of active hydrogen of DDE (50 g / eq),
TDA의 총 활성수소 당량은 TDA의 총 중량 (g)을 TDA의 활성수소 단위 당량 (54g/eq)으로 나눈 값이고,  The total active hydrogen equivalent of TDA is the total weight of TDA (g) divided by the unit equivalent of TDA (54 g / eq),
XD-1000의 총 에폭시 당량은 XD— 1000의 총 중량 (g)을 XD— 1000와 에폭 시 단위당량 (253g/eq)으로 나눈 값이고, The total epoxy equivalent of the XD-1000 is the total weight ( g ) of XD—1000 divided by XD—1000 and the epoxy unit equivalent (253 g / eq),
NC— 3000H의 총 에폭시 당량은 NC— 3000H의 총 중량 (g)을 NC-3000H의 에폭시 단위당량 (290g/eq)으로 나눈 값이고，  The total epoxy equivalent of NC—3000H is the total weight (g) of NC—3000H divided by the epoxy unit equivalent (290 g / eq) of NC-3000H.
HP— 6000의 총 에폭시 당량은 HP— 6000의 총 중량 (g)을 HP-6000의 에폭 시 단위당량 (250g/eq)으로 나눈 값이고,  The total epoxy equivalent of HP—6000 is the total weight (g) of HP—6000 divided by the epoxy unit equivalent (250g / eq) of HP-6000,
BMI— 2300의 총 말레이미드 당량은 BMI-2300의 총 중량 (g)을 BMI-2300 의 말레이미드 단위당량 ( 179g/eq)으로 나눈 값이다.  The total maleimide equivalent of BMI-2300 is the total weight (g) of BMI-2300 divided by the maleimide equivalent of BMI-2300 (179 g / eq).
【표 2】 Table 2
반도체 패키지용 수지 조성물의 조성  Composition of Resin Composition for Semiconductor Package
Figure imgf000026_0001
Figure imgf000027_0001
제
Figure imgf000026_0001
Figure imgf000027_0001
My
당량비 (열경화성 수 1.87 1.87 1.84 1.71 1.49 0.63 지 당량 기준. 아민 Equivalence ratio (Thermosetting number 1.87 1.87 1.84 1.71 1.49 0.63 equivalent equivalent basis .
경화제 당량비율) Curing agent equivalent ratio)
* DDS: 4 , 41 -d i am i nod i heny 1 sulfone * DDS: 4, 4 1 -di am i nod i heny 1 sulfone
* TFB: 2,2 -bis(trif luoromethyDbenzidine; 2,2'- Bis(tri f luoromethyl ) -4 , 4 ' -b i heny 1 d i am i ne  * TFB: 2,2 -bis (trif luoromethyDbenzidine; 2,2'- Bis (tri f luoromethyl) -4, 4 '-b i heny 1 d i am i ne
* DDM: 4,4' -diaminodiphenyl methane  * DDM: 4,4 '-diaminodiphenyl methane
* DDE: 4 , 4 ' -d i am i nod i heny 1 ether  * DDE: 4, 4 '-d i am i nod i heny 1 ether
* TDA: 4,4'-Thiodiani line; 4,4' -diaminodiphenyl sulfide  TDA: 4,4'-Thiodiani line; 4,4'-diaminodiphenyl sulfide
* XD-1000: 에폭시 수지 (Nippon kayaku사)  * XD-1000: epoxy resin (Nippon kayaku)
* NC-3000H: 에폭시 수지 (Nippon kayaku사)  * NC-3000H: epoxy resin (Nippon kayaku)
* HP 6000: 에폭시 수지 (DIC사)  * HP 6000: Epoxy Resin (DIC Corporation)
* BMI-2300: 비스말레이미드계 수지 (DAIWA KASEI사)  * BMI-2300: Bismaleimide Resin (DAIWA KASEI Co., Ltd.)
