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Organic compound and application thereof

An organic compound, selected technology, applied in silicon organic compounds, organic chemistry, compounds of group 4/14 elements of the periodic table, etc., to achieve the effects of reducing concentration quenching, prolonging working life, and high luminous efficiency

Pending Publication Date: 2021-12-21
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, few TADF materials have been found so far, and their luminous performance has great room for improvement. Therefore, it is urgent to develop more types of TADF materials with higher performance and lower cost in this field to further improve the comprehensive performance of OLED devices. performance

Method used

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  • Organic compound and application thereof
  • Organic compound and application thereof
  • Organic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0118] A kind of organic compound M1, the structure is as follows:

[0119]

[0120] The preparation method of this organic compound M1 comprises the steps:

[0121] (1)

[0122] Add compound A01 (30mmol) into a three-necked flask, stir and dissolve with 200mL tetrahydrofuran, protect with nitrogen, cool down to -78°C, then slowly add 15mL of 2M n-butyllithium (n-BuLi) solution dropwise, and stir for 0.5h after the addition. Then, a solution of compound B01 (30 mmol) in tetrahydrofuran (THF) was dropped into the reaction solution. After dropping, warm up to room temperature, stir for 2 h, add saturated ammonium chloride solution to quench, add water, concentrate the organic phase to obtain an oil, add 100 mL of acetic acid and 20 mL of HCl to the oil, and stir to reflux for 12 h. After cooling, saturated brine was added and extracted with dichloromethane to obtain an organic phase. The organic phase was washed three times with water. The solvent was removed by evapora...

Embodiment 2

[0127] A kind of organic compound M19, the structure is as follows:

[0128]

[0129] The preparation method of this organic compound M19 comprises the steps:

[0130]

[0131] In a 250mL round bottom flask, M01-1 (10mmol), C19 (12mmol) and Na 2 CO 3 (80mmol) were added to toluene / EtOH / H 2 In O (75 / 25 / 50, mL) solvent, a mixed solution was formed, and then Pd(PPh 3 ) 4 (0.48mmol) was added in the above-mentioned mixed solution, and the intermediate obtained by reflux reaction for 20h under a nitrogen atmosphere was cooled to room temperature, added to water, then filtered through a diatomaceous earth pad, extracted with dichloromethane simultaneously, then washed with water, and After drying over anhydrous magnesium sulfate, filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain the target product M19.

[0132] The elemental analysis result of organic compound M19 (molecular formula C 55 h 35 B 2 NO): theoretical v...

Embodiment 3

[0134] An organic compound M39 with the following structure:

[0135]

[0136] The preparation method of this organic compound M39 comprises the steps:

[0137] (1)

[0138] 50 mmol B39 was dissolved in 250 mL THF, 50 mmol A39 was dissolved in 750 mL THF, the solution of B39 was added dropwise to the solution of A39, and the resulting mixture was stirred at room temperature for 16 h. After removing the solvent under vacuum, the residue was dissolved in 250 mL of dichloromethane, washed three times with 200 mL of distilled water, dried over sodium sulfate, the organic phase was evaporated, and the residue was recrystallized five times with dioxane to obtain compound M39- 1.

[0139] (2)

[0140] In a 250mL round bottom flask, M39-1 (10mmol), C01 (12mmol) and Na 2 CO 3 (80mmol) were added to toluene / EtOH / H 2 In O (75 / 25 / 50, mL) solvent, a mixed solution was formed, and then Pd(PPh 3 ) 4 (0.48mmol) was added in the above-mentioned mixed solution, and the intermedia...

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Abstract

The invention provides an organic compound and application thereof. The organic compound has a structure as shown in a formula I, through the design of a molecular structure, the compound is endowed with proper HOMO energy level and LUMO energy level, so that energy level matching of compounds in adjacent layers is facilitated, and efficient exciton recombination is realized; the organic compound has the advantages that the HOMO / LUMO energy level overlapping is small, the singlet state energy level ES and the triplet state energy level ET are high, the energy level difference delta EST is low, the anti-intersystem crossing process is facilitated, and the higher luminous efficiency is realized; meanwhile, the organic compound is high in molecular stability and small in stacking degree, concentration quenching reduction is facilitated, and the organic compound has excellent thermal stability and film stability. The organic compound is suitable for being used as a TADF material, is applied to an OLED device, facilitates preparation of the OLED device, and can improve the luminous efficiency and stability of the device, reduce the turn-on voltage and prolong the service life of the device.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic compound and its application. Background technique [0002] Organic electroluminescent technology is one of the most promising optoelectronic technologies. Since the rise of organic electroluminescent devices (Organic Light Emitting Diode, OLED) in 1987, it has attracted great attention from the scientific and industrial circles. Compared with inorganic electroluminescent devices, organic electroluminescent devices have the advantages of self-luminescence, high contrast, wide color gamut, flexibility, and low power consumption. They have been successfully applied commercially and are widely used in flexible displays and flat panel displays. and solid-state lighting and other fields. [0003] OLED devices usually have a sandwich-like stack structure, including a cathode, an anode, and an organic layer sandwiched between the two ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07F7/08C07F7/10C09K11/06H01L51/50H01L51/54
CPCC07F5/027C07F7/0816C09K11/06C09K2211/1007C09K2211/1014C09K2211/1011C09K2211/1096C09K2211/1029C09K2211/1059C09K2211/1088C09K2211/1033C09K2211/1044C09K2211/1037C09K2211/1092C09K2211/104H10K85/615H10K85/631H10K85/636H10K85/654H10K85/6576H10K85/657H10K85/6574H10K85/40H10K85/6572H10K50/11H10K85/658H10K2101/20H10K85/322H10K2101/10H10K2101/30H10K2101/40
Inventor 邓东阳刘营张磊高威
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD