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Thermally activated delayed fluorescent material and preparation method thereof

A technology of thermally activated delayed and fluorescent materials, applied in the fields of luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problem of low efficiency and so on

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

AI Technical Summary

Problems solved by technology

[0003] The invention provides a thermally activated delayed fluorescent material and a preparation method thereof, which solves the technical problems that the existing TADF small molecule blue light material and its electroluminescent device have low efficiency and are prone to aggregation quenching luminescence effect

Method used

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  • Thermally activated delayed fluorescent material and preparation method thereof
  • Thermally activated delayed fluorescent material and preparation method thereof
  • Thermally activated delayed fluorescent material and preparation method thereof

Examples

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Embodiment 1

[0016] At room temperature, the 1,3,3a 1 , 4,6,7,9-Naphthalene (1.73g, 10mmol) was added to a 100ml single-port reaction flask, and then an appropriate amount of solvent DMF was added until 1,3,3a 1 , 4,6,7,9-Naphthalene was completely dissolved (about 80ml), liquid bromine (2ml, 40mmol) was dissolved in 3ml of DMF solution, added dropwise to the reaction system, and reacted in the dark for 4 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 was separated and purified by column chromatography to obtain 2,5,8-tribromo-1,3,3a 1 , 4,6,7,9-heptaazyridine (3.07g, yield 76%), its chemical reaction equation is:

[0017]

Embodiment 2

[0019] N, N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (18.56g, 50mmol) 2,5 ,8-Tribromo-1,3,3a 1 , 4,6,7,9-heptaazyridine (4.09g, 10mmol) and catalyst Pd(PPh 3 ) 4 (0.74 g, 0.6 mmol) were mixed in toluene (80 mL). Will K 2 CO 3 Aqueous solution (5.2 g, 38.5 mmol) was slowly added to the reaction mixture, and after bubbling nitrogen for 30 min, the reaction mixture was heated to 80° C. under nitrogen and refluxed for 10 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 (compound 1) (5.02g, productive rate 65%) shown in formula (I), its chemical reaction equation is:

[0020]

Embodiment 3

[0022] The difference between this example and Example 2 is: the reaction time of Example 2 was 10 h, and the reaction time of this example was 14 h, and compound 2 (5.41 g, yield 64%) was finally obtained.

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Abstract

The invention belongs to the technical field of photoelectric display devices, and particularly relates to a thermally activated delayed fluorescent material and a preparation method thereof. The structural formula of the thermally activated delayed fluorescent material is shown as a formula (I). The invention also provides the preparation method of the thermally activated delayed fluorescent material. The preparation method comprises the following step: reacting N, N-diphenyl-4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl)aniline with 2, 5, 8-tribromo-1, 3, 3a1, 4, 6, 7, 9-heptaazanaphthalene to obtain the compound as shown in the formula (I). The invention provides the thermally activated delayed fluorescence material and the preparation method thereof to solve the technical problems that the efficiency of the existing TADF micromolecule blue light material and the electroluminescent device thereof is not high, and the aggregation quenching luminescence effect is easy to generate.

Description

technical field [0001] The invention belongs to the technical field of photoelectric display devices, and in particular relates to a thermally activated 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. In 2012, Professor Adachi of Kyushu University in Japan discovered a thermally activated delayed fluorescence (TADF) new material based on triplet-singlet transition, which has an efficiency close to 100% and can solve the problem of blue light. This new material has just been disco...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/16C09K11/06
CPCC07D487/16C09K11/06C09K2211/1007C09K2211/1014C09K2211/1074
Inventor 樊嘉政
Owner 广州万物物联科技有限公司
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