Novel polyamideimide having low thermal expansion coefficient

Patent metadata

Field	Value
Publication number	US-2016194449-A1
Application number	US-201314758312-A
Country	US
Kind code	A1
Filing date	Oct 31, 2013
Priority date	Dec 27, 2012
Publication date	Jul 7, 2016
Grant date	—

Abstract

The present invention relates to a polyamideimide comprising an asymmetric dicarboxylic acid derivative wherein, from among a cyclic group A and a cyclic group B, two substitutents groups R and R′ are bonded only to the cyclic group A on one side. A polymer produced by means of the present invention can have adequate solubility with respect to organic solvents, high thermal stability, a high glass transition temperature, high transparency and a low thermal expansion coefficient, and is able not only to satisfy requirements for core substrate materials of flexible displays but also to be used as a material for various soft electronic data devices.

First claim

1 . An asymmetric dicarboxylic acid derivative, alkali metal salts or its alkaline earth metal salts thereof, represented by Formula A, having two substituents R and R′ attached to only cyclic group A of both cyclic group A and B of Formula A:

wherein R and R′ are identical to or different from each other, and are independently selected from the group consisting of C1 to C12 alkyl group unsubstituted or substituted with one or more halogen; C1 to C12 alkoxy group unsubstituted or substituted with one or more halogen; C4 to C30 cycloalkyl group unsubstituted or substituted with one or more halogen; C6 to C30 aryl group unsubstituted or substituted with one or more halogen, C1 to C12 alkyl group, C1 to C12 alkoxy group, C1 to C12 halogenated alkyl group and/or C1 to C12 halogenated alkoxy group; C3 to C30 heteroaryl group unsubstituted or substituted with one or more halogen, C1 to C12 alkyl group, C1 to C12 alkoxy group, C1 to C12 halogenated alkyl group and/or C1 to C12 halogenated alkoxy group; and C6 to C30 arylalkyl group unsubstituted or substituted with one or more halogen, C1 to C12 alkyl group, C1 to C12 alkoxy group, C1 to C12 halogenated alkyl group and/or C1 to C12 halogenated alkoxy group;
X1, X2 and X3 are identical to or different from each other, and are independently selected from the group consisting of hydrogen; halogen; C1 to C12 alkyl group unsubstituted or substituted with one or more halogen; C1 to C12 alkoxy group unsubstituted or substituted with one or more halogen; C4 to C30 cycloalkyl group unsubstituted or substituted with one or more halogen; C6 to C30 aryl group unsubstituted or substituted with one or more halogen, C1 to C12 alkyl group, C1 to C12 alkoxy group, C1 to C12 halogenated alkyl group and/or C1 to C12 halogenated alkoxy group; C3 to C30 heteroaryl group unsubstituted or substituted with one or more halogen, C1 to C12 alkyl group, C1 to C12 alkoxy group, C1 to C12 halogenated alkyl group and/or C1 to C12 halogenated alkoxy group; and C6 to C30 arylalkyl group unsubstituted or substituted with one or more halogen, C1 to C12 alkyl group, C1 to C12 alkoxy group, C1 to C12 halogenated alkyl group and/or C1 to C12 halogenated alkoxy group;
L1 represents a direct bond, —O—, —S—, —C(═O)O—, —OC(═O)—, —C(═O)—, —SO2-, —C(R1)(R2)-, —NR3, where R1, R2 and R3 are identical to or different from each other, and are independently selected from the group consisting of hydrogen; C1 to C12 alkyl group unsubstituted or substituted with one or more halogen; C4 to C20 cycloalkyl group unsubstituted or substituted with one or more halogen; C6 to C20 aryl group unsubstituted or substituted with one or more halogen; and C3 to C20 heteroaryl group unsubstituted or substituted with one or more halogen; and
said cyclic group

and

each independently represent C5 to C30 arylene or cycloalkylene unsubstituted or substituted with 5-membered or 6-membered ring which is unsubstituted or substituted or more halogen; or C5 to C30 heteroarylene or heterocycloalkylene unsubstituted or substituted with 5-membered or 6-membered ring which is unsubstituted or substituted or more halogen.

2 . The asymmetric dicarboxylic acid derivatives, alkali metal salts or its alkaline earth metal salts thereof according to claim 1 , wherein R and R′ are identical to or different from each other, and are hydrocarbyl group comprising fluorine.

