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Organic light-emitting material containing benzo[c][1,2,5]thiadiazole derivative receptor structural unit and application

A technology of light-emitting materials and structural units, applied in the fields of light-emitting materials, organic chemistry, electrical components, etc., can solve the problems of limited resources and high prices, and achieve the effect of convenient adjustment

Active Publication Date: 2020-07-31
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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  • Organic light-emitting material containing benzo[c][1,2,5]thiadiazole derivative receptor structural unit and application
  • Organic light-emitting material containing benzo[c][1,2,5]thiadiazole derivative receptor structural unit and application
  • Organic light-emitting material containing benzo[c][1,2,5]thiadiazole derivative receptor structural unit and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0051]

[0052] Synthesis of Intermediate 1: Combine 3-methyl-1,2-phenylenediamine (30.53g, 249.87mmol, 1.0 equivalent), triethylamine (138.92mL, 999.47mmol, 4.0 equivalent) and dichloromethane (300mL) Add a dry three-necked flask equipped with magnetic stirring and place in an ice bath. The mixture was stirred for more than 1 hour, and then thionyl chloride (36.25 mL, 499.74 mmol, 2.0 equivalents) and dichloromethane (100 mL) were slowly added dropwise. The mixture was stirred at this temperature for 1 hour and then the mixture was placed in an oil bath. After stirring for 20 hours at 40°C, the reaction was monitored by thin layer chromatography until the reaction was completed. The reaction was stopped and the resulting mixture was cooled to room temperature and quenched by adding water. The mixture was extracted three times with ethyl acetate. The combined organic phase was washed with ...

Embodiment 2

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

[0061]

[0062] Synthesis of 2-Br: 3,6-di-tert-butylcarbazole (3.19g, 11.41mmol, 1.0 equivalent), 1-bromo-4-iodobenzene (3.55g, 12.55mmol, 1.1 equivalent), iodide Copper (217.2mg, 1.14mmol, 0.1 equivalent), L-proline (262.6mg, 2.28mmol, 0.2 equivalent) and potassium carbonate (2.63g, 22.81mmol, 2.0 equivalent) were added to a dry three-necked flask equipped with magnetic stirring. in. The nitrogen was pumped three times, and then dimethyl sulfoxide (60 mL) was added under the protection of nitrogen. The mixture was placed in an oil bath and heated to 100°C for reaction. After 36 hours, the reaction was monitored by thin layer chromatography until the reaction was complete. 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 layer was dried o...

Embodiment 3

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

[0067]

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

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Abstract

The invention provides an organic light-emitting material based on a donor-receptor structure of a benzo[c][1,2,5]thiadiazole-4-aldehyde group receptor and a 2-(benzo[c][1,2,5]thiadiazole-4-methylene)malononitrile receptor and application thereof. The organic light-emitting material is a receptor-donor separation system, wherein the receptor is benzo[c][1,2,5]thiadiazole-4-aldehyde or 2-(benzo[c][1,2,5]thiadiazole-4-methylene) malononitrile, and a donor is carbazole and a derivative or benzoxazine and the like. The lowest unoccupied molecular orbital (LUMO) in the material is located in the receptor, and the highest occupied molecular orbital (HOMO) in the material is located in the donor, so that the molecular orbital energy level of the luminescent material can be effectively regulated and controlled through electrical regulation of the receptor structure and the donor. By regulating and controlling the structure of the light-emitting material or the electron donating capability of the donor, the light-emitting color of material molecules can be conveniently regulated. The organic light-emitting material has the characteristic that the light-emitting color is easy to adjust, andcan be used as a light-emitting material for preparing an OLED device.

Description

Technical field [0001] The present invention relates to the field of organic light-emitting materials, in particular to benzo[c][1,2,5]thiadiazole-4-aldehyde groups and 2-(benzo[c][1,2,5]thiadiazole 4-Methylene) malononitrile acceptor structural unit as a luminescent material and its application. Background technique [0002] OLED stands for Organic Light-Emitting Diode (Organic Light-Emitting Diode) or Organic Light-Emitting Device. It is an independent light-emitting material without a backlight; it has all-solid-state, wide viewing angle, low temperature resistance, vivid color, and driving voltage. Low, fast response speed, high contrast and definition, ultra-thin, easy to flexible display, etc., can also use low-cost glass, flexible metal and plastic as the substrate; in addition, it also has high energy efficiency, low energy consumption, extensive material sources, Many advantages such as simple production process, flat luminescence, and large-area production. As a new g...

Claims

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Application Information

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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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