TW201338856A - Resin composition for optical semiconductor sealing material - Google Patents

Abstract

Provided is a resin composition for an optical semiconductor sealing material. The resin composition has a low viscosity, and is capable of achieving a cured product having a high refractive index and exhibiting excellent optical transparency and heat resistance. The resin composition for an optical semiconductor sealing material includes zirconium oxide particles having an average particle size in the range of 1-30nm, a dispersant represented by formula (1), and an epoxy compound, on condition that, in formula (1), R represents a branched-chain C3-24 alkyl and/or alkenyl group, AO represents a C1-4 oxyalkylene group, n represents a value in the range of 5-30 expressing the average number of moles of alkylene oxide added, and X repressents a linking group comprising carbon, hydrogen, and/or oxygen.

Description

Resin composition for optical semiconductor sealing material

The present invention relates to a resin composition for an optical semiconductor sealing material, and more particularly to a resin composition for an optical semiconductor sealing material, which is used for forming a resin having high transparency and high refractive index at the time of curing and excellent heat resistance.

Conventionally, a sealing material used in an optical semiconductor such as an LED (Light Emitting Diode) or a photodiode is light transmissive using, for example, an epoxy resin or a silicone resin. Or a resin excellent in heat resistance. However, in recent years, for applications such as indoor lighting, a sealant having high brightness is required. Therefore, it is necessary to increase the refractive index of the sealant to achieve improvement in light emission efficiency. As a solution thereto, it has been studied to disperse zirconia fine particles in a resin. However, in order to ensure the transparency of the sealant, it is necessary to use zirconia which is formed of nanoparticles having a smaller particle diameter, and to disperse the zirconia nanoparticle, an alkyl carboxylic acid such as neodecanoic acid is used. (Patent Document 1).

However, a nano-sized particle having an average particle diameter of several tens of nm or less tends to have an extremely high agglomeration property due to a high surface energy, so that the amount of blending cannot be increased. In other words, when a large amount of zirconia nanoparticles is blended in order to further increase the refractive index, even if a large amount of the dispersant described in Patent Document 1 is used, the particles are not sufficiently dispersed to have light transmission. Sexuality will be greatly reduced.

[Previous Technical Literature] (Patent Literature)

Patent Document 1: Japanese Patent Laid-Open Publication No. 2008-106260

The present invention has been made in view of such problems in the prior art, and an object thereof is to provide an optical semiconductor sealing material composition which has low viscosity, excellent light transmittance and heat resistance, and high refractive index.

The resin composition for an optical semiconductor sealing material of the present invention, comprising: zirconia particles having an average particle diameter of 1 to 30 nm, a dispersant represented by the following formula (1), and an epoxy compound;

Here, R of the formula (1) is an alkyl group or an alkenyl group having a branched chain and having a carbon number of 3 to 24, and AO of the formula (1) is an oxyalkylene group having a carbon number of 1 to 4. n is a value indicating that the average addition molar number of the alkylene oxide is in the range of 5 to 30, and X of the formula (1) is a linking group composed of a carbon atom, a hydrogen atom and/or an oxygen atom. .

Here, in the above dispersant, X of the above formula (1) is preferably an alkylene group having a carbon number of 1 to 15.

Further, in the above dispersing agent, X of the above formula (1) may be a linking group represented by the following formula (2):

Wherein Y of the formula (2) is any one selected from the group consisting of an alkylene group having 1 to 15 carbon atoms, a vinyl group, a phenylene group, and a phenyl group having a carboxyl group.

In the resin composition for an optical semiconductor sealing material, when the total amount of the resin composition for a photo-semiconductor sealing material is 100% by weight, the amount of the zirconia particles blended is preferably from 0.5 to 80% by weight. Thus, the resin composition for an optical semiconductor sealing material of the present invention is a dispersion The increase in the viscosity of the dispersion is suppressed and the blending ratio of the zirconia nanoparticles can be increased, so that the refractive index of the obtained resin can be increased. Further, it is also excellent in dispersion stability.

The optical semiconductor of the present invention is characterized in that the resin composition for any of the above-described optical semiconductor sealing materials is used.

