Compound, poly(imide-amide) copolymer, and an article including the poly(imide-amide) copolymer

Patent metadata

Field	Value
Publication number	US-9873660-B2
Application number	US-201615268826-A
Country	US
Kind code	B2
Filing date	Sep 19, 2016
Priority date	Nov 25, 2013
Publication date	Jan 23, 2018
Grant date	Jan 23, 2018

Abstract

A compound represented by Chemical Formula 1:

wherein in Chemical Formula 1,
R 1 and R 2 are the same or different, and are each independently an electron-withdrawing group,
R 3 to R 6 are the same or different, and are each independently selected from a hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, and a substituted or unsubstituted C6 to C20 aryl group, and
n11 and n12 are the same or different, and are each independently an integer from 1 to 4.

First claim

What is claimed is:

1. A compound represented by Chemical Formula 1:

wherein in Chemical Formula 1,
R 1 and R 2 are the same or different, and are each independently-CF 3 , —CCl 3 , —CBr 3 , —Cl 3 , —C 3 F 7 , —C 2 F 5 , —COOH, —COOMe, —COOEt, —OMe, —OEt, —SF 6 , —F, —Cl, or —Br,
R 3 to R 6 are the same or different, and are each independently selected from a hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, and a substituted or unsubstituted C6 to C20 aryl group, and
n11 and n12 are the same or different, and are each independently an integer from 1 to 4.

2. The compound according to claim 1 , wherein both R 1 and R 2 are —CF 3 , and R 3 to R 6 are all hydrogens.

3. A poly(imide-amide) copolymer represented by Chemical Formula 8:

wherein in Chemical Formula 8,

is represented by Chemical Formula 5-1:

wherein in Chemical Formula 5-1,
R 10 is a substituted or unsubstituted C1 to C30 aliphatic group, a substituted or unsubstituted C3 to C30 alicyclic organic group, a substituted or unsubstituted C6 to C30 aromatic organic group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
R 12 and R 13 are the same or different and are each independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic group, a substituted or unsubstituted C6 to C20 aromatic group, an alkoxy group of formula —OR 205 , wherein R 205 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 a hydrogen or a C1 to C10 aliphatic organic group, and
n7 and n8 are the same or different and are each independently an integer ranging from 0 to 3;
wherein in Chemical Formula 8,

is represented by Chemical Formula 2-1, Chemical Formula 3-1, or Chemical Formula 4-1:

wherein in Chemical Formula 2-1,
R a is a substituted or unsubstituted C3 to C30 alicyclic organic group, a substituted or unsubstituted C6 to C30 aromatic organic group, or a substituted or unsubstituted C2 to C30 heterocyclic group, or a substituted or unsubstituted C13 to C20 fluorenylene group,
R 7 and R 8 are the same or different and are each independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic group, a substituted or unsubstituted C6 to C20 aromatic 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 a hydrogen or a C1 to C10 aliphatic organic group, and
n1 and n2 are the same or different and are each independently an integer ranging from 0 to 4;
Chemical Formula 3-1

wherein in Chemical Formula 3-1,
R 26 and R 27 are the same or different and are each independently an electron withdrawing group,
R 28 and R 29 are the same or different, and 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 the same or different, and are each independently a 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, and
n6 is an integer ranging from 0 to 3,
provided that n4+n6 is an integer ranging from 1 to 4;

wherein in Chemical Formula 4-1,
R 14 is —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 substituted or unsubstituted 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 two or more moieties linked through a single bond or through a functional group selected from 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—,
R 16 and R 17 are the same or different, and 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 212 , wherein R 212 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR 213 R 214 R 215 , wherein R 213 , R 214 , and R 215 are the same or different, and are each independently a hydrogen or a C1 to C10 aliphatic organic group, and
n9 and n10 are each independently an integer ranging from 0 to 4,
wherein in Chemical Formula 8,

is represented by Chemical Formula 9:

wherein in Chemical Formula 9,
R 1 and R 2 are the same or different, and are each independently-CF 3 , —CCl 3 , —CBr 3 , —Cl 3 , —C 2 F 5 , —C 3 F 7 , —COOH, —COOMe, —COOEt, —OMe, —OEt, —SF 6 , —F, —Cl, or —Br,
both R 3 and R 4 are hydrogens, and
n11 and n12 are the same or different, and are each independently an integer from 1 to 4.

4. The poly(imide-amide) copolymer according to claim 3 , wherein in Chemical Formula 8, 0.01≦x≦0.10.

5. The poly(imide-amide) copolymer according to claim 3 , wherein Chemical Formula 5-1 is represented by Chemical Formula 6-1, or Chemical Formula 7-1:

In Chemical Formulae 6-1 and 7-1,
R 12 and R 13 are the same or different, and are each independently a halogen, a hydroxy group, a substituted or unsubstituted 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 an integer ranging from 0 to 3.

6. The poly(imide-amide) copolymer according to claim 3 , wherein in Chemical Formula 2-1, R a is selected from the chemical formulae:

Assignees

• Samsung Electronics Co Ltd

Inventors

• Androsov Dmitry
• Kovalev Mikhail
• Kiryushchenkov Evgeny
• Kalinina Fedosya

Classifications

• C08G73/10

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

• C08G69/32

  from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound · CPC title

• C08G73/14 Primary

  Polyamide-imides · CPC title

• C07C237/40 Primary

  having the nitrogen atom of the carboxamide group bound to a carbon atom of a six-membered aromatic ring · CPC title

• C08L79/08

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