* SC2050MTO: 페닐아미노실란 처리된 슬러리 타입의 마이크로 실리카， 평균입경 0.5 (Admantechs사)  * SC2050MTO: Slurry type micro silica with phenylaminosilane treatment, average particle size 0.5 (Admantechs)
* 당량비 ： 상기 표 1과 동일한 수학식 1을 통해 계산됨  * Equivalence Ratio: Calculated through Equation 1 identical to Table 1 above
<실험예： 실시예 및 비교예에서 얻어진 반도체 패키지용 수지 조성 물 프리프레그 및 동박 적층판의 물성 측정 > <Experimental example: Measurement of the physical property of the resin composition prepreg and copper foil laminated board for semiconductor packages obtained by the Example and the comparative example>
상기 실시예 및 비교예에서 얻어진 반도체 패키지용 수지 조성물， 프 리프레그 및 동박 적충판의 물성을 하기 방법으로 측정하였으며, 그 결과를 표 3에 나타내었다.  The physical properties of the resin composition for semiconductor package, the prepreg and the copper foil-filled plate obtained in the above Examples and Comparative Examples were measured by the following method, and the results are shown in Table 3.
1. 열팽창계수 (CTE) 1.Coefficient of Thermal Expansion (CTE)
상기 실시예 및 비교예에서 얻어진 동박 적층판의 동박층을 에칭하여 제거한 후， MD방향으로 시험편을 제작하여, TMA(TA Instruments, Q400)를 이용하여, 30 °C에서 260 °C까지， 승온 속도 10 t:Anin 조건으로 측정한 후， 50 °C 에서 150 °C 범위의 측정값을 열팽창계수로 기록하였다. 2. 수지 흐름성 (Resin flow, RF) After etching and removing the copper foil layer of the copper foil laminate obtained in the above Examples and Comparative Examples, to prepare a test piece in the MD direction, using a TMA (TA Instruments, Q400), from 30 ° C to 260 ° C, temperature increase rate 10 After measurement under the t: Anin condition, the measured value in the range of 50 ° C. to 150 ° C. was recorded as the coefficient of thermal expansion. 2. Resin flow (RF)
(1) 초기 수지 흐름성  (1) initial resin flowability
IPC-TM-650 (2.3.17)에 따라, 상기 실시예 및 비교예에서 얻어진 프 리프레그 상태에서 카바프레스 (Carver사， #3893.4NE0000)를 이용하여 RF를 측정하였다.  According to IPC-TM-650 (2.3.17), RF was measured using Carbapress (Carver, # 3893.4NE0000) in the prepreg state obtained in the above Examples and Comparative Examples.
(2) 1달 후 수지 흐름성  (2) resin flowability after 1 month
IPC-TM-650 (2.3.17)에 따라， 상기 실시예 및 비교예에서 얻어진 프 리프레그를 상온에서 1달간 보관한 후의 상태에서 카바프레스 (Carver사， #3893.4NE0000)를 이용하여. RF를 측정하였다. According to IPC-TM-650 (2.3.17), using Carbapress (Carver, # 3893.4NE0000) in the state after storing the prepreg obtained in the above Examples and Comparative Examples for 1 month at room temperature . RF was measured.
3. 회로패턴 채움성 3. Filling of circuit pattern
상기 실시예 및 비교예에서 얻어진 프리프레그를， 회로패턴 (패턴높이 10um,잔동률 50%)의 양면에 위치시키고， 그 위에 동박 (두께 l /m, Mitsui 사 제조)을 위치시켜， 220 °C 및 35 kg/cm'의 조건으로 100분간 프레스한 후, 양면의 동박을 에칭하여, 다음 기준 하에 회로패턴 채움성을 평가하였다. The prepregs obtained in the above examples and comparative examples were placed on both sides of the circuit pattern (pattern height 10um, residual ratio 50%), and copper foil (thickness l / m, manufactured by Mitsui) was placed thereon at 220 ° C. After pressing for 100 minutes under the condition of 35 kg / cm ', the copper foil of both surfaces was etched and the circuit pattern fillability was evaluated on the following reference | standard.
