Hardened siloxane resin composition

Abstract

To provide a curable siloxane composition that is suitable for printed circuit boards for high-frequency communication electronic devices and features low dielectric constant and dielectric loss in the high-frequency range, low water absorption, superior machinability, and high copper foil peel strength.SOLUTION: A curable siloxane composition includes organic alkoxysilanes having an asymmetric structure with respect to silicon, and organic alkoxysilanes having a symmetric structure with respect to silicon.SELECTED DRAWING: None

Description

Technical Field

[0001] Provided are a curable siloxane resin composition having a low dielectric constant and a low dielectric loss, and a method for producing the same.

Background Art

[0002] Recently, with the development of electronic communication technologies such as smartphones, Internet of Things (IoT), augmented reality (AR), virtual reality (VR), and autonomous vehicles, the organic interaction between electronic devices has gradually increased, making high-speed transmission and reception of large-capacity data important. Therefore, the frequency bands used for ultra-high-speed data transfer have been extended from extremely ultra-high frequency (UHF, 300 - 3000 MHz) to super-high frequency (SHF, 3 - 30 GHz) and extremely high frequency (EHF, 30 - 300 GHz). However, in the case of the epoxy composite (FR-4) used in the printed circuit boards of existing communication electronic devices, it is not suitable for use in high-frequency communication as it has a high dielectric constant and a high dielectric loss. Also, as the frequency increases, the loss during the transmission of electrical signals increases rapidly. Therefore, the development of a substrate material having a low dielectric constant and a low dielectric loss and a printed circuit board using the same is essential and required.

[0003] To date, many materials such as polyimide resins, fluorine-based polymer resins, and liquid crystalline polymer resins have been proposed for application to printed circuit boards for high-frequency communication electronic devices, but their properties still do not fully meet the requirements. For example, polyimide films are not suitable for application to printed circuit boards for high-frequency communication electronic devices due to their high moisture absorption rate, dielectric constant, and dielectric loss. To overcome this, International Publication Patent 2019-221343 and US Registered Patent 10299378 formed fine pores inside the polyimide film in different ways to ensure a low dielectric constant, but there are no specific embodiments for dielectric loss, so the compatibility as a material for printed circuit boards for high-frequency communication electronic devices cannot be determined.

[0004] As another example, fluorine-based polymer resins have low dielectric constant and dielectric loss in the high-frequency region, but have low copper foil peel strength and are difficult to apply to printed circuit boards. Therefore, in order to increase the copper foil peel strength, International Publication Patent 2020-138642 adjusted the content of resins formed by mixing fluorine-based elastomers and styrene-based elastomers and inorganic and organic fillers, but no specific examples thereof were presented, and the compatibility as a material for printed circuit boards for high-frequency communication electronic devices could not be determined.

[0005] Liquid crystalline polymer resins also have low dielectric constant and dielectric loss, but have low copper foil peel strength and are difficult to apply to printed circuit boards. Therefore, in U.S. Registered Patent 10765001, the surface roughness of the liquid crystalline polymer and the copper foil was unevenly formed to increase the copper foil peel strength. However, not only does it require an additional processing process to make the surface roughness uneven, but when the surface roughness of the copper foil is uneven, the surface resistance may increase and the data processing speed may be significantly reduced, making it unsuitable as a material for printed circuit boards for high-frequency communication electronic devices.

[0006] In addition to the materials described above, many materials such as the polyphenylene ether resin composition proposed in U.S. Registered Patent 10645806 and the epoxy resin composition proposed in U.S. Published Patent 2020-0115554 have been proposed as materials for printed circuit boards for high-frequency communication electronic devices, but they are not suitable due to high dielectric constant and dielectric loss.

[0007] Therefore, considering such characteristics, it is difficult to apply only the materials proposed so far to printed circuit boards for high-frequency communication electronic devices. Therefore, there is a need to develop a new substrate material with low dielectric constant and low dielectric loss for high-frequency communication electronic devices that meets these requirements.

Prior Art Documents

Patent Documents

[0008]

Patent Document 1

Patent Document 2

[0009] An object of one embodiment is to provide a curable siloxane resin composition having low dielectric constant, low dielectric loss, and low hygroscopicity, which has physical properties suitable for application to printed circuit boards for high - frequency communication electronic devices.

[0010] Embodiments according to the present invention can be used to achieve other problems not specifically mentioned in addition to the above problems. [Means for Solving the Problems]

[0011] One embodiment provides a curable siloxane resin composition in which an organoalkoxysilane having an asymmetric structure based on silicon and an organoalkoxysilane having a symmetric structure based on silicon are mixed to produce a siloxane resin.

[0012] Also, one embodiment provides a cured product of a siloxane resin composition produced through heat treatment of a curable siloxane resin composition

[0013] Also, one embodiment provides a glass fiber reinforced plastic (GFRP) film or sheet containing glass cloth in a cured product of a curable siloxane resin composition.

[0014] In addition, one embodiment provides a copper clad laminate (CCL) or a flexible copper clad laminate (FCCL) including a glass fiber reinforced plastic film or sheet.

[0015] In addition, one embodiment provides a printed circuit board (PCB) or a flexible printed circuit board (FPCB) including a copper clad laminate or a flexible copper clad laminate.

Advantages of the Invention

[0016] The curable siloxane resin composition according to one embodiment has low dielectric constant and dielectric loss in the high frequency region, low water absorption, excellent processability, and high copper foil peel strength, and thus can provide physical properties suitable for application to printed circuit boards for high frequency communication electronic devices.

Embodiments for Carrying Out the Invention

[0017] Examples of the present invention will be described in detail so that those having ordinary knowledge in the technical field to which the present invention pertains can easily implement the present invention. The present invention can be embodied in various different forms and is not limited to the embodiments described herein. In the case of well-known publicly known technologies, specific descriptions thereof will be omitted.

[0018] Throughout the specification, when a part includes a certain component, this means that other components can be further included, rather than excluding other components, unless otherwise stated to the contrary.

[0019] Throughout the specification, the term "these combinations" included in the Markush-form expression means one or more mixtures or combinations selected from the group consisting of the components described in the Markush-form expression, and means including one or more selected from the group consisting of the components.

[0020] Throughout the specification, the term "alkyl group" can each independently include a linear or branched C1-7 alkyl group or a C1-20 alkyl group, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosanyl, or all possible isomers thereof, but may not be limited thereto.

[0021] Throughout the specification, the term "alkenyl group" means a monovalent hydrocarbon group in which at least one carbon-carbon double bond is included in an alkyl group having 2 or more carbon atoms, and can include a linear or branched C2-20 alkenyl group, but may not be limited thereto.

