# US 12,215,115 B2 · Platinum (II) tetradentate ONNO complex luminescent material, preparation method and application thereof in organic light emitting diode > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,215,115 B2 - Document ID: US12215115B2 - Status: Granted - Kind: B2 - Application number: 17/297,741 - Filed: 2019-11-02 - Published: 2022-03-17 - Granted: 2025-02-04 - Earliest claimed: 2018-12-17 - Assignees: Guangdong Aglaia Optoelectronic Materials Co., Ltd - Applicants: Guangdong Aglaia Optoelectronic Materials Co., Ltd - Inventors: Jiahuan Peng; Huiyang Li; Lei Dai; Lifei Cai - Web page: https://patentgrep.com/patent/US12215115B2 ## CPC - C07F 15/0086: {Platinum compounds} - C09K 11/06: containing organic luminescent materials - C07D 405/14: containing three or more hetero rings - C07F 15/0093: {without a metal-carbon linkage} - H10K 85/346: {comprising platinum} - H10K 50/11: characterised by the electroluminescent [EL] layers - 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) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract The invention relates to a platinum (ii) tetradentate onno complex luminescent material, preparation method and application thereof in organic light emitting diode. A platinum (II) tetradentate pyridine diphenol ONNO complex light-emitting material having the chemical structure of Formula (I) can be used for manufacturing organic light-emitting diodes emitting pure red light. The light-emitting material of the invention, because the end of the left side thereof is connected to benzofuran, has more red shift than the emission spectrum of the bipyridyl phenol ONNO-Pt(II) complex without a benzofuran group, and the anti-aggregation performance of the platinum(II) complex is effectively increased, as a B group is introduced on the phenolic ring on the right side thereof, so the self-quenching rate constant is low, and the color purity emitting deep red light and better luminous efficiency can be maintained in a certain range of doping concentration, which is more suitable for industrial preparation systems. ## Claims ### Claim 1 A platinum (II) tetradentate ONCN complex light-emitting material having a chemical structure of Formula (I), wherein: R1-R10 are independently a hydrogen atom, a deuterium atom, a halogen, a hydroxyl group, an unsubstituted alkyl group, a halogenated alkyl group, a deuterated alkyl group, a cycloalkyl group, an unsubstituted aryl group, a halogenated aryl group, an acyl group, an alkoxyl group, an acyloxyl group, an amino group, a nitro group, an acylamino group, an aralkyl group, a cyano group, a carboxyl group, a sulfonyl group, a styryl group, an amino carboxyl group, a carbamoyl group, an aryloxy carboxyl group, a phenoxy carboxyl or epoxy carboxyl group, a carbazole group or a diphenylamine group, or R1-R10 independently form a 5-8 membered ring with adjacent groups, and R1-R10 are not hydrogen at the same time; B presents an anti-aggregation group, and wherein R11-R15 are independently a hydrogen atom, a deuterium atom, a halogen, an unsubstituted alkyl group, a halogenated alkyl group, a deuterated alkyl group, a cycloalkyl group, an unsubstituted aryl group, a halogenated aryl group, a C1-C10 alkyl substituted aryl group, a cyano group, a carbazolyl group, or a C1-C10 alkyl substituted carbazolyl group. ### Claim 2 (depends on 1) The light-emitting material according to claim 1, wherein: R1-R10 are independently a hydrogen atom, a deuterium atom, a halogen, a hydroxyl group, an unsubstituted alkyl group having 1 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, a deuterated alkyl group having 1 to 2 carbon atoms, a five- or six-membered cycloalkyl group, an unsubstituted aryl group having 6 to 10 carbon atoms, a halogenated aryl group having 6 to 10 carbon atoms, an alkoxyl group having 1 to 6 carbon atoms, an amino group, a nitro group, a cyano group, a carbazolyl group, or a diphenylamine group, or R1-R10 independently form a 5-8 membered ring with adjacent groups, and R11-R15 are independently a hydrogen atom, a deuterium atom, a halogen, an unsubstituted alkyl group having 1 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, a five-or six-membered cycloalkyl group, an unsubstituted aryl group having 6 to 10 carbon atoms, a halogenated aryl group having 6 to 10 carbon atoms, a C1-C4 alkyl substituted aryl group having 6 to 10 carbon atoms, a cyano group, a carbazolyl group, or a C1-C4 alkyl substituted carbazolyl group. ### Claim 3 (depends on 2) The light-emitting material according to claim 2, wherein R7, R8 are independently a hydrogen atom. ### Claim 4 (depends on 3) The light-emitting material according to claim 3, wherein R6, R9 and R10 are independently a hydrogen atom, a fluorine atom, an unsubstituted alkyl group having 1 to 4 carbon atoms, a trifluoromethyl group or a phenyl group. ### Claim 5 (depends on 4) The light-emitting material according to claim 4, wherein: R1-R5 are independently a hydrogen atom, a deuterium atom, a fluorine atom, an unsubstituted alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, a five- or six-membered cycloalkyl group, an unsubstituted aryl group having 6 to 10 carbon atoms, a fluorinated aryl group having 6 to 10 carbon atoms, and R11-R15 are independently a hydrogen atom, a deuterium atom, a fluorine atom, an unsubstituted alkyl group having 1 to 4 carbon atoms, a fluorinated alkyl group having 1 to 4 carbon atoms, a five- or six-membered cycloalkyl group, an unsubstituted aryl group having 6 to 10 carbon atoms, a halogenated aryl group having 6 to 10 carbon atoms, a C1-C4 alkyl substituted aryl group having 6 to 10 carbon atoms, a carbazolyl group, or a C1-C4 alkyl substituted carbazolyl group. ### Claim 6 (depends on 5) The light-emitting material according to claim 5, wherein R1-R5 are independently a hydrogen atom, a fluorine atom, an unsubstituted alkyl group having 1 to 4 carbon atoms, a trifluoromethyl group or a phenyl group. ### Claim 7 (depends on 6) The light-emitting material according to claim 6, wherein: R1, R3 and R5 are independently a hydrogen atom, and R2 and R4 are independently a hydrogen atom, a fluorine atom, an unsubstituted alkyl group having 1 to 4 carbon atoms, a trifluoromethyl group or a phenyl group. ### Claim 8 (depends on 7) The light-emitting material according to claim 7, wherein R11-R15 are independently a hydrogen atom, an unsubstituted alkyl group having 1 to 4 carbon atoms, a trifluoromethyl group or a phenyl group. ### Claim 9 (depends on 5) The light-emitting material according to claim 5, wherein: R12 and R14 are independently a hydrogen atom, and R11, R13 and R15 are independently a hydrogen atom, a fluorine atom, an unsubstituted alkyl group having 1 to 4 carbon atoms, a trifluoromethyl group, a phenyl group, a 4-tert-butylphenyl group, a naphthyl group or a carbazolyl group. ### Claim 10 A platinum (II) tetradentate ONCN complex light-emitting material having one of the following chemical structural formulas: ### Claim 11 (depends on 1) A ligand of said light-emitting material according to claim 1, having the following chemical structure: where ### Claim 12 (depends on 1) A preparation method of said light-emitting material according to claim 1, comprising: using a substituted o-methoxydibenzo[b,d] furan ethyl ketone compound A and a substituted or unsubstituted benzaldehyde compound B as raw material to obtain a substituted or unsubstituted chalcone compound C under alkaline KOH conditions, mixing a substituted or unsubstituted 6-bromopyridyl ethyl ketone compound D with such pyridine as a solvent to obtain a pyridine salt intermediate E under iodine simple substance conditions, obtaining a pyridine ring intermediate F from the substituted or unsubstituted chalcone compound C and the pyridine salt intermediate E under ammonium acetate conditions, coupling the pyridine ring intermediate F with a o-methoxyphenyl boronic ester compound H by way of metal coupling to obtain an intermediate I, obtaining a ligand J from the intermediate I by way of demethylation reaction, and reacting the ligand J with a platinum compound under alkaline conditions to obtain a platinum (II) tetradentate ONCN complex light-emitting material after being purified, the chemical equations thereof being as follows: ### Claim 13 (depends on 12) The preparation method according to claim 12, wherein said coupling reaction is carried out by using Pd(PPh3)4 as a catalyst under K2CO3 basic conditions. ### Claim 14 (depends on 12) The preparation method according to claim 12, wherein said ligand J reacts with platinum compound potassium tetrachloroplatinate in sodium tert-butoxide and solvent DMSO at 130° C. ### Claim 15 (depends on 1) An application of said light-emitting material according to claim 1 in organic electroluminescent devices. ### Claim 16 (depends on 2) A ligand of said light-emitting material according to claim 2, having the following chemical structure: where ### Claim 17 (depends on 2) A preparation method of said light-emitting material according to claim 2, comprising: using a substituted o-methoxydibenzo[b,d] furan ethyl ketone compound A and a substituted or unsubstituted benzaldehyde compound B as raw material to obtain a substituted or unsubstituted chalcone compound C under alkaline KOH conditions, mixing a substituted or unsubstituted 6-bromopyridyl ethyl ketone compound D with such pyridine as a solvent to obtain a pyridine salt intermediate E under iodine simple substance conditions, obtaining a pyridine ring intermediate F from the substituted or unsubstituted chalcone compound C and the pyridine salt intermediate E under ammonium acetate conditions, coupling the pyridine ring intermediate F with a o-methoxyphenyl boronic ester compound H by way of metal coupling to obtain an intermediate I, obtaining a ligand J from the intermediate I by way of demethylation reaction, and reacting the ligand J with a platinum compound under alkaline conditions to obtain a platinum (II) tetradentate ONCN complex light-emitting material after being purified, the chemical equations thereof being as follows: ### Claim 18 (depends on 17) The preparation method according to claim 17, wherein said coupling reaction is carried out by using Pd(PPh3)4 as a catalyst under K2CO3 basic conditions. ### Claim 19 (depends on 17) The preparation method according to claim 17, wherein said ligand J reacts with platinum compound potassium tetrachloroplatinate in sodium tert-butoxide and solvent DMSO at 130° C. ### Claim 20 (depends on 10) An application of said light-emitting material according to claim 10 in organic electroluminescent devices.