WO2013030998A1 - Composition de résine, feuille de résine, feuille de résine dotée d'une feuille métallique, feuille de résine durcie, structure et dispositif à semi-conducteur pour une source d'énergie ou de lumière - Google Patents

Composition de résine, feuille de résine, feuille de résine dotée d'une feuille métallique, feuille de résine durcie, structure et dispositif à semi-conducteur pour une source d'énergie ou de lumière Download PDF

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Publication number
WO2013030998A1
WO2013030998A1 PCT/JP2011/069845 JP2011069845W WO2013030998A1 WO 2013030998 A1 WO2013030998 A1 WO 2013030998A1 JP 2011069845 W JP2011069845 W JP 2011069845W WO 2013030998 A1 WO2013030998 A1 WO 2013030998A1
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Prior art keywords
resin
epoxy resin
resin composition
resin sheet
cured
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PCT/JP2011/069845
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English (en)
Japanese (ja)
Inventor
高橋　裕之
智雄 西山
敏明 白坂
桑野　敦司
竹澤　由高
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日立化成工業株式会社
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Application filed by 日立化成工業株式会社 filed Critical 日立化成工業株式会社
Priority to PCT/JP2011/069845 priority Critical patent/WO2013030998A1/fr
Priority to KR1020187002450A priority patent/KR101970771B1/ko
Priority to KR1020197010761A priority patent/KR102081876B1/ko
Priority to KR1020147007771A priority patent/KR101825259B1/ko
Priority to CN201180073184.9A priority patent/CN103764713B/zh
Priority to JP2013530974A priority patent/JP5850056B2/ja
Priority to TW105112040A priority patent/TWI585147B/zh
Priority to TW101131781A priority patent/TWI548692B/zh
Publication of WO2013030998A1 publication Critical patent/WO2013030998A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/28—Nitrogen-containing compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/31—Structure, shape, material or disposition of the layer connectors after the connecting process
    • H01L2224/33—Structure, shape, material or disposition of the layer connectors after the connecting process of a plurality of layer connectors
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/42—Wire connectors; Manufacturing methods related thereto
    • H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
    • H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
    • H01L2224/481—Disposition
    • H01L2224/48151—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
    • H01L2224/48221—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
    • H01L2224/48245—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic
    • H01L2224/48247—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic connecting the wire to a bond pad of the item
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/73—Means for bonding being of different types provided for in two or more of groups H01L2224/10, H01L2224/18, H01L2224/26, H01L2224/34, H01L2224/42, H01L2224/50, H01L2224/63, H01L2224/71
    • H01L2224/732—Location after the connecting process
    • H01L2224/73251—Location after the connecting process on different surfaces
    • H01L2224/73265—Layer and wire connectors
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/10—Details of semiconductor or other solid state devices to be connected
    • H01L2924/11—Device type
    • H01L2924/13—Discrete devices, e.g. 3 terminal devices
    • H01L2924/1304—Transistor
    • H01L2924/1305—Bipolar Junction Transistor [BJT]
    • H01L2924/13055—Insulated gate bipolar transistor [IGBT]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/10—Details of semiconductor or other solid state devices to be connected
    • H01L2924/11—Device type
    • H01L2924/13—Discrete devices, e.g. 3 terminal devices
    • H01L2924/1304—Transistor
    • H01L2924/1306—Field-effect transistor [FET]
    • H01L2924/13091—Metal-Oxide-Semiconductor Field-Effect Transistor [MOSFET]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
    • H01L2924/181—Encapsulation

Definitions

  • the present invention relates to a resin composition, a resin sheet, a resin sheet with a metal foil, a cured resin sheet, a structure, and a semiconductor device for power or light source.
  • heat sinks and heat dissipation fins are indispensable for heat dissipation for stable operation of semiconductor devices used for central processing units of personal computers and motors of electric vehicles.
  • a material that can achieve both insulation and thermal conductivity.
  • organic materials are widely used for insulating materials such as printed boards on which semiconductor devices are mounted. Although these organic materials have high insulating properties, their thermal conductivity is low and their contribution to heat dissipation from semiconductor devices and the like has not been significant.
  • inorganic materials such as inorganic ceramics are sometimes used for heat dissipation of semiconductor devices and the like. Although these inorganic materials have high thermal conductivity, their insulating properties are not sufficient compared to organic materials, and materials that can achieve both high insulating properties and thermal conductivity are required.
  • JP 2008-13759 A discusses a composite material in which an epoxy resin containing a mesogen skeleton and alumina as a filler having high thermal conductivity are mixed.
  • a cured product composed of a composite system of a general bisphenol A type epoxy resin and an alumina filler is known, and the obtained thermal conductivity is 3.8 W / m ⁇ K, temperature wave thermal analysis in the xenon flash method. According to the law, 4.5 W / m ⁇ K can be achieved (see Japanese Patent Application Laid-Open No. 2008-13759).
  • a cured product composed of a composite system of an epoxy resin containing mesogen, an amine curing agent, and alumina is known, and the thermal conductivity is 9.4 W / m ⁇ K, temperature wave heat in the xenon flash method. According to the analysis method, 10.4 W / m ⁇ K can be achieved.
  • the cured product described in International Publication No. 02/094905 does not have a sufficient thermal conductivity in practical use.
  • the cured product described in JP-A-2008-13759 has a problem that it is inferior in flexibility because an amine-based curing agent is used, and the semi-cured sheet is easily broken.
  • the present invention relates to a resin composition having flexibility before curing and capable of achieving high thermal conductivity after curing, a resin sheet formed using the resin composition, a resin sheet with a metal foil, and a resin cured product It is an object to provide a sheet, a structure, and a semiconductor device for power or light source.
  • a first aspect of the present invention includes an epoxy resin containing a polyfunctional epoxy resin, a curing agent containing a novolac resin having a structural unit represented by the following general formula (I), and an inorganic filler containing nitride particles; , Containing.
  • polyfunctional means that the number of functional groups in one molecule is 3 or more.
  • R 1 and R 2 each independently represents a hydrogen atom or a methyl group, m represents an average value of 1.5 to 2.5, and n represents an average value of 1 to 15.
  • the resin composition preferably contains 50% to 85% by volume of the inorganic filler. And it is preferable that the said resin composition contains the said polyfunctional epoxy resin 20 mass% or more in all the epoxy resins.
  • the polyfunctional epoxy resin preferably contains a branched structure from the viewpoint of the crosslinking density and glass transition temperature of the cured resin, and specifically, a triphenylmethane type epoxy resin, a tetraphenylethane type epoxy resin, and dihydroxybenzene. It is preferably at least one selected from a novolac type epoxy resin and a glycidylamine type epoxy resin. In particular, at least one selected from a triphenylmethane type epoxy resin and a dihydroxybenzene novolak type epoxy resin containing a branched structure in the repeating unit is more preferable.
  • the polyfunctional epoxy resin preferably further contains a liquid or semisolid epoxy resin
  • the liquid or semisolid epoxy resin is a bisphenol A type epoxy resin or a bisphenol F type epoxy. It is preferably at least one selected from resins, bisphenol A-type and F-type mixed epoxy resins, bisphenol F-type novolac epoxy resins, naphthalene diol-type epoxy resins, and glycidylamine-type epoxy resins.
  • liquid means that the melting point or softening point is less than room temperature
  • “semi-solid” means that the melting point or softening point is 40 ° C. or less.
  • the curing agent preferably contains 20% by mass to 70% by mass of at least one selected from mononuclear dihydroxybenzene.
  • the inorganic filler contains 50% to 95% by volume of the nitride particles.
  • the nitride particles are preferably aggregates or pulverized products of hexagonal boron nitride, and the ratio of the major axis to the minor axis is preferably 2 or less.
  • the resin composition preferably further contains a coupling agent. Furthermore, it is also preferable to contain a dispersing agent.
