Flame-retardant resin composition and article produced therefrom

Abstract

(a) A free-radical polymerizable monomer or oligomer; and (b) 4-vinylbenzyldiphenylphosphine oxide represented by formula (I), a flame-retardant halogen-free resin composition containing the same, wherein the composition does not contain a maleimide resin is provided herein. Also provided is an article that can be made from this composition, and this article can be a prepreg, resin film, laminate, or printed circuit board. The article has a low dielectric loss at very high frequencies. 【Chemical 1】 TIFF2025523233000011.tif82168

Description

Technical Field

[0001] The present invention relates to a resin composition, and more specifically, to a flame-retardant resin composition used in the field of electronics, which has low dielectric loss, high Tg, and high heat resistance.

Background Art

[0002] With the popularization of 5G communication technology, electronic products are being improved day by day, and higher data transmission speeds and higher system operating frequencies are required. At the same time, lead-free soldering requires materials that are resistant to higher temperatures. To meet higher requirements, high-frequency, high-speed, low-loss, high-Tg copper-clad laminates need to meet the basic conditions for such applications.

[0003] The epoxy phenolic resin system commonly used in copper-clad laminates (CCL) has high dielectric loss and is limited in application in the fields of high frequency and high speed. Many of the resins developed as alternatives to the epoxy system are more flammable than the epoxy system, and in order to meet the requirements of electronic communication technology, it is necessary to use a very efficient flame retardant. Many of such flame retardants have an adverse effect on electrical properties.

[0004] For example, polyphenylene oxide (PPO) resin is widely used in the production of copper-clad laminates with low dielectric constant. However, copper-clad laminates made only of PPO resin have a low glass transition temperature (Tg), and also, since PPO resin has low compatibility with other resins, it has a high coefficient of thermal expansion and poor heat resistance. As a result, polyphenylene oxide resin alone cannot meet the requirements of new-generation high-frequency and low-dielectric-constant circuit boards.

[0005] An object of the present invention is to provide a flame retardant that is compatible with PPO resin, maintains a high thermal stability with a decomposition start temperature exceeding 370 °C while providing a composition having a Df of less than 0.003 and a Dk of less than 2.8 at a very high frequency of 80 GHz.

[0006] Bismaleimide has been introduced for the purpose of reducing the coefficient of thermal expansion in resin systems and enhancing heat resistance. However, as a result of this solution, the dielectric properties of the resin deteriorated. Therefore, vinyl-terminated PPO has been used to chemically bond with resins such as polybutadiene, SBR rubber, or C5 aliphatic resin. This eliminated the compatibility problem. The low Tg has been addressed by using crosslinking agents such as triallyl isocyanurate.

[0007] The problem is that such resin combinations have very high flammability. Finding a flame retardant that is compatible with such crosslinked resins and does not deteriorate the electrical properties and thermal stability is a difficult problem. Additive flame retardants must have a very high melting point so as not to lower the Tg. Also, they must be easily dispersible in the varnish. To disperse a high melting point additive flame retardant well in the varnish, grinding is necessary. This operation aims to make the particle size less than a few microns. Such fine grinding requires specially designed and expensive equipment and involves loss of the ground product. On the other hand, reactive flame retardants can be uniformly dispersed in the resin, so the problem of dispersibility does not occur. Finding a compound that does not adversely affect the electrical properties, Tg, and thermal stability is a major challenge. Furthermore, the compatibility between the flame retardant and other varnish components is equally important.

[0008] Therefore, it is necessary to develop a material for copper-clad laminates that overcomes most of the aforementioned technical problems.

Summary of the Invention

[0009] (Summary of the Invention) The present invention belongs to the technical field of laminates and relates to a thermosetting resin composition, a prepreg, and a copper-clad laminate using the thermosetting resin composition.

