Silane compound including fluorine-containing (poly)ether group, composition including the same, film formed from the composition, display device comprising the film, and article comprising the composition

Patent metadata

Field	Value
Publication number	US-11525040-B2
Application number	US-202117164672-A
Country	US
Kind code	B2
Filing date	Feb 1, 2021
Priority date	Feb 26, 2020
Publication date	Dec 13, 2022
Grant date	Dec 13, 2022

Abstract

Disclosed are a composition comprising a silane compound having a fluorine-containing (poly)ether group represented by Formula 1, a film formed from the composition, a display device including the film, and an article including a coating product of the composition:Rf-(L1)p1(L)a-C(═O)NR-(L2)p2-Si(R1)(R2)(R3)   Formula 1wherein in Formula 1, R is -(L3)p3-Si(R4)(R5)(R6),L is —CH2— or —CH2—O—CH2—,Rf is a fluorine-containing (poly)ether group, andL1 to L3, p1 to p3, and R1 to R6 are the same as defined in the detailed description.

First claim

What is claimed is:

1. A silane compound comprising a fluorine-containing ether group, wherein the silane compund is
CF 3 O(CF 2 CF 2 O) n (CF 2 O) m —(CH 2 )—C(═O)N{(CH 2 ) 3 —Si(OCH 3 )(OCH 3 )(OCH 3 )} 2 ,
CF 3 O(CF 2 O) m (CF 2 CF 2 O) n —(CH 2 )—C(═O)N{(CH 2 ) 3 —Si(OCH 3 )(OCH 3 )(OCH 3 )} 2 ,
CF 3 CF 2 O(CF 2 CF 2 O) n (CF 2 O) m —(CH 2 )—C(═O)N{(CH 2 ) 3 —Si(OCH 3 )(OCH 3 )(OCH 3 )} 2 ,
CF 3 CF 2 O(CF 2 O) m (CF 2 CF 2 O) n —(CH 2 )—C(═O)N{(CH 2 ) 3 —Si(OCH 3 )(OCH 3 )(OCH 3 )} 2 ,
CF 3 CF 2 O(CF 2 CF 2 O) n (CF 2 O) m —(CH 2 )—C(═O)N{(CH 2 ) 3 —Si(OCH 3 )(OCH 3 )(OCH 3 )} 2 ,
a compound of Formula 2-1,
a compound of Formula 2-2,
a compound of Formula 2-3, or
a combination thereof,
wherein n and m are each independently an integer of 1 to 100

2. The silane compound of claim 1 , having a weight average molecular weight of about 2,000 grams per mol to about 10,000 grams per mol.

3. A composition comprising the silane compound including a fluorine-containing ether group of claim 1 .

4. The composition of claim 3 , further comprising a compound represented by Formula 3:
A-L 6 -Si(R 1 )(R 2 )(R 3 )  Formula 3

wherein in Formula 3,
A is a halogen atom, a thiol group, an isocyanate group, an amino group, an allylamino group, or —NH(L 7 -Si(R 4 )(R 5 )(R 6 )),
L 6 and L 7 are each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof, and
R 1 to R 6 are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,
with the proviso that at least one of R 1 to R 3 and at least one of R 4 to R 6 are each independently a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, or a hydroxy group.

5. The composition of claim 4 , wherein a mixing ratio by mol of the silane compound comprising a fluorine-containing ether group of claim 1 to a compound of Formula 3 is about 1:0.003 to about 1:3.

6. The composition of claim 4 , wherein the compound of Formula 3 is
H 2 N—(CH 2 ) 3 —Si(OCH 3 )(OCH 3 )(OCH 3 ),
H 2 N—(CH 2 ) 3 —Si(OCH 2 CH 3 )(OCH 2 CH 3 )(OCH 2 CH 3 ),
H 2 N—(CH 2 ) 3 —Si(OCH 3 )(OCH 3 )(CH 3 ),
H 2 N—(CH 2 ) 3 —Si(OCH 2 CH 3 )(OCH 2 CH 3 )(CH 2 CH 3 ),
HN—{(CH 2 ) 3 —Si(OCH 3 )(OCH 3 )(OCH 3 )} 2 ,
HN—{(CH 2 ) 3 —Si(OCH 2 CH 3 )(OCH 2 CH 3 )(OCH 2 CH 3 )} 2 ,
HN—{(CH 2 ) 3 —Si(OCH 3 )(OCH 3 )(CH 3 )} 2 ,
HN—{(CH 2 ) 3 —Si(OCH 2 CH 3 )(OCH 2 CH 3 )(CH 2 CH 3 )} 2 ,
a compound of Formula 3-1,
a compound of Formula 3-2, or
a combination thereof,

