Poly(amide-imide) copolymer, composition for preparing poly(amide-imide) copolymer, article including poly(amide-imide) copolymer, and display device including the article

Patent metadata

Field	Value
Publication number	US-10927218-B2
Application number	US-201816126270-A
Country	US
Kind code	B2
Filing date	Sep 10, 2018
Priority date	Sep 8, 2017
Publication date	Feb 23, 2021
Grant date	Feb 23, 2021

Abstract

A poly(amide-imide) copolymer that is a reaction product of a substituted or unsubstituted aromatic diamine having a maximum absorption wavelength in a range from 500 nanometers (nm) to 650 nm in a visible light region, a diamine represented by Chemical Formula 1, a dicarbonyl compound represented by Chemical Formula 2, and a tetracarboxylic acid dianhydride represented by Chemical Formula 3:

wherein, in Chemical Formulae 1 to 3, A, R 3 , R 10 , R 12 , R 13 , X, n7 and n8 are the same as defined in the specification.

First claim

What is claimed is:

1. A poly(amide-imide) copolymer that is a reaction product of a substituted or unsubstituted aromatic diamine having a maximum absorption wavelength in a range from 500 nanometers to 700 nanometers in a visible light region, and is represented by Chemical Formula 4, a diamine represented by Chemical Formula 1, a dicarbonyl compound represented by Chemical Formula 2, and a tetracarboxylic acid dianhydride represented by Chemical Formula 3:
NH 2 -A-NH 2   Chemical Formula 1

wherein in Chemical Formula 1,
A is a ring system including two or more C6 to C30 aromatic rings linked by a single bond, wherein each of the two or more aromatic rings is independently unsubstituted or substituted by an electron-withdrawing group;

wherein, in Chemical Formula 2,
R 3 is a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene group, and each X is an identical or a different halogen atom,

wherein, in Chemical Formula 3,
R 10 is a single bond, —O—, —S—, —C(═O)—, —CH(OH)—, —C(═O)NH—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p —, —(CF 2 ) q —, —C(C n H 2n+1 ) 2 —, —C(C n F 2n+1 ) 2 —, —(CH 2 ) p C(C n H 2n+1 ) 2 (CH 2 ) q —, or —(CH 2 ) p C(C n F 2n+1 ) 2 (CH 2 ) q — wherein 1≤n≤10, 1≤p≤10, and 1≤q≤10,
R 12 and R 13 are each independently a halogen, a hydroxy group, a substituted or unsubstituted C1 to C10 aliphatic organic group, a substituted or unsubstituted C6 to C20 aromatic organic group, an alkoxy group of formula —OR 201 , wherein R 201 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR 210 R 2113 R 212 , wherein R 210 , R 211 , and R 212 are each independently hydrogen or a C1 to C10 aliphatic organic group,
n7 and n8 are each independently an integer ranging from 0 to 3, and

wherein, in Chemical Formula 4,
R 1 is represented by —C(═O)— or -(L 1 )-N═N-(L 2 )-, wherein L 1 and L 2 are each independently a single bond, a C1 to C20 alkylene group, a C2 to C20 alkenylene group, a C3 to C20 cycloalkylene group, a C6 to C20 arylene group, —O—, —S—, —C(═O)—, —C(═O)O—, —CH(OH)—, —C(═O)NH—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CF 2 ) q —, wherein, 1≤q≤10, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, or a combination thereof, and
R a to R j are each independently hydrogen, deuterium, a halogen, hydroxyl group, cyano group, an amino group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a (meth)acryl group, a(meth)acrylate group, an epoxy group, a glycidoxypropyl group, a —OR 201 , wherein, R 201 is a C1 to C10 aliphatic organic group, or —SiR 210 R 211 R 212 , wherein R 210 , and R 211 , and R 212 are each independently hydrogen, or a C1 to C10 aliphatic organic group, or optionally, R e and R f are linked to each other to form —C(═O),
provided that two of R a to R e , or two of R f to R j are amino groups.

