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WO2019199033A1 - Composite de résine thermodurcissable pour stratifié plaqué de métal, et stratifié plaqué de métal - Google Patents

Composite de résine thermodurcissable pour stratifié plaqué de métal, et stratifié plaqué de métal Download PDF

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Publication number
WO2019199033A1
WO2019199033A1 PCT/KR2019/004223 KR2019004223W WO2019199033A1 WO 2019199033 A1 WO2019199033 A1 WO 2019199033A1 KR 2019004223 W KR2019004223 W KR 2019004223W WO 2019199033 A1 WO2019199033 A1 WO 2019199033A1
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WIPO (PCT)
Prior art keywords
thermosetting resin
group
metal foil
resin composite
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/KR2019/004223
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English (en)
Korean (ko)
Inventor
심창보
민현성
심희용
문화연
송승현
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LG Chem Ltd
Original Assignee
LG Chem Ltd
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Filing date
Publication date
Priority claimed from KR1020190036078A external-priority patent/KR102245724B1/ko
Priority claimed from KR1020190036079A external-priority patent/KR102246974B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to US16/764,831 priority Critical patent/US12091510B2/en
Priority to JP2020526329A priority patent/JP7078215B2/ja
Priority to CN201980005842.7A priority patent/CN111372997B/zh
Priority to EP19784661.1A priority patent/EP3750957B1/fr
Publication of WO2019199033A1 publication Critical patent/WO2019199033A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/56—Amines together with other curing agents
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/18—Homopolymers or copolymers of nitriles
    • C08L33/20—Homopolymers or copolymers of acrylonitrile
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L47/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions 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 C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate

Definitions

  • the present application is the Korean Patent Application No. 10-2018-0041697 dated April 10, 2018, Korea Patent Application No. 10-2018-0071076 dated June 20, 2018, Korea Patent Application No. 10-2019 dated March 28, 2019 -0036079, and the benefit of priority based on Korean Patent Application No. 10-2019-0036078 filed March 28, 2019, all the contents disclosed in the documents of the relevant Korean patent applications are incorporated as part of this specification.
  • the present invention relates to a thermosetting resin composite and a metal foil laminate for a metal foil laminate, and more particularly, has excellent flowability in the prepreg stage or the semi-cured state, can realize low glass transition temperature, modulus, low thermal expansion rate, and whip
  • the present invention relates to a thermosetting resin composite for a metal foil laminate and a metal foil laminate including the same.
  • Copper clad laminate used in the conventional printed circuit board is a prepreg by impregnating the substrate of the glass fiber (Gl ass Fabr ic) in the varnish of the thermosetting resin and then semi-cured, it is heated together with the copper foil It is prepared by pressing.
  • the prepreg is used again to construct a circuit pattern on the copper foil laminate and to build up thereon.
  • 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.
  • This warpage phenomenon is a phenomenon in which the printed circuit board does not become rolled back through a high temperature process such as reflow. Deepen.
  • the present invention provides a thermosetting resin composite for a metal foil laminate for a semiconductor package which has excellent flowability in a prepreg stage or a semi-cured state, can realize low glass transition temperature, modulus, low thermal expansion rate, and minimize warpage. It is to provide.
  • the present invention is to provide a metal foil laminate comprising the thermosetting resin composite for the metal foil laminate.
  • thermosetting resin composite for metal foil laminated plates whose thermal stress factor of following General formula 1 is 25 Mpa or less is provided.
  • the thermal stress factor, storage modulus and thermal expansion coefficient are respectively defined or measured in the range of 30 ° C to 260 ° C.
  • thermosetting resin composite for metal foil laminated plates which has a sheet shape; And a metal foil formed on at least one surface of the thermosetting resin composite for the metal foil laminate.
  • thermosetting resin composite and a metal foil laminate for a metal foil laminate according to a specific embodiment of the present invention will be described in detail.
  • thermosetting resin composite for a metal foil laminate having a thermal stress factor of 25 Mpa or less.
  • the thermal stress factor, storage modulus and thermal expansion coefficient are values defined or measured in the range of 30 ° C to 260 ° C, respectively.
  • warpage of the semiconductor package occurs due to the difference in thermal expansion between the semiconductor chip and the printed circuit board in the thinning process of the semiconductor package, and this warpage phenomenon is intensified through high temperature processes such as reflow. In order to improve this, only a method of lowering the thermal expansion coefficient of the substrate is known.
