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Thermally activated delayed fluorescence material, preparation method thereof and organic electroluminescent 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 affecting the stability of OLED devices, fast efficiency decay speed, OLED device efficiency decline, etc., to achieve enhanced absorption The effect of electronic ability, reduction of interaction, and improvement of light extraction efficiency

Active Publication Date: 2020-06-12
WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The embodiments of the present application provide a thermally activated delayed fluorescent material and its preparation method and an organic electroluminescent device to solve the problem that the efficiency of the existing thermally activated delayed fluorescent material dedicated to OLED devices decays quickly, resulting in a significant drop in the efficiency of OLED devices. , which in turn affects the technical issues of the stability of OLED devices

Method used

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  • Thermally activated delayed fluorescence material, preparation method thereof and organic electroluminescent device
  • Thermally activated delayed fluorescence material, preparation method thereof and organic electroluminescent device
  • Thermally activated delayed fluorescence material, preparation method thereof and organic electroluminescent device

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preparation example Construction

[0040] Such as figure 1 As shown, based on the above purpose, the embodiment of the present application also provides a preparation method of the above-mentioned thermally activated delayed fluorescent material, which includes the following steps:

[0041] S10, adding a catalyst, a basic substance, and a solvent to the first reactant and the second reactant, the first reactant being a bromide of cyclopentane[def]fluorene-4,8-dione;

[0042] S20, a substitution reaction occurs between the first reactant and the second reactant to obtain a reaction solution;

[0043] S30, performing impurity removal treatment on the reaction solution to obtain the general structural formula: The thermally activated delayed fluorescence material, R 1 -R 6 is the electron donor unit.

[0044] The second reactant can be R 1 hydride, R 2 hydride, R 3 hydride, R 4 hydride, R 5 The hydride, and R 6 Any one or more combinations of the hydrides.

[0045] The catalyst may be a palladium catal...

Embodiment 1

[0054] The first reactant in this example is 2,6-dibromocyclopentane[def]fluoren-4,8-dione, and the second reactant is 9,10-dihydro-9,9-dimethyl Acridine, the catalyst is three (dibenzylideneacetone) dipalladium, the catalyst ligand is two (2-diphenylphosphophenyl) ethers, and the molar ratio of the first reactant and the second reactant is 1:2.1 . The first reactant and the second reactant have a substitution reaction to synthesize the target compound 1, and the structural formula of the target compound 1 is: The synthetic route of target compound 1 is as follows:

[0055]

[0056] Specifically, 2,6-dibromocyclopentane[def]fluorene-4,8-dione (3.64g, 10mmol), 9,10-dihydro-9,9-dimethyl Acridine (4.40g, 21mmol), tris(dibenzylideneacetone)dipalladium (92mg, 0.1mmol), bis(2-diphenylphosphophenyl)ether (108mg, 0.2mmol) and sodium tert-butoxide (2.0g, 21mmol), pumped three times, injected 80mL of anhydrous toluene under argon atmosphere, and then reacted at 80°C for 24 hours....

Embodiment 2

[0068] The synthesis method of the target compound 2 provided in this example is the same as in Example 1, except that the first reactant is 1,7-dibromocyclopentane[def]fluorene-4,8-dione, and the target compound The structural formula of 2 is The synthetic route of target compound 2 is as follows:

[0069]

[0070]Specifically, 1,7-dibromocyclopentane[def]fluorene-4,8-dione (3.64g, 10mmol), 9,10-dihydro-9,9-dimethyl Acridine (4.40g, 21mmol), tris(dibenzylideneacetone)dipalladium (92mg, 0.1mmol), bis(2-diphenylphosphophenyl)ether (108mg, 0.2mmol) and sodium tert-butoxide (2.0g, 21mmol), pumped three times, injected 80mL of anhydrous toluene under argon atmosphere, and then reacted at 80°C for 24 hours. After the reaction was cooled to room temperature, the reaction solution was poured into 200 mL of saturated brine, and a red solid was obtained by suction filtration, which was separated and purified by column chromatography (eluent: dichloromethane:n-hexane, v:v, 1:1), ...

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Abstract

The invention relates to a thermally activated delayed fluorescence material, a preparation method thereof and an organic electroluminescent device. The preparation method comprises the following steps: adding a catalyst, an alkaline substance and a solvent into a first reactant and a second reactant, wherein the first reactant is a bromide of cyclopenta[def]fluorene-4,8-dione; carrying out a substitution reaction on the first reactant and the second reactant to obtain a reacted solution; and carrying out impurity removal treatment on the reacted solution to obtain the thermally activated delayed fluorescence material with a structural general formula shown in the specification. Cyclopenta[def]fluorene-4,4'-dicarboxylic acid is used as a receptor unit, the triplet state energy level of thereceptor unit can be reduced, and the intramolecular charge transfer state property of the receptor unit can be enhanced to achieve luminescent red shift of molecules; and in addition, the interaction between luminescent molecules is reduced by adjusting the number of donor units and the binding positions of the donor units and the receptor unit, so the light extraction efficiency of the luminescent molecules is improved.

Description

technical field [0001] The present application relates to the field of display technology, in particular to a thermally activated delayed fluorescent material, a preparation method thereof, and an organic electroluminescence device. Background technique [0002] Photoelectric conversion efficiency is an important parameter for evaluating OLED (Organic Light-Emitting Diode, organic light-emitting diode). Since the advent of organic light-emitting diodes, in order to improve the luminous efficiency of organic light-emitting diodes, various light-emitting material systems based on fluorescence and phosphorescence have been developed. . OLEDs based on fluorescent materials have the characteristics of high stability, but are limited by the law of quantum statistics. Under the action of electric activation, the ratio of singlet excited state excitons to triplet excited state excitons is 1:3, so traditional The internal electroluminescent quantum efficiency of fluorescent material...

Claims

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Application Information

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IPC IPC(8): C07D219/02C09K11/06H01L51/54H01L51/50
CPCC07D219/02C09K11/06C09K2211/1011C09K2211/1029H10K85/622H10K85/6572H10K50/11H10K2101/20C09K2211/1007C07D401/10C07D401/14C09K2211/1096
Inventor 吴凯龙张曲
Owner WUHAN CHINA STAR OPTOELECTRONICS SEMICON DISPLAY TECH CO LTD
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