O: Void 발생 없음  O: No void
X： Void 발생  X ： Void occurrence
4. 점도 - 상기 실시예 및 비교예에서 얻어진 프리프레그에 대하여, 레오미터4. Viscosity-Rheometer for the prepreg obtained in the above Examples and Comparative Examples
(Anton Paar사， Modular compact Rheometer MCR 302)를 이용하여， 50 °C에 서 200 °C까지, 승온 속도 5 °C/min, Normal Force 5N, Frequency 10Hz, amplitude 0.5% 조건으로 측정하여 점도를 평가하였고, 최소점도 및 최소점 도를 나타내는 온도를 기록하였다. (Anton Paar, Modular compact Rheometer MCR 302), the viscosity was measured at 50 ° C to 200 ° C, heating rate 5 ° C / min, Normal Force 5N, Frequency 10 Hz, amplitude 0.5% And the temperature indicating the minimum viscosity and minimum viscosity was recorded.
5. 인장신율 (Tensile Elongation)측정 5. Tensile Elongation Measurement
상기 실시예 및 비교예에서 얻어진 프리프레그를 유리섬유의 MD 및 TD방향이 일치하도톡 10매를 적층하여， 220 °C 및 35 kg/cuf의 조건으로 100 분간 프레스 한 후, IPC-TM-650 (2.4.18.3)에 따라, Universal Testing Machine(Instron 3365)장비를 이용하여 MD방향의 인장신율을 측정하였다. 【표 3] The prepregs obtained in the above examples and comparative examples were laminated with 10 sheets of MD having the same direction as the MD and TD directions of the glass fibers, pressed for 100 minutes under conditions of 220 ° C. and 35 kg / cuf, and then IPC-TM-650 According to (2.4.18.3), tensile elongation in the MD direction was measured using a Universal Testing Machine (Instron 3365). [Table 3]
실험예 결과  Experimental Results
Figure imgf000030_0001
Figure imgf000030_0001
상기 표 3에 나타난 바와 같이， 실시예의 반도체 패키지용 수지 조성 물 및 이로부터 얻어진 프리프레그, 동박 적층판은 9.0 내지 10.5 ppm/ °C로 열팽창계수가 낮아 저열팽창 특성을 가지면서， 최소점도가 158 내지 163 °C 범위에서 260 내지 312 Paᅳ s로 측정되어 , 15 내지 23%로 높은 수지흐름성 을 가질 수 있어, 우수한 회로패턴 채움성을 확보할 수 있다. 뿐만 아니라 1달이 지난 후에도 1~2%의 수지 흐름성 감소가 나타나는데 그쳐 , 보관안정 성 또한 우수한 것을 확인할 수 있다. 또한, 인장신율 측정결과 2.4 내지 2.9%의 높은 인성 (Toughness)을 가져 우수한 기계적 물성을 구현할 수 있음 을 확인할 수 있었다. As shown in Table 3, the resin composition for a semiconductor package of the embodiment and the prepreg, copper foil laminate obtained therefrom has a low thermal expansion coefficient of 9.0 to 10.5 ppm / ° C, low thermal expansion characteristics, minimum viscosity of 158 to It is measured at 260 to 312 Pa 3 s in the range of 163 ° C., and may have a high resin flowability of 15 to 23%, thereby ensuring excellent circuit pattern fillability. In addition, after 1 month, the flow rate of resin was decreased by 1 ~ 2%, and the storage stability was also excellent. In addition, the tensile elongation measurement result was found to have a high toughness (Toughness) of 2.4 to 2.9% to implement excellent mechanical properties.
한편 , 전자끌기 (Elect ron Wi thdrawing Group , EWG)를 갖는 아민 경화 제 (DDS 또는 TFB)가 함유되지 않은 비교예 1 내지 4의 반도체 패키지용 수 지 조성물 및 이로부터 얻어진 프리프레그， 동박 적층판은 최소점도가 119 내지 124 °C 범위에서 810 내지 987 Pa · s로 실시예에 비해 현저히 높아, 3.0 내지 4.7%의 매우 낮은 수지흐름성을 나타내어， 희로패턴 채움성이 현 저히 불량함을 확인할 수 있다. . On the other hand, the water for semiconductor packages of Comparative Examples 1 to 4 containing no amine curing agent (DDS or TFB) having an electron drawing (EWG) The resin composition and the prepreg and copper foil laminate obtained therefrom are significantly higher than those of the examples with a minimum viscosity of 810 to 987 Pa · s in the range of 119 to 124 ° C., showing very low resin flow of 3.0 to 4.7%. It can be seen that the pattern fill is very poor. .
한편， 열경화성 수지 성분 및 아민경화제 성분의 합계 100 중량부에 대해 무기 첨가제의 첨가량이 36 중량부로 현저히 감소한 비교예 5의 반도 체 패키지용 수지 조성물 및 이로부터 얻어진 프리프레그， 동박 적층판은 열팽창계수가 18 ppm/ °C로 높아지는 한계가 있음을 확인할 수 있다. On the other hand, the resin composition for a semiconductor package of Comparative Example 5 and the prepreg and copper foil laminate obtained therefrom were significantly reduced in the amount of the inorganic additive added to 36 parts by weight with respect to 100 parts by weight of the thermosetting resin component and the amine curing agent component in total. It can be seen that there is a limit rising to pp m / ° C.
그리고, 아민 경화제 100 중량부 대비 625 중량부의 열경화성 수지가 포함되어, 열경화성 수지 당량 기준 아민 경화제 당량비율이 0.63인 비교예 6의 반도체 패키지용 수지 조성물 및 이로부터 얻어진 프리프레그, 동박 적 층판은 인장신율이 1 .7%로 실시예 대비 감소하여， 인성 (Toughness)에 한계 가 있음을 확인할 수 있다.  In addition, the resin composition for a semiconductor package of Comparative Example 6 and a prepreg and copper foil laminated plate obtained therefrom are 625 parts by weight of a thermosetting resin with respect to 100 parts by weight of an amine curing agent, and the amine curing agent equivalent ratio based on the thermosetting resin equivalent is 0.63. This decrease to 1.7% compared with the embodiment, it can be seen that there is a limit in toughness (Toughness).
이에 따라, 실시예와 같이 전자끌기 (El ectron Wi thdrawing Group , EWG)를 갖는 아민 경화제 100 중량부 대비 400 중량부 이하의 열경화성 수 지를 포함하고， 열경화성 수지 당량 기준 아민 경화제 당량비율인 당량비가 1.4 이상을 만족하면서, 무기 첨가제의 첨가량을 수지 성분 및 아민 경화제 성분 함량 합계 대비 과량으로 첨가된 경우, 우수한 저열팽창 특성， 유동성， 기계적 물성 및 보관 안정성을 확보할 수 있음을 확인하였다.  Accordingly, the equivalent ratio of the thermosetting resin of 400 parts by weight or less with respect to 100 parts by weight of the amine curing agent having an electron drawing (El ectron Withdrawing Group, EWG), and the equivalent amine curing agent equivalent ratio based on the thermosetting resin equivalent, is 1.4 or more. While satisfying the above, it was confirmed that when the added amount of the inorganic additive was added in excess of the total content of the resin component and the amine curing agent component, excellent low thermal expansion properties, fluidity, mechanical properties, and storage stability could be ensured.