[0010] This specification includes (a) a free-radical polymerizable monomer or oligomer; and (b) Formula (I):

Chemical formula

[0011] Also provided herein is a process for making a laminate comprising the composition described herein, the process comprising impregnating the composition into a filler to form a prepreg, then treating the prepreg at a high temperature to promote partial curing to the B-stage, and then laminating two or more of the prepregs under high temperature and high pressure to form a laminate. The laminate has a low dielectric loss at very high frequencies.

[0012] (Detailed Description of the Invention) Herein, the inventors have found that 4-vinylbenzyldiphenylphosphine oxide shown in the structure of formula (I) above is involved in the curing process together with a free radical polymerizable monomer or oligomer (a), most preferably vinyl-terminated PPO in an amount of at least 40% by weight. This curing process produces a composition having an unexpectedly low Df at high frequencies such as 80 GHz. 4-Vinylbenzyldiphenylphosphine oxide does not need to have a high melting point because it is incorporated into the vinyl-terminated PPO resin during the curing process.

[0013] In the present invention, 4-vinylbenzyldiphenylphosphine oxide is added to a varnish and co-cured with the free radical polymerizable monomer or oligomer described herein. As a result, a resin composition is obtained which is a composite material having a low coefficient of thermal expansion, high heat resistance, high glass transition temperature, a low dielectric constant of 2.72 or less at 80 GHz, and an unexpectedly low dielectric tangent of 0.0022 at 80 GHz.

[0014] It is understood herein that all ranges herein include all sub-ranges therebetween and any combination of the endpoints of said ranges.

[0015] Unless otherwise specified, all weight percentages in this specification are based on the total weight of the reaction components.

[0016] Unless otherwise specified, all temperatures in this specification are at room temperature.

[0017] All viscosity measurements described in this specification are carried out at 25 °C using a Brookfield capillary viscometer. All pressures shown in this specification are 1 atmosphere at sea level and 25 °C, unless otherwise specified.

[0018] The free-radically polymerizable monomer or oligomer (a) described in this specification contains one or more unsaturated bonds per molecule. Unless otherwise specified, the unsaturated bonds of the free-radically polymerizable monomer or oligomer (a) are reactive unsaturated bonds, for example, double bonds that have the potential to crosslink with other functional groups, for example, unsaturated carbon-carbon double bonds that have the potential to crosslink with other functional groups, but are not limited thereto.

[0019] In one embodiment, the free-radically polymerizable monomer or oligomer comprises a vinyl-terminated polyphenylene ether resin. The vinyl-terminated PPO resin is capped with vinyl groups at both ends. Examples of the vinyl-terminated polyphenylene ether resin include vinylbenzyl-terminated polyphenylene ether resin (e.g., OPE-2st available from Mitsubishi Gas Chemical Company, Inc.), methacrylate-terminated polyphenylene ether resin (e.g., SA9000 available from Sabic), vinylbenzyl-modified bisphenol A polyphenylene ether resin, vinyl-containing chain-extended polyphenylene ether resin, or combinations thereof, but are not limited thereto. For example, the vinyl-terminated polyphenylene ether resin can be added to 4-vinylbenzyldiphenylphosphine oxide represented by formula (I) in any ratio as described above.

[0020] Most preferably, the free-radically polymerizable monomer or oligomer (a) described in this specification can contain vinyl-terminated PPO in an amount of at least 40% by weight.

[0021] In addition to vinyl-terminated PPO in an amount of at least 40% by weight, the free-radically polymerizable monomer or oligomer (a) described herein may further contain other components as described hereinbelow.

[0022] In one embodiment of the present specification, the free-radically polymerizable monomer or oligomer (a) may further contain a vinyl group or an allyl group, preferably an alkene monomer or a diene monomer or an alkene oligomer or a diene oligomer. More preferably, the free-radically polymerizable monomer or oligomer is selected from the group consisting of vinyl-containing compounds, allyl-containing compounds, acrylate resins, polyolefins, and combinations thereof.

