WO2019127391A1 - Composition de résine maléimide, préimprégné, stratifié et carte de circuit imprimé - Google Patents

Composition de résine maléimide, préimprégné, stratifié et carte de circuit imprimé Download PDF

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Publication number
WO2019127391A1
WO2019127391A1 PCT/CN2017/119906 CN2017119906W WO2019127391A1 WO 2019127391 A1 WO2019127391 A1 WO 2019127391A1 CN 2017119906 W CN2017119906 W CN 2017119906W WO 2019127391 A1 WO2019127391 A1 WO 2019127391A1
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Prior art keywords
resin
group
epoxy resin
maleimide
mass
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PCT/CN2017/119906
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English (en)
Chinese (zh)
Inventor
李鸿杰
唐军旗
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广东生益科技股份有限公司
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Priority to KR1020207012855A priority Critical patent/KR102325101B1/ko
Priority to PCT/CN2017/119906 priority patent/WO2019127391A1/fr
Publication of WO2019127391A1 publication Critical patent/WO2019127391A1/fr

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    • 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
    • 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
    • B32B15/082—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 comprising vinyl resins; comprising acrylic resins
    • 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
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014—Nitrogen containing compounds
    • C08G59/4042—Imines; Imides
    • 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
    • C08G59/5046—Amines heterocyclic
    • C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
    • C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
    • 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
    • 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
    • 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
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • 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
    • H05K1/0313—Organic insulating material
    • 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
    • B32B2305/00—Condition, form or state of the layers or laminate
    • B32B2305/07—Parts immersed or impregnated in a matrix
    • B32B2305/076—Prepregs
    • 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
    • B32B2457/00—Electrical equipment
    • B32B2457/08—PCBs, i.e. printed circuit boards
    • 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
    • C08J2379/00—Characterised by the use 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 C08J2361/00 - C08J2377/00
    • C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • C08J2400/00—Characterised by the use of unspecified polymers
    • C08J2400/24—Thermosetting resins
    • 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
    • C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins

Definitions

  • the present invention relates to the field of electronic product technology, and in particular to a maleimide resin composition useful as an insulating layer material for a printed circuit board, and a prepreg, a laminate, and a printed circuit board using the same.
  • the form is also accelerating toward high integration and high-density mounting. Accordingly, the requirements for multilayer printed wiring boards also involve various aspects. From the consideration of environmental issues, it is required to be based on halogen-free, phosphorus-free, lead-free, standardized flame retardancy, high heat resistance, and the like. characteristic.
  • a halogen-based flame retardant or a phosphorus-based flame retardant may be used in combination, however, a halogen compound or a phosphorus-based compound is likely to generate a toxic compound upon burning.
  • a halogen compound or a phosphorus-based compound is likely to generate a toxic compound upon burning.
  • As another method for improving flame retardancy in the conventional example, an example in which a large amount of inorganic filler is used in combination with a semiconductor encapsulating material is disclosed.
  • it is necessary to fill a large amount of inorganic filler it is necessary to fill a large amount of inorganic filler, and the performance in terms of resin fluidity and drilling processability is very poor.
  • the multilayer printed wiring board has been reduced in size and density, research into thinning a laminated board used in a multilayer printed wiring board has been actively conducted.
  • the thinning since the reflow soldering process needs to be heated to 260 ° C or higher in the manufacturing process of the printed wiring board, if the glass transition temperature of the laminate is low, the laminate and the encapsulating resin are caused by the decrease in the thermal expansion coefficient.
  • the increase in the difference in the coefficient of thermal expansion between the faces in the surface direction causes a problem that the mounting reliability is lowered and the warpage of the multilayer printed circuit board is increased. Therefore, the resin composition which is a material of the laminate requires a low thermal expansion coefficient and a high glass transition. temperature.
  • a method of increasing the glass transition temperature of a laminate there is a method of using a component having a high glass transition temperature in a resin composition for a laminate, such as a maleimide having a more functional group structure and a larger molecular space type. Resin, but this is likely to result in poor lamination processability.
  • a common method is to use a blend of a cyanate resin and a bismaleimide.
  • a cyanate ester compound a novolac type cyanate resin is usually used.
  • the curing conditions of the novolac type cyanate resin are extremely extreme, and it is easy to cure under normal conditions, and there is a problem that the obtained cured product has a large water absorption rate.
