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1,2,4-thiadiazole compound and preparation method and application thereof

A compound and an independent technology, applied in the field of 1,2,4-thiadiazole compounds and their preparation, can solve the problems of inability to solve the loss of light, the material of the light emitting layer needs to be improved, etc., to ensure thermal stability and compactness. The effect of improving the performance and improving the current efficiency

Active Publication Date: 2019-02-22
湖北尚赛光电材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In the prior art, the design of OLED light-emitting layer materials including 1,2,4 thiadiazole structures mainly focuses on releasing light through the "recombination" of anode holes and cathode electrons in the light-emitting layer, thereby improving the light emission of electrons / holes. The conversion ratio is used to improve the efficiency of the device, but it cannot solve the loss of light caused by total reflection and absorption of light inside the device.
Therefore, the existing light-extracting layer materials of OLEDs still need to be improved.

Method used

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  • 1,2,4-thiadiazole compound and preparation method and application thereof
  • 1,2,4-thiadiazole compound and preparation method and application thereof
  • 1,2,4-thiadiazole compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064]

[0065] (1) In a 500mL three-necked flask, put 5-bromo-3-chloro-1,2,4-thiadiazole (19.94g, 100mmol), phenanthrene-9-ylboronic acid (22.20g, 100mmol), cesium carbonate (48.87g, 150mmol), add 200mL toluene, under nitrogen atmosphere, add [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1.46g, 2mmol), heat up to 50~ React at 100°C for 4 to 48 hours, monitor the completion of the reaction by liquid phase monitoring, cool to room temperature, wash with water, filter, concentrate, and separate by column chromatography to obtain 5-bromo-3-(phenanthrene-9-yl)-1,2,4- Thiadiazole 25.25g, yield 74%;

[0066] (2) In a 500mL three-necked flask, put 5-bromo-3-(phenanthrene-9-yl)-1,2,4-thiadiazole (17.06g, 50mmol), 4-tert-butylphenylboronic acid (8.90 g, 50mmol), potassium carbonate (13.82g, 100mmol), add 150mL toluene, 50mL ethanol and 50mL water, under nitrogen atmosphere, add tetrakis (triphenylphosphine) palladium (0.12g, 0.1mmol), heat up to 50~ React at 100°C fo...

Embodiment 2

[0069]

[0070]According to the same method as Example 1, prepare the target compound in the above formula (compared with Example 1, the reactant of each corresponding step can be different, but the reactant molar ratio, reaction conditions are identical), obtain final product 17.62g, Yield 85%. Mass spectrometer MALDI-TOF-MS (m / z) = 414.5266, theoretical molecular weight: 414.5260; Anal.Calcd for C 28 h 18 N 2 (%): C 81.13, H 4.38, N 6.67, Found: C 81.14, H 4.38, N 6.65.

Embodiment 3

[0072]

[0073] According to the same method as Example 1, prepare the target compound in the above formula (compared with Example 1, the reactant of each corresponding step can be different, but the reactant molar ratio, reaction conditions are identical), obtain final product 20.52g, Yield 81%. Mass spectrometer MALDI-TOF-MS (m / z) = 506.6664, theoretical molecular weight: 506.6670; Anal.Calcd for C 35 h 26 N 2 (%): C 82.97, H 5.17, N 5.53, Found: C 82.95, H 5.18, N 5.53.

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Abstract

The invention discloses a 1,2,4-thiadiazole compound and a preparation method and an application thereof. The 1,2,4-thiadiazole compound serving as a light emitting layer material of an OLED apparatuscan improve the performance, for example, the light emitting strength, the current power, the power efficiency, the outer quantum efficiency, the chroma and etc obviously, and prolong the service life of the apparatus.

Description

technical field [0001] The present invention relates to the field of optoelectronic materials, in particular, the present invention relates to 1,2,4-thiadiazole compounds as light-extracting layer materials and their preparation methods and applications. Background technique [0002] OLED stands for Organic Light Emitting Diode, also known as Organic Laser Display. OLED has the characteristics of self-illumination. It uses a very thin organic material coating and glass substrate. When the current passes through, the organic material will emit light, and the OLED display screen has a large viewing angle and can significantly save power. Therefore, OLED is regarded as One of the most promising products of the 21st century. However, so far, OLED devices have not been widely used, and the efficiency of the device is an important reason for restricting their popularization. [0003] An important parameter to characterize OLED efficiency is the external quantum efficiency (η EQ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/08C07D417/04C07D417/10C07D417/14C07D471/04C09K11/06H01L51/54
CPCC09K11/06C07D285/08C07D417/04C07D417/10C07D417/14C07D471/04C09K2211/1044C09K2211/1051C09K2211/1011C09K2211/1088C09K2211/1092H10K85/615H10K85/622H10K85/626H10K85/654H10K85/656H10K85/657H10K85/6572H10K85/6574H10K85/6576
Inventor 穆广园庄少卿任春婷
Owner 湖北尚赛光电材料有限公司