WO2018181838A1 - Composition destinée des éléments de dissipation de chaleur, élément de dissipation de chaleur, dispositif électronique, et procédé de production d'un élément de dissipation de chaleur - Google Patents

Composition destinée des éléments de dissipation de chaleur, élément de dissipation de chaleur, dispositif électronique, et procédé de production d'un élément de dissipation de chaleur Download PDF

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WO2018181838A1
WO2018181838A1 PCT/JP2018/013501 JP2018013501W WO2018181838A1 WO 2018181838 A1 WO2018181838 A1 WO 2018181838A1 JP 2018013501 W JP2018013501 W JP 2018013501W WO 2018181838 A1 WO2018181838 A1 WO 2018181838A1
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inorganic filler
coupling agent
polymerizable compound
compound
composition
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PCT/JP2018/013501
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Japanese (ja)
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研人 氏家
武 藤原
國信　隆史
和宏 滝沢
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Jnc株式会社
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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
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/34—Arrangements for cooling, heating, ventilating or temperature compensation ; Temperature sensing arrangements
    • H01L23/36—Selection of materials, or shaping, to facilitate cooling or heating, e.g. heatsinks
    • H01L23/373—Cooling facilitated by selection of materials for the device or materials for thermal expansion adaptation, e.g. carbon
    • 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
    • H05K7/00—Constructional details common to different types of electric apparatus
    • H05K7/20—Modifications to facilitate cooling, ventilating, or heating

Definitions

  • the composition for heat radiating members according to the third aspect of the present invention is the composition for heat radiating members according to the first aspect or the second aspect of the present invention, wherein the first inorganic filler and the second inorganic filler are used.
  • the fillers are boron nitride, boron carbide, boron boron nitride, graphite, carbon fiber, carbon nanotube, graphene, alumina, aluminum nitride, silica, silicon nitride, silicon carbide, zinc oxide, magnesium oxide, magnesium hydroxide, cordier, respectively. It is at least one selected from light or iron oxide materials.
  • the inorganic filler has a high thermal conductivity, and the thermal expansion coefficient is positive, very small, or negative, and by combining with these fillers, the intended composition for a heat dissipation member can be obtained. can get.
  • the composition for a heat radiating member according to the fourth aspect of the present invention is the composition for a heat radiating member according to any one of the first aspect to the third aspect of the present invention.
  • a third inorganic filler having a coefficient of thermal expansion different from that of the second inorganic filler.
  • R 7 to R 10 are each independently hydrogen or alkylene having 1 to 20 carbon atoms. If comprised in this way, it is a heat radiating member containing the inorganic filler which couple
  • the heat radiating member of this application it is a conceptual diagram which shows the coupling
  • any —CH 2 — in alkyl may be replaced by —O—” or “any —CH 2 CH 2 — may be replaced by —CH ⁇ CH—, etc.”
  • the meaning is shown in the following example.
  • a group in which any —CH 2 — in C 4 H 9 — is replaced by —O— or —CH ⁇ CH— includes C 3 H 7 O—, CH 3 —O— (CH 2 ) 2 —, CH 3 —O—CH 2 —O— and the like.
  • composition for heat dissipation member is a composition that forms a heat radiating member by curing and bonding inorganic fillers via a coupling agent and a bifunctional or higher functional polymerizable compound.
  • FIG. 1 shows an example in which boron nitride is used as an inorganic filler.
  • boron nitride h-BN
  • boron nitride there is no reactive group in the plane of the particle, so that the coupling agent binds only around the periphery.
  • Boron nitride treated with a coupling agent can form a bond with the polymerizable compound. Therefore, as shown in FIG.
  • the heat radiating member composition according to the first embodiment of the present invention is, for example, as shown in FIG. 1 and FIG. 2, a first thermally conductive material coupled to one end of a plurality of first coupling agents 1.
  • a thermally conductive second inorganic filler 2 bonded to one end of a plurality of second coupling agents 12, wherein the other end of the second coupling agent 12 is further bifunctional or higher.
  • a second inorganic filler to which the polymerizable compound 22 is bonded As shown in FIG. 2, when the heat radiating member composition is cured, the other end of the coupling agent 11 bonded to the first inorganic filler 1 is bonded to the polymerizable compound 22 of the second inorganic filler 2. In this way, a bond between inorganic fillers is formed.
  • the bifunctional or higher functional polymerizable compound may be a non-liquid crystalline compound.
  • the bifunctional or higher functional polymerizable compound has a functional group capable of forming a bond with a coupling agent.
  • Examples of the bifunctional or higher polymerizable compound include polymerizable compounds represented by the following formula (1-1).
  • R a is the following formulas (2-1) to (2-2), amino, vinyl, carboxylic anhydride residues, or any polymerizable group containing these structures
  • Rx represents naphthalene-2,6-diyl, or naphthalene-2,7-diyl represented by the following formulas (2-3) to (2-6), biphenyl-2,2 ′, biphenyl-2,4 ', One of biphenyl-3,3'
  • n is an integer from 1 to 3
  • R 6 and R 11 are each independently a single bond or alkylene having 1 to 20 carbon atoms.
  • R b is hydrogen, halogen, —CF 3 , or alkyl having 1 to 5 carbons, and q is 0 or 1.
  • R 7 to R 10 are each independently hydrogen or alkylene having 1 to 20 carbon atoms.
  • each Ra should just be a functional group which can couple
  • combinations of functional groups that form a bond between Ra and a coupling agent include combinations of oxiranyl and amino, vinyls, methacryloxys, carboxy or carboxylic anhydride residues and amines, imidazole and oxiranyl, and the like.
  • Any combination of functional groups capable of forming a bond between the polymerizable compound and the coupling agent may be used. A combination with high heat resistance is more preferable.
  • the bifunctional or higher polymerizable compound may be a liquid crystal compound.
  • the bifunctional or higher functional polymerizable compound having liquid crystallinity include a polymerizable liquid crystal compound represented by the following formula (1-2).
  • the polymerizable liquid crystal compound has a liquid crystal skeleton and a polymerizable group, and has high polymerization reactivity, a wide liquid crystal phase temperature range, good miscibility, and the like. This compound (1-2) tends to be uniform when mixed with other liquid crystalline compounds or polymerizable compounds.
  • Terminal group R a has the same meaning as R a defined in the above formula (1-1).
  • Preferred examples of A include 1,4-cyclohexylene, 1,4-cyclohexenylene, 2,2-difluoro-1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4 -Phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2 , 3,5-trifluoro-1,4-phenylene, pyridine-2,5-diyl, 3-fluoropyridine-2,5-diyl, pyrimidine-2,5-diyl, pyridazine-3,6-diyl, naphthalene -2,6-diyl, tetrahydronaphthalene-2,6-diyl, fluorene-2,7-diyl, 9
  • A is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene and the like.
  • Particularly preferred A is 1,4-cyclohexylene and 1,4-phenylene.
  • the linking group Z of the compound (1-2) is a single bond, — (CH 2 ) 2 —, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH ⁇ CH
  • —, —CF ⁇ CF— or — (CH 2 ) 4 — in particular, a single bond, — (CH 2 ) 2 —, —CF 2 O—, —OCF 2 —, —CH ⁇ CH— or —
  • the viscosity becomes small.
  • Preferred Z is a single bond, — (CH 2 ) 2 —, — (CF 2 ) 2 —, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, — OCF 2 —, —CH ⁇ CH—, —CF ⁇ CF—, —C ⁇ C—, — (CH 2 ) 4 —, — (CH 2 ) 3 O—, —O (CH 2 ) 3 —, — ( CH 2 ) 2 COO—, —OCO (CH 2 ) 2 —, —CH ⁇ CH—COO—, —OCO—CH ⁇ CH— and the like.
  • the compound (1-2) may be optically active or optically inactive.
  • the compound (1-2) may have an asymmetric carbon or an axial asymmetry.
  • the configuration of the asymmetric carbon may be R or S.
  • the asymmetric carbon may be located at either Ra or A, and when it has an asymmetric carbon, the compatibility of the compound (1-2) is good.
  • the compound (1-2) has axial asymmetry, the twist-inducing force is large.
  • the light application property may be any.
  • a compound having desired physical properties can be obtained by appropriately selecting the terminal group R a , the type of the ring structure A and the bonding group Z, and the number of rings.
  • A, Z and R a have the same meaning as A, Z and R a defined in the above formula (1-2), and P represents the following formula (2- 1) to (2-2) represents a polymerizable group, cyclohexene oxide, phthalic anhydride, or succinic anhydride, and Y is a single bond or alkylene having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms.
  • arbitrary —CH 2 — may be replaced by —O—, —S—, —CO—, —COO—, —OCO— or —CH ⁇ CH—.
  • Y is alkylene in which —CH 2 — at one or both ends of alkylene having 1 to 10 carbon atoms is replaced by —O—.
  • m is an integer of 1 to 6, preferably an integer of 2 to 6, and more preferably an integer of 2 to 4.
  • R b is hydrogen, halogen, —CF 3 , or alkyl having 1 to 5 carbons, and q is 0 or 1.
  • R a , P and Y are as defined in the above formulas (1-a) and (1-b).
  • Z 1 is each independently a single bond, — (CH 2 ) 2 —, — (CF 2 ) 2 —, — (CH 2 ) 4 —, —CH 2 O—, —OCH 2 —, — (CH 2 ) 3 O—, —O (CH 2 ) 3 —, —COO—, —OCO—, —CH ⁇ CH—, —CF ⁇ CF—, —CH ⁇ CHCOO—, —OCOCH ⁇ CH—, — (CH 2 ) 2 COO—, —OCO (CH 2 ) 2 —, —C ⁇ C—, —C ⁇ C—COO—, —OCO—C ⁇ C—, —C ⁇ C—CH ⁇ CH—, —CH ⁇ CH —C ⁇ C—, —CH ⁇ N—, —N ⁇ CH—,
  • Z 3 is each independently a single bond, alkyl having 1 to 10 carbon atoms, — (CH 2 ) a —, —O (CH 2 ) a O—, —CH 2 O—, —OCH 2 —, —O (CH 2 ) 3 —, — (CH 2 ) 3 O—, —COO—, —OCO—, —CH ⁇ CH—, —CH ⁇ CHCOO—, —OCOCH ⁇ CH—, — (CH 2 ) 2 COO— , —OCO (CH 2 ) 2 —, —CF ⁇ CF—, —C ⁇ C—, —CH ⁇ N—, —N ⁇ CH—, —N ⁇ N—, —OCF 2 — or —CF 2 O— And the plurality of Z 3 may be the same or different.
  • a is an integer of 1 to 20.
  • X is a substituent of 1,4-phenylene and fluorene-2,7-diyl in which arbitrary hydrogen may be replaced by halogen, alkyl or fluorinated alkyl, and represents halogen, alkyl or fluorinated alkyl.
  • More preferred compound (1-2) can be represented by the following formula (1-c) or (1-d).
  • A, Y, Z, R a and m are as defined above, and P 1 represents a polymerizable group represented by the following formulas (2-1) to (2-2).
  • two P 1 represent the same polymerizable group (2-1) to (2-2)
  • two Y represent the same group
  • two Y are symmetrical. Combine to be.
  • the compounds (1-1) and (1-2) can be synthesized by combining known methods in organic synthetic chemistry. Methods for introducing the desired end groups, ring structures and linking groups into the starting materials are described, for example, by Houben-Wyle, Methods of Organic Chemistry, Georg Thieme Verlag, Stuttgart, Organic Syntheses, John Books such as Wily & Sons, Inc., Organic Reactions, John Wily & Sons Inc., Comprehensive Organic Synthesis, Pergamon Press, New Experimental Chemistry Course (Maruzen) It is described in. Reference may also be made to JP-A-2006-265527.
  • the bifunctional or higher functional polymerizable compound may be a polymerizable compound other than the polymerizable compound represented by the above formulas (1-1) and (1-2).
  • polymerizable compound may be a polymerizable compound other than the polymerizable compound represented by the above formulas (1-1) and (1-2).
  • the liquid crystallinity is insufficient. Examples of the compound that were not present.
  • the polymerizable compound can be synthesized by combining known methods in organic synthetic chemistry.
  • the polymerizable compound used in the present invention preferably has a bifunctional or higher functional group in order to form a bond with a coupling agent, and includes a case where the functional group is trifunctional or higher, or tetrafunctional or higher. Furthermore, a compound having a functional group at both ends of the long side of the polymerizable compound is preferable because it can form a linear bond. If the surface modification with a polymerizable compound or the like is too little, the strength of the resin becomes strong because the number of molecules binding between the fillers is too few and the strength is lowered. Therefore, it is desirable to appropriately adjust the surface modification amount according to the required characteristics.
  • Examples of the first inorganic filler and the second inorganic filler include nitrides, carbides, carbon materials, metal oxides, and silicate minerals.
  • the first inorganic filler and the second inorganic filler may be the same or different.
