JP2008019422A - Epoxy-silicone mixed resin composition and light emitting semiconductor device - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an epoxy-silicone mixed resin composition suitable as a light emitting semiconductor covering protective material having, as basic properties, transparency, no surface tackiness, and excellent transparency in the reflow test; and a light emitting semiconductor device covered by the same. <P>SOLUTION: The epoxy-silicone mixed resin composition comprises, as essential ingredients, (A) an organopolysilsesquioxane resin having at least two epoxy functional groups or oxetanyl groups in one molecule, (B) an epoxy resin having at least two epoxy functional groups in one molecule, (C) a curing agent, and (D) a curing catalyst, characterized in that the curing catalyst contains at least one quaternary phosphonium salt. As for the epoxy-silicone mixed resin composition of the invention, a cured material thereof is used to protectively cover a light emitting semiconductor element to thereby inhibit discoloration in the reflow test, and accordingly, a light emitting semiconductor device excellent in mounting reliability can be provided, which gives enormous industrial merits. Further, a cured material having a glass transition point of 130°C or higher is particularly utterly free of dust adhesion on the surface of the cured material and has excellent crack resistance in a heat resistance test. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention is an epoxy-silicone hybrid resin composition that is effective as a light-emitting semiconductor coating protective material excellent in transparency in a reflow test while maintaining transparency and no surface tack as a basic performance, and using the same The present invention relates to a light emitting semiconductor device formed by coating a light emitting semiconductor element.

As a resin composition for protecting a light-emitting semiconductor element such as a light-emitting diode (LED), the cured product is required to have transparency, and is generally an epoxy such as a bisphenol A type epoxy resin or an alicyclic epoxy resin. What is obtained using resin and an acid anhydride type hardening | curing agent is used (patent document 1: patent 3241338 gazette, patent document 2: Unexamined-Japanese-Patent No. 7-25987).
However, even in such a transparent epoxy resin, the moisture absorption resistance of the resin is high, so the moisture resistance durability is low, particularly the light resistance to low-wavelength light is low, so the light resistance is low, or it is colored due to light deterioration. Had.

Therefore, it consists of an organic compound containing at least two carbon-carbon double bonds reactive with SiH groups in one molecule, a silicon compound containing at least two SiH groups in one molecule, and a hydrosilylation catalyst. Resin compositions for protecting the coating of optical semiconductor elements have also been proposed (see Patent Document 3: Japanese Patent Laid-Open No. 2002-327126, Patent Document 4: Japanese Patent Laid-Open No. 2002-338833).
However, such a silicone-based cured product generally has a drawback that when it is intended to improve crack resistance, tack remains on the surface of the cured product, dust easily adheres, and impairs light transmission.
Therefore, what uses the high hardness silicone resin for protective coating is proposed (refer patent document 5: Unexamined-Japanese-Patent No. 2002-314139, patent document 6: Unexamined-Japanese-Patent No. 2002-314143).

  However, these high-hardness silicone resins still have poor adhesion, and in case-type light-emitting semiconductor devices in which light-emitting elements are arranged in a ceramic and / or plastic housing and the inside of the housing is filled with silicone resin, In the thermal shock test at 120 ° C., there has been a problem that the silicone resin is peeled off from the ceramic or plastic of the casing.

  In addition, as a composition that can compensate for these drawbacks, the epoxy and silicone composition disclosed in JP-A-52-107049 (see Patent Document 7) also has problems of adhesive strength and discoloration.

  In recent years, due to market demands such as miniaturization, thinning, and environmental friendliness of optical semiconductor element packages, mounting by lead-free solder is required, and high mounting reliability, particularly high-temperature reflow resistance is required. Yes. In particular, for optical semiconductor applications, it is important to maintain transparency during the reflow test.

  On the other hand, as for silsesquioxane, which is a network-type oligomer containing silicon, for example, a sealing resin for light-emitting diodes obtained by cationically curing an epoxy group and / or oxetanyl group-containing silsesquioxane is known ( Patent Document 8: Japanese Patent Application Laid-Open No. 2004-238589).

  However, a cured product with a cationic curing agent is poor in flexibility, and when such a resin is used as a sealing material for a light emitting diode, a large stress occurs between the light emitting element and the sealing resin during heating or cooling, Resin cracking, peeling of the sealing resin from the housing, bonding wire breakage, etc. are induced, leading to a reduction in output or failure of the light emitting diode.

  Further, a resin composition for encapsulating an optical semiconductor comprising a silsesquioxane having at least two epoxy rings, an epoxy resin, an acid anhydride-based curing agent, and a curing catalyst and B-staged is disclosed (patent) Reference 9: Japanese Patent Laid-Open No. 2005-263869), regarding the selection of the curing catalyst, there is no disclosure or suggestion regarding the possibility of coloring during the reflow test.

Japanese Patent No. 3241338 JP 7-25987 A JP 2002-327126 A JP 2002-338833 A JP 2002-314139 A JP 2002-314143 A JP-A 52-107049 JP 2004-238589 A JP 2005-263869 A

  The present invention has been made in view of the above circumstances, and is an epoxy / silicone hybrid resin composition suitable as a light-emitting semiconductor coating protective material that is transparent as a basic performance, has no surface tackiness, and has excellent transparency during a reflow test. It is an object of the present invention to provide an object and a light emitting semiconductor device coated with the object.

As a result of intensive studies to achieve the above object, the present inventor has (A) an organopolysilsesquioxane resin having at least two epoxy functional groups or oxetanyl groups in one molecule, and (B) in one molecule. An epoxy resin having at least two epoxy functional groups, (C) a curing agent, and (D) an epoxy-silicone hybrid resin composition containing the curing catalyst as essential components, one kind of a quaternary phosphonium salt as a curing catalyst An epoxy / silicone hybrid resin composition using the above, particularly an epoxy / silicone hybrid resin composition containing a compound represented by the following formula (1) and / or a compound represented by the following formula (2) as a quaternary phosphonium salt: It has been found that a light-emitting semiconductor device excellent in reliability can be obtained by sealing and protecting.

Therefore, the present invention
(A) an organopolysilsesquioxane resin having at least two epoxy functional groups or oxetanyl groups in one molecule;
(B) an epoxy resin having at least two epoxy functional groups in one molecule;
(C) a curing agent,
(D) An epoxy / silicone hybrid resin composition comprising a curing catalyst as an essential component, which comprises at least one quaternary phosphonium salt as a curing catalyst. In this case, the quaternary phosphonium salt preferably contains a compound represented by the above formula (1) and / or a compound represented by the above formula (2). Moreover, it is preferable that the glass transition point of the hardened | cured material is 130 degreeC or more.
The present invention also provides a light emitting semiconductor device in which a light emitting semiconductor element is sealed and protected with a transparent cured product of the above epoxy / silicone hybrid resin composition.

  The epoxy / silicone hybrid resin composition of the present invention can provide a light emitting semiconductor device having excellent mounting reliability because it does not discolor due to a reflow test by covering and protecting the light emitting semiconductor element with the cured product. The above benefits are enormous. In this case, the cured product having a glass transition point of 130 ° C. or higher has no dust adhesion particularly on the surface of the cured product, and has excellent crack resistance in the heat resistance test.

  The epoxy-silicone hybrid resin composition suitably used for the coating protective material for coating and protecting the light emitting semiconductor of the present invention is (A) an organopolysilsesqui having at least two epoxy functional groups or oxetanyl groups in one molecule. The essential components are an oxan resin, (B) an epoxy resin having at least two epoxy functional groups in one molecule, (C) a curing agent, and (D) a curing catalyst.