7. The composition of claim 3 , further comprising a compound represented by Formula 4:
FpE-(L 2 ) p1 -LG-(L 3 ) p2 -SiR a R b R c   Formula 4

wherein in Formula 4,
FpE is a fluorine-containing (poly)ether moiety,
R a , R b and R c are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, with the proviso that at least one of R a , R b and R c is a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, or a hydroxy group,
LG is a linking group having a hydrogen-bonding functional group,
L 2 and L 3 are each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof, and
p1 and p2 are each independently an integer of 0 to 10.

8. The composition of claim 7 , wherein the compound of Formula 4 is a compound represented by Formula 4A-1 or 4B-1:
CF 3 O(CF 2 CF 2 O) n (CF 2 O) m CF 2 -(C q H 2q OC q H 2q ) p1 —C(═O)NH—(C r H 2r ) p2 —SiR a R b R c   Formula 4A-1

CF 3 O(CF 2 CF 2 O) n (CF 2 O) m CH 2 —(C q H 2q OC q H 2q ) p1 —C(═O)NH—(C r H 2r ) p2 —SiR a R b R c   Formula 4B-1

wherein in Formula 4A-1 and 4B-1,
R a , R b and R c are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, with the proviso that at least one of R a , R b and R c is a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, or a hydroxy group,
n, m are each independently 0 or an integer of 1 to 100, and
p1 and p2 are each independently an integer of 0 to 10.

9. The composition of claim 7 , wherein the compound of Formula 4 is a compound of Formula 4-1 or 4-2:

wherein in Formula 4-1,
n is a number of 1 to 100, and m is a number of 1 to 100, and

wherein in Formula 4-2,
n is a number of 1 to 100, and
m is a number of 1 to 100.

10. A film comprising a hydrolysis and polycondensation product of the silane compound having a fluorine-containing ether group of claim 1 .

11. The film of claim 10 , further comprising a compound represented by Formula 3, a compound represented by Formula 4, or a combination thereof:
A-L 6 -Si(R 1 )(R 2 )(R 3 )  Formula 3

wherein in Formula 3,
A is a halogen atom, a thiol group, an isocyanate group, an amino group, an allylamino group, or —NH(L 7 -Si(R 4 )(R 5 )(R 6 )),
L 6 and L 7 are each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof, and
R 1 to R 6 are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof,
with the proviso that at least one of R 1 to R 3 and at least one of R 4 to R 6 are each independently a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, or a hydroxy group.
FpE-(L 2 ) p1 -LG-(L 3 ) p2 -SiR a R b R c   Formula 4

wherein in Formula 4,
FpE is a fluorine-containing (poly)ether moiety,
R a , R b and R c are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, with the proviso that at least one of R a , R b and R c is a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, or a hydroxy group,
LG is a linking group having a hydrogen-bonding functional group,
L 2 and L 3 are each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof, and
p1 and p2 are each independently an integer of 0 to 10.

12. A film comprising
a combination of a hydrolysis and polycondensation product of the silane compound having a fluorine-containing ether group according to claim 1 , and a compound being represented by Formula

Assignees

• Samsung Electronics Co Ltd

Inventors

• Park Byungha
• Jung Woncheol
• Kong Hyeyoung
• Kim Inki
• Kim Hana
• Androsov Dmitry
• Ju Kyeongsik
• Chae Jungha
• Kalinina Fedosya

Classifications

• C09D183/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C08K5/54

  Silicon-containing compounds {(C08K5/0091 takes precedence)} · CPC title

• C08G77/24 Primary

  halogen-containing groups · CPC title

• C08G65/007

  containing fluorine · CPC title