# US 8,772,485 B2 · Palladium complexes for organic light-emitting diodes > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,772,485 B2 - Document ID: US8772485B2 - Status: Granted - Kind: B2 - Application number: 13/682,035 - Filed: 2012-11-20 - Published: 2013-06-13 - Granted: 2014-07-08 - Earliest claimed: 2011-12-09 - Assignees: The University of Hong Kong - Applicants: Chi Ming Che; Chi Fai Kui; Pui Keong Chow - Inventors: Chi Ming Che; Chi Fai Kui; Pui Keong Chow - Web page: https://patentgrep.com/patent/US8772485B2 ## CPC - H10K 85/331: {Metal complexes comprising an iron-series metal, e.g. Fe, Co, Ni} - C07F 15/006: {Palladium compounds} - C09K 11/06: containing organic luminescent materials - H10K 85/341: {Transition metal complexes, e.g. Ru(II)polypyridine complexes (H10K85/331 takes precedence)} - 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 50/11: characterised by the electroluminescent [EL] layers - H10K 85/324: {comprising aluminium, e.g. Alq3} - 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 ## Abstract Subject matter disclosed herein relates to a series of palladium based materials, their preparation method and their applications in an organic light-emitting diode (OLED). ## Claims ### Claim 1 An organometallic complex having a chemical structure of Structure I: wherein each R1-R14 is independently selected from hydrogen, halogen, hydroxyl, an unsubstituted alkyl including from 1 to 10 carbon atoms, a substituted alkyl including from 1 to 20 carbon atoms, cycloalkyl including from 1 to 20 carbon atoms, an unsubstituted aryl including from 1 to 20 carbon atoms, a substituted aryl including from 1 to 20 carbon atoms, acyl including from 1 to 20 carbon atoms, alkoxy including from 1 to 20 carbon atoms, acyloxy including from 1 to 20 carbon atoms, amino, nitro, acylamino including from 1 to 20 carbon atoms, aralkyl including from 1 to 20 carbon atoms, cyano, carboxyl including from 1 to 20 carbon atoms, thio, styryl, aminocarbonyl including from 1 to 20 carbon atoms, carbamoyl including from 1 to 20 carbon atoms, aryloxycarbonyl including from 1 to 20 carbon atoms, phenoxycarbonyl including from 1 to 20 carbon atoms, or an alkoxycarbonyl group including from 1 to 20 carbon atoms, and wherein each X1-X20 is independently selected from the group consisting of boron, carbon, nitrogen, oxygen, and silicon. ### Claim 2 (depends on 1) The organometallic complex of claim 1, wherein the individual R1-R14 groups independently form 5 to 8 member rings with adjacent R groups. ### Claim 3 (depends on 2) The organometallic complex of claim 2, wherein the individual R1-R14 independently comprise a same atom as an adjacent R groups. ### Claim 4 (depends on 1) The organometallic complex of claim 1, wherein the individual R1-R14 form a 5 member ring with four of the X atoms to form a complex having a chemical structure of Structure II: wherein R1-R14 groups and X1-X20 are as defined in Structure I and each of R15-R16 is independently selected from hydrogen, halogen, hydroxyl, an unsubstituted alkyl including from 1 to 20 carbon atoms, a substituted alkyl including from 1 to 20 carbon atoms, cycloalkyl including from 1 to 20 carbon atoms, an unsubstituted aryl including from 1 to 20 carbon atoms, a substituted aryl including from 1 to 20 carbon atoms, acyl including from 1 to 20 carbon atoms, alkoxy including from 1 to 20 carbon atoms, acyloxy including from 1 to 20 carbon atoms, amino, nitro, acylamino including from 1 to 20 carbon atoms, aralkyl including from 1 to 20 carbon atoms, cyano, carboxyl, thio, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or an alkoxycarbonyl group. ### Claim 5 (depends on 1) The organometallic complex of claim 1, further comprising one of Complex 101, Complex 102, Complex 103, Complex 104, Complex 105, and Complex 106 as follows: ### Claim 6 (depends on 1) The organometallic complex of claim 1, wherein the organometallic complex is incorporated in an organic light-emitting