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WO2018174447A1 - Composition de résine pour boîtier de semi-conducteur, préimpregné faisant appel à celle-ci et plaque stratifiée de feuille métallique - Google Patents

Composition de résine pour boîtier de semi-conducteur, préimpregné faisant appel à celle-ci et plaque stratifiée de feuille métallique Download PDF

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Publication number
WO2018174447A1
WO2018174447A1 PCT/KR2018/002780 KR2018002780W WO2018174447A1 WO 2018174447 A1 WO2018174447 A1 WO 2018174447A1 KR 2018002780 W KR2018002780 W KR 2018002780W WO 2018174447 A1 WO2018174447 A1 WO 2018174447A1
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WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
resin composition
resin
weight
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
Application number
PCT/KR2018/002780
Other languages
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 KR1020180018019A external-priority patent/KR102057255B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to EP18772360.6A priority Critical patent/EP3480245B1/fr
Priority to US16/333,082 priority patent/US11091630B2/en
Priority to CN201880003409.5A priority patent/CN109661421B/zh
Priority to JP2019506370A priority patent/JP6852249B2/ja
Publication of WO2018174447A1 publication Critical patent/WO2018174447A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Definitions

  • the present invention relates to a resin composition for a semiconductor package having high compatibility between internal components, low thermal expansion characteristics and excellent mechanical properties, and a prepreg and a metal foil laminate using the same. More specifically, a thermosetting resin composition for a semiconductor package capable of manufacturing a prepreg and a metal foil laminate having excellent physical properties even after a reflow process of a printed circuit board (PCB) and a prepreg using the same It is about.
  • PCB printed circuit board
  • Copper clad laminates used in conventional printed circuit boards are prepregs when the substrate of glass fiber (Gl ass Fabr ic) is impregnated with 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 to construct a circuit pattern on the copper foil laminate and to build up thereon.
  • the present invention is to provide a resin composition for a semiconductor package having a high miscibility between the internal components, low thermal expansion characteristics and excellent mechanical properties.
  • the present invention is to provide a prepreg and a metal foil laminate using the resin composition for a semiconductor package.
  • Sulfonated carbonyl groups Halogen group.
  • An amine curing agent including at least one functional group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an alkylene group having 1 to 20 carbon atoms; Thermosetting resins; The thermosetting resin comprising an inorganic layer filler containing a first inorganic filler having an average particle diameter of 0.1 M to 100 and a second inorganic filler having an average particle diameter of 1 im to 90 im, and based on 100 parts by weight of the amine curing agent.
  • the content is 400 parts by weight or less, the alkyl group of 1 to 20 carbon atoms, the alkyl group of 1 to 20 carbon atoms, the aryl group of 6 to 20 carbon atoms, and the alkylene group of 1 to 20 carbon atoms contained in the amine curing agent are each independently a nitro group.
  • a resin composition for a semiconductor package which is substituted with at least one functional group selected from the group consisting of a cyano group and a halogen group.
  • This specification also provides the prepreg obtained by impregnating the said resin composition for semiconductor packages in a fiber base material.
  • a metal foil laminate comprising the prepreg: and a metal foil comprising the prepreg integrated with the prepreg; to provide. .
  • a resin composition for a semiconductor package and a prepreg and a metal foil laminate using the same according to a specific embodiment of the present invention will be described in detail.
  • An amine curing agent including at least one functional group selected from the group consisting of a heteroaryl group having 2 to 30 carbon atoms and an alkylene group having 1 to 20 carbon atoms; Thermosetting resins; An inorganic ' filler containing a first inorganic filler having an average particle diameter of 0.1 ⁇ ⁇ to 100 and a second inorganic filler having an average particle diameter of 1 rim to 90 ⁇ , wherein the filler is added to 100 parts by weight of the amine curing agent.
  • the thermosetting resin content is 400 parts by weight or less.
  • 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 composed of a nitro group, a cyano group and a halogen group
  • a resin composition for a semiconductor package substituted with one or more functional groups selected from the group.
