Thermosetting resin compositions, cured products thereof, laminates, metal-based substrates, and power modules

Abstract

A thermosetting resin composition that can achieve high thermal conductivity and high heat resistance is provided. [Solution] The thermosetting resin composition of the present invention contains a bismaleimide compound that does not contain a mesogenic group in the molecule and that contains a conjugated structure in which the nitrogen atom of the maleimide group is conjugated with an aromatic ring, a curing agent for the bismaleimide compound, and a thermally conductive filler that has a thermal conductivity of 20 W / m·K or more.

Description

[Technical Field]

[0001] The present invention relates to thermosetting resin compositions, cured products thereof, laminates, metal-based substrates, and power modules. [Background technology]

[0002] Insulating materials that make up electrical and electronic equipment are required to have heat dissipation properties. Various developments have been made regarding the heat dissipation properties of insulating materials. As an example of this type of technology, the technology described in Patent Document 1 is known. Patent Document 1 describes that an insulating material with high thermal conductivity can be provided by using a resin layer containing an epoxy resin having a mesogenic skeleton, a curing agent, and an inorganic filler. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2014-139021 [Overview of the Initiative] [Problems that the invention aims to solve]

[0004] However, as a result of the inventor's investigation, it was found that the resin layer described in Patent Document 1 has room for improvement in terms of achieving both high thermal conductivity and high heat resistance. [Means for solving the problem]

[0005] Further investigation by the inventors revealed that while using an epoxy resin having a mesogenic skeleton could improve thermal conductivity, it conversely reduced heat resistance. Based on this finding, further intensive research led to the discovery that by employing a bismaleimide compound having a predetermined conjugated structure within the molecule, it was possible to improve thermal conductivity while suppressing the decrease in heat resistance, thus completing the present invention.

[0006] According to the present invention, A bismaleimide compound that does not contain a mesogenic group within the molecule and contains a conjugated structure in which the nitrogen atom of the maleimide group is conjugated with an aromatic ring, The curing agent of the bismaleimide compound, A thermosetting resin composition is provided, comprising a thermally conductive filler having a thermal conductivity of 20 W / m·K or higher.

[0007] Furthermore, according to the present invention, A bismaleimide compound containing a mesogenic group, The curing agent of the bismaleimide compound, A thermosetting resin composition is provided, comprising a thermally conductive filler.

[0008] Furthermore, according to the present invention, a cured product of the above-mentioned thermosetting resin composition is provided.

[0009] Furthermore, according to the present invention, Adhesive layer, The adhesive layer comprises an insulating layer provided on the adhesive layer, A laminate is provided in which the insulating layer is composed of a resin layer made of the thermosetting resin composition described above.

[0010] Furthermore, according to the present invention, A metal substrate and An insulating layer provided on the metal substrate, It comprises a metal layer provided on the insulating layer, A metal-based substrate is provided, wherein the insulating layer is composed of one selected from the group consisting of a resin layer made of the thermosetting resin composition and the laminate.

[0011] Furthermore, according to the present invention, The above metal base substrate, A power module is provided comprising electronic components provided on the metal base substrate. [Effects of the Invention]

[0012] According to the present invention, there are provided a thermosetting resin composition capable of achieving high thermal conductivity and high heat resistance, a cured product using the same, a laminate, a metal base substrate, and a power module.

Brief Description of the Drawings

[0013] [Figure 1] It is a cross-sectional view showing the configuration of the metal base substrate according to the present embodiment. [Figure 2] It is a cross-sectional view showing the configuration of the power module according to the present embodiment.

Modes for Carrying Out the Invention

[0014] Hereinafter, embodiments of the present invention will be described with reference to the drawings. In all the drawings, the same components are denoted by the same reference numerals, and the description will be omitted as appropriate. Also, the figures are schematic and do not match the actual dimensional ratios.

[0015] The outline of the thermosetting resin composition of the present embodiment will be described. The thermosetting resin composition of the first embodiment can contain a bismaleimide compound that does not contain a mesogenic group in the molecule and contains a conjugated structure in which the nitrogen atom of the maleimide group is conjugated with an aromatic ring, a curing agent for the bismaleimide compound, and a thermally conductive filler having a thermal conductivity of 20 W / m·K or more.

[0016] The thermosetting resin composition of the second embodiment can contain a bismaleimide compound containing a mesogenic group, a curing agent for the bismaleimide compound, and a thermally conductive filler.

[0017] According to the inventors' findings, it has been discovered that by employing a bismaleimide compound having a predetermined conjugated structure within the molecule, a heat dissipation material with improved heat resistance and thermal conductivity can be realized. Although the detailed mechanism is not clear, it is thought that the conjugated structure in which the nitrogen atom of the maleimide group is conjugated with the aromatic ring, or the conjugated structure in the mesogenic group, enhances thermal conductivity, and the thermosetting crosslinking group having a maleimide skeleton with excellent heat resistance enhances heat resistance. In other words, it is thought that the thermal conductivity of the matrix resin constituting the three-dimensional crosslinking structure can be increased, and heat resistance can be improved by a maleimide-based crosslinking structure that differs from epoxy-based crosslinking structures.

[0018] The thermosetting resin composition of this embodiment can be used as a heat-dissipating insulating material for electrical and electronic equipment. This heat-dissipating insulating material can be used, for example, as a substrate material for mounting electronic components.

[0019] Electrical and electronic equipment can use, for example, conventional semiconductor devices (electronic devices equipped with semiconductor elements as electronic components) and power modules (electronic devices equipped with power semiconductor elements as electronic components). Power semiconductor elements use wide-bandgap materials such as SiC, GaN, Ga2O3, or diamond, and are designed for use with high voltage and high current. Therefore, they generate more heat than conventional silicon chips (semiconductor elements) and operate in even higher temperature environments. Power semiconductor elements are required to be used for long periods in high-temperature operating environments, such as 200°C or above, or 250°C or above. Specific examples of power semiconductor elements include rectifier diodes, power transistors, power MOSFETs, insulated-gate bipolar transistors (IGBTs), thyristors, gate-turn-off thyristors (GTOs), and triacs.

[0020] According to the inventors' findings, the softening point can be used as an indicator of the heat resistance of a heat-dissipating insulating material (thermosetting resin composition). For example, by using a softening point of 150°C as an indicator, the heat resistance under normal semiconductor device operating conditions can be evaluated, and by using a softening point of 200°C as an indicator, the heat resistance under power module operating conditions can be evaluated.

[0021] The softening point of the thermosetting resin composition of this embodiment is, for example, 100°C or higher, preferably 150°C or higher, more preferably 180°C or higher, and even more preferably 200°C or higher. By setting the softening point to 150°C or higher, it can be suitably used in ordinary semiconductor devices, and by setting the softening point to 200°C or higher, a heat dissipation insulating material suitable for use in power modules can be realized. The upper limit of the softening point is not particularly limited, but for example, it may be 400°C or lower.

[0022] The thermosetting resin composition of this embodiment provides a heat-dissipating insulating material that can be used in power modules.

[0023] Each component of the thermosetting resin composition of this embodiment will be described in detail.

[0024] The thermosetting resin composition according to the first embodiment includes a bismaleimide compound containing a mesogenic group in its molecule (hereinafter also referred to as a mesogenic bismaleimide compound) as the thermosetting resin.

[0025] The thermosetting resin composition according to the second embodiment includes a bismaleimide compound (hereinafter also referred to as a non-mesogenic bismaleimide compound) as the thermosetting resin, which does not contain a mesogenic group in its molecule and contains a conjugated structure in which the nitrogen atom of the maleimide group is conjugated with an aromatic ring.

[0026] The above-mentioned non-mesogenic bismaleimide compounds may include bismaleimide compounds that do not contain a mesogenic group, including the compound represented by the following general formula (A). [ka] (In the above general formula (A), n1 is an integer between 0 and 10, and X1 is independently an alkylene group having 1 to 10 carbon atoms, a group represented by the following formula (1a), a group represented by the formula "-SO2-", a group represented by "-CO-", an oxygen atom Child (Yes, R1 is an independent hydrocarbon group with 1 to 6 carbon atoms, a is an independent integer between 0 and 4, and b is an independent integer between 0 and 3.) [ka] (In formula (1a) above, Y is a hydrocarbon group having an aromatic ring with 6 to 30 carbon atoms, and n2 is an integer greater than or equal to 0.)

[0027] In the above general formula (A), the skeletal portion where the nitrogen atom of the maleimide group and aromatic rings such as benzene rings are adjacent forms a conjugated structure, which is thought to enhance thermal conductivity, although the detailed mechanism is not clear. Furthermore, in the above general formula (A), X1 preferably has a predetermined conjugated structure, but other -CH2- groups are also acceptable.

[0028] The alkylene group in X1 of the above general formula (A), which is between 1 and 10, is not particularly limited, but may be a linear or branched alkylene group. Examples of these linear alkylene groups include methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decanylene, trimethylene, tetramethylene, pentamethylene, and hexamethylene groups.

[0029] In general formula (A) above, the number of carbon atoms in the alkylene group X1 may be between 1 and 10, but is preferably between 1 and 7, and more preferably between 1 and 3. Specifically, examples of alkylene groups having such a number of carbon atoms include the methylene group, ethylene group, propylene group, and isopropylene group. Among these, the methylene group is preferred from the viewpoint of heat resistance.

[0030] Furthermore, in the above general formula (A), R1 is independently a hydrocarbon group having 1 to 6 carbon atoms, but it is preferable that it be a hydrocarbon group having 1 or 2 carbon atoms, specifically a methyl group or an ethyl group. Furthermore, a is an integer between 0 and 4, preferably between 0 and 2, and more preferably 0. Also, b is an integer between 0 and 3, preferably 0 or 1, and more preferably 0.

[0031] Furthermore, in the above general formula (A), n1 is an integer between 0 and 10, preferably between 0 and 6, more preferably between 0 and 4, and particularly preferably between 0 and 3. Moreover, it is more preferable that the maleimide compound contains at least one compound in formula (A) where n1 is 1 or more. As a result, the insulating layer obtained from the thermosetting resin composition exhibits superior heat resistance.

[0032] In formula (1a) above, Y is a hydrocarbon group having an aromatic ring with 6 to 30 carbon atoms, and n2 is an integer greater than or equal to 0.

[0033] In formula (1a), the hydrocarbon group having an aromatic ring with 6 to 30 carbon atoms may consist solely of an aromatic ring, or it may also have hydrocarbon groups other than an aromatic ring. Y may have one aromatic ring or two or more, and if there are two or more, these aromatic rings may be the same or different. Furthermore, the aromatic ring may have either a monocyclic or polycyclic structure. Specifically, examples of hydrocarbon groups having an aromatic ring and between 6 and 30 carbon atoms include divalent groups obtained by removing two hydrogen atoms from the nucleus of aromatic compounds such as benzene, biphenyl, naphthalene, anthracene, fluorene, phenanthrene, indacene, terphenyl, acenaphthylene, and phenalene. Furthermore, these aromatic hydrocarbon groups may have substituents. Here, an aromatic hydrocarbon group having substituents means that some or all of the hydrogen atoms constituting the aromatic hydrocarbon group are substituted by substituents. Examples of substituents include alkyl groups. The alkyl group used as the substituent is preferably a chain-like alkyl group. Furthermore, its carbon number is preferably 1 to 10, more preferably 1 to 6, and particularly preferably 1 to 4. Specific examples include methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, and sec-butyl groups.

[0034] Such a group Y preferably has two hydrogen atoms removed from benzene or naphthalene, and the group represented by formula (1a) above is preferably a group represented by either formula (1a-1) or (1a-2) below. As a result, the insulating layer obtained from the thermosetting resin composition exhibits better heat resistance.

[0035] [ka] In the above formulas (1a-1) and (1a-2), R4 is independently a hydrocarbon group having 1 to 6 carbon atoms. e is independently an integer between 0 and 4, more preferably 0.

[0036] Furthermore, in the base represented by the above formula (1a), n2 may be any integer greater than or equal to 0, but is preferably an integer between 0 and 5, more preferably an integer between 1 and 3, and particularly preferably 1 or 2.

[0037] From the above, it is preferable that the maleimide compound represented by formula (A) above has X1 as a linear or branched alkylene group having 1 to 3 carbon atoms, R1 as a hydrocarbon group with 1 or 2 carbon atoms, a as an integer between 0 and 2, b as 0 or 1, and n1 as an integer between 1 and 4. Alternatively, it is preferable that X1 is a group represented by either formula (1a-1) or (1a-2) above, and e is 0. As a result, the insulating layer obtained from the thermosetting resin composition exhibits better low thermal shrinkage and chemical resistance.

[0038] A preferred specific example of the maleimide compound represented by formula (A) above is, for example, the maleimide compound represented by the following formula (1-1), which is particularly preferred.

