WO2025134854A1 - 樹脂組成物、樹脂フィルム、プリプレグ、積層板、プリント配線板及び半導体パッケージ - Google Patents

樹脂組成物、樹脂フィルム、プリプレグ、積層板、プリント配線板及び半導体パッケージ Download PDF

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WO2025134854A1
WO2025134854A1 PCT/JP2024/043512 JP2024043512W WO2025134854A1 WO 2025134854 A1 WO2025134854 A1 WO 2025134854A1 JP 2024043512 W JP2024043512 W JP 2024043512W WO 2025134854 A1 WO2025134854 A1 WO 2025134854A1
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Prior art keywords
resin composition
component
resin
mass
composition according
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French (fr)
Japanese (ja)
Inventor
志織 吉澤
祥汰 中村
抗太 岩永
裕太 中野
圭芸 日▲高▼
史貴 上野
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Resonac Corp
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Resonac Corp
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Priority to JP2025565264A priority Critical patent/JPWO2025134854A1/ja
Priority to CN202480028619.5A priority patent/CN121079354A/zh
Publication of WO2025134854A1 publication Critical patent/WO2025134854A1/ja
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F287/00—Macromolecular compounds obtained by polymerising monomers on to block polymers
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
    • 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

  • This disclosure relates to resin compositions, resin films, prepregs, laminates, printed wiring boards, and semiconductor packages.
  • Patent Document 1 a resin composition containing a specific polyphenylene ether derivative, a specific thermosetting resin, and a styrene-based thermoplastic elastomer (see Patent Document 1) has been proposed with the objective of providing a resin composition that has particularly good compatibility, high frequency characteristics, high adhesion to conductors, excellent heat resistance, a high glass transition temperature, low thermal expansion, and high flame retardancy.
  • prepregs containing a resin composition and a fiber base material are cut to the desired size and then used to manufacture laminates.
  • Prepregs manufactured using conventional resin compositions sometimes generate powder when cut.
  • the prepregs rub against each other and generate powder. If the generated powder adheres to the prepregs, it will fall into the equipment when stacking the prepregs to manufacture a laminate, which can cause contamination when manufacturing laminates using prepregs with different components.
  • the powder adheres to the blade used during cutting the powder will adhere when cutting prepregs with different components, which can also cause contamination. For this reason, it is necessary to clean the entire manufacturing line, including the prepreg cutting equipment and the inside of the laminate manufacturing equipment, which reduces production efficiency.
  • the present disclosure aims to provide a resin composition that can suppress the generation of powder in prepregs and can suppress an increase in the minimum melt viscosity, as well as to provide resin films, prepregs, laminates, printed wiring boards, and semiconductor packages that use the resin composition.
  • the present disclosure provides a resin composition that can suppress the generation of powder in prepregs and can suppress an increase in the minimum melt viscosity, and can provide resin films, prepregs, laminates, printed wiring boards, and semiconductor packages that use the resin composition.
  • FIG. 1 is a photograph showing the state of a cutter when dust generation is evaluated as A in an example.
  • 13 is a photograph showing the state of a cutter when the evaluation of powder generation was B in the comparative example.
  • 13 is a photograph showing the state of a cutter when dust generation was evaluated as C in the comparative example.
  • the upper or lower limit of the numerical range may be replaced with the values shown in the examples.
  • the lower and upper limits of a numerical range may be arbitrarily combined with the lower or upper limit of another numerical range.
  • the numerical values AA and BB at both ends are included in the numerical range as the lower and upper limits, respectively.
  • the description "10 or more” means 10 and a numerical value exceeding 10, and the same applies when the numerical values are different.
  • the description "10 or less” means 10 and a numerical value less than 10, and the same applies when the numerical values are different.
  • each component and material exemplified in this disclosure may be used alone or in combination of two or more.
  • the content of each component in the resin composition means the total amount of the multiple substances present in the resin composition when multiple substances corresponding to each component are present in the resin composition, unless otherwise specified.
  • the term "resin component” refers to all components among the solid contents constituting the resin composition, excluding inorganic compounds such as inorganic fillers described below.
  • the term “solid content” refers to components other than the organic solvent described below, and components that are liquid at 25° C. are also considered to be solid content.
  • the expression "containing XX” described in the present disclosure means that it may be in either an embodiment that XX is contained in a reacted state when XX is capable of reacting, or that XX is simply contained. Any combination of the descriptions in this disclosure is also included in this disclosure and this embodiment.
  • the resin composition of the present embodiment is as follows.
  • a resin composition containing a maleimide resin (A) and a block copolymer (B) the component (A) contains a maleimide resin (A1) having an indane skeleton and a maleimide resin (A2) not having an indane skeleton,
  • components that may be contained in the resin composition of the present embodiment will be described.
  • the maleimide resin (A) includes a maleimide resin (A1) having an indane skeleton and a maleimide resin (A2) not having an indane skeleton.
  • the indane skeleton contained in the component (A1) preferably has a divalent group represented by general formula (a1-1) shown below.
  • R a1 represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group; and n1 represents an integer of 0 to 3.
  • R a2 to R a4 each independently represent an alkyl group having 1 to 10 carbon atoms. * represents a bonding site.