  • the resin composition for a semiconductor package of the said embodiment is a sulfone group.
  • Carbonyl group Halogen group, substituted C1-C20 alkyl group.
  • Strong electron withdrawing groups such as one or more functional groups selected from the group consisting of a substituted 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.
  • thermosetting resin content 400 parts by weight or less based on 100 parts by weight of the amine curing agent. It prevents the change of physical properties of the thermosetting resin due to the filler added in a high content, and induces the thermosetting resin to be uniformly curable to a sufficient level without the influence of the filler, the final product Reliability can be improved and mechanical properties such as toughness can also be increased.
  • thermosetting resin content in an amount of 400 parts by weight or less with respect to 100 parts by weight of the amine curing agent, when the amine curing agent is added in a relatively excessive amount, the limit of fluidity and formability decreases due to excessive curing of the thermosetting resin. there was.
  • excess amounts of certain ' amine hardeners with reduced reaction properties including electron drawer groups (EWG) as described above. Due to reduced reactivity of the curing agent. Rapid increase in the curing rate of the thermosetting resin can be suppressed, and high flowability can be exhibited even during long-term storage in the resin composition for a semiconductor package or the prepreg state obtained therefrom, thereby having excellent fluidity. Also.
  • fillers can be filled to a high content inside the prepreg.
  • a low thermal expansion coefficient can be realized and the fluidity of the filler is improved to improve the separation of the thermosetting resin and the filler during the lamination process.
  • the resin composition for a semiconductor package of the embodiment is a sulfone group ⁇ carbonyl group.
  • Halogen group An alkyl group having 1 to 20 carbon atoms may include an amine curing agent including at least one functional group selected from the group consisting of 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.
  • 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.
  • At least one functional group selected from the group consisting of a cyano group and a halogen group may be substituted.
  • the sulfone group contained in the said amine hardener Carbonyl group. Halogen group. Substituted C1-C20 alkyl group. Substituted aryl group having 6 to 20 carbon atoms. At least one functional group selected from the group consisting of substituted heteroaryl groups having 2 to 30 carbon atoms and substituted alkylene groups having 1 to 20 carbon atoms is a strong electron withdrawing group (EWG).
  • EWG electron withdrawing group
  • the electron withdrawal functional group The included amine curing agent can reduce the reaction properties compared to the amine curing agent containing no electron withdrawing functional group, thereby easily controlling the curing reaction of the resin composition.
  • 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 improve circuit pattern fillability. Can be.
  • 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 sulfone.
  • 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 heteroaryl group having 2 to 20 carbon atoms are each independently selected from the group consisting of a nitro group, a cyano group and a halogen group Substituted with the above functional groups,
  • ⁇ to Y s 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 ', R4 and R 4' 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, and m is an integer of 1 to 10.
  • An aryl group having 6 to 15 carbon atoms and a 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,
  • Zi to Z 4 are each independently a nitro group.
  • 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.
  • the alkyl group Monovalent functional groups derived from alkane, for example. Straight, branched or cyclic, methyl, ethyl, propyl. Isobutyl, sec-butyl, tert-butyl pentyl, nuclear chamber and the like.
  • the alkylene group With divalent functional groups derived from alkane. For example, a methylene group as a straight chain, branched or cyclic. Ethylene group, propylene group, isobutylene group. sec-butylene group, ter t-butylene group. Pentyl . Rengi. It may be a nuclear silane group.
  • 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 Monovalent functional groups derived from arene, 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. Polycyclic aryl groups include naphthyl, anthryl and phenanthryl groups. Pyrenyl group. Perylyl group. It may be a crysenyl group or a fluorenyl group, but is not limited thereto. At least one hydrogen atom of such an aryl group may be each substituted with the same substituent as in the alkyl group.
  • the heteroaryl group is a hetero ring 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.
  • heterocyclic groups include thiophene groups. Furan group, pyrrole group, imidazole group ⁇ thiazole group, oxazole group, oxadiazole group. Triazole. Pyridyl groups. Bipyridyl groups. Triazines. Acridyl and pyridazine groups. Quinolinyl group. Isoquinoline group, indole group. Carbazole group, benzoxazole group.
  • Benzoimidazole group benzothiazole group, benzocarbazole group, benzothiophene group.
  • Dibenzothiophene group Benzofuranyl group and dibenzofuran group. It is not limited only to these. At least one hydrogen atom of such a heteroaryl group may be each substituted with the same substituent as in the alkyl group.
  • substituted means that another functional group is bonded to the hydrogen atom in the compound.
  • the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position at which the substituent is substituted, and is substituted at least two. 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:
  • Formula 1-1 examples include 4,4'-diaminocliphenyl sulfone (In Formula 1-1, A is a sulfone group, Xi to X 8 , R L IV , R 2 and R 2 'are each independently a hydrogen atom, n is 1). bisC4-aminophenynmethanone (In Formula 1-1, A is a carbonyl group. X 2, R u 2 and R 2 ′ each independently represent a hydrogen atom, and n is 1).
  • Xi to, Ri, R 1 ', R 2 and R 2 ' are each independently a hydrogen atom.
  • N is 1).
  • Formula 2 may include a compound represented by Formula 2-1.
  • Chemical Formula 2-1 include 2,2 ′, 3.3 ′, 5.5 ′, 6,6′-oc taf 1 uor ob i heny 1-4, 4′-di am i ne
  • Y 8 is a halogen, a fluorine group
  • R 4 and R 4 ′ each independently represent a hydrogen atom
  • m is 1.
  • 2, 2'-bis (tr if liioromethyl) biphenyl-4.4'-diamine (Y 2 and ⁇ 7 are respectively Trifluoromethyl group, YL Y 3 . Y 4 . Y 5 . 6 Y, Ys is a hydrogen atom,.
  • R 4 ′ are each independently a hydrogen atom.
  • m is 1).
  • Formula 3 may include a compound represented by Formula 3′1.
  • Chemical Formula 3-1 examples include 2.3.5.6-tetrafluorobenzene-l, 4-diamine (I, Z to Z 4 in Chemical Formula 3-1 is a fluorine group , R 5.
  • R 6 and ' are each independently a hydrogen atom). Etc.).
  • thermosetting resin to 400 parts by weight or less, or 150 parts by weight to 400 parts by weight based on 0 parts by weight of the amine curing agent K) 0. 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.
  • the thermosetting resin the mixture content is also 400 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 based on 100 parts by weight of the amine curing agent mixture. Parts by weight, or 180 parts by weight to 290 parts by weight, or 190 parts by weight to 290 parts by weight.
  • thermosetting resin content based on 100 parts by weight of the amine curing agent
  • thermosetting resin When the amount is excessively increased to more than 400 parts by weight, it is difficult to uniformly harden the thermosetting resin to a more sufficient level due to the effect of the filler. The reliability of the final product can be reduced. Mechanical properties such as toughness also have the disadvantage that they can be reduced.
  • the resin composition for a semiconductor package is calculated by the following equation
  • the equivalent ratio is at least 1.4, 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.
  • Equation 1 the total active hydrogen equivalent contained in the amine curing agent, the total weight (unit: g ) of the amine curing agent divided by the unit equivalent of the active hydrogen of the amine curing agent (g / eci) Means.
  • 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. It means a hydrogen atom contained in the amino group (-NH 2 ) present in the amine curing agent, the active hydrogen can form a cured structure through reaction with the curable functional group of the thermosetting resin.
  • the total curable functional group equivalent contained in the thermosetting resin means 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. do .
  • thermosetting resin When the thermosetting resin is two or more kinds of mixtures, the value obtained by dividing the weight (unit: g) by the compound equivalent (g / eq) of the curable functional group for each compound is obtained. By the sum of these values, the total curable functional group equivalents contained in the thermosetting resin of Equation 1 can be obtained.
  • 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 type of the thermosetting resin.
  • the curable functional group contained in the epoxy resin may be an epoxy group
  • the curable functional group contained in the bismaleimide resin may be an epoxy group
  • the functional group can be a maleimide group.
