# US 8,784,692 B2 · Water dispersible polythiophenes made with polymeric acid colloids > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,784,692 B2 - Document ID: US8784692B2 - Status: Granted - Kind: B2 - Application number: 13/786,800 - Filed: 2013-03-06 - Published: 2013-08-01 - Granted: 2014-07-22 - Earliest claimed: 2002-09-24 - Assignees: E. I. Du Pont de Nemours and Company - Applicants: E I Du Pont De Nemours and Company - Inventors: Che-Hsiung Hsu; Yong Cao; Sunghan Kim; Daniel David Lecloux; Chi Zhang - Web page: https://patentgrep.com/patent/US8784692B2 ## CPC - C08G 61/126: {with a five-membered ring containing one sulfur atom in the ring} - B82Y 10/00: Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic - B82Y 30/00: Nanotechnology for materials or surface science, e.g. nanocomposites - 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 1/127: {comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes} - H10K 85/113: {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene} - H10K 85/1135: {Polyethylene dioxythiophene [PEDOT]; Derivatives thereof} - C08L 27/12: containing fluorine atoms - C08L 81/08: Polysulfonates - H10K 10/464: {Lateral top-gate IGFETs comprising only a single gate} - H10K 50/17: Carrier injection layers - H10K 71/60: Forming conductive regions or layers, e.g. electrodes - Y02E 10/549: Organic PV cells - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - 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}) - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION ## Abstract Compositions are provided comprising a continuous liquid aqueous medium having dispersed therein a polydioxythiophene and at least one colloid-forming fluorinated polymeric acid. Films from invention compositions are useful as buffer layers in organic electronic devices, including electroluminescent devices, such as, for example, organic light emitting diodes (OLED) displays. ## Claims ### Claim 1 A stable colloid particle containing composition comprising a continuous liquid aqueous medium having dispersed therein a polydioxythiophene and at least one colloid-forming fluorinated polymeric acid, and further comprising an additional material selected from the group consisting of polymers, dyes, carbon nanotubes, metal nanowires, coating aids, organic and inorganic conductive inks and pastes, charge transport materials, crosslinking agents, and combinations thereof, wherein said polydioxythiophene has the structure: wherein: R1 and R1′ are each independently selected from hydrogen and alkyl having 1 to 4 carbon atoms, or R1 and R1′ taken together form an alkylene chain having 1 to 4 carbon atoms, which may optionally be substituted by alkyl or aromatic groups having 1 to 12 carbon atoms, or a 1,2-cyclohexylene radical, and n is greater than about 6; wherein the composition does not re-disperse in an aqueous medium after it has been dried. ### Claim 2 (depends on 1) A composition according to claim 1, wherein R1 and R1′ together form an alkylene chain having 1 to 4 carbon atoms. ### Claim 3 (depends on 2) A composition according to claim 2, wherein said polydioxythiophene comprises poly(3,4-ethylenedioxythiophene). ### Claim 4 (depends on 1) A composition according to claim 1, wherein said colloid-forming fluorinated polymeric acid is selected from polymeric sulfonic acids, polymeric carboxylic acids, and polymeric phosphoric acids. ### Claim 5 (depends on 1) A composition according to claim 1, wherein said fluorinated polymeric acid comprises a polymeric sulfonic acid. ### Claim 6 (depends on 5) A composition according to claim 5, wherein said polymeric sulfonic acid is perfluorinated. ### Claim 7 (depends on 5) A composition according to claim 5, wherein said polymeric sulfonic acid is a perfluoroalkylenesulfonic acid. ### Claim 8 (depends on 7) A composition according to claim 7, wherein said polymeric sulfonic acid is perfluoroethylenesulfonic acid. ### Claim 9 (depends on 1) The composition of claim 1, wherein the colloid-forming fluorinated polymeric acid includes a highly fluorinated carbon backbone and side chains represented by the formula —(O—CF2CFRf)a—O—CF2CFR′fSO3X wherein Rf and R′f are independently selected from F, Cl or a perfluorinated alkyl group having 1 to 10 carbon atoms, a=0, 1 or 2, and X is H. ### Claim 10 (depends on 1) The composition of claim 1, wherein the additional material is a conductive polymer selected from the group consisting of polythiophenes, polyanilines, polyamines, polypyrroles, polyacetylenes, and combinations thereof. ### Claim 11 An organic electronic device having at least one active layer made from a stable colloid particle containing composition comprising a continuous liquid aqueous medium having dispersed therein a polydioxythiophene and at least one colloid-forming fluorinated polymeric acid, and further comprising an additional material selected from the group consisting of polymers, dyes, carbon nanotubes, metal nanowires, coating aids, organic and inorganic conductive inks and pastes, charge transport materials, crosslinking agents, and combinations thereof, wherein said polydioxythiophene has the structure: wherein: R1 and R′1 are each independently selected from hydrogen and alkyl having 1 to 4 carbon atoms, or R1 and R′1 taken together form an alkylene chain having 1 to 4 carbon atoms, which may optionally be substituted by alkyl or aromatic groups having 1 to 12 carbon atoms, or a 1,2-cyclohexylene radical, and n is greater than about 6; wherein the composition does not re-disperse in an aqueous medium after it has been dried.