Poly(amide-imide) copolymer, method of manufacturing the same, poly(amide-imide) copolymer film, window for display device, and display device

Patent metadata

Field	Value
Publication number	US-11739183-B2
Application number	US-202016919353-A
Country	US
Kind code	B2
Filing date	Jul 2, 2020
Priority date	Feb 22, 2017
Publication date	Aug 29, 2023
Grant date	Aug 29, 2023

Abstract

A poly(amide-imide) copolymer including an amide structural unit having an amide bond in a polymer main chain and an imide structural unit having an imide bond in a polymer main chain, wherein at least one imide structural unit includes a moiety cross-linked to an adjacent polymer main chain through an amide bond.

First claim

What is claimed is:

1. A poly(amide-imide) copolymer, comprising:
an amide structural unit comprising an amide bond included in a polymer main chain, and imide structural units comprising an imide bond included in the polymer main chain,
wherein the imide structural units comprise:
a first imide structural unit comprising a moiety cross-linked to an adjacent polymer main chain through an amide bond, and
a second imide structural unit, which is not cross-linked to an adjacent polymer main chain,
wherein the first imide structural unit comprises a structural unit represented by Chemical Formula 2

wherein, in Chemical Formula 2,
X is the same or different in each structural unit and is independently a substituted or unsubstituted C6 to C20 monocyclic aromatic group, a substituted or unsubstituted C4 to C20 monocyclic non-aromatic group, a substituted or unsubstituted C8 to C20 condensed polycyclic aromatic group, a substituted or unsubstituted C6 to C20 condensed polycyclic non-aromatic group, a substituted or unsubstituted C6 to C20 non-condensed polycyclic aromatic group, a substituted or unsubstituted C6 to C20 non-condensed polycyclic non-aromatic group, or a combination thereof, wherein each of the substituted or unsubstituted C6 to C20 non-condensed polycyclic aromatic group and the substituted or unsubstituted C6 to C20 non-condensed polycyclic non-aromatic group are linked by a single bond or a linking group comprising a substituted or unsubstituted fluorenylene group, O, S, C(═O), OC(═O), S(═O), S(═O) 2 , C(═O)NH, CR a (OH), SiR b R c , or (CR d R e ) p (1≤p≤10), wherein R a to R e are independently hydrogen, a C1 to C30 alkyl group, a C1 to C30 haloalkyl group, a halogen, or a hydroxy group,
Y is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C3 to C20 heterocycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C3 to C20 heteroarylene group, or a combination thereof, and
R 11 is the same or different in each structural unit and is independently a single bond or a divalent organic group comprising a substituted or unsubstituted C6 to C30 aromatic or non-aromatic ring group, wherein the substituted or unsubstituted C6 to C30 aromatic or non-aromatic ring group is present:
as a single aromatic or non-aromatic ring;
as two or more aromatic or non-aromatic rings that are condensed to provide a condensed polycyclic aromatic group; or
as two or more aromatic or non-aromatic rings that are linked by a single bond or a linking group comprising a substituted or unsubstituted fluorenylene group, O, S, C(═O), OC(═O), S(═O), S(═O) 2 , C(═O)NH, CR f (OH), SiR g R h , or (CR i R j ) p (1≤p≤10) to provide a non-condensed polycyclic aromatic group, wherein R f to R j are independently hydrogen, a C1 to C30 alkyl group, a C1 to C30 haloalkyl group, a halogen, or a hydroxy group, and
* is a linking point of the polymer main chain.

2. The poly(amide-imide)copolymer of claim 1 , wherein the structural unit represented by Chemical Formula 2 comprises a structural unit represented by Chemical Formula 2a:

wherein, in Chemical Formula 2a,
R 10 is the same or different in each structural unit and is independently a single bond or a linking group comprising a fluorenylene group, O, S, C(═O), OC(═O), S(═O), S(═O) 2 , C(═O)NH, CR a (OH), SiR b R c , or (CR d R e ) p (1≤p≤10), wherein R a to R e are independently hydrogen, a C1 to C30 alkyl group, a C1 to C30 haloalkyl group, a halogen, or a hydroxy group,
Y is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C3 to C20 heterocycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C3 to C20 heteroarylene group, or a combination thereof,
R 11 is the same or different in each structural unit and is independently a single bond or a divalent organic group comprising a substituted or unsubstituted C6 to C30 aromatic or non-aromatic ring group, wherein the substituted or unsubstituted C6 to C30 aromatic or non-aromatic ring group is present:
as a single aromatic or non-aromatic ring;
as two or more aromatic or non-aromatic rings that are condensed to provide a condensed polycyclic aromatic group; or
as two or more aromatic or non-aromatic rings that are linked by a single bond or a linking group comprising a substituted or unsubstituted fluorenylene group, O, S, C(═O), OC(═O), S(═O), S(═O) 2 , C(═O)NH, CR f (OH), SiR g R h , or (CR i R j ) p (1≤p≤10) to provide a non-condensed polycyclic aromatic group, wherein R f to R j are independently hydrogen, a C1 to C30 alkyl group, a C1 to C30 haloalkyl group, a halogen, or a hydroxy group,
R 12 and R 13 are the same or different in each structural unit and are independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 haloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a halogen, a cyano group, a hydroxy group, a nitro group, or a combination thereof,
n7 and n8 are the same or different in each structural unit and are independently an integer ranging from 0 to 3, and
* is a linking point of the polymer main chain.

3. The poly(amide-imide)copolymer of claim 2 , wherein the structural unit represented by Chemical Formula 2a comprises at least one of a structural unit represented by Chemical Formula 2aa or a structural unit represented by Chemical Formula 2ab:

4. The poly(amide-imide) copolymer of claim 1 , wherein the second imide structural unit comprises a structural unit represented by Chemical Formula 3:

wherein, in Chemical Formula 3,
X is a substituted or unsubstituted C6 to C20 monocyclic aromatic group, a substituted or unsubstituted C4 to C20 monocyclic non-aromatic group, a substituted or unsubstituted C8 to C20 condensed polycyclic aromatic group, a substituted or unsubstituted C6 to C20 condensed polycyclic non-aromatic group, a substituted or unsubstituted C6 to C20 non-condensed polycyclic aromatic group, a substituted or unsubstituted C6 to C20 non-condensed polycyclic non-aromatic group, or a combination thereof, wherein each of the substituted or unsubstituted C6 to C20 non-condensed polycyclic aromatic group and the substituted or unsubstituted C6 to C20 non-condensed polycyclic non-aromatic group are linked by a single bond or a linking group comprising a substituted or unsubstituted fluorenylene group, O, S, C(═O), OC(═O), S(═O), S(═O) 2 , C(═O)NH, CR a (OH), SiR b R c , or (CR d R e ) p (1≤p≤10), wherein R a to R e are independently hydrogen, a C1 to C30 alkyl group, a C1 to C30 haloalkyl group, a halogen, or a hydroxy group,
R 11 is a single bond or a divalent organic group comprising a substituted or unsubstituted C6 to C30 aromatic or non-aromatic ring group, wherein the substituted or unsubstituted C6 to C30 aromatic or non-aromatic ring group is present:

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Jeon Hyunjeong
• Jee Sang Soo
• Ju Kyeong-Sik

Classifications

• C08G73/14 Primary

  Polyamide-imides · CPC title

• C08G18/603

  Polyamides · CPC title

• C08G18/6438

  Polyimides or polyesterimides · CPC title

• C08G18/73

  acyclic · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title