TWI879901B - Resin composition, prepreg, resin sheet, laminate, metal foil-clad laminate, and printed wiring board - Google Patents

Abstract

A resin composition containing a cyanate ester compound (A), a filler (B), a molybdenum compound (C), and zinc oxide (D), wherein the molybdenum compound (C) contains molybdenum compound particles, and the amount of the zinc oxide (D) in the resin composition is 5% by mass or less relative to the total mass of the molybdenum compound particles.

Description

Resin composition, prepreg, resin sheet, laminate, metal-clad laminate, and printed wiring board

The present invention relates to a resin composition, and a prepreg, a resin sheet, a laminate, a metal-clad laminate, a printed wiring board, etc. using the resin composition.

In recent years, the semiconductors widely used in electronic equipment, communication equipment, personal computers, etc. have been increasingly integrated, highly functionalized, and mounted at high density. Therefore, compared with the past, the requirements for high performance of the laminates used in semiconductor plastic packages, such as low thermal expansion, drilling processability, heat resistance, and flame retardancy, are becoming higher and higher.

In addition, especially in recent years, there is a strong demand for reducing the thermal expansion coefficient of the laminate in the surface direction. The reason is that if the difference in thermal expansion coefficient between the semiconductor element and the printed wiring board for the semiconductor plastic package is large, when a thermal shock is applied, the difference in thermal expansion coefficient will cause the semiconductor plastic package to warp, and poor connection will occur between the semiconductor element and the printed wiring board for the semiconductor plastic package, and between the semiconductor plastic package and the installed printed wiring board.

In the past, in order to meet the various properties required for laminated boards and reduce the thermal expansion rate, there is a method of mixing more inorganic fillers into the resin composition constituting the laminated board (for example, refer to patent documents 1 and 2). However, in these methods, the hardened resin composition becomes hard and brittle, and when the laminated board obtained by using the method is drilled, there will be problems such as reduced hole position accuracy, faster wear of the drill bit, increased frequency of drill bit replacement, and easy breakage of the drill bit, which deteriorates the drilling processability.

On the other hand, as a method for improving the drilling processability of laminated boards, there is a known method of mixing a molybdenum compound such as zinc molybdate or calcium molybdate into a resin composition (for example, refer to Patent Document 3). [Prior Art Document] [Patent Document]

Patent document 1: Japanese Patent Publication No. 2004-059643 Patent document 2: Japanese Patent Publication No. 2009-120702 Patent document 3: International Publication No. 2013/047203

(The problem to be solved)

However, when the molybdenum compound described in Patent Document 3 is mixed with a resin composition, the molybdenum compound or zinc oxide contained therein as an impurity acts as a hardening catalyst for the cyanate compound, generating pores and causing a problem of deteriorating the appearance of the molded product.

In view of the above-mentioned problem, the present invention aims to provide a resin composition that takes both drilling processability and appearance into consideration, and molded products such as prepregs, resin sheets, laminates, metal-clad laminates, and printed wiring boards using the composition. (Method for solving the problem)

The inventors of this case have made great efforts to solve this problem and have found that the above-mentioned problem can be solved by containing at least a cyanate compound, a filler, a molybdenum compound, and zinc oxide, and the content of zinc oxide in the resin composition is below a specific range, thereby completing the present invention.

That is, the present invention is as follows. [1] A resin composition comprising a cyanate compound (A), a filler (B), a molybdenum compound (C), and zinc oxide (D), the molybdenum compound (C) comprising molybdenum compound particles, the content of zinc oxide (D) in the resin composition is 5% by mass or less relative to the total mass of the molybdenum compound particles. [2] The resin composition of [1], wherein the content of the filler (B) is 10 to 500 parts by mass relative to 100 parts by mass of the total resin solid components in the resin composition. [3] The resin composition of [1] or [2], wherein the content of the molybdenum compound (C) is 0.2 to 30 parts by mass relative to 100 parts by mass of the total resin solid components in the resin composition. [4] The resin composition of any one of [1] to [3], wherein the content of the zinc oxide (D) is 0.1% by mass or more and 5% by mass or less relative to the total mass of the molybdenum compound particles. [5] The resin composition of any one of [1] to [4], wherein the zinc oxide (D) is contained in the molybdenum compound particles. [6] The resin composition of any one of [1] to [5], wherein the shape of the molybdenum compound particles is spherical. [7] The resin composition of [6], wherein the circularity of the molybdenum compound particles is 0.90 to 1.00. [8] The resin composition of any one of [1] to [7], wherein the average particle size of the molybdenum compound particles is 0.1 to 10 μm. [9] The resin composition of any one of [1] to [8], wherein the molybdenum compound (C) is one or more selected from the group consisting of zinc molybdate, ammonium molybdate, sodium molybdate, calcium molybdate, potassium molybdate, molybdenum disulfide, molybdenum trioxide, and molybdenum hydrate. [10] The resin composition of any one of [1] to [9], wherein the cyanate compound (A) is at least one selected from the group consisting of phenol novolac type cyanate compounds, naphthol aralkyl type cyanate compounds, naphthyl ether type cyanate compounds, xylene resin type cyanate compounds, bisphenol M type cyanate compounds, bisphenol A type cyanate compounds, diallyl bisphenol A type cyanate compounds, and biphenyl aralkyl type cyanate compounds. [11] The resin composition of any one of [1] to [10], wherein the filler (B) is at least one inorganic filler selected from the group consisting of silica, alumina, aluminum nitride, boron nitride, alumina, aluminum hydroxide, and titanium oxide. [12] The resin composition of any one of [1] to [11], wherein the filler (B) is one or more organic fillers selected from the group consisting of silicone rubber powder and silicone composite powder. [13] The resin composition of any one of [1] to [12], further comprising one or more compounds selected from the group consisting of maleimide compounds (M), epoxy compounds (E), phenol compounds (F), alkenyl-substituted nadic acid imide compounds (K), cyclohexane resins (G), benzophenone compounds (H), and compounds having polymerizable unsaturated groups (I). [14] The resin composition of [13], wherein the maleimide compound (M) is one or more selected from the group consisting of bis(4-maleimidephenyl)methane, 2,2-bis{4-(4-maleimidephenoxy)-phenyl}propane, bis(3-ethyl-5-methyl-4-maleimidephenyl)methane, a maleimide compound represented by the following formula (2), and a maleimide compound represented by the following formula (3);

[Chemistry 1]

In formula (2), ^R1 each independently represents a hydrogen atom or a methyl group, and n1 is 1 to 10;

[Chemistry 2]

In formula (3), the multiple ^R2s present each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group, and n2 is an average value, which represents 1＜n2≦5. [15] The resin composition of [13] or [14], wherein the epoxy compound (E) is one or more selected from the group consisting of biphenyl aralkyl type epoxy compounds, naphthalene type epoxy compounds, and naphthyl ether type epoxy resins. [16] The resin composition of any one of [1] to [15] is used for printed wiring board applications. [17] A prepreg comprising: a substrate; and the resin composition of any one of [1] to [15] impregnated in or coated on the substrate. [18] A resin sheet obtained by forming a resin composition as described in any one of [1] to [15] into a sheet. [19] A resin sheet with a support, comprising: a support; and a resin composition as described in any one of [1] to [15] disposed on the support. [20] A laminated board obtained by laminating one or more selected from the group consisting of a prepreg as described in [17], a resin sheet as described in [18], and a resin sheet with a support as described in [19]. [21] A metal foil-clad laminate comprising: one or more selected from the group consisting of a prepreg such as [17], a resin sheet such as [18], and a resin sheet with a support such as [19]; and metal foil disposed on one or both sides of at least one selected from the group consisting of the prepreg, the resin sheet, and the resin sheet with a support. [22] A printed wiring board comprising: an insulating layer comprising a cured product of a resin composition such as any one of [1] to [15]; and a conductive layer formed on the surface of the insulating layer. (Effect of the invention)

According to the present invention, a resin composition that takes both drilling processability and appearance into consideration, and molded products such as prepregs, resin sheets, laminates, metal-clad laminates, and printed wiring boards using the composition can be provided.

The following is a detailed description of an embodiment of the present invention (hereinafter referred to as "this embodiment"), but the present invention is not limited thereto and can be variously modified within the scope of the gist thereof.

[Resin composition] The resin composition of this embodiment contains a cyanate compound (A), a filler (B), a molybdenum compound (C), and zinc oxide (D). The molybdenum compound (C) contains molybdenum compound particles. The content of zinc oxide (D) in the resin composition is less than 5% by mass relative to the total mass of the molybdenum compound particles.

The resin composition of this embodiment contains a molybdenum compound (C) and zinc oxide (D), and the content of zinc oxide (D) is adjusted to be 5% by mass or less relative to the total mass of the molybdenum compound particles. When the content of zinc oxide (D) is 5% by mass or less when converted to ZnO, pores generated by the reaction of zinc oxide and cyanate compound can be suppressed, and the appearance of the molded product becomes good.

From the same viewpoint, the content of zinc oxide (D) contained in the resin composition is preferably 4% by mass or less relative to the total mass of the molybdenum compound particles. The lower limit of the content of zinc oxide (D) contained in the resin composition is not particularly limited, but from the viewpoint of suppressing the manufacturing cost, it is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, more preferably 0.3% by mass or more, more preferably 0.5% by mass or more, and particularly preferably 1% by mass or more.

In addition, the content of zinc oxide (D) contained in the resin composition referred to herein is the total mass of zinc oxide (D) contained in the resin composition. When zinc oxide (D) is mainly contained in the molybdenum compound particles, it refers to the content of zinc oxide contained in the molybdenum compound particles. When zinc oxide (D) is not contained in the molybdenum compound particles, it refers to the content of zinc oxide contained in the resin composition other than the molybdenum compound particles. When zinc oxide (D) is contained in both the molybdenum compound particles and the resin composition other than the molybdenum compound particles, it refers to the total amount of zinc oxide contained in the molybdenum compound particles and the zinc oxide contained in the resin composition other than the molybdenum compound particles.