  • the resin composition for a semiconductor package is calculated by the formula If the equivalent ratio satisfies 1.4 or more, it means that the curable functional groups contained in all the thermosetting resins contain a sufficient level of amine curing agent to cause curing reaction. Therefore, when the equivalent ratio calculated by Equation 1 in the resin composition for semiconductor package is reduced to less than 1.4. Changes in the properties of thermosetting resins caused by fillers in high content occur, and it is difficult for the thermosetting resins to be uniformly cured to a more granular level under the influence of fillers, which may reduce the reliability of the final product and reduce mechanical properties. There are drawbacks to this.
  • 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. .
  • epoxy resin those used in a resin composition for a semiconductor package can be used without limitation, and the kinds thereof are not limited, and are bisphenol A type epoxy resins and phenol novolac epoxy resins.
  • the epoxy resin is a bisphenol-type epoxy resin represented by the formula (5).
  • At least one selected from the group consisting of a biphenyl type epoxy resin represented by the following formula (11), and a dicyclopentadiene type epoxy resin represented by the following formula (12) may be used.
  • n is 0 or an integer from 1 to 50.
  • the epoxy resin of the formula (5) according to the type of R.
  • bisphenol S type It may be an epoxy resin.
  • R is H or C3 ⁇ 4.
  • 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 from 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.
  • 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 bismaleimide resin represented by the following formula (13), a phenylene type bismaleimide resin represented by the following formula (14) bisphenol A diphenyl represented by the following formula (15) Ether bismaleimide resins.
  • Ri and 3 ⁇ 4 are each independently. H. CH 3 or C 2 3 ⁇ 4.
  • n is 0 or an integer from 1 to 50.
  • the cyanate ester resin can be used without limitation, which is 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 dicyclopentadiene type cyanate resin represented by the following formula (18), and a bisphenol type cyanate resin represented by the following formula (19). And some triazineized 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 the formula (19) is bisphenol A type cyanate resin, respectively, depending on the type of R.
  • the mall bismaleimide-triazine resin can be used without limitation what is normally used in the resin composition for semiconductor packages. The kind is not limited.
  • the resin composition for a semiconductor package of the embodiment may include an inorganic filler.
  • the inorganic layer thickener can be used without limitation that is usually used in the resin composition for semiconductor packages, specific examples are silica, aluminum trihydroxide, magnesium hydroxide. Molybdenum oxide. Zinc molybdate, zinc borate, zinc stannate, alumina, clay. kaoline. Talc. Calcined kaolin. Calcined talc. Mica, short glass fiber, fine glass powder and hollow glass, and may be one or more selected from the group consisting of these.
  • the resin composition for a semiconductor package of the embodiment has an average particle diameter of 0.1 mi to 100 /. first inorganic filler, which is ⁇ ; And a second inorganic filler having an average particle diameter of 1 nm to 90 nm. 1 to 50 parts by weight, or 5 parts by weight of the second inorganic filler content having an average particle diameter of 1 niu to 90 nm with respect to 100 parts by weight of the first inorganic filler having an average particle diameter of 0.01 to 100 / ztu To 50 parts by weight, or 20 parts by weight to 50 parts by weight.
  • the packing density may be increased by increasing the packing density by using the small size of the nano particle size and the large size of the micro particle size. Liquidity Can be increased.
  • the first inorganic layer filler or the second inorganic filler may use silica surface-treated with a silane coupling agent from the viewpoint of improving moisture resistance and dispersibility.
  • 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 part by weight of the silane coupling agent based on 100 parts by weight of the silica particles.
  • the silane coupling agent is 3-aminopropyltriethoxysilane
  • Aminosilane coupling agents such as N-phenyl—3-aminopropyltrimethoxysilane and N— 2— (aminoethyl) -3-aminopropyltrimethoxysilane; epoxy such as 3—glycidoxypropyltrimethoxysilane Silane coupling agents, vinyl silane coupling agents such as 3-methacryloxypropyl trimethoxysilane, cationic silane coupling agents such as N-2- (N-vinylbenzylaminoethyl) -3-aminopropyltrimethoxysilane hydrochloride And phenyl silane coupling agents, and the silane coupling agent may be used alone or in combination of at least two silane coupling agents as necessary.