  • thermosetting resin composite for metal foil laminate and metal foil laminate formed by curing it the thermal stress factor defined by the general formula 1 in the temperature range of 30 ° C to 260 C
  • thermosetting resin composite for a metal foil laminate having a value of 25 Mpa or less, or 10 to 25 Mpa, or 12 to 21 Mpa can prevent warpage.
  • the thermal stress factor (Thermal Stress? & 01) of the general formula 1 is a numerical value obtained by multiplying the coefficient of thermal expansion and storage modulus at each temperature in units of 1 ° C from 30 to 2601: and then adds them together.
  • the coefficient of thermal expansion at each temperature is related to the strain of the thermosetting resin composite for metal foil laminates
  • the storage modulus at each temperature is related to the ratio of strain to strain (stress or stress) of the thermosetting resin composite for metal foil laminates. do.
  • the value of the product of the coefficient of thermal expansion and the storage modulus at each temperature is related to the strain (stress or stress) of the t-curable resin composite for the metal foil laminate, and accordingly, in units of TC from 30 ° C to 260 ° C.
  • the thermal stress factor of the general formula 1 which is a value obtained by multiplying the coefficient of thermal expansion and the storage modulus at each temperature and adding them together, represents the total strain (stress or stress) from 30 ° C to 260 ° C. Since printed wiring boards made of a thermosetting resin composite for laminated boards exhibit strain (stress or stress) applied to a semiconductor package. 2019/199033 1 »(: 1 ⁇ 1 ⁇ 2019/004223
  • the warp of the semiconductor package 3 ⁇ 3 ⁇ 6) is directly or indirectly factor showing.
  • thermosetting resin composite for the metal foil laminate of the embodiment may be formed by curing the prepreg.
  • the resultant obtained by etching the copper foil layer of a copper foil laminated board can be called "the thermosetting resin composite for metal foil laminated boards.” This is formed by curing at high temperature the prepreg obtained by hot air drying the thermosetting resin composition as described above.
  • the thermosetting resin composite for metal foil laminates has a thermal stress factor of 25 1 ⁇ 3 or less, or 10 to 10, in the temperature range of 30 ° to 260 ° ( : Can bend accordingly
  • thermosetting resin composite for metal foil laminates having the same or lower thermal expansion coefficient as the thermosetting resin composite for metal foil laminates of the above embodiment the thermal stress factor value defined by the general formula (1) is When the condition was not satisfied, it was confirmed that the semiconductor package manufactured by using the same produced relatively high warpage.
  • the storage elastic modulus at 30 ° 0 and 180 ° ( : of the thermosetting resin composite for metal foil laminates may be 16 ⁇ ⁇ 1 or less, respectively, specifically the storage elastic modulus at 30 ⁇ of the thermosetting resin composite for metal foil laminates is 12 And the storage modulus at 180 ⁇ of the thermosetting resin composite for the metal foil laminate is 7 Gpa to have.
  • thermosetting resin composite for the metal foil laminate It has a low storage modulus of less than below, and thus may have a relatively low thermal stress factor at the same coefficient of thermal expansion, so that the warpage of the semiconductor package may have a relatively low characteristic at a low temperature range such as 30 ⁇ and 180 ° (:). .
  • thermosetting resin composite material for the metal foil-clad laminate on
  • thermosetting resin composite for the metal foil laminate is described above at 260 °.
  • thermosetting resin composite for the metal foil laminate is described above at 260 °.
  • the warpage of the semiconductor package is low in the temperature range from 30 ° C to 260 ° C.
  • the thermal expansion coefficient of the thermosetting resin composite for the metal foil laminate may be 12 ppm / ° C. or less, or 5 to 12 mM / ° C, or 10 ⁇ m / ° C or less, or 4 to 10 ppm / ° C.
  • the thermosetting resin composite for the metal foil laminate has a low coefficient of thermal expansion, the thermal stress factor of the general formula 1 is 25 Mpa or less, the semiconductor package manufactured by using the thermosetting resin composite for the metal foil laminate Only relatively low levels of warpage can be seen.
  • the thermosetting resin composite for the metal foil laminate may include a thermosetting resin composition and a fiber substrate.
