WO2023276379A1 - 樹脂組成物、ワニス、積層板、プリント配線基板および成形品 - Google Patents

樹脂組成物、ワニス、積層板、プリント配線基板および成形品 Download PDF

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WO2023276379A1
WO2023276379A1 PCT/JP2022/015425 JP2022015425W WO2023276379A1 WO 2023276379 A1 WO2023276379 A1 WO 2023276379A1 JP 2022015425 W JP2022015425 W JP 2022015425W WO 2023276379 A1 WO2023276379 A1 WO 2023276379A1
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resin composition
mass
resin
parts
composition according
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English (en)
French (fr)
Japanese (ja)
Inventor
達也 川崎
侑花 仲澤
健 加藤
珠奈 松田
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PRINTEC Corp
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PRINTEC Corp
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Priority to KR1020237040786A priority Critical patent/KR20240026127A/ko
Priority to CN202280042315.5A priority patent/CN117500880A/zh
Priority to JP2023531448A priority patent/JP7836816B2/ja
Priority to TW111116145A priority patent/TWI914527B/zh
Publication of WO2023276379A1 publication Critical patent/WO2023276379A1/ja
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    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/12—Unsaturated polyimide precursors
    • C08G73/121—Preparatory processes from unsaturated precursors and polyamines
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C08K5/34924—Triazines containing cyanurate groups; Tautomers thereof
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
    • C08K5/357—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L45/00—Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; 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
    • C08L45/00—Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers
    • C08L45/02—Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers of coumarone-indene 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
    • 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 invention is a resin having low dielectric properties (low dielectric constant, low dielectric loss tangent), which is used as laminates, printed wiring boards, adhesives, sealants, paints, molded articles, etc. in electronic and electrical parts. Regarding the composition.
  • thermosetting resins such as epoxy resins, polyimide resins, unsaturated polyester resins, and phenolic resins have been used as heat-resistant resins in the field of electronic materials. These thermosetting resins are used properly according to their uses and characteristics. Among these resins, polyimide resins are particularly excellent in heat resistance and moisture-heat resistance (heat resistance after moisture absorption), and are therefore widely used in applications requiring high heat resistance. Modified polyimide resins are also used, which are improved in performance by combining polyimide resins with other resins such as epoxy resins.
  • Patent Document 1 describes a resin composition obtained by melting a component containing a polymaleimide compound.
  • an object of the present invention is to provide a resin composition containing a bismaleimide compound with further improved low dielectric properties.
  • Another object of the present invention is to provide a resin composition containing a bismaleimide compound that has good solubility and curability in low boiling point solvents and is easy to handle.
  • the resin composition of the present invention is a resin composition obtained by melting a resin mixture containing (A) a bismaleimide compound, wherein the (A) bismaleimide compound is a fat represented by formula (1)
  • a resin composition comprising a group bismaleimide compound and an aromatic bismaleimide compound represented by formula (2).
  • R 1 is an alkylene group having 6 to 12 carbon atoms.
  • R 2 is a hydrocarbon group having 6 to 30 carbon atoms and having an aromatic ring
  • X 1 is each independently an oxygen atom or a single bond
  • R 3 and R 4 each have 1 carbon atom.
  • a and b are integers of 0 or more and 3 or less.
  • the resin composition By containing the aliphatic bismaleimide compound and the aromatic bismaleimide compound in the resin composition, it is possible to improve the heat resistance of the cured product while maintaining low dielectric properties. Therefore, it is possible to provide a resin composition having excellent low dielectric properties (low dielectric constant, low dielectric loss tangent) while maintaining heat resistance, which generally has a trade-off relationship with low dielectric properties.
  • the resin composition of the present embodiment contains (A) 30 to 65 parts by mass of a bismaleimide compound, (B) 5 to 25 parts by mass of a cumarone resin, and (C) an amine compound 1 in 100 parts by mass of the resin component of the resin mixture. It is a resin composition obtained by melting a resin mixture containing up to 30 parts by mass.
