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

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 two C6 to C12 aromatic rings is 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, or a C1 to C6 ester group.

8. The poly(amide-imide) copolymer according to claim 1 , wherein the diamine represented by Chemical Formula 1 comprises at least one diamine represented by chemical formulae:

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

10. The poly(amide-imide) copolymer according to claim 1 , wherein in Chemical Formula 2, R 3 is a phenylene group, and each X is independently Cl or Br.

11. The poly(amide-imide) copolymer according to claim 1 , wherein the tetracarboxylic acid dianhydride represented by Chemical Formula 3 comprises at least one selected from 3,3′,4,4′-biphenyl tetracarboxylic dianhydride, 3,3′,4,4′-diphenylsulfone tetracarboxylic dianhydride, 4,4′-(hexafluoroisopropylidene)diphthalic anhydride, and 4,4′-oxydiphthalic anhydride.

12. The poly(amide-imide) copolymer according to claim 1 , wherein the tetracarboxylic acid dianhydride represented by Chemical Formula 3 comprises a combination of 3,3′,4,4′-biphenyl tetracarboxylic dianhydride and 4,4′-(hexafluoroisopropylidene)diphthalic anhydride.

13. The poly(amide-imide) copolymer according to claim 1 , wherein an amount of the aromatic diamine represented by Chemical Formula 4 is less than or equal to 200 parts per million based on the total weight of the poly(amide-imide) copolymer.

14. A composition for preparing a poly(amide-imide) copolymer comprising a diamine represented by Chemical Formula 5, and a tetracarboxylic acid dianhydride represented by Chemical Formula 3:

wherein, in Chemical Formula 5,

R 1 is represented by —C(═O)— or -(L 1 )-N═N-(L 2 )-, wherein L 1 and L 2 are each independently 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

when R 1 is represented by —C(═O)—,

R e and R f are linked to each other to form —C(═O)—, and

R b , R c , 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; and

when R 1 is represented by -(L 1 )-N═N-(L 2 )-,

R b , R c , and R e 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;

R 3 is a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene group,

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;

n1 and n2 are the same or different, and each independently a number greater than or equal to 0, provided that both n1 and n2 are not simultaneously 0;

wherein, in Chemical Formula 3,

R 10 is a single bond, —O—, —S—, —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 211 R 212 , wherein R 210 , R 211 , and R 212 are each independently hydrogen or a C1 to C10 aliphatic organic group, and

n7 and n8 are each independently an integer ranging from 0 to 3.

15. The composition for preparing a poly(amide-imide) copolymer according to claim 14 , wherein the composition further comprises a diamine represented by Chemical Formula 5-1:

wherein in Chemical Formula 5-1,

R 3 is a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene group,

Ar 1 and Ar 2 are each independently 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, and n0 is a number greater than or equal to 0.

16. The composition for preparing a poly(amide-imide) copolymer according to claim 14 ,

wherein R 1 of Chemical Formula 5 is —C(═O)—,

R b , R c , and R g to R j 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,

A is a ring system including two phenylene groups linked by a single bond, wherein each of the two phenylene groups is independently substituted by an electron-withdrawing group selected from a halogen atom, nitro group, cyano group, a C1 to C2 haloalkyl group, a C2 to C6 alkanoyl group, and a C1 to C6 ester group.

17. The composition for preparing a poly(amide-imide) copolymer according to claim 14 , wherein the tetracarboxylic acid dianhydride represented by Chemical Formula 3 comprises a combination of the compound represented by Chemical Formula 3-1, and the compound represented by Chemical Formula 3-2:

18. An article comprising a poly(amide-imide) copolymer according to claim 1 .

19. The article according to claim 18 , wherein the article comprises a film, wherein the film has a* of −3.0 to 3.0 and b* of −3.0 to 3.0 at the color coordinate.

20. The article according to claim 18 , wherein the article comprises a film, wherein the film has a transmittance of greater than or equal to 85%, and a Yellowness Index of −4.0 to 3.0.

21. A display device comprising the article according to claim 18 .