That is, in the resin composition of the present embodiment, the zinc oxide (D) may be in a form in which the zinc oxide (D) is mainly contained in the molybdenum compound particles, in a form in which the zinc oxide (D) is not contained in the molybdenum compound particles but is contained in the resin composition other than the molybdenum compound particles, or in a form in which the zinc oxide (D) is contained in both the molybdenum compound particles and the resin composition other than the molybdenum compound particles.

Zinc oxide (D) is mainly in the form of being contained in molybdenum compound particles, for example, when a resin composition is prepared using a molybdenum compound (C') containing molybdenum compound particles containing zinc oxide described later.

The zinc oxide (D) is not contained in the molybdenum compound particles but is contained in the resin composition other than the molybdenum compound particles. For example, a resin composition is prepared by adding a molybdenum compound (C) not containing zinc oxide and zinc oxide (D) separately.

The zinc oxide (D) is contained in both the molybdenum compound particles and the resin composition other than the molybdenum compound particles. For example, the molybdenum compound particles and the zinc oxide are mixed by kneading in advance, and then the resin composition is prepared using the mixture. In this case, zinc oxide is sometimes dispersed in the resin composition when the resin composition is prepared, so zinc oxide tends to be contained in both the molybdenum compound particles and the resin composition other than the molybdenum compound particles.

Among these forms, the form in which zinc oxide (D) is mainly contained in the molybdenum compound particles, and the form in which zinc oxide (D) is contained in both the molybdenum compound particles and the resin composition other than the molybdenum compound particles are preferred. More specifically, the form in which the resin composition is prepared using the molybdenum compound (C') containing the molybdenum compound particles containing zinc oxide described later, and the form in which the resin composition is prepared using a mixture prepared by kneading the molybdenum compound particles and zinc oxide in advance.

When the resin composition is prepared by adding the molybdenum compound (C) not containing zinc oxide and the zinc oxide (D), the zinc oxide is not particularly limited, and zinc oxides of various properties and particle sizes can be appropriately selected, and commercially available zinc oxides can be used.

When zinc oxide and molybdenum compound particles are mixed to prepare a mixture in advance, the zinc oxide is not particularly limited, and zinc oxides of various properties and particle sizes can be appropriately selected, and commercially available zinc oxides can be used.

At this time, the content of zinc oxide (D) can be calculated from the feed ratio and usage amount of molybdenum compound particles (molybdenum compound (C)) and zinc oxide as raw materials when preparing the molybdenum component to be mixed with the resin component. In this case, the content of zinc oxide (D) can be adjusted by, for example, changing the feed ratio and usage amount of molybdenum compound particles (molybdenum compound (C)) and zinc oxide as raw materials when preparing the molybdenum component to be mixed with the resin component.

On the other hand, the content of zinc oxide contained in the molybdenum compound particles can be measured by X-ray photoelectron spectroscopy (XPS) described below. The content of zinc oxide contained in the molybdenum compound particles can be adjusted by, for example, changing the feed ratio of the molybdenum-containing raw material and the zinc-containing raw material when producing the molybdenum compound (C).

[Molybdenum compound (C)] The molybdenum compound (C) is a compound containing molybdenum in the molecule, and is preferably a molybdenum oxide or a molybdenum sulfide. Specific examples of the molybdenum compound (C) include, but are not limited to, molybdenum compounds such as zinc molybdate (e.g., ZnMoO ₄ , Zn ₃ Mo ₂ O ₉ , etc.), ammonium molybdate, sodium molybdate, calcium molybdate, potassium molybdate, molybdenum disulfide, molybdenum trioxide, and molybdenum hydrate. One of these compounds may be used alone or two or more thereof may be used in combination. Molybdenum hydrates, such as molybdenum acid monohydrate (MoO ₃ ･H ₂ O), ammonium molybdate tetrahydrate ((NH ₄ ) ₆ Mo7O ₂₄ ･4H ₂ O), zinc molybdate pentahydrate (Zn ₅ Mo ₂ O ₁₁ ･5H ₂ O), etc. Among the above, zinc molybdenum acid, molybdenum disulfide, and molybdenum hydrate are preferred from the perspective of drilling processability.

The content of the molybdenum compound (C) in the resin composition of the present embodiment can be appropriately set according to the intended use and performance, and is not particularly limited. However, from the perspective of heat resistance, flame retardancy, and drilling processability, it is preferably 0.2 to 30 parts by mass, more preferably 0.5 to 15 parts by mass, and even more preferably 1 to 10 parts by mass relative to 100 parts by mass of the total resin solid components in the resin composition. In addition, in the present embodiment, "resin solid components in the resin composition", unless otherwise specified, refer to components other than solvents and fillers in the resin composition. In addition, "100 parts by mass of resin solid components" refers to 100 parts by mass of the total components other than solvents and fillers in the resin composition.

(Molybdenum compound particles) The molybdenum compound (C) contains molybdenum compound particles. The molybdenum compound particles are particles constituting the molybdenum compound (C), for example, particles containing the compounds listed as specific examples of the molybdenum compound (C) above. The content of the molybdenum compound particles contained in the molybdenum compound (C) is not particularly limited, but is preferably 50 to 100 mass%, more preferably 70 to 100 mass%, still more preferably 90 to 100 mass%, and still more preferably 95 to 100 mass%. If the content of the molybdenum compound particles contained in the molybdenum compound (C) is within the above range, the effect of the present invention tends to be more pronounced.

The shape of the molybdenum compound particles is not particularly limited. Since the filling property of the molybdenum compound (C) in the resin composition and the molded product using the composition is improved, the drilling processability tends to be more significantly improved, so a spherical shape is preferred. When the aforementioned molybdenum compound particles are spherical, the circularity is preferably 0.88 to 1.00, preferably 0.90 to 1.00, and more preferably 0.92 to 1.00. Here, the circularity is an index represented by circularity = 4π×(area) ÷(circumference) ² , and the closer the value is to 1, the more true the circle is. The circularity can be measured by a wet flow particle size and shape analyzer. More specifically, it can be measured according to the method described in the embodiment.

The average particle size (D50) of the molybdenum compound particles can be appropriately set according to the desired performance without special restrictions. If the drilling processability and the dispersibility of the resin component are taken into consideration, the average particle size (D50) is preferably 0.1 to 10 μm, and more preferably 0.5 to 8 μm. Here, in this specification, the average particle size (D50) refers to the median particle diameter, which is the value when the volume of the larger side and the volume of the smaller side are equal when the particle size distribution of the powder to be measured is divided into two parts. The average particle size (D50) refers to the value obtained by measuring the particle size distribution of a predetermined amount of powder in a water dispersion medium using a laser diffraction scattering particle size distribution measuring device, and accumulating the volume from the smallest particle until it reaches 50% of the total volume.

The molybdenum compound (C) containing the molybdenum compound particles can be produced by various known methods such as calcination method and precipitation method, and the production method is not particularly limited. In addition, commercially available products can also be used.

(Molybdenum compound particles containing zinc oxide) For molybdenum compound particles, molybdenum compound particles containing zinc oxide are preferred. That is, as one aspect of this embodiment, the resin composition of this embodiment contains at least a cyanate compound (A), a filler (B), and a molybdenum compound (C), and the molybdenum compound (C) includes molybdenum compound particles containing zinc oxide, and the content of zinc oxide contained in the molybdenum compound particles is preferably 5% by mass or less when converted to ZnO. In this case, the content of zinc oxide contained in the molybdenum compound particles is 5% by mass or less when converted to ZnO. If the content of zinc oxide is 5% by mass or less when converted to ZnO, the pores generated by the reaction of zinc oxide and cyanate compound will be suppressed, and the appearance of the molded product will become good. From the same viewpoint, the content of zinc oxide contained in the molybdenum compound particles is preferably 4% by mass or less when converted to ZnO. In addition, the content of zinc oxide contained in the above-mentioned molybdenum compound particles is relative to the total mass of the molybdenum compound particles. Here, "containing zinc oxide" refers to the form of zinc oxide entering the inside of the molybdenum compound particles and adhering to the surface of the molybdenum compound particles.

The lower limit of the content of zinc oxide contained in the molybdenum compound particles is not particularly limited, but from the viewpoint of suppressing the manufacturing cost, it is preferably 0.1 mass % or more, more preferably 0.2 mass % or more, more preferably 0.3 mass % or more, more preferably 0.5 mass % or more, and particularly preferably 1 mass % or more. That is, the content of zinc oxide contained in the molybdenum compound particles is preferably 0.1 to 5 mass %, more preferably 0.2 to 5 mass %, more preferably 0.3 to 5 mass %, and even more preferably 0.5 to 4 mass %.

The content of zinc oxide in the molybdenum compound particles can be measured by X-ray photoelectron spectroscopy (XPS). More specifically, it can be measured according to the method described in the embodiments.

The content of zinc oxide in the molybdenum compound particles can be adjusted by changing the feed ratio of the molybdenum-containing raw material and the zinc-containing raw material when producing the molybdenum compound (C') containing the molybdenum compound particles containing zinc oxide.

The shape and average particle size of the molybdenum compound particles containing zinc oxide are the same as the shape and average particle size of the above-mentioned molybdenum compound particles.

The molybdenum compound (C') containing zinc oxide-containing molybdenum compound particles can be produced by using a molybdenum-containing raw material and a zinc-containing raw material, and utilizing various known methods such as calcination method and precipitation method. The production method is not particularly limited. In addition, commercially available products can also be used. [Resin component]

The resin composition of this embodiment, in addition to the above-mentioned molybdenum compound (C) and zinc oxide (D), also contains at least a cyanate compound (A) and a filler (B). The cyanate compound (A) and the filler (B) used here can be appropriately selected from known products according to the purpose and performance, and the type and amount of each material are not particularly limited. For example, when used as electrical and electronic materials, electrical insulation materials, working machine materials, and adhesives, they can be appropriately selected from various materials known in various technical fields.

