WO2024004525A1 - 窒化ホウ素材料、その応用製品、および窒化ホウ素材料の製造方法 - Google Patents

窒化ホウ素材料、その応用製品、および窒化ホウ素材料の製造方法 Download PDF

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WO2024004525A1
WO2024004525A1 PCT/JP2023/020739 JP2023020739W WO2024004525A1 WO 2024004525 A1 WO2024004525 A1 WO 2024004525A1 JP 2023020739 W JP2023020739 W JP 2023020739W WO 2024004525 A1 WO2024004525 A1 WO 2024004525A1
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boron nitride
silicon
containing polymer
nitride material
polydopamine
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French (fr)
Japanese (ja)
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和輝 会田
輝彦 齊藤
鉄平 細川
穂波 伊延
貴裕 濱田
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Panasonic Intellectual Property Management Co Ltd
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Panasonic Intellectual Property Management Co Ltd
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Priority to JP2024530601A priority Critical patent/JPWO2024004525A1/ja
Priority to CN202380046155.6A priority patent/CN119365415A/zh
Publication of WO2024004525A1 publication Critical patent/WO2024004525A1/ja
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B21/00—Nitrogen; Compounds thereof
    • C01B21/06—Binary compounds of nitrogen with metals, with silicon, or with boron, or with carbon, i.e. nitrides; Compounds of nitrogen with more than one metal, silicon or boron
    • C01B21/064—Binary compounds of nitrogen with metals, with silicon, or with boron, or with carbon, i.e. nitrides; Compounds of nitrogen with more than one metal, silicon or boron with boron
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/42—Introducing metal atoms or metal-containing groups
    • 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
    • C08J5/10—Reinforcing macromolecular compounds with loose or coherent fibrous material characterised by the additives used in the polymer mixture
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/38—Boron-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C08L101/10—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—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 an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/02—Homopolymers or copolymers of hydrocarbons
    • C08L25/04—Homopolymers or copolymers of styrene
    • C08L25/08—Copolymers of styrene
    • C08L25/10—Copolymers of styrene with conjugated dienes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; 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
    • C08L87/00—Compositions of unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate

Definitions

  • the present disclosure relates to boron nitride materials, applied products thereof, and methods for producing boron nitride materials.
  • 5G 5th generation mobile communication system
  • 5G uses higher frequency bands to provide faster communication speeds than previous generations. Therefore, high frequency compatible wiring boards are required for electronic devices.
  • the transmission loss in the transmission path of a wiring board depends on the frequency, and increases as the signal frequency increases. Transmission loss depends on dielectric constant and dielectric loss tangent. Therefore, in order to reduce the transmission loss of high-frequency signals, the material constituting the insulating layer of the wiring board is required to have a low dielectric constant and a low dielectric loss tangent.
  • the transmission distance of radio waves is short because high frequency bands are used. Therefore, it is necessary to increase the output of electronic devices.
  • the packaging density of circuits will also increase. Attempting to satisfy these needs increases the amount of heat generated per unit area of the wiring board. Therefore, wiring boards are required to have high heat dissipation properties.
  • the material that makes up the insulating layer of wiring boards contains fillers with excellent thermal conductivity to increase the thermal conductivity of wiring boards. .
  • the boron nitride material of the present disclosure includes: boron nitride, polydopamine attached to the boron nitride; A silicon-containing polymer.
  • the heat resistance of the filler can be improved.
  • FIG. 1 is a diagram showing a schematic configuration of a boron nitride material in Embodiment 1.
  • FIG. 2 is a flowchart illustrating an example of a method for manufacturing a boron nitride material according to the first embodiment.
  • FIG. 3 is a diagram showing a schematic structure of a resin composition in Embodiment 4.
  • FIG. 4 is a cross-sectional view of a resin-coated film in Embodiment 6.
  • FIG. 5 is a cross-sectional view of the resin-coated metal foil in Embodiment 7.
  • FIG. 6 is a cross-sectional view of a metal-clad laminate in Embodiment 8.
  • FIG. 7 is a cross-sectional view of a wiring board in Embodiment 9.
  • FIG. 8 is a diagram showing an example of a transmission electron microscope (TEM) image of a cross section perpendicular to the thickness direction of particles of the boron nitride material in the first embodiment.
  • filler in the resin composition If the content of filler in the resin composition is increased in order to improve the heat dissipation of the wiring board, mechanical properties such as flexibility are impaired and the insulating layer tends to become brittle. This is considered to be because the filler aggregates in the resin composition. Chemical modification of the filler surface is effective in improving dispersibility while suppressing filler aggregation.
  • Boron nitride is a material with high thermal conductivity, excellent heat dissipation, and excellent electrical insulation. Therefore, in recent years, boron nitride has attracted attention as a filler for insulating layers of wiring boards (for example, Patent Document 1). However, the amount of functional groups present on the surface of boron nitride particles is small, and most of the surface is inert. Therefore, it has been difficult to directly treat the surface of boron nitride particles by a method such as silane coupling to improve the dispersibility of the particles in a resin composition.
  • the dopamine-containing protein secreted from the byssus gland of the mussel exhibits stable adhesive strength even in seawater and is known as a natural adhesive.
