TWI403556B - A resin composition, and a prepreg, a laminate, and a circuit board comprising the resin composition - Google Patents

Abstract

This invention discloses a resin composition mainly containing: cyanate ester resins, an oxazolidinone compound, and a polyphenylene ether resin. The resin composition may be applied in the semi-solid prepreg or circuit board insulating layers, and has features of low dielectric constant and low dielectric loss. Additionally, this invention also discloses a semi-solid prepreg, laminated plate and circuit board containing the resin composition.

Description

Resin composition and semi-cured film, laminate and circuit board containing the same

The present invention relates to a resin composition, in particular to a thermosetting resin composition applicable to a prepreg or a circuit substrate insulating layer, which mainly comprises a cyanate ester resin and a nitrogen oxide heterocyclic compound. And polyphenylene ether (PPE) or polyphenylene oxide (PPO) resin.

With the rapid advancement of communication and broadband application technologies, materials used in conventional printed circuit boards (such as FR-4 grades) have been unable to meet advanced applications, especially for high frequency printed circuit boards.

Basically, in order to achieve high-frequency and high-speed telecommunication transmission characteristics of high-frequency printed circuit boards, and at the same time avoid loss or interference of data during transmission, the substrate materials used should preferably meet the needs of process technology and market applications. Electrical properties, heat resistance, water absorption, mechanical properties, dimensional stability, chemical resistance, etc.

In terms of electrical properties, the main considerations include the dielectric constant of the material and the dielectric loss (also known as the loss factor). In general, since the signal transmission speed of the substrate is inversely proportional to the square root of the dielectric constant of the substrate material, the dielectric constant of the substrate material is generally as small as possible; on the other hand, the smaller the dielectric loss represents the loss of signal transmission. The less the material, the lower the dielectric loss, the better the transmission quality.

Therefore, how to develop materials with low dielectric constant and low dielectric loss and apply them to the manufacture of high-frequency printed circuit boards is a problem that manufacturers of printed circuit board materials are trying to solve at this stage.

A main object of the present invention is to provide a resin composition mainly comprising a cyanate resin, a nitrogen oxide heterocyclic compound, and a polyphenylene ether resin.

In the resin composition of the present invention, the cyanate resin may be a compound having an (Ar-OC≡N) structure, wherein Ar may be substituted or unsubstituted benzene, biphenyl, naphthalene, phenol novolac. ), bisphenol A, bisphenol A novolac, bisphenol F, bisphenol F novolac, etc.; in addition, the cyanate resin may also have (-OC≡N) a substituted or unsubstituted dicyclopentadiene of a functional group.

More specifically, the cyanate resin is preferably selected from at least one of the following groups:

Wherein X ₁ and X ₂ are each independently at least one R, Ar, SO ₂ or O; and R is selected from the group consisting of -C(CH ₃ ) ₂ -, -CH(CH ₃ )-, -CH ₂ - and substituted or not Substituted dicyclopentadienyl; Ar is selected from substituted or unsubstituted benzene, biphenyl, naphthalene, phenolic, bisphenol A, bisphenol A phenolic, bisphenol F and bisphenol F phenolic n is an integer greater than or equal to 1; Y is an aliphatic functional group or an aromatic functional group.

In the resin composition of the present invention, the nitrogen-oxygen heterocyclic compound has a ring structure substituted with nitrogen and oxygen at the same time, and is preferably selected from at least one of the following groups:

Wherein X ₃ is R' or Ar; R' is selected from -C(CH ₃ ) ₃ , -CH ₂ (CH ₃ ), -CH ₃ and substituted or unsubstituted dicyclopentadienyl; Ar Selected from substituted or unsubstituted benzene, biphenyl, naphthalene, phenolic, bisphenol A, bisphenol A phenol, bisphenol F and bisphenol F phenolic; X ₄ and X ₅ are each independently R, Ar or -SO ₂ -; R is selected from -C(CH ₃ ) ₂ -, -CH(CH ₃ )-, -CH ₂ - and substituted or unsubstituted dicyclopentadienyl; n is greater than or equal to 1. An integer; Y is an aliphatic functional group or an aromatic functional group.

In the present invention, the inventors discovered through research and experiments that the nitrogen-oxygen heterocyclic compound can be directly bonded to the cyanate resin. Compared with the prior art, the cyanate resin needs to be effectively bonded to the resin by a catalyst, and the resin composition of the present invention can be crosslinked with or without a catalyst.

When the nitrogen-oxygen heterocyclic compound is bonded to the cyanate resin, the reaction rate can be increased by increasing the temperature. For example, the nitrogen-oxygen heterocyclic compound and the cyanate resin can be heated in a high-temperature furnace at 150 to 190 ° C. It takes 2 to 10 minutes to react quickly to form a semi-cured state or a cured state.

Since the cyanate resin has a low dielectric constant characteristic and the oxynitride compound has a low dielectric loss characteristic, the resin composition of the present invention can provide a low dielectric constant and a low dielectric loss. In addition, since the C atom and the N atom in the -OC≡N functional group may be directly bonded to the O atom and the C atom in the nitrogen heterocycle, respectively, during the bonding of the nitrogen-oxygen heterocyclic compound and the cyanate resin (O atom) The C atom between the N atom and the N atom generates a bond, so that a hydroxyl group which is easily bonded to water molecules to increase water absorption is not formed during the bonding process, and therefore, the resin composition of the present invention also has low hygroscopicity. Compared with the general FR4 material, the water absorption can be reduced by about 40% or more.

In the resin composition of the present invention, the polyphenylene ether resin is preferably selected from at least one of the following groups:

Wherein X ₆ is selected from the group consisting of a covalent bond, -SO ₂ -, -C(CH ₃ ) ₂ -, -CH(CH ₃ )-, -CH ₂ -; Z ₁ to Z ₁₂ are each independently selected from the group consisting of hydrogen and W is a hydroxyl group, a vinyl group, a styryl group, a propenyl group, a butenyl group, a butadienyl group or an epoxy functional group; and n is an integer greater than or equal to 1.

In the present invention, since the polyphenylene ether resin can effectively improve the dielectric properties of the resin composition, the addition of the polyphenylene ether resin to the nitrogen-oxygen heterocyclic compound and the cyanate resin can further reduce the composition of the resin composition. The electrical constant and the dielectric loss value, and the effect thereof is more remarkable at high frequencies (such as 1 GHz to 10 GHz). Further, since the polyphenylene ether resin also has flame resistance, the resin composition of the present invention can also achieve the V-1 flame retardant effect of the UL94 specification.

In the resin composition of the present invention, the preferred content ratio of each component is: (a) 100 parts by weight of a cyanate resin; (b) 1 to 1000 parts by weight of a nitrogen oxide heterocyclic compound; (c) 5 to 1000 parts by weight of the polyphenylene ether resin. Further, at a frequency of one billion hertz, the resin composition of the present invention has a dielectric constant of less than 3.5 and a dielectric loss of less than 0.005, but is not limited thereto.

In a preferred embodiment, the resin composition of the present invention is added with 10 to 500 parts by weight of a nitrogen oxide heterocyclic compound relative to 100 parts by weight of the cyanate resin to effectively achieve a low dielectric constant and a low dielectric loss. And other characteristics.

In a preferred embodiment, the resin composition of the present invention is a polyphenylene ether resin added in an amount of 50 to 500 parts by weight based on 100 parts by weight of the cyanate resin to effectively achieve a low dielectric constant and a low dielectric loss. characteristic.

In order to further improve the flame retardant properties of the resin composition, in the preferred embodiment, the present invention may optionally additionally add at least one specific flame retardant compound. The flame retardant compound selected may be a phosphate compound or a nitrogen-containing phosphate compound, but is not limited thereto. More specifically, the flame retardant compound preferably includes at least one of the following compounds: bisphenol diphenyl phosphate, ammonium polyphosphate, hydroquinone-bis-(biphenyl) Hydroquinone bis-(diphenyl phosphate), bisphenol A bis-(diphenylphosphate), tris(2-carboxyethyl)phosphine (tri(2) -carboxyethyl)phosphine, TCEP), tris(isopropyl chloride) phosphate, trimethyl phosphate (TMP), dimethyl methyl phosphonate (DMMP), resorcinol Resorcinol dixylenyl phosphate (RDXP (such as PX-200)), melamine polyphosphate, phosphazene (such as SPB-100), azo phosphate, 9,10-two 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, DOPO, and its derivatives or resins, melamine cyanurate ( Melamine cyanurate) and tri-hydroxy ethyl isocyanurate, but not limited thereto.