  • thermosetting resin composition 1) sulfone group; Carbonyl group; Halogen group; An alkyl group having 1 to 20 carbon atoms which is substituted or unsubstituted with a nitro group, cyano group or halogen group; An aryl group having 6 to 20 carbon atoms or unsubstituted or substituted with a nitro, cyano or halogen group; A heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a nitro group, cyano group, or halogen group; And an alkylene group having 1 to 20 carbon atoms unsubstituted or substituted with a nitro group, cyano group, or halogen group; an amine compound including at least one functional group selected from the group consisting of: 2) thermosetting resins, 3) thermoplastic resins, and 4 ) May contain inorganic fillers.
  • thermosetting resin composition may have a glass transition temperature of 230 ° C or less.
  • thermosetting resin composition may contain the above-mentioned amine compound including the strong electron withdrawing group It exhibits a relatively low reactivity as included, thereby making it possible to easily control the curing reaction of the thermosetting resin composition.
  • the thermosetting resin composition includes the thermosetting resin content in an amount of 400 parts by weight or less based on 100 parts by weight of the amine compound, and induces the thermosetting resin to be uniformly curable to a sufficient level without the influence of the filler charged in a high content. to, and can improve the reliability of the final product to be produced, it can increase mechanical properties such as toughness (toughness) also has a glass transition temperature of 230 ° (: can be reduced to less than a.
  • 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 flowability and moldability due to excessive curing of the thermosetting resin decreases There was.
  • thermosetting resin even when an excessive amount of a specific amine curing agent having reduced reactivity, including the electron withdrawing group ( ⁇ 3 ⁇ 4) as described above, is added, an increase in the curing rate of the thermosetting resin is suppressed due to a decrease in the reactivity of the curing agent. It is possible to exhibit high flowability even during long-term storage in the resin composition for semiconductor packages or in the prepreg state obtained therefrom, thereby having excellent moldability.
  • the thermosetting resin composition is 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, or 180 parts by weight to 290 parts by weight based on 100 parts by weight of the amine curing agent. Or 190 parts by weight to 290 parts by weight.
  • the thermosetting resin 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 of 300 parts by weight, based on 100 parts by weight of the amine curing agent mixture, Or 180 parts by weight to 290 parts by weight, or 190 parts by weight to 290 parts by weight.
  • thermosetting resin When the content of the thermosetting resin is excessively increased to more than 400 parts by weight based on 100 parts by weight of the amine curing agent, it is difficult to uniformly cure the thermosetting resin to a more sufficient level due to the increase of the curing density and the effect of the filler charged at a high content.
  • the reliability of the product being manufactured may be reduced, Mechanical properties such as toughness can also be reduced.
  • thermosetting resin composition may satisfy the equivalent ratio of 1.4 or more, 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.
  • Equivalence ratio total active hydrogen equivalents contained in the amine curing agent / total curable functional group equivalents contained in the thermosetting resin More specifically, in Equation 1, the total active hydrogen equivalents contained in the amine curing agent is the total amount of the amine curing agent
  • the weight (unit: g) means the unit weight of the active hydrogen of the amine curing agent (g / eq).
  • 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 refers to a hydrogen atom contained in the amino group (-N3 ⁇ 4) present in the amine curing agent, and the active hydrogen may 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 is a mixture of two or more kinds
  • the value obtained by dividing the weight (unit: g) by the unit equivalent (g / eq) of the curable functional group for each compound is obtained, and the sum thereof is contained in the thermosetting resin of Equation 1 above.
  • the total curable functional group equivalent 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 thermosetting resin type.
  • the curable functional group contained in the epoxy resin may be epoxy, 2019/199033 1 »(: 1 ⁇ 1 ⁇ 2019/004223
  • the curable functional group contained in the bismaleimide resin may be a maleimide group.
  • thermosetting resin composition satisfies that the equivalent ratio calculated by Equation (1) is equal to or greater than 1.4, wherein the amine curing agent of a sufficient level is contained so that the curable functional groups contained in all the thermosetting resins can cause a curing reaction. Means. Therefore, when the equivalent ratio calculated by Equation 1 in the thermosetting resin composition is reduced to less than 1.4, it is difficult to uniformly cure the thermosetting resin to a more sufficient level under the influence of the filler charged in a high content, the final product The reliability of can be reduced, mechanical properties also have the disadvantage that can be reduced.
  • the amine compound may be a sulfone group; Carbonyl group; Halogen group; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with a nitro group, cyano group, or halogen group; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with a nitro group, cyano group, or halogen group; A heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a nitro group, cyano group, or halogen group; And an alkylene group having 1 to 20 carbon atoms unsubstituted or substituted with a nitro group, cyano group, or halogen group; an aromatic amine compound containing at least one functional group selected from the group consisting of 2 to 5 amine groups have.
