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Thermally activated delayed fluorescent material and preparation method thereof, and organic electroluminescent 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

Active Publication Date: 2021-08-24
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 with the above conditions are still relatively scarce compared with heavy metal Ir complexes, and heavy metal complex phosphorescent materials have yet to break through in the field of deep red light. Therefore, it is particularly important to develop deep red light TADF materials with high performance. the meaning of

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] 9,10-dihydro-9,9-dimethylacridine (2.51g, 12mmol) was added into a 100mL two-necked flask, and then sodium hydride NaH (0.48g, 12mmol) was added in the glove box. Add 40 mL of tetrahydrofuran (THF) that had been dehydrated and deoxygenated beforehand, react at 60°C for 2 hours, then add raw material 1 (5mmol, 1.35g), and react at 60°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 2.0 g of compound 1 as orange-red powder, yield 62%.

[0047] 1HNMR (300 MHz, CD 2 Cl 2 ,δ): 8.74 (s, 4H), 7.19-7.14 (m, 12H), 6.98-6.93 (m, 4H), 1.69 (s, 12H).

[0048] MS(EI)m / z:[M] + calcd for C 42 h 32 N 8 , 648.27; found, 648.18.

Embodiment 2

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

[0051]

[0052] Add phenoxazine (2.20g, 12mmol) into a 100mL two-necked bottle, then add NaH (0.48g, 12mmol) into the glove box, inject 40mL of tetrahydrofuran that has been dehydrated and deoxygenated beforehand under an argon atmosphere, and put it at 60°C After reacting for 2 hours, raw material 1 (5 mmol, 1.35 g) was added, and reacted at 60° 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 1.9 g of compound 2 as a red powder, yield 64%.

[0053] 1 H NMR (300MHz, CD 2 Cl 2 ,δ): 8.74 (s, 4H), 7.14-7.06 (m, 4H), 7.01-6.95 (m, 12H).

[0054] MS(EI)m / z:[M] + calcd for C 36 h 20 N 8 o 2 , 596.17; found, 596.16.

Embodiment 3

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

[0057]

[0058] Add phenothiazine (2.39g, 12mmol) into a 100mL two-necked flask, then add NaH (0.48g, 12mmol) into the glove box, inject 40mL of tetrahydrofuran that has been dehydrated and deoxygenated beforehand under an argon atmosphere, and put it at 60°C After reacting for 2 hours, raw material 1 (5 mmol, 1.35 g) was added, and reacted at 60° 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 1.5 g of compound 3 as dark red powder, yield 48%.

[0059] 1 H NMR (300MHz, CD 2 Cl 2 ,δ): 8.74 (s, 4H), 7.21-7.13 (m, 12H), 6.97-6.88 (m, 4H).

[0060] MS(EI)m / z:[M] + calcd for C 36 h 20 N 8 S 2 , 628.13; found, 628.10.

[0061] figure 1 shows the orbital arrangement of compoun...

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Abstract

The present invention relates to a thermally activated delayed fluorescent material, a preparation method thereof and an organic electroluminescent diode device. The general structural formula of the thermally activated delayed fluorescent material is shown in the following formula 1: in the above formula 1, R represents The chemical group of the donor. In the present invention, a strong electron-withdrawing group with a large conjugated plane is used as an electron acceptor, and by combining the electron acceptor with a strong electron donor, a deep red photothermally activated delayed fluorescence with significant TADF characteristics and low energy level is designed Material. The thermally activated delayed fluorescent material of the present invention is a deep red TADF material with lower single triplet energy level difference, ultrafast reverse intersystem crossing rate and high luminous efficiency, when it is used as a luminescent material in organic electroluminescence When used as a diode device, the luminous efficiency of the organic electroluminescent diode device can be effectively improved, and the organic electroluminescent diode device based on the thermally activated delayed fluorescent material of the present invention has 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 Patents(China)
IPC IPC(8): C07D487/14C07F7/08C09K11/06H01L51/50H01L51/54
CPCC07D487/14C07F7/0816C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104C09K2211/1044C09K2211/1096H10K85/657H10K85/6572H10K85/40H10K50/11
Inventor 罗佳佳李先杰顾宇黄金昌王煦
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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