Dispersing particles

In the resin composition for an optical semiconductor sealing material of the present invention, the dispersoid particles are zirconia nanoparticles, specifically, zirconia having an average particle diameter of 1 to 30 nm. Further, the zirconia nanoparticles in the present invention may be crystalline or amorphous. Further, the dispersed particles dispersed by the dispersing agent of the present invention may be isotropy particles or anisotropic particles or may be fibrous.

In the present invention, as the dispersed zirconia nanoparticle, those obtained by a conventional method can be used. As a method of preparing fine particles, there is a top-down method in which coarse particles are mechanically pulverized and refined, and a plurality of unit particles are formed by The cluster state in which the agglutination is formed forms two ways of the bottom-up method of the particles, but any one of the methods is suitable for use. Further, the methods may be any one of a wet method and a dry method. In addition, from the bottom up, there are physical methods and chemical methods, which can be according to any method. The dispersing agent in the present invention may be used in a step of mechanically pulverizing and refining coarse particles, or may be in a cluster state in which a plurality of unit particles are formed and aggregated. Used in the step of forming a particle in a bottom-up manner; or a particle may be used, after the microparticles are prepared in advance by the foregoing method, in order to stably take out the dispersed particle from the medium, it is called a surface modifier or a surface protective agent. The conventional protective agent is removed by coating or impregnation. As a protective agent, it can be used instead of the above-mentioned conventional dispersing agent.

In the present invention, the zirconia nanoparticle as the dispersion particle has a function of increasing the refractive index as a sealant, whereby the light emission efficiency can be improved, and a sealant having high luminance can be obtained.

The total blending amount of the zirconia nanoparticles is from 0.5 to 80% by weight, more preferably from 30 to 70% by weight, still more preferably from 35 to 60, based on the total amount of the resin composition for an optical semiconductor sealing material of the present invention. weight%. As described above, since the resin composition for an optical semiconductor sealing material of the present invention can increase the blending ratio of the zirconia nanoparticles, the refractive index of the obtained resin can be improved. Moreover, it does not impair the dispersion stability of the composition.

2. About the hydrophobic group of the dispersant (R)

The hydrophobic group (R) of the dispersing agent in the present invention is an alkyl group or an alkenyl group having a branched chain and having a carbon number of 3 to 24. The content of the alkyl group or the alkenyl group having a branched chain and having a carbon number of 3 to 24 is preferably 70% by weight or more based on the total of R.

The carbon number of the starting alcohol used to form R may be a mixture of alcohols of a single or different carbon number. Further, the starting material alcohol may be a mixture derived from synthesis or derived from nature, and its chemical structure may be a single composition or a complex isomer.

The starting alcohol which can be used may be selected from conventional ones, and specific examples thereof are butanol, isobutanol, pentanol and/or its isomer, hexanol and/or its isomer, heptanol derived from synthesis. And / or its isomer, octanol and / or its isomer, 3,5,5-trimethyl-1-hexanol, higher olefin derived from propylene or butene, or a mixture thereof Isodecyl alcohol, isodecyl alcohol, is undecyl alcohol, isododecyl alcohol, isotridecyl alcohol produced by the oxo process, NEODOL 23, 25, 45 manufactured by Shell Chemicals Corp. SAFOL 23 manufactured by Sasol Corp., EXXAL 7, EXXAL 8N, EXXAL 9, EXXAL 10, EXXAL 11 and EXXAL 13 manufactured by Exxon Mobil Corporation are also suitable alcohols for use. An example. Also, derived from natural octanol, decyl alcohol, lauryl alcohol (1-dodecanol), myristyl alcohol (1-tetradecanol), cetyl alcohol (1-hexadecanol), stearyl alcohol (1- Octadecanol), oleyl alcohol (cis-9-octadecen-1-ol) and the like are also examples of higher alcohols that can be used. In addition, it has a 2-alkyl-1-alkanol type A single composition of the chemical structure of Guerbet Alcohol, or a mixture thereof, etc., is also an example of a higher alcohol suitable for use, such as 2-ethyl-1-hexanol, 2-propyl- 1-hexanol, 2-butyl-1-hexanol, 2-ethyl-1-heptanol, 2-propyl-1-heptanol, 2-ethyl-1-octanol, 2-hexyl-1 - decyl alcohol, 2-heptyl-1-undecyl alcohol, 2-octyl-1-dodecanol, 2-mercapto-1-tetradecyl alcohol, and isostearyl alcohol derived from branched alcohol . Further, the above various alcohols may be used in combination of two or more kinds. However, in the dispersant of the present invention, the hydrophobic group (R) is a branched alkyl group and/or alkenyl group having a carbon number of 3 to 24 as described above.