[0039] [ka]

[0040] Furthermore, the maleimide compound may include a maleimide compound of a different type than the maleimide compound represented by formula (A) above. Examples of such maleimide compounds include aliphatic maleimide compounds such as 1,6'-bismaleimide-(2,2,4-trimethyl)hexane, hexamethylenediaminebismaleimide, N,N'-1,2-ethylenebismaleimide, N,N'-1,3-propylenebismaleimide, and N,N'-1,4-tetramethylenebismaleimide; and imide-extended bismaleimides. Among these, 1,6'-bismaleimide-(2,2,4-trimethyl)hexane and imide-extended bismaleimides are particularly preferred. Maleimide compounds may be used alone or in combination of two or more types.

[0041] The above-mentioned mesogenic bismaleimide compounds may include, for example, bismaleimide compounds containing a mesogenic group represented by the following general formula (a). [ka]

[0042] In the general formula (a) above, each R is a mesogenic group represented by the general formula -A 1 -x-A 2 -. In the general formula, A 1 and A 2 each independently represent a substituent selected from an aromatic group, a condensed aromatic group, an alicyclic group, and an alicyclic heterocyclic group. x is a linking group, which is a direct bond or a divalent substituent selected from the group consisting of -O-, -S-, -C=C-, -C≡C-, -CO-, -CO-O-, -CO-NH-, -CH=N-, -CH=N-N=CH-, -N=N-, and -N(O)=N-.

[0043] Here, A 1 and A 2 are each independently preferably selected from a hydrocarbon group having 6 to 12 carbon atoms and having a benzene ring, a hydrocarbon group having 10 to 20 carbon atoms and having a naphthalene ring, a hydrocarbon group having 12 to 24 carbon atoms and having a biphenyl structure, a hydrocarbon group having 12 to 36 carbon atoms and having 3 or more benzene rings, a hydrocarbon group having 12 to 36 carbon atoms and having a condensed aromatic group, and an alicyclic heterocyclic group having 4 to 36 carbon atoms.

[0044] Specific examples of A 1 and A 2 in the mesogenic group include, for example, phenylene, biphenylene, naphthylene, anthracenylene, cyclohexyl, pyridyl, pyrimidyl, thiophenylene, etc. Further, these may be unsubstituted or derivatives having substituents such as an aliphatic hydrocarbon group, a halogen group, a cyano group, a nitro group, etc.

[0045] As x corresponding to the linking group in the mesogenic group, for example, a direct bond or a divalent substituent selected from the group consisting of -C=C-, -C≡C-, -CO-O-, -CO-NH-, -CH=N-, -CH=N-N=CH-, -N=N-, and -N(O)=N- is preferable. Here, the direct bond is a single bond or A 1 and A 2This means that they are interconnected and form a ring structure.

[0046] The molecular structure of the above-mentioned mesogenic bismaleimide compound can be one that has thermally crosslinkable groups on both sides via a mesogenic group. This can enhance the thermal crosslinking properties. Furthermore, in the molecular structure of the above-mentioned mesogenic bismaleimide compound, it is preferable that the mesogenic group or the bonding group X within the mesogenic group has a structure in which it is directly bonded to an aromatic ring such as a benzene ring. Although the detailed mechanism is not clear, it is thought that the thermal conductivity can be enhanced by the conjugated structure. In addition, it is thought that the thermal conductivity can be further enhanced if the mesogenic group containing an aromatic ring having a π-electron conjugated structure has a rigid structure in which the movement of molecules such as biphenyl structures is suppressed. Furthermore, in the molecular structure of the above mesogenic bismaleimide compound, it is preferable that the group bonded to the mesogenic group or the group bonded to bonded group X has a nitrogen atom that forms a resonance structure, for example, a heterocycle having a nitrogen atom. Although the detailed mechanism is not clear, it is thought that the thermal conductivity can be enhanced by the conjugated structure.

[0047] The above thermosetting resin composition may include other thermosetting resins that do not contain mesogenic groups in their molecules. Examples of other thermosetting resins include epoxy resins, cyanate resins, polyimide resins, benzoxazine resins, unsaturated polyester resins, phenolic resins, melamine resins, silicone resins, bismaleimide resins, and acrylic resins. These may be used individually or in combination of two or more.

[0048] The content of the thermosetting resin is preferably, for example, 1% by mass or more and 30% by mass or less, and more preferably 5% by mass or more and 28% by mass or less, relative to the total solid content of the thermosetting resin composition. If it is above the lower limit, handling properties are improved and it becomes easier to form the resin layer. If it is below the upper limit, the strength and flame retardancy of the resin layer are further improved, and the thermal conductivity of the resin layer is further improved.

[0049] Regarding the content of the non-mesogenic bismaleimide compound or mesogenic bismaleimide compound mentioned above, the lower limit may be 25% by mass or more, 50% by mass or more, or 75% by mass or more relative to the total thermosetting resin, while the upper limit may be 100% by mass or less. This can improve thermal conductivity and heat resistance.

[0050] In this embodiment, "solid content of thermosetting resin composition" refers to the non-volatile content in the resin composition, which is the remainder after removing volatile components such as water and solvents.

[0051] The thermosetting resin composition of this embodiment may optionally contain a curing agent. The curing agent mentioned above is selected according to the type of bismaleimide compound, and is not particularly limited as long as it is a curing agent of a bismaleimide compound that reacts with it.

[0052] The curing agent for the bismaleimide compound may include, for example, one or more selected from the group consisting of benzoxazine compounds, epoxy resins, cyanate compounds, phenol compounds, and amine compounds. These may be used individually or in combination of two or more.

[0053] As the amine compound mentioned above, at least one selected from aromatic diamine compounds and monoamine compounds can be used.

[0054] Examples of aromatic diamine compounds include o-dianisidine, o-tolidine, 3,3'-dihydroxy-4,4'-diaminobiphenyl, 4,4'-bis(4-aminophenoxy)biphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, m-phenylenediamine, p-phenylenediamine, o-xylenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylpropane, 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, 1,5-diaminonaphthalene, 4,4'-(p-phenylenediisopropylidene)dianiline, 2,2-[4-(4-aminophenoxy)phenyl]propane, 4,4'-diamino-3,3'-dimethyl-diphenylmethane, and bis(4-(4-aminophenoxy)phenyl)sulfone.

[0055] Examples of monoamine compounds include o-aminophenol, m-aminophenol, p-aminophenol, o-aminobenzoic acid, m-aminobenzoic acid, p-aminobenzoic acid, o-aminobenzenesulfonic acid, m-aminobenzenesulfonic acid, p-aminobenzenesulfonic acid, 3,5-dihydroxyaniline, 3,5-dicarboxyaniline, o-aniline, m-aniline, p-aniline, o-methylaniline, m-methylaniline, p-methylaniline, o-ethylaniline, m-ethylaniline, p-ethylaniline, o-vinylaniline, m-vinylaniline, p-vinylaniline, o-allylaniline, m-allylaniline, and p-allylaniline.

