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Thermal activated delayed fluorescence material, preparation method and electroluminescence device

A technology of heat-activated delayed and fluorescent materials, applied in the direction of luminescent materials, electric solid devices, chemical instruments and methods, etc., can solve the problems of lack of heavy metal Ir complexes, etc., and achieve high efficiency, high luminous efficiency, and increased luminous efficiency.

Active Publication Date: 2019-08-30
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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  • Thermal activated delayed fluorescence material, preparation method and electroluminescence device
  • Thermal activated delayed fluorescence material, preparation method and electroluminescence device
  • Thermal activated delayed fluorescence material, preparation method and electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthetic fluorescent material compound 1, the synthetic route is as follows:

[0047]

[0048] Synthetic steps:

[0049] Add raw material 1 to a 100mL two-necked bottle (proportioning 4.00g, molar weight 5mmol), carbazole (proportioning 1.00g, molar weight 6mmol), palladium acetate (Pd(OAc) 2 ) (proportion 45mg, molar weight 0.2mmol) and tri-tert-butylphosphine tetrafluoroborate ((t-Bu) 3 HPBF 4 ) (proportioning 0.17g, molar weight 0.6mmol), then, in the glove box, add NaOt-Bu (proportioning 0.58g, molar weight 6mmol), inject 50mL of toluene that dehydrates and deoxygenates in advance 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, 1:3), to obtain Light blue powder 2.6g, yield 59%. After mass spectrometry ...

Embodiment 2

[0051] Synthetic fluorescent material compound 2, the synthetic route is as follows:

[0052]

[0053] Synthetic steps:

[0054] Add raw material 1 to a 100mL two-necked bottle (Proportioning 4.00g, molar weight 5mmol), diphenylamine (1.01g, 6mmol), palladium acetate (Pd(OAc) 2 ) (proportioning 45mg, molar weight 0.2mmol) and tri-tert-butylphosphine tetrafluoroborate ((t-Bu) 3 HPBF 4 ) (proportioning 0.17g, molar weight 0.6mmol), then, in the glove box, add NaOt-Bu (proportioning 0.58g, molar weight 6mmol), inject 50mL of toluene that dehydrated and deoxygenated in advance 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, 1:3) to obtain Light blue powder 2.2g, yield 50%. After mass spectrometry analysis, MS (EI) m / z...

Embodiment 3

[0056] Synthetic fluorescent material compound 3, the synthetic route is as follows:

[0057]

[0058] Add raw material 1 to a 100mL two-necked bottle (proportion 4.00g, molar weight 5mmol), 9,9'-dimethylacridine (2.51g, 6mmol), palladium acetate (Pd(OAc) 2 ) (ratio 45mg, molar weight 0.2mmol) and tri-tert-butylphosphine tetrafluoroborate ((t-Bu) 3 HPBF 4 ) (proportioning 0.17g, molar weight 0.6mmol), then, in the glove box, add NaOt-Bu (proportioning 0.58g, molar weight 6mmol), inject 50mL of toluene that dehydrates and deoxygenates in advance 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, 1:3) to obtain Light blue powder 2.9g, yield 63%. After mass spectrometry analysis, MS (EI) m / z: 928.28.

[0059] Theoretica...

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Abstract

The invention provides an improved thermal activated delayed fluorescence material, a preparation method and an electroluminescence device. On the basis of a structure of tribenzonitrile, two dihydrophenazine groups are connected as electron-donating groups, different electron-donating units are further connected to adjust an overall charge transfer intensity, and a series of blue light thermal activated delayed fluorescence materials which are low in single triplet state energy difference, high in light emission efficiency and rapid in reverse intersystem crossing constant are synthesized.

Description

technical field [0001] The invention relates to the field of optoelectronic technology, in particular to a thermally activated delayed fluorescent material, a preparation method and an electroluminescent device. 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. [0003] 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 theoretical internal quantum efficiency (IQ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D401/14C07D241/48C09K11/06H01L51/50H01L51/54
CPCC07D403/14C07D401/14C07D241/48C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044H10K85/6572H10K50/11
Inventor 罗佳佳
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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