Diamine compound, polyimide precursor and polyimide film using the same, and use thereof

Patent metadata

Field	Value
Publication number	US-12410281-B2
Application number	US-202217735811-A
Country	US
Kind code	B2
Filing date	May 3, 2022
Priority date	May 4, 2021
Publication date	Sep 9, 2025
Grant date	Sep 9, 2025

Abstract

Provided a diamine compound, a polyimide precursor and a polyimide film using the same, and a use thereof. The diamine compound may be very useful as a monomer for manufacturing a polyimide film having excellent transparency, high heat resistance, and low retardation.

First claim

What is claimed is:

1. A diamine compound represented by the following Chemical Formula 1:

wherein
L 1 to L 4 are independently of one another a single bond or C1-C10 alkylene;
R 1 to R 4 are independently of one another hydrogen, halogen, C1-C10 alkyl, haloC1-C10 alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, or C6-C20 aryl, or R 1 and R 3 may be linked to each other by —NR′—, —O—, or —S— to form a ring;
R′ is hydrogen, C1-C10 alkyl, C3-C10 cycloalkyl, or C6-C20 aryl;
ring A and ring B are independently of each other a C6-C20 aromatic ring;
R a and R b are independently of each other halogen, C1-C10 alkyl, haloC1-C10 alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, or C6-C20 aryl;
a and b are independently of each other an integer of 0 to 3; and
m and n are independently of each other an integer of 1 to 10.

2. The diamine compound of claim 1 , wherein L 1 and L 3 are independently of each other a single bond or C1-C5 alkylene; L 2 and L 4 are independently of each other C1-C5 alkylene; and ring A and ring B are independently of each other benzene or naphthalene.

3. The diamine compound of claim 2 , wherein the diamine compound is represented by the following Chemical Formula 2 or 3:

wherein
L 1 to L 4 are independently of one another C1-C5 alkylene;
X is —NR′—, —O—, or —S—;
R′ is hydrogen or C1-C5 alkyl;
R a and R b are independently of each other halogen, C1-C5 alkyl, haloC1-C5 alkyl, C1-C5 alkoxy, C3-C7 cycloalkyl, or C6-C12 aryl;
a and b are independently of each other an integer of 0 or 1; and
m and n are independently of each other an integer of 1 to 5.

4. The diamine compound of claim 3 , wherein the diamine compound is represented by the following Chemical Formula 4 or 5:

wherein
X is —O— or —S—;
R a and R b are independently of each other halogen, C1-C5 alkyl, or haloC1-C5 alkyl;
a and b are independently of each other an integer of 0 or 1; and
c and d are independently of each other an integer of 1 or 2.

5. The diamine compound of claim 4 , wherein the diamine compound is selected from the following:

wherein R c and R d are independently of each other hydrogen, fluoro, or trifluoromethyl.

6. The diamine compound of claim 1 , wherein the diamine compound is used for synthesizing a polyimide-based polymer.

7. A method of preparing the diamine compound of claim 1 , the method comprising the steps of:
reacting compounds represented by the following Chemical Formulae B-1 and B-2 with a compound of the following Chemical Formula C to prepare a dinitro compound of the following Chemical Formula A; and
reducing the dinitro compound of Chemical Formula A to prepare a diamine compound represented by the following Chemical Formula 1:

wherein L 1 to L 4 , R 1 to R 4 , ring A, ring B, R a , R b , a, b, m, and n are as defined in claim 1 .

8. The method of claim 7 , wherein the reducing of the dinitro compound of Chemical Formula A is performed in the presence of hydrogen and one or two or more selected from Pd/C, raney-nickel, Rh/C, Pt/C, and Ru/C, or in the presence of iron and acid.

Assignees

• Sk Innovation Co Ltd
• Sk Ie Tech Co Ltd

Inventors

• Lee Joo Hyun
• Park Sang Yoon
• Lee So Young

Classifications

• C08G73/1067

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

• C07D498/08 Primary

  Bridged systems · CPC title

• C07D295/16

  acylated on ring nitrogen atoms · CPC title

• C08J2379/08

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

• C08J5/18

  Manufacture of films or sheets · CPC title