CN111448258A - Resin composition, prepreg, and laminate - Google Patents

Resin composition, prepreg, and laminate Download PDF

Info

Publication number
CN111448258A
CN111448258A CN201880055617.XA CN201880055617A CN111448258A CN 111448258 A CN111448258 A CN 111448258A CN 201880055617 A CN201880055617 A CN 201880055617A CN 111448258 A CN111448258 A CN 111448258A
Authority
CN
China
Prior art keywords
resin composition
thermosetting resin
weight
parts
maleimide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201880055617.XA
Other languages
Chinese (zh)
Inventor
窪山典人
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Risho Kogyo Co Ltd
Original Assignee
Risho Kogyo Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Risho Kogyo Co Ltd filed Critical Risho Kogyo Co Ltd
Publication of CN111448258A publication Critical patent/CN111448258A/en
Pending legal-status Critical Current

Links

Images

Classifications

    • 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
    • C08L79/085—Unsaturated 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
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
    • C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
    • 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
    • B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
    • 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
    • B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
    • B32B27/281—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42 comprising polyimides
    • 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
    • B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
    • B32B27/285—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42 comprising polyethers
    • 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
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • 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
    • C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
    • 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
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • 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
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • 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
    • C08K5/14—Peroxides
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/16—Solid spheres
    • C08K7/18—Solid spheres inorganic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; 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
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08L71/12—Polyphenylene oxides
    • 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
    • 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
    • C08L79/02—Polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/12—Mountings, e.g. non-detachable insulating substrates
    • H01L23/14—Mountings, e.g. non-detachable insulating substrates characterised by the material or its electrical properties
    • 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
    • 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
    • H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
    • 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
    • H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
    • H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics
    • 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
    • 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
    • C08J2471/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C08J2471/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08J2471/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08J2471/12—Polyphenylene oxides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Computer Hardware Design (AREA)
  • Power Engineering (AREA)
  • Reinforced Plastic Materials (AREA)
  • Laminated Bodies (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The invention provides a thermosetting resin composition which has greatly improved heat resistance compared with the prior high heat-resistant substrate and can ensure that the curing condition is the same as that of the condition using epoxy resin, a prepreg using the thermosetting resin and a laminated plate using the prepreg. The thermosetting resin composition contains: a maleimide compound having at least 2 maleimide groups in 1 molecule, a polyphenylene ether compound having at least 2 reactive organic groups in 1 molecule, a curing accelerator, and an inorganic filler.

