Compounds, compositions including the same, and layered structures and devices prepared from the compositions

Patent metadata

Field	Value
Publication number	US-10920014-B2
Application number	US-201816029104-A
Country	US
Kind code	B2
Filing date	Jul 6, 2018
Priority date	Jul 7, 2017
Publication date	Feb 16, 2021
Grant date	Feb 16, 2021

Abstract

A composition including a perfluoropolyether compound, and an organic solvent configured to dissolve or disperse the perfluoropolyether compound, wherein the perfluoropolyether compound includes a first end and a second end facing each other and a perfluoropolyether moiety disposed between the first end and the second end, wherein the first end includes an organic group having 6 or more carbon atoms, and wherein the second end includes a hydrolysable silicon-containing residual group.

First claim

What is claimed is:

1. A composition, comprising:
a perfluoropolyether compound; and
an organic solvent configured to dissolve or disperse the perfluoropolyether compound,
wherein the perfluoropolyether compound comprises a first end and a second end facing each other and a perfluoropolyether moiety disposed between the first end and the second end,
wherein the first end comprises an organic group comprising 5 or more carbon atoms, and does not include fluorine, and
the second end comprises a hydrolysable silicon-containing moiety,
wherein the organic group comprises a C5 to C60 substituted or unsubstituted aromatic hydrocarbon group, or a C6 to C60 substituted or unsubstituted aliphatic hydrocarbon group wherein at least one methylene is replaced by sulfonyl (—S(═O) 2 —), carbonyl (—C(═O)—), sulfide (—S—), sulfoxide (—S(═O)—), ester (—C(═O)O—), amide (—C(═O)NR—) (wherein, R is hydrogen or a C1 to C10 linear or branch alkyl group), imine (—NR—) (wherein, R is hydrogen or a C1 to C10 linear or branch alkyl group), or a combination thereof, a substituted or unsubstituted poly(alkylene oxide) residual group, a substituted or unsubstituted polyester residual group, or a combination thereof.

2. The composition of claim 1 , wherein the organic group is a C6 to C60 substituted or unsubstituted aryl group, a C7 to C60 substituted or unsubstituted arylalkyl group, a polyester moiety comprising a repeating unit represented by —RC(═O)O— (wherein, R is a C2 to C10 substituted or unsubstituted alkylene group), or a combination thereof.

3. The composition of claim 1 , wherein the organic group does not comprise a polyurethane residual group.

4. The composition of claim 1 , wherein the second end comprises —SiX 3 (wherein, X is the same or different and each independently comprises a C1 to C3 alkyl group, a C1 to C3 alkoxy group, a hydroxy group, C1, or a combination thereof).

5. The composition of claim 1 , wherein
the perfluoropolyether compound comprises a first linker between the first end and the perfluoropolyether moiety, and
the first linker comprise at least one moiety selected from a single bond, a C1 to C10 alkylene group, —O—, —C(═O), —C(═O)O—, —OC(═O)O—, —NHC(═O)O—, —OC(═O)NHS(═O)O—, —C(═O)NH— and —RC(═O)— (wherein, R is a C1 to C5 alkylene, a C6 to C20 arylene, or a combination thereof).

6. The composition of claim 5 , wherein
the perfluoropolyether compound comprises a second linker between the second end and the perfluoropolyether moiety, and
the second linker comprises at least one moiety selected from a single bond, a C1 to C10 alkylene, —O—, —C(═O)—, —C(═O)O—, —OC(═O)O—, —NHC(═O)OR— (wherein, R is a C1 to C10 substituted or unsubstituted alkylene group), —C(═O)NH—, —OC(═O)NHS(═O)O—, and a polyester moiety comprising two or more repeating units represented by —RC(═O)O—(wherein, R is a C3 to C10 substituted or unsubstituted alkylene group).

7. The composition of claim 1 , wherein the perfluoropolyether moiety comprises a repeating unit represented by Chemical Formula 1, a repeating unit represented by Chemical Formula 2, optionally a repeating unit represented by Chemical Formula 3, or a combination thereof:
* CR 2 CF 2 O *  Chemical Formula 1

wherein, R is the same or different and is each independently F or CF 3 and * is a portion linked to an adjacent atom in a main chain;
* CF 2 O *  Chemical Formula 2

wherein, * is a portion linked to an adjacent atom in a main chain; and
* CR 2 *  Chemical Formula 3

wherein, R is the same or different and each independently is hydrogen, F, CH 3 , or CF 3 , and * is a portion linked to an adjacent atom in a main chain.

8. The composition of claim 1 , wherein the perfluoropolyether compound has a weight average molecular weight of greater than or equal to about 500 Daltons and less than or equal to about 50,000 Daltons.

