WO2021090629A1 - Composition de résine isolante, article durci de résine isolante, stratifié et carte de circuit imprimé - Google Patents

Composition de résine isolante, article durci de résine isolante, stratifié et carte de circuit imprimé Download PDF

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WO2021090629A1
WO2021090629A1 PCT/JP2020/038030 JP2020038030W WO2021090629A1 WO 2021090629 A1 WO2021090629 A1 WO 2021090629A1 JP 2020038030 W JP2020038030 W JP 2020038030W WO 2021090629 A1 WO2021090629 A1 WO 2021090629A1
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insulating resin
mass
resin composition
amine
inorganic filler
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PCT/JP2020/038030
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English (en)
Japanese (ja)
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裕紀 木元
良太 熊谷
八島　克憲
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デンカ株式会社
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Priority to CN202080063653.8A priority Critical patent/CN114364738A/zh
Priority to JP2021554850A priority patent/JPWO2021090629A1/ja
Publication of WO2021090629A1 publication Critical patent/WO2021090629A1/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
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • B32B15/01—Layered products comprising a layer of metal all layers being exclusively metallic
    • B32B15/017—Layered products comprising a layer of metal all layers being exclusively metallic one layer being formed of aluminium or an aluminium alloy, another layer being formed of an alloy based on a non ferrous metal other than aluminium
    • 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
    • B32B33/00—Layered products characterised by particular properties or particular surface features, e.g. particular surface coatings; Layered products designed for particular purposes not covered by another single class
    • 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
    • C08G59/5006—Amines aliphatic
    • C08G59/502—Polyalkylene polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • 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
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/24—Derivatives of hydrazine
    • C08K5/25—Carboxylic acid hydrazides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • 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
    • H05K1/05—Insulated conductive substrates, e.g. insulated metal substrate
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2227—Oxides; Hydroxides of metals of aluminium
    • 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
    • C08K3/38—Boron-containing compounds
    • C08K2003/382—Boron-containing compounds and nitrogen
    • C08K2003/385—Binary compounds of nitrogen with boron

Definitions

  • the present invention relates to an insulating resin composition and a cured product thereof, which are suitably used for manufacturing a metal-based circuit board.
  • the present invention also relates to a laminate and a circuit board formed by using an insulating resin composition.
  • Circuit boards have been put into practical use as circuit boards for forming mixed integrated circuits by mounting electronic and electrical components such as semiconductor elements.
  • Circuit boards are classified into resin circuit boards, ceramic circuit boards, metal-based circuit boards, and the like based on the substrate material.
  • resin circuit boards are inexpensive, they have low thermal conductivity, so they are limited to applications that are used with relatively small power. Ceramic circuit boards are suitable for applications where they are used with relatively large power because of their high electrical insulation characteristics and high heat resistance, but they have the disadvantage of being expensive.
  • metal-based circuit boards have intermediate properties between the two, and are used for general-purpose applications that are used with relatively large amounts of electric power, such as refrigerator power supplies, household air conditioner power supplies, automobile power supplies, and high-speed railway power supplies. Suitable for applications such as power supplies.
  • Patent Document 1 a circuit board composition having a specific epoxy resin, a curing agent, and an inorganic filler as essential components is used to provide a circuit board having excellent stress relaxation resistance, heat resistance, moisture resistance, and heat dissipation. The method of obtaining is disclosed.
  • An object of the present invention is to provide an insulating resin composition capable of forming an insulating layer having both excellent adhesiveness and insulating properties and a low elastic modulus in a high temperature and high humidity environment, and a cured product thereof.
  • Another object of the present invention is to provide a circuit board provided with an insulating layer made of a cured product of the insulating resin composition and having excellent moisture insulation resistance, thermal conductivity and heat cycle resistance.
  • One aspect of the present invention relates to an insulating resin composition containing an organic material and an inorganic filler.
  • the organic material contains an epoxy resin, an amine-based curing agent, a phosphoric acid ester compound having one or more hydroxyl groups in one molecule, and a heavy metal inactivating agent.
  • the content of the inorganic filler is 50% by mass or more and 95% by mass or less.
  • the amine-based curing agent may contain a first amine-based curing agent having an amine equivalent of 300 or less and a second amine-based curing agent having an amine equivalent of 800 or more.
  • the content of the phosphoric acid ester compound may be 0.05 to 0.4% by mass based on the total amount of the organic material and the inorganic filler.
  • the content of the heavy metal inactivating agent may be 0.01 to 0.5% by mass based on the total amount of the organic material and the inorganic filler.
  • the melting point of the heavy metal inactivating agent may be 250 ° C. or lower.
  • Another aspect of the present invention relates to an insulating resin cured product, which is a cured product of the insulating resin composition.
  • the insulating resin cured product according to one embodiment may have a storage elastic modulus of 500 MPa or less at 85 ° C.
  • Yet another aspect of the present invention is a laminate comprising a metal plate, the insulating resin cured body arranged on the metal plate, and a metal foil arranged on the insulating resin cured body. Regarding.
  • Yet another aspect of the present invention is a circuit board comprising a metal plate, the insulating resin cured body arranged on the metal plate, and a circuit portion arranged on the insulating resin cured body. Regarding.
  • an insulating resin composition capable of forming an insulating layer having both excellent adhesiveness and insulating properties and a low elastic modulus in a high temperature and high humidity environment, and a cured product thereof. Further, according to the present invention, there is provided a circuit board provided with an insulating layer made of a cured product of the insulating resin composition and excellent in moisture insulation resistance, thermal conductivity and heat cycle resistance.
  • the insulating resin composition of the present embodiment is a composition containing an organic material and an inorganic filler, and the content of the inorganic filler is 50% by mass or more and 95% by mass or less. Further, the insulating resin composition of the present embodiment contains, as organic materials, an epoxy resin, an amine-based curing agent, a phosphoric acid ester compound having one or more hydroxyl groups in one molecule, and a heavy metal inactivating agent. , Contain.
  • the insulating resin composition it is possible to form a cured product (insulating layer) having both excellent adhesiveness and insulating properties and a low elastic modulus in a high temperature and high humidity environment. Therefore, the insulating resin composition can be suitably used for forming an insulating layer for a circuit board (particularly a metal-based circuit board). The reason why the above effect is obtained in this embodiment is not always clear, but it is considered as follows.
  • the phosphoric acid ester compound improves the dispersibility and adhesion between the resin component and the inorganic filler due to the presence of hydroxyl groups in the molecule, and improves the moisture-resistant adhesiveness.
  • the phosphate ester compound traps OH radicals generated under high temperature and high humidity environment and under the condition of applying DC voltage, thereby suppressing the deterioration of moisture insulation resistance due to oxidative deterioration of the insulating layer. Conceivable.
  • ionic impurities into the insulating layer can be considered as a cause of deterioration of adhesiveness and insulating property.
  • metal ions are trapped by the heavy metal inactivating agent, and the adverse effect of migration is suppressed. It is thought that it will be done.
  • metal ions for example, copper ions
  • the insulating resin composition of the present embodiment According to the above, it is possible to form an insulating layer capable of maintaining excellent moisture-resistant adhesiveness and moisture-insulating insulation even when adjacent to a metal plate.
  • the crosslinked structure of the epoxy resin and the amine-based curing agent is formed in the cured product, so that the effect of the above-mentioned phosphoric acid ester compound and heavy metal inactivating agent can be remarkably obtained, and the cured product can be obtained. It is considered that the elastic modulus of
  • the epoxy resin may be one that is cured by an amine-based curing agent to exhibit an adhesive action.
  • the epoxy resin include bifunctional epoxy resins such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, and bisphenol A / F type epoxy resin; novolak type epoxy resins such as phenol novolac type epoxy resin and cresol novolac type epoxy resin.
  • Polyfunctional epoxy resin such as trisphenol methane type epoxy resin; Glycidylamine type epoxy resin; Heterocyclic ring-containing epoxy resin such as triglycidyl isocyanurate, hydrogenated bisphenol A type epoxy resin, hydrogenated bisphenol F type epoxy resin and other fats Ring-type epoxy resin and the like can be mentioned.
  • a bifunctional epoxy resin (bifunctional aromatic epoxy resin) and an alicyclic epoxy resin can be preferably used as the epoxy resin.
  • the insulating resin composition according to the present embodiment may contain at least one of a bifunctional epoxy resin and an alicyclic epoxy resin, and may contain both a bifunctional epoxy resin and an alicyclic epoxy resin. May be good.
  • the ratio of the alicyclic epoxy resin content A 2 to the bifunctional epoxy resin content A 1 may be, for example, 1.5 or more, preferably 2.0 or more, and more preferably 2.5 or more.
  • the ratio (A 2 / A 1 , mass ratio) may be, for example, 8.0 or less, preferably 6.0 or less, and more preferably 4.0 or less. As a result, the insulating property and adhesiveness of the cured product tend to be further improved.
  • ratios (A 2 / A 1 , mass ratio) are, for example, 1.5 to 8.0, 1.5 to 6.0, 1.5 to 4.0, 2.0 to 8.0, 2 It may be 0.0 to 6.0, 2.0 to 4.0, 2.5 to 8.0, 2.5 to 6.0 or 2.5 to 4.0.