  • the silane compound may include an aromatic amino silane or a (meth) acrylsilane, and as the first inorganic filler having an average particle diameter of 0.01 kPa to 100, silica treated with aromatic amino silane may be used.
  • silica treated with (meth) acryl silane may be used.
  • the aromatic amino silane-treated silica include SC2050MTO (Actaantechs).
  • Specific examples of the (meth) acrylsilane-treated silica may include AC4130Y (N i ssan chemi ca l). The (meth) acryl was used to mean both acryl or methacryl.
  • the inorganic filler may be dispersed in the resin composition for the semiconductor package.
  • Dispersion of the inorganic filler in the resin composition for a semiconductor package means that the inorganic filler and the resin composition for the semiconductor package are other.
  • a component a thermosetting resin or an amine curing agent, etc. means a state in which each component is not separated and mixed. In other words.
  • the inorganic filler and the thermosetting resin may be evenly mixed to form a dispersed phase without forming a separate phase such as an inorganic filler separate phase composed of two or more inorganic fillers or a resin separated phase composed of a thermosetting resin. Accordingly, even when the inorganic filler is filled with a high content, the prepreg has an appropriate level of flowability and a low coefficient of thermal expansion. And high mechanical properties can be achieved.
  • 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. 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 and thus reflows (ref low) . The whip phenomenon is deepened during the process, and the rigidity of the printed circuit board is reduced.
  • the resin composition for a semiconductor package of the embodiment can be used as a solution by adding a solvent as necessary.
  • the solvent is not particularly limited as long as it exhibits good solubility in the resin component.
  • Alcohol system Ether type, ketone type.
  • Amide type aromatic hydrocarbon type.
  • Ester system. Nitrile-based or the like 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 may be impregnated into the glass fiber during prepreg manufacture.
  • the resin composition of the present invention may further include various high-molecular compounds such as thermosetting resins, thermoplastic resins, and oligomers and elastomers thereof, and other flame retardant compounds or additives, so long as the properties of the resin composition are not impaired. .
  • additives include ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent brighteners, photosensitizers, and pigments. dyes. Thickeners, lubricants, antifoams. Dispersant. Leveling agents, polishes, etc. It is also possible to use them in combination to meet the purpose.
  • the resin composition for a semiconductor package of the embodiment has a coefficient of thermal expansion (CTE) 15 ppm / 0 C or less or 5 p P m / ° C. to 15 ppm / ° C.
  • CTE coefficient of thermal expansion
  • the coefficient of thermal expansion is removed by etching the copper foil layer in the state of the copper foil laminated plate obtained from the resin composition for semiconductor package, to prepare a test piece in the MD direction, using TMA (TA Ins t rument s. Q400) 30 It means the measured value in the range of 50 ° C to 150 ° C after measuring at the temperature increase rate of 10 ° C / min, from ° C to 260 ° C.
  • the resin composition for a semiconductor package has a low coefficient of thermal expansion as described above, warpage of the semiconductor package caused by a difference in thermal expansion coefficient between the chip and the printed circuit board during a metal laminate or a build-up process is generated. Since it can be minimized, 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 may have a resin flowability measured by IPC-TM-650 (2.3.17) of 1OT to 25%, or 15% to 25%. Specifically.
  • the resin flowability can be measured according to IPC-TM-650 (2.3.17) using carbapress in a prepreg state obtained from the resin composition for semiconductor package.
  • the resin composition for a semiconductor package has the above-mentioned level of resin flowability.
  • the metal laminated plate including the prepreg can be usefully used as a build-up of a printed circuit board for a semiconductor package because the metal laminate can be made or the flow can be secured during the build-up process. .
  • 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 lamination voids (Voi d) and the number and efficiency of processes may be reduced. Also.
