KR101751541B1 - Composition for encapsulating optical semiconductor element - Google Patents
Composition for encapsulating optical semiconductor element Download PDFInfo
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- KR101751541B1 KR101751541B1 KR1020100090262A KR20100090262A KR101751541B1 KR 101751541 B1 KR101751541 B1 KR 101751541B1 KR 1020100090262 A KR1020100090262 A KR 1020100090262A KR 20100090262 A KR20100090262 A KR 20100090262A KR 101751541 B1 KR101751541 B1 KR 101751541B1
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Abstract
The present invention further improves a composition comprising an epoxy-modified silicone resin having a predetermined linear polysiloxane structure in terms of thermal shock resistance and available time.
The composition for sealing an optical semiconductor device of the present invention is a branched silicone resin produced by the addition reaction of (A) an unsaturated group-containing epoxy compound with an organopolysiloxane having SiH groups, wherein at least three epoxy groups per molecule, (B) a non-aromatic epoxy resin (A) having two or more epoxy groups per molecule, and (B) a non-aromatic epoxy resin having at least two epoxy groups per molecule, (A) and (B) is from 0.4 to 1.5 moles per mole of the total of 1 mole of the epoxy groups of the curing agents (A) and (B), (D) And 0.01 to 3 parts by mass based on 100 parts by mass of the total of the components (A) to (C).
Description
The present invention relates to a composition for sealing an optical semiconductor element such as an LED, and more particularly to a composition for sealing an optical semiconductor element such as an LED, which comprises a branched silicone resin in which an epoxy group is introduced into a silicon chain by an addition reaction, To a composition for providing cargo.
BACKGROUND ART [0002] Epoxy resin compositions are widely used for sealing optical semiconductor elements. The epoxy resin composition usually contains an alicyclic epoxy resin, a curing agent, and a curing catalyst. The optical semiconductor element is sealed by pouring the composition into a mold in which the optical semiconductor element is placed by a molding method such as casting or transfer molding and curing. However, the deterioration of the discoloration of the epoxy resin becomes a problem due to the brightness and power-up of the LED. Particularly, since the alicyclic epoxy resin is yellowed by blue light or ultraviolet light, there is a problem that the lifetime of the LED element is shortened.
Therefore, there has been proposed a composition comprising an epoxy-modified silicone in which silicon excellent in heat-resistant light resistance is modified with an epoxy compound. Examples of the epoxy-modified silicone include resins synthesized by condensing a silane with an epoxy group (Patent Document 1), silsesquioxane having at least two epoxy rings (Patent Document 2), monofunctional siloxane And an epoxy group is introduced into an organopolysiloxane containing units (M units) and tetraphotactic siloxane units (Q units) (Patent Document 3).
However, the composition containing these silicone resins has a low elastic modulus and is fragile. For this reason, the LED sealed with the composition has a problem that cracks tend to occur in the resin in the temperature cycle test.
In order to solve the above problems, the present inventors have invented a composition comprising an epoxy-modified silicone resin having a predetermined linear polysiloxane structure (Japanese Patent Application No. 2008-195122). The present invention aims at further improving the above composition in terms of thermal shock resistance and available time.
As a result of various investigations, the inventors of the present invention have found that the above object can be achieved by introducing an epoxy group into a silicon chain by an addition reaction, and have accomplished the present invention. That is, the present invention is a composition for sealing optical semiconductor devices comprising (A), (B), (C) and (D)
(A) an unsaturated group-containing epoxy compound, a branched silicone resin produced by the addition reaction of an organopolysiloxane having an SiH, three or more epoxy groups, at least one per molecule (R 1 SiO 3/2) units, at least 3 ( R 2 R 3 R 4 SiO 1 /2) units, and more than 3 (R 2 R 3 SiO) n (n is a branched silicone resin having an integer between 1 and 20) structure 100 parts by weight
[R 1 is a monovalent organic group of C 1 -20, R 2 and R 3 are independently a monovalent organic C 1 -20 of the device from each other, R 4 is being a monovalent organic Kii of 1 -20 C, only Wherein at least 3 of R < 4 > in one molecule is an epoxy group-
(B) a non-aromatic epoxy resin having two or more epoxy groups per molecule: 50 parts by mass or less based on 100 parts by mass of the total of the component (A) and the component (B)
(C) a curing agent (A) and (B) in which the amount of the reactive group with the epoxy group is from 0.4 to 1.5 mol based on 1 mol of the total of the epoxy group
(D) 0.01 to 3 parts by mass relative to 100 parts by mass of the total amount of the curing catalyst (A), the component (B) and the component (C)
The composition for sealing an optical semiconductor device of the present invention has a long usable time and does not increase viscosity during storage. Also, the cured product of the composition has high hardness and excellent thermal shock resistance, thereby forming a good optical semiconductor package.
In the composition of the present invention, the (A) branched silicone resin is produced by an addition reaction of an unsaturated group-containing epoxy compound and an organopolysiloxane having SiH groups. As a result, a longer usable time can be achieved as compared with the case where a silicone resin containing an epoxy group is introduced by the condensation reaction. The addition reaction is carried out in the presence of a platinum catalyst according to a conventional method.
(A) The branched silicone resin has 3 or more epoxy groups per molecule. The epoxy group is contained in R 4 , which will be described later, and is a bond saturated by the addition reaction, for example, an ethylene group derived from a vinyl group, a propylene group derived from an allyl group, and a group connecting a saturated bond and an epoxy group, Atoms. The epoxy equivalent of the (A) branched silicone resin is 200 to 1500 g / eq, preferably 200 to 1200 g / eq.
(A) the branched silicone resin is a resin having at least one (R 1 SiO 3/2 ) unit, at least 3 (R 2 R 3 R 4 SiO 1/2 ) units and at least 3 (R 2 R 3 SiO) n ( and n is an integer of 1 to 20). Since it has branches, the hardness of the cured product is high.
R 1 , R 2 , R 3 and R 4 are a monovalent organic group of C 1 -20 , with at least three of R 4 in one molecule being an epoxy group-containing group. Examples of the C 1 -20 monovalent organic group include alkyl groups such as a methyl group, ethyl group, propyl group and butyl group, alicyclic groups such as cyclopentyl group, cyclohexyl group and norbornyl group, and aryl groups such as phenyl group. Preferably, R 1 is a phenyl group, and R 2 and R 3 are methyl groups.
Examples of the epoxy group-containing group of R 4 include? -Glycidoxyethyl group and? - (3,4-epoxycyclohexyl) ethyl group, and combinations thereof. And is preferably? - (3,4-epoxycyclohexyl) ethyl group.
Preferably, the (A) branched silicone resin is represented by the following formula (2).
In the formulas, R 1 to R 4 are as defined above, p, q and r are integers of 1 to 20, preferably 1 to 10, and s is an integer of 1 to 5, preferably 1 to 2.
(A) branched silicone resin is prepared by adding an epoxy compound having an unsaturated group such as a vinyl group to an organopolysiloxane having SiH groups in the presence of a metal catalyst such as platinum as described above. For example, the formula (2) can be obtained by an addition reaction of an epoxy compound having an unsaturated group to an organopolysiloxane having a SiH group at a terminal represented by the following formula (3).
(Wherein R 1 to R 4 , p, q, r and s are as defined above)
Examples of the epoxy compound having an unsaturated group include vinylcyclohexene monoxide (Celloxide 2000Z, manufactured by Daicel Chemical Industries, Ltd.).
The organopolysiloxane of the above formula (3) can be obtained, for example, by reacting an organosilicon compound represented by R 1 SiX 3 or HR 2 R 3 SiX (X is a hydrolyzable group such as an alkoxy group) and (R 2 R 3 SiO) n n = 1 to 20), and adding an organopolysiloxane having a hydrolyzable group at the terminal thereof to the hydrolysis and condensation reaction.
(B) Examples of the nonaromatic epoxy resin having two or more epoxy groups per molecule include alicyclic epoxy resins such as (3,4-epoxycyclohexane) methyl 3 ', 4'-epoxycyclohexylcarboxylate; Epoxy resins such as bisphenol A type epoxy resins, bisphenol F type epoxy resins, phenol novolak type epoxy resins, cresol novolak type epoxy resins, naphthalene type epoxy resins, biphenyl type epoxy resins, aralkyl type epoxy resins and biphenyl aralkyl type epoxy resins A hydrogenated epoxy resin obtained by hydrogenating an aromatic ring; And dicyclopentadiene type epoxy resins. Of these, alicyclic epoxy resins are preferred from the viewpoint of light resistance.
The blending amount of the epoxy resin (B) is 50 parts by mass, preferably 40 parts by mass or less based on 100 parts by mass of the total of the components (A) and (B). If it exceeds 50 parts by mass, the light resistance tends to be lowered.
As the curing agent (C), any curing agent of an epoxy resin can be used, and examples thereof include an amine curing agent, a phenol curing agent and an acid anhydride curing agent. An acid anhydride-based curing agent is preferably used. Examples of the acid anhydride-based curing agent include phthalic anhydride, maleic anhydride, trimellitic anhydride, pyromellitic anhydride, hexahydrophthalic anhydride, 3-methylhexahydrophthalic anhydride, 4-methylhexahydrophthalic anhydride, - a mixture of hexahydrophthalic anhydride and 4-methylhexahydrophthalic anhydride, tetrahydrophthalic anhydride, anhydrous nadic acid, anhydrous methylnadic acid, norbornane-2,3-dicarboxylic anhydride, methylnorbornane- 2,3-dicarboxylic acid anhydride and the like.
The blending amount of the (C) curing agent is 0.4 to 1.5 moles per 1 mole of the total of the epoxy groups of the component (A) and the component (B) in the composition, that is, 0.4 to 1.5 equivalents of the curing agent relative to 1 equivalent of the total epoxy resin, To 1.0 equivalents.
Examples of (D) curing catalysts include quaternary phosphonium salts such as tetrabutylphosphonium O, O-diethylphosphorodithioate and tetraphenylphosphonium tetraphenylborate, triphenylphosphine, diphenylphosphine and the like Tertiary amine curing catalysts such as 1,8-diazabicyclo (5,4,0) undecene-7, triethanolamine and benzyldimethylamine, 2-methylimidazole, 2-phenyl Imidazoles such as methylimidazole, and the like. Of these, quaternary phosphonium salts are preferable.
The blending amount of the (D) curing catalyst is 0.01 to 3 parts by mass based on 100 parts by mass of the total of the components (A), (B) and (C). If the compounding amount of the curing catalyst is less than the above lower limit value, there is a possibility that the effect of accelerating the reaction between the epoxy resin and the curing agent can not be sufficiently obtained. On the other hand, if the blending amount of the curing catalyst is higher than the upper limit value, there is a fear of causing discoloration during curing or reflow test.
In addition to the above components, additives such as an antioxidant, a discoloration inhibitor, an anti-deterioration agent, an inorganic filler such as silica, a silane-based coupling agent, a modifier, a plasticizer, a diluent And the like. Further, a light-scattering agent such as a phosphor, a titanium oxide fine powder, silica or the like for changing the wavelength may be added.
The composition of the present invention can be produced by blending (A) a silicone resin, (B) an epoxy resin, (C) a curing agent and (D) a curing catalyst and, if necessary, various additives and melt mixing. The melt mixing may be a known method, for example, a method in which the aforementioned components are put into a reactor and melt-mixed in a batch manner, and a method in which the above components are continuously melted and mixed by being introduced into a kneader such as a kneader or a thermal three- Method.
The obtained molten mixture may be solidified at a predetermined temperature in the state of being injected into a mold in the B stage to be used for use.
The embodiment of sealing the light emitting semiconductor with the composition of the present invention is not particularly limited. For example, the light emitting semiconductor disposed in the case having the opening portion may be covered and the composition may be filled in the case and cured to seal the case. Alternatively, the LED substrate may be sealed on the matrix substrate by printing, transfer molding, injection molding, compression molding, or the like. When the light-emitting semiconductor element such as an LED is coated by potting or injection, the composition of the present invention is preferably in a liquid state, and is preferably 10 to 1,000,000 mPa · s, more preferably 100 to 1,000,000 mPa · s s. On the other hand, in the case of manufacturing a light emitting semiconductor device by transfer molding or the like, the above-mentioned liquid resin can be used, but it can also be produced by thickening the liquid resin to solidify (B stage), pelletizing and molding.
<Examples>
Hereinafter, the present invention will be described by way of examples, but the present invention is not limited to these examples.
≪ Synthesis Example 1: (A) Synthesis of branched silicone resin >
The reaction vessel was charged with 112.71 g (0.908 mol) of Celloxide-2000 (manufactured by Daicel Chemical Industries, Ltd.), 208 ml of toluene and 2% octyl alcohol solution of chloroplatinic acid (20 ppm of Pt) 100 g (0.303 mol) of the organopolysiloxane (n = 1) and 61 ml of toluene were added dropwise, and the mixture was heated under reflux for 16 hours.
After the completion of the reaction, toluene was removed under reduced pressure and filtration was carried out to obtain a desired resin (Resin 1). The epoxy equivalent of resin 1 was 262 g / eq.
<Formula a>
In the 1 H-NMR (300 MHz, CDCl 3 ) of the organopolysiloxane represented by the above formula (a), peaks were observed at 0.38 ppm, 4.98 ppm (Si-H), 7.50 ppm and 7.75 ppm. On the other hand, in the 1 H-NMR (300 MHz, CDCl 3 ) of the resin 1, peaks were observed at 0.09 ppm, 0.51 ppm, 1.15 ppm, 1.29 ppm, 2.12 ppm, 3.12 ppm, and 7.24 ppm and the alicyclic epoxy group . Further, peaks were observed at -76 to -80 ppm (PhSiO 3/2 ) and 8 to 11 ppm (Me 2 SiO) in 29 Si-NMR (60 MHz, CDCl 3 ) of Resin 1, It was confirmed that there was no alkoxy group normally observed in the resin.
≪ Synthesis Example 2: (A) Synthesis of branched silicone resin >
After adding 74.51 g (0.600 mole) of Celllockide-2000 (manufactured by Daicel Chemical Industries, Ltd.), 150 ml of toluene and a 2% octyl alcohol solution of chloroplatinic acid (20 ppm of Pt) into the reaction vessel, 161 g (0.200 mol) of an organopolysiloxane (n = 5), and 40 ml of toluene were added dropwise and the mixture was refluxed for 16 hours. After completion of the reaction, toluene was removed under reduced pressure, and filtration was carried out to obtain the desired resin (Resin 2). The epoxy equivalent of resin 2 was 546 g / eq.
≪ Synthesis Example 3: (A) Synthesis of branched silicone resin >
After adding 74.51 g (0.600 mole) of Celllockide-2000 (manufactured by Daicel Chemical Industries, Ltd.), 150 ml of toluene and a 2% octyl alcohol solution of chloroplatinic acid (20 ppm of Pt) into the reaction vessel, , 520 g (0.200 mol) of an organopolysiloxane (n = 10), and 100 ml of toluene were added dropwise, and the mixture was heated under reflux for 16 hours. After completion of the reaction, toluene was removed under reduced pressure, and filtration was carried out to obtain the intended resin (Resin 3). The epoxy equivalent of resin 3 was 1023 g / eq.
≪ Synthesis Example 4: (A) Synthesis of branched silicone resin >
The reaction vessel was charged with 99.35 g (0.800 mole) of Celloxide-2000 (manufactured by Daicel Chemical Industries, Ltd.), 180 ml of toluene and 2% octyl alcohol solution of chloroplatinic acid (20 ppm of Pt) (0.200 mole) of organopolysiloxane and 40 ml of toluene were added dropwise, and the mixture was heated to reflux. After completion of the reaction, the toluene was removed under reduced pressure and filtration was carried out to obtain the intended resin (Resin 4). The epoxy equivalent of resin 4 was 269 g / eq.
<Formula b>
In the 1 H-NMR (300 MHz, CDCl 3 ) of the organopolysiloxane represented by the above formula (b), peaks were observed at 0.31 ppm, 4.85 ppm (Si-H), 7.39 ppm and 7.76 ppm. On the other hand, in the 1 H-NMR (300 MHz, CDCl 3 ) of Resin 4, peaks were observed at 0.02 ppm, 0.43 ppm, 1.07 ppm, 1.53 ppm, 1.90 ppm, 2.06 ppm, 3.10 ppm, and 7.17 ppm, It was confirmed that an epoxy group was bonded. A peak was observed at -74 to -83 ppm (PhSiO 3/2 ) and 7 to 11 ppm (Me 2 SiO) in 29 Si-NMR (60 MHz, CDCl 3 ) of Resin 4, It was confirmed that there was no alkoxy group normally observed.
≪ Comparative Synthesis Example 5: Production of branched silicone resin by condensation reaction >
MeO the reaction vessel (Me) 2 (Me 2 SiO ) SiO n Si (Me) 2 OMe (n = about 1.5 dog) 596.82 g (2.10 mol) of phenyltrimethoxysilane (manufactured by high-Etsu Chemical Co., a new school KBM103 ) And 1250 ml of isopropyl alcohol were added, and then 21.75 g of a 25% aqueous solution of tetramethylammonium hydroxide and 195.75 g of water were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, 1250 ml of toluene was added to the system, and neutralized with an aqueous solution of sodium hydrogen dihydrogen phosphate. The residue was washed with hot water using a separatory funnel. Toluene was removed under reduced pressure to obtain an oligomer. Further, 517.44 g (2.10 mol) of 3- (3,4-epoxycyclohexyl) ethyltrimethoxysilane (KBM303, manufactured by Shinetsu Chemical Co., Ltd.) and 600 ml of isopropyl alcohol were added to the oligomer and tetramethyl 21.75 g of 25% aqueous solution of ammonium and 195.75 g of water were added and stirred at room temperature for 3 hours. After completion of the reaction, 1250 ml of toluene was added to the system, and neutralized with an aqueous solution of sodium hydrogen dihydrogen phosphate. The residue was washed with hot water using a separatory funnel. The toluene was removed under reduced pressure to obtain a desired resin (referred to as "resin 5"). The epoxy equivalent of resin 5 was 441 g / eq.
In addition, 29 Si-NMR of the resin 5 (60 MHz, CDCl 3) in the -64 to -56 ppm (PhSiO 3/2), -52 to -44 ppm (completely condensed units T Si portions), -41 to -36 (alkoxy-containing T unit Si part), -4 to 3 ppm (complete condensation D unit Si part), and 6 to 10 ppm (alkoxy-containing D unit Si part), and alkoxy groups remained .
A composition was prepared using the obtained resin and the following components.
(B) Epoxy resin: (3,4-epoxycyclohexane) methyl 3 ', 4'-epoxycyclohexylcarboxylate (Celloxide 2021P, manufactured by Daicel Chemical Industries, Ltd.)
(C) Hardener: Methyl hexahydrophthalic anhydride (MH, Shin-Nippon Chemical Co., Ltd.)
(D) Curing catalyst: Organophosphonium salt (UCAT-5003, manufactured by San A Pro Co., Ltd.)
Adhesion aid: 3-mercaptopropylmethyldimethoxysilane (KBM-803, manufactured by Shin-Etsu Chemical Co., Ltd.)
≪ Examples 1 to 4, Comparative Example 1 >
The composition was prepared according to the prescription (mass part) shown in Table 1.
The resulting composition was subjected to post curing at 100 占 폚 for 2 hours and further at 150 占 폚 for 4 hours to obtain a bar-shaped cured product having a thickness of 5 mm. The bar-shaped cured product was evaluated for appearance, bending elastic modulus and bending strength (JIS K-6911) and appearance after light fastness test. In the light resistance test, the transmittance after UV irradiation (high-pressure mercury lamp 30 mW / cm 2, 365 nm) for 12 hours was obtained when the initial transmittance at 400 nm was 100%. The viscosity ratio after storage at 23 캜 for 8 hours against the initial viscosity at 23 캜 was also measured. The results are shown in Table 1 below.
LED device
Using the compositions of Examples 2 and 3 and Comparative Example 1, three LED devices were produced in the following manner. The InGaN-based blue light emitting device was fixed to the pre-molded package for LED with a thickness of 1 mm, a side of 3 mm, an opening of 2.6 mm in diameter, and a silver coating on the bottom side by silver paste. Subsequently, the external electrode and the light emitting element were connected with a gold wire. Each composition was injected into the package opening. And then cured at 100 DEG C for 1 hour and further at 150 DEG C for 2 hours to prepare an LED device. The manufactured LED device was subjected to a temperature cycle test under the following conditions and an LED lighting test under a condition of 65 deg. C / 95% RH for 3000 hours to visually observe adhesion failure, presence or absence of cracks and discoloration at the package interface Respectively. The results are shown in Table 2 below.
As can be seen from Table 1, the viscosity of the composition of Comparative Example 1 including the resin 5 obtained by the condensation reaction was remarkable. Further, as can be seen from Table 2, the package obtained from the composition of Comparative Example 1 had lower heat shock resistance and light resistance than the cured product obtained from the composition of Example.
The composition for sealing an optical semiconductor device of the present invention is useful for forming an optical semiconductor device having a long usable time and excellent in light resistance and thermal shock resistance.
Claims (6)
(A) 100 parts by mass of a branched silicone resin represented by the following formula (2), which is produced by the addition reaction of an unsaturated group-containing epoxy compound with an organopolysiloxane having SiH groups
(2)
( Wherein R 1 is a C 1-20 monovalent organic group, R 2 and R 3 are each independently a C 1-20 monovalent organic group, and R 4 is a C 1-20 monovalent organic group P, q and r are integers of 1 to 20, and s is an integer of 1 to 5, provided that at least three of R < 4 > in one molecule are epoxy group-
(B) a non-aromatic epoxy resin having two or more epoxy groups per molecule: 50 parts by mass or less based on 100 parts by mass of the total of the component (A) and the component (B)
(C) a curing agent (A) and (B) in which the amount of the reactive group with the epoxy group is from 0.4 to 1.5 mol based on 1 mol of the total of the epoxy group
(D) 0.01 to 3 parts by mass relative to 100 parts by mass of the total amount of the curing catalyst (A), the component (B) and the component (C)
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| JPJP-P-2009-214499 | 2009-09-16 | ||
| JP2009214499A JP5293525B2 (en) | 2009-09-16 | 2009-09-16 | Composition for sealing an optical semiconductor element |
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| KR20110030368A KR20110030368A (en) | 2011-03-23 |
| KR101751541B1 true KR101751541B1 (en) | 2017-06-27 |
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| KR (1) | KR101751541B1 (en) |
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| TW (1) | TWI481671B (en) |
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| JP6332907B2 (en) | 2013-02-14 | 2018-05-30 | 東京応化工業株式会社 | Resin composition for sealing, display device, and optical semiconductor device |
| JP2014227544A (en) * | 2013-05-27 | 2014-12-08 | 信越化学工業株式会社 | Resin composition for sealing optical semiconductor element, and optical semiconductor device using the same |
| JP6098531B2 (en) * | 2014-01-23 | 2017-03-22 | 信越化学工業株式会社 | Resin composition, resin film, semiconductor device and manufacturing method thereof |
| WO2015125803A1 (en) * | 2014-02-19 | 2015-08-27 | 信越化学工業株式会社 | Silicone-modified epoxy resin, composition containing said epoxy resin, and cured product thereof |
| JP6523780B2 (en) | 2014-09-29 | 2019-06-05 | 東京応化工業株式会社 | Film-forming composition and method for producing cured film using the same |
| JP6404110B2 (en) | 2014-12-18 | 2018-10-10 | 信越化学工業株式会社 | Epoxy resin containing silicone-modified epoxy resin and polyvalent carboxylic acid compound and cured product thereof |
| TW202037667A (en) * | 2019-01-30 | 2020-10-16 | 日商日立化成股份有限公司 | Sealing resin composition, electronic component device and method of producing electronic component device |
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|---|---|---|---|---|
| WO2012066743A1 (en) | 2010-11-15 | 2012-05-24 | コニカミノルタオプト株式会社 | Hard coating film and image display device |
| JP2014514284A (en) | 2011-03-23 | 2014-06-19 | ビーエーエスエフ ソシエタス・ヨーロピア | Compositions containing polymeric ionic compounds containing imidazolium groups |
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| BE655303A (en) * | 1963-11-12 | 1965-03-01 | ||
| JPH01188516A (en) * | 1988-01-22 | 1989-07-27 | Asahi Glass Co Ltd | Curable composition |
| JPH03236393A (en) * | 1990-02-13 | 1991-10-22 | Sumitomo Durez Co Ltd | Silicone-modified phenol compound, production thereof and epoxy derivative |
| US5863970A (en) * | 1995-12-06 | 1999-01-26 | Polyset Company, Inc. | Epoxy resin composition with cycloaliphatic epoxy-functional siloxane |
| JP3851441B2 (en) * | 1998-04-23 | 2006-11-29 | 日東電工株式会社 | Epoxy resin composition for optical semiconductor element sealing and optical semiconductor device |
| DE10107985C1 (en) * | 2001-02-19 | 2002-04-18 | 3M Espe Ag | Polymerizable formulation used for coating and/or bonding substrates or as dental formulation, contains organosilicon compound with aliphatic and cycloaliphatic epoxide groups, filler and initiator, inhibitor and/or accelerator |
| JP4198091B2 (en) * | 2004-06-02 | 2008-12-17 | 旭化成株式会社 | Resin composition for sealing light emitting device |
| US20070299165A1 (en) * | 2006-06-27 | 2007-12-27 | Gelcore Llc | Phenyl-containing silicone epoxy formulations useful as encapsulants for LED applications |
| US20080160317A1 (en) * | 2006-12-29 | 2008-07-03 | Deborah Ann Haitko | Optoelectronic device |
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| WO2012066743A1 (en) | 2010-11-15 | 2012-05-24 | コニカミノルタオプト株式会社 | Hard coating film and image display device |
| JP2014514284A (en) | 2011-03-23 | 2014-06-19 | ビーエーエスエフ ソシエタス・ヨーロピア | Compositions containing polymeric ionic compounds containing imidazolium groups |
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| CN102020853B (en) | 2014-07-02 |
| JP2011063686A (en) | 2011-03-31 |
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| KR20110030368A (en) | 2011-03-23 |
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