  • the component (A1) is preferably a bismaleimide resin.
  • a bismaleimide resin represented by the following general formula (a1-2) is preferable, from the viewpoints of dielectric constant (Dk), adhesion to a conductor, heat resistance, and ease of production.
  • R a1 to R a4 and n1 are the same as those in the general formula (a1-1).
  • Each R a5 independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a nitro group, a hydroxyl group, or a mercapto group; each n2 independently represents an integer of 0 to 4, and n3 represents a number of 0.95 to 10.0.)
  • the bismaleimide resin represented by the general formula (a1-2) is more preferably a bismaleimide resin represented by the following general formula (a1-3) or a bismaleimide resin represented by the following general formula (a1-4) from the viewpoints of dielectric constant (Dk), adhesion to conductors, solvent solubility, and ease of manufacture.
  • Dk dielectric constant
  • R a1 to R a5 , n1 and n3 are the same as those in the general formula (a1-2).
  • R a1 to R a4 , n1 and n3 are the same as those in the general formula (a1-2).
  • component (A1) There are no particular limitations on the method for producing component (A1), and known methods can be used as reference or adapted.
  • the component (A1) may be, or may not be, an addition reaction product with an amine compound such as a monoamine compound or a diamine compound.
  • the monoamine compound include monoamine compounds having an acidic substituent, such as o-aminophenol, m-aminophenol, p-aminophenol, o-aminobenzoic acid, m-aminobenzoic acid, p-aminobenzoic acid, o-aminobenzenesulfonic acid, m-aminobenzenesulfonic acid, p-aminobenzenesulfonic acid, 3,5-dihydroxyaniline, and 3,5-dicarboxyaniline.
  • aromatic diamine compounds in which an amino group is bonded to an aromatic hydrocarbon group such as 3,3'-dihydroxy-4,4'-diaminodiphenylmethane, 2,2',6,6'-tetramethyl-4,4'-diaminodiphenylmethane, 3,3'-dichloro-4,4'-diaminodiphenylmethane, 3,3'-dibromo-4,4'-diaminodiphenylmethane, 2,2',6,6'-tetrachloro-4,4'-diaminodiphenylmethane, and 2,2',6,6'-tetrabromo-4,4'-diaminodiphenylmethane; siloxane diamines.
  • the component (A2) is not particularly limited as long as it does not contain an indane skeleton, and any maleimide resin other than the component (A1) can be used.
  • the following description of the component (A2) is based on the premise that it does not contain an indane skeleton, unless otherwise specified.
  • the component (A2) is preferably at least one selected from the group consisting of maleimide resins having one or more (preferably two or more) N-substituted maleimide groups and derivatives thereof.
  • the maleimide resin having one or more N-substituted maleimide groups is not particularly limited, and examples thereof include aromatic maleimide resins preferably having one N-substituted maleimide group bonded to an aromatic ring, such as N-phenylmaleimide, N-(2-methylphenyl)maleimide, N-(4-methylphenyl)maleimide, N-(2,6-dimethylphenyl)maleimide, N-(2,6-diethylphenyl)maleimide, N-(2-methoxyphenyl)maleimide, and N-benzylmaleimide; bis(4-maleimidophenyl)methane, bis(4-maleimidophenyl)ether, bis(4-maleimidophenyl)sulfone, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, and the like.
  • aromatic bismaleimide resins preferably having two N-substituted maleimide groups bonded to an aromatic ring, such as polyphenylmethane maleimide and biphenyl aralkyl-type maleimide; aromatic polymaleimide resins preferably having three or more N-substituted maleimide groups bonded to an aromatic ring, such as N-dodecylmaleimide, N-isopropylmaleimide, N-cyclohexylmaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane and pyrrolidine binder-type long-chain alkyl bismaleimide.
  • the (A2) component is preferably a maleimide resin having two or more N-substituted maleimide groups, more preferably an aromatic maleimide resin having two or more N-substituted maleimide groups, and furthermore, from the viewpoint of heat resistance and flame retardancy, an aromatic maleimide resin having three or more N-substituted maleimide groups is even more preferable, and particularly preferably an aromatic polymaleimide resin having three or more N-substituted maleimide groups bonded to an aromatic ring.
  • the aromatic maleimide resin having three or more N-substituted maleimide groups is more preferably a maleimide resin represented by the following general formula (A2-1).
  • X A2-1 is a divalent hydrocarbon group having 1 to 20 carbon atoms (but does not contain an indane skeleton), and n A2-1 is an integer of 2 to 5.
  • Examples of the divalent hydrocarbon group having 1 to 20 carbon atoms represented by X A2-1 in the general formula (A2-1) include divalent aliphatic hydrocarbon groups such as an alkylene group having 1 to 5 carbon atoms and an alkylidene group having 2 to 5 carbon atoms, and divalent hydrocarbon groups containing an aromatic hydrocarbon group represented by the following general formula (A2-2), etc.
  • the divalent hydrocarbon group having 1 to 20 carbon atoms does not contain an indane skeleton.
  • Examples of the alkylene group having 1 to 5 carbon atoms include a methylene group, a 1,2-dimethylene group, a 1,3-trimethylene group, a 1,4-tetramethylene group, a 1,5-pentamethylene group, etc.
  • an alkylene group having 1 to 5 carbon atoms an alkylene group having 1 to 3 carbon atoms is preferable, an alkylene group having 1 or 2 carbon atoms is more preferable, and a methylene group is even more preferable.
  • the alkylidene group having 2 to 5 carbon atoms is preferably an alkylidene group having 2 to 4 carbon atoms, more preferably an alkylidene group having 2 or 3 carbon atoms, and further preferably an isopropylidene group.
  • Ar A2-2 is a divalent aromatic hydrocarbon group
  • X A2-2 and X A2-3 are each independently a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms. * represents a bonding site.
  • Examples of the divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by X A2-2 and X A2-3 in the general formula (A2-2) include the same alkylene groups having 1 to 5 carbon atoms and alkylidene groups having 2 to 5 carbon atoms as exemplified as X A2-1 in the general formula (A2-1). Among these, a methylene group is preferred.
  • Examples of the divalent aromatic hydrocarbon group represented by Ar A2-2 in the general formula (A2-2) include a phenylene group, a naphthylene group, a biphenylene group, and an anthranylene group. Of these, a biphenylene group is preferable.
  • biphenylene group examples include a 4,2'-biphenylene group, a 4,3'-biphenylene group, a 4,4'-biphenylene group, and a 3,3'-biphenylene group. Of these, a 4,4'-biphenylene group is preferable.
  • X A2-1 in general formula (A2-1) is preferably a divalent hydrocarbon group containing an aromatic hydrocarbon group represented by general formula (A2-2), and more preferably a divalent hydrocarbon group in which X A2-2 and X A2-3 are methylene groups and Ar A2-2 is a 4,4'-biphenylene group in general formula (A2-2).
  • n A2-1 is an integer of 2 to 5, preferably an integer of 2 to 4, and more preferably 2 or 3.
  • examples of derivatives of the maleimide resin include addition reaction products of the maleimide resin having one or more (preferably two or more) N-substituted maleimide groups and an amine compound such as a monoamine compound or a diamine compound.
  • examples of the monoamine compound and diamine compound include the same monoamine compound and diamine compound described in the description of component (A1).
  • the content of component (A) in the resin composition of the present embodiment is not particularly limited, but from the viewpoints of high frequency characteristics, heat resistance, low thermal expansion property, and moldability, it is preferably 20 to 90 parts by mass, more preferably 40 to 90 parts by mass, even more preferably 50 to 85 parts by mass, and particularly preferably 55 to 80 parts by mass, relative to 100 parts by mass of the resin component in the resin composition of the present embodiment.
  • the content ratio of the component (A1) to the component (A2) [(A1)/(A2)] is not particularly limited, but from the viewpoint of a balance between high frequency characteristics, heat resistance, low thermal expansion property, moldability, heat resistance and flame retardancy, it is preferably 10/90 to 90/10, more preferably 30/70 to 90/10, even more preferably 50/50 to 90/10, particularly preferably 55/45 to 90/10, and most preferably 65/35 to 85/15.
  • the resin composition of the present embodiment contains the block copolymer (B), which makes it possible to suppress the generation of powder when cutting the prepreg, and when the cut prepregs are stacked and transported, and when they are stacked during the production of a laminate.
  • the block copolymer (B) has a block (b1) containing a structural unit derived from an aromatic hydrocarbon compound and a block (b2) containing a structural unit derived from a conjugated diene compound.
  • the aromatic vinyl compounds in the structural units derived from the aromatic hydrocarbon compounds include styrene, ⁇ -methylstyrene, 2,4-dimethylstyrene, 1-vinylnaphthalene, 4-methoxystyrene, monochlorostyrene, divinylbenzene, etc. Among these, styrene is preferred.
  • examples of the structural unit derived from the conjugated diene compound include 1,3-butadiene (hereinafter sometimes simply referred to as butadiene), isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, 2-phenyl-1,3-butadiene, 1,3-hexadiene, etc.
  • the conjugated diene compound is preferably one or more selected from the group consisting of butadiene and isoprene, more preferably contains butadiene, and even more preferably is butadiene.
  • the structural unit derived from the conjugated diene compound is not particularly limited, and examples thereof include a 1,2-bond unit of butadiene, a 1,4-bond unit of butadiene, a 3,4-bond unit of isoprene, a 1,4-bond unit of isoprene, and bond units obtained by hydrogenating these bond units.
  • bond units obtained by hydrogenating these bond units include, as shown in the structural formula below, a "butylene unit” which is a bond unit obtained by hydrogenating a 1,2-bond unit of butadiene, an "ethylene unit” which is a bond unit obtained by hydrogenating a 1,4-bond unit of butadiene (generally referred to as such in consideration of the structural unit enclosed in parentheses in the structural formula below.
