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Thermally activated delayed fluorescence compound and its preparation method and organic electroluminescent diode device

A technology of heat-activated delayed and fluorescent compounds, which is applied in the fields of electric solid-state devices, chemical instruments and methods, organic chemistry, etc., can solve the problems of lack of heavy metal Ir complexes, achieve high device efficiency, and improve the effect of luminous efficiency

Active Publication Date: 2020-06-02
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 and its preparation method and organic electroluminescent diode device
  • Thermally activated delayed fluorescence compound and its preparation method and organic electroluminescent diode device
  • Thermally activated delayed fluorescence compound and its preparation method and organic electroluminescent 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 (2.56g, 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%.

[0046] 1H NMR (300MHz, CD2Cl2, δ): 7.19-7.14 (m, 18H), 6.95 (d, J=6.9Hz, 6H), 1.69 (s, 18H).

[0047] MS(EI)m / z:[M] + calcd for C...

Embodiment 2

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

[0050]

[0051] 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%.

[0052] 1 H NMR (300MHz, CD 2 Cl 2 ,δ): 7.14 (d, J=7.2Hz, 6H), 7.01-6.96 (m, 18H).

[0053] MS(EI)m / z:[M] + calcd for C 45 h 24 f 9 N 3 o 3 , 825.17; found, 8...

Embodiment 3

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

[0056]

[0057] 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%.

[0058] 1 H NMR (300MHz, CD 2 Cl 2 ,δ):7.16-7.08(m,12H),7.04-6.98(m,12H).

[0059] 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 present invention relates to a thermally activated delayed fluorescent compound and its preparation method and an organic electroluminescent diode device. The general structural formula of the thermally activated delayed fluorescent compound is shown in the following formula 1: Formula 1 R represents a chemical group as an electron donor group. The present invention adopts trifluoromethyl (-CF 3 ) as a strong electron acceptor group, by matching different functional groups, changing the electron donor group, studying the influence of the strength of the electron donor on the material properties, and designing a thermal activation of sky blue light with significant TADF characteristics Delayed fluorescence compounds. The thermally activated delayed fluorescence compound of the present invention is a sky blue light TADF compound with ultrafast reverse intersystem crossing rate and high luminous efficiency. Therefore, when it is used as a luminescent material in an organic electroluminescent device, it can effectively improve the efficiency. Luminous Efficiency of Electromechanical Luminescent Devices Organic electroluminescent devices based on thermally activated delayed fluorescence compounds of the present invention have very high device efficiencies.

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 Patents(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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