# US 2021/0280797 A1 · Efficient blue-green to orange-red thermally activated delayed fluorescence material, manufacture method, and application thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2021/0280797 A1 - Document ID: US20210280797A1 - Status: Published application - Kind: A1 - Application number: 16/622,955 - Filed: 2019-11-25 - Published: 2021-09-09 - Earliest claimed: 2019-05-31 - Assignees: Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. - Applicants: Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. - Inventors: Jiajia LUO; Xianjie LI; Jinchang HUANG; Yu GU; Lin YANG; Yamei BAI - Web page: https://patentgrep.com/patent/US20210280797A1 ## CPC - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - C07D 417/04: directly linked by a ring-member-to-ring-member bond - C09K 11/06: containing organic luminescent materials - H10K 85/652: {Cyanine dyes} - H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons} - C09K 2211/1007: Non-condensed systems - C09K 2211/1018: Heterocyclic compounds - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 2101/20: Delayed fluorescence emission - H10K 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract An efficient blue-green to orange-red thermally activated delayed fluorescence material, a manufacture method, and an application thereof are provided. This disclosure solves the technical problems in the art by cleverly synthesizing a series of thermally activated delayed fluorescence materials, which have lower singlet-triplet energy difference, high luminous efficiency, and fast reverse intersystem crossing constant, and simultaneously fine-tuning the structure to cover the spectrum from blue-green light to orange-red light. Further, their structures are confirmed by nuclear magnetic resonance and mass spectroscopy, and their photophysical properties are also determined. Therefore, these luminescent thermally activated delayed fluorescence (TADF) materials are applied to light-emitting layer for manufacturing a series of organic light-emitting diodes (OLEDs) having high performance, which have great application prospects and economic value. ## Claims ### Claim 1 An efficient blue-green to orange-red thermally activated delayed fluorescence material, comprising a compound represented by formula I below: wherein R1 is one of the following structures: and R2 is one of the following structures: ### Claim 2 (depends on 1) A method of manufacturing the efficient blue-green to orange-red thermally activated delayed fluorescence material according to claim 1, comprising: mixing a raw material 1, a raw material 2, palladium acetate, and tri-tert-butylphosphine tetrafluoroborate; and adding NaOt-Bu, followed by adding toluene under argon for a reaction, and obtaining a crude efficient blue-green to orange-red thermally activated delayed fluorescence material; wherein the raw material 1 is 5-bromo-2,3-difluoro-8-phenylquino-6,7-dicarbonitrile, and the raw material 2 is 9,10-dihydro-9,9-diphenyl acridine, phenoxazine, or phenothiazine. ### Claim 3 (depends on 2) The method of manufacturing the efficient blue-green to orange-red thermally activated delayed fluorescence material according to claim 2, wherein a molar ratio of the raw material 1 to the raw material 2 is 1:1 to 1:3. ### Claim 4 (depends on 2) The method of manufacturing the efficient blue-green to orange-red thermally activated delayed fluorescence material according to claim 2, wherein a molar ratio of the palladium acetate, the tri-tert-butylphosphine tetrafluoroborate, and the NaOt-Bu is 1:(3 to 6):(30 to 60). ### Claim 5 (depends on 2) The method of manufacturing the efficient blue-green to orange-red thermally activated delayed fluorescence material according to claim 2, wherein a molar volume ratio of the raw material 1 to toluene is 1:5 to 1:20. ### Claim 6 (depends on 2) The method of manufacturing the efficient blue-green to orange-red thermally activated delayed fluorescence material according to claim 2, wherein a temperature for the reaction is 80 to 160° C., and a time for the reaction is 12 to 48 hours. ### Claim 7 (depends on 2) The method of manufacturing the efficient blue-green to orange-red thermally activated delayed fluorescence material according to claim 2, further comprising: cooling the crude efficient blue-green to orange-red thermally activated delayed fluorescence material; extracting the crude efficient blue-green to orange-red thermally activated delayed fluorescence material with dichloromethane; combining organic phases; mixing with a silica gel under a spinning condition; and separating and purifying by column chromatography, thereby obtaining the efficient blue-green to orange-red thermally activated delayed fluorescence material. ### Claim 8 (depends on 1) A method of manufacturing the efficient blue-green to orange-red thermally activated delayed fluorescence material according to claim 1, comprising: mixing a raw material 1, a raw material 2, palladium acetate, and tri-tert-butylphosphine tetrafluoroborate; adding NaOt-Bu, following by adding toluene under argon for a reaction, and obtaining a crude efficient blue-green to orange-red thermally activated delayed fluorescence material; cooling the crude efficient blue-green to orange-red thermally activated delayed fluorescence material to a room temperature, following by pouring into ice water; extracting the crude efficient blue-green to orange-red thermally activated delayed fluorescence material with dichloromethane; combining organic phases; mixing with a silica gel under a spinning condition; and separating and purifying by column chromatography, and obtaining the efficient blue-green to orange-red thermally activated delayed fluorescence material; wherein the raw material 1 is 5-bromo-2,3-difluoro-8-phenylquino-6,7-dicarbonitrile, and the raw material 2 is 9,10-dihydro-9,9-diphenyl acridine, phenoxazine, or phenothiazine; wherein a molar ratio of the raw material 1 to the raw material 2 is 1:1 to 1:3, a molar ratio of the palladium acetate, the tri-tert-butylphosphine tetrafluoroborate, and the NaOt-Bu is 1:(3 to 6):(30 to 60); a molar volume ratio of the raw material 1 to toluene is 1:5 to 1:20; and wherein a reaction temperature is 80 to 160° C., a reaction time is 12 to 48 hours, and a frequency of the extracting with dichloromethane is 2 to 4. ### Claim 9 (depends on 1) A use of the efficient blue-green to orange-red thermally activated delayed fluorescence material according to claim 1. ### Claim 10 (depends on 9) The use according to claim 9, wherein the efficient blue-green to orange-red thermally activated delayed fluorescence material is used for manufacturing an organic light-emitting diode (OLED) device. ### Claim 11 (depends on 10) The use according to claim 10, wherein the efficient blue-green to orange-red thermally activated delayed fluorescence material is used for manufacturing a light-emitting layer of the OLED device.