WO2019044646A1 - Composition pour 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 pour 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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Publication number
WO2019044646A1
WO2019044646A1 PCT/JP2018/031108 JP2018031108W WO2019044646A1 WO 2019044646 A1 WO2019044646 A1 WO 2019044646A1 JP 2018031108 W JP2018031108 W JP 2018031108W WO 2019044646 A1 WO2019044646 A1 WO 2019044646A1
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inorganic filler
heat dissipation
composition
silane coupling
coupling agent
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PCT/JP2018/031108
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English (en)
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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Priority to JP2019539423A priority Critical patent/JP7060021B2/ja
Priority to CN201880050456.5A priority patent/CN111051466A/zh
Priority to KR1020207002876A priority patent/KR20200044789A/ko
Publication of WO2019044646A1 publication Critical patent/WO2019044646A1/fr

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    • 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 present invention relates to a composition capable of forming a heat dissipating member used in an electronic device such as an electronic substrate. Further, the present invention relates to a heat dissipating member capable of dissipating heat by efficiently conducting and transmitting the heat generated by the electronic device.
  • the operating temperature of semiconductor devices for power control such as hybrid cars and electric cars, CPUs for high-performance computers, etc. has risen due to the use of wide gap semiconductors and the like.
  • the operating temperature is 200 ° C. or higher, and therefore the package material is required to have high heat resistance of 250 ° C. or higher.
  • thermal strain is generated due to the difference in the coefficient of thermal expansion between the materials used in the package, and the reduction in life due to peeling of the wiring is also a problem.
  • Patent Document 2 discloses a heat dissipation member in which an organic material and an inorganic material are compounded, and the heat dissipation member in which inorganic materials are connected by a silane coupling agent and a polymerizable liquid crystal compound. By connecting the silane coupling agent and the polymerizable liquid crystal compound, it has become possible to extremely enhance the thermal conductivity between the inorganic materials.
  • the heat dissipating member obtained by these methods uses a liquid crystal compound, although the heat conductivity is high, the heat resistance is not sufficient.
  • an object of the present invention is to provide a composition capable of forming a heat dissipating member simultaneously having high thermal conductivity and high heat resistance, and a heat dissipating member obtained using the composition.
  • the present inventors diligently studied to solve the above problems. As a result, instead of adding an inorganic material such as boron nitride to the resin, the inorganic material and an organic material such as a silane coupling agent are combined and added to the resin in such an aspect as connecting the inorganic materials. It has been found that the heat dissipating member having a high thermal conductivity can be formed and the heat resistance can be further improved by using it as the present invention.
  • composition for a heat dissipation member according to the first aspect of the present invention comprises a first inorganic filler bonded to one end of a first silane coupling agent, and a second inorganic bonded to one end of a second silane coupling agent. It contains a filler and a bifunctional or higher functional carboxylic acid anhydride. For example, as shown in FIG.
  • a first inorganic filler 1 bonded to one end of a first silane coupling agent 11 and a second inorganic filler 2 bonded to one end of a second silane coupling agent 12 A composition for a heat dissipation member, wherein the other end of the first silane coupling agent 11 and the other end of the second silane coupling agent 12 are each bonded to a bifunctional or higher functional carboxylic acid anhydride 21 by curing treatment. It is a thing.
  • the "one end” and the “other end” may be the edge or the end of the shape of the molecule, and may or may not be both ends of the long side of the molecule.
  • the heat dissipating member can be formed by combining the inorganic fillers with each other via the silane coupling agent and the carboxylic acid anhydride. Therefore, since the phonon which is a main element of heat conduction can be directly propagated, the heat dissipation member obtained from the composition for heat dissipation member can have extremely high thermal conductivity and extremely high heat resistance. .
  • composition for heat dissipation member according to the second aspect of the present invention is the composition for heat dissipation member according to the first aspect of the present invention, wherein the first inorganic filler combined with one end of the first silane coupling agent
  • the other end of the first silane coupling agent is bonded to a bifunctional or higher functional carboxylic acid anhydride.
  • the heat dissipating member can be easily formed by combining the inorganic fillers with each other via the silane coupling agent and the carboxylic acid anhydride.
  • composition for heat dissipation member according to the third aspect of the present invention is the composition for heat dissipation member according to the first aspect or the second aspect of the present invention, wherein the bifunctional or higher carboxylic acid anhydride is anhydrous It is at least one selected from the group consisting of phthalic acid, succinic anhydride, maleic anhydride, acetic anhydride, propionic anhydride and benzoic anhydride.
  • the carboxylic anhydride is thermosetting, can be cured without being affected by the amount of the filler, and is further excellent in heat resistance.
  • the molecular structure is considered to be advantageous for the conduction of phonons because of its symmetry and linearity.
  • composition for heat dissipation member according to the fourth aspect of the present invention is the composition for heat dissipation member according to the first aspect or the second aspect of the present invention, wherein the bifunctional or higher carboxylic acid anhydride has the formula (1) At least one compound selected from the group of compounds represented by Formula (2) and Formula (3).
  • R 1 is independent of a single bond, alkyl having 1 to 20 carbons, cycloalkyl having 4 to 8 carbons, aryl and arylalkyl having 7 to 20 carbons And the group selected.
  • composition for heat dissipation member according to the fifth aspect of the present invention is the composition for heat dissipation member according to the first aspect or the second aspect of the present invention, wherein the bifunctional or higher carboxylic acid anhydride has the formula (4) and at least one compound selected from the group of compounds represented by formula (5).
  • R 2 is independently selected from a single bond, alkyl having 1 to 20 carbons, cycloalkyl having 4 to 8 carbons, aryl and arylalkyl having 7 to 20 carbons Group.
  • R 3 is independently carbon or nitrogen.
  • composition for heat dissipation member according to the sixth aspect of the present invention is the composition for heat dissipation member according to the first aspect or the second aspect of the present invention, wherein the bifunctional or higher carboxylic acid anhydride has the formula It is at least one compound selected from the group of compounds represented by (6).
  • R 4 and R 5 are groups independently selected from cycloalkyl having 4 to 8 carbon atoms, aryl and arylalkyl having 7 to 20 carbon atoms.
  • n is independently 1 to 4.
  • the composition for heat dissipation member according to the seventh aspect of the present invention is the composition for heat dissipation member according to any one of the first aspect to the sixth aspect of the present invention, which comprises:
  • the second inorganic filler is a nitride, a metal oxide, a silicate compound, or a carbon material. If comprised in this way, a thermal radiation member can contain a more preferable compound as an inorganic filler.
  • the composition for heat dissipation member according to the eighth aspect of the present invention is the composition for heat dissipation member according to any one of the first aspect to the seventh aspect of the present invention, wherein the first inorganic filler And the second inorganic filler is at least one selected from boron nitride, aluminum nitride, boron carbide, boron carbon nitride, graphite, carbon fiber, carbon nanotube, alumina and cordierite.
  • the composition for a heat dissipation member according to a ninth aspect of the present invention is the composition for a heat dissipation member according to any one of the first to eighth aspects of the present invention, wherein the first inorganic filler And a third inorganic filler having a thermal expansion coefficient different from that of the second inorganic filler.
  • the composition for the heat dissipation member is compounded.
  • the physical properties of matter also produce large anisotropy.
  • the third inorganic filler By adding the third inorganic filler, there is an advantage that the orientation of the first and second inorganic fillers is relaxed and the anisotropy is reduced. Furthermore, when the thermal expansion coefficient of the first and second inorganic fillers is very small or negative, by adding the third inorganic filler having a positive thermal expansion coefficient, the thermal expansion coefficient is made negative by the mixing ratio. Positive control makes it possible to control precisely. Although there is no restriction
  • the composition for heat dissipation member according to the tenth aspect of the present invention is the composition for heat dissipation member according to any one of the first to ninth aspects of the present invention, wherein the first inorganic filler And a polymerizable compound or a macromolecular compound not bound to the second inorganic filler.
  • the first inorganic filler And a polymerizable compound or a macromolecular compound not bound to the second inorganic filler.
  • a heat dissipation member according to an eleventh aspect of the present invention is the composition according to any one of the first to tenth aspects of the present invention, wherein the heat dissipation member composition is cured. It is a heat dissipation member.
  • the heat dissipation member has a bond between the inorganic fillers, and this bond does not cause molecular vibration or phase change as in ordinary resins, so that the thermal expansion has high linearity and further high thermal conductivity. You can have
  • An electronic device is the heat dissipation member according to the eleventh aspect of the present invention, comprising: a heat dissipation member; and an electronic device having a heat generation portion, the heat dissipation member contacting the heat generation portion An electronic device, which is disposed in the electronic device.
  • the heat dissipation member has high heat resistance and can control the thermal expansion coefficient to a high temperature, so that the thermal distortion that may occur in the electronic device can be suppressed.
  • the method for producing a composition for heat dissipation member according to a thirteenth aspect of the present invention comprises the steps of: bonding a first inorganic filler to one end of a first silane coupling agent; And bonding the other end of the first silane coupling agent and the other end of the second silane coupling agent with each other.
  • a process for producing a heat sink composition comprising the steps of: According to this structure, it is possible to manufacture a heat dissipating member in which the inorganic fillers are bonded to the silane coupling agent by a carboxylic acid anhydride.
  • the heat dissipation member formed from the composition for heat dissipation member of the present invention simultaneously has extremely high thermal conductivity and heat resistance. Furthermore, they have excellent properties such as controllability of thermal expansion, chemical stability, hardness and mechanical strength.
  • the heat dissipating member is suitable for, for example, a heat dissipating substrate, a heat dissipating plate (planar heat sink), a heat dissipating sheet, a heat dissipating coating, a heat dissipating adhesive, and the like.
  • FIG. 7 is a conceptual view showing that two ends of the carboxylic acid anhydride 21 are combined with the first silane coupling agent 11 and the second silane coupling agent 12 by the curing treatment of the composition for heat dissipation member.
  • Conceptual view showing that the other end of the carboxylic acid anhydride 21 bonded to the first silane coupling agent 11 is bonded to the other end of the second silane coupling agent 12 by the curing treatment of the composition for heat dissipation member
  • It is. 5 is a graph showing measurement results by the thermomechanical analyzer of Example 1.
  • FIG. 7 is a graph showing measurement results by the thermomechanical analyzer of Example 2.
  • FIG. 15 is a graph showing the measurement results by the thermomechanical analyzer of Example 4. It is a graph which shows the measurement result by the thermomechanical analyzer of the comparative example 1.
  • FIG. 5 is a graph showing measurement results by the thermomechanical analyzer of Example 1.
  • FIG. 7 is a graph showing measurement results by the thermomechanical analyzer of Example 2.
  • the compound represented by Formula (1) may be described as a compound (1).
  • the compounds represented by other formulas may be similarly simplified and referred to.
  • the expression “any A may be replaced by B or C” means that at least one A is B, in addition to the case where at least one A is replaced by B and the at least one A is replaced by C. Means that at least one other A may be replaced by C at the same time.
  • the display data of the electronic balance is shown using g (gram) which is a mass unit. Weight percent and weight ratio are data based on such numerical values.