  • boron nitride, boron carbide, boron nitride, graphite, and the like are used as inorganic fillers having high thermal conductivity and a very small or negative coefficient of thermal expansion. Examples thereof include carbon fibers and carbon nanotubes.
  • alumina, silica, magnesium oxide, zinc oxide, iron oxide, ferrite, mullite, cordierite, silicon nitride, and silicon carbide can be given.
  • an inorganic filler having the following high thermal conductivity and a positive coefficient of thermal expansion may be used for either one of the first and second inorganic fillers.
  • the third inorganic filler may be unmodified, may be modified with a coupling agent, or may be modified with a coupling agent and a polymerizable compound.
  • the inorganic filler is preferably boron nitride, aluminum nitride, silicon nitride, silicon carbide, graphite, carbon fiber, or carbon nanotube.
  • hexagonal boron nitride (h-BN) and graphite are preferable.
  • Boron nitride and graphite are preferable because they have a very high thermal conductivity in the plane direction, and boron nitride has a low dielectric constant and high insulation.
  • the use of plate-like crystal boron nitride is preferable because the plate-like structure is easily oriented along the mold by the flow and pressure of the raw material during molding and curing.
  • the average particle size of the inorganic filler is preferably 0.1 to 200 ⁇ m. More preferably, it is 1 to 100 ⁇ m. When it is 0.1 ⁇ m or more, the thermal conductivity is good, and when it is 200 ⁇ m or less, the filling rate can be increased.
  • the average particle size is based on particle size distribution measurement by a laser diffraction / scattering method. That is, when the powder is divided into two from a certain particle size by the wet method using the analysis based on the Franhofer diffraction theory and Mie's scattering theory, the larger side and the smaller side are equivalent (volume basis). Was the median diameter.
  • the ratio of the inorganic filler, the coupling agent, and the polymerizable compound depends on the amount of the coupling agent to be combined with the inorganic filler to be used.
  • the compound used as the first and second inorganic fillers for example, boron nitride
  • the reaction amount of the coupling agent to the inorganic filler varies mainly depending on the size of the inorganic filler and the reactivity of the coupling agent used.
  • the larger the inorganic filler the smaller the amount of modification because the area ratio of the side surface of the inorganic filler decreases.
  • the volume ratio of the coupling agent and polymerizable compound in the heat radiating member to the inorganic component is preferably in the range of 5:95 to 30:70, more preferably 10:90 to 25:75. desirable.
  • An inorganic component is an inorganic raw material before performing a silane coupling agent process.
  • the coupling agent to be bonded to the inorganic filler has a functional group that can be bonded to the functional group of the bifunctional or higher polymerizable compound.
  • Examples of the coupling agent include silane coupling agents represented by the following formula (3-1).
  • R 1 is H—, or CH 3 — (CH 2 ) 0-4 — ;
  • R 2 is — (CH 2 ) 0-3 —O—;
  • R 3 is 1,3-phenylene, 1,4-phenylene, naphthalene-2,6-diyl, or naphthalene-2,7-diyl;
  • R 4 is — (NH) 0-1 — (CH 2 ) 0-3 — ;
  • R 5 is H—, or CH 3 — (CH 2 ) 0-7 — ;
  • Ry is oxiranyl, oxetanyl, amino, vinyl, carboxylic anhydride residue, or any polymerizable group containing these structures;
  • j is an integer from 0 to 3;
  • k is an integer from 0 to
  • the functional group possessed by the bifunctional or higher polymerizable compound is oxiranyl, an acid anhydride residue, or the like, it preferably reacts with these functional groups, and therefore preferably has an amine-based reactive group at the terminal.
  • Silica Ace (registered trademark) S310, S320, S330, and S360 are available from JNC Corporation, and KBM903 and KBE903 are available from Shin-Etsu Chemical Co., Ltd.
  • the terminal of the bifunctional or higher polymerizable compound is an amine, a coupling agent having oxiranyl or the like at the terminal is preferable.
  • the product manufactured by JNC Corporation includes Sila Ace (registered trademark) S510, S530, and the like.
  • combinations of functional groups that form a bond between a coupling agent and a polymerizable compound include, for example, combinations of oxiranyl and amino, vinyls, methacryloxys, carboxy or carboxylic anhydride residues and amines, imidazole and oxiranyl, etc. It can be mentioned, but is not limited to these. Any combination of functional groups capable of forming a bond between the coupling agent and the polymerizable compound may be used. A combination with high heat resistance is more preferable. Modification of the inorganic filler with a coupling agent is more preferable as the number of bonds increases as the number increases.
