# US 9,437,345 B2 · Methods for fabricating and treating doped conjugated polymer film

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- Number: US 9,437,345 B2
- Document ID: US9437345B2
- Status: Granted
- Kind: B2
- Application number: 13/490,305
- Filed: 2012-06-06
- Published: 2013-05-02
- Granted: 2016-09-06
- Earliest claimed: 2011-10-28
- Assignees: National Central University
- Applicants: Chun-Guey Wu; Chien-Hung Chiang
- Inventors: Chun-Guey Wu; Chien-Hung Chiang
- Web page: https://patentgrep.com/patent/US9437345B2

## CPC

- H01B 1/127: {comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes}
- C08G 61/126: {with a five-membered ring containing one sulfur atom in the ring}
- C08G 73/0266: {Polyanilines or derivatives thereof}
- H01B 1/128: {comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes}
- 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 2261/3327: alkene-based
- C08G 2261/344: containing heteroatoms
- C08G 2261/51: Charge transport
- C08G 2261/794: with polymeric dopants
- 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})
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A method for fabricating a doped conjugated polymer film includes the steps of: mixing a polar substance, a polar solvent and a doped conjugated polymer to form a doped conjugated polymer solution, and forming a conjugated polymer film with the doped conjugated polymer solution. In addition, a method for treating a doped conjugated polymer film includes the steps of: providing a doped conjugated polymer film, and adding a mixed solution which contains a polar substance and a polar solvent to the doped conjugated polymer film. In these cases, the polar substance is selected from the group consisting of formula (1), formula (2), inorganic acids, benzene-containing organic acids, or their combinations. The polar solvent is selected from the group consisting of water, ethers, alcohols, sulfoxides, alcohol ethers, ketones, amines, nitriles, carboxylic acids, amides, or their combinations.

## Claims

### Claim 1

A method for fabricating a doped conjugated polymer film, comprising the steps of:
mixing a polar substance, a polar solvent and a doped conjugated polymer to form a doped conjugated polymer solution, wherein the polar substance is selected from the group consisting of formula (1), formula (2), inorganic acids, benzene-containing organic acids, or their combinations, and the polar solvent is selected from the group consisting of water, ethers, alcohols, sulfoxides, alcohol ethers, ketones, amines, nitriles, carboxylic acids, amides, or their combinations; and
forming the doped conjugated polymer film with the doped conjugated polymer solution,
wherein e of the formula (1) is an integral between 0 and 5, each of R1 to R8 of the formula (1) and R9 to R14 of the formula (2) is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, amino, formyl, carboxyl, OCjH2j+1, CjH2j+1, SCjH2j+1, N(CjH2j+1)2, CjH2j+1SO3H, or CjH2jPO3H2, and j is an integral between 0 and 8,
wherein at least one of R1 to R8 of the formula (1) or R9 to R14 of the formula (2) comprises at least one halogen,
wherein the doped conjugated polymer is selected from the group consisting of formulas (4) and (5), or their derivatives, copolymers, or combinations,
wherein n of the formulas (4) and (5) is an integral between 3 and 5000, each of R1 to R6 of the formulas (4) and (5) is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, amino, formyl, carboxyl, OCjH2j+1, CjH2j+1, SCjH2j+1, N(CjH2j+1)2, CjH2j+1SO3H, or CjH2jPO3H2, j is an integral between 0 and 8, p of the formula (4) is an integral between 1 and 3, m of the formulas (4) and (5) is an integral between −5000 and 5000, a of the formulas (3) to (5) is an integral between 5000 and −5000, and Aa of the formulas (4) and (5) is an organic cation, an organic anion, an inorganic cation, an inorganic anion, or an ionic polymer.

### Claim 2 (depends on 1)

The method of claim 1, wherein the mixing step is to mix the polar solvent and the doped conjugated polymer, and then to add the polar substance.

### Claim 3 (depends on 1)

The method of claim 1, wherein the concentration of the doped conjugated polymer is between 0.1 and 30 weight %.

### Claim 4 (depends on 1)

The method of claim 1, wherein the concentration of the polar substance is between 0.001 and 50 weight %.