[Cyanate compound (A)] The cyanate compound (A) may be any compound having two or more cyanate groups (cyano groups) directly bonded to an aromatic ring in one molecule, and known compounds may be used appropriately.

Such cyanate compounds (A) are not particularly limited. Considering the viewpoints of formability and surface hardness, for example, phenol novolac type cyanate compounds, naphthol aralkyl type cyanate compounds, naphthyl ether type cyanate compounds, xylene resin type cyanate compounds, bisphenol M type cyanate compounds, bisphenol A type cyanate compounds, diallyl bisphenol A type cyanate compounds, and biphenyl aralkyl type cyanate compounds are examples of more ideal compounds. Cyanate compounds (A) can be used alone or in combination of two or more in any combination and ratio. Among them, considering the viewpoints of formability, surface hardness and further considering heat resistance, flame retardancy, low dielectric properties (low dielectric constant, low dielectric tangent), bisphenol A type cyanate compounds, diallyl bisphenol A type cyanate compounds, naphthol aralkyl type cyanate compounds are more ideal, and naphthol aralkyl type cyanate compounds are particularly preferred.

The naphthol aralkyl type cyanate compound is not particularly limited, and for example, the compound represented by the following formula (1) is preferred.

[Chemistry 3]

In the above formula (1), ^R3 each independently represents a hydrogen atom or a methyl group, wherein a hydrogen atom is preferred. In the above formula (1), n3 is 1 to 10.

The content of the cyanate compound (A) in the resin composition of the present embodiment is preferably 1 to 99.9 parts by mass, more preferably 3 to 90 parts by mass, and even more preferably 5 to 80 parts by mass, and may also be 10 to 70 parts by mass, 20 to 60 parts by mass, or 25 to 50 parts by mass, relative to 100 parts by mass of the total resin solid components in the resin composition. When the content of the cyanate compound (A) is within the above range, there is a tendency to have better heat resistance, low dielectric constant, low dielectric tangent, etc.

Furthermore, when the resin composition of the present embodiment contains the maleimide compound (M) described below in addition to the cyanate compound (A), the content of the cyanate compound (A) is preferably 30 to 90 parts by mass, more preferably 40 to 80 parts by mass, and even more preferably 50 to 70 parts by mass relative to 100 parts by mass of the total amount of the cyanate compound (A) and the maleimide compound (M). When the content of the cyanate compound (A) is within the above range, in addition to heat resistance, low dielectric constant, low dielectric tangent, etc., formability and copper foil peeling strength tend to be better.

[Filler (B)] The resin composition of this embodiment contains a filler (B). The filler (B) is not particularly limited, and may be, for example, an inorganic filler or an organic filler. The filler (B) may be used alone or in combination of two or more.

The inorganic filler is not particularly limited, and may be, for example, one or more selected from the group consisting of silicon dioxide, aluminum oxide, aluminum nitride, boron nitride, alumina, aluminum hydroxide, and titanium oxide. Among these, silicon dioxide is preferably used from the viewpoint of low thermal expansion, and aluminum oxide and aluminum nitride are preferably used from the viewpoint of high thermal conductivity.

The organic filler is not particularly limited, for example: styrene type powder, butadiene type powder, acrylic type powder and other rubber powders; core shell type rubber powder; polysilicone resin powder; polysilicone rubber powder; polysilicone composite powder, etc. Among the above, considering the viewpoint of low thermal expansion and flame retardancy, one or more selected from the group consisting of polysilicone rubber powder and polysilicone composite powder is preferred.

The content of the filler (B) in the resin composition of the present embodiment is preferably 10 to 500 parts by mass, more preferably 50 to 300 parts by mass, further preferably 75 to 250 parts by mass, and further preferably 100 to 200 parts by mass, relative to 100 parts by mass of the total resin solid components in the resin composition.

The resin composition in the present embodiment may further contain one or more compounds selected from the group consisting of a maleimide compound (M), an epoxy compound (E), a phenol compound (F), an alkenyl-substituted nadiimide compound (K), an oxycyclobutane resin (G), a benzophenone compound (H), and a compound having a polymerizable unsaturated group (I).

[Maleimide compound (M)] The maleimide compound (M) may be a compound having one or more maleimide groups in one molecule, and known compounds may be used appropriately, and the type thereof is not particularly limited. The number of maleimide groups per molecule of the maleimide compound (M) is 1 or more, preferably 2 or more.

The maleimide compound (M) is not particularly limited, and examples thereof include N-phenylmaleimide, N-hydroxyphenylmaleimide, bis(4-maleimidephenyl)methane, 2,2-bis{4-(4-maleimidephenoxy)-phenyl}propane, bis(3,5-dimethyl-4-maleimidephenyl)methane, bis(3-ethyl-5-methyl-4-maleimidephenyl)methane, bis(3,5-diethyl-4-maleimidephenyl)methane, a maleimide compound represented by the following formula (2), a maleimide compound represented by the following formula (3), prepolymers of these maleimide compounds, and prepolymers of the above maleimide compounds and amine compounds. The maleimide compound (M) may be used alone or in combination of two or more in any combination and ratio. By including such a maleimide compound (M), the thermal expansion coefficient of the obtained cured product tends to be lower and the heat resistance tends to be better.

Among them, one or more selected from the group consisting of bis(4-maleimidephenyl)methane, 2,2-bis{4-(4-maleimidephenoxy)-phenyl}propane, bis(3-ethyl-5-methyl-4-maleimidephenyl)methane, a maleimide compound represented by the following formula (2), and a maleimide compound represented by the following formula (3) are more preferable from the viewpoint of low thermal expansion and heat resistance.

[Chemistry 4]

In formula (2), R1 ^'s each independently represent a hydrogen atom or a methyl group, and n1 is 1 to 10.

[Chemistry 5]

In formula (3), the multiple R ² present each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group, and n2 is an average value, which represents 1＜n2≦5.

When the resin composition of the present embodiment contains a maleimide compound (M), the content of the maleimide compound (M) is preferably 1 to 99 parts by mass, more preferably 3 to 90 parts by mass, and even more preferably 5 to 80 parts by mass, and may also be 10 to 70 parts by mass, 20 to 60 parts by mass, or 25 to 50 parts by mass, relative to 100 parts by mass of the total resin solid components in the resin composition. When the content of the maleimide compound (M) is within the above range, heat resistance and the like tend to be better.

Furthermore, when the resin composition of the present embodiment contains a cyanate compound (A) and a maleimide compound (M), the content of the maleimide compound (M) is preferably 10 to 70 parts by mass, more preferably 20 to 60 parts by mass, and even more preferably 30 to 50 parts by mass relative to 100 parts by mass of the total amount of the cyanate compound (A) and the maleimide compound (M). When the content of the maleimide compound (M) is within the above range, in addition to heat resistance, formability, and copper foil peeling strength also tend to be better.

[Epoxy compound (E)] The epoxy compound (E) may be any compound having one or more epoxy groups in one molecule, and known compounds may be used appropriately. The type of epoxy compound (E) is not particularly limited. The number of epoxy groups per molecule of the epoxy compound (E) is 1 or more, preferably 2 or more.

The epoxy compound (E) is not particularly limited, and conventionally known epoxy compounds and epoxy resins can be used. For example, biphenyl aralkyl epoxy compounds, naphthalene epoxy compounds, bis-naphthalene epoxy compounds, polyfunctional phenol epoxy resins, naphthyl ether epoxy resins, phenol aralkyl epoxy resins, phenol novolac epoxy resins, cresol novolac epoxy resins, xylene novolac epoxy resins, naphthalene skeleton modified phenolic resins, Varnish type epoxy resin, dicyclopentadiene novolac type epoxy resin, biphenyl novolac type epoxy resin, phenol aralkyl novolac type epoxy resin, naphthol aralkyl novolac type epoxy resin, aralkyl novolac type epoxy resin, aromatic hydrocarbon formaldehyde type epoxy compound, anthraquinone type epoxy compound, anthracene type epoxy resin, naphthalene Phenol aralkyl type epoxy compounds, dicyclopentadiene type epoxy resins, Xyloc type epoxy compounds, bisphenol A type epoxy resins, bisphenol E type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, bisphenol A novolac type epoxy resins, phenol type epoxy compounds, biphenyl type epoxy resins, aralkyl novolac The epoxy resins include epoxy resins of the type epoxide, tris(II) skeleton epoxy compounds, triglycidyl isocyanurate, aliphatic epoxy resins, polyol epoxy resins, glycidylamine, glycidyl ester resins, compounds obtained by epoxidation of double bonds of double bond-containing compounds such as butadiene, and compounds obtained by reaction of hydroxyl-containing polysilicone resins with epichlorohydrin. Among these, biphenyl aralkyl epoxy compounds, naphthalene epoxy compounds, and naphthalene ether epoxy resins are preferably used from the viewpoint of moldability and surface hardness. The epoxy compound (E) may be used alone or in combination of two or more in any combination and ratio.

When the resin composition of the present embodiment contains an epoxy compound (E), the content of the epoxy compound (E) is preferably 1 to 99.9 parts by mass, more preferably 3 to 90 parts by mass, and even more preferably 4 to 80 parts by mass, and may also be 10 to 70 parts by mass, 20 to 60 parts by mass, or 30 to 50 parts by mass, relative to 100 parts by mass of the total resin solid components in the resin composition. When the content of the epoxy compound (E) is within the above range, there is a tendency for better adhesion, flexibility, etc.

When the resin composition of the present embodiment contains the phenol compound (F) and the epoxy compound (E) described below, the content of the epoxy compound (E) is preferably 20 to 80 parts by mass, more preferably 30 to 70 parts by mass, and even more preferably 40 to 60 parts by mass relative to 100 parts by mass of the total amount of the phenol compound (F) and the epoxy compound (E). When the content of the epoxy compound (E) is within the above range, in addition to the adhesion and flexibility, the heat resistance also tends to be better.