  • Non-Patent Document 1 when a substrate is immersed in an aqueous dopamine solution, a thin film of polydopamine is formed on the surface of the substrate due to self-oxidation polymerization of dopamine.
  • Non-Patent Document 2 describes that by utilizing this property and coating boron nitride with polydopamine, the dispersibility of boron nitride as a filler was improved.
  • the present inventors have conducted extensive research into improving the heat resistance of boron nitride. As a result, we came up with the boron nitride material of the present disclosure.
  • a boron nitride material according to a first aspect of the present disclosure includes boron nitride, polydopamine attached to the boron nitride, and a silicon-containing polymer. According to the above configuration, the heat resistance of the boron nitride material can be improved.
  • the silicon-containing polymer may be attached to the polydopamine. According to the above configuration, the heat resistance of the boron nitride material can be improved.
  • the silicon-containing polymer includes a first side chain containing a silicon atom and an oxygen atom
  • the silicon-containing polymer includes a first side chain containing a silicon atom and an oxygen atom. It may be bonded to the polydopamine via an oxygen atom. According to the above configuration, the heat resistance of the boron nitride material can be improved.
  • the silicon-containing polymer is selected from the group consisting of carbon-carbon double bonds and carbon-carbon triple bonds.
  • a second side chain containing at least one selected side chain may be included.
  • the second side chain may consist only of a chain structure. According to the above configuration, when a boron nitride material is used as a filler, the heat dissipation properties of the filler are improved.
  • the silicon-containing polymer is selected from the group consisting of styrene units, butadiene units, ethylene units, and siloxane units.
  • the main chain may include at least one selected one. According to the above configuration, the heat resistance of the boron nitride material is improved.
  • the silicon-containing polymer may include a main chain containing the butadiene unit. According to the above configuration, the heat resistance of the boron nitride material is improved.
  • the silicon-containing polymer may include a copolymer containing the styrene unit and the butadiene unit. According to the above configuration, the heat resistance of the boron nitride material is further improved.
  • the silicon-containing polymer does not contain a functional group represented by -SiR 3-n (OX) n .
  • n is an integer from 1 to 3
  • X is a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a moiety bonded to the polydopamine, or a silicon atom other than the silicon atom of the functional group. Represents connected parts. At least one of X is a moiety that binds to the polydopamine. R represents a hydrocarbon group having 1 to 10 carbon atoms.
  • the silicon-containing polymer may be represented by the following formula (1) containing a plurality of repeating units.
  • a and d represent a number greater than or equal to 0, and b and c represent a number greater than 0.
  • the order of the plurality of repeating units is arbitrary. According to the above configuration, the heat resistance of the boron nitride material is further improved.
  • the boron nitride material according to the tenth aspect may satisfy 0.050 ⁇ c/(b+c+d) in the formula (1). According to the above configuration, the heat resistance of the boron nitride material is further improved.
  • the filler according to the twelfth aspect of the present disclosure includes the boron nitride material according to any one of the first to eleventh aspects. According to the above configuration, the heat resistance of the filler can be improved.
  • the resin composition according to the thirteenth aspect of the present disclosure includes the filler according to the twelfth aspect. According to the thirteenth aspect, it is possible to provide a resin composition that exhibits a low dielectric loss tangent and has excellent heat resistance.
  • the prepreg according to the fourteenth aspect of the present disclosure includes the resin composition of the thirteenth aspect or a semi-cured product of the resin composition.
  • the resin-coated film according to the fifteenth aspect of the present disclosure is A resin layer containing the resin composition of the thirteenth aspect or a semi-cured product of the resin composition, a support film; It is equipped with
  • the resin-coated metal foil according to the sixteenth aspect of the present disclosure includes: A resin layer containing the resin composition of the thirteenth aspect or a semi-cured product of the resin composition, metal foil and It is equipped with
  • the metal clad laminate according to the seventeenth aspect of the present disclosure includes: an insulating layer comprising a cured product of the resin composition of the thirteenth aspect or a cured product of the prepreg of the fourteenth aspect; metal foil and It is equipped with
  • an insulating layer comprising a cured product of the resin composition of the thirteenth aspect or a cured product of the prepreg of the fourteenth aspect; wiring and We are prepared.
  • a method for producing a boron nitride material includes preparing a base material containing boron nitride and polydopamine attached to the surface of the boron nitride, and applying a silicon-containing polymer to the base material. contacting. According to the above configuration, a boron nitride material with excellent heat resistance can be manufactured.
  • the number average molecular weight of the silicon-containing polymer may be 1200 or more. According to the above configuration, the heat resistance of the boron nitride material is improved.
  • Embodiment 1 Embodiment 1 will be described below with reference to FIGS. 1 and 2.
  • FIG. 1 is a diagram showing a schematic configuration of a boron nitride material 10 in the first embodiment.
  • Boron nitride material 10 includes boron nitride 1, polydopamine 2 attached to boron nitride 1, and silicon-containing polymer 3.
  • Boron nitride material 10 contains silicon-containing polymer 3 in addition to polydopamine 2, and polydopamine 2 is attached to boron nitride 1, so that adsorption of atmospheric moisture to polydopamine 2 is suppressed. Ru.