  • parentheses are for explanatory purposes and are not intended to separate structural units), an "ethylene-butylene unit” having both the butylene unit and the ethylene unit, an “isopentene unit” which is a bond unit obtained by hydrogenating a 3,4-bond unit of isoprene ("3-methyl-1-butene unit”), and an "ethylene-propylene unit” which is a bond unit obtained by hydrogenating a 1,4-bond unit of isoprene (generally referred to as such in consideration of the structural unit enclosed in parentheses in the structural formula below. Note that the parentheses are for explanatory purposes and are not intended to separate structural units) (see the structural formula below).
  • the structural units derived from the conjugated diene compound are preferably butylene units, ethylene units, and ethylene-butylene units, and more preferably ethylene-butylene units.
  • the content of the structural unit derived from an aromatic hydrocarbon compound is preferably 80% by mass or more, more preferably 90% by mass or more, even more preferably 95% by mass or more, particularly preferably 98% by mass or more, and may be 100% by mass.
  • the content of the structural unit derived from a conjugated diene compound is preferably 80% by mass or more, more preferably 90% by mass or more, even more preferably 95% by mass or more, particularly preferably 98% by mass or more, and may be 100% by mass.
  • the content of the block (b1) in the (B) component is 15% by mass or more, so that the generation of powder in the prepreg can be suppressed and the increase in the minimum melt viscosity can be suppressed.
  • the content of the block (b1) in the (B) component is preferably 18% by mass or more, more preferably 20% by mass or more, even more preferably 25% by mass or more, particularly preferably 28% by mass or more, and may be 30% by mass or more or may be 35% by mass or more.
  • the upper limit of the content of the block (b1) in the (B) component may be 70% by mass or less, 65% by mass or less, 60% by mass or less, 55% by mass or less, 50% by mass or less, or 45% by mass or less.
  • the content of the block (b1) in the (B) component may be 15 to 70% by mass, and the lower and upper limits of the numerical range can be changed according to the above explanation.
  • the content of the block (b1) in the component (B) is 15 to 35% by mass, and further 25 to 35% by mass, the effect of reducing the minimum melt viscosity tends to be even greater.
  • the total content of "block (b1) containing a structural unit derived from an aromatic hydrocarbon compound and block (b2) containing a structural unit derived from a conjugated diene compound” in the (B) component is not particularly limited, and may be 20% by mass or more, 40% by mass or more, 50% by mass or more, 80% by mass or more, 90% by mass or more, 95% by mass or more, 98% by mass or more, or 100% by mass, based on the entire (B) component.
  • the hydrogenation rate is preferably 70 mol% or more, more preferably 80 mol% or more, even more preferably 90 mol% or more, and particularly preferably 95 mol% or more.
  • the hydrogenation rate may be 100 mol% or less, or 99 mol% or less. In other words, the hydrogenation rate may be 70 to 100 mol%.
  • the number average molecular weight of the component (B) is not particularly limited, but is preferably 10,000 to 120,000, more preferably 30,000 to 110,000, even more preferably 50,000 to 100,000, particularly preferably 55,000 to 90,000, and most preferably 55,000 to 85,000. By having the number average molecular weight of the component (B) within the above range, there is a tendency that an increase in the minimum melt viscosity is easily suppressed.
  • the molecular weight distribution (Mw/Mn) of the component (B) is not particularly limited, but is preferably 1.00 to 3.50, may be 1.05 to 3.00, may be 1.05 to 2.00, may be 1.05 to 1.50, or may be 1.05 to 1.30.
  • the weight average molecular weight (Mw) and number average molecular weight (Mn) are values calculated from a calibration curve using standard polystyrene by gel permeation chromatography (GPC), and more specifically, are values determined by the measurement method described in the Examples.
  • the component (B) may be modified with an acid anhydride such as maleic anhydride.
  • the acid value of the acid-modified component (B) is not particularly limited, but is preferably 2 to 20 mg CH 3 ONa/g, more preferably 5 to 15 mg CH 3 ONa/g, and even more preferably 7 to 13 mg CH 3 ONa/g.
  • the content of component (B) is not particularly limited, but is preferably 1 to 45 parts by mass, more preferably 3 to 35 parts by mass, and even more preferably 5 to 30 parts by mass, and may be 5 to 15 parts by mass, or may be 10 to 25 parts by mass, or may be 15 to 25 parts by mass, relative to 100 parts by mass of the resin components in the resin composition.
  • the content of component (B) is equal to or greater than the lower limit, the high frequency characteristics are good and the generation of powder in the prepreg tends to be easily suppressed, and when the content is equal to or less than the upper limit, the heat resistance, flame retardancy, etc. tend to be easily maintained.
  • the resin composition of the present embodiment further contains a crosslinking agent (C), mainly from the viewpoint of improving the compatibility between the components (A) and (B).
  • the crosslinking agent (C) is preferably a compound having a structure derived from a maleimide skeleton and a structure derived from butadiene, and more preferably a compound having a structure derived from the component (A1) and a structure derived from butadiene.
  • the preferred aspects of the component (A1) in the structure derived from the component (A1) are the same as those described above.
  • a compound having a structure derived from a maleimide skeleton and a structure derived from butadiene can be produced by reacting a maleimide resin with butadiene in the presence of an organic peroxide.
  • the organic peroxide is not particularly limited, but examples include benzoyl peroxide, dicumyl peroxide, methyl ethyl ketone peroxide, and t-butyl perbenzoate.
  • the amount of organic peroxide used is preferably 0.1 to 10 parts by mass per 100 parts by mass of the total amount of the maleimide resin and butadiene.
  • the butadiene used in the production of a compound having a structure derived from a maleimide skeleton and a structure derived from butadiene preferably has a number average molecular weight of 200 to 10,000, more preferably 500 to 5,000, even more preferably 500 to 2,500, and particularly preferably 800 to 2,000.
  • the content of the (C) component is not particularly limited, but is preferably 1 to 40 parts by mass, more preferably 3 to 35 parts by mass, even more preferably 5 to 30 parts by mass, and particularly preferably 5 to 25 parts by mass, relative to 100 parts by mass of the resin components in the resin composition. If the content of the (C) component is equal to or more than the lower limit, the compatibility of the (A) component and the (B) component tends to be good, and if it is equal to or less than the upper limit, the heat resistance, flame retardancy, etc. tend to be easily maintained.
  • the resin composition of the present embodiment When the resin composition of the present embodiment further contains an inorganic filler (D), the resin composition tends to have improved low thermal expansion properties, heat resistance, and flame retardancy.
  • the (D) component is not particularly limited, but includes silica, alumina, titanium oxide, mica, beryllia, barium titanate, potassium titanate, strontium titanate, calcium titanate, aluminum carbonate, magnesium hydroxide, aluminum hydroxide, aluminum silicate, calcium carbonate, calcium silicate, magnesium silicate, silicon nitride, boron nitride, clay (calcined clay, etc.), molybdic acid compounds (zinc molybdate, etc.), talc, aluminum borate, silicon carbide, etc.
  • the (D) component may be used alone or in combination of two or more.
  • silica, alumina, mica, and talc are preferred, silica and alumina are more preferred, and silica is even more preferred.
  • Examples of silica include crushed silica, fumed silica, and fused silica (fused spherical silica).
  • the shape and particle size of component (D) are not particularly limited, but the particle size is preferably 0.01 to 20 ⁇ m, more preferably 0.1 to 10 ⁇ m, even more preferably 0.2 to 1 ⁇ m, and particularly preferably 0.3 to 0.8 ⁇ m.
  • particle size refers to the average particle size, and is the particle size at the point corresponding to 50% volume when a cumulative frequency distribution curve is calculated based on particle size, with the total volume of the particles being 100%.
  • the particle size of component (D) can be measured using a particle size distribution measuring device using a laser diffraction scattering method.
  • the content of the component (D) is not particularly limited, but from the viewpoints of low thermal expansion property, heat resistance, and flame retardancy, it is preferably 5 to 70 volume %, more preferably 15 to 60 volume %, even more preferably 20 to 55 volume %, and particularly preferably 25 to 50 volume %, based on the total amount of solids in the resin composition.
  • the (D) component may be an inorganic filler that has been previously surface-treated with a coupling agent by a dry or wet method.
  • a coupling agent there is no particular limitation on the coupling agent, and for example, a silane coupling agent or a titanate coupling agent can be appropriately selected and used.
  • One type of coupling agent may be used alone, or two or more types may be used in combination.
  • the coupling agent may be the coupling agent (G) described below.
  • component (D) when component (D) is used in this embodiment, in order to improve the dispersibility of component (D) in the resin composition, component (D) may be used as a slurry in which it is dispersed in an organic solvent beforehand, if necessary.
  • organic solvent include the same organic solvents as those described below.
  • the resin composition of the present embodiment tends to have improved curability and to have better high-frequency characteristics, heat resistance, adhesion to a conductor, elastic modulus, and glass transition temperature.
  • a suitable curing accelerator (E) may be appropriately selected depending on the type of the thermosetting resin (B) component used.
  • the curing accelerator (E) may be used alone or in combination of two or more kinds.
  • Examples of the component (E) include amine-based curing accelerators, imidazole-based curing accelerators, phosphorus-based curing accelerators, organometallic salts, acid catalysts, organic peroxides, etc.
  • imidazole-based curing accelerators are not classified as amine-based curing accelerators.
  • Examples of the amine-based curing accelerator include amine compounds having primary to tertiary amines, such as triethylamine, pyridine, tributylamine, dicyandiamide, and N-2-(aminoethyl)-3-aminopropyltrimethoxysilane; and quaternary ammonium compounds.
  • imidazole-based curing accelerator examples include imidazole compounds such as methylimidazole, phenylimidazole, 2-undecylimidazole, and isocyanate-masked imidazole (eg, an addition reaction product of hexamethylene diisocyanate resin and 2-ethyl-4-methylimidazole).
  • examples of the phosphorus-based curing accelerator include tertiary phosphines such as triphenylphosphine; and quaternary phosphonium compounds such as an addition product of p-benzoquinone and tri-n-butylphosphine.
  • the organic metal salts include carboxylates of manganese, cobalt, zinc, etc.
  • the acid catalyst includes p-toluenesulfonic acid and the like.
  • organic peroxides include dicumyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyne-3,2,5-dimethyl-2,5-bis(t-butylperoxy)hexane, t-butylperoxyisopropyl monocarbonate, and ⁇ , ⁇ '-di(t-butylperoxy)diisopropylbenzene.
  • imidazole-based curing accelerators are preferred, and imidazole-based curing accelerators are more preferred, from the viewpoint of obtaining better high-frequency characteristics, heat resistance, adhesion to a conductor, elastic modulus, and glass transition temperature. Also preferred is an embodiment in which an imidazole-based curing accelerator is used in combination with an organic peroxide.
  • the content of the component (E) is not particularly limited, but is preferably 0.01 to 10 parts by mass, more preferably 0.05 to 6 parts by mass, even more preferably 0.1 to 4 parts by mass, particularly preferably 0.5 to 4 parts by mass, most preferably 1.0 to 4 parts by mass, and may be 1.5 to 3.5 parts by mass, relative to 100 parts by mass of the total of the components (A) and (B).
  • the content of the component (E) is within the above range, the high frequency characteristics, heat resistance, storage stability, and moldability tend to be good.
  • the resin composition of the present embodiment may further contain, as necessary, one or more optional components such as a resin material other than the above-mentioned components, a flame retardant, a flame retardant assistant, a coupling agent, an antioxidant, a heat stabilizer, an antistatic agent, an ultraviolet absorber, a pigment, a colorant, and a lubricant.
  • a resin material other than the above-mentioned components e.g., a flame retardant, a flame retardant assistant, a coupling agent, an antioxidant, a heat stabilizer, an antistatic agent, an ultraviolet absorber, a pigment, a colorant, and a lubricant.
  • the optional components described above may each be used alone or in combination of two or more. Examples of the resin material other than each of the above components include thermosetting resins other than maleimide resins, etc.
  • the thermosetting resin preferably contains at least one selected from the group consisting of epoxy resins, phenolic resins, polyimide resins, cyanate resins, isocyanate resins, benzoxazine resins, oxetane resins, amino resins, unsaturated polyester resins, allyl resins, dicyclopentadiene resins, silicone resins, triazine resins, and melamine resins.
  • the resin composition of the present embodiment contains the optional components described above, their contents are not particularly limited, and may be 0.01 mass% or more, 0.1 mass% or more, 0.5 mass% or more, or 30 mass% or less, 10 mass% or less, 5 mass% or less, or 1 mass% or less, relative to the total amount of the resin components. Furthermore, the resin composition of the present embodiment may not contain the optional components described above, depending on the desired performance.
  • the resin composition of the present embodiment may be a resin composition containing an organic solvent, that is, a so-called resin varnish, from the viewpoint of facilitating handling and facilitating production of a prepreg, which will be described later.
  • the organic solvent include alcohol-based solvents such as ethanol, propanol, butanol, methyl cellosolve, butyl cellosolve, and propylene glycol monomethyl ether; ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ether-based solvents such as tetrahydrofuran; aromatic solvents such as toluene, xylene, and mesitylene; nitrogen-containing solvents such as dimethylformamide, dimethylacetamide, and N-methylpyrrolidone; sulfur-containing solvents such as dimethylsulfoxide; and ester-based solvents such as ⁇ -butyrolactone.
  • the resin composition of this embodiment contains an organic solvent
  • its content is not particularly limited, but is preferably such that the solids concentration of the resin composition of this embodiment is 30 to 90 mass%, more preferably 40 to 80 mass%, and even more preferably 50 to 70 mass%.
  • the organic solvent content is within the above range, the resin composition is easy to handle, and the impregnation of the substrate and the appearance of the produced prepreg are good. Furthermore, it becomes easy to adjust the solids concentration of the resin in the prepreg, which will be described later, and it tends to be easier to produce a prepreg having the desired thickness.
  • the minimum melt viscosity when the resin composition of this embodiment is prepared into a test piece by the method described in the examples below is not particularly limited, but is preferably 10,000 Pa ⁇ s or less, may be 1,000 to 10,000 Pa ⁇ s, may be 3,000 to 10,000 Pa ⁇ s, may be 4,000 to 9,000 Pa ⁇ s, may be 4,000 to 8,000 Pa ⁇ s, may be 4,000 to 7,000 Pa ⁇ s, or may be 4,500 to 7,000 Pa ⁇ s.
  • the minimum melting temperature when the resin composition of this embodiment is prepared into a test piece by the method described in the examples described later is not particularly limited, but may be 100 to 140°C, 115 to 135°C, or 120 to 135°C.
  • the resin composition of this embodiment can be produced by mixing components (A) and (B) and, if necessary, other components, by a known method. At this time, each component may be dissolved or dispersed in the organic solvent while stirring.
  • the mixing order, temperature, time, and other conditions are not particularly limited and can be set as desired.
  • the resin film of the present embodiment is a resin film containing the resin composition of the present embodiment or a semi-cured product of the resin composition.
  • the resin film of the present embodiment can be produced, for example, by applying a resin composition containing an organic solvent, i.e., a resin varnish, to a support, drying by heating, and semi-curing (B-staging) as necessary.
  • the thickness of the resin film is not particularly limited, but is preferably 1 to 100 ⁇ m, more preferably 3 to 70 ⁇ m, and even more preferably 5 to 35 ⁇ m.