  • the content of the epoxy resin in the insulating resin composition may be, for example, 50% by mass or more, preferably 55% by mass or more, more preferably 60% by mass or more, still more preferably 65% by mass or more, based on the total amount of the organic material. It is mass% or more.
  • the content of the epoxy resin may be, for example, 90% by mass or less, preferably 85% by mass or less, more preferably 80% by mass or less, and further preferably 75% by mass or less, based on the total amount of the organic material.
  • the content of the epoxy resin in the insulating resin composition is, for example, 50 to 90% by mass, 50 to 85% by mass, 50 to 80% by mass, 50 to 75% by mass, 55 to 55 to 90% by mass, based on the total amount of the organic material.
  • % 65-85% by mass, 65-80% by mass or 65-75% by mass.
  • the amine-based curing agent may be any curing agent having an amino group and capable of curing the epoxy resin.
  • examples of the amine-based curing agent include aromatic amine-based curing agents, aliphatic amine-based curing agents, and dicyandiamide.
  • an aliphatic amine-based curing agent is preferable from the viewpoint of further improving the heat cycle resistance of the circuit board.
  • the amine-based curing agent preferably contains a first amine-based curing agent having an amine equivalent of 300 or less and a second amine-based curing agent having an amine equivalent of 800 or more.
  • the amine-based curing agent preferably contains an amine-based curing agent having a polyether chain, and at least one of the first amine-based curing agent and the second amine-based curing agent has a polyether chain. Is more preferable, and it is further preferable that both the first amine-based curing agent and the second amine-based curing agent have a polyether chain. Since an amine-based curing agent having a polyether chain has excellent compatibility with an epoxy resin, it is easy to obtain a cured product having further excellent adhesiveness and heat resistance by using such an amine-based curing agent.
  • the polyether chain is preferably a polyoxyalkylene chain, and more preferably a polyoxyalkylene chain having an alkylene group selected from the group consisting of an ethylene group and a propylene group.
  • both the first amine-based curing agent and the second amine-based curing agent are aliphatic amine-based curing agents.
  • first amine-based curing agent and the second amine-based curing agent are both curing agents having two amino groups in one molecule.
  • the ratio of the content B 2 of the second amine-based curing agent to the content B 1 of the first amine-based curing agent in the insulating resin composition (B 2 / B 1 , mass ratio) is, for example, 0.2. It may be more than that, preferably 0.25 or more, and more preferably 0.3 or more. As a result, the heat cycle resistance of the circuit board tends to be further improved.
  • the ratio (B 2 / B 1 , mass ratio) may be, for example, 2.0 or less, preferably 1.5 or less, and more preferably 1.0 or less. As a result, the insulating property, adhesiveness and heat resistance of the cured product tend to be further improved.
  • ratios (B 2 / B 1 , mass ratio) are, for example, 0.2 to 2.0, 0.2 to 1.5, 0.2 to 1.0, 0.25 to 2.0, 0. It may be .25 to 1.5, 0.25 to 1.0, 0.3 to 2.0, 0.3 to 1.5 or 0.3 to 1.0.
  • the amount of the curing agent added may be determined based on the ratio (C 2 / C 1 ) of the active hydrogen equivalent (C 2 ) of the amine-based curing agent to the epoxy equivalent (C 1) of the epoxy resin.
  • the ratio (C 2 / C 1 ) is preferably 0.1 or more, more preferably 0.2 or more, still more preferably 0.3 or more.
  • the ratio (C 2 / C 1 ) is preferably 2.5 or less, more preferably 2.0 or less, still more preferably 1.5 or less. That is, the ratio (C 2 / C 1 ) is, for example, 0.1 to 2.5, 0.1 to 2.0, 0.1 to 1.5, 0.2 to 2.5, 0.2 to 2. It may be 0.0, 0.2 to 1.5, 0.3 to 2.5, 0.3 to 2.0 or 0.3 to 1.5.
  • the phosphate ester compound has one or more hydroxyl groups in one molecule.
  • the phosphoric acid ester compound has an effect of improving the dispersibility and adhesion between the resin component and the inorganic filler and improving the moisture-resistant adhesiveness due to the presence of the hydroxyl group in the molecule. Be done.
  • the above-mentioned phosphoric acid ester compound has an effect of suppressing a decrease in moisture insulation resistance due to oxidative deterioration of the insulating layer by trapping OH radicals generated in a high temperature and high humidity environment and under the condition of applying a DC voltage. Is also considered to have.
  • the number of hydroxyl groups contained in the phosphoric acid ester compound is more preferably 1 to 2 in one molecule, and further preferably 2 in one molecule.
  • the phosphoric acid ester compound preferably has a hydroxyl group directly bonded to a phosphorus atom. Further, it is more preferable that the phosphoric acid ester compound has two hydroxyl groups directly bonded to the phosphorus atom.
