Diamine compound, and polyimide precursor and polyimide film using same

Patent metadata

Field	Value
Publication number	US-11926706-B2
Application number	US-202017276526-A
Country	US
Kind code	B2
Filing date	Jan 22, 2020
Priority date	Jan 25, 2019
Publication date	Mar 12, 2024
Grant date	Mar 12, 2024

Abstract

Disclosed is a novel diamine compound in which an imide ring is directly bonded to a (hetero)aryl ring in a molecule, and a polyimide film prepared by polymerizing the novel diamine compound exhibits improved thermal properties and storage stability.

First claim

What is claimed is:

1. A diamine compound represented by the following formula 1:

In the formula 1,
L is a linker selected from

Ar 1 and Ar 2 are each independently a divalent organic group selected from

R 1 to R 11 are each independently hydrogen, deuterium, a halogen atom, a cyano group, a hydroxy group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthiol group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a —COOH group, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, an amide group, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio group having 1 to 30 carbon atoms, an ester group, —CD 3 , an azide group, a nitro group, or a substituted or unsubstituted (3-30 membered) heteroaryl group comprising at least one selected from B, N, O, S, P (═O), Si and P,
Y is selected from

l, m, n, o, p, q, r, s, t, u and v are each an integer of 0 to 4, and when l, m, n, o, p, q, r, s, t, u and v are integers of 2 to 4, each of R 1 to R 11 is the same or different.

2. The diamine compound according to claim 1 , wherein L in the formula 1 is a linker selected from—

Ar 1 and Ar 2 are each independently

R 1 to R 8 are each independently a halogen atom, or an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, which are unsubstituted or substituted with a halogen atom,
R 9 is a halogen atom, or an alkyl group having 1 to 6 carbon atoms which is unsubstituted or substituted with a halogen atom,
Y is selected from and

l, m, n, o, p, q, r, s and t are each an integer of 0 to 2.

3. The diamine compound according to claim 1 , wherein L in the formula 1 is phenyl which is unsubstituted or substituted with one or more substituents selected from the group consisting of trifluoromethyl, methyl, chlorine (Cl) and methoxy; biphenyl which is unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, trifluoromethyl and chlorine (Cl); terphenyl which is unsubstituted or substituted with trifluoromethyl; bis(trifluoromethylphenyl)sulfone, bis(methylphenyl)sulfone, {(trifluoromethylphenyl)sulfonyl}phenyl, diphenylsulfide, bis(methylphenyl)sulfide, bis(trifluoromethylphenyl)sulfide or diphenyl ether,
Ar 1 and Ar 2 are each independently phenyl which is unsubstituted or substituted with one or more substituents selected from the group consisting of methyl, trifluoromethyl and chlorine (Cl),
l is an integer of 0 to 2, and
m, n, o, p, q, r, s and t are each an integer of 0 or 1.

4. The diamine compound according to claim 1 , wherein the diamine compound of formula 1 is selected from compounds of the following structural formulae 1 to 21:

5. A polyimide precursor comprising a polymerized product of a composition comprising the diamine compound of formula 1 according to claim 1 and at least one acid dianhydride.

6. The polyimide precursor according to claim 5 , wherein the acid anhydride comprises BPDA (biphenyl-tetracarboxylic acid dianhydride), 6-FDA (4,4′-(hexafluoroisopropylidene)diphthalic anhydride) or a mixture thereof.

7. A polyimide film formed from the polyimide precursor according to claim 5 .

8. A flexible device including the polyimide film according to claim 7 as a substrate.

9. A polyimide precursor comprising a polymerized product of a composition comprising the diamine compound of formula 1 according to claim 2 and at least one acid dianhydride.

10. A polyimide precursor comprising a polymerized product of a composition comprising the diamine compound of formula 1 according to claim 3 and at least one acid dianhydride.

11. A polyimide precursor comprising a polymerized product of a composition comprising the diamine compound of formula 1 according to claim 4 and at least one acid dianhydride.

12. The polyimide precursor according to claim 9 , wherein the acid anhydride comprises BPDA (biphenyl-tetracarboxylic acid dianhydride), 6-FDA (4,4′-(hexafluoroisopropylidene)diphthalic anhydride) or a mixture thereof.

13. The polyimide precursor according to claim 10 , wherein the acid anhydride comprises BPDA (biphenyl-tetracarboxylic acid dianhydride), 6-FDA (4,4′-(hexafluoroisopropylidene)diphthalic anhydride) or a mixture thereof.

14. The polyimide precursor according to claim 11 , wherein the acid anhydride comprises BPDA (biphenyl-tetracarboxylic acid dianhydride), 6-FDA (4,4′-(hexafluoroisopropylidene)diphthalic anhydride) or a mixture thereof.

15. A polyimide film formed from the polyimide precursor according to claim 9 .

16. A polyimide film formed from the polyimide precursor according to claim 10 .

17. A polyimide film formed from the polyimide precursor according to claim 11 .

18. A flexible device including the polyimide film according to claim 15 as a substrate.

19. A flexible device including the polyimide film according to claim 16 as a substrate.

20. A flexible device including the polyimide film according to claim 17 as a substrate.

Assignees

• Lg Chemical Ltd

Inventors

• Kim Minju
• Park Jinyoung
• Lee Hoyong
• Song Cheol Jun

Classifications

• C08G73/1067 Primary

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

• C07D209/48

  with oxygen atoms in positions 1 and 3, e.g. phthalimide · CPC title

• C08G73/1032

  characterised by the solvent(s) used · CPC title

• C08G73/1064

  containing sulfur · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title