TW201807072A - Silicon-containing curable composition and cured object obtained therefrom - Google Patents

Abstract

A silicon-containing curable composition characterized by comprising a compound having a carbon-carbon double bond that has reactivity with an SiH group, as component (A), a siloxane compound having an SiH group as component (B), a silane compound represented by the following general formula (1) as component (C), and a filler as component (D). (In formula (1), R1 represents a hydrogen atom or a C1-4 alkyl group, A represents a C1-10 alkanediyl group, and k represents a number of 2 or 3).

Description

Sturdy composition containing bismuth and cured product thereof

The present invention relates to a hardenable composition containing cerium and a cured product obtained by hardening it. The cerium-containing curable composition of the present invention and the cured product thereof can be used for a package or lead frame suitable for a material for a semiconductor, particularly for an LED (Light Emitting Diode).

Various studies have been conducted on compounds containing ruthenium, and polyoxyalkylene compounds typified by polyoxyxylene resins have been used in the industry. However, since the polyoxymethylene resin is excellent in heat resistance and flexibility, but has a large amount of outgassing components (volatile components), it is limited in use in the manufacturing steps of electronic components and the like due to contamination problems. In addition, in the field of electronic information, in the field of electronic information, with the development of technology, high-performance performance is required for various materials to be used. Therefore, research has been carried out to maximize the heat resistance, physical and electrical properties. Material. Among them, various techniques for producing a useful compound by a hydrogenation reaction of a ruthenium compound have been studied. Moreover, in the component manufacturing steps in the field of electronic information, the lithography step is often used, and high alkali resistance and solvent resistance are required. Therefore, a material which maintains high alkali resistance and solvent resistance while satisfying a high degree of heat resistance and crack resistance is sought. In view of these requirements, various curable compositions containing ruthenium have been proposed (for example, refer to Patent Documents 1 to 7 and the like). However, although the technologies proposed by the above-mentioned technologies have their own characteristics, they are not related to the heat resistance, light resistance, crack resistance, coloring property, and adhesion property of materials in the field of electronic information. The law is satisfactory. Among them, the poor adhesion to a silver base or a copper base has become a problem. [PRIOR ART DOCUMENT] [Patent Document 1] US Patent No. 5,645,941 [Patent Document 2] Japanese Patent Laid-Open No. Hei 8-73743 (Patent Document 3) Japanese Patent Laid-Open No. 2004-107577 [Patent Document 5] US Patent Application Publication No. 2009/012256 [Patent Document 6] Japanese Patent Laid-Open No. 2007-332259 (Patent Document 7) Japanese Patent Laid-Open Bulletin 2009-120732

In view of the above, it is an object of the present invention to provide a curable composition containing ruthenium which is excellent in adhesion to a silver base or a copper base and which can be used for a cured product such as an electric/electronic material. The inventors of the present invention have focused on the structure and prepolymer of a specific compound containing ruthenium, and have made efforts to solve the above problems, and have completed the present invention. That is, the present invention provides a curable composition containing cerium, which comprises the following component: a compound containing a carbon-carbon double bond having reactivity with an SiH group as the component (A), and a component (B) A siloxane compound having a SiH group, a decane compound represented by the following formula (1) as the component (C), and a filler as the component (D). [Chemical 1] (wherein R ¹ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, A represents an alkanediyl group having 1 to 10 carbon atoms, and k represents a number of 2 or 3) Further, the present invention provides a A method of hardening a curable composition of cerium, which comprises the step of heating the above-mentioned sclerosing composition containing cerium. Further, the present invention provides a cured product obtained by curing the above-mentioned curable composition containing cerium.

Hereinafter, the curable composition containing bismuth of the present invention and the cured product obtained by curing the same will be described in detail. In the curable composition containing cerium according to the present invention, the component (A) is a compound containing a carbon-carbon double bond having reactivity with an SiH group. The bonding position of the carbon-carbon double bond having reactivity with the SiH group is not particularly limited, and may be any position in the molecule. The carbon-carbon double bond having reactivity with the SiH group is not particularly limited, and examples thereof include a group represented by the following formula (2) and an alicyclic ring represented by the following formula (3). base. When the alicyclic group represented by the following formula (3) is used, the heat resistance of the cured product is high, which is preferable. [Chemical 2] (in the formula, L ¹ Represents hydrogen or methyl, * means bond key) [Chemical 3] (in the formula, L ² It means hydrogen or methyl group, and * means a bond bond.) In the group represented by the formula (2), it is particularly preferably L in terms of good reactivity. ¹ For hydrogen. In the group forming the alicyclic ring represented by the formula (3), it is particularly preferably L in terms of good reactivity. ² For hydrogen. The compound containing a carbon-carbon double bond having reactivity with an SiH group is exemplified by an organic compound containing a carbon-carbon double bond having reactivity with an SiH group (hereinafter, abbreviated as (A-α). Or a polyfluorene oxide compound (hereinafter, abbreviated as (A-β)) which has a carbon-carbon double bond having reactivity with an SiH group, as a compound which can be preferably used. (A-α) may be used alone or in combination of plural compounds having different structures. (A-β) may use only one compound, and a plurality of compounds having different structures may also be used. Further, (A-α) and (A-β) may be used in combination. The above (A-α) is not particularly limited as long as it is an organic compound containing a carbon-carbon double bond having reactivity with an SiH group, and preferably does not contain C, H, N, O, S and halogen. An element other than the organic compound constituting the element. As a preferable (A-α), trimethylallyl isocyanurate or triallyl isocyanurate can be mentioned. These are commercially available as Taic and Taic derivatives (manufactured by Nippon Kasei Co., Ltd.), and in the present invention, these commercially available products can be used as (A-α). The (A-β) is not particularly limited as long as it is a polyfluorene oxide compound having a carbon-carbon double bond having reactivity with an SiH group, and examples thereof include a unit represented by the following formula (4). A polymer containing ruthenium. [Chemical 4] (where, R ² An alkenyl group having 2 to 6 carbon atoms, * represents a bonding bond) as R in the above formula (4) ² Examples of the alkenyl group having 2 to 6 carbon atoms represented by a vinyl group include a vinyl group, a 2-propenyl group, and a 3-butenyl group. In terms of reactivity, R ² It is preferably a vinyl group. The ruthenium-containing polymer containing the unit represented by the above formula (4) can be produced, for example, by hydrolyzing and condensing only one or more kinds of the organic decane represented by the following formula (A-1). Or one or more types of the organic decane represented by the following general formula (A-1), and an organic decane represented by the following general formula (A-2) and the following general formula (A-3) A mixture of at least one organic decane in the organic decane is hydrolyzed and