[0023] More preferably, the free-radical polymerizable monomer or oligomer may further be selected from the group consisting of styrene, t-butylstyrene, divinylbenzene, bis(vinylbenzyl) ether, bis(vinylphenyl)ethane, 1,2,4-trivinylcyclohexane, vinyl-terminated polyphenylene ether resin, vinylbenzyl-terminated polyphenylene ether resin, methacrylate-terminated polyphenylene ether resin, vinylbenzyl-modified bisphenol A polyphenylene ether resin, polybutadiene, isoprene, polyisoprene, piperylene, trans-1,3-pentadiene, cis-1,3-pentadiene, 2-methyl-2-butene, dicyclopentadiene, cyclopentadiene, cyclopentene, triallyl isocyanurate, triallyl cyanurate, diallyl bisphenol A, allyl-modified tetramethylbiphenol, allyl-containing novolak resin, allyl-containing dicycloisoprene novolak resin, dodecyl methacrylate, octadecyl methacrylate, 2-phenoxyethyl methacrylate, tricyclodecane dimethanol diacrylate, tricyclodecane di(meth)acrylate, 1,1-dodecanediol dimethacrylate, trimethylolpropane trimethacrylate, styrene-butadiene-divinylbenzene terpolymer, vinyl-polybutadiene-urethane oligomer, styrene-butadiene copolymer, hydrogenated styrene-butadiene copolymer, styrene-isoprene copolymer, polybutadiene, methylstyrene copolymer, styrene-ethylene copolymer, styrene-propylene copolymer, styrene-butadiene-isoprene terpolymer, hydrogenated styrene-butadiene terpolymer, hydrogenated styrene-isoprene copolymer, hydrogenated styrene-butadiene-isoprene terpolymer, and combinations thereof.

[0024] According to the present disclosure, the type of the free-radical polymerizable monomer or oligomer resin is not particularly limited as long as it contains 40% by weight of vinyl-terminated PPO, and may include a low-molecular vinyl-containing compound, an allyl-containing compound, an acrylate resin, a polyolefin, or a combination thereof.

[0025] In one embodiment, the free radical polymerizable monomer or oligomer includes a low molecular weight vinyl-containing compound. As used herein, the low molecular weight vinyl-containing compound refers to a vinyl-containing compound having a molecular weight of 1,000 or less, preferably 100 to 900, more preferably 100 to 800. According to the present disclosure, the low molecular weight vinyl-containing compound may include, but is not limited to, divinylbenzene (DVB), bis(vinylbenzyl) ether (BVBE), bis(vinylphenyl) ethane (BVPE), 1,2,4-trivinylcyclohexane (TVCH), or combinations thereof.

[0026] In one embodiment, the free radical polymerizable monomer or oligomer includes an allyl-containing compound. The allyl-containing compound is a compound having an allyl group and is not particularly limited. Preferably, it is an allyl-containing resin having two or more allyl groups per molecule. Further, the allyl-containing resin may have other functional groups such as an epoxy group or a hydroxyl group. Examples of the allyl-containing compound include, but are not limited to, triallyl isocyanurate (TAIC), triallyl cyanurate (TAC), diallyl bisphenol A, allyl-modified tetramethylbiphenol, allyl-containing novolak resin, allyl-containing dicycloisoprene novolak resin, or combinations thereof. Preferably, the allyl-containing compound includes allyl-modified tetramethylbiphenol, allyl-containing dicycloisoprene novolak resin, or combinations thereof.

[0027] In one embodiment, the free radical polymerizable monomer or oligomer includes an acrylate resin. The acrylate resin may include, but is not limited to, a monofunctional acrylate resin, a difunctional acrylate resin, or a trifunctional acrylate resin. For example, the monofunctional acrylate resin may include, but is not limited to, dodecyl methacrylate, octadecyl methacrylate, 2-phenoxyethyl methacrylate, or combinations thereof. The difunctional acrylate resin may include, but is not limited to, tricyclodecane dimethanol diacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, 1,12-dodecanediol dimethacrylate, or combinations thereof. The trifunctional acrylate resin may include trimethylolpropane trimethacrylate.