  • the resin flowability of the resin composition for the semiconductor package is excessively increased, the thickness irregularity of the printed circuit board may occur due to the excessive flow of the resin during the lamination process, or may be thinner than the designed thickness, thereby reducing the rigidity.
  • the resin composition for a semiconductor package of the 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 can be measured using a Modular Rheometer (Model MCR 302) of Anton Paar in the prepreg state obtained from the resin composition for semiconductor package.
  • the laminate 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
  • Tensile elongation measured by (2.4.18.3) is not less than 2.0%. Or 2.0% to 5.0%, or 2.0% to 3.0%, or 2.5% to 3.0%.
  • the tensile elongation is laminated in 10 sheets in the prepreg state obtained from the resin composition for semiconductor package to match the MD and TD direction of the glass fiber, press for 100 minutes under the conditions of 220 "C and 35 kg / cuf After that, the tensile elongation in the MD direction can be measured using a Universa Test Test Machine (Inst ron 3365) equipment according to IPC-TM-650 (2.4.18.3).
  • a prepreg prepared by impregnating the resin composition for a semiconductor package on a fiber substrate may be provided.
  • the prepreg means that the resin composition for semiconductor package is impregnated into the fiber base material in a semi-cured state.
  • a glass fiber base material is not limited, A glass fiber base material.
  • Polyester resin fibers Aromatic polyester resin fibers.
  • Polyester resin fiber such as a wholly aromatic polyester resin fiber.
  • Fluoroplastic fiber and so on Synthetic fiber bases composed of woven or nonwoven fabrics as the main ingredient, kraft paper, cotton substrates such as cotton linter paper and linter and kraft paper pulp, etc. may be used.
  • a glass fiber substrate is 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 substrate forms are typically woven. Non-woven, roving, chopped strand mat or sur facing mat. The thickness of the glass substrate is not particularly limited, and about 0.01 to 0.3 mm may be used. Of the above substances. 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. It may be prepared by a method well known in the art.
  • the prepreg manufacturing method may be an impregnation method, a coating method using a variety of coaters, spray injection 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 can be mixed with the resin component and has good solubility. Specific examples thereof include ketones such as acetone, methyl ethyl keron, methyl isobutyl ketone and cyclonucleanone. Aromatic ' hydrocarbons such as benzene, toluel and xylene. And amides such as dimethylformamide and dimethylacetamide. Methyl Cellosolve. Aliphatic alcohols such as butyl cellosolve.
  • the solvent used is 80% by weight or more It is preferable to volatilize. For this reason, there is no restriction in manufacturing method or drying conditions, and the temperature at the time of drying is about 80 ° C to 200 ° C. The time is not particularly limited by 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 substrate.
  • the prepreg of the other embodiment has a coefficient of thermal expansion (CTE) of 15 ppm / ° C or less. Or 5 ppm / t to 15 p irc.
  • CTE coefficient of thermal expansion
  • Information on the thermal expansion coefficient includes the above-described information in the resin composition for a semiconductor package of the embodiment.
  • the prepreg of the other embodiment has a resin flowability of 10% to 25% as measured by IPOTM-650 (2.3.17). Or 15% to 25%.
  • 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 V 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 PaPa s. Or 250 Pa-s to 320 Pa-s.
  • the content of the viscosity includes the above-described content in the resin composition for a semiconductor package of the embodiment.
  • the prepreg of the other embodiment has a tensile elongation of 2.0% or more, or 2.0% to 5.0%, or 2.0% to 3.0%, or 2.5% to 3.0, as measured by IPC-TM-650 ⁇ (2.4.18.3). May be%. 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 containing plate integrated with the prepreg by heating and pressurizing.
  • the metal foil is copper foil; Aluminum foil; Nickel, nickel-phosphorus, nickel-tin alloys, nickel-iron alloys, lead or lead-tin alloys as interlayers, and on both sides Composite foil having a three-layer structure including copper layers of different thicknesses; Or the composite foil of the two-layered structure which combined aluminum and copper foil.
  • Copper foil or aluminum foil is used for the metal foil used for this invention, although what has a thickness of about 2-200 can be used, It is preferable that the thickness is about 2-35 /.