  • the amine compound may include one or more compounds selected from the group consisting of the following Chemical Formulas 1 to 3.
  • urine is a sulfone group, a carbonyl group, or an alkylene group having 1 to 10 carbon atoms
  • 3 ⁇ 4 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.
  • a heteroaryl group having 2 to 20 carbon atoms 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, II may be 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 heteroaryl group having 2 to 20 carbon atoms are each independently selected from the group consisting of nitro group, cyano group and halogen group It may be substituted with the above functional groups.
  • 1 to 3 ⁇ 4 are each independently a nitro group, 2019/199033 1 »(: 1 ⁇ 1 ⁇ 2019/004223
  • 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 And 3 ⁇ 4 '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 of 1 to 6 carbon atoms, 6 to 6 carbon atoms
  • the aryl group of 15 and the heteroaryl group having 2 to 20 carbon atoms may each be independently substituted with one or more functional groups selected from the group consisting of nitro groups, cyano groups, and halogen groups.
  • the alkyl group is a monovalent functional group derived from alkane (13 ⁇ 4116), and is, for example, linear, branched or cyclic, methyl, ethyl, propyl, isobutyl, Acebutyl, pentyl, nuclear chamber and the like. At least one hydrogen atom included in the alkyl group may be substituted with each substituent.
  • the alkylten group is a divalent functional group derived from alkane (13 ⁇ 411 ⁇ 2), and is, for example, linear, branched or cyclic, methylene group, ethylene group, propylten group, isobutyltene group, It may be a la butylten group, a pentylten 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), and may be, for example, monocyclic or polycyclic.
  • the monocyclic aryl group may be a phenyl group, a bar 0 phenyl group, terphenyl group, stilbenyl group and the like, but is not limited thereto.
  • the polycyclic aryl group include naphthyl group, anthryl group, phenanthryl group, pyrenyl group, perrylenyl group, chrysenyl group, fluorenyl group, and the like, but are 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 heterocyclic group containing 0, N or 3 as a hetero atom, and the carbon number is not particularly limited, but may be 2 to 30 carbon atoms.
  • heterocyclic groups 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 , 02019/199033 1 »(: 1 ⁇ 1 ⁇ 2019/004223
  • Dibenzothiophene group benzofuranyl group, dibenzofuran group and the like, but are not limited thereto.
  • At least one hydrogen atom of such a heteroaryl group may be each substituted with a substituent as in the alkyl group.
  • substituted means that another functional group is bonded to a hydrogen atom in the compound, and the position to be substituted is not limited to a position where a hydrogen atom is substituted, that is, a position where a substituent may be substituted.
  • the substituents may be the same or different from each other.
  • Formula 1 may include a compound represented by the following Formula 1-1.
  • Chemical Formula 2 may include a compound represented by Chemical Formula 2-1. 2019/199033 1 1/10 ⁇ 019/004223
  • the information about! 11 includes the above-described information in Chemical Formula 2.
  • Chemical Formula 2-1 examples include 2,2 ', 3,3', 5,5 ', 6,6'-
  • Chemical Formula 3 may include a compound represented by Chemical Formula 3-1.
  • thermosetting resin composition may include an amine compound, a thermosetting resin, a thermoplastic resin, and an inorganic filler. 2019/199033 1 »(: 1/10 ⁇ 019/004223
  • the content of the components is not particularly limited, the above-described components may be included in consideration of the physical properties of the final product manufactured from the thermosetting resin composition, and the content ratio between these components is as described below.
  • the thermosetting resin may include an epoxy resin.
  • the epoxy resin those used in the thermosetting resin composition for a semiconductor package can be used without limitation, and the type thereof is not limited, and bisphenol show type epoxy resin, phenol novolac epoxy resin, phenyl aralkyl epoxy resin, tetra It may be at least one selected from the group consisting of phenyl ethane epoxy resin, naphthalene epoxy resin, biphenyl epoxy resin, dicyclopentadiene epoxy resin, and a mixture of dicyclopentadiene epoxy resin and naphthalene epoxy resin.
  • 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), tetraphenyl represented by the formula (8) 1 selected from the group consisting of an ethane type epoxy resin, a naphthalene type epoxy resin represented by Formulas 9 and 10, a biphenyl type epoxy resin represented by Formula 11, and a dicyclopentadiene type epoxy resin represented by Formula 12: More than one species can be used.
