# US 12,604,600 B2 · Organic electroluminescent element and novel iridium complex > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,604,600 B2 - Document ID: US12604600B2 - Status: Granted - Kind: B2 - Application number: 18/174,983 - Filed: 2023-02-27 - Published: 2023-07-06 - Granted: 2026-04-14 - Earliest claimed: 2011-09-30 - Assignees: UDC Ireland Limited - Applicants: Udc Ireland Limited - Inventors: Kousuke Watanabe; Yuichirou Itai - Web page: https://patentgrep.com/patent/US12604600B2 ## CPC - H10K 50/11: characterised by the electroluminescent [EL] layers - C07F 15/0033: {Iridium compounds} - C09K 11/06: containing organic luminescent materials - H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} - H10K 85/342: {comprising iridium} - H10K 85/652: {Cyanine dyes} - C09K 2211/1007: Non-condensed systems - C09K 2211/1029: containing one nitrogen atom as the heteroatom - C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd - H10K 2101/10: Triplet emission - H10K 2102/302: {of OLED structures} - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL ## Abstract An iridium complex which has a phenylpyridine bidentate ligand containing a group represented by the following general formula (A): (In the general formula (A), X represents a cyano group or a halogenated alkyl group. L represents a single bond or a divalent linking group. R represents a substituent. n represents an integer of 0 to 4. * represents a binding site to a phenylpyridine bidentate ligand.) ## Claims ### Claim 1 A compound represented by the following General Formula (1) wherein R111 to R134 each independently represent a hydrogen atom or a substituent; at least two adjacent groups out of R112 to R114, R114 and R115, at least two adjacent groups out of R115 to R118, at least two adjacent groups out of R120 to R122, R122 and R123, at least two adjacent groups out of R123 to R126, at least two adjacent groups out of R128 to R130, R130 and R131, or at least two adjacent groups out of R131 to R134 may be bonded to each other to form a ring, provided that one of R127 to R134 comprises a group represented by the following General Formula (A), and the number of the groups out of R111 to R134 in General Formula (1) which comprises a group represented by General Formula (A) is 1: X represents a cyano group; L represents a single bond or a divalent linking group; n represents an integer of 0 to 4; * represents a binding site; and R represents a substituent, wherein when a plurality of R's are present, they may be the same as or different from each other; wherein the compound is heteroleptic. ### Claim 2 (depends on 1) The compound of claim 1, wherein the compound represented by the General Formula (1) is a compound represented by the following General Formula (2): wherein R111 to R123, R125, R126, and R211 to R215 each independently represent a hydrogen atom or a substituent; two groups out of R111 to R118 may be each the same as or different from each other, at least two adjacent groups out of R112 to R114, R114 and R115, at least two adjacent groups out of R115 to R118, or at least two adjacent groups out of R120 to R122, R122 and R123, R125 and R126 may be bonded to each other to form a ring; L represents a single bond or a divalent linking group, provided that at least one of R211 to R215 represents a cyano group. ### Claim 3 (depends on 1) The compound of claim 1, wherein the compound represented by the General Formula (1) is a compound represented by the following General Formula (4): wherein R111 to R120, R122 to R126, and R411 to R415 each independently represent a hydrogen atom or a substituent; two groups out of R111 to R118 may be each the same as or different from each other; at least two adjacent groups out of R112 to R114, R114 and R115, at least two adjacent groups out of R115 to R118, R122 and R123, or at least two adjacent groups out of R123 to R126 may be bonded to each other to form a ring; L represents a single bond or a divalent linking group, provided that at least one of R411 to R415 represents a cyano group. ### Claim 4 (depends on 1) The compound of claim 1, wherein the compound represented by the General Formula (1) is a compound represented by the following General Formula (6): wherein R111 to R124, R126, and R611 to R615 each independently represent a hydrogen atom or a substituent; two groups out of R111 to R118 may be each the same as or different from each other; at least two adjacent groups out of R112 to R114, R114 and R115, at least two adjacent groups out of R115 to R118, or at least two adjacent groups out of R120 to R122, R122 and R123, R123 and R124 may be bonded to each other to form a ring; L represents a single bond or a divalent linking group, provided that at least one of R611 to R615 represents a cyano group. ### Claim 5 (depends on 1) The compound of claim 1, wherein L represents a single bond. ### Claim 6 (depends on 1) The compound of claim 1, wherein L represents a divalent linking group. ### Claim 7 (depends on 1) The compound of claim 1, wherein R131 represents a group represented by the General Formula (A). ### Claim 8 (depends on 1) The compound of claim 1, wherein R132 represents a group represented by the General Formula (A). ### Claim 9 (depends on 1) The compound of claim 1, wherein R133 represents a group represented by the General Formula (A). ### Claim 10 (depends on 1) The compound of claim 1, wherein X in General Formula (A) is para to L. ### Claim 11 (depends on 1) The compound of claim 1, wherein X in General Formula (A) is meta to L. ### Claim 12 (depends on 1) The compound of claim 1, wherein X in General Formula (A) is ortho to L. ### Claim 13 (depends on 1) The compound of claim 1, wherein at least two adjacent groups out of R112 to R114, R114 and R115, at least two adjacent groups out of R115 to R118, at least two adjacent groups out of R120 to R122, R122 and R123, at least two adjacent groups out of R123 to R126, at least two adjacent groups out of R128 to R130, R130 and R131, or at least two adjacent groups out of R131 to R134 are bonded to each other to form a ring. ### Claim 14 A compound represented by the following General Formula (1): wherein R111 to R134 each independently represent a hydrogen atom or a substituent; at least two adjacent groups out of R112 to R114, R114 and R115, at least two adjacent groups out of R115 to R118, at least two adjacent groups out of R120 to R122, R122 and R123, at least two adjacent groups out of R123 to R126, at least two adjacent groups out of R128 to R130, R130 and R131, or at least two adjacent groups out of R131 to R134 may be bonded to each other to form a ring, provided that one of R131 to R134 comprises a group represented by the following General Formula (A), and the number of the groups out of R111 to R134 in the general formula (1) which comprises a group represented by General Formula (A) is 1: X represents a cyano group; L represents a single bond or a divalent linking group; n represents an integer of 0 to 4; * represents a binding site; and R represents a substituent, wherein when a plurality of R's are present, they may be the same as or different from each other; wherein the compound is heteroleptic. ### Claim 15 (depends on 14) The compound of claim 14, wherein L represents a single bond. ### Claim 16 (depends on 14) The compound of claim 14, wherein L represents a divalent linking group. ### Claim 17 (depends on 14) The compound of claim 14, wherein R131 represents a group represented by the General Formula (A). ### Claim 18 (depends on 14) The compound of claim 14, wherein R132 represents a group represented by the General Formula (A). ### Claim 19 (depends on 14) The compound of claim 14, wherein X in General Formula (A) is para to L. ### Claim 20 (depends on 14) The compound of claim 14, wherein at least two adjacent groups out of R112 to R114, R114 and R115, at least two adjacent groups out of R115 to R118, at least two adjacent groups out of R120 to R122, R122 and R123, at least two adjacent groups out of R123 to R126, at least two adjacent groups out of R128 to R130, R130 and R131, or at least two adjacent groups out of R131 to R134 are bonded to each other to form a ring.