# US 12,009,115 B2 · Conductor material > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,009,115 B2 - Document ID: US12009115B2 - Status: Granted - Kind: B2 - Application number: 17/922,108 - Filed: 2021-04-27 - Published: 2023-06-01 - Granted: 2024-06-11 - Earliest claimed: 2020-05-01 - Assignees: The University of Tokyo; Daicel Corporation - Applicants: The University of Tokyo; Daicel Corporation - Inventors: Toshihiro Okamoto; Tadanori Kurosawa; Yu Yamashita; Junichi Takeya; Daiji Ikeda; Takeshi Yokoo; Yasuyuki Akai - Web page: https://patentgrep.com/patent/US12009115B2 ## CPC - H01B 1/127: {comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes} - 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}) ## Abstract Provided is a conductor material having high conductivity. The conductor material according to an embodiment of the present disclosure has a configuration in which a conjugated polymeric compound having an electron donating group containing a heteroatom in a side chain is doped with a dopant containing an anion selected from a nitrogen anion, a boron anion, a phosphorus anion and an antimony anion, and a counter cation. The anion is preferably an anion represented by Formula (1) below: where R1 and R2 are identical or different, and each represent an electron withdrawing group; and R1 and R2 may be bonded to each other to form a ring with an adjacent nitrogen atom. ## Claims ### Claim 1 A conductor material having a configuration in which a conjugated polymeric compound having an electron donating group containing a heteroatom in a side chain is doped with a dopant containing an anion selected from a nitrogen anion, a boron anion, a phosphorus anion and an antimony anion, and a counter cation, wherein the conjugated polymeric compound is a polymeric compound having a thienothiophene ring. ### Claim 2 (depends on 1) The conductor material according to claim 1, wherein the anion is represented by Formula (1): wherein R1 and R2 are identical or different, and each represent an electron withdrawing group; and R1 and R2 may be bonded to each other to form a ring with an adjacent nitrogen atom. ### Claim 3 (depends on 1) The conductor material according to claim 1, wherein the anion is represented by Formula (1a): wherein R3 and R4 are identical or different, and each represent a halogen atom or a haloalkyl group; and R3 and R4 may be bonded to each other to form a haloalkylene group. ### Claim 4 (depends on 1) The conductor material according to claim 1, wherein the conjugated polymeric compound is a polymeric compound having a repeating unit represented by Formula (2) wherein L1 and L4 are identical or different, and each represent an element of Groups 13 to 16; L2 and L3 each represent a sulfur atom; and D1 to D4 are identical or different, and each represent an electron donating group containing a heteroatom, or a hydrogen atom, provided that at least one of D1 to D4 is an electron donating group containing a heteroatom. ### Claim 5 (depends on 1) The conductor material according to claim 1, wherein the electron donating group containing a heteroatom is a group represented by Formula (d): wherein D represents at least one heteroatom selected from elements of Groups 14 to 16; R5 represents an aliphatic hydrocarbon group having from 5 to 30 carbon atoms; and a bond indicated by a wavy line in the formula is bonded to a backbone of the conjugated polymeric compound. ### Claim 6 (depends on 1) An electronic device comprising the conductor material described in claim 1. ### Claim 7 A conductor material having a configuration in which a conjugated polymeric compound having an electron donating group containing a heteroatom in a side chain is doped with a dopant containing an anion and a counter cation, wherein the anion is represented by Formula (1a): wherein R3 and R4 are identical or different, and each represent a halogen atom or a haloalkyl group; and R3 and R4 may be bonded to each other to form a haloalkylene group. ### Claim 8 A conductor material having a configuration in which a conjugated polymeric compound is doped with a dopant, wherein the conjugated polymeric compound is a polymeric compound having a repeating unit represented by Formula (2): wherein L1 to L4 are identical or different, and each represent an element of Groups 13 to 16; and D1 to D4 are identical or different, and each represent an electron donating group containing a heteroatom, or a hydrogen atom, provided that at least one of D1 to D4 is an electron donating group containing a heteroatom; and the dopant is a dopant containing an anion selected from a nitrogen anion, a boron anion, a phosphorus anion and an antimony anion, and a counter cation. ### Claim 9 A conductor material having a configuration in which a conjugated polymeric compound having an electron donating group containing a heteroatom in a side chain is doped with a dopant containing an anion selected from a nitrogen anion, a boron anion, a phosphorus anion and an antimony anion, and a counter cation, wherein the conductor material is a p-type conductor material. ### Claim 10 A conductor material having a configuration in which a conjugated polymeric compound having an electron donating group containing a heteroatom in a side chain is doped with a dopant containing an anion selected from a nitrogen anion, a boron anion, a phosphorus anion and an antimony anion, and a counter cation, wherein a conductivity of the conductor material is 250 S/cm or greater, the conductivity being measured under the following measurement conditions: film thickness of the conductor material: 64.3 nm; sweeping