Description

Resin composition, prepreg, and laminate
Technical Field
The present invention relates to a resin composition technology, and more particularly, to a resin composition, a prepreg using the resin composition, and a laminate using the prepreg.
Background
In recent years, demands for power saving, energy saving, and efficiency improvement of electronic devices have been increasing due to electric equipment of automobiles or popularization of Electric Vehicles (EVs), and power semiconductors, which are key devices in power electronics technology, play an important role in power saving, energy saving, and efficiency improvement. In order to exhibit the performance of a high-power device, it is important not to limit the operating temperature of a semiconductor, and therefore, an insulating substrate on which a power semiconductor is mounted is required to have heat resistance.
As a substrate on which a power semiconductor is mounted, a ceramic substrate having high heat resistance, such as an alumina substrate or an aluminum nitride substrate, is used (see patent document 1). However, the bonding with a dissimilar material such as a heat dissipation metal plate required for mounting a power semiconductor on a ceramic substrate, and the miniaturization and thinning of the substrate have problems.
Therefore, a high heat-resistant organic substrate may be used as a substrate for mounting a power semiconductor instead of a ceramic substrate, but a conventional high heat-resistant organic substrate is formed of a composition containing an epoxy resin as a main component and a resin having high heat resistance such as a bismaleimide resin, a modified imide resin, an isocyanate resin, and a benzoxazine resin (see patent documents 2, 3, and 4).
However, an organic substrate mainly composed of an epoxy resin has a limited improvement in heat resistance, and it is difficult to maintain bonding with a dissimilar material such as a metal foil in a high-temperature atmosphere. However, if heat resistance is regarded as important and the resin is made of only a resin having high heat resistance such as bismaleimide resin, the resin exhibits very excellent performance in terms of heat resistance, but does not have handling easiness as in an epoxy resin, and further requires a high temperature and a long time for curing, which causes a problem of increase in production cost.
Prior art documents:
patent document 1 Japanese patent No. 6154383
Patent document 2 Japanese patent laid-open publication No. 2015-199905
Patent document 3 Japanese laid-open patent publication No. 2016-
Patent document 4 Japanese patent laid-open publication No. 2018-48347
Disclosure of Invention
In view of the above-described problems, an object of the present invention is to provide a thermosetting resin composition which has a significantly improved heat resistance as compared with conventional high heat resistant substrates and can be cured under conditions similar to those in the case of using an epoxy resin, a prepreg using the thermosetting resin, and a laminate using the prepreg.
The thermosetting resin composition of the present invention is characterized by containing: a maleimide compound having at least 2 maleimide groups in 1 molecule, a polyphenylene ether compound having at least 2 reactive organic groups in 1 molecule, a curing accelerator, and an inorganic filler.
The polyphenylene ether compound is contained in an amount of 10 to 100 parts by weight and the curing accelerator is contained in an amount of 1 to 30 parts by weight based on 100 parts by weight of the maleimide compound.
The maleimide compound is preferably a polyfunctional maleimide resin or a bisphenol A maleimide resin.
The maleimide compound may be a liquid maleimide compound obtained by adding a solvent.
The polyphenylene ether compound preferably has a weight average molecular weight Mw of 1000 to 50000.
The curing accelerator is imidazole, a phosphorus compound or an organic peroxide having a peroxy group.
The inorganic filler is contained in an amount of 100 to 400 parts by weight based on 100 parts by weight of the maleimide compound.
The inorganic filler contains silicon dioxide, sodium hydroxide, magnesium hydroxide, aluminum oxide, titanium dioxide, boron nitride, or aluminum nitride.
The inorganic filler is preferably spherical.
The prepreg of the present invention is a prepreg comprising the thermosetting resin composition and a fiber base material, wherein the fiber base material is impregnated with the thermosetting resin composition and semi-cured.
The fiber substrate is formed of glass fibers, liquid crystal polymer fibers, aramid fibers, carbon fibers, polyester fibers, nylon fibers, acrylic fibers, or vinylon fibers.
The laminate of the present invention is characterized by being formed by heating and pressing 1 or more sheets of the above-described prepregs stacked one on another.
Further, a metal foil is disposed on at least one surface of a material in which 1 or more prepregs are stacked.
Alternatively, a metal foil is disposed on at least one surface of a material in which 1 or more prepregs are stacked, and a heat radiating metal plate is disposed on the other surface, and the material in which 1 or more prepregs are stacked becomes an insulating layer.
The thermosetting resin composition of the present invention contains: the maleimide compound having at least 2 maleimide groups in 1 molecule, the polyphenylene ether compound having at least 2 reactive organic groups in 1 molecule, the curing accelerator and the inorganic filler are free from the epoxy resin, and thus a laminate having excellent heat resistance can be realized, and further, the production cost can be made to the same extent as in the prior art under the same curing conditions as the epoxy resin.
The prepreg of the present invention is a prepreg formed of the thermosetting resin composition and a fiber base material, wherein the thermosetting resin composition is impregnated into the fiber base material and semi-cured, and the prepregs are laminated to form a laminate, whereby a laminate having excellent heat resistance can be formed.
The laminate sheet of the present invention is obtained by heating and pressing 1 or more sheets of the above prepreg, and thus can realize excellent heat resistance and can be used as a highly heat-resistant substrate for mounting a power semiconductor.
Drawings
FIG. 1 is a schematic sectional view of a metal foil-clad laminate obtained by laminating the laminate of the present invention.