Here, the organopolysilsesquioxane resin having at least two epoxy functional groups or oxetanyl groups in one molecule as the component (A) will be described.
Organopolysilsesquioxane resin (hereinafter sometimes simply referred to as silsesquioxane) is usually RSiX ₃ (where R is an unsubstituted alkyl group having 1 to 20 carbon atoms, aryl group, alkenyl group, An unsubstituted monovalent hydrocarbon group such as an aralkyl group, or at least one hydrogen atom of the unsubstituted monovalent hydrocarbon group is an epoxy functional group such as an epoxy group or a glycidoxy group, an oxetanyl group, or a triorganosiloxy group Wherein at least two of R are substituted monovalent hydrocarbon groups substituted with an epoxy functional group or an oxetanyl group, and X is a hydrous such as a halogen or an alkoxy group. Polysiloxane resin having RSiO _1.5 unit as a basic structural unit, synthesized by hydrolysis and condensation (heavy) of trifunctional organosilicon compound represented by It is. The molecular arrangement of organopolysilsesquioxane resin is typically an amorphous structure (three-dimensional network structure), a ladder type structure, a cage type (fully condensed cage type) structure, or a partially cleaved structure (cage type). A structure in which a part of silicon atoms is missing from a structure or a structure in which a silicon-oxygen bond in a part of a cage structure is broken) is known. The basic structural unit is usually 80 mol% or more (80 to 100 mol%), preferably 90 mol% or more (90 to 100 mol%) in the organopolysilsesquioxane resin constituting the component (A). ), More preferably 95 mol% or more (95 to 100 mol%), and still more preferably 98 mol% or more (98 to 100 mol%) represents the RSiO _1.5 unit. The remaining units other than the basic structural unit in the organopolysilsesquioxane resin are R ₃ SiO _1/2 unit, R ₂ SiO _2/2 unit, SiO _4/2 unit, (OH) R _2. SiO _1/2 units, (OH) ₂ RSiO _1/2 units, (OH) RSiO _2/2 units and the like may be contained as appropriate.

  The silsesquioxane used in the present invention may be of any structure among these silsesquioxane compounds, or may be a mixture thereof.

In the present invention, silsesquioxane is an organic group in which at least two of the eight organic groups R contain an epoxy functional group or an oxetanyl group when converted to the (RSiO _1.5 ) ₈ structure (that is, the above epoxy functional group). Or a monovalent hydrocarbon group substituted with an oxetanyl group. The type of the remaining organic group R is not particularly limited as long as it has no or low chemical reactivity, and may be the same or different. The remaining 6 or less organic groups R are preferably alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 5 to 12 carbon atoms, aryl groups having 6 to 12 carbon atoms such as phenyl groups, and triorganosiloxy groups. It is at least 1 type selected from the group which consists of a C1-C12 monovalent hydrocarbon group to contain.

  Here, as the monovalent hydrocarbon group substituted with an epoxy functional group or an oxetanyl group, for example, an epoxymethyl group, a 2-epoxyethyl group, a glycidoxymethyl group, a γ-glycyloxypropyl group, a β- ( 3,4-epoxycyclohexyl) ethyl group, 2-oxetanylbutyl group, carbon substituted with epoxy functional group such as γ- (2-oxetanylbutyloxy) propyl group or oxetanyl group, which may contain oxygen atom Examples thereof include an alkyl group of 1 to 10.

Moreover, as a C1-C20 alkyl group, a methyl group, an ethyl group, a propyl group, a butyl group etc. are mentioned.
Examples of the cycloalkyl group having 5 to 12 carbon atoms include a cyclopentyl group, a cyclohexyl group, and a norbornyl group.
As a C1-C12 hydrocarbon group containing a triorganosiloxy group, it is C1-C12 normally, such as a methylene group, ethylene group, a propylene group, butylene group etc., Preferably it is about C1-C6. A triorganosiloxy group (for example, R ¹ ₃ SiO group, wherein R ¹ is the number of carbon atoms other than the triorganosiloxy group-substituted monovalent hydrocarbon group in R) And triorganosiloxy-substituted alkyl groups to which 1-20 monovalent hydrocarbon groups, epoxy functional groups or substituted monovalent hydrocarbon groups substituted with oxetanyl groups) are bonded.

