WO2020256005A1 - 熱硬化性樹脂組成物、樹脂シートおよび金属ベース基板 - Google Patents

熱硬化性樹脂組成物、樹脂シートおよび金属ベース基板 Download PDF

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Publication number
WO2020256005A1
WO2020256005A1 PCT/JP2020/023728 JP2020023728W WO2020256005A1 WO 2020256005 A1 WO2020256005 A1 WO 2020256005A1 JP 2020023728 W JP2020023728 W JP 2020023728W WO 2020256005 A1 WO2020256005 A1 WO 2020256005A1
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Prior art keywords
resin composition
thermosetting resin
group
composition according
epoxy
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Ceased
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PCT/JP2020/023728
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English (en)
French (fr)
Japanese (ja)
Inventor
智将 樫野
佳樹 西川
忠相 遠藤
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Sumitomo Bakelite Co Ltd
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Sumitomo Bakelite Co Ltd
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Publication date
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Priority to US17/619,265 priority Critical patent/US20220372208A1/en
Priority to DE112020002972.7T priority patent/DE112020002972T5/de
Priority to JP2020556988A priority patent/JP6908199B2/ja
Priority to CN202080045469.0A priority patent/CN113993947A/zh
Publication of WO2020256005A1 publication Critical patent/WO2020256005A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • 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
    • C08G59/20—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 epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B32B15/092—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising 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
    • B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
    • 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
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • 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
    • B32B27/38—Layered products comprising a layer of synthetic resin comprising 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
    • 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
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014—Nitrogen containing compounds
    • C08G59/4028—Isocyanates; Thioisocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/5046—Amines heterocyclic
    • C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
    • C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • 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
    • B32B2250/00—Layers arrangement
    • B32B2250/03—3 layers
    • 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
    • B32B2250/00—Layers arrangement
    • B32B2250/40—Symmetrical or sandwich layers, e.g. ABA, ABCBA, ABCCBA
    • 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
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/20—Properties of the layers or laminate having particular electrical or magnetic properties, e.g. piezoelectric
    • B32B2307/206—Insulating
    • 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
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/30—Properties of the layers or laminate having particular thermal properties
    • B32B2307/302—Conductive
    • 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
    • C08K3/38—Boron-containing compounds
    • C08K2003/382—Boron-containing compounds and nitrogen
    • C08K2003/385—Binary compounds of nitrogen with boron
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/001—Conductive additives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/08—Materials not undergoing a change of physical state when used
    • C09K5/14—Solid materials, e.g. powdery or granular

Definitions

  • thermosetting resin composition containing an epoxy resin or the like As described above, an attempt to form a heat radiating member by a thermosetting resin composition containing an epoxy resin or the like is known. However, according to the findings of the present inventors, there is still room for improvement in the conventional heat radiating member. For example, when a heat-dissipating member in a power module is formed by using a conventional thermosetting resin composition for forming a heat-dissipating member, there is still room for improvement in terms of heat-dissipating property and insulating property. This is a problem, especially for power modules that require high reliability.
  • ⁇ 200 when metal particles are used as the heat conductive particles, ⁇ 200 can be easily designed to be 12 W / (m ⁇ K) or more. In that case, however, designing the R 200 to conductive metal particles than 1.0 ⁇ 10 10 ⁇ ⁇ m is not easy.
  • the fact that R200 is 1.0 ⁇ 10 10 ⁇ ⁇ m or more means that the suitable use of the thermosetting resin composition of the present embodiment is an “insulating material”, and from the viewpoint of insulating properties. It can also be said that the absence of unwanted metal particles is expressed numerically.
  • the curing accelerator examples include imidazoles, organophosphorus compounds, organometallic salts, tertiary amines, phenol compounds, organic acids and the like. These may be used alone or in combination of two or more. Among these, from the viewpoint of heat resistance, it is selected from the group consisting of an organic phosphorus compound, a complex of an organic phosphorus compound and an organic boron compound, and a compound having an intramolecular polarization obtained by adding a compound having a ⁇ bond to the organic phosphorus compound. At least one of the above can be used. Examples of the compound having a ⁇ bond include maleic anhydride, a quinone compound, diazophenylmethane, a phenol resin and the like.
  • the mesogen structure-containing phenoxy resin can be obtained by subjecting a mesogen structure-containing phenol compound having two or more phenol groups in the molecule to an addition polymerization reaction in epichlorohydrin. That is, the mesogen structure-containing phenoxy resin can contain an addition polymer of a mesogen structure-containing phenol compound.
  • R 5 and R 7 each independently represent a glycidyl ether group.
  • R 6 and R 8 each independently represent one selected from a hydrogen atom, a chain or cyclic alkyl group having 1 to 6 carbon atoms, a phenyl group and a halogen atom.
  • e and g are independently integers of 1 to 3 and f and h are independently integers of 0 to 2. However, e + f and g + h are each of 1 to 3.
  • Examples of the polyfunctional phenol compound having three or more hydroxy groups in the molecule can include polyphenols or polyphenol derivatives.
  • a polyphenol is typically a compound containing three or more phenolic hydroxy groups in one molecule.
  • the polyphenol preferably has the above-mentioned mesogen structure in the molecule.
  • mesogen structure a biphenyl skeleton, a phenylbenzoate skeleton, an azobenzene skeleton, a stilbene skeleton, or the like can be used.
  • the polyphenol derivative includes a polyphenol compound having three or more phenolic hydroxy groups and a mesogen structure, which is changed to another substituent at a substitutable position of the compound.
  • a combination of a trifunctional phenol compound and a bifunctional epoxy compound or a combination of a trifunctional phenol compound, a bifunctional phenol compound and a bifunctional epoxy compound may be used.
  • a trifunctional phenol compound for example, resveratrol represented by the following chemical formula can be used.
  • a branched reaction compound (branched phenoxy resin) can be obtained by the combination of the trifunctional phenol compound and the bifunctional epoxy compound as described above, or the combination of the trifunctional phenol compound, the bifunctional phenol compound and the bifunctional epoxy compound. ..
  • the bifunctional phenol compound a compound in which the hydroxy groups of R 1 and R 3 are bonded to the para position of each benzene ring can be used.
  • the bifunctional epoxy compound a compound in which the glycidyl ether groups of R 5 and R 7 are bonded to the para position of each benzene ring can be used.
  • the bifunctional phenol compound has a naphthalene ring as a condensed ring, the hydroxy groups of R 1 and R 3 are at the 1-position and 3-position, 1-position and 4-position, 1-position and 5-position, and 1-position and 6-position of the naphthalene ring.
  • FIG. 1 is a cross-sectional view showing an example of the configuration of the metal base substrate 100.
  • the metal base substrate 100 can include a metal substrate 101, an insulating layer 102 provided on the metal substrate 101, and a metal layer 103 provided on the insulating layer 102. ..
  • the insulating layer 102 can be composed of one selected from the group consisting of a resin layer made of a thermosetting resin composition, a cured product of a thermosetting resin composition, and a laminated board.
  • the metal substrate 101 has a role of dissipating heat accumulated in the metal base substrate 100.
  • the metal substrate 101 is not particularly limited as long as it is a heat-dissipating metal substrate.
  • the metal substrate 101 is, for example, a copper substrate, a copper alloy substrate, an aluminum substrate, or an aluminum alloy substrate, preferably a copper substrate or an aluminum substrate, and more preferably a copper substrate.
  • a copper substrate or an aluminum substrate By using a copper substrate or an aluminum substrate, the heat dissipation of the metal substrate 101 can be improved.
  • Embodiments of the present invention will be described in detail based on Examples and Comparative Examples. The present invention is not limited to the examples.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Physics & Mathematics (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Insulated Metal Substrates For Printed Circuits (AREA)
PCT/JP2020/023728 2019-06-21 2020-06-17 熱硬化性樹脂組成物、樹脂シートおよび金属ベース基板 Ceased WO2020256005A1 (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US17/619,265 US20220372208A1 (en) 2019-06-21 2020-06-17 Thermosetting resin composition, resin sheet, and metal base substrate
DE112020002972.7T DE112020002972T5 (de) 2019-06-21 2020-06-17 Wärmehärtbare harzzusammensetzung, harzplatte und metallgrundsubstrat
JP2020556988A JP6908199B2 (ja) 2019-06-21 2020-06-17 熱硬化性樹脂組成物、樹脂シートおよび金属ベース基板
CN202080045469.0A CN113993947A (zh) 2019-06-21 2020-06-17 热固性树脂组合物、树脂片及金属基基板

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Application Number Priority Date Filing Date Title
JP2019115337 2019-06-21
JP2019-115337 2019-06-21

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US (1) US20220372208A1 (https=)
JP (2) JP6908199B2 (https=)
CN (1) CN113993947A (https=)
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WO (1) WO2020256005A1 (https=)

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WO2021172387A1 (ja) * 2020-02-27 2021-09-02 住友ベークライト株式会社 熱硬化性樹脂組成物、樹脂シートおよび金属ベース基板
JPWO2022176448A1 (https=) * 2021-02-18 2022-08-25
JP2022142755A (ja) * 2021-03-16 2022-09-30 三菱ケミカル株式会社 エポキシ樹脂組成物、硬化物及び電気・電子回路用積層板
JP2022165611A (ja) * 2021-04-20 2022-11-01 住友ベークライト株式会社 フェノキシ樹脂、熱硬化性樹脂組成物、熱伝導性シート、樹脂基板、積層板、および電子装置
JP2023009926A (ja) * 2021-07-08 2023-01-20 住友ベークライト株式会社 熱硬化性樹脂組成物、樹脂シート、金属ベース基板、および電子装置
JP2023009966A (ja) * 2021-07-08 2023-01-20 住友ベークライト株式会社 熱硬化性樹脂組成物、樹脂シート、金属ベース基板、および電子装置
JP2023180728A (ja) * 2022-06-10 2023-12-21 住友ベークライト株式会社 熱硬化性樹脂組成物、樹脂シート、熱伝導性部材、金属ベース基板、及び電子装置
JP2023180727A (ja) * 2022-06-10 2023-12-21 住友ベークライト株式会社 レスベラトロール型エポキシ樹脂、熱硬化性樹脂組成物、樹脂シート、熱伝導性部材、金属ベース基板、及び電子装置
WO2026074903A1 (ja) * 2024-10-02 2026-04-09 日本発條株式会社 絶縁材料とその製造方法

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* Cited by examiner, † Cited by third party
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DE112020006048T5 (de) * 2019-12-09 2022-09-29 Sumitomo Bakelite Co., Ltd. Wärmehärtbare harzzusammensetzung, harzplatte und metallgrundsubstrat
WO2023007894A1 (ja) * 2021-07-29 2023-02-02 昭和電工株式会社 熱伝導性樹脂組成物、硬化物、熱伝導部材及び電子機器

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WO2013065758A1 (ja) * 2011-11-02 2013-05-10 日立化成株式会社 樹脂組成物、並びにそれを用いた樹脂シート、プリプレグ、積層板、金属基板、プリント配線板及びパワー半導体装置
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