Poly(imide-amide) copolymer, article containing poly(imide-amide) copolymer, and electronic device including same

Patent metadata

Field	Value
Publication number	US-10100153-B2
Application number	US-201615291603-A
Country	US
Kind code	B2
Filing date	Oct 12, 2016
Priority date	Oct 13, 2015
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

Abstract

A poly(imide-amide) copolymer includes: an imide structural unit which is a reaction product of a first diamine and a dianhydride, and an amide structural unit which is a reaction product of a second diamine and a diacyl halide, wherein each of the first diamine and the second diamine includes 2,2′-bis-trifluoromethyl-4,4′-biphenyldiamine, and at least one of the first diamine and the second diamine further includes a compound represented by Chemical Formula 1, wherein the dianhydride includes 3,3′,4,4′-biphenyltetracarboxylic dianhydride and 4,4′-hexafluoroisopropylidene diphthalic anhydride, wherein the diacyl halide includes terephthaloyl chloride (TPCl), and wherein an amount of the compound represented by Chemical Formula 1 is less than or equal to about 10 mole percent based on the total amount of the first diamine and the second diamine:

NH 2 -A-NH 2   Chemical Formula 1
wherein in Chemical Formula 1, A is the same as described in the detailed description.

First claim

What is claimed is:

1. A poly(imide-amide) copolymer comprising:
an imide structural unit which is a reaction product of a first diamine and a dianhydride, and
an amide structural unit which is a reaction product of a second diamine and a diacyl halide,
wherein each of the first diamine and the second diamine comprises 2,2′-bis-trifluoromethyl-4,4′-biphenyldiamine,
wherein at least one of the first diamine and the second diamine further comprises a compound represented by Chemical Formula 1,
wherein the dianhydride is a mixture of 3,3′,4,4′-biphenyltetracarboxylic dianhydride and 4,4′-hexafluoroisopropylidene diphthalic anhydride,
wherein the diacyl halide comprises terephthaloyl chloride, and
wherein the amount of the compound represented by Chemical Formula 1 is greater than 0 mole percent and less than or equal to about 10 mole percent based on the total moles of the first diamine and the second diamine:
NH 2 -A-NH 2   Chemical Formula 1

wherein, in Chemical Formula 1,
A is represented by the following chemical formula:

wherein, in the chemical formula,
L is a single bond or a linking group selected from —C(═O)—, —S(═O) 2 —, and —CRR′— (wherein, R and R′ are the same or different, and are independently a C1 to C4 alkyl group substituted with at least one fluorine atom), and
* is a portion linked to a nitrogen atom.

2. The poly(imide-amide) copolymer of claim 1 , wherein A is represented by Chemical Formula 2 or Chemical Formula 3:

wherein, in Chemical Formulae 2 and 3,
* is a portion linked to a nitrogen atom.

3. The poly(imide-amide) copolymer of claim 1 , wherein the amount of the diamine represented by Chemical Formula 1 is about 0.1 mole percent to about 8.0 mole percent based on the total moles of the first diamine and the second diamine of the poly(imide-amide) copolymer.

4. The poly(imide-amide) copolymer of claim 1 , wherein the mole ratio of the imide structural unit and the amide structural unit is about 0.2 to 0.8:about 0.8 to 0.2.

5. The poly(imide-amide) copolymer of claim 1 , wherein the mole ratio of the imide structural unit and the amide structural unit is about 0.2 to 0.4:about 0.8 to 0.6.

6. The poly(imide-amide) copolymer of claim 1 , wherein the poly(imide-amide) copolymer comprises:
(i) a structural unit represented by Chemical Formula 4,
(ii) a structural unit represented by Chemical Formula 5,
(iii) a structural unit represented by Chemical Formula 6, and
(iv) at least one of a structural unit represented by Chemical Formula 7, a structural unit represented by Chemical Formula 8, and a structural unit represented by Chemical Formula 9,
wherein the total amount of the (iv) at least one of the structural unit represented by Chemical Formula 7, the structural unit represented by Chemical Formula 8, and the structural unit represented by Chemical Formula 9 is less than or equal to about 10 mole percent based on the total moles of the structural units (i) to (iv):

wherein, in Chemical Formulae 4 to 9,
* is a portion linked to a nitrogen atom or a carbon atom.

