Polyimide-based solution and polyimide-based film produced using same

Patent metadata

Field	Value
Publication number	US-10647883-B2
Application number	US-201816176603-A
Country	US
Kind code	B2
Filing date	Oct 31, 2018
Priority date	May 30, 2014
Publication date	May 12, 2020
Grant date	May 12, 2020

Abstract

The present invention relates to a polyimide-based solution that can be used to produce an isotropic transparent polyimide-based film with high heat resistance and excellent mechanical properties as well as high transmittance. A coating of the polyimide-based solution on a substrate has a haze of 1% or less after storage at a temperature of 30° C. and a humidity of 70% for 30 minutes.

First claim

What is claimed is:

1. A display substrate comprising a polyimide-based film obtained from a solvent having a positive partition coefficient (Log P) at 25° C. and a polyamic acid having a structure of Formula 2:

wherein X is a tetravalent organic group derived from an acid dianhydride and Y is divalent organic group derived from a diamine;
wherein a coating of the polyimide-based solution on a substrate has a haze of 1% or less after storage at a temperature of 30° C. and a humidity of 70% for 30 minutes; and
wherein the diamine is at least one selected from the group consisting of 4,4′-diaminodiphenyl ether, 4,4′-diaminodiphenylsulfide, 4,4′-diaminodiphenylsulfone, 4,4′-diaminobenzophenone, bis[4-(4-aminophenoxy)phenyl]methane, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 2,2-bis[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, 1,3-bis(4-aminophenoxy)benzene, 4,4′-bis(4-aminophenoxy)biphenyl, bis[4-(4-aminophenoxy)phenyl]ketone, bis[4-(4-aminophenoxy)phenyl]sulfoxide, bis[4-(4-aminophenoxy)phenyl]sulfone, bis[4-(4-aminophenoxy)phenyl]ether, 4,4′-bis(4-aminophenylsulfonyl)diphenyl ether, 4,4′-bis(4-aminothiophenoxy)diphenylsulfone, 1,4-bis[4-(4-aminophenoxy)benzoyl]benzene, 3,3′-diaminodiphenyl ether, 3,3-diaminodiphenylsulfide, 3,3′-diaminodiphenylsulfone, 3,3′-diaminobenzophenone, bis[4-(3-aminophenoxy)-phenyl]methane, 2,2-bis[4-(3-aminophenoxy)phenyl]propane, 2,2-bis[4-(3-aminophenoxy)phenyl-1,1,1,3,3,3-hexafluoropropane, 1,3-bis(3-aminophenoxy)benzene, 4,4′-bis(3-aminophenoxy)biphenyl, bis[4-(3-aminophenoxy)phenyl]ketone, bis[4-(3-aminophenoxy)phenyl]sulfide, bis[4-(3-aminophenoxy)phenyl]sulfone, bis[4-(3-aminophenoxy)phenyl]ether, 4,4′-bis(3-aminophenylsulfonyl)diphenyl ether, 4,4′-bis(3-aminothiophenoxy)diphenylsulfone, 1,4-bis[4-(3-aminophenoxy)benzoyl]benzene, 2,2′-bis(trifluoromethyl)benzidine, 2,2-bis[4-(-aminophenoxy)phenyl]hexafluoropropane, para-phenylene diamine, meta-phenylene diamine, and 4,4′-(9-fluorenylene)dianiline,
wherein Y in the polyamic acid comprises both a divalent organic group having a fluorine atom-containing substituent and a divalent organic group having no fluorine atom-containing substituent, and
wherein the molar ratio of the divalent organic group having a fluorine atom-containing substituent to all divalent organic groups in Y is from 0.1:1 to 0.9:1.

2. The display substrate comprising a polyimide-based film according to claim 1 , wherein X comprises a tetravalent organic group having a fluorine atom-containing substituent.

3. The display substrate comprising a polyimide-based film according to claim 1 , wherein the divalent organic groups are each independently selected from divalent aromatic organic groups, divalent alicyclic organic groups, divalent aliphatic organic groups, and combinations thereof and the tetravalent organic groups are each independently selected from tetravalent aromatic organic groups, tetravalent alicyclic organic groups, tetravalent aliphatic organic groups, and combinations thereof.

4. The display substrate comprising a polyimide-based film according to claim 1 , wherein Y comprises a divalent monocyclic or polycyclic aromatic organic group, a divalent monocyclic or polycyclic alicyclic organic group, or a divalent organic group having a structure in which two or more divalent organic groups selected from divalent monocyclic or polycyclic aromatic organic groups and divalent monocyclic or polycyclic alicyclic organic groups are linked to each other via a single bond or a linking group.

5. The display substrate comprising a polyimide-based film according to claim 1 , wherein the divalent organic group having a fluorine atom-containing substituent is a divalent monocyclic or polycyclic aromatic organic group, a divalent monocyclic or polycyclic alicyclic organic group, or a divalent organic group having a structure in which two or more divalent organic groups selected from divalent monocyclic or polycyclic aromatic organic groups and divalent monocyclic or polycyclic alicyclic organic groups are linked to each other via a single bond or a linking group, and the fluorine atom-containing substituent is directly substituted on the aromatic or alicyclic ring or is substituted on the linking group.

6. The display substrate comprising a polyimide-based film according to claim 1 , wherein the divalent organic group having a fluorine atom-containing substituent is derived from 2,2′-bis(trifluoromethyl)benzidine or 2,2-bis[4-(-aminophenoxy)phenyl]hexafluoropropane.

7. The display substrate comprising a polyimide-based film according to claim 1 , wherein the divalent organic group having no fluorine atom-containing substituent is derived from at least one compound selected from 4,4′-oxydianiline, 4,4′-(9-fluorenylidene)dianiline, para-phenylenediamine, and meta-phenylenediamine.

8. The display substrate comprising a polyimide-based film according to claim 1 , wherein X in the polyamic acid comprises a tetravalent organic group having a fluorine atom-containing substituent and a tetravalent organic group having no fluorine atom-containing substituent.

9. The display substrate comprising a polyimide-based film according to claim 2 , wherein the molar ratio of the tetravalent organic group having a fluorine atom-containing substituent to all tetravalent organic groups in X is from 0.1:1 to 1:1.

10. The display substrate comprising a polyimide-based film according to claim 1 , wherein X comprises a tetravalent monocyclic or polycyclic aromatic organic group, a tetravalent monocyclic or polycyclic alicyclic organic group, or a tetravalent organic group having a structure in which two or more tetravalent organic groups selected from tetravalent monocyclic or polycyclic aromatic organic groups and tetravalent monocyclic or polycyclic alicyclic organic groups are linked to each other via a single bond or a linking group.

11. The display substrate comprising a polyimide-based film according to claim 2 , wherein the tetravalent organic group having a fluorine atom-containing substituent is a tetravalent monocyclic or polycyclic aromatic organic group, a tetravalent monocyclic or polycyclic alicyclic organic group, or a tetravalent organic group having a structure in which two or more tetravalent organic groups selected from tetravalent monocyclic or polycyclic aromatic organic groups and tetravalent monocyclic or polycyclic alicyclic organic groups are linked to each other via a single bond or a linking group, and the fluorine atom-containing substituent is directly substituted on the aromatic or alicyclic ring or is substituted on the linking group.

12. The display substrate comprising a polyimide-based film according to claim 2 , wherein the tetravalent organic group having a fluorine atom-containing substituent is derived from 4,4′-(hexafluoroisopropylidene)diphthalic anhydride.

13. The display substrate comprising a polyimide-based film according to claim 8 , wherein the tetravalent organic group having no fluorine atom-containing substituent is derived from at least one compound selected from 3,3′,4,4′-biphenyltetracarboxylic dianhydride, 2,3,3′,4′-biphenyltetracarboxylic dianhydride, pyromellitic anhydride, 1,2,4,5-cyclohexanetetracarboxylic dianhydride, 4,4′-oxydiphthalic anhydride, and 2,3,3′,4′-oxydiphthalic anhydride.

14. The display substrate comprising a polyimide-based film according to claim 1 , wherein the polyimide-based solution has a viscosity of 400 cP to 50,000 cP, as measured using a Brookfield rotational viscometer at 25° C.

15.

Assignees

• Lg Chemical Ltd

Inventors

• Yun Cheolmin
• Shin Bora
• Jeong Hye Won
• Kim Kyungjun
• Park Hangah

Classifications

• C09D179/08 Primary

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

• C08G73/1003

  Preparatory processes · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08G73/1032

  characterised by the solvent(s) used · CPC title

• C08G73/1071

  Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain · CPC title