  • the components (A) to (C) and other components that the resin composition may contain are described below.
  • the numerical range "A to B" means "above A and below B”.
  • a mixture before melt-mixing each component is called a "resin mixture”
  • a mixture after cooling after melt-mixing is called a "resin composition”.
  • the bismaleimide compound is a compound having two maleimide groups and contains an aliphatic bismaleimide compound represented by the formula (1) shown in the section of Means for Solving the Problems.
  • R 1 is preferably an alkylene group having 7 to 11 carbon atoms, and R 1 is preferably an alkylene group having 9 carbon atoms, from the viewpoint of obtaining a cured product with low dielectric properties. more preferred.
  • an aliphatic bismaleimide compound having a melting point of 120° C. or less is preferable.
  • aliphatic bismaleimide compounds examples include 1,6-bismaleimide(2,2,4-trimethyl)hexane, hexamethylenediaminebismaleimide, N,N'-1,2-ethylenebismaleimide, N, N'-1,3-propylenebismaleimide, N,N'-1,4-tetramethylenebismaleimide and the like.
  • examples of commercially available aliphatic bismaleimide compounds include BMI-TMH (product name, manufactured by Daiwa Kasei Kogyo Co., Ltd.).
  • the bismaleimide compound further contains an aromatic bismaleimide compound represented by formula (2) shown in the section of Means for Solving the Problems.
  • An aromatic bismaleimide compound having a melting point of 130° C. or higher is more preferable.
  • aromatic bismaleimide compound represented by formula (2) examples include 4,4′-diphenylmethanebismaleimide, bisphenol A diphenyletherbismaleimide, 3,3′-dimethyl-5,5′-diethyl-4,4′- diphenylmethane bismaleimide and the like.
  • aromatic bismaleimide compounds include BMI-1000, BMI-4000, BMI-5000, and BMI-5100 (all product names, manufactured by Daiwa Kasei Kogyo Co., Ltd.).
  • R 2 in formula (2) is preferably a group represented by formula (3) from the viewpoint of heat resistance of the cured product.
  • aromatic bismaleimide compounds include bisphenol A diphenyl ether bismaleimide.
  • the mass ratio of the content of the aliphatic bismaleimide compound to the content of the aromatic bismaleimide compound is preferably 3.0:7.0 to 7.0:3.0, more preferably 4.0:6.0 to 6.0:4.0, 4.5:5.5 to 5.5:4.5 are more preferred.
  • the content of the bismaleimide compound in 100 parts by mass of the resin component of the resin mixture is 30 to 65 parts by mass.
  • the content of the bismaleimide compound in 100 parts by mass of the resin component is more preferably 40 to 62 parts by mass, more preferably 50 to 60 parts by mass, from the viewpoint of achieving both high heat resistance and low dielectric properties of the cured product.
  • Two or more kinds of bismaleimide compounds are used in combination.
  • Components (B) to (I) and other components described below can be used singly or in combination of two or more.
  • Coumaron resin is a copolymer resin composed mainly of coumarone, indene and styrene.
  • Commercially available products include G-90, V-120, L-5, L-20, H-100 (all product names, manufactured by Nichinori Kagaku Co., Ltd.).
  • a coumarone resin having a softening point of 100° C. or less is preferable from the viewpoint of low dielectric properties of the cured product. From the same point of view, the weight average molecular weight is preferably 850 or less, more preferably 800 or less.
  • a coumarone resin that is beaded (solid) at ambient temperature is preferred over one that is liquid at ambient temperature.
  • the content of the coumarone resin in 100 parts by mass of the resin component of the resin mixture is preferably 5 to 25 parts by mass, more preferably 10 to 20 parts by mass, more preferably 13 to 18 parts by mass, from the viewpoint of high heat resistance and low dielectric properties of the cured product. Parts by mass are more preferred.
