# US 8,569,486 B2 · Organometal complex and light-emitting element using the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,569,486 B2 - Document ID: US8569486B2 - Status: Granted - Kind: B2 - Application number: 13/609,970 - Filed: 2012-09-11 - Published: 2013-01-03 - Granted: 2013-10-29 - Earliest claimed: 2003-12-02 - Assignees: Semiconductor Energy Laboratory Co., Ltd. - Applicants: Hideko Inoue; Satoshi Seo; Satoko Shitagaki; Hiroko Abe - Inventors: Hideko Inoue; Satoshi Seo; Satoko Shitagaki; Hiroko Abe - Web page: https://patentgrep.com/patent/US8569486B2 ## CPC - H10K 85/342: {comprising iridium} - 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} - C09K 2211/1044: containing two nitrogen atoms as heteroatoms - C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 2101/10: Triplet emission - 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 organometallic complex according to the present invention comprises a structure represented by the following general formula (1). In the formula, R1 to R5 are any one selected from the group consisting of hydrogen, a halogen element, an acyl group, an alkyl group, an alkoxy group, an aryl group, a cyano group, and a heterocyclic group, Ar is an aryl group having an electron-withdrawing group or a heterocyclic group having electron-drawing group, and M is an element of Group 9 or an element of Group 10. ## Claims ### Claim 1 A light-emitting element comprising: an organometallic complex comprising a structure represented by the following formula (1), wherein each of R1 to R5 comprises any one selected from the group of hydrogen, a halogen, an alkyl group, an alkoxy group, an aryl group and a cyano group, wherein Ar comprises an aryl group, and wherein M comprises an element of Group 9 or 10. ### Claim 2 (depends on 1) The light-emitting element according to claim 1, wherein the M is an iridium atom or a platinum atom. ### Claim 3 (depends on 1) The light-emitting element according to claim 1, wherein further comprising a light-emitting layer including the organometallic complex. ### Claim 4 (depends on 1) The light-emitting element according to claim 1, wherein the organometallic complex is included in a light-emitting layer as a guest material, and wherein a quinoxaline derivative is included in the light-emitting layer as a host material. ### Claim 5 A light-emitting element comprising: an organometallic complex comprising a structure represented by the following formula (2), wherein each of R1 to R9 comprises any one selected from the group of hydrogen, a halogen, an alkyl group, an alkoxy group, an aryl group, and a cyano group, and wherein M comprises an element of Group 9 or 10. ### Claim 6 (depends on 5) The light-emitting element according to claim 5, wherein the M is an iridium atom or a platinum atom. ### Claim 7 (depends on 5) The light-emitting element according to claim 5, further comprising a light-emitting layer including the organometallic complex. ### Claim 8 (depends on 5) The light-emitting element according to claim 5, wherein the organometallic complex is included in a light-emitting layer as a guest material, and wherein a quinoxaline derivative is included in the light-emitting layer as a host material. ### Claim 9 A light-emitting element comprising: an organometallic complex represented by the following formula (3), wherein each of R1 to R5 comprises any one selected from the group of hydrogen, a halogen, an alkyl group, an alkoxy group, an aryl group, and a cyano group, wherein Ar comprises an aryl group, wherein M comprises an element of Group 9 or an element of Group 10, wherein n is 2 when the M comprises the element of Group 9 while n is 1 when the M comprises the element of Group 10, and wherein L comprises any one of a monoanionic ligand having a β-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, and a monoanionic bidentate chelate ligand having a phenolic hydroxyl group. ### Claim 10 (depends on 9) The light-emitting element according to claim 9, wherein the L is any one of monoanionic bidentate chelate ligands shown by the following structure formulas (5) to (11). ### Claim 11 (depends on 9, 10) The light-emitting element according to claim 9 or 10, wherein the M is an iridium atom or a platinum atom. ### Claim 12 (depends on 9, 10) The light-emitting element according to claim 9 or 10, further comprising a light-emitting layer including the organometallic complex. ### Claim 13 (depends on 9, 10) The light-emitting element according to claim 9 or 10, wherein the organometallic complex is included in a light-emitting layer as a guest material, and wherein a quinoxialinc quinoxaline derivative is included in the light-emitting layer as a host material. ### Claim 14 A light-emitting element comprising: an organometallic complex represented by the following formula (4), wherein each of R1 to R9 comprises any one selected from the group of hydrogen, a halogen, an alkyl group, an alkoxy group, an aryl group, and a cyano group, wherein M comprises an element of Group 9 or an element of Group 10, wherein n is 2 when the M comprises the element of Group 9 while n is 1 when the M comprises the element of Group 10, and wherein L comprises any one of a monoanionic ligand having a β-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, and a monoanionic bidentate chelate ligand having a phenolic hydroxyl group. ### Claim 15 (depends on 14) The light-emitting element according to claim 14, wherein the L is any one of monoanionic bidentate chelate ligands shown by the following structure formulas (5) to (11) ### Claim 16 (depends on 14, 15) The light-emitting element according to claim 14 or 15, wherein the M is an iridium atom or a platinum atom. ### Claim 17 (depends on 14, 15) The light-emitting element according to claim 14 or 15, further comprising a light-emitting layer including the organometallic complex. ### Claim 18 (depends on 14, 15) The light-emitting element according to claim 14 or 15, wherein the organometallic complex is included in a light-emitting layer as a guest material, and wherein a quinoxaline derivative is included in the light-emitting layer as a host material. ### Claim 19 A light-emitting element comprising: an organometallic complex comprising a structure represented by the following formula (12), wherein each of R2 to R14 comprises any one selected from the group of hydrogen, a halogen, an alkyl group, an alkoxy group, an aryl group, and a cyano group, and wherein M is an element of Group 9 or 10. ### Claim 20 (depends on 19) The light-emitting element according to claim 19, wherein the M is an iridium atom or a platinum atom. ### Claim 21 (depends on 19) The light-emitting element according to claim 19, further comprising a light-emitting layer including the organometallic complex. ### Claim 22 (depends on 19) The light-emitting element according to claim 19, wherein the organometallic complex is included in a light-emitting layer as a guest material, and wherein a quinoxialino quinoxaline derivative is included in the light-emitting layer as a host material. ### Claim 23 A light-emitting element comprising: an organometallic complex comprising a structure represented by the following formula (13), wherein R15 or R16 comprises any one selected from the group of hydrogen, a halogen, and a haloalkyl group, and wherein M comprises an element of Group 9 or 10. ### Claim 24 (depends on 23) The light-emitting element according to claim 23, wherein the M is an iridium atom or a platinum atom. ### Claim 25 (depends on 23) The light-emitting element according to claim 23, further comprising a light-emitting layer including the organometallic complex. ### Claim 26 (depends on 23) The light-emitting element according to claim 23, wherein the organometallic complex is included in a light-emitting layer as a guest material, and wherein a quinoxaline derivative is included in the light-emitting layer as a host material. ### Claim 27 A light-emitting element comprising: an organometallic complex represented by the following formula (14), wherein each of R2 to R14 comprises any one selected from the group of hydrogen, a halogen, an alkyl group, an alkoxy group, an aryl group, and a cyano group, wherein M comprises an element of Group 9 or an element of Group 10, wherein n is 2 when the M comprises the element of Group 9 while n is 1 when the M comprises the element of Group 10, and wherein L comprises any one of a monoanionic ligand having a β-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, and a monoanionic bidentate chelate ligand having a phenolic hydroxyl group. ### Claim 28 (depends on 27) The light-emitting element according to claim 27, wherein the L is any one of monoanionic bidentate chelate ligands shown by the following structure formulas (5) to (11) ### Claim 29 (depends on 27, 28) The light-emitting element according to claim 27 or 28, wherein the M is an iridium atom or a platinum atom. ### Claim 30 (depends on 27, 28) The light-emitting element according to claim 27 or 28, further comprising a light-emitting layer including the organometallic complex. ### Claim 31 (depends on 27, 28) The light-emitting element according to claim 27 or 28, wherein the organometallic complex is included in a light-emitting layer as a guest material, and wherein a quinoxaline derivative is included in the light-emitting layer as a host material. ### Claim 32 A light-emitting element having an organometallic complex represented by the following formula (15), wherein R15 or R16 comprises any one selected from the group of hydrogen, a halogen, and a haloalkyl group, wherein M comprises an element of Group 9 or an element of Group 10, wherein n is 2 when the M comprises the element of Group 9 while n is 1 when the M comprises the element of Group 10, and wherein L comprises any one of a monoanionic ligand having a β-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, and a monoanionic bidentate chelate ligand having a phenolic hydroxyl group. ### Claim 33 (depends on 32) The light-emitting element according to claim 32, wherein the L is any one of monoanionic bidentate chelate ligands shown by the following structure formulas (5) to (11) ### Claim 34 (depends on 32, 33) The light-emitting element according to claim 32 or 33, wherein the M is an iridium atom or a platinum atom. ### Claim 35 (depends on 32, 33) The light-emitting element according to claim 32 or 33, further comprising a light-emitting layer including the organometallic complex. ### Claim 36 (depends on 32, 33) The light-emitting element according to claim 32 or 33, wherein the organometallic complex is included in a light-emitting layer as a guest material, and wherein a quinoxaline derivative is included in the light-emitting layer as a host material.