  • An object of the present invention is to provide a printed circuit which achieves good flame retardancy, low water absorption by halogen-free, phosphorus-free, and can be cured at a usual temperature and achieves a high glass transition temperature and a high modulus of elasticity at a high temperature.
  • the present invention has been found to provide, as a resin composition for a printed circuit board, a maleimide compound having a specific structure, an imidazole compound having a specific structure, an epoxy resin, and a thermosetting resin.
  • the obtained metal foil-clad laminate is excellent in flame retardancy, low water absorption, high glass transition temperature, and peel strength. The present invention has thus been completed.
  • the present invention includes the following technical solutions.
  • a maleimide resin composition characterized in that the maleimide resin composition comprises:
  • R is a group, a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms or an aralkyl group having 7 to 24 carbon atoms
  • R 1 is an arylene group having 6 to 18 carbon atoms
  • R 2 and R 3 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms or an aralkyl group having 7 to 24 carbon atoms
  • n is 1 to 20 carbon atoms.
  • Ar is a phenyl group, a naphthyl group, a biphenyl group or a hydroxy group thereof; and R 4 and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, and 6 carbon atoms; Aryl groups of -18 or their hydroxy substitutions, provided that at least one of R 4 and R 5 is phenyl, naphthyl, biphenyl or a hydroxy substituent thereof, or at least one carbon atom having a hydroxy substituent An alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 18 carbon atoms having a hydroxy substituent.
  • n is an integer of from 1 to 15, preferably n.
  • R is a group or a hydrogen atom
  • R 1 is a phenylene group, a naphthylene group or a biphenylylene group, and further preferably R1 is a biphenylylene group;
  • R 2 and R 3 are a hydrogen atom.
  • thermosetting resin (D) is selected from the group consisting of a phenol resin, a cyanate resin, an acid anhydride compound, and styrene-maleic anhydride.
  • Copolymer resin, active ester resin, benzoxazine resin, polyphenylene ether resin, silicone resin, amine compound, dicyclopentadiene resin and copolymerization with epoxy resin and/or maleimide resin At least one of the compounds.
  • maleimide resin composition according to any one of 1 to 4, wherein the maleimide resin composition further comprises an inorganic filler (E), and the inorganic filler (E) is preferably It is at least one selected from the group consisting of silica, boehmite, alumina, magnesium hydroxide, and talc.
  • a prepreg comprising a substrate and a maleimide resin composition as described in any one of 1 to 6 which is adhered to the substrate after impregnation and drying.
  • a laminate characterized in that said laminate comprises at least one prepreg as described in 7.
  • said laminate is a metal foil laminate, said metal foil laminate comprising at least one prepreg as described in 7, and overlying prepreg A metal foil on one or both sides of the material.
  • a printed wiring board characterized in that said printed wiring board comprises at least one prepreg as described in 7.
  • the maleimide resin composition of the present invention is a thermosetting resin composition which can form a resin varnish having good storage stability, and a prepreg obtained by impregnating or coating with a resin varnish has good curability. Moreover, high temperature and long-time treatment are not required at the time of curing, and the obtained laminate is excellent in chemical resistance and heat resistance. At the same time, the metal foil-clad laminate obtained by the prepreg has the characteristics of excellent flame retardancy, low water absorption, high glass transition temperature and excellent peel strength, and is particularly suitable for printing requiring high heat resistance and high reliability. Materials for circuit boards.
  • the resin composition of the present invention comprises a specific maleimide compound (A), a specific imidazole compound (B), an epoxy resin (C), a thermosetting resin (D), an optional inorganic filler (E), and Solvent (F), etc.
  • A specific maleimide compound
  • B specific imidazole compound
  • C epoxy resin
  • D thermosetting resin
  • E optional inorganic filler
  • F Solvent
  • the maleimide compound (A) having an unsaturated maleimide group used in the present invention is represented by the following formula (I), and the method for synthesizing the maleimide compound (A) is not particularly limited.
  • Those skilled in the art can make their own choices according to the prior art in combination with their own expertise. Specifically, for example, it can be obtained by reacting maleic anhydride with an amine compound having at least two primary amino groups in one molecule. This reaction is preferably carried out in an organic solvent.
  • an organic solvent As an example of the product, there is MIR-3000 manufactured by Nippon Kayaku Co., Ltd.
  • the cured product is excellent in flame retardancy, and the compound has a similar structure of a novolac and a large number of crosslinking points, so that the glass transition temperature of the cured product can be effectively increased.