[0056] The thermosetting resin composition of this embodiment may optionally contain a curing accelerator. The type and amount of the curing accelerator mentioned above are not particularly limited, but an appropriate one can be selected from the standpoint of reaction rate, reaction temperature, and storage properties.

[0057] Examples of the curing accelerators mentioned above include imidazoles, organophosphorus compounds, organometallic salts, tertiary amines, phenolic compounds, and organic acids. These may be used individually or in combination of two or more. Among these, nitrogen atom-containing compounds such as imidazoles are preferred from the viewpoint of improving heat resistance.

[0058] Examples of the imidazoles mentioned above include 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenyl-4-methylimidazole, 2,4-diethylimidazole, 2-phenyl-4-methyl-5-hydroxyimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 1-cyanoethyl-2-phenylimidazole, and 1-cyanoethyl-2-phenylimidazolium trimellitate.

[0059] Examples of the organometallic salts mentioned above include zinc naphthenate, cobalt naphthenate, tin octoate, cobalt octoate, bisacetylacetonate cobalt(II), and trisacetylacetonate cobalt(III). Examples of the above-mentioned tertiary amines include triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, and 1,8-diazabicyclo(5,4,0)undecene-7. Examples of the phenolic compounds mentioned above include phenol, bisphenol A, nonylphenol, and 2,2-bis(3-methyl-4-hydroxyphenyl)propane. Examples of the above-mentioned organic acids include acetic acid, benzoic acid, salicylic acid, and p-toluenesulfonic acid.

[0060] The content of the curing accelerator may be 0.1% to 20% by mass, 0.1% to 5% by mass, or 0.2% to 1.5% by mass, based on 100% by mass of the total of the thermosetting resin and the curing agent.

[0061] The thermosetting resin composition of this embodiment may contain an inorganic filler. The above inorganic filler may include at least one thermally conductive filler selected from alumina, aluminum nitride, silicon carbide, boron nitride, silicon nitride, magnesium oxide, aluminum hydroxide, and barium sulfate. These may be used individually or in combination of two or more. The thermally conductive filler is not particularly limited as long as it has high thermal conductivity, but for example, one having a thermal conductivity of 20 W / m·K or higher is preferred (the upper limit of thermal conductivity is not particularly limited).

[0062] . Among these, from the viewpoint of thermal conductivity, the inorganic filler preferably contains boron nitride or aluminum nitride. This boron nitride may include monodisperse particles, aggregated particles, or mixtures thereof of flaky boron nitride. Furthermore, from the viewpoint of balancing thermal conductivity and insulation, at least one of magnesium oxide or alumina can be used.

[0063] The shape of the inorganic filler described above is not particularly limited, but it can usually be spherical.

[0064] The inorganic filler described above is preferably a mixture of two or more inorganic fillers with different volume-average particle sizes. That is, the particle size distribution curve of the inorganic filler may have at least two peaks, or at least three peaks.

[0065] The content of the inorganic filler is 50% to 90% by volume, preferably 60% to 90% by volume, and more preferably 60% to 85% by volume, based on the total solid content of the thermosetting resin composition.

[0066] The total content of the inorganic filler is, for example, 1% to 90% by mass, 5% to 85% by mass, and preferably 10% to 85% by mass, relative to the total solid content of the thermosetting resin composition. Setting it above the lower limit can improve thermal conductivity. Setting it below the upper limit can suppress a decrease in processability.

[0067] The thermosetting resin composition of this embodiment may contain a silane coupling agent. This improves the compatibility of the inorganic filler in the thermosetting resin composition. The coupling agent may be added to the thermosetting resin composition or used by treating the surface of the inorganic filler.

[0068] The silane coupling agent mentioned above may include, for example, one or more selected from the group consisting of epoxy silane coupling agents, amino silane coupling agents, mercapto silane coupling agents, ureido silane coupling agents, cationic silane coupling agents, titanate coupling agents, and silicone oil type coupling agents. These may be used individually or in combination of two or more. Among these, silane coupling agents having at least one of the following functional groups can be used: epoxy group, amino group, mercapto group, ureido group, or hydroxyl group. Furthermore, from the viewpoint of improving compatibility with resin components, silane coupling agents having non-reactive phenyl groups can be used.

[0069] Specific examples of silane coupling agents having the above-mentioned functional groups include, for example, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-(2-aminoethyl)aminopropyltrimethoxysilane, 3-(2-aminoethyl)aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptotriethoxysilane, and 3-ureidopropyltriethoxysilane. Examples of silane coupling agents containing the phenyl group mentioned above include 3-phenylaminopropyltrimethoxysilane, 3-phenylaminopropyltriethoxysilane, N-methylanilinopropyltrimethoxysilane, N-methylanilinopropyltriethoxysilane, 3-phenyliminopropyltrimethoxysilane, 3-phenyliminopropyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, triphenylmethoxysilane, and triphenylethoxysilane.

[0070] The amount of the coupling agent added is preferably, for example, 0.05% to 3% by mass, and particularly preferably 0.1% to 2% by mass, based on 100% by mass of the inorganic filler.

[0071] The thermosetting resin composition of this embodiment may contain a phenoxy resin. This can improve flexibility. Examples of the phenoxy resins mentioned above include phenoxy resins having a bisphenol skeleton, phenoxy resins having a naphthalene skeleton, phenoxy resins having an anthracene skeleton, and phenoxy resins having a biphenyl skeleton. The phenoxy resin content may be 3% to 10% by mass relative to the total solid content of the thermosetting resin composition.

[0072] The thermosetting resin composition of this embodiment may contain other components besides those described above. Examples of these other components include antioxidants and leveling agents.

[0073] For example, the following method can be used to produce the thermosetting resin composition of this embodiment. A resin varnish (a varnish-like thermosetting resin composition) can be prepared by dissolving, mixing, and stirring each of the above components, excluding the inorganic filler, in a solvent. Various mixing machines can be used for this mixing, such as ultrasonic dispersion, high-pressure impact dispersion, high-speed rotation dispersion, bead mill, high-speed shear dispersion, and rotational dispersion. The above-mentioned solvents are not particularly limited, but examples include methyl ethyl ketone, methyl isobutyl ketone, propylene glycol monomethyl ether, and cyclohexanone.

