JP2004339482A - Curable silicone resin composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a curable silicone resin composition capable of giving a cured product having high hardness and strength and excellent optical transparency in a short wavelength area, and useful as a material for an optical device or an optical part, an insulating material for an electronic device or an electronic part, or a coating material. <P>SOLUTION: This curable silicone resin composition contains (A) an aromatic hydrocarbon compound having at least two hydrogen atoms combining with silicon atoms in such a state that each of the silicon atoms combines with a hydrocarbon skeletal structure of the compound, (B) a cyclic siloxane compound having at least two alkenyl groups combining with silicon atoms, and (C) a hydrosilylation catalyst, or the composition contains (D) an aromatic hydrocarbon compound having at least two alkenyl groups combining with silicon atoms in such a state that each of the silicon atoms combines with a hydrocarbon skeletal structure of the compound, (E) a cyclic siloxane compound having at least two hydrogen atoms combining with silicon atoms, and (C) the hydrosilylation catalyst. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to a curable silicone resin composition useful as an optical device or optical component material, an electronic device or electronic component insulating material or a coating material.

  2. Description of the Related Art Conventionally, an epoxy resin is generally used as a material for an optical device or an optical component, particularly, a sealing material for a light emitting diode (LED) element. In addition, silicone resin has been attempted to be used as a molding material for LED elements (see Patent Documents 1 and 2) and as a color filter material (see Patent Document 3). There are few use cases.

  In recent years, while attention has been paid to white LEDs, problems such as yellowing of the epoxy encapsulant, which was not a problem until now, due to ultraviolet rays, and cracks due to an increase in heat generation due to miniaturization have occurred. It is urgent. As a countermeasure for these, use of a cured silicone resin having a large amount of phenyl groups in the molecule has been studied. However, there is a tendency to use light sources of shorter wavelengths as light sources for future LEDs, and epoxy encapsulants and phenyl group-containing silicone resin encapsulants transmit light in the short wavelength region. Because of its poor performance, application to LEDs that generate light in the short wavelength region has been problematic.

JP-A-10-228249 JP-A-10-242513 JP 2000-123981 A

  The present invention has been made in view of the above circumstances, and is useful as a material for an optical device or an optical component, an insulating material or a coating material for an electronic device or an electronic component, having high hardness and strength, and light in a short wavelength region. An object of the present invention is to provide a curable silicone resin composition that gives a cured product having excellent permeability.

  The present inventors have made intensive efforts to achieve the above object, and as a result, an aromatic hydrocarbon compound having a hydrogen atom or an alkenyl group bonded to a silicon atom in a state where the silicon atom is bonded to a hydrocarbon skeleton. And, in combination with a cyclic siloxane compound having an alkenyl group or a hydrogen atom bonded to a silicon atom, by using a silicone resin composition that is cured by a hydrosilylation reaction, it has been found that a cured product having the above properties can be obtained, Based on this finding, the present invention has been completed.

That is, the present invention firstly
(A) an aromatic hydrocarbon compound having at least two hydrogen atoms bonded to a silicon atom in a state where the silicon atom is bonded to a hydrocarbon skeleton;
(B) a cyclic siloxane compound having at least two alkenyl groups bonded to silicon atoms, and
(C) A curable silicone resin composition containing a hydrosilylation reaction catalyst is provided (hereinafter referred to as "first invention").

Furthermore, the present invention provides, secondly,
(D) an aromatic hydrocarbon compound having at least two alkenyl groups bonded to a silicon atom, wherein the silicon atom is bonded to a hydrocarbon skeleton;
(E) a cyclic siloxane compound having at least two hydrogen atoms bonded to a silicon atom, and
(C) A curable silicone resin composition containing a hydrosilylation reaction catalyst is provided (hereinafter, referred to as "second invention").

(Hereinafter, a hydrogen atom bonded to a silicon atom may be referred to as a “SiH group”.
Further, in the second invention, the —CH 2CH ₂ group in the alkenyl group bonded to the silicon atom in the aromatic hydrocarbon compound and the SiH group in the cyclic siloxane compound, In one invention, the SiH group of the aromatic hydrocarbon compound and the —CH = CH ₂ group in the alkenyl group bonded to the silicon atom of the cyclic siloxane compound are combined with a hydrosilylation addition known to those skilled in the art. Both are equivalent in that they undergo a reaction and together form the same connected structure to give a cured product. )

  The curable silicone resin composition of the present invention has a high hardness and strength, a high light transmittance even for light in a short wavelength region, and can provide a cured product having excellent transparency. Therefore, it can be suitably used for applications such as protection, sealing or adhesion of a light emitting diode element, wavelength change or adjustment, or a lens. Further, it can be used as a lens material, a sealing material for optical devices or optical components, various optical materials such as display materials, an insulating material for electronic devices or electronic components, and a coating material.

  Hereinafter, the present invention will be described in more detail.

First invention [(A) aromatic hydrocarbon compound]
The component (A) is an aromatic hydrocarbon compound having at least two SiH groups in a state where the silicon atom is bonded to a hydrocarbon skeleton.
As the component (A), for example, the following general formula (1):

HR ¹ R ² Si-A-SiR ³ R ⁴ H (1)
(Wherein, R ¹ , R ² , R ³ and R ⁴ independently represent a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 12 carbon atoms other than an alkenyl group, preferably 1 to 6) A group selected from the group consisting of substituted monovalent hydrocarbon groups having 1 to 12, preferably 1 to 6, carbon atoms other than alkenyl groups, and alkoxy groups having 1 to 6, preferably 1 to 4 carbon atoms. A is a divalent aromatic ring-containing hydrocarbon group having 6 to 12 carbon atoms, preferably 6 to 10 carbon atoms)
The compound represented by is preferred.

When R ^{1 to} R ⁴ are a monovalent hydrocarbon group other than an alkenyl group, they include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, pentyl group, isopentyl Alkyl groups such as a phenyl group, a hexyl group and a sec-hexyl group; aryl groups such as a phenyl group, o-, m- and p-tolyl groups; aralkyl groups such as a benzyl group and a 2-phenylethyl group; Halogenation of, for example, a chloromethyl group, a 3-chloropropyl group, a 3,3,3-trifluoropropyl group or the like in which one or more hydrogen atoms have been substituted with a halogen atom, a cyano group, an epoxy group-containing group, or the like; Examples thereof include an alkyl group, a 2-cyanoethyl group, and a 3-glycidoxypropyl group.

When R ^{1 to} R ⁴ are alkoxy groups, examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, and a tert-butoxy group. .
Among the compounds of the above general formula (1), those in which all of the above R ^{1 to} R ⁴ are methyl groups are preferred because they are easily produced industrially and are easily available.

  Examples of the aromatic ring-containing hydrocarbon group of A include o-, m-, p-phenylene, tolylene, o-, m-, p-xylylene, and divalent arylene represented by the following formula: And the like.

Preferred specific examples of the component (A) are shown below, but are not limited thereto. Hereinafter, "Me" represents a methyl group, "Et" represents an ethyl group, "Ph" represents a phenyl group, "- p-C ₆ H ₄ -" is a para-phenylene group, also "-m-C ₆ H ₄ - "is a metaphenylene group means.

HMe ₂ Si-p-C ₆ H ₄ -SiMe ₂ H
HMe ₂ Si-m-C ₆ H ₄ -SiMe ₂ H
HMePhSi-p-C ₆ H ₄ -SiMePhH
HMePhSi-m-C ₆ H ₄ -SiMePhH
HPh ₂ Si-p-C ₆ H ₄ -SiPh ₂ H
HPh ₂ Si-m-C ₆ H ₄ -SiPh ₂ H
HMeEtSi-p-C ₆ H ₄ -SiMeEtH
HMeEtSi-m-C ₆ H ₄ -SiMeEtH
H (MeO) ₂ Si-p-C ₆ H ₄ -Si (OMe) ₂ H
H (MeO) ₂ Si-m-C ₆ H ₄ -Si (OMe) ₂ H
HMe ₂ Si-CH ₂ -pC ₆ H ₄ -CH ₂ -SiMe ₂ H
HMe ₂ Si-CH ₂ -mC ₆ H ₄ -CH ₂ -SiMe ₂ H
_{HMePhSi-CH 2 -p-C 6} H 4 -CH 2 -SiMePhH
HMePhSi-CH ₂ -mC ₆ H ₄ -CH ₂ -SiMePhH
The component (A) can be used alone or in combination of two or more.

[(B) Cyclic siloxane compound]
Component (B) is a cyclic siloxane compound having at least two silicon-bonded alkenyl groups that undergoes a hydrosilylation addition reaction with component (A).
As the component (B), for example, the following general formula (2):

(R ^a R ⁵ SiO) n (R ⁶ R ⁷ SiO) m (2)
(Wherein, R ^a is an alkenyl group having 2 to 6, preferably 2 to 3 carbon atoms, and R ⁵ , R ⁶ and R ⁷ are each independently an unsubstituted or substituted C 1 to C 12, Preferably, it is a monovalent hydrocarbon group of 1 to 6, n is an integer of 2 to 10, m is an integer of 0 to 8, provided that n + m is an integer of 3 to 10, preferably 3 to 6. )
The cyclic siloxane compound represented by is preferred.

Examples of the ^Ra include a vinyl group, an allyl group, a propenyl group, an isopropenyl group, a butenyl group, a pentenyl group, a hexenyl group, and the like. Among them, a vinyl group and an allyl group are preferable, and a vinyl group is particularly preferable.
Examples of R ^{5 to} R ⁷ include the alkenyl groups exemplified for R ^a and the monovalent hydrocarbon groups exemplified for R ^{1 to} R ⁴ .

Preferred specific examples of the component (B) are shown below, but are not limited thereto. Hereinafter, "Vi" means a vinyl group, "Allyl" means an allyl group, and "Pr" means an n-propyl group.
(ViMeSiO) ₃
(ViMeSiO) ₄
(AllylMeSiO) ₃
(AllylMeSiO) ₄
(ViMeSiO) ₂ (Me ₂ SiO) ₂
(ViMeSiO) ₃ (Me ₂ SiO) ₁
(ViMeSiO) ₂ (PrMeSiO) ₂
(ViMeSiO) ₃ (PrMeSiO) ₁
The component (B) can be used alone or in combination of two or more.

  The content of the component (A) and the component (B) in the composition of the first invention is preferably such that the amount of the SiH group in the component (A) is 0.5 to 1 mol of the alkenyl group present in the whole composition. The amount is 2.0 mol, more preferably 0.8 to 1.5 mol. At this time, the ratio of the alkenyl group in the component (B) to the alkenyl group present in the whole composition is preferably at least 10 mol%, particularly preferably at least 30 mol%. When only the component (B) is present as a component having an alkenyl group in the composition, the amount of the SiH group in the component (A) is preferably 0.5 to 1 mol of the alkenyl group contained in the component (B). To 2.0 mol, more preferably 0.8 to 1.5 mol.

[(C) hydrosilylation reaction catalyst]
As the hydrosilylation reaction catalyst of the component (C), any conventionally known hydrosilylation catalyst can be used. Specific examples include, for example, platinum black, platinous chloride, chloroplatinic acid, a reaction product of chloroplatinic acid and a monohydric alcohol, a complex of chloroplatinic acid and an olefin, and a platinum-based compound such as platinum bisacetoacetate. Catalyst: Platinum group metal-based catalysts such as palladium-based catalysts and rhodium-based catalysts are exemplified.
The compounding amount of the component (C) may be any effective amount as a catalyst. It is usually preferable to add about 1 to 500 ppm, especially about 2 to 100 ppm, as a platinum group metal atom, based on the total weight of the components (A) and (B).

Second invention [(D) aromatic hydrocarbon compound]
The component (D) is an aromatic hydrocarbon compound having at least two alkenyl groups bonded to a silicon atom in a state where the silicon atom is bonded to a hydrocarbon skeleton.
As the component (D), for example, the following general formula (3):

^{R a R 8 R 9 Si-} A-SiR 10 R 11 R b (3)
Wherein R ^a and R ^b are independently an alkenyl group having 2 to 6, preferably 2 to 3 carbon atoms, and R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ are each independently unsubstituted A monovalent hydrocarbon group having 1 to 12 carbon atoms, preferably 1 to 6, a substituted monovalent hydrocarbon group having 1 to 12 carbon atoms, preferably 1 to 6, and 1 to 6 carbon atoms, preferably Is a group selected from the group consisting of 1 to 4 alkoxy groups, and A is the same as defined for the above formula (1))
Is preferred.
Examples of the above R ^a and R ^b include the groups exemplified for R ^a defined with respect to the above formula (2). Examples of R ^{8 to} R ¹¹ include the groups exemplified for R ^a defined with respect to the above formula (2) and the groups exemplified for R ^{1 to} R ⁴ defined for the above formula (1) (however, hydrogen (Excluding atoms).

Preferred specific examples of the component (D) are shown below, but are not limited thereto.
ViMe ₂ Si-p-C ₆ H ₄ -SiMe ₂ Vi
ViMe ₂ Si-m-C ₆ H ₄ -SiMe ₂ Vi
ViMePhSi-p-C ₆ H ₄ -SiMePhVi
ViMePhSi-m-C ₆ H ₄ -SiMePhVi
ViMe ₂ Si-CH ₂ -pC ₆ H ₄ -CH ₂ -SiMe ₂ Vi
ViMe ₂ Si-CH ₂ -mC ₆ H ₄ -CH ₂ -SiMe ₂ Vi
ViMePhSi-CH ₂ -pC ₆ H ₄ -CH ₂ -SiMePhVi
ViMePhSi-CH ₂ -mC ₆ H ₄ -CH ₂ -SiMePhVi
_{ViMe (MeO) -CH 2 -p-} C 6 H 4 -CH 2 -Si (OMe) MeVi
_{ViMe (MeO) -CH 2 -m-} C 6 H 4 -CH 2 -Si (OMe) MeVi
_{ViMe (EtO) -CH 2 -p-} C 6 H 4 -CH 2 -Si (OEt) MeVi
_{ViMe (EtO) -CH 2 -m-} C 6 H 4 -CH 2 -Si (OEt) MeVi
The component (D) can be used alone or in combination of two or more.

[(E) Cyclic siloxane compound]
The component (E) is a cyclic siloxane compound having at least two SiH groups, which undergoes a hydrosilylation addition reaction together with the component (D).
As the component (E), for example, the following general formula (4):

(HR ¹² SiO) n (R ¹³ R ¹⁴ SiO) m (4)
(Wherein, R ¹² , R ¹³ and R ¹⁴ are each independently a hydrogen atom, or an unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms, preferably 1 to 6 other than an alkenyl group) , N is an integer from 2 to 10, m is an integer from 0 to 8, provided that n + m is an integer from 3 to 10, preferably from 3 to 6.
The cyclic siloxane compound represented by is preferred.
Examples of the above R ^{12 to} R ¹⁴ include the groups exemplified for R ^{1 to} R ⁴ defined with respect to the above formula (1) (excluding the alkoxy group).

Preferred specific examples of the component (E) are shown below, but are not limited thereto.
(HMeSiO) ₃
(HMeSiO) ₄
(HMeSiO) ₂ (Me ₂ SiO) ₁
(HMeSiO) ₃ (Me ₂ SiO) ₁
(HMeSiO) ₄ (Me ₂ SiO) ₁
The component (E) can be used alone or in combination of two or more.

  The content of the component (D) and the component (E) in the composition of the second invention is preferably such that the amount of the SiH group in the whole composition per 1 mol of the alkenyl group contained in the component (D) is 0.5. To 2.0 mol, more preferably 0.8 to 1.5 mol. At this time, the ratio of the SiH groups in the component (E) to the SiH groups present in the entire composition is preferably at least 10 mol%, particularly preferably at least 30 mol%. When only the component (E) is present as a component having a SiH group in the composition, the amount of the SiH group in the component (E) is preferably 0.5 to 1 mol of the alkenyl group contained in the component (D). To 2.0 mol, more preferably 0.8 to 1.5 mol.

[(C) hydrosilylation reaction catalyst]
As the hydrosilylation reaction catalyst of the component (C), the same ones as described above are exemplified. The preferred amount of component (C) relative to the total weight of component (D) and component (E) is the same as described above.

Other Compounding Components In addition to the above components (A) to (E), it is optional to add other components to the composition of the present invention as long as the effects of the present invention are not impaired.
For example, in order to adjust the viscosity of the composition, the hardness of the cured product, etc., a linear diorganopolysiloxane or network organopolysiloxane having an alkenyl group or SiH group bonded to a silicon atom, a non-reactive linear Alternatively, a cyclic diorganopolysiloxane or the like may be blended.

Above all, when a network organopolysiloxane composed of a monofunctional structural unit having an alkenyl group or a SiH group bonded to a silicon atom and a tetrafunctional structural unit (SiO ₂ ) is blended, high transparency and weather resistance are obtained. It is preferable because the applied cured product can be obtained.

  In the first invention, (F1) when blending a network organopolysiloxane having an alkenyl group bonded to a silicon atom, the blending amount thereof, the alkenyl group of the component (F1) and the alkenyl of the component (B) The amount of the SiH group contained in the component (A) is preferably 0.5 to 2.0 mol, more preferably 0.8 to 1.5 mol, per 1 mol of the total amount of the group. Further, when the (F2) reticulated organopolysiloxane having a SiH group is compounded, the compounding amount is such that the total amount of the SiH group of the component (F2) and the SiH group of the component (A) is as described above ( The amount is preferably 0.5 to 2.0 mol, more preferably 0.8 to 1.5 mol, per 1 mol of the alkenyl group contained in the component (B).

  On the other hand, in the second invention, when (F1) a network organopolysiloxane having an alkenyl group bonded to a silicon atom is compounded, the compounding amount is such that the alkenyl group of the component (F1) and the component (D) The amount of the SiH group contained in the component (E) is preferably 0.5 to 2.0 mol, more preferably 0.8 to 1.5 mol, per 1 mol of the total amount of the compound and the alkenyl group. Further, when the (F2) reticulated organopolysiloxane having a SiH group is compounded, the compounding amount is such that the total amount of the SiH group of the component (F2) and the SiH group of the component (E) is (( The amount is preferably 0.5 to 2.0 mol, more preferably 0.8 to 1.5 mol, per 1 mol of the alkenyl group contained in the component (D).

Further, in order to secure a necessary pot life, a reaction control agent such as 1-ethynylcyclohexanol and 3,5-dimethyl-1-hexyn-3-ol can be blended. Further, within a range that does not affect the transparency, an inorganic filler such as fumed silica may be blended to improve the strength of the cured product, and, if necessary, a dye, a pigment, a flame retardant, and the like. You may mix.
The curing conditions of the composition of the present invention vary depending on the amount thereof, and are not particularly limited. However, it is usually preferable to set the conditions at 60 to 180 ° C. for 5 to 180 minutes.

  The composition of the present invention can be cured by heating under the above conditions after being applied to a predetermined substrate according to the application.

  Hereinafter, the present invention will be described specifically with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.

[Example 1]
(A) HMe ₂ Si-p-C ₆ H ₄ -SiMe ₂ H: 53 parts by weight,
(B) (ViMeSiO) ₄ : 47 parts by weight (SiH in (A) / Vi (molar ratio) in (B) = 1.0), and
1-ethynylcyclohexanol: 0.03 parts by weight are uniformly mixed, and
(C) Platinum-vinylsiloxane complex: A platinum metal atom was added in an amount of 20 ppm based on the total amount of (A) and (B), and the mixture was further uniformly mixed to obtain a composition. This composition was poured into a mold assembled from glass plates so as to have a thickness of 4 mm, and heated at 150 ° C. for 2 hours to obtain a cured product.

[Example 2]
Instead of the components (A) and (B) described in Example 1,
(D) ViMe ₂ Si-p-C ₆ H ₄ -SiMe ₂ Vi: 67 parts by weight, and
(E) (HMeSiO) ₄ : 33 parts by weight (SiH in (E) / Vi (molar ratio) in (D) = 1.0)
A composition was prepared in the same manner as in Example 1 except for using, and a cured product was obtained.

[Example 3]
Instead of the components (A) and (B) described in Example 1,
(A) HMe ₂ Si-p-C ₆ H ₄ -SiMe ₂ H: 23 parts by weight,
(B) (ViMeSiO) ₄ : 17 parts by weight, and
(F1) Compositional formula: (ViMe ₂ SiO _1/2 ) ₃ (Me ₃ SiO _1/2 ) ₁₈ (SiO ₂ ) Silicone resin having a number average molecular weight of 3600 represented by ₂₅ : 60 parts by weight ((A) SiH / Vi in (B) and Vi in (F1) (molar ratio) = 1.0)
A composition was prepared in the same manner as in Example 1 except for using, and a cured product was obtained.

[Example 4]
Instead of the components (A) and (B) described in Example 1,
(D) ViMe ₂ Si-p-C ₆ H ₄ -SiMe ₂ Vi: 33 parts by weight,
(E) (HMeSiO) ₄ : 7 parts by weight, and
(F2) Compositional formula: (HMe ₂ SiO _1/2 ) ₅ (Me ₃ SiO _1/2 ) ₁₅ (SiO ₂ ) Silicone resin having a number average molecular weight of 2300 represented by ₁₀ : 60 parts by weight ((E) (SiH in (F2) / Vi (molar ratio) in (D) = 1.0)
A composition was prepared in the same manner as in Example 1 except for using, and a cured product was obtained.

[Comparative Example 1]
(HMeSiO) ₄ : 41 parts by weight, (ViMeSiO) ₄ : 59 parts by weight, and 1-ethynylcyclohexanol: 0.03 part by weight were uniformly mixed. To this mixture was added a platinum-vinylsiloxane complex: an amount of 20 ppm as a platinum metal atom based on the total amount of the cyclic siloxane compound, and the mixture was further uniformly mixed to obtain a composition. Using this composition, a cured product was obtained in the same manner as in Example 1.

[Comparative Example 2]
A bisphenol A type epoxy resin (trade name: Pernox ME-540, manufactured by Pernox) was poured into a mold formed of glass plates in the same manner as in Example 1 so as to have a thickness of 4 mm, and heated at 150 ° C. for 8 hours. A cured product was obtained.

[Comparative Example 3]
A phenyl silicone resin-based curable composition (trade name: X-34-1195, manufactured by Shin-Etsu Chemical Co., Ltd., phenyl group content: about 50 mol%) was placed in a mold assembled with a glass plate in the same manner as in Example 1. The mixture was poured to a thickness of 4 mm and heated at 150 ° C. for 8 hours to obtain a cured product.

<Performance evaluation method>
The performance of the cured products obtained in the above Examples and Comparative Examples was evaluated according to the following method.
The appearance of each cured product was observed and is shown in Table 1.
hardness
The hardness (Shore D) of each cured product was measured according to ASTM D 2240. Table 1 shows the measurement results.
A test piece of 10 mm x 100 mm was prepared from each cured product having an elastic modulus of 4 mm, and the elastic modulus (MPa) was measured by a three-point bending test according to JIS K-66911. Table 1 shows the measurement results.

Light transmittance The light transmittance of each cured product was measured using a spectrophotometer at four points of measurement wavelengths: 800, 600, 400 nm, and 350 nm (ultraviolet region). Table 2 shows the measurement results.

[Evaluation]
The cured product of Comparative Example 1 was so soft that hardness and the like could not be measured. Further, as compared with the cured products of Comparative Example 2 and Comparative Example 3, the cured products of the Examples were all excellent in hardness and elastic modulus, and particularly in light transmittance at a short wavelength of 350 nm (ultraviolet region). It can be seen that is also excellent.

Claims (11)

(A) an aromatic hydrocarbon compound having at least two hydrogen atoms bonded to a silicon atom in a state where the silicon atom is bonded to a hydrocarbon skeleton;
(B) a cyclic siloxane compound having at least two alkenyl groups bonded to silicon atoms, and
(C) A curable silicone resin composition containing a hydrosilylation reaction catalyst. The component (A) has the following general formula (1):
HR ¹ R ² Si-A-SiR ³ R ⁴ H (1)
(Wherein, R ¹ , R ² , R ³ and R ⁴ independently represent a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 12 carbon atoms other than an alkenyl group, and a substituent other than an alkenyl group. Is a group selected from the group consisting of a monovalent hydrocarbon group having 1 to 12 carbon atoms and an alkoxy group having 1 to 6 carbon atoms, and A is a divalent aromatic ring-containing carbon atom having 6 to 12 carbon atoms. Is a hydrogen group)
The curable silicone resin composition according to claim 1, which is an aromatic hydrocarbon compound represented by the formula: The component (B) is represented by the following general formula (2):
(R ^a R ⁵ SiO) n (R ⁶ R ⁷ SiO) m (2)
(Wherein, R ^a is an alkenyl group having 2 to 6 carbon atoms, and R ⁵ , R ⁶ and R ⁷ are each independently an unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms, n is an integer of 2 to 10, m is an integer of 0 to 8, provided that n + m is an integer of 3 to 10.
The curable silicone resin composition according to claim 1, which is a cyclic siloxane compound represented by the formula: (D) an aromatic hydrocarbon compound having at least two alkenyl groups bonded to a silicon atom, wherein the silicon atom is bonded to a hydrocarbon skeleton;
(E) a cyclic siloxane compound having at least two hydrogen atoms bonded to a silicon atom, and
(C) A curable silicone resin composition containing a hydrosilylation reaction catalyst. The component (D) is represented by the following general formula (3):
^{R a R 8 R 9 Si-} A-SiR 10 R 11 R b (3)
(Wherein, R ^a and R ^b are each independently an alkenyl group having 2 to 6 carbon atoms, and R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ are each independently an unsubstituted carbon atom having 1 to 6 carbon atoms. 12 is a group selected from the group consisting of 12 monovalent hydrocarbon groups, substituted monovalent hydrocarbon groups having 1 to 12 carbon atoms, and alkoxy groups having 1 to 6 carbon atoms; 12 divalent aromatic ring-containing hydrocarbon groups)
The curable silicone resin composition according to claim 4, which is an aromatic hydrocarbon compound represented by the following formula: The component (E) is represented by the following general formula (4):
(HR ¹² SiO) n (R ¹³ R ¹⁴ SiO) m (4)
(Wherein, R ¹² , R ¹³ and R ¹⁴ are each independently a hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms other than an alkenyl group, and n is 2 to 10 And m is an integer of 0 to 8, provided that n + m is an integer of 3 to 10.
The curable silicone resin composition according to claim 4, which is a cyclic siloxane compound represented by the formula:   The curable silicone resin composition according to any one of claims 1 to 6, further comprising (F1) a network organopolysiloxane having an alkenyl group bonded to a silicon atom.   The curable silicone resin composition according to any one of claims 1 to 6, further comprising (F2) a network organopolysiloxane having a hydrogen atom bonded to a silicon atom.   The component (A) and the component (B) are such that the amount of hydrogen atoms bonded to silicon atoms in the component (A) is 0.5 to 2.0 mol per 1 mol of the alkenyl group contained in the component (B). The curable silicone resin composition according to any one of claims 1 to 3, wherein the curable silicone resin composition is present in an amount, and the component (C) is present in an effective amount as a catalyst.   The component (D) and the component (E) have an amount of hydrogen atoms bonded to silicon atoms in the component (E) of 0.5 to 2.0 mol per 1 mol of the alkenyl group contained in the component (D). The curable silicone resin composition according to any one of claims 4 to 6, wherein the curable silicone resin composition is present in an amount, and the component (C) is present in an effective amount as a catalyst. A cured product obtained by curing the curable silicone resin composition according to any one of claims 1 to 10.