  • the second aspect of the present invention is a resin sheet that is an uncured body or a semi-cured body of the resin composition.
  • the 3rd aspect of this invention is a resin sheet with a metal foil which has the said resin sheet and metal foil.
  • a fourth aspect of the present invention is a cured resin sheet that is a cured product of the resin composition.
  • the cured resin sheet preferably has a thermal conductivity of 10 W / m ⁇ K or more.
  • a fifth aspect of the present invention is a structure having the resin sheet or the cured resin sheet and a metal plate provided in contact with one or both surfaces of the resin sheet or the cured resin sheet.
  • a sixth aspect of the present invention is a power or light source semiconductor device having the resin sheet, the resin sheet with metal foil, the cured resin sheet, or the structure.
  • ADVANTAGE OF THE INVENTION According to this invention, it has a softness
  • process indicates a range including numerical values described before and after that as a minimum value and a maximum value, respectively.
  • process is not limited to an independent process, and even if it cannot be clearly distinguished from other processes, the term “process” is used as long as the intended action of the process is achieved. included.
  • amount of each component in the composition in the present specification when there are a plurality of substances corresponding to each component in the composition, the plurality of the components present in the composition unless otherwise specified. It means the total amount of substance.
  • the resin composition of the present invention includes an epoxy resin containing a polyfunctional epoxy resin, a curing agent containing a novolak resin having a structural unit represented by the following general formula (I), an inorganic filler containing nitride particles, Containing. With such a configuration, it is possible to form an insulating resin cured product having flexibility before curing and having excellent thermal conductivity after curing.
  • R 1 and R 2 each independently represents a hydrogen atom or a methyl group, m represents an average value of 1.5 to 2.5, and n represents an average value of 1 to 15.
  • phonons are dominant in heat conduction in an epoxy resin cured product obtained from an epoxy resin and a curing agent, and the thermal conductivity is about 0.15 W / m ⁇ K to 0.22 W / m ⁇ K.
  • the thermal conductivity is about 0.15 W / m ⁇ K to 0.22 W / m ⁇ K.
  • the cured epoxy resin is amorphous and does not have a structure that can be called an ordered structure, and that there are fewer covalent bonds that bring about the harmony of lattice vibration than metals and ceramics. Therefore, phonon scattering is large in the cured epoxy resin, and the mean free path of phonon is as short as about 0.1 nm for the cured epoxy resin, for example, compared to 100 nm for crystalline silica, which causes low thermal conductivity. ing.
  • the present inventors have found that in order to increase the thermal conductivity, increasing the number of covalent bonds that bring about the harmonicity of lattice vibration and reducing dynamic phonon scattering are effective in improving the thermal conductivity.
  • the present invention has been reached.
  • a structure having a large number of covalent bonds that bring about harmonicity of lattice vibration can be obtained by shortening the distance between the branch points of the resin skeleton and forming a fine mesh. That is, in the thermosetting resin, a structure having a small molecular weight between crosslinking points is preferable. With such a configuration, the crosslink density is increased, and even when the anisotropic structure is not formed in the cured epoxy resin containing no mesogen, it is effective in improving the thermal conductivity.
  • a polyfunctional epoxy resin is used as the epoxy resin, and the above-mentioned as a curing agent.
  • a novolak resin having a structural unit represented by the general formula (I) is used, and nitride particles are used as an inorganic filler.
  • the resin composition of the present invention contains a polyfunctional epoxy resin as an epoxy resin.
  • a polyfunctional epoxy resin By including a polyfunctional epoxy resin, the crosslinking density can be increased.
  • the polyfunctional epoxy resin can be prepared from a polyfunctional epoxy resin monomer.
  • the polyfunctional epoxy resin may have a linear structure or a branched structure.
  • the polyfunctional epoxy resin having a branched structure and a skeleton having a reactive epoxy group at a side chain or a terminal has a branched structure. Since the molecular weight between the crosslinking points decreases and the crosslinking density increases because the part becomes a crosslinking point, it is particularly preferable that the repeating unit of the multimer contains a branched structure. This will be described by comparing an epoxy resin having a repeating unit represented by the following formula (II) with an epoxy resin having a repeating unit represented by the following formula (III).
  • An epoxy resin (epoxy equivalent 165 g / eq) having a repeating unit represented by the following formula (II) has a linear structure.
  • the repeating structure (2) and a repeating epoxy chain end group (1) containing a reactive epoxy terminal group (1) in the branched side chain moiety and having substantially the same epoxy equivalent as the formula (II) are shown below.
  • an epoxy resin having a unit (epoxy equivalent: 168 g / eq) it is estimated that the cross-linking network is finer, and it is expected that the cross-linking density is further increased.
  • an epoxy resin having a repeating unit represented by the above formula (II) or (III) reactive epoxy terminal group (1): p-position
  • a structural unit represented by the general formula (I) according to the present invention as a curing agent
  • the polyfunctional epoxy resin is preferably an epoxy resin having a repeating unit represented by the formula (III).
  • the polyfunctional epoxy resin preferably has a small epoxy equivalent.
  • a small epoxy equivalent indicates a high crosslink density.
  • the epoxy equivalent is preferably 200 g / eq or less, and more preferably 170 g / eq or less.
  • the polyfunctional epoxy resin does not have a residue such as an alkyl group or a phenyl group that does not participate in crosslinking. Residues not involved in the reaction are considered to cause phonon scattering by being converted into phonon reflection and thermal motion of the residues in phonon conduction.
  • the polyfunctional epoxy resin examples include phenol novolac epoxy resin, triphenylmethane type epoxy resin, tetraphenylethane type epoxy resin, dihydroxybenzene novolac epoxy resin, and glycidylamine type epoxy resin. From the viewpoint of the branched structure, it is more preferable that it is at least one selected from triphenylmethane type epoxy resin, tetraphenylethane type epoxy resin and glycidylamine type epoxy resin, and from the viewpoint of crosslinking density, a reactive terminal is added to the repeating unit. A triphenylmethane type epoxy resin having a branched structure is more preferable. Further, even with a linear type curing agent, a dihydroxybenzene novolac type epoxy resin having a reactive end larger than 1 in the repeating unit is preferable from the viewpoint of the crosslinking density.
  • the polyfunctional epoxy resin is preferably contained in an amount of 20% by mass or more, more preferably 30% by mass or more, and still more preferably 50% by mass or more in the total epoxy resin.
  • the epoxy resin in the present invention preferably further contains a liquid or semi-solid epoxy resin.
  • Liquid and semi-solid epoxy resins may give the effect of lowering the softening point of the resin composition.
  • liquid and semi-solid epoxy resins liquid epoxy resins are preferred from the viewpoint of the effect of lowering the softening point.
  • liquid or semi-solid epoxy resins examples include bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol A type and F type mixed epoxy resins, bisphenol F novolak type epoxy resins, naphthalenediol type epoxy resins, and glycidylamine. It is preferable to use at least one selected from type epoxy resins.
  • the liquid or semi-solid epoxy resin is selected from bisphenol F type epoxy resin, bisphenol A type and F type mixed epoxy resin, bisphenol F type novolac epoxy resin, and glycidylamine type epoxy resin. It is preferable to use at least one of the above.
  • the liquid or semi-solid epoxy resin is often a bifunctional epoxy resin, and in the case of a bifunctional epoxy resin monomer, it does not have a branched structure and extends between the cross-linking points, thereby reducing the cross-linking density. Should not be much. Therefore, the bifunctional liquid or semi-solid epoxy resin is preferably contained at 50% by mass or less of the total epoxy resin, more preferably at 30% by mass or less, and further at 20% by mass or less. preferable.
  • a bisphenol F type novolac epoxy resin or a glycidylamine type epoxy resin which is a polyfunctional liquid or semi-solid epoxy resin.