  • copper foil is used as said metal foil.
  • nickel as the metal foil. Nickel-phosphorus, nickel-tin alloys, nickel-iron alloys, lead. Or a lead-tin alloy or the like, and a three-layered composite foil or a two-layered composite foil in which a copper layer of 0.5 to 15 / and a copper layer of 10 to 300 are provided on both surfaces thereof. You can also use
  • 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 multi-layer printed circuit board by circuit processing the metal foil stacked plate, the circuit processing can be applied to a method performed in a general double-sided or multi-layer printed circuit board manufacturing process.
  • a resin composition for a semiconductor package having low thermal expansion characteristics and excellent mechanical properties, and a prepreg and a metal foil laminate using the same may be provided.
  • each component was added to methyl ethyl ketone according to a solid content of 65%, mixed, and then stirred at room temperature at 400 rpm for one day to prepare the resin compositions for semiconductor packages of Examples 1 to 5 and Comparative Examples 1 to 4 (resin Varnish) was prepared.
  • the specific compositions of the resin compositions prepared in Examples 1 to 5 are as described in Table 1 below
  • the specific compositions of the resin compositions prepared in Comparative Examples 1 to 4 are as described in Table 2 below.
  • TFB 2,2 -bis (tr i f 1 nor ome hy 1) benzidine; 2,2'— Bis (trif kioromethyl) -4.4 '-bi henyl diamine
  • Amine curing agent equivalent ratio to thermosetting resin (total active hydrogen equivalent of DDS + total active hydrogen equivalent of TFB + total active hydrogen equivalent of DDM + total active hydrogen equivalent of DDE) I ⁇ (total epoxy equivalent of XD-1000 + NC-3000H) Total epoxy equivalent of + total epoxy equivalent of HP-6000) + (total maleimide equivalent of BMI-2300) ⁇
  • Equation 1 the total active hydrogen equivalent weight of the DDS is obtained by dividing the total weight (g) of the DDS by the unit equivalent weight of the active hydrogen of the DDS (62 g / eq),
  • the total active hydrogen equivalent of TFB is the total weight of TFB (g) divided by the unit equivalent of TFB (80 g / eci),
  • the total active hydrogen equivalent of DDM is the total weight of DDM divided by the unit equivalent of active hydrogen of DDM (49.5 g / eq),
  • the 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 epoxy equivalent of the XD-1000 is the total weight (g) of the XD-1000 divided by the epoxy unit equivalent (253 g / eq) of XE ) -1000,
  • the total epoxy equivalent of NC-3000H is the total weight (g) of NC—3000H divided by the epoxy unit equivalent of NC-3000H (290 g / eq),
  • the total epoxy equivalent of HP-6000 is the total weight of HP-6000 divided by the epoxy equivalent of HP-6000 (250 g / eq).
  • the total maleimide equivalent of BMI-2300 is the total weight (g) of BMI-2300 divided by the male equivalent of BMI-2300 (179 g / eq).
  • Table 2 The total maleimide equivalent of BMI-2300 is the total weight (g) of BMI-2300 divided by the male equivalent of BMI-2300 (179 g / eq).
  • TFB 2.2 " -bis (tr if luoromethyl) benzidine; 2.2'- B is (trif 1 uor ome thyl) -4,4'-bi pheny 1 di am i ne
  • AC4130Y Slurry type nano silica treated with methacrylsilane. Average particle size 50nni (Nissan chemical company)
  • test piece After etching and removing the copper foil layer of the copper foil laminated board obtained by the said Example and comparative example. After etching and removing the copper foil layer of the copper foil crushing plate obtained by the said Example and the comparative example, the test piece was produced to MD direction. Using TMA (TA Instruments, Q400). After measuring at 30 ° C to 260 ° C, heating rate 10 ° C / niin conditions. The measured values ranging from 50 ° C. to 150 ° C. were recorded as thermal expansion coefficients.
