# US 9,752,045 B2 · Conductive polymer composite and substrate

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- Number: US 9,752,045 B2
- Document ID: US9752045B2
- Status: Granted
- Kind: B2
- Application number: 15/225,221
- Filed: 2016-08-01
- Published: 2017-03-02
- Granted: 2017-09-05
- Earliest claimed: 2015-08-25
- Assignees: Shin-Etsu Chemical Co., Ltd.
- Applicants: Shin-Etsu Chemical Co., Ltd.
- Inventors: Jun Hatakeyama; Takayuki Nagasawa; Koji Hasegawa
- Web page: https://patentgrep.com/patent/US9752045B2

## CPC

- C09D 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C08F 12/20: Fluorine
- C08F 12/22: Oxygen
- C08F 12/30: Sulfur
- C08F 20/28: containing no aromatic rings in the alcohol moiety
- C08F 20/38: Esters containing sulfur
- C08F 22/24: Esters containing sulfur
- C08F 212/20: {Fluorine}
- C08F 212/22: {Oxygen}
- C08F 212/30: {Sulfur}
- C08L 33/14: of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- C08L 35/02: Homopolymers or copolymers of esters (C08L35/06, C08L35/08 take precedence)
- C09D 5/24: Electrically-conducting paints {(conductive materials H01B1/00)}
- C09D 7/65: macromolecular (C09D7/41-C09D7/48 take precedence)
- C09D 125/18: Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
- C09D 135/02: Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence)
- H01B 1/12: organic substances {(organic macromolecular compounds or compositions C08)}
- H01B 1/125: {comprising aliphatic main chains, e.g. polyactylenes}
- H01B 1/127: {comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes}
- H10K 30/82: Transparent electrodes, e.g. indium tin oxide [ITO] electrodes
- C08F 12/24: Phenols or alcohols
- C08F 212/24: {Phenols or alcohols}
- C08F 2500/04: Broad molecular weight distribution, i.e. Mw/Mn > 6
- C08F 2500/26: Use as polymer for film forming
- C08L 2201/10: Transparent films; Clear coatings; Transparent materials
- C08L 2203/16: used for films
- C08L 2203/20: use in electrical or conductive gadgets
- H10K 85/113: {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene}
- Y02E 10/549: Organic PV cells
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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

The present invention provides a conductive polymer composite including: (A) a π-conjugated polymer, and (B) a dopant polymer which contains a repeating unit “a” shown by the following general formula (1) and having a weight-average molecular weight in the range of 1,000 to 500,000. There can be provided a conductive polymer composite which has excellent filterability and film-formability by spin coating, and can form a conductive film having high transparency and excellent flatness. wherein R1 represents a hydrogen atom or a methyl group; R2 represents any of a single bond, an ester group, and a linear, branched, or cyclic hydrocarbon group having 1 to 12 carbon atoms, the hydrocarbon group optionally containing an ether group, an ester group, or both; “Z” represents any of a single bond, a phenylene group, a naphthylene group, an ether group, and an ester group; and “a” is a number satisfying 0<a≦1.0.

## Claims

### Claim 1

A conductive polymer composite comprising:
(A) a π-conjugated polymer, and
(B) a dopant polymer which contains a repeating unit shown by the following general formula (1) and having a weight-average molecular weight in the range of 1,000 to 500,000,
wherein R1 represents a hydrogen atom or a methyl group; R2 represents any of a single bond, an ester group, and a linear, branched, or cyclic hydrocarbon group having 1 to 12 carbon atoms, the hydrocarbon group optionally containing either or both of an ether group and an ester group; “Z” represents any of a single bond, a phenylene group, a naphthylene group, an ether group, and an ester group; and “a” is a number satisfying 0<a≦1.0.

### Claim 2 (depends on 1)

The conductive polymer composite according to claim 1, wherein the repeating unit shown by the general formula (1) in the component (B) includes one or more kinds selected from repeating units respectively shown by the following general formulae (1-1) to (1-4),
wherein R1 has the same meaning as defined above; and a1, a2, a3, and a4 are each a number satisfying 0≦a1≦1.0, 0≦a2≦1.0, 0≦a3≦1.0, 0≦a4≦1.0, and 0<a1+a2+a3+a4≦1.0.

### Claim 3 (depends on 2)

The conductive polymer composite according to claim 2, wherein the component (B) further contains a repeating unit shown by the following general formula (2),
wherein “b” is a number satisfying 0<b<1.0.

### Claim 4 (depends on 3)

The conductive polymer composite according to claim 3, wherein the component (B) is a block copolymer.

### Claim 5 (depends on 2)

The conductive polymer composite according to claim 2, wherein the component (B) is a block copolymer.

### Claim 6 (depends on 2)

The conductive polymer composite according to claim 2, wherein the component (A) is a polymer formed by polymerization of one or more precursor monomers selected from the group consisting of pyrrole, thiophene, selenophene, tellurophene, aniline, a polycyclic aromatic compound, and a derivative thereof.

### Claim 7 (depends on 2)

The conductive polymer composite according to claim 2, wherein the conductive polymer composite has dispersibility in water or in an organic solvent.

### Claim 8 (depends on 2)

A substrate having a conductive film formed thereon, wherein the conductive film is formed from the conductive polymer composite according to claim 2.

### Claim 9 (depends on 1)

The conductive polymer composite according to claim 1, wherein the component (B) further contains a repeating unit shown by the following general formula (2),
wherein “b” is a number satisfying 0<b<1.0.

### Claim 10 (depends on 9)

The conductive polymer composite according to claim 9, wherein the component (B) is a block copolymer.

### Claim 11 (depends on 9)

The conductive polymer composite according to claim 9, wherein the component (A) is a polymer formed by polymerization of one or more precursor monomers selected from the group consisting of pyrrole, thiophene, selenophene, tellurophene, aniline, a polycyclic aromatic compound, and a derivative thereof.

### Claim 12 (depends on 9)

The conductive polymer composite according to claim 9, wherein the conductive polymer composite has dispersibility in water or in an organic solvent.

### Claim 13 (depends on 9)

A substrate having a conductive film formed thereon, wherein the conductive film is formed from the conductive polymer composite according to claim 9.

### Claim 14 (depends on 1)

The conductive polymer composite according to claim 1, wherein the component (B) is a block copolymer.

### Claim 15 (depends on 14)

The conductive polymer composite according to claim 14, wherein the component (A) is a polymer formed by polymerization of one or more precursor monomers selected from the group consisting of pyrrole, thiophene, selenophene, tellurophene, aniline, a polycyclic aromatic compound, and a derivative thereof.

### Claim 16 (depends on 14)

The conductive polymer composite according to claim 14, wherein the conductive polymer composite has dispersibility in water or in an organic solvent.

### Claim 17 (depends on 1)

The conductive polymer composite according to claim 1, wherein the component (A) is a polymer formed by polymerization of one or more precursor monomers selected from the group consisting of pyrrole, thiophene, selenophene, tellurophene, aniline, a polycyclic aromatic compound, and a derivative thereof.

### Claim 18 (depends on 1)

The conductive polymer composite according to claim 1, wherein the conductive polymer composite has dispersibility in water or in an organic solvent.

### Claim 19 (depends on 1)

A substrate having a conductive film formed thereon, wherein the conductive film is formed from the conductive polymer composite according to claim 1.

### Claim 20 (depends on 19)

The substrate according to claim 19, wherein the conductive film functions as a transparent electrode layer.