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

Patent metadata

Field	Value
Publication number	US-11535711-B2
Application number	US-202016891328-A
Country	US
Kind code	B2
Filing date	Jun 3, 2020
Priority date	Jun 4, 2019
Publication date	Dec 27, 2022
Grant date	Dec 27, 2022

Abstract

A poly(amide-imide) copolymer that is a reaction product of a diamine represented by Chemical Formula 1, a tetracarboxylic acid dianhydride including a compound represented by Chemical Formula 2, and a compound represented by Chemical Formula 3:wherein, in Chemical Formulae 1 to 4, R1 to R4, A, and X 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 diamine comprising a compound represented by Chemical Formula 1,
a tetracarboxylic acid dianhydride comprising a compound represented by Chemical Formula 2, and
a compound represented by Chemical Formula 3:

wherein in Chemical Formula 1,
R 1 is a halogen-substituted C1 to C10 alkyl group;

wherein in Chemical Formula 2,
R 2 and R 3 are each independently hydrogen, or a halogen-substituted or an unsubstituted C1 to C10 alkyl group;

wherein, in Chemical Formula 3,
R 4 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, and
each X is an identical or a different halogen atom.

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

wherein in Chemical Formula 4,
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 with an electron-withdrawing group.

3. The poly(amide-imide) copolymer according to claim 1 , wherein the tetracarboxylic acid dianhydride further comprises a compound represented by Chemical Formula 5:

wherein, in Chemical Formula 5,
R 5 and R 6 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, a 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 211 R 212 , wherein R 210 , R 211 , and R 212 are each independently hydrogen or a C1 to C10 aliphatic organic group, and
R 7 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, and
n1 and n2 are each independently an integer ranging from 0 to 3.

4. The poly(amide-imide) copolymer according to claim 1 , wherein in Chemical Formula 1, R 1 is a fluoro-substituted C1 to C4 alkyl group.

5. The poly(amide-imide) copolymer according to claim 1 , wherein in Chemical Formula 2, R 2 and R 3 are each independently hydrogen, or a fluoro-substituted or unsubstituted C1 to C4 alkyl group.

6. The poly(amide-imide) copolymer according to claim 2 , wherein in Chemical Formula 4, A is a ring system comprising two C6 to C14 aromatic rings linked by a single bond, wherein each of the two or more aromatic rings are independently substituted with a halogen atom, a nitro group, a cyano group, a C1- or C2-haloalkyl group, a C2- to C6-alkanoyl group, or a C2 to C6 acyloxy group.

7. The poly(amide-imide) copolymer according to claim 2 , wherein the compound represented by Chemical Formula 4 is represented by one or more of the following chemical formulae:

8. The poly(amide-imide) copolymer according to claim 3 , wherein in Chemical Formula 5, n1 and n2 are both zero, and R 7 is —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).

9. The poly(amide-imide) copolymer according to claim 3 , wherein in Chemical Formula 5, n1 and n2 are both be zero, and R 7 is —O—, —S—, —C(═O)—, —CH(OH)—, —C(═O)NH—, —S(═O) 2 —, or —C(C n F 2n+1 ) 2 (wherein 1≤n≤3).

10. The poly(amide-imide) copolymer according to claim 1 , in Chemical Formula 3, R 4 is an unsubstituted phenylene group, and each X is C1.

11. The poly(amide-imide) copolymer according to claim 1 , wherein the compound represented by Chemical Formula 1 is included in an amount of less than or equal to 55 mole percent based on a total mole number of the diamine.

12. The poly(amide-imide) copolymer according to claim 1 , wherein the compound represented by Chemical Formula 2 is included in an amount of greater than or equal to about 30 mole percent and less than or equal to about 70 mole percent based on a total mole number of the tetracarboxylic acid dianhydride.

13. The poly(amide-imide) copolymer according to claim 1 , wherein the tetracarboxylic acid dianhydride is included in an amount of greater than or equal to about 25 mole percent and less than or equal to about 90 mole percent based on a total mole number of the tetracarboxylic acid dianhydride and the compound represented by Chemical Formula 3.

14. A composition for preparing a poly(amide-imide) copolymer comprising a compound represented by Chemical Formula 1, a compound represented by Chemical Formula 2, and a compound represented by Chemical Formula 6:

wherein in Chemical Formula 1,
R 1 is a halogen-substituted C1 to C10 alkyl group;

wherein in Chemical Formula 2,
R 2 and R 3 are each independently hydrogen, or a halogen-substituted or an unsubstituted C1 to C10 alkyl group;

wherein, in Chemical Formula 6,
n0 is an integer of greater than or equal to 1,
R 4 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, and
Ar 1 and Ar 2 are, each independently, represented by Chemical Formula 7:

wherein, in Chemical Formula 7,
R 8 and R 9 are each independently —CF 3 , —CCl 3 , —CBr 3 , —Cl 3 , —NO 2 , —CN, —C(═O)CH 3 , and —CO 2 C 2 H 5 , and
n3 and n4 are each independently an integer ranging from 1 to 4.

15. The composition for preparing a poly(amide-imide) copolymer according to claim 14 , wherein the composition further comprises a compound represented by Chemical Formula 5:

wherein, in Chemical Formula 5,
R 5 and R 6 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, a 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 212 , wherein R 210 , R 211 , and R 212 are each independently hydrogen or a C1 to C10 aliphatic organic group,
R 7 is a single bond, —O—, —S—, —C(═)—, —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 )

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Sohn Byunghee
• Choi Sungwon
• Song Sun Jin
• Ahn Chanjae

Classifications

• C08G73/14 Primary

  Polyamide-imides · CPC title

• C08G73/1078

  wholly aromatic in the diamino moiety · CPC title

• C08L79/08

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

• G02F1/133305

  Flexible substrates, e.g. plastics, organic film · CPC title

• C09D179/08

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