[0028] For example, the monofunctional acrylate resin may be a monofunctional long-chain alkyl acrylate sold under the trade names SR313A, SR313B, SR313NS, SR324NS, SR335, and SR489D from Sartomer. For example, the difunctional acrylate resin may be a difunctional acrylate sold under the trade names SR-833S, SR-238NS, SR-239, and SR-262 from Sartomer. For example, the trifunctional acrylate resin may be a trifunctional acrylate sold under the trade name SR-350NS from Sartomer.

[0029] In one embodiment, the free radical polymerizable monomer or oligomer includes a polyolefin. Examples of the polyolefin include polymers having one or more monomers selected from ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 4-methyl-1-pentene, 1-octene, 1-decene, etc., or random polypropylene, ethylene-ethyl acrylate copolymer, etc., but are not limited thereto. Examples include styrene-butadiene-divinylbenzene terpolymer, styrene-butadiene-maleic anhydride terpolymer, vinyl-polybutadiene-urethane oligomer, styrene-butadiene copolymer, styrene-isoprene copolymer, polybutadiene (homopolymer of butadiene), maleic anhydride-butadiene copolymer, methylstyrene copolymer, styrene-ethylene copolymer, styrene-propylene copolymer, styrene-butadiene-isoprene terpolymer, or combinations thereof.

[0030] Preferably, the polyolefin includes a polyolefin having an elongation rate (elongation %) of 500% or more. For example, D-1117, D-1118, G-1652, G-1701, G-1702, G-1750, G-1765, G-1780, etc. are included, but are not limited thereto. Further, the polyolefin preferably has an elongation rate in the range of 500% to 1,500%.

[0031] The free radical polymerizable monomer or oligomer (a) and 4-vinylbenzyldiphenylphosphine oxide (b) represented by formula (I) can be present in any ratio. For example, the free radical polymerizable monomer or oligomer can be present in the composition in an amount of 40 to about 95% by weight, preferably about 55 to about 90% by weight, most preferably about 65 to about 85% by weight, and the 4-vinylbenzyldiphenylphosphine oxide represented by formula (I) can be present in an amount of 5 to about 60% by weight, preferably about 10 to about 45% by weight, most preferably about 15 to about 35% by weight.

[0032] In one embodiment, the composition according to the present disclosure may further optionally include, but is not limited to, an epoxy resin, an amine curing agent, a phenolic curing agent, an anhydride curing agent, a benzoxazine resin, a cyanate ester resin, or any combination thereof.

[0033] Also, the composition according to the present disclosure may further optionally include an inorganic filler, a curing accelerator, a solvent, a silane coupling agent, a colorant, or a combination thereof.

[0034] In one embodiment of the present disclosure, the composition may further optionally include an inorganic filler, a curing accelerator, a solvent, a molecular weight regulator, a polymerization inhibitor, a reinforcing agent, a coupling agent, or a combination thereof. Unless otherwise specified, based on 100 parts by weight in total of the free radical polymerizable monomer or oligomer and the additives, the content of the component may be 1 to 200 parts by weight, for example, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 150, or 200 parts by weight.

[0035] For example, the composition of the present disclosure may further contain an inorganic filler to enhance the dimensional stability of an article made from the resin composition. The inorganic filler may be any inorganic filler known in the field related to the present disclosure. Examples include, but are not limited to, silica (fused type, non-fused type, porous type, or hollow type), aluminum oxide, aluminum hydroxide, magnesium oxide, magnesium hydroxide, calcium carbonate, aluminum nitride, boron nitride, aluminum silicon carbide, silicon carbide, titanium dioxide, zinc oxide, zirconium oxide, mica, boehmite (AlOOH), calcined talc, talc, silicon nitride, calcined kaolin, or a combination thereof. Further, the inorganic filler may be spherical, fibrous, plate-like, particulate, sheet-like, or whisker-like and may optionally be pretreated with a silane coupling agent.