  • II is 0 or an integer from 1 to 50.
  • the epoxy resin of Formula 5 may be a bisphenol show type epoxy resin, a bisphenol I 7 type epoxy resin, a bisphenol type epoxy resin, or a bisphenol type epoxy resin, respectively, according to the type of urine.
  • 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 I?
  • II is 0 or an integer from 1 to 50.
  • thermosetting 'resins are bismaleimide resins, cyanate ester resins and bismaleimide-can be further comprising at least one resin selected from the group consisting of a triazine resin.
  • the bismaleimide resin is usually a thermosetting resin for a semiconductor package 2019/199033 1 »(: 1 ⁇ 1 ⁇ 2019/004223
  • 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), and a bisphenol show diphenyl ether represented by the following formula (15). It may be at least one selected from the group consisting of a bismaleimide resin and a bismaleimide resin composed of an oligomer of diphenylmethane bismaleimide and phenylmethane type maleimide resin represented by the following formula (16).
  • 3 ⁇ 4 and 3 ⁇ 4 are each independently (: 3 ⁇ 4 or 3 ⁇ 43 ⁇ 4).
  • II is 0 or an integer from 1 to 50.
  • the cyanate-based resins include cyanate ester resins, and those commonly used in thermosetting resin compositions for semiconductor packages may be used without limitation, and the type thereof 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.
  • II 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 urine. .
  • the bismaleimide-triazine resin may be exemplified as the bismaleimide resin, and the bismaleimide-triazine resin may be used without limitation in the thermosetting resin composition for a semiconductor package.
  • the thermoplastic resin has the effect of increasing the toughness (Toughness) after curing of the prepreg, and may serve to reduce the warpage of the semiconductor package by lowering the coefficient of thermal expansion and elastic modulus.
  • a (meth) acrylate type polymer is mentioned.
  • Examples of the (meth) acrylate-based polymer are not particularly limited, and for example, an acrylic ester containing a repeating unit derived from a (meth) acrylate monomer and a repeating unit derived from a (meth) acrylonitrile. 2019/199033 1 »(: 1 ⁇ 1 ⁇ 2019/004223
  • the (meth) acrylate-based polymer is a monomer such as butyl acrylate, ethyl acrylate, acrylonitrile, methyl methacrylate, glycidyl methacrylate in the range of 1 to 40% by weight ( Relative to the total weight of the entire monomer).
  • the (meth) acrylate-based polymer may have a weight average molecular weight of 500, 000 to 1,000, 000. If the weight average molecular weight of the (meth) acrylate-based polymer is too small, it may be technically disadvantageous after curing because the effect is decreased in increasing the toughness of the thermosetting resin composite for the metal foil laminate or decreasing the thermal expansion and elastic modulus. In addition, when the weight average molecular weight of the (meth) acrylate-based polymer is too large, the flowability of the prepreg can be reduced.
  • the thermoplastic resin may determine the content used in consideration of the use and properties of the final product, for example, the thermosetting resin composition for a semiconductor package includes 10 to 200 parts by weight of the thermoplastic resin relative to 100 parts by weight of the thermosetting resin. can do.
  • the thermosetting resin composition may include the amine compound described above, and may further include an additional curing agent other than the amine compound. More specifically, the thermosetting resin composition is selected from the group consisting of a second amine compound, an acid anhydride resin, a bismaleimide resin, a cyanate resin, a phenol novolak resin and a benzoxazine resin different from the amine compound. It may further comprise one or more curing agents.
  • the thermosetting resin composition may include an inorganic filler.
  • the inorganic filler can be used in the thermosetting resin composition for the semiconductor package usually without limitation, and specific examples include silica, aluminum trihydroxide, magnesium hydroxide, molybdenum oxide, zinc molybdate, zinc borate , Zinc stannate , Alumina, Clay, kaolin, talc, calcined kaolin, calcined talc, mica, short glass fiber, glass fine powder and hollow glass, and may be one or more selected from the group consisting of these.
  • the thermosetting resin composition may include 30 to 300 parts by weight, or 30 to 200 parts by weight, or 50 to 150 parts by weight of the inorganic filler relative to a total of 100 parts by weight of the thermosetting resin, the thermoplastic resin, and the amine compound. If the content of the inorganic filler is too small, the coefficient of thermal expansion is increased, so that warpage intensifies during the reflow process, and the rigidity of the printed circuit board is reduced. In addition, when the surface-treated filler is used, the packing density may be increased by using a small size of the nano particle size and a large size of the micro particle size to increase the packing density.
