KR101594343B1 - Curable composition and method for producing thereof, cured product, and optical semiconductor device - Google Patents

Abstract

(C) A curable composition characterized by containing a polysiloxane (A) having an alkenyl group, a saturated hydrocarbon compound (B) and a polysiloxane (D) having at least two silicon atom-bonded hydrogen atoms per molecule.
(Effect) The curable composition of the present invention can form a cured product having sufficiently reduced tackiness. The optical semiconductor device having a cured product formed of the curable composition of the present invention as an encapsulating material or the like is less likely to adhere to dust or the like on the surface of the cured product and the packages are adhered to each other in a part feeder used for sorting products There is little concern that such problems will occur.

Description

TECHNICAL FIELD [0001] The present invention relates to a curable composition, a method of producing the same, a cured product, and a optical semiconductor device,

The present invention relates to a curable composition, a method for producing the same, a cured product, and an optical semiconductor device.

The addition-curable silicone rubber composition is used in various applications such as package encapsulant for LED in that it forms a cured product having excellent properties such as weather resistance, heat resistance, hardness and elongation. However, there is a problem that dust adheres to the surface of the cured product, and the packages adhere to each other in a parts feeder used for sorting products.

In order to eliminate the tack, a hard silicone resin may be used, but the cured product thereof has a low impact resistance, and cracks tend to occur particularly due to thermal shock.

Thus, a method of improving the strength of the cured product by compounding an organopolysiloxane in the form of a resin to the addition-curing type silicone rubber composition using the properties of both, and a method of coating a resin on the cured product of the addition curing type silicone rubber composition, etc. (Patent Documents 1 and 2).

Japanese Patent Application Laid-Open No. 2007-99835 Japanese Patent Application Laid-Open No. 2007-103494

An object of the present invention is to provide a curable composition capable of obtaining a cured product having reduced tackiness, a process for producing the same, a cured product obtained from the curable composition, and an optical semiconductor device having the cured product.

The present invention for achieving the above object is as follows.

[1] A curable composition containing a polysiloxane (A) having an alkenyl group, a saturated hydrocarbon compound (B) and a polysiloxane (D) having at least two silicon atom-bonded hydrogen atoms per molecule.

[2] The curable composition according to the above [1], wherein the boiling point of the saturated hydrocarbon compound (B) is 50 ° C to 150 ° C under 1 atm.

[3] The curable composition according to [1] or [2], wherein the content of the saturated hydrocarbon compound (B) is 0.1 to 5000 ppm.

[4] The curable composition according to any one of [1] to [3], wherein the saturated hydrocarbon compound (B) is a saturated alicyclic hydrocarbon compound.

[5] The curable composition according to any one of [1] to [4], wherein the polysiloxane (A) having an alkenyl group is a polysiloxane having an aryl group.

[6] A process for producing a curable composition comprising a polysiloxane (A) having an alkenyl group, a saturated hydrocarbon compound (B) and a polysiloxane (D) having at least two silicon atom-bonded hydrogen atoms per molecule, ) And the polysiloxane (D) are synthesized by using the saturated hydrocarbon compound (B) as a synthesis solvent, and a concentrate of the obtained polysiloxane-containing synthesis solution is used.

[7] A cured product obtained by curing the curable composition according to any one of [1] to [5].

[8] A semiconductor optical device having a semiconductor light emitting element and the cured body according to [7], which covers the semiconductor light emitting element.

The curable composition of the present invention can form a cured product having sufficiently reduced tackiness. The optical semiconductor device having a cured product formed of the curable composition of the present invention as an encapsulating material or the like is less likely to adhere to dust or the like on the surface of the cured product and the packages are adhered to each other in a part feeder used for sorting products There is little concern that such problems will occur.

1 is a schematic view showing one specific example of a photosemiconductor device.

(Mode for carrying out the invention)

≪ Curable composition >

The curable composition of the present invention contains a polysiloxane (A) having an alkenyl group, a saturated hydrocarbon compound (B) and a polysiloxane (D) having at least two silicon atom-bonded hydrogen atoms per molecule. The curable composition of the present invention may further contain a catalyst (C) for hydrosilylation reaction and an additive.