diode (OLED). ### Claim 7 (depends on 1) The organometallic complex of claim 1, wherein the organometallic complex is incorporated in a polymer light-emitting diode (PLED). ### Claim 8 (depends on 6) The organometallic complex of claim 6, wherein the OLED is fabricated by thermal deposition. ### Claim 9 (depends on 6) The organometallic complex of claim 6, wherein the OLED is fabricated by spin coating. ### Claim 10 (depends on 6) The organometallic complex of claim 6, wherein the OLED is fabricated by printing. ### Claim 11 (depends on 7) The organometallic complex of claim 7, wherein the PLED is fabricated by spin coating. ### Claim 12 (depends on 7) The organometallic complex of claim 7, wherein the PLED is fabricated by printing. ### Claim 13 (depends on 8) The organometallic complex of claim 8, wherein the OLED emits a relatively narrow color emission spectrum originating from the organometallic complex. ### Claim 14 (depends on 11) The organometallic complex of claim 11, wherein the PLED emits a relatively narrow color emission spectrum originating from the organometallic complex. ### Claim 15 (depends on 8) The organometallic complex of claim 8, wherein the OLED emits a white emission comprising an emission from the organometallic complex and one or more different emission components from other emitting materials. ### Claim 16 (depends on 11) The organometallic complex of claim 11, wherein the PLED emits a white emission comprising an emission from said organometallic complex and one or more different emission components from other emitting materials. ### Claim 17 A method of preparing an organometallic complex, comprising: producing a chemical structure of Structure I, wherein each R1-R14 is independently selected from hydrogen, halogen, hydroxyl, an unsubstituted alkyl including from 1 to 10 carbon atoms, a substituted alkyl including from 1 to 20 carbon atoms, cycloalkyl including from 1 to 20 carbon atoms, an unsubstituted aryl including from 1 to 20 carbon atoms, a substituted aryl including from 1 to 20 carbon atoms, acyl including from 1 to 20 carbon atoms, alkoxy including from 1 to 20 carbon atoms, acyloxy including from 1 to 20 carbon atoms, amino, nitro, acylamino including from 1 to 20 carbon atoms, aralkyl including from 1 to 20 carbon atoms, cyano, carboxyl including from 1 to 20 carbon atoms, thio, styryl, aminocarbonyl including from 1 to 20 carbon atoms, carbamoyl including from 1 to 20 carbon atoms, aryloxycarbonyl including from 1 to 20 carbon atoms, phenoxycarbonyl including from 1 to 20 carbon atoms, or an alkoxycarbonyl group including from 1 to 20 carbon atoms, and wherein each X1-X20 is independently selected from the group consisting of boron, carbon, nitrogen, oxygen, and silicon. ### Claim 18 (depends on 17) The method of claim 17, wherein the individual R1-R14 groups form 5 to 8 member rings with adjacent R groups. ### Claim 19 (depends on 18) The method of claim 18, wherein the individual R1-R14 comprise a same atom as an adjacent R group. ### Claim 20 (depends on 18) The method of claim 18, wherein the individual R1-R14 form a 5 member ring with four of said X1-X20 atoms to form a complex with a chemical structure of Structure II: wherein R1-R14 groups and X1-X20 are as defined in Structure I and each of R15-R16 is independently selected from hydrogen, halogen, hydroxyl, an unsubstituted alkyl including from 1 to 20 carbon atoms, a substituted alkyl including from 1 to 20 carbon atoms, cycloalkyl including from 1 to 20 carbon atoms, an unsubstituted aryl including from 1 to 20 carbon atoms, a substituted aryl including from 1 to 20 carbon atoms, acyl including from 1 to 20 carbon atoms, alkoxy including from 1 to 20 carbon atoms, acyloxy including from 1 to 20 carbon atoms, amino, nitro, acylamino including from 1 to 20 carbon atoms, aralkyl including from 1 to 20 carbon atoms, cyano, carboxyl, thio, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or an alkoxycarbonyl group.