[0074] Furthermore, a thermosetting resin composition in the B-stage state can be obtained by adding an inorganic filler to the resin varnish and kneading it using a three-roll press or the like. Adding the inorganic filler during kneading allows for more uniform dispersion of the inorganic filler in the thermosetting resin, but this is not the only option. The inorganic filler may be added during kneading, or it may be added when mixing the resin varnish. From the viewpoint of dispersibility, it is preferable to add nanoparticles dispersed in a predetermined solvent (nanoparticle dispersion) to the resin varnish.

[0075] (Resin substrate) The resin substrate of this embodiment comprises an insulating layer made of a cured product of the thermosetting resin composition described above. This resin substrate can be used as a material for a substrate used to mount electronic components such as semiconductor elements and power semiconductors.

[0076] (Laminated board) The laminate of this embodiment comprises an adhesive layer and an insulating layer provided on the adhesive layer. The insulating layer in the laminate is composed of a resin layer made of the thermosetting resin composition described above. This resin layer can be made of a thermosetting resin composition in the B stage. Furthermore, this adhesive layer can improve the adhesion between the insulating layer and various metal members such as metal plates and heat sinks on its surface.

[0077] The adhesive layer described above is not particularly limited as long as it has electrical insulating properties and can bond the insulating layer to the adherend (metal member), but it may include at least one selected from epoxy resin, polyamide resin, polyamide-imide resin, and modified polyamide-imide resin. These may be used individually or in combination of two or more. The adhesive layer may also contain inorganic fillers, curing agents, etc., depending on the purpose.

[0078] (Metal-based substrate) The metal base substrate 100 of this embodiment will be described with reference to Figure 1. Figure 1 is a cross-sectional view showing an example of the configuration of the metal base substrate 100. As shown in Figure 1, the metal base substrate 100 may comprise a metal substrate 101, an insulating layer 102 provided on the metal substrate 101, and a metal layer 103 provided on the insulating layer 102. The insulating layer 102 can be composed of one selected from the group consisting of a resin layer made of the thermosetting resin composition and a laminate. Each of these resin layers and laminates may be made of a thermosetting resin composition in a B-stage state before circuit processing of the metal layer 103, and may be a cured body obtained by curing it after circuit processing.

[0079] The metal layer 103 is provided on the insulating layer 102 and subjected to circuit processing. Examples of metals constituting the metal layer 103 include one or more selected from copper, copper alloys, aluminum, aluminum alloys, nickel, iron, tin, etc. Among these, the metal layer 103 is preferably a copper layer or an aluminum layer, and particularly preferably a copper layer. Using copper or aluminum improves the circuit processability of the metal layer 103. The metal layer 103 may be made of metal foil available in sheet form or metal foil available in roll form.

[0080] The lower limit of the thickness of the metal layer 103 is, for example, 0.01 mm or more, preferably 0.10 mm or more, and more preferably 0.25 mm or more. If the thickness is above these values, heat generation of the circuit pattern can be suppressed even in applications requiring high current. Furthermore, the upper limit of the thickness of the metal layer 103 is, for example, 2.0 mm or less, preferably 1.5 mm or less, and more preferably 1.0 mm or less. If the thickness is below these values, circuit processability can be improved, and the overall thickness of the substrate can be reduced.

[0081] The metal substrate 101 has the role of dissipating heat accumulated in the metal base substrate 100. The metal substrate 101 is not particularly limited as long as it is a heat-dissipating metal substrate, but for example, it may be a copper substrate, a copper alloy substrate, an aluminum substrate, or an aluminum alloy substrate, with a copper substrate or an aluminum substrate being preferred, and a copper substrate being more preferred. By using a copper substrate or an aluminum substrate, the heat dissipation performance of the metal substrate 101 can be improved.

[0082] The thickness of the metal substrate 101 can be set as appropriate, as long as the objective of the present invention is not impaired. The upper limit of the thickness of the metal substrate 101 is, for example, 20.0 mm or less, and preferably 5.0 mm or less. By using a metal substrate 101 with a thickness of this value or less, the overall thickness of the metal base substrate 100 can be reduced. In addition, the processability of the metal base substrate 100 in processes such as external shaping and cutting can be improved. Furthermore, the lower limit of the thickness of the metal substrate 101 is, for example, 0.1 mm or more, preferably 1.0 mm or more, and more preferably 2.0 mm or more. By using a metal substrate 101 with a thickness of this value or greater, the heat dissipation performance of the metal base substrate 100 as a whole can be improved.

[0083] In this embodiment, the metal base substrate 100 can be used for various substrate applications, but because it has excellent thermal conductivity and heat resistance, it can be used as a power module substrate for power modules. The metal base substrate 100 may have a metal layer 103 that has been processed with a circuit by etching or the like. In this metal base substrate 100, a solder resist (not shown) may be formed on the outermost layer, and connection electrode portions may be exposed so that electronic components can be mounted by exposure and development.

[0084] (Power module) The power module of this embodiment will be described with reference to Figure 2. Figure 2 is a cross-sectional view showing the configuration of the power module 11. The power module 11 of this embodiment may include the metal base substrate 100 described above and electronic components provided on the metal base substrate 100. As the electronic components, the power semiconductor elements described above can be used. In addition to power semiconductor elements, other electronic components may be mounted on the metal base substrate 100. The metal base substrate 100 can function as a heat spreader against heat generated by the electronic components (various heat-generating elements) during operation.

[0085] An example of a power module 11, as shown in Figure 2, has a power semiconductor element 2 mounted on a metal layer 103a (a patterned metal layer 103) of a power module circuit board (metal base substrate 100) via an adhesive layer 3. The power semiconductor element 2 is electrically connected to the metal layer 103b via a bonding wire 7. The power semiconductor element 2, bonding wire 7, and metal layers 103a and 103b are sealed with a sealing material 6.

[0086] Furthermore, the power module 11 may include other electronic components such as chip capacitors 8 and chip resistors 9 mounted on the metal layer 103 of the metal base substrate 100. The power module 11 may also have a structure in which the metal substrate 101 is connected to the heat dissipation fins 5 via a known thermal conductive grease 4.