In the present invention, "polysiloxane" means a compound having a molecular skeleton in which two or more siloxane units (Si-O) are bonded.

Polysiloxane  (A)

The polysiloxane (A) is a polysiloxane having an alkenyl group. The polysiloxane (A) is the main component of the composition and is cured by the hydrosilylation reaction with the polysiloxane (D) to become the main component of the cured product.

The polysiloxane (A) is not particularly limited as long as it can be cured by a hydrosilylation reaction with the polysiloxane (D).

The polysiloxane (A) may be the same compound as the polysiloxane (D). That is, the polysiloxane (A) and the polysiloxane (D) may be a polysiloxane having an alkenyl group and at least two silicon-bonded hydrogen atoms in the same molecule. Such a polysiloxane functions as a main agent and a crosslinking agent of the present composition.

Examples of the alkenyl group of the polysiloxane (A) include vinyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, heptenyl, . Of these, a vinyl group, an allyl group and a hexenyl group are preferable.

The content of the alkenyl group in the polysiloxane (A) is preferably from 3 to 50 mol%, more preferably from 5 to 40 mol%, based on 100 mol% of all the Si atoms contained in the polysiloxane (A) Mol%, and more preferably 10 to 30 mol%. When the content of the alkenyl group is within the above range, the hydrosilylation reaction between the polysiloxane (A) and the polysiloxane (D) proceeds appropriately, and a cured product having high strength can be obtained.

The polysiloxane (A) is preferably a polysiloxane having an aryl group.

When the polysiloxane (A) has an aryl group, a characteristic that a high luminance is obtained when used as an LED encapsulant is exhibited. When the total number of Si atoms contained in the polysiloxane (A) is 100 mol%, the content of the aryl group in the polysiloxane (A) is preferably 30 to 120 mol%, more preferably 50 to 110 mol% %, More preferably 70 to 100 mol%. When the content of the aryl group is within the range of 30 to 120 mol%, a cured film having a high luminance and a high refractive index can be obtained from the composition. Examples of the aryl group include a phenyl group, a tolyl group, a xylyl group, and a naphthyl group.

The polysiloxane (A) is preferably a polysiloxane represented by the following formula (1). When the polysiloxane (A) has a siloxane unit in which two aryl groups are bonded to the same silicon atom constituting the polysiloxane chain, the humidity resistance of the cured product obtained from the curable composition of the present invention is enhanced.

(Wherein R ¹ , R ² and R ³ each independently represent an alkyl group, an alkenyl group, an aryl group or a glycidoxyalkyl group;

R ^Ar1 represents an aryl group;

X represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms;

a, c, e and f each independently represent an integer of 0 or more;

b and d each independently represent an integer of 1 or more)

In the formula (1), R ¹ , R ² and R ³ each independently represent an alkyl group, an alkenyl group, an aryl group or a glycidoxyalkyl group;

That is, with respect to one siloxane unit (structural unit) to which the symbol a is attached, the three R ^{1 s} present may be, independently of each other, an alkyl group, an alkenyl group, an aryl group or glycidoxyalkyl. For example, when two or more R < ^{1 >} of three R < ^{1 >} are alkyl groups, the alkyl groups may be the same alkyl group or different alkyl groups. When the symbol a is an integer of 2 or more, the siloxane units attached with the symbol a may be the same or different. R ² and R ³ are also the same as R ¹ .

However, R ^3, at least two of the dog by the numeral R ² and the sign of a is present in R ^1, the siloxane units of the sign c attached present in the attached siloxane units, d present on the attached siloxane units is an alkenyl group, the formula (1 ) Of at least two alkenyl groups in one molecule of the polysiloxane (A). For example, ^{one out} of three R &^lt; 1 > groups present in one siloxane unit attached with the symbol a is an alkenyl group and two or more siloxane units may be present. Two or more of the three R < ¹ > s present in one siloxane unit attached with the symbol a may be an alkenyl group, and at least one siloxane unit may be present. ^One of the three R ^{1 s} present in one siloxane unit attached with the symbol a is an alkenyl group, one siloxane unit is present, and one of the two R ² groups present in one siloxane unit, And one or more siloxane units may be present.

Further, when two of R ^2, R ² is an aryl group of one of the coupling for the siloxane units, a code c attached, to the same silicon atoms, R ² and the other terminal is not an aryl group.

Examples of the alkyl group include a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, And adamantyl group. Among these, a methyl group is preferable.

Examples of the alkenyl group include vinyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, heptenyl, hexenyl and cyclohexenyl. Of these, a vinyl group, an allyl group and a hexenyl group are preferable.

Examples of the aryl group include a phenyl group, a tolyl group, a xylyl group, and a naphthyl group. Among them, a phenyl group is preferable.

Examples of the glycidoxyalkyl group include glycidoxypropyl and the like.

In the formula (1), R ^Ar1 represents an aryl group. The aryl group represented by R ^Ar1 is the same as the aryl group represented by R ¹ , R ² and R ³ .

In the formula (1), X represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

In the formula (1), a, c, e and f each independently represent an integer of 0 or more. b and d each independently represent an integer of 1 or more.

The polysiloxane (A) has a siloxane unit bonded with the symbol b, that is, a siloxane unit in which two aryl groups are bonded to the same silicon atom constituting the polysiloxane chain, whereby the moisture resistance of the cured product obtained from the present curable composition is improved.

When the sum of a, b, c, d, e and f is 100%, the ratio of a is preferably 0 to 70%, more preferably 0 to 40%. b is preferably from 1 to 70%, more preferably from 1 to 40%. c is preferably 0 to 70%, and more preferably 0 to 40%. d is preferably from 1 to 80%, more preferably from 30 to 70%. The proportion of e is preferably 0 to 50%, more preferably 0 to 20%. The ratio of f is preferably 0 to 40%, more preferably 0 to 10%.

The polysiloxane (A) preferably has a weight average molecular weight in terms of polystyrene measured by gel permeation chromatography in the range of 100 to 50000, more preferably 500 to 5000. When the weight average molecular weight of the polysiloxane (A) is within the above range, the sealant is easily handled when the sealant is produced using the composition, and the cured product obtained from the composition has sufficient strength as the optical semiconductor encapsulant.

As a method for producing the polysiloxane (A), there are known methods for producing the polysiloxane (A) in JP-A 6-9659, JP-A 2003-183582, JP-A 2007-008996, JP-A 2007-106798, 2007-169427 and JP-A-2010-059359, for example, a method of co-hydrolyzing chlorosilane or alkoxysilane as each unit source in a suitable synthesis solvent, and a method of co- And a method in which the decomposition product is subjected to equilibration reaction with an alkali metal catalyst or the like. When the polysiloxane (A) is synthesized by using the saturated hydrocarbon compound (B) as the synthetic solvent, the resulting polysiloxane (A) -containing synthetic solution contains the saturated hydrocarbon compound (B) , The operation of adding the saturated hydrocarbon compound (B) can be omitted.

The saturated hydrocarbon compound (B)

The curable composition of the present invention contains a saturated hydrocarbon compound (B) together with the polysiloxane (A) and the polysiloxane (D), whereby a cured product having sufficiently reduced tackiness can be formed.

Examples of the saturated hydrocarbon compound (B) include saturated aliphatic hydrocarbon compounds such as n-pentane (36 ° C), n-hexane (69 ° C), n-heptane (98 ° C) and n-octane (126 ° C);

Saturated alicyclic hydrocarbons such as methyl cyclohexane (101 DEG C), cyclohexane (81 DEG C), ethyl cyclohexane (130 DEG C), dimethyl cyclohexane (124 DEG C), cycloheptane (118 DEG C) compound;

(Parentheses indicate the boiling point under 1 atm). Among these, a saturated alicyclic hydrocarbon compound is preferred because it can more effectively reduce the tack of the cured product.

The boiling point of the saturated hydrocarbon compound (B) is preferably 50 占 폚 to 150 占 폚, more preferably 70 to 140 占 폚, and even more preferably 80 to 130 占 폚 under 1 atm. If the boiling point of the saturated hydrocarbon compound (B) is 50 占 폚 to 150 占 폚 under 1 atm, the tack of the cured product can be further reduced.

In the curable composition of the present invention, the content ratio of the saturated hydrocarbon compound (B) is preferably 0.1 to 5000 ppm, more preferably 0.1 to 1000 ppm, and still more preferably 0.1 to 100 ppm. When the content of the saturated hydrocarbon compound (B) is within the above range, the curing product can be more effectively reduced.

Polysiloxane  (D)

The polysiloxane (D) is a polysiloxane having at least two silicon-bonded hydrogen atoms per molecule. That is, the polysiloxane (D) has at least two Si-H groups (hydrosilyl groups) per molecule. The polysiloxane (D) is a crosslinking agent for the polysiloxane (A) and forms a cured product by a hydrosilylation reaction with the polysiloxane (A).

The polysiloxane (D) may be a polysiloxane having at least two silicon-bonded hydrogen atoms per molecule, which is used as a crosslinking agent in a conventional hydrosilyl-based polysiloxane composition.

As described above, the polysiloxane (D) may be the same compound as the polysiloxane (A).

Specific examples of the polysiloxane (D) include organohydrogenpolysiloxanes described in Patent Documents 1 to 3 and the like.

The polysiloxane (D) can be produced, for example, by reacting an alkoxysilane such as phenyltrimethoxysilane or diphenyldimethoxysilane with a hydrogen siloxane such as 1,1,3,3-tetramethyldisiloxane by a known method In a suitable synthetic solvent. When the polysiloxane (D) is synthesized by using the saturated hydrocarbon compound (B) as the synthetic solvent, the resulting polysiloxane (D) -containing synthetic solution contains the saturated hydrocarbon compound (B) , The operation of adding the saturated hydrocarbon compound (B) can be omitted.

The content of the polysiloxane (D) in the curable composition of the present invention is preferably such that the molar ratio of the amount of silicon atom-bonded hydrogen atoms in the polysiloxane (D) to the amount of alkenyl groups in the polysiloxane (A) is 0.1 to 5, Preferably 0.5 to 2, and more preferably 0.7 to 1.4. When the content of the polysiloxane (D) is within the above range, the curing of the composition proceeds sufficiently, and the obtained cured product has sufficient heat resistance.

Hydrosilylation  The reaction catalyst (C)

The hydrosilylation reaction catalyst (C) is a catalyst for promoting the hydrosilylation reaction.

The hydrosilylation reaction catalyst (C) can be used without particular limitation, as long as it is a catalyst that is used as a hydrosilylation reaction catalyst in a conventional hydrosilyl-based polysiloxane composition.

Specific examples of the hydrosilylation reaction catalyst (C) include platinum-based catalysts, rhodium-based catalysts, and palladium-based catalysts. Among these, platinum-based catalysts are preferable from the viewpoint of promoting curing of the composition. Platinum-based catalysts include platinum-alkenylsiloxane complexes and the like. Examples of the alkenylsiloxane include 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetravinyl Cyclotetrasiloxane, and the like. Particularly, from the viewpoint of stability of the complex, 1,3-divinyl-1,1,3,3-tetramethyldisiloxane is preferable.

The catalyst (C) for the hydrosilylation reaction in the curable composition of the present invention is an amount such that the hydrosilylation reaction between the polysiloxane (A) and the polysiloxane (D) proceeds practically, for example, 0.01 ppm to 10000 ppm .

additive

As long as the object of the present invention is achieved, the curable composition of the present invention may contain, for example, inorganic fillers such as fine particulate silica such as fumed silica and quartz powder, titanium oxide, zinc oxide, , A reaction retarder such as cyclo-tetramethyltetravinyltetrasiloxane, a diluent such as diphenylbis (dimethylvinylsiloxy) silane, phenyltris (dimethylvinylsiloxy) silane or diphenylbis (dimethylhydroxysiloxy) silane , Pigments, flame retardants, heat resistance agents, antioxidants, and the like.

Method for producing a composition

The curable composition of the present invention is obtained by mixing the above components, that is, the polysiloxane (A), the saturated hydrocarbon compound (B), the polysiloxane (D), the catalyst for hydrosilylation reaction (C) And then mixing them uniformly.

It is also possible to synthesize a polysiloxane such as polysiloxane (A) or polysiloxane (D) by using a saturated hydrocarbon compound (B) as a synthesis solvent, and to concentrate the obtained polysiloxane-containing synthesis solution in a hydrosilylation reaction catalyst (C) , And the like.

The viscosity of the curable composition of the present invention at 25 占 폚 is preferably 1 to 1000000 mPa 占 퐏, and more preferably 10 to 10000 mPa 占 퐏. When the viscosity is within this range, the operability of the composition is improved.

The curable composition of the present invention may be prepared as a single solution, or may be prepared by dividing into two solutions, and two solutions may be mixed at the time of use. If necessary, a small amount of a curing inhibitor such as acetylene alcohol may be added.

<Hard goods>

A cured product can be obtained by curing the curable composition of the present invention.

Examples of the method of curing the curable composition of the present invention include a method of applying the curable composition on a substrate and then heating at 100 to 180 캜 for 1 to 13 hours.

<Optical Semiconductor Device>

The optical semiconductor device of the present invention has a semiconductor light emitting element and the cured product covering the semiconductor light emitting element. The optical semiconductor device of the present invention is obtained by covering the curable composition with a semiconductor light emitting element and curing the composition. The method of curing the curable composition is as described above.

Examples of the optical semiconductor device include an LED (Light Emitting Diode) and an LD (Laser Diode).

1 is a schematic view of one embodiment of the optical semiconductor device of the present invention. The optical semiconductor device 1 includes an electrode 6, a semiconductor light emitting element 2 provided on the electrode 6 and electrically connected to the electrode 6 by a wire 7, And a sealing material 4 filled in the reflector 3 and sealing the semiconductor light emitting element 2. The sealing material 4 is obtained by curing the curable composition of the present invention. Particles 5 such as silica and fluorescent material are dispersed in the sealing material 4.

As described above, since the tackiness of the encapsulating material (cured product) obtained by curing the curable composition of the present invention is small, there is little concern that dust or the like adheres to the encapsulating material, and in the part feeder used for sorting products, It is unlikely that the packages will stick together.

(Example)

One. Polysiloxane  synthesis

1-1. Structural analysis

The structure of the polysiloxane was analyzed by ²⁹ Si NMR and ¹³ C NMR.

1-2. Weight average molecular weight

The weight average molecular weight (Mw) was determined by gel permeation chromatography (GPC) under the following conditions and was found as a polystyrene reduced value.

Device: HLC-8120C (manufactured by Toso Co., Ltd.)

Column: TSK-gel MultiporeHXL-M (manufactured by Toso Co., Ltd.)

Eluent: THF, flow rate 0.5 mL / min, loading 5.0%, 100 μL

1-3. Polysiloxane  synthesis

[Synthesis Example 1] Synthesis of polysiloxane (A-1)

Necked flask equipped with a stirrer, a reflux condenser, an inlet, and a thermometer was charged with 37.3 g of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 234 g of phenyltrimethoxysilane, 97.7 g of diphenyldimethoxysilane 55 g of water, 0.3 g of trifluoromethanesulfonic acid, and 146 g of methylcyclohexane as a polymerization solvent were added and mixed, and the mixture was heated under reflux for 1 hour. After cooling, the lower layer was separated and removed, and the upper layer of the methyl cyclohexane solution layer was water-filtered. To the water-washed methylcyclohexane solution layer were added 30 g of water, 0.3 g of potassium hydroxide and 4.4 g of 3-glycidoxypropylmethyldimethoxysilane, and the mixture was heated under reflux for 1 hour. Then, the methanol was distilled off, and excess water was removed by azeotropic dehydration. The mixture was heated under reflux for 4 hours. After the reaction, the methylcyclohexane solution was cooled, neutralized with 0.3 g of acetic acid, and then water-filtered. After removal of water, evaporated methylcyclohexane under reduced pressure, methylcyclohexyl concentrating the hexane solution, the average unit expression, and _{(ViMe 2 SiO 1/2)} 20 (PhSiO 3/2) 59 (Ph 2 SiO 2/2) ₂₀ (EpMeSiO _{2/2) 1,} to obtain a methyl cyclohexane solution containing polysiloxane (a-1) represented by (Vi is a vinyl group, Me is a methyl group, Ph is a phenyl group, Ep represents an glycidoxypropyltrimethoxysilane). The weight average molecular weight of the polysiloxane (A-1) was 1,600.

[Synthesis Example 2] Synthesis of polysiloxane (A-2)

Necked flask equipped with a stirrer, a reflux condenser, an inlet, and a thermometer was charged with 37.3 g of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 234 g of phenyltrimethoxysilane, 97.7 g of diphenyldimethoxysilane , 55 g of water, 0.3 g of trifluoromethanesulfonic acid and 146 g of toluene as a polymerization solvent were added and mixed, and the mixture was heated under reflux for 1 hour. After cooling, the lower layer was separated and removed, and the upper toluene solution layer was water-filtered. To the water-washed toluene solution layer were added 30 g of water, 0.3 g of potassium hydroxide and 4.4 g of 3-glycidoxypropylmethyldimethoxysilane, and the mixture was heated under reflux for 1 hour. Then, the methanol was distilled off, and excess water was removed by azeotropic dehydration. The mixture was heated under reflux for 4 hours. After the reaction, the toluene solution was cooled, neutralized with 0.3 g of acetic acid, and water-filtered. After removal of water, to distil off the toluene under reduced pressure to concentrate the toluene solution, and the average unit _{expression, (ViMe 2 SiO 1/2} ) 20 (PhSiO 3/2) 59 (Ph 2 SiO 2/2) 20 (EpMeSiO 2 _{/ 2} ) ₁ (Vi is a vinyl group, Me is a methyl group, Ph is a phenyl group, and Ep is a glycidoxypropyl group). The weight-average molecular weight of the polysiloxane (A-2) was 1,600.

[Synthesis Example 3] Synthesis of polysiloxane (D-1)

220 g of diphenyldimethoxysilane and 0.6 g of trifluoromethanesulfonic acid were added to a four-necked flask equipped with a stirrer, a reflux condenser, an inlet and a thermometer, and 60.5 g of 1,1,3,3-tetramethyldisiloxane was added thereto While stirring, 108 g of acetic acid was added dropwise over 30 minutes. After completion of dropwise addition, the mixture was heated to 50 캜 while stirring, and reacted for 3 hours. Subsequently, the temperature was raised to 80 DEG C and the reaction was carried out for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, toluene and water were added, mixed well and allowed to stand, and the aqueous layer was separated and removed. The toluene solution layer as the upper layer was washed with water three times and then concentrated under reduced pressure to obtain a polysiloxane (D-1) represented by the following formula (2).

[Synthesis Example 4] Synthesis of polysiloxane (A-3)

81 g of diphenyldimethoxysilane and 0.2 g of trifluoromethanesulfonic acid were added to a four-necked flask equipped with a stirrer, a reflux condenser, an inlet, and a thermometer, followed by mixing to obtain 1,3-divinyl-1,1,3,3-tetra 62 g of methyldisiloxane were added and 60 g of acetic acid was added dropwise over 30 minutes while stirring. After completion of dropwise addition, the mixture was heated to 50 캜 while stirring, and reacted for 3 hours. After the completion of the reaction, the mixture was cooled to room temperature, toluene and water were added, mixed well, and the aqueous layer was separated and removed. The toluene solution layer as the upper layer was washed with water three times and then concentrated under reduced pressure to obtain diphenylbis (dimethylvinylsiloxy) silane (hereinafter referred to as polysiloxane (A-3)).

2. Preparation of a curable composition

2-1. Of methylcyclohexane  Content ratio

The content ratio of methylcyclohexane and toluene was measured by gas column chromatography (GC) under the following conditions.

Device: Agilent Technologies 7890A

Column: DB-1701

Detector: FID.

2-2. Preparation of curable composition

[Example 1]

The methyl cyclohexane solution of the polysiloxane (A-1) obtained in Synthesis Example 1 was concentrated to obtain a concentrate (1) containing polysiloxane (A-1). The polysiloxane (A-1) containing concentrate (1), polysiloxane (A-3), the following C-1, the following D-1 and the following E-1 component were mixed in the ratios shown in the following Table 1, A composition was obtained. The methylcyclohexane (component B) contained in the curable composition was derived from the polymerization solvent of Synthesis Example 1. [

[Examples 2 and 3]

The methylcyclohexane solution of the polysiloxane (A-1) obtained in Synthesis Example 1 was concentrated to obtain a concentrate 2 containing the polysiloxane (A-1) having a high degree of concentration from the concentrate 1 containing the polysiloxane (A- And a concentrate (3) containing polysiloxane (A-1) having a higher degree of concentration were obtained. The components were mixed in the proportions shown in the following Table 1 in the same manner as in Example 1 except that the polysiloxane (A-1) -containing concentrated liquid 2 was used in place of the polysiloxane (A-1) The curable composition of Example 2 was obtained. The components were mixed in the proportions shown in the following Table 1 in the same procedure as in Example 1 except that the polysiloxane (A-1) -containing concentrate 3 was used in place of the polysiloxane (A-1) A curable composition of Example 3 was obtained. The methylcyclohexane (component B) contained in each of the curable compositions is derived from the polymerization solvent of Synthesis Example 1. [

[Comparative Example 1]

Toluene was distilled off from the toluene solution of the polysiloxane (A-2) obtained in Synthesis Example 2 to obtain a polysiloxane (A-2). Each component was mixed at the ratios shown in Table 1 below to obtain a curable composition of Comparative Example 1 containing no methylcyclohexane (component B).

Details of each component in Table 1 are as follows.

C-1: Complex of platinum with 1,3-divinyl-1,1,3,3-tetramethyldisiloxane (amount of platinum metal: 4% by mass)

E-1: Ethynyl cyclohexanol

3. Evaluation of the curable composition

The curable compositions of Examples 1 to 3 and Comparative Example 1 were evaluated by the following methods 3-1 to 3-3. The evaluation results are shown in Table 1 above.

3-1. Viscosity

The viscosity of the curable composition was measured at 25 캜 using an E-type viscometer.

3-2. Hardness

The curable composition was coated on a flat plate of Teflon (trade name) with a 2 mm thick rim to have a rim height, and heated in a hot air circulating oven at 150 캜 for 5 hours to prepare a 50 mm long, 50 mm wide, A cured product was produced. The hardness of the cured product was measured by a Type D durometer specified in JIS K6253.

3-3-1. Tack (evaluation by facilitation)

The curable composition was coated on a flat plate of Teflon with a rim of 2 mm in thickness so as to have a rim height and heated in a hot air circulating oven at 150 캜 for 5 hours to obtain a cured product having a length of 50 mm, . The surface of the cured product was touched with a finger, and its tack was evaluated based on the following criteria.

A: No stickiness

B: Sticky

3-3-2. Tack (Evaluation by tack testing device)

The curable composition was coated on a smooth substrate to a thickness of 100 mu m and heated in a hot air circulating oven at 150 DEG C for 5 hours to prepare a cured product. The obtained cured product was measured by a tester. Details of the measurement method are as follows.

Device name: TAC-1000 (manufactured by Resca Co., Ltd.)

Terminal: SUS 10mmφ

Terminal temperature: 25 ℃

Suction pressure: 0.05 MPa

Indentation time: 60 seconds

Claims (8)

(A) having an alkenyl group, a saturated hydrocarbon compound (B) and a polysiloxane (D) having at least two silicon atom-bonded hydrogen atoms per molecule, wherein the polysiloxane (A) has an aryl group and the polysiloxane Wherein the content of the aryl group is 30 to 120 mol% when the total number of Si atoms contained in the compound (A) is 100 mol%. The method according to claim 1,
Wherein the boiling point of the saturated hydrocarbon compound (B) is 50 占 폚 to 150 占 폚 under 1 atm. The method according to claim 1,
Wherein the content ratio of the saturated hydrocarbon compound (B) based on the total weight of the curable composition is 0.1 to 5000 ppm. The method according to claim 1,
Wherein the saturated hydrocarbon compound (B) is a saturated alicyclic hydrocarbon compound. delete delete A cured product obtained by curing the curable composition according to any one of claims 1 to 4. A semiconductor optical device having a semiconductor light emitting element and the cured body according to claim 7 which covers the semiconductor light emitting element.

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