Thermally-activated delayed fluorescent material, preparation method thereof, and organic light-emitting diode device

A technology for heat-activated delayed and fluorescent materials, applied in luminescent materials, electrical solid devices, chemical instruments and methods, etc., can solve problems such as the lack of heavy metal Ir complexes, achieve low singlet triplet energy level difference, improve luminous efficiency, and high Effect of Device Efficiency

Inactive Publication Date: 2019-07-12
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, preparation method thereof, and organic light-emitting diode device
  • Thermally-activated delayed fluorescent material, preparation method thereof, and organic light-emitting diode device
  • Thermally-activated delayed fluorescent material, preparation method thereof, and organic light-emitting diode device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The synthetic route of target compound 1 is as follows:

[0044]

[0045] Add raw material 1 (2.09g, 5mmol) in 100mL two-necked flask, 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, 3:2) to obtain 1.8 g of compound 1 as grass-green powder, yield 66%.

[0046] 1HNMR (300MHz, CD 2 Cl 2 ,δ): 8.73 (s, 2H), 8.36 (d, J=6.3Hz, 2H), 7.14-6.90 (m, 18H).

[0047] MS(EI)m / z:[M] + calcd for C 35 h 22 N 4 o 3 ...

Embodiment 2

[0049] The synthetic route of target compound 2 is as follows:

[0050]

[0051] Add raw material 2 (2.09g, 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, 3:2) to obtain 1.6 g of compound 2 as grass-green powder, yield 59%.

[0052] 1 H NMR (300MHz, CD 2 Cl 2 ,δ): 8.41 (s, 2H), 8.24 (s, 2H), 7.68 (s, 2H), 7.14-6.90 (m, 16H).

[0053] MS(EI)m / z:[M] + calcd for C 35 h 22 N 4 o 3 , 546...

Embodiment 3

[0055] The synthetic route of target compound 3 is as follows:

[0056]

[0057] Add raw material 3 (2.09g, 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, 3:2) to obtain 1.3 g of compound 3 as a green powder, yield 48%.

[0058] 1 H NMR (300MHz, CD 2 Cl 2 ,δ): 8.17 (s, 2H), 7.72 (d, J=6.3Hz, 2H), 7.14-6.90 (m, 16H), 6.75 (d, J=6.6Hz, 2H).

[0059] MS(EI)m / z:[M] + calcd for C 35 h 22...

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Abstract

The invention relates to a thermally-activated delayed fluorescent material, a preparation method thereof, and an organic light-emitting diode device. The structural general formula of the thermally-activated delayed fluorescent material is represented by formula 1 shown in the description; and in the formula 1, R represents a chemical group used as an electron donor, the R is located at the firstposition, the third position, the fourth position or the fifth position of a pyridyl group, and X is one of formulas also shown in the description. The thermally-activated delayed fluorescent material has an ultrafast reverse intersystem crossing rate and a high luminous efficiency, is a blue-green light TADF material having remarkable TADF characteristics, and can effectively improve the luminous efficiency of the organic light-emitting diode device when applied to the organic light-emitting diode device as a luminescent layer material, and the organic light-emitting diode device based on the thermally-activated delayed fluorescent material has a 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 Applications(China)
IPC IPC(8): C07D413/14C09K11/06H01L51/50H01L51/54
CPCC07D413/14C09K11/06C09K2211/1029C09K2211/1033H10K85/657H10K50/11
Inventor 罗佳佳
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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