Poly(amide-imide) copolymer, article including poly(amide-imide) copolymer, and display device including the same

Patent metadata

Field	Value
Publication number	US-10619045-B2
Application number	US-201815958549-A
Country	US
Kind code	B2
Filing date	Apr 20, 2018
Priority date	Apr 20, 2017
Publication date	Apr 14, 2020
Grant date	Apr 14, 2020

Abstract

A poly(amide-imide) copolymer including a reaction product of at least one tetracarboxylic acid dianhydride, at least one diamine, and at least one dicarboxylic acid derivative, wherein the at least one tetracarboxylic acid dianhydride includes a tetracarboxylic acid dianhydride represented by Chemical Formula 1, the at least one diamine includes a diamine represented by Chemical Formula 2, and the at least one dicarboxylic acid derivative includes a dicarboxylic acid derivative represented by Chemical Formula 3:

wherein, R 1 to R 3 , X 1 and X 2 are the same as defined in the specification.

First claim

What is claimed is:

1. A poly(amide-imide) copolymer comprising a reaction product of at least one tetracarboxylic acid dianhydride, at least one diamine, and at least one dicarboxylic acid derivative,
wherein the at least one tetracarboxylic acid dianhydride comprises a tetracarboxylic acid dianhydride represented by Chemical Formula 1, the at least one diamine comprises a diamine represented by Chemical Formula 2, and the at least one dicarboxylic acid derivative comprises a dicarboxylic acid derivative represented by Chemical Formula 3; wherein an amount of the diamine represented by Chemical Formula 2 is less than or equal to 30 mole percent based on the total amount of the at least one diamine:

wherein, in Chemical Formula 1, R 1 is a substituted or unsubstituted tetravalent C4 to C12 saturated or unsaturated aliphatic hydrocarbon ring group;
NH 2 —R 2 —NH 2   Chemical Formula 2

wherein, in Chemical Formula 2,
R 2 comprises two or more substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring groups, wherein the two or more substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring groups comprise two or more aromatic hydrocarbon rings linked through a functional group selected from —O—, —S—, —C(═O)—, —CH(OH)—, —S(═O) 2 —, —(CH 2 ) p — wherein 1≤p≤10, —(CF 2 ) q — wherein 1≤q≤10, —Si(C n H 2n+1 ) 2 —, —C(C n H 2n+1 ) 2 —, —C(C n F 2n+1 ) 2 —, wherein 1≤n≤10, —C(═O)NH—, and a combination thereof;

wherein, in Chemical Formula 3,
R 3 comprises a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring group, wherein the substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring group comprises one aromatic hydrocarbon ring, two or more aromatic hydrocarbon rings fused together to provide a condensed ring system, or two or more moieties independently selected from the foregoing linked through a single bond or through a functional group selected from —O—, —S—, —C(═O)—, —CH(OH)—, —S(═O) 2 —, —(CH 2 ) p — wherein 1≤p≤10, —(CF 2 ) q — wherein 1≤q≤10, —Si(C n H 2n+1 ) 2 —, —C(C n H 2n+1 ) 2 —, —C(C n F 2n+1 ) 2 —, wherein 1≤n≤10, —C(═O)NH—, and a combination thereof; and
X 1 and X 2 are the same or different, and are each independently selected from a halogen, hydroxy group, or a C1 to C4 alkoxy group.

2. The poly(amide-imide) copolymer according to claim 1 , wherein in Chemical Formula 1, R 1 is a tetravalent C4 to C8 saturated aliphatic hydrocarbon ring group.

3. The poly(amide-imide) copolymer according to claim 1 , wherein in Chemical Formula 2, R 2 comprises a substituted or unsubstituted two or more phenylene groups linked through a functional group selected from —O—, —S—, —C(═O)—, or —CH(OH)—, wherein the substitution of each of the two or more phenylene groups is substituted by any one selected from —OH, —CF 3 , —CCl 3 , —CBr 3 , —CI 3 , —NO 2 , —CN, —COCH 3 and —CO 2 C 2 H 5 .

4. The poly(amide-imide) copolymer according to claim 1 , wherein the at least one diamine further comprises a diamine represented by Chemical Formula 2A:
NH 2 —R 2′ —NH 2   Chemical Formula 2A

wherein, in Chemical Formula 2A,
R 2′ comprises substituted or unsubstituted two or more C6 to C30 aromatic hydrocarbon rings linked through a single bond.

5. The poly(amide-imide) copolymer according to claim 4 ,
wherein in Chemical Formula 2A, R 2′ comprises two or more phenylene groups linked through a single bond, and
wherein each of the phenylene group is substituted with any one selected from —CF 3 , —CCl 3 , or —CBr 3 .

6. The poly(amide-imide) copolymer according to claim 4 , wherein the at least one diamine comprises the diamine represented by Chemical Formula 2A and the diamine represented by Chemical Formula 2, wherein R 2′ of Chemical Formula 2A comprises two or more phenylene groups linked through a single bond, wherein each of the two or more phenylene groups are substituted with —CF 3 , and wherein R 2 of Chemical Formula 2 comprises two or more unsubstituted phenylene groups linked through —O—.

7. The poly(amide-imide) copolymer according to claim 4 , wherein the at least one diamine comprises the diamine represented by Chemical Formula 2A and the diamine represented by Chemical Formula 2, wherein R 2′ of Chemical Formula 2A comprises two phenylene groups linked through a single bond, wherein each of the two phenylene groups are substituted with —CF 3 , and wherein R 2 of Chemical Formula 2 comprises two unsubstituted phenylene groups linked through —O—.

8. The poly(amide-imide) copolymer according to claim 4 , wherein an amount of the diamine represented by Chemical Formula 2 is less than an amount of the diamine represented by Chemical Formula 2A.

9. The poly(amide-imide) copolymer according to claim 4 , wherein a mole ratio of the diamine represented by Chemical Formula 2 and the diamine represented by Chemical Formula 2A is from 30:70 to 1:99.

10. The poly(amide-imide) copolymer according to claim 1 , wherein an amount of the diamine represented by Chemical Formula 2 is less than or equal to 20 mole percent based on the total amount of the at least one diamine.

11. The poly(amide-imide) copolymer according to claim 1 , wherein an amount of the diamine represented by Chemical Formula 2 is less than or equal to 10 mole percent based on the total amount of the at least one diamine.

12. The poly(amide-imide) copolymer according to claim 1 , wherein in Chemical Formula 3, R 3 is an unsubstituted phenylene group, and X 1 and X 2 are each independently selected from —Cl, —OH, or —OCH 3 .

13. The poly(amide-imide) copolymer according to claim 1 , wherein in Chemical Formula 1, R 1 is a tetravalent C4 saturated aliphatic hydrocarbon ring group.

14. The poly(amide-imide) copolymer according to claim 1 , which is the reaction product of the at least one tetracarboxylic acid dianhydride, the at least one diamine, and the at least one dicarboxylic acid derivative in a mole ratio of 40 to 80:100:60 to 20, respectively.

15. The poly(amide-imide) copolymer according to claim 1 , which is the reaction product of the at least one tetracarboxylic acid dianhydride, the at least one diamine, and the at least one dicarboxylic acid derivative in a mole ratio of 50 to 70:100:50 to 30, respectively.

16. An article comprising the poly(amide-imide) copolymer according to claim 1 .

17. The article according to claim 16 , wherein the article is a film having a tensile modulus of greater than or equal to 6.5 Giga Pascal and an average light transmittance of greater than or equal to 87.5 percent in a wavelength range of 350 nanometers to 750 nanometers, when the thickness of the film is about 50 micrometers to 100 micrometers (μm).

18. A window film for a display device comprising a poly(amide-imide) copolymer according to claim 1 .

19. A display device comprising the article according to claim 16 .

20. The display device according to claim 19 , wherein the display device is a flexible display device.

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Ahn Chanjae
• Chae Jungha
• Chang Won Suk
• Jo A Ra
• Jee Sang Soo
• Choi Sungwon

Classifications

• C08L79/08 Primary

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C08L2203/20

  use in electrical or conductive gadgets · CPC title

• C08J2379/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C08G73/1039

  comprising halogen-containing substituents · CPC title

• C08G73/14 Primary

  Polyamide-imides · CPC title