Claims

【청구범위】 [Claim]
【청구항 11  [Claim 11
술폰기 , 카보닐기， 할로겐기 , 탄소수 1 내지 20의 알킬기， 탄소수 6 내지 20의 아릴기, 탄소수 2 내지 30의 헤테로아릴기 및 탄소수 1 내지 20 의 알킬렌기로 이루어진 군에서 선택된 1종 이상의 작용기를 포함한 아민 경화제;  At least one functional group selected from the group consisting of a sulfone group, a carbonyl group, a halogen group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, and an alkylene group having 1 to 20 carbon atoms Amine curing agents including;
열경화성 수지; 및  Thermosetting resins; And
무기 층진제를 포함하고，  Including inorganic layering agent ，
상기 아민 경화제 및 열경화성 수지 100 중량부에 대하여 상기 무기 충진제 함량이 200 중량부 이상이며，  The inorganic filler content is 200 parts by weight or more based on 100 parts by weight of the amine curing agent and the thermosetting resin,
상기 아민 경화제 100 중량부에 대하여 상기 열경화성 수지 함량이 400 중량부 이하이고,  The thermosetting resin content is 400 parts by weight or less based on 100 parts by weight of the amine curing agent,
상기 아민 경화제에 포함된 탄소수 1 내지 20의 알킬기， 탄소수 6 내 지 20의 아릴기, 탄소수 2 내지 30의 헤테로아릴기 및 탄소수 1 내지 20의 알킬렌기는 각각 독립적으로 니트로기， 시아노기 및 할로겐기로 이루어진 군에서 선택된 1종 이상의 작용기로 치환된， 반도체 패키지용 수지 조성물ᅳ  The alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms, the heteroaryl group having 2 to 30 carbon atoms and the alkylene group having 1 to 20 carbon atoms included in the amine curing agent are each independently a nitro group, a cyano group and a halogen group. Resin composition for semiconductor package substituted with one or more functional groups selected from the group consisting of
【청구항 2】 [Claim 2]
■제 1항에 있어서, ■ according to claim 1,
하기 수학식 1로 계산되는 당량비가 1.4 이상인 , 반도체 패키지용. 수 지 조성물:  For a semiconductor package, the equivalent ratio calculated by the following formula (1) is 1.4 or more. Resin composition:
[수학식 1]  [Equation 1]
당량비 = 상기 아민 경화제에 함유된 총 활성수소 당량 / 상기 열경 화성 수지에 함유된 총 경화성 작용기 당량.  Equivalence ratio = total active hydrogen equivalents contained in said amine curing agent / total curable functional group equivalents contained in said thermosetting resin.
【청구항 3】 [Claim 3]
제 1항에 있어서，  The method of claim 1,
상기 아민 경화제는 하기 화학식 1 내지 3으로 이루어진 군에서 선택 된 1종 이상의 화합물을 포함하는 , 반도체 패키지용 수지 조성물:  The amine curing agent comprises at least one compound selected from the group consisting of the following Chemical Formulas 1 to 3, a resin composition for a semiconductor package:
[화학식 1]
Figure imgf000033_0001
상기 화학식 1에서, [Formula 1]
Figure imgf000033_0001
In Chemical Formula 1,
A는 술폰기 , 카보닐기, 또는 탄소수 1 내지 10의 알킬렌기이며 ,  A is a sulfone group, a carbonyl group, or an alkylene group having 1 to 10 carbon atoms,
Xi 내지 ¾는 각각 독립적으로 니트로기， 시아노기， 수소원자， 할로 겐기 , 탄소수 1 내지 6의 알킬기， 탄소수 6 내지 15의 아릴기， 또는 탄소수 2 내지 20의 해테로아릴기이고,  Xi to ¾ are each independently a nitro group, cyano group, hydrogen atom, halogen group, alkyl group of 1 to 6 carbon atoms, aryl group of 6 to 15 carbon atoms, or heteroaryl group of 2 to 20 carbon atoms,
