IP Library Granted Patent US 9,735,004
Granted Patent B2
US 9,735,004 · App. 15/229,049 · Granted Aug 15, 2017

PVDF-TrFE co-polymer having improved ferroelectric properties, methods of making a PVDF-TrFE co-polymer having improved ferroelectric properties and methods of changing the end group of a PVDF-TrFE co-polymer

Inventors: Jakob Nilsson (Linkoping, SE); Christian Brox-Nilsen (Linkoping, SE)
Assignee: Thin Film Electronics ASA
H01L21/0212C08F8/00C08F8/04C08F8/12C08F8/20C08F8/26H01L27/1159H01L27/11507H01L37/025H01L41/193C08F214/182C08F214/22C08F2500/02C08F2810/40
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Quick Facts
Patent No.
US 9,735,004
App. No.
15/229,049
Granted
Aug 15, 2017
Kind
B2
Abstract

A method of exchanging or transforming end groups in and/or improving the ferroelectric properties of a PVDF-TrFE co-polymer is disclosed. A bulky or chemically dissimilar end group, such as an iodine, sulfate, aldehyde or carboxylic acid end group, may be transformed to a hydrogen, fluorine or chlorine atom. A method of making a PVDF-TrFE co-polymer is disclosed, including polymerizing a mixture of VDF and TrFE using an initiator, and transforming a bulky or chemically dissimilar end group to a hydrogen, fluorine or chlorine atom. A PVDF-TrFE co-polymer or other fluorinated alkene polymer is also disclosed. The co-polymer may be used as a ferroelectric, electromechanical, piezoelectric or dielectric material in an electronic device.

Claims (10)

1. A method of exchanging an end group of a polyvinylidene fluoride-trifluoroethylene (PVDF-TrFE) co-polymer, comprising:

exchanging an iodine or hydroxyl end group on a polyvinylidene fluoride-trifluoroethylene (PVDF-TrFE) co-polymer with hydrogen, fluorine or chlorine, and

isolating or purifying the PVDF-TrFE co-polymer having the hydrogen, fluorine or chlorine end group.

2. The method according to claim 1 , wherein the PVDF-TrFE co-polymer has the iodine end group, and exchanging the iodine end group comprises reacting the PVDF-TrFE co-polymer having the iodine end group with a tin hydride complex.

3. The method according to claim 1 , wherein the PVDF-TrFE co-polymer has the hydroxy end group, and exchanging the hydroxy end group comprises reacting the PVDF-TrFE co-polymer having the hydroxy end group with a source of hydrogen, fluorine or chlorine.

4. The method according to claim 3 , wherein the PVDF-TrFE co-polymer has the hydroxy end group, and exchanging the hydroxy end group comprises reacting the PVDF-TrFE co-polymer having the hydroxy end group with a source of hydrogen.

5. The method according to claim 3 , further comprising converting a PVDF-TrFE, co-polymer having a carboxyl, sulfonyl or sulfate end group to the PVDF-TrFE co-polymer having the hydroxy end group.

6. The method according to claim 5 , wherein converting the PVDF-TrFE co-polymer having the carboxyl, sulfonyl or sulfate end group to the PVDF-TrFE co-polymer having the hydroxy end group comprises hydrolyzing the carboxyl, sulfonyl or sulfate end group.

7. The method according to claim 5 , wherein the carboxyl end group has the formula R 1 —C(═O)O—, the sulfonyl end group has the formula R 2 —S(═O) 2 O—, and the sulfate end group has the formula —OS(═O) 2 O − , where R 1 and R 2 are independently alkyl, aryl, or aralkyl, which may be substituted or unsubstituted.

8. The method according to claim 7 , wherein R 1 and R 2 are independently C 1 -C 6 alkyl, C 6 -C 10 aryl, or C 6 -C 10 aryl substituted with from 1 to 3 methyl groups substituted with 0 to 3 fluorine atoms.

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 14, 2025
From: XEROX CORPORATION
To: GENESEE VALLEY INNOVATIONS, LLC
Reel/Frame 073562/0677 →
SECOND LIEN NOTES PATENT SECURITY AGREEMENT Recorded Jul 2, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 071785/0550 →
FIRST LIEN NOTES PATENT SECURITY AGREEMENT Recorded Apr 11, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 070824/0001 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT RF 064095/0455 Recorded Feb 13, 2024
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: XEROX CORPORATION
Reel/Frame 066566/0438 →
SECURITY INTEREST Recorded Feb 13, 2024
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 066741/0001 →
SECURITY INTEREST Recorded Nov 20, 2023
From: XEROX CORPORATION
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 065628/0019 →
SECURITY INTEREST Recorded Jun 28, 2023
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 064095/0455 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 22, 2023
From: THIN FILM ELECTRONICS ASA
To: XEROX CORPORATION
Reel/Frame 064033/0554 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2016
From: NILSSON, JAKOB; BROX-NILSEN, CHRISTIAN
To: THIN FILM ELECTRONICS ASA
Reel/Frame 039496/0799 →
Continuity (2)
Provisional Application 62201366 · Aug 5, 2015
Related Publication 20170040156A1 · Feb 9, 2017