  • R is a group, a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms or an aralkyl group having 7 to 24 carbon atoms
  • R 1 is an arylene group having 6 to 18 carbon atoms
  • R 2 and R 3 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms or an aralkyl group having 7 to 24 carbon atoms
  • n is 1 to 20 carbon atoms. Integer.
  • n is an integer of from 1 to 15, more preferably n is an integer of from 1 to 10;
  • R is a group or a hydrogen atom
  • R 1 is a phenylene group, a naphthylene group or a biphenylylene group, and further preferably R1 is a biphenylylene group;
  • R 2 and R 3 are a hydrogen atom.
  • the content of the maleimide compound (A) is not particularly limited, and is relative to the maleimide compound (A), the epoxy resin (C), and the thermosetting property from the viewpoints of glass transition temperature and water absorption.
  • the total amount of the resin resin (D) is 100 parts by mass, preferably 10 to 80 parts by mass, more preferably 20 to 60 parts by mass.
  • the imidazole compound (B) used in the present invention is a compound having a structure represented by the formula (II).
  • the curing reaction of the resin composition can be promoted, and the glass transition temperature and the curability of the cured product can be improved.
  • the elastic modulus of the cured product at a high temperature can also be increased.
  • Ar is a phenyl group, a naphthyl group, a biphenyl group or a hydroxy group thereof, and each of R 4 and R 5 is independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, and 6 carbon atoms.
  • alkyl group having 1 to 6 carbon atoms or the aryl group having 6 to 18 carbon atoms having a hydroxy substituent means that the alkyl group having 1 to 6 carbon atoms or the aryl group having 6 to 18 carbon atoms further contains a hydroxyl group.
  • the substituent for example, an alkyl group having 1 to 6 carbon atoms having a hydroxy substituent includes a methylol group, a hydroxyethyl group, a hydroxypropyl group or the like, and a hydroxymethyl group is preferred.
  • the imidazole compound (B) may have a structure represented by the general formula (III):
  • Ar is a phenyl group, a naphthyl group, a biphenyl group, or a hydroxy group thereof.
  • the imidazole compound (B) is 4-hydroxymethyl-5-methyl-2-phenylimidazole or 2,4,5-triphenylimidazole.
  • the content of the imidazole compound (B) represented by the formula (II) is not particularly limited, and is relative to the horse from the viewpoint of storage stability of the prepreg and formability at the time of processing of the metal foil-clad laminate.
  • the total mass of the imide compound (A), the epoxy resin (C), and the thermosetting resin (D) is preferably in the range of 0.01 to 10 parts by mass, and more preferably in the range of 0.1 to 5 parts by mass.
  • the epoxy resin (C) according to the present invention is not particularly limited, and is selected from compounds having at least two epoxy groups in a molecular structure, and may be selected from bisphenol A type epoxy resins and bisphenol F type epoxy resins.
  • the epoxy resin according to the present invention is further preferably a novolac type epoxy resin, a cresol novolac type epoxy resin, a naphthol type epoxy resin, or a naphthalene.
  • Phenolic novolac type epoxy resin bismuth type epoxy resin, phenolphthalein type epoxy resin, biphenyl type epoxy resin, aralkyl type epoxy resin, aralkyl phenolic type epoxy resin, arylene ether in molecule Any one of the structural epoxy resins or a mixture of at least two, particularly preferably a novolac type epoxy resin, a cresol novolac type epoxy resin, a naphthol novolac type epoxy resin, a fluorene type epoxy resin, a phenolphthalein type Any one or a mixture of at least two of an epoxy resin, an aralkyl novolac type epoxy resin, and an epoxy resin having an arylene ether structure in its molecule.
  • the epoxy resin (C) may be used singly or in combination of at least two types of epoxy resins (C) as needed.
  • the content of the epoxy resin (C) is not particularly limited, and is relative to the maleimide compound (A) and the epoxy resin from the viewpoints of flame retardancy, glass transition temperature, water absorption, and elastic modulus. (C) and a total of 100 parts by mass of the thermosetting resin (D), the amount of the epoxy resin (C) is 10 to 70 parts by weight, preferably 20 to 60 parts by mass, more preferably 20 to 50 parts by mass. .
