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Thermally activated delayed fluorescent material and its preparation method and organic electroluminescent diode device

A technology of heat-activated delayed and fluorescent materials, applied in the direction of luminescent materials, electrical solid devices, chemical instruments and methods, etc., can solve the problem of lack of heavy metal Ir complexes and other problems

Active Publication Date: 2020-10-30
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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  • Thermally activated delayed fluorescent material and its preparation method and organic electroluminescent diode device
  • Thermally activated delayed fluorescent material and its preparation method and organic electroluminescent diode device
  • Thermally activated delayed fluorescent material and its preparation method and organic electroluminescent diode device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The synthetic route of target compound 1 is as follows:

[0045]

[0046] In the 100mL two-necked flask, add raw material 1 (2.00g, 5mmol), phenoxazine (2.2g, 12mmol), palladium acetate Pb (OAc) (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate ( t-Bu) 3 HPBF 4 (0.34g, 1.2mmol), then sodium tert-butoxide NaOt-Bu (1.16g, 12mmol) was added in the glove box, and 60mL of toluene that had been dehydrated and deoxygenated was injected 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, 2:1) to obtain 1.6 g of compound 1 as a green powder, yield 53%.

[0047] 1HNMR (300MHz, CD 2 Cl 2 ,δ): 8.54(s,2H), 8.04(s,2H), 7.62-7.48(m,5H), 7.14-7.07(m,4H), 7.03-6.96(m,12H).

[0048] MS(EI)m / z:[M] + calcd for C ...

Embodiment 2

[0050]The synthetic route of target compound 2 is as follows:

[0051]

[0052] Add raw material 2 (2.00g, 5mmol), phenoxazine (2.2g, 12mmol), palladium acetate (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate (0.34g, 1.2mmol) in 100mL two-necked flask mmol), then sodium tert-butoxide (1.16 g, 12 mmol) was added into the glove box, and 60 mL of toluene previously 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, 2:1) to obtain 2.2 g of compound 2 as a green powder, yield 72%.

[0053] 1 H NMR (300MHz, CD 2 Cl 2 ,δ): 8.11 (s, 2H), 7.62-7.48 (m, 5H), 7.14-7.07 (m, 4H), 7.03-6.96 (m, 12H), 6.70 (s, 2H).

[0054] MS(EI)m / z:[M] + calcd for C 40 ...

Embodiment 3

[0056] The synthetic route of target compound 3 is as follows:

[0057]

[0058] Add raw material 3 (2.00g, 5mmol), phenoxazine (2.2g, 12mmol), palladium acetate (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate (0.34g, 1.2mmol) in 100mL two-necked flask mmol), then sodium tert-butoxide (1.16 g, 12 mmol) was added into the glove box, and 60 mL of toluene previously 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, 2:1) to obtain 1.3 g of compound 3 as a green powder, yield 43%.

[0059] 1 H NMR (300MHz, CD 2 Cl 2 ,δ): 8.14 (s, 2H), 7.92 (d, J=6.3Hz, 1H), 7.14-7.07 (m, 4H), 7.03-6.96 (m, 13H).

[0060] MS(EI)m / z:[M] + calcd for C 40 h 25 N ...

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Abstract

The present invention involves a thermal activation delayed fluorescent material and its preparation method and the mechanical electrical light emitting diode device.group.The thermal activation delayed fluorescence material of the present invention has a high -speed reverse system and a high -retirement efficiency. It is a green TADF material with a significant TADF characteristic.It can effectively improve the luminous efficiency of the mechanical and electrical light -emitting diode device, and the mechanical electrical light -emitting diode device based on thermal activation delayed fluorescent materials based on the invention has very high device efficiency.

Description

technical field [0001] The invention belongs to the technical field of electroluminescent materials, and in particular relates to a thermally activated delayed fluorescent material, a preparation method thereof and an organic electroluminescent diode device. Background technique [0002] Organic light-emitting diode (Organic Light-Emitting Diode, OLED) display panel does not need a backlight source for its active light emission, high luminous efficiency, large viewing angle, fast response speed, wide temperature range, relatively simple production and processing technology, and easy to drive. The advantages of low voltage, low energy consumption, lighter and thinner, flexible display and huge application prospects have attracted the attention of many researchers. [0003] The principle of an OLED device is that under the action of an electric field, holes and electrons are injected from the anode and cathode respectively, pass through the hole injection layer, the hole trans...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/14C09K11/06H01L51/50H01L51/54
CPCC07D471/14C09K11/06C09K2211/1029C09K2211/1033H10K85/657H10K85/6572H10K50/12H10K50/11H10K50/16H10K50/15H10K50/17
Inventor 罗佳佳严舒星
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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