  • the content of the coumarone resin is more preferably 15 parts by mass or more, more preferably 20 parts by mass or more, relative to 100 parts by mass of the bismaleimide compound (A). More preferred. From the viewpoint of obtaining a cured product with good heat resistance, the content of the coumarone resin is more preferably 50 parts by mass or less, even more preferably 40 parts by mass or less with respect to 100 parts by mass of the bismaleimide compound.
  • the aliphatic bismaleimide compound represented by Formula (1) has a problem that once dissolved, it does not solidify and becomes liquid.
  • the resin composition of the present embodiment contains 1 to 30 parts by mass of an amine compound in 100 parts by mass of the resin component in addition to the aliphatic bismaleimide compound.
  • the content of the amine compound is preferably 2 to 15 parts by mass, more preferably 3 to 8 parts by mass, from the viewpoints of curability of the resin composition and low dielectric properties and heat resistance of the cured product.
  • Examples of the amine compound include aromatic amines such as bisaniline and 1,3-bis(3-aminophenoxy)benzene, and bisaniline is preferable from the viewpoint of making a resin composition with good handling properties as a prepreg.
  • Commercially available products include Bisaniline M and Bisaniline-P (manufactured by Mitsui Chemicals Fine Co., Ltd.); ODA, BODA, BAPP, HFBAPP, BAPB, TPE-M and TPE-Q (both manufactured by Seika Co., Ltd.); Kayabond C -200S (manufactured by Nippon Kayaku Co., Ltd.), BAN (manufactured by Nippon Kayaku Co., Ltd.), and the like.
  • Bisaniline is more preferably an aromatic amine represented by formula (4).
  • R 5 is a hydrocarbon group having 6 to 30 carbon atoms and having an aromatic ring, and each X 1 is independently an oxygen atom or a single bond.
  • Bisanilines represented by formula (4) include 4,4′-[dimethylmethylenebis(4,1-phenyleneoxy)]bisaniline and 4,4′-[biphenyl-4,4′-diylbis(oxy)].
  • Bisaniline represented by formula (4) includes commercially available products such as Bisaniline M and Bisaniline-P (manufactured by Mitsui Chemicals Fine Co., Ltd.); BODA, BAPP and BAPB (manufactured by Seika Co., Ltd.).
  • (D) Benzoxazine compound may have at least one or more benzoxazine rings in the molecule, but dihydrobenzoxazine compounds represented by the following general formula (5) or (6) A pd-type dihydrobenzoxazine represented by the following general formula (6) is preferred, and more preferred.
  • R 6 and R 7 represent a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 3 carbon atoms.
  • the content of the benzoxazine compound in 100 parts by mass of the resin component of the resin mixture is 5 to 20 parts by mass from the viewpoint of the high heat resistance and low dielectric properties of the cured product and the solubility of the resin composition in low boiling point solvents. is preferred, 10 to 20 parts by weight is more preferred, and 15 to 20 parts by weight is even more preferred.
  • the content of the benzoxazine compound is more preferably 15 parts by mass or more, more preferably 20 parts by mass with respect to 100 parts by mass of the bismaleimide compound. The above is more preferable. From the viewpoint of obtaining a cured product with good heat resistance, the content of the benzoxazine compound is more preferably 50 parts by mass or less, still more preferably 40 parts by mass or less with respect to 100 parts by mass of the bismaleimide compound.
  • Bisphenol A-type cyanate ester is a bisphenol A-type cyanate ester (triazine) that forms a triazine ring and cures. Curability of the resin mixture is improved by containing the bisphenol A type cyanate ester.
  • Bisphenol A-type cyanate esters include monomers and (homo)polymers (polymers), and bisphenol A-type cyanate ester monomers are preferred from the viewpoint of obtaining cured products with excellent low dielectric properties.
  • the content of the bisphenol A-type cyanate ester in 100 parts by mass of the resin component of the resin mixture is preferably 0.1 to 3 parts by mass. 0.5 to 2 parts by weight is more preferred, and 0.7 to 1.3 parts by weight is even more preferred.