[0087] It should be noted that the present invention is not limited to the embodiments described above, and any modifications, improvements, etc., that can achieve the objectives of the present invention are included in the present invention. Examples of reference formats are provided below. 1. A bismaleimide compound that does not contain a mesogenic group within the molecule and contains a conjugated structure in which the nitrogen atom of the maleimide group is conjugated with an aromatic ring, The curing agent of the bismaleimide compound, A thermosetting resin composition comprising a thermally conductive filler having a thermal conductivity of 20 W / m·K or higher. 2. A bismaleimide compound containing a mesogenic group, The curing agent of the bismaleimide compound, A thermosetting resin composition comprising a thermally conductive filler. 3. The thermosetting resin composition described in 1. A thermosetting resin composition comprising a bismaleimide compound that does not contain the mesogenic group, which is represented by the compound of the above general formula (A). (In the above general formula (A), n1 is an integer between 0 and 10, and X1 is independently an alkylene group having 1 to 10 carbon atoms, a group represented by the above formula (1a), a group represented by the formula "-SO2-", a group represented by "-CO-", an oxygen atom Child(Yes, R1 is an independent hydrocarbon group with 1 to 6 carbon atoms, a is an independent integer between 0 and 4, and b is an independent integer between 0 and 3.) (In formula (1a) above, Y is a hydrocarbon group having an aromatic ring with 6 to 30 carbon atoms, and n2 is an integer greater than or equal to 0.) 4.2. A thermosetting resin composition as described above, A thermosetting resin composition comprising a bismaleimide compound containing the mesogenic group, the compound represented by the above general formula (a). (In the above general formula (a), R is the same as in general formula -A 1 -xA 2 - is a mesogenic group represented by the above general formula. 1 and A 2 Each of these independently represents a substituent selected from aromatic groups, condensed aromatic groups, alicyclic groups, and alicyclic heterocyclic groups. x is a bonding group and represents a divalent substituent selected from the group consisting of a direct bond, -CH2-, -C(CH3)2-, -O-, -S-, -CH2-CH2-, -C=C-, -C≡C-, -CO-, -CO-O-, -CO-NH-, -CH=N-, -CH=NN=CH-, -N=N-, or -N(O)=N-. 5. A thermosetting resin composition according to any one of 1 to 4, A thermosetting resin composition wherein the curing agent comprises one or more selected from the group consisting of benzoxazine compounds, epoxy resins, cyanate compounds, and amine compounds. 6. A thermosetting resin composition according to any one of 1 to 5, A thermosetting resin composition having a softening point of 100°C or higher. 7. A thermosetting resin composition according to any one of 1 to 6, The thermally conductive filler is a thermosetting resin composition comprising at least one selected from alumina, aluminum nitride, silicon carbide, boron nitride, silicon nitride, magnesium oxide, and aluminum hydroxide and barium sulfate. 8.7. A thermosetting resin composition as described above, The boron nitride is a thermosetting resin composition comprising monodisperse particles, aggregated particles, or mixtures thereof of flaky boron nitride. 9. A thermosetting resin composition according to any one of 1 to 8, A thermosetting resin composition further comprising a curing accelerator. 10.9. A thermosetting resin composition as described above, A thermosetting resin composition wherein the curing accelerator contains a nitrogen atom-containing compound. 11. A thermosetting resin composition according to any one of 1 to 10, A thermosetting resin composition in the B-stage state. 12. A cured product of a thermosetting resin composition described in any one of items 1 to 11. 13. The adhesive layer, The adhesive layer comprises an insulating layer provided on the adhesive layer, A laminate in which the insulating layer is composed of a resin layer made of the thermosetting resin composition described in any one of 1 to 11. 14. Metal substrate and, An insulating layer provided on the metal substrate, It comprises a metal layer provided on the insulating layer, A metal-based substrate wherein the insulating layer is composed of a resin layer made of any one of the thermosetting resin compositions described in 1 to 11, and a laminate described in 13, selected from the group. 15. A metal-based substrate as described in 14. A metal-based substrate in which the aforementioned metal layer is composed of a copper layer or an aluminum layer. 16. A metal-based substrate as described in 14. or 15. A metal-based substrate in which the aforementioned metal substrate is composed of a copper substrate or an aluminum substrate. 17. A metal base substrate as described in any one of 14. to 16., A power module comprising electronic components provided on the aforementioned metal base substrate. [Examples]

[0088] The present invention will be described in detail below with reference to examples, but the present invention is not limited in any way to the descriptions of these examples.

[0089] (Preparation of thermosetting resin compositions that do not contain inorganic fillers) According to the mixing ratios shown in Table 1, a thermosetting resin, a curing agent, and, if necessary, a curing accelerator were melted and mixed on a hot plate, cooled, and then pulverized to obtain a thermosetting resin composition.

[0090] (Preparation of thermosetting resin varnish containing inorganic fillers) According to the mixing ratios shown in Table 1, a thermosetting resin, a curing agent, and, if necessary, a curing accelerator were added to cyclohexanone, which was used as the solvent, and the mixture was stirred to obtain a solution of the thermosetting resin composition. Next, an inorganic filler was added to this solution and pre-mixed, and then mixed using a planetary mixer or disperser to obtain a varnish-like thermosetting resin composition in which the inorganic filler was uniformly dispersed. In Table 1, the inorganic filler content was 60% by volume relative to 100% by volume of the total solid content of the thermosetting resin composition.

[0091] The components listed in Table 1 are as follows: (thermosetting resin) Bismaleimide compound 1: A bismaleimide compound represented by the following chemical formula (n is between 0 and 3, manufactured by Yamato Chemical Industries, Ltd., BMI-2300, Mw=750)

[0092] [ka]

[0093] Bismaleimide compound 2: A mesogenic group-containing bismaleimide compound represented by the following chemical formula.

[0094] [ka]

[0095] Bismaleimide compound 3: A mesogenic group-containing bismaleimide compound represented by the following chemical formula.

[0096] [ka]

[0097] Bismaleimide compound 4: A mesogenic group-containing bismaleimide compound represented by the following chemical formula.

[0098] [ka]

[0099] Bismaleimide compound 5: A mesogenic group-containing bismaleimide compound represented by the following chemical formula.

[0100] [ka]

[0101] Epoxy compound 1: Bisphenol A diglycidyl ether (DGEBA), represented by the following chemical formula (an epoxy compound that does not contain a mesogenic group, manufactured by Tokyo Chemical Industry Co., Ltd.)

[0102] [ka] Epoxy compound 2: A terephthalylidene-type epoxy resin (DGETAM, an epoxy compound containing a mesogenic group) represented by the following chemical formula.

[0103] [ka]

[0104] (Hardening agent) Hardener 1: Novolac-type cyanate resin (Lonza Japan Co., Ltd., PT-30) Hardener 2: 4,4'-diaminodiphenylethane (DDEt, manufactured by Tokyo Chemical Industry Co., Ltd.) Hardening agent 3: Pd-type benzoxazine (manufactured by Shikoku Chemicals Co., Ltd., Pd), represented by the following chemical formula.

