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Thermally-activated delayed fluorescent material, preparation method thereof, and organic light-emitting diode device

A technology of heat-activated delayed and fluorescent materials, applied in the direction of luminescent materials, electrical solid devices, chemical instruments and methods, etc., can solve the problems of lack of heavy metal Ir complexes, etc., achieve high device efficiency and improve luminous efficiency

Active Publication Date: 2019-07-12
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, preparation method thereof, and organic light-emitting diode device
  • Thermally-activated delayed fluorescent material, preparation method thereof, and organic light-emitting diode device
  • Thermally-activated delayed fluorescent material, preparation method thereof, and organic light-emitting 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 invention relates to a thermally-activated delayed fluorescent material, a preparation method thereof, and an organic light-emitting diode device. The structural general formula of the thermally-activated delayed fluorescent material is represented by formula 1 shown in the description; and R in the formula 1 represents a chemical group used as an electron donor. A strong electron-withdrawinggroup with a large conjugate plane, which is used as an electron acceptor, is combined with a strong electron donor to design the dark red thermally-activated delayed fluorescent material with remarkable TADF characteristics and a low energy level. The thermally-activated delayed fluorescent material is the dark red TADF material with a low single-triplet state energy level difference, an ultrafast reverse intersystem crossing rate and a high luminous efficiency, and can effectively improve the luminous efficiency of the organic light-emitting diode device when applied to the organic light-emitting diode device as a luminescent material, and the organic light-emitting diode device based on the thermally-activated delayed fluorescent material has a 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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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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