  • Epoxy resin The resin composition may contain an epoxy resin, if necessary, for the purpose of complementing various properties such as flame retardancy.
  • the inclusion of the epoxy resin may improve the interlaminar adhesion and insulating properties of a laminate obtained by stacking prepregs, which are sheets impregnated with a resin composition, on a base material and performing pressurization and heat treatment.
  • the epoxy resin may be a compound having an epoxy group, but from the viewpoint of achieving both heat resistance and low dielectric properties of the cured product, a biphenyl aralkyl type epoxy resin, an epoxy resin containing a naphthalene ring, and having three epoxy groups. Compounds and the like are preferred.
  • the epoxy resin containing a naphthalene ring an ⁇ -naphthol type epoxy resin is preferable.
  • Examples of commercially available epoxy resins containing naphthalene rings include ESN-475V (product name, ⁇ -naphthol type epoxy resin manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) in which each naphthalene ring has two epoxy groups.
  • VG3101L product name, manufactured by Printec Co., Ltd.
  • Epoxy resins other than the above include bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, novolak type epoxy resin, cresol novolak type epoxy resin, bisphenol A novolak type epoxy resin, bisphenol F novolak type epoxy resin. , triphenylol-type epoxy resins, dicyclopentadiene-type epoxy resins, and the like.
  • the heat resistance of the cured product is improved by suppressing the content of the bisphenol A type epoxy resin in the resin component of the resin mixture. Therefore, from the viewpoint of improving the heat resistance of the cured product, it is preferable that the resin mixture does not contain a bisphenol A type epoxy resin.
  • “not containing a bisphenol A type epoxy resin” means substantially not containing it, that is, not containing an amount of a bisphenol A type epoxy resin that affects the properties of the resin mixture.
  • the content of the bisphenol A type epoxy resin in 100 parts by mass of the resin component of the resin mixture is 1 part by mass or less, depending on the case, 0.3 parts by mass or less or 0.1 part by mass or less, a resin with low dielectric properties It has no effect on the properties of the mixture.
  • the content of the epoxy resin in 100 parts by mass of the resin component of the resin mixture is preferably 1 to 12 parts by mass, more preferably 2 to 10 parts by mass, and 3 to 8 parts by mass, from the viewpoint of high heat resistance and low dielectric properties of the cured product. Parts by mass are more preferred.
  • the resin composition of the present embodiment is a resin composition obtained by melting a resin mixture containing (A) a bismaleimide compound, wherein (A) the bismaleimide compound is and an aliphatic bismaleimide compound represented by formula (1) and an aromatic bismaleimide compound represented by formula (2).
  • the resin composition can improve the heat resistance of the cured product while maintaining the low dielectric properties of the cured product.
  • the bismaleimide compound description of items common to the first embodiment will be omitted, and different items will be described below.
  • the resin composition is such that the mass ratio of the content of the two types of bismaleimide compounds in the resin mixture is 25:55 as the aliphatic bismaleimide compound:aromatic bismaleimide compound. 45:35 is preferable, and 27:53 to 47:38 is more preferable.
  • the resin composition contains triallyl isocyanurate in the resin mixture from the viewpoint of increasing the solubility in low boiling point solvents.
  • the content of triallyl isocyanurate in 100 parts by mass of the resin component of the resin mixture is preferably 16 to 26 parts by mass, more preferably 18 to 24 parts by mass.
  • the resin composition can be prepared as a 60% by mass methyl ethyl ketone solution and has high solubility in a low boiling point solvent.
  • Commercial products of triallyl isocyanurate include TAIC (trademark, manufactured by Mitsubishi Chemical Corporation).
  • the resin composition preferably further contains an amine compound and a carboxylic acid dianhydride from the viewpoint of making the state in the B-stage a solid rather than a viscous solid so that it is easy to handle.
  • (C) Amine Compound The same amine compound as in the first embodiment can be used as the amine compound.
