Diamine compound, and polyimide precursor and polyimide film using same

Patent metadata

Field	Value
Publication number	US-12084545-B2
Application number	US-201917277366-A
Country	US
Kind code	B2
Filing date	Dec 11, 2019
Priority date	Dec 12, 2018
Publication date	Sep 10, 2024
Grant date	Sep 10, 2024

Abstract

The present invention discloses a novel diamine that has a structure bearing an intramolecular imide group and additionally an amide-substituted aromatic ring group at opposite sides of the imide group. The use of the novel diamine as a polymerization ingredient in polyimide production can provide a polyimide film which has remarkably improved mechanical and thermal properties while maintaining optical properties.

First claim

What is claimed is:

1. A diamine having a structure of the following formula 1:

in the formula 1,
Z 1 to Z 8 are each independently a carbon atom or a nitrogen atom, with the proviso that not all of Z 1 to Z 8 are nitrogen atoms at the same time, R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 18 carbon atoms, n 1 , n 2 , n 3 and n 4 are each independently an integer of 0 to 4, and X is a single bond or a functional group selected from the group consisting of O, S, S—S, C(═O), —C(═O)O—, CH(OH), S(═O) 2 , Si(CH 3 ) 2 , CR′R″, C(═O)NH and a combination thereof, wherein R′ and R″ are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms and a fluoroalkyl group having 1 to 10 carbon atoms.

2. The diamine according to claim 1 , wherein at least one of Z 1 to Z 4 is a carbon atom, and at least one of Z 5 to Z 8 is a carbon atom.

3. The diamine according to claim 1 , wherein R 1 and R 2 are each independently an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, or n 1 and n 2 are each independently 0.

4. The diamine according to claim 1 , wherein Z 1 to Z 4 are all carbon atoms.

5. The diamine according to claim 1 , wherein at least one of Z 1 to Z 4 is a nitrogen atom or at least one of Z 5 to Z 8 is a nitrogen atom.

6. The diamine according to claim 1 , wherein at least one of Z 1 to Z a is a nitrogen atom and at least one of Z 5 to Z 8 is a nitrogen atom.

7. The diamine according to claim 1 , wherein the diamine of the formula 1 is selected from compounds of the formulae 1-1 to 1-20

8. A polyimide precursor comprising a polymerized product of a composition comprising at least one diamine and at least one acid dianhydride, wherein the diamine comprises the diamine according to claim 1 .

9. A polyimide film manufactured from the polyimide precursor according to claim 8 .

10. A polyimide film manufactured by a method comprising applying a polyimide precursor composition comprising the polyimide precursor according to claim 8 on a carrier substrate; and heating and curing the polyimide precursor composition.

11. A flexible device comprising the polyimide film according to claim 9 as a substrate.

12. A process for producing a flexible display comprising:
applying a polyimide precursor composition comprising the polyimide precursor according to claim 8 on a carrier substrate;
heating the polyimide precursor composition to imidize polyamic acid, thereby forming a polyimide film;
forming a device on the polyimide film; and
peeling off the polyimide film on which the device is formed from the carrier substrate.

13. The process for producing a flexible display according to claim 12 , wherein the process comprises an LTPS (low temperature polysilicon) process, an ITO process or an oxide process.

14. A method for preparing a diamine having a structure of the formula 1, the method comprising the steps of:
reacting a compound of the formula (i) with a compound of the formula (ii) to obtain a compound of the formula (iii);
reacting the compound of the formula (iii) with a compound of the formula (iv) to obtain a compound of the formula (v); and
reducing the compound of the formula (v) to obtain the diamine of the formula 1:

wherein,
Z a to Z d are each independently a carbon atom or a nitrogen atom, with the proviso that not all of Z a to Z d are nitrogen atoms at the same time, R 1 , R 2 and R a are each independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 18 carbon atoms, n 1 , n 2 and n are each independently an integer of 0 to 4, and X is a single bond or a functional group selected from the group consisting of O, S, S—S, C(═O), —C(═O)O—, CH(OH), S(═O) 2 , Si(CH 3 ) 2 , CR′R″, C(═O)NH and a combination thereof, wherein R′ and R″ are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms and a fluoroalkyl group having 1 to 10 carbon atoms.

Assignees

• Lg Chemical Ltd

Inventors

• Koo Kichul
• Kim Kyunghwan

Classifications

• C08J2379/08

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

• C08J5/18

  Manufacture of films or sheets · CPC title

• C07D403/14 Primary

  containing three or more hetero rings · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C09D179/08

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