  • the polyfunctional liquid or semi-solid epoxy resin is preferably contained at 50% by mass or less of the total epoxy resin, more preferably at 30% by mass or less, and further preferably at 20% by mass or less.
  • the modification functions and skeletons listed here are only examples and are not limited.
  • the resin composition of this invention contains the novolak resin which has a structural unit represented by the following general formula (I) as a hardening
  • a novolak resin used as the curing agent in the present invention having a smaller hydroxyl equivalent as in the case of the epoxy resin.
  • concentration of the hydroxyl group which is a reactive group becomes high.
  • a novolak resin contains as little residue as possible not involved in crosslinking.
  • the novolak resin used as the curing agent has a structural unit represented by the following general formula (I).
  • R 1 and R 2 each independently represents a hydrogen atom or a methyl group, m represents an average value of 1.5 to 2.5, and n represents an average value of 1 to 15 .
  • the novolak resin preferably has a small hydroxyl equivalent, and in the novolak resin having the structural unit represented by the general formula (I), m is 1.5 or more on average, so that the hydroxyl equivalent is appropriately reduced. ing. On the other hand, if the hydroxyl equivalent is too small, the resulting cured product tends to be brittle, so m is an average value of 2.5 or less. Accordingly, m in the general formula (I) is an average value of 1.5 to 2.5, and more preferably 1.7 to 2.2.
  • the valence m of the hydroxyl group may be an average value.
  • the monovalent phenol and divalent resorcinol are used in equimolar amounts as raw materials to adjust the average valence to 1.5 to 2.5. May be.
  • n in the general formula (I) is an average value of 1 to 15, and from the viewpoint of flow viscosity at the time of heating such as pressure bonding of the resin composition processed into a sheet shape, n is preferably an average value of 1 to 10.
  • n may be an average value, that is, as a curing agent skeleton containing a repeating unit, for example, in the general formula (I), a hydrogen atom and m-valent phenol (—Ph— (OH) m) at both ends are used.
  • n may be 1 to 15 on average.
  • the synthesis may be a case where the novolak resin becomes a mixture having different molecular weights to obtain an average value of n of 1 to 15, or a novolak resin having a different molecular weight is mixed to obtain an average value of n of 1 to 15. It may be a case where it is adjusted to.
  • the aldehyde and ketone used for synthesizing the novolak resin are preferably formaldehyde from the viewpoint of hydroxyl equivalent, but acetaldehyde may be selected from the viewpoint of heat resistance, or acetone may be selected for ease of synthesis. Furthermore, in order to achieve both hydroxyl equivalent and heat resistance, at least two of formaldehyde, acetaldehyde, and acetone may be used in combination.
  • the novolak resin is preferably a novolak resin obtained by condensing a mononuclear phenol compound having a divalent phenolic hydroxyl group as a monomer and formaldehyde, acetaldehyde or acetone as an aldehyde.
  • the novolak resin having the structural unit represented by the general formula (I) has another structure as long as it has the structural unit represented by the general formula (I) in the molecule. You may do it.
  • a skeleton derived from a phenol compound a condensed ring structure of a phenol compound such as an alkylphenol, an aralkyl skeleton, or a xanthene skeleton may be present in the molecule.
  • the novolak resin having the structural unit represented by the general formula (I) may be a random polymer or a block copolymer.
  • the novolak resin having the structural unit represented by the general formula (I) preferably has a content of the structural unit represented by the general formula (I) in the molecule of 50% by mass or more, and 70% by mass. More preferably, it is more preferably 80% by mass or more.
  • the hydroxyl group equivalent of the novolak resin having the structural unit represented by the general formula (I) is preferably 100 g / eq or less, more preferably 80 g / eq or less, and 70 g / eq from the viewpoint of crosslinking density. The following is more preferable.
  • the curing agent may further contain other novolak resin, a mononuclear phenol compound (monomer) having a divalent or higher hydroxyl group, an aralkyl resin, and the like for modification.
  • a mononuclear phenol compound (monomer) having a divalent or higher hydroxyl group an aralkyl resin, and the like for modification.
  • curing agent contains the said monomer, it becomes suppressed that a resin hardened
  • the curing agent containing the monomer can be obtained by adding a monomer to the curing agent or leaving unreacted monomer at the time of synthesis.
  • the monomer is preferably a raw material phenol compound used to synthesize the novolak resin having the structural unit represented by the general formula (I), but may further include another mononuclear phenol compound. .
  • mononuclear phenol compounds mononuclear dihydric phenol compounds (mononuclear dihydroxybenzene) are preferable. Mononuclear dihydroxybenzene may be used individually by 1 type, or may use 2 or more types together. It is preferable to add mononuclear dihydroxybenzene because the effect of suppressing the decrease in the crosslinking density can be obtained while lowering the softening point of the resin composition.
  • Examples of the mononuclear dihydroxybenzene include catechol, resorcinol, and hydroquinone, and among these three types, resorcinol that is difficult to be oxidized is preferable.
  • the skeletons listed here are examples and are not limited.
  • the total content of at least one selected from the mononuclear dihydroxybenzene compound is preferably 20% by mass to 70% by mass in the total curing agent from the viewpoint of thermal conductivity and softening point, and is particularly preferable for the semi-cured sheet. From the viewpoint of flexibility and the crosslinking density of the cured product, 30% by mass to 50% by mass is preferable. Within the above range, the number of functional groups not involved in crosslinking is suppressed, so that dynamic scattering of phonons is suppressed, and a decrease in the thermal conductivity of the cured resin is suppressed.
  • the hydroxyl equivalent of the entire curing agent is preferably 80 g / eq or less, more preferably 70 g / eq or less.
  • the content of the curing agent in the resin composition of the present invention is preferably adjusted so that the ratio of the hydroxyl group equivalent in the curing agent to the epoxy equivalent of the poxy resin is close to 1.
  • the equivalent ratio is preferably 0.8 to 1.2, more preferably 0.9 to 1.1, and 0.95 to 1. More preferably, it is 05.
  • an imidazole curing accelerator or an amine curing accelerator in which chain polymerization of epoxy groups occurs as a curing accelerator unreacted epoxy groups are unlikely to remain. May be added in excess.
  • the resin composition of the present invention contains nitride particles as an inorganic filler from the viewpoint of thermal conductivity.
  • nitride particles include particles such as boron nitride, silicon nitride, and aluminum nitride, and boron nitride is preferable.
  • boron nitride is used as an inorganic filler in the resin composition, a decrease in the glass transition temperature can be suppressed. The reason is considered as follows.
  • the cured epoxy resin containing an inorganic filler mainly composed of aluminum oxide, aluminum hydroxide, silicon oxide or the like has a lower glass transition temperature than the cured epoxy resin containing no inorganic filler.
  • the epoxy resin system having a high crosslinking density according to the present invention it is considered that the influence appears remarkably.
  • boron nitride has low polarity and does not have a hydroxyl group on the surface, so it is difficult to adsorb water, and does not cause curing inhibition to the epoxy resin caused by these hydroxyl groups or adsorbed water. And the curing reaction of the curing agent proceeds to give a high crosslinking density. Thereby, it is considered that the glass transition temperature of the cured epoxy resin containing the inorganic filler mainly composed of boron nitride is equivalent to the cured epoxy resin not containing the inorganic filler.
  • boron nitride is contained in the resin composition can be confirmed by, for example, energy dispersive X-ray analysis (EDX), and particularly in combination with a scanning electron microscope (SEM). It is also possible to confirm the distribution state of boron nitride in the cross section.
  • EDX energy dispersive X-ray analysis
  • SEM scanning electron microscope
  • the crystal form of the boron nitride may be any of hexagonal, cubic, and rhombohedral, but hexagonal is preferable because the particle diameter can be easily controlled. Two or more types of boron nitride having different crystal forms may be used in combination.