  • composition for heat dissipation member is a composition capable of forming heat dissipation members by directly bonding inorganic fillers with a silane coupling agent and a bifunctional or higher functional carboxylic acid anhydride by curing.
  • FIG. 1 shows an example in which boron nitride is used as the inorganic filler.
  • boron nitride h-BN
  • silane coupling agent is bonded only around the boron nitride because there is no reactive group in the plane of the particle.
  • Boron nitride treated with a silane coupling agent can form a bond with a bifunctional or higher functional carboxylic acid anhydride.
  • boron nitride By combining the other end of the silane coupling agent bonded to boron nitride with the other end of the carboxylic acid anhydride further bonded to the silane coupling agent bonded to boron nitride (see FIG. 2), boron nitride They are mutually connected as shown in FIG.
  • the heat-radiating member after curing has extremely high thermal conductivity, and inorganic It is possible to produce a composite material that directly reflects the coefficient of thermal expansion of the components.
  • the composition for a heat dissipation member according to the first embodiment of the present invention is, for example, as shown in FIG. 2, a thermally conductive first inorganic filler 1 combined with one end of a first silane coupling agent 11 And a thermally conductive second inorganic filler 2 bonded to one end of the silane coupling agent 12.
  • a thermally conductive first inorganic filler 1 combined with one end of a first silane coupling agent 11
  • a thermally conductive second inorganic filler 2 bonded to one end of the silane coupling agent 12.
  • the other end of the first silane coupling agent 11 is bonded to one end of the carboxylic acid anhydride 21 to form the second silane coupling agent 12.
  • the other end bonds with the other end of the carboxylic acid anhydride 21 for example, as shown in FIG.
  • one end of the carboxylic anhydride 21 is bonded to the other end of the first silane coupling agent 11. However, the other end of the carboxylic acid anhydride 21 is not bonded to the other end of the second silane coupling agent 12. As shown in FIG. 3, when the composition for heat dissipation member is cured, the other end of the second silane coupling agent 12 is bonded to the other end of the carboxylic acid anhydride 21. In this way, bonds between the inorganic fillers are formed. In the present invention, it is important in the present invention to realize such bonding between inorganic fillers, and before bonding the silane coupling agent to the inorganic filler, the silane coupling agent and the bifunctional or higher carboxylic acid anhydride are previously prepared. May be reacted using organic synthesis techniques.
  • the bifunctional or higher carboxylic acid anhydride is at least one of phthalic acid anhydride, succinic acid anhydride, maleic acid anhydride, acetic acid anhydride, propionic acid anhydride, or a carboxylic acid anhydride having benzoic acid anhydride.
  • R 1 is a single bond or alkyl having 1 to 20 carbon atoms, cycloalkyl having 4 to 8 carbon atoms, aryl and arylalkyl having 7 to 20 carbon atoms It is a group independently selected.
  • the preferred carbon number of this alkyl is 1 to 10. More preferable R 1 is a linear mesogen (eg, liquid crystal compound).
  • R 2 is independently selected from a single bond or alkyl having 1 to 20 carbon atoms, cycloalkyl having 4 to 8 carbon atoms, aryl and arylalkyl having 7 to 20 carbon atoms Group.
  • the preferred carbon number of this alkyl is 1 to 10.
  • R 3 is independently carbon or nitrogen. More preferred R 2 is a linear mesogen (eg, liquid crystal compound).
  • R 4 and R 5 are groups selected from cycloalkyl having 4 to 8 carbon atoms, aryl and arylalkyl having 7 to 20 carbon atoms, and may be independent.
  • the preferred carbon number of this alkyl is 1 to 10.
  • n is independently an integer of 1 to 4;
  • -Phthalic anhydride examples include compounds (1-1) to (1-4) shown below.
  • m is an integer of 1 to 20, preferably an integer of 1 to 10, more preferably an integer of 4 to 8.
  • n is an integer of 0 to 6, and preferably an integer of 1 to 6.
  • q is an integer of 0 to 4, preferably an integer of 0 to 2.
  • R 6 is a group selected from cycloalkyl having 4 to 8 carbon atoms, aryl and arylalkyl having 7 to 20 carbon atoms, and may be independent.
  • m is an integer of 1 to 20, preferably an integer of 1 to 10, more preferably an integer of 4 to 8.
  • n is an integer of 0 to 6, and preferably an integer of 1 to 6.
  • q is an integer of 0 to 4, preferably an integer of 0 to 2.
  • R 6 is a group selected from cycloalkyl having 4 to 8 carbon atoms, aryl and arylalkyl having 7 to 20 carbon atoms, and may be independent.
  • Examples of preferred formula (3) include compounds (3-1) to (3-4) shown below.
  • m is an integer of 1 to 20, preferably an integer of 1 to 10, and more preferably an integer of 4 to 8.
  • n is an integer of 0 to 6, and preferably an integer of 1 to 6.
  • q is an integer of 0 to 4, preferably an integer of 0 to 2.
  • R 6 is a group selected from cycloalkyl having 4 to 8 carbon atoms, aryl and arylalkyl having 7 to 20 carbon atoms, and may be independent.
  • Acetic anhydride examples include compounds (4-1) to (4-8) shown below.
  • m is an integer of 1 to 20, preferably an integer of 1 to 10, and more preferably an integer of 4 to 8.
  • n is an integer of 0 to 6, and preferably an integer of 1 to 6.
  • q is an integer of 0 to 4, preferably an integer of 0 to 2.
  • R 6 is a group selected from cycloalkyl having 4 to 8 carbon atoms, aryl and arylalkyl having 7 to 20 carbon atoms, and may be independent.
  • Examples of preferable formula (5) include compounds (5-1) to (5-8) shown below.
  • m is an integer of 1 to 20, preferably an integer of 1 to 10, and more preferably an integer of 4 to 8.
  • n is an integer of 0 to 6, and preferably an integer of 1 to 6.
  • q is an integer of 0 to 4, preferably an integer of 0 to 2.
  • R 6 is a group selected from cycloalkyl having 4 to 8 carbon atoms, aryl and arylalkyl having 7 to 20 carbon atoms, and may be independent.
  • Benzoic anhydride examples include compounds (6-1) to (6-6) shown below.
  • Carboxylic Anhydrides Preferred examples include the compounds (7-1) to (7-9) shown below.
  • m is an integer of 0 to 2;
  • n is an integer of 0 to 6, preferably an integer of 0 to 4, and more preferably an integer of 0 to 2.
  • R 6 is a group selected from cycloalkyl having 4 to 8 carbon atoms, aryl and arylalkyl having 7 to 20 carbon atoms, and may be independent.
  • first inorganic filler and the second inorganic filler examples 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.
  • inorganic fillers having high thermal conductivity and a very small or negative coefficient of thermal expansion can be used. Specifically, boron nitride, boron carbide, boron carbon nitride, Graphite, carbon fiber, carbon nanotube can be mentioned.
  • alumina, silica, magnesium oxide, zinc oxide, iron oxide, ferrite, mullite, cordierite, silicon nitride, and silicon carbide can be mentioned.
  • an inorganic filler having a high thermal conductivity and a positive coefficient of thermal expansion described below may be used for either the first or second inorganic filler.
  • an inorganic filler having a high thermal conductivity, a positive coefficient of thermal expansion, or a size smaller than the first and second inorganic fillers can be used.
  • the structure of the carboxylic acid anhydride preferably has a shape and a length capable of efficiently directly bonding between the inorganic fillers.
  • the type, shape, size, addition amount, etc. of the inorganic filler can be appropriately selected according to the purpose.
  • the heat dissipating member to be obtained requires insulation, it may be an inorganic filler having conductivity as long as desired insulation is maintained.
  • the shape of the inorganic filler include plate-like, spherical, amorphous, fibrous, rod-like and cylindrical.
  • boron nitride aluminum nitride, silicon nitride, silicon carbide, graphite, carbon fibers, and carbon nanotubes.
  • 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 planar direction and boron nitride has a low dielectric constant and high insulation.
  • it is preferable to use plate-like crystal boron nitride because the plate-like structure is easily oriented along the mold due to the flow or pressure of the raw material at the time of 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. A thermal conductivity is good in it being 0.1 micrometer or more, and a filling factor can be raised as it is 200 micrometers or less.
  • the average particle diameter 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 diameter by a wet method using analysis based on the franhofer diffraction theory and Mie's scattering theory, the diameter at which the large side and the small side become equivalent (volume based) As the median diameter.
  • the proportions of the inorganic filler, the silane coupling agent and the carboxylic anhydride depend on the amount of silane coupling agent to be combined with the inorganic filler used.
  • the compound (for example, boron nitride) used as a 1st, 2nd inorganic filler does not have a reactive group on the surface as mentioned above, and a reactive group exists only on the side. It is preferable to bind as many silane coupling agents as possible to the few reactive groups, and to bind a carboxylic acid anhydride having the same number or a few more reactive groups as the number of reactive groups.
  • the reaction amount of the silane coupling agent to the inorganic filler mainly changes depending on the size of the inorganic filler and the reactivity of the silane coupling agent used. For example, as the size of the inorganic filler increases, the area ratio of the side surfaces of the inorganic filler decreases, so the amount of modification is small. It is preferable to react as many silane coupling agents as possible with the inorganic filler, but it is preferable to balance the smaller inorganic filler particles, as the thermal conductivity of the product is reduced.
  • the volume ratio of the silane coupling agent and carboxylic acid anhydride in the heat radiation member which is a cured product to the inorganic filler is preferably in the range of 5:95 to 30:70, more preferably 10:90 to 25. : 75.
  • the silane coupling agent to be bonded to the inorganic filler is preferably a silane coupling agent having an amine reactive group at the end, since it is preferable to react with a bifunctional or higher functional carboxylic acid anhydride.
  • a silane coupling agent having an amine reactive group at the end since it is preferable to react with a bifunctional or higher functional carboxylic acid anhydride.
  • CYRA ACE registered trademark
  • KBM 903 and KBE 903 manufactured by Shin-Etsu Chemical Co., Ltd. may be mentioned.
  • the first silane coupling agent and the second silane coupling agent may be the same or different.
  • the first inorganic filler can be used after being treated with a silane coupling agent and further surface-modified with a bifunctional or higher functional carboxylic acid anhydride.
  • the inorganic coupling agent is a carboxylic acid by further binding a bifunctional or higher functional carboxylic acid anhydride to the silane coupling agent. It is surface modified with acid anhydride.
  • the first inorganic filler surface-modified with carboxylic acid anhydride can form a bond with the second inorganic filler with the carboxylic acid anhydride and the silane coupling agent, as shown in FIG.
  • the first inorganic filler may be one that has been subjected to coupling treatment with a silane coupling agent that has been previously bonded to a bifunctional or higher functional carboxylic acid anhydride.
  • the bifunctional or higher carboxylic acid anhydride is preferably a bifunctional or higher carboxylic acid anhydride represented by the above formulas (1) and (2).
  • other carboxylic acid anhydrides may be used.
  • the carboxylic acid anhydride is a polycycle, heat resistance is high, and when the carboxylic acid anhydride is high in linearity, there is little elongation or fluctuation due to heat between the inorganic fillers, and the heat phonon conduction is efficiently transmitted. It is preferable because The surface modification with carboxylic acid anhydride or the like is preferable because the more the surface modification, the more the bonding.
  • the composition for heat dissipation member may further contain an organic compound (for example, a polymerizable compound or a polymer compound) not bound to the first inorganic filler and the second inorganic filler, that is, not contributing to the binding. , And may contain a polymerization initiator, a solvent, and the like.
  • an organic compound for example, a polymerizable compound or a polymer compound
  • the composition for heat dissipation members may contain a carboxylic acid anhydride (in this case, it may not necessarily be bifunctional or more) which is not bonded to the inorganic filler.
  • a carboxylic acid anhydride a compound which does not interfere with the thermal curing of the organic compound modified to the inorganic filler and which does not evaporate or bleed out by heating is preferable.
  • the polymerizable compounds are classified into compounds having no liquid crystallinity and compounds 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 and itaconic acid derivatives. It is preferable to prepare a composition for a heat-dissipation member which does not contain a compound which is not bonded first, to measure its porosity, and to add an amount of the compound capable of filling the porosity.
  • the composition for heat dissipation member may have a polymer compound not bound to the inorganic filler as a component.
  • a polymer compound which does not reduce film formability and mechanical strength is preferable.
  • the polymer compound may be an inorganic filler, a silane coupling agent, and a polymer compound which does not react with the carboxylic acid anhydride.
  • the carboxylic acid anhydride has an oxiranyl group and the silane coupling agent has an amino group
  • polyolefin resins, polyvinyl resins, silicone resins, waxes and the like are examples of the carboxylic acid anhydride.
  • composition for a heat dissipation member which does not contain a polymerizable compound which is not bonded, measure its porosity, and add a polymer compound in an amount capable of filling the porosity.
  • the composition for heat dissipation members may contain a liquid crystal compound having no polymerizable group.
  • non-polymerizable liquid crystalline compounds are described in Liquist (LiqCryst, LCI Publisher GmbH, Hamburg, Germany), which is a database of liquid crystalline compounds, and the like.
  • composite materials of the compound (1) (2) and the liquid crystal compound can be obtained by polymerizing the composition containing the non-polymerizable liquid crystal compound.
  • a nonpolymerizable liquid crystal compound is present in the polymer network.
  • it is a liquid crystal compound having such a property that it does not flow in the temperature range to be used.
  • the inorganic filler may be compounded by a method of injecting into the voids in a temperature range showing an isotropic phase, or the amount of the liquid crystal compound calculated to fill the voids in the inorganic filler in advance. After mixing, the inorganic fillers may be polymerized.
  • the composition for heat dissipation members may contain a solvent.
  • the polymerization may be carried out in a solvent or in the absence of a solvent.
  • the composition containing a solvent may be coated on a substrate by, for example, spin coating, and then the solvent may be removed and then photopolymerization may be performed. Further, after photocuring, post-treatment may be performed by heating to a suitable temperature and heat curing.
  • Preferred solvents include, for example, benzene, toluene, xylene, mesitylene, hexane, heptane, octane, nonane, decane, tetrahydrofuran, ⁇ -butyrolactone, N-methylpyrrolidone, dimethylformamide, dimethylsulfoxide, cyclohexane, methylcyclohexane, cyclopentanone , Cyclohexanone, PGMEA and the like.
  • the above solvents may be used singly or in combination of two or more. There is no point in limiting the use ratio of the solvent at the time of polymerization, and it may be determined for each case in consideration of the polymerization efficiency, solvent cost, energy cost and the like.
  • a stabilizer may be added to the composition for heat dissipation member in order to facilitate handling.
  • a stabilizer known ones can be used without limitation, and examples thereof include hydroquinone, 4-ethoxyphenol and 3,5-di-t-butyl-4-hydroxytoluene (BHT).
  • BHT 3,5-di-t-butyl-4-hydroxytoluene
  • an additive such as an oxide
  • fine powders of titanium oxide for making white, carbon black for making black, and fine powder of silica for adjusting viscosity can be mentioned.
  • additives may be added to further increase the mechanical strength.
  • inorganic fibers or cloths such as glass fibers, carbon fibers, carbon nanotubes or the like, or as polymer additives, fibers or long molecules such as polyvinyl formal, polyvinyl butyral, polyester, polyamide, polyimide and the like can be mentioned.
  • the second inorganic filler is subjected to a coupling process, and one end of the second silane coupling agent is bonded to the second inorganic filler to form a second silane coupling agent. Let it be a second inorganic filler bonded to one end.
  • a well-known method can be used for a coupling process. As an example, first, the inorganic filler and the silane coupling agent are added to the solvent. After stirring using a stirrer etc., it dries.
  • the mixing ratio of the first inorganic filler and the second inorganic filler is, for example, when the bonding group forming the bond between the first inorganic filler and the second inorganic filler is each amine: epoxy, the weight of only the inorganic filler is, for example, And preferably 1: 1 to 1:30, more preferably 1: 3 to 1:20.
  • the mixing ratio is determined by the number of terminal bonding groups that form a bond between the first inorganic filler and the second inorganic filler, and, for example, secondary amines can react with two oxiranyl groups, so The amount may be small compared to the base side, and the oxiranyl side may be open, and it is preferable to use a larger amount calculated from the epoxy equivalent.
  • (4) Manufacturing a Heat Dissipation Member As an example, a method of manufacturing a film as a heat dissipation member using a composition for a heat dissipation member will be described. The composition for heat dissipation member is sandwiched in a heating plate using a compression molding machine, and oriented and 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 at curing is preferably high. However, it is preferable to appropriately change the pressure in accordance with the fluidity in the mold and the desired physical properties (such as which direction of thermal conductivity is to be emphasized).