7. The poly(imide-amide) copolymer of claim 6 , wherein the poly(imide-amide) copolymer comprises:
(i) the structural unit represented by Chemical Formula 4,
(ii) the structural unit represented by Chemical Formula 5,
(iii) the structural unit represented by Chemical Formula 6, and
(iv) at least one of the structural unit represented by Chemical Formula 8 and the structural unit represented by Chemical Formula 9,
wherein the total amount of the (iv) at least one of the structural unit represented by Chemical Formula 8 and the structural unit represented by Chemical Formula 9 is about 0.1 mol % to about 8.0 mol % based on the total moles of the structural units (i) to (iv).

8. An article comprising the poly(imide-amide) copolymer of claim 1 .

9. The article of claim 8 ,
wherein the article is a film, and
wherein the film has a yellowness index of less than or equal to 3.5 and a tensile modulus of greater than or equal to 4.0 gigapascals at a thickness of about 50 micrometers to about 100 micrometers.

10. An electronic device comprising the article of claim 8 .

11. A poly(imide-amide) copolymer comprising:
a reaction product of a compound represented by Chemical Formula 10, a diamine represented by Chemical Formula 1, and a dianhydride mixture comprising 3,3′,4,4′-biphenyltetracarboxylic dianhydride and 4,4′-hexafluoroisopropylidene diphthalic anhydride, wherein the amount of the diamine represented by Chemical Formula 1 is greater than 0 mole percent and less than or equal to about 10 mole percent based on the total moles of the diamines used in the reaction:

wherein, in Chemical Formula 10, n 0 is an integer of 1 or more,
NH 2 -A-NH 2   Chemical Formula 1

wherein, in Chemical Formula 1,
A is represented by the following chemical formula:

wherein, in the chemical formula,
L is a single bond or a linking group selected from —C(═O)—, —S(═O) 2 —, and —CRR′— (wherein, R and R′ are the same or different, and are independently a C1 to C4 alkyl group substituted with at least one fluorine), and
* is a portion linked to a nitrogen atom.

12. The poly(imide-amide) copolymer of claim 11 , wherein A is represented by Chemical Formula 2 or Chemical Formula 3:

wherein, in Chemical Formulae 2 and 3,
* is a portion linked to a nitrogen atom.

13. A method of preparing a poly(imide-amide) copolymer comprising:
reacting 2,2′-bis-trifluoromethyl-4,4′-biphenyldiamine with terephthaloyl chloride to prepare a compound represented by Chemical Formula 10, and
reacting the prepared compound of Chemical Formula 10 with a diamine represented by Chemical Formula 1, and a mixture of 3,3′,4,4′-biphenyltetracarboxylic dianhydride, and 4,4′-hexafluoroisopropylidene diphthalic anhydride to prepare a poly(amic acid-amide) copolymer, and
imidizing the obtained poly(amic acid-amide) copolymer to prepare the poly(imide-amide) copolymer:

wherein, in Chemical Formula 10, n 0 is an integer of 1 or more,
NH 2 -A-NH 2   Chemical Formula 1

wherein, in Chemical Formula 1,
A is represented by the following chemical formula:

wherein, in the chemical formula,
L is a single bond or a linking group selected from —C(═O)—, —S(═O) 2 —, and —CRR′— (wherein, R and R′ are the same or different, and are independently a C1 to C4 alkyl group substituted with at least one fluorine atom), and
* is a portion linked to a nitrogen atom.

14. The method of claim 13 , wherein the amount of the diamine represented by Chemical Formula 1 is greater than 0 mole percent and less than or equal to about 10 mole percent based on the total moles of 2,2′-bis-trifluoromethy

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Jee Sang Soo
• Jeon Hyunjeong
• Choi Sungwon
• Sohn Byunghee
• Ju Kyeong-Sik

Classifications

• C08G73/1067

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

• C08G73/1042

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

• C08J2379/08

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

• C08G73/1028

  characterised by the process itself, e.g. steps, continuous · CPC title

• C08G73/1039

  comprising halogen-containing substituents · CPC title