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WO2018174446A1 - Composition de résine pour boîtier de semi-conducteur, préimpregné l'utilisant et plaque stratifiée de feuille métallique - Google Patents

Composition de résine pour boîtier de semi-conducteur, préimpregné l'utilisant et plaque stratifiée de feuille métallique 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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WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
resin
resin composition
semiconductor package
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
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PCT/KR2018/002779
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English (en)
Korean (ko)
Inventor
심창보
심희용
민현성
김영찬
송승현
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Chem Ltd
Original Assignee
LG Chem Ltd
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.)
Filing date
Publication date
Priority claimed from KR1020180018018A external-priority patent/KR102049024B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to US16/334,201 priority Critical patent/US11214677B2/en
Priority to EP18770850.8A priority patent/EP3480244B1/fr
Priority to JP2019506376A priority patent/JP6756083B2/ja
Priority to CN201880003433.9A priority patent/CN109661422B/zh
Publication of WO2018174446A1 publication Critical patent/WO2018174446A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
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    • 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
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    • 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
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    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
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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

La présente invention concerne une composition de résine qui est destinée à un boîtier de semi-conducteur et qui présente une aptitude à l'écoulement élevée, de faibles propriétés de dilatation thermique et d'excellentes propriétés mécaniques, un préimprégné l'utilisant, et une plaque stratifiée de feuille métallique.
PCT/KR2018/002779 2017-03-22 2018-03-08 Composition de résine pour boîtier de semi-conducteur, préimpregné l'utilisant et plaque stratifiée de feuille métallique Ceased WO2018174446A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
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 (fr) 2017-03-22 2018-03-08 Composition de résine pour boîtier de semi-conducteur, préimpregné l'utilisant et plaque stratifiée de feuille métallique
JP2019506376A JP6756083B2 (ja) 2017-03-22 2018-03-08 半導体パッケージ用樹脂組成物とこれを用いたプリプレグおよび金属箔積層板
CN201880003433.9A CN109661422B (zh) 2017-03-22 2018-03-08 用于半导体封装的树脂组合物、使用其的预浸料和金属包层层合体

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20170036104 2017-03-22
KR10-2017-0036104 2017-03-22
KR1020180018018A KR102049024B1 (ko) 2017-03-22 2018-02-13 반도체 패키지용 수지 조성물과 이를 이용한 프리프레그 및 금속박 적층판
KR10-2018-0018018 2018-02-13

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WO2018174446A1 true WO2018174446A1 (fr) 2018-09-27

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002121358A (ja) * 2000-10-12 2002-04-23 Sumitomo Bakelite Co Ltd 熱硬化性液状封止樹脂組成物、半導体素子の組立方法及び半導体装置
JP2002249753A (ja) * 2001-02-23 2002-09-06 Toray Ind Inc 半導体装置用接着剤組成物およびそれを用いた半導体装置用接着剤シート、半導体接続用基板ならびに半導体装置
JP2006303119A (ja) * 2005-04-19 2006-11-02 Kyocera Chemical Corp 半導体装置の製造方法及び半導体封止用樹脂シート
KR20140087015A (ko) * 2011-11-02 2014-07-08 히타치가세이가부시끼가이샤 수지 조성물, 및 그것을 이용한 수지 시트, 프리프레그, 적층판, 금속 기판, 프린트 배선판 및 파워 반도체 장치
WO2016017751A1 (fr) * 2014-08-01 2016-02-04 日本化薬株式会社 Composition de résine époxy, feuille de résine, pré-imprégné, carte stratifiée gainée de métal, carte de circuit imprimé et dispositif à semi-conducteur

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002121358A (ja) * 2000-10-12 2002-04-23 Sumitomo Bakelite Co Ltd 熱硬化性液状封止樹脂組成物、半導体素子の組立方法及び半導体装置
JP2002249753A (ja) * 2001-02-23 2002-09-06 Toray Ind Inc 半導体装置用接着剤組成物およびそれを用いた半導体装置用接着剤シート、半導体接続用基板ならびに半導体装置
JP2006303119A (ja) * 2005-04-19 2006-11-02 Kyocera Chemical Corp 半導体装置の製造方法及び半導体封止用樹脂シート
KR20140087015A (ko) * 2011-11-02 2014-07-08 히타치가세이가부시끼가이샤 수지 조성물, 및 그것을 이용한 수지 시트, 프리프레그, 적층판, 금속 기판, 프린트 배선판 및 파워 반도체 장치
WO2016017751A1 (fr) * 2014-08-01 2016-02-04 日本化薬株式会社 Composition de résine époxy, feuille de résine, pré-imprégné, carte stratifiée gainée de métal, carte de circuit imprimé et dispositif à semi-conducteur

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