[Phenol compound (F)] The phenol compound (F) may be any compound having two or more phenolic hydroxyl groups in one molecule, and any known compound may be used without any particular limitation on the type.

The phenol compound (F) is not particularly limited, and examples thereof include cresol novolac type phenolic resins, biphenyl aralkyl type phenolic resins represented by the following formula (4), naphthol aralkyl type phenolic resins represented by the following formula (5), aminotriazine novolac type phenolic resins, naphthalene type phenolic resins, phenol novolac resins, alkylphenol novolac resins, bisphenol A type novolac resins, dicyclopentadiene type phenolic resins, Xyloc type phenolic resins, terpene-modified phenolic resins, and polyvinylphenols. The phenol compound (F) may be used alone or in combination of two or more in any combination and ratio.

Among them, cresol novolac type phenolic resins, biphenyl aralkyl type phenolic resins represented by the following formula (4), naphthol aralkyl type phenolic resins represented by the following formula (5), aminotriazine novolac type phenolic resins, and naphthalene type phenolic resins are more desirable from the viewpoint of moldability and surface hardness, and biphenyl aralkyl type phenolic resins represented by the following formula (4) and naphthol aralkyl type phenolic resins represented by the following formula (5) are more desirable.

[Chemistry 6]

In formula (4), each of the multiple R ^4's independently represents a hydrogen atom or a methyl group, and n4 is 1-10.

[Chemistry 7]

In formula (5), the multiple R ⁵ present each independently represents a hydrogen atom or a methyl group, and n5 is 1-10.

When the resin composition of the present embodiment contains a phenol compound (F), the content of the phenol compound (F) is preferably 1 to 99 parts by mass, more preferably 3 to 90 parts by mass, and even more preferably 5 to 80 parts by mass, and may also be 10 to 70 parts by mass, 20 to 60 parts by mass, or 30 to 50 parts by mass, relative to 100 parts by mass of the total resin solid components of the resin composition. When the content of the phenol compound (F) is within the above range, there is a tendency for better adhesion, flexibility, etc.

When the resin composition in the present embodiment contains a phenol compound (F) and an epoxy compound (E), the content of the phenol compound (F) is preferably 20 to 80 parts by mass, more preferably 30 to 70 parts by mass, and even more preferably 40 to 60 parts by mass relative to 100 parts by mass of the total amount of the phenol compound (F) and the epoxy compound (E). When the content of the phenol compound (F) is within the above range, in addition to adhesion and flexibility, the peeling strength of the copper foil also tends to be better.

[Alkenyl-substituted nadic acid imide compound (K)] The alkenyl-substituted nadic acid imide compound (K) is not particularly limited as long as it is a compound having one or more alkenyl-substituted nadic acid imide groups in one molecule, for example, a compound represented by the following formula (2d). The resin composition of this embodiment tends to have improved heat resistance by containing an alkenyl-substituted nadic acid imide compound (K).

[Chemistry 8]

In the formula, each of the multiple _R1s independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms (e.g., a methyl group or an ethyl group), and _R2 represents an alkylene group having 1 to 6 carbon atoms, a phenylene group, a biphenylene group, a naphthylene group, or a group represented by the following formula (6) or (7).

[Chemistry 9]

In formula (6), R ₃ represents a methylene group, an isopropylene group, CO, O, S or SO ₂ .

[Chemistry 10]

In formula (7), a plurality of R _4's each independently represent an alkylene group having 1 to 4 carbon atoms or a cycloalkylene group having 5 to 8 carbon atoms.

The alkenyl-substituted nadic acid imide compound (K) may be a commercial product or a product produced by a known method. Examples of commercial products include "BANI-M" and "BANI-X" produced by Maruzen Petrochemical Co., Ltd.

When the resin composition of the present embodiment contains an alkenyl-substituted nadic acid imide compound (K), the content of the alkenyl-substituted nadic acid imide compound (K) is preferably 1 to 99 parts by mass, more preferably 3 to 90 parts by mass, and even more preferably 5 to 80 parts by mass, and may also be 10 to 70 parts by mass, 20 to 60 parts by mass, or 30 to 50 parts by mass, relative to 100 parts by mass of the total resin solid components of the resin composition. When the content of the alkenyl-substituted nadic acid imide compound (K) is within the above range, heat resistance and the like tend to be better.

[Oxycyclobutane resin (G)] Oxycyclobutane resin (G) is not particularly limited, and generally known products can be used. Specific examples of the cyclohexane resin (G) include cyclohexane, 2-methylcyclohexane, 2,2-dimethylcyclohexane, 3-methylcyclohexane, 3,3-dimethylcyclohexane and other alkylcyclohexanes, 3-methyl-3-methoxymethylcyclohexane, 3,3-bis(trifluoromethyl)perfluorocyclohexane, 2-chloromethylcyclohexane, 3,3-bis(chloromethyl)cyclohexane, biphenyl-type cyclohexane, OXT-101 (trade name of Toa Gosei Co., Ltd.), OXT-121 (trade name of Toa Gosei Co., Ltd.), and the like. The oxycyclobutane resins (G) may be used alone or in combination of two or more.

[Benzotriol compound (H)] The benzotriol compound (H) is not particularly limited as long as it is a compound having two or more dihydrobenzotriol rings in one molecule, and generally known products can be used. Specific examples of the benzotriol compound (H) include bisphenol A type benzotriol BA-BXZ (trade name of Konishi Chemical), bisphenol F type benzotriol BF-BXZ (trade name of Konishi Chemical), bisphenol S type benzotriol BS-BXZ (trade name of Konishi Chemical), etc. These benzotriol compounds (H) can be used alone or in combination of two or more.

[Compound (I) having a polymerizable unsaturated group] The compound (I) having a polymerizable unsaturated group is not particularly limited, and generally known compounds can be used. Specific examples of the compound (I) having a polymerizable unsaturated group include vinyl compounds such as ethylene, propylene, styrene, divinylbenzene, and divinylbiphenyl, (meth)acrylate esters of monohydric or polyhydric alcohols such as methyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, polypropylene glycol di(meth)acrylate, trihydroxymethylpropane di(meth)acrylate, trihydroxymethylpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, epoxy (meth)acrylates such as bisphenol A type epoxy (meth)acrylate, bisphenol F type epoxy (meth)acrylate, and benzocyclobutene resins. The compound (I) having a polymerizable unsaturated group may be used alone or in combination of two or more.

[Hardening accelerator] The resin composition of this embodiment may further contain a hardening accelerator. The hardening accelerator is not particularly limited, for example: imidazoles such as triphenylimidazole; organic peroxides such as benzoyl peroxide, lauryl peroxide, acetyl peroxide, p-chlorobenzoyl peroxide, di-tert-butyl diperoxyphthalate; azo compounds such as azobisnitrile; N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2-N-ethylanilinoethanol, tri-n-butylamine, pyridine, quinoline, N-methyl iodine, triethanolamine, triethylenediamine, tetramethylbutanediamine , N-methylpiperidine and other tertiary amines; phenols such as phenol, xylenol, cresol, resorcinol, catechol and other phenols; organic metal salts such as lead cycloalkanoate, lead stearate, zinc cycloalkanoate, zinc octanoate, manganese octanoate, tin oleate, dibutyltin apple acid, manganese cycloalkanoate, cobalt cycloalkanoate, iron acetylacetonate; organic metal salts dissolved in phenol, bisphenol and other hydroxyl compounds; inorganic metal salts such as tin chloride, zinc chloride, aluminum chloride; organic tin compounds such as dioctyltin oxide, other alkyl tin, alkyl tin oxide, etc. Among them, triphenylimidazole promotes the hardening reaction and has a higher glass transition temperature, so it is particularly ideal.

[Silane coupling agent and wetting dispersant] The resin composition of this embodiment may further contain a silane coupling agent and a wetting dispersant. The silane coupling agent is not particularly limited as long as it is a silane coupling agent generally used for surface treatment of inorganic substances, for example: amino silane compounds such as γ-aminopropyl triethoxysilane and N-β-(aminoethyl)-γ-aminopropyl trimethoxysilane; epoxy silane compounds such as γ-glycidoxypropyl trimethoxysilane; acrylic silane compounds such as γ-acryloxypropyl trimethoxysilane; cationic silane compounds such as N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyl trimethoxysilane hydrochloride; phenyl silane compounds, etc. The silane coupling agent may be used alone or in combination of two or more. The wetting dispersant is not particularly limited as long as it is a dispersing stabilizer used for coating applications, for example: DISPERBYK-110, 111, 118, 180, 161, BYK-W996, W9010, W903, etc. manufactured by BYK Chemie Japan Co., Ltd.

[Surface Conditioner] The resin composition of this embodiment may further contain a surface conditioner. The surface conditioner is not particularly limited. For example, a surface conditioner whose main component is polyester-modified polydimethylsiloxane can exhibit a varnish surface tension reduction effect when the prepreg is coated. The surface conditioner may also be a surface conditioner used for coating purposes, such as BYK-310, 313, etc. manufactured by BYK Chemie Japan Co., Ltd.

[Solvent] The resin composition of this embodiment may further contain a solvent. By containing a solvent, the viscosity of the resin composition during preparation is reduced, the workability is better, and the impregnation property of the substrate described below is better. The solvent is not particularly limited as long as it can dissolve part or all of the resin components in the resin composition, for example: ketones such as acetone, methyl ethyl ketone, and methyl cellulose; aromatic hydrocarbons such as toluene and xylene; amides such as dimethylformamide; propylene glycol monomethyl ether and its acetate, etc. The solvent may be used alone or in combination of two or more.

[Other ingredients] The resin composition of the present embodiment may contain ingredients other than those mentioned above within the range that does not impair the expected properties. Such arbitrary admixtures include, for example, various polymer compounds such as thermosetting resins other than those mentioned above, thermoplastic resins and their oligomers, elastomers, flame retardant compounds, various additives, etc. They can be used by general users without any special restrictions. For example, flame retardant compounds include bromine compounds such as 4,4'-dibromobiphenyl, phosphate esters, melamine phosphate, phosphorus-containing epoxy resins, melamine, nitrogen-containing compounds such as benzoguanamine, thiophene-containing compounds, silicon-based compounds, etc. In addition, various additives include ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent whitening agents, photosensitizers, dyes, pigments, thickeners, lubricants, defoamers, dispersants, leveling agents, glossing agents, polymerization inhibitors, etc., but are not particularly limited to these. These arbitrary admixtures can be used alone or in combination of two or more.

[Manufacturing method of resin composition] The manufacturing method of the resin composition of the present embodiment is not particularly limited, for example: a method of mixing a cyanate compound (A), a filler (B), a molybdenum compound (C), zinc oxide (D), and any of the above components, and stirring them thoroughly. At this time, in order to make each component dissolve or disperse uniformly, known treatments such as stirring, mixing, and kneading can be implemented. Specifically, by using a stirring tank equipped with a stirrer with appropriate stirring capacity to carry out stirring and dispersing treatment, the dispersion of the filler in the resin composition can be made better. The above-mentioned stirring, mixing, and kneading treatment can be appropriately carried out using, for example, a device for mixing such as a ball mill, a bead mill, or a known device such as a mixing device of a revolving or rotating type.

Furthermore, when preparing the resin composition, a solvent may be used as needed. The type of solvent is not particularly limited as long as it can dissolve the resin in the resin composition. The specific examples are as described above.

[Application] The resin composition of this embodiment is suitable for use as a cured product, a prepreg, a film-like bottom layer filler, a resin sheet, a laminate, a build-up material, a non-conductive film, a metal-clad laminate, a printed wiring board, a fiber-reinforced composite material, or a semiconductor device. The following describes these.

[Cured material] The cured material of this embodiment is obtained by curing the above-mentioned resin composition. The method for producing the cured material is not particularly limited, and the cured material can be obtained by, for example, melting or dissolving the resin composition in a solvent, pouring it into a mold, and curing it under normal conditions using heat, light, etc. In the case of thermal curing, the curing temperature is not particularly limited, but from the perspective of efficiently carrying out the curing and preventing the obtained cured material from deteriorating, the range of 120°C to 300°C is preferred. In the case of light curing, the wavelength range of the light is not particularly limited, but it is preferably a range of 100nm to 500nm, which allows efficient curing using a photopolymerization initiator, etc.

[Prepreg] The prepreg of this embodiment has a substrate, and the resin composition of this embodiment impregnated or coated on the substrate. The method for manufacturing the prepreg can be carried out according to the conventional method without special restrictions. For example, after the resin composition of this embodiment is impregnated or coated on the substrate, it is heated in a dryer at 100 to 200°C for 1 to 30 minutes to semi-harden it (B stage), thereby manufacturing the prepreg of this embodiment.

In the prepreg, the content of the resin composition of the present embodiment (including the filler) is preferably 30 to 90% by mass, more preferably 35 to 85% by mass, and even more preferably 40 to 80% by mass, relative to the total amount of the prepreg. When the content of the resin composition is within the above range, the moldability tends to be better.

The base material is not particularly limited, and various known materials for printed wiring boards can be appropriately selected depending on the intended use and performance. Specific examples of the fiber constituting the substrate are not particularly limited, and examples include glass fibers such as E glass, D glass, S glass, Q glass, spherical glass, NE glass, L glass, and T glass; inorganic fibers other than glass such as quartz; wholly aromatic polyamides such as poly(p-phenylene terephthalamide) (Kevlar (registered trademark), manufactured by DuPont), copoly(p-phenylene terephthalamide) (Technora (registered trademark), manufactured by Teijin Technoproducts Co., Ltd.), 2,6-hydroxynaphthoic acid (naphthoic acid) and p-hydroxybenzoic acid (Vectran (registered trademark), manufactured by Kuraray Co., Ltd.), Zxion (registered trademark, KB Organic fibers such as polyester (Zylon (registered trademark), manufactured by Toyobo Co., Ltd.), polyimide, etc. These base materials may be used alone or in combination of two or more.

Among them, at least one selected from the group consisting of E glass cloth, T glass cloth, S glass cloth, Q glass cloth, and organic fiber is preferred.

The shape of the substrate is not particularly limited, and examples include woven fabric, non-woven fabric, coarse yarn, chopped strand felt, and surface felt. The weaving method of the fabric is not particularly limited, and examples thereof include plain weave, basket weave, and twill weave, and one of these known fabrics can be appropriately selected for use according to the intended use or performance. In addition, glass fabrics obtained by fiber opening treatment or surface treatment with a silane coupling agent or the like are preferably used. The thickness or mass of the substrate is not particularly limited, and generally, a thickness of about 0.01 to 0.3 mm is preferably used. In particular, considering the strength and water absorption, the substrate is preferably a glass woven fabric with a thickness of less than 200 μm and a mass of less than 250 g/m ² , and more preferably a glass woven fabric composed of glass fibers of E glass, S glass and T glass.

[Resin sheet] The resin sheet of this embodiment can be used to form an insulating layer of a metal-clad laminate, a printed wiring board, etc., and includes both the resin sheet and the resin sheet with a support.

The resin sheet of the present embodiment is obtained by forming the resin composition of the present embodiment into a sheet. The method for manufacturing the resin sheet can be carried out according to a conventional method without special restrictions. For example, it can be obtained by peeling off or etching the support from the resin sheet with the support described later. Alternatively, the resin composition of the present embodiment can be dissolved in a solvent to form a solution, and then supplied to a mold having a sheet-shaped cavity and dried to form a sheet, thereby obtaining a resin sheet without using a sheet substrate such as a support.

The resin sheet with support of this embodiment has a support and the resin composition disposed on the support. The resin sheet with support can be produced by directly coating the resin composition on a support such as copper foil or resin film and drying it.

The support is not particularly limited, and known materials used in various printed wiring board materials can be used. For example: organic film substrates such as polyimide film, polyamide film, polyester film, polyethylene terephthalate (PET) film, polybutylene terephthalate (PBT) film, polypropylene (PP) film, polyethylene (PE) film, polycarbonate film, ethylene tetrafluoroethylene copolymer film, and release films coated with release agents on the surface of these films, conductive foils such as copper foil, glass plates, SUS plates, plate-shaped inorganic films such as FPR. Among them, electrolytic copper foil and PET film are preferred.

The coating method includes, for example, dissolving the resin composition of the present embodiment in a solvent to form a solution, and then coating the solution on a support using a coating rod, a die coater, a scraper, a Baker applicator, or the like.

The resin sheet with support is preferably prepared by applying the resin composition to a support and semi-hardening it (B-stage). Specifically, for example, the resin composition is applied to a support such as copper foil, and then semi-hardened in a dryer at 100 to 200°C for 1 to 60 minutes to prepare the resin sheet with support. The amount of the resin composition attached to the support is preferably in the range of 1 to 300 μm based on the resin thickness of the resin sheet with support.

[Laminated board] The laminated board of this embodiment is formed by laminating one or more selected from the group consisting of the above-mentioned prepreg, resin sheet, and resin sheet with a support. The laminated board can be obtained by laminating and forming a prepreg with other layers. The other layers are not particularly limited, for example: a wiring board for the inner layer made separately.

[Metal foil-clad laminate] The metal foil-clad laminate of this embodiment has: one or more selected from the group consisting of the above-mentioned prepreg, resin sheet, and resin sheet with a support; and metal foil arranged on one or both sides of at least one selected from the group consisting of the above-mentioned prepreg, resin sheet, and resin sheet with a support. The metal foil-clad laminate of this embodiment is, for example, a copper foil-clad laminate obtained by laminating and hardening the above-mentioned prepreg and copper foil.

The copper foil used here is not particularly limited as long as it is used in printed wiring board materials, and is preferably a known copper foil such as a rolled copper foil or an electrolytic copper foil. In addition, the thickness of the conductor layer is not particularly limited, but is preferably 1 to 70 μm, and more preferably 1.5 to 35 μm.

The forming method and forming conditions of the metal-clad laminate are not particularly limited, and the forming method and conditions of the general laminate for printed wiring boards and multi-layer boards can be adopted. For example, a multi-stage press, a multi-stage vacuum press, a continuous forming machine, a high-pressure autoclave forming machine, etc. can be used for forming the metal-clad laminate. In addition, when forming the metal-clad laminate, generally speaking, the temperature is 100 to 350°C, the pressure is a surface pressure of 2 to 100 kgf/ ^cm2 , and the heating time is in the range of 0.05 to 5 hours. Furthermore, if necessary, post-hardening can also be performed at a temperature of 150 to 350°C. Furthermore, a multi-layer board can be manufactured by combining and stacking the above-mentioned prepreg, copper foil, and a separately manufactured wiring board for the inner layer.

[Printed wiring board] The printed wiring board of this embodiment includes an insulating layer and a conductive layer formed on the surface of the insulating layer, wherein the insulating layer includes a cured product of the resin composition. The metal-clad laminate can be used as a printed wiring board by forming a predetermined wiring pattern. The metal-clad laminate has good formability and chemical resistance, and is particularly effective as a printed wiring board for a semiconductor package that requires such performance.