  • the first coupling agent and the second coupling agent may be the same or different.
  • the composition for heat dissipation member may further contain an organic compound (for example, a polymerizable compound or a polymer compound) that is not bonded to the first inorganic filler and the second inorganic filler, that is, does not contribute to the bonding. Further, it may contain a polymerization initiator, a solvent and the like.
  • an organic compound for example, a polymerizable compound or a polymer compound
  • it may contain a polymerization initiator, a solvent and the like.
  • the composition for a heat radiating member may include a polymerizable compound (in this case, not necessarily bifunctional or higher) that is not bonded to an inorganic filler as a constituent element.
  • a polymerizable compound a compound which does not hinder the thermosetting of the inorganic filler and does not evaporate or bleed out by heating is preferable.
  • This polymerizable compound is classified into a compound having no liquid crystallinity and a compound having liquid crystallinity.
  • Examples of the polymerizable compound having no liquid crystallinity include vinyl derivatives, styrene derivatives, (meth) acrylic acid derivatives, sorbic acid derivatives, fumaric acid derivatives, itaconic acid derivatives, and the like.
  • the content first, it is desirable to prepare a composition for a heat dissipation member that does not contain an unbonded polymerizable compound, measure its porosity, and add an amount of the polymerizable compound that can fill the void.
  • the composition for a heat radiating member may include a polymer compound that is not bonded to an inorganic filler as a constituent element.
  • a polymer compound a compound that does not lower the film formability and the mechanical strength is preferable.
  • the polymer compound may be a polymer compound that does not react with an inorganic filler, a coupling agent, and a polymerizable compound.
  • the polymerizable compound is oxiranyl and the silane coupling agent has amino, a polyolefin resin , Polyvinyl resin, silicone resin, wax and the like.
  • the inorganic filler After the inorganic filler is cured, it may be compounded by a method such as injecting into the void in a temperature range showing an isotropic phase, and an amount of liquid crystal compound calculated so as to fill the void in the inorganic filler in advance. It may be mixed and the inorganic fillers may be polymerized.
  • the composition for heat radiating members may contain a polymerization initiator as a constituent element.
  • a polymerization initiator for example, a radical photopolymerization initiator, a cationic photopolymerization initiator, a thermal radical polymerization initiator, or the like may be used depending on the components of the composition and the polymerization method.
  • a thermal radical polymerization initiator is preferable.
  • Preferred initiators for thermal radical polymerization include, for example, benzoyl peroxide, diisopropyl peroxydicarbonate, t-butylperoxy-2-ethylhexanoate, t-butylperoxypivalate, di-t-butylperoxide.
  • Oxide (DTBPO) t-butylperoxydiisobutyrate, lauroyl peroxide, dimethyl 2,2′-azobisisobutyrate (MAIB), azobisisobutyronitrile (AIBN), azobiscyclohexanecarbonitrile (ACN), etc.
  • DTBPO diisopropyl peroxydicarbonate
  • t-butylperoxy-2-ethylhexanoate t-butylperoxypivalate
  • di-t-butylperoxide Oxide
  • MAIB dimethyl 2,2′-azobisisobutyrate
  • AIBN azobisisobuty
  • the composition for heat radiating members may contain a solvent.
  • the polymerization may be performed in a solvent or without a solvent.
  • the composition containing a solvent may be applied onto a substrate by, for example, a spin coating method and then photopolymerized after removing the solvent.
  • post-treatment may be performed by heat curing after heating to an appropriate temperature.
  • fibers or long molecules such as polyvinyl formal, polyvinyl butyral, polyester, polyamide, and polyimide can be used as inorganic fibers and cloth such as glass fibers, carbon fibers, and carbon nanotubes, or polymer additives.
  • a coupling process is performed on the first inorganic filler, and one end of the coupling agent and the first inorganic filler are bonded together.
  • a known method can be used for the coupling treatment.
  • an inorganic filler and a coupling agent are added to a solvent. After stirring using a stirrer etc., it dries. After drying the solvent, heat treatment is performed under vacuum conditions using a vacuum dryer or the like.
  • a solvent is added to the inorganic filler and pulverized by ultrasonic treatment. The solution is separated and purified using a centrifuge.