[0022] Throughout the specification, the term "aryl group" means a monovalent functional group formed by removing a hydrogen atom present in one or more rings of an arene, and can include a C6-20 aryl group, for example, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, or all possible isomers thereof, but may not be limited thereto. An arene is a hydrocarbon group having an aromatic ring, including a monocyclic or polycyclic hydrocarbon group, and the polycyclic hydrocarbon group can include one or more aromatic rings, and may include an aromatic ring or a non-aromatic ring as an additional ring, but may not be limited thereto.

[0023] Throughout the specification, the term "alkoxy group or alkoxy" refers to a form in which an alkyl group is bonded to an oxygen atom, and may include a C1-20 alkoxy group. For example, it may include, but is not limited to, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy, eicosanyloxy, or all possible isomers thereof.

[0024] Throughout the specification, the term "siloxane resin composition" means a composition containing raw materials for producing a siloxane resin or a composition containing a siloxane resin.

[0025] Throughout the specification, the copper-clad laminate can include all rigid copper-clad laminates or flexible copper-clad laminates.

[0026] Throughout the specification, the printed circuit board can include all rigid printed circuit boards or flexible printed circuit boards.

[0027] Hereinafter, a curable siloxane resin composition according to an embodiment will be described in detail.

[0028] One embodiment is a siloxane resin composition in which an organoalkoxysilane having an asymmetric structure based on silicon and an organoalkoxysilane having a symmetric structure based on silicon are mixed to produce a siloxane resin.

[0029] The organoalkoxysilane having a symmetric structure based on silicon acts as an important element having dielectric properties suitable for application to printed circuit boards for electronic devices.

[0030] More specifically, when the molecular structure of the entire polymer has a high degree of symmetry based on the main chain in the high-frequency region, the polarization rate of the entire polymer decreases and the dipole moment decreases. Therefore, it is advantageous to have characteristics of low dielectric constant and low dielectric loss. Further, when the dipole moment of the side chain itself that is symmetric with respect to the main chain is small, the polarization rate of the entire polymer decreases and the dipole moment decreases. Therefore, it is advantageous to have characteristics of low dielectric constant and low dielectric loss.

[0031] For example, when the molar amount of the organoalkoxysilane having a symmetric structure based on silicon is smaller than that of the organoalkoxysilane having an asymmetric structure based on silicon, dielectric properties suitable for application to a printed circuit board for high-frequency communication electronic devices cannot be obtained. Further, among organoalkoxysilanes having a symmetric structure based on silicon, the larger the molar amount of the organosiloxane having a symmetric structure based on silicon containing an aryl group, the lower the dipole moment and the more suitable dielectric properties for application to a printed circuit board for high-frequency communication electronic devices. This is confirmed by the experimental results of Examples and Comparative Examples described later.

[0032] For example, the organoalkoxysiloxane having a symmetric structure based on silicon includes the organoalkoxysiloxane having a symmetric structure based on silicon containing an aryl group, whereby the low dielectric constant and low dielectric loss performance of the siloxane resin can be improved. Further, the organoalkoxysiloxane having a symmetric structure based on silicon can further selectively include the organoalkoxysiloxane having a symmetric structure based on silicon containing an alkyl group. In this case, the low dielectric constant and low dielectric loss performance of the siloxane resin can be further improved. Note that when the organoalkoxysiloxane having a symmetric structure based on silicon containing an aryl group is used more than the organoalkoxysiloxane having a symmetric structure based on silicon containing an alkyl group, the dipole moment decreases and the low dielectric constant and low dielectric loss performance of the siloxane resin can be maximized.

[0033] For example, the first organoalkoxysilane having an asymmetric structure based on silicon can be represented by the following Chemical Formula 1.

[0034] [Chemical Formula 1] R 1 a R 2 b Si(OR 3 )2 In Chemical Formula 1, R 1 contains a linear or branched C 2-20 alkenyl group, R 2 is H, a linear or branched C 1-20 alkyl group, a C 6-20 aryl group, or a C 2-20 alkenyl group, R 3 contains a linear or branched C 1-7 alkyl group, 1 ≦ a ≦ 2, 0 ≦ b ≦ 1, and a + b = 2.

[0035] The first organoalkoxysilane having an asymmetric structure based on silicon can be vinylmethyldimethoxysilane, vinylmethyldiethoxysilane, vinylphenyldimethoxysilane, vinylphenyldiethoxysilane, divinyldimethoxysilane, divinyldiethoxysilane, allyldimethoxysilane, allylmethyldimethoxysilane, allylmethyldiethoxysilane, dimethoxymethyl(4 - vinylphenyl)silane, or can contain one or more of these.

[0036] For example, the second organoalkoxysilane and the third organoalkoxysilane having a symmetric structure based on silicon can be represented by the following Chemical Formula 2 and Chemical Formula 3, respectively.

[0037] [Chemical Formula 2] R 4 2Si(OR 5 )2 In the above Chemical Formula 2, R 4 contains a C 6-20 aryl group, R5 contains a linear or branched C 1-7 alkyl group. [Chemical Formula 3] R 6 2Si(OR 7 )2 In the above Chemical Formula 3, R 6 contains a linear, branched or cyclic C 1-20 alkyl group, R 7 contains a linear or branched C 1-7 alkyl group.

[0038] The second organoalkoxysilane having a symmetric structure based on the silicon represented by the above Chemical Formula 2 may be diphenyldimethoxysilane, diphenyldiethoxysilane, bis(4-methylphenyl)dimethoxysilane, bis(4-methylphenyl)diethoxysilane, bis(o-tolyl)dimethoxysilane, bis(o-tolyl)diethoxysilane, bis(m-tolyl)diethoxysilane, bis(m-tolyl)dimethoxysilane, di(naphthalen-1-yl)dimethoxysilane, di(naphthalen-1-yl)diethoxysilane, or may contain one or more of these.

[0039] The third organoalkoxysilane having a symmetric structure based on the silicon represented by the above Chemical Formula 3 may be dimethyldimethoxysilane, dimethyldiethoxysilane, diisobutyldimethoxysilane, diisobutyldiethoxysilane, diisopropyldimethoxysilane, diisopropyldiethoxysilane, di-n-butyldimethoxysilane, di-n-butyldiethoxysilane, di-n-propyldimethoxysilane, di-n-propyldiethoxysilane, dicyclopentyldimethoxysilane, dicyclopentyldiethoxysilane, or may contain one or more of these.

[0040] A siloxane resin can be produced by hydrolysis and condensation reactions of a first organoalkoxysilane having an asymmetric structure based on silicon, a second organoalkoxysilane having a symmetric structure based on silicon, and a third organoalkoxysilane having a symmetric structure based on silicon. The produced siloxane resin can be represented by the following Chemical Formula 4.

[0041] [Chemical Formula 4] (R 1 a R 2 b SiO) x (R 4 2SiO) y (R 6 2SiO) z In the above Chemical Formula 4, R 1 is a linear or branched C 2-20 alkenyl group, R 2 is H, a linear or branched C 1-20 alkyl group, a C 6-20 aryl group, or a C 2-20 alkenyl group, R 4 is a C 6-20 aryl group, R 6 is a linear, branched or cyclic C 1-20 alkyl group, 1 ≦ a ≦ 2, 0 ≦ b ≦ 1, and a + b = 2, 1 ≦ x, 1 ≦ y, 1 ≦ z, and x ≦ y + z.

[0042] The method for producing a siloxane resin includes the steps of mixing a first organoalkoxysilane having an asymmetric structure based on silicon, a second organoalkoxysilane having a symmetric structure based on silicon, a third organoalkoxysilane having a symmetric structure based on silicon, and an acid or base catalyst to produce a mixture, stirring the mixture to carry out a condensation reaction at 40°C to 300°C, removing the acid or base catalyst, and adding a peroxide radical polymerization initiator. When producing a siloxane resin by the hydrolysis and condensation reaction of an organic alkoxysilane, the dielectric constant and dielectric loss of the siloxane resin composition can be rapidly decreased by obtaining the effect that the degree of condensation of the siloxane resin increases significantly and the rigidity increases. For example, when producing a resin by the non-hydrolytic condensation reaction of an organic alkoxysilane and an organic silanediol, the degree of condensation decreases and the resin has a higher dielectric constant and dielectric loss than the siloxane resin composition. When producing a siloxane resin, it can be carried out by adjusting reaction conditions such as the reaction temperature, reaction atmosphere, amount of water, type and amount of an acid or base catalyst during the hydrolysis and condensation reaction of the organic alkoxysilane.

[0043] The acid catalyst can include hydrochloric acid, sulfuric acid, nitric acid, formic acid, acetic acid, toluenesulfonic acid, butyric acid, palmitic acid, oxalic acid, tartaric acid, or one or more of these.

[0044] The base catalyst can include an alkali metal compound, an alkaline earth metal compound, a quaternary ammonium compound, ammonia, an amine compound, or one or more of these. For example, it can include one or more selected from the group consisting of an alkali metal compound selected from sodium hydroxide, potassium hydroxide, and lithium hydroxide, an alkaline earth metal compound selected from barium hydroxide monohydrate, barium hydroxide octahydrate, calcium hydroxide, and magnesium hydroxide, a quaternary ammonium compound selected from tetraalkylammonium silanolate, tetraethylammonium hydroxide, tetramethylammonium chloride, and tetrabutylammonium fluoride, ammonia, an amine compound, and combinations thereof.

[0045] For example, when producing a siloxane resin through the hydrolysis and condensation reaction of an organic alkoxysilane, a mixture of the organic alkoxysilane, water, an acid or a base catalyst can be stirred at 40 to 300 °C for 2 to 48 hours under a nitrogen atmosphere. At this time, water in the mixture can be contained in a content of 0.5 to 10 moles per 1 mole of the organic alkoxysilane, and the acid or base catalyst can be contained in a content of 0.001 to 0.1 moles per 1 mole of the organic alkoxysilane, but it may not be limited to this.

[0046] When adding an acid and a base catalyst during the hydrolysis-condensation reaction of the organic alkoxysilane, the acid and base catalysts can be removed by commonly known physical or chemical methods, but not limited to this, in order to ensure the electrical stability through the reduction of the moisture absorption rate of the produced siloxane resin.

[0047] The siloxane resin composition can contain an additional crosslinking agent to make its physical properties suitable for a printed circuit board for high-frequency communication electronic devices, but it may not be limited to this.

[0048] The crosslinking agent is vinyltetramethyldisiloxane, vinylpentamethyldisiloxane, 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane, 1,3-divinyltetraphenyldisiloxane, 1,1,3,3-tetravinyldimethyldisiloxane, 1,3-divinyltetraethoxydisiloxane, 1,3-divinyltetrakis(trimethylsiloxy)disiloxane, 1,3-divinyltetramethyldisiloxane, 1,3-diphenyltetrakis(dimethylsiloxy)disiloxane, hexamethyldisiloxane, 1,5-divinyl-3,3-diphenyl-1,1,5,5-tetramethyltrisiloxane, 1,5-divinyl-3-phenylpentamethyltrisiloxane, 1,3,5-trivinyl-1,1,3,5,5-pentamethyltrisiloxane, 2,4,6-trivinyl-2,4,6-trimethylcyclotrisiloxane, 2,4,6,8-tetravinyl-2,4,6,8-Tetramethylcyclotetrasiloxane, octavinyl-T8-silsesquioxane, phenyltris(trimethylsiloxy)silane, phenyltris(dimethylsiloxy)silane, tris(trimethylsiloxy)silane, tris(vinyldimethylsiloxy)methylsilane, tris(vinyldimethylsiloxy)phenylsilane, tris(dimethylsiloxy)silane, divinylbenzene, p-divinylbenzene, vinyldimethylsilane, vinyltrimethylsilane, vinyltriethylsilane, vinyltriphenylsilane, vinyl-t-butyldimethylsilane, vinyl-di-n-octylmethylsilane, vinylphenylmethylsilane, vinylphenyldimethylsilane, divinyldimethylsilane, trivinylsilane, trivinylmethylsilane, tetravinylsilane, vinyldimethylmethoxysilane, vinylphenylmethylmethoxysilane, vinyldimethylethoxysilane, vinyldiphenylethoxysilane, vinylmethyldimethoxysilane, vinylmethyldiethoxysilane, vinylphenyldiethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltriisopropoxysilane, vinyltri-t-butoxysilane, vinyltriisopropenoxysilane, vinyltriphenoxysilane, vinyltris(2-methoxyethoxy)silane, vinyltris(methoxypropoxy)silane, trivinylmethoxysilane, trivinylethoxysilane, vinylmethylbis(trimethylsiloxy)silane, vinyltris(dimethylsiloxy)silane, vinyltris(trimethylsiloxy)silane, tetrakis(vinyldimethylsiloxy)silane, vinylmethyldiacetoxysilane, vinyltriacetoxysilane, 2-propenyltrimethylsilane, (1-methoxyvinyl)trimethylsilane, 1,2-divinyltetramethyldisilane, 1,4-divinyltetramethyldisilylethane, 1,4-bis(vinyldimethylsilyl)benzene, 1-allyl-1,1,3,3-tetramethyldisiloxane, 1,3-diallyltetramethyldisiloxane and 1,3-Diallyltetrakis(trimethylsiloxy)disiloxane, allyldimethylsilane, allyltrimethylsilane, allyltriisopropylsilane, allyltriphenylsilane, diallyldimethylsilane, diallyldiphenylsilane, triallylmethylsilane, tetraallylsilane, allyldimethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, allyltriphenoxysilane, allyltris(trimethylsiloxy)silane, 2,4,6,8-Tetramethylcyclotetrasiloxane, octamethyl-T8-silsesquioxane, 1,1-bis(trimethylsilylmethyl)ethylene, 1,1-bis(trimethoxysilylmethyl)ethylene, methallyltrimethylsilane, diethoxymethylsilane, dimethoxymethylsilane, n-octadecylmethyldiethoxysilane, n-octadecyldimethylethoxysilane, n-octadecyldimethylmethoxysilane, n-octadecylmethyldimethoxysilane, n-octadecyldimethylsilane, n-octylmethyldiethoxysilane, n-octylmethyldimethoxysilane, n-octyldimethylmethoxysilane, n-octyldimethylethoxysilane, isobutylmethyldimethoxysilane, bis(trimethylsiloxy)methylmethoxysilane, tris(trimethylsilyl)silane, 1,2-diethoxytetramethyldisilane, phenyldimethylethoxysilane, n-propylmethyldimethoxysilane, n-propyldimethylmethoxysilane, methyltriethoxysilane, methyltrimethoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, phenylmethyldimethoxysilane, phenylmethyldiethoxysilane, phenylethyltrimethylsilane, diphenylmethylethoxysilane, diphenylmethylmethoxysilane, diphenylmethylsilane, phenyldimethylsilane, 1,3-dimethyltetramethoxydisiloxane, tetrakis(dimethylsiloxy)silane, methyltris(methoxyethoxy)silane, ethyldimethylsilane, dimethylethoxysilane, tris(trimethylsiloxy)silane, tert-butyldimethylsilane, di-tert-butylsilane, 1,1,2,2-tetramethyldisilane, 1,1,3,3,5,5-hexamethyltrisiloxane, 1,It can contain one or more selected from the group consisting of 5 - diethoxyhexamethyltrisiloxane, phenyltrimethylsilane, 1,4 - bis(4 - vinylphenoxy)butane, di - 4 - vinylbenzyl ether, divinyldiphenyl, divinylnaphthalene, 1 - heptene, 1 - octene, 1,4 - pentadiene, 1,5 - hexadiene, 1,6 - heptadiene, 1,7 - octadiene, 1,9 - decadiene, and combinations thereof.,

[0049] The siloxane resin composition can contain a peroxide radical polymerization initiator for the polymerization of the alkenyl groups contained in the siloxane and the cross - linking agent.,

[0050] Peroxide radical polymerization initiators include 2,3-dimethyl-2,3-diphenylbutane, tert-butyl hydroperoxide, tert-amyl hydroperoxide, cumyl hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, isopropylcumyl hydroperoxide, isopropylbenzene hydroperoxide, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexyne-3, 3,6,9-triethyl-3,6,9-trimethyl-1,4,7-triperoxonane, di(tert-butyl)-peroxide, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane, di(tert-butylperoxy-isopropyl)benzene, tert-butyl cumyl peroxide, di-(tert-amyl)-peroxide, dicumyl peroxide, butyl 4,4-di(tert-butylperoxy)valerate, tert-butyl peroxybenzoate, 2,2-di(tert-butylperoxy)butane, tert-amyl peroxy-benzoate, tert-butyl peroxy-acetate, tert-butyl peroxy-(2-ethylhexyl) carbonate, tert-butyl peroxyisopropyl carbonate, tert-butyl peroxy-3,5,5-trimethyl-hexanoate, 1,1-di(tert-butylperoxy)cyclohexane, tert-amyl peroxyacetate, tert-amyl peroxy-(2-ethylhexyl) carbonate, 1,1-di(tert-butylperoxy)-3,5,5-trimethylcyclohexane, 1,1-di(tert-amylperoxy)cyclohexane, tert-butyl-mono-peroxy-maleate, 1,1'-azodi(hexahydrobenzonitrile), tert-butyl peroxy-isobutyrate, tert-butyl peroxy diethylacetate, tert-butyl peroxy-2-ethylhexanoate, dibenzoyl peroxide, tert-amyl peroxy-2-ethylhexanoate, di(3-methylbenzoyl) peroxide, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, ammonium peroxodisulfate, 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane, 2,It can contain one or more selected from the group consisting of 2'-azodi(2-methylbutyronitrile), 2,2'-azodi(isobutyronitrile), didecanoyl peroxide, dilauroyl peroxide, di(3,5,5-trimethylhexanoyl) peroxide, tert-amyl peroxypivalate, tert-butyl peroxyneoheptanoate, 1,1,3,3-tetramethylbutyl peroxypivalate, tert-butyl peroxypivalate, dicetyl peroxydicarbonate, dimyristyl peroxydicarbonate, di(2-ethylhexyl) peroxydicarbonate, di(4-tert-butylcyclohexyl) peroxydicarbonate, diisopropyl peroxydicarbonate, tert-butyl peroxyneodecanoate, di-sec-butyl peroxydicarbonate, tert-amyl peroxyneodecanoate, cumyl peroxyneoheptanoate, di(3-methoxybutyl) peroxydicarbonate, 1,1,3,3-tetramethylbutyl peroxyneodecanoate, cumyl peroxyneodecanoate, diisobutyryl peroxide, and combinations thereof.,

[0051] The peroxide radical polymerization initiator acts as an important factor for the siloxane resin composition to have a copper foil peel strength suitable for application to printed circuit boards for electronic devices.,

[0052] For example, when curing is carried out by the initiation of a peroxide radical polymerization initiator in a state where the siloxane resin composition is in contact with the copper foil, a chemical bond between the hydroxyl groups on the copper foil surface and the alkenyl groups in the siloxane resin composition is induced, so that a high-strength bond can be formed between the copper foil and the siloxane resin composition, and a high copper foil peel strength can be obtained.,

[0053] The peroxide radical polymerization initiator can be contained in an amount of 0.01 part by weight to 5 parts by weight or less based on 100 parts by weight of an organoalkoxysilane having an asymmetric structure based on silicon and an organoalkoxysilane having a symmetric structure based on silicon.,

[0054] The peroxide radical polymerization initiator can be carried out by heat treatment at a temperature range of 40°C to 300°C.

[0055] The heat treatment can be carried out in a time range of 5 minutes to 6 hours, but it may not be limited to this. By using the peroxide radical polymerization initiator, a siloxane resin composition can be cured to produce a siloxane cured product.

[0056] The siloxane cured product can have the characteristics that the dielectric constant at 10 GHz frequency is 3.2 or less and the dielectric loss at 10 GHz frequency is 0.005 or less, which are dielectric characteristics suitable for application to printed circuit boards for high-frequency communication electronic devices.

[0057] After physically and chemically removing the acid or base catalyst added to the siloxane resin, when the siloxane resin composition is cured to produce a siloxane cured product with low dielectric constant and low dielectric loss, it can have the characteristic that the moisture absorption rate is 0.1% or less, which is a moisture absorption rate characteristic suitable for application to printed circuit boards for high-frequency communication electronic devices. For example, the step of removing the acid or base catalyst can include adding an organic solvent to dissolve the siloxane resin, and then separating the organic solvent in which the siloxane resin is dissolved from the acid or base catalyst by a layer separation method.

[0058] One embodiment can provide a glass fiber reinforced plastic film or sheet by including a glass cloth in the siloxane cured product.

[0059] The glass cloth can include, but is not necessarily limited to, a woven glass fabric, a non-woven glass fabric, or a mixture thereof made of glass fibers containing one or more selected from the group consisting of A glass, C glass, D glass, E glass, AR glass, R glass, S glass, S-2 glass, T glass, NE glass, E-CR glass, quartz, and combinations thereof.

[0060] When manufacturing a glass fiber reinforced plastic film or sheet by including a glass cloth in a siloxane cured product, it is advantageous for thermal processing by significantly reducing the coefficient of thermal expansion, and an additional effect of reducing dielectric loss can also be expected.

[0061] One embodiment can provide a copper-clad laminate or a flexible copper-clad laminate including a glass fiber reinforced plastic film or sheet.

[0062] When manufacturing a copper-clad laminate or a flexible copper-clad laminate, if it is manufactured under heat treatment conditions with a copper foil adhered to a siloxane resin composition containing a glass cloth, it can have excellent copper foil peel strength without an additional adhesive as described above, which is a copper foil peel strength characteristic suitable for application to printed circuit boards for high-frequency communication electronic devices.

[0063] One embodiment can provide a printed circuit board or a flexible printed circuit board including a copper-clad laminate or a flexible copper-clad laminate.

[0064] The curable siloxane resin composition has properties such as moisture absorption resistance, thermal processability, heat resistance, high adhesion to copper foil, low dielectric constant, and low dielectric loss, and can achieve a well-balanced physical property suitable for printed circuit boards for high-frequency communication electronic devices.

[0065] Hereinafter, the present invention will be described in more detail with reference to examples. However, the following examples are merely examples of the present invention, and the present invention is not limited to the following examples.

[0066] Example 1 Vinylmethyldimethoxysilane (Dimethoxymethylvinylsilane, Gelest), diphenyldimethoxysilane (Dimethoxydiphenylsilane, Gelest) and an aqueous sodium hydroxide solution (NaOH(aq), Samchun) are mixed in a molar ratio of 1:1:2. Next, the mixture is stirred at 80 °C for 12 hours under a nitrogen atmosphere. In order to remove the base catalyst with the siloxane resin obtained after stirring, the mixture is mixed with methyl isobutyl ketone (MIBK, Samchun) and water (H2O) in a weight ratio of 1:2:1. Due to the difference in solubility, the MIBK layer in which the siloxane is dissolved and the aqueous layer in which the base catalyst is dissolved are separated. Only the MIBK layer is obtained and the MIBK is evaporated at -0.1 MPa and 120 °C for 2 hours using a vacuum evaporator, and finally a siloxane resin is obtained.

[0067] 1 part by weight of di(tert-butyl)-peroxide (DTBP, Sigma Aldrich) is added to 100 parts by weight of the siloxane resin to produce a siloxane composition for curing.

[0068] The produced siloxane composition for curing is heat-treated (4 hr, 150 °C) to produce a siloxane cured product.

[0069] Example 2 A siloxane cured product is produced in the same manner as in Example 1 described above, except that vinylmethyldimethoxysilane, diphenyldimethoxysilane and an aqueous sodium hydroxide solution are mixed in a molar ratio of 0.4:0.6:1.

[0070] Example 3 A siloxane cured product is produced in the same manner as in Example 1 described above, except that vinylmethyldimethoxysilane, diphenyldimethoxysilane, and an aqueous sodium hydroxide solution are mixed at a molar ratio of 0.3:0.7:1.

[0071] Example 4 A siloxane cured product is produced in the same manner as in Example 1 described above, except that vinylmethyldimethoxysilane, diphenyldimethoxysilane, dimethoxydimethylsilane (from Gelest), and an aqueous sodium hydroxide solution are mixed at a molar ratio of 0.15:0.3:0.05:1.

[0072] Example 5 A siloxane composition is produced in the same manner as in Example 1 described above, and then a siloxane cured product is produced, except that vinylmethyldimethoxysilane, diphenyldimethoxysilane, and hydrochloric acid (HCl( aq ) from Samchun) are mixed at a molar ratio of 0.4:0.6:1.

[0073] Example 6 A siloxane cured product is produced in the same manner as in Example 1 described above, except that octavinyl-T8-silsesquioxane (from Hybrid Plastics) is added as a crosslinking agent to the siloxane composition produced in Example 1 described above.

[0074] Example 7 The siloxane composition produced in Example 1 described above is impregnated into a glass cloth (NE-glass, #1037, from Nittobo) and then cured to produce a glass fiber reinforced plastic film.

[0075] Example 8 The siloxane composition produced in Example 2 described above is impregnated into a glass cloth (NE-glass, #1037) and then cured to produce a glass fiber-reinforced plastic film.

[0076] Example 9 The siloxane composition produced in Example 3 described above is impregnated into a glass cloth (NE-glass, #1037) and then cured to produce a glass fiber-reinforced plastic film.

[0077] Example 10 The siloxane composition produced in Example 4 described above is impregnated into a glass cloth (NE-glass, #1037) and then cured to produce a glass fiber-reinforced plastic film.

[0078] Example 11 The siloxane composition produced in Example 2 described above is impregnated into a glass cloth (Quartz glass, SQX 2116C-04, ShinEtsu) and then cured to produce a glass fiber-reinforced plastic film.

[0079] Example 12 The siloxane composition produced in Example 2 described above is impregnated into a glass cloth (NE-glass, #1037), and then cured with copper foils covering both sides to produce a copper-clad laminate.

[0080] Comparative Example 1 A siloxane composition is produced and a siloxane cured product is produced in the same manner as in Example 1 described above, except that vinylmethyldimethoxysilane and an aqueous sodium hydroxide solution are mixed at a molar ratio of 1:2.

[0081] Comparative Example 2 A siloxane composition is produced and a siloxane cured product is produced in the same manner as in Example 1 described above, except that vinylmethyldimethoxysilane, diphenylsilanediol (Diphenylsilandiol, Gelest), and barium hydroxide monohydrate (Ba(OH)₂H₂O, Sigma Aldrich) are mixed at a molar ratio of 1:1:0.002.

[0082] Comparative Example 3 A siloxane resin composition is produced and a siloxane cured product is produced in the same manner as in Example 1 described above, except for the process of removing the base catalyst.

[0083] Comparative Example 4 A siloxane composition is produced and a siloxane cured product is produced in the same manner as in Example 1 described above, except that vinylmethyldimethoxysilane, dimethyldimethoxysilane, and an aqueous sodium hydroxide solution are mixed at a molar ratio of 1:1:2.

[0084] Comparative Example 5 The siloxane composition produced in Comparative Example 1 described above is impregnated into a glass cloth (NE-glass, #1037) and then cured to produce a glass fiber reinforced plastic film.

[0085] Comparative Example 6 The siloxane composition produced in Comparative Example 2 described above is impregnated into a glass cloth (NE-glass, #1037) and then cured to produce a glass fiber reinforced plastic film.

[0086] Comparative Example 7 The siloxane composition produced in Comparative Example 3 described above is impregnated into a glass cloth (NE-glass, #1037) and then cured to produce a glass fiber reinforced plastic film.

[0087] Experimental Example 1 - Experiment on Measuring Dielectric Constant and Dielectric Loss The dielectric constant and dielectric loss at 10 GHz of the siloxane cured products and glass fiber reinforced plastic films produced according to Examples 1 to 9, 11, 12 and Comparative Examples 1 to 6 were measured using a vector network analyzer (Keysight, N5222B) and a resonator (Split post dielectric resonator, QWED, for 10 GHz), and the measurement results are shown in Table 1 below.

[0088] Experimental Example 2 - Experiment on Measuring Moisture Absorption Resistance The moisture absorption resistance of the siloxane cured products and glass fiber reinforced plastic films produced according to Examples 1 to 9, 11, 12 and Comparative Examples 1 to 6 was measured according to ASTM D570 standard, and the measurement results are shown in Table 1 below.

[0089] Experimental Example 3 - Experiment on Measuring Coefficient of Thermal Expansion The coefficient of thermal expansion of the siloxane cured products and glass fiber reinforced plastic films produced according to Examples 1 to 9, 11, 12 and Comparative Examples 1 to 6 was measured using a TMA (Thermo Mechanical Analyzer, SS6100, SII Co.). The measurement standard is to heat to about 225 °C at a heating rate of about 5 °C / min in a nitrogen atmosphere and measure the coefficient of thermal expansion value in the temperature range of about 50 to 150 °C, and the measurement results are shown in Table 1 below.

[0090] Experimental Example 4 - Experiment on Measuring Copper Foil Peel Strength The peel strength between the copper foil of the copper-clad laminate and the glass fiber reinforced plastic film produced according to Example 10 was measured according to ASTM D6862 standard, and the measurement results are shown in Table 1 below.

[0091]

Table 1

[0092] Referring to Table 1, the siloxane cured products or glass fiber reinforced plastics according to Examples 1 to 11 all have a dielectric constant of 3.3 or less and a dielectric loss of 0.005 or less at 10 GHz, and thus have excellent low dielectric properties.

[0093] Referring to Table 1, the glass fiber reinforced plastics according to Examples 7 to 11 all have a lower dielectric loss than the siloxane cured products according to Examples 1 to 6 at 10 GHz. Therefore, when manufacturing a glass fiber reinforced plastic film or sheet by including a glass cloth in the siloxane cured product, an additional effect of reducing the dielectric loss appears.

[0094] Referring to Table 1, the siloxane cured products or glass fiber reinforced plastics according to Examples 1 to 11 all have a moisture absorption of 0.1% or less for the films, and thus have excellent moisture resistance.

[0095] Referring to Table 1, the thermal expansion coefficients of the siloxane cured products according to Examples 1 to 6 are all 50 ppm / °C or more, while the thermal expansion coefficients of the glass fiber reinforced plastics according to Examples 7 to 11 are 15 ppm / °C or less. Therefore, when manufacturing a glass fiber reinforced plastic film or sheet by including a glass cloth in the siloxane cured product, characteristics very suitable for application to a printed circuit board for high-frequency communication electronic devices appear in terms of thermal processing.

[0096] Referring to Table 1, the copper foil peel strength of the copper-clad laminate according to Example 12 is 1.5 N / mm and has excellent adhesion. Therefore, such a copper-clad laminate is very suitable for a printed circuit board for high-frequency communication electronic devices.

[0097] On the contrary, referring to Table 1, the siloxane cured products or glass fiber reinforced plastic films according to Comparative Examples 1 to 6 all have a dielectric loss of 0.005 or more at 10 GHz, and thus are not suitable for application to a printed circuit board for high-frequency communication electronic devices.

[0098] Also, referring to Table 1, the siloxane cured products or glass fiber reinforced plastic films according to Comparative Examples 3 and 7 have a hygroscopicity of 0.1% or more, and thus are not suitable for application to printed circuit boards for high-frequency communication electronic devices.

[0099] The preferred embodiments of the present invention have been described in detail above. However, the scope of the rights of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the claims also belong to the scope of the rights of the present invention.

Claims

1. A first organic alkoxysilane represented by the following chemical formula 1, [Chemical formula 1] R １ ａ R ２ ｂ Si(OR ３ ) ２ In the above chemical formula 1, R １ is linear or branched C ２－２０ and contains an alkenyl group, R ２ is H, a linear or branched C １－２０ alkyl group, C ６－２０ aryl group, or C ２－２０ alkenyl group, and contains R ３ is linear or branched C １－７ alkyl group-containing, 1 ≤ a < 2, 0 < b ≤ 1, and a + b = 2, A second organic alkoxysilane represented by the following chemical formula 2, [Chemical formula 2] R ４ ２ Si(OR ５ ) ２ In the above chemical formula 2, R ４ contains a C ６－２０ aryl group, R ５ is linear or branched C １－７ alkyl group-containing, A siloxane resin produced from the first organic alkoxysilane and the second organic alkoxysilane mixed in a molar ratio of 1:1 to 3:7 represented by the following chemical formula 3, and [Chemical formula 3] (R １ ａ R ２ ｂ SiO) ｘ (R ４ ２ SiO) ｙ In the above chemical formula 3, 1 ≤ x, 1 ≤ y, and x ≤ y, Containing a radical polymerization initiator, Not containing a base catalyst, A siloxane resin composition.

2. The first organic alkoxysilane is vinylmethyldimethoxysilane, vinylmethyldiethoxysilane, vinylphenyldimethoxysilane, vinylphenyldiethoxysilane, divinyldimethoxysilane, divinyldiethoxysilane, allyldimethoxysilane, allylmethyldimethoxysilane, allylmethyldiethoxysilane, dimethoxymethyl(4 - vinylphenyl)silane, or one or more thereof, and the siloxane resin composition according to Claim 1.

3. The second organic alkoxysilane is diphenyldimethoxysilane, diphenyldiethoxysilane, bis(4 - methylphenyl)dimethoxysilane, bis(4 - methylphenyl)diethoxysilane, bis(o - tolyl)dimethoxysilane, bis(o - tolyl)diethoxysilane, bis(m - tolyl)diethoxysilane, bis(m - tolyl)dimethoxysilane, di(naphthalen - 1 - yl)dimethoxysilane, di(naphthalen - 1 - yl)diethoxysilane, or one or more thereof, and the siloxane resin composition according to Claim 1.

4. Further comprising a third organic alkoxysilane represented by the following chemical formula 4, [Chemical formula 4] R ６ ２ Si(OR ７ ) ２ In the above chemical formula 4, R ６ is linear, branched or cyclic C １－２０ alkyl group-containing, R ７ is linear or branched C １－７ alkyl group-containing, Further comprising a siloxane resin produced from the first organic alkoxysilane, the second organic alkoxysilane, and the third organic alkoxysilane represented by the following chemical formula 5, [Chemical formula 5] (R １ ａ R ２ ｂ SiO) ｘ (R ４ ２ SiO) ｙ (R ６ ２ SiO) ｚ In the above chemical formula 5, 1 ≤ x, 1 ≤ y, 1 ≤ z, and x ≤ y + z, The total of the molar content of the second organic alkoxysilane and the molar content of the third organic alkoxysilane is greater than the molar content of the first organic alkoxysilane, and the molar content of the second organic alkoxysilane is greater than the molar content of the third organic alkoxysilane. The siloxane resin composition according to claim 1.

5. The siloxane resin composition according to claim 4, wherein the third organic alkoxysilane is dimethyldimethoxysilane, dimethyldiethoxysilane, diisobutyldimethoxysilane, diisobutyldiethoxysilane, diisopropyldimethoxysilane, diisopropyldiethoxysilane, di-n-butyldimethoxysilane, di-n-butyldiethoxysilane, di-n-propyldimethoxysilane, di-n-propyldiethoxysilane, dicyclopentyldimethoxysilane, dicyclopentyldiethoxysilane, or one or more thereof.

6. The siloxane resin composition according to claim 1, further comprising a crosslinking agent.

7. The crosslinking agent is vinyltetramethyldisiloxane, vinylpentamethyldisiloxane, 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane, 1,3-divinyltetraphenyldisiloxane, 1,1,3,3-tetravinyldimethyldisiloxane, 1,3-divinyltetraethoxydisiloxane, 1,3-divinyltetrakis(trimethylsiloxy)disiloxane, 1,3-divinyltetramethyldisiloxane, 1,3-diphenyltetrakis(dimethylsiloxy)disiloxane, hexamethyldisiloxane, 1,5-divinyl-3,3-diphenyl-1,1,5,5-tetramethyltrisiloxane, 1,5-divinyl-3-phenylpentamethyltrisiloxane, 1,3,5-trivinyl-1,1,3,5,5-pentamethyltrisiloxane, 2,4,6-trivinyl-2,4,6-trimethylcyclotrisiloxane, 2,4,6,8-tetravinyl-2,4,6,8-Tetramethylcyclotetrasiloxane, octavinyl-T8-silsesquioxane, phenyltris(trimethylsiloxy)silane, phenyltris(dimethylsiloxy)silane, tris(trimethylsiloxy)silane, tris(vinyldimethylsiloxy)methylsilane, tris(dimethylsiloxy)phenylsilane, tris(dimethylsiloxy)silane, divinylbenzene, p-divinylbenzene, vinyldimethylsilane, vinyltrimethylsilane, vinyltriethylsilane, vinyltriphenylsilane, vinyl-t-butyldimethylsilane, vinyl-di-n-octylmethylsilane, vinylphenylmethylsilane, vinylphenyldimethylsilane, divinyldimethylsilane, trivinylsilane, trivinylmethylsilane, tetravinylsilane, vinyldimethylmethoxysilane, vinylphenylmethylmethoxysilane, vinyldimethylethoxysilane, vinyldiphenylethoxysilane, vinylmethyldimethoxysilane, vinylmethyldiethoxysilane, vinylphenyldiethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltriisopropoxysilane, vinyltri-t-butoxysilane, vinyltriisopropenoxysilane, vinyltriphenoxysilane, vinyltris(2-methoxyethoxy)silane, vinyltris(methoxypropoxy)silane, trivinylmethoxysilane, trivinylethoxysilane, vinylmethylbis(trimethylsiloxy)silane, vinyltris(dimethylsiloxy)silane, vinyltris(trimethylsiloxy)silane, tetrakis(vinyldimethylsiloxy)silane, vinylmethyldiacetoxysilane, vinyltriacetoxysilane, 2-propenyltrimethylsilane, (1-methoxyvinyl)trimethylsilane, 1,2-divinyltetramethyldisilane, 1,4-divinyltetramethyldisilylethane, 1,4-bis(vinyldimethylsilyl)benzene, 1-allyl-1,1,3,3-tetramethyldisiloxane, 1,3-diallyltetramethyldisiloxane and 1,3 - Diallyltetrakis(trimethylsiloxy)disiloxane, allyldimethylsilane, allyltrimethylsilane, allyltriisopropylsilane, allyltriphenylsilane, diallyldimethylsilane, diallyldiphenylsilane, triallylmethylsilane, tetraallylsilane, allyldimethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, allyltriphenoxysilane, allyltris(trimethylsiloxy)silane, 2,4,6,8 - Tetramethylcyclotetrasiloxane, octamethyl - T8 - silsesquioxane, 1,1 - bis(trimethylsilylmethyl)ethylene, 1,1 - bis(trimethoxysilylmethyl)ethylene, methallyltrimethylsilane, diethoxymethylsilane, dimethoxymethylsilane, n - octadecylmethyldiethoxysilane, n - octadecyldimethylethoxysilane, n - octadecyldimethylmethoxysilane, n - octadecylmethyldimethoxysilane, n - octadecyldimethylsilane, n - octylmethyldiethoxysilane, n - octylmethyldimethoxysilane, n - octyldimethylmethoxysilane, n - octyldimethylethoxysilane, isobutylmethyldimethoxysilane, bis(trimethylsiloxy)methylmethoxysilane, tris(trimethylsilyl)silane, 1,2 - diethoxytetramethyldisilane, phenyldimethylethoxysilane, n - propylmethyldimethoxysilane, n - propyldimethylmethoxysilane, methyltriethoxysilane, methyltrimethoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, phenylmethyldimethoxysilane, phenylmethyldiethoxysilane, phenylethyltrimethylsilane, diphenylmethylethoxysilane, diphenylmethylmethoxysilane, diphenylmethylsilane, phenyldimethylsilane, 1,3 - dimethyltetramethoxydisiloxane, tetrakis(dimethylsiloxy)silane, methyltris(methoxyethoxy)silane, ethyldimethylsilane, dimethylethoxysilane, tris(trimethylsiloxy)silane, tert - butyldimethylsilane, di - tert - butylmethylsilane, 1,1,2,2 - tetramethyldisilane, 1,1,3,3,5,5 - hexamethyltrisiloxane, 1,The siloxane resin composition according to claim 6, comprising one or more selected from the group consisting of 5 - diethoxyhexamethyltrisiloxane, phenyltrimethylsilane, 1,4 - bis(4 - vinylphenoxy)butane, di - 4 - vinylbenzyl ether, divinyldiphenyl, divinylnaphthalene, 1 - heptene, 1 - octene, 1,4 - pentadiene, 1,5 - hexadiene, 1,6 - heptadiene, 1,7 - octadiene, 1,9 - decadiene, and combinations thereof.,

8. The siloxane resin composition according to claim 1, wherein the radical polymerization initiator comprises a peroxide radical polymerization initiator.

9. The peroxide radical polymerization initiator is 2,3-dimethyl-2,3-diphenylbutane, tert-butyl hydroperoxide, tert-amyl hydroperoxide, cumyl hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, isopropylcumyl hydroperoxide, isopropylbenzene hydroperoxide, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexyne-3, 3,6,9-triethyl-3,6,9-trimethyl-1,4,7-triperoxonane, di(tert-butyl)-peroxide, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane, di(tert-butylperoxy-isopropyl)benzene, tert-butyl cumyl peroxide, di-(tert-amyl)-peroxide, dicumyl peroxide, butyl 4,4-di(tert-butylperoxy)valerate, tert-butyl peroxybenzoate, 2,2-di(tert-butylperoxy)butane, tert-amyl peroxy-benzoate, tert-butyl peroxy-acetate, tert-butyl peroxy-(2-ethylhexyl) carbonate, tert-butyl peroxy isopropyl carbonate, tert-butyl peroxy-3,5,5-trimethyl-hexanoate, 1,1-di(tert-butylperoxy)cyclohexane, tert-amyl peroxyacetate, tert-amyl peroxy-(2-ethylhexyl) carbonate, 1,1-di(tert-butylperoxy)-3,5,5-trimethylcyclohexane, 1,1-di(tert-amylperoxy)cyclohexane, tert-butyl-mono-peroxy-maleate, 1,1'-azodi(hexahydrobenzonitrile), tert-butyl peroxy-isobutyrate, tert-butyl peroxy diethylacetate, tert-butyl peroxy-2-ethylhexanoate, dibenzoyl peroxide, tert-amyl peroxy-2-ethylhexanoate, di(3-methylbenzoyl) peroxide, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, ammonium peroxodisulfate, 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane, 2,The siloxane resin composition according to claim 8, comprising one or more selected from the group consisting of 2'-azodi(2-methylbutyronitrile), 2,2'-azodi(isobutyronitrile), didecanoyl peroxide, dilauroyl peroxide, di(3,5,5-trimethylhexanoyl) peroxide, tert-amyl peroxypivalate, tert-butyl peroxyneoheptanoate, 1,1,3,3-tetramethylbutyl peroxypivalate, tert-butyl peroxypivalate, dicetyl peroxydicarbonate, dimyristyl peroxydicarbonate, di(2-ethylhexyl) peroxydicarbonate, di(4-tert-butylcyclohexyl) peroxydicarbonate, diisopropyl peroxydicarbonate, tert-butyl peroxyneodecanoate, di-sec-butyl peroxydicarbonate, tert-amyl peroxyneodecanoate, cumyl peroxyneoheptanoate, di(3-methoxybutyl) peroxydicarbonate, 1,1,3,3-tetramethylbutyl peroxyneodecanoate, cumyl peroxyneodecanoate, diisobutyryl peroxide, and combinations thereof.

10. The cured product of the siloxane resin composition has a dielectric constant of 3.3 or less at a frequency of 10 GHz and a dielectric loss of 0.005 or less at a frequency of 10 GHz, according to claim 1.

11. The cured product of the siloxane resin composition has a moisture absorption of 0.1% or less as measured by ASTM D570 standard, according to claim 1.

12. The following Chemical Formula 1: R １ ａ R ２ ｂ Si(OR ３ ) ２ (In the Chemical Formula 1, R １ is linear or branched C ２－２０ alkenyl group-containing, R ２ is H, a linear or branched C １－２０ alkyl group, C ６－２０ aryl group, or C ２－２０ alkenyl group, and contains R ３ is linear or branched C １－７ alkyl group-containing, 1 ≦ a < 2, 0 < b ≦ 1, and a + b = 2) a first organic alkoxysilane represented by, the following Chemical Formula 2: R ４ ２ Si(OR ５ ) ２ (In the Chemical Formula 2, R ４ contains a C ６－２０ aryl group, R ５ is linear or branched C １－７ alkyl group-containing) a second organic alkoxysilane represented by, the following Chemical Formula 4: R ６ ２ Si(OR ７ ) ２ (In the Chemical Formula 4, R ６ is linear, branched or cyclic C １－２０ alkyl group-containing, R ７ is linear or branched C １－７ alkyl group-containing) a third organic alkoxysilane represented by, mixing an acid or base catalyst to produce a mixture, stirring the mixture to carry out a condensation reaction at 40°C to 300°C, removing the acid or base catalyst, and adding a peroxide radical polymerization initiator comprising, wherein the total of the molar content of the second organic alkoxysilane and the molar content of the third organic alkoxysilane is greater than the molar content of the first organic alkoxysilane, and the molar content of the second organic alkoxysilane is greater than the molar content of the third organic alkoxysilane, A method for producing a siloxane resin composition.

13. The acid catalyst is hydrochloric acid, sulfuric acid, nitric acid, formic acid, acetic acid, toluenesulfonic acid, butyric acid, palmitic acid, oxalic acid, tartaric acid, or a composition containing one or more of these, and is a method for producing the siloxane resin composition according to claim 12.

14. The base catalyst is an alkali metal compound, an alkaline earth metal compound, a quaternary ammonium compound, ammonia, an amine compound, or a composition containing one or more of these, and is a method for producing the siloxane resin composition according to claim 12.

15. The step of removing the base catalyst includes adding an organic solvent to dissolve the siloxane, and then separating the organic solvent in which the siloxane resin is dissolved from the base catalyst by a layer separation method, and is a method for producing the siloxane resin composition according to claim 12.

16. A glass fiber reinforced plastic (GFRP) film containing a cured product of the siloxane resin composition according to any one of claims 1 to 11 and a glass cloth.

17. A sheet containing a cured product of the siloxane resin composition according to any one of claims 1 to 11 and a glass cloth.

18. A copper clad laminate (CCL) containing the sheet according to claim 17.

19. A printed circuit board (PCB) containing the copper clad laminate according to claim 18.

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