The printed wiring board of this embodiment can be specifically manufactured according to the following method, for example. First, prepare the copper-clad foil laminate mentioned above. Then, perform etching treatment on the surface of the copper-clad foil laminate and form an inner circuit to manufacture an inner substrate. The inner circuit surface of this inner substrate is subjected to surface treatment as needed to improve the bonding strength, and then the required number of prepregs are stacked on the inner circuit surface, and then copper foil for the outer circuit is stacked on the outside, and the prepreg is heated and pressurized to form an integral body. In this way, a multi-layer laminate is manufactured in which an insulating layer composed of a base material and a cured product of a resin composition is formed between the copper foil for the inner circuit and the outer circuit. Then, after the multi-layer laminate is processed for opening through holes and vias, a desmearing treatment is performed to remove the resin residue, i.e., the resin residue, from the resin component contained in the hardened material. After that, a plated metal film is formed on the wall of the hole to connect the inner circuit with the copper foil for the outer circuit, and then the copper foil for the outer circuit is etched to form the outer circuit, thus making a printed wiring board.

The printed wiring board obtained in the above manufacturing example has an insulating layer and a conductive layer formed on the surface of the insulating layer, and the insulating layer contains the resin composition of the above-mentioned embodiment, that is, the above-mentioned prepreg (substrate and the above-mentioned resin composition attached thereto) and the resin composition layer of the metal foil-clad laminate (a layer composed of the above-mentioned resin composition) constitute the insulating layer containing the above-mentioned resin composition.

Furthermore, when a metal-clad laminate is not used, a conductor layer forming a circuit may be formed on the prepreg, the resin sheet, or the resin composition to produce a printed wiring board. In this case, the conductor layer may be formed by electroless plating.

The printed wiring board of this embodiment can be used particularly effectively as a printed wiring board for a semiconductor package because the thermal conductivity of the insulating layer is excellent in isotropy.

[Build-up material] The resin composition of this embodiment can be used as a build-up material. Here, "build-up" means stacking prepregs or resin sheets and repeating hole processing, wiring formation, etc. layer by layer to produce a printed wiring board with a multi-layer structure.

More specifically, a prepreg, a resin sheet, a resin sheet with a support, or a metal-clad laminate using the resin composition of the present embodiment can be used as a build-up material for a printed wiring board. In a printed wiring board formed using the prepreg or resin sheet of the present embodiment, the prepreg or resin sheet constitutes an insulating layer. In a printed wiring board formed using a metal-clad laminate, the prepreg (base material and the resin composition attached thereto) and the resin sheet used in manufacturing the metal-clad laminate constitute an insulating layer.

Specifically, when the prepreg of this embodiment is used as a build-up material, the metal-clad laminate is first manufactured using the prepreg according to the above-mentioned method for manufacturing the metal-clad laminate, and then the printed wiring board of this embodiment can be obtained using the above-mentioned method. Alternatively, the prepreg can be directly used as a build-up material and used as a material for a multi-layer printed wiring board.

When the resin sheet of the present embodiment is used as a build-up material, the printed wiring board of the present embodiment can be obtained by performing surface treatment on the resin composition layer (insulating layer) of the resin sheet according to a conventional method and forming a wiring pattern (conductor layer) on the surface of the insulating layer by plating.

Furthermore, when the metal foil-clad laminate of the present embodiment is used as a build-up material, the metal foil of the metal foil-clad laminate is etched according to the conventional method, the layer composed of the prepreg (insulating layer) is surface treated, and a wiring pattern (conductor layer) is formed on the surface of the insulating layer by plating, thereby obtaining the printed wiring board of the present embodiment.

In any case, other various steps (such as hole opening processing to form through holes, vias, etc.) may be added as needed.

[Non-conductive film] The resin composition of this embodiment can be used as a non-conductive film (NCF). Here, "non-conductive film" refers to a thin film connection material that has both bonding and insulating functions. It is a film-type adhesive used when packaging electronic components or parts. For example, non-conductive film can be used to bond the electrode surface of a semiconductor chip to the surface of a substrate, and can also serve as a bottom layer filler.

The non-conductive film may be in any form, for example, a resin sheet containing the resin composition of the present embodiment, or a resin sheet with a support having a layer containing the resin composition of the present embodiment. The non-conductive film may be prepared by conventional methods without any particular limitation. For example, the non-conductive film may be obtained by forming a layer containing the resin composition on a support and removing the support.

[Fiber-reinforced composite material] The fiber-reinforced composite material of the present embodiment includes the resin composition of the present embodiment and reinforcing fibers. The reinforcing fibers may be generally known products without particular limitation. Specific examples thereof include glass fibers such as E glass, D glass, L glass, S glass, T glass, Q glass, UN glass, NE glass, spherical glass, carbon fibers, aromatic polyamide fibers, boron fibers, PBO fibers, high-strength polyethylene fibers, alumina fibers, and silicon carbide fibers. The shape and arrangement of the reinforcing fibers are not particularly limited and may be appropriately selected from woven fabrics, nonwoven fabrics, felt, knitted fabrics, braided ropes, unidirectional strands, coarse yarns, cut strands, and the like. In addition, as for the form of the reinforced fiber, a preform (a fiber structure such as a laminated fabric base cloth composed of the reinforced fiber, a fiber structure such as a three-dimensional fabric or a woven fabric) can also be used.

The manufacturing method of these fiber-reinforced composite materials can be appropriately adopted by generally known methods without special restrictions. Specific examples include liquid composite forming method, resin film fusion method, fiber winding method, manual arrangement method, extrusion forming method, etc. Among them, the resin transfer forming method, which is a type of liquid composite forming, can place materials other than preforms such as metal plates, cores, and honeycomb cores in the forming mold in advance, so it can cope with various uses and can produce composite materials with more complex shapes in a short time and in large quantities, so it is more ideal.

[Thin-film bottom filler] The thin-film bottom filler of the present embodiment has a layer containing the above-mentioned resin composition. By using a thin-film bottom filler, when connecting the semiconductor chip and the circuit substrate during semiconductor chip mounting such as flip-chip mounting, the bottom filler can be filled in the space between the semiconductor chip and the circuit substrate. In particular, compared to using a liquid bottom filler, it is less likely that air bubbles will appear between the semiconductor chip and the circuit substrate by using a thin-film bottom filler. Therefore, even if the number of bumps has increased in recent years, the bump pitch has become narrower, and the gap between the bump heights has become narrower, the use of a thin-film bottom filler can still suppress the appearance of air bubbles between the semiconductor chip and the circuit substrate.

The film-like bottom filling material may have a release layer laminated on the layer in addition to the layer containing the resin composition. The release layer has the function of protecting the layer containing the resin composition until it is used for semiconductor mounting processing, for example, it is removed when a semiconductor device is attached to the bottom filling insulating film.

[Semiconductor device] The semiconductor device of this embodiment has the above-mentioned hardened material or film-like bottom layer filling material. The semiconductor device of this embodiment can be manufactured by installing a semiconductor chip in the conductive part of the above-mentioned printed wiring board. Here, the conductive part refers to the part where the electric signal is transmitted in the multi-layer printed wiring board, and the position can be on the surface or in the buried part. In addition, the semiconductor chip can be any electrical circuit component made of semiconductor as the material, without any special restrictions.

The semiconductor chip mounting method when manufacturing the semiconductor device of this embodiment is not particularly limited as long as the semiconductor chip can function effectively. Specifically, there can be listed a wire bonding mounting method, a flip chip mounting method, a mounting method using a bumpless build-up layer (BBUL), a mounting method using anisotropic conductive film (ACF), a mounting method using non-conductive film (NCF), etc. [Example]

The present invention is described in more detail below using examples and comparative examples. The present invention is not limited to the following examples. In the following examples and comparative examples, the measurement and evaluation of various physical properties are performed in the following manner.

<Evaluation method of molybdenum compound particles> (Zinc oxide content) The element ratios constituting the molybdenum compound particles were measured using X-ray photoelectron spectroscopy (XPS). The zinc oxide content in terms of ZnO was calculated from the measured element ratios. Measuring machine: QuanteraII manufactured by ULVAC-PHI Co., Ltd. X-ray source: Monochromatic Al-Kα ray Measuring range: 1000×1000μm Vacuum degree: 4.0×10 ^-6 Pa (Circularity) The circumference and area of the molybdenum compound particles were measured using a wet flow particle size and shape analyzer, and the circularity was calculated. Measuring machine: FPIA-3000S manufactured by SYSMEX Co., Ltd. Sheath liquid: Isopropyl alcohol Measuring mode: HPF Counting method: Total count 36,000 (average particle size) The particle size distribution of the molybdenum compound particles is measured using a particle size distribution measuring device, and the average particle size (D50) is calculated. Measuring machine: Microtrac MT3300EXII manufactured by MicrotracBEL Co., Ltd. Measuring solvent: Isopropyl alcohol

<Evaluation method of resin varnish> (Resin curing time measurement) Use a micropipette to inject the resin varnish with a solid content concentration of 75% by mass prepared in the example or comparative example into the following measuring machine, and measure the time until the resin cures. If the resin curing time is 200 seconds or more, it is judged to be qualified. Measuring machine: MADOKA, automatic curing time measuring device manufactured by Matsuo Sangyo Co., Ltd. Hot plate temperature: 170°C Torque judgment value: 15% Rotation speed: 190rpm Revolution speed: 60rpm Gap value: 0.3mm Averaging score: 50 Injection volume: 500μL

<Method for evaluating metal foil laminates> (Appearance evaluation) For the metal foil laminates produced in the embodiments or comparative examples, the copper foils on both sides were etched away to obtain samples in which the copper foils on the surface were completely removed. The samples were visually observed, and those with no pores were rated as "○", and those with pores were rated as "×".

(Drill bit life (number of drill bit breakage holes)) The pad, the metal foil laminated plate made in the embodiment or comparative example, and the auxiliary plate are stacked in order from bottom to top to obtain an evaluation sample. This sample is drilled 10,000 times from the top of the sample under the following drilling conditions, and the back of the metal foil laminated plate is observed with a hole analyzer (manufactured by Viamechanics Co., Ltd.) to count the number of holes. Processing machine: Viamechanics ND-1 V212 Auxiliary plate: Mitsubishi Gas Chemical LE900 Pad: SPB-W, Decoluxe Japan Drill bit: Uniontool MC L517AW 0.105mm×1.8mm

(Hole Position Accuracy) After drilling 10,000 times under the same drilling conditions as above, the positional deviation between the hole position on the back of the metal foil laminate and the specified coordinates was measured using a hole analyzer (manufactured by Viamechanics Co., Ltd.). The positional deviation of the processed holes of each drill was measured, and the average value and standard deviation (σ) were calculated, and the average value of the positional deviation + 3σ was calculated.

