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Red delayed fluorescent material based on pyrene unit and preparation method thereof

A delayed fluorescence and red technology, which is applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of few types of red light materials and low device efficiency, so as to improve the utilization rate of excitons and promote backgap crossing The effect of jumping and reducing the energy level difference

Inactive Publication Date: 2021-08-10
南昌万季科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The invention provides a red delayed fluorescent material based on a pyrene unit and a preparation method thereof, which solves the technical problems that the existing red light materials have few types and the device efficiency is not high

Method used

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  • Red delayed fluorescent material based on pyrene unit and preparation method thereof
  • Red delayed fluorescent material based on pyrene unit and preparation method thereof
  • Red delayed fluorescent material based on pyrene unit and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Pyrene (2.02g, 10mmol) was dissolved in 50ml of hydrogen peroxide, and hydrogen bromide (1.21g, 15mmol), a mixed solution of ether and methanol (volume ratio=1:2) was added to the above solution, at 0°C After stirring for 8h, the obtained product was recrystallized in ethanol to obtain the product 1-bromopyrene (2.38g, yield 85%), and its chemical reaction equation was:

[0021]

Embodiment 2

[0023] 1-bromopyrene (2.81g, 10mmol), 2-(dimethyl-13-oxyoxyalkyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborin (3.46gg, 20mmol), 100ml of anhydrous tetrahydrofuran and butyllithium (40mmol) were added to a 250ml three-necked flask, and after argon gas was introduced for 10 minutes, the temperature was lowered to -78°C for 28 hours of reaction. After the reaction was completed, extraction and purification were performed to obtain The product 4,4,5,5-tetramethyl-2-(pyran-1-yl)-1,3,2-dioxaborolane (2.33g, yield 71%), its chemical reaction equation is :

[0024]

Embodiment 3

[0026] 4,4,5,5-Tetramethyl-2-(pyran-1-yl)-1,3,2-dioxaborolane (4.92g, 15mmol), dibromothiofluorene (5.61g , 15mmol) 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 gas for 30 min, the reaction mixture was heated to reflux under nitrogen gas 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 Drying, filtration, and removal of the solvent in vacuo afforded the product compound of formula (III) (5.05 g, 65% yield).

[0027]

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Abstract

The invention relates to the technical field of photoelectric display devices, in particular to a red delayed fluorescent material based on a pyrene unit and a preparation method thereof. The invention provides the red delayed fluorescent material based on the pyrene unit. The structural formula of the red delayed fluorescent material is shown as a formula (I). The invention also provides the preparation method of the red delayed fluorescent material based on the pyrene unit. The preparation method comprises the step of carrying out substitution reaction on the compound as shown in the formula (III) and the compound as shown in the formula (II) to prepare the compound as shown in the formula (I). The invention provides the red delayed fluorescent material based on the pyrene unit and the preparation method thereof, and solves the technical problems of fewer types of existing red light materials and low device efficiency.

Description

technical field [0001] The invention belongs to the technical field of photoelectric display devices, and in particular relates to a red delayed fluorescent material based on a pyrene unit 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 electroluminescent three-primary color materials, it is difficult to synthesize red TADF material molecules. Therefore, there are relatively few types of red light molecules, and their device efficiency is not high. Con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06
CPCC07D491/107C09K11/06C09K2211/1011C09K2211/1033C09K2211/1092
Inventor 方一文
Owner 南昌万季科技有限公司
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