  • the support may be a plastic film, a metal foil, or a release paper.
  • the drying temperature and drying time may be appropriately determined depending on the amount of the organic solvent used, the boiling point of the organic solvent used, and the like, but a resin film can be suitably formed by drying at 50 to 200° C. for about 1 to 10 minutes.
  • the prepreg of this embodiment is a prepreg containing the resin composition of this embodiment or a semi-cured product of the resin composition. It can also be said that the prepreg of this embodiment is a prepreg containing one or more selected from the group consisting of the resin composition of this embodiment, the semi-cured product of the resin composition, the resin film of this embodiment, and the semi-cured product of the resin film. More specifically, the prepreg of this embodiment contains one or more selected from the group consisting of the resin composition of this embodiment, the semi-cured product of the resin composition, the resin film of this embodiment, and the semi-cured product of the resin film, and a sheet-like fiber substrate.
  • the prepreg is formed using the resin composition or the resin film of this embodiment and a sheet-like fiber substrate.
  • the resin composition or the resin film of this embodiment is impregnated into a sheet-like fiber substrate, and then heated and dried to semi-cure (B-stage) as necessary.
  • the prepreg of this embodiment can be produced by, for example, semi-curing (B-stage) by heating and drying in a drying oven at 80 to 200 ° C. for 1 to 30 minutes.
  • B-stage refers to a state of B-stage defined in JIS K6900 (1994).
  • the amount of the resin composition used can be appropriately determined so that the solid content concentration derived from the resin composition in the prepreg after drying is 30 to 90 mass %. By setting the solid content concentration in this range, better moldability tends to be obtained when the laminate is made.
  • the material of the sheet-like fiber substrate may be inorganic fibers such as E glass, D glass, S glass, Q glass, etc.; organic fibers such as polyimide, polyester, tetrafluoroethylene, etc.; mixtures thereof, etc.
  • These sheet-like fiber substrates have shapes such as woven fabric, nonwoven fabric, roving, chopped strand mat, surfacing mat, etc.
  • the thickness of the sheet-like fiber substrate is not particularly limited, but may be 1 to 100 ⁇ m, 3 to 70 ⁇ m, 5 to 55 ⁇ m, 15 to 55 ⁇ m, or 25 to 55 ⁇ m.
  • the laminate of the present embodiment is a laminate having a cured product of the resin composition of the present embodiment and a metal foil. It can also be said that the laminate of the present embodiment is a laminate having one or more selected from the group consisting of the cured product of the resin composition of the present embodiment, the cured product of the resin film of the present embodiment, and the cured product of the prepreg of the present embodiment, and a metal foil.
  • the laminate of the present embodiment can be produced, for example, by disposing a metal foil on one or both sides of a single resin film of the present embodiment, or by disposing a metal foil on one or both sides of a laminate obtained by stacking two or more resin films of the present embodiment, and then molding the laminate under heat and pressure.
  • the resin film of the present embodiment is C-staged.
  • Another embodiment of the laminate of this embodiment can be produced, for example, by disposing metal foil on one or both sides of a single prepreg of this embodiment, or by disposing metal foil on one or both sides of a laminate obtained by stacking two or more prepregs of this embodiment, and then molding the laminate under heat and pressure.
  • the prepreg of this embodiment is C-staged.
  • C-staging refers to bringing the laminate into a C-stage state as defined in JIS K6900 (1994). Note that a laminate having a metal foil is sometimes called a metal-clad laminate.
  • the metal of the metal foil is not particularly limited, but from the viewpoint of electrical conductivity, it may be copper, gold, silver, nickel, platinum, molybdenum, ruthenium, aluminum, tungsten, iron, titanium, chromium, or an alloy containing one or more of these metal elements, with copper and aluminum being preferred, and copper being more preferred.
  • the method for carrying out the hot and pressure molding is not particularly limited, but examples thereof include a method in which the hot and pressure molding is carried out under conditions of a temperature of 100 to 300° C., a pressure of 0.2 to 10 MPa, and a time of 0.1 to 5 hours.
  • the hot and pressure molding can be carried out by using a vacuum press or the like to maintain a vacuum state for 0.5 to 5 hours.
  • the printed wiring board of the present embodiment has a cured product of the resin composition of the present embodiment. It can also be said that the printed wiring board of the present embodiment has one or more selected from the group consisting of a cured product of the thermosetting resin composition of the present embodiment, a cured product of the resin film of the present embodiment, a cured product of the prepreg of the present embodiment, and a laminate of the present embodiment.
  • the printed wiring board of this embodiment can be manufactured by performing a circuit formation process such as drilling, metal plating, and etching of metal foil by a known method using one or more selected from the group consisting of the prepreg of this embodiment, the resin film of this embodiment, and the laminate of this embodiment.
  • a multilayer printed wiring board can be manufactured by further performing a multilayer adhesive process as necessary.
  • the prepreg of this embodiment and the resin film of this embodiment are C-staged.
  • the semiconductor package of the present embodiment is a semiconductor package having the printed wiring board of the present embodiment and a semiconductor element.
