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Thermally activated delayed fluorescence material and organic light-emitting diode prepared by using same

A heat-activated delayed, light-emitting diode technology, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problem of lack of heat-activated delayed fluorescent materials, and achieve low singlet triplet energy level difference, high luminous efficiency, high light Effect of Luminescent Quantum Yield

Active Publication Date: 2020-04-17
WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, thermally activated delayed fluorescence materials that meet the above conditions are still relatively scarce compared to heavy metal complexes.

Method used

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  • Thermally activated delayed fluorescence material and organic light-emitting diode prepared by using same
  • Thermally activated delayed fluorescence material and organic light-emitting diode prepared by using same
  • Thermally activated delayed fluorescence material and organic light-emitting diode prepared by using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Preparation of thermally activated delayed fluorescent material with the following structural formula

[0028]

[0029] The synthesis steps are as follows:

[0030]

[0031] First, add raw material 1 (3.0g, 5mmol), carbazole (2.0g, 12mmol), palladium acetate (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate (0.34g, 1.2 mmol). Then, put the two-necked bottle into the glove box, and add NaOt-Bu (1.16 g, 12 mmol) into the two-necked bottle. Next, under an argon atmosphere, pour 100 mL of toluene that had been dehydrated and deoxygenated into the two-neck flask, and react at 120° C. for 48 hours to obtain a reaction liquid. After cooling to room temperature, the reaction solution in the two-neck flask was poured into 300 mL of ice water. Subsequently, the reaction solution was extracted with dichloromethane. After three extractions, the organic phases obtained from each extraction were combined and separated and purified by column chromatogra...

Embodiment 2

[0032] Example 2: Preparation of thermally activated delayed fluorescent material with the following structural formula

[0033]

[0034] The synthesis steps are as follows:

[0035]

[0036] First, add raw material 1 (3.0g, 5mmol), 9,9-dimethylacridine (2.5g, 12mmol), palladium acetate (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroethylene to a 250mL two-necked flask Borate (0.34 g, 1.2 mmol). Then, put the two-necked bottle into the glove box, and add NaOt-Bu (1.16 g, 12 mmol) into the two-necked bottle. Next, under an argon atmosphere, pour 100 mL of toluene that had been dehydrated and deoxygenated into the two-neck flask, and react at 120° C. for 48 hours to obtain a reaction liquid. After cooling to room temperature, the reaction solution in the two-neck flask was poured into 300 mL of ice water. Subsequently, the reaction solution was extracted with dichloromethane. After three extractions, the organic phases obtained from each extraction were combined...

Embodiment 3

[0037] Example 3: Preparation of thermally activated delayed fluorescent material with the following structural formula

[0038]

[0039] The synthesis steps are as follows:

[0040]

[0041] First, add raw material 1 (3.0g, 5mmol), phenoxazine (2.2g, 12mmol), palladium acetate (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate (0.34g , 1.2 mmol). Then, put the two-necked bottle into the glove box, and add NaOt-Bu (1.16g, 12mmol) into the two-necked bottle. Next, under an argon atmosphere, pour 100 mL of toluene that had been dehydrated and deoxygenated into the two-neck flask, and react at 120° C. for 48 hours to obtain a reaction liquid. After cooling to room temperature, the reaction solution in the two-neck flask was poured into 300 mL of ice water. Subsequently, the reaction solution was extracted with dichloromethane, extracted three times, and the organic phases obtained by each extraction were combined, and separated and purified by column chromatog...

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Abstract

The invention discloses a thermally activated delayed fluorescence material. The thermally activated delayed fluorescence material comprises a structure represented by formula (I), and has low singletriplet state energy level difference, high reverse intersystem crossing constant and high photoluminescence quantum yield. The invention further discloses an organic light-emitting diode. The organiclight-emitting diode comprises an anode, a cathode, and a light-emitting layer and an organic functional layer which are located between the anode and the cathode, and one or both of the light-emitting layer and the organic functional layer comprises the thermally activated delayed fluorescence material of formula (I).

Description

technical field [0001] The present invention relates to the technical field of organic light-emitting materials, in particular to a heat-activated delayed fluorescent material and an organic light-emitting diode prepared by using the heat-activated delayed fluorescent material. Background technique [0002] Organic light-emitting diodes (organic light-emitting diodes, OLEDs) have broad application prospects in the fields of solid-state lighting and flat panel display, and the luminescent guest material is the main factor affecting the luminous efficiency of organic light-emitting diodes. In the early days, the light-emitting guest materials used in organic light-emitting diodes were fluorescent materials, and the ratio of excitons in singlet and triplet states in organic light-emitting diodes was 1:3, so the internal quantum efficiency (internal quantum efficiency) of organic light-emitting diodes is theoretically efficiency, IQE) can only reach 25%, so that the application ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C09K11/06H01L51/50H01L51/54
CPCC07D495/04C09K11/06C09K2211/1092C09K2211/1029C09K2211/1033H10K85/657H10K85/6576H10K85/6572H10K50/12
Inventor 罗佳佳
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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