FIG. 2 is a schematic sectional view of a metal-clad metal foil laminate produced from the laminate of the present invention.
Detailed Description
The thermosetting resin composition, prepreg and laminate of the present invention will be described. First, the thermosetting resin composition of the present invention will be explained.
The thermosetting resin composition of the present invention is a resin composition used by impregnating a fiber base material with the resin composition when a prepreg is formed, and is characterized by containing: the curing agent comprises a maleimide compound having at least 2 maleimide groups in 1 molecule, a polyphenylene ether compound having at least 2 reactive organic groups in 1 molecule, a curing accelerator and an inorganic filler, and comprises 10 to 100 parts by weight of the polyphenylene ether compound, 1 to 30 parts by weight of the curing accelerator and 100 to 400 parts by weight of the inorganic filler per 100 parts by weight of the maleimide compound.
As the maleimide compound, a polyfunctional maleimide resin, a bisphenol A maleimide resin or the like is used. The maleimide compound is used in a liquid state by adding a solvent or the like as needed. The maleimide compound is preferably a compound having excellent solvent solubility.
The polyphenylene ether compound preferably has a weight average molecular weight Mw of 1000 to 50000, more preferably 1000 to 10000. When the polyphenylene ether compound has a large molecular weight, the solubility in a solvent and the reactivity are lowered, and therefore, in consideration of this, it is necessary to use the polyphenylene ether compound having a predetermined molecular weight.
The curing accelerator may be imidazole, a phosphorus compound, or an organic peroxide having a peroxy group, and an organic peroxide having a peroxy group is particularly preferable. When the curing accelerator is less than 1 part by weight, the reactivity is insufficient, and when it is 30 parts by weight or more, the characteristics are deteriorated, so that it is preferable to contain 1 to 30 parts by weight based on 100 parts by weight of the maleimide compound as described above.
The inorganic filler may include silica, sodium hydroxide, magnesium hydroxide, alumina, titania, boron nitride, aluminum nitride, or the like, and a spherical inorganic filler is preferably used. As described above, the maleimide compound is preferably contained in an amount of 100 to 400 parts by weight, more preferably 150 to 350 parts by weight, based on 100 parts by weight of the maleimide compound. When the compounding ratio of the inorganic filler is less than 100 parts by weight, the thermal conductivity may be reduced when the thermosetting resin composition is used for a laminated plate, and when the compounding ratio of the inorganic filler exceeds 400 parts by weight, the productivity of a laminated plate using the thermosetting resin composition may be reduced.
The thermosetting resin composition of the present invention is formed by mixing an inorganic filler with a thermosetting resin containing a maleimide compound, a polyphenylene ether compound and a curing accelerator, and dispersing the mixture by stirring, kneading or the like. In this case, if necessary, a surfactant such as a higher fatty acid ester or a copolymer having a functional group may be used, and a solvent may be used. The thermosetting resin composition of the present invention is not a material mainly composed of an epoxy resin in the prior art.
Next, a prepreg of the present invention using the thermosetting resin composition will be described. The prepreg of the present invention is obtained by impregnating a fiber base material in the form of woven fabric, nonwoven fabric or the like with the above thermosetting resin composition, and then heating and drying the impregnated fiber base material to semi-cure the thermosetting resin.
Specific examples of the fiber base material used in the prepreg of the present invention include glass woven fabric and the like. As the fibers of the fiber base material, glass fibers, liquid crystal polymer fibers, aramid fibers, carbon fibers, polyester fibers, nylon fibers, acrylic fibers, vinylon fibers, and the like are used.
Next, a laminated board of the present invention using the prepreg will be described. The laminate of the present invention is obtained by laminating 1 or more sheets of the above-described prepregs, sandwiching the laminated material between metal plates serving as heating and pressurizing means, and performing heat and pressure molding at a predetermined temperature and pressure. As described above, the laminate of the present invention can realize excellent heat resistance by using a thermosetting resin composition containing the maleimide compound and the polyphenylene ether compound, instead of using a conventional resin composition containing an epoxy resin as a main component.
A metal foil-clad laminate 1, which is 1 embodiment of the laminate of the present invention, will be explained. The metal foil-clad laminate 1 is obtained by disposing a metal foil 3 on at least one surface of a material obtained by laminating 1 or more prepregs 2, and then performing heat-pressure molding. The metal foil 3 is not particularly limited, and copper foil, aluminum foil, or the like is mainly used.
Fig. 1 shows an embodiment in which 2 prepregs 2 are stacked and metal foils 3 are disposed on both surfaces, as an example of the metal foil clad laminate 1. In the metal foil-clad laminate 1, first, a glass woven fabric as a fiber base material is impregnated with the thermosetting resin composition. Then, the thermosetting resin composition impregnated into the glass woven fabric is dried by heating, thereby obtaining a prepreg 2 in which the thermosetting resin composition is in a semi-cured state.
Then, 2 sheets of the prepreg 2 were stacked, and 2 sheets of the metal foil 3 were stacked on each of both surfaces of the 2 sheets of the stacked prepreg 2. Then, the metal foil-clad laminate 1 having the cross-sectional structure shown in fig. 1 is completed by performing heat and pressure molding at a predetermined temperature and pressure while sandwiching the laminate between metal plates as heating and pressure means.
