Bipolar thermal activation delayed fluorescent material, preparation method thereof and organic electroluminescent diode device

A thermal activation delay, fluorescent material technology, applied in the direction of luminescent materials, electrical solid devices, chemical instruments and methods, etc., can solve the problems of unbalanced OLED turn-on voltage and life, single carrier transport properties, high turn-on voltage, etc. Achieve the effects of improving efficiency and stability, improving exciton utilization, and carrier transport balance

Inactive Publication Date: 2019-07-05
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

[0007] Traditional host materials usually only have a single carrier transport property, and this unbalanced carrier transport property has been shown to be detrimental to the turn-on voltage and lifetime of OLEDs.
The development of new host materials must have good bipolar carrier (hole and electron) injection and transport properties to avoid the accumulation of carriers between the light-emitting layer and the charge-transport layer, causing the exciplexes at the interface to emit light , resulting in low external quantum efficiency, power efficiency, current efficiency and other main parameters of the device, high turn-on voltage, and spectral instability.

Method used

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  • Bipolar thermal activation delayed fluorescent material, preparation method thereof and organic electroluminescent diode device
  • Bipolar thermal activation delayed fluorescent material, preparation method thereof and organic electroluminescent diode device
  • Bipolar thermal activation delayed fluorescent material, preparation method thereof and organic electroluminescent diode device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The synthetic route of target compound 1 is as follows:

[0052]

[0053] Add raw material 1 (1.93g, 5mmol), 9,10-dihydro-9,9-dimethylacridine (1.25g, 6mmol), palladium acetate Pb (OAc) (45mg, 0.2mmol) in 100mL two-necked flask ) and tri-tert-butylphosphine tetrafluoroborate (t-Bu) 3 HPBF 4 (0.17g, 0.6mmol), then add sodium tert-butoxide NaOt-Bu (0.58g, 6mmol) in the glove box, inject 40mL of toluene that has been dehydrated and deoxygenated in advance under an argon atmosphere, and 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, 3:2) to obtain 2.3 g of compound 1 as a white powder, yield 89%.

[0054] 1HNMR (300MHz, CD2Cl2, δ): 7.62(d, J=6.3Hz, 2H), 7.35(d, J=6.6Hz, 2H), 7.19-7.14(m, 6H), 6.95-6.90(m, 2H) ,1.69(s,6H).

[0055] MS(EI)m...

Embodiment 2

[0057] The synthetic route of target compound 2 is as follows:

[0058]

[0059] Add raw material 2 (1.93g, 5mmol), 9,10-dihydro-9,9-dimethylacridine (1.25g, 6mmol), palladium acetate (45mg, 0.2mmol) and three tert-tert Butylphosphine tetrafluoroborate (0.17g, 0.6mmol), then sodium tert-butoxide (0.58g, 6mmol) was added in the glove box, and 40mL of toluene, which had been dehydrated and deoxygenated in advance, was injected 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, 3:2) to obtain 1.7 g of compound 2 as white powder, yield 66%.

[0060] 1 H NMR (300MHz, CD 2 Cl 2 ,δ): 7.69 (d, J=6.0Hz, 1H), 7.52-7.44 (m, 3H), 7.19-7.14 (m, 6H), 6.95-6.90 (m, 2H), 1.69 (s, 6H).

[0061] MS(EI)m / z:[M] + calcd for C 27 h 18 f ...

Embodiment 3

[0063] The synthetic route of target compound 3 is as follows:

[0064]

[0065] Add raw material 3 (1.93g, 5mmol), 9,10-dihydro-9,9-dimethylacridine (1.25g, 6mmol), palladium acetate (45mg, 0.2mmol) and three tert-tert Butylphosphine tetrafluoroborate (0.17g, 0.6mmol), then sodium tert-butoxide (0.58g, 6mmol) was added in the glove box, and 40mL of toluene, which had been dehydrated and deoxygenated in advance, was injected 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, 3:2) to obtain 1.1 g of compound 3 as a white powder, yield 43%.

[0066] 1 H NMR (300MHz, CD 2 Cl 2 ,δ): 7.72 (d, J=6.3Hz, 2H), 7.35-7.29 (m, 3H), 7.19-7.14 (m, 6H), 6.95-6.90 (m, 2H), 1.69 (s, 6H).

[0067] MS(EI)m / z:[M] + calcd for C 27 h 18 f...

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Abstract

The invention relates to a bipolar thermal activation delayed fluorescent material, a preparation method thereof and an organic electroluminescent diode device. The bipolar thermal activation delayedfluorescent material has the general structure shown in formula 1, the top of the formula 1, the middle of the formula 1, wherein R1 represents a chemical group taken as an electron acceptor and R2represents a chemical group taken as an electron donor: According to the invention, 100% of internal quantum utilization efficiency of a TADF material is utilized, and the bipolar thermal activation delayed fluorescent material is used as a main materialof the traditional fluorescent material andis applied to the organic electroluminescent diode device, so that a fluorescent device can achieve the device efficiency comparable to that of a phosphorescent device of a phosphorescent heavy metal complex, the exciton utilization rate is greatly improved, meanwhile, the problems of poor color gamut, long exciton service life and the like caused by directly using the TADF material as a luminescent layer material are solved.

Description

technical field [0001] The invention belongs to the technical field of electroluminescent materials, and in particular relates to a bipolar 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 ho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02C09K11/06H01L51/50H01L51/54
CPCC07D219/02C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029H10K85/6572H10K50/121
Inventor 罗佳佳严舒星
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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