For example, the flame retardant compound may be a DOPO compound, a DOPO resin (such as DOPO-HQ, DOPO-PN, DOPO-BPN), a DOPO bonded epoxy resin, etc., wherein the DOPO-BPN may be DOPO-BPAN, DOPO. - Biphenol phenolic compounds such as BPFN and DOPO-BPSN, as shown in the following formula:

Wherein n is an integer greater than or equal to 1; X is a DOPO functional group: Y is a covalent bond, an aliphatic functional group or an aromatic functional group; and Z is a hydrogen, an aliphatic functional group or an aromatic functional group. Further, X and Z may be bonded to any substituent position on the benzene ring structure, and each benzene ring is not limited to only one X or Z substituent; for example, the benzene ring may have two or more X structures. a substituent, or two or more Z substituents. In addition, not every benzene ring structure needs to have X and Z substituents, and some benzene ring structures have X and Z substituents or X and Z substituents, respectively, and some benzene rings have no structural structure. X and Z substituents.

In the resin composition of the present invention, the addition of the flame-retardant compound has an advantage in that the flame retardancy of the resin composition and the cured product thereof can be increased. By the addition of the flame-retardant compound, the resin composition of the present invention can achieve the V-0 flame resistance effect of the UL94 specification, and the laminate and the circuit board to which the resin composition is applied have a good flame retarding effect.

With respect to the addition ratio, the flame retardant compound is preferably contained in an amount of 10 to 200 parts by weight based on 100 parts by weight of the cyanate resin, and the preferred content not only can significantly improve the flame retarding effect, but also is less likely to be composed of the resin. The physical properties of the substance and its cured product have an adverse effect.

Further, the resin composition of the present invention may optionally further comprise at least one compound selected from the group consisting of epoxy resins, phenol resins, phenol resins, styrene resins, polybutadiene resins, and the like. , an acid anhydride crosslinking agent and an amine based crosslinking agent.

Among them, the epoxy resin may be bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, novolac epoxy resin, bisphenol A phenolic epoxy resin, o-cresol (o -cresol novolac) epoxy resin, trifunctional epoxy resin, tetrafunctional epoxy resin, multifunctional epoxy resin, dicyclopentadiene epoxy resin (DCPD) Epoxy resin), phosphorus-containing epoxy resin, p-xylene epoxy resin, naphthalene epoxy resin or benzopyran epoxy resin, biphenol aldehyde ( Biphenyl novolac) epoxy resin, phenol aralkyl novolac epoxy resin, and the like. By the addition of the epoxy resin, the properties of the resin composition of the present invention such as crosslinkability and heat resistance can be further improved.

The acid anhydride crosslinking agent may be methyl tetrahydrophthalic anhydride (MTHPA), phthalic anhydride (PA), nadic methyl anhydride (NMA), a compound such as styrene maleic anhydride (SMA); the amine-based crosslinking agent may be a guanamine resin, dicyandiamide, bisaminodiphenyl hydrazine, bisaminodiphenylmethane, and malaysia Amine resin, amine base An amino triazine novolac resin or the like.

Further, the resin composition of the present invention may further optionally contain an additive such as an inorganic filler, a surfactant, a toughening agent, a curing accelerator or a solvent.

The main function of adding the inorganic filler is to increase the thermal conductivity of the resin composition, to improve the thermal expansion property and mechanical strength, and the inorganic filler is preferably uniformly distributed in the resin composition; the main purpose of adding the surfactant is The inorganic filler can be uniformly dispersed in the resin composition; the main purpose of adding the toughening agent is to improve the toughness of the resin composition; the main purpose of adding the hardening accelerator is to increase the reaction rate of the resin composition; and the main purpose of adding the solvent It is to change the solid content of the resin composition and adjust the viscosity of the resin composition.

Wherein, the inorganic filler may comprise ceria (molten or non-molten), alumina, magnesia, magnesium hydroxide, calcium carbonate, talc, clay, aluminum nitride, boron nitride, aluminum hydroxide, aluminum carbide At least one of cerium, cerium carbide, sodium carbonate, titanium dioxide, zinc oxide, zirconium oxide, quartz, diamond powder, diamond powder, graphite or calcined kaolin, and the inorganic filler may be spherical or irregular, and may be selected The pretreatment is via an surfactant. The inorganic filler may be a particle powder having a particle diameter of 100 μm or less, and is preferably a particle powder having a particle diameter of 1 to 20 μm, preferably a nano-sized particle powder having a particle diameter of 1 μm or less.