  • the inorganic filler may include two or more inorganic fillers having different average particle diameters. Specifically, at least one of the two or more inorganic fillers may be an inorganic filler having an average particle diameter of 0.1 m to 100 _, and the other one may be an inorganic filler having an average particle diameter of 1 nm to 90.
  • the inorganic filler having an average particle diameter of 1 nm to 90 ran may be 1 part by weight to 30 parts by weight based on 100 parts by weight of the inorganic filler having an average particle diameter of 0.1 m to 100 ran.
  • the 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 cudling 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 may include amino such as 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-2-aminoethyl) -3 aminopropyltrimethoxysilane.
  • Vinyl benzylaminoethyl) -3 cationic silane coupling agent such as 3-aminopropyltrimethoxysilane hydrochloride and phenyl silane coupling agent, and the silane coupling agent may be used alone, or at least two silanes as necessary. Coupling agents can be used in combination.
  • the silane compound is an aromatic amino silane or
  • (Meth) acrylsilane may be included, and as the inorganic filler having an average particle diameter of 0.1 _ to 100 !, silica having an aromatic amino silane treated may be used, and the average particle diameter of 11 to 90 11 As the inorganic filler, silica treated with (meth) acryl silane can be used.
  • the aromatic amino silane-treated silica include 205 (1 ' 0 (111 6 ( ⁇ 3)), and the specific example of the (meth) acryl silane-treated silica is shown in Show0413 (g). Can be mentioned.
  • the said (meth) acryl was used by the meaning containing all acryl or methacryl.
  • the thermosetting resin composition may be used as a solution by adding a solvent as necessary.
  • the additive solvent is not particularly limited as long as it shows good solubility in the resin component, and alcohol, ether, ketone, amide, aromatic hydrocarbon, ester, and nitrile may be used. Or you may use the mixed solvent which used 2 or more types together.
  • 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.
  • thermosetting resin composition may further include various high molecular compounds such as other thermosetting resins, thermoplastic resins and oligomers and elastomers thereof, other flame retardant compounds or additives, so long as the properties inherent in the resin composition are not impaired. These are not particularly limited as long as they are selected from those commonly used.
  • the additives include UV absorbers, antioxidants, photopolymerization initiators, optical brighteners, photosensitizers, pigments, dyes, thickeners, lubricants, antifoaming agents, dispersants, leveling agents, and brightening agents.
  • the thermosetting resin composite for a metal foil laminate means that the thermosetting resin composition for a semiconductor package is impregnated into a fiber substrate in a cured state.
  • the fiber base is not particularly limited in kind, but may be a polyamide resin fiber such as a glass fiber base, a polyamide resin fiber, an aromatic polyamide resin fiber, a polyester resin fiber, an aromatic polyester resin fiber, a wholly aromatic polyester, etc.
  • Synthetic fiber base kraft paper, cotton linter paper, linter and kraft pulp composed of woven or nonwoven fabrics mainly composed of polyester resin fibers such as resin fibers, polyimide resin fibers, polybenzoxazole fibers, and fluorine resin fibers
  • Paper substrates based on honcho 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 fiber substrate 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, and Q glass. If desired, the glass-based material may be selected depending on the intended use or performance. Glass-based forms are typically woven, nonwoven, roving, chopped strand mats or surfacing mats. The thickness of the glass base material is not particularly limited, and about 0.01 to 0.3 mm may be used. Of these materials, glass fiber materials are more preferred in terms of strength and water absorption properties.
  • the method for preparing the prepreg is not particularly limited and may be prepared by a method well known in the art.
  • the method of manufacturing the prepreg may be an impregnation method, a coating method using various coaters, a spray injection method, or the like.
  • the fiber substrate is varnished 2019/199033 1 »(: 1 ⁇ 1 ⁇ 2019/004223
  • Prepreg can be prepared by impregnation.
  • 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 ketone, methyl isobutyl ketone and cyclonuxanone, aromatic hydrocarbons such as benzene, toluene and xylene, and amides such as dimethylformamide and dimethylacetamide, methylcello Solv, aliphatic alcohols such as butyl cellosolve.
  • the solvent used is volatilized by 80% by weight or more.
  • the temperature at the time of drying is about 80 To 200 ° 0, the time is not particularly limited in balance with the gelation time of the varnish.