[0036] For example, the composition of the present disclosure may further include a curing accelerator to enhance the reactivity of the components in the composition. The curing accelerator (including a curing initiator) may be any curing accelerator known in the field related to the present disclosure, and examples include, but are not limited to, catalysts such as Lewis bases, Lewis acids, or combinations thereof. The Lewis base may include any one or more of imidazole, boron trifluoride-amine complex, ethyltriphenylphosphonium chloride, 2-methylimidazole (2MI), 2-phenyl-1H-imidazole (2PZ), 2-ethyl-4-methylimidazole (2E4MI), triphenylphosphine (TPP), and 4-dimethylaminopyridine (DMAP). The Lewis acid may include a metal salt compound (salts of metals such as manganese, iron, cobalt, nickel, copper, and zinc), for example, zinc octoate, or cobalt octoate, etc. The curing accelerator also includes a curing initiator such as a peroxide capable of generating free radicals. Examples of the curing initiator include, but are not limited to, dicumyl peroxide, tert-butyl peroxybenzoate, dibenzoyl peroxide, 2,5-dimethyl-2,5-di(tert-butylperoxy)-3-hexyne, bis(tert-butylperoxyisopropyl)benzene, or combinations thereof.

[0037] For example, the composition of the present disclosure may further include a solvent to adjust the viscosity of the varnish formed therefrom. Examples of the solvent include, but are not limited to, methanol, ethanol, ethylene glycol monomethyl ether, acetone, butanone (methyl ethyl ketone), methyl isobutyl ketone, cyclohexanone, toluene, xylene, methoxyethyl acetate, ethoxyethyl acetate, propoxyethyl acetate, ethyl acetate, dimethylformamide, dimethylacetamide, propylene glycol methyl ether, or mixtures thereof.

[0038] For example, the composition of the present disclosure may further include a silane coupling agent to promote the dispersion of the inorganic filler. The silane coupling agent may include silane (such as siloxane, but not limited thereto), and depending on the functional group, it can be further classified into aminosilane, epoxidesilane, vinylsilane, acrylatesilane, methacrylatesilane, hydroxylsilane, isocyanatesilane, methacryloxy silane, and acryloxy silane.

[0039] The composition according to the present disclosure can be processed to produce various articles including, but not limited to, prepregs, resin films, laminates, or printed circuit boards.

[0040] For example, a resin film can be produced using the present composition by coating the composition on a carrier and then heating and baking to semi-cure the composition. The carrier may include a polyethylene terephthalate film (PET film), a polyimide film (PI film), a copper foil, or a resin-coated copper (RCC). For example, the composition can be selectively coated on a polyethylene terephthalate film (PET film), a polyimide film (PI film), a copper foil, or a resin-coated copper (RCC), and then heated and baked to semi-cure the composition to form a resin film.

[0041] For example, the composition can be used to produce a laminate including two metal foils and an insulating layer disposed between the metal foils. Here, the insulating layer is produced by curing a phosphorus-containing resin composition to the C stage under high temperature and high pressure. The suitable curing temperature is, for example, 150°C to 220°C, preferably 190°C to 210°C, and the suitable curing time is 90 to 180 minutes, preferably 90 to 150 minutes. The insulating layer can be obtained by curing the prepreg or the resin film. The metal foil may include copper, aluminum, nickel, platinum, silver, gold, or their alloys, and an example is a copper foil. For example, the laminate can be a copper-clad laminate (CCL).

[0042] Furthermore, the laminate can be further processed by a trace forming process to provide a printed circuit board (also known as a circuit board).

[0043] Generally, the composition according to the present disclosure or an article made from the composition can achieve one or more of the following features.

[0044] An article made from the composition disclosed herein has the following properties: The glass transition temperature measured using a dynamic mechanical analyzer with reference to IPC-TM-650 2.4.24.4 is 216 °C or higher, for example, 216 °C to 240 °C or 220 °C to 230 °C; the coefficient of thermal expansion in the Z-axis direction measured using a thermomechanical analyzer with reference to IPC-TM-650 2.4.24.5 is 2.70% or less, for example, 2.20% to 2.70%; the copper foil peel strength measured using a tensile strength tester with reference to IPC-TM-650 2.4.8 is 3.0 lb / in or more, for example, 3.0 lb / in to 3.8 lb / in; no delamination occurs after measurement after 5 hours of moisture absorption with reference to IPC-TM-650 2.6.16.1 and then a solder dipping test with reference to IPC-TM-650 2.4.23; the dielectric tangent is 0.0030 or less at 80 GHz when measured with reference to JIS C2565; the dielectric constant is 3.10 or less, for example, 2.50 to 3.10, or 3.05 to 3.10 when measured with reference to JIS C2565; the tack resistance measured by visually inspecting the tackiness of a plurality of prepregs vacuum-packed in an aluminum foil bag and stored at a constant temperature of 35 °C for 48 hours is good (no tackiness between prepregs); and the storage period of the varnish made from the resin composition measured from the resin composition left standing at 5 to 35 °C and visually inspected for precipitation, turbidity, or layer separation is 1 day or more (no precipitation, turbidity, or layer separation after 1 day), for example, 2 days, 3 days, 5 days, 7 days, 9 days, 11 days, or 15 days or more. It may have at least one, preferably at least two, more, or all of them.

[0045] Most preferably, the composition comprises 40 to 80 parts by weight of vinyl-terminated PPO; and 10 to 50 parts by weight of polybutadiene and 1 to 15 parts by weight of triallyl isocyanurate, wherein the flame retardant is 4-vinylbenzyldiphenylphosphine oxide, the PPO resin is SA9000 from Sabic, and the polybutadiene is a liquid resin having a number average of less than 5000, a minimum vinyl content of 20%, a viscosity of less than 2000 poise at 45 °C, and a Li ion content of less than 100 ppm.

Example

[0046]

Chemical formula

[0047] Performance examples are shown in Table 1 below. The compounding components were mixed at the ratios shown in Table 1, B-staged at 150 °C for 3 minutes, pulverized, cured at 175 °C for 2 hours, and then cured at 190 °C for 1 hour.

[0048]

Table 1

[0049] Preparation of samples: Samples of the FR compound were combined with the PPE resin SA9000, the crosslinking agent B-1000 and TAIC and cured on a small scale. The composition of the small-scale samples is shown in Table 1 above. The total P% (Total%P) was approximately 2.4%. Toluene was used as the solvent. The samples were cured at 175 °C for 2 hours and post-cured at 190 °C for 1 hour. The thermal stability of the samples was investigated using DSC and TGA.

[0050]

Table 2

[0051] Surprisingly, the preparation of a uniform film using the compounds of Comparative Example 1 and Comparative Example 2 was difficult as seen above, while the preparation of a film using the compound of Example 1 was easy and a very uniform film was formed.

[0052]

Table 3

[0053]

Chemical formula

[0054]

Chemical formula

[0055]

Chemical formula

[0056] The present invention has been described with reference to specific means, materials and embodiments. However, from the foregoing description, those skilled in the art can easily grasp the essential features of the present invention and can make various changes and modifications to adapt to various uses and characteristics without departing from the spirit and scope of the present invention described above.

Claims

1. (a) A free-radically polymerizable monomer or oligomer; and (b) 4-Vinylbenzyldiphenylphosphine oxide represented by formula (I): 【Chemical 1】 A composition containing the compound, wherein the composition does not contain a maleimide resin.

