Poly(imide-amide) copolymer and composition including poly(imide-amide) copolymer

Patent metadata

Field	Value
Publication number	US-9353224-B2
Application number	US-201314088881-A
Country	US
Kind code	B2
Filing date	Nov 25, 2013
Priority date	Aug 26, 2013
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

A composition including a plurality of oligomers including at least one selected from a repeating unit represented by Chemical Formula 1, a repeating unit represented by Chemical Formula 2, and a combination thereof; and at least one selected from a repeating unit represented by Chemical Formula 3, a repeating unit represented by Chemical Formula 3A, and a combination thereof; wherein at least a part of the plurality of oligomers includes at least one terminal end having an amino group, and wherein at least a part of the plurality of oligomers including at least one terminal end having an amino group is a diamine having a pKa value of equal to or less than 3 at 25° C.:

wherein the variables in Chemical Formulae 1, 2, 3, and 3A are described in the specification.

First claim

What is claimed is:

1. A composition comprising a plurality of oligomers, each oligomer comprising
(i) a structural unit selected from a structural unit represented by Chemical Formula 1, a structural unit represented by Chemical Formula 2, and a combination thereof; and
(ii) a structural unit selected from a structural unit represented by Chemical Formula 3, a structural unit represented by Chemical Formula 3A, and a combination thereof;
wherein at least one of the oligomers comprises at least one terminal amino group (—NH 2 ), and
wherein the at least one terminal amino group (—NH 2 ) is derived from a diamine having a pKa value of equal to or less than 3 at 25° C.:

wherein, in Chemical Formula 1,
R 1 is the same or different in each structural unit, and is each independently a C3 to C30 alicyclic organic group, a C6 to C30 aromatic organic group, or a C2 to C30 heterocyclic group
R 2 is the same or different in each structural unit, and is each independently a C6 to C30 aromatic organic group,
R 3 and R 4 are the same or different and are each independently a halogen, a hydroxy group, a C1 to C10 aliphatic organic group, a C6 to C20 aromatic organic group, an alkoxy group of formula —OR 200 (wherein R 200 is a C1 to C10 aliphatic organic group), or a silyl group of formula —SiR 201 R 202 R 203 (wherein R 201 , R 202 , and R 203 are the same or different, and are each independently hydrogen or a C1 to C10 aliphatic organic group), and
n1 and n2 are each independently integers ranging from 0 to 4,

wherein, in Chemical Formula 2,
R 5 is the same or different in each structural unit, and is each independently a C6 to C30 aromatic organic group,
R 6 and R 7 are the same or different and are each independently —CF 3 , —CCl 3 , —CBr 3 , —Cl 3 , —NO 2 , —CN, a C1 to C2 alkanoyl group, or a C1 to C6 ester group,
R 8 and R 9 are the same or different, and are each independently a halogen, a hydroxy group, a C1 to C10 aliphatic organic group, a 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 the same or different, and 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,
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,

wherein, in Chemical Formulae 3 and 3A,
R 10 is the same or different in each structural unit, and is each independently a single bond, a C1 to C30 aliphatic organic group, a C3 to C30 alicyclic organic group, a C6 to C30 aromatic organic group, or a C2 to C30 heterocyclic group,
R 11 is the same or different in each structural unit, and each independently comprises a C6 to C30 aromatic organic group, wherein the aromatic organic group comprises one aromatic ring, two or more aromatic rings fused together to provide a condensed ring system, or a combination of two or more aromatic rings linked through a single bond or through a fluorenylene group, —O—, —S—, —C(═O)—, —CH(OH)—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p —, wherein 1≦p≦10, —(CF 2 ) q —, wherein 1≦q≦10, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, and C(═O)NH—, or a combination thereof,
R 12 and R 13 are the same or different, and are each independently a halogen, a hydroxy group, a C1 to C10 aliphatic organic group, a C6 to C20 aromatic organic group, an alkoxy group of formula —OR 208 (wherein R 208 is a C1 to C10 aliphatic organic group), or a silyl group of formula —SiR 209 R 210 R 211 (wherein R 209 , R 210 , and R 211 are the same or different, and are each independently hydrogen or a C1 to C10 aliphatic organic group), and
n7 and n8 are each independently integers ranging from 0 to 3.

2. The composition according to claim 1 , wherein the diamine having a pKa value of equal to or less than 3 at 25° C. is represented by Chemical Formula 4:

wherein, in Chemical Formula 4,
X is a single bond, —O—, —S—, —C(═O)—, —CH(OH)—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p —, wherein 1≦p≦10, —(CF 2 ) q —, wherein 1≦q≦10, —C(CH 3 ) 2 —, —C(═O)NH—, —C(CF 3 ) 2 —, —C(CCl 3 ) 2 —, —C(CBr 3 ) 2 —, or —C(Cl 3 ) 2 —,
R a to R h are the same or different, and are each independently a halogen, a hydroxy group, a C1 to C10 aliphatic organic group, a C6 to C20 aromatic organic group, an alkoxy group of formula —OR 208 (wherein R 208 is a C1 to C10 aliphatic organic group), or a silyl group of formula —SiR 209 R 210 R 211 (wherein R 209 , R 210 , and R 211 are the same or different, and are each independently hydrogen or a C1 to C10 aliphatic organic group),
provided that when X is a single bond, two or more of R a to R d and two or more or R e to R h are not hydrogen.

3. The composition according to claim 1 , wherein the diamine having a pKa value of equal to or less than 3 at 25° C. is represented by one or more of Chemical Formula c to Chemical Formula h:

4. The composition according to claim 1 , comprising an oligomer comprising two terminal ends and further comprising an anhydride group disposed at each of the two terminal ends, an oligomer comprising two terminal ends and further comprising an amino group (—NH 2 ) disposed at each of the two terminal ends, and an oligomer comprising two terminal ends and further comprising an amino group (—NH 2 ) disposed at one terminal end and an anhydride group disposed at the other terminal end, wherein the ratio between the total mole number of the anhydride group disposed at the terminal ends and the total mole number of the amino group (—NH 2 ) disposed at the terminal ends is about 1:1.

5. The composition according to claim 1 , comprising an oligomer comprising two terminal ends and further comprising an anhydride group disposed at each of the two terminal ends, and an oligomer comprising two terminal ends and further comprising an amino group disposed at each of the two terminal ends, wherein the ratio between the total mole number of the anhydride group disposed at the terminal ends and the total mole number of the amino group disposed at the terminal ends is about 1:1.

6. The composition according to claim 1 , wherein the diamine having a pKa value of equal to or less than 3 at 25° C. is present in an amount of equal to or less than about 30 mole % based on the total mole number of the structural units contained in the plurality of oligomers in the composition.

7. The composition according to claim 1 , wherein each oligomer in the composition has a weight average molecular weight of about 10,000 gram/mole to about 20,000 gram/mole.

8. The composition according to claim 1 , wherein each oligomer comprises about 1 to 1,000 of each of the structural units represented by Chemical Formula 1, Chemical Formula 2, or a combination of Chemical Formula 1 and Chemical Formula 2; and the structural unit represented by the Chemical Formula 3.

Assignees

• Samsung Electronics Co Ltd

Inventors

• Cho Chung Kun
• Kalinina Fedosya
• Kravchuk Dmitry
• Androsov Dmitry
• Kovalev Mikhail

Classifications

• C08G73/1064

  containing sulfur · CPC title

• C08L79/08 Primary

  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

• C08J5/18

  Manufacture of films or sheets · CPC title