(Synthesis Example 1) Synthesis of 1-naphthol aralkyl cyanate resin (SNCN) 300 g (1.28 mol in terms of hydroxyl (OH) group) of α-naphthol aralkyl resin (SN495V, OH group equivalent: 236 g/eq., manufactured by Nippon Steel Chemical Co., Ltd.) and 194.6 g (1.92 mol) of triethylamine (1.5 mol per 1 mol of hydroxyl group) were dissolved in 1800 g of dichloromethane, and the mixture was named Solution 1.

125.9 g (2.05 mol) of cyanogen chloride (1.6 mol relative to 1 mol of hydroxyl), 293.8 g of dichloromethane, 194.5 g (1.92 mol) of 36% hydrochloric acid (1.5 mol relative to 1 mol of hydroxyl), and 1205.9 g of water were stirred and kept at a liquid temperature of -2 to -0.5°C for 30 minutes to add solution 1. After the addition of solution 1 was completed, the mixture was stirred at the same temperature for 30 minutes, and then 65 g (0.64 mol) of triethylamine (0.5 mol relative to 1 mol of hydroxyl) dissolved in 65 g of dichloromethane was added for 10 minutes to obtain a solution (solution 2). After the addition of solution 2 was completed, the mixture was stirred at the same temperature for 30 minutes to complete the reaction.

The reaction solution was then allowed to stand to separate the organic phase and the aqueous phase. The obtained organic phase was washed five times with 1300 g of water. The electrical conductivity of the waste water after the fifth water washing was 5 μS/cm, confirming that the removable ionic compounds were fully removed by water washing.

The organic phase after washing was concentrated under reduced pressure and finally concentrated and dried at 90°C for 1 hour to obtain 331 g of the target 1-naphthol aralkyl type cyanate compound (SNCN) (orange viscous substance). The mass average molecular weight Mw of the obtained SNCN was 600. In addition, the infrared absorption spectrum of SNCN showed absorption at 2250 cm ^-1 (cyanate group) and no absorption of hydroxyl group.

(Synthesis Example 2) Synthesis of diallyl bisphenol A type cyanate compound (DABPACN) 11.7 g of diallyl bisphenol A (hydroxyl equivalent 154.21 g/eq.) (0.076 mol in terms of hydroxyl (OH) group) ("DABPA" manufactured by Yamato Chemical Industries, Ltd.) and 7.8 g (0.076 mol) of triethylamine (1.0 mol per 1 mol of hydroxyl group) were dissolved in 138.1 g of dichloromethane to obtain solution A.

Under stirring of 7.0g (0.114mol) of cyanogen chloride (1.5mol relative to 1mol of hydroxyl), 58.4g of dichloromethane, 11.8g (0.116mol) of 36% hydrochloric acid (1.53mol relative to 1mol of hydroxyl), and 153.6g of water, solution A was added over 10 minutes while maintaining the liquid temperature at -2 to -0.5°C. After the addition of solution A was completed, the mixture was stirred at the same temperature for 30 minutes, and then solution B was added after 5 minutes by dissolving 8.8g (0.086mol) of triethylamine (1.1mol relative to 1mol of hydroxyl) in 9.3g of dichloromethane. After the addition of solution B was completed, the mixture was stirred at the same temperature for 30 minutes to complete the reaction.

The reaction solution was then allowed to stand to separate the organic phase and the aqueous phase. The obtained organic phase was washed with 40 g of 0.1 N hydrochloric acid and then washed three times with 40 g of water. The electrical conductivity of the waste water after the third water washing was 17 μS/cm, confirming that the removable ionic compounds were fully removed by water washing.

The organic phase after washing was concentrated under reduced pressure and finally concentrated and dried at 90°C for 1 hour to obtain 13.2 g of the target diallylbisphenol A type cyanate compound DABPACN (light yellow liquid). The IR spectrum of the obtained DABPACN showed absorption at 2264 cm ^-1 (cyanate group) and no absorption of hydroxyl group. The cyanate group equivalent of the obtained cyanate compound DABPACN was 179 g/eq.

(Example 1) 35 parts by mass of the 1-naphthol aralkyl cyanate compound (cyanate group equivalent: 261 g/eq.) obtained in Synthesis Example 1, 25 parts by mass of polyphenylmethane maleimide (BMI-2300, manufactured by Yamato Chemical Industries, Ltd.), 40 parts by mass of naphthalene ether type epoxy resin (HP-6000, epoxy group equivalent: 250 g/eq., manufactured by DIC Corporation), molten spherical silica (SC4053-SQ, A A resin varnish was obtained by mixing 60 parts by mass of molten spherical silica (SFP-330MC, manufactured by Denka Co., Ltd.), 140 parts by mass of spherical zinc molybdate (ZnO content in the molybdenum compound particles is 3.7% by mass, circularity is 0.92, average particle size is 1.0 μm, manufactured by Admatechs Co., Ltd.), 3 parts by mass of a silane coupling agent (KBM-403, manufactured by Shin-Etsu Chemical Co., Ltd.), 3 parts by mass of a wetting dispersant (manufactured by BYK Chemie Japan Co., Ltd.), 1 part by mass of a surface conditioner (manufactured by BYK Chemie Japan Co., Ltd.), and 1 part by mass of 2,4,5-triphenylimidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a resin varnish. According to the above method, the heat curing time of the obtained resin varnish was measured. The results are shown in Table 1.

The obtained resin varnish was further diluted with methyl ethyl ketone (solvent) and impregnated onto E glass cloth with a thickness of 90 μm. It was then heated and dried at 160°C for 4 minutes to obtain a prepreg with a thickness of 0.1 mm (resin composition content 50%). Then, 8 sheets of the obtained prepreg were stacked to form a laminate, and electrolytic copper foil (3EC-VLP, manufactured by Mitsui Metal Mining Co., Ltd.) with a thickness of 12μm was placed on the upper and lower sides of the obtained laminate, and vacuum pressing was performed for 120 minutes at a pressure of 20kgf/ ^cm2 and a temperature of 220℃ to perform laminate forming to produce a 0.8mm thick metal foil laminate (double-sided copper-clad laminate). The appearance evaluation, drill bit life, and hole position accuracy of the obtained metal foil laminate were evaluated. The results are shown in Table 1.

(Example 2) 29 parts by mass of the diallylbisphenol A cyanate compound (DABPACN, cyanate group equivalent: 179 g/eq.) obtained in Synthesis Example 2, 28 parts by mass of polyphenylmethane maleimide (BMI-2300, manufactured by Yamato Chemical Industries, Ltd.), 43 parts by mass of naphthyl ether epoxy resin (HP-6000, epoxy group equivalent: 250 g/eq., manufactured by DIC Corporation), and molten spherical silica (SC4053- A resin varnish was obtained by mixing 60 parts by mass of SQ (manufactured by Admatechs Co., Ltd.), 140 parts by mass of molten spherical silica (SFP-330MC, manufactured by Denka Co., Ltd.), 3 parts by mass of spherical zinc molybdate (ZnO content in molybdenum compound particles: 3.7% by mass, circularity: 0.92, average particle size: 1.0 μm, manufactured by Admatechs Co., Ltd.), 5 parts by mass of a silane coupling agent (KBM-403, manufactured by Shin-Etsu Chemical Co., Ltd.), 3 parts by mass of a wetting dispersant (manufactured by BYK Chemie Japan Co., Ltd.), 1 part by mass of a surface conditioner (manufactured by BYK Chemie Japan Co., Ltd.), and 1 part by mass of 2,4,5-triphenylimidazole (manufactured by Tokyo Chemical Industry Co., Ltd.). The heat curing time of the resin varnish obtained by the above method was measured. The results are shown in Table 1.

The obtained resin varnish was further diluted with methyl ethyl ketone and impregnated on 90μm thick E glass cloth, and dried at 160℃ for 9 minutes to obtain a 0.1mm thick prepreg (resin composition content 50%). Then 8 sheets of the obtained prepreg were stacked to form a laminate, and a 12μm thick electrolytic copper foil (3EC-VLP, Mitsui Metal Mining Co., Ltd.) was placed on the upper and lower sides of the obtained laminate, and vacuum pressing was performed for 120 minutes at a pressure of 20kgf/ ^cm2 and a temperature of 220℃ to perform lamination forming to produce a 0.8mm thick metal foil laminate (double-sided copper laminate). The appearance evaluation, drill bit life, and hole position accuracy of the obtained metal foil laminate were evaluated. The results are shown in Table 1.

(Example 3) 25 parts by mass of a bisphenol A cyanate compound (manufactured by LONZA Co., Ltd., Primaset (registered trademark) BADCy, cyanate group equivalent: 139 g/eq.), 33 parts by mass of polyphenylmethane maleimide (BMI-2300, manufactured by Yamato Chemical Industries, Ltd.), 42 parts by mass of a naphthyl ether type epoxy resin (HP-6000, epoxy group equivalent: 250 g/eq., manufactured by DIC Co., Ltd.), and molten spherical silica (S C4053-SQ, manufactured by Admatechs Co., Ltd.), 60 parts by mass of molten spherical silica (SFP-330MC, manufactured by Denka Co., Ltd.), 140 parts by mass of spherical zinc molybdate (ZnO content in molybdenum compound particles: 3.7% by mass, circularity: 0.92, average particle size: 1.0 μm, manufactured by Admatechs Co., Ltd.), 3 parts by mass of silane coupling agent (KBM-403, manufactured by Shin-Etsu Chemical Co., Ltd.), 3 parts by mass of wetting dispersant (manufactured by BYK Chemie Japan Co., Ltd.), 1 part by mass of surface conditioner (manufactured by BYK Chemie Japan Co., Ltd.), and 1 part by mass of 2,4,5-triphenylimidazole (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed to obtain a resin varnish. The heat curing time of the resin varnish obtained by the above method was measured. The results are shown in Table 1.