  • the phosphoric acid ester compound preferably contains a polyether chain from the viewpoint of excellent compatibility with the epoxy resin and the amine-based curing agent and from the viewpoint of further improving the adhesion between the inorganic filler and the resin component.
  • the polyether chain is preferably a polyoxyalkylene chain, and more preferably a polyoxyalkylene chain having an alkylene group selected from the group consisting of an ethylene group and a propylene group.
  • the phosphoric acid ester compound preferably contains an oxycarbonyl group from the viewpoint of excellent compatibility with the epoxy resin and the amine-based curing agent and further improving the adhesion between the inorganic filler and the resin component.
  • the number average molecular weight of the phosphoric acid ester compound is preferably 200 or more, and more preferably 400 or more.
  • the number average molecular weight of the phosphoric acid ester compound is preferably 2000 or less, and more preferably 1000 or less.
  • the number average molecular weight of the phosphate ester compound indicates a value measured by size exclusion chromatography (GPC). That is, the number average molecular weight of the phosphoric acid ester compound may be, for example, 200 to 2000, 200 to 1000, 400 to 2000 or 400 to 1000.
  • the phosphoric acid ester compound may be, for example, a compound represented by the following formula (1).
  • R represents a monovalent group having a polyether chain.
  • R may further have a polyester chain.
  • the content of the phosphoric acid ester compound in the insulating resin composition may be, for example, 0.05% by mass or more, preferably 0.1% by mass or more, based on the total amount of the organic material and the inorganic filler. .. As a result, the above-mentioned effect of the phosphoric acid ester compound is more prominently exhibited.
  • the content of the phosphoric acid ester compound in the insulating resin composition may be, for example, 0.4% by mass or less, preferably 0.3% by mass or less, based on the total amount of the organic material and the inorganic filler. Is.
  • the content of the phosphoric acid ester compound in the insulating resin composition is, for example, 0.05 to 0.4% by mass and 0.05 to 0.3% by mass based on the total amount of the organic material and the inorganic filler. , 0.1-0.4% by mass or 0.1-0.3% by mass.
  • the heavy metal inactivating agent may be, for example, one capable of chelating and capturing metal ions (for example, copper ions) in an insulating resin composition or a cured product thereof.
  • a nitrogen-containing inactivating agent such as a hydrazine-based heavy metal inactivating agent or a triazole-based heavy metal inactivating agent can be preferably used.
  • heavy metal inactivating agent examples include bis dodecanedioate [N2- (2-hydroxybenzoyl) hydrazide] (product name "CDA-6", manufactured by ADEKA), N- (2H-1,2,4-triazole). -5-yl) salicylamide (product name "CDA-1”, manufactured by ADEKA), N, N'-bis ⁇ 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionyl ⁇ hydrazine (product) Names "CDA-10", manufactured by ADEKA), 3-amino-1,2,4-triazole and the like can be mentioned.
  • the heavy metal inactivating agent one having a low melting point is preferable from the viewpoint of further improving the dispersibility in the insulating resin composition.
  • the melting point of the heavy metal inactivating agent may be, for example, 250 ° C. or lower, preferably 240 ° C. or lower, more preferably 230 ° C. or lower, still more preferably 220 ° C. or lower.
  • the content of the heavy metal inactivating agent in the insulating resin composition may be, for example, 0.01% by mass or more, preferably 0.03% by mass or more, based on the total amount of the organic material and the inorganic filler. More preferably, it is 0.05% by mass or more. As a result, the above-mentioned effects of the heavy metal inactivating agent are more prominently exhibited, and the moisture-resistant adhesiveness tends to be further improved.
  • the content of the heavy metal inactivating agent in the insulating resin composition may be, for example, 0.5% by mass or less, preferably 0.3% by mass, based on the total amount of the organic material and the inorganic filler. Hereinafter, it is more preferably 0.2% by mass or less.
  • the content of the heavy metal inactivating agent in the insulating resin composition is, for example, 0.01 to 0.5% by mass and 0.01 to 0.3% by mass based on the total amount of the organic material and the inorganic filler. %, 0.01 to 0.2% by mass, 0.03 to 0.5% by mass, 0.03 to 0.3% by mass, 0.03 to 0.2% by mass, 0.05 to 0.5% by mass %, 0.05 to 0.3% by mass or 0.05 to 0.2% by mass.
  • the insulating resin composition may further contain components other than the above as an organic material.
  • components other than the above as an organic material include surface modifiers such as coupling agents, leveling agents, defoaming agents, wetting agents, stabilizers, curing accelerators and the like.
  • the inorganic filler is not particularly limited, and a known inorganic filler used for applications requiring insulation and thermal conductivity can be used without particular limitation.
  • the inorganic filler examples include an inorganic filler composed of aluminum oxide, silica, aluminum nitride, silicon nitride, boron nitride and the like.
  • the inorganic filler contains an inorganic material selected from the group consisting of aluminum oxide, silica, silicon nitride and boron nitride as a main component from the viewpoint of suppressing a decrease in moisture insulation resistance due to hydrolysis of the inorganic material. Is preferable.
  • the content of the inorganic material in the inorganic filler is preferably 60% by mass or more, more preferably 70% by mass or more, still more preferably 80% by mass or more, based on the total amount of the inorganic filler.
  • the inorganic filler when the inorganic filler contains a large amount of aluminum nitride, the aluminum nitride may be hydrolyzed in a high temperature and high humidity environment, and the insulating property may be lowered. Therefore, the content of aluminum nitride in the inorganic filler is preferably 40% by mass or less, more preferably 30% by mass or less, still more preferably 20% by mass or less, based on the total amount of the inorganic filler. As described above, by using an inorganic material selected from the group consisting of aluminum oxide, silica, silicon nitride and boron nitride as a main component, the decrease in insulating property due to such hydrolysis is remarkably suppressed. ..
  • the shape of the inorganic filler is not particularly limited, and may be particle-like, scaly, polygonal, or the like, and is preferably particle-like.
  • the maximum particle size of the inorganic filler may be, for example, 250 ⁇ m or less, preferably 200 ⁇ m or less, and more preferably 150 ⁇ m or less. As a result, the insulating property of the cured product tends to be further improved.
  • the minimum particle size of the inorganic filler is not particularly limited, but from the viewpoint of further improving the thermal conductivity, it may be, for example, 0.05 ⁇ m or more, preferably 0.1 ⁇ m or more. In the present specification, the maximum particle size and the minimum particle size of the inorganic filler indicate the d90 diameter and the d10 diameter in the volume-based particle size distribution, and these are measured by a laser diffraction type particle size distribution measuring device.
  • the inorganic filler may contain two or more kinds of inorganic fillers having different average particle diameters.
  • the inorganic filler may contain a first inorganic filler having an average particle diameter of 25 ⁇ m or more and a second inorganic filler having an average particle diameter of 4 ⁇ m or less.
  • the filling density is increased and the thermal conductivity of the cured product is further improved by filling the gap between the first inorganic filler with the second inorganic filler.
  • the average particle size of the inorganic filler indicates the d50 diameter in the volume-based particle size distribution.
  • the volume-based particle size distribution is measured with a laser diffraction type particle size distribution measuring device.
  • the average particle size of the first inorganic filler is preferably 30 ⁇ m or more, more preferably 40 ⁇ m or more.
  • the average particle size of the first inorganic filler may be, for example, 200 ⁇ m or less, preferably 150 ⁇ m or less. With such an average particle size, the above-mentioned effect is more prominently exhibited. That is, the average particle size of the first inorganic filler may be, for example, 30 to 200 ⁇ m, 30 to 150 ⁇ m, 40 to 200 ⁇ m, or 40 to 150 ⁇ m.
  • the average particle size of the second inorganic filler is preferably 3.5 ⁇ m or less, more preferably 3 ⁇ m or less.
  • the average particle size of the second inorganic filler may be, for example, 0.05 ⁇ m or more, preferably 0.1 ⁇ m or more.
  • the average particle size of the second inorganic filler may be, for example, 0.05 to 3.5 ⁇ m, 0.05 to 3 ⁇ m, 0.1 to 3.5 ⁇ m, or 0.1 to 3 ⁇ m.
  • the inorganic filler may further contain a third inorganic filler having an average particle size of more than 4 ⁇ m and less than 25 ⁇ m. According to such a third inorganic filler, the above-mentioned effect is more prominently exhibited.
  • the content of the inorganic filler in the insulating resin composition is 50% by mass or more, preferably 55% by mass or more, and more preferably 60% by mass or more, based on the total amount of the insulating resin composition. As a result, the moisture resistance and thermal conductivity of the cured product tend to be further improved.
  • the content of the inorganic filler in the insulating resin composition is 95% by mass or less, preferably 90% by mass or less, and more preferably 85% by mass or less based on the total amount of the insulating resin composition. .. This makes it easier to obtain a cured product having improved adhesiveness and insulating properties in a high temperature and high humidity environment, and tends to further improve the heat cycle resistance of the circuit board.
  • the content of the inorganic filler in the insulating resin composition is, for example, 50 to 95% by mass, 50 to 90% by mass, 50 to 85% by mass, 55 to 95% by mass based on the total amount of the insulating resin composition. %, 55-90% by mass, 55-85% by mass, 60-95% by mass, 60-90% by mass or 60-85% by mass.
  • the cured insulating resin according to the present embodiment is a cured product of the above-mentioned insulating resin composition.
  • the heat insulating resin cured product can form an insulating layer having both excellent adhesiveness and insulating properties and a low elastic modulus in a high temperature and high humidity environment.
  • the storage elastic modulus of the cured insulating resin at 85 ° C. is preferably 500 MPa or less, more preferably 400 MPa or less, further preferably 300 MPa or less, and even more preferably 200 MPa or less. According to such an insulating resin cured product, a circuit board having further excellent heat cycle resistance can be realized.
  • the method for producing the cured insulating resin is not particularly limited.
  • the cured insulating resin can be produced by heat-treating and curing the insulating resin composition.
  • the heat treatment may be performed in one step or in two steps. By performing the heat treatment in two steps, an insulating resin cured product can be formed via the semi-cured product of the insulating resin composition.
  • the heat treatment temperature may be, for example, 150 to 250 ° C., preferably 160 to 240 ° C.
  • the heat treatment time may be, for example, 2 to 15 hours, preferably 2. . 5-10 hours.
  • the temperature of the first stage heat treatment may be, for example, 60 to 130 ° C., preferably 65 to 100 ° C.
  • the heat treatment time is, for example, 0.3 to 8 hours. It is preferably 0.5 to 5 hours.
  • the temperature of the second stage heat treatment may be, for example, 150 to 250 ° C., preferably 160 to 240 ° C., and the heat treatment time may be, for example, 2 to 15 hours, preferably 2.5. ⁇ 10 hours.
  • an insulating resin cured product having a predetermined shape By performing heat treatment while maintaining the insulating resin composition or its semi-cured body in a predetermined shape, an insulating resin cured product having a predetermined shape can be obtained.
  • a layered insulating resin cured product can be formed on the metal plate by applying the insulating resin composition on the metal plate, laminating the metal foil as needed, and curing the metal foil.
  • the laminate according to the present embodiment includes a metal plate, an insulating resin cured body arranged on the metal plate, and a metal foil arranged on the insulating resin cured body.
  • the metal plate and the metal foil may be separated by an insulating resin cured body, and the insulating resin cured body may function as an insulating layer.
  • the metal material constituting the metal plate is not particularly limited, and examples thereof include aluminum, aluminum alloy, copper, copper alloy, iron, and stainless steel.
  • the metal plate may be composed of one kind of metal material, or may be composed of two or more kinds of metal materials. Further, the metal plate may have a single-layer structure or a multi-layer structure.
  • the thickness of the metal plate is not particularly limited, and may be, for example, 0.5 to 3.0 mm from the viewpoint of being suitable for producing a circuit board.
  • the metal material constituting the metal foil is not particularly limited, and examples thereof include copper, aluminum, and nickel.
  • the metal leaf may be composed of one kind of metal material, or may be composed of two or more kinds of metal materials. Further, the metal foil may have a single-layer structure or a multi-layer structure.
  • the thickness of the metal foil is not particularly limited, and may be, for example, 5 ⁇ m to 1 mm from the viewpoint of being suitable for producing a circuit board.
  • the thickness of the cured insulating resin is not particularly limited, and may be, for example, 50 ⁇ m to 300 ⁇ m from the viewpoint of being suitable for producing a circuit board.
  • the manufacturing method of the laminated body is not particularly limited.
  • the laminate is a step of applying an insulating resin composition on a metal plate and curing or semi-curing, and a cured or semi-cured insulating resin composition (that is, an insulating resin cured body or semi-cured body).
  • a cured or semi-cured insulating resin composition that is, an insulating resin cured body or semi-cured body.
  • the method may further include a step of curing the semi-cured body of the insulating resin composition.
  • the metal foils may be joined by, for example, a roll laminating method, a laminated pressing method, or the like.
  • the laminate is a step of applying an insulating resin composition on a metal foil and curing or semi-curing, and a cured or semi-cured insulating resin composition (that is, an insulating resin cured body or a semi-cured body). )
  • a cured or semi-cured insulating resin composition that is, an insulating resin cured body or a semi-cured body.
  • FIG. 1 is a cross-sectional view showing a preferred embodiment of the laminated body.
  • the laminate 10 shown in FIG. 1 includes a metal plate 1, a metal foil 3, and an insulating layer 2 composed of an insulating resin cured body interposed between the metal plate 1 and the metal foil 3.
  • a circuit board can be easily formed by processing the metal foil 3 of the laminated body 10 into a predetermined pattern.
  • the circuit board according to the present embodiment includes a metal plate, an insulating resin cured body arranged on the metal plate, and a circuit unit arranged on the insulating resin cured body.
  • the metal plate and the circuit portion may be separated by an insulating resin cured body, and the insulating resin cured body may function as an insulating layer.
  • the circuit part may be made of a metal material.
  • the metal material constituting the circuit portion include the same metal materials as those constituting the above-mentioned metal foil.
  • the circuit unit may be a metal leaf processed into a predetermined pattern.
  • the thickness of the circuit portion is not particularly limited, and may be, for example, 5 ⁇ m to 1 mm from the viewpoint of heat resistance and workability.
  • the thickness of the cured insulating resin is not particularly limited, and may be, for example, 50 ⁇ m to 300 ⁇ m from the viewpoint of thermal conductivity and insulating properties.
  • the circuit board has a volume resistivity between the circuit unit and the metal plate at 85 ° C. 85% RH after a voltage of 500 V DC is continuously applied between the circuit unit and the metal plate in an environment of 85 ° C. 85% RH for 1000 hours.
  • it is preferably 1.0 ⁇ 10 9 ⁇ ⁇ cm or more, and more preferably 5.0 ⁇ 10 9 ⁇ ⁇ cm or more.
  • Such a circuit board can be said to be a circuit board having particularly excellent moisture insulation resistance.
  • the manufacturing method of the circuit board is not particularly limited.
  • the circuit board can be manufactured by a method including a step of processing the metal foil of the above-mentioned laminate into a predetermined pattern.
  • the method of processing (etching) the metal foil is not particularly limited, and a conventionally known method may be applied.
  • FIG. 2 is a cross-sectional view showing a preferred embodiment of the circuit board.
  • the circuit board 20 shown in FIG. 2 includes a metal plate 1, a circuit unit 4, and an insulating layer 2 composed of an insulating resin cured body interposed between the metal plate 1 and the circuit unit 4.
  • the circuit board 20 may be, for example, a metal foil 3 of the laminated body 10 processed into a circuit portion 4.
  • Tetrahydrofuran was used as the mobile phase, and the measurement was carried out with an RI detector (refractive index method) under the condition of a flow rate of 1.0 ml / min, and a polystyrene-converted value was obtained.
  • the hydroxyl group bonded to the phosphorus atom was confirmed by comparing the result of size exclusion chromatography of the obtained sample with the result of mass spectrometry by LC / MS and the result of structural analysis by 1 H-NMR and 13 C-NMR.
  • An insulating resin composition is applied onto an aluminum plate having a thickness of 1.5 mm (manufactured by Amano Aluminum Co., Ltd., "A1050 1.5 mm thickness") and dried at 120 ° C. for 15 minutes in a B stage (semi-cured) state. And said. The amount of the insulating resin composition applied was adjusted so that the thickness of the insulating layer after curing was 100 ⁇ m.
  • a copper foil with a thickness of 70 ⁇ m (manufactured by Furukawa Electric Co., Ltd., “electrolytic copper foil 70 ⁇ m thickness”) was placed on a semi-cured body of the insulating resin composition, and was subjected to a heat press method in a laminated state 180 The semi-cured product was cured by heat treatment at ° C. for 6 hours to obtain a laminated product.
  • the copper foil was etched using a sulfuric acid-hydrogen peroxide mixed solution as an etching solution.
  • a circuit board having a circuit portion made of copper foil was obtained.
  • Example 3> The addition amount of "YD-6020” is 1.2 parts by mass, the addition amount of “YX8000” is 3.6 parts by mass, the addition amount of “D400” is 1.2 parts by mass, and the addition amount of "D2000” is 0.
  • Example 4 An insulating resin composition and a circuit board were obtained in the same manner as in Example 1 except that the amount of the heavy metal inactivating agent added was changed to 0.4 parts by mass.
  • Example 5 An insulating resin composition and a circuit board were obtained in the same manner as in Example 1 except that the amount of the heavy metal inactivating agent added was changed to 0.02 parts by mass.
  • Example 6 An insulating resin composition and a circuit board were obtained in the same manner as in Example 1 except that the addition amount of "D400” was changed to 3.2 parts by mass and the addition amount of "D2000” was changed to 0.8 parts by mass. It was.
  • Example 7 As the heavy metal inactivating agent, 0.1 part by mass of 3-amino-1,2,4-triazole (melting point 159 ° C.) was used instead of "CDA-6". Except for the above, an insulating resin composition and a circuit board were obtained in the same manner as in Example 1.
  • Example 8 As the heavy metal inactivating agent, 0.1 part by mass of "CDA-10" (manufactured by ADEKA, melting point 227 ° C.) was used instead of "CDA-6". Except for the above, an insulating resin composition and a circuit board were obtained in the same manner as in Example 1.
  • Example 9 As the heavy metal inactivating agent, 0.1 part by mass of "CDA-1” (manufactured by ADEKA, melting point 320 ° C.) was used instead of "CDA-6". Except for the above, an insulating resin composition and a circuit board were obtained in the same manner as in Example 1.
  • Tables 1 and 2 show the formulations of the insulating resin compositions of Examples and Comparative Examples.
  • the maximum particle size and the average particle size of the inorganic filler used in Examples and Comparative Examples were determined by the following methods.
  • the measurement was performed using a "laser diffraction type particle size distribution measuring device SALD-200" manufactured by Shimadzu Corporation. Specifically, 50 cc of pure water and 5 g of an inorganic filler were added to a glass beaker, stirred with a spatula, and then dispersed with an ultrasonic cleaner for 10 minutes. The dispersion of the inorganic filler was added drop by drop to the sampler part of the device with a dropper, and the mixture was waited for stabilization until the absorbance became measurable. The measurement was performed when the absorbance became stable. In the laser diffraction type particle size distribution measuring device, the particle size distribution was calculated from the data of the light intensity distribution of the diffracted / scattered light by the particles detected by the sensor. The maximum particle size was d90 and the average particle size was d50.
  • the insulating resin composition obtained in Examples and Comparative Examples and the circuit board obtained in Example 1 were evaluated by the following methods. The results are shown in Tables 1 and 2.
  • the thermal conductivity was calculated from the thermal diffusivity, specific gravity and specific heat. Specifically, first, the thermal conductivity was determined by a laser flash method using a measurement sample obtained by processing an insulating resin cured product into a width of 10 mm, a length of 10 mm, and a thickness of 1 mm. A xenon flash analyzer (LFA447 NanoFlash manufactured by NETZSCH) was used as the measuring device. The specific weight was determined using the Archimedes method. The specific heat was determined by using a differential scanning calorimeter (manufactured by TA Instruments, Inc., “Q2000”) and raising the temperature from room temperature to 300 ° C. in a nitrogen atmosphere at a heating rate of 10 ° C./min.
  • an insulating layer having both a low elastic modulus and a high thermal conductivity can be formed, and a circuit board having excellent moisture insulation resistance, moisture adhesion resistance and heat cycle resistance can be obtained. It was confirmed that.
  • the present invention it is possible to form an insulating layer having both excellent adhesiveness and insulating properties and a low elastic modulus in a high temperature and high humidity environment.
  • a circuit board provided with the above-mentioned insulating layer and excellent in moisture insulation resistance, thermal conductivity and heat cycle resistance can be obtained. Therefore, the present invention can be suitably used in fields where heat cycle resistance, moisture insulation resistance, heat dissipation, etc. are required (for example, circuit boards for in-vehicle fillers).

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Laminated Bodies (AREA)

Abstract

L'invention concerne une composition de résine isolante comprenant un matériau organique et une charge inorganique, le matériau organique comprenant une résine époxyde, un agent de durcissement de type amine, un composé ester de phosphate ayant au moins un groupe hydroxyle dans chaque molécule, et un désactivateur de métaux lourds, et la teneur en charge inorganique est de 50 à 95 % en masse.
PCT/JP2020/038030 2019-11-08 2020-10-07 Composition de résine isolante, article durci de résine isolante, stratifié et carte de circuit imprimé WO2021090629A1 (fr)

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CN202080063653.8A CN114364738A (zh) 2019-11-08 2020-10-07 绝缘性树脂组合物、绝缘性树脂固化物、层合体及电路基板
JP2021554850A JPWO2021090629A1 (fr) 2019-11-08 2020-10-07

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WO2011125712A1 (fr) * 2010-03-31 2011-10-13 リンテック株式会社 Composition adhésive, feuille adhésive et procédé de fabrication de dispositif semiconducteur
CN108410133A (zh) * 2018-03-16 2018-08-17 苏州生益科技有限公司 树脂组合物及应用其制备的低流胶半固化片

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JPH10242606A (ja) * 1997-02-27 1998-09-11 Hitachi Chem Co Ltd 金属ベース基板
JP2002012653A (ja) * 2000-07-03 2002-01-15 Denki Kagaku Kogyo Kk 硬化性樹脂組成物及びそれを用いた金属ベース回路基板
JP2004075817A (ja) * 2002-08-15 2004-03-11 Denki Kagaku Kogyo Kk 回路基板用樹脂組成物とそれを用いた金属ベース回路基板
JP2005353974A (ja) * 2004-06-14 2005-12-22 Hitachi Chem Co Ltd 金属ベース回路基板
JP2008088302A (ja) * 2006-10-02 2008-04-17 Shin Etsu Chem Co Ltd 難燃性接着剤組成物、ならびにそれを用いた接着剤シート、カバーレイフィルムおよびフレキシブル銅張積層板
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