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S-triazine derivatives and application thereof to organic electroluminescence devices

A technology of s-triazine and derivatives, applied in the field of s-triazine derivatives, can solve the problems of reducing luminous efficiency, limiting applications, reducing the efficiency of OLEDs, etc., and achieving the effect of high fluorescence quantum yield

Inactive Publication Date: 2014-01-29
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Blue fluorescent materials are mainly some conjugated molecular systems. However, many organic fluorescent materials show high fluorescence quantum yield in solution, but in the solid state due to strong intermolecular stacking, the fluorescence quenching is greatly reduced. Its luminous efficiency limits its application in OLEDs
In addition, the hole-transport capacity of many organic fluorescent materials is much higher than their electron-transport capacity, which reduces the efficiency of their OLEDs.

Method used

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  • S-triazine derivatives and application thereof to organic electroluminescence devices
  • S-triazine derivatives and application thereof to organic electroluminescence devices
  • S-triazine derivatives and application thereof to organic electroluminescence devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The synthesis of embodiment 1 compound TAr1 series compound

[0025] Synthesis of compound TAr1-1

[0026]

[0027] Under nitrogen protection, magnesium chips (1.152g, 48mmol) and anhydrous tetrahydrofuran (30mL) were placed in a three-necked flask, and a solution of bromobenzene (6.24g, 40mmol) in tetrahydrofuran (50mL) was added dropwise at reflux temperature. Reflux for 3 hours and cool to room temperature. Under nitrogen protection, the Grignard reagent was dropped into a solution of 1,3,5-trichloro-s-triazine (3.68g, 20mmol) in anhydrous tetrahydrofuran (40mL) at zero temperature, and the reaction was carried out at 20°C for 12 hours. After cooling to room temperature, the reaction was quenched with ammonium chloride solution. Extracted three times with dichloromethane, combined the organic phases, washed with water and saturated brine successively, dried over anhydrous sodium sulfate, filtered and concentrated to obtain the crude product, and separated by col...

Embodiment 2

[0077] The synthesis of embodiment 2 compound TAr2 series compounds

[0078] Synthesis of compound TAr2-1

[0079]

[0080] Under nitrogen protection, magnesium chips (1.152g, 48mmol) and anhydrous tetrahydrofuran (30mL) were placed in a three-necked flask, and a solution of bromobenzene (6.24g, 40mmol) in tetrahydrofuran (50mL) was added dropwise at reflux temperature. Reflux for 3 hours and cool to room temperature. Under the protection of nitrogen, the Grignard reagent was dropped into a solution of 1,3,5-trichloro-s-triazine (2.44 g, 13.33 mmol) in anhydrous tetrahydrofuran (40 mL), and reacted at 40° C. for 12 hours after the dropping was completed. After cooling to room temperature, the reaction was quenched with ammonium chloride solution. The organic solvent was removed by rotary evaporation, dichloromethane (100mL) was added, washed with water and saturated brine successively, dried over anhydrous sodium sulfate, filtered and concentrated to obtain the crude prod...

Embodiment 3

[0130] The synthesis of embodiment 3TAr3 series compound

[0131] Synthesis of compound TAr3-1

[0132]

[0133] Under nitrogen protection, magnesium chips (1.152g, 48mmol) and anhydrous tetrahydrofuran (30mL) were placed in a three-necked flask, and a solution of p-bromotoluene (6.8g, 40mmol) in tetrahydrofuran (50mL) was added dropwise at reflux temperature. , refluxed for 3 hours and then cooled to room temperature. Under the protection of nitrogen, the Grignard reagent was dropped into a solution of 1,3,5-trichloro-s-triazine (1.83 g, 10 mmol) in anhydrous tetrahydrofuran (30 mL). After the dropping was completed, the reaction was refluxed for 12 hours. After cooling to room temperature, the reaction was quenched with ammonium chloride solution. The organic solvent was removed by rotary evaporation, dichloromethane (100 mL) was added, washed with water and saturated brine successively, dried over anhydrous sodium sulfate, filtered and concentrated to obtain a crude pr...

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Abstract

The invention relates to s-triazine derivatives which not only can be used as organic light-emitting layers, but also can be used as main materials of phosphor materials to be applied to organic electroluminescence devices. The glass transition temperature of the s-triazine derivatives provided by the invention ranges from 70 DEG C to 180 DEG C, the triplet-state energy of the s-triazine derivatives is over 2.7eV, the molecular structure of the s-triazine derivatives contains an s-triazine group, and the s-triazine derivatives have the structural general formula I shown in the specification. The s-triazine derivatives provided by the invention have higher fluorescence quantum yield, high stability and higher steric hindrance so that the solid fluorescence quenching is avoided, and the brightness and efficiency of the devices can be well increased when the s-triazine derivatives are used as the light-emitting layers to be applied to the organic electroluminescence devices; in addition, the s-triazine derivatives have higher triplet-state energy and can be used as the main materials to effectively transfer the triplet-state energy to green and red phosphorescent materials, so that the brightness and efficiency of the organic electroluminescence devices made of the phosphor materials can be increased.

Description

technical field [0001] The invention relates to a class of s-triazine derivatives, which can be used as organic light-emitting layers and host materials of phosphorescent materials in organic electroluminescent devices. Background technique [0002] Under the environment of global energy shortage and climate warming, governments of various countries have vigorously developed sustainable high-tech energy-saving industries one after another. Organic electroluminescent devices (OLEDs) have attracted much attention because of their advantages such as wide vision, high brightness, low energy consumption, and the ability to prepare flexible displays. They are known as key technologies that will dominate the future display world. Therefore, governments and enterprises of various countries have laid out OLEDs industry one after another, such as Kodak and UDC in the United States, Philips in the Netherlands, Siemens in Germany, Sony in Japan, Samsung and LG in South Korea, etc. [0...

Claims

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Application Information

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IPC IPC(8): C07D251/24C07D403/14C07D409/14C07D409/04C07D403/10C09K11/06H01L51/54
CPCC09K11/06C07D251/24C07D403/10C07D403/14C07D409/04C07D409/14C09K2211/1092C09K2211/1059H10K85/655H10K85/631H10K85/654H10K85/6572
Inventor 李承辉游效曾郑佑轩刘建滕明瑜
Owner NANJING UNIV
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