### Claim 5 (depends on 1)

The method of claim 1, wherein the polar substance is selected from the group consisting of hexafluoroisopropanol, 1,1,1,3,3,3-hexafluoro-2-phenyl-2-propanol, 1,1,1,3,3,3-hexafluoro-2-(p-tolyl)-propanol, heptafluoroisopropyl iodide, tetrafluoropropanol, pentafluoropropanol, hexafluoropropanol, 1H,1H,3H-hexafluoro-2-butanol, nonafluorovaleric acid, perfluorohexenoic acid, hexafluoro benzene, perfluoropropane, sulfuric acid, hydrochloric acid, perchloric acid, nitric acid, benzoic acid, and their combinations.

### Claim 6 (depends on 1)

The method of claim 1, wherein the polar solvent is selected from the group consisting of: water, ethyl ether, ethyl propyl ether, propyl ether, diisopropyl ether, dibutyl ether, methyl tert-butyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, benzyl methyl ether, isochroman, 2-phenylethylmethyl ether, n-butyl ethyl ether, 1,2-diethoxyethane, sec-butyl ether, isodibutyl ether, ethyl n-propyl ether, ethyl isopropyl ether, n-hexyl methyl ether, n-butyl methyl ether, methyl n-propyl ether, methanol, ethanol, ethylene glycol, 1-propanol, 2-propanol (isopropanol), glycerol, 1-butanol, 2-butanol, 2-methyl-1-propanol (isobutanol), 2-methyl-2-propanol (tert-butanol), 1-pentanol, 2-pentanol, 3-pentanol, 2,2-dimethyl-1-propanol, 1-hexanol, cyclopentanol, 3-methyl-1-butanol, 3-methyl-2-butanol, 2-methyl-1-butanol, 3-hexanol, 2-hexanol, 4-methyl-2-pentanol, 2-methyl-1-butanol, 2,2-dimethyl-1-propanol, 3-hexanol, 2-hexanol, 4-methyl-2-pentanol, 2-methyl-1-pentanol, 2-ethyl butanol, 2,4-dimethyl-3-pentanol, 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 2-ethyl-1-hexanol, 2,6-dimethyl-4-heptanol, 2-dimethyl cyclohexanol, 3-dimethyl cyclohexanol, 4-dimethyl cyclohexanol, 2-butoxyethanol, 1-methoxy-2-propanol, 2-methoxyethanol, 2-ethoxyethanol, 1-methoxy-2-butanol, ethylene glycol monopropyl ether, 1-ethoxy-2-propanol, 3-methoxy-1-butanol, ethylene glycol monoisobutyl ether, ethylene glycol mono-n-butyl ether, 3-methoxy-3-methyl butanol, ethylene glycol mono-tert-butyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, isopropyl ketone, 2-pentanone, 3-pentanone, 3-hexanone, diisopropanone, 2-dihexanone, cyclopentanone, 4-heptanone, isoamyl ketone, 3-heptanone, 2-heptanone, 4-methoxy-4-methyl-2-pentanone, 5-methyl-3-heptanone, 2-methyl cyclohexanone, diisobutyl ketone, 5-methyl-2-octanone, 3-methyl cyclohexanone, 2-cyclohexene-1-one, 4-methyl cyclohexanone, cycloheptanone, 4-tert-butyl cyclohexanone, isophorone, benzylacetone, acetonitrile, acrylonitrile, trichloroacetonitrile, propionitrile, neo-pentanenitrile, isobutyronitrile, n-butyronitrile, methoxyacetonitrile, 2-methylbutyronitrile, isopentanenitrile, n-pentanenitrile, n-hexanenitrile, 3-methoxypropionitrile, 3-ethoxypropionitrile, 3,3-oxydipropionitrile, n-heptanenitrile, glycolonitrile, benzonitrile, ethylene cyanohydrin, butanedinitrile, acetone cyanohydrin, 3-n-butoxypropionitrile, dimethyl sulfoxide, dibutyl sulfoxide, methyl phenyl sulfoxide, dimethylformamide, dimethylacetamide, acrylamide, 2-acetamidoethanol, N,N-dimethyl-n-benzylformamide, trifluoroacetamide, N,N-dimethylformamide, N,N-diethyl lauroylamide, ε-caprolactam, N,N-dimethyl ethylamide, N-tert-butylformamide, formamide, neo-pentanamide, N-butyramide, N,N-dimethylacetylacetamide, N-methylformamide, N,N-diethylformamide, N-carbonylethylamine, acetamine, N,N-diisopropylformamine, 1-formylpiperidine, N-methyl-N-formylaniline, monoalkylamine, dialkylamine, trialkylamine, cycloamine, aromatic amine, C6 carboxylic acid, and their combinations.