Dopant and conductor material

Patent metadata

Field	Value
Publication number	US-12049540-B2
Application number	US-202117917491-A
Country	US
Kind code	B2
Filing date	Apr 15, 2021
Priority date	Apr 17, 2020
Publication date	Jul 30, 2024
Grant date	Jul 30, 2024

Abstract

Provided is a dopant with which a conductor material having high electrical conductivity can be formed. The present disclosure relates to a dopant containing a radical cation represented by Formula (1) and a counter anion. In Formula (1), R 1 to R 3 may be the same or different, and each denotes a monovalent aromatic group or a group represented by Formula (r). at least one of R 1 to R 3 is a group represented by Formula (r), and n indicates the valence of the radical cation and is equal to the quantity (n) of nitrogen atoms in the formula. In Formula (r), Ar 1 , Ar 2 , and Ar 3 may be the same or different, and each denotes a divalent aromatic group, and Ar 4 , Ar 5 , Ar 6 , and Ar 7 may be the same or different, and each denotes a monovalent aromatic group optionally having a substituent represented by Formula (sb) below. Furthermore, m and n may be the same or different, and each represents an integer of 0 or greater.

First claim

The invention claimed is:

1. A dopant comprising a radical cation represented by Formula (1) and a counter anion:

where R 1 to R 3 may be the same or different, and each denotes a monovalent aromatic group or a group represented by Formula (r), at least one of R 1 to R 3 is a group represented by Formula (r), and n indicates a valence of the radical cation and is equal to a quantity (n) of nitrogen atoms in the formula;

where Ar 1 denotes a divalent aromatic group comprising a structure represented by Formula (ar-3):

 and
Ar 2 and Ar 3 may be the same or different, and each denotes a divalent aromatic group, and Ar 4 , Ar 5 , Ar 6 , and Ar 7 may be the same or different, and each denotes a monovalent aromatic group optionally having a substituent represented by Formula (sb), m and n may be the same or different and each represents an integer of 0 or greater, and a bond indicated by a wavy line in Formula (r) bonds to the nitrogen atom in Formula (1); and

where Ar 8 and Ar 9 may be the same or different, and each denotes a divalent aromatic group, Ar 10 , Ar 11 , Ar 12 , and Ar 13 may be the same or different, and each denotes a monovalent aromatic group, s and t may be the same or different, and each represents an integer of 0 or greater, and a bond indicated by a wavy line in Formula (sb) is bonded to the monovalent aromatic group.

2. The dopant according to claim 1 , wherein the counter anion is a nitrogen anion, a boron anion, a phosphorus anion, or an antimony anion.

3. The dopant according to claim 1 , wherein the counter anion is an anion represented by Formula (2):

where R 6 and R 7 may be the same or different, and each denotes an electron-withdrawing group, and R 6 and R 7 may bond with each other and form a ring together with the adjacent nitrogen atom.

4. The dopant according to claim 1 , wherein the counter anion is an anion represented by Formula (2a):

where R 8 and R 9 may be the same or different and denote a halogen atom or a haloalkyl group, and R 8 and R 9 may be bonded together to form a haloalkylene group.

5. A conductor material having a configuration in which a conjugated polymer compound is doped with a dopant, wherein the dopant comprises a radical cation represented by Formula (1) and a counter anion:

where R 1 to R 3 may be the same or different, and each denotes a monovalent aromatic group or a group represented by Formula (r), at least one of R 1 to R 3 is a group represented by Formula (r), and n indicates a valence of the radical cation and is equal to a quantity (n) of nitrogen atoms in the formula;

where Ar 1 , Ar 2 , and Ar 3 may be the same or different, and each denotes a divalent aromatic group, and Ar 4 , Ar 5 , Ar 6 , and Ar 7 may be the same or different, and each denotes a monovalent aromatic group optionally having a substituent represented by Formula (sb), m and n may be the same or different and each represents an integer of 0 or greater, and a bond indicated by a wavy line in Formula (r) bonds to the nitrogen atom in Formula (1); and

where Ar 8 and Ar 9 may be the same or different, and each denotes a divalent aromatic group, Ar 10 , Ar 11 , Ar 12 , and Ar 13 may be the same or different, and each denotes a monovalent aromatic group, s and t may be the same or different, and each represents an integer of 0 or greater, and a bond indicated by a wavy line in Formula (sb) is bonded to the monovalent aromatic group.

6. An electronic device comprising the conductor material described in claim 5 .

7. The conductor material according to claim 5 , wherein the conjugated polymer compound is a π-conjugated polymer compound.

8. The conductor material according to claim 5 , wherein the conjugated polymer compound is a heterocyclic conjugated polymer compound.

9. The conductor material according to claim 5 , wherein the conjugated polymer compound is a heterocyclic conjugated polymer compound containing a nitrogen atom or a sulfur atom as a heteroatom.

10. The conductor material according to claim 5 , wherein the conjugated polymer compound is a conjugated polymer compound containing a thiophene ring structure.

11. The conductor material according to claim 5 , wherein the conjugated polymer compound is a polymer compound having a repeating unit represented by Formula (3):

where R a to R d may be the same or different, and each denotes a hydrogen atom or an alkyl group having from 6 to 18 carbons.

12. The conductor material according to claim 5 , wherein the electrical conductivity is 500 S/cm or higher.

13. The conductor material according to claim 5 , wherein the counter anion is a nitrogen anion, a boron anion, a phosphorus anion, or an antimony anion.

14. The conductor material according to claim 5 , wherein the counter anion is an anion represented by Formula (2):

where R 6 and R 7 may be the same or different, and each denotes an electron-withdrawing group, and R 6 and R 7 may bond with each other and form a ring together with the adjacent nitrogen atom.

15. The conductor material according to claim 5 , wherein the counter anion is an anion represented by Formula (2a):

where R 8 and R 9 may be the same or different and denote a halogen atom or a haloalkyl group, and R 8 and R 9 may be bonded together to form a haloalkylene group.

16. A method for producing a conductor material, the method comprising doping a conjugated polymer compound with a dopant to produce a conductor material having a configuration in which the conjugated polymer compound is doped with the dopant, wherein the dopant comprises a radical cation represented by Formula (1) and a counter anion:

where R 1 to R 3 may be the same or different, and each denotes a monovalent aromatic group or a group represented by Formula (r), at least one of R 1 to R 3 is a group represented by Formula (r), and n indicates a valence of the radical cation and is equal to a quantity (n) of nitrogen atoms in the formula;

where Ar 1 , Ar 2 , and Ar 3 may be the same or different, and each denotes a divalent aromatic group, and Ar 4 , Ar 5 ,

Assignees

• Univ Tokyo
• Daicel Corp

Inventors

• Okamoto Toshihiro
• KUROSAWA Tadanori
• Takeya Junichi
• Ikeda Daiji
• Yokoo Takeshi
• Akai Yasuyuki

Classifications

• H01B1/12

  organic substances {(organic macromolecular compounds or compositions C08)} · CPC title

• C08K5/18

  with aromatically bound amino groups · CPC title

• H10K85/113

  Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene · CPC title

• H10K85/631 Primary

  Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine · CPC title

• H01B1/122

  Ionic conductors · CPC title