condensed. [Chemical 5] (where, R ³ An alkenyl group having 2 to 6 carbon atoms, R ⁴ , R ⁵ And R ⁶ Respectively represent a hydrogen atom or a hydrocarbon group, respectively, X ¹ a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms or a halogen atom) as R in the above formula (A-1) ³ Examples of the alkenyl group having 2 to 6 carbon atoms represented by a vinyl group include a vinyl group, a 2-propenyl group, and a 3-butenyl group. In terms of reactivity, R ³ It is preferably a vinyl group. As the above formula (A-2) and the above formula (A-3), R ⁴ , R ⁵ And R ⁶ The hydrocarbon group represented by the group includes an aliphatic hydrocarbon group such as an alkyl group, an alkenyl group or an alkynyl group; an alicyclic hydrocarbon group such as a cycloalkyl group; and an aromatic hydrocarbon group such as an aryl group or an arylalkyl group. As the hydrocarbon group, those having 1 to 10 carbon atoms are preferred. Further, as the above formula (A-1), the above formula (A-2), and the above formula (A-3), X ¹ Examples of the alkoxy group having 1 to 6 carbon atoms represented by a methoxy group, an ethoxy group, a propoxy group, a butoxy group, etc. ¹ Examples of the halogen atom include a chlorine atom, a bromine atom, and an iodine atom. In terms of reactivity, X ¹ It is preferably a methoxy group or an ethoxy group. Furthermore, each of the above formulas (A-1) to (A-3) ¹ There are different situations and different situations. In these, it is particularly preferred to use a ruthenium-containing polymer obtained by hydrolyzing and condensing an organic decane mixture containing 5 to 50 mol% of the above formula (A-1). The organic decane represented by the following formula (A-4) which is one or more kinds of organic decane (hereinafter sometimes abbreviated as (a)) and 0 to 50 mol% (hereinafter sometimes referred to simply as (b) (1) or more, 0 to 50 mol% of the organic decane (hereinafter, abbreviated as (c)) represented by the following formula (A-5), which is one or more and 0 to 40 mol%. One or more kinds of organic decane (hereinafter sometimes abbreviated as (d)) represented by the following general formula (A-6) and 0 to 40 mol% of the following general formula (A-7) One or more kinds of organic decane (hereinafter sometimes abbreviated as (e)), and the sum of the organic decane (b) and the organic decane (c) is 5 to 60 mol%. [Chemical 6] (where, R ⁷ Represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R ⁸ And R ⁹ Each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms, R ⁷ , R ⁸ And R ⁹ At least one of them is a methyl group, R ¹⁰ A phenyl group which is also substituted with an alkyl group having 1 to 6 carbon atoms, R ¹¹ An epoxy group having 2 to 10 carbon atoms, X ² a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms or a halogen atom), in the above formula (A-4), R ⁷ The alkyl group having 1 to 6 carbon atoms represented by the above may be any of a straight chain, a branched chain, and a cyclic group, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group. The second butyl group, the third butyl group, the isobutyl group, the pentyl group, the isopentyl group, the third pentyl group, the hexyl group, the cyclohexyl group and the like. In terms of reactivity, R ⁷ It is preferably a methyl group. As the above R in the general formula (A-5) ⁸ And R ⁹ The alkyl group having 1 to 6 carbon atoms and also having R ⁸ And R ⁹ The alkyl group having 1 to 6 carbon atoms in the case where the phenyl group is substituted is exemplified as the above R ⁷ The persons listed are the same. As R ⁸ And R ⁹ The alkenyl group having 2 to 6 carbon atoms represented by the above may be cited as the above R ³ The persons listed are the same. In terms of industrial accessibility, R ⁸ And R ⁹ Preferred is a methyl group, an unsubstituted phenyl group, and particularly preferably a methyl group. As the above formula (A-6), there is also a pair of R ¹⁰ The alkyl group having 1 to 6 carbon atoms in the case where the phenyl group is substituted is exemplified as the above R ⁷ The persons listed are the same. In terms of industrial accessibility, R ¹⁰ Preferred is an unsubstituted phenyl group. In the above formula (A-7), R ¹¹ The epoxy group having 2 to 10 carbon atoms is a substituent having a cyclic ether of a three-membered ring, and examples thereof include an epoxy group, a glycidyl group, and a 2,3-epoxybutyl group. 4-epoxybutyl, epoxyethylphenyl, 4-epoxyethylphenylethyl, 3,4-epoxycyclohexyl, 2-(3,4-epoxycyclohexyl)ethyl, 2 , 3-epoxy drop 𦯉 base ethyl and the like. In terms of imparting adhesion to dissimilar materials, R ¹¹ Preferred is glycidyl, 3,4-epoxycyclohexyl or 2-(3,4-epoxycyclohexyl)ethyl. X in the above formula (A-4) to (A-7) ² Examples of the alkoxy group having 1 to 6 carbon atoms represented by a methoxy group, an ethoxy group, a propoxy group, a butoxy group, etc. ² Examples of the halogen atom include a chlorine atom, a bromine atom, and an iodine atom. In terms of reactivity, X ² It is preferably a methoxy group or an ethoxy group. Furthermore, X in the above formula (A-1) ¹ And each of the above formulas (A-4) to (A-7) ² There are different situations and different situations. For using X ¹ And X ² When the alkoxy group having 1 to 6 carbon atoms (alkoxydecane) is used as the above five components, the hydrolysis and condensation reaction of the alkoxydecane may be carried out by a so-called sol-gel reaction. The sol-gel reaction can be carried out by a method in which a hydrolysis or a condensation reaction is carried out by a catalyst such as an acid or a base in a solvent-free state or in a solvent. The solvent to be used herein is not particularly limited, and specific examples thereof include water, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, acetone, and methylethyl. The ketone, dioxane, tetrahydrofuran, toluene, and the like may be used alone or in combination of two or more. The hydrolysis and condensation reaction of the alkoxydecane described above is carried out by alkoxydecane forming a stanol group (Si-OH) by hydrolysis based on water, and the resulting stanol groups are each or a stanol group. Condensation with an alkoxy group. In order to carry out the reaction, it is preferred to add an appropriate amount of water, water may be added to the solvent, or the catalyst may be dissolved in water to be added. Further, the hydrolysis and condensation reaction are also carried out by moisture in the air or a trace amount of water contained in the solvent. The catalyst such as an acid or an alkali to be used in the hydrolysis and condensation reaction is not particularly limited as long as it promotes hydrolysis or condensation reaction, and specific examples thereof include inorganic acids such as hydrochloric acid, phosphoric acid, and sulfuric acid; acetic acid, oxalic acid, and An organic acid such as toluenesulfonic acid or monoisopropyl phosphate; an inorganic base such as sodium hydroxide, potassium hydroxide, lithium hydroxide or ammonia; an amine compound such as trimethylamine, triethylamine, monoethanolamine or diethanolamine; Titanium esters such as tetraisopropyl ester and tetrabutyl titanate; tin carboxylates such as dibutyltin laurate and tin octylate; boron compounds such as trifluoroboron; chlorides of metals such as iron, cobalt, manganese and zinc or One type of these may be used, and two or more types may be used in combination, such as a metal carboxylate such as a naphthenate or an octanoate; or an aluminum compound such as aluminum triacetate. The hydrolysis and condensation reaction of the alkoxydecane described above is preferably a method in which a polycondensation reaction is carried out by adding an alkali catalyst to a base (pH 7 or more). Further, an acid catalyst may be added to carry out hydrolysis and dehydration polycondensation under acidic conditions (pH 7 or less). Further, in the case of performing the above hydrolysis and condensation reaction, it is preferred to stir the reaction system, and the reaction can be promoted by heating to 40 to 150 °C. The order of the above hydrolysis and condensation reaction is not particularly limited, and for example, an alkoxydecane having an alkenyl group (R) can be used. ³ Si(X ¹ ) ₃ ) with other alkoxy decanes (R ⁷ Si(X ² ) ₃ , R ⁸ R ⁹ Si(X ² ) ₂ , R ¹⁰ Si(X ² ) ₃ , R ¹¹ Si(X ² ) ₃ The two are mixed and hydrolyzed or condensed, and may be hydrolyzed or condensed to the extent that one of the five components is separately carried out, and then other alkoxy decane is added to further hydrolyze. , condensation reaction. As the above five components, X can also be used in combination. ¹ Or X ² For hydroxyl and X ¹ Or X ² For alkoxy groups, in this case, X ¹ And X ² It can be used without being hydrolyzed as a hydroxyl group. For the use of halogenated decane such as chlorodecane (X of the above five components) ¹ And X ² In the case of a halogen atom, hydrolysis and condensation may be carried out in the same manner as in the case of alkoxysilane. In order to obtain the produced ruthenium-containing polymer from the reaction after completion of the hydrolysis and condensation reaction, the reaction solvent, water, and catalyst may be removed, for example, by adding a solvent such as toluene for solvent extraction, and then flowing under a nitrogen stream. The extraction solvent can be distilled off under reduced pressure. In the above organic decane mixture, the organic decane (a) is preferably from 10 to 40 mol% in terms of controlling the crosslinking density at the time of hardening. The organic decane (b) and (c) may be used in an amount of 5 to 60 mol% as long as the sum of the organodecane (b) and the organodecane (c) is not used, and the crosslinking density at the time of curing is controlled. The organic decane (b) is preferably from 20 to 40 mol%, and the organic decane (c) is preferably from 10 to 25 mol% in terms of imparting flexibility to the resin. The organic decane (d) may not be used, but it is preferably from 5 to 45 mol% in terms of controlling the melting temperature of the resin. The organic decane (e) may not be used, but it is preferably 5 to 25 mol% in terms of imparting adhesion to the dissimilar material. Further, in terms of controlling the crosslinking density at the time of hardening, the sum of the organic decane (b) and the organic decane (c) is preferably 25 to 55 mol%. Further, in terms of controlling the molecular weight of the polymer containing ruthenium, the organic decane contained in the above organic decane mixture is preferably only organic decane (a), (b), (c), (d) and e) 5 ingredients. In the ruthenium-containing polymer containing the unit represented by the above formula (4), for example, it is derived from the organic decane (a), (b), (c), (d), and (e), respectively. ³ SiO _3/2 ), (R ⁷ SiO _3/2 ), (R ⁸ R ⁹ SiO), (R ¹⁰ SiO _3/2 ) and (R ¹¹ SiO _3/2 The five constituent units indicated are randomly connected in two dimensions and three dimensions, and the ends of each are OH groups and X. ¹ And X ² Any of them. X ¹ And X ² It is derived from the group of organodecane (a), (b), (c), (d) or (e). Furthermore, the above (R ³ SiO _3/2 ) also contains (R ³ SiX'O _2/2 ), above (R ⁷ SiO _3/2 ) also contains (R ⁷ SiX'O _2/2 ), above (R ¹⁰ SiO _3/2 ) also contains (R ¹⁰ SiX'O _2/2 ), above (R ¹¹ SiO _3/2 ) also contains (R ¹¹ SiX'O _2/2 ). The X' and the organic decane (a), (b), (d) and (e) respectively contain X ¹ And X ² The same, or represents the OH group. In the ruthenium-containing polymer containing the unit represented by the above formula (4), it is preferred that the ratio of the phenyl groups in all the organic components (components other than ruthenium) is 50% by mass or less, especially 40% by mass. In the following, it is preferred that the ratio of the methyl group is 85% by mass or less, particularly preferably 70% by mass or less. When the ratio of the phenyl group is large, the melting point of the polymer containing ruthenium becomes high, and it is difficult to melt at the temperature at the time of molding, and it is difficult to make the molecular weight of the cured product (polymer) large at the time of molding. Therefore, it is preferred that the ratio of the phenyl group is small, the ratio of the methyl group is large, and the ratio of the ratio of the phenyl group to the methyl group (the former: the latter) is preferably from 30:50 to 30:80. In the polymer containing ruthenium containing the unit represented by the above formula (4), a polymer having a weight average molecular weight of 300 to 100,000 in terms of polystyrene is preferred, and the weight average molecular weight is more preferably 800~ Within 50,000. Here, if the weight average molecular weight of the polymer containing cerium is less than 300, the thermal stability may be deteriorated, and if it is more than 100,000, it may be melted at the processing temperature in the transfer molding, or even if it is melted, The viscosity of the resin is also low at high viscosity, and the formability is lowered. The ruthenium containing polymer containing the unit represented by the above formula (4) can also be modified and used. The modification to the above-mentioned ruthenium-containing polymer is not particularly limited, and various modifications can be carried out in order to make the polyfluorene oxide resin a reactive polyoxymethylene resin. More specifically, it can be conventionally The method comprises amine modification, epoxy modification, carboxyl modification, methanol modification, methacrylyl sulfhydryl modification, sulfhydryl modification, phenol modification and the like. The ruthenium-containing polymer containing the unit represented by the above formula (4) as described above may be used singly or in combination of two or more kinds. In addition, examples of the polyfluorene oxide compound which can be preferably used as the above-mentioned (A-β) include, for example, a helium oxygen having one or more carbon-carbon double bonds having reactivity with a Si—H group in one molecule. Alkane compound. The oxoxane compound is not particularly limited as long as it is a siloxane compound having one or more carbon-carbon double bonds having reactivity with the Si—H group in one molecule, and for example, a linear chain can be used. Various types such as a shape, a ring shape, a branch shape, and a partial network structure. In the above, a siloxane compound having two or more carbon-carbon double bonds having reactivity with the Si—H group in one molecule is preferably contained in one molecule and two or more -H-based reactive carbon-carbon double bond linear siloxane compound or cyclic oxime containing two or more carbon-carbon double bonds having reactivity with Si-H groups in one molecule In the case of an alkane compound, a curable composition containing cerium having a higher adhesion can be obtained, which is particularly preferable. The linear siloxane compound having two or more carbon-carbon double bonds having reactivity with the Si-H group in one molecule contains two or more molecules having reactivity with the Si-H group. A linear aramidane copolymer of a carbon-carbon double bond. The linear alkane copolymer may be a random copolymer or a block copolymer. The number of carbon-carbon double bonds having reactivity with the Si-H group is preferably from 2 to 10, more preferably from 2 to 6 in terms of the crosslinking density of the cured product. Further, examples of the carbon-carbon double bond include an alkenyl group such as a vinyl group, a 2-propenyl group or a 3-butenyl group, and a vinyl group bonded to a ruthenium atom is preferred in terms of good reactivity ( Si-CH=CH ₂ base). In the case of a linear aramidane copolymer containing two or more carbon-carbon double bonds having reactivity with a Si—H group in one molecule, it is particularly preferable in terms of physical properties of the cured product. The linear alkane copolymer represented by the following general formula (A-8) is mentioned. [Chemistry 7] (where, R ¹² And R ³¹ Each independently represents an alkenyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms, an epoxy group having 2 to 10 carbon atoms or a trimethyldecyl group, and R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ²⁰ , R ^{twenty four} , R ²⁸ , R ²⁹ And R ³⁰ Respectively represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R ¹⁷ , R ¹⁸ And R ¹⁹ Indicates phenyl, R ^{twenty one} , R ^{twenty two} And R ^{twenty three} Independently represent an alkenyl group having 2 to 6 carbon atoms, R ²⁵ , R ²⁶ And R ²⁷ Respectively represent an epoxy group having 2 to 10 carbon atoms, respectively, in R ¹² And R ³¹ When it is an alkyl group having 1 to 6 carbon atoms, v≧1 or v+w≧2, in R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ²⁰ , R ^{twenty four} , R ²⁸ , R ²⁹ And R ³⁰ When at least one of them is a hydrogen atom, v≧1 or w≧1, p R ¹⁵ And R ¹⁶ There are different situations, and there are different situations, q R ¹⁷ And R ¹⁸ , r R ¹⁹ And R ²⁰ , v R ^{twenty one} And R ^{twenty two} , w R ^{twenty three} And R ^{twenty four} , x R ²⁵ And R ²⁶ , y R ²⁷ And R ²⁸ There are also different situations and different situations. p, q, r, v, w, x, and y each independently represent a number from 0 to 3000, and p+q+r+v+w+x+y≧1) as the above formula (A-8) R ¹² And R ³¹ And R ^{twenty one} , R ^{twenty two} And R ^{twenty three} The alkenyl group having 2 to 6 carbon atoms represented by the above may be cited as the above R ³ The persons listed are the same. Also, as R ¹² And R ³¹ And R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ²⁰ , R ^{twenty four} , R ²⁸ , R ²⁹ And R ³⁰ The alkyl group having 1 to 6 carbon atoms represented by the above may be cited as the above R ⁷ The persons listed are the same. Also, as R ¹² And R ³¹ And R ²⁵ , R ²⁶ And R ²⁷ The epoxy group having 2 to 10 carbon atoms represented by the above may be cited as the above R ¹¹ The persons listed are the same. In the above formula (A-8), in terms of reactivity, R ¹² And R ³¹ Preferred is vinyl or 2-propenyl, in terms of industrial availability, R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ²⁰ , R ^{twenty four} , R ²⁸ , R ²⁹ And R ³⁰ Preferred is methyl or ethyl, in terms of industrial availability, R ^{twenty one} , R ^{twenty two} And R ^{twenty three} It is preferably a vinyl group or a 2-propenyl group. In the above-mentioned preferred examples of the linear aramidane copolymer having two or more carbon-carbon double bonds having reactivity with the Si-H group in one molecule, the following formula (hereinafter, A-9) A linear siloxane compound represented by ~(A-17). [化8] (wherein, p, q and r are synonymous with the above formula (A-8)) [Chemical 9] [化10] (wherein, r and q are synonymous with the above formula (A-8)) [Chem. 11] (wherein, p is synonymous with the above formula (A-8)) [Chemical 12] (wherein p and q are synonymous with the above formula (A-8)) [Chemical 13] (wherein p and w are synonymous with the above formula (A-8)) [Chem. 14] (wherein, p, r and w are synonymous with the above formula (A-8)) [Chem. 15] (wherein, p, r and w are synonymous with the above formula (A-8)) [Chem. 16] (wherein p, r and w are synonymous with the above formula (A-8)), and a ring containing two or more carbon-carbon double bonds having reactivity with the Si-H group in the above one molecule The amount of the carbon-carbon double bond is preferably from 2 to 10, and more preferably from 2 to 6, in terms of a high crosslinking density of the cured product. Further, examples of the carbon-carbon double bond include an alkenyl group such as a vinyl group, a 2-propenyl group or a 3-butenyl group, and a vinyl group bonded to a ruthenium atom is preferred in terms of good reactivity ( Si-CH=CH ₂ base). In the cyclic siloxane compound having two or more carbon-carbon double bonds having reactivity with the Si-H group in one molecule, in terms of physical properties of the cured product, particularly preferred A cyclic siloxane compound represented by the following formula (A-18). [化17] (where, R ³² , R ³³ And R ³⁴ Respectively represent an alkyl or phenyl group having 1 to 6 carbon atoms, and n R ³² In the same situation, there are different situations, m R ³³ , m R ³⁴ There are also different situations and different situations. n represents the number of 2~10, m represents the number of 0~8, and m+n≧2) as the above R ³² , R ³³ And R ³⁴ The alkyl group having 1 to 6 carbon atoms represented by the above may be cited as the above R ⁷ The persons listed are the same. In the above formula (A-18), in terms of industrial availability, R ³² , R ³³ And R ³⁴ It is preferably a methyl group or a phenyl group. In terms of good crosslink density, n is preferably from 2 to 4, and m is preferably from 1 to 3 in terms of viscosity. In the above, a preferred specific example of the cyclic aramidane copolymer containing two or more carbon-carbon double bonds having reactivity with the Si—H group in one molecule is exemplified by the following formula (A). -19) ~ (A-21) is a cyclic oxane compound. [化18] [Chemistry 19] [Chemistry 20] Further, in the case where the compound having a carbon-carbon double bond having reactivity with the SiH group also has a SiH group (for example, a compound represented by the above formula (A-17)), the compound is regarded as the component (A). , not the component (B). The component (B) does not contain a carbon-carbon double bond having reactivity with the SiH group. The component (B) in the cerium-containing curable composition of the present invention is a SiH-based oxoxane compound. The component (B) is not particularly limited as long as it is a siloxane compound having one or more SiH groups in one molecule, and a siloxane compound having two or more SiH groups in one molecule can be preferably used. The content of the component (B) in the curable composition containing cerium of the present invention is preferably in the range of 0.1 to 100 parts by mass, more preferably in the range of 1 to 60 parts by mass, per 100 parts by mass of the component (A). More preferably, it is in the range of 5 to 40 parts by mass. In the oxoxane compound having two or more SiH groups in the above-mentioned one molecule, one or more selected from the group consisting of cyclic oxoxane compounds represented by the following formula (B-1) can be preferably used. One molecule obtained by performing a hydrazine hydrogenation reaction with at least one selected from the group consisting of a compound represented by the following formula (B-2), the following formula (B-3) or the following formula (B-4) A decane compound having two or more SiH groups (hereinafter sometimes referred to simply as (B-α)). [Chem. 21] (where, R ³⁵ , R ³⁶ And R ³⁷ Each of which independently represents an alkyl group having 1 to 6 carbon atoms or a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms, and f R ³⁵ In the same situation, there are different situations, g R ³⁶ , g R ³⁷ There are also different situations and different situations. f represents the number of 2~10, g represents the number of 0~8, and f+g≧2) [化22] (where, R ³⁸ An alkenyl group having 2 to 10 carbon atoms, R ³⁹ And R ⁴⁰ Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an epoxy group having 2 to 10 carbon atoms, and h is 1 or 2) in the above formula (B-1). Medium, R ³⁵ , R ³⁶ And R ³⁷ The alkyl group having 1 to 6 carbon atoms represented by the above may be any of a straight chain, a branched chain, and a cyclic group, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group. The second butyl group, the third butyl group, the isobutyl group, the pentyl group, the isopentyl group, the third pentyl group, the hexyl group, the cyclohexyl group and the like. In the above formula (B-1), R ³⁵ Preferred is methyl, R ³⁶ And R ³⁷ It is preferably a methyl group or a phenyl group. f is preferably 4 to 6, and g is preferably 0 to 1 in terms of the crosslinking density of the hardening reaction. In the case of both methyl and phenyl, in R ³⁵ ~R ³⁷ In terms of the number of all substituents, the ratio of the number of methyl groups to the number of phenyl groups (the former: the latter) is preferably in the range of 4:1 to 1:4. In the above formula (B-4), as R ³⁸ , R ³⁹ And R ⁴⁰ Examples of the alkenyl group having 2 to 10 carbon atoms represented by a vinyl group include a vinyl group, a 2-propenyl group, and a 3-butenyl group. In the above formula (B-4), R ³⁹ And R ⁴⁰ The alkyl group having 1 to 10 carbon atoms represented by the above may be any of a straight chain, a branched chain, and a cyclic group, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group. Second butyl, tert-butyl, isobutyl, pentyl, isopentyl, third pentyl, hexyl, cyclohexyl, heptyl, octyl, decyl, decyl, ethylhexyl and the like. In the above formula (B-4), R ³⁹ And R ⁴⁰ The epoxy group having 2 to 10 carbon atoms is a substituent having a cyclic ether of a three-membered ring, and examples thereof include an epoxy group, a glycidyl group, and a 2,3-epoxybutyl group. 4-epoxybutyl, epoxyethylphenyl, 4-epoxyethylphenylethyl, 3,4-epoxycyclohexyl, 2-(3,4-epoxycyclohexyl)ethyl, 2 , 3-epoxy drop 𦯉 base ethyl and the like. Examples of the cyclic oxirane compound represented by the above formula (B-1) include 1,3,5,7-tetramethylcyclotetraoxane, 1,3,5,7,9- Pentamethylcyclopentaoxane, 1,3,5,7,9,11-hexamethylcyclohexaoxane, etc., preferably 1,3,5,7-tetramethylcyclotetraoxane . The cyclic siloxane compound represented by the above formula (B-1) may be used singly or in combination of two or more. The compound represented by the above formula (B-2), when h is 1, represents divinylbenzene, which may be any of o-divinylbenzene, m-divinylbenzene or p-divinylbenzene. When h is 2, it means trivinylbenzene, and may be any of 1,2,3-trivinylbenzene, 1,2,4-trivinylbenzene, and 1,3,5-trivinylbenzene. The compound represented by the above formula (B-2) has a functional group other than a vinyl group (for example, an alkyl group such as a methyl group) bonded to a benzene ring, and is also a mixture of the above. Among the compounds represented by the above formula (B-2), the above formula (B-3) and the above formula (B-4), divinylbenzene is preferred. The compound represented by the above formula (B-2), the above formula (B-3), and the above formula (B-4) may be used singly or in combination of two or more. The above (B-α) may be one or more selected from the group consisting of the cyclic oxirane compounds represented by the above formula (B-1) and the above formula (B-2) and the above formula (B). -3) or one or more of the compounds represented by the above formula (B-4) are obtained by a hydrazine hydrogenation reaction. One or more selected from the group consisting of the cyclic oxoxane compounds represented by the above formula (B-1) and selected from the above formula (B-2), the above formula (B-3) or the above formula (B-) 4) The compounding ratio of one or more of the compounds to be represented is not particularly limited as long as it has two or more SiH groups in one molecule. The amount of the SiH group contained in one or more selected from the group consisting of the cyclic siloxane compounds represented by the above formula (B-1) is preferably selected from the above formula (B-2) and the above formula ( The ratio of the number of carbon-carbon double bonds having reactivity with the SiH group contained in one or more of the compounds represented by the above formula (B-4) (the former: the latter) is 10 : Range of 1~2:1, more preferably range of 4:1~2:1. The concentration of the SiH group of the above (B-α) is preferably from 0.0001 mmol/g to 100 mmol/g, and more preferably from 0.01 mmol/g to 20 mmol/g, in terms of good hardenability. The weight average molecular weight of the above (B-α) is preferably from 500 to 500,000, and more preferably from 1,000 to 300,000 in terms of good heat resistance. The weight average molecular weight may be measured by GPC (gel permeation chromatography), and it may be obtained by polystyrene conversion. The above hydrogenation reaction may be carried out using a platinum-based catalyst. As the platinum-based catalyst, a known catalyst containing one or more of platinum, palladium, and rhodium may be used to promote the hydrogenation reaction. Examples of the platinum-based catalyst used as a catalyst for the hydrogenation reaction include platinum-carbonylvinylmethyl complex, platinum-divinyltetramethyldioxane complex, and platinum-ring. A platinum-based catalyst such as a vinyl methyl oxane complex or a platinum-octanal complex is used, and a platinum-based metal such as palladium or rhodium is used instead of platinum, and one of these may be used alone. Alternatively, two or more kinds may be used in combination. Particularly preferably, in terms of hardenability, platinum is contained, and specifically, platinum-divinyltetramethyldioxane complex (Karstedt catalyst), platinum-carbonyl vinyl group is preferred. Base complex (Ossko catalyst). Further, in the present invention, a so-called Wilkinson catalyst containing a platinum-based metal such as tris(triphenylphosphine)iridium chloride (I) is also contained in the platinum-based catalyst. In terms of reactivity, the amount of the platinum-based catalyst to be used is preferably one or more selected from the group consisting of cyclic oxirane compounds represented by the above formula (B-1) and selected from the above formula ( B-2), the total amount of one or more of the compounds represented by the above formula (B-3) or the above formula (B-4) is 5% by mass or less, more preferably 0.0001 to 1.0% by mass. The hydrogenation reaction conditions are not particularly limited, and may be carried out under previously known conditions using the above-mentioned catalyst, and in terms of curing rate, it is preferably carried out at room temperature to 130 ° C, and may be carried out at the time of reaction. A previously known solvent such as toluene, xylene, hexane, MIBK (methyl isobutyl ketone, methyl isobutyl ketone), cyclopentanone, PGMEA (propylene glycol methyl ether acetate) or the like is used. Further, the catalyst may be removed after the hydrazine hydrogenation reaction, or may be directly used for the curable composition containing hydrazine without being removed. The component (C) in the cerium-containing curable composition of the present invention is a decane compound represented by the above formula (1). By using the component (C), the component (B), and the component (D) in combination, it is possible to obtain a cured product containing cerium which has excellent adhesion to a silver matrix or a copper matrix. A curable composition of bismuth. The content of the component (C) in the cerium-containing curable composition of the present invention is preferably 0.001 to 0.1 part by mass based on 100 parts by mass of the component (A). In the case of less than 0.001 part by mass, it is difficult to express the effect of addition. Further, even if it is added in an amount of more than 0.1 part by mass, the effect of blending is hardly improved. As the above R in the general formula (1) ¹ Examples of the alkyl group having 1 to 4 carbon atoms represented by a molecule include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a second butyl group, and a third butyl group. In view of the fact that the obtained cured product has a high effect of having excellent adhesion to a silver base or a copper base, among these, a methyl group or an ethyl group is preferable. Examples of the alkanediyl group having 1 to 10 carbon atoms represented by A in the above formula (1) include a methylene group, an exoethyl group, a propyl group, a butyl group, an isobutyl group, and a butyl group. Base, extension of the base, extension of the base, extension of Xinji and so on. In view of the fact that the obtained cured product has a high effect of having excellent adhesion to a silver base or a copper base, it is more preferably an alkanediyl group having 1 to 5 carbon atoms, and particularly preferably a stretched propyl group. In the above formula (1), k represents a number of 2 or 3. k is preferably 3 in terms of the effect that the obtained cured product has a high adhesion to the silver base or the copper base. Preferable specific examples of the compound represented by the formula (1) include compounds represented by the following chemical formulas No. 1 to No. 20. Further, in the following chemical formulas No. 1 to No. 20, "Me" represents a methyl group, and "Et" represents an ethyl group. [化23] [Chem. 24] [化25] The component (D) in the cerium-containing curable composition of the present invention is a filler. By using the component (D) in combination with the above components (A) to (C), the obtained cured product can be colored into a desired color, and the hardness of the obtained cured product can be improved. As the filler, a transparent filler, a white pigment, and an inorganic filler are preferable. The content of the component (D) in the cerium-containing curable composition of the present invention is preferably from 100 to 1,500 parts by mass, more preferably from 100 to 1400 parts by mass, based on 100 parts by mass of the component (A). It is 300~1350 parts by mass. In the curable composition containing cerium according to the present invention, it is also preferred to use the above white pigment and the above inorganic filler as the component (D). The white pigment is formulated to improve the whiteness as a white colorant. For example, titanium oxide is preferably used, and the unit cell of the titanium oxide may be any one of a rutile type, an anatase type, and a brookite type. When considering light resistance, a rutile type is preferably used. Further, the average particle diameter or shape is not limited, and the average particle diameter is usually 0.05 to 5.0 μm. In order to improve the compatibility with the resin or the inorganic filler, the titanium oxide may be subjected to surface treatment in advance by an aqueous oxide such as Al or Si. Furthermore, the average particle diameter can be a mass average value D in the particle size distribution measurement by the laser light diffraction method. ₅₀ The form of (or median particle size) is determined. Further, as the white pigment, potassium titanate, zirconium oxide, zinc sulfide, aluminum oxide, zinc oxide, magnesium oxide, cerium oxide, barium sulfate or the like may be used in addition to titanium oxide. Among these, magnesium oxide and zinc oxide are preferred. These white pigments may be used singly or in combination with titanium oxide. The inorganic filler can be usually used in a sealing material such as a polyoxyxylene resin composition or an epoxy resin composition. For example, molten cerium oxide, molten spherical cerium oxide, crystalline cerium oxide, colloidal cerium oxide, smoked cerium oxide, cerium oxide or the like; cerium oxide; aluminum oxide, iron oxide, titanium oxide, and the like a metal oxide such as cerium oxide; a ceramic such as tantalum nitride, aluminum nitride, boron nitride or tantalum carbide; a mineral such as mica or montmorillonite; a metal hydroxide such as aluminum hydroxide or magnesium hydroxide or organically modified Such as the treatment of the treatment, etc.; metal carbonate such as calcium carbonate, calcium citrate, magnesium carbonate, cesium carbonate or the like by organic modification treatment; etc.; metal borate , carbon black and other pigments; carbon fiber, graphite, whiskers, kaolin, talc, glass fiber, glass beads, glass microspheres, cerium oxide glass, layered clay minerals, clay, tantalum carbide, quartz, aluminum, zinc, etc. Further, as the filler (D), an organic filler such as acrylic beads, polymer fine particles, transparent resin beads, wood chips, pulp, or cotton sheets may be used. The average particle diameter or shape of the inorganic filler and the organic filler is not particularly limited, and the average particle diameter is usually 0.1 to 80 μm. Furthermore, the average particle diameter can be a mass average value D in the particle size distribution measurement by the laser light diffraction method. ₅₀ The form of (or median particle size) is determined. The inorganic filler is preferably a cerium oxide, a metal oxide or a metal carbonate or a pigment which is modified in terms of moldability and strength of the resin, and more preferably molten cerium oxide. , molten spherical cerium oxide, crystalline cerium oxide, polyoxynized beads, colloidal cerium oxide, aluminum oxide, titanium oxide, calcium carbonate, magnesium carbonate, carbon black, kaolin, glass fiber. As the inorganic filler, in particular, in terms of moldability of the resin, a composite of molten cerium oxide, molten spherical cerium oxide, titanium oxide, and calcium carbonate is preferably used. Further, the particle diameter thereof is not particularly limited, and is preferably 4 to 40 μm, particularly preferably 7 to 35 μm, in terms of moldability and fluidity. Further, in order to obtain high fluidity, it is preferable to use a combination of a fine region of 3 μm or less, a median diameter region of 4 to 8 μm, and a coarse region of 10 to 40 μm. Further, in the curable composition containing cerium according to the present invention, an organic peroxide, a metal catalyst, a bonding aid, a radical scavenger, and various known ones may be blended insofar as the target properties of the present invention are not impaired. Any component such as resin, mold release agent, and additive. The amount of the optional component to be used is not particularly limited, and in the curable composition containing cerium according to the present invention, it is preferably in a range of 10% by mass or less, more preferably 5% by mass or less. . As the organic peroxide, for example, a general user can be used for curing the polyoxyxene rubber composition, and examples thereof include benzamidine peroxide, o-methylbenzhydryl peroxide, and p-methylbenzophenone peroxide. Bismuth, peroxy-o-monomethylbenzhydrazide, peroxy-p-monomethylbenzhydrazide, peroxy-2,4-dichlorobenzamide, 2,4-diisopropylphenylbenzhydryl peroxide, Di-tert-butyl benzamidine oxide, tert-butyl benzoate, tributyl cumyl benzamidine peroxide, 1,1-bis(tert-butylperoxy-3)-3,3, 5-trimethylcyclohexane, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, 1,6-bis(t-butylcarboxyperoxy)hexane, Dicumyl peroxide, dimyristyl peroxycarbonate, tert-butyl peroxy 2-ethylhexyl carbonate, dicyclododecyl peroxydicarbonate, general formula (5) or (5) ') Compounds and the like. Among these, a benzamidine-based peroxide compound is preferred in terms of reactivity and workability, and particularly preferably benzamidine peroxide or 2,4-diisopropylphenylbenzene peroxide. Hyperthyroidism. [Chem. 26] (wherein R and R' are each independently a hydrocarbon group having 3 to 10 carbon atoms) as R in the above formulae (5) and (5') and R' in the above formula (5') Examples of the hydrocarbon group having 3 to 10 carbon atoms include a propyl group, an isopropyl group, a butyl group, a second butyl group, a tert-butyl group, an isobutyl group, a pentyl group, an isopentyl group, a third pentyl group, and a hexyl group. , cyclohexyl, cyclohexylmethyl, 2-cyclohexylethyl, heptyl, isoheptyl, third heptyl, n-octyl, isooctyl, trioctyl, 2-ethylhexyl, decyl, An alkyl group such as isodecyl or fluorenyl; vinyl, 1-methylvinyl, 2-methylvinyl, propenyl, butenyl, isobutenyl, pentenyl, hexenyl, heptenyl, octyl Alkenyl, nonenyl, 1-phenylpropen-3-yl and the like alkenyl; phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl , 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4-tert-butylphenyl, 2,3-dimethylphenyl 2,4-Dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl , 2,4-di-t-butylphenyl, etc. An alkylaryl group; an arylalkyl group such as a benzyl group, a 2-phenylpropan-2-yl group, a styryl group or a cinnamyl group; and the like, wherein the ether bond or the thioether bond is interrupted, for example, 2-methoxy Ethyl ethyl, 3-methoxypropyl, 4-methoxybutyl, 2-butoxyethyl, methoxyethoxyethyl, methoxyethoxyethoxyethyl, 3 -methoxybutyl, 2-phenoxyethyl, 3-phenoxypropyl, 2-methylthioethyl, 2-phenylthioethyl, and further, the alkoxy group A case where an alkenyl group, a nitro group, a cyano group, a halogen atom or the like is substituted. The content in the case of using the above organic peroxide is preferably 0.0001 to 10 parts by mass, more preferably 0.01 to 5 parts by mass, per 100 parts by mass of the component (A). Examples of the metal catalyst include a platinum-based catalyst, aluminum tris(2,4-pentanedionate), aluminum triisopropoxide, and Al (ClO). ₄ ) ₃ , titanium tetraisopropoxide, titanium tetraisobutoxide, tin dibutyl bis(2,4-pentanedionate), Bu ₂ Sn(C ₇ H ₁₅ COO) ₂ Metal catalysts such as Al-based, Ti-based, and Sn-based. Among these, in terms of reactivity and coloring property, a platinum-based catalyst or an Al-based catalyst is preferred, and a platinum-carbonylvinylmethyl complex (Ossko catalyst) or platinum is preferred. Divinyltetramethyldioxane complex (Karstedt complex), tris(2,4-pentanedionate) aluminum. The content in the case of using the above metal catalyst is preferably 1 × 10 based on 100 parts by mass of the above component (A). ^-4 ~0.5 parts by mass, and more preferably 1 x 10 ^-3 ~0.2 parts by mass. As the above-mentioned adhesion aid, for example, a compound having a cyanuric acid structure can be used. As the compound having a cyanuric acid structure, for example, iso-cyanuric acid, triallyl cyanurate, 1,3,5-triglycidyl isocyanate or iso-cyanuric acid can be used. Tris(2-hydroxyethyl) ester, tris(2,3-dihydroxypropyl) isocyanurate, tris(2,3-epoxypropyl) isocyanurate, and Japanese patent No. 2,768, 426, Japanese Patent Laid-Open No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei. Further, these compounds are also subjected to various modification treatments such as polyoxymethylene modification, ethylene oxide modification, and propylene oxide modification by a conventional method. In the case of using a compound having a cyanuric acid structure, the content of the compound in the cerium-containing curable composition of the present invention is preferably 0.0001 to 10% by mass, and more preferably 0.01 to 1.0% by mass. Examples of the radical scavenger include antioxidants such as antioxidants and stabilizers. For example, triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], dibutylhydroxytoluene (BHT), 2,6- Di-t-butyl-p-cresol (DBPC) and the like. In the case of using a radical scavenger, it is preferred in the curable composition containing cerium according to the present invention in terms of heat resistance, electrical properties, hardenability, mechanical properties, storage stability, and handleability. 0.1 to 10% by mass, more preferably 1 to 5% by mass. Examples of the various resins include polybutadiene resin and modified product thereof, modified acrylonitrile copolymer, polystyrene resin, polyethylene resin, fluororesin, polyimine resin, and polyethylene. A polyether resin such as an alcohol, a polyphenylene ether or a polypropylene glycol, a polyurethane resin, an epoxy resin, a phenol resin, a polyester resin, a melamine resin, a polyamide resin, a polyphenylene sulfide resin or the like. As the above-mentioned release agent, for example, carnauba wax, fatty acid ester, glycerate, stearic acid, montanic acid, behenic acid and a metal salt thereof, an alkali metal compound, an organic titanium, an organic zirconium, an organotin compound, or the like can be used. Imidazole compound, carboxyl group-containing polyolefin, polyethylene-polyoxyethylene resin, Brazilian palm, and the like. Examples of the above-mentioned additives which can be arbitrarily formulated include a glossing agent, a wax, an ultraviolet absorber, an antistatic agent, an antioxidant, a deterioration preventing agent, a modifier, a decane coupling agent, a defoaming agent, a dye, and a cis. An enediamine compound, a cyanate compound, a polyoxymethylene gel, a polyoxygenated oil, or the like. Since the curable composition containing cerium of the present invention is solid at room temperature (25 ° C), it is excellent in handleability. The curable composition containing cerium of the present invention may be in the form of a powder, a granule or a tablet, or may be dissolved in a solvent and used. The melting point of the cerium-containing curable composition of the present invention is preferably 50 ° C or more and 150 ° C or less, and more preferably 50 ° C or more and 120 ° C or less. The cerium-containing curable composition of the present invention is preferably melted at 50 ° C to 150 ° C and then cured by heat. Moreover, the cured product containing the curable composition containing cerium of the present invention is excellent in adhesion to the silver base and the copper base, and is also excellent in heat resistance and adhesion. In the heat resistance, in detail, it is preferable to obtain a cured product having a temperature at which the weight loss of 5 mass% of the cured product is 400 ° C or higher, and more preferably 500 ° C or higher. Further, from the curable composition containing bismuth of the present invention, it is possible to preferably obtain a cured product having less cracking. The curable composition containing cerium of the present invention can be uniform and transparent. In this case, light transmittance such as ultraviolet light is also preferable, and photohardening can be carried out by adding a photoreactive catalyst. Of course, a photoreactive monomer or resin may be further prepared, and any one or more of the components in the curable composition containing cerium may have a photoreactive group. Further, from the curable composition containing cerium of the present invention, weather resistance, hardness, stain resistance, flame retardancy, moisture resistance, gas barrier property, flexibility, elongation or strength, and electrical insulation can be obtained. A material excellent in mechanical properties such as low dielectric constant, optical properties, and electrical properties. Next, the cured product of the present invention will be described. The curable composition containing cerium of the present invention can be hardened by heating to obtain a cured product. The hardening reaction can be carried out by mixing and heating the compounding component of the curable composition containing cerium of the present invention, or by mixing all the components in advance and heating during the hardening reaction. The method is carried out. The heating temperature at the time of hardening is preferably a temperature at which the resin is melted, for example, 35 to 350 ° C, more preferably 50 to 250 ° C. The hardening time is preferably from 2 to 60 minutes, more preferably from 2 to 10 minutes. Further, it may be annealed or formed after curing. Annealing varies depending on the temperature, and if it is 150 ° C, it is preferably treated for about 5 to 60 minutes. By the hardening reaction under the hardening reaction conditions, a cured product having excellent properties such as heat resistance, durability, adhesion, and the like can be obtained from the curable composition containing cerium of the present invention. As the molding method, a known method such as transfer molding, compression molding, or casting molding can be used, and in terms of workability and dimensional stability, transfer molding is preferred. Transfer forming is preferably carried out using a transfer molding machine at a forming pressure of 5 to 20 N/mm. ² The molding temperature is 120 to 190 ° C for 30 to 500 seconds, especially 150 to 185 ° C for 30 to 180 seconds. The compression molding method is preferably carried out by using a compression molding machine at a molding temperature of 120 to 190 ° C for 30 to 600 seconds, particularly at 130 to 160 ° C for 120 to 300 seconds. In any of the forming methods, the curing can be carried out at 150 to 185 ° C for 2 to 20 hours. Further, when the curable composition containing cerium of the present invention is cured, a film forming method such as spin coating, pouring, or immersion can be suitably applied. The curable composition containing cerium of the present invention can be used as a cured product, and has excellent excellent adhesion to a silver matrix and a copper matrix, and is excellent in various physical properties such as heat resistance, light resistance, crack resistance, and coloring property. A curable composition. The curable composition and cured product containing bismuth according to the present invention can be used as a sealing material for display materials, optical materials, recording materials, printed substrates, semiconductors, solar cells, etc. in the field of electrical and electronic materials; high voltage insulating materials, Various materials for the purpose of insulation, vibration, water and moisture. In addition, it can also be used as a prototype for plastic parts, a coating material, an interlayer insulating film, a prepreg, a gasket for insulation, a heat shrinkable rubber tube, an O-ring, a sealant for a display device, and a protective material. , optical waveguide, optical fiber protective material, optical lens, adhesive for optical equipment, high heat resistant adhesive, elastic adhesive, adhesive, adhesive, high heat dissipation material, high heat resistant sealing material, solar cell, fuel cell A solid electrolyte for a member, a battery, an insulating coating material, a photosensitive drum for a photocopier, and a gas separation membrane. Moreover, it can also be applied to concrete protection materials, lining, soil injection agents, sealants, thermal storage materials, glass coatings, foams, paints, etc. in the field of civil engineering and building materials, and further, in the field of medical materials. It can also be applied to pipes, sealing materials, coating materials, printed circuit board applications, sealing materials for sterilization treatment devices, contact lenses, oxygen-rich films, and the like. In addition, it can be applied to films, gaskets, casting materials, various molding materials, rust-proof and waterproof sealants for wire mesh glass, automotive parts, and various mechanical parts. [Examples] Hereinafter, the present invention will be further illustrated by examples, but the present invention is not limited by the examples and the like. Furthermore, the "parts" or "%" in the examples are based on the quality benchmark. [Table 1] [Production Example 1] Synthesis of A-1 In a 2000 ml four-necked flask equipped with a cooling tube and a stirring device, 0.5 mol of vinyltrimethoxydecane as component (a) and methyl group as component (b) were placed. 0.5 mol of trimethoxydecane, 0.25 mol of dimethyldimethoxydecane as component (c), 1.0 mol of phenyltrimethoxydecane as component (d), and 650 g of toluene, while stirring for 30 31.4 g of a 0.5% aqueous sodium hydroxide solution was added dropwise thereto, and dehydration polymerization was carried out at 60 to 65 ° C for 3 hours. After cooling to room temperature, 600 g of toluene and 1500 g of ion-exchanged water were added to extract the oil layer, and after washing to neutrality, the solvent was removed, thereby obtaining 232.6 g of the polymer A-1 containing ruthenium as the component (A). White powder). The weight average molecular weight (Mw) of the polymer A-1 containing ruthenium was analyzed by GPC under the following conditions, and as a result, Mw = 15000 (in terms of polystyrene). (Measurement conditions of GPC) Column: SuperMultipore HZ-M Development solvent: tetrahydrofuran [Production Example 2] Synthesis of B-1, 100 parts of 1,3,5,7-tetramethylcyclotetraoxane, divinyl 100 parts of benzene, 60 parts of toluene, and 0.0005 parts of a platinum-carbonylvinylmethyl complex (Ossko catalyst) were stirred and refluxed for 5 hours. The solvent was distilled off under reduced pressure from the reaction liquid at 70 ° C to obtain a prepolymer B-1 as a component (B). The analysis was carried out by GPC under the above conditions, and the weight average molecular weight of the prepolymer B-1 was Mw = 140,000 (in terms of polystyrene), and the content of hydroquinone (Si-H group) was determined. ¹ H-NMR was 5.3 mmol/g. [化27] [Example 1] Production of curable composition containing bismuth Using the compounds shown in Table 1, the composition compositions Nos. 1 to 28 were produced in the composition of Table 2. [Table 2] [Comparative Example 1] Comparative Production Compositions 1 to 30 were prepared by using the compounds shown in Table 1 and the following Comparative Compounds 1 to 3 for the production of the curable composition containing cerium. [化28] [table 3] [Example 2] Production of cured product 1 Example compositions No. 1 to No. 28 were respectively flown into a mold set on a silver substrate (length 50 mm × width 55 mm × thickness 0.25 mm) at 170 ° C Heating was carried out under conditions of 180 seconds (forming step), followed by heating at 150 ° C for 2 hours (post-baking step), thereby forming a pudding cup having a diameter of 3.5 mm × a height of 4 mm. Examples of hardened materials No. 1~28. [Comparative Example 2] Production of Comparative Hardened Material 1 Comparative Example Composition No. 1 to No. 30 were respectively flown into a mold set on a silver substrate (length 50 mm × width 55 mm × thickness 0.25 mm) at 170 Heating was carried out under conditions of 180 seconds (forming step) at ° C, followed by heating at 150 ° C for 2 hours (post-baking step), thereby forming a pudding cup having a diameter of 3.5 mm × a height of 4 mm. Comparative examples of cured materials 1 to 30. [Evaluation Example 1] Pudding Cup Test 1 (Silver Substrate) The pudding cup test was carried out on the cured products Nos. 1 to 28 and the cured products 1 to 30 of the comparative examples in the following manner. That is, the adhesion force between the silver matrix and the molding resin is measured using an adhesion tester, and the adhesion is higher than 20 kg/cm. ² The situation is set to ++ and will be 5~20 kg/cm ² The range of the range is set to +, which will be less than 5 kg/cm ² The case was set to - and the adhesion was evaluated. When the evaluation result is +, it means that the excellent adhesion is exhibited, and in the case of ++, it means that the adhesion is particularly excellent. The results are shown in Tables 3-1 to 3-4. [Table 3-1] [Table 3-2] [Table 3-3] [Table 3-4] According to Tables 3-1 to 3-4, the adhesion of the cured products 1 to 30 of the comparative examples was inferior. On the other hand, the cured articles Nos. 1 to 28 of the examples using the curable composition containing bismuth of the present invention have good adhesion to the silver base. Among them, the cured articles Nos. 1 to 18 of the examples have very high adhesion. [Example 3] Production of cured product 2 Example compositions No. 1 to No. 28 were respectively flown into a mold set on a copper substrate (length 50 mm × width 55 mm × thickness 0.25 mm) at 170 ° C Heating was carried out under conditions of 180 seconds (forming step), followed by heating at 150 ° C for 2 hours (post-baking step), thereby forming a pudding cup having a diameter of 3.5 mm × a height of 4 mm. Examples of hardened materials No. 29~56. [Comparative Example 3] Production of Comparative Cured Product 2 Comparative Example Composition No. 1 to No. 30 were respectively flown into a mold set on a copper substrate (length 50 mm × width 55 mm × thickness 0.25 mm) at 170 Heating was carried out under conditions of 180 seconds (forming step) at ° C, followed by heating at 150 ° C for 2 hours (post-baking step), thereby forming a pudding cup having a diameter of 3.5 mm × a height of 4 mm. Comparative examples of cured products 31 to 60. [Evaluation Example 2] Pudding cup test 2 (copper substrate) The pudding cup test was carried out on the cured products Nos. 29 to 56 and the cured products 31 to 60 of the comparative examples in the following manner. That is, the adhesion force between the copper substrate and the molding resin is measured using an adhesion tester, and the adhesion is higher than 20 kg/cm. ² The situation is set to ++ and will be 5~20 kg/cm ² The range of the range is set to +, which will be less than 5 kg/cm ² The case was set to - and the adhesion was evaluated. When the evaluation result is +, it means that the excellent adhesion is exhibited, and in the case of ++, it means that the adhesion is particularly excellent. The results are shown in Tables 4-1 to 4-4. [Table 4-1] [Table 4-2] [Table 4-3] [Table 4-4] According to Tables 4-1 to 4-4, the adhesion of the cured products 31 to 60 of the comparative examples was inferior. On the other hand, the cured articles Nos. 29 to 56 of the examples using the cerium-containing curable composition of the present invention have good adhesion to the copper substrate. [Industrial Applicability] According to the present invention, it is possible to provide a curable composition containing ruthenium which is excellent in adhesion to a silver base or a copper base and which can be used for a cured product such as an electric/electronic material. The curable composition containing cerium has good curability, and can be molded by a die such as transfer molding or injection molding, and the cured product is preferably used for heat resistance, crack resistance, and mechanical strength. A sealing material for a semiconductor, a sealing material for an LED, a molding material for a package for a white LED, and the like.

Claims (3)

A curable composition containing cerium, which comprises the following components: a compound containing a carbon-carbon double bond having reactivity with an SiH group as the component (A) and a SiH group as a component (B) An oxane compound, a decane compound represented by the following formula (1) as a component (C), and a filler as the component (D), (wherein R ¹ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, A represents an alkanediyl group having 1 to 10 carbon atoms, and k represents a number of 2 or 3). A method of hardening a curable composition containing cerium, which comprises the step of heating a curable composition containing cerium according to claim 1 to harden the sclerosing composition containing cerium. A cured product obtained by hardening a curable composition containing cerium according to claim 1.