  • the inorganic filler subjected to the coupling treatment after purification is dried using an oven.
  • the second inorganic filler is subjected to a coupling treatment (or the first inorganic filler subjected to the coupling treatment may be used as a second inorganic filler), and a coupling agent A bifunctional or higher functional polymerizable compound is further bonded to the other end of the substrate.
  • the inorganic filler subjected to the coupling treatment and the bifunctional or higher functional polymerizable compound are mixed using an agate mortar or the like, and then kneaded using two rolls or the like.
  • the first inorganic filler and the second inorganic filler are weighed, for example, so that the weight of the inorganic filler alone is 1: 1, and mixed in an agate mortar or the like. Then, it mixes using 2 rolls etc. and the composition for heat radiating members is obtained.
  • the mixing ratio of the first inorganic filler and the second inorganic filler is such that when the bonding group forming a bond between the first inorganic filler and the second inorganic filler is amine: epoxy, the weight of the inorganic filler alone is, for example, The weight ratio is preferably 1: 1 to 1:30, more preferably 1: 3 to 1:20.
  • the mixing ratio is determined by the number of terminal linking groups that form a bond between the first inorganic filler and the second inorganic filler. For example, if it is a secondary amine, it can react with two oxiranyls. A small amount may be used, and the oxiranyl side may be ring-opened, and it is preferable to use a larger amount calculated from the epoxy equivalent.
  • Manufacturing a heat radiating member As an example, a method for manufacturing a film as a heat radiating member using the composition for a heat radiating member will be described. The heat radiating member composition is sandwiched between hot plates using a compression molding machine, and oriented / cured by compression molding.
  • the pressure at the time of compression molding is preferably 50 ⁇ 200kgf / cm 2, more preferably 70 ⁇ 180kgf / cm 2.
  • the pressure during curing is preferably high.
  • the pressure is appropriately changed depending on the fluidity of the mold and the target physical properties (which direction of thermal conductivity is important) and an appropriate pressure is applied.
  • the composition is applied onto a substrate, and the solvent is removed by drying to form a coating layer having a uniform film thickness.
  • the coating method include spin coating, roll coating, caten coating, flow coating, printing, micro gravure coating, gravure coating, wire bar coating, dip coating, spray coating, meniscus coating, and the like.
  • the solvent can be removed by drying, for example, by air drying at room temperature, drying on a hot plate, drying in a drying furnace, blowing hot air or hot air, and the like.
  • the conditions for removing the solvent are not particularly limited, and it may be dried until the solvent is almost removed and the fluidity of the coating layer is lost.
  • the substrate examples include metal substrates such as copper, aluminum, and iron; inorganic semiconductor substrates such as silicon, silicon nitride, gallium nitride, and zinc oxide; glass substrates such as alkali glass, borosilicate glass, and flint glass; alumina; Inorganic insulating substrates such as aluminum nitride; polyimide, polyamideimide, polyamide, polyetherimide, polyetheretherketone, polyetherketone, polyketonesulfide, polyethersulfone, polysulfone, polyphenylenesulfide, polyphenyleneoxide, polyethyleneterephthalate, polybutyleneterephthalate , Polyethylene naphthalate, polyacetal, polycarbonate, polyarylate, acrylic resin, polyvinyl alcohol, polypropylene, cellulose, Triacetyl cellulose or partially saponified product thereof, epoxy resins, phenolic resins, and a plastic film substrate such as norbornene resins.
  • the film substrate may be a uniaxially stretched film or a biaxially stretched film.
  • the film substrate may be subjected to surface treatment such as saponification treatment, corona treatment, or plasma treatment in advance.
  • the material used as the protective layer include polyvinyl alcohol.
  • an anchor coat layer may be formed in order to improve the adhesion between the protective layer and the substrate.
  • Such an anchor coat layer may be any inorganic or organic material as long as it improves the adhesion between the protective layer and the substrate.
  • the bond between the inorganic fillers is configured by the coupling-processed inorganic filler and the coupling-processed inorganic filler modified with the polymerizable compound has been described.
  • the first inorganic filler is subjected to a coupling treatment with an amino-containing silane coupling agent.
  • the second inorganic filler is coupled with the silane coupling agent. Finally, the amino on the first inorganic filler side is bonded to the epoxy contained in the polymerizable compound on the second inorganic filler side.