9. The composition of claim 1 , wherein the perfluoropolyether compound comprises a compound represented by Chemical Formula 4:
R 1 —L 1 —PFPE—L 2 —SiX 3   Chemical Formula 4

wherein,
R 1 comprises a C6 to C60 substituted or unsubstituted aromatic hydrocarbon group, a C5 to C60 substituted or unsubstituted aliphatic hydrocarbon group wherein at least one methylene is replaced by sulfonyl (—S(═O) 2 —), carbonyl (—C(═O)—), sulfide (—S—), sulfoxide (—S(═O)—), ester (—C(═O)O—), amide (—C(═O)NR—) (wherein, R is hydrogen or a C1 to C10 linear or branch alkyl group), imine (—NR—) (wherein, R is hydrogen or a C1 to C10 linear or branch alkyl group), or a combination thereof, a substituted or unsubstituted poly(alkylene oxide) residual group, a substituted or unsubstituted polyester residual group, or a combination thereof,
L 1 comprises a single bond, a C1 to C10 alkylene, —O—, —C(═O)—, —C(═O)O—, —OC(═O)O—, —NHC(═O)OR—(wherein, R is a C1 to C10 substituted or unsubstituted alkylene group), —OC(═O)NHS(═O)O—, —RC(═O)— (wherein, R is a C1 to C5 alkylene, a C6 to C20 arylene, or a combination thereof), —C(═O)NH—, or a combination thereof,
PFPE is a perfluoropolyether moiety,
L 2 comprises a single bond, a C1 to C10 alkylene, —O—, —C(═O)—, —C(═O)O—, —OC(═O)O—, —NHC(═O)OR— (wherein, R is a C1 to C10 substituted or unsubstituted alkylene group), —C(═O)NH—, —OC(═O)NHS(═O)O—, a polyester moiety comprising two or more repeating units represented by —RC(═O)O— (wherein, R is a C1 to C10 substituted or unsubstituted alkylene group), or a combination thereof, and
X is the same or different and each independently comprises a C1 to C3 alkyl group, a C1 to C3 alkoxy group, a hydroxy group, C1, or a combination thereof.

10. The composition of claim 9 , wherein the perfluoropolyether compound comprises a compound represented by Chemical Formula 4-1, a compound represented by Chemical Formula 4-2, a compound represented by Chemical Formula 4-3, or a combination thereof:
R—COO—PFPE—OCONH—(CR′ 2 ) n —SiX 3   Chemical Formula 4-1

wherein,
R is a C5 to C60 substituted or unsubstituted alkyl group, a C5 to C60 substituted or unsubstituted alkenyl group, or a C5 to C60 substituted or unsubstituted alkyl group or alkenyl group wherein at least one methylene is replaced by sulfonyl (—S(═O) 2 —), carbonyl (—C(═O)—), ether (—O—), sulfide (—S—), sulfoxide (—S(═O)—), ester (—C(═O)O—), amide (—C(═O)NR—) (wherein, R is hydrogen or a C1 to C10 linear or branch alkyl group), imine (—NR—) (wherein, R is hydrogen or a C1 to C10 linear or branch alkyl group), or a combination thereof,
PFPE is a perfluoropolyether moiety,
R′ is the same or different and each independently is hydrogen or a C1 to C3 alkyl group,
n is 1 to 10, and
X is the same or different and each independently comprises a C1 to C3 alkyl group, a C1 to C3 alkoxy group, a hydroxy group, C1, or a combination thereof,
R—COO—Ar—COO—PFPE—OCONH—(CR′ 2 ) n —SiX 3   Chemical Formula 4-2

wherein,
R is a C5 to C60 substituted or unsubstituted alkyl group, a C5 to C60 substituted or unsubstituted alkenyl group, or a C5 to C60 substituted or unsubstituted alkyl group or alkenyl group wherein at least one methylene is replaced by sulfonyl (—S(═O) 2 —), carbonyl (—C(═O)—), ether (—O—), sulfide (—S—), sulfoxide (—S(═O)—), ester (—C(═O)O—), amide (—C(═O)NR—) (wherein, R is hydrogen or a C1 to C10 linear or branch alkyl group), imine (—NR—) (wherein, R is hydrogen or a C1 to C10 linear or branch alkyl group), or a combination thereof,
Ar is a substituted or unsubstituted phenylene or —(CR″ 2 ) a —Ph—(wherein, R″ are independently hydrogen or a C1 to C3 alkyl group, Ph is a substituted or unsubstituted phenylene group, and a is 0 to 10),
PFPE is a perfluoropolyether moiety,
R′ is the same or different and each independently is hydrogen or a C1 to C3 alkyl group,
n is 1 to 10, and
X is th

Assignees

• Samsung Electronics Co Ltd

Inventors

• Jung Won Cheol
• Park Byung Ha
• Hong Sung Hun
• Kwon Myong Jong
• Kim Ginam
• Yoon Du Seop

Classifications

• C08G65/336 Primary

  containing silicon · CPC title

• C08G65/007 Primary

  containing fluorine · CPC title

• B32B27/285

  comprising polyethers · CPC title

• B32B7/10

  at least one layer having inter-reactive properties · CPC title

• B32B2457/20

  Displays, e.g. liquid crystal displays, plasma displays · CPC title