  • the content of the amine compound in 100 parts by mass of the resin component of the resin mixture is is preferably 8 to 20 parts by mass, more preferably 10 to 18 parts by mass, even more preferably 12 to 16 parts by mass.
  • (I) Carboxylic acid dianhydride examples include BPADA, 6FDA, SFDA, BzDA: Enehyde (trademark, manufactured by ENEOS), TAHQ (see Examples for abbreviations), and the like. From the viewpoint of making a resin composition that becomes solid in the B stage and has high solubility in a low boiling point solvent, when the resin mixture contains triallyl isocyanurate, carboxylic acid dianhydride in 100 parts by mass of the resin component of the resin mixture The content is preferably 10 to 35 parts by mass, more preferably 15 to 30 parts by mass, even more preferably 20 to 27 parts by mass.
  • a curing accelerator may be added. Timing for adding the curing accelerator includes, for example, when the resin composition is dissolved in a solvent to form a varnish, when the varnish is prepregized, or when a substrate or laminate is produced. The following description is common to the resin compositions of the first and second embodiments.
  • Curing accelerators include, for example, imidazoles such as dicumyl peroxide, 4,4'-diaminodiphenylmethane, 2-methylimidazole, 2-ethyl-4-methylimidazole, and 2-heptylimidazole; triethanolamine, triethylenediamine, Amines such as N-methylmorpholine; Organic phosphines such as triphenylphosphine and tritolylphosphine; Tetraphenylboron salts such as tetraphenylphosphonium tetraphenylborate and triethylammonium tetraphenylborate; ,4,0) undecene-7 and its derivatives; organic metal salts such as lead naphthenate, lead stearate, zinc naphthenate, tin oleate, manganese naphthenate, cobalt naphthenate and cobalt octylate.
  • the curing accelerator is blended in the varnish or prepreg at a content that gives the desired gelling time.
  • the curing accelerator is used in the range of 0.01 to 5 parts by mass with respect to the total 100 parts by mass of the resin components contained in the resin composition.
  • the resin composition and the resin mixture before melt mixing may contain components other than the above (A) to (I).
  • organic or inorganic fillers can be used to cure the resin composition to obtain a substrate for molding.
  • fillers include oxides such as silica, diatomaceous earth, alumina, zinc chloride, titanium oxide, calcium oxide, magnesium oxide, iron oxide, tin oxide, antimony oxide, and ferrites; calcium hydroxide, magnesium hydroxide, hydroxide Hydroxides such as aluminum and basic magnesium carbonate; carbonates such as calcium carbonate, magnesium carbonate, zinc carbonate, barium carbonate, dawsonite and hydrotalcite; sulfates such as calcium sulfate, barium sulfate and gypsum fiber; calcium silicate (wollastonite, xonotlite), talc, clay, mica, montmorillonite, bentonite, activated clay, sepiolite, imogolite, sericite, glass fiber, glass beads, silicates such as silic
  • the shape of the filler is preferably spherical or scaly. If necessary, use a silane coupling agent with two or more different reactive groups in the molecule (one reactive group that chemically reacts with inorganic materials, the other that chemically reacts with organic materials). You may
  • the content is preferably 5.0 to 250 parts by mass with respect to 100 parts by mass of the resin component of the resin mixture.
  • a flame retardant can be added to the resin composition as needed.
  • Flame retardants include organic flame retardants such as bromine compounds such as brominated epoxy resins and phosphorus compounds such as condensed phosphoric acid esters, and inorganic flame retardants such as aluminum hydroxide, magnesium hydroxide, tin compounds and antimony compounds. .
  • the flame retardant is a content that realizes sufficient flame retardancy (for example, passing the V-0 condition in UL94 standard) without impairing the heat resistance and moist heat resistance of the cured product obtained by curing the resin composition.
  • an organic flame retardant for example, 1 to 20 parts by mass with respect to a total of 100 parts by mass of the resin components including the organic flame retardant in the resin composition. It is used in an amount of 10 to 300 parts by mass.
