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An organic light-emitting material containing an acceptor structural unit of a benzo[c][1,2,5]thiadiazole derivative and its application

A technology of thiadiazole derivatives and light-emitting materials, applied in light-emitting materials, organic chemistry, electrical components, etc., can solve problems such as high price and limited resources

Active Publication Date: 2022-07-26
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although metal-organic phosphorescent materials have made great progress so far, and red and green metal iridium complex phosphorescent materials have been applied in commercial electronic products, the price of phosphorescent materials is high due to the use of rare and expensive precious metals. Expensive and extremely limited resources

Method used

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  • An organic light-emitting material containing an acceptor structural unit of a benzo[c][1,2,5]thiadiazole derivative and its application
  • An organic light-emitting material containing an acceptor structural unit of a benzo[c][1,2,5]thiadiazole derivative and its application
  • An organic light-emitting material containing an acceptor structural unit of a benzo[c][1,2,5]thiadiazole derivative and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1: The synthetic route of luminescent material BTN-1 is as follows:

[0051]

[0052] Synthesis of Intermediate 1: Combine 3-methyl-1,2-phenylenediamine (30.53 g, 249.87 mmol, 1.0 equiv), triethylamine (138.92 mL, 999.47 mmol, 4.0 equiv) and dichloromethane (300 mL) A dry three-necked flask equipped with magnetic stirring was sequentially added and placed in an ice bath. The mixture was stirred for more than 1 hour, after which thionyl chloride (36.25 mL, 499.74 mmol, 2.0 equiv) and dichloromethane (100 mL) were slowly added dropwise, the mixture was stirred at this temperature for 1 hour, and the mixture was placed in an oil bath, Stir at 40°C for 20 hours and monitor the reaction by thin layer chromatography until the reaction is complete. The reaction was quenched and the resulting mixture was cooled to room temperature and quenched with water. The mixture was extracted three times with ethyl acetate. The combined organic phases were washed with wate...

Embodiment 2

[0060] Embodiment 2: The synthetic route of luminescent material BTN-2 is as follows:

[0061]

[0062] Synthesis of 2-Br: 3,6-di-tert-butylcarbazole (3.19 g, 11.41 mmol, 1.0 equiv), 1-bromo-4-iodobenzene (3.55 g, 12.55 mmol, 1.1 equiv), iodide Copper (217.2 mg, 1.14 mmol, 0.1 equiv), L-proline (262.6 mg, 2.28 mmol, 0.2 equiv) and potassium carbonate (2.63 g, 22.81 mmol, 2.0 equiv) were sequentially added to a dry three-necked flask equipped with magnetic stirring middle. The nitrogen was purged three times, then dimethyl sulfoxide (60 mL) was added under nitrogen protection, and the mixture was placed in an oil bath and heated to 100°C to react. After 36 hours, the reaction was monitored by thin layer chromatography until completion. The resulting mixture was cooled to room temperature and diluted with dichloromethane. The mixture was washed three times with brine and extracted three times with dichloromethane. The combined organic layers were dried over anhydrous sodi...

Embodiment 3

[0066] Embodiment 3: The synthetic route of luminescent material BTN-3 is as follows:

[0067]

[0068]Synthesis of 3-Br: 3,6-diphenylcarbazole (3.33 g, 10.42 mmol, 1.0 equiv), 1-bromo-4-iodobenzene (3.24 g, 11.46 mmol, 1.1 equiv), cuprous iodide (39.7 mg, 0.21 mmol, 0.02 equiv) and sodium tert-butoxide (2.00 g, 20.81 mmol, 2.0 equiv) were sequentially added to a dry three-necked flask equipped with magnetic stirring. The nitrogen was purged three times, then 1,2-trans-cyclohexanediamine (0.13 mL, 1.04 mmol, 0.1 equiv) and 1,4-dioxane (100 mL) were added under nitrogen protection, and the mixture was placed in an oil bath and stirring the reaction at 100 °C. The reaction was monitored by thin layer chromatography until completion and was stopped after 48 hours. The resulting mixture was cooled to room temperature and quenched by the addition of water. The mixture was extracted three times with dichloromethane. The combined organic layers were washed with water, dried ov...

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Abstract

The invention provides a kind based on benzo[c][1,2,5]thiadiazole-4-aldehyde group acceptor and 2-(benzo[c][1,2,5]thiadiazole-4 -Methylene) malononitrile acceptor donor-acceptor structure organic light-emitting material and its application. The organic light-emitting material is an acceptor-donor separation system, wherein the acceptor is benzo[c][1,2,5]thiadiazole-4-aldehyde group or 2-(benzo[c][1 , 2,5] thiadiazole-4-methylene) malononitrile, donor is carbazole and derivative or benzoxazine etc. In the material, the lowest unoccupied orbital (LUMO) is in the acceptor, and the highest occupied orbital (HOMO) is in the donor. Therefore, the molecular orbital energy level of the light-emitting material can be adjusted by adjusting the structure of the acceptor and the electrical properties of the donor. effective control. By adjusting the structure of the light-emitting material or the electron-donating ability of the donor, the light-emitting color of the material molecule can be easily adjusted. The organic light-emitting material of the present invention has the characteristics of easily adjustable light-emitting color, and can be used as a light-emitting material for the preparation of OLED devices.

Description

technical field [0001] The present invention relates to the field of organic light-emitting materials, in particular to a group containing benzo[c][1,2,5]thiadiazole-4-aldehyde and 2-(benzo[c][1,2,5]thiadiazole Light-emitting materials and applications of -4-methylene)malononitrile acceptor structural unit. Background technique [0002] OLED is an organic light-emitting diode (Organic Light-Emitting Diode) or an organic light-emitting device (Organic Light-Emitting Device). It has the advantages of low cost, fast response speed, high contrast and definition, ultra-thin, easy flexible display, etc. It can also use low-cost glass, flexible metal and plastic as the substrate; in addition, it also has high energy efficiency, low energy consumption, wide material sources, The production process is simple, the plane emits light, and it can be produced in a large area. As a new generation of lighting and display technology, OLED has been used in mobile phones, tablets, cameras, T...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/10C07D285/14C09K11/06H01L51/50H01L51/54
CPCC07D417/10C07D285/14C09K11/06C09K2211/1029C09K2211/1033C09K2211/1051H10K85/6572H10K85/657H10K50/11
Inventor 李贵杰曹丽娜佘远斌邵宗周郑建兵
Owner ZHEJIANG UNIV OF TECH
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