Ri, Ri ' , R2 및 '는 각각 독립적으로 수소원자， 할로겐기 , 탄소수 1 내지 6의 알킬기, 탄소수 6 내지 15의 아릴기， 또는 탄소수 2 내지 20의 헤 테로아릴기이며， Ri, Ri ', R 2 and' are each independently a hydrogen atom, a halogen group, an alkyl group of 1 to 6 carbon atoms, an aryl group of 6 to 15 carbon atoms, or a heteroaryl group of 2 to 20 carbon atoms,
n은 1 내지 10의 정수이고,  n is an integer from 1 to 10,
상기 탄소수 1 내지 10의 알킬렌기, 탄소수 1 내지 6의 알킬기， 탄소 수 6 내지 15의 아릴기， 및 탄소수 2 내지 20의 헤테로아릴기는 각각 독립 적으로 니트로기 , 시아노기 및 할로겐기로 이루어진 군에서, 선택된 1종 이 상의 작용기로 치환되며,  In the group consisting of an alkylene group of 1 to 10 carbon atoms, an alkyl group of 1 to 6 carbon atoms, an aryl group of 6 to 15 carbon atoms, and a heteroaryl group of 2 to 20 carbon atoms, independently from the group consisting of a nitro group, a cyano group and a halogen group, Is substituted with one or more selected functional groups,
Figure imgf000033_0002
Figure imgf000033_0002
상기 화학식 2에서,  In Chemical Formula 2,
Yi 내지 Y8는 각각 독립적으로 니트로기, 시아노기， 수소원자， 할로 겐기， 탄소수 1 내지 6의 알킬기, 탄소수 6 내지 15의 아릴기， 또는 탄소수 2 내지 20의 헤테로아릴기이고, Yi to Y 8 are each independently a nitro group, a cyano group, a hydrogen atom, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms,
R3, R3 ' , R4 및 '는 각각 독립적으로 수소원자， 할로겐기 , 탄소수 1 내지 6의 알킬기, 탄소수 6 내지 15의 아릴기 , 또는 탄소수 2 내지 20의 헤 테로아릴기이며, m은 1 내지 10의 정수이고, R 3 , R 3 ', R 4 and' are each independently a hydrogen atom, a halogen group, an alkyl group of 1 to 6 carbon atoms, an aryl group of 6 to 15 carbon atoms, or a heteroaryl group of 2 to 20 carbon atoms, m is an integer from 1 to 10,
상기 탄소수 1 내지 6의 알킬기 , 탄소수 6 내지 15의 아릴기, 및 탄 소수 2 내지 20의 해테로아릴기는 각각 독립적으로 니트로기， 시아노기 및 할로겐기로 이루어진 군에서 선택된 1종 이상의 작용기로 치환되며,  The alkyl group having 1 to 6 carbon atoms, the aryl group having 6 to 15 carbon atoms, and the heteroaryl group having 2 to 20 carbon atoms are each independently substituted with at least one functional group selected from the group consisting of a nitro group, a cyano group and a halogen group,
[화학식 3]  [Formula 3]
Figure imgf000034_0001
상기 화학식 3에서,
Figure imgf000034_0001
In Chemical Formula 3,
Ζι 내지 Z4는 각각 독립적으로 니트로기， 시아노기， 수소원자， 할로 겐기 , 탄소수 1 내지 6의 알킬기, 탄소수 6 내지 15의 아릴기 , 또는 탄소수 2 내지 20의 해테로아릴기이고， 내지 ι to Z 4 are each independently a nitro group, cyano group, hydrogen atom, halogen group, alkyl group having 1 to 6 carbon atoms, aryl group having 6 to 15 carbon atoms, or heteroaryl group having 2 to 20 carbon atoms,
R5, Re 및 '는 각각 독립적으로 수소원자， 할로겐기， 탄소수 1 내지 6의 알킬기， 탄소수 6 내지 15의 아릴기 , 또는 탄소수 2 내지 20의 헤 테로아릴기이며， R 5 , Re and 'are each independently a hydrogen atom, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms,
상기 탄소수 1 내지 6의 알킬기， 탄소수 6 내지 15의 아릴기, 및 탄 소수 2 내지 20의 헤테로아릴기는 각각 독립적으로 니트로기， 시아노기 및 할로겐기로 이루어진 군에서 선택된 1종 이상의 작용기로 치환된다.  The alkyl group having 1 to 6 carbon atoms, the aryl group having 6 to 15 carbon atoms, and the heteroaryl group having 2 to 20 carbon atoms are each independently substituted with at least one functional group selected from the group consisting of a nitro group, a cyano group and a halogen group.