  • the hexagonal boron nitride particles are preferably pulverized or agglomerated.
  • the particle shape of the hexagonal boron nitride include a round shape, a spherical shape, a flake shape, and an agglomerated particle.
  • the ratio of the major axis to the minor axis is preferably 3 or less. Is preferably 2 or less round or spherical, more preferably spherical.
  • the agglomerated boron hexagonal boron nitride has many gaps and is easily crushed and deformed by applying pressure.
  • the filling rate of the inorganic filler is lowered in consideration of the coating properties of the varnish of the resin composition.
  • the particle shape is considered to have more contact points in the round shape or scale shape than the spherical shape, Spherical particles are preferable in view of the balance between the above-described filling properties and the thixotropic viscosity of the resin composition.
  • the said boron nitride particle from which particle shape differs may be used individually by 1 type, or may use 2 or more types together.
  • an inorganic filler other than boron nitride may be used in combination to fill the gap. Although it will not have a restriction
  • Specific examples of inorganic fillers other than boron nitride include beryllium oxide, aluminum oxide, magnesium oxide, silicon oxide, aluminum nitride, silicon nitride, talc, mica, aluminum hydroxide, barium sulfate and the like. Among these, aluminum oxide, aluminum nitride, and silicon nitride are preferable from the viewpoint of thermal conductivity.
  • the volume average particle diameter of the inorganic filler is not particularly limited, but is preferably 100 ⁇ m or less from the viewpoint of moldability, and more preferably 20 ⁇ m to 100 ⁇ m from the viewpoint of thermal conductivity and thixotropic properties of the varnish. More preferably, it is more preferably 20 ⁇ m to 60 ⁇ m from the viewpoint of insulation.
  • the inorganic filler may be a particle size distribution having a single peak or a particle size distribution having two or more peaks.
  • an inorganic filler showing a particle size distribution having two or more peaks is preferable.
  • the particle size distribution of the inorganic filler having a particle size distribution having two or more peaks is, for example, an average of 0.1 ⁇ m to 0.8 ⁇ m as a small particle size when showing a particle size distribution having three peaks. It is preferable to have a particle size, an average particle size of 1 ⁇ m to 8 ⁇ m as a medium particle size particle, and an average particle size of 20 ⁇ m to 60 ⁇ m as a large particle size particle.
  • the filling rate of the inorganic filler is further improved, and the thermal conductivity is further improved.
  • the large particle size particles preferably have an average particle size of 30 ⁇ m to 50 ⁇ m, and the medium particle size particles are preferably 1/4 to 1/10 of the average particle size of the large particle size particles.
  • the particles are preferably 1 ⁇ 4 to 1/10 of the average particle size of the medium-sized particles.
  • the nitride particles are preferably used as the large particle size particles.
  • the medium-sized particles and the small-sized particles may be nitride particles or other particles, and are preferably aluminum oxide particles from the viewpoint of thermal conductivity and thixotropic properties of the varnish. .
  • the content of the nitride particles in the total amount of the inorganic filler is preferably 50% by volume to 95% by volume from the viewpoint of moldability, and 60% by volume to 95% by volume from the viewpoint of fillability. More preferably, it is more preferably 65% by volume to 92% by volume from the viewpoint of thermal conductivity.
  • the content of the inorganic filler in the resin composition of the present invention is preferably 50% by volume to 85% by volume from the viewpoint of moldability, and 60% by volume to 85% by volume from the viewpoint of thermal conductivity. More preferably, it is more preferably 65% by volume to 75% by volume from the viewpoint of thixotropy of the varnish.
  • the content of the inorganic filler on the volume basis is within the above range, an insulating resin cured product having flexibility before curing and having excellent thermal conductivity after curing can be formed.
  • the volume-based content of the inorganic filler in the resin composition is measured as follows. First, the mass (Wc) of the resin composition at 25 ° C. was measured, and the resin composition was baked in the air at 400 ° C. for 2 hours, then at 700 ° C. for 3 hours, and the resin content was decomposed and burned off. Thereafter, the mass (Wf) of the remaining inorganic filler at 25 ° C. is measured. Next, the density (df) of the inorganic filler at 25 ° C. is obtained using an electronic hydrometer or a specific gravity bottle. Next, the density (dc) of the resin composition at 25 ° C. is measured by the same method.
  • the volume (Vc) of the resin composition and the volume (Vf) of the remaining inorganic filler are obtained, and the volume of the remaining inorganic filler is divided by the resin composition volume as shown in (Equation 1). Obtained as the volume ratio (Vr) of the inorganic filler.
  • Vc volume of the resin composition (cm 3 )
  • Wc mass of the resin composition
  • dc Density of resin composition (g / cm 3 )
  • Vf Volume of inorganic filler (cm 3 )
  • Wf Mass of inorganic filler
  • df density of the inorganic filler (g / cm 3 )
  • Vr Volume ratio of inorganic filler
  • the mass ratio is not particularly limited as long as the inorganic filler is contained within the volume ratio.
  • the inorganic filler can be contained in the range of 1 part by mass to 99 parts by mass, and in the range of 50 parts by mass to 97 parts by mass. It is preferably contained, more preferably 80 to 95 parts by mass. When the content of the inorganic filler is within the above range, higher thermal conductivity can be achieved.
  • the resin composition of the present invention can contain other components as needed in addition to the above components.
  • examples of other components include a curing accelerator, a coupling agent, a dispersant, an organic solvent, and a curing accelerator.
  • the epoxy resin or the curing agent does not have nitrogen atoms and basicity
  • the effect similar to an amine hardening accelerator can be anticipated when the nitrogen atom is contained in the molecule
  • the curing accelerator examples include phosphorus-based curing accelerators such as triphenylphosphine (manufactured by Hokuko Chemical) and PPQ (manufactured by Hokuko Chemical); phosphonium salt-based curing accelerators such as TPP-MK (manufactured by Hokuko Chemical); EMZ- Organoboron curing accelerators such as K (made by Hokuko Chemical); 2E4MZ (made by Shikoku Chemicals), 2E4MZ-CN (made by Shikoku Chemicals), 2PZ-CN (made by Shikoku Chemicals), 2PHZ (made by Shikoku Chemicals) It is possible to use imidazole-based curing accelerators such as triethylamine, N, N-dimethylaniline, amine-based curing accelerators such as 4- (N, N-dimethylamino) pyridine, hexamethylenetetramine, and the like.
  • phosphorus-based curing accelerators such as
  • phosphorus-based curing accelerators and phosphonium salt-based curing accelerators are suitable because they can suppress homopolymerization of the epoxy resin monomer, and thus facilitate the reaction between the curing agent and the epoxy resin.
  • the epoxy equivalent / hydroxyl equivalent is greater than 1, especially 1.2 or more, an unreacted epoxy group is generated, which may cause phonon scattering that lowers the thermal conductivity as described above.
  • an imidazole curing accelerator or an amine curing accelerator capable of homopolymerizing an epoxy group is preferable to add.
  • the resin composition contains a coupling agent, so that the bondability between the resin component containing the epoxy resin and the novolak resin and the inorganic filler is further improved, and higher thermal conductivity and stronger adhesion can be achieved. it can.
  • the coupling agent is not particularly limited as long as it is a compound having a functional group that binds to the resin component and a functional group that binds to the inorganic filler, and a commonly used coupling agent can be used.
  • Examples of the functional group bonded to the resin component include an epoxy group, an amino group, a mercapto group, a ureido group, and an N-phenylamino group. From the viewpoint of storage stability, the coupling agent preferably has an epoxy group or N-phenylamino group functional group having a slow reaction rate.
  • Examples of the functional group bonded to the inorganic filler include an alkoxy group and a hydroxyl group.
  • Examples of the coupling agent having such a functional group include a silane coupling having a dialkoxysilane or a trialkoxysilane. And titanate coupling agents having an alkoxy titanate.