The component (A) has a polystyrene equivalent weight average molecular weight of 2 × 10 ³ or more, typically 2 × 10 ³ to 1 × 10 ⁵ , more typically 4 × 10 ³ to 1 × 10 ^4. It is. If it is less than 2 × 10 ³ , crystallization occurs, and a remelting step may be required at the time of blending. On the other hand, if it exceeds 1 × 10 ⁵ , the compatibility with the epoxy resin is lowered, and there is a possibility that a transparent cured product cannot be obtained. The “weight average molecular weight in terms of polystyrene” is the weight average molecular weight in the molecular weight distribution by gel permeation chromatography analysis. When the molecular weight distribution shows a distribution shape having two or more peaks, the maximum molecular weight in the distribution shape The weight average value for the peak of.

Next, the epoxy resin having at least two epoxy functional groups in one molecule as component (B) is bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin. , Aromatic epoxy resins such as naphthalene type epoxy resins, biphenyl type epoxy resins, phenol aralkyl type epoxy resins, biphenyl aralkyl type epoxy resins, hydrogenated epoxy resins obtained by hydrogenating aromatic rings of the above various epoxy resins, dicyclopentadiene Type epoxy resin, alicyclic epoxy resin, non-aromatic epoxy resin such as triglycidyl isocyanurate, etc., but if there are at least two epoxy functional groups in one molecule, it is limited to the above resin. It is not something. These epoxy resins may be used alone or in combination of two or more.
Of these, non-aromatic epoxy resins such as hydrogenated epoxy resins, alicyclic epoxy resins, and triglycidyl isocyanurate are preferably used in order to prevent deterioration due to light.

  The amount of the epoxy resin blended (that is, the ratio of the component (B) to the total of the components (A) and (B)) is preferably 5 to 80% by mass. If it is less than 5% by mass, the cured product strength of the epoxy / silicone hybrid resin composition cannot be sufficiently obtained, and when a light emitting semiconductor device is sealed with this kind of material, cracks are easily generated in tests such as a temperature cycle. There is a risk of poor adhesion. On the other hand, when the content exceeds 80% by mass, the epoxy resin content increases, and when the light emitting element emits ultraviolet rays or the like, the cured product of the epoxy / silicone hybrid resin composition may be deteriorated by ultraviolet light. For this reason, it is more desirably 10 to 70% by mass, and particularly desirably 20 to 60% by mass.

  In the present invention, a curing agent (component (C)) can be used to form a crosslinked product by reaction with an epoxy functional group and / or an oxetanyl group. As such a curing agent, a curing agent used for an epoxy resin can be used, and any of an amine curing agent, a phenol curing agent, and an acid anhydride curing agent may be used. A combination of a functional group and an acid anhydride can be preferably used.

  Such curing agents include phthalic anhydride, maleic anhydride, trimellitic anhydride, pyromellitic anhydride, hexahydrophthalic anhydride, 3-methyl-hexahydrophthalic anhydride, 4-methyl-hexahydrophthalic anhydride, or A mixture of 3-methyl-hexahydrophthalic anhydride and 4-methyl-hexahydrophthalic anhydride, tetrahydrophthalic anhydride, nadic anhydride, methyl nadic anhydride, norbornane-2,3-dicarboxylic anhydride, methylnorbornane-2 , 3-dicarboxylic acid anhydride. As for the compounding quantity of a hardening | curing agent, 0.5-1.5 mol is preferable with respect to a total of 1 mol of the epoxy functional group and oxetanyl group in (A) component, and the epoxy functional group in (B) component, More preferably, it is 0.8-1.2 mol.

  In the present invention, as the curing catalyst (component (D)), one or more quaternary phosphonium salts, particularly a compound represented by the following formula (1) and / or a compound represented by the following formula (2): 1 type (s) or 2 or more types are used among the quaternary phosphonium salts containing. As a result, the basic performance is transparent, there is no surface tackiness, no discoloration during the reflow test, and high mounting reliability can be obtained. Specific examples of the quaternary phosphonium salts other than the compounds represented by the following formulas (1) and (2) include “U-CAT5003” manufactured by San Apro, which is a bromide salt of quaternary phosphonium.

  Further, as the curing catalyst, at least one or more of the compounds represented by the above formula (1), the compounds represented by the above formula (2), and quaternary phosphonium salts other than these compounds are used. The curing catalyst can also be used. Examples of such other curing catalysts include organic phosphine-based curing catalysts such as triphenylphosphine and diphenylphosphine, 1,8-diazabicyclo (5,4,0) undecene-7, triethanolamine, benzyldimethylamine and the like. And tertiary amine-based curing catalysts, and imidazoles such as 2-methylimidazole and 2-phenyl-4-methylimidazole.

  The blending amount of the curing catalyst of the component (D) is preferably 0.05 to 3 parts by mass with respect to 100 parts by mass of the total amount of the components (A), (B), and (C). If the amount of the curing catalyst is less than 0.05 parts by mass, the effect of promoting the reaction between the epoxy resin and the curing agent may not be sufficiently obtained. On the other hand, if the blending amount of the curing catalyst is more than 3 parts by mass, it may cause discoloration during curing or reflow test.

  The epoxy-silicone hybrid resin composition of the present invention can be easily produced by mixing the components (A), (B), (C) and (D). In addition, a light scattering agent such as a phosphor for changing the wavelength or fine powder of titanium oxide may be added to the epoxy-silicone hybrid resin composition of the present invention.

  Furthermore, as long as they do not deviate from the object of the present invention, as other components, antioxidants, discoloration inhibitors, deterioration inhibitors, silica and other inorganic fillers, silane coupling agents, modifiers, plasticizers, diluents Etc. can be used together as necessary.

  When the coating protective material containing the components (A), (B), (C) and (D) as essential components for protecting the light-emitting semiconductor of the present invention is used in potting or injection, it must be liquid. The viscosity at 25 ° C. is preferably about 10 to 1,000,000 mPa · s, particularly about 100 to 1,000,000 mPa · s as measured by a rotational viscometer. On the other hand, when the light emitting semiconductor device is manufactured by transfer molding, the above-mentioned liquid resin can be used. However, the liquid resin can be thickened by solidification, pelletized, and then molded by molding. it can.

  The epoxy / silicone hybrid resin composition of the present invention is suitably used as a coating protective material for coating and protecting a light emitting semiconductor. In this case, examples of the light emitting semiconductor include a light emitting diode (LED), an organic electroluminescent element (organic EL), a laser diode, and an LED array. The mode of covering and protecting the light emitting semiconductor is not particularly limited, but a method of covering the light emitting semiconductor disposed in the housing having the opening, filling the housing with a coating protecting material, and curing the method is adopted. obtain. Moreover, what mounted LED on the matrix-ized board | substrate can also be manufactured by a printing method, transfer molding, injection molding, etc.

In the present invention, the curing conditions for the coating protective material are arbitrary at 25 ° C. for 72 hours to 200 ° C. for 3 minutes depending on the working conditions, and balance between productivity and light-emitting element and housing heat resistance. Can be selected as appropriate. In the case of transfer molding or injection molding, it can be easily produced by molding at a temperature of 150 to 180 ° C. and a pressure of ^{20 to} 50 kgf / cm ² for 1 to 5 minutes. Further, post-curing (secondary curing or post-curing) can be performed at 150 to 200 ° C. for 1 to 4 hours.

  The epoxy-silicone hybrid resin composition of the present invention preferably has a cured product having a glass transition point of 130 ° C. or higher, usually 130 to 180 ° C., particularly 135 to 165 ° C. In this case, the glass transition point is a value (temperature) defined as the inflection point of the linear expansion coefficient in the thermomechanical analysis (TMA) measurement method.

  Here, as a specific means for setting the glass transition point of the cured product of the present invention to 130 ° C. or higher, an epoxy resin, in particular, a dicyclopentadiene type epoxy resin, an alicyclic epoxy resin, or triglycidyl isocyanurate, etc. The blending amount of the non-aromatic epoxy resin (that is, the proportion of the component (B) in the total of the components (A) and (B)) is adjusted to 10 to 70% by mass, particularly 20 to 60% by mass. Can be achieved. If the blending ratio is less than 10% by mass, the glass transition point may not reach 130 ° C. or higher, and cracks may easily occur in the temperature cycle test, or adhesion failure may occur. When it exceeds 70 mass%, the cured product may be inferior in ultraviolet resistance.

  EXAMPLES Hereinafter, although an Example and a comparative example are shown and this invention is demonstrated concretely, this invention is not restrict | limited to the following Example.

First, the evaluation method of the coating protective material of an Example and a comparative example is shown.
The resin composition is cured at 100 ° C. for 2 hours and then at 150 ° C. for 4 hours as a sealing material for a rod-shaped light emitting semiconductor device in which the LED chip and the lead frame are arranged in a rod shape having a thickness of 5 mm. The items were evaluated.
The surface tacky rod-shaped cured product was palpated to evaluate the presence or absence of surface tackiness.
Appearance of discoloration in the cured product appearance bar-shaped cured product and the produced light emitting semiconductor device was visually evaluated.
The light-emitting semiconductor device produced with reflow resistance was subjected to a 260 ° C. peak reflow test process five times, and the presence or absence of discoloration was visually evaluated.
It measured based on JIS K6301 with respect to hardness rod-shaped hardened | cured material (Shore D).
A glass transition point bar-like cured product was cut into a width of 4 mm and a length of 10 mm, and the inflection point of the expansion coefficient was determined as the glass transition point (Tg) by thermomechanical analysis (TMA) measurement.
Thermal Shock Test The light-emitting semiconductor device produced was subjected to 200 cycles of a thermal shock test at a low temperature side of −40 ° C. and a high temperature side of 120 ° C., and the number of appearance cracks was measured.

  Silsesquioxane (component (A)) having at least two epoxy functional groups or oxetanyl groups in one molecule was prepared by the following method.

[Production Example] Synthesis of silsesquioxane having an epoxy functional group After charging 900 g of isopropyl alcohol, 13 g of a 25% aqueous solution of tetramethylammonium hydroxide and 91 g of water, γ-glycidoxypropyltrimethoxysilane (Shin-Etsu Chemical) 255 g of Kogyo KBM403) was added and stirred at room temperature for 20 hours.
After completion of the reaction, 1,200 g of toluene was put into the system, and isopropyl alcohol and the like were removed under reduced pressure. The residue was washed with hot water using a separatory funnel. After washing until the aqueous layer became neutral, the toluene layer was dehydrated with anhydrous sodium sulfate. Anhydrous sodium sulfate was removed by filtration, and toluene was removed under reduced pressure to obtain the desired resin (resin 1). The epoxy equivalent was 185 g / mol.

Moreover, as an epoxy resin (component (B)) having at least two epoxy functional groups in one molecule, “Celoxide 2021P” manufactured by Daicel Chemical Industries, which is an alicyclic epoxy resin, was used.
Further, as a curing agent (component (C)), “MH” manufactured by Shin Nippon Rika Co., Ltd., which is methylhexahydrophthalic anhydride, was used.
Further, as a curing catalyst (component (D)), “Hishicolin PX-4MP” manufactured by Nippon Chemical Industry Co., Ltd., which is a compound represented by the above formula (1), and Nippon Chemical Industry Co., Ltd., which is a compound represented by the above formula (2). "Hishicolin PX-4ET" manufactured by San-Apro, which is a quaternary phosphonium salt, 2-ethyl-4-methylimidazole (2E4MZ) and 2,3-dihydro-1H-pyrrolo [1,2- a] Benzimidazole (TBZ) (both manufactured by Shikoku Kasei Kogyo Co., Ltd.) was used.

[Examples 1 to 3 and Comparative Examples 1 and 2]
In the blending amounts shown in Table 1 below, the components (A), (B), (C) and (D) are blended, and a cured product and a light-emitting semiconductor device are produced under the above conditions. The cured product appearance and reflow resistance were measured. The results are also shown in Table 1.

  Next, the properties (surface tackiness, hardness, glass transition point) and the light emitting semiconductor device (thermal shock test) of the cured products obtained in Example 1 and Comparative Examples 3 and 4 were measured according to the above evaluation methods. The results are shown in Table 2.

[Comparative Example 3]
YX-8000 (50 parts by mass), MH (40 parts by mass), and PX-4MP (1 part by mass) were blended, and a cured product and a light emitting semiconductor device were produced under the above conditions.
[YX-8000: Hydrogenated bisphenol A type epoxy resin (Japan Epoxy Resin Co., Ltd.)
MH: Methylhexahydrophthalic anhydride (manufactured by Shin Nippon Chemical Co., Ltd.)
PX-4MP: Organic phosphonium salt (manufactured by Nippon Chemical Industry Co., Ltd.)]

[Comparative Example 4]
Using KJR-632, a cured product and a light-emitting semiconductor device were manufactured under the above conditions.
[KJR-632: Silicone resin (manufactured by Shin-Etsu Chemical Co., Ltd.)]

Claims (7)

(A) an organopolysilsesquioxane resin having at least two epoxy functional groups or oxetanyl groups in one molecule;
(B) an epoxy resin having at least two epoxy functional groups in one molecule;
(C) a curing agent,
(D) An epoxy / silicone hybrid resin composition comprising a curing catalyst as an essential component, wherein the curing catalyst contains one or more quaternary phosphonium salts. The epoxy-silicone hybrid resin composition according to claim 1, wherein the quaternary phosphonium salt contains a compound represented by the following formula (1) and / or a compound represented by the following formula (2).

Organopolysilsesquioxane resin (A) having at least two epoxy functional groups or oxetanyl groups in one molecule is RSiO _1.5 unit (where R is an unsubstituted monovalent hydrocarbon having 1 to 20 carbon atoms) A substituted monovalent hydrocarbon group in which at least one hydrogen atom of the group or the unsubstituted monovalent hydrocarbon group is substituted with an epoxy functional group, an oxetanyl group, or a triorganosiloxy group, The epoxy-silicone hybrid resin composition according to claim 1 or 2, wherein two are a monovalent hydrocarbon group substituted with an epoxy functional group or an oxetanyl group). Organopolysilsesquioxane resin (A) having at least two epoxy functional groups or oxetanyl groups in one molecule is represented by the following formula RSiX ₃
(However, R is as described above. X represents a hydrolyzable group.)
The epoxy-silicone hybrid resin composition according to claim 3, which is obtained by hydrolysis and condensation of a trifunctional organosilicon compound represented by the formula:   The epoxy-silicone hybrid resin composition according to any one of claims 1 to 4, wherein the curing catalyst (D) is an acid anhydride.   The epoxy-silicone hybrid resin composition according to any one of claims 1 to 5, wherein the cured product has a glass transition point of 130 ° C or higher.   A light emitting semiconductor device, wherein the light emitting semiconductor element is sealed and protected with a transparent cured product of the epoxy-silicone hybrid resin composition according to any one of claims 1 to 6.