Conductive material and substrate

Patent metadata

Field	Value
Publication number	US-10047237-B2
Application number	US-201615352975-A
Country	US
Kind code	B2
Filing date	Nov 16, 2016
Priority date	Dec 22, 2015
Publication date	Aug 14, 2018
Grant date	Aug 14, 2018

Abstract

The present invention provides a conductive material including: (A) a π-conjugated polymer, (B) a dopant polymer which contains one or more repeating units selected from “a1” to “a4” respectively shown by the following general formula (1) and has a weight-average molecular weight in the range of 1,000 to 500,000, and (C) one or more salts selected from the group consisting of a metal salt of carboxylic acid, a metal salt of β-diketone, a metal nitrate, a metal carbonate, a metal bicarbonate, a metal halide, and a metal hydroxide, with the metal being selected from the group consisting of cesium, rubidium, barium, and strontium. There can be provided a conductive material which is neutral and highly suitable for a printer, superior in film-formability, and also can form a conductive film having high transparency and conductivity, excellent flexibility and flatness when the film is formed from the material.

First claim

What is claimed is:

1. A conductive material comprising:
(A) a π-conjugated polymer,
(B) a dopant polymer which contains one or more repeating units shown by the following general formula (1) and has a weight-average molecular weight in the range of 1,000 to 500,000, and
(C) one or more salts selected from the group consisting of a metal salt of carboxylic acid, a metal salt of β-diketone, a metal nitrate, a metal carbonate, a metal bicarbonate, a metal halide, and a metal hydroxide, with the metal being selected from the group consisting of cesium, rubidium, barium, and strontium,

wherein R 1 , R 3 , R 5 , and R 8 independently represent a hydrogen atom or a methyl group; R 2 , R 4 , and R 6 independently represent a single bond, an ester group, or a linear, branched, or cyclic hydrocarbon group having 1 to 12 carbon atoms and optionally containing either or both of an ether group and an ester group; R 7 represents a linear or branched alkylene group having 1 to 4 carbon atoms in which 1 or 2 hydrogen atoms in R 7 are optionally substituted with a fluorine atom; R 9 represents a fluorine atom or a trifluoromethyl group; Z 1 , Z 2 , and Z 3 independently represent a single bond, a phenylene group, a naphthylene group, an ether group, or an ester group; Z 4 represents a single bond, an ether group, or an ester group; “Y” represents an oxygen atom or an NH group; “m” is an integer of 1 to 4; 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.

2. The conductive material 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.

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

4. The conductive material according to claim 3 , 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.

5. The conductive material according to claim 4 , wherein the component (C) is one or more salts selected from those shown by the following general formulae (3-1) to (3-4),

wherein “M” represents cesium or rubidium; “Q” represents barium or strontium; “p” is an integer of 1 to 6; when “p” is 1, R 10 represents a hydrogen atom, a linear, branched, or cyclic alkyl group having 1 to 30 carbon atoms, a linear, branched, or cyclic alkenyl group having 2 to 30 carbon atoms, a linear, branched, or cyclic alkynyl group having 2 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and R 10 optionally contains a halogen atom, a nitrogen atom, a hydroxy group, an ether group, an ester group, an amino group, an amide group, a carbamate group, a carbonate group, a sulfonate ester group, a thiol group, a sulfide group, a carbonyl group, a sulfonyl group, a lactone group, a lactam group, a sultone group, or a nitro group; when “p” is 2, R 10 represents a single bond, a linear, branched, or cyclic alkylene group having 1 to 30 carbon atoms, a linear, branched, or cyclic alkenylene group having 2 to 30 carbon atoms, a linear, branched, or cyclic alkynylene group having 2 to 30 carbon atoms, or an arylene group having 6 to 30 carbon atoms, and R 10 optionally contains a hydroxy group, an ether group, an amino group, a sulfide group, or a carbonyl group; when “p” is any of 3 to 6, R 10 represents a linear, branched, or cyclic saturated hydrocarbon group having 1 to 30 carbon atoms, a linear, branched, or cyclic unsaturated hydrocarbon group having 2 to 30 carbon atoms, or an aromatic hydrocarbon group having 6 to 30 carbon atoms, and R 10 optionally contains a halogen atom, a nitrogen atom, a hydroxy group, an ether group, an ester group, an amino group, an amide group, a carbamate group, a carbonate group, a sulfonate ester group, a thiol group, a lactone group, a lactam group, a sultone group, or a nitro group; R 11 and R 12 independently represent a linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and R 11 and R 12 optionally contain a hydroxy group, an alkoxy group, an ether group, an ester group, an amino group, an amide group, a sulfonate ester group, a halogen atom, a cyano group, a nitro group, a carbonate group, a carbamate group, a thiol group, a sulfide group, a thioketone group, or a heteroaromatic ring; and R 13 represents a hydrogen atom, a linear, branched, or cyclic alkyl group having 1 to 8 carbon atoms, or a phenyl group.

6. The conductive material according to claim 3 , wherein the component (C) is one or more salts selected from those shown by the following general formulae (3-1) to (3-4),

wherein “M” represents cesium or rubidium; “Q” represents barium or strontium; “p” is an integer of 1 to 6; when “p” is 1, R 10 represents a hydrogen atom, a linear, branched, or cyclic alkyl group having 1 to 30 carbon atoms, a linear, branched, or cyclic alkenyl group having 2 to 30 carbon atoms, a linear, branched, or cyclic alkynyl group having 2 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and R 10 optionally contains a halogen atom, a nitrogen atom, a hydroxy group, an ether group, an ester group, an amino group, an amide group, a carbamate group, a carbonate group, a sulfonate ester group, a thiol group, a sulfide group, a carbonyl group, a sulfonyl group, a lactone group, a lactam group, a sultone group, or a nitro group; when “p” is 2, R 10 represents a single bond, a linear, branched, or cyclic alkylene group having 1 to 30 carbon atoms, a linear, branched, or cyclic alkenylene group having 2 to 30 carbon atoms, a linear, branched, or cyclic alkynylene group having 2 to 30 carbon atoms, or an arylene group having 6 to 30 carbon atoms, and R 10 optionally contains a hydroxy group, an ether group, an amino group, a sulfide group, or a carbonyl group; when “p” is any of 3 to 6, R 10 represents a linear, branched, or cyclic saturated hydrocarbon group having 1 to 30 carbon atoms, a linear, branched, or cyclic unsaturated hydrocarbon group having 2 to 30 carbon atoms, or an aromatic hydrocarbon group having 6 to 30 carbon atoms, and R 10 optionally contains a halogen atom, a nitrogen atom, a hydroxy group, an ether group, an ester group, an amino group, an amide group, a carbamate group, a carbonate group, a sulfonate ester group, a thiol group, a lactone group, a lactam group, a sultone group, or a nitro group; R 11 and R 12 independently represent a linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and R 11 and R 12 optionally contain a hydroxy group, an alkoxy group, an ether group, an ester group, an amino group, an amide group, a sulfonate ester group, a halogen atom, a cyano group, a nitro group, a carbonate group, a carbamate group, a thiol group, a sulfide group, a thioketone group, or a heteroaromatic ring; and R 13 represents a hydrogen atom, a linear, branched, or cyclic alkyl group having 1 to 8 carbon atoms, or a phenyl gr

Assignees

• Shinetsu Chemical Co

Inventors

• Hatakeyama Jun
• Nagasawa Takayuki

Classifications

• C08F212/30

  Sulfur · CPC title

• C08F212/20

  Fluorine · CPC title

• C08F212/22

  Oxygen · CPC title

• C08F112/30

  Sulfur · CPC title

• C08F112/20

  Fluorine · CPC title