  • silane coupling agent examples include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl).
  • Ethyltrimethoxysilane 3-aminopropyltriethoxysilane, 3- (2-aminoethyl) aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3- (2-aminoethyl) aminopropyltrimethoxysilane, Examples thereof include N-phenyl-3-aminopropyltrimethoxysilane, 3-mercaptotriethoxysilane, and 3-ureidopropyltriethoxysilane.
  • a silane coupling agent oligomer represented by SC-6000KS2 (manufactured by Hitachi Chemical Coated Sands Co., Ltd.) can also be used.
  • a titanate coupling agent having a terminal amino group (Ajinomoto Fine Techno Preact KR44) can be used. These coupling agents can be used alone or in combination of two or more.
  • the content of the coupling agent in the resin composition is not particularly limited, but from the viewpoint of thermal conductivity, it is 0.02% by mass to 0.83% by mass with respect to the total mass of the resin composition. It is preferably 0.04% by mass to 0.42% by mass.
  • the content of the coupling agent is preferably 0.02% by mass to 1% by mass with respect to the inorganic filler from the viewpoint of thermal conductivity and insulation, and 0.05% by mass to 0.5% by mass. % Is more preferable.
  • the resin composition contains a dispersant, the dispersibility of the inorganic filler in the resin component including the epoxy resin and the novolac resin is further improved, and the inorganic filler is uniformly dispersed, so that it is higher. Thermal conductivity and stronger adhesion can be achieved.
  • the dispersant can be appropriately selected from those commonly used.
  • ED-113 manufactured by Enomoto Kasei Co., Ltd.
  • DISPERBYK-106 manufactured by BYK-Chemie GmbH
  • DISPERBYK-111 manufactured by BYK-Chemie GmbH
  • Azisper PN-411 manufactured by Ajinomoto Fine Techno
  • REB122-4 Hade by Kasei Kogyo
  • These dispersants may be used alone or in combination of two or more.
  • the content of the dispersant in the resin composition is not particularly limited, but is preferably 0.01% by mass to 2% by mass with respect to the inorganic filler from the viewpoint of thermal conductivity. More preferably, the content is from 1% by mass to 1% by mass.
  • a usual method for producing a resin composition can be used without particular limitation.
  • an inorganic filler and a coupling agent as necessary are mixed, and in addition to the epoxy resin and curing agent dissolved or dispersed in a suitable organic solvent, other curing accelerators or the like added as necessary It can be obtained by mixing the components.
  • the organic solvent for dissolving or dispersing the curing agent can be appropriately selected according to the novolak resin used.
  • alcohols such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-propanol, cellosolve, methyl cellosolve, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, and butyl acetate
  • An ester solvent such as ethyl lactate, an ether solvent such as dibutyl ether, tetrahydrofuran or methyltetrahydrofuran, or a nitrogen solvent such as dimethylformamide or dimethylacetamide can be preferably used.
  • the resin sheet of this invention can be obtained by shape
  • the resin sheet of the present invention may be an uncured body or a semi-cured body.
  • semi-curing refers to a state generally referred to as a B stage state, where the viscosity at room temperature (25 ° C.) is 10 4 to 10 5 Pa ⁇ s, whereas the viscosity at 100 ° C. is 10 2 to It means a state where the viscosity decreases to 10 3 Pa ⁇ s.
  • the viscosity can be measured by a torsional dynamic viscoelasticity measuring device or the like.
  • the resin sheet of the present invention may be one in which a resin layer made of the resin composition is provided on a support.
  • the thickness of the resin layer can be appropriately selected according to the purpose. For example, it is 50 ⁇ m to 500 ⁇ m, and is preferably thinner from the viewpoint of thermal resistance and thicker from the viewpoint of insulation. Preferably, the thickness is 70 ⁇ m to 300 ⁇ m, more preferably 100 ⁇ m to 250 ⁇ m.
  • the support examples include an insulating support and a conductive support.
  • the insulating support include plastic films such as polytetrafluoroethylene film, polyethylene terephthalate film, polybutylene terephthalate, polyethylene naphthalate, polyethylene film, polypropylene film, polymethylpentene film, polyamide film, and polyimide film.
  • the conductive support a metal such as copper foil or aluminum foil or a metal-deposited plastic film can be used.
  • the insulating support may be subjected to surface treatment such as primer coating, UV treatment, corona discharge treatment, polishing treatment, etching treatment, mold release treatment.
  • the conductive support may also be subjected to surface treatment such as primer coating, coupling treatment, UV treatment, etching treatment, mold release treatment and the like.
  • a resin layer may be provided on the roughened surface by polishing treatment or electrolytic foil.
  • the said support body may be arrange
  • the film thickness of the support is not particularly limited, and is determined based on the knowledge of those skilled in the art as appropriate depending on the film thickness of the resin composition layer, the use of the resin sheet, and the production equipment. In view of excellent handling properties, the thickness is preferably 10 ⁇ m to 150 ⁇ m, more preferably 40 ⁇ m to 110 ⁇ m.
  • the resin sheet of the present invention can be produced, for example, by applying and drying the resin composition on the support.
  • a method that is usually used can be appropriately selected without particular limitation.
  • examples of the coating method include a comma coater, a die coater, and dip coating.
  • a box-type hot air dryer can be used for batch processing, and a multi-stage hot air dryer can be used for continuous processing with a coating machine.
  • the heating conditions for drying but when using a hot air dryer, the hot air of the dryer is lower than the boiling point of the solvent from the viewpoint of preventing the resin composition coating from swelling. It is preferable to include the process of heat-processing in the range.
  • the method for semi-curing is not particularly limited and a commonly used method can be appropriately selected.
  • the resin composition is semi-cured by heat treatment.
  • the temperature range for the semi-curing can be appropriately selected according to the epoxy resin constituting the resin composition. From the viewpoint of the strength of the B-stage sheet, it is preferable to proceed the curing reaction slightly by heat treatment, and the temperature range of the heat treatment is preferably 80 ° C. to 150 ° C., more preferably 100 ° C. to 120 ° C. .
  • the heat treatment time for semi-curing is not particularly limited, but can be appropriately selected from the viewpoints of the curing speed of the resin of the B-stage sheet and the fluidity and adhesiveness of the resin. Heating is preferably performed within 30 minutes, more preferably 3 to 10 minutes.
  • thermocompression bonding can be selected depending on the softening point and melting point of the resin, but is preferably 80 ° C. to 180 ° C., more preferably 100 ° C. to 150 ° C.
  • the pressurization during thermocompression bonding is preferably performed under vacuum, more preferably 4 MPa to 20 MPa under vacuum, and still more preferably 5 MPa to 15 MPa.
  • the cured resin sheet of the present invention can be obtained by curing the resin composition.
  • the resin cured material excellent in heat conductivity can be comprised.
  • the method used normally can be selected suitably, For example, the said resin composition is hardened
  • the specific temperature range can be appropriately selected according to the epoxy resin constituting the resin composition, but is preferably 80 ° C to 180 ° C, more preferably 100 ° C to 150 ° C. By performing the heat treatment in such a temperature range, higher thermal conductivity can be achieved. When the temperature is 150 ° C. or lower, curing is prevented from proceeding too quickly, and when the temperature is 80 ° C. or higher, the resin is melted and curing proceeds.
  • the time for the heat treatment in the specific temperature range is not particularly limited, but it is preferable to heat within 30 seconds to 15 minutes.
  • the heat treatment at a higher temperature is preferably performed at 120 ° C. to 250 ° C., more preferably 120 ° C. to 200 ° C. If the temperature is too high, the resin is likely to oxidize and cause coloring.
  • the heat treatment time is preferably 30 minutes to 8 hours, more preferably 1 hour to 5 hours. Furthermore, this heat treatment is preferably carried out in multiple stages from a low temperature to a high temperature within the above temperature range.