  • the thermosetting resin (D) may be selected from the group consisting of a phenol resin, a cyanate resin, an acid anhydride compound, a styrene-maleic anhydride copolymer resin, an active ester resin, a benzoxazine resin, a polyphenylene ether resin, and a silicone resin. At least one of an amine compound, a dicyclopentadiene resin, and a compound which can be copolymerized with an epoxy resin and/or a maleimide resin.
  • the active ester resin is obtained by reacting a phenolic compound linked by an aliphatic cyclic hydrocarbon structure, a difunctional carboxylic acid aromatic compound or an acid halide, and a monohydroxy compound.
  • the amount of the difunctional carboxylic acid aromatic compound or acid halide is 1 mol
  • the amount of the phenolic compound linked by the aliphatic cyclic hydrocarbon structure is 0.05 to 0.75 mol
  • the amount of the monohydroxy compound is 0.25 to 0.95 mol.
  • the active ester resin may comprise an active ester of the formula:
  • X is a benzene or naphthalene ring
  • j is 0 or 1
  • k is 0 or 1
  • n represents an average repeating unit of 0.25 to 1.25.
  • the thermosetting resin (D) is preferably a phenol resin, a cyanate resin, an acid anhydride compound, a styrene-maleic anhydride copolymer resin, an active ester resin, a benzoxazine resin, or an amine. Class of compounds. Further, from the viewpoints of flame retardancy and heat resistance, a phenol resin, a cyanate resin, and a benzoxazine resin are particularly preferable.
  • the phenol resin used in the present embodiment may be any resin having two or more phenolic hydroxyl groups in one molecule, and a known one may be appropriately used, and the type thereof is not particularly limited. Specific examples thereof include a cresol novolac type phenol resin, a naphthol aralkyl type phenol resin, a biphenyl aralkyl type phenol resin, an aminoditriazine novolac type phenol resin, and a naphthol type phenol resin.
  • a phenol novolak resin an alkylphenol novolak resin, a bisphenol A novolak resin, a dicyclopentadiene type phenol resin, a Xylock type phenol resin, a terpene modified phenol resin, and a polyvinyl phenol.
  • the phenol resin is preferably a cresol novolak type phenol resin, a biphenyl aralkyl type phenol resin, a naphthol aralkyl type phenol resin, from the viewpoint of water absorbability and heat resistance of the obtained cured product.
  • the aminotriazine novolac type phenol resin and the naphthalene type phenol resin are more preferably a biphenyl aralkyl type phenol resin or a naphthol aralkyl type phenol resin from the viewpoint of flame retardancy.
  • the content of the thermosetting resin (D) is not particularly limited, and is relative to the maleimide compound (A) and the epoxy resin (C) from the viewpoints of flame retardancy, glass transition temperature, and water absorption.
  • the amount of the thermosetting resin (D) is from 1 to 70 parts by weight, preferably from 5 to 60 parts by mass, more preferably from 10 to 50 parts by mass, per 100 parts by mass of the total of the thermosetting resin (D).
  • an inorganic filler generally used for a resin composition for a circuit board can be used, and examples thereof include natural silica, fused silica, amorphous silica, and hollow.
  • Silicas such as silica, metal hydrates such as aluminum hydroxide, boehmite, magnesium hydroxide, molybdenum compounds such as molybdenum oxide and zinc molybdate, zinc borate, zinc stannate, alumina, clay, kaolin, talc
  • the calcined clay, the calcined kaolin, the calcined talc, the mica, the glass short fibers (glass fine powder such as E glass or D glass), the hollow glass, the spherical glass, or the like, may be used alone or in combination of two or more.
  • silica, gangue, magnesium hydroxide, alumina, and talc are preferable, and boehmite and silica are more preferable.
  • fused silica or/and boehmite is preferable.
  • fused silica has a characteristic of a low coefficient of thermal expansion, and boehmite is preferred because it is excellent in flame retardancy and heat resistance.
  • spherical fused silica which has characteristics such as a low coefficient of thermal expansion and good dielectric properties, has good dispersibility and fluidity, and is therefore preferred.
  • the average particle diameter (D50) of the inorganic filler (E) is not particularly limited, but is preferably from 0.01 to 10.0 ⁇ m, more preferably from 0.1 to 5.0 ⁇ m, from the viewpoint of improving the manufacturability of the prepreg, and more preferably 0.2 to 3.0 ⁇ m.
