Polyimide precursor solution and polyimide film produced using same

Patent metadata

Field	Value
Publication number	US-11479643-B2
Application number	US-201816617379-A
Country	US
Kind code	B2
Filing date	Jun 27, 2018
Priority date	Sep 29, 2017
Publication date	Oct 25, 2022
Grant date	Oct 25, 2022

Abstract

The present invention relates to the production of a polyimide precursor, whereby, by using an amide-based organic solvent having a positive-number partition coefficient (Log P) and a density of at most 1 g/cm3, an interaction between the organic solvent and polyamic acid, which is a polyimide precursor, may be mitigated, thereby enabling the decrease of the viscosity of a polyimide precursor solution, and thus enabling a polyimide precursor solution having high solid content and low viscosity to be obtained.

First claim

What is claimed is:

1. A polyimide precursor solution comprising a polyimide precursor and an amide-based organic solvent, wherein the organic solvent has a positive distribution coefficient (Log P) at 25° C. and a density of 1 g/cm 3 or less,
wherein the organic solvent comprises diethylpropionamide (DEPA).

2. The polyimide precursor solution according to claim 1 , wherein the polyimide precursor solution has a solid content of 10 to 25% by weight and a viscosity of 7000 cP or less.

3. The polyimide precursor solution according to claim 1 , wherein the polyimide precursor is a polyamic acid having a repeating structure of the following formula 1:

wherein,
X is a tetravalent organic group selected from the group of aromatic, alicyclic, and aliphatic tetravalent organic groups derived from tetracarboxylic dianhydride, and
Y comprises a divalent organic group selected from the group of aromatic, alicyclic, and aliphatic divalent organic groups derived from diamine.

4. The polyimide precursor solution according to claim 3 , wherein X is a tetravalent organic group selected from the group of the following formulae 2a to 2g:

in formulas 2a to 2g,
R 31 to R 42 are each independently an alkyl group having 1 to 10 carbon atoms or a fluoroalkyl group having 1 to 10 carbon atoms,
a 1 is an integer of 0 to 2, b 1 is an integer of 0 to 4, c 1 is an integer of 0 to 8, d 1 and e 1 are each independently an integer of 0 to 3, f 1 and g 1 are each independently an integer of 0 to 4, h 1 and j 1 are each independently an integer of 0 to 3, i 1 is an integer of 0 to 4, k 1 and l 1 are each independently an integer of 0 to 4,
A 1 , A 2 and A 3 are each independently selected from the group consisting of a single bond, —O—, —CR 46 R 47 —, —C(═O)—, —C(═O)O—, —C(═O)NH—, —S—, —SO 2 —, a phenylene group, and a combination thereof, wherein R 46 and R 47 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.

5. The polyimide precursor solution according to claim 3 , wherein Y is a divalent organic group selected from the group of the following formulae 4a to 4d:

in formula 4b, L 1 is a single bond, —O—, —CO—, —S—, —SO 2 —, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —CONH—, —COO—, —(CH 2 )n 1 -, —O(CH 2 )n 2 O—, —OCH 2 —C(CH 3 ) 2 —CH 2 O— or —COO(CH 2 )n 3 OCO—, and n 1 , n 2 and n 3 are each an integer of 1 to 10,

in formula 4c, L 2 and L 3 , which are the same or different from each other, are each independently a single bond, —O—, —CO—, —S—, —SO 2 —, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —CONH—, —COO—, —(CH 2 )n 1 -, —O(CH 2 )n 2 O—, —OCH 2 —C(CH 3 ) 2 —CH 2 O— or —COO(CH 2 )n 3 OCO—, and n 1 , n 2 and n 3 are each an integer of 1 to 10,

in formula 4d, L 4 , L 5 and L 6 , which are the same or different from each other, are each independently a single bond, —O—, —CO—, —S—, —SO 2 —, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —CONH—, —COO—, —(CH 2 )n 1 -, —O(CH 2 )n 2 O—, —OCH 2 —C(CH 3 ) 2 —CH 2 O— or —COO(CH 2 )n 3 OCO—, and n 1 , n 2 and n 3 are each an integer of 1 to 10,
wherein at least one hydrogen atom contained in the aromatic rings of formulas 4a to 4d is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or a fluoroalkyl group having 1 to 10 carbon atoms.

6. The polyimide precursor solution according to claim 1 , wherein the polyimide precursor further comprises a structure of the following formula 6 in the molecular structure:

wherein, p and q are molar fractions, and when p+q=100, p is 70 to 90 and q is 10 to 30.

Assignees

• Lg Chemical Ltd

Inventors

• Yun Cheolmin
• Park Jinyoung
• Shin Bora
• Kim Kyungjun

Classifications

• G02F1/1337

  Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers · CPC title

• C08G73/1067

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

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08J2379/08

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

• C08G73/1032 Primary

  characterised by the solvent(s) used · CPC title