  • additives When using the resin composition, other additives can be added depending on the application.
  • examples of other additives include various silicone oils, thermoplastic resins, synthetic rubbers such as NBR, and leveling agents.
  • Other additives are used, for example, in a content of 0.0001 to 5 parts by mass in a total of 100 parts by mass of the other additives and the resin component in the resin composition.
  • the resin composition of the present invention is produced by a melt-mixing process in which a resin mixture is heated and mixed in a molten state.
  • Usual mixing means can be used for the melt-mixing step.
  • a mixing means a kneader, a twin-screw kneader, or the like is preferable.
  • the temperature during melt-mixing may be the temperature at which the resin mixture melts or higher and 400°C or lower, preferably 130 to 230°C, more preferably 150 to 210°C, and even more preferably 170 to 190°C.
  • the melt-mixing step is preferably carried out under conditions such that the weight average molecular weight of the resin composition obtained by heating the resin mixture is 1,000 to 2,500, more preferably 1,200 to 1,800.
  • the time for the melt-mixing step is, for example, about 0.1 to 10 minutes, and it is preferable to set conditions such as temperature in the melt-mixing step so as to be about 0.5 to 4 minutes.
  • the resin composition of the present invention is obtained by cooling by natural cooling or forced cooling.
  • the cooling method can be appropriately selected from known methods. For example, a method of natural cooling in an environment of 0 to 40° C. or a method of forced cooling using a refrigerant can be employed. Further, after melting and mixing, it may be placed in an environment of 30 to 300° C. in a constant temperature device and then cooled. After cooling, the resulting resin composition can be used in subsequent steps as a solid resin composition.
  • the aliphatic bismaleimide compound, the aromatic bismaleimide compound, and other components in the resin mixture react with each other, so that at least part of the bismaleimide compound is modified.
  • a resin composition having high heat resistance, low dielectric properties, good solubility in low boiling point solvents, and good curability can be produced.
  • the resin composition produced by the melt-mixing process has a component with a molecular weight of 4,500 to 4,800.
  • the ratio of the component having a molecular weight of 4500 to 4800 in 100% by mass of the resin composition is preferably 10 to 20% by mass, more preferably 12 to 18% by mass.
  • the proportion of components with a molecular weight of 4500-4800 can be determined by gel permeation chromatography (GPC) measurement.
  • the resin composition varnish according to the present invention is obtained by dissolving the resin composition obtained by the above-described production method in a solvent having a boiling point of 120° C. or less and a dielectric constant of 10 to 30.
  • solvents having a boiling point of 120° C. or less and a dielectric constant of 10 to 30 include ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone, ether solvents such as propylene glycol monomethyl ether, ethanol, 1-propanol and 2-propanol. , and alcohol solvents such as 1-butanol.
  • a ketone solvent is preferably used in consideration of operability and the like. Solvents other than those exemplified above may be contained.
  • the content of the resin composition in 100 parts by mass of the varnish is usually 40 to 80 parts by mass, preferably 50 to 70 parts by mass.
  • the varnish can be obtained by dissolving the resin composition in a solvent at normal temperature (room temperature) or under heating. When dissolving under heating, the conditions for dissolving are, for example, a temperature of about 50 to 200° C. and a time of about 0.1 to 24 hours, depending on the boiling point of the solvent.
  • a prepreg is produced by coating or impregnating a base material with the above varnish and then drying it to remove the solvent.
  • known substrates used in conventional prepregs such as glass nonwoven fabric, glass cloth, carbon fiber cloth, organic fiber cloth, and paper, can be used.
  • the prepreg After coating or impregnating the base material with the varnish, the prepreg is manufactured through a drying process, but the coating method, impregnation method, and drying method are not particularly limited, and conventionally known methods can be adopted.
  • the drying conditions are appropriately determined according to the boiling point of the solvent used, but too high a temperature is not preferable. It is desirable to dry so that the solvent remaining in 100 parts by mass of the prepreg is 3 parts by mass or less.