In addition, the thermal resistance in the thickness direction can be reduced by the thinning, and the heat dissipation performance can be improved, and the thermal resistance is obtained by a heat dissipation characteristic evaluation method specified in the test method in JPCA-TMC-L ED 02T-2010 of the JPCA standard, for example.
Further, a metal-clad metal foil laminate 10 as another embodiment of the laminate of the present invention will be explained. The metal-clad metal foil laminate 10 is obtained by disposing a metal foil 3 on one surface of a material obtained by laminating 1 or more prepregs 2, disposing a metal substrate plate 4 for heat dissipation on the other surface, and then performing heat and pressure molding. The metal-clad metal foil laminate 10 shown in fig. 2 is obtained by disposing a metal foil 3 on one surface of a material obtained by laminating 2 sheets of prepregs 2, disposing a metal substrate plate 4 for heat dissipation on the other surface, and performing heat and pressure molding.
In the metal-clad metal base metal foil laminate 10, a material obtained by laminating 2 sheets of the prepreg 2 is an insulating layer. When the prepreg 2 is used as an insulating layer, the metal-clad substrate metal foil laminate 10 can be obtained at a lower cost while maintaining the same heat dissipation property and having not only a white appearance but also a small variation in insulating strength, as compared with the case where only a resin composition is used as an insulating layer.
The laminate of the present invention will be described with reference to examples. Examples 1 to 5 and comparative examples 1 to 3 will be described in order below.
< example 1>
A first resin varnish is prepared, the first resin varnish being a thermosetting resin composition in which 200 parts by weight of spherical silica as an inorganic filler is uniformly dispersed with respect to a thermosetting resin containing, with respect to 100 parts by weight of a polyfunctional maleimide resin: 100 parts by weight of a polyphenylene ether resin (weight average molecular weight Mw: 1000 to 10000) and 10 parts by weight of imidazole as a curing accelerator.
The amount of the first resin varnish impregnated into the molded article was 105g/m, the thickness of which was 0.1mm2The glass fiber woven fabric of (1) is dried by heating and semi-cured to obtain a first prepreg. After 8 sheets of the first prepreg were stacked and copper foils having a thickness of 0.035mm were disposed on both outer layers, the resultant was subjected to heat and pressure molding (temperature: 200 ℃ C., pressure: 2MPa), thereby obtaining a metal foil-clad laminate of example 1 having a thickness of 0.8 mm.
< example 2>
A second resin varnish is prepared, the second resin varnish being a thermosetting resin composition in which 200 parts by weight of spherical silica as an inorganic filler is uniformly dispersed with respect to a thermosetting resin containing, with respect to 100 parts by weight of a polyfunctional maleimide resin: 100 parts by weight of a polyphenylene ether resin (weight average molecular weight Mw: 1000 to 10000) and 10 parts by weight of an organic peroxide as a curing accelerator.
Then, the second resin varnish was impregnated with the molded resin in the same manner as in example 1 to give a plateau having a thickness of 0.1mm and a weight of 105g/m2The glass fiber woven fabric of (1) is dried by heating and semi-cured to obtain a second prepreg. After 8 sheets of the second prepreg were stacked and copper foils having a thickness of 0.035mm were disposed on both outer layers, the resultant was subjected to heat and pressure molding (temperature: 200 ℃ C., pressure: 2MPa), thereby obtaining a metal foil-clad laminate of example 2 having a thickness of 0.8 mm.
< example 3>
Preparing a third resin varnish which is a thermosetting resin composition in which 200 parts by weight of spherical silica as an inorganic filler is uniformly dispersed with respect to a thermosetting resin containing, with respect to 100 parts by weight of a polyfunctional maleimide resin: 100 parts by weight of a polyphenylene ether resin (weight average molecular weight Mw: 20000 to 50000) and 5 parts by weight of an organic peroxide as a curing accelerator.
Then, the third resin varnish was impregnated with the molded resin in the same manner as in example 1 to form a plateau having a thickness of 0.1mm and a weight of 105g/m2The glass fiber woven fabric of (1) is dried by heating and semi-cured to obtain a third prepreg. After 8 sheets of the third prepreg were stacked and copper foils having a thickness of 0.035mm were disposed on both outer layers, the laminate was heated and pressed (temperature: 200 ℃ C., pressure: 2MPa) to obtain a metal foil-clad laminate of example 3 having a thickness of 0.8 mm.
< example 4>
Preparing a fourth resin varnish which is a thermosetting resin composition in which 200 parts by weight of spherical silica as an inorganic filler is uniformly dispersed with respect to a thermosetting resin containing, with respect to 100 parts by weight of a bisphenol a type maleimide resin: 50 parts by weight of a polyphenylene ether resin (weight average molecular weight Mw: 1000 to 10000) and 10 parts by weight of a phosphorus compound as a curing accelerator.
Then, the fourth resin varnish was impregnated with the molded resin in the same manner as in example 1 to give a plateau having a thickness of 0.1mm and a weight of 105g/m2The glass fiber woven fabric of (1) is dried by heating and semi-cured to obtain a fourth prepreg. After 8 sheets of the fourth prepreg were stacked and copper foils having a thickness of 0.035mm were disposed on both outer layers, the resultant was subjected to heat and pressure molding (temperature: 200 ℃ C., pressure: 2MPa), thereby obtaining a metal foil-clad laminate of example 4 having a thickness of 0.8 mm.
< example 5>
Preparing a fifth resin varnish which is a thermosetting resin composition in which 200 parts by weight of spherical silica as an inorganic filler is uniformly dispersed with respect to a thermosetting resin containing, with respect to 100 parts by weight of a bisphenol a type maleimide resin: 50 parts by weight of a polyphenylene ether resin (weight average molecular weight Mw: 20000 to 50000) and 5 parts by weight of an organic peroxide as a curing accelerator.
