Composition, film prepared therefrom, display device prepared therefrom, article prepared therefrom, and method of preparing article

Patent metadata

Field	Value
Publication number	US-11920051-B2
Application number	US-202016941987-A
Country	US
Kind code	B2
Filing date	Jul 29, 2020
Priority date	Feb 21, 2020
Publication date	Mar 5, 2024
Grant date	Mar 5, 2024

Abstract

A composition comprising a silane compound represented by Formula 1 comprising a fluorine-containing (poly)ether group; and an amine compound represented by Formula 2 comprising a fluorine-containing (poly)ether group:

Rf a -(L1) p1 -Q1-(L2) p2 -Si(R 1 )(R 2 )(R 3 )   Formula 1

Rf b -(L3) p3 -Q2-(L4) p4 -N(R 4 )(R 5 )   Formula 2

wherein Rf a , Rf b , Q1, Q2, L1 to L4, R 1 to R 3 , R 4 to R 5 , and p1 to p4 are as disclosed herein.

First claim

What is claimed is:

1. A composition comprising:
a silane compound represented by Formula 1 comprising a fluorine-containing (poly)ether group; and
an amine compound represented by Formula 2 comprising a fluorine-containing (poly)ether group:
Rf a -(L1) p1 -Q1-(L2) p2 —Si(R 1 )(R 2 )(R 3 )   Formula 1

Rf b -(L3) p3 -Q2-(L4) p4 —N(R 4 )(R 5 )   Formula 2

wherein, in Formulae 1 and 2,
Rf a and Rf b are each independently the fluorine-containing (poly)ether group,
Q1 is —N(R a )—C(═O)O—, —C(═O)—N(R a )—, —N(R a )—S(═O)O—, —S(═O)—N(R a )—, —OS(═O)—N(R a )—C(═O)O—, or —OC(═O)—N(R a )—S(═O)O—,
Q2 is —N(R b )—C(═O)O—, —C(═O)—N(R b )—, —N(R b )—S(═O)O—, —S(═O)—N(R b )—, —OS(═O)—N(R b )—C(═O)O—, or —OC(═O)—N(R b )—S(═O)O—,
R a is a hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -(L5) p5 —Si(R 7 )(R 8 )(R 9 ),
R b is a hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -(L6) p6 —N(R 11 )(R 12 ),
L1, L2, L3, L4, L5, and L6 are each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof,
p1, p2, p3, p4, p5, and p6 are each independently an integer of 1 to 10,
R 1 , R 2 , R 3 , R 7 , R 8 , and R 9 are each independently a hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
R 4 , R 5 , R 6 , R 10 , R 11 , and R 12 are each independently a hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
wherein at least one of Ru, R 2 , and R 3 is a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, or a hydroxyl group; and at least one of R 7 , R 8 , and R 9 is a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, or a hydroxyl group.

2. The composition of claim 1 , wherein Rf a and Rf b are each independently a perfluoro(poly)ether group.

3. The composition of claim 1 , wherein
the fluorine-containing (poly)ether group has a CF 3 (CF 2 ) h O— group at a terminal end, wherein a —(CF 2 CF 2 O), group, a —(CF 2 O) j — group, and a —(CH 2 O) k — group are each bound directly or indirectly to the CF 3 (CF 2 ) h O— group, and
h and k are each independently an integer of 0 to 10, and i and j are each independently an integer of 1 to 100.

4. The composition of claim 1 , wherein
Rf a and Rf b are each independently
CF 3 O—(CF 2 CF 2 O) i —(CF 2 O) j —(CH 2 O) k —,
CF 3 O—(CF 2 O) j —(CF 2 CF 2 O) i —(CH 2 O) k —,
CF 3 CF 2 O—(CF 2 CF 2 O) i —(CF 2 O) j —(CH 2 O) k —,
CF 3 CF 2 O—(CF 2 O) j —(CF 2 CF 2 O) i —(CH 2 O) k —,
CF 3 CF 2 CF 2 O—(CF 2 CF 2 O) i —(CF 2 O) j —(CH 2 O) k —, or
CF 3 CF 2 CF 2 O—(CF 2 O) j —(CF 2 CF 2 O) i —(CH 2 O) k —,

wherein k is an integer of 0 to 10, and i and j are each independently an integer of 1 to 100.

5. The composition of claim 1 , wherein the silane compound of Formula 1 is represented by one of Formulae 3 and 4:
CF 3 (CF 2 ) h O(CF 2 CF 2 O) i (CF 2 O) j (CH 2 O) k —(CR 13 R 14 ) p1 —C(═O)—NH—(CH 2 ) p2 —Si(R 1 )(R 2 )(R 3 )   Formula 3

CF 3 (CF 2 ) h O—(CF 2 CF 2 O) i —(CF 2 O) j —(CH 2 O) k —(CR 13 R 14 ) p1 —C(═O)—N((CH 2 ) p2 —Si(R 1 )(R 2 )(R 3 ))((CH 2 ) p5 —Si(R 7 )(R 8 )(R 9 ))   Formula 4

wherein, in Formulae 3 and 4,
R 13 and R 14 are each independently a hydrogen, a C1-C5 alkyl group, a fluorine, or a fluorinated C1-C5 alkyl group,
p1, p2, and p5 are each independently an integer of 1 to 10,
h and k are each independently an integer of 0 to 10, and i and j are each independently an integer of 1 to 100,
R 1 , R 2 , R 3 , R 7 , R 8 , and R 9 are each independently a hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
wherein at least one of R 1 , R 2 , and R 3 is a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, or a hydroxyl group; and at least one of R 7 , R 8 , and R 9 is a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, or a hydroxyl group.

