# US 2017/0288160 A1 · Organic electroluminescent materials and devices > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2017/0288160 A1 - Document ID: US20170288160A1 - Status: Published application - Kind: A1 - Application number: 15/623,491 - Filed: 2017-06-15 - Published: 2017-10-05 - Earliest claimed: 2011-06-08 - Assignees: Universal Display Corporation - Applicants: Universal Display Corporation - Inventors: Chun LIN; Chuanjun XIA; Jui-Yi TSAI; Bin MA - Web page: https://patentgrep.com/patent/US20170288160A1 ## CPC - C07F 15/0033: {Iridium compounds} - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 85/342: {comprising iridium} - H10K 50/12: comprising dopants - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - H10K 2101/10: Triplet emission - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract Novel heteroleptic iridium carbene complexes are provided, which contain at least two different carbene ligands. Selective substitution of the carbene ligands provides for phosphorescent compounds that are suitable for use in a variety of OLED devices. ## Claims ### Claim 1 A compound comprising a heteroleptic iridium complex having the formula: wherein X is selected from the group consisting of CRR′, SiRR′, C═O, N—R, B—R, O, S, SO, SO2, and Se; wherein R2, Rx, R5, and R6 represent mono, di, tri, tetra substitutions or no substitution; wherein R, R′, R1, R2, Rx, R4, R5, and R6 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any two adjacent substituents are optionally joined together to form a ring, which may be further substituted; and wherein n is 1 or 2. ### Claim 2 (depends on 1) The compound of claim 1, wherein X is O or S. ### Claim 3 (depends on 1) The compound of claim 1, wherein the compound has the formula: wherein Y5 to Y8 is CR3 or N; wherein each R3 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein any two adjacent substituents of R3 are optionally joined to form into ring and may be further substituted. ### Claim 4 (depends on 1) The compound of claim 1, wherein R1 is alkyl or cycloalkyl. ### Claim 5 (depends on 1) The compound of claim 1, wherein R1 is aryl or substituted aryl. ### Claim 6 (depends on 5) The compound of claim 5, wherein R1 is a 2,6-disubstituted aryl. ### Claim 7 (depends on 1) The compound of claim 1, wherein the compound has the formula: wherein Y1 to Y4 is CR7 or N; and wherein each R7 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. ### Claim 8 (depends on 7) The compound of claim 7, wherein at least one of Y1 to Y4 is N. ### Claim 9 (depends on 7) The compound of claim 7, wherein the compound has the formula: wherein Y5 to Y8 is CR3 or N; and wherein each R3 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein any two adjacent substituents of R3 are optionally joined together to form a ring, which may be further substituted. ### Claim 10 (depends on 9) The compound of claim 9, wherein at least one of Y1 to Y4 is N. ### Claim 11 A first device comprising an organic light emitting device, further comprising: an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising a compound having the formula: wherein X is selected from the group consisting of CRR′, SiRR′, C═O, N—R, B—R, O, S, SO, SO2, and Se; wherein R2, Rx, R5, and R6 may represent mono, di, tri, tetra substitutions or no substitution; wherein R, R′, R1, R2, Rx, R4, R5, and R6 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any two adjacent substituents are optionally joined together to form a ring, which may be further substituted; and wherein n is 1 or 2. ### Claim 12 (depends on 11) The first device of claim 11, wherein the organic layer is an emissive layer and the compound is an emissive dopant. ### Claim 13 (depends on 11) The first device of claim 11, wherein the organic layer further comprises a host that comprises at least one of the chemical groups selected from the group consisting of carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene; or the host is a metal complex. ### Claim 14 (depends on 13) The first device of claim 13, wherein the host is a metal carbene complex selected from the group consisting of: ### Claim 15 (depends on 14) The first device of claim 14, wherein the device further comprises a second organic layer that is a non-emissive layer between anode and the emissive layer; and wherein the material in the second organic layer is a metal carbene complex. ### Claim 16 (depends on 15) The first device of claim 15, wherein the device further comprises a third organic layer that is a non-emissive layer between cathode and the emissive layer; and wherein the material in the third organic layer is a metal carbene complex. ### Claim 17 (depends on 11) The first device of claim 11, wherein the device further comprises a second organic layer that is a non-emissive layer and the compound of Formula I is a material in the second organic layer. ### Claim 18 (depends on 17) The first device of claim 17, wherein the second organic layer is a hole transporting layer and the compound of Formula I is a transporting material in the second organic layer. ### Claim 19 (depends on 17) The first device of claim 17, wherein the second organic layer is a blocking layer and the compound having Formula I is a blocking material in the second organic layer. ### Claim 20 (depends on 11) The first device of claim 11, wherein the first device is a consumer product selected from the group consisting of flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, vehicles, a large area wall, theater or stadium screen, or a sign.