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D-A type light-emitting small molecule containing acridine and phenanthroimidazole and application thereof in electroluminescent device

A technology of phenanthroimidazole and small molecules, applied in D-A type luminescent small molecules and its application in electroluminescent devices, can solve the problems of only 62.5% exciton utilization rate, unfavorable practical application, and efficiency roll-off, etc. Achieve high exciton utilization, high carrier mobility, and high fluorescence quantum yield

Inactive Publication Date: 2020-09-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the first two types of materials rarely have high-efficiency materials that meet the blue light color coordinate CIEy<0.15. In addition, these two types of materials also face serious efficiency roll-off problems, which are not conducive to practical applications (Science China Chemistry, 2014, 57, 335– 345; Journal of Materials Chemistry C, 2018, 6, 5577–5596)
The TTA fluorescent material forms a singlet exciton by fusing two triplet excitons, and the exciton utilization rate is only 62.5%.

Method used

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  • D-A type light-emitting small molecule containing acridine and phenanthroimidazole and application thereof in electroluminescent device
  • D-A type light-emitting small molecule containing acridine and phenanthroimidazole and application thereof in electroluminescent device
  • D-A type light-emitting small molecule containing acridine and phenanthroimidazole and application thereof in electroluminescent device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation of compound M1

[0027] The structural formula and synthetic route of compound M1 are shown in the figure below, and the specific synthetic method is as follows:

[0028]

[0029] (1) Synthesis of compound 1

[0030] Under the protection of nitrogen, 9,10-dihydro-9,9-diphenylacridine (10mmol), 9,10-dibromoanthracene (10mmol), sodium tert-butoxide (25mmol), catalyst tridibenzylidene Dipalladium acetone (Pd 2 (dba) 3 , 0.5mmol) and ligand tri-tert-butylphosphine (1mmol) were added to 50ml of toluene, stirring was started and heated to 120°C, and reacted for 10 hours. After the reaction, the product was extracted with ethyl acetate, washed three times with saturated sodium chloride solution, dried with anhydrous sodium sulfate, the dried solution was filtered, and the solvent was spin-dried by a rotary evaporator to obtain a crude product. The crude product was separated and purified by silica gel chromatography column, and the eluent was a mixed solvent...

Embodiment 2

[0038] Preparation of Compound M2

[0039] The structural formula and synthetic route of compound M2 are shown in the figure below, and the specific synthetic method is as follows:

[0040]

[0041] (1) Synthesis of Compound 4

[0042] Under the protection of nitrogen, 9,10-dihydro-9,9-dimethylacridine (10mmol), 1,4-dibromobenzene (10mmol), sodium tert-butoxide (25mmol), catalyst tridibenzylidene Dipalladium acetone (Pd 2 (dba) 3 , 0.5mmol) and ligand tri-tert-butylphosphine (1mmol) were added to 50ml of toluene, stirring was started and heated to 120°C, and reacted for 10 hours. After the reaction, the product was extracted with ethyl acetate, washed three times with saturated sodium chloride solution, dried with anhydrous sodium sulfate, the dried solution was filtered, and the solvent was spin-dried by a rotary evaporator to obtain a crude product. The crude product was separated and purified by silica gel chromatography column, and the eluent was a mixed solvent of ...

Embodiment 3

[0050] Preparation of compound M3

[0051] The structural formula and synthetic route of compound M3 are shown below, and the specific synthetic method is as follows:

[0052]

[0053] (1) Synthesis of Compound 7

[0054] Under the protection of nitrogen, 9,10-dihydro-9,9-dimethylacridine (10mmol), 1,3-dibromobenzene (10mmol), sodium tert-butoxide (25mmol), catalyst tridibenzylidene Dipalladium acetone (Pd 2 (dba) 3 , 0.5mmol) and ligand tri-tert-butylphosphine (1mmol) were added to 50ml of toluene, stirring was started and heated to 120°C, and reacted for 10 hours. After the reaction, the product was extracted with ethyl acetate, washed three times with saturated sodium chloride solution, dried with anhydrous sodium sulfate, the dried solution was filtered, and the solvent was spin-dried by a rotary evaporator to obtain a crude product. The crude product was separated and purified by silica gel chromatography column, and the eluent was a mixed solvent of petroleum ethe...

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Abstract

The invention discloses an electron donor-acceptor D-A type light-emitting small molecule containing acridine and phenanthroimidazole and application thereof in an electroluminescent device. An acridine electron donor unit and a phenanthroimidazole electron acceptor unit are respectively connected to two sides of an anthracene unit with large steric hindrance, the donor unit and the acceptor unitin the constructed molecule have large torsion angles, charge transfer with moderate intensity is realized, a hybrid local charge transfer (HLCT) excited state is further formed, high-energy triplet-state to singlet-state inverse intersystem crossing can be realized, and 100% utilization of exciton is realized. In addition, acridine and phenanthroimidazole have the characteristics of wide band gap, high fluorescence quantum yield and high carrier mobility, and the light-emitting small molecule containing acridine and phenanthroimidazole can be used for preparing a high-efficiency blue organiclight-emitting device.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a class of D-A type light-emitting small molecules containing acridine and phenanthroimidazole and their application in electroluminescent devices. Background technique [0002] Organic light-emitting diodes (OLEDs) have attracted extensive attention due to their advantages of flexibility, active light emission, high efficiency, low-voltage drive, and easy fabrication of large-area devices. OLED-related research can be traced back to the 1960s. In 1963, Professor Pope of New York University discovered the electroluminescence phenomenon of organic molecular single crystal anthracene for the first time, and then some single crystal structure materials have electroluminescence properties. However, due to the high driving voltage of the device at that time, it failed to attract widespread attention. It wasn't until 1987 that Deng Qingyun and other...

Claims

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Application Information

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IPC IPC(8): C07D401/10C09K11/06H01L51/54H01L51/50
CPCC07D401/10C09K11/06C09K2211/1044C09K2211/1029C09K2211/1011H10K85/615H10K85/6572H10K50/12H10K50/11
Inventor 马於光胡德华应磊郭婷
Owner SOUTH CHINA UNIV OF TECH
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