  • the method of manufacturing the film as a heat radiating member using the composition for heat radiating members containing a solvent is demonstrated concretely.
  • 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, curtain coating, flow coating, printing, microgravure coating, gravure coating, wire bar coating, wire coating, dip coating, spray coating, and meniscus coating.
  • the solvent can be dried and removed by, for example, air drying at room temperature, drying on a hot plate, drying in a drying oven, spraying of warm air or hot air, or the like.
  • the conditions for solvent removal are not particularly limited, and the solvent may be generally removed and the film may be dried until 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; polyimides, polyamideimides, polyamides, polyetherimides, polyetheretherketones, polyetherketones, polyketone sulfides, polyethersulfones, polysulfones, polysulfones, polyphenylene sulfides, polyphenylene oxides, polyethylene terephthalates, polybutylene terephthalates , 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
  • 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.
  • a protective layer which is not corroded by the solvent contained in the said composition for thermal radiation members on these film substrates.
  • a material used as a protective layer polyvinyl alcohol is mentioned, for example.
  • an anchor coat layer may be formed to enhance the adhesion between the protective layer and the substrate.
  • Such an anchor coat layer may be any of inorganic and organic materials as long as the adhesion between the protective layer and the substrate is enhanced.
  • the bond between the inorganic fillers is constituted by the coupling-treated inorganic filler and the coupling-treated inorganic filler further modified with a carboxylic acid anhydride.
  • the second inorganic filler is subjected to coupling treatment with a silane coupling agent having an amino.
  • the first inorganic filler is coupled with a silane coupling agent having an amino, and then bonded to one end of the amino and a compound having a carboxylic acid anhydride at both ends.
  • the amino on the second inorganic filler side is bonded to the other of the COO groups possessed by the carboxylic acid anhydride on the first inorganic filler side.
  • the inorganic filler side may have an epoxy, and the carboxylic acid anhydride side may have a carboxylic acid.
  • the first and second inorganic fillers treated with a silane coupling agent may be mixed and pressed with a bifunctional or higher carboxylic acid anhydride calculated from the modification amount of the silane coupling agent.
  • a bifunctional or higher carboxylic acid anhydride calculated from the modification amount of the silane coupling agent.
  • the carboxylic anhydride has fluidity and soaks into the gaps of the inorganic filler. Further heating allows the carboxylic anhydride to bond with the silane coupling agent to form a bond (ie, cure) between the first inorganic filler and the second inorganic filler.
  • the bond between the inorganic coupling agents may form a bond between the inorganic fillers.
  • the first inorganic filler is coupled with a silane coupling agent having an amino.
  • the second inorganic filler is coupled with a silane coupling agent having a carboxylic acid.
  • the amino on the first inorganic filler side and the epoxy on the second inorganic filler side are bonded.
  • the silane coupling agent bound to the first inorganic filler and the silane coupling agent bound to the second inorganic filler each have a functional group for binding the silane coupling agents to each other.
  • the functional group on the side of the first inorganic filler and the functional group on the side of the second inorganic filler may be a combination of different ones or a combination of the same ones as long as bonding between the silane coupling agents becomes possible.
  • Examples of combinations of functional groups forming bonds between silane coupling agents include combinations of oxiranyl and amino, vinyls, methacryloxys, carboxy or carboxylic anhydride residues and amino, imidazole and oxiranyl, etc. It can, but is not limited to these. A combination of highly heat resistant functional groups is more preferred.
  • At least one of the silane coupling agents contains a carboxylic acid anhydride in the structure.
  • the first inorganic filler and the second inorganic filler can be connected, and the heat dissipation member composition of the present invention has extremely high thermal conductivity. It is possible to obtain a heat dissipating member having the controllability of the heat resistance and the coefficient of thermal expansion.
  • said functional group is an illustration, and as long as the effect of this invention is acquired, it is not restricted to said functional group.
  • the heat radiating member of the present invention is a cured product obtained by curing the heat radiating member composition and molding it according to the use.
  • This cured product can be suitably used as a heat dissipation member because it has high thermal conductivity and high heat resistance at the same time.
  • the cured product can have a negative or very low coefficient of thermal expansion, and is excellent in chemical stability, hardness and mechanical strength.
  • the mechanical strength includes Young's modulus, tensile strength, tear strength, flexural strength, flexural modulus, impact strength and the like.
  • the heat dissipating member is useful for a heat dissipating plate, a heat dissipating sheet, a heat dissipating film, a heat dissipating adhesive, a heat dissipating molded product, and the like.
  • the thermal conductivity can be evaluated by the thermal conductivity in the vertical direction.
  • the vertical direction generally indicates the thickness direction of the sample.
  • the thermal conductivity of the heat radiating member of the present invention in the vertical direction is preferably 5 (W / mK) or more, more preferably 9 (W / mK) or more, when boron nitride is used. If it is this range, since it is excellent in heat conduction, it can utilize suitably for a heat sink etc.
  • the heat resistance can be evaluated by measuring the 5% weight loss temperature.
  • the 5% weight loss temperature of the heat dissipation member of the present invention is preferably 280 ° C. or higher, more preferably 290 ° C.
  • the thermal expansion can be evaluated by the thermal expansion coefficient.
  • the coefficient of thermal expansion indicates the elongation in the plane direction of the sample in the range of 50 to 200 ° C.
  • the thermal expansion coefficient of the heat dissipation member of the present invention is preferably ⁇ 20 to 50 (ppm / K), and more preferably ⁇ 5 to 20 (ppm / K). If it is this range, since it is excellent in non-thermal expansion property, it can utilize suitably for the die attachment etc. to the metal substrate which generates heat.
