Composition for preparing article containing poly(imide-amide), method of preparing the same, and article containing poly(imide-amide)

Patent metadata

Field	Value
Publication number	US-2016222249-A1
Application number	US-201514744621-A
Country	US
Kind code	A1
Filing date	Jun 19, 2015
Priority date	Jan 30, 2015
Publication date	Aug 4, 2016
Grant date	—

Abstract

A composition for preparing an article including a poly(imide-amide) copolymer, the composition including (i) a copolymer obtained by reacting a tetracarboxylic acid dianhydride represented by Chemical Formula 1, a diamine represented by Chemical Formula 2, and a carboxylic acid dichloride to form a reaction product, followed by removing hydrochloric acid from the reaction product, (ii) an acid anhydride, and (iii) a solvent:

Wherein group R 1 in Chemical Formula 1 and group R 2 in Chemical Formula 2 are the same as described in the specification.

First claim

What is claimed is:

1 . A composition for preparing an article comprising a poly(imide-amide) copolymer, the composition comprising:
(i) a copolymer obtained by reacting a tetracarboxylic acid dianhydride represented by Chemical Formula 1, a diamine represented by Chemical Formula 2, and a carboxylic acid dichloride to form a reaction product, followed by removing hydrochloric acid from the reaction product, (ii) an acid anhydride, and (iii) a solvent:

wherein in Chemical Formula 1 and Chemical Formula 2,
R 1 and R 2 are the same or different, and are each independently a substituted or unsubstituted C4 to C20 alicyclic organic group, or a substituted or unsubstituted C6 to C30 aromatic organic group, wherein the C6 to C30 aromatic organic group comprises one aromatic ring, two or more aromatic rings fused together to provide a condensed ring system, or two or more aromatic rings 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 —, —C(═O)NH—, a substituted or unsubstituted C3 to C10 cycloalkylene group, and a substituted or unsubstituted C6 to C15 arylene group.

2 . The composition for preparing an article according to claim 1 , wherein the tetracarboxylic acid dianhydride represented by Chemical Formula 1 is at least one selected from 3,3′,4,4′-biphenyltetracarboxylic dianhydride, bicycle[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, 3,3′,4,4′-diphenylsulfone tetracarboxylic dianhydride, 4,4′-(hexafluoroisopropylidene)diphthalic anhydride, 4,4′-oxydiphthalic anhydride, pyromellitic dianhydride, and 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride.

3 . The composition for preparing an article according to claim 1 , wherein the diamine represented by Chemical Formula 2 is at least one selected from chemical formulae:

in the above chemical formulae,
R 32 to R 45 are the same or different and may each independently be hydrogen, a halogen, a nitro group, a substituted or unsubstituted C1 to C15 alkyl group, a substituted or unsubstituted C1 to C15 alkoxy group, a substituted or unsubstituted C1 to C15 fluoroalkyl group, a substituted or unsubstituted C3 to C15 cycloalkyl group, a substituted or unsubstituted C3 to C15 heterocycloalkyl group, a substituted or unsubstituted C3 to C15 cycloalkoxy group, a substituted or unsubstituted C6 to C15 aryl group, a substituted or unsubstituted C6 to C15 aryloxy group, or a substituted or unsubstituted C2 to C15 heteroaryl group,
X 2 to X 10 are the same or different and may each independently be a single bond, a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C10 cycloalkylene group, a substituted or unsubstituted C5 to C40 heterocycloalkylene group, a substituted or unsubstituted C6 to C15 arylene group, a substituted or unsubstituted C3 to C40 heteroarylene group, —SO 2 —, —O—, —C(═O)—, or a combination thereof,
n35 to n37, and n40 to n49, are integers ranging from 0 to 4, and
n38 and n39 are integers ranging from 0 to 3.

4 . The composition for preparing an article according to claim 1 , wherein the diamine is at least one selected from the compounds represented by chemical formulae:

5 . The composition for preparing an article according to claim 1 , wherein the carboxylic acid dichloride is at least one selected from terephthaloyl chloride, isophthaloyl chloride, biphenyl dicarbonyl chloride, naphthalene dicarbonyl chloride, terphenyl dicarbonyl chloride, and 2-fluoro-terephthaloyl chloride.

6 . The composition for preparing an article according to claim 1 , wherein the acid anhydride is at least one selected from acetic anhydride, maleic anhydride, phthaloic anhydride, glutaric anhydride, benzoic anhydride, hexanoic acid anhydride, and naphthanoic acid anhydride.

7 . The composition for preparing an article according to claim 1 , wherein the solvent is at least one selected from:
a sulfoxide solvent comprising dimethyl sulfoxide, diethyl sulfoxide, or a combination thereof; a formamide solvent comprising N,N-dimethyl formamide, N,N-diethyl formamide, or a combination thereof; an acetamide solvent, comprising N,N-dimethyl acetamide, N,N-diethyl acetamide, or a combination thereof; a pyrrolidone solvent comprising N-methyl-2-pyrrolidone, N-vinyl-2-pyrrolidone, or a combination thereof; a phenolic solvent comprising phenol, o-, m-, or p-cresol, xylenol, halogenated phenol, catechol, or a combination thereof; and an aprotic bipolar solvent comprising hexamethyl phosphoramide, γ-butyrolactone, or a combination thereof.

8 . The composition for preparing an article according to claim 1 , wherein an amount of the acid anhydride in the composition is about 1 percent by weight to about 30 percent by weight based on weight of the copolymer.

9 . The composition for preparing an article according to claim 1 , wherein the composition further comprises pyridine.

10 . The composition for preparing an article according to claim 9 , wherein an amount of the pyridine in the composition is about 1 percent by weight to about 30 percent by weight based on weight of the copolymer.

11 . An article comprising poly(imide-amide) copolymer, wherein an amount of a terminal amino group in the copolymer is less than or equal to about 0.01 millimoles per gram.

12 . The article according to claim 11 , wherein the poly(imide-amide) copolymer is a reaction product of a tetracarboxylic acid dianhydride represented by Chemical Formula 1, a diamine represented by Chemical Formula 2, and a carboxylic acid dichloride:

wherein in Chemical Formula 1 and Chemical Formula 2,
R 1 and R 2 are the same or different, and are each independently a substituted or unsubstituted C4 to C20 alicyclic organic group, or a substituted or unsubstituted C6 to C30 aromatic organic group, wherein the C6 to C30 aromatic organic group comprises one aromatic ring, two or more aromatic rings fused together to provide a condensed ring system, or two or more aromatic rings 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 —, —C(═O)NH—, a substituted or unsubstituted C3 to C10 cycloalkylene group, and a substituted or unsubstituted C6 to C15 arylene group.

13 . An article comprising poly(imide-amide) copolymer, which is a product of the composition according to claim 1 .

14 . The article according to claim 13 , wherein the article is a film, fiber, coating material, or an adhesive.

15 . The article according to claim 13 , wherein an amount of a terminal amine group in the copolymer is less than or equal to about 0.01 millimoles per gram.

16 . A display device comprising

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Choi Sungwon
• Ahn Chanjae
• Hong Sungwoo
• Sohn Byunghee
• Jeon Hyunjeong
• Ju Kyeong-Sik

Classifications

• C09D179/08 Primary

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

• C08G73/1042

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

• C08G73/14 Primary

  Polyamide-imides · CPC title

• C08G73/1067

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

• C08J5/18

  Manufacture of films or sheets · CPC title