Then, the fifth resin varnish was impregnated with the molded resin in the same manner as in example 1 to give a plateau having a thickness of 0.1mm and a weight of 105g/m2The glass fiber woven fabric of (1) is dried by heating and semi-cured to obtain a fifth prepreg. After 8 sheets of the fifth prepreg were stacked and copper foils having a thickness of 0.035mm were disposed on both outer layers, the resultant was subjected to heat and pressure molding (temperature: 200 ℃ C., pressure: 2MPa), thereby obtaining a metal foil-clad laminate of example 5 having a thickness of 0.8 mm.
Comparative example 1
Preparing a sixth resin varnish which is a thermosetting resin composition in which 200 parts by weight of spherical silica as an inorganic filler is uniformly dispersed with respect to a thermosetting resin containing, with respect to 100 parts by weight of a polyfunctional maleimide resin: 100 parts by weight of an epoxy resin, and 5 parts by weight of imidazole as a curing accelerator.
Then, the sixth resin varnish was impregnated with the molded resin in the same manner as in example 1 to give a plateau having a thickness of 0.1mm and a weight of 105g/m2The glass fiber woven fabric of (1) is dried by heating and semi-cured to obtain a sixth prepreg. After 8 sheets of the sixth prepreg were stacked and copper foils having a thickness of 0.035mm were disposed on both outer layers, the resultant was subjected to heat and pressure molding (temperature: 200 ℃ C., pressure: 2MPa), thereby obtaining a metal foil-clad laminate having a thickness of 0.8mm in comparative example 1.
Comparative example 2
Preparing a seventh resin varnish which is a thermosetting resin composition in which 200 parts by weight of spherical silica as an inorganic filler is uniformly dispersed with respect to a thermosetting resin containing, with respect to 100 parts by weight of an epoxy resin: 200 parts by weight of a polyphenylene ether resin (weight average molecular weight Mw: 1000 to 10000) and 5 parts by weight of imidazole as a curing accelerator.
Then, the seventh resin varnish was impregnated with the molded resin in the same manner as in example 1 to give a plateau having a thickness of 0.1mm and a weight of 105g/m2The glass fiber woven fabric of (1) is dried by heating and semi-cured to obtain a seventh prepreg. After 8 sheets of the seventh prepreg were laminated and copper foils having a thickness of 0.035mm were disposed on both outer layers, the laminate was heated and pressed (temperature: 200 ℃ C., pressure: 2MPa), thereby obtaining a metal foil-clad laminate of comparative example 2 having a thickness of 0.8 mm.
Comparative example 3
Preparing an eighth resin varnish which is a thermosetting resin composition in which 200 parts by weight of spherical silica as an inorganic filler is uniformly dispersed with respect to a thermosetting resin containing, with respect to 100 parts by weight of an epoxy resin: 200 parts by weight of a polyphenylene ether resin (weight average molecular weight Mw: 20000 to 50000) and 5 parts by weight of imidazole as a curing accelerator.
Then, the eighth resin varnish was impregnated with the terrace in an amount of 105g/m in a thickness of 0.1mm after molding in the same manner as in example 12In the glass fiber woven fabric, the glass fiber woven fabric is heated, dried and semi-cured to obtain an eighth pre-cureAnd (5) soaking the materials. 8 sheets of the eighth prepreg were stacked, and copper foils having a thickness of 0.035mm were disposed on both outer layers, followed by heating and pressing (temperature: 200 ℃ C., pressure: 2MPa), to thereby obtain a metal foil-clad laminate of comparative example 3 having a thickness of 0.8 mm.
The metal foil-clad laminates obtained in examples 1 to 5 and comparative examples 1 to 3 were evaluated by the following methods, and the results are shown in table 1.
Determination of the glass transition temperature (Tg)
The copper foil of the metal foil-clad laminate thus obtained was removed by etching, and a 10 × 60mm evaluation substrate was prepared and subjected to thermomechanical analysis using a dynamic viscoelasticity measuring apparatus (DMA) to measure the glass transition temperature (Tg).
Heat resistance T-288, T-300, T-350
From the obtained metal foil-clad laminate, an evaluation substrate of 5 × 5mm was prepared, and thermomechanical analysis was performed by a compression method using a TMA test apparatus.
Measurement of thermal expansion Rate
The copper foil of the obtained metal foil-clad laminate was removed by etching, and then an evaluation substrate of 5 × 5mm was prepared, and thermo-mechanical analysis was performed using a dynamic viscoelasticity measuring apparatus (DMA) to measure the thermal expansion ratio.
Copper foil peel strength
A predetermined sample was prepared from the obtained metal foil-clad laminate by a method in accordance with JIS C6481, one end of the copper foil of the sample was peeled off by an appropriate length, and then the sample was attached to a supporting member, and the tip of the peeled copper foil was sandwiched by a jig, and was continuously peeled off by about 50mm at a speed of about 50mm per minute in a direction perpendicular to the surface of the copper foil. The lowest value of the load during this period was expressed as the peel strength in kN/m.
Flammability
Using a method based on the vertical burning test method of U L-94, a sample was prepared from the obtained metal foil-clad laminate, and the flammability was determined by performing 2 times of operation of 10 seconds of flame contact.
< Table 1>
Figure BDA0002393089100000071
Figure BDA0002393089100000081
As is clear from table 1, the metal foil-clad laminates of examples 1 to 5 have a high glass transition temperature and excellent heat resistance, while the metal foil-clad laminates of comparative examples 1 to 3 have a high glass transition temperature because they contain an epoxy resin, but are far inferior to examples 1 to 5 in heat resistance.
The laminate of the present invention has an excellent effect of greatly improving heat resistance as compared with a conventional highly heat-resistant substrate by using, as a thermosetting resin composition for a prepreg, a maleimide compound having at least 2 maleimide groups in 1 molecule and a polyphenylene ether compound having at least 2 reactive organic groups in 1 molecule, instead of a conventional epoxy resin. Even if the epoxy resin is not used, the curing conditions can be set to the same extent as in the case of using the epoxy resin.
[ notation ] to show
1 … laminated sheet with metal foil
2 … prepreg
3 … Metal foil
4 … sheet metal base
10 … laminated metal foil with metal base material