  • the varnish impregnation amount is preferably such that the resin solid content of the varnish is about 30 to 80% by weight based on the total amount of the resin solid content of the varnish and the base material.
  • 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 the composite foil of the two-layered structure which combined aluminum and copper foil.
  • the metal foil may be a copper foil or an aluminum foil, and a metal having a thickness of about 2 to 200 — may be used, but the thickness thereof is preferably about 2 to 35.
  • copper foil is used as said metal foil.
  • nickel, nickel-phosphorus, nickel-tin alloy, nickel-iron alloy, lead, lead-tin alloy, or the like may be used as an intermediate layer.
  • the metal laminated plate containing the thermosetting resin composite for metal foil laminated plates thus manufactured can be used for manufacture of single-sided, double-sided, or multilayer printed circuit boards.
  • the metal foil laminate may be processed to fabricate a single-sided or double-sided or multilayer printed circuit board, and the circuit processing may be performed by a general single-sided, double-sided or multilayer printed circuit board manufacturing process.
  • thermosetting resin for a metal foil laminate for a semiconductor package which has excellent flowability in a prepreg stage or a semi-cured state, can realize low glass transition temperature and modulus, low thermal expansion rate, and minimize warp large size seedling phenomenon.
  • a metal foil laminate comprising a composite and the thermosetting resin composite for the metal foil laminate may be provided.
  • each component was added to methyl ethyl ketone according to the solid content of 40% and mixed, and then stirred at room temperature at a rate of 400 days for 1 day to prepare a resin composition for a semiconductor package of Example and Comparative Example (resin Varnish) was prepared.
  • the specific composition of the resin composition prepared in Example is as shown in Table 1 below
  • the specific composition of the resin composition prepared in Comparative Example is as shown in Table 2 below.
  • thermosetting resin composites for metal foil laminates and copper foil laminates After impregnating the resin composition (resin varnish) for the semiconductor package prepared in 13_ glass fiber (T-gl ass # 1010, manufactured by Ni ttobo Co., Ltd.), hot-air dried at a temperature of 170 ° C for 2-5 minutes. A prepreg of 18 // m was prepared. After the two prepregs prepared above were laminated, copper foil (thickness 12 sun), manufactured by Mi tsui) was placed on both sides thereof, and laminated, and cured for 100 minutes under conditions of 220 ° C. and 35 kg / cuf. Laminates were prepared.
  • thermosetting resin composition for semiconductor packages the prepreg, the thermosetting resin composite for metal foil laminated sheets, and the copper foil laminated sheets obtained by the Example and the comparative example>
  • thermosetting resin composition for a semiconductor package the prepreg, the thermosetting resin composite for a metal foil laminated sheet, and the copper foil laminated sheet obtained by the said Example and the comparative example were measured by the following method, and the result is shown in Table 3.
  • CTE Coefficient of thermal expansion
  • the test piece was produced in MD direction, and it heated up at 30 degrees (: to 260 degrees (:) up to 30 degrees using TMA (TA Instruments, Q400). After measuring at a rate of 10 ° C / min, the measured value in the range of 50 ° C to 150 ° C was recorded as the coefficient of thermal expansion.
  • thermosetting resin composite for metal foil laminated sheets which is formed by curing the prepreg obtained by hot air drying the thermosetting resin composition as described above.
  • the test piece (thermosetting resin composite for metal foil laminated sheets) was produced in MD direction, and it was 5 degrees in tension mode using DMA (TA Instruments, Q800).
  • the peak temperature of tan del ta was measured as the glass transition temperature by measuring from 25 ° C. to 300 ° C. under an elevated temperature condition of C / min. 3.
  • test piece thermosetting resin composite for metal foil laminated boards
  • storage modulus was measured from 25 ° C to 300 ° C at a temperature rise of / min.
  • the prepregs obtained in the above examples and comparative examples are placed on both sides of the circuit pattern (pattern height 7 m, residual ratio 50%), and copper foil (thickness 12 / zm,
  • the printed wiring board was manufactured (thickness 90 *).
  • a semiconductor package (14.5mm x 14.5mm x 390um) was manufactured by mounting a semiconductor chip (11.5mm x 11.5mm x thickness 80um) on the manufactured printed wiring board.
  • the warpage was measured on the basis of the Shadow Moire measurement theory using a warpage measuring device (Therm0ire PS100 by AKR0METRIX). Warpage measures the semiconductor package from 30 ° C. to 260 ° C. and thereafter When cooled to 30 ° C, the difference between the maximum value and the minimum value of the warpage was obtained, and the warpage of the semiconductor package was evaluated based on the following criteria.
