Conductive polymer composite comprising a sulfo group-containing dopant polymer

Patent metadata

Field	Value
Publication number	US-9601229-B2
Application number	US-201514803916-A
Country	US
Kind code	B2
Filing date	Jul 20, 2015
Priority date	Aug 28, 2014
Publication date	Mar 21, 2017
Grant date	Mar 21, 2017

Abstract

A conductive polymer composite including a π-conjugated polymer and a dopant polymer contain a repeating unit “a” represented by the following formula (1) and has a weight-average molecular weight with range of 1,000 to 500,000,

wherein R 1 represents a hydrogen atom or methyl group; R 2 represents a single bond, ether group, ester group, or a linear, branched, or cyclic hydrocarbon group having 1-12 carbon atoms and optionally containing an ether group and ester group; R 3 represents a linear or branched alkylene group having 1-4 carbon atoms wherein 1 or 2 hydrogen atoms in R 3 may be substituted with a fluorine atom; Z represents a phenylene group, naphthylene group, or ester group; and “a” is a number satisfying 0<a≦1.0. A conductive polymer composite has excellent filterability and film-formability by spin coating, and can form a conductive film having high transparency and flatness when film is formed from the composite.

First claim

What is claimed is:

1. A conductive polymer composite comprising:
(A) a π-conjugated polymer and
(B) a dopant polymer which contains a repeating unit “a” represented by the following general formula (1) and has a weight-average molecular weight in the range of 1,000 to 500,000,

wherein R 1 represents a hydrogen atom or a methyl group; R 2 represents a single bond, an ether group, 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 3 represents a linear or branched alkylene group having 1 to 4 carbon atoms in which 1 or 2 hydrogen atoms in R 3 are optionally substituted with a fluorine atom; Z represents a phenylene group, a naphthylene group, or an ester group; and “a” is a number satisfying 0<a≦1.0 representing a relative fractional amount of the repeating unit “a”.

2. The conductive polymer composite according to claim 1 , wherein the repeating unit “a” in the component (B) contains one or more repeating units selected from “a1” to “a4” respectively represented by the following general formulae (1-1) to (1-4),

wherein R 1-1 , R 1-2 , R 1-3 , and R 1-4 independently represent a hydrogen atom or a methyl group;
R 3-1 , R 3-2 , R 3-3 , and R 3-4 independently represent a linear or branched alkylene group having 1 to 4 carbon atoms in which 1 or 2 hydrogen atoms in R 3-1 , R 3-2 , R 3-3 , and R 3-4 are optionally independently substituted with a fluorine atom; 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 and each represent a relative fractional amount of their respective repeating units.

3. The conductive polymer composite according to claim 1 , wherein the component (B) further contains a repeating unit “b” represented by the following general formula (2),

wherein “b” is a number satisfying 0<b<1.0 representing a relative fractional amount of the repeating unit “b”.

4. The conductive polymer composite according to claim 2 , wherein the component (B) further contains a repeating unit “b” represented by the following general formula (2),

wherein “b” is a number satisfying 0<b<1.0 representing a relative fractional amount of the repeating unit “b”.

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

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

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

8. The conductive polymer composite according to claim 4 , wherein the component (B) is a block copolymer.

9. 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.

10. 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.

11. The conductive polymer composite 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.

12. The conductive polymer composite according to claim 4 , 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.

13. The conductive polymer composite according to claim 5 , 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.

14. The conductive polymer composite according to claim 6 , 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.

15. The conductive polymer composite according to claim 7 , 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.

16. The conductive polymer composite according to claim 8 , 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.

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

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

19. A substrate having a conductive film formed thereon by using the conductive polymer composite according to claim 1 .

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

Assignees

• Shinetsu Chemical Co

Inventors

• Hatakeyama Jun
• Hasegawa Koji
• Nagasawa Takayuki

Classifications

• C08F212/30

  Sulfur · CPC title

• C08F120/38

  Esters containing sulfur · CPC title

• C08F20/38

  Esters containing sulfur · CPC title

• C08F20/22

  Esters containing halogen · CPC title

• H01B1/125 Primary

  comprising aliphatic main chains, e.g. polyactylenes · CPC title