Claims (14)

1. A thermosetting resin composition comprising: a maleimide compound having at least 2 maleimide groups in 1 molecule, a polyphenylene ether compound having at least 2 reactive organic groups in 1 molecule, a curing accelerator, and an inorganic filler.
2. The thermosetting resin composition as claimed in claim 1, wherein said polyphenylene ether compound is contained in an amount of 10 to 100 parts by weight and said curing accelerator is contained in an amount of 1 to 30 parts by weight based on 100 parts by weight of said maleimide compound.
3. The thermosetting resin composition claimed in claim 1 or 2, wherein said maleimide compound is a polyfunctional maleimide resin or a bisphenol a maleimide resin.
4. The thermosetting resin composition according to claim 1 to 3, wherein the maleimide compound is a liquid maleimide compound obtained by adding a solvent.
5. The thermosetting resin composition as claimed in any one of claims 1 to 4, wherein the polyphenylene ether compound has a weight average molecular weight Mw of 1000 to 50000.
6. The thermosetting resin composition claimed in any one of claims 1 to 5, wherein the curing accelerator is imidazole, a phosphorus compound or an organic peroxide having a peroxy group.
7. The thermosetting resin composition claimed in any one of claims 1 to 6, wherein said inorganic filler is contained in an amount of 100 to 400 parts by weight based on 100 parts by weight of said maleimide compound.
8. The thermosetting resin composition claimed in any one of claims 1 to 7, wherein the inorganic filler comprises silica, sodium hydroxide, magnesium hydroxide, alumina, titanium dioxide, boron nitride or aluminum nitride.
9. The thermosetting resin composition claimed in any one of claims 1 to 8, wherein the inorganic filler is spherical.
10. A prepreg comprising the thermosetting resin composition according to any one of claims 1 to 9 and a fibrous base material, wherein the fibrous base material is impregnated with the thermosetting resin composition and semi-cured.
11. The prepreg of claim 10, in which the fibrous substrate is formed of glass fibers, liquid crystal polymer fibers, aramid fibers, carbon fibers, polyester fibers, nylon fibers, acrylic fibers, or vinylon fibers.
12. A laminate sheet obtained by laminating 1 or more prepregs according to claim 10 or 11 and heat-press molding the same.
13. A laminate according to claim 12, wherein a metal foil is provided on at least one surface of a material in which 1 or more prepregs are laminated.
14. The laminate according to claim 12, wherein a metal foil is disposed on at least one surface of a material in which 1 or more prepregs are stacked, and a heat radiating metal plate is disposed on the other surface, and the material in which 1 or more prepregs are stacked becomes an insulating layer.
CN201880055617.XA 2018-11-16 2018-11-29 Resin composition, prepreg, and laminate Pending CN111448258A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2018-215592 2018-11-16
JP2018215592A JP2020083931A (en) 2018-11-16 2018-11-16 Resin composition, prepreg, and, laminate sheet
PCT/JP2018/044081 WO2020100314A1 (en) 2018-11-16 2018-11-29 Resin composition, prepreg, and laminated plate

