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-11898012-B2
Application number	US-202117246926-A
Country	US
Kind code	B2
Filing date	May 3, 2021
Priority date	Sep 8, 2017
Publication date	Feb 13, 2024
Grant date	Feb 13, 2024

Abstract

A poly(amide-imide) copolymer that is a reaction product of a substituted or unsubstituted linear aliphatic diamine including two terminals, 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 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 composition for preparing a poly(amide-imide) copolymer comprising a substituted or unsubstituted linear aliphatic diamine, a compound represented by Chemical Formula 4, and a tetracarboxylic acid dianhydride comprising a combination of a compound represented by Chemical Formula 3-1 and a compound represented by Chemical Formula 3-2, and a solvent:

wherein, in Chemical Formula 4,
R 3 is a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene group,
n0 is a number greater than or equal to 1, and
Ar 1 and Ar 2 are each independently represented by Chemical Formula 5:

wherein, in Chemical Formula 5,
R 6 and R 7 are each independently an electron withdrawing group selected from —CF 3 , —CCl 3 , —CBr 3 , —Cl 3 , —NO 2 , —CN, —C(═O)CH 3 , and —CO 2 C 2 H 5 ,
R 8 and R 9 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 204 , wherein R 204 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR 205 R 206 R 207 wherein —R 205 , R 206 , and R 207 are each independently hydrogen or a C1 to C10 aliphatic organic group,
n3 is an integer ranging from 1 to 4, n5 is an integer ranging from 0 to 3, provided that n3+n5 is an integer ranging from 1 to 4, and
n4 is an integer ranging from 1 to 4, n6 is an integer ranging from 0 to 3, provided that n4+n6 is an integer ranging from 1 to 4;

2. The composition for preparing a poly(amide-imide) copolymer according to claim 1 , wherein the substituted or unsubstituted linear aliphatic diamine comprises two terminals, wherein the substituted or unsubstituted linear aliphatic diamine comprises an amino group located at each end of the two terminals thereof, and wherein the substituted or unsubstituted linear aliphatic diamine is a substituted or unsubstituted C1 to C30 saturated or unsaturated linear aliphatic diamine.

3. The composition for preparing a poly(amide-imide) copolymer according to claim 1 , wherein the substituted or unsubstituted linear aliphatic diamine comprises two terminals, wherein the substituted or unsubstituted linear aliphatic diamine comprises an amino group located at each end of the two terminals thereof, and wherein the substituted or unsubstituted linear aliphatic diamine is a substituted or unsubstituted C1 to C20 saturated linear aliphatic diamine.

4. The composition for preparing a poly(amide-imide) copolymer according to claim 1 , wherein the substituted or unsubstituted linear aliphatic diamine is selected from methylene diamine, ethylene diamine, 1,3-propane diamine, 1,4-tetramethylene diamine, 1,5-pentamethylene diamine, 1,6-hexamethylene diamine, 1,7-heptamethylene diamine, 1,8-octamethylene diamine, 1,9-nanomethylene diamine, 1,10-decamehtylene diamine, 1,11-undecamethylene diamine, 1,12-dodecamethylene diamine, and a combination thereof.

5. The composition for preparing a poly(amide-imide) copolymer according to claim 1 , wherein the composition further comprises a diamine represented by Chemical Formula 1:
NH 2 -A-NH 2    Chemical Formula 1

wherein in Chemical Formula 1,
A is a ring system comprising 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.

6. The composition for preparing a poly(amide-imide) copolymer according to claim 5 , wherein the diamine represented by Chemical Formula 1 comprises a ring system comprising two C6 to C12 aromatic rings linked by a single bond, wherein each of the two C6 to C12 aromatic rings are independently substituted by an electron-withdrawing group selected from a halogen atom, a nitro group, a cyano group, a C1 or C2 haloalkyl group, a C2 to C6 alkanoyl group, and a C2 to C6 ester group.

7. The composition for preparing a poly(amide-imide) copolymer according to claim 5 , wherein the diamine represented by Chemical Formula 1 comprises at least one selected from the diamines represented by chemical formulae:

8. The composition for preparing a poly(amide-imide) copolymer according to claim 5 , wherein the diamine represented by Chemical Formula 1 comprises a diamine represented by Chemical Formula A:

9. The composition for preparing a poly(amide-imide) copolymer according to claim 1 , wherein in Chemical Formula 4, R 3 is a phenylene group.

10. The composition for preparing a poly(amide-imide) copolymer according to claim 1 , wherein the compound represented by Chemical Formula 3-1 comprises 4,4-(hexafluoroisopropylidene)diphthalic anhydride (6FDA), and the compound represented by Chemical Formula 3-2 comprises 3,3′,4,4′-biphenyl tetracarboxylic dianhydride (BPDA).

11. The composition for preparing a poly(amide-imide) copolymer according to claim 1 , wherein the compound represented by Chemical Formula 4 is prepared by reacting a diamine represented by Chemical Formula 1 and a dicarbonyl compound represented by Chemical formula 2, and wherein the substituted or unsubstituted linear aliphatic diamine is present in an amount of greater than 20 mole percent and less than 90 mol percent based on the total mole numbers of diamines that include the diamine represented by Chemical Formula 1 to be used to prepare the compound represented by Chemical Formula 4 and the substituted or unsubstituted linear aliphatic diamine present in the composition:
NH 2 -A-NH 2    Chemical Formula 1

wherein in Chemical Formula 1,
A is a ring system comprising 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 different halogen atom.

12. An article comprising a poly(amide-imide) copolymer prepared from the composition according to claim 1 .

13. The article according to claim 12 , wherein the article comprises a film, and wherein the film has a toughness of greater than or equal to 1,000 Joules×reverse cubic meters×10 4 (Joul·m −3 ·10 4 ), when the film has a thickness of about 30 micrometers to about 100 micrometers.

14. A window film for a display device comprising a poly(amide-imide) copolymer prepared from the composition according to claim 1 .

15. A display device comprising the article according to claim 12 .

16. The display device according to claim 6 , wherein the display device comprises a flexible display device.

17. A display device comprising the window film according to claim 14 .

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Jo A Ra
• Ahn Chanjae
• Choi Sungwon
• Chang Won Suk
• Jeong Boreum

Classifications

• C08G73/14 Primary

  Polyamide-imides · CPC title

• B29C41/003

  characterised by the choice of material · CPC title

• B29C41/46

  Heating or cooling · CPC title

• 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