The obtained resin varnish was further diluted with methyl ethyl ketone and impregnated on 90μm thick E glass cloth, and dried at 160℃ for 5 minutes to obtain a 0.1mm thick prepreg (resin composition content 50%). Then 8 sheets of the obtained prepreg were stacked to form a laminate, and a 12μm thick electrolytic copper foil (3EC-VLP, Mitsui Metal Mining Co., Ltd.) was placed on the upper and lower sides of the obtained laminate, and vacuum pressing was performed for 120 minutes at a pressure of 20kgf/ ^cm2 and a temperature of 220℃ to perform lamination forming to produce a 0.8mm thick metal foil laminate (double-sided copper-clad laminate). The appearance evaluation, drill bit life, and hole position accuracy of the obtained metal foil laminate were evaluated. The results are shown in Table 1.

(Example 4) Instead of using spherical zinc molybdate, 3 parts by mass of a mixture of zinc molybdate (produced by Koshin Chemical Research Institute Co., Ltd., circularity 0.91, average particle size 3.8 μm) and zinc oxide (produced by Koshin Chemical Research Institute Co., Ltd.) as a molybdenum compound (ZnO content 0.3% by mass) was used. The same procedure as in Example 1 was followed except that the above procedure was used. The obtained resin varnish was further diluted with methyl ethyl ketone and impregnated onto an E glass cloth having a thickness of 90 μm. The mixture was dried by heating at 130°C for 3 minutes to obtain a prepreg having a thickness of 0.1 mm. Using the obtained prepreg, a metal-clad laminate having a thickness of 0.8 mm was obtained in the same manner as in Example 1. The physical properties of the obtained resin varnish and metal foil laminate are shown in Table 1.

(Example 5) Instead of using spherical zinc molybdate, 12 parts by mass of a mixture of molybdenum disulfide (M-5 powder, manufactured by DAIZO Co., Ltd., circularity 0.91, average particle size 2.9 μm) and zinc oxide (manufactured by Kojun Chemical Research Institute Co., Ltd.) as a molybdenum compound (ZnO content 1.0 mass%) was used. The same procedure as in Example 1 was followed except that the above procedure was used. The obtained resin varnish was further diluted with methyl ethyl ketone and impregnated onto an E glass cloth having a thickness of 90 μm. The mixture was dried by heating at 130°C for 3 minutes to obtain a prepreg having a thickness of 0.1 mm. Using the obtained prepreg, a metal-clad laminate having a thickness of 0.8 mm was obtained in the same manner as in Example 1. The physical properties of the obtained resin varnish and metal foil laminate are shown in Table 1.

(Comparative Example 1) Example 1 does not use the spherical zinc molybdate, and the same procedure as Example 1 is followed to obtain a resin varnish. The obtained resin varnish is further diluted with methyl ethyl ketone, and is impregnated and coated on a 90μm thick E glass cloth, and is dried by heating at 160°C for 10 minutes to obtain a prepreg with a thickness of 0.1mm. Using the obtained prepreg, a metal foil-clad laminate with a thickness of 0.8mm is obtained in the same manner as Example 1. The physical property measurement results of the obtained resin varnish and metal foil-clad laminate are shown in Table 1.

(Comparative Example 2) In Example 1, 3 parts by mass of alkaline zinc molybdate (produced by Japan Inorganic Chemical Industry Co., Ltd.) obtained by heating at 300°C for 1 hour (ZnO content in molybdenum compound particles: 27.6% by mass, circularity: 0.87, average particle size: 2.5μm) was used instead of spherical zinc molybdate as the molybdenum compound. The same procedure as in Example 1 was followed to obtain a resin varnish. The obtained resin varnish was further diluted with methyl ethyl ketone and impregnated onto an E glass cloth having a thickness of 90μm. The prepreg having a thickness of 0.1mm was obtained by heating and drying at 130°C for 3 minutes. The obtained prepreg was used to obtain a metal foil-clad laminate having a thickness of 0.8 mm in the same manner as in Example 1. The results of the physical property measurements of the obtained resin varnish and the metal foil-clad laminate are shown in Table 1.

[Table 1] Evaluation items Embodiment 1 Embodiment 2 Embodiment 3 Embodiment 4 Embodiment 5 Comparison Example 1 Comparison Example 2 Resin curing time [seconds] 464 563 235 334 204 771 191 Appearance evaluation ○ ○ ○ ○ ○ ○ × Drill life ＞10000 ＞10000 ＞10000 ＞10000 ＞10000 ＞10000 ＞10000 Hole position accuracy (average deviation + 3σ) [μm] twenty three 26 25 twenty four twenty three 37 twenty three It can be confirmed from Table 1 that the metal foil-clad laminated plates obtained using the resin compositions of Examples 1 to 5 have excellent drilling processability and appearance evaluation. The metal foil-clad laminated plates obtained using the resin composition of Comparative Example 1 have poor hole position accuracy during drilling, and the metal foil-clad laminated plates obtained using the resin composition of Comparative Example 2 have poor appearance evaluation.

This application is based on a Japanese patent application filed with the Japan Patent Office on March 25, 2020 (Japanese Patent Application No. 2020-054954), the contents of which are incorporated herein by reference. [Industrial Applicability]

The resin composition of the present invention has industrial applicability as a material for prepreg and the like.

Claims (19)

A resin composition comprising a cyanate compound (A), a filler (B), a molybdenum compound (C), and zinc oxide (D); The filler (B) is one or more selected from a group consisting of an inorganic filler and an organic filler; The molybdenum compound (C) contains molybdenum compound particles; The contents of the cyanate compound (A), the filler (B), and the molybdenum compound (C) are 1 to 99.9 parts by mass, 10 to 500 parts by mass, and 0.2 to 30 parts by mass, respectively, relative to a total of 100 parts by mass of the resin solid component in the resin composition; The content of zinc oxide (D) in the resin composition is 0.1% by mass to 5% by mass relative to the total mass of the molybdenum compound particles. The resin composition of claim 1, wherein the zinc oxide (D) is contained in the molybdenum compound particles. The resin composition of claim 1 or 2, wherein the molybdenum compound particles are spherical in shape. The resin composition of claim 3, wherein the circularity of the molybdenum compound particles is 0.90 to 1.00. The resin composition of claim 1 or 2, wherein the average particle size of the molybdenum compound particles is 0.1 to 10 μm. The resin composition of claim 1 or 2, wherein the molybdenum compound (C) is at least one selected from the group consisting of zinc molybdate, ammonium molybdate, sodium molybdate, calcium molybdate, potassium molybdate, molybdenum disulfide, molybdenum trioxide, and molybdenum hydrate. A resin composition as claimed in claim 1 or 2, wherein the cyanate compound (A) is one or more selected from the group consisting of phenol novolac type cyanate compounds, naphthol aralkyl type cyanate compounds, naphthyl ether type cyanate compounds, xylene resin type cyanate compounds, bisphenol M type cyanate compounds, bisphenol A type cyanate compounds, diallylbisphenol A type cyanate compounds, and biphenyl aralkyl type cyanate compounds. The resin composition of claim 1 or 2, wherein the filler (B) is one or more inorganic fillers selected from the group consisting of silicon dioxide, aluminum oxide, aluminum nitride, boron nitride, alumina, aluminum hydroxide, and titanium oxide. The resin composition of claim 1 or 2, wherein the filler (B) is one or more organic fillers selected from the group consisting of polysilicone rubber powder and polysilicone composite powder. The resin composition of claim 1 or 2 further contains one or more compounds selected from the group consisting of a maleimide compound (M), an epoxy compound (E), a phenol compound (F), an alkenyl-substituted nadic acid imide compound (K), an oxycyclobutane resin (G), a benzophenone compound (H), and a compound having a polymerizable unsaturated group (I). The resin composition of claim 10, wherein the maleimide compound (M) is one or more selected from the group consisting of bis(4-maleimidephenyl)methane, 2,2-bis{4-(4-maleimidephenoxy)-phenyl}propane, bis(3-ethyl-5-methyl-4-maleimidephenyl)methane, a maleimide compound represented by the following formula (2), and a maleimide compound represented by the following formula (3); In formula (2), ^R1 each independently represents a hydrogen atom or a methyl group, and n1 is 1 to 10; In formula (3), the multiple R ² present each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group, and n2 is an average value, which represents 1＜n2≦5. The resin composition of claim 10, wherein the epoxy compound (E) is at least one selected from the group consisting of biphenyl aralkyl epoxy compounds, naphthalene epoxy compounds, and naphthyl ether epoxy resins. The resin composition of claim 1 or 2 is used for printed wiring board applications. A prepreg comprises: a substrate; and a resin composition as described in any one of claims 1 to 12 impregnated in or coated on the substrate. A resin sheet is obtained by forming the resin composition according to any one of claims 1 to 12 into a sheet. A resin sheet with a support, comprising: a support; and a resin composition as described in any one of claims 1 to 12 disposed on the support. A laminated board is formed by laminating one or more selected from the group consisting of a prepreg as claimed in claim 14, a resin sheet as claimed in claim 15, and a resin sheet with a support as claimed in claim 16. A metal foil-clad laminate having: one or more selected from the group consisting of a prepreg as in claim 14, a resin sheet as in claim 15, and a resin sheet with a support as in claim 16; and Metal foil disposed on one or both sides of at least one selected from the group consisting of the prepreg, the resin sheet, and the resin sheet with a support. A printed wiring board comprising: an insulating layer comprising a cured product of the resin composition of any one of claims 1 to 12; and a conductive layer formed on a surface of the insulating layer.