The surfactant may include a decane compound, a decane compound, an amino decane compound or a polymer of the above compound.

The toughening agent may comprise a rubber resin, a polybutadiene or a core-shell polymer, and the like.

The hardening accelerator may include a catalyst such as Lewis base or Lewis acid. Among them, the Lewis base may comprise imidazole, boron trifluoride amine complex, ethyltriphenyl phosphonium chloride, 2-methylimidazole (2MI), 2-benzene. 2-phenyl-1H-imidazole (2PZ), 2-ethyl-4-methylimidazole (2E4MZ), triphenylphosphine (TPP) and 4-dimethyl One or more of 4-dimethylaminopyridine (DMAP). The Lewis acid system may contain a metal salt compound such as a metal salt compound such as manganese, iron, cobalt, nickel, copper or zinc.

Further, the resin composition of the present invention may optionally contain other kinds of resins other than the cyanate resin and the nitrogen-oxygen heterocyclic compound. In this case, the resin composition may further be further provided with a curing accelerator to bond with the resin and the cyanate resin and the nitrogen-oxygen heterocyclic compound resin. For example, the resin composition may further comprise an epoxy resin and at least one curing accelerator, and the curing accelerator may effectively promote the ring opening action of the epoxy resin and the resin such as a cyanate resin and a nitrogen oxide heterocyclic compound. Bonding is performed.

The solvent may include methanol, ethanol, ethylene glycol monomethyl ether, methyl ethyl ketone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, toluene, xylene, methoxy ethyl acetate, A solvent such as ethoxyethyl acetate, propoxyethyl acetate, ethyl acetate, dimethylformamide or propylene glycol methyl ether or a mixed solvent thereof.

Still another object of the present invention is to disclose a semi-cured film which has low dielectric properties, heat-resistant flame retardancy, low moisture absorption, halogen-free properties, and the like, and can be applied to an insulating layer material of a laminate and a circuit board.

The semi-cured film of the present invention is a resin composition as described above, wherein the resin composition is formed into a semi-cured state via a heating process. For example, the resin composition can be placed on a polyethylene terephthalate (PET) film and heated to form a semi-cured film.

Still another object of the present invention is to disclose a laminate comprising at least one metal foil laminate and at least one insulating layer. The metal foil laminate may comprise a metal such as copper, aluminum, nickel, platinum, silver, gold or the like, or an alloy thereof, and is preferably a copper foil plate. The PET film is removed by laminating the prepreg film disclosed in the present invention on at least one piece of the metal foil layer, and the semi-cured film and the metal foil layer are heated and cured under high temperature and high pressure to form and The metal foil laminate is intimately bonded to the insulating layer.

Still another object of the present invention is to disclose a semi-cured film having high mechanical strength, low dielectric constant and low dielectric loss, heat and flame resistance, low moisture absorption, and halogen-free properties. Accordingly, the prepreg film disclosed in the present invention may comprise a reinforcing material and a resin composition as described above, wherein the resin composition is attached to the reinforcing material and is heated to a semi-cured state by high temperature. Among them, the reinforcing material may be a fiber material, a woven fabric and a non-woven fabric, such as a glass fiber cloth, etc., which may increase the mechanical strength of the prepreg film. In addition, the reinforcing material may be optionally pretreated with a decane coupling agent or a decane coupling agent, such as a glass fiber cloth pretreated with a decane coupling agent.

The aforementioned prepreg film can be cured by high temperature heating or high temperature and high pressure to form a cured film or a solid insulating layer, wherein if the resin composition contains a solvent, the solvent is volatilized and removed in a high temperature heating process.

Another object of the present invention is to disclose a laminate having low dielectric properties, heat and flame resistance, low moisture absorption, high mechanical strength and halogen-free characteristics, and is particularly suitable for high-speed and high-frequency signal transmission. Circuit board. Accordingly, the present invention provides a laminate comprising two or more metal foil laminates and at least one insulating layer. Wherein, the metal foil laminate may comprise a metal such as copper, aluminum, nickel, platinum, silver or gold or an alloy thereof: the insulating layer is formed by curing the above-mentioned semi-cured film under high temperature and high pressure, or overlapping the semi-cured film. It is formed by pressing between two metal foil laminates under high temperature and high pressure.

