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A class of organic electrogenerated standard saturated red-light-emitting materials, preparation method and OLED application thereof

An electromechanical and standard technology, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of lack of high-efficiency red-light AIE materials, and achieve high yield, stable structure, and simple synthesis methods.

Pending Publication Date: 2021-12-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, OLED devices with standard saturated red light have not been reported, mainly due to the lack of high-efficiency and good chromaticity red AIE materials.

Method used

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  • A class of organic electrogenerated standard saturated red-light-emitting materials, preparation method and OLED application thereof
  • A class of organic electrogenerated standard saturated red-light-emitting materials, preparation method and OLED application thereof
  • A class of organic electrogenerated standard saturated red-light-emitting materials, preparation method and OLED application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Preparation of saturated red material (TNZTPE).

[0051]

[0052] The synthetic route is as follows:

[0053]

[0054](1) Under nitrogen atmosphere, tetrakis (triphenylphosphine) palladium (57.75mg, 0.05mmol), 4-triphenylamine borate (1.45g, 5mmol) and 4,9-dibromonaphthothiadiazole (1.7 g, 5mmol) was dissolved in 60mL of toluene solution, mixed uniformly and heated to 90°C. Potassium carbonate aqueous solution (2.4M, 24mL) was injected into the above solution and heated to 110°C, and reacted at this temperature for 24h. Cool down to room temperature, extract with dichloromethane and water three times, dry over anhydrous magnesium sulfate for 2 h, concentrate, stir evenly with silica gel powder and pass through the column to obtain purple black powder (1.27 g), yield 51%.

[0055] In the case of the same reaction raw material ratio, the heating reaction temperature is set to 90°C, the reaction time is 24h, the reaction solvent is toluene, and the reaction lye is ...

Embodiment 2

[0071] Preparation of saturated red light material (TNZTPETPA).

[0072]

[0073] The synthetic route is as follows:

[0074]

[0075] (1) Under nitrogen atmosphere, tetrakis(triphenylphosphine)palladium (57.75mg, 0.05mmol), raw material 2 (1.69g, 3.33mmol) and raw material 3 (3.51g, 5mmol) were dissolved in 60mL of toluene solution , mix well and heat up to 90°C. Potassium carbonate aqueous solution (2.4M, 24mL) was injected into the above solution and heated to 110°C, and reacted at this temperature for 24h. Cool down to room temperature, extract with dichloromethane and water three times, dry over anhydrous magnesium sulfate for 2 hours, concentrate, stir evenly with silica gel powder and pass through the column to obtain a red powder (2.02g), with a yield of 74%.

[0076] In the case of the same reaction raw material ratio, the heating reaction temperature was set to 90°C, the reaction time was 24h, the reaction solvent was toluene, and the reaction lye was potassi...

Embodiment 3

[0084] Research on performance optimization of OLEDs based on saturated red material (TNZTPE).

[0085] Utilize the TNZTPE (solid-state fluorescence quantum efficiency=50%) prepared in Example 1 to prepare non-doped devices as luminescent materials, and test and characterize its device performance, the results are shown in Figure 1~3 .

[0086] Non-doped device structure: ITO / HATCN(5nm) / TAPC(60nm) / TNZTPE(20nm) / TmPyPB(50nm) / LiF(1nm) / Al(120nm);

[0087] figure 1 It is based on the electroluminescence spectrum of the OLEDs device obtained in Example 1. It can be seen from the figure that the maximum electroluminescence wavelength is located at 658nm. figure 2 It is based on the J-V-L curve diagram of the OLEDs device obtained in Example 1, as can be seen from the figure, the device turn-on voltage is 3.3V and the maximum brightness is 1469cd / m 2 . image 3 It is a graph based on the efficiency of the obtained OLEDs device of embodiment 1 with brightness variation, as can be...

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Abstract

The invention provides a class of organic electrogenerated standard saturated red-light-emitting materials, a preparation method and OLED application thereof. The preparation method of the material comprises the following steps: (1) dissolving a tetra-coordinated palladium catalyst, 4-boric acid triphenylamine and 4, 9-dibromo-naphthothiadiazole in a solvent, uniformly mixing, heating, adding an aqueous alkali solution into the solution, and carrying out a heating reaction to obtain a corresponding bromine-containing unilateral substitution product; and (2) dissolving a tetra-coordinated palladium catalyst, the bromine-containing unilateral substitution product obtained in the step (1) and an arylboronic acid compound in a solvent, uniformly mixing, heating, adding an aqueous alkali solution into the solution, and carrying out a heating reaction to obtain the final organic electrogenerated standard saturated red light material. The material has the advantages of simple preparation method, easily available raw materials, high yield, stable structure, simple storage, AIE characteristic, solid-state fluorescence quantum efficiency up to 50%, and good device performance, and has important application potential in display devices.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a class of organic electro-induced standard saturated red light materials, a preparation method thereof and OLED applications. Background technique [0002] Organic electroluminescent devices (OLEDs) have attracted much attention due to their advantages such as adjustable light color, easy processing, low cost, and flexible folding. Due to faster response and low efficiency roll-off, pure organic light-emitting materials are expected to replace organic phosphorescent display technology. The three primary colors of red, green, and blue are one of the most important components of full-color display technology. Although there have been many reports on high-efficiency green and blue light devices, and even deep red and near-infrared devices have continued to record high efficiencies, they have good Organic materials with red chromaticity are still...

Claims

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Application Information

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IPC IPC(8): C07D285/14C09K11/06H01L51/54H01L51/50
CPCC07D285/14C09K11/06C09K2211/1051C09K2211/1007C09K2211/1014H10K85/631H10K85/657H10K50/11
Inventor 唐本忠王志明万清张兵
Owner SOUTH CHINA UNIV OF TECH
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