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Thermally activated delayed fluorescence compound, preparation method thereof and organic light emitting diode device

A technology of thermally activated delayed and fluorescent compounds, which is applied in the fields of electric solid state devices, chemical instruments and methods, electrical components, etc., can solve the problem of lack of heavy metal Ir complexes, etc., and achieve high device efficiency and improve luminous efficiency.

Active Publication Date: 2019-03-22
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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  • Thermally activated delayed fluorescence compound, preparation method thereof and organic light emitting diode device
  • Thermally activated delayed fluorescence compound, preparation method thereof and organic light emitting diode device
  • Thermally activated delayed fluorescence compound, preparation method thereof and organic light emitting diode device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The synthetic route of target compound 1 is as follows:

[0043]

[0044] Add raw material 1 (2.56g, 5mmol), 9,10-dihydro-9,9-dimethylacridine (3.76g, 18mmol), palladium acetate Pb (OAc) (135mg, 0.6mmol) in 100mL two-necked flask ) and tri-tert-butylphosphine tetrafluoroborate (t-Bu) 3 HPBF 4 (0.51g, 1.8mmol), then sodium tert-butoxide NaOt-Bu (1.74g, 18mmol) was added in the glove box, and 40mL 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, 1:1) to obtain 3.0 g of compound 1 as blue-white powder, yield 66%.

[0045] 1H NMR (300MHz, CD2Cl2, δ): 7.19-7.14 (m, 18H), 6.95 (d, J=6.9Hz, 6H), 1.69 (s, 18H).

[0046] MS(EI)m / z:[M] + calcd for C...

Embodiment 2

[0048] The synthetic route of target compound 2 is as follows:

[0049]

[0050]Add raw material 1 (2.56g, 5mmol), phenoxazine (3.30g, 18mmol), palladium acetate (135mg, 0.6mmol) and tri-tert-butylphosphine tetrafluoroborate (0.51g, 1.8mmol) in 100mL two-necked flask mmol), then sodium tert-butoxide (1.74 g, 18 mmol) was added into the glove box, and 40 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, 1:1) to obtain 2.7 g of compound 2 as blue-white powder, yield 65%.

[0051] 1 H NMR (300MHz, CD 2 Cl 2 ,δ): 7.14 (d, J=7.2Hz, 6H), 7.01-6.96 (m, 18H).

[0052] MS(EI)m / z:[M] + calcd for C 45 h 24 f 9 N 3 o 3 , 825.17; found, ...

Embodiment 3

[0054] The synthetic route of target compound 3 is as follows:

[0055]

[0056] Add raw material 1 (2.56g, 5mmol), phenothiazine (3.59g, 18mmol), palladium acetate (135mg, 0.6mmol) and tri-tert-butylphosphine tetrafluoroborate (0.51g, 1.8mmol) into a 100mL two-necked flask. mmol), then sodium tert-butoxide (1.74 g, 18 mmol) was added into the glove box, and 40 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, 1:1) to obtain 2.8 g of compound 3 as blue-white powder, yield 64%.

[0057] 1 H NMR (300MHz, CD 2 Cl 2 ,δ):7.16-7.08(m,12H),7.04-6.98(m,12H).

[0058] MS(EI)m / z:[M] + calcd for C 45 h 24 f 9 N 3 S 3 ,873.10; found, 87...

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Abstract

The invention relates to a thermally activated delayed fluorescence compound, a preparation method thereof and an organic light emitting diode device. The structural general formula of the thermally activated delayed fluorescence compound is shown in formula I as shown in specification, and R shows a chemical group as an electron donor. Trifluoromethyl (-CF3) serves as a strong electron donor group, the electron donor group is changed by matching different functional groups, influences of the intensity of the electron donor to properties of a material are researched, and the sky blue thermallyactivated delayed fluorescence compound with remarkable TADF characteristic is designed. The thermally activated delayed fluorescence compound is a sky blue TADF compound with ultra-fast reverse intersystem crossing rate and high luminous efficiency, therefore, when the thermally activated delayed fluorescence compound as a luminous material is applied to the organic light emitting diode device,the luminous efficiency of the organic light emitting diode device can be improved effectively, and the organic light emitting diode device based on the thermally activated delayed fluorescence compound has quite 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 compound, 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): C07D219/14C07D265/38C07D279/26C09K11/06H01L51/54
CPCC09K11/06C07D219/14C07D265/38C07D279/26C09K2211/1033C09K2211/1037C09K2211/1029H10K85/657H10K85/6572
Inventor 罗佳佳
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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