  • TMA TA Instruments, Q400
  • the resin composition for a semiconductor package of the embodiment, and the prepreg and copper foil-filled plate obtained therefrom have a low coefficient of thermal expansion of 9.1 to 10.5 P pm / ° C., having low thermal expansion characteristics, and a minimum viscosity of 157 to 164 ° C. Measured from 256 to 315 Pa.s. 15 to 23% can have a high resin flow properties, it can ensure excellent miscibility. Also. Tensile elongation measurement results showed that it has high toughness of 2.6 to 2.9% and can realize excellent mechanical properties.
  • the amine having an electron draw (EWG) the resin composition for semiconductor packages of Comparative Examples 1 to 3 containing no curing agent and the prepreg and copper foil laminate obtained therefrom have a minimum viscosity of 120 to 125 810 to 987 Pa ⁇ s in the range of ° C is significantly higher than that of the embodiment, showing a very low resin flow of 3 to 4. 7%, and the poor compatibility of the resin and inorganic fillers such as separation occurs You can check it.
  • the resin composition for a semiconductor package of Comparative Example 4, wherein the amine curing agent equivalent ratio is 0.63 based on the thermosetting resin equivalent, and the prepreg and copper foil laminated plates obtained therefrom are 625 parts by weight based on 100 parts by weight of the amine curing agent.
  • thermosetting resin 400 parts by weight or less with respect to 100 parts by weight of the amine curing agent having an electron draw (El ect ron Wi thdrawing Group. EWG). While the equivalent ratio which is a thermosetting resin equivalent reference amine curing agent equivalent ratio satisfies 1.4 or more. Excellent low thermal expansion properties when two inorganic additives are used in combination. liquidity. It was confirmed that mechanical properties and miscibility can be secured.

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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 miscibilité élevée entre des composants internes, de faibles propriétés de dilatation thermique et d'excellentes propriétés mécaniques, un préimprégné faisant appel à celle-ci et une plaque stratifiée de feuille métallique.
PCT/KR2018/002780 2017-03-22 2018-03-08 Composition de résine pour boîtier de semi-conducteur, préimpregné faisant appel à celle-ci et plaque stratifiée de feuille métallique Ceased WO2018174447A1 (fr)

Priority Applications (4)

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EP18772360.6A EP3480245B1 (fr) 2017-03-22 2018-03-08 Composition de résine pour boîtier de semi-conducteur, préimpregné faisant appel à celle-ci et plaque stratifiée de feuille métallique
US16/333,082 US11091630B2 (en) 2017-03-22 2018-03-08 Resin composition for semiconductor package, prepreg, and metal clad laminate using the same
CN201880003409.5A CN109661421B (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
JP2019506370A JP6852249B2 (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

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KR10-2017-0036105 2017-03-22
KR20170036105 2017-03-22
KR10-2018-0018019 2018-02-13
KR1020180018019A KR102057255B1 (ko) 2017-03-22 2018-02-13 반도체 패키지용 수지 조성물과 이를 이용한 프리프레그 및 금속박 적층판

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JP2022505282A (ja) * 2018-10-18 2022-01-14 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 誘電コポリマー材料

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JP2012087250A (ja) * 2010-10-21 2012-05-10 Panasonic Corp 熱伝導性樹脂組成物、樹脂シート、プリプレグ、金属積層板およびプリント配線板
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
KR20140090991A (ko) * 2011-11-07 2014-07-18 미츠비시 가스 가가쿠 가부시키가이샤 수지 조성물, 이것을 사용한 프리프레그 및 적층판
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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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
JP2012087250A (ja) * 2010-10-21 2012-05-10 Panasonic Corp 熱伝導性樹脂組成物、樹脂シート、プリプレグ、金属積層板およびプリント配線板
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
KR20140090991A (ko) * 2011-11-07 2014-07-18 미츠비시 가스 가가쿠 가부시키가이샤 수지 조성물, 이것을 사용한 프리프레그 및 적층판
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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Publication number Priority date Publication date Assignee Title
JP2022505282A (ja) * 2018-10-18 2022-01-14 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 誘電コポリマー材料
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