【청구항 4】 [Claim 4]
제 1항에 있어서,  The method of claim 1,
상기 아민 경화제 및 열경화성 수지 100 중량부에 대하여 상기 무기 층진제 함량이 200 중량부 내지 500 중량부인， 반도체 패키지용 수지 조성 물 ·  Resin composition for semiconductor packages, wherein the inorganic layering agent content is 200 parts by weight to 500 parts by weight with respect to 100 parts by weight of the amine curing agent and the thermosetting resin.
【청구항 5】 [Claim 5]
제 1항에 있어서,  The method of claim 1,
상기 무기 충진제는 실리카， 알루미늄 트리하이드록사이드, 마그네슘 하이드록사이드， 몰리브데늄 옥사이드, 징크 몰리브데이트, 징크 보레이트， 징크 스타네이트， 알루미나; 클레이， 카을린, 탈크, 소성 카을린, 소성 탈 크， 마이카, 유리 단섬유， 글라스 미세 파우더 및 중공 글라스로 이루어진 군에서 선택된 1종 이상을 포함하는, 반도체 패키지용 수지 조성물. The inorganic filler is silica, aluminum trihydroxide, magnesium Hydroxide, molybdenum oxide, zinc molybdate, zinc borate, zinc stannate, alumina; A resin composition for a semiconductor package comprising at least one selected from the group consisting of clay, chlorine, talc, calcined chlorine, calcined talc, mica, short glass fiber, glass fine powder, and hollow glass.
【청구항 6】 [Claim 6]
제 5항에 있어서,  The method of claim 5,
상기 실리카는 표면에 실란 화합물이 결합한 평균 입경 0. 1 m 내지 100 인 실리카를 포함하는， 반도체 패키지용 수지 조성물.  The silica is a resin composition for a semiconductor package comprising a silica having an average particle size of 0.01 m to 100 bonded to the surface of the silane compound.
【청구항 7] [Claim 7]
제 6항에 있어서,  The method of claim 6,
상기 실란 화합물은 아미노 실란 커플링제, 에폭시 실란 커플링저)， 비닐 실란 커플링제, 양이온 실란 커플링제 및 페닐 실란 커플링제로 이루 어진 군에서 선택된 1종 이상의 실란 커플링제를 포함하는, 반도체 패키지 용 수지 조성물.  The silane compound includes at least one silane coupling agent selected from the group consisting of an amino silane coupling agent, an epoxy silane coupling agent), a vinyl silane coupling agent, a cationic silane coupling agent, and a phenyl silane coupling agent. .
【청구항 8】 [Claim 8]
제 1항에 있어서,  The method of claim 1,
상기 열경화성 수지는 에폭시 수지, 비스말레이미드 수지， 시아네이 트 에스터 수지 및 비스말레이미드-트리아진 수지로 이루어진 군으로부터 선택되는 1종 이상의 수지를 포함하는， 반도체 패키지용 수지 조성물.  The thermosetting resin comprises at least one resin selected from the group consisting of an epoxy resin, a bismaleimide resin, a cyanate ester resin, and a bismaleimide-triazine resin.
【청구항 9】 [Claim 9]
제 1항에 있어서, _  The method of claim 1, wherein
상기 반도체 패키지용 수지 조성물은 IPC— TM— 650 (2.3. 17)에 의해 측 정한 수지 흐름성이 10% 내지 25%인， 반도체 패키자용 수지 조성물.  The resin composition for a semiconductor package is a resin composition for a semiconductor packager having a resin flowability of 10% to 25% measured by IPC-TM-650 (2.3.17).
【청구항 10] [Claim 10]
제 1항에 있어서 상기 반도체 패키지용 수지 조성물은 140 °C 이상에서 최소점도를 가 지며， 상기 최소점도가 100 Pa · s 내지 500 Pa · s 인 반도체 패키지용 수지 조성물. The method of claim 1 The resin composition for a semiconductor package has a minimum viscosity at 140 ° C or more, the minimum viscosity is 100 Pa · s to 500 Pa · s resin composition for a semiconductor package.
