Curable composition

Patent metadata

Field	Value
Publication number	US-9355926-B2
Application number	US-201314030562-A
Country	US
Kind code	B2
Filing date	Sep 18, 2013
Priority date	Jul 27, 2012
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

Provided are a curable composition and its use. The curable composition can exhibit excellent processability and workability. The curable composition exhibits excellent light extraction efficiency, hardness, thermal and shock resistance, moisture resistance, gas permeability, and adhesiveness, after curing. In addition, the curable composition can provide a cured product that exhibits long-lasting durability and reliability even under harsh conditions and that does not cause whitening or surface stickiness.

First claim

What is claimed is:

1. A curable composition, comprising:
a polymerization product of a mixture comprising: a compound represented by Formula 7; a polyorganosiloxane having an average empirical formula of Formula 10 or 11; and a compound represented by Formula 12,
wherein the polymerized product comprises:
a partially-crosslinked polyorganosiloxane having a functional group comprising an aliphatic unsaturated bond, which has an average empirical formula of Formula 4 or Formula 5,
a linear polyorganosiloxane having a functional group comprising an aliphatic unsaturated bond, which has an average empirical formula of Formula 4 or Formula 5 and wherein c, d and h in Formula 4 or Formula 5 are zero, b/(b+c+d) and (f+g)/(f+g+h) in Formula 4 or Formula 5 are 1, and f and g in Formula 5 are 0.65 to 0.97, of which a ratio of a mole number of the aryl group included in a D unit to a mole number of a silicon atom included in total D units is 0.3 or more to 0.65 or less; and
a cyclic compound and of which a molar ratio (Ak/Si) of functional groups including the aliphatic unsaturated bond (Ak) to total silicon atoms (Si) in the polyorganosiloxane is 0.02 to 0.15, which comprises a compound represented by Formula 6 and of which a weight average molecular weight of 800 or less, the cyclic compound being comprised in the polymerization product in an amount of more than 0 weight % and 7 weight % or less, and
wherein the polymerized product, the partially-crosslinked polyorganosiloxane or the linear polyorganosiloxane have an acid value obtained by KOH titration of 0.02 to less; and
a silicon compound comprising a hydrogen atom binding to a silicon atom[H] 2
(R 4 3 SiO 1/2 ) a (R 4 2 SiO 2/2 ) b (R 4 SiO 3/2 ) c (SiO 4/2 ) d   [Formula 4]

wherein R 4 's are each independently an epoxy group or a monovalent hydrocarbon group, with the proviso that at least one of R 4 's is an alkenyl group and at least one of R 4 's is an aryl group and R 4 in T units is an epoxy group; a is a positive number, b is a positive number, c is a positive number and d is 0, when the sum (a+b+c+d) of the molar ratios is adjusted to be 1, a is 0.01 to 0.15, b is 0.65 to 0.97, c is 0.01 to 0.30, and b/(b+c+d) is 0.65 or more,
(R 5 R 6 2 SiO 1/2 ) e (R 7 R 8 SiO 2/2 ) f (R 9 2 SiO 2/2 ) g (R 10 SiO 3/2 ) h   [Formula 5]

wherein R 5 is a monovalent hydrocarbon group, R 6 is an alkyl group having 1 to 4 carbon atoms, R 7 and R 8 are each independently an alkyl group, an alkenyl group, or an aryl group, R 9 is an aryl group, R 10 is an epoxy group, e is a positive number, f, g, and h are a positive number, when the sum (e+f+g+h) of the molar ratios is adjusted to be 1, e is 0.01 to 0.15, f is 0 to 0.97, g is 0 to 0.97, h is 0.01 to 0.30, and (f+g)/(f+g+h) is 0.65 or more,

wherein R a and R b are each independently an epoxy group or a monovalent hydrocarbon group, R e is an aryl group, m is 0 to 10, n is 0 to 10, and the sum (m+n) of m and n is 2 to 20,

wherein R d and R e are each independently an epoxy group or a monovalent hydrocarbon group, and o is 3 to 6,
[R j SiO 3/2 ][Formula 10]
[R k R l 2 SiO 1/2 ] p [R m SiO 3/2 ] q   [Formula 11]

(R n R o 2 Si) 2 O  [Formula 12]

wherein R j , R k , R m , R n and R o are each independently an epoxy group or a monovalent hydrocarbon group, R l is an alkyl group having 1 to 4 carbon atoms, p is 1 to 3, q is 1 to 10.

2. The curable composition according to claim 1 , wherein R a and R b are each independently an alkyl group.

3. The curable composition according to claim 1 , wherein the partially-crosslinked polyorganosiloxane or the linear polyorganosiloxane of the polymerized product comprises a unit of Formula 2 and a unit of Formula 3:
(R 1 R 2 SiO 2/2 )  [Formula 2]

(R 3 2 SiO 2/2 )  [Formula 3]

wherein R 1 and R 2 are each independently an epoxy group or a monovalent hydrocarbon group, and R 3 is an aryl group.

4. The curable composition according to claim 1 , wherein a molar ratio of aryl groups with respect to the entire functional groups in the partially-crosslinked polyorganosiloxane or the linear polyorganosiloxane of the polymerized product is from 30% to 60%.

5. The curable composition according to claim 3 , wherein a ratio of a mole number of the siloxane unit of Formula 3 with respect to bifunctional siloxane units comprising an aryl group in the partially-crosslinked polyorganosiloxane or the linear polyorganosiloxane is 70% or more.

6. The curable composition according to claim 1 , wherein the cyclic compound has a weight average molecular weight of 750 or less.

7. The curable composition according to claim 1 , wherein the polymerization product is a polymerization product of a mixture comprising a compound of Formula 8 and a compound of Formula 9:

wherein R f and R g are each an epoxy group or an alkyl group, R h and R i are each an epoxy group or an aryl group, p is a number of 3 to 6, and q is a number of 3 to 6.

8. The curable composition according to claim 1 , further comprising a polyorganosiloxane having an average empirical formula of Formula 13:
(R 11 3 SiO 1/2 ) a (R 11 2 SiO 2/2 ) b ( 11 SiO 3/2 ) c (SiO 4/2 ) d   [Formula 13]

wherein R 11 's are each independently an epoxy group or a monovalent hydrocarbon group, with the proviso that at least one of R 11 s is an alkenyl group and at least one of R 11 's is an aryl group; a is a positive number, b is 0 or a positive number, c is a positive number, d is 0 or a positive number, b/(b+c+d) is less than 0.65, and c/(c+d) is 0.8 or more.

9. The curable composition according to claim 1 , further comprising a compound of Formula 14 or a compound having an average empirical formula of Formula 15:
R 12 3 SiO(R 12 2 SiO) n SiR 12 3   [Formula 14]

(R 13 3 SiO 1/2 ) a (R 13 2 SiO 2/2 ) b (R 13 SiO 3/2 ) c (SiO 2 ) d   [Formula 15]

where R 12 's are each independently hydrogen or a monovalent hydrocarbon group, with the proviso that at least two of R 12 's are hydrogen atoms and at least one of R 12 's is an aryl group; n is 1 to 100; R 13 's are each independently hydrogen or a monovalent hydrocarbon group, with the proviso that at least two of R 13 's are hydrogen atoms and at least one of R 13 's is an aryl group; and a is a positive number, b is 0 or a positive number, c is a positive number, and d is 0 or a positive number.

10. A photonic semiconductor encapsulated by the cured curable composition of claim 1 .

11. A liquid crystal display comprising the photonic semiconductor of claim 10 in a backlight unit.

12. A lighting apparatus comprising the photonic semiconductor of claim 10 .

13. The curable composition according to claim 1 , wherein the polymerization product has a ratio of an area of a peak derived from an alkoxy group binding to a silicon atom with respect to an area of a peak derived from a functional group containing the aliphatic unsaturated bond binding to silicon in a spectrum obtained by 1 H NMR of 0.01 or less.

Assignees

• Lg Chemical Ltd

Inventors

• Ko Min Jin
• Choi Bum Gyu
• Jung Jae Ho
• Kang Dae Ho
• Kim Min Kyoun
• Cho Byung Kyu

Classifications

• H10W74/476 Primary

  Organic materials comprising silicon · CPC title

• C08L83/06

  containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence) · CPC title

• C08L83/00

  Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers · CPC title

• C08G77/12

  containing silicon bound to hydrogen · CPC title

• C08G77/14

  containing silicon bound to oxygen-containing groups · CPC title