  • the conditions for the pre-curing for curing the composition for heat dissipation member by thermal polymerization include a thermosetting temperature in the range of room temperature to 350 ° C., preferably room temperature to 300 ° C., more preferably 120 ° C. to 250 ° C. Is in the range of 5 seconds to 10 hours, preferably 1 minute to 5 hours, more preferably 5 minutes to 1 hour. After polymerization, slow cooling is preferable to suppress stress and strain. Further, reheating treatment may be performed to reduce distortion and the like.
  • the heat dissipation member is used in the form of a sheet, a film, a thin film, a fiber, a molded body or the like.
  • Preferred shapes are plates, sheets, films and thin films.
  • the thickness of the sheet in the present specification is 1 mm or more, the thickness of the film is 5 ⁇ m or more, preferably 10 to 500 ⁇ m, more preferably 20 to 300 ⁇ m, and the thickness of the thin film is less than 5 ⁇ m.
  • the film thickness may be appropriately changed according to the application.
  • the composition for a heat dissipation member can also be used as an adhesive or a filler as it is.
  • An electronic device of the present invention includes the heat dissipation member of the present invention, and an electronic device having a heat generating portion or a cooling portion.
  • the heat dissipation member is disposed in the electronic device so as to contact the heat generating portion.
  • the shape of the heat dissipating member may be any of a heat dissipating electronic substrate, a heat dissipating plate, a heat dissipating sheet, a heat dissipating film, a heat dissipating adhesive, a heat dissipating molded product, and the like.
  • a semiconductor module can be mentioned as an electronic device.
  • the heat-radiating member of the present invention has high thermal conductivity, high heat resistance, and high insulation properties in addition to low thermal expansion, so it is an insulated gate bipolar that requires a more efficient heat dissipation mechanism for high power among semiconductor elements. It is particularly effective for a transistor (Insulated Gate Bipolar Transistor, IGBT).
  • IGBT Insulated Gate Bipolar Transistor
  • the IGBT is one of the semiconductor elements, and is a bipolar transistor in which a MOSFET is incorporated in the gate portion, and is used in power control applications.
  • Examples of electronic devices equipped with IGBTs include a main conversion element of a large power inverter, an uninterruptible power supply, a variable voltage variable frequency controller of an AC motor, a controller of a railway vehicle, an electric transportation device such as a hybrid car and an electric car, IH A cooker etc. can be mentioned.
  • the second inorganic filler obtained by the coupling treatment of the present invention and the first inorganic filler further modified with the carboxylic anhydride after the coupling treatment are combined to form a bond between the inorganic fillers, resulting in low heat.
  • the heat dissipating member having the expansibility, high thermal conductivity and high heat resistance has been described, the present invention is not limited thereto.
  • a second inorganic filler modified with a carboxylic acid anhydride may be combined with the first inorganic filler subjected to the coupling treatment to form a bond between the inorganic fillers.
  • the carboxylic acid anhydrides may be bonded with an appropriate polymerization initiator or the like using only the inorganic filler modified with the carboxylic acid anhydride to form a bond between the inorganic fillers.
  • an appropriate polymerization initiator or the like using only the inorganic filler modified with the carboxylic acid anhydride to form a bond between the inorganic fillers.
  • the material which comprises the thermal radiation member used for the Example of this invention is as follows.
  • 1,3-Isobenzobenzofurandione 5,5 ′-(1,8-octanediyl) bis-5,5 ′-(1,8-octanediyl) bis [1,3-isobenzofurandione]: Compound represented by (8-2) (manufactured by JNC Co., Ltd.)
  • Liquid crystalline epoxy compound a compound represented by the following formula (9-1) (manufactured by JNC Co., Ltd.). The compound can be synthesized by the method described in Japanese Patent No. 5084148.
  • Silane coupling agent 1 N- (2-aminoethyl) -3-aminopropyltrimethoxysilane represented by the following formula (10-1) (manufactured by JNC Co., Ltd., (trade name) SYRAACE S320)
  • -Silane coupling agent 2 3-aminopropyltrimethoxysilane represented by the following formula (10-2) (Shin-Etsu Chemical Co., Ltd. product, (trade name) KBM-903)
  • Example 1 Preparation of heat dissipation member> Below, the preparation example of a thermal radiation member is shown. -Preparation of silane coupling agent-treated boron nitride particles 15 g of boron nitride particles (PTX-25 manufactured by Momentive Performance Materials Japan) and 2.25 g of silane coupling agent 1 are added to 100 mL of toluene, and 500 rpm using a stirrer The resulting mixture was dried at 40 ° C. for 4 hours. Furthermore, it heat-processed under vacuum conditions for 5 hours using the vacuum dryer set to 120 degreeC after solvent drying. The obtained particles were used as a second inorganic filler (BN).
  • BN second inorganic filler
  • the resulting mixture is added to 45 mL of tetrahydrofuran, and after sufficient stirring, insolubles are precipitated with a centrifuge (High speed cooling centrifuge model CR22 manufactured by Hitachi Koki Co., Ltd., 4,000 rotation x 10 minutes x 25 ° C) Then, the solution containing the portion in which the unreacted acid anhydride was dissolved was removed by decantation. Thereafter, 45 mL of acetone was added, and the same operation as described above was performed. Further, the same operation was repeated in the order of tetrahydrofuran and acetone. The particles obtained by drying the insolubles were used as the first inorganic filler.
  • the coverage of the first inorganic filler and the second inorganic filler with respect to the silane coupling agent or acid anhydride of BN is determined using a thermogravimetric / differential thermal analyzer (TG-8121 manufactured by Rigaku Corporation)). Calculated from weight loss on heating at 900 ° C.