2. The composition according to claim 1, wherein the free-radically polymerizable monomer or oligomer has a vinyl group or an allyl group.

3. The composition according to claim 1, wherein the free-radically polymerizable monomer or oligomer is an alkene monomer or a diene monomer or an alkene oligomer or a diene oligomer.

4. The composition according to claim 1, wherein the free-radically polymerizable monomer or oligomer contains at least 40 weight percent vinyl-terminated PPO.

5. The composition according to claim 4, wherein the free-radically polymerizable monomer or oligomer further contains a further component selected from the group consisting of vinyl-containing compounds, allyl-containing compounds, acrylate resins, polyolefins, and combinations thereof.

6. ​ The free radical polymerizable monomer or oligomer is styrene, t-butylstyrene, divinylbenzene, bis(vinylbenzyl) ether, bis(vinylphenyl) ethane, 1,2,4-trivinylcyclohexane, polybutadiene, isoprene, polyisoprene, piperylene, trans-1,3-pentadiene, cis-1,3-pentadiene, 2-methyl-2-butene, dicyclopentadiene, cyclopentadiene, cyclopentene, triallyl isocyanurate, triallyl cyanurate, diallyl bisphenol A, allyl-modified tetramethylbiphenol, allyl-containing novolak resin, allyl-containing dicycloisoprene novolak resin, dodecyl methacrylate, octadecyl methacrylate, 2-phenoxyethyl methacrylate, tricyclodecane dimethanol diacrylate, tricyclodecane di(meth)acrylate, 1,1-dodecanediol dimethacrylate, trimethylolpropane trimethacrylate, styrene-butadiene-divinylbenzene terpolymer, vinyl-polybutadiene-urethane oligomer, styrene-butadiene copolymer, hydrogenated styrene-butadiene copolymer, styrene-isoprene copolymer, polybutadiene, methylstyrene copolymer, styrene-ethylene copolymer, styrene-propylene copolymer, styrene-butadiene-isoprene terpolymer, hydrogenated styrene-butadiene terpolymer, hydrogenated styrene-isoprene copolymer, hydrogenated styrene-butadiene-isoprene terpolymer, and combinations thereof, and further comprises a further component selected from the group consisting of: the composition according to claim 4.

7. The composition according to claim 1, further comprising at least one of a flame retardant, an inorganic filler, a curing accelerator, a solvent, a molecular weight regulator, a polymerization inhibitor, a reinforcing agent, a coupling agent, or combinations thereof.

8. The composition according to claim 1, which is cured.

9. Any one coating formulation, encapsulant, composite material, adhesive, molded article, bonding sheet, or laminate comprising the composition according to claim 1.

10. An article comprising the composition according to claim 1.

11. The article according to claim 10, which can be used in lead-free soldering applications and electronic devices.

12. The article according to claim 10, further comprising a copper foil.

13. The article according to claim 10, which is a printed circuit board.

14. A prepreg comprising the composition of claim 1.

15. The prepreg according to claim 14, having a dielectric loss of 0.0030 or less at 80 GHz, a glass transition temperature of 180 °C or higher, and a thermal stability shown as a weight loss rate of 5% or less at 370 °C or higher in TGA.

16. A laminate or bonding sheet comprising the composition of claim 1.

17. A printed wiring board comprising the prepreg according to claim 14.

18. A printed wiring board comprising the prepreg according to claim 14, having a dielectric loss of 0.0025 or less at 80 GHz, a glass transition temperature of 180 °C or higher, and a thermal stability shown as a weight loss rate of 5% or less at 370 °C or higher in TGA.

19. A printed wiring board comprising the laminate according to claim 16.

20. A method for manufacturing a laminate comprising the composition of claim 1, comprising: impregnating the composition into a filler to form a prepreg, then treating the prepreg at a high temperature to promote partial curing to the B-stage, and then laminating two or more of the prepregs under high pressure and high temperature to form a laminate. A method comprising the above steps.

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