  • examples of the method for forming a cured product of the resin composition into a sheet include a method in which the resin sheet is molded and then cured, and a method in which the resin composition is cured and then sliced into a sheet.
  • the structure of the present invention includes the resin sheet or the cured resin sheet (hereinafter sometimes collectively referred to as “the sheet of the present invention”) and a metal provided in contact with one or both sides of the sheet of the present invention. And a board.
  • the metal plate examples include a copper plate, an aluminum plate, and an iron plate.
  • the thickness of a metal plate or a heat sink is not specifically limited.
  • a resin sheet with metal foil what has the said metal foil on the single side
  • the thickness of the metal plate is preferably set as appropriate depending on the usage pattern and the thermal conductivity of the metal plate. Specifically, the average thickness is preferably 5 ⁇ m to 300 ⁇ m, and preferably 15 ⁇ m to 200 ⁇ m. Is more preferable, and it is preferably 30 ⁇ m to 150 ⁇ m.
  • the structure can be produced by a production method including a step of obtaining a laminate by disposing a metal plate on at least one surface of the sheet of the present invention.
  • a method for arranging the metal plate on the sheet of the present invention a commonly used method can be used without any particular limitation.
  • a method of bonding a metal plate on at least one surface of the sheet of the present invention can be exemplified.
  • the bonding method include a pressing method and a laminating method. The conditions for the pressing method and the laminating method can be appropriately selected according to the configuration of the resin sheet.
  • the structure may have a metal plate on one surface of the sheet of the present invention and an adherend on the other surface.
  • the adherend is not particularly limited, and examples of the material of the adherend include a composite material that is a metal, a resin, a ceramic, and a mixture thereof.
  • the structure can be used for a semiconductor device for power or light source.
  • 1 to 7 show configuration examples of a power semiconductor device, an LED light bar, and an LED bulb that are configured using the sheet of the present invention as examples of the structure.
  • FIG. 1 a resin sheet 110 with a metal foil in which a semi-cured resin sheet 112 and a metal support 114 are laminated as a protective layer of the semi-cured resin sheet 112 is used.
  • FIG. 1 shows that the power semiconductor chip 102 is disposed on a copper or copper alloy lead frame 106 through a solder layer 104, and is sealed and fixed with a sealing resin 108, whereby the resin with metal foil of the present invention is used.
  • the semi-cured resin sheet 112 in the sheet 110 is pressure-bonded and cured with the lead frame 106, the metal support 114 is configured as a protective layer for the semi-cured resin sheet 112, and the heat sink 120 is interposed via a heat conductive material 122 such as heat radiation grease.
  • It is a schematic sectional drawing which shows the structural example of the power semiconductor device 100 arrange
  • the resin sheet 110 with metal foil of the present invention it is possible to electrically insulate between the lead frame 106 and the heat sink 120 and to efficiently dissipate heat generated in the power semiconductor chip 102 to the heat sink 120.
  • a thick metal plate can be used for the lead frame 106 in order to improve heat dissipation.
  • the heat sink 120 can be configured by using copper or aluminum having thermal conductivity, and can further efficiently transfer heat to a fluid such as air or water by forming cooling fins and water channels.
  • Examples of power semiconductor chips include IGBTs, MOS-FETs, diodes, and integrated circuits. In the following FIGS. 2 to 7, the members described in FIG. 1 are denoted by the same reference numerals and description thereof is omitted.
  • FIG. 2 shows the present invention in a so-called individual semiconductor component in which a power semiconductor chip 102 is disposed on a copper lead frame 106 via a solder layer 104 and sealed and fixed with a sealing resin 108 and a heat sink 120.
  • 2 is a schematic cross-sectional view showing a configuration example of a power semiconductor device 150 in which a semi-cured resin sheet 112 is pressure-bonded and heat-cured and disposed via a heat conductive material 122.
  • FIG. 3 the power semiconductor chip 102 is disposed on a lead frame 106 made of copper or copper alloy via a solder layer 104, and the lead frame 106 made of copper or copper alloy is crimped to the heat sink 120 via the resin sheet 112 of the present invention.
  • FIG. 6 is a schematic cross-sectional view showing a configuration example of a power semiconductor device 160 that is sealed with a sealing resin 108. As in FIG. 1, it is possible to achieve both insulation and heat dissipation.
  • FIG. 4 is a schematic cross-sectional view showing a configuration example of a power semiconductor device 200 configured by disposing heat sinks 120 on both surfaces of the power semiconductor chip 102. Between each heat sink 120 and the lead frame 106, the resin sheet 110 with a metal foil of the present invention is disposed. The spacer 107 is disposed between the power semiconductor chip 102 and the lead frame 106 via the solder layer 104. With this configuration, it is possible to obtain a high cooling effect as compared with the single-sided cooling structure of FIGS.
  • FIG. 5 is a schematic cross-sectional view showing a configuration example of a power semiconductor device 210 configured by arranging cooling members on both surfaces of the power semiconductor chip 102. Since the resin sheet 112 of the present invention bonds the lead frame 106 and the heat sink 120, the spacer 107 is not necessary, and a higher cooling effect than the configuration of FIG. 4 can be obtained.
  • FIG. 6 is a schematic cross-sectional view showing an example of the configuration of an LED light bar 300 configured using a structure 115 in which a cured resin sheet 112 of the present invention is sandwiched between a circuit-formed copper foil 116 and an aluminum plate 118.
  • the LED light bar 300 includes a housing 132, a heat conductive material 122, a structure 115 of the present invention, and an LED individual component 130 arranged in this order.
  • the LED individual component 130 that is a heating element can efficiently dissipate heat while having aluminum electrical insulation properties through the circuit-formed copper foil 116 and the cured resin sheet 112 of the present invention.
  • the housing 132 can be made of metal to function as a heat sink.
  • FIG. 7 is a schematic cross-sectional view showing an example of a configuration of an LED bulb 400 configured using a structure 115 in which a cured resin sheet 112 of the present invention is sandwiched between a circuit-formed copper foil 116 and an aluminum plate 118.
  • the LED bulb 400 has an LED drive circuit 142, and the cap 146 on one side, the heat conductive material 122 on the other side, the structure 115 of the present invention, and the individual LED component 130 are arranged in this order via the bulb casing 140.
  • the LED individual component 130 is covered with a lens 146.
  • the LED individual component 130 that is a heating element is disposed on the light bulb housing 140 via the structure 115 of the present invention, so that heat can be efficiently radiated.
  • TPM-Ep Triphenylmethane epoxy resin (Nippon Kayaku EPPN-502H, multifunctional / branched solid epoxy resin, epoxy equivalent 168 g / eq)
  • PhN-Ep Bisphenol F novolak type epoxy resin (Mitsubishi Chemical Corporation jER 152, polyfunctional, linear liquid epoxy resin, epoxy equivalent of 165 g / eq)
  • BisAF-Ep Liquid bisphenol A type epoxy resin and bisphenol F type epoxy resin mixture (manufactured by Nippon Steel Chemical Co., Ltd. ZX-1059, bifunctional liquid epoxy resin, epoxy equivalent 165 g / eq)
  • TPP Triphenylphosphine (Wako Pure Chemical Industries, Ltd.)
  • PAM N-phenyl-3-aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBM-573)
  • PET Single-sided release-treated polyethylene terephthalate film (Fujimori Kogyo Co., Ltd., film binder 75E-0010CTR-4)
  • GTS Electrolytic copper foil (Furukawa Electric Co., Ltd., thickness 80 ⁇ m, GTS grade)
  • Resorcinol novolak resin (ReN) was measured for molecular weight by GPC, the monomer content was 8% by mass, and the number average molecular weight of the reaction product excluding the monomer was 900. 1 H NMR measurement showed that the repeating unit contained 2.0 hydroxyl groups on average. By dividing the number average molecular weight by the molecular weight 122 of the structural unit of the formula (I), the average number of repeating units n was calculated as 7.4. The hydroxyl equivalent was 62 g / eq.
