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

A technology of heat-activated delay and fluorescent materials, which is applied in the direction of luminescent materials, electric solid devices, chemical instruments and methods, etc., can solve the problems of limited applications, and achieve the effects of poor color gamut, high yield and high device efficiency

Active Publication Date: 2021-06-01
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

And because the TADF material has a very wide spectrum and a microsecond-scale exciton lifetime, its application in mass-produced device structures is greatly limited.

Method used

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  • Thermally activated delayed fluorescent material and preparation method thereof and organic electroluminescent diode device
  • Thermally activated delayed fluorescent material and preparation method thereof and organic electroluminescent diode device
  • Thermally activated delayed fluorescent material and preparation method thereof 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] Add raw material 1 (2.68g, 5mmol), 9,10-dihydro-9,9-diphenylacridine (2.00g, 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 200 mL of 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, 3:1) to obtain 2.0 g of compound 1 as blue-white powder, yield 51%.

[0047] 1HNMR (300MHz, CD 2 Cl 2 ,δ): 7.73 (d, J=6.3Hz, 2H), 7.38 (d, J=6.9Hz, 2H), 7.26-7.07 (m, 14H), 6.95-6.83 (m, 4H).

[0048]MS(E...

Embodiment 2

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

[0051]

[0052] Add raw material 2 (2.68g, 5mmol), 9,10-dihydro-9,9-diphenylacridine (2.00g, 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 200 mL of 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, 3:1) to obtain 1.6 g of compound 2 as blue-white powder, yield 41%.

[0053] 1 H NMR (300MHz, CD 2 Cl 2 ,δ): 7.57 (s, 1H), 7.43-7.33 (m, 3H), 7.26-7.07 (m, 14H), 6.95-6.83 (m, 4H).

[0054] MS(EI)m / z:[M] + calcd for C 43 h 22 f 10 NOP, 789.1...

Embodiment 3

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

[0057]

[0058] Add raw material 3 (2.68g, 5mmol), 9,10-dihydro-9,9-diphenylacridine (2.00g, 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 200 mL of 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, 3:1) to obtain 1.0 g of compound 3 as blue-white powder, yield 25%.

[0059] 1 H NMR (300MHz, CD 2 Cl 2 ,δ):7.73(d,J=6.9Hz,1H),7.54-7.38(m,2H),7.32(d,J=6.3Hz,1H),7.26-7.07(m,14H),6.95-6.83( m, 4H).

[0060] MS(EI)m / z:[M] + calcd for C 43 h 2...

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Abstract

The present invention relates to a thermally activated delayed fluorescent material and its preparation method and an organic electroluminescent diode device. The general structural formula of the thermally activated delayed fluorescent material is shown in the following formula 1: Formula 1 R represents a chemical group as an electron donor group. The thermally activated delayed fluorescent material of the present invention has an ultrafast reverse intersystem crossing rate and high luminous efficiency, and is a blue light TADF material with significant TADF characteristics and high energy level. The present invention utilizes the 100% internal quantum utilization efficiency of the TADF material to The thermally activated delayed fluorescent material is used as the main material of traditional fluorescent materials in organic electroluminescent diode devices, which enables fluorescent devices to achieve device efficiency comparable to phosphorescent devices of phosphorescent heavy metal complexes, and greatly improves the utilization rate of excitons. , At the same time, it solves the problems of poor color gamut and long lifetime of excitons caused by directly using TADF material as the material of the light-emitting layer.

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): C07F9/64C09K11/06H01L51/54
CPCC07F9/64C09K11/06
Inventor 罗佳佳严舒星
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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