The laminate of the present invention has at least one of the following advantages: excellent heat and flame resistance, low moisture absorption, low dielectric constant and low dielectric loss, high thermal conductivity, preferred thermal expansion, and better mechanical properties. Strength and halogen-free environmental protection. The laminate is further processed by a manufacturing process or the like to form a circuit board, and the circuit board is bonded to the electronic component and operated in a severe environment such as high temperature and high humidity without affecting the quality thereof.

Still another object of the present invention is to disclose a circuit board having low dielectric properties, heat and flame resistance, low moisture absorption, high mechanical strength, and halogen-free characteristics, and is suitable for signal transmission at high speed and high frequency. Wherein, the circuit board comprises at least one of the aforementioned laminates, and the circuit board can be fabricated by a conventional circuit board process.

The present invention will be further described in the following examples, in which the present invention may be practiced by those of ordinary skill in the art. It is to be understood that the following examples are merely illustrative of the invention and are not intended to limit the scope of the invention, and that Modifications and variations are possible within the scope of the invention.

Embodiment 1

A resin composition comprising the following ingredients:

(A) 100 parts by weight of cyanate resin shown below

(B) 100 parts by weight of a nitrogen-oxygen heterocyclic compound as shown below, wherein X5 is as defined above

(C) 50 parts by weight of a polyphenylene ether resin as shown below, wherein n is an integer greater than or equal to

Embodiment 2

A resin composition comprising the following ingredients:

(A) 100 parts by weight of cyanate resin shown below

(B) 50 parts by weight of a nitrogen-oxygen heterocyclic compound shown below

(C) 150 parts by weight of a polyphenylene ether resin as shown below, wherein n is an integer greater than 1 or equal to

(D) 100 parts by weight of bisphenol A epoxy resin

(E) 50 parts by weight of flame retardant compound RDXP

(F) 0.1 part by weight of a cobalt metal salt compound

(G) 0.2 parts by weight of diphenylimidazole

(H) 50 parts by weight of molten cerium oxide

(I) 1 part by weight of a siloxane compound

(J) 30 parts by weight of toluene

(K) 20 parts by weight of methyl ethyl ketone

Embodiment 3

A resin composition comprising the following ingredients:

(A) 100 parts by weight of cyanate resin shown below

(B) 50 parts by weight of a nitrogen-oxygen heterocyclic compound shown below

(C) 150 parts by weight of a polyphenylene ether resin as shown below, wherein n is an integer greater than or equal to 1

(D) 100 parts by weight of DOPO-BPAN resin

(E) 50 parts by weight of a phosphorus-nitrogen compound

(F) 50 parts by weight of spherical alumina powder

(G) 1 part by weight of a siloxane compound

(H) 30 parts by weight of toluene

(I) 20 parts by weight of methyl ethyl ketone

Embodiment 4

A resin composition comprising the following ingredients:

(A) 100 parts by weight of a polyphenylene ether modified cyanate resin as shown below

(B) 50 parts by weight of a nitrogen-oxygen heterocyclic compound shown below

(C) 50 parts by weight of flame retardant compound RDXP

Embodiment 5

A semi-cured film obtained by mixing the resin composition disclosed in the second embodiment in a stirring tank and then coating it on a PET film and baking it into a semi-cured state by heating.

Embodiment 6

A semi-cured film, wherein the resin composition disclosed in the third embodiment is uniformly mixed in a stirring tank, placed in a dipping tank, and the glass fiber cloth is passed through the impregnation tank to adhere the resin composition to the glass fiber cloth. And heating and baking into a semi-cured state.

Example 7

A laminate comprising a half-cured film and a copper foil and a circuit substrate, wherein the semi-cured film is combined with a circuit substrate by a plane of the pre-cured film without the PET film, as described in Embodiment 5, The PET film is removed, and the surface of the prepreg film is removed from the PET film and bonded to a copper foil, and then pressed at a high temperature and a high pressure to cure the prepreg film to form an insulating layer between the copper foil and the circuit substrate.

Example eight

A laminate comprising four sheets of semi-cured film and two sheets of copper foil according to the sixth embodiment, which are laminated in the order of copper foil, four-stage semi-cured film and copper foil, and then pressed through a high temperature and high pressure process. The four-ply semi-cured film is cured to form an insulating layer between the two copper foils.

Example nine

A circuit board comprising a plurality of laminates and a plurality of prepreg films, wherein the laminates are laminated according to the eighth embodiment and then subjected to a photolithography process to form a surface circuit, and the prepreg film is as described in Embodiment 6. The plurality of laminates and the plurality of prepreg films are interleaved between the two copper foils, and the laminated structure is further formed into a circuit board substrate by a high temperature and high pressure pressing process, and the circuit board substrate can be further passed through a conventional circuit board. The manufacturing process is formed to form a circuit board, and no further description is made here.

Example ten

A circuit board whose main structure is as described in Embodiment 9, except that the laminated board is further subjected to a drilling process to form a blind hole.

Claims (12)

A resin composition comprising: a cyanate resin; a nitrogen oxide heterocyclic compound; and a polyphenylene ether resin; wherein the nitrogen oxide heterocyclic compound is selected from at least one of the following groups: Wherein X ₄ and X ₅ are each independently R, Ar or -SO ₂ -; R is selected from -C(CH ₃ ) ₂ -, -CH(CH ₃ )-, -CH ₂ - and substituted or unsubstituted Dicyclopentadienyl; n is an integer greater than or equal to 1; Y is an aliphatic functional group or an aromatic functional group. The resin composition according to claim 1, wherein the cyanate resin is selected from at least one of the following groups: Wherein X ₁ and X ₂ are each independently at least one R, Ar, SO ₂ or O; and R is selected from the group consisting of -C(CH ₃ ) ₂ -, -CH(CH ₃ )-, -CH ₂ - and substituted or not Substituted dicyclopentadienyl; Ar is selected from substituted or unsubstituted benzene, biphenyl, naphthalene, phenolic, bisphenol A, bisphenol A phenol, bisphenol F and bisphenol F phenolic; n is An integer greater than or equal to 1; Y is an aliphatic functional group or an aromatic functional group. The resin composition according to claim 1, wherein the polyphenylene ether resin is selected from at least one of the following groups: Wherein X ₆ is selected from the group consisting of a covalent bond, -SO ₂ -, -C(CH ₃ ) ₂ -, -CH(CH ₃ )-, -CH ₂ -; Z ₁ to Z ₁₂ are each independently selected from the group consisting of hydrogen and W is a hydroxyl group, a vinyl group, a styryl group, a propenyl group, a butenyl group, a butadienyl group or an epoxy functional group; and n is an integer greater than or equal to 1. The resin composition according to claim 1, further comprising at least one flame retardant compound selected from the group consisting of bisphenol biphenyl phosphate, ammonium polyphosphate, hydroquinone-double -(diphenylphosphate), bisphenol A-bis-(diphenylphosphate), tris(2-carboxyethyl)phosphine, tris(isopropylchloro)phosphate, trimethylphosphate, two Methyl-methyl phosphate, resorcinol bis-xylyl phosphate, melamine polyphosphate, phosphorus-nitrogen compound, azo-phosphorus compound, 9,10-dihydro-9-oxa-10-phosphanthene- 10-oxide and its derivatives or resins, melamine cyanurate and tris-hydroxyethyl isocyanurate. The resin composition according to claim 1, further comprising at least one compound selected from the group consisting of: an epoxy resin, a phenol resin, a phenol resin, a styrene resin, and a polybutylene. A diene resin, an acid anhydride crosslinking agent, and an amine based crosslinking agent. The resin composition according to claim 1, further comprising at least one additive selected from the group consisting of an inorganic filler, an interfacial active agent, a toughening agent, a hardening accelerator, and a solvent. The resin composition according to any one of claims 1 to 6, which has a dielectric constant of less than 3.5 at a frequency of one billion Hz and a dielectric loss of less than 0.005. The resin composition according to any one of claims 1 to 6, wherein the oxynitride compound and the polyphenylene ether resin are each 1 to 1000 parts by weight based on 100 parts by weight of the cyanate resin. And 5 to 1000 parts by weight. A semi-cured film comprising the resin composition according to any one of claims 1 to 8, wherein the resin composition is formed into a semi-cured state by heating. The semi-cured film of claim 9, further comprising a glass fiber cloth coated with a semi-cured resin composition. A laminate comprising at least one metal foil laminate and at least one insulating layer cured by the semi-cured film of any one of claims 9 to 10. A circuit board comprising at least one laminate as described in claim 11 of the patent application.