  • the content of the inorganic filler (E) in the resin composition is not particularly limited, and from the viewpoint of lowering thermal expansion of the insulating layer and obtaining high peel strength, relative to the maleimide compound (A), epoxy
  • the total amount of the resin (C) and the thermosetting resin (D) is preferably 10 to 400% by mass, more preferably 30 to 300% by mass, still more preferably 50 to 250% by mass.
  • the resin composition of the present invention may further contain a solvent (F) to prepare a solvent-free resin composition (resin varnish) in a form suitable for coating or impregnation.
  • a solvent (F) which can be used in the present invention is not particularly limited as long as it can dissolve various resin components and does not separate upon mixing, and examples thereof include methanol, ethanol, ethylene glycol, acetone, methyl ethyl ketone, and methyl ethyl group.
  • One or more solvents can be used.
  • the content of the solvent (F) in the resin composition is not particularly limited, and for example, the solvent (F) may be used in an amount of 5 to 50 parts by weight, for example, 10 parts by weight per 100 parts by weight of the resin composition (excluding the solvent). 50, 20-50, 30-40 parts by weight, and the like.
  • the resin composition of the present invention may further contain other additives such as other curing accelerators, wetting and dispersing agents, silane coupling agents, leveling agents, antioxidants, heat stabilizers, antistatic agents, ultraviolet absorbers, pigments, Additives, colorants or lubricants. These various additives may be used singly or in combination of two or more kinds. However, the resin composition of the present invention preferably contains no halogen or halide and a phosphorus-containing compound. The amount of the other additives can be arbitrarily adjusted within the range not detracting from the effects of the present invention.
  • the resin composition of the present invention may be used in combination with a maleimide compound other than the maleimide compound (A) having a structure of the formula (I) as long as it does not impair the inherentity of the maleimide resin composition.
  • Performance can be. They can be used singly or in combination of plural kinds as needed.
  • thermosetting resin composition of the present invention an auxiliary molybdenum compound may be contained in order to ensure the processability of the resin composition.
  • molybdenum compound examples include molybdenum dioxide, zinc molybdate, ammonium molybdate, magnesium molybdate, calcium molybdate, barium molybdate, sodium molybdate, potassium molybdate, phosphomolybdic acid, ammonium phosphomolybdate, and phosphorus.
  • Molybdenum oxide such as sodium molybdate or silicomolybdic acid, molybdenum acid compound, molybdenum boride, molybdenum disilide, molybdenum nitride or molybdenum carbide. One type of these may be used or two or more types may be used in combination.
  • zinc molybdate, calcium molybdate, and magnesium molybdate are preferred from the viewpoint of good effects of low toxicity, electrical insulation, and drilling processability.
  • the molybdenum compound can be used by being supported on talc, silica, zinc oxide, calcium carbonate, magnesium hydroxide or the like to dissolve the resin composition. Prevents sedimentation and dispersibility during organic solvent varnishing.
  • the content of the molybdenum compound is preferably 0.05 to 20% by mass, and more preferably 0.1 to 10% by mass based on the total amount of the resin composition.
  • the prepreg, the laminate, the metal foil-clad laminate, and the printed circuit board of the present invention are each formed using the above resin composition.
  • the prepreg of the present invention comprises a substrate and the above-described maleimide resin composition adhered to the substrate by impregnation and drying.
  • a fiber sheet-shaped reinforcing base material is preferable, and for example, a well-known material used for various laminated sheets for electrical insulating materials can be used.
  • the material thereof include inorganic fibers such as E glass, D glass, S glass, and Q glass, organic fibers such as polyimide, polyester, and tetrafluoroethylene, and mixtures thereof.
  • these base materials have a shape of, for example, a woven fabric, a nonwoven fabric, a roving, a chopped strand mat, and a surface felt, the material and shape can be selected according to the use and performance of the intended molded article, and can be individually or in combination as needed. Two or more materials and shapes.
  • the thickness of the substrate is not particularly limited, and for example, about 0.03 to 0.5 mm can be used. From the viewpoint of heat resistance, moisture resistance, and workability, a substrate surface-treated with a silane coupling agent or the like, or a substrate subjected to mechanical fiber opening treatment is preferable.
  • the amount of the resin composition to be adhered to the substrate is preferably 20 to 90% by mass based on the resin content of the dried prepreg.
  • the prepreg of the present invention is obtained by heating and drying at a temperature of 100 to 200 ° C for 1 to 30 minutes to semi-cure (B-stage).