  • Resorcinol / catechol novolak resin was measured for molecular weight by GPC, the monomer content was 8% by mass, and the number average molecular weight of the reaction product excluding the monomer was 600. 1 H NMR measurement revealed that the repeating unit contained 1.8 hydroxyl groups on average. The hydroxyl equivalent was 62 g / eq. Further, when the structure was confirmed by FD-MS, at least one xanthene skeleton derivative represented by any of the following formulas (VIIIa) to (VIIId) was contained. By ignoring the xanthene skeleton derivative and dividing the number average molecular weight by the molecular weight 119 of the structural unit of formula (I), the average number of repeating units n was calculated to be 5.0.
  • hydroxyl equivalent was measured by acetyl chloride-potassium hydroxide titration method. The determination of the titration end point was performed by potentiometric titration rather than coloration with an indicator because the solution color was dark. Specifically, the hydroxyl group of the measurement resin was acetylated in a pyridine solution, the excess reagent was decomposed with water, and the resulting acetic acid was titrated with a potassium hydroxide / methanol solution.
  • the crosslink density of the cured resin can be obtained from (Equation 2) from the storage elastic modulus minimum value (E'min) of the rubber-like flat region of the cured resin according to the classical rubber elasticity theory.
  • n Crosslink density (mol / cm 3 )
  • Mc Average molecular weight between crosslink points (g / mol)
  • E′min minimum value of tensile storage modulus (Pa)
  • ⁇ density (g / cm 3 )
  • ⁇ front coefficient ( ⁇ 1)
  • R gas constant (J / K ⁇ mol)
  • T Absolute temperature of E'min (K)
  • Example 1 In a 250 mL plastic bottle, 10.0 g (100 parts) of TPM-Ep as a polyfunctional epoxy resin main agent, 3.7 g (37 parts) of ReN as a curing agent, and 0.11 g (1.1 parts of TPP as a curing accelerator) ), 56 g (560 parts) of HP-40 as the inorganic filler, 11.3 g (113 parts) of AA-04, 0.07 g (0.7 parts) of PAM as the coupling agent, and BYK-106 as the dispersant.
  • the obtained resin composition varnish was applied onto the release surface of a PET film (75E-0010CTR-4, manufactured by Fujimori Kogyo Co., Ltd.) using an applicator with a gap of 400 ⁇ m, and then immediately a box oven at 100 ° C. For 10 minutes.
  • a B-stage sheet was obtained as a resin sheet having a resin composition layer thickness of 200 ⁇ m.
  • the PET film is peeled off from both sides of the obtained B stage sheet, and both sides are sandwiched between the roughened surfaces of the GTS copper foil having a thickness of 80 ⁇ m, and vacuum hot press (hot plate temperature 150 ° C., vacuum degree ⁇ 1 kPa, pressure 10 MPa, processing time) 10 minutes), followed by secondary curing in a box-type oven at 160 ° C. for 2 hours and 190 ° C. for 2 hours to obtain a structure having copper foil on both sides.
  • vacuum hot press hot plate temperature 150 ° C., vacuum degree ⁇ 1 kPa, pressure 10 MPa, processing time
  • Example 2 In place of HP-40 and AA-04, the inorganic filler of Example 1 was 84.9 g (849 parts) of AA-18, 30.9 g (309 parts) of AA-3, and 12.9 g of AA-04 A cured resin was obtained in the same manner as in Example 1 except that (129 parts) was used.
  • Comparative Example 3 instead of HP-40 and AA-04, the inorganic filler of Comparative Example 1 was 84.9 g (849 parts) of AA-18, 30.9 g (309 parts) of AA-3 and 12.9 g of AA-04. A cured resin was obtained in the same manner as in Comparative Example 1 except that (129 parts) was used.
  • Examples 2 to 12 Comparative Examples 4 to 5> According to the procedure of Example 1, the materials shown in Table 2 were blended to obtain a cured resin. In addition, the hardening accelerator, the coupling agent, and the dispersing agent which are materials not described in Table 2 were blended in the same amounts as in Example 1.
  • the produced B-stage sheet was cut out to a length of 100 mm and a width of 10 mm, and the PET film on the surface was removed.
  • the sample is applied to a jig made of aluminum and having a diameter of 20 to 140 mm and 20 mm increments stacked in multiple stages, and the minimum diameter that can be bent without breaking at 25 ° C. is 20 mm.
  • it was evaluated as ⁇ , in the case of 80 mm or 100 mm, ⁇ in the practical limit, and in the case of 120 mm or more, x was evaluated as inappropriate.
  • a copper foil-removed resin sheet cured product sample was placed in a metal container, and an electrode (aluminum flat round electrode, diameter 25 mm, contact surface 20 mm) was placed in a sheet shape. Subsequently, Fluorinert insulating oil (FC-40 manufactured by 3M) was poured, and the dielectric breakdown voltage at 25 ° C. was measured using DAC-6032C manufactured by Sokenden in a state immersed in Fluorinert. The measurement conditions were a constant speed boost with a frequency of 50 Hz and a boost speed of 500 V / sec.
  • Examples 1 to 12 have superior flexibility before curing as compared with Comparative Examples 1 to 5, and show high thermal conductivity after curing.
  • TPM-Ep, PhN-Ep, and BisAF-Ep have almost the same hydroxyl equivalent weight and the same amount. Thermal conductivity is greatly different.
  • TPM-Ep is a resin skeleton that has a branched structure at the reactive end in the repeating unit and has a high crosslink density. Therefore, compared to PhN-Ep and bifunctional Bis-AF with polyfunctional and linear structures, It can be said that the effect of improving the conductivity has appeared.
  • the results of Comparative Examples 1, 4, and 5 are considered to be due to the lower thermal conductivity compared to Example 1 and the low crosslink density of the epoxy resin composition.
  • Example 11 From the results of Examples 8 to 10, it can be said that boron nitride can be reduced and the proportion of aluminum oxide can be increased to 34% by volume of the inorganic filler as compared with Examples 1, 6, and 7. From the results of Example 11, it can be said that the heat conductivity of the cured resin can be improved when aluminum nitride having a higher thermal conductivity than aluminum oxide is used as the small particle size filler as compared with Example 1.
  • 102 Power semiconductor chip
  • 104 Solder layer
  • 106 Metal plate for wiring (lead frame, bus bar)
  • 107 Spacer
  • 108 Sealing resin
  • 110 Resin sheet with metal foil
  • 112 Resin sheet or cured resin Sheet
  • 114 Metal foil support
  • 115 Structure
  • 116 Circuit processed metal foil
  • 118 Metal plate
  • 120 Heat sink
  • 122 Thermal conductive material (heat radiation grease, heat radiation sheet, phase change sheet)
  • 130 LED individual parts
  • 132 housing
  • 140 LED bulb housing
  • 142 LED drive circuit
  • 144 lens
  • 146 base

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Abstract

L'invention porte sur une composition de résine qui contient une résine époxyde contenant une résine époxyde multifonctionnelle, un agent durcisseur contenant une résine novolaque ayant un motif de structure représenté par la formule générale (I) et une charge inorganique contenant des particules de nitrure. Dans la formule générale (I) : R1 et R2 représentent chacun indépendamment un atome d'hydrogène ou un groupe méthyle ; m présente une valeur moyenne de 1,5 à 2,5 ; et n présente une valeur moyenne de 1 à 15.