2. The poly(amide-imide) copolymer according to claim 1 , wherein the substituted or unsubstituted aromatic diamine having a maximum absorption wavelength in a visible light region comprises a maximum absorption wavelength in a range from 550 nanometers to 650 nanometers.

3. The poly(amide-imide) copolymer according to claim 1 , wherein if R 1 is represented by —C(═O)— in the aromatic diamine represented by Chemical Formula 4
then R e and R f are linked to each other to form —C(═O)—, and
R a to R d and R g to R j are each independently hydrogen, deuterium, a halogen, hydroxyl group, cyano group, an amino group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a (meth)acryl group, a(meth)acrylate group, an epoxy group, a glycidoxypropyl group, a —OR 201 , wherein, R 201 is a C1 to C10 aliphatic organic group, or —SiR 210 R 211 R 212 , wherein, R 210 , R 211 , and R 212 are each independently hydrogen, or a C1 to C10 aliphatic organic group,
provided that two of R a to R d , or two of R g to R j are amino groups; or
if R 1 is represented by -(L 1 )-N═N-(L 2 )- in the aromatic diamine represented by Chemical Formula 4, then L 1 and L 2 are each independently single bond, a C1 to C20 alkylene group, a C2 to C20 alkenylene group, a C6 to C20 arylene group, —O—, —S—, —C(═O)—, —C(═O)O—, —CH(OH)—, —C(═O)NH—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CF 2 ) q —, wherein, 1≤q≤10, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, or a combination thereof.

4. The poly(amide-imide) copolymer according to claim 3 , wherein the aromatic diamine represented by Chemical Formula 4 is represented by at least one of Chemical Formula 4-1 or Chemical Formula 4-2:

wherein, in Chemical Formulae 4-1 and 4-2,
R k to R p are each independently hydrogen, deuterium, a halogen, hydroxyl group, cyano group, an amino group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a (meth)acryl group, a(meth)acrylate group, an epoxy group, a glycidoxypropyl group, a —OR 201 , wherein, R 201 is a C1 to C10 aliphatic organic group, or —SiR 210 R 211 R 212 , wherein, R 210 , R 211 , and R 212 are each independently hydrogen, or a C1 to C10 aliphatic organic group, and
wherein in Chemical Formula 4-2,
L 1 and L 2 are each independently single bond, a C1 to C20 alkylene group, a C2 to C20 alkenylene group, a C6 to C20 arylene group, —O—, —S—, —C(═O)—, —C(═O)O—, —CH(OH)—, —C(═O)NH—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CF 2 ) q —, wherein, 1≤q≤10, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, or a combination thereof.

5. The poly(amide-imide) copolymer according to claim 4 , wherein in Chemical Formulae 4-1 and 4-2, R k and R l are each independently hydrogen, deuterium, a halogen, hydroxyl group, cyano group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, and all of R m to R p are hydrogen atoms.

6. The poly(amide-imide) copolymer according to claim 1 , wherein the diamine represented by Chemical Formula 4 comprises a diamine represented by Chemical Formula 4-1:

wherein, in Chemical Formula 4-1,
R k and R l are each independently hydrogen, deuterium, a halogen, cyano group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, and all of R m to R p are hydrogen atoms.

7. The poly(amide-imide) copolymer according to claim 1 , wherein the diamine represented by Chemical Formula 1 comprises a ring system that includes two C6 to C12 aromatic rings linked by a single bond, wherein each of the

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Jeong Boreum
• Jee Sang Soo
• Chang Won Suk
• Ju Kyeong-Sik
• Ahn Chanjae
• Jo A Ra
• Choi Sungwon

Classifications

• C08G73/1039

  comprising halogen-containing substituents · CPC title

• C08G73/1042

  Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds · CPC title

• C08G73/1067 Primary

  Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound · CPC title

• C08G73/14 Primary

  Polyamide-imides · CPC title

• C08G73/1007

  from tetracarboxylic acids or derivatives and diamines · CPC title