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High-performance sky blue light thermal activation delayed fluorescence material, preparation method and application thereof

A technology of heat-activated delayed and fluorescent materials, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of lack of heavy metal Ir complexes, and achieve improved synthesis efficiency, great application prospects and economic value, and low unit cost. The effect of the triplet energy level difference

Active Publication Date: 2020-05-22
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

At present, TADF materials that meet the above conditions are still relatively scarce compared to heavy metal Ir complexes.

Method used

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  • High-performance sky blue light thermal activation delayed fluorescence material, preparation method and application thereof
  • High-performance sky blue light thermal activation delayed fluorescence material, preparation method and application thereof
  • High-performance sky blue light thermal activation delayed fluorescence material, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] The synthetic route of target compound 1 is as follows:

[0061]

[0062] Synthetic steps: Add raw material 1 (2.3g, 5mmol), phenoxazine (1.1g, 6mmol), palladium acetate (45mg, 0.2mmol) and tri-tert-butylphosphine tetrafluoroborate (0.17 g, 0.6mmol), then NaOt-Bu (0.58g, 6mmol) was added into the glove box, and 60mL of toluene that had been dehydrated and deoxygenated was poured into the glove box under an argon atmosphere, and reacted at 120°C for 24 hours. Cool to room temperature, pour the reaction solution into 200mL ice water, extract three times with dichloromethane, combine the organic phases, spin into silica gel, and separate and purify by column chromatography (dichloromethane:n-hexane, v:v, 1:2) to obtain Light blue powder 1.3g, yield 47%. MS (EI) m / z: 559.01.

Embodiment 2

[0064] The synthetic route of target compound 2 is as follows:

[0065]

[0066] Synthesis steps: Add raw material 1 (2.3g, 5mmol), 1,8,9,9'-tetramethylacridine (1.4g, 6mmol), palladium acetate (45mg, 0.2mmol) and three Tert-butylphosphine tetrafluoroborate (0.17g, 0.6mmol), then NaOt-Bu (0.58g, 6mmol) was added in the glove box, and 60mL of toluene that had been dehydrated and deoxygenated in advance was injected under an argon atmosphere. React at 120°C for 24 hours. Cool to room temperature, pour the reaction solution into 200mL ice water, extract three times with dichloromethane, combine the organic phases, spin into silica gel, and separate and purify by column chromatography (dichloromethane:n-hexane, v:v, 3:2) to obtain Light blue powder 1.1g, yield 34%. MS (EI) m / z: 613.08.

Embodiment 3

[0068] The synthetic route of target compound 3 is as follows:

[0069]

[0070] Synthesis steps: Add raw material 1 (2.3g, 5mmol), 1,3,6,8,9,9'-hexamethylacridine (1.6g, 6mmol), palladium acetate (45mg, 0.2 mmol) and tri-tert-butylphosphine tetrafluoroborate (0.17g, 0.6mmol), then NaOt-Bu (0.58g, 6mmol) was added into the glove box, and 60mL of water and oxygen were removed in advance under an argon atmosphere. of toluene at 120°C for 24 hours. Cool to room temperature, pour the reaction solution into 200mL ice water, extract three times with dichloromethane, combine the organic phases, spin into silica gel, and separate and purify by column chromatography (dichloromethane:n-hexane, v:v, 3:2) to obtain Light blue powder 1.2g, yield 37%. MS (EI) m / z: 641.00.

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Abstract

The invention relates to a high-performance sky blue light thermal activation delayed fluorescence material, a preparation method and applications thereof. According to the invention, the problems inthe prior art are solved; a series of sky blue light thermal activation delayed fluorescent materials with low single triplet state energy level difference, high luminous efficiency and rapid reverseintersystem crossing constant are synthesized through ingenious molecular design while fine adjustment of a structure is achieved so as to achieve fine adjustment of a spectrum; and the structure of the material is confirmed through mass spectrometry analysis, the photophysical properties of the material are researched in detail, and finally the sky blue light TADF materials are applied to a light-emitting layer to prepare a series of high-performance OLEDs so as to achieve huge application prospects and economic value.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent diodes, and in particular relates to a high-performance sky-blue light thermally activated delayed fluorescent material, as well as its preparation method and application. Background technique [0002] Organic light-emitting diodes (organic light-emitting diodes, OLEDs) do not need a backlight source for their active light emission, high luminous efficiency, large viewing angle, fast response speed, wide temperature range, relatively simple production and processing technology, and low driving voltage. , low energy consumption, lighter and thinner, flexible display and other advantages, as well as huge application prospects, have attracted the attention of many researchers. In OLEDs, the dominant light-emitting guest material is crucial. The luminescent guest materials used in early OLEDs are fluorescent materials. Since the ratio of singlet and triplet excitons in OLEDs is 1:3, the theo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10C07D409/10C09K11/06H01L51/54
CPCC07D413/10C07D409/10C09K11/06C09K2211/1092C09K2211/1033C09K2211/1029H10K85/6576H10K85/657H10K85/6572H10K50/11C09K2211/1007C09K2211/1018
Inventor 罗佳佳
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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