Publications (1)

Publication Number Publication Date
CN111448258A true CN111448258A (en) 2020-07-24

Family

ID=70731122

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201880055617.XA Pending CN111448258A (en) 2018-11-16 2018-11-29 Resin composition, prepreg, and laminate

Country Status (5)

Country Link
JP (1) JP2020083931A (en)
KR (1) KR102141432B1 (en)
CN (1) CN111448258A (en)
TW (1) TWI788549B (en)
WO (1) WO2020100314A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112848544B (en) * 2021-01-14 2023-03-31 中车青岛四方机车车辆股份有限公司 Fiber metal laminated plate and preparation method thereof
KR20230160853A (en) * 2021-03-24 2023-11-24 파나소닉 아이피 매니지먼트 가부시키가이샤 Resin composition, prepreg, resin-added film, resin-added metal foil, metal-clad laminate, and wiring board
JP2023112261A (en) * 2022-02-01 2023-08-14 利昌工業株式会社 Resin composition, adhesive sheet, prepreg, and laminate

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106255713A (en) * 2014-04-04 2016-12-21 日立化成株式会社 Polyphenyl ether derivative, hot curing resin composition, resin varnish, prepreg, plywood and multilayer printed wiring board
JP2017066280A (en) * 2015-09-30 2017-04-06 日立化成株式会社 Thermosetting resin composition and manufacturing method therefor, and prepreg, metal-clad laminate and multilayer printed board having the thermosetting resin composition
JP2018131519A (en) * 2017-02-15 2018-08-23 三菱瓦斯化学株式会社 Resin composition, resin sheet and printed wiring board