voltage: from −0.1 to 0.1 V (0.01 V/step); wiring width: 612 μm; and channel length: 500 μm. ### Claim 11 A conductor material having a configuration in which a conjugated polymeric compound having an electron donating group containing a heteroatom in a side chain is doped with a dopant containing an anion selected from a nitrogen anion, a boron anion, a phosphorus anion and an antimony anion, and a counter cation, wherein a conductivity of the conductor material is 250 S/cm or greater, and a ratio of decrease in conductivity when the conductor material is stored at 25° C. for 14 days is 5% or less, the conductivity being measured under the following measurement conditions: film thickness of the conductor material: 64.3 nm; sweeping voltage: from −0.1 to 0.1 V (0.01 V/step); wiring width: 612 μm; and channel length: 500 μm. ### Claim 12 A conductor material having a configuration in which a conjugated polymeric compound having an electron donating group containing a heteroatom in a side chain is doped with a dopant containing an anion selected from a nitrogen anion, a boron anion, a phosphorus anion and an antimony anion, and a counter cation, wherein a ratio of decrease in conductivity when the conductor material is stored at 25° C. for 14 days is 5% or less, and a ratio of decrease in conductivity when the conductor material is stored at 25° C. for 56 days is 20% or less. ### Claim 13 A conductor material having a configuration in which a conjugated polymeric compound having an electron donating group containing a heteroatom in a side chain is doped with a dopant containing an anion selected from a nitrogen anion, a boron anion, a phosphorus anion and an antimony anion, and a counter cation, wherein the conjugated polymeric compound is a polymeric compound having a repeating unit represented by Formula (2b): wherein L1 to L4 each represent a sulfur atom; D1 to D4 are identical or different, and each represent a group represented by Formula (d) or a hydrogen atom, provided that at least one of D1 to D4 is a group represented by Formula (d): wherein D represents an oxygen atom; and R5 represents an alkyl group having from 10 to 20 carbon atoms. ### Claim 14 (depends on 1) A method for producing a conductor material, the method comprising doping a conjugated polymeric compound having an electron donating group containing a heteroatom in a side chain with a dopant containing an anion selected from a nitrogen anion, a boron anion, a phosphorus anion and an antimony anion, and a counter cation, to produce the conductor material described in claim 1, wherein the conjugated polymeric compound is a polymeric compound having a thienothiophene ring. ### Claim 15 (depends on 14) The method for producing a conductor material according to claim 14, wherein the anion is represented by Formula (1): wherein R1 and R2 are identical or different, and each represent an electron withdrawing group; and R1 and R2 may be bonded to each other to form a ring with an adjacent nitrogen atom. ### Claim 16 (depends on 14) The method for producing a conductor material according to claim 14, wherein the anion is represented by Formula (1a): wherein R3 and R4 are identical or different, and each represent a halogen atom or a haloalkyl group; and R3 and R4 may be bonded to each other to form a haloalkylene group. ### Claim 17 (depends on 14) The method for producing a conductor material according to claim 14, wherein the conjugated polymeric compound is a polymeric compound having a repeating unit represented by Formula (2): wherein L1 and L4 are identical or different, and each represent an element of Groups 13 to 16; L2 and L3 each represent a sulfur atom; and D1 to D4 are identical or different, and each represent an electron donating group containing a heteroatom, or a hydrogen atom, provided that at least one of D1 to D4 is an electron donating group containing a heteroatom. ### Claim 18 (depends on 14) The method for producing a conductor material according to claim 14, wherein the electron donating group containing a heteroatom is a group represented by Formula (d): wherein D represents at least one heteroatom selected from elements of Groups 14 to 16; R5 represents an aliphatic hydrocarbon group having from 5 to 30 carbon atoms; and a bond indicated by a wavy line in the formula is bonded to a backbone of the conjugated polymeric compound. ### Claim 19 (depends on 14) The method for producing a conductor material according to claim 14, wherein the counter cation contained in the dopant is a radical cation represented by Formula (3): wherein R11 to R13 are identical or different, and each represent a monovalent aromatic group or a group represented by Formula (r); and n represents valence of the radical cation and is equal to the number (n) of nitrogen atoms in the formula: wherein Ar1, Ar2, and Ar3 are identical or different, and each represent a divalent aromatic group; Ar4, Ar5, Ar6, and Ar7 are identical or different, and each represent a monovalent aromatic group which may have a substituent represented by Formula (sb); s and t are identical or different, and each represent an integer of 0 or more; and a bond indicated by a wavy line in the formula is bonded to the nitrogen atom in Formula (3), wherein Ar8 and Ar9 are identical or different, and each represent a divalent aromatic group; Ar10, Ar11, Ar12, and Ar13 are identical or different, and each represent a monovalent aromatic group; u and v are identical or different, and each represent an integer of 0 or more; and a bond indicated by a wavy line in the formula is bonded to the monovalent aromatic group.