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-10072180-B2
Application number	US-201514744621-A
Country	US
Kind code	B2
Filing date	Jun 19, 2015
Priority date	Jan 30, 2015
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

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. An article comprising a polymer, the polymer consisting of a poly(imide-amide) copolymer, the poly(imide-amide) copolymer having a terminal amino group in an amount of less than or equal to about 0.01 millimole per gram, and the poly(imide-amide) copolymer obtained from a reaction of a tetracarboxylic acid dianhydride, a diamine, and a carboxylic acid dichloride, wherein the tetracarboxylic acid dianhydride consists of 3,3′,4,4′-biphenyltetracarboxylic dianhydride and 2,2-bis-(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, the diamine consists of 2,2′-bis(trifluoromethyl)benzidine, and the carboxylic acid dichloride consists of terephthaloyl chloride.

2. The article according to claim 1 , wherein the article is a film, fiber, coating material, or an adhesive.

3. A display device comprising the article according to claim 1 .

4. The display device according to claim 3 , wherein the display device is a flexible display device.

5. A method of preparing an article comprising a poly(imide-amide) copolymer, the poly(imide-amide) copolymer having an amount of a terminal amino group of less than or equal to about 0.01 millimole per gram, the method comprising:
reacting a tetracarboxylic acid dianhydride represented by Chemical Formula 1, a diamine, and a carboxylic acid dichloride to form a reaction product;
removing hydrochloric acid (HCl) from the reaction product to obtain an HCl-removed reaction product;
adding a solvent and an acid anhydride to the HCl-removed reaction product to produce a mixture; and
heating the mixture to about 300° C. to remove the solvent and provide an article comprising a poly(imide-amide) copolymer having an amount of a terminal amino group of less than or equal to about 0.01 millimole per gram:

wherein in Chemical Formula 1,
R 1 is a 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 C3 to C10 cycloalkylene group, and a C6 to C15 arylene group, and
wherein the diamine is at least one selected from the following chemical formulae:

wherein in the above chemical formulae,
R 32 to R 41 and R 45 are the same or different and are each independently a halogen, a nitro group, a C1 to C15 alkyl group, a C1 to C15 alkoxy group, a C1 to C15 fluoroalkyl group, a C3 to C15 cycloalkyl group, a C3 to C15 heterocycloalkyl group, a C3 to C15 cycloalkoxy group, a C6 to C15 aryl group, a C6 to C15 aryloxy group, or a C2 to C15 heteroaryl group,
X 2 to X 6 and X 8 to X 10 are the same or different and are each independently a single bond, a C1 to C10 alkylene group, a C3 to C10 cycloalkylene group, a C5 to C40 heterocycloalkylene group, a C6 to C15 arylene group, a C3 to C40 heteroarylene group, —SO 2 —, —O—, —C(═O)—, or a combination thereof,
n35 to n37, n40 to n42, and n46 to n49, are integers ranging from 0 to 4, and
n38 and n39 are integers ranging from 0 to 3.

6. The method according to claim 5 , wherein the adding a solvent and an acid anhydride to the HCl-removed reaction product to produce a mixture comprises:
adding a solvent to the HCl-removed reaction product to produce a mixture comprising about 5 percent by weight to about 30 percent by weight of the HCl-removed reaction product and about 95 percent by weight to about 70 percent by weight % of the solvent in the mixture, and
adding an acid anhydride to the mixture in an amount of about 1 percent by weight to about 30 percent by weight of the acid anhydride based on weight of the HCl-removed reaction product.

7. The method according to claim 5 , wherein the adding a solvent and an acid anhydride to the HCl-removed reaction product further comprises adding pyridine to the mixture in an amount of about 1 percent by weight to about 30 percent by weight based on weight of the HCl-removed reaction product.

8. The method according to claim 5 , 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.

9. The method according to claim 5 , 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.

10. An article prepared by the method according to claim 5 , wherein the article comprising a polymer, the polymer consisting of a poly(imide-amide) copolymer, the poly(imide-amide) copolymer having a terminal amino group in an amount of less than or equal to about 0.01 millimole per gram.

11. The article according to claim 10 , wherein the article is a film, a fiber, a coating material, or an adhesive.

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

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

Classifications

• C08G73/1042

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

• C08G73/1028

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

• C08G73/1067

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

• C09D179/08 Primary

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

• C08G73/1039

  comprising halogen-containing substituents · CPC title