3 . The asymmetric dicarboxylic acid derivatives, alkali metal salts or its alkaline earth metal salts thereof according to claim 1 , wherein L is anyone selected from the group consisting of a direct bond, —O—, and —S—.

4 . The asymmetric dicarboxylic acid derivatives, alkali metal salts or its alkaline earth metal salts thereof according to claim 3 , wherein L is a direct bond, R and R′ represent C1 to C5 alkyl substituted with fluorine, X1 to X3 are identical to or different from each other, and are selected from the group consisting of hydrogen; halogen; trifluromethyl, pentafluoroethyl, C1 to C5 alkyl, said cyclic group

and

represent C6 to C12 arylene unsubstituted or substituted with one or more halogen.

5 . The asymmetric dicarboxylic acid derivatives, alkali metal salts or its alkaline earth metal salts thereof according to claim 4 , represented as Formula A-1, wherein R and R′ are each CF 3 or C 2 F 5 :

6 . A process for producing an asymmetrical dicarboxylic acid derivative represented as [Formula A] in Reaction 1, comprising reaction between diamine compound represented as Formula A-2 and compound represented as Formula A-3 in imidization reaction:

wherein R and R′ are identical to or different from each other, and are independently selected from the group consisting of C1 to C12 alkyl group unsubstituted or substituted with one or more halogen; C1 to C12 alkoxy group unsubstituted or substituted with one or more halogen; C4 to C30 cycloalkyl group unsubstituted or substituted with one or more halogen; C6 to C30 aryl group unsubstituted or substituted with one or more halogen, C1 to C12 alkyl group, C1 to C12 alkoxy group, C1 to C12 halogenated alkyl group and/or C1 to C12 halogenated alkoxy group; C3 to C30 heteroaryl group unsubstituted or substituted with one or more halogen, C1 to C12 alkyl group, C1 to C12 alkoxy group, C1 to C12 halogenated alkyl group and/or C1 to C12 halogenated alkoxy group; and C6 to C30 arylalkyl group unsubstituted or substituted with one or more halogen, C1 to C12 alkyl group, C1 to C12 alkoxy group, C1 to C12 halogenated alkyl group and/or C1 to C12 halogenated alkoxy group;
X1, X2 and X3 are identical to or different from each other, and are independently selected from the group consisting of hydrogen; halogen; C1 to C12 alkyl group unsubstituted or substituted with one or more halogen; C1 to C12 alkoxy group unsubstituted or substituted with one or more halogen; C4 to C30 cycloalkyl group unsubstituted or substituted with one or more halogen; C6 to C30 aryl group unsubstituted or substituted with one or more halogen, C1 to C12 alkyl group, C1 to C12 alkoxy group, C1 to C12 halogenated alkyl group and/or C1 to C12 halogenated alkoxy group; C3 to C30 heteroaryl group unsubstituted or substituted with one or more halogen, C1 to C12 alkyl group, C1 to C12 alkoxy group, C1 to C12 halogenated alkyl group and/or C1 to C12 halogenated alkoxy group; and C6 to C30 arylalkyl group unsubstituted or substituted with one or more halogen, C1 to C12 alkyl group, C1 to C12 alkoxy group, C1 to C12 halogenated alkyl group and/or C1 to C12 halogenated alkoxy group;
L1 represents a direct bond, —O—, —S—, —C(═O)O—, —OC(═O)—, —C(═O)—, —SO2-, —C(R1)(R2)-, —NR3, where R1, R2 and R3 are identical to or different from each other, and are independently selected from the group consisting of hydrogen; C1 to C12 alkyl group unsubstituted or substituted with one or more halogen; C4 to C20 cycloalkyl group unsubstituted or substituted with one or more halogen; C6 to C20 aryl group unsubstituted or substituted with one or more halogen; and C3 to C20 heteroaryl group unsubstituted or substituted with

Assignees

• Korea Advanced Inst Sci & Tech

Inventors

• Kim Sang Youl
• Kim Sun Dal

Classifications

• C07C211/45

  Monoamines · CPC title

• C08G73/14 Primary

  Polyamide-imides · CPC title

• C08J2379/08

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

• C07D209/48

  with oxygen atoms in positions 1 and 3, e.g. phthalimide · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title