6. The composition of claim 1 , wherein the amine compound comprising a fluorine-containing (poly)ether group is represented by Formula 2; and the amine compound comprising a fluorine-containing (poly)ether group is represented by one of Formulae 5 and 6:
CF 3 (CF 2 ) h O(CF 2 CF 2 O) i (CF 2 O) j (CH 2 O) k —(CR 15 R 16 ) p3 —C(═O)—NH—(CH 2 ) p4 —N(R 4 )(R 5 )   Formula 5

CF 3 (CF 2 ) h O(CF 2 CF 2 O) i (CF 2 O) j (CH 2 O) k —(CR 15 R 16 ) p3 —C(═O)—N(CH 2 ) p4 —N(R 4 )(R 5 ))((CH 2 ) p6 —N(R 11 )(R 12 ))   Formula 6

wherein, in Formulae 5 and 6,
R 15 and R 16 are each independently a hydrogen, a C1-C5 alkyl group, a fluorine, or a fluorinated C1-C5 alkyl group,
p3, p4, and p6 are each independently an integer of 1 to 10,
h and k are each independently an integer of 0 to 10, i and j are each independently an integer of 1 to 100, and
R 4 , R 5 , R 6 , R 10 , R 11 , and R 12 are each independently a hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

7. The composition of claim 1 , wherein the silane compound represented by Formula 1 is
CF 3 O(CF 2 CF 2 O) i (CF 2 O) j —(CH 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 O(CF 2 CF 2 O) i (CF 2 O) j —(CH 2 OCH 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 O(CF 2 CF 2 O) i (CF 2 O) j —(CF 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 O(CF 2 CF 2 O) i (CF 2 O) j —(CH 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(CH 3 ), CF 3 O(CF 2 CF 2 O)(CF 2 O) j —(CH 2 OCH 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(CH 3 ), CF 3 O(CF 2 CF 2 O) i (CF 2 O) j —(CF 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(CH 3 ), CF 3 CF 2 O(CF 2 CF 2 O) i (CF 2 C)—(CH 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 CF 2 O(CF 2 CF 2 O) i (CF 2 O) j —(CH 2 OCH 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 CF 2 O(CF 2 CF 2 O) i (CF 2 O) j —(CF 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 CF 2 O(CF 2 CF 2 O) i (CF 2 O) j —(CH 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(CH 3 ), CF 3 CF 2 O(CF 2 CF 2 O) i (CF 2 O) j —(CH 2 OCH 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(CH 3 ), CF 3 CF 2 O(CF 2 CF 2 O) i (CF 2 O) j —(CF 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(CH 3 ), CF 3 CF 2 CF 2 O(CF 2 CF 2 O)(CF 2 O) j —(CH 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 CF 2 CF 2 O(CF 2 CF 2 O)(CF 2 O) j —(CH 2 OCH 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 CF 2 CF 2 O(CF 2 CF 2 O) i (CF 2 O) j —(CF 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 CF 2 CF 2 O(CF 2 CF 2 O) i (CF 2 O) j —(CH 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(CH 3 ), CF 3 CF 2 CF 2 O(CF 2 CF 2 O) i (CF 2 O) j —(CH 2 OCH 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(CH 3 ), CF 3 CF 2 CF 2 O(CF 2 CF 2 O) i (CF 2 O) j —(CF 2 )—C(═O)NH—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(CH 3 ), CF 3 O(CF 2 CF 2 O) i (CF 2 O) j —(CH 2 )—C(═O)N(—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(OCH 3 )) 2 , CF 3 O(CF 2 CF 2 O) i (CF 2 O) j —(CH 2 OCH 2 )—C(═O)N(—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(OCH 3 )) 2 , CF 3 O(CF 2 CF 2 O) i (CF 2 O) j —(CF 2 )—C(═O)N(—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(OCH 3 )) 2 , CF 3 O(CF 2 CF 2 O) i (CF 2 O) j —(CH 2 )—C(═O)N(—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(CH 3 )) 2 , CF 3 O(CF 2 CF 2 O) i (CF 2 O) j —(CH 2 OCH 2 )—C(═O)N(—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(CH 3 )) 2 , CF 3 O(CF 2 CF 2 O) i (CF 2 O) j —(CF 2 )—C(═O)N(—(CH 2 ) 2 —Si(OCH 3 )(OCH 3 )(CH 3 )) 2 , CF 3 CF 2 O(CF 2

Assignees

• Samsung Electronics Co Ltd

Inventors

• Han Jungim
• Kim Inki
• Park Byungha

Classifications

• C09D171/02 Primary

  Polyalkylene oxides · CPC title

• C09D5/00

  Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes · CPC title

• C08G65/007 Primary

  containing fluorine · CPC title

• C08G77/46 Primary

  containing polyether sequences · CPC title

• C08G65/336

  containing silicon · CPC title