Electrically Conductive Films Formed From Dispersions Comprising Conductive Polymers and Polyurethanes

• US 20100270055A1
• Filed: 04/27/2009
• Published: 10/28/2010
• Est. Priority Date: 04/27/2009
• Status: Abandoned Application

• Current Assignee: Samsung Electronics Co. Ltd. (Samsung Group)
• Original Assignee: Air Products and Chemicals Incorporated (Linde Plc)
• Inventors: Fazel, Shafiq Nisarali, Zheng, Shiying
• Application Number:
  US12/430,368
• Publication Number:
  US 20100270055A1
• Time in Patent Office: Days
• US Class Current: 174/126.100
• CPC Class Codes: C08G 18/0828 containing sulfonate groups or groups forming them
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/3857 having nitrogen in addition to sulfur
• CPC Class Codes: C08G 18/4833 Polyethers containing oxyethylene units
• CPC Class Codes: C08G 18/5015 having fluorine atoms
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/6685 with compounds of group C08G18/3225 or polyamines of C08G18/38
• CPC Class Codes: C08G 18/73 acyclic
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/765 alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring
• CPC Class Codes: C08G 2261/3221 containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
• CPC Class Codes: C08G 2261/3223 containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
• CPC Class Codes: C08G 2261/5222 electrofluorescent
• CPC Class Codes: C08G 2261/91 Photovoltaic applications
• CPC Class Codes: C08G 2261/92 TFT applications
• CPC Class Codes: C08L 2205/02 containing two or more polymers of the same C08L -group
• CPC Class Codes: C08L 25/18 Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 27/18 Homopolymers or copolymers or tetrafluoroethene
• CPC Class Codes: C08L 65/00 Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain C08L7/00 - C08L57/00, C08L61/00 take precedence; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 75/04 : Polyurethanes
• CPC Class Codes: C09K 11/06 : containing organic luminescent materials
• CPC Class Codes: C09K 2211/14 : Macromolecular compounds
• CPC Class Codes: H10K 50/17 : Carrier injection layers
• CPC Class Codes: H10K 71/12 : using liquid deposition, e.g. spin coating
• CPC Class Codes: H10K 71/15 : characterised by the solvent used
• CPC Class Codes: H10K 85/113 : Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/141 : comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
• CPC Class Codes: Y02E 10/549 : Organic PV cells

Abstract

An aqueous dispersion and a method for making an aqueous dispersion. The dispersion including at least one conductive polymer such as a polythienothiophene, at least one polyurethane polymer and optionally at least one colloid-forming polymeric acid and one non-fluorinated polymeric acid. Devices utilizing layers formed of the inventive dispersions are also disclosed.

Claims

1. An aqueous dispersion comprising:

at least one electrically conductive polymer, and

at least one polyurethane polymer;

wherein the polyurethane polymer is at least partially water soluble or water dispersible.

2. The dispersion of claim 1 wherein the electrically conductive polymer selected from the group consisting of a polyaniline, polypyrroles, polythiophene, polyselenophenes, derivatives of polyaniline, polypyrroles, polyselenophenes, polythiophene and combinations thereof.

3. The dispersion of claim 1 wherein the electrically conductive polymer comprises at least one member selected from the group consisting of polyacetylenes, polythienothiophene/polystyrenesulfonic acid, polydioxythiophene/polystyrenesulfonic acid, polyaniline-polymeric-acid-colloids, PEDOT, PEDOT-polymeric-acid-colloids, and mixtures thereof.

4. The dispersion of claim 1, wherein the electrically conductive polymer comprises poly(thieno[3,4-b]thiophene).

5. The dispersion of claim 1 comprising at least one colloid-forming polymeric acid and at least one non-fluorinated polymer acid.

6. The dispersion of claim 1, wherein the dispersion comprises a colloid-forming polymeric acid that comprises at least one fluorinated sulfonic acid polymer.

7. The dispersion of claim 1, wherein the dispersion is treated with basic ion exchange resin.

8. The dispersion of claim 1, wherein the dispersion is treated with at least one basic compound.

9. The dispersion of claim 8, wherein the basic compound comprises at least one member selected from the group consisting of sodium hydroxide, ammonium hydroxide, tetra-methylammonium hydroxide, tetra-ethylammonium hydroxide, calcium hydroxide, cesium hydroxide, and combinations thereof.

10. The dispersion of claim 1 wherein the polyurethane polymer includes at least one sulfonic acid, phosphonic acid, boronic acid, or carboxylic acid, either in the acid form or in the neutralized form, or combination thereof.

11. The dispersion of claim 1 wherein the polyurethane polymer comprises silicon and florine atoms.

12. The dispersion of claim 1, wherein the polyurethane polymer comprises fluorinated alkylene oxide moiety.

13. The dispersion of claim 1 wherein the polyurethane polymer comprises siloxane moiety.

14. The dispersion of claim 1 wherein the polyurethane polymer comprises polyalkylene oxide moiety.

15. The dispersion of claim 1, wherein the polyurethane polymer includes at least 5 mol % of repeat units incorporating pendent side chain sulfonic acid, phosphonic acid, boronic acid, or carboxylic acid, either in the acid form or in the neutralized form, or combination thereof, based on the total repeat units of the polyurethane.

16. An electronic device comprising:

a polyurethane polymer dispersed electrically conductive film comprising polyaniline, polypyrroles, polythiophene, polyselenophenes, derivatives of polyaniline, polypyrroles, polyselenophenes, polythiophene and combinations thereof.

17. The device of claim 16, further comprising at least one polythiophene and at least one electrically conductive electrode in contact with the electrically conductive film.

18. The device of claim 16, wherein the device comprises an organic electronic device.

19. The device of claim 16, wherein the device comprises at least one member selected from the group consisting of organic light emitting diodes, organic optoelectronic devices, organic photovoltaic devices, diodes, and transistors.

20. The method for producing an aqueous dispersion comprising at least one conductive polymer, and at least one polyurethane polymer, comprises the following:

(a) providing an aqueous solution comprising one or more of an oxidant and a catalyst;

(b) providing an aqueous dispersion comprising an effective amount of the polyurethane polymer;

(c) combining the aqueous solution of the oxidant and/or catalyst with the aqueous dispersion of the polyurethane polymer;

(d) adding a monomer or a precursor of the conductive polymer to the combined aqueous dispersion of step (c);

(e) polymerizating the monomer or precursor containing polyurethane dispersion to form a polymeric dispersion; and

(f) contacting the polymeric dispersions with ion exchange resin(s) to remove impurities.

21. The method of claim 20, further comprising adjusting the pH of the polymer dispersion using ion exchange resin or a basic solution.

22. The method for producing an aqueous dispersion comprising at least one conductive polymer, and at least one polyurethane polymer, comprises the following:

(a) providing an aqueous solution comprising at least one oxidant and/or at least one catalyst;

(b) providing an aqueous dispersion comprising an effective amount of the polyurethane polymer;

(c) adding the aqueous dispersion of polyurethane polymer of step (b) to a monomer or a precursor of the conductive polymer;

(d) adding the oxidant and/or catalyst solution of step (a) to the combined mixture of step (c);

(e) polymerizating the monomer or precursor containing polyurethane dispersion to form a conductive polymeric dispersion; and

(f) contacting the polymeric dispersions with ion exchange resin(s) to remove impurities

23. The method of claim 22, further comprising adjusting the pH of the polymer dispersion using ion exchange resin or a basic solution.