  • the laminate of the present invention is a laminate formed by using one or more of the aforementioned prepregs.
  • a laminate metal foil-clad laminate
  • the metal foil is not particularly limited as long as it is used for electrical insulating materials, and examples thereof include metal foils such as copper and aluminum.
  • a copper foil is preferred.
  • an electrolytic copper foil, a rolled copper foil, or the like can be suitably used.
  • a known surface treatment such as nickel treatment or cobalt treatment can be applied to the metal foil.
  • the thickness of the metal foil can be appropriately adjusted within a range suitable as a material of the printed circuit board, and is preferably 2 to 35 ⁇ m.
  • the molding conditions can be applied to laminates and multilayer boards for electrical insulating materials, for example, multi-stage press, multi-stage vacuum press, continuous forming, autoclave molding machine, etc., at a temperature of 100 to 250 ° C and a pressure of 2 to 100 kg/cm 2 .
  • the molding is carried out under the conditions of a heating time of 0.1 to 5 hours.
  • prepreg and the inner layer wiring board of the present invention may be combined and laminated to form a multilayer board.
  • the printed circuit board of the present invention comprises a laminate formed by laminating the aforementioned prepreg, and the prepreg comprises the above resin composition.
  • the printed circuit board can be produced by using the above prepreg or metal foil-clad laminate as a laminate material. That is, a printed circuit board is produced by using them as a build-up material, and the prepreg constitutes an insulating layer containing a resin composition.
  • the prepreg when used as a laminate material, the prepreg is subjected to surface treatment by a conventional method, and a wiring pattern (conductor layer) is formed by plating on the surface of the insulating layer, whereby a printed circuit board can be obtained.
  • the metal foil of the metal foil-clad laminate is etched by a conventional method, and the layer (insulation layer) made of the prepreg is surface-treated by plating.
  • a wiring pattern is formed on the surface of the insulating layer, so that a printed circuit board can be obtained.
  • a metal foil-clad laminate can be produced by using the prepreg by the above-described method for producing a metal foil-clad laminate, and then a printed circuit board can be obtained by the above method.
  • the prepreg when used as a material for a multilayer printed circuit board, the prepreg can also be directly used as a laminate material.
  • each component was calculated as a solid matter.
  • thermomechanical analyzer TA 2980 manufactured by TA INSTRUMENTS LTD.
  • a copper clad laminate sample having a thickness of 0.8 mm was used, and after cutting into a 100 mm ⁇ 100 mm square, a sample obtained by etching the copper foil was prepared.
  • the sample was treated with a pressure cooker at 121 ° C and 2 atm for 6 hours, and then the water absorption of the laminate was evaluated. Then, the sample was immersed in a solder bath at 288 ° C for 300 seconds, and the appearance change was visually observed for abnormality. Three tests were performed, and for each piece, the case where no abnormality was recorded was "pass", and the case where the bursting occurred was referred to as "fail".
  • the flexural modulus of the material was measured at a temperature of 200 ° C using a universal material testing machine.
  • the copper plating peel strength (adhesive strength) was measured three times according to the IPC-TM-650 method (copper foil peeling resistance meter), and the average value of the peeling strength was determined. .
  • the copper foil laminate samples prepared in the examples and the comparative examples were etched away from the copper foil to have a size of 4 mm ⁇ 60 mm, and the thermal expansion coefficient (400A) of the sample was measured by a thermomechanical analysis method (TMA), wherein the test direction was measured.
  • TMA thermomechanical analysis method
  • the coefficient of thermal expansion in the plane direction from 50 ° C to 130 ° C was measured in the direction of the warp of the glass fiber cloth at a temperature rising rate of 10 ° C / min from room temperature 25 ° C to 300 ° C.
  • the thickness of the test sample was 0.1 mm.
  • a maleimide compound (MIR-3000, manufactured by Nippon Kayaku Co., Ltd.) having a structure of the formula (I)
  • a maleimide compound (MIR-3000, manufactured by Nippon Kayaku Co., Ltd.) having a structure of the formula (I)
  • 30 parts by mass of a phenol biphenyl aralkyl type epoxy resin (NC-3000-H) 20 parts by mass of phenol biphenyl aralkyl phenol resin (MEHC-7851-H, Mingwa Kasei Co., Ltd.) was dissolved and mixed with methyl ethyl ketone, and 150 parts by mass of spherical fused silica (SC2500) was further mixed.