  • a filler other than the resin composition described above may be added to the varnish when producing the prepreg.
  • fillers include silica particles, alumina particles, and polyphenylene ether resins.
  • the amount of the filler used in preparing the prepreg is 10 to 100 parts per 100 parts by mass of the resin component of the resin composition. Parts by weight are preferred, 10 to 50 parts by weight are more preferred, and 20 to 40 parts by weight are even more preferred.
  • silica particles and alumina particle fillers examples include the ADMAFINE series (product name, manufactured by Admatechs Co., Ltd.), and commercially available polyphenylene ether resins SA90, SA120, and SA9000 (product names, all manufactured by SABIC Japan LLC. ) and the like.
  • the resin composition of the present invention is suitable for printed wiring boards, and the present invention can be implemented as a molded product obtained by curing the resin composition.
  • molded articles include cured products obtained by curing only the resin composition, composite materials combined with other raw materials, laminates, and the like.
  • the composite material and laminate can be obtained by heating and curing one sheet of prepreg under pressure using a hot press or the like, or by laminating a plurality of prepregs and heating and integrating them under pressure.
  • the heating and pressurizing conditions for producing the composite material are not particularly limited, but the heating temperature is 100 to 300° C., preferably 150 to 250° C., more preferably 200 to 250° C., and the pressure is 10 to 100 kg/ cm 2 , preferably 20 to 40 kg/cm, and heating/pressing time is 10 to 300 minutes, preferably 30 to 180 minutes.
  • Copper, aluminum, iron, stainless steel, etc. can be used as the metal foil or metal plate.
  • a laminate using copper as a metal foil is a copper clad laminate (CCL).
  • the conditions for heat curing are preferably the same as the conditions for producing the composite material.
  • the present invention can also be implemented as adhesives, sealants and paints containing the resin composition described above.
  • Test method [Solvent solubility (MEK solubility)] 60 parts by mass of a measurement sample (resin composition) and 40 parts by mass of methyl ethyl ketone (solvent) are mixed under conditions of 50° C. or less, and the dissolved state after applying ultrasonic vibration for a predetermined time is measured using the following criteria. It was evaluated visually. ⁇ : Brown transparent liquid at the time of applying ultrasonic vibration for 100 minutes, with no undissolved residue, separation, or turbidity. x: Undissolved, separated or turbid after applying ultrasonic vibration for 100 minutes.
  • Glass transition point (Tg)] [Thermal expansion coefficient: CTE (ppm/°C)]
  • CTE thermal expansion coefficient
  • Measurement mode heat flux type (TMA) Measuring equipment: Thermo plus TMA8310 manufactured by Rigaku Sample dimensions: length (vertical) 19 mm x width (horizontal) 5 mm x thickness 0.1 mm Atmosphere: N2 Measurement temperature: 30 to 350°C Temperature rising rate: 10°C/min. Measurement mode: Tensile
  • Raw material (A) Polymaleimide compound BMI-TMH (product name, manufactured by Daiwa Kasei Kogyo Co., Ltd., 1,6-bismaleimide-(2,2,4-trimethyl)hexane, melting point 73 to 110°C) ⁇ BMI-4000 (product name, manufactured by Daiwa Kasei Kogyo Co., Ltd., bisphenol A diphenyl ether bismaleimide, melting point 134 to 163 ° C.) ⁇ BMI-2300 (product name, manufactured by Daiwa Kasei Kogyo Co., Ltd., polyphenylmethane polymaleimide, melting point 70 to 145 ° C.)
  • the glass cloth 2116 was impregnated with a filler (SC2500-SXJ) added and dispersed in a proportion of 100 parts by mass with respect to 100 parts by mass of the resin component in the resin composition in the varnish. (1 Ply) prepreg was produced. In other Examples 43 to 67 and Comparative Examples 5 to 7, prepregs were produced by impregnating the glass cloth 2116 in a single layer without adding polyphenylene ether to the varnish.