  • the semiconductor package of the present embodiment can be manufactured by mounting a semiconductor element such as a semiconductor chip or a memory at a predetermined position on the printed wiring board of the present embodiment.
  • the resin composition, resin film, prepreg, laminate, printed wiring board, and semiconductor package of this embodiment can be suitably used in electronic devices that handle high-frequency signals of 10 GHz or more.
  • the printed wiring board is useful as a printed wiring board for millimeter-wave radar.
  • the weight average molecular weight (Mw) and number average molecular weight (Mn) were measured by the following methods.
  • the values were calculated from a calibration curve using standard polystyrene by gel permeation chromatography (GPC).
  • the calibration curve was approximated by a third-order equation using standard polystyrene: TSKstandard POLYSTYRENE (Type: A-2500, A-5000, F-1, F-2, F-4, F-10, F-20, F-40) [manufactured by Tosoh Corporation, product name].
  • TSKstandard POLYSTYRENE Type: A-2500, A-5000, F-1, F-2, F-4, F-10, F-20, F-40 [manufactured by Tosoh Corporation, product name].
  • the measurement conditions for GPC are shown below.
  • the mixture was reacted under a nitrogen atmosphere at 90 to 100°C for 5 hours with stirring to obtain a maleimide-modified polybutadiene solution (solid content concentration: 35% by mass).
  • the number average molecular weight (Mn) of the obtained maleimide-modified polybutadiene was 2,000.
  • the solution containing the polybutadiene and the maleimide resin (A1-1) before the start of the reaction and the solution after the reaction were subjected to GPC measurement by the above-mentioned method, and the peak areas derived from the maleimide resin before and after the reaction were determined.
  • the vinyl group modification rate of the maleimide resin was calculated by the following formula.
  • the vinyl group modification rate corresponds to the rate of decrease in the peak area derived from the maleimide resin due to the reaction.
  • Vinyl group modification rate (%) [(peak area derived from maleimide resin before reaction) ⁇ (peak area derived from maleimide resin after reaction)] ⁇ 100/(peak area derived from maleimide resin before reaction)
  • the vinyl group modification rate calculated from the above formula was 40%.
  • the prepreg prepared in each example was kneaded to obtain a resin powder.
  • the obtained resin powder was heated at a constant temperature increase rate, and the minimum melt viscosity and the temperature at which the minimum melt viscosity was observed (minimum melting temperature) were measured.
  • the details of the measurement method and measurement conditions are as follows. Measurement sample: The resin powder was molded by uniaxial molding and adjusted to a thickness of 1 mm to prepare a measurement sample.
  • Measurement conditions Using the above-mentioned measurement sample, measurements were performed using DISCOVERY HR-2 (manufactured by TA Instruments Japan Co., Ltd.) under conditions of a temperature increase rate of 4°C/min in the temperature range from 30°C to 200°C and a constant pressure of 0.2 N.
  • Crosslinking agent (C-1) Maleimide-modified polybutadiene obtained in Production Example 1
  • Curing accelerator (E-1) ⁇ , ⁇ '-di(t-butylperoxy)diisopropylbenzene
  • Curing accelerator (E-2) Isocyanate masked imidazole

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WO2022102781A1 (ja) * 2020-11-16 2022-05-19 昭和電工マテリアルズ株式会社 マレイミド樹脂組成物、プリプレグ、積層板、樹脂フィルム、プリント配線板及び半導体パッケージ
WO2022102782A1 (ja) * 2020-11-16 2022-05-19 昭和電工マテリアルズ株式会社 マレイミド樹脂組成物、プリプレグ、積層板、樹脂フィルム、プリント配線板及び半導体パッケージ
JP2022146808A (ja) * 2021-03-22 2022-10-05 味の素株式会社 樹脂シート
JP2023094261A (ja) * 2021-12-23 2023-07-05 株式会社レゾナック 熱硬化性樹脂組成物、プリプレグ、樹脂フィルム、積層板、プリント配線板及び半導体パッケージ
JP2023110554A (ja) * 2022-01-28 2023-08-09 株式会社レゾナック 樹脂組成物、プリプレグ、積層板、樹脂フィルム、プリント配線板及び半導体パッケージ

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022102781A1 (ja) * 2020-11-16 2022-05-19 昭和電工マテリアルズ株式会社 マレイミド樹脂組成物、プリプレグ、積層板、樹脂フィルム、プリント配線板及び半導体パッケージ
WO2022102782A1 (ja) * 2020-11-16 2022-05-19 昭和電工マテリアルズ株式会社 マレイミド樹脂組成物、プリプレグ、積層板、樹脂フィルム、プリント配線板及び半導体パッケージ
JP2022146808A (ja) * 2021-03-22 2022-10-05 味の素株式会社 樹脂シート
JP2023094261A (ja) * 2021-12-23 2023-07-05 株式会社レゾナック 熱硬化性樹脂組成物、プリプレグ、樹脂フィルム、積層板、プリント配線板及び半導体パッケージ
JP2023110554A (ja) * 2022-01-28 2023-08-09 株式会社レゾナック 樹脂組成物、プリプレグ、積層板、樹脂フィルム、プリント配線板及び半導体パッケージ

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