Polyimide Precursor, Polyimide Precursor Composition, Polyimide Film, Method for Preparing the Same, and Use Thereof

Patent metadata

Field	Value
Publication number	US-2022010071-A1
Application number	US-202117371428-A
Country	US
Kind code	A1
Filing date	Jul 9, 2021
Priority date	Jul 13, 2020
Publication date	Jan 13, 2022
Grant date	—

Abstract

Provided are a polyimide precursor, a polyimide precursor solution, a polyimide film, a method for preparing the same, and a use thereof. According to an exemplary embodiment of the present invention, a polyimide film having excellent thermal resistance and satisfying transparency and a low coefficient of linear thermal expansion may be provided, and thus, may be usefully applied in a flexible display field requiring high dimensional stability and the like.

First claim

What is claimed is:

1 . A polyimide precursor solution comprising: a polyimide precursor derived from a tetracarboxylic acid dianhydride represented by the following Chemical Formula 1:

wherein
Q 1 is a single bond, —C(═O)—, —C(═O)O—, —C(═O)NH—, —NR′—, —S—, —SO 2 —, —CH 2 —, or a combination thereof, wherein R′ is hydrogen or C1-C10 alkyl;
R 1 and R 2 are independently of each other a halogen, hydroxy, thiol, nitro, cyano, C1-C10 alkyl, C1-C10 alkoxy, C6-C20 aryl, or a combination thereof, or may be connected to an adjacent substituent to form a ring; and
n and m are independently of each other an integer selected from 0 to 4, and when n and m are an integer of 2 or more, R 1 and R 2 may be the same as or different from each other.

2 . The polyimide precursor solution of claim 1 , wherein the tetracarboxylic acid dianhydride is selected from compounds represented by the following Chemical Formulae 2 to 5:

wherein
R 1 , R 2 , R′, n, and m are as defined in Chemical Formula 1 of claim 1 .

3 . The polyimide precursor solution of claim 1 , wherein the polyimide precursor solution includes: a polymerization component including the tetracarboxylic acid dianhydride represented by Chemical Formula 1 and a diamine; and an organic solvent.

4 . The polyimide precursor solution of claim 3 , wherein the diamine includes a unit represented by the following Chemical Formula 6:

wherein
R 3 is hydrogen, C1-C10 alkyl, or C1-C10 fluoroalkyl; and
p is an integer of 1 or 2.

5 . The polyimide precursor solution of claim 3 , wherein the organic solvent is selected from amides.

6 . The polyimide precursor solution of claim 5 , wherein the organic solvent is N,N-diethylacetamide, N,N-diethylformamide, N-ethylpyrrolidone, N,N-dimethylpropionamide, N,N-diethylpropionamide, or a combination thereof.

7 . The polyimide precursor solution of claim 3 , wherein a tetracarboxylic acid dianhydride selected from compounds represented by the following Chemical Formulae 7 and 8 is further included as the polymerization component:

wherein
Q 2 and Q 3 are a single bond, —O—, —C(═O)—, —C(═O)O—, —C(═O)NH—, —NR′—, —S—, —SO 2 —, phenylene, or a combination thereof, wherein R′ is hydrogen or C1-C10 alkyl.

8 . A polyimide precursor derived from a tetracarboxylic acid dianhydride represented by the following Chemical Formula 1 and a diamine:

wherein
Q 1 is a single bond, —C(═O)—, —C(═O)O—, —C(═O)NH—, —NR′—, —S—, —SO 2 —, —CH 2 —, or a combination thereof, wherein R′ is hydrogen or C1-C10 alkyl;
R 1 and R 2 are independently of each other a halogen, hydroxy, thiol, nitro, cyano, C1-C10 alkyl, C1-C10 alkoxy, C6-C20 aryl, or a combination thereof, or may be connected to an adjacent substituent to form a ring; and
n and m are independently of each other an integer selected from 0 to 4, and when n and m are an integer of 2 or more, R 1 and R 2 may be the same as or different from each other.

9 . The polyimide precursor of claim 8 , wherein the polyimide precursor includes a repeating unit represented by the following Chemical Formula a:

wherein
Q 1 is a single bond, —C(═O)—, —C(═O)O—, —C(═O)NH—, —NR′—, —S—, —SO 2 —, —CH 2 —, or a combination thereof, wherein R′ is hydrogen or C1-C10 alkyl;
R a and R b are independently of each other hydrogen or C1-C10 alkyl;
R 1 and R 2 are independently of each other a halogen, hydroxy, thiol, nitro, cyano, C1-C10 alkyl, C1-C10 alkoxy, C6-C20 aryl, or a combination thereof, or may be connected to an adjacent substituent to form a ring;
R 3 is hydrogen, C1-C10 alkyl, or C1-C10 fluoroalkyl;
p is an integer of 1 or 2; and
n and m are independently of each other an integer selected from 0 to 4, and when n and m are an integer of 2 or more, R 1 and R 2 may be the same as or different from each other.

10 . The polyimide precursor of claim 9 , wherein the polyimide precursor includes 10 to 100 mol % of the repeating unit represented by Chemical Formula a, based on total repeating units.

11 . A polyimide film comprising a repeating unit represented by the following Chemical Formula b:

wherein
Q 1 is a single bond, —C(═O)—, —C(═O)O—, —C(═O)NH—, —NR′—, —S—, —SO 2 —, —CH 2 —, or a combination thereof, wherein R′ is hydrogen or C1-C10 alkyl;
R 1 and R 2 are independently of each other a halogen, hydroxy, thiol, nitro, cyano, C1-C10 alkyl, C1-C10 alkoxy, C6-C20 aryl, or a combination thereof, or may be connected to an adjacent substituent to form a ring;
R 3 is hydrogen, C1-C10 alkyl, or C1-C10 fluoroalkyl;
p is an integer of 1 or 2; and
n and m are independently of each other an integer selected from 0 to 4, and when n and m are an integer of 2 or more, R 1 and R 2 may be the same as or different from each other.

12 . The polyimide film of claim 11 , wherein the polyimide film further includes a repeating unit represented by the following Chemical Formula c or d:

wherein
R 3 is hydrogen, C1-C10 alkyl, or C1-C10 fluoroalkyl; and
p is an integer of 1 or 2.

13 . The polyimide film of claim 11 , wherein the polyimide film has a coefficient of thermal expansion (CTE) of 50 ppm/° C. or less at 100 to 450° C.

14 . The polyimide film of claim 11 , wherein the polyimide film has
YI in accordance with ASTM E313 of 15 or less; a haze in accordance with ASTM D1003 of 2 or less; and a total light transmittance in a region of 380 to 780 nm in accordance with ASTM D1746 of 80% or more.

15 . The polyimide film of claim 11 , wherein the polyimide film has a modulus in accordance with ASTM D882 of 5.0 or more and an elongation of 15% or more.

16 . The polyimide film of claim 11 , wherein the polyimide film has
a coefficient of thermal expansion of 50 ppm/° C. or less at 100 to 450° C.; YI in accordance with ASTM E313 of 15 or less; a haze in accordance with ASTM D1003 of 2 or less; an average light transmittance in a region of 380 to 780 nm in accordance with ASTM D1746 of 80% or more; and a modulus in accordance with ASTM D882 of 8.0 or less and an elongation of 15% or more.

17 . A multilayer structure comprising the polyimide film of claim 11 .

18 . A photoelectric device comprising the polyimide film of claim 11 as a flexible substrate.

19 . A flexible display comprising the polyimide film of claim 11 as a flexible substrate.

20 . A method for preparing a polyimide film comprising: applying and coating the polyimide precursor solution of claim 1 on a substrate and then performing

Assignees

• Sk Innovation Co Ltd
• Sk Ie Tech Co Ltd

Inventors

• Kim Jong Chan
• Lee So Young

Classifications

• B32B2307/306

  Resistant to heat · CPC title

• B32B27/281

  comprising polyimides · CPC title

• B32B2307/558

  Impact strength, toughness · CPC title

• B32B2457/20

  Displays, e.g. liquid crystal displays, plasma displays · CPC title

• B32B27/06

  as the main or only constituent of a layer, {which is} next to another layer of {the same or of} a {different material (next to a layer of a particular substance B32B9/045; next to a bituminous or tarry layer B32B11/046; next to a water setting substance layer B32B13/12; next to a metal layer B32B15/08; next to a glass layer B32B17/10; next to a layer formed of natural mineral fibres or particles B32B19/045; next to a wood layer B32B21/08; next to a cellulosic plastic layer B32B23/08; next to a natural or synthetic rubber layer B32B25/08)} · CPC title