IP Library Granted Patent US 11,603,440
Granted Patent B2
US 11,603,440 · App. 16/912,654 · Granted Mar 14, 2023

Polyimide films and electronic devices

Inventors: Kostantinos Kourtakis (Media, PA); Gene M Rossi (Wilmington, DE); Joseph Casey Johnson (Pickerington, OH); Michael Thomas Kwasny (Columbus, OH)
Assignee: DUPONT ELECTRONICS, INC.
C08J5/18C08G73/1007C08J2379/08C08J2479/08C08K3/36C08K2003/2227C08K2003/2237C08K2003/2244
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Quick Facts
Patent No.
US 11,603,440
App. No.
16/912,654
Granted
Mar 14, 2023
Kind
B2
Abstract

In a first aspect, a polyimide film includes a dianhydride and a diamine. The dianhydride, the diamine or both the dianhydride and the diamine include an alicyclic monomer, an aliphatic monomer or both an alicyclic monomer and an aliphatic monomer. The polyimide film has a b* of 1.25 or less and a yellowness index of 2.25 or less for a film thickness of 50 μm. The polyimide film is formed by: (a) polymerizing the dianhydride and the diamine in the presence of a first solvent to obtain a polyamic acid solution; (b) imidizing the polyamic acid solution to form a substantially imidized solution; (c) casting the substantially imidized solution to form a film; and (d) drying the film.

Claims (19)

1. A polyimide film comprising:

a dianhydride and a diamine, wherein:

the dianhydride, the diamine or both the dianhydride and the diamine comprise an alicyclic monomer, an aliphatic monomer or both an alicyclic monomer and an aliphatic monomer; and

the polyimide film has an L* of at least 90, a b* of 1.25 or less, a yellowness index of 2.25 or less and a haze of less than 1% for a film thickness of 50 μm; and the polyimide film is formed by:

(a) polymerizing the dianhydride and the diamine in the presence of a first solvent to obtain a polyamic acid solution;

(b) imidizing the polyamic acid solution to form a substantially imidized solution, wherein greater than 85% of the amic acid groups are converted to polyimide, as determined by infrared spectroscopy;

(c) casting the substantially imidized solution to form a film; and

(d) drying the film.

2. The polyimide film of claim 1 , wherein after (b) and before (c), the substantially imidized solution is filtered to remove insoluble constituents of the solution.

3. The polyimide film of claim 1 , wherein the dianhydride is selected form the group consisting of 4,4′-(hexafluoroisopropylidene)diphthalic anhydride, 3,3′,4,4′-biphenyltetracarboxylic dianhydride, 3,3′,4,4′-benzophenonetetracarboxylic dianhydride, 3,3′,4,4′-diphenylsulfonetetracarboxylic dianhydride and mixtures thereof.

4. The polyimide film of claim 3 , wherein the dianhydride further comprises an alicyclic dianhydride selected from the group consisting of cyclobutane-1,2,3,4-tetracarboxylic dianhydride, 1,2,4,5-cyclohexanetetracarboxylic dianhydride, 1,2,3,4-cyclohexanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, hexahydro-4,8-ethano-1H,3H-benzo[1,2-c:4,5-c′]difuran-1,3,5,7-tetrone, 3-(carboxymethyl)-1,2,4-cyclopentanetricarboxylic 1,4:2,3-dianhydride and meso-butane-1,2,3,4-tetracarboxylic dianhydride.

5. The polyimide film of claim 1 , wherein the diamine comprises a fluorinated aromatic diamine.

6. The polyimide film of claim 5 , wherein the fluorinated aromatic diamine comprises 2,2′-bis(trifluoromethyl) benzidine.

7. The polyimide film of claim 1 , wherein the diamine comprises an aliphatic diamine selected from the group consisting of 1,2-diaminoethane, 1,6-diaminohexane, 1,4-diaminobutane, 1,5 diaminopentane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, 1,11-diaminoundecane, 1,12-diaminododecane, 1,16-hexadecamethylenediamine, 1,3-bis(3-aminopropyl)-tetramethyldisiloxane, isophoronediamine, bicyclo[2.2.2]octane-1,4-diamine and mixtures thereof.

8. The polyimide film of claim 1 , wherein the diamine comprises an alicyclic diamine selected from the group consisting of cis-1,3-diaminocyclobutane trans-1,3-diaminocyclobutane, 6-amino-3-azaspiro[3.3]heptane, and 3,6-diaminospiro[3.3]heptane, bicyclo[2.2.1]heptane-1,4-diamine, isophoronediamine, bicyclo[2.2.2]octane-1,4 diamine, cis-1,4 cyclohexane diamine, trans-1,4 cyclohexane diamine, 1,4-bis(aminomethyl)cyclohexane, 4,4′-methylenebis(cyclohexylamine), 4,4′-methylenebis(2-methyl-cyclohexylamine), bis(aminomethyl)norbornane and mixtures thereof.

9. The polyimide film of claim 1 , wherein the polyimide film has a thickness in the range of from 10 to 150 μm.

10. An electronic device comprising the polyimide film of claim 1 .

11. The polyimide film of claim 1 , wherein the polyimide film has a b* of 1.0 or less for a film thickness of 50 μm.

12. The polyimide film of claim 1 , wherein the polyimide film has a yellowness index of 2.0 or less for a film thickness of 50 μm.

Assignments (4)
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 073515/0243 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 073517/0298 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 7, 2021
From: KOURTAKIS, KOSTANTINOS; ROSSI, GENE M; JOHNSON, JOSEPH CASEY; KWASNY, MICHAEL THOMAS
To: DUPONT ELECTRONICS INC
Reel/Frame 057732/0285 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 11, 2021
From: KOURTAKIS, KOSTANTINOS; ROSSI, GENE M.; JOHNSON, JOSEPH CASEY; KWASNY, MICHAEL THOMAS
To: DUPONT ELECTRONICS, INC.
Reel/Frame 055569/0200 →
Continuity (2)
Provisional Application 62899379 · Sep 12, 2019
Related Publication 20210079181A1 · Mar 18, 2021