IP Library Granted Patent US 9,453,158
Granted Patent B2
US 9,453,158 · App. 14/767,717 · Granted Sep 27, 2016

Curable silicone composition, cured product thereof, and optical semiconductor device

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Quick Facts
Patent No.
US 9,453,158
App. No.
14/767,717
Granted
Sep 27, 2016
Kind
B2
Abstract

The present invention relates to a curable silicone composition comprising: (A) an organopolysiloxane having at least two alkenyl groups in a molecule; (B) an organopolysiloxane represented by a general formula; (C) an organopolysiloxane having at least two silicon-bonded hydrogen atoms in a molecule; (D) a phosphor; and (E) a hydrosilylation reaction catalyst, to a cured product obtained by curing said composition, and to an optical semiconductor device in which a light emitting element is sealed or coated with a cured product of the aforementioned composition. The curable silicone composition has excellent fluidity and cures to form a cured product in which phosphors are homogeneously dispersed and which has a high refractive index.

Claims (45)

1. A curable silicone composition comprising:

(A) an organopolysiloxane having at least two alkenyl groups in a molecule, and excluding component (B) mentioned below;

(B) an organopolysiloxane represented by the general formula:

wherein, R 1 are the same or different and are each an alkenyl group having from 2 to 12 carbons, R 2 are the same or different and are each an aryl group having from 6 to 20 carbons or an aralkyl group having from 7 to 20 carbons, R 3 are the same or different and are each an alkyl group having from 1 to 12 carbons, and p is an integer from 1 to 100;

(C) an organopolysiloxane having at least two silicon-bonded hydrogen atoms in a molecule, in an amount that the amount of silicon-bonded hydrogen atoms in component (C) is from 0.1 to 5 moles per 1 mol of total alkenyl groups in components (A) and (B);

(D) a phosphor; and

(E) an effective amount of a hydrosilylation reaction catalyst;

the content of component (A) being from 20 to 80 mass %, the content of component (B) being from 0.1 to 20 mass % and the content of component (D) being from 0.1 to 70 mass %, each relative to the total amount of components (A) to (E).

2. The curable silicone composition according to claim 1 , wherein

component (A) is

(A 1 ) an organopolysiloxane which has at least two alkenyl groups in a molecule and which is represented by the average unit formula:

(R 1 R 4 2 SiO 1/2 ) a (R 5 2 SiO 2/2 ) b (R 2 SiO 3/2 ) c

wherein, R 1 is an alkenyl group having from 2 to 12 carbons, R 2 is an aryl group having from 6 to 20 carbons or an aralkyl group having from 7 to 20 carbons, R 4 are the same or different and are each an alkyl group having from 1 to 12 carbons, an alkenyl group having from 2 to 12 carbons, an aryl group having from 6 to 20 carbons, or an aralkyl group having from 7 to 20 carbons, R 5 are the same or different and are each an alkyl group having from 1 to 12 carbons, an alkenyl group having from 2 to 12 carbons, or a phenyl group, and a, b, and c are numbers that satisfy such that

0.01≦a≦0.5, 0≦b≦0.7, 0.1≦c<0.9, and a+b+c=1, or

a mixture of component (A 1 ) and (A 2 ) an organopolysiloxane represented by the general formula:

wherein, R 1 and R 2 are synonymous with the groups described above, R 3 is an alkyl group having from 1 to 12 carbons, R 6 are the same or different and are each an alkyl group having from 1 to 12 carbons, an aryl group having from 6 to 20 carbons, or an aralkyl group having from 7 to 20 carbons, m is an integer from 1 to 100, and n is an integer from 0 to 50, where m≧n and 1≦m+n≦100, in the content of component (A 2 ) is at most 50 mass % relative to the total amount of components (A) to (E).

3. The curable silicone composition according to claim 1 , wherein

component (C) is

(C 1 ) an organopolysiloxane represented by the general formula:

HR 3 R 6 SiO(R 6 2 SiO) s SiR 3 R 6 H

wherein, R 3 are the same or different and are each an alkyl group having from 1 to 12 carbons, R 6 are the same or different and are each an alkyl group having from 1 to 12 carbons, an aryl group having from 6 to 20 carbons, or an aralkyl group having from 7 to 20 carbons, and s is an integer from 0 to 100,

(C 2 ) an organopolysiloxane having at least two silicon-bonded hydrogen atoms in a molecule, which is represented by the average unit formula:

(HR 3 R 6 SiO 1/2 ) d (HR 3 2SiO 1/2 ) e (R 6 2 SiO 2/2 ) f (R 2 SiO 3/2 ) g

wherein, R 2 is an aryl group having from 6 to 20 carbons or an aralkyl group having from 7 to 20 carbons, R 3 and R 6 are synonymous with the groups described above, and d, e, f, and g are numbers that satisfy such that 0.01≦d≦0.7, 0≦e≦0.5, 0≦f≦0.7, 0.1≦g<0.9, and d+e+f+g=1, or

a mixture of components (C 1 ) and (C 2 ).

4. The curable silicone composition according to claim 2 , wherein R 2 in component (A 1 ) is a phenyl group or a naphthyl group.

5. The curable silicone composition according to claim 1 , wherein R 2 in component (B) is a phenyl group or a naphthyl group.

6. The curable silicone composition according to claim 3 , wherein at least one R 6 in component (C 1 ) is a phenyl group or a naphthyl group.

7. The curable silicone composition according to claim 3 , wherein R 2 in component (C 2 ) is a phenyl group or a naphthyl group.

8. The curable silicone composition according to claim 3 , wherein in the mixture of components (C 1 ) and (C 2 ), the mass ratio of component (C 1 ) and component (C 2 ) is from 0.5:9.5 to 9.5:0.5.

9. The curable silicone composition according to claim 1 , further comprising (F) an adhesion-imparting agent in an amount of 0.01 to 10 parts by mass per 100 parts total mass of components (A) to (E).

10. A cured product produced by curing the curable silicone composition of claim 1 .

11. An optical semiconductor device comprising a light emitting element sealed or coated with a cured product of the curable silicone composition described in claim 1 .

12. The curable silicone composition according to claim 2 , wherein

component (C) is

(C 1 ) an organopolysiloxane represented by the general formula:

HR 3 R 6 SiO(R 6 2 SiO) s SiR 3 R 6 H

wherein, R 3 are the same or different and are each an alkyl group having from 1 to 12 carbons, R 6 are the same or different and are each an alkyl group having from 1 to 12 carbons, an aryl group having from 6 to 20 carbons, or an aralkyl group having from 7 to 20 carbons, and s is an integer from 0 to 100,

(C 2 ) an organopolysiloxane having at least two silicon-bonded hydrogen atoms in a molecule, which is represented by the average unit formula:

(HR 3 R 6 SiO 1/2 ) d (HR 3 2 SiO 1/2 ) e (R 6 2 SiO 2/2 ) f (R 2 SiO 3/2 ) g

wherein, R 2 is an aryl group having from 6 to 20 carbons or an aralkyl group having from 7 to 20 carbons, R 3 and R 6 are synonymous with the groups described above, and d, e, f, and g are numbers that satisfy such that 0.01≦d≦0.7, 0≦e≦0.5, 0≦f≦0.7, 0.1≦g<0.9, and d+e+f+g=1, or

a mixture of components (C 1 ) and (C 2 ).

13. The curable silicone composition according to claim 2 , wherein R 2 in component (B) is a phenyl group or a naphthyl group.

14. The curable silicone composition according to claim 3 , wherein R 2 in component (B) is a phenyl group or a naphthyl group.

15. The curable silicone composition according to claim 4 , wherein R 2 in component (B) is a phenyl group or a naphthyl group.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 16, 2025
From: DUPONT TORAY SPECIALTY MATERIALS KABUSHIKI KAISHA
To: DUROPTIX MATERIALS KABUSHIKI KAISHA
Reel/Frame 073229/0238 →
CHANGE OF NAME Recorded May 12, 2025
From: DOW CORNING TORAY COMPANY, LTD.
To: DUPONT TORAY SPECIALTY MATERIALS KABUSHIKI KAISHA
Reel/Frame 071080/0537 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 25, 2015
From: SAGAWA, TAKASHI; AMAKO, MASAAKI; ITOH, MAKI; SUTO, MICHITAKA; IIMURA, TOMOHIRO
To: DOW CORNING TORAY CO., LTD.
Reel/Frame 036408/0079 →