PCT/JP2011/069845 2011-08-31 2011-08-31 Composition de résine, feuille de résine, feuille de résine dotée d'une feuille métallique, feuille de résine durcie, structure et dispositif à semi-conducteur pour une source d'énergie ou de lumière WO2013030998A1 (fr)

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PCT/JP2011/069845 WO2013030998A1 (fr) 2011-08-31 2011-08-31 Composition de résine, feuille de résine, feuille de résine dotée d'une feuille métallique, feuille de résine durcie, structure et dispositif à semi-conducteur pour une source d'énergie ou de lumière
KR1020187002450A KR101970771B1 (ko) 2011-08-31 2011-08-31 수지 조성물, 수지 시트, 금속박 구비 수지 시트, 수지 경화물 시트, 구조체, 및 동력용 또는 광원용 반도체 디바이스
KR1020197010761A KR102081876B1 (ko) 2011-08-31 2011-08-31 수지 조성물, 수지 시트, 금속박 구비 수지 시트, 수지 경화물 시트, 구조체, 및 동력용 또는 광원용 반도체 디바이스
KR1020147007771A KR101825259B1 (ko) 2011-08-31 2011-08-31 수지 조성물, 수지 시트, 금속박 구비 수지 시트, 수지 경화물 시트, 구조체, 및 동력용 또는 광원용 반도체 디바이스
CN201180073184.9A CN103764713B (zh) 2011-08-31 2011-08-31 树脂组合物、树脂片、带金属箔的树脂片、树脂固化物片、结构体、以及动力用或光源用半导体装置
JP2013530974A JP5850056B2 (ja) 2011-08-31 2011-08-31 樹脂組成物、樹脂シート、金属箔付き樹脂シート、樹脂硬化物シート、構造体、および動力用又は光源用半導体デバイス
TW105112040A TWI585147B (zh) 2011-08-31 2012-08-31 樹脂組成物、樹脂片、附有金屬箔的樹脂片、樹脂硬化物片、結構體以及動力用或光源用半導體元件
TW101131781A TWI548692B (zh) 2011-08-31 2012-08-31 樹脂組成物、樹脂片、附有金屬箔的樹脂片、樹脂硬化物片、結構體以及動力用或光源用半導體元件

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CN103959488A (zh) * 2013-03-28 2014-07-30 日东电工株式会社 系统、制造条件决定装置以及制造管理装置
CN104076760A (zh) * 2013-03-28 2014-10-01 日东电工株式会社 远程控制系统及中央控制装置、客户端和信息采集装置
WO2016002846A1 (fr) * 2014-07-02 2016-01-07 住友ベークライト株式会社 Dispositif semi-conducteur
JP2016138194A (ja) * 2015-01-28 2016-08-04 日立化成株式会社 樹脂組成物、樹脂シート及び樹脂シート硬化物
JP2018162335A (ja) * 2017-03-24 2018-10-18 株式会社豊田中央研究所 熱伝導性複合材料
WO2020004225A1 (fr) * 2018-06-26 2020-01-02 京セラ株式会社 Substrat organique, stratifié plaqué de métal et tableau de connexions
WO2020067364A1 (fr) * 2018-09-28 2020-04-02 富士フイルム株式会社 Composition pour former des matériaux thermoconducteurs, matériau thermoconducteur, feuille thermoconductrice, dispositif avec couche thermoconductrice, et film
JP2021161205A (ja) * 2020-03-31 2021-10-11 味の素株式会社 樹脂組成物、樹脂組成物の硬化物、樹脂シート、プリント配線板、半導体チップパッケージ及び半導体装置
JP2021161206A (ja) * 2020-03-31 2021-10-11 味の素株式会社 樹脂組成物、樹脂ペースト、硬化物、樹脂シート、プリント配線板、半導体チップパッケージ及び半導体装置
US20220219357A1 (en) * 2019-05-03 2022-07-14 3M Innovative Properties Company Film usable for roll-to-roll processing of flexible electronic devices comprising a composite material of a polymer and boron nitride
WO2023189610A1 (fr) * 2022-03-31 2023-10-05 デンカ株式会社 Composition de résine, corps durci en résine isolante, stratifié et substrat de circuit
WO2023189609A1 (fr) * 2022-03-31 2023-10-05 デンカ株式会社 Composition de résine, corps durci en résine isolante, stratifié et substrat de circuit

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JP6222209B2 (ja) * 2015-12-04 2017-11-01 日立化成株式会社 樹脂組成物、樹脂シート、金属箔付き樹脂シート、樹脂硬化物シート、構造体、および動力用又は光源用半導体デバイス
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CN103959488A (zh) * 2013-03-28 2014-07-30 日东电工株式会社 系统、制造条件决定装置以及制造管理装置
CN104076760A (zh) * 2013-03-28 2014-10-01 日东电工株式会社 远程控制系统及中央控制装置、客户端和信息采集装置
WO2016002846A1 (fr) * 2014-07-02 2016-01-07 住友ベークライト株式会社 Dispositif semi-conducteur
JPWO2016002846A1 (ja) * 2014-07-02 2017-04-27 住友ベークライト株式会社 半導体装置
JP2016138194A (ja) * 2015-01-28 2016-08-04 日立化成株式会社 樹脂組成物、樹脂シート及び樹脂シート硬化物
JP2018162335A (ja) * 2017-03-24 2018-10-18 株式会社豊田中央研究所 熱伝導性複合材料
JPWO2020004225A1 (ja) * 2018-06-26 2021-07-08 京セラ株式会社 有機基板、金属張積層板および配線基板
WO2020004225A1 (fr) * 2018-06-26 2020-01-02 京セラ株式会社 Substrat organique, stratifié plaqué de métal et tableau de connexions
US11661495B2 (en) 2018-06-26 2023-05-30 Kyocera Corporation Organic board, metal-clad laminate, and wiring board
WO2020067364A1 (fr) * 2018-09-28 2020-04-02 富士フイルム株式会社 Composition pour former des matériaux thermoconducteurs, matériau thermoconducteur, feuille thermoconductrice, dispositif avec couche thermoconductrice, et film
US20220219357A1 (en) * 2019-05-03 2022-07-14 3M Innovative Properties Company Film usable for roll-to-roll processing of flexible electronic devices comprising a composite material of a polymer and boron nitride
JP2021161205A (ja) * 2020-03-31 2021-10-11 味の素株式会社 樹脂組成物、樹脂組成物の硬化物、樹脂シート、プリント配線板、半導体チップパッケージ及び半導体装置
JP2021161206A (ja) * 2020-03-31 2021-10-11 味の素株式会社 樹脂組成物、樹脂ペースト、硬化物、樹脂シート、プリント配線板、半導体チップパッケージ及び半導体装置
JP7424168B2 (ja) 2020-03-31 2024-01-30 味の素株式会社 樹脂組成物、樹脂ペースト、硬化物、樹脂シート、プリント配線板、半導体チップパッケージ及び半導体装置
JP7424167B2 (ja) 2020-03-31 2024-01-30 味の素株式会社 樹脂組成物、樹脂組成物の硬化物、樹脂シート、プリント配線板、半導体チップパッケージ及び半導体装置
WO2023189610A1 (fr) * 2022-03-31 2023-10-05 デンカ株式会社 Composition de résine, corps durci en résine isolante, stratifié et substrat de circuit
WO2023189609A1 (fr) * 2022-03-31 2023-10-05 デンカ株式会社 Composition de résine, corps durci en résine isolante, stratifié et substrat de circuit

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TW201625735A (zh) 2016-07-16
KR20180012343A (ko) 2018-02-05
KR102081876B1 (ko) 2020-02-26
TWI548692B (zh) 2016-09-11
JPWO2013030998A1 (ja) 2015-03-23
CN103764713B (zh) 2016-08-24
KR101825259B1 (ko) 2018-02-02
KR20140071377A (ko) 2014-06-11
CN103764713A (zh) 2014-04-30
TWI585147B (zh) 2017-06-01
JP5850056B2 (ja) 2016-02-03
KR20190042109A (ko) 2019-04-23
KR101970771B1 (ko) 2019-04-22

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