[0105] [ka]

[0106] Hardener 4: Bisphenol A diglycidyl ether (DGEBA, an epoxy compound that does not contain a mesogenic group, manufactured by Tokyo Chemical Industry Co., Ltd.) represented by the above formula. Hardener 5: Terephthalylidene type epoxy resin (DGETAM, epoxy compound containing a mesogenic group) represented by the above formula. Hardener 6: Paraphenylenediamine (PPDA, manufactured by Tokyo Chemical Industry Co., Ltd.) Hardener 7: Diaminodiphenylmethane (DDM, manufactured by Tokyo Chemical Industry Co., Ltd.)

[0107] (Curing accelerator) Curing accelerator 1: 2,2-bis(3-methyl-4-hydroxyphenyl)propane (BPC, manufactured by Tokyo Chemical Industry Co., Ltd.) Curing accelerator 2: 2-methylimidazole (2MZ, manufactured by Tokyo Chemical Industry Co., Ltd.) Curing accelerator 3: Novolac-type phenolic resin (manufactured by Sumitomo Bakelite Co., Ltd., product name: PR-51470)

[0108] (Inorganic filler) Inorganic filler 1: Aggregated boron nitride prepared by the following procedure • Preparation of aggregated boron nitride: A mixture of melamine borate and flaky boron nitride powder was added to an aqueous solution of ammonium polyacrylate and mixed for 2 hours to prepare a spray slurry. This slurry was then supplied to a spray granulator and sprayed at an atomizer speed of 15,000 rpm, a temperature of 200°C, and a slurry supply rate of 5 ml / min to produce composite particles. The resulting composite particles were then calcined under a nitrogen atmosphere at 2,000°C to obtain aggregated boron nitride.

[0109] [Table 1]

[0110] The obtained thermosetting resin compositions were evaluated based on the following evaluation criteria. The evaluation results are shown in Table 1.

[0111] (Liquid crystal) The thermosetting resin compositions shown in Table 1, consisting of predetermined amounts of thermosetting resin, curing agent, and curing accelerator, were melted and mixed on a hot plate, then pulverized after cooling. The resulting resin powder was sandwiched between glass slides and placed on a heating stage. Birefringence was observed using a polarizing microscope, and the resulting powder was judged to be liquid crystalline. In Table 1, ◎ indicates that birefringence was clearly visible, ○ indicates that birefringence was slightly visible, and × indicates that birefringence was not visible.

[0112] (softening point) The softening point (°C) was measured for the obtained thermosetting resin composition that did not contain inorganic fillers. The method for measuring the softening point involved observing the thermal expansion characteristics of the evaluation substrate using a TMA (Thermal Mechanical Analyzer) test apparatus (TMA / SS6100, manufactured by Seiko Instruments Co., Ltd.) under the conditions of a heating rate of 5°C / min, a load of 0.05N, compression mode, and a measurement temperature range of 30 to 320°C. The temperature at the inflection point of the thermal expansion curve was determined by extrapolation and defined as the softening point. In Table 1, a softening point of 150°C or lower was judged as ×, a softening point between 150°C and 200°C was judged as ○, and a softening point above 200°C was judged as ◎.

[0113] (Td5: 5% weight loss temperature) Using a differential thermogravimetric analyzer (Seiko Instruments, TG / DTA6200 model), the temperature at which a sample loses 5% of its weight (Td5) was calculated by heating the sample from 30°C to 650°C under dry nitrogen airflow and a heating rate of 10°C / min. The sample used was a thermosetting resin composition without inorganic fillers, heated to 220°C for 90 minutes to obtain a cured product, and then dried at 100°C for 1 hour before measurement. In Table 1, Td5 of 300°C or less was judged as △, Td5 of 300°C to 350°C was judged as ○, and Td5 of 350°C or more was judged as ◎.

[0114] (Thermal conductivity of resins, thermal conductivity of composites) • Fabrication of resin molded products The thermosetting resin composition without inorganic fillers obtained above was set in a mold coated with a release agent, and compression molding was performed at 220°C for 15 minutes to obtain a resin molded product with a diameter of 10 mm and a thickness of 1 mm. Subsequently, curing was performed in an oven at 220°C for 90 minutes to obtain a resin molded body (sample 1 for thermal conductivity measurement).

[0115] • Fabrication of composite molded bodies The thermosetting resin composition varnish containing the inorganic filler obtained above was applied to a copper foil with a thickness of 18 μm and dried to prepare a copper foil with a resin layer. The resin layer of this copper foil was sandwiched between other copper foils and stacked, and compression molding was performed at 220°C for 90 minutes to obtain a composite molded body (sample 2 for thermal conductivity measurement) measuring 15 cm in length, 22 cm in width, and 0.2 mm in thickness.

[0116] • Resin molded products, composite molded products density density Measurements were performed in accordance with JIS K 6911 (General Test Methods for Thermosetting Plastics). Test specimens were cut from the above-mentioned resin molded or composite molded articles to a size of 2 cm (length) x 2 cm (width) x 2 mm (thickness). density (SP) units are g / cm 3 Let's assume that.

[0117] • Specific heat of resin molded articles and composite molded articles The specific heat (Cp) of the obtained resin molded articles or composite molded articles was measured by the DSC method.

[0118] • Measurement of thermal conductivity of resin molded articles and composite molded articles. From each of the above-mentioned resin molded and composite molded products obtained, specimens measuring 10 mm in diameter and 0.2 mm in thickness were cut out and used as test pieces for thickness direction measurement. Next, the thermal diffusivity (α) in the longitudinal direction of the plate-shaped test pieces was measured using the laser flash method with a ULVAC Xe flash analyzer TD-1RTV. The measurements were performed under atmospheric conditions at 25°C. For the resin molded article and the composite molded article, the obtained thermal diffusivity (α), specific heat (Cp), density The thermal conductivity was calculated from the (SP) measurement values ​​based on the following formula. Thermal conductivity [W / m·K]=α[m 2 / s] × Cp[J / kg·K] × Sp[g / cm 3 ] In Table 1, the thermal conductivity of a resin molded body is referred to as "resin thermal conductivity," and the thermal conductivity of a composite molded body is referred to as "composite thermal conductivity."

[0119] In Table 1, a resin thermal conductivity of 0.15 W / m·k or less was judged as △, a resin thermal conductivity of greater than 0.15 W / m·k but 0.28 W / m·k or less was judged as ○, and a resin thermal conductivity of greater than 0.28 W / m·k was judged as ◎. In Table 1, a composite material with a thermal conductivity of 15 W / m·k or less was judged as △, a composite material with a thermal conductivity of more than 15 W / m·k but 18 W / m·k or less was judged as ○, and a composite material with a thermal conductivity of more than 18 W / m·k was judged as ◎.