  • One, four, and eight sheets of the above prepreg were laminated, and an electrolytic copper foil having a thickness of 18 ⁇ m was pressed on both sides thereof, and solidified in a press for 2 hours, and the curing pressure was 45 kg/cm 2 .
  • the curing temperature was 200 ° C, and a copper-clad laminate having a thickness of 0.1, 0.4, and 0.8 mm was obtained.
  • a copper-clad laminate was obtained in the same manner as in Example 2 except that 50 parts by mass of MIR-3000 was used instead of the above.
  • a maleimide compound (MIR-3000, manufactured by Nippon Kayaku Co., Ltd.) having a structure of the formula (I), and 24 parts by mass of a phenol biphenyl aralkyl type epoxy resin (NC-3000-H) (manufactured by Nippon Kayaku Co., Ltd.) and 16 parts by mass of a phenol biphenyl aralkyl phenol resin (MEHC-7851-H, Megumi Kasei Co., Ltd.) were dissolved and mixed with methyl ethyl ketone, and the same operation as in Example 1 was carried out. A copper clad laminate was obtained.
  • MIR-3000 manufactured by Nippon Kayaku Co., Ltd.
  • NC-3000-H phenol biphenyl aralkyl type epoxy resin
  • MEHC-7851-H phenol biphenyl aralkyl phenol resin
  • NC-3000-H phenol biphenyl aralkyl type epoxy resin
  • EPICLON EXA-4710 tetrafunctional naphthalene type epoxy resin
  • a copper-clad laminate was obtained in the same manner as in Example 2 except that 20 parts by mass of a naphthol aralkyl phenol resin (SN485, manufactured by Nippon Steel Chemical Co., Ltd.) was used instead of MEHC-7851-H.
  • a naphthol aralkyl phenol resin SN485, manufactured by Nippon Steel Chemical Co., Ltd.
  • Example 2 In the same manner as in Example 2 except that 20 parts by mass of a novolac type cyanate resin (manufactured by PRIMASET PT-30, manufactured by LONZA.J APAN INC.) was used instead of MEHC-7851-H and 0.02 parts by mass of zinc octoate was added thereto. The operation yields a copper clad laminate.
  • a novolac type cyanate resin manufactured by PRIMASET PT-30, manufactured by LONZA.J APAN INC.
  • Example 15 15 parts by mass of a phenol biphenyl aralkyl phenol resin (MEHC-7851-H, Mingwa Kasei Co., Ltd.), and 5 parts by mass of a styrene-maleic anhydride copolymer (SMA EF-40, manufactured by Sartomer, USA) were used instead.
  • a copper-clad laminate was obtained in the same manner as in Example 1 except that 20 parts by mass of MEHC-7851-H was used.
  • Example 1 15 parts by mass of phenol biphenyl aralkyl phenol resin (MEHC-7851-H, Mingwa Kasei Co., Ltd.), and 5 parts by mass of dicyclopentadiene type active ester (HPC-8000-65T, Japan DIC Co., Ltd.) were used instead of 20
  • MEHC-7851-H phenol biphenyl aralkyl phenol resin
  • HPC-8000-65T dicyclopentadiene type active ester
  • Example 1 15 parts by mass of a phenol biphenyl aralkyl phenol resin (MEHC-7851-H, Mingwa Kasei Co., Ltd.), and 5 parts by mass of a polyphenylene ether resin (manufactured by SA90, Sabic) were used instead of 20 parts by mass of MEHC-7851-H. Otherwise, a copper clad laminate was obtained in the same manner as in Example 1.
  • Example 2 In the same manner as in Example 1, except that 120 parts by mass of spherical fused silica (SC2500-SQ, manufactured by Admatechs Company Limited) was used instead of 120 parts by mass of spherical fused silica (SC2500-SQ, manufactured by Admatechs Company Limited). The operation yields a copper clad laminate.
  • SC2500-SQ spherical fused silica
  • a maleimide compound (MIR-3000, manufactured by Nippon Kayaku Co., Ltd.) having a structure of the formula (I)
  • a maleimide compound (MIR-3000, manufactured by Nippon Kayaku Co., Ltd.) having a structure of the formula (I)
  • 30 parts by mass of a phenol biphenyl aralkyl type epoxy resin (NC-3000-H) 20 parts by mass of phenol biphenyl aralkyl phenol resin (MEHC-7851-H, Mingwa Kasei Co., Ltd.) was dissolved and mixed with methyl ethyl ketone, and 150 parts by mass of spherical fused silica (SC2500) was further mixed.
