# US 8,784,690 B2 · Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels and foams > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,784,690 B2 - Document ID: US8784690B2 - Status: Granted - Kind: B2 - Application number: 13/199,134 - Filed: 2011-08-19 - Published: 2012-02-23 - Granted: 2014-07-22 - Earliest claimed: 2010-08-20 - Assignees: Rhodia Operations - Applicants: Chantal Badre; Lawrence Hough; Ahmed Alsayed - Inventors: Chantal Badre; Lawrence Hough; Ahmed Alsayed - Web page: https://patentgrep.com/patent/US8784690B2 ## CPC - H01B 1/127: {comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes} - C08L 25/18: Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen - 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 - H01B 1/122: {Ionic conductors} - H01B 13/0026: {Apparatus for manufacturing conducting or semi-conducting layers, e.g. deposition of metal} - H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene} - H10K 85/113: {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene} - H10K 85/1135: {Polyethylene dioxythiophene [PEDOT]; Derivatives thereof} - C08G 2261/1424: containing ether groups, including alkoxy - C08G 2261/3223: containing one or more sulfur atoms as the only heteroatom, e.g. thiophene - C08G 2261/51: Charge transport - C08G 2261/794: with polymeric dopants - C08K 5/3445: Five-membered rings - H10K 50/81: Anodes - Y02E 10/549: Organic PV cells - Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product - H01B: CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES (selection for magnetic properties H01F1/00; waveguides H01P {; printed circuits H05K}) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## 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 ### Claim 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. ### Claim 2 (depends on 1) 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. ### Claim 3 (depends on 1) 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. ### Claim 4 (depends on 1) 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. ### Claim 5 (depends on 1) 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. ### Claim 6 (depends on 1) 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. ### Claim 7 (depends on 1) The polymer film of claim 1, wherein the one or more electrically conductive polymers comprise poly(3,4-ethylenedioxythiophene). ### Claim 8 (depends on 1) 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. ### Claim 9 (depends on 1) 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. ### Claim 10 (depends on 1) The polymer film of claim 1, wherein the ionic liquid comprises 1-ethyl-3-methyl-imidazolium tetracyanoborate. ### Claim 11 (depends on 1) An electronic device, comprising at least one polymer film according to claim 1. ### Claim 12 (depends on 11) 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. ### Claim 13 (depends on 12) 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. ### Claim 14 (depends on 12) An electronic device according to claim 12, wherein the device is an organic light emitting diode device. ### Claim 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. ### Claim 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.