[0120] The thermosetting resin compositions of Examples 1 to 13 were found to have superior thermal conductivity, as evidenced by their excellent resin thermal conductivity and composite thermal conductivity compared to Comparative Example 1, and superior heat resistance, as evidenced by their higher softening point and Td5 temperature compared to Comparative Example 2. Therefore, it was found that the thermosetting resin compositions of Examples 1 to 13 can be suitably used not only as substrates for ordinary semiconductor devices, but also as substrates for power modules, etc., where heat resistance in high-temperature environments is required. [Explanation of Symbols]

[0121] 2 Power semiconductor elements 3 Adhesive layer 4. Thermal conductive grease 5 heat dissipation fins 6. Sealing material 7 Bonding wire 8 chip capacitors 9 chip resistors 10 Solder Resist 11 Power Modules 100 Metal base substrate 101 Metal substrate 102 Insulating layer 103 Metal layer 103a Metal layer 103b Metal layer

Claims

1. A bismaleimide compound containing a mesogenic group, The curing agent of the bismaleimide compound, It contains a thermally conductive filler, The bismaleimide compound containing the mesogenic group includes a compound represented by the following general formula (a): The curing agent comprises one or more selected from the group consisting of benzoxazine compounds, epoxy resins, cyanate compounds, and amine compounds. The amine compound comprises at least one selected from aromatic diamine compounds and monoamine compounds. The aromatic diamine compound is selected from o-tolidine, 3,3'-dihydroxy-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, m-phenylenediamine, p-phenylenediamine, o-xylenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylethane, 4,4'-diaminodiphenylpropane, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, 1,5-diaminonaphthalene, 4,4'-(p-phenylenediisopropylidene)dianiline, and 4,4'-diamino-3,3'-dimethyl-diphenylmethane. A thermosetting resin composition, The 5% weight loss temperature (Td5), measured according to the following procedure, is greater than 300°C. The thermal conductivity of the resin measured according to the following measurement procedure is greater than 0.15 W. Thermosetting resin composition. (Procedure for measuring the 5% weight loss temperature) The thermosetting resin composition, which does not contain the aforementioned thermally conductive filler, is heated at 220°C for 90 minutes to obtain a cured product, and then dried at 100°C for 1 hour before measurement. This cured product is used as the sample. Using a differential thermogravimetric simultaneous measurement device, the temperature at which the sample loses 5% of its weight (Td5) is calculated by heating the sample from 30°C to 650°C under conditions of a dry nitrogen flow and a heating rate of 10°C / min. (Procedure for measuring the thermal conductivity of resin) The thermosetting resin composition, which does not contain the inorganic filler containing the aforementioned thermally conductive filler, is set in a mold coated with a release agent, and compression molding is performed at 220°C for 15 min to obtain a resin molded product with a diameter of 10 mm and a thickness of 1 mm. Thereafter, curing is performed in an oven at 220°C for 90 min to obtain a resin molded body (sample 1 for thermal conductivity measurement). • Density of the resin molded product Density measurements were performed in accordance with JIS K 6911 (General Test Methods for Thermosetting Plastics). Test specimens were cut from the aforementioned resin molded body to a size of 2 cm (length) x 2 cm (width) x 2 mm (thickness). The unit of density (SP) was g / cm³. ３ Let's assume that. Specific heat of resin molded products The specific heat (Cp) of the aforementioned resin molded article is measured by the DSC method. Measurement of resin molded products A test specimen measuring 10 mm in diameter and 0.2 mm in thickness is cut from the aforementioned resin molded body. Next, the thermal diffusivity (α) in the longitudinal direction of the plate-shaped test specimen is measured using the laser flash method with a ULVAC Xe flash analyzer TD-1RTV. The measurement is performed under atmospheric conditions at 25°C. For the aforementioned resin molded body, the thermal conductivity is calculated from the measured values ​​of the thermal diffusivity (α), specific heat (Cp), and density (SP) obtained above, based on the following formula. Thermal conductivity [W / m·K] = α [m] ２ / s]×Cp[J / kg・K]×Sp[g / cm ３ ] 【Chemistry 1】 (In the above general formula (a), R is the same as in general formula -A) １ -x-A ２ It is a mesogenic group represented by -. In the above general formula, A １ and A ２ Each of these independently represents a substituent selected from phenylene, biphenylene, naphthylene, anthracenylene, cyclohexyl, pyridyl, pyrimidyl, and thiophenylene (however, it may be unsubstituted, or substituted with an aliphatic hydrocarbon group, halogen group, cyano group, or nitro group). x is a bonding group and represents a divalent substituent selected from the group consisting of a direct bond, -C=C-, -C≡C-, -CO-O-, -CO-NH-, -CH=N-, -CH=N-N=CH-, -N=N-, or -N(O)=N-.

2. A thermosetting resin composition according to claim 1, A thermosetting resin composition having a softening point of 100°C or higher.

3. A thermosetting resin composition according to claim 1 or 2, The thermally conductive filler is a thermosetting resin composition comprising at least one selected from alumina, aluminum nitride, silicon carbide, boron nitride, silicon nitride, magnesium oxide, and aluminum hydroxide and barium sulfate.

4. A thermosetting resin composition according to claim 3, The boron nitride is a thermosetting resin composition comprising monodisperse particles, aggregated particles, or mixtures thereof of flaky boron nitride.

5. A thermosetting resin composition according to any one of claims 1 to 4, A thermosetting resin composition further comprising a curing accelerator.

6. A thermosetting resin composition according to claim 5, A thermosetting resin composition wherein the curing accelerator contains a nitrogen atom-containing compound.

7. A thermosetting resin composition according to any one of claims 1 to 6, A thermosetting resin composition in the B-stage state.

8. A cured product of a thermosetting resin composition according to any one of claims 1 to 7.

9. Adhesive layer, The adhesive layer comprises an insulating layer provided on the adhesive layer, A laminate in which the insulating layer is composed of a resin layer made of the thermosetting resin composition described in any one of claims 1 to 7.

10. A metal substrate and An insulating layer provided on the metal substrate, It comprises a metal layer provided on the insulating layer, A metal-based substrate wherein the insulating layer is composed of one selected from the group consisting of a resin layer made of a thermosetting resin composition according to any one of claims 1 to 7 and a laminate according to claim 9.

11. A metal base substrate according to claim 10, A metal-based substrate in which the aforementioned metal layer is composed of a copper layer or an aluminum layer.

12. A metal base substrate according to claim 10 or 11, A metal-based substrate in which the aforementioned metal substrate is composed of a copper substrate or an aluminum substrate.

13. A metal base substrate according to any one of claims 10 to 12, A power module comprising electronic components provided on the aforementioned metal base substrate.

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