  • Example 4 was operated in the same manner to obtain a copper clad laminate.
  • Example 4 The operation was carried out in the same manner as in Example 4 except that 0.25 parts by mass of 2-phenylimidazole (2PZ, manufactured by Shikoku Chemicals Co., Ltd.) was used instead of 0.25 parts by mass of 2-phenyl-4-methyl-5-hydroxymethylimidazole. A copper clad laminate was obtained.
  • Comparative Example 1 when the imidazole compound having the same amount and structure was inconsistent as in Example 1, the gelation time was too short to cause no processability; in Comparative Example 7, the maleimide having the same amount and inconsistent structure as in Example 1 was added. In the case of a compound, since the solid content of the varnish is too low, the processability is not obtained, and when the solid content is appropriate, there is a problem that the maleimide compound cannot be completely dissolved, and the processability is not obtained.
  • Comparative Example 2-6 differs from Examples 1-4 in that the imidazole compound is different, Example 1-4 employs the imidazole compound of the present invention, and Comparative Example 2-6 employs an imidazole compound different from the present invention, and the former has a remarkable advantage.
  • Comparative Examples 8-10 differ from Example 6 in that the maleimide compound is different when the maleimide compound of the formula I is not used (comparison In Examples 8-10), the flame retardancy and moisture absorption heat resistance were poor, and the water absorption rate was remarkably high.
  • the maleimide resin composition of the present invention is more easily cured, has higher heat resistance, mechanical properties and lower water absorption at the same curing temperature, without using the horse of the present invention.
  • the comparative examples of the imide resin composition even when cured at a higher curing temperature (Comparative Example 11-12), the characteristics of high heat resistance, mechanical properties, and low water absorption of the present invention could not be attained.

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Abstract

La présente invention concerne une composition de résine maléimide et un préimprégné, un stratifié et une carte de circuit imprimé utilisant celle-ci. La composition de résine maléimide selon la présente invention comprend : un composé maléimide (A) présentant une structure de formule (I) ; un composé imidazole (B) présentant une structure de formule générale (II) ; une résine époxyde (C) ; et une résine thermodurcissable (D).
PCT/CN2017/119906 2017-12-29 2017-12-29 Composition de résine maléimide, préimprégné, stratifié et carte de circuit imprimé WO2019127391A1 (fr)

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PCT/CN2017/119906 WO2019127391A1 (fr) 2017-12-29 2017-12-29 Composition de résine maléimide, préimprégné, stratifié et carte de circuit imprimé

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CN114672166A (zh) * 2020-12-24 2022-06-28 广东生益科技股份有限公司 一种无卤阻燃型树脂组合物及其制成的预浸料和印制电路用层压板
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WO2023038035A1 (fr) * 2021-09-09 2023-03-16 株式会社レゾナック Composition de résine d'étanchéité, dispositif de composant électronique et procédé de fabrication de dispositif de composant électronique

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KR20230092125A (ko) 2021-12-17 2023-06-26 주식회사 나노코 저유전 특성을 갖는 신규 비스말레이미드계 열경화성 수지 및 이를 포함하는 복합수지

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WO2022052106A1 (fr) * 2020-09-14 2022-03-17 穗晔实业股份有限公司 Composition de résine thermodurcissable exempte d'halogène et son utilisation
CN114672166A (zh) * 2020-12-24 2022-06-28 广东生益科技股份有限公司 一种无卤阻燃型树脂组合物及其制成的预浸料和印制电路用层压板
CN114672166B (zh) * 2020-12-24 2023-08-15 广东生益科技股份有限公司 一种无卤阻燃型树脂组合物及其制成的预浸料和印制电路用层压板
CN114685935A (zh) * 2020-12-25 2022-07-01 衡所华威电子有限公司 一种低介电常数树脂组合物及其制备方法与应用
CN114685935B (zh) * 2020-12-25 2024-02-27 衡所华威电子有限公司 一种低介电常数树脂组合物及其制备方法与应用
WO2023038035A1 (fr) * 2021-09-09 2023-03-16 株式会社レゾナック Composition de résine d'étanchéité, dispositif de composant électronique et procédé de fabrication de dispositif de composant électronique

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