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Multifunctional delayed fluorescence material and preparation method thereof

A delayed fluorescence and multifunctional technology, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the problem of low efficiency of TADF small molecule red light materials, and achieve the improvement of external quantum efficiency and luminous intensity , Improve the effect of charge transfer effect

Inactive Publication Date: 2021-08-31
广州万物物联科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The invention provides a multifunctional delayed fluorescent material and a preparation method thereof, which solves the technical problem that the efficiency of the existing TADF small molecule red light material is not high, and it is easy to produce aggregation quenching luminescent effect

Method used

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  • Multifunctional delayed fluorescence material and preparation method thereof
  • Multifunctional delayed fluorescence material and preparation method thereof
  • Multifunctional delayed fluorescence material and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0022] At room temperature, the compound (2.69g, 10mmol) shown in the formula (V) was added in a 100ml single-port reaction flask, and then an appropriate amount of solvent THF was added until the compound shown in the formula (V) was completely dissolved (about 80ml), and the liquid bromine ( 2ml, 40mmol) was dissolved in 3ml of THF solution, added dropwise to the reaction system, and reacted in the dark for 8 hours. Add water to stop the reaction, extract with DCM, wash several times with a large amount of deionized water, collect the organic liquid, and concentrate. The crude product is separated and purified by column chromatography to obtain compound (2.089g, yield 60%) shown in formula (IV), and its chemical reaction equation is:

[0023]

Embodiment 2

[0025] With 4,4,5,5-tetramethyl-2-(pyran-1-yl)-1,3,2-dioxaborane (4.92g, 15mmol), compound shown in formula (IV) ( 3.48g, 10mmol) and catalyst Pd (PPh 3 ) 4 (0.62 g, 0.5 mmol) were mixed in toluene (80 mL). Will K 2 CO 3 Aqueous solution (2.03 g, 15 mmol) was slowly added to the reaction mixture, and after bubbling nitrogen for 30 min, the reaction mixture was heated to 85° C. under nitrogen and refluxed for 12 h (reaction progress was monitored by TLC). After the reaction was complete, it was diluted with ethyl acetate (150 mL). The organic layer was washed with brine solution, water and washed with anhydrous Na 2 SO 4 Dry, filter, and remove solvent in vacuo, obtain compound (3.18g, productive rate 68%) shown in product formula (III), its chemical reaction equation is:

[0026]

Embodiment 3

[0028] Add the compound represented by formula (III) (11.7g, 25mmol), glacial acetic acid (25ml) and concentrated sulfuric acid (75ml) into a 500ml single-necked bottle at 0-5°C, and stir in the dark. Then N-bromosuccinimide (NBS) (13.9 g, 80 mmol) was added three times, and then gradually raised to room temperature, and reacted overnight. The reaction solution was diluted with a large amount of water, the solid was separated, and then repeatedly washed with NaHCO 3 Aqueous solution, methanol wash several times, after drying, purify with hot chlorobenzene solvent, obtain the compound (13.76g, productive rate 75%) shown in formula (II), its chemical reaction equation is:

[0029]

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Abstract

The invention belongs to the technical field of photoelectric display devices, and particularly relates to a multifunctional delayed fluorescence material and a preparation method thereof. The invention provides the multifunctional delayed fluorescent material, and the structure of the material is shown as a formula (I) shown in the specification. The invention also provides a preparation method of the multifunctional delayed fluorescent material, and the preparation method comprises the following steps: reacting a compound shown as a formula (II) with dibenzoquinoxaline-2,3-dicarbonitrile to prepare the compound shown as the formula (I). The invention provides the multifunctional delayed fluorescence material and the preparation method thereof, and solves the technical problems that an existing TADF micromolecule red light material is not high in efficiency and easily generates an aggregation quenching luminescence effect.

Description

technical field [0001] The invention belongs to the technical field of photoelectric display devices, and in particular relates to a multifunctional delayed fluorescent material and a preparation method thereof. Background technique [0002] In recent years, due to the low efficiency of conventional fluorescent OLEDs and the high cost of phosphorescent OLEDs, scientists have become interested in the development of a new generation of delayed organic electroluminescent materials based on the conversion of triplet excitons to singlet excitons. , such as new organic electroluminescent materials with triplet-triplet delayed fluorescence effect and thermally activated delayed fluorescence effect. Among them, TADF material develops the fastest. Among the existing TADF materials, the current TADF small molecule red light devices still need breakthroughs in the aspects of turn-on voltage, maximum external quantum efficiency and efficiency attenuation, and the device structure is re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/16C09K11/06H01L51/50H01L51/54
CPCC07D491/16C09K11/06C09K2211/1011C09K2211/1044C09K2211/1048H10K85/622H10K85/657H10K85/6572H10K50/11
Inventor 樊嘉政
Owner 广州万物物联科技有限公司
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