  • a filler SC2500-SXJ
  • the prepreg of each example and comparative example was cured under press conditions: 180 ° C. x 30 kg/cm 2 x 1 hour, main curing conditions: 230 ° C. x 2 hours.
  • Tables 1 to 8 show the results of measuring dielectric constant (Dk) and dielectric loss tangent (Df). Examples 48 and 49 were not used for measurement because the resin had large scratches when the prepreg was manufactured.
  • the amine compound is preferably one or more selected from the group consisting of APB-N, BAN, and BAPP, and (I) carboxylic Acid dianhydride is preferably one or more selected from the group consisting of BPDA, 6FDA and SFDA.
  • a cured product with low dielectric properties is produced from a prepreg using a resin composition obtained by melting a resin mixture containing components (A) to (C) in 100 parts by mass of the resin component of the resin mixture. could be manufactured.
  • a resin composition having good handleability as a prepreg was obtained.
  • a resin composition obtained by melting a resin mixture containing (A) BMI-TMH and BMI-4000 as polymaleimide compounds and (C) BAPP as an amine compound has heat resistance (Tg (DSC)). and low dielectric properties (Df (after 24 hours)) were good.
  • a cured product with a low CTE was obtained by setting the mass ratio of the contents of BMI-TMH and BMI-4000 to 3.0:7.0 to 7.0:3.0.
  • G-90 By setting the content of G-90 to 12 parts by mass or less in 100 parts by mass of the resin mixture, it was possible to increase the heat resistance (Tg) of the cured product.
  • a cured product having excellent heat resistance was obtained regardless of the triazine content. Since the resin mixture contained triazine, the viscosity (hardness) of the resin mixture was increased and the handleability was improved.
  • the triazine content in 100 parts by mass of the resin mixture is preferably 2.0 parts by mass or less, and more preferably 1.0 parts by mass or less. Cured products with excellent heat resistance and low dielectric properties were obtained regardless of the epoxy content.
  • Example 67 in which SC2500-SXJ was dispersed as a filler, could achieve the best low dielectric properties. This is presumed to be due to the fact that dense molecular bonding was obtained as a result of the filler inhibiting and eliminating the molecular bonding due to aggregation.
  • FIG. 1 shows the results of GPC of the resin composition with a synthesis time of 2.5 minutes.
  • Table 9 shows the effect of synthesis time on the properties of the resin composition.
  • Synthesis conditions Resin temperature 170°C ⁇ 10°C [gel time] Measurement of curing time on a hot plate at 171°C [peak area]
  • GPC gel permeation chromatography
  • the weight average molecular weight of the resin composition was determined by GPC measurement. Solvent solubility was evaluated using the following criteria. 60 parts by mass of a measurement sample (resin composition) and 40 parts by mass of methyl ethyl ketone (solvent) are mixed under conditions of 50° C. or less, and the dissolved state after applying ultrasonic vibration for a predetermined time is measured using the following criteria. It was evaluated visually. [MEK solubility (168 hours)] An MEK solution of the resin was prepared by the method of solvent solubility (MEK solubility) described above, and the state of the measurement sample after standing for a predetermined time was visually evaluated using the following criteria. ⁇ : No precipitation of resin after standing at room temperature for 168 hours. x: Precipitation of resin after standing for 168 hours at room temperature.
  • a resin composition with good MEK solubility was obtained by setting the ratio of the component having a molecular weight of 4500 to 4800 corresponding to the peak marked with 1 in the graph of FIG. 1 to 10 to 20% of the total. By setting the weight average molecular weight to 1100 to 2500, a resin composition having good MEK solubility was obtained.
  • the resin composition of the present invention has good solubility in solvents, low dielectric properties (low dielectric constant and low dielectric loss tangent), and high heat resistance. It can be used as a raw material for adhesives, sealants, paints, moldings, laminates and printed wiring boards that are excellent in heat resistance and low dielectric properties and suitable for various electronic devices.

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