Further, the hydrophobic group (R) is in the case of hydrogen or a hydrocarbon group having 1 to 2 carbon atoms, when the carbon number is more than 25, and the carbon number of the hydrophobic group (R) is in the range of 3 to 24. In the case where the content of the linear alkyl group and/or the alkenyl group is more than 30% by weight, the dispersion may not be stably dispersed in the dispersion medium or the selection of the dispersible medium that can be used. The range is limited, or replacement or mixing of the dispersing medium for the dissimilar medium occurs in the preparation step of the dispersion. As a result, the stability of the dispersion is remarkably lowered, and the precipitate is immediately generated, or the stability with time is remarkably lowered to lower the added value of the final product, the productivity is lowered, the processing property is lowered, and the quality is deteriorated. In order to avoid such problems and to make the action of the dispersant particularly effective in the present invention, the hydrophobic group (R) is more preferably a branched alkyl group having a carbon number of 8 to 18.

3. Oxidation alkenyl (AO) _{n of the} dispersant

The alkylene oxide species suitable as a dispersing agent in the present invention will be described. AO in the formula (1) is an oxyalkylene group having a carbon number of 1 to 4, and specifically, an alkylene oxide having 2 carbon atoms is ethylene oxide. The alkylene oxide having a carbon number of 3 is propylene oxide. The alkylene oxide having a carbon number of 4 is tetrahydrofuran or butylene oxide, preferably 1,2-butylene oxide or 2,3-butylene oxide. The oxyalkylene chain (-(AO) _n -) in the dispersing agent is introduced for the purpose of adjusting the dispersing agent affinity of the dispersing agent, and the alkylene oxide may be a single polymeric chain or two or more. A random polymeric chain or a block polymeric chain of alkylene oxides, and combinations thereof can also be used. The n of the average addition mole number of the alkylene oxide of the formula (1) is in the range of 5 to 30, preferably in the range of 5 to 20.

4. The linking group of the dispersing agent (X)

The linking group (X) may be selected from a conventional structure composed of a carbon atom, a hydrogen atom or an oxygen atom, and is preferably composed of a saturated hydrocarbon group, an unsaturated hydrocarbon group, an ether group, a carbonyl group or an ester group, and It may have an alicyclic structure, an aromatic ring structure, and may also have a repeating unit. When the linking group X contains a nitrogen atom and/or a sulfur atom and/or a phosphorus atom or the like, it has an effect of weakening the affinity of the carboxyl group for the dispersing substance, and is not suitable as a structural factor of the dispersing agent in the present invention.

Further, X of the formula (1) is preferably an alkylene group having a carbon number of 1 to 15, more preferably an alkylene group having a carbon number of 1 to 8.

Further, X of the formula (1) is preferably a substance represented by the above formula (2). However, Y in the formula (2) is any one selected from the group consisting of an alkylene group having 1 to 15 carbon atoms, a vinyl group, a phenyl group, and a phenyl group having a carboxyl group.

5. Better dispersant

In the present invention, it is more preferred to use a dispersing agent of the following formula (3).

Wherein R in the formula (3) is preferably an alkyl group having a carbon number of 8 to 18 and having a branched chain, and n is an average addition mole number of ethylene oxide, and preferably 3 to 20 The scope. Since the composition of the dispersing agent is within this range, the range of selection of the dispersing medium for the preparation of the dispersion can be expanded, and the applicability to the mixing and replacement of the dispersing dispersing medium can be improved. As described above, by limiting the composition range of the dispersant, it is more suitable for the stability of the dispersion over time, and as a result, the added value of the final product can be improved, the productivity can be improved, the processing characteristics can be improved, and the quality can be stabilized.