【청구항 11】 [Claim 11]
제 1항에 있어서,  The method of claim 1,
상기 반도체 패키지용 수지 조성물숀 IPC-TM-650 (2.4. 18.3)에 의해 측정한 인장신율이 2.0 % 이상인， 반도체 패키지용 수지 조성물.  The resin composition for semiconductor packages whose tensile elongation measured by the said resin composition Sean IPC-TM-650 (2.4.18.3) for said semiconductor packages is 2.0% or more.
【청구항 12】 [Claim 12]
저 U항에 따른 반도체 패키지용 수지 조성물을 섬유 기재에 함침시켜 얻어진'프리프레그. It was impregnated to a resin composition for semiconductor package according to a low-U, wherein the fiber base material thus obtained, the prepreg.
【청구항 13】 [Claim 13]
제 12항에 따른 프리프레그; 및 가열 및 가압에 의해 상기 프리프레그 와 일체화된 포함하는 금속박；을 포함하는 금속박 적층판.  A prepreg according to claim 12; And a metal foil comprising integrally with the prepreg by heating and pressurizing.
PCT/KR2018/002779 2017-03-22 2018-03-08 Resin composition for semiconductor package, prepreg using same, and metal foil laminated plate WO2018174446A1 (en)

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CN201880003433.9A CN109661422B (en) 2017-03-22 2018-03-08 Resin composition for semiconductor encapsulation, prepreg using same, and metal clad laminate
US16/334,201 US11214677B2 (en) 2017-03-22 2018-03-08 Resin composition for semiconductor package, prepreg and metal clad laminate using the same
EP18770850.8A EP3480244B1 (en) 2017-03-22 2018-03-08 Resin composition for semiconductor package, prepreg using same, and metal foil laminated plate

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KR1020180018018A KR102049024B1 (en) 2017-03-22 2018-02-13 Resin composition for semiconductor package, prepreg and metal clad laminate using the same
KR10-2018-0018018 2018-02-13

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002121358A (en) * 2000-10-12 2002-04-23 Sumitomo Bakelite Co Ltd Resin composition for thermosetting liquid sealing, assembling technique of semiconductor element and semiconductor device
JP2002249753A (en) * 2001-02-23 2002-09-06 Toray Ind Inc Adhesive composition for semiconductor device and adhesive sheet for semiconductor device using the same, substrate for connecting semiconductor and semiconductor device
JP2006303119A (en) * 2005-04-19 2006-11-02 Kyocera Chemical Corp Method of manufacturing semiconductor device and semiconductor sealing resin sheet
KR20140087015A (en) * 2011-11-02 2014-07-08 히타치가세이가부시끼가이샤 Resin composition, and resin sheet, prepreg, laminate, metal substrate, printed circuit board and power semiconductor device using same
WO2016017751A1 (en) * 2014-08-01 2016-02-04 日本化薬株式会社 Epoxy resin composition, resin sheet, and prepreg, and metal-clad laminate board, printed circuit board, and semiconductor device

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002121358A (en) * 2000-10-12 2002-04-23 Sumitomo Bakelite Co Ltd Resin composition for thermosetting liquid sealing, assembling technique of semiconductor element and semiconductor device
JP2002249753A (en) * 2001-02-23 2002-09-06 Toray Ind Inc Adhesive composition for semiconductor device and adhesive sheet for semiconductor device using the same, substrate for connecting semiconductor and semiconductor device
JP2006303119A (en) * 2005-04-19 2006-11-02 Kyocera Chemical Corp Method of manufacturing semiconductor device and semiconductor sealing resin sheet
KR20140087015A (en) * 2011-11-02 2014-07-08 히타치가세이가부시끼가이샤 Resin composition, and resin sheet, prepreg, laminate, metal substrate, printed circuit board and power semiconductor device using same
WO2016017751A1 (en) * 2014-08-01 2016-02-04 日本化薬株式会社 Epoxy resin composition, resin sheet, and prepreg, and metal-clad laminate board, printed circuit board, and semiconductor device

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