IP Library Granted Patent US 8,784,690
Granted Patent B2
US 8,784,690 · App. 13/199,134 · Granted Jul 22, 2014

Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels and foams

Inventors: Chantal Badre (Guttenberg, PA); Lawrence Hough (Philadelphia, PA); Ahmed Alsayed (Cherry Hill, NJ)
Assignee: Rhodia Operations
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Quick Facts
Patent No.
US 8,784,690
App. No.
13/199,134
Granted
Jul 22, 2014
Kind
B2
Abstract

A polymer film, polymer gel, and polymer foam each contain an electrically conductive polymer and an ionic liquid and are each useful as a component of an electronic device.

Claims (42)

1. A polymer film, comprising:

(a) one or more electrically conductive polymers selected from polythiophene polymers, polyselenophene polymers, polytelurophene polymers, polypyrrole polymers, polyaniline polymers, fused heterocyclic heteroaromatic polymers and mixtures thereof, and, optionally, further comprising one or more water soluble polymeric acid dopants, and

(b) an ionic liquid,

wherein the ionic liquid comprises one or more compounds comprising:

(i) an imidazolium cation, and

(ii) a tetracyanoborate anion.

2. The polymer film of claim 1 , wherein the amount of ionic liquid is effective to provide a film having a sheet resistance of less than or equal to about 500 Ohms per square.

3. The polymer film of claim 1 , wherein the amount of ionic liquid is effective to provide a film having a conductivity of greater than 500 Siemens per centimeter.

4. The polymer film of claim 1 , wherein the polymer film comprises, based on 100 parts by weight of the polymer film:

(a) from about 10 to about 80 parts by weight of the one or more electrically conductive polymers, and

(b) from about 20 to about 90 parts by weight of the ionic liquid.

5. The polymer film of claim 1 , wherein the electrically conductive polymer comprises a mixture of one or more electrically conductive polythiophene polymers and one or more water soluble polymeric acid dopants.

6. The polymer film of claim 1 , wherein the electrically conductive polymer comprises, based on 100 pbw of the electrically conductive polymer, a mixture of:

(i) from about 20 to about 50 parts by weight of one or more electrically conductive polythiophene polymers, and

(ii) from about 50 to about 80 parts by weight, of one or more water soluble polymeric acid dopants.

7. The polymer film of claim 1 , wherein the one or more electrically conductive polymers comprise poly(3,4-ethylenedioxythiophene).

8. The polymer film of claim 1 , wherein the one or more electrically conductive polymers comprise poly(3,4-ethylenedioxythiophene) and a poly(styrene sulfonic acid) dopant.

9. The polymer film of claim 1 , wherein the ionic liquid comprises one or more compounds comprising an imidazolium cation selected from 1,3-dimethyl-imidazolium, 1-benzyl-3-methyl-imidazolium, 1-butyl-3-methyl-imidazolium, 1-ethyl-3-methyl-imidazolium, 1-hexyl-3-methyl-imidazolium, 1-methyl-3-propyl-imidazolium, 1-methyl-3-octyl-imidazolium, 1-methyl-3-tetradecyl-imidazolium, 1-methyl-3-phenyl-imidazolium, 1,2,3-trimethyl-imidazolium, 1,2-methyl-3-octyl-imidazolium, 1-butyl-2,3-dimethyl-imidazolium, 1-hexyl-2,3-methyl-imidazolium, and 1-(2-hydroxyethyl)-2,3-dimethyl-imidazolium cations.

10. The polymer film of claim 1 , wherein the ionic liquid comprises 1-ethyl-3-methyl-imidazolium tetracyanoborate.

11. An electronic device, comprising at least one polymer film according to claim 1 .

12. An electronic device according to claim 11 , wherein the device comprises:

(a) an anode or combined anode and buffer layer 101 ,

(b) a cathode layer 106 ,

(c) an electroactive layer 104 , disposed between anode layer 101 and cathode layer 106 ,

(d) optionally, a buffer layer 102 , disposed between anode layer 101 and electroactive layer 104 ,

(e) optionally, a hole transport layer 105 , disposed between anode layer 101 and electroactive layer 104 , or if buffer layer 102 is present, between buffer layer 102 and electroactive layer 104 , and

(f) optionally an electron injection layer 105 , disposed between electroactive layer 104 and cathode layer 106 .

13. An electronic device according to claim 12 , wherein the device is a light-emitting diode, a light emitting diode display, a diode laser, a liquid crystal display, a lighting panel, a photodetector, a photoconductive cell, a photoresistor, a photoswitch, a phototransistor, a phototube, an infrared detector, a biosensor, a touch screen display device, a photovoltaic device, a solar cell, a transistor, or a diode.

14. An electronic device according to claim 12 , wherein the device is an organic light emitting diode device.

15. A polymer film, comprising, based on 100 parts by weight of the polymer film:

(a) from about 10 to about 80 parts by weight of an electrically conductive polymer, said electrically conductive polymer comprising, based on 100 parts by weight of the electrically conductive polymer:

(i) from about 20 to about 50 parts by weight of one or more electrically conductive polymers comprising poly(3,4-ethylenedioxythiophene), and

(ii) from about 50 to about 80 parts by weight of one or more water soluble polymeric acid dopants comprising a poly(styrene sulfonic acid) dopant, and

(b) from about 20 to about 90 parts by weight of an ionic liquid,

wherein the ionic liquid comprises 1-ethyl-3-methyl-imidazolium tetracyanoborate.

16. A polymer composition, comprising:

(a) a liquid carrier,

(b) an electrically conductive polymer dissolved or dispersed in the liquid carrier, said electrically conductive polymer comprising, based on 100 parts by weight of the electrically conductive polymer:

(i) from about 20 to about 50 parts by weight of one or more electrically conductive polymers comprising poly(3,4-ethylenedioxythiophene), and

(ii) from about 50 to about 80 parts by weight of one or more water soluble polymeric acid dopants comprising a poly(styrene sulfonic acid) dopant, and

(c) an ionic liquid dissolved or dispersed in the liquid carrier,

wherein the ionic liquid comprises 1-ethyl-3-methyl-imidazolium tetracyanoborate.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2012
From: BADRE, CHANTAL; HOUGH, LAWRENCE; ALSAYED, AHMED
To: RHODIA OPERATIONS; CENTRE NATIONALE DE LA RECHERCHE SCIENTIFIQUE
Reel/Frame 028636/0001 →
Continuity (4)
Provisional Application 61401856 · Aug 20, 2010
Provisional Application 61402135 · Aug 24, 2010
Provisional Application 61571568 · Jun 30, 2011
Related Publication 20120043530A1 · Feb 23, 2012