  • the inorganic filler modified with the polymerizable compound after the coupling treatment may be used to bond the polymerizable compounds with an appropriate polymerization initiator or the like to form a bond between the inorganic fillers.
  • the above compound (1-2) is preferable as a heat dissipation material because it has a larger number of rings and is less likely to be softened at a higher temperature.
  • the heat resistance is high, and when the linearity is high, the elongation and fluctuation due to heat between the inorganic fillers are small, and furthermore, heat phonon conduction can be efficiently transmitted, which is preferable.
  • polycyclic and high linearity often develops liquid crystallinity as a result, it can be said that the liquid crystallinity improves heat conduction.
  • the heat radiating member according to the second embodiment of the present invention is formed by molding a cured product obtained by curing the composition for heat radiating member according to the first embodiment.
  • the cured product has high thermal conductivity and high heat resistance, and has a negative or very small thermal expansion coefficient, and is excellent in chemical stability, hardness, mechanical strength, and the like.
  • the mechanical strength includes Young's modulus, tensile strength, tear strength, bending strength, bending elastic modulus, impact strength, and the like.
  • the heat radiating member of the present invention is useful for a heat radiating plate, a heat radiating sheet, a heat radiating film, a heat radiating adhesive, a heat radiating molded product, and the like.
  • thermosetting temperature ranges from room temperature to 350 ° C., preferably from room temperature to 250 ° C., more preferably from 50 ° C. to 200 ° C.
  • curing time is 5 ° C.
  • the range is from second to 10 hours, preferably from 1 minute to 5 hours, more preferably from 5 minutes to 1 hour.
  • reheating treatment may be performed to reduce strain and the like.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Thermal Sciences (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Computer Hardware Design (AREA)
  • Power Engineering (AREA)
  • Combustion & Propulsion (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyethers (AREA)
  • Epoxy Resins (AREA)

Abstract

La présente invention concerne une composition qui est susceptible de former un élément de dissipation de chaleur présentant une grande conductivité thermique et une grande résistance à la chaleur, tout en pouvant être régulée pour ce qui est du coefficient de dilatation thermique. Une composition destinée à des éléments de dissipation de chaleur selon la présente invention contient : une première charge inorganique (1) conductrice de chaleur, qui est liée à une extrémité d'un premier agent d'accouplement ; et une seconde charge inorganique conductrice de chaleur (2), qui est liée à une extrémité d'un second agent d'accouplement, l'autre extrémité du second agent d'accouplement étant liée à un composé polymérisable (22) bifonctionnel ou à fonctionnalité plus élevée. Le composé polymérisable bifonctionnel ou à fonctionnalité plus élevée est un composé non-cristal liquide ; et au moins un groupe fonctionnel du composé polymérisable peut être lié à l'autre extrémité du premier agent d'accouplement.
PCT/JP2018/013501 2017-03-31 2018-03-29 Composition destinée des éléments de dissipation de chaleur, élément de dissipation de chaleur, dispositif électronique, et procédé de production d'un élément de dissipation de chaleur WO2018181838A1 (fr)

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WO2016031888A1 (fr) * 2014-08-27 2016-03-03 Jnc株式会社 Composition pour éléments de dissipation de chaleur, élément de dissipation de chaleur, dispositif électronique, et procédé de production d'élément de dissipation de chaleur

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TWI522340B (zh) * 2010-01-29 2016-02-21 Nippon Kayaku Kk Phenol compounds, epoxy resins, epoxy resin compositions, prepregs and the like
JP2012031402A (ja) * 2010-07-02 2012-02-16 Hitachi Chem Co Ltd 樹脂組成物、ｂステージシート、樹脂付金属箔、金属基板及びｌｅｄ基板
CN105264022A (zh) * 2013-05-30 2016-01-20 住友电木株式会社 疏水性无机颗粒、散热部件用树脂组合物和电子部件装置
JP2015017165A (ja) * 2013-07-10 2015-01-29 住友ベークライト株式会社 封止用エポキシ樹脂組成物、及び半導体装置
JP2015059130A (ja) * 2013-09-17 2015-03-30 明和化成株式会社 エポキシ樹脂組成物、その用途及びエポキシ樹脂組成物用充填材

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WO2016031888A1 (fr) * 2014-08-27 2016-03-03 Jnc株式会社 Composition pour éléments de dissipation de chaleur, élément de dissipation de chaleur, dispositif électronique, et procédé de production d'élément de dissipation de chaleur

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