  • the silicon-containing polymer 3 itself is less likely to evaporate by heating than, for example, a silicon-containing low-molecular compound such as methacrylsilane.
  • the boron nitride material 10 is less likely to generate bubbles due to heating in the solder reflow process, and as a result has high heat resistance.
  • "silicon-containing low molecular compound” means an organosilicon compound with a molecular weight of less than 1,200.
  • Polydopamine 2 and silicon-containing polymer 3 may be attached to the surface of boron nitride 1.
  • polydopamine 2 may be attached to the surface of boron nitride 1 by chemically modifying the surface of boron nitride 1 with polydopamine 2.
  • Polydopamine 2 may cover at least a portion of the surface of boron nitride 1.
  • Polydopamine 2 may cover the entire surface of boron nitride 1, or may cover only a portion of the surface of boron nitride 1.
  • Silicon-containing polymer 3 may be attached to polydopamine 2.
  • Silicon-containing polymer 3 may be attached to polydopamine 2 attached to the surface of boron nitride 1.
  • FIG. 8 is an example of a transmission electron microscope (TEM) image of a cross section perpendicular to the thickness direction of the particles of the boron nitride material 10 (magnification: 50,000 times). Note that the TEM image in FIG. 8 is an image obtained by TEM observation of a sample of a resin composition produced by kneading particles of the boron nitride material 10 and a polyphenylene ether resin. As shown in FIG. 8, according to the TEM image, it can be confirmed that polydopamine 2 is attached to boron nitride 1, and that silicon-containing polymer 3 is attached to polydopamine 2.
  • TEM transmission electron microscope
  • boron nitride hexagonal boron nitride (h-BN) having a graphite-type layered structure, diamond-shaped cubic boron nitride (c-BN), amorphous boron nitride (a-BN), etc. can be used. . h-BN is particularly useful because it can be synthesized relatively easily and has excellent thermal conductivity, electrical insulation, chemical stability, and heat resistance.
  • boron nitride particles can be used. Boron nitride particles usually have a white color.
  • the shape of the boron nitride particles is not particularly limited. The shape of the boron nitride particles may be, for example, scale-like, spherical, ellipsoidal, rod-like, or the like.
  • the average particle size of the boron nitride particles is not particularly limited.
  • the average particle size of the boron nitride particles may be, for example, 0.05 ⁇ m or more and 100 ⁇ m or less, or 0.1 ⁇ m or more and 50 ⁇ m or less.
  • the average particle size of boron nitride particles means the median diameter.
  • the median diameter means the particle diameter (d50) when the cumulative volume in the volume-based particle size distribution is equal to 50%.
  • the volume-based particle size distribution is measured using, for example, a laser diffraction measuring device.
  • Polydopamine 2 is a polymer of dopamine, and may have, for example, one or both of two repeating units represented by the following formula (2). However, in the following formula (2), the indoline skeleton portion may be an indole skeleton.
  • n is an integer of 1 or more. In the above formula (2), n may be an integer of 2 or more.
  • Polydopamine 2 may have a thin film shape on the surface of the boron nitride 1 particles.
  • the thickness of the polydopamine 2 thin film is, for example, 1 nm to 300 nm.
  • the polydopamine 2 thin film covers at least a portion of the surface of the boron nitride 1 particles.
  • the thin film of polydopamine 2 may cover the entire surface of the particles of boron nitride 1, as illustrated in FIG.
  • the adhesion of polydopamine to boron nitride 1 can be confirmed by the fact that the surface of the particles of boron nitride 1 is colored blackish brown.
  • a polymer is treated as "polydopamine" even if some of the functional groups derived from dopamine in the polymer are changed due to bonding with other substances.
  • An example of a change in a functional group is the disappearance of a hydroxyl group due to dehydration condensation between the hydroxyl group of polydopamine and the hydroxyl group of another substance. Note that this dehydration condensation is a typical example of a chemical reaction that results in bonding with the silicon-containing polymer 3 described below.
  • Silicon-containing polymer 3 The structure of the silicon-containing polymer 3 is not particularly limited as long as it contains a silicon atom, and includes, for example, a main chain and a side chain branching from the main chain. Silicon-containing polymer 3 may include multiple side chains.
  • the main chain may include a first main chain made up of carbon atoms bonded to each other. The first main chain can function to prevent the surface of boron nitride 1 from having excessive hydrophilicity.
  • the silicon-containing polymer 3 may include a side chain containing a silicon atom together with the first main chain.
  • the silicon-containing polymer 3 may include a first side chain having a silicon atom and an oxygen atom. Silicon-containing polymer 3 may be bonded to polydopamine 2 via a silicon atom and an oxygen atom. More specifically, silicon-containing polymer 3 may contain oxygen atoms that bond to silicon atoms and polydopamine 2. The silicon-containing polymer 3 may be bonded to the benzene ring of the polydopamine 2 via an oxygen atom, for example. This bond can be formed through at least dehydration condensation. As in this example, the bond may be a chemical bond such as a covalent bond.
  • the silicon-containing polymer 3 may have a functional group represented by -SiR 3-n (OX) n .
  • n is an integer from 1 to 3
  • X is a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a bond bonded to polydopamine, or a silicon atom other than the silicon atom of the above functional group. Represents a joint that is connected.
  • the bonding portion X can also be represented by a single bond (-).
  • a hydrocarbon group having 1 to 10 carbon atoms is, for example, an alkyl group having 1 to 10 carbon atoms, especially 1 to 3 carbon atoms. At least one of X is a binding moiety that binds to polydopamine 2.
  • R represents a hydrocarbon group having 1 to 10 carbon atoms.
  • the silicon-containing polymer 3 When containing a bond bonded to another silicon atom, the silicon-containing polymer 3 includes a siloxane unit represented by Si--O--Si.
  • the silicon-containing polymer 3 may include a second main chain composed of siloxane units.
  • R may be an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms.
  • the alkyl group having 1 to 10 carbon atoms may have a linear, cyclic, or branched structure.
  • alkyl groups having 1 to 10 carbon atoms include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, t-butyl group, n-pentyl group, n-hexyl group.
  • aryl group having 6 to 10 carbon atoms examples include phenyl group, ⁇ -naphthyl group, ⁇ -naphthyl group, and the like.
  • the silicon-containing polymer 3 When the silicon-containing polymer 3 has a functional group represented by -SiR 3-n (OX) n and includes a bond where X is bonded to another silicon atom, the silicon-containing polymer 3 has a functional group represented by -SiR 3-n (OX) n.
  • the silicon-containing polymer 3 may include a second main chain composed of siloxane units.
  • the silicon-containing polymer 3 having such a structure may have a network structure in which siloxane units (Si--O--Si) are spread out in a network.
  • the silicon-containing polymer 3 may include a second side chain having at least one selected from the group consisting of a carbon-carbon double bond and a carbon-carbon triple bond.
  • the carbon-carbon double bond or the carbon-carbon triple bond reacts with the reactive residue of the resin of the insulating layer to form a bond, so that the adhesion between the boron nitride material 10 and the resin is improved. will improve. This reduces the thermal resistance at the interface between the boron nitride material 10 and the resin, and improves the thermal conductivity of the insulating layer. As a result, the heat dissipation of the wiring board is improved.
  • Examples of the carbon-carbon double bond include a vinyl group, methallyl group, and acryloyl group.
  • the silicon-containing polymer 3 may have one type selected from these, or may have two or more types. From the viewpoint of easy reactivity, the carbon-carbon double bond is preferably a vinyl group.
  • Examples of the reactive residue of the resin of the insulating layer include a vinyl group, a methallyl group, an acryloyl group, and the like.
  • Examples of the carbon-carbon triple bond include an ethynyl group and a propargyl group.
  • the silicon-containing polymer 3 may have one type selected from these, or may have two or more types.
  • Examples of reactive residues in the resin of the insulating layer include ethynyl groups and propargyl groups. At least one selected from the group consisting of carbon-carbon double bonds and carbon-carbon triple bonds may be located at the end of the second side chain.
  • the second side chain may consist only of a chain structure.
  • the silicon-containing polymer 3 may further include side chains other than the first side chain and the second side chain.
  • the side chains other than the first side chain and the second side chain may have, for example, a cyclic structure.
  • the cyclic structure of the side chain is, for example, an aryl group.
  • the silicon-containing polymer 3 may include a main chain having at least one selected from the group consisting of styrene units, butadiene units, ethylene units, and siloxane units. According to the above configuration, the hydrophobicity of the silicon-containing polymer 3 is improved, so that the heat resistance of the boron nitride material 10 is improved.
  • the silicon-containing polymer 3 may include a main chain having a butadiene unit. According to the above configuration, the hydrophobicity of the silicon-containing polymer 3 is further improved, so that the heat resistance of the boron nitride material 10 is further improved.
  • the silicon-containing polymer 3 may include a copolymer having styrene units and butadiene units. According to the above configuration, the hydrophobicity of the silicon-containing polymer 3 is further improved, so that the heat resistance of the boron nitride material 10 is further improved.
  • the silicon-containing polymer 3 may be represented by the following formula (1) containing multiple repeating units. According to the above configuration, the heat resistance of the boron nitride material 10 is further improved.
  • a and d represent a number greater than or equal to 0, and b and c represent a number greater than 0.
  • the order of the plurality of repeating units is arbitrary.
  • the functional group represented by -SiR 3-n (OX) n is as explained above.
  • the bond shown by the wavy line means either trans or cis, or a mixture of both.
  • the silicon-containing polymer 3 may satisfy 0 ⁇ a ⁇ 500, 1 ⁇ b ⁇ 500, 1 ⁇ c ⁇ 500, 0 ⁇ d ⁇ 500, and 5 ⁇ a ⁇ 300, 5 The following may be satisfied: ⁇ b ⁇ 300, 1 ⁇ c ⁇ 100, and 5 ⁇ d ⁇ 300.
  • the silicon-containing polymer 3 may satisfy 5 ⁇ a ⁇ 100, 5 ⁇ b ⁇ 100, 1 ⁇ c ⁇ 80, 5 ⁇ d ⁇ 100, and 5 ⁇ a ⁇ 20, 5 ⁇ b ⁇ 50, 1 ⁇ c ⁇ 60, and 5 ⁇ d ⁇ 40.
  • c represents the repeating number of butadiene units having silicon and oxygen in their side chains.
  • (b+c+d) represents the total of a butadiene unit having a repeating number b, a butadiene unit having a repeating number c, and a butadiene unit having a repeating number d.
  • the silicon-containing polymer 3 may satisfy 0.050 ⁇ c/(b+c+d) in the above formula (1).
  • the value calculated by 100 ⁇ c/(b+c+d) ⁇ may be 5.0% or more. According to the above configuration, the heat resistance of the boron nitride material 10 is further improved.
  • the dielectric properties of the boron nitride material 10 are also improved.
  • the value calculated by 100 ⁇ c/(b+c+d) ⁇ may be 15.0% or more, or may be 17.7% or more.
  • the value calculated by 100 ⁇ c/(b+c+d) ⁇ may be 30.0% or more, or may be 50.0% or more.
  • the upper limit of the value calculated by 100 ⁇ c/(b+c+d) ⁇ is, for example, 80%.
  • FIG. 2 is a flowchart illustrating an example of a method for manufacturing a boron nitride material in the first embodiment.
  • the method for manufacturing the boron nitride material 10 includes preparing a base material containing boron nitride 1 and polydopamine 2 attached to the surface of the boron nitride 1 (step S1), and applying a silicon-containing polymer 3 to the base material. contacting (step S2).
  • a base material containing boron nitride 1 and polydopamine 2 attached to the surface of boron nitride 1 can be obtained by attaching polydopamine 2 to the surface of boron nitride 1 using self-oxidation polymerization of dopamine. can. Specifically, by bringing a dopamine solution into contact with particles of boron nitride 1 and oxidatively polymerizing dopamine, polydopamine 2 is attached to the surface of the particles of boron nitride 1 to form a thin film of polydopamine 2. Can be done.
  • a dopamine solution can be obtained by adding dopamine hydrochloride to a Tris-HCl solution whose pH has been adjusted to 8.5 and stirring.
  • concentration of the dopamine solution ranges from 0.01 mg/mL to 30 mg/mL, for example.
  • the pH of the dopamine solution ranges from pH 6 to pH 11, and may range from pH 8 to pH 10.
  • the pH of the dopamine solution can be adjusted by mixing a Tris-HCl solution or the like.
  • the temperature of the dopamine solution during oxidative polymerization is, for example, 10°C to 100°C.
  • the polymerization time is, for example, 1 hour to 48 hours.
  • the thickness of the polydopamine 2 thin film is, for example, 1 nm to 300 nm. The thickness of the polydopamine 2 thin film can be controlled by controlling the polymerization time.
  • the silicon-containing polymer 3 represented by the above formula (1) is represented by the following formula (3) before being bonded to polydopamine 2.
  • R 1 and R 2 independently represent a hydrocarbon group having 1 to 10 carbon atoms.
  • m represents an integer from 1 to 3.
  • a and d represent a number greater than or equal to 0, and
  • b and c represent a number greater than 0.
  • R 1 and R 2 may independently represent an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms.
  • the alkyl group having 1 to 10 carbon atoms and the aryl group having 6 to 10 carbon atoms are as described for the functional group represented by -SiR 3-n (OX) n .
  • the alkyl group having 1 to 10 carbon atoms is preferably an alkyl group having 1 to 5 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms.
  • R 1 and R 2 are preferably linear alkyl groups, more preferably methyl or ethyl groups, independently of each other.
  • the dielectric loss tangent of the wiring board material largely depends on the orientation polarization of organic molecules contained in the wiring board material. Therefore, the hydroxyl group of polydopamine can increase the dielectric loss tangent.
  • the silicon-containing polymer represented by the above formula (3) binds to polydopamine by acting on the hydroxyl group of polydopamine.
  • the silicon-containing polymer after bonding is represented by the above formula (1).
  • the boron nitride material 10 since the number of hydroxyl groups of polydopamine is reduced, an increase in the dielectric loss tangent of the boron nitride material 10 is suppressed.
  • the silicon-containing polymer represented by the above formula (3) can be obtained through the reaction shown in the scheme below. Specifically, a styrene-butadiene copolymer represented by the following formula (4) and an organosilicon compound represented by the following formula (5) are combined, preferably in the presence of a platinum compound-containing catalyst and a platinum compound-containing catalyst. Hydrosilylation occurs in the presence of a cocatalyst. Thereby, a silicon-containing polymer represented by the above formula (3) can be obtained.
  • the styrene-butadiene copolymer represented by the above formula (4) can be synthesized by a known method such as emulsion polymerization or solution polymerization using butadiene and styrene as raw material monomers.
  • the styrene-butadiene copolymer represented by the above formula (4) can also be obtained as a commercial product.
  • Commercially available products include, for example, Ricon 100, Ricon 181, Ricon 184 (all manufactured by Clay Valley), L-SBR-820, L-SBR-841 (all manufactured by Kuraray), 1,2-SBS (all manufactured by Nippon Soda). (manufactured by), etc.
  • organosilicon compound represented by the above formula (5) examples include trimethoxysilane, methyldimethoxysilane, dimethylmethoxysilane, triethoxysilane, methyldiethoxysilane, and dimethylethoxysilane.
  • the silylation rate calculated by 100 x ⁇ c/(b+c+d) ⁇ is the same as the silylation rate calculated by 100 x ⁇ c/(b+c+d) ⁇ in the above equation (1). It can be considered as
  • the number average molecular weight of the silicon-containing polymer may be 1200 or more, or 5000 or more. According to the above configuration, the hydrophobicity of the silicon-containing polymer 3 is improved, so that the heat resistance of the boron nitride material 10 is improved.
  • the upper limit of the number average molecular weight of the silicon-containing polymer before binding to polydopamine is not particularly limited.
  • the upper limit of the number average molecular weight of the silicon-containing polymer before bonding to polydopamine 2 is, for example, 10,000 or less. Note that in the present disclosure, the number average molecular weight is a polystyrene-equivalent number average molecular weight calculated using gel permeation chromatography (GPC).
  • silicon-containing polymer 3 may be bonded to polydopamine 2.
  • silicon-containing polymer 3 can be bonded to polydopamine 2 by a silane coupling reaction.
  • the silane coupling reaction proceeds as follows. First, the silicon-containing polymer represented by the above formula (3) is hydrolyzed to generate silanol groups (Si-OH). Next, the silanol group is bonded to polydopamine 2 partially through dehydration condensation with the hydroxyl group of polydopamine 2. At this time, the silicon-containing polymer has siloxane units (Si-O-Si) formed by dehydration condensation. Thereafter, by applying heat treatment, dehydration condensation progresses, and silicon-containing polymer 3 is bonded to the benzene ring of polydopamine 2 via silicon atoms and oxygen atoms.
  • the heat dissipation gap filler according to the present embodiment includes the boron nitride material 10 according to the first embodiment.
  • a heat dissipation gap filler is a filler used to dissipate heat from an electronic component by applying it to an electronic component such as a substrate material to fill air pockets or gaps.
  • the heat dissipation gap filler is a hardening type heat dissipation paste that hardens from a paste form to a sheet form. According to the heat dissipation gap filler according to this embodiment, the heat resistance of the filler can be improved.
  • the heat dissipation gap filler according to the present embodiment is manufactured by, for example, kneading the boron nitride material 10 according to Embodiment 1 with an epoxy resin, a silicone resin, or a non-silicone acrylic resin or a ceramic resin. It can be done.
  • the filler for thermal grease according to the present embodiment includes the boron nitride material 10 according to the first embodiment.
  • a filler for heat-radiating grease is a filler used for heat-radiating grease.
  • Thermal grease is a non-hardening thermal paste used to dissipate heat from electronic components by applying them to electronic components, such as substrate materials, to fill air pockets or gaps. According to the filler for thermal grease according to the present embodiment, the heat resistance of the filler can be improved.
  • the filler for thermal grease according to the present embodiment is manufactured by, for example, kneading the boron nitride material 10 according to Embodiment 1 with an epoxy resin, a silicone resin, or a non-silicone acrylic resin or a ceramic resin. It can be done.
  • FIG. 3 is a diagram showing a schematic configuration of a resin composition 20 in Embodiment 4.
  • the resin composition 20 includes, for example, a filler 22 and a curable resin 24.
  • the filler 22 includes the boron nitride material 10 described in the first embodiment. According to this embodiment, it is possible to provide a resin composition 20 that exhibits a low dielectric loss tangent and has excellent heat resistance. As the filler 22, the boron nitride material 10 alone may be used, or other filler materials such as silica particles may be used in combination with the boron nitride material 10.
  • curable resin 24 examples include epoxy resins, cyanate ester compounds, maleimide compounds, phenol resins, acrylic resins, polyamide resins, polyamideimide resins, thermosetting polyimide resins, and polyphenylene ether resins.
  • epoxy resins cyanate ester compounds
  • maleimide compounds phenol resins
  • acrylic resins acrylic resins
  • polyamide resins polyamideimide resins
  • thermosetting polyimide resins thermosetting polyimide resins
  • polyphenylene ether resins examples include epoxy resins, cyanate ester compounds, maleimide compounds, phenol resins, acrylic resins, polyamide resins, polyamideimide resins, thermosetting polyimide resins, and polyphenylene ether resins.
  • the curable resin 24 one kind or a combination of two or more kinds selected from these can be used.
  • the resin composition 20 may contain other components.
  • Other ingredients include curing agents, flame retardants, ultraviolet absorbers, antioxidants, reaction initiators, silane coupling agents, optical brighteners, photosensitizers, dyes, pigments, thickeners, lubricants, and erasers.
  • Examples include foaming agents, dispersants, leveling agents, brighteners, antistatic agents, polymerization inhibitors, and organic solvents. If necessary, one kind or a combination of two or more kinds selected from these can be used.
  • the prepreg according to Embodiment 5 includes the resin composition 20 of Embodiment 4 shown in FIG. 3 or a semi-cured product thereof, and a fibrous base material.
  • the fibrous base material is present in the matrix of the resin composition 20 or a semi-cured product thereof.
  • Prepreg is a composite material of the resin composition 20 and a fibrous base material. According to this embodiment, it is possible to provide a prepreg suitable for high-frequency wiring boards.
  • the semi-cured material refers to a material that is partially cured to the extent that the resin composition 20 can be further cured. That is, the semi-cured material is a material obtained by semi-curing the resin composition 20. For example, when the resin composition 20 is heated, its viscosity gradually decreases. If heating is continued, curing will then begin and its viscosity will gradually increase. In such a case, the semi-cured state includes the state of the resin composition 20 during the period from the time when the viscosity starts to increase until the time when it is completely cured.
  • the fibrous base material known materials used in various electrically insulating material laminates can be used.
  • the fibrous base material include glass cloth, aramid cloth, polyester cloth, glass nonwoven fabric, aramid nonwoven fabric, polyester nonwoven fabric, pulp paper, and linter paper.
  • the resin composition 20 is impregnated into the fibrous base material through treatments such as dipping and coating.
  • a pre-cured or semi-cured prepreg according to the present embodiment can be obtained.
  • FIG. 4 is a cross-sectional view of a resin-coated film 30 in Embodiment 6.
  • the resin-coated film 30 includes a resin layer 32 containing the resin composition 20 or a semi-cured product thereof, and a support film 34.
  • a resin-coated film 30 suitable for an insulating layer can be provided.
  • the resin layer 32 is supported by a support film 34.
  • a support film 34 is placed on the surface of the resin layer 32.
  • another layer such as an adhesive layer may be provided between the resin layer 32 and the support film 34.
  • the resin layer 32 contains the resin composition 20 of Embodiment 4 shown in FIG. 3 or a semi-cured product thereof, and may or may not contain a fibrous base material.
  • the fibrous base material the same material as the fibrous base material of the prepreg can be used.
  • the resin layer 32 hardens and changes into an insulating layer.
  • An example of such an insulating layer is an insulating layer of a wiring board.
  • any support film used for resin-coated films can be used without limitation.
  • the support film 34 include resin films such as polyester films and polyethylene terephthalate films.
  • FIG. 5 is a cross-sectional view of resin-coated metal foil 40 in Embodiment 7.
  • the resin-coated metal foil 40 includes a resin layer 42 containing the resin composition 20 or a semi-cured product thereof, and a metal foil 44.
  • a resin layer 42 is supported by a metal foil 44.
  • a resin-coated metal foil 40 suitable for electronic circuit components such as wiring boards can be provided.
  • a metal foil 44 is placed on the surface of the resin layer 42.
  • another layer such as an adhesive layer may be provided between the resin layer 42 and the metal foil 44.
  • the resin layer 42 contains the resin composition of Embodiment 4 shown in FIG. 3 or a semi-cured product thereof, and may or may not contain a fibrous base material.
  • the fibrous base material the same material as the fibrous base material of the prepreg can be used.
  • the resin layer 42 hardens and changes into an insulating layer.
  • An example of such an insulating layer is an insulating layer of a wiring board.
  • metal foil 44 resin-coated metal foil and metal foil used for metal-clad laminates can be used without limitation.
  • the metal foil include copper foil and aluminum foil.
  • FIG. 6 is a cross-sectional view of a metal-clad laminate 50 in Embodiment 8.
  • Metal-clad laminate 50 includes an insulating layer 52 and at least one metal foil 54 .
  • a metal-clad laminate 50 suitable for a wiring board can be provided.
  • the insulating layer 52 includes a cured product of the resin composition 20 of the fourth embodiment shown in FIG. 3 or a cured product of the prepreg of the fifth embodiment.
  • Metal foil 54 is placed on the surface of insulating layer 52. In this embodiment, metal foils 54 are placed on each of the front and back surfaces of the insulating layer 52.
  • the metal-clad laminate 50 is typically manufactured using the prepreg of Embodiment 5.
  • a laminate is formed by stacking 1 to 20 sheets of prepreg.
  • a metal-clad laminate 50 is obtained by placing metal foil on one or both sides of the prepreg laminate and heating and pressurizing the prepreg laminate.
  • the metal foil 54 include copper foil, aluminum foil, and the like.
  • the molding conditions used when manufacturing a laminate for electrically insulating materials and a multilayer board can be applied to the molding conditions when manufacturing the metal-clad laminate 50.
  • FIG. 7 is a cross-sectional view of wiring board 60 in the ninth embodiment.
  • Wiring board 60 includes an insulating layer 62 and wiring 64.
  • a wiring board 60 suitable for high frequencies can be provided.
  • the insulating layer 62 includes a cured product of the resin composition 20 of the fourth embodiment shown in FIG. 3 or a cured product of the prepreg of the fifth embodiment.
  • the wiring 64 is supported by the insulating layer 62. Specifically, the wiring 64 is arranged on the insulating layer 62. Wiring 64 may be formed by partially removing the metal foil.
  • a wiring board 60 in which wiring 64 forming a circuit is provided on the surface of the insulating layer 62 can be obtained. That is, the wiring board 60 is obtained by partially removing the metal foil 54 on the surface of the metal-clad laminate 50 so that a circuit is formed.
  • a new laminate may be formed by laminating the prepreg of Embodiment 5 on at least one surface of the wiring board 60 and applying heat and pressure.
  • a multilayer wiring board can be obtained by patterning the metal foil on the surface of the obtained laminate to form wiring.
  • boron nitride As boron nitride, h-BN (manufactured by Denka Corporation, product number: SGP, average particle size: 18 ⁇ m) was used. A dopamine solution (concentration: 23 mg/mL) was obtained by adding dopamine hydrochloride to a Tris-HCl solution whose pH was adjusted to 8.5 and stirring. 4.5 g of boron nitride was added to the obtained dopamine solution. The solution temperature was set at 80°C, and the mixture was stirred using a magnetic stirrer for 24 hours. Thereafter, a solid was obtained by filtration. The obtained solid was washed with water and then dried.
  • polydopamine-coated boron nitride As a result, boron nitride to which polydopamine was attached (hereinafter referred to as polydopamine-coated boron nitride for convenience) was obtained. Adhesion of polydopamine was confirmed by the fact that the surface of the boron nitride particles was colored blackish brown.
  • the silylation rate of the silicon-containing polymer was 6.5%.
  • the silylation rate was measured using nuclear magnetic resonance spectrometry (NMR) to determine whether the functional group represented by -SiR 2 3-m (OR 1 ) m was introduced at the end and the terminal at which no functional group was introduced. This was confirmed by calculating the terminal ratio.
  • NMR nuclear magnetic resonance spectrometry
  • 1 g of silicon-containing polymer was dissolved in toluene to obtain a toluene solution with a concentration of 100 mg/mL.
  • 2 g of polydopamine-coated boron nitride was added to the resulting solution.
  • the solution temperature was set at 100° C., and the solution was stirred using a magnetic stirrer for 3 hours. Thereafter, a solid was obtained by filtration. The obtained solid was washed with a toluene solution and then dried. As a result, particles of the boron nitride material of Example 1 were obtained.
  • the silylation rate of the silicon-containing polymer was 12.9%. Except for this, particles of the boron nitride material of Example 2 were obtained in the same manner as in Example 1.
  • the silylation rate of the silicon-containing polymer was 17.7%.
  • the number average molecular weight of the silicon-containing polymer was 5,900. Except for this, particles of the boron nitride material of Example 3 were obtained in the same manner as in Example 1.
  • the silylation rate of the silicon-containing polymer was 50.0%. Except for this, particles of the boron nitride material of Example 4 were obtained in the same manner as in Example 1.
  • the silylation rate of the silicon-containing polymer was 71.0%. Except for this, particles of the boron nitride material of Example 5 were obtained in the same manner as in Example 1.
  • the silylation rate of the silicon-containing polymer was 1.6%. Except for this, particles of the boron nitride material of Example 6 were obtained in the same manner as in Example 1.
  • the silylation rate of the silicon-containing polymer was 3.2%. Except for this, particles of the boron nitride material of Example 7 were obtained in the same manner as in Example 1.
  • ⁇ Comparative example 1 ⁇ In place of the silicon-containing polymer, 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product number: KBM-503) was used. Methacrylsilane is one of the common silane coupling agents made of a silicon-containing low-molecular compound. The molecular weight of 3-methacryloxypropyltrimethoxysilane was 248.4. 1 g of 3-methacryloxypropyltrimethoxysilane was dissolved in toluene to obtain a toluene solution having a concentration of 0.1 mg/mL.
  • ⁇ Comparative example 2 Trimethoxyvinylsilane (manufactured by Tokyo Kasei Kogyo Co., Ltd., product number: V0042) was used in place of the silicon-containing polymer. Vinylsilane is one of the common silane coupling agents made of silicon-containing low-molecular compounds. The molecular weight of trimethoxyvinylsilane was 148.2. 1 g of trimethoxyvinylsilane was dissolved in toluene to obtain a toluene solution having a concentration of 0.1 mg/mL. Particles of Comparative Example 2 were obtained by the same method as Comparative Example 1 except for this.
  • the heat resistance of each particle group was evaluated based on the measured 1% weight loss temperature. It was determined that the heat resistance was good if the 1% weight loss temperature was 220°C or higher, and particularly good if the temperature was 250°C or higher.
  • the dielectric loss tangent at a frequency of 1 GHz was measured for each particle group obtained in Examples and Comparative Examples.
  • a cavity resonator manufactured by AET, MS46122B was used as a measuring device.
  • the dielectric loss tangent of the particles of the example and other comparative examples was normalized by setting the dielectric loss tangent of Comparative Example 3 to 1. It was determined that the dielectric loss tangent was good if it was less than 1, and particularly good if it was 0.5 or less.
  • Example 1 to 5 in which the silylation rate was 5.0% or more, the 1% weight loss temperature was 250° C. or more, and the heat resistance was particularly good.
  • Examples 3 to 5 in which the silylation rate was 15.0% or more higher heat resistance and lower dielectric loss tangent were realized.
  • the silylation rate in which the silylation rate is 30.0% or more, the 1% weight loss temperature is 300°C or more, showing even higher heat resistance, and the dielectric loss tangent is 0.5 or less. The tangent was particularly good.
  • the boron nitride material of the present disclosure can realize a filler with excellent heat resistance, so it can be used for applications such as wiring boards of electronic devices used for large-capacity communications.

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