  • thermosetting resin composition for semiconductor packages and physical properties of thermosetting resin composites for metal foil laminates of Examples (per unit)
  • Acrylic rubber B (Mw 800,000): PARACR0N KG_3015P (Negami chemical industrial Co., LTD)
  • the total active hydrogen equivalent of DDS is the total weight in g divided by the unit equivalent of active hydrogen in DDS (62 g / eq),
  • the total active hydrogen equivalent of TFB is the total weight (g) of TFB divided by the unit equivalent of active hydrogen (80 g / eq) of TFB,
  • the total active hydrogen equivalent of DDM is the total weight of DDM divided by the unit equivalent of DDM (49.5 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 the XD-1000.
  • 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 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 maleimide equivalent of BMI-2300 (179 g / eq).
  • the thermosetting resin composite for a metal foil laminate formed from a prepreg containing an amine compound having an electron attracting (Electron Withdrawing Group, CTG) as in Example has a glass transition temperature of 230 ° C or less, It was confirmed that the circuit pattern fillability was excellent while having a low coefficient of thermal expansion of 10 ppm / ° C or less.
  • thermosetting resin of 290 parts by weight or less relative to 100 parts by weight of the amine compound having an electron draw (EWG) as in the embodiment, and the equivalent ratio of the equivalent amine compound equivalent ratio based on the thermosetting resin equivalent satisfies 1.4 or more
  • the amount of the inorganic additive is added in an amount of 150 parts by weight in an amount of 50 parts by weight based on 100 parts by weight of the total amount of the thermosetting resin, the thermoplastic resin and the amine compound, the thermal properties bonded to the semiconductor packaging, excellent low thermal expansion properties, flowability and It was confirmed that mechanical properties can be secured.
  • thermosetting resin composites for metal foil laminates obtained in the examples is 21 Mpa or less, and the semiconductor package manufactured using the thermosetting resin composites for metal foil laminates having such thermal stress factors is relatively As a result, only low levels of warpage were found.
  • thermosetting resin composites for metal foil laminates obtained in the comparative examples is greater than 25 Mpa, and the semiconductor package manufactured by using the thermosetting resin composites for metal foil laminates having such a high thermal stress factor is relatively high. It was confirmed that high whip occurred.

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Abstract

La présente invention concerne un composite de résine thermodurcissable pour un stratifié plaqué de métal et un stratifié plaqué de métal et, plus spécifiquement, un composite de résine thermodurcissable pour un stratifié plaqué de métal ayant une valeur de facteur de contrainte thermique prédéterminée et un stratifié plaqué de métal comprenant le composite de résine thermodurcissable pour un stratifié plaqué de métal.
PCT/KR2019/004223 2018-04-10 2019-04-09 Composite de résine thermodurcissable pour stratifié plaqué de métal, et stratifié plaqué de métal Ceased WO2019199033A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US16/764,831 US12091510B2 (en) 2018-04-10 2019-04-09 Thermosetting resin composite and metal clad laminate using the same
JP2020526329A JP7078215B2 (ja) 2018-04-10 2019-04-09 金属箔積層板用熱硬化性樹脂複合体および金属箔積層板
CN201980005842.7A CN111372997B (zh) 2018-04-10 2019-04-09 用于金属包层层合体的热固性树脂复合材料及使用其的金属包层层合体
EP19784661.1A EP3750957B1 (fr) 2018-04-10 2019-04-09 Composite de résine thermodurcissable pour stratifié plaqué de métal, et stratifié plaqué de métal

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KR10-2018-0041697 2018-04-10
KR20180041697 2018-04-10
KR20180071076 2018-06-20
KR10-2018-0071076 2018-06-20
KR1020190036078A KR102245724B1 (ko) 2018-06-20 2019-03-28 금속박 적층판용 열경화성 수지 복합체 및 금속박 적층판
KR1020190036079A KR102246974B1 (ko) 2018-04-10 2019-03-28 반도체 패키지용 열경화성 수지 조성물, 프리프레그 및 금속박 적층판
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PCT/KR2019/004223 Ceased WO2019199033A1 (fr) 2018-04-10 2019-04-09 Composite de résine thermodurcissable pour stratifié plaqué de métal, et stratifié plaqué de métal

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