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1508993A (en) 1974-04-18 1978-04-26 Mars Ltd Food product and method
KR100280911B1 (en) * 1996-06-07 2001-02-01 야마모토 카즈모토 Resin-carrying metal foil for multilayered wiring board, process for manufaturing the same, multilayered wiring board, and electronic device
KR102039874B1 (en) 2011-01-18 2019-11-04 히타치가세이가부시끼가이샤 Prepreg, and laminate board and printed wiring board using same
KR20150115523A (en) 2014-04-04 2015-10-14 삼성전기주식회사 Insulating resin composition for printed circuit board and products using the same
JP6705446B2 (en) * 2015-04-30 2020-06-03 日立化成株式会社 Thermosetting resin composition, prepreg, laminated board and multilayer printed wiring board
JP7106819B2 (en) * 2017-06-22 2022-07-27 昭和電工マテリアルズ株式会社 Resin varnish, resin composition, prepreg, laminate, multilayer printed wiring board, and storage method for resin varnish
JP6863126B2 (en) * 2017-06-22 2021-04-21 昭和電工マテリアルズ株式会社 Resin composition, prepreg, laminated board, multilayer printed wiring board and semiconductor package

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106255713A (en) * 2014-04-04 2016-12-21 日立化成株式会社 Polyphenyl ether derivative, hot curing resin composition, resin varnish, prepreg, plywood and multilayer printed wiring board
JP2017066280A (en) * 2015-09-30 2017-04-06 日立化成株式会社 Thermosetting resin composition and manufacturing method therefor, and prepreg, metal-clad laminate and multilayer printed board having the thermosetting resin composition
JP2018131519A (en) * 2017-02-15 2018-08-23 三菱瓦斯化学株式会社 Resin composition, resin sheet and printed wiring board

Also Published As

Publication number Publication date
KR20200060292A (en) 2020-05-29
TWI788549B (en) 2023-01-01
TW202030260A (en) 2020-08-16
WO2020100314A1 (en) 2020-05-22
JP2020083931A (en) 2020-06-04
KR102141432B1 (en) 2020-08-05

Similar Documents

Publication Publication Date Title
US5686172A (en) Metal-foil-clad composite ceramic board and process for the production thereof
CA2649841C (en) Resin composition, prepreg, laminate, and wiring board
CN111448258A (en) Resin composition, prepreg, and laminate
US9745443B2 (en) Inorganic filler-containing epoxy resin cured product and laminate including the same
CN115139589B (en) High-heat-conductivity copper-clad plate and preparation method thereof
CN107429067B (en) Laminate for insulation
KR20090109114A (en) Interlayer insulating film having carrier material, and multilayer printed circuit board using the interlayer insulating film
JP2002187937A (en) Epoxy resin composition, prepreg, and metal-clad laminate
CN112710534A (en) Copper foil and characterization method thereof, and copper-clad plate
TWI839701B (en) Resin composition, adhesive sheet, prepreg and laminate
JP4192870B2 (en) Laminated board and wiring board
JP2006082370A (en) Laminate and wiring board
JP2004335661A (en) Pre-preg for printed wiring, and plate stack
JPH0263821A (en) Laminated plate
JP3211608B2 (en) Manufacturing method of copper-clad laminate
WO2019208402A1 (en) Layered plate, printed circuit board, multilayer printed circuit board, layered body, and layered plate production method
JP4254705B2 (en) Wiring board
JP2007009089A (en) Prepreg, laminated board and printed wiring board
JP6086182B2 (en) Resin composition, and resin sheet and laminate using the same
KR20240034188A (en) Manufacturing method and composite sheet of composite sheet
JP2022181861A (en) Metallic foil laminated resin sheet and method for manufacturing the same
CN114536923A (en) Fluorine-containing resin-based high-thermal-conductivity high-frequency copper-clad plate with high dielectric constant
CN117715959A (en) Method for manufacturing composite sheet and composite sheet
JP2002012834A (en) Thermosetting adhesive film
JP2004106274A (en) Copper-clad laminated plate and its production method

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination