IP Library Granted Patent US 8,475,912
Granted Patent B2
US 8,475,912 · App. 12/385,688 · Granted Jul 2, 2013

Coating composition for forming low-refractive-index layer, antireflective film using the same, and image display device including the antireflective film

Inventors: Yun Jeong Seong (Seoul, KR); Kyoung Ku Kang (Nonsan-si, KR); Hyoung Tae Lim (Uiwang-si, KR); Young Cheol Lee (Suwon-si, KR)
Assignee: Cheil Industries, Inc.
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Quick Facts
Patent No.
US 8,475,912
App. No.
12/385,688
Filed
Apr 16, 2009
Granted
Jul 2, 2013
Kind
B2
Art Unit
1783
USPC
428/212
Abstract

A coating composition for forming a low-refractive-index layer includes a first fluorine compound represented by Formula 1 below, (CH 2 ═CR 1 COO) 2 R f   Formula 1 and a reactive silicon compound, a (meth)acrylate compound, a polymerization initiator, and a solvent. The first fluorine compound represented by Formula 1, the reactive silicon compound, the (meth)acrylate compound, the polymerization initiator, and the solvent may each be different from one another, and in Formula 1, R f may be a C 1-19 perfluoro group, and R 1 may be a hydrogen atom or a methyl group.

Claims (52)

1. A coating composition for forming a low-refractive-index layer, the composition comprising:

about 70 to about 95 parts by weight of a fluorine compound including a first fluorine compound represented by Formula 1 below;

(CH 2 ═CR 1 COO) 2 R f   Formula 1

about 0.1 to about 15 parts by weight of a reactive silicon compound;

about 1 to about 20 parts by weight of a (meth)acrylate compound;

about 0.1 to about 10 parts by weight of a polymerization initiator; and

a solvent, wherein:

the first fluorine compound represented by Formula 1, the reactive silicon compound, the (meth)acrylate compound, the polymerization initiator, and the solvent are each different from one another,

in Formula 1, R 1 is a hydrogen atom or a methyl group and the R f in Formula 1 is a moiety represented by one of Formulae 2(a)-(e) below:

in Formula 2(a)-(e), R f1 is a linear C 1-10 perfluoro group, and R f2 , R f3 , R f4 , and R f5 are each independently a linear C 1-14 perfluoro group, and

all parts by weight are based on 100 parts by weight of a total solid content of the composition.

2. The composition as claimed in claim 1 , wherein the fluorine compound further includes a second fluorine compound represented by Formula 1, wherein:

the second fluorine compound represented by Formula 1 is different from the first fluorine compound, and

in the first fluorine compound and the second fluorine compound, each R f is independently a moiety represented by one of Formulae 2(a)-(e).

3. The composition as claimed in claim 2 , wherein the first fluorine compound and the second fluorine compound are each present in an amount of about 10 or more parts by weight, based on 100 parts by weight of a total weight of the first fluorine compound and the second fluorine compound represented by Formula 1.

4. The composition as claimed in claim 1 , wherein the fluorine compound further includes a third fluorine compound represented by Formula 3 below:

R f —O-A O—CO—CR 2 ═CH 2 ] a   Formula 3

wherein, in Formula 3, R f is a C 1-18 perfluoro group, A is a dehydrated polyhydric alcohol residue, R 2 is a hydrogen atom or a methyl group, and a is an integer from 1 to 3.

5. The composition as claimed in claim 4 , wherein:

the first fluorine compound represented by Formula 1 is present in an amount of about 50 to about 80 parts by weight, based on 100 parts by weight of a total solid content of the composition, and

the third fluorine compound represented by Formula 3 is present in an amount of about 5 to about 40 parts by weight, based on 100 parts by weight of a total solid content of the composition.

6. The composition as claimed in claim 1 , wherein the (meth)acrylate compound is present in an amount of about 3 to about 10 parts by weight, based on 100 parts by weight of a total weight of the first fluorine compound represented by Formula 1 and the (meth)acrylate compound.

7. The composition as claimed in claim 1 , wherein:

the total solid content of the composition is the total weight of the fluorine compound, the reactive silicon compound, the (meth)acrylate compound, and the polymerization initiator in the composition, and

the total solid content is about 1 to about 20 parts by weight, based on 100 parts by weight of a total weight of the composition.

8. The composition as claimed in claim 1 , wherein the reactive silicon compound is present in an amount of about 0.2 to about 10 parts by weight, based on 100 parts by weight of a total solid content of the composition.

9. The composition as claimed in claim 1 , wherein:

the reactive silicon compound is represented by Formula 5 below:

wherein, in Formula 5, X 1 , X 2 , and X 3 are each hydrogen or a methyl group, X 1 , X 2 , and X 3 are the same as or different from each other, at least one of R 3 and R 4 is a curable reactive group, R 3 and R 4 are the same as or different from each other, and b is an integer from 3 to 1000, or

the reactive silicon compound is represented by Formula 6 below:

wherein, in Formula 6, X 4 and X 5 are each hydrogen or a methyl group, X 4 and X 5 are the same as or different from each other, at least one of R 5 and R 6 is a curable reactive group, R 5 and R 6 are the same as or different from each other, and c is an integer from 3 to 1,000.

10. The composition as claimed in claim 1 , further comprising colloidal silica modified by a fluorine silane coupling agent.

11. An antireflective film, comprising:

a substrate;

a hard coating layer;

a high-refractive-index layer; and

a low-refractive-index layer, wherein:

the low-refractive-index layer is formed using the composition as claimed in claim 1 .

12. The antireflective film as claimed in claim 11 , wherein the antireflective film has an average reflectance of less than about 3% in a visible light range of 380 to 780 nm.

13. The antireflective film as claimed in claim 11 , wherein the antireflective film has a minimum reflectance of less than about 1% in a light wavelength range of 550 to 650 nm.

14. An image display device, comprising the antireflective film as claimed in claim 11 .

15. A coating composition for forming a low-refractive-index layer, the composition comprising:

a first fluorine compound represented by Formula 1 below;

(CH 2 ═CR 1 COO) 2 R f   Formula 1

a second fluorine compound represented by Formula 1;

a reactive silicon compound;

a (meth)acrylate compound;

a polymerization initiator; and

a solvent, wherein:

the first fluorine compound represented by Formula 1, the second fluorine compound, the reactive silicon compound, the (meth)acrylate compound, the polymerization initiator, and the solvent are each different from one another,

in the first fluorine compound and the second fluorine compound represented by Formula 1, R 1 is a hydrogen atom or a methyl group and the R f in Formula 1 is a moiety represented by one of Formulae 2(a)-(e) below:

in Formula 2(a)-(e), R f1 is a linear C 1-10 perfluoro group, and R f2 , R f3 , R f4 , and R f5 are each independently a linear C 1-14 perfluoro group.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2026
From: WUXI HENGXIN OPTOELECTRONIC MATERIALS CO., LTD.
To: HOARDSUN HENGXIN(WUXI) MATERIALS CO., LTD.
Reel/Frame 075049/0450 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2025
From: SAMSUNG SDI CO., LTD.
To: WUXI HENGXIN OPTOELECTRONIC MATERIALS CO., LTD.
Reel/Frame 073062/0496 →
MERGER Recorded Jun 16, 2025
From: CHEIL INDUSTRIES INC.
To: SAMSUNG SDI CO., LTD.
Reel/Frame 071636/0099 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 16, 2009
From: SEONG, YUN JEONG; KANG, KYOUNG KU; LIM, HYOUNG TAE; LEE, YOUNG CHEOL
To: CHEIL INDUSTRIES, INC.
Reel/Frame 022611/0768 →
Priority Claims (2)
KR 10-2006-0100262 · Oct 16, 2006 · national
KR 10-2006-0108903 · Nov 6, 2006 · national
Continuity (2)
Continuation PCTKR2006005615 · Dec 21, 2006
Related Publication 20090202802A1 · Aug 13, 2009