6. Dispersant blending amount

The blending amount of the dispersing agent in the present invention is not particularly limited, and may be 0.1 to 300% by weight, preferably 0.5 to 20% by weight, more preferably 1 to 15 with respect to the zirconia particles as the dispersed particles. The weight% is further more preferably 2 to 10% by weight.

7. Method for producing dispersant

The dispersant in the present invention can be produced by a known method. For example, a general nonionic surfactant compound which is added to an alcohol, an amine or a mercaptan as a raw material by a conventional method, and a monohalogenated lower carboxylic acid or a salt thereof, in the presence of a base and an epoxy A method in which a hydroxyl group at the end of the alkene is reacted; or an acid anhydride is used and produced by a ring-opening reaction with a hydroxyl group at the terminal of the alkylene oxide, but is not limited thereto.

Further, since the optimum composition is selected by specifically limiting the type of the hydrophobic group, the alkylene species and the addition form thereof, the amount of addition moles, the linking group, and the like in the above range, it is more dispersible than the conventional dispersant. A wide variety of dispersoids and dispersion of the dispersoids in a wider variety of dispersing media have a large industrial value.

Further, the dispersing agent used in the present invention can reduce the ion species contained in the conventional refining method, particularly the contents of ions of alkali metal ions, alkaline earth metal ions, heavy metal ions, and halogen ions. use. Ionic species in the dispersant, dispersion stability, corrosion resistance, oxidation resistance, electrical properties of the cured product (conductive properties, insulating properties), stability over time, heat resistance, low humidity The weather resistance has a large influence, and the content of the above ions can be appropriately determined, but it is preferably less than 10 ppm in the dispersant.

Further, the resin composition for an optical semiconductor sealing material of the present invention can be prepared by a conventional stirring method, homogenization method, or dispersion method. Examples of the dispersing machine that can be used include a roll mill of a two-roll type roll, a three roll type roll, a ball mill of a ball mill, a vibratory ball mill, a paint shaker, and the like. A bead-mill of a continuous disk type bead ball mill, a continuous ring type bead ball mill, a sand mill, a jet mill, or the like. Further, dispersion treatment can also be carried out in an ultrasonic generation bath.

8. Epoxy compound

In the resin composition for an optical semiconductor sealing material of the present invention, the epoxy compound to be used has a compound having an epoxy group. Such a compound can be exemplified by the following.

Examples of the aliphatic epoxy compound include triglycidyl isocyanurate, butylepoxypropyl ether, 1,6-hexanediol diepoxypropyl ether, and neopentyl glycol diepoxypropane. Ethyl ether, polypropylene glycol diepoxypropyl ether, trimethylolpropane triepoxypropyl ether, dimer acid polyepoxypropyl ether, and the like. Examples of the alicyclic epoxy compound include 3,4-epoxycyclohexenylmethyl-3', 4'-epoxycyclohexenecarboxylate, and bis(3,4-epoxycyclohexyl). Adipate, cyclohexanedimethanol diepoxypropyl ether, 3,4-epoxycyclohexenylmethyl-3',4'-epoxycyclohexane modified by ε-caprolactone The urethane, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, hydrogenated bisphenol S diglycidyl ether, and hydrogenated novolak type epoxy compound.

As the aromatic epoxy compound, for example, bisphenol A epoxide Propyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, and novolak type epoxy compound.

Among these, the aliphatic epoxy compound and the alicyclic epoxy compound are preferred because they can improve light resistance and heat discoloration resistance. Further, these epoxy compounds may be used singly or in combination of two or more. Further, the epoxy compound may be an oligomer of the above compound.

In the resin composition for an optical semiconductor sealing material of the present invention, a curing agent can be further used. As such a hardening agent, any of a polyaddition molding, a catalyst type, and a condensation type can be used, and examples thereof include diaminodiphenylmethane, diaminodiphenylanthracene, and di-ethylidene. An amine compound such as an amine or a tri-ethyltetramine, a decylamine compound such as polydecylamine or dicyandiamide, hexahydrophthalic anhydride or methyltetrahydrophthalic anhydride. An acid anhydride such as methylbicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride or bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, and among them, an acid anhydride is preferred. The blending amount of the hardener is not particularly limited and is 25 to 180% by weight, more preferably 80 to 130% by weight based on the epoxy compound of the present invention. The amount of the epoxy compound or the mixture of the epoxy compound and the hardener is preferably 20 to 80% by weight, more preferably 25 to 75% by weight based on the total amount of the resin composition for an optical semiconductor sealing material of the present invention. Further more preferably 30 to 70% by weight.

9. Optional ingredients

The resin composition for an optical semiconductor sealing material of the present invention may be added to the above-mentioned respective components without any particular limitation, and is usually used for a coating material. Various resins, oligomers, and monomers for use in bonding or molding. Specifically, an acrylic resin, a polyester resin, an alkyd resin, a urethane resin, an anthrone resin, a fluororesin, an epoxy resin, a polycarbonate resin, a polyvinyl chloride resin, a polyvinyl alcohol, or the like may be added. . Further, an organic solvent having a boiling point of less than 100 ° C at 1 atm may also be added.

10. How to use

The resin composition for an optical semiconductor sealing material of the present invention can be cured by heating, ultraviolet irradiation, or electron beam irradiation. In this case, since a thick sealing material can be formed, it is preferably hardened by heating.

When the resin composition for an optical semiconductor sealing material of the present invention is used, a cured product having high transparency and high refractive index and excellent heat resistance can be obtained.

"Embodiment"

Hereinafter, examples and comparative examples of the invention will be described. In addition, hereinafter, "parts" indicating the blending amount means "parts by weight", and "%" means "% by weight". It is needless to say that the present invention is not limited to the following embodiments, and may be appropriately modified or modified without departing from the technical scope of the invention.

<Synthesis of Dispersant> [Production Example 1 (Synthesis of Dispersant A)]

In a toluene solvent, a branched C11-14 alkyl alcohol (product name: EXXAL 13, manufactured by ExxonMobil) ethylene oxide 10 molar addition product 640 g (1 mol) and sodium monochloroacetate 152 grams (1.3 moles), fed to the reactor and stirred to homogeneity. Next, 52 g of sodium hydroxide was added under the conditions of a reaction system temperature of 60 °C. Next, the temperature of the reaction system was raised to 80 ° C and allowed to mature for 3 hours. After the ripening, a white suspension solution was obtained by dropwise adding 117 g (1.2 mol) of 98% sulfuric acid under the condition that the reaction system was 50 °C. Next, the white suspension solution was washed with distilled water, and the solvent was removed by distillation under reduced pressure to obtain a dispersant A (R: branched C11-14 alkyl group, AO: ethylene oxide, n: 10, X: CH ₂ ).

[Production Example 2 (Synthesis of Dispersant B)]

Except for the branched C11-14 alkyl alcohol oxide 10 molar addition product in Production Example 1, instead of 598 g (1 mol) of isodecyl alcohol ethylene oxide 10 molar addition product The rest was carried out in the same manner as in Production Example 1, to obtain a dispersant B (R: isodecyl group, AO: ethylene oxide, n: 10, X: CH ₂ ).

[Production Example 3 (Synthesis of Dispersant C)]

In addition to the branched C11-14 alkyl alcohol oxide 10 molar addition product in Production Example 1, instead of the branched C11-14 alkyl alcohol oxide 5 molar addition product 420 g ( Except for 1 mol, the rest was carried out in the same manner as in Production Example 1, to obtain a dispersant C (R: branched C11-14 alkyl group, AO: ethylene oxide, n:5, X:CH ₂ ).

[Production Example 4 (Synthesis of Dispersant D)]

640 g (1 mol) of a branched C11-14 alkyl alcohol oxide 10 mol addition product and 100 g (1 mol) of succinic anhydride were reacted at 120 ° C for 2 hours to obtain a dispersant D ( R: branched C11-14 alkyl, AO: ethylene oxide, n: 10, X: COCH ₂ CH ₂ ).

[Production Example 5 (Synthesis of Dispersant E)]

In addition to the branched C11-14 alkyl alcohol oxide 10 molar addition in Production Example 1, instead of 2-ethylhexanol ethylene oxide 10 molar addition 570 g (1 Mo Other than the ear, the rest was carried out in the same manner as in Production Example 1, to obtain a dispersant E (R: 2-ethylhexyl group, AO: ethylene oxide, n: 10, X: CH ₂ ).

[Production Example 6 (Synthesis of Dispersant a)]

Except for the branched C11-14 alkyl alcohol oxide 10 molar addition product in Production Example 1, instead of the methanol ethylene oxide 10 molar addition product 472 g (1 m), the rest Then, it carried out in the same manner as in Production Example 1, and a dispersing agent a (R: methyl group, AO: ethylene oxide, n: 10, X: CH ₂ ) was obtained.

[Example 1]

Commercially available zirconia dispersion (Sakai Chemical) 100 parts of a trade name SZR-M manufactured by Industry Co., Ltd., a primary particle diameter of 3 nm, a methanol dispersion containing 30% by weight of zirconia, and 3 parts of a dispersant A produced in Production Example 1, 1, 6-hexanediol diepoxypropyl ether (trade name: DENACOL EX-212, manufactured by Nagase ChemteX Corp.) 13.5 parts, methylbicyclo[2.2.1]heptane-2,3 a mixture of dicarboxylic anhydride and bicyclo [2.2.1] heptane-2,3-dicarboxylic anhydride (trade name: RIKACID HNA-100, manufactured by New Japan Chemical Co., Ltd.) 13.5 parts Mix it. This was obtained by subjecting methanol to a reduced pressure by using a rotary evaporator to obtain an optical semiconductor sealing material composition of the present invention.

[Example 2]

The optical semiconductor sealing material composition was obtained in the same manner as in Example 1 except that 3 parts of the dispersing agent A was used instead of the dispersing agent B described in Production Example 2.

[Example 3]

The photo-semiconductor sealing material composition was obtained in the same manner as in Example 1 except that 3 parts of the dispersing agent A was used instead of the dispersing agent C described in Production Example 3.

[Example 4]

The photo-semiconductor sealing material composition was obtained in the same manner as in Example 1 except that the dispersing agent A was replaced by 3 parts and the dispersing agent D was used in the production example 4.

[Example 5]

The photo-semiconductor sealing material composition was obtained in the same manner as in Example 1 except that the dispersing agent A was replaced by 3 parts and the dispersing agent E was used in the production example 5.

[Example 6]

In addition to changing the dispersant A to 4.5 parts, the carboxylic anhydride hardener to be used in an amount of 12.75 parts, and 1,6-hexanediol diepoxypropyl ether 13.5 parts instead of 1,4-cyclohexane. The photo-semiconductor sealing material composition was obtained in the same manner as in Example 1 except that 12.75 parts of dimethanol diglycidyl ether (trade name: RIKARESIN DME-100, manufactured by Nippon Chemical Co., Ltd.) was used.

[Example 7]

The amount of the dispersant A used was changed to 4.5 parts, the amount of the carboxylic anhydride hardener used was 12.75 parts, and 13.5 parts of 1,6-hexanediol diepoxypropyl ether was replaced by RIKARESIN HBE-100 (trade name). In the same manner as in Example 1, except that 12.75 parts of the main component: hydrogenated bisphenol A diglycidyl ether and Nippon Chemical Co., Ltd.) were obtained, a photo-semiconductor sealing material composition was obtained.

[Example 8]

In addition to changing the amount of dispersant A used is 4.5 parts, 1,6-hexanediol II The photo-semiconductor sealing material composition was obtained in the same manner as in Example 1 except that the epoxy propyl ether was used in an amount of 7 parts and the carboxylic anhydride curing agent was used in an amount of 7 parts.

[Comparative Example 1]

The same procedure as in Example 1 was carried out except that 3 parts of the dispersant A was used instead of 3 parts of 2-ethylhexanoic acid.

[Comparative Example 2]

The same procedure as in Example 1 was carried out except that 3 parts of the dispersant A was used instead of 3 parts of lauric acid.

[Comparative Example 3]

The same procedure as in Example 1 was carried out except that 3 parts of the dispersant A was used instead of the dispersant a 3 described in Production Example 6.

[Comparative Example 4]

The same procedure as in Example 1 was carried out, except that 3 parts of the dispersant A was used instead of 3 parts of phenyltriethoxydecane (trade name: KBE-103, manufactured by Shin-Etsu Silicone Co., Ltd.). Way to proceed.

<Evaluation of characteristics of dispersion (dispersion)>

The dispersibility and viscosity of the optical semiconductor sealing material compositions of the above examples and comparative examples were evaluated, and the results are shown in Table 1. evaluation method As follows.

(dispersion)

The presence or absence of the precipitate was visually confirmed, and was ○ when there was no precipitate, and X when there was a precipitate.

(viscosity)

The viscosity of the dispersion at 25 ° C was measured according to JIS K5600-2-3 using an E-type viscometer (manufactured by Toki Sangyo Co., Ltd., RE80R).

<Evaluation of characteristics of hardened materials>

The photo-semiconductor sealing material compositions of the above examples and comparative examples were placed in a box made of a glass plate having a spacer of 25 μm therebetween, and were allowed to stand at 100 ° C for 1 hour and at 150 ° C for 1 hour. Heating in hours to obtain a cured product having a thickness of 25 μm. The results of the appearance, the refractive index, the haze, and the light transmittance at 450 nm before and after the heat resistance test are shown in Table 1 for this cured product. The evaluation method is as follows.

(appearance of hardened material)

The appearance of the cured product was visually observed, and when no precipitate or crack was observed, it was ○, and when precipitates or cracks were observed, it was X.

(refractive index)

The refractive index at a wavelength of 589 nm was measured using a prism coupler (METRICON(R) coupler model 2010 manufactured by Metricon Corporation).

(haze)

The haze of the cured product was measured using a haze calculator (manufactured by Suga Manufacturing Co., Ltd., HZ-2) in accordance with JIS K7136.

(heat resistance test)

The light transmittance of the obtained cured product at a wavelength of 450 nm after standing at 150 ° C for 12 hours was measured.

<Result>

As can be understood from Table 1, the optical semiconductor sealing material composition of each of the examples was excellent in dispersibility, and the viscosity was also a level which was not problematic in use. On the other hand, the compositions of Comparative Examples 1 and 2 were inferior in dispersibility, and the compositions of all the comparative examples had high viscosity, and in particular, the compositions of Comparative Examples 3 and 4 could not obtain a cured product due to no fluidity. . Further, the cured product obtained from the optical semiconductor sealing material composition of each of the examples had a good appearance, and had no problem with respect to haze, and the refractive index showed a high value. Further, the change in light transmittance after the initial stage and the heat resistance test was small, and excellent results were exhibited.

[Industrial use possibility]

The optical semiconductor sealing material composition of the present invention is excellent in light transmittance and heat resistance and has a high refractive index, and can be used as a sealing material such as an LED (light emitting diode) or a photodiode.

The present application is based on Japanese Patent Application No. 2011-257923, filed on Jan.

Claims (5)

A resin composition for an optical semiconductor sealing material comprising: zirconia particles having an average particle diameter of 1 to 30 nm, a dispersant represented by the following formula (1), and an epoxy compound; Wherein R of the formula (1) is an alkyl or alkenyl group having a branched chain and having a carbon number of 3 to 24, AO is an oxyalkylene group having a carbon number of 1 to 4, and n is an average addition of an alkylene oxide. The number of ears is a value in the range of 5 to 30, and X is a linking group composed of a carbon atom, a hydrogen atom and/or an oxygen atom. The resin composition for an optical semiconductor sealing material according to claim 1, wherein X in the above formula (1) is an alkylene group having a carbon number of 1 to 15. The resin composition for a photo-semiconductor sealing material according to the above aspect, wherein, in the dispersing agent, X in the formula (1) is a linking group represented by the following formula (2): Wherein Y of the formula (2) is any one selected from the group consisting of an alkylene group having 1 to 15 carbon atoms, a vinyl group, a phenylene group, and a phenyl group having a carboxyl group. The resin composition for an optical-semiconductor sealing material according to any one of the present invention, wherein the zirconia particles are oxidized when the total amount of the resin composition for a photo-semiconductor sealing material is 100% by weight. The blending amount is from 0.5 to 80% by weight. An optical semiconductor obtained by using the resin composition for an optical semiconductor sealing material according to any one of claims 1 to 4.