  • the resulting mixture is held in a stainless steel plate using a metal frame so as not to be oxidized, and pressurized to 30 MPa using a compression molding machine (IMC-19EC manufactured by Imoto Machinery Co., Ltd.) set at 150 ° C. for 15 minutes
  • a compression molding machine IMC-19EC manufactured by Imoto Machinery Co., Ltd.
  • the amounts of the metal frame and the sample were adjusted so that the thickness of the sample was about 500 ⁇ m.
  • curing was performed at 80 ° C. for 3 hours and at 200 ° C. for 14 hours using a vacuum oven. The sample obtained by this operation is used as a heat dissipation member.
  • the coating amount of the obtained sample on the inorganic filler was calculated from the heat loss at 900 ° C. using a thermal weight and differential thermal measurement device (TG-8121 manufactured by Rigaku Corporation) .
  • the 5% weight loss temperature of the heat dissipation member was calculated from the temperature when it decreased by 5 wt% when the amount of decrease from 140 ° C. to 900 ° C. was 100 wt%, using the above-mentioned measuring apparatus.
  • the thermal conductivity is determined in advance by the specific heat of the heat dissipation member (Rigaku Co., Ltd. DSC-8231, measured with a DSC-type input-compensated differential scanning calorimeter) and the specific gravity (a specific gravity meter AG204 manufactured by METTLER TOLEDO
  • the thermal conductivity is measured in the vertical direction by multiplying the thermal diffusivity obtained by using ai-Phase Mobile 1u thermal diffusivity measuring device by measuring the density measurement kit). I asked.
  • Example 2 A sample was prepared and measured in the same manner as in Example 1 except that Formula (8-2) was used instead of Formula (8-1).
  • Example 3 A sample was prepared and measured in the same manner as in Example 1 except that formula (8-3) was used instead of formula (8-1).
  • Example 4 A sample was prepared and measured in the same manner as in Example 1 except that Formula (8-4) was used instead of Formula (8-1).
  • Comparative Example 1 A sample was prepared and measured in the same manner as in Example 1 except that formula (9-1) was used instead of formula (8-1). After precuring, curing was performed at 150 ° C. for 5 hours using a vacuum oven.
  • thermomechanical analyzer of Examples 1, 2 and 4 and Comparative Example 1 are summarized in FIGS. 4 to 7.
  • the first and second behaviors were almost the same for each measurement. It can be seen that the repeated stability of the heat resistance temperature and the temperature cycle is good.
  • Comparative Example 1 In the method of dispersing an ordinary high thermal conductivity filler in an epoxy resin and a curing agent, for example, as in Comparative Example 1, the coefficient of thermal expansion changes largely before and after the glass transition temperature.
  • Comparative Example 1 since a liquid crystalline epoxy compound excellent in heat resistance and thermal expansion is used, a relatively high thermal expansion coefficient and heat resistance temperature are shown, but a normal bisphenol type epoxy compound and silica are used.
  • the composite material of a diamine curing agent has a coefficient of thermal expansion of about 50 ⁇ 10 ⁇ 6 / K and a heat resistance temperature of about 120 ° C.
  • the heat dissipating member formed from the composition for heat dissipating member of the present invention has extremely high thermal conductivity and heat resistance at the same time, so for example, a heat dissipating substrate, a heat dissipating plate (planar heat sink), a heat dissipating sheet, a heat dissipating coating, It can be used as a heat dissipating adhesive.
  • first inorganic filler 2 second inorganic filler 11 first silane coupling agent 12 second silane coupling agent 21 bifunctional or higher carboxylic anhydride 3 first silane coupling agent and bifunctional or higher The site where the carboxylic anhydride and the second silane coupling agent are bound

Abstract

La présente invention concerne une composition qui permet la formation d'un élément de dissipation de chaleur qui a une résistance à la chaleur élevée et simultanément une conductivité thermique élevée. Une composition pour des éléments de dissipation de chaleur selon la présente invention contient : une première charge inorganique (1) qui est liée à une extrémité d'un premier agent de couplage au silane (11) ; une seconde charge inorganique (2) qui est liée à une extrémité d'un second agent de couplage au silane (12) ; et un anhydride d'acide carboxylique (21) qui a une fonctionnalité d'au moins 2.
PCT/JP2018/031108 2017-08-30 2018-08-23 Composition pour éléments de dissipation de chaleur, élément de dissipation de chaleur, dispositif électronique et procédé de production d'un élément de dissipation de chaleur WO2019044646A1 (fr)

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CN201880050456.5A CN111051466A (zh) 2017-08-30 2018-08-23 放热构件用组合物、放热构件、电子机器、放热构件的制造方法
KR1020207002876A KR20200044789A (ko) 2017-08-30 2018-08-23 방열 부재용 조성물, 방열 부재, 전자 기기, 방열 부재의 제조 방법

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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
JP2016153500A (ja) * 2016-03-29 2016-08-25 グンゼ株式会社 絶縁性熱伝導ポリイミド樹脂組成物
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WO2017150589A1 (fr) * 2016-03-02 2017-09-08 Jnc株式会社 Composition pour élément de dissipation de chaleur, élément de dissipation de chaleur, instrument électronique et procédé de fabrication d'élément de dissipation de chaleur

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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
JP2017095566A (ja) * 2015-11-20 2017-06-01 株式会社巴川製紙所 熱伝導性熱硬化型接着剤組成物及び熱伝導性熱硬化型接着シート
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CN112029273B (zh) * 2020-09-07 2022-04-29 北京航天凯恩化工科技有限公司 具有石墨烯-碳纳米管复合结构的导电尼龙母粒及其制备方法

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