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Aggregation-induced emissive blue-ray molecule by construction of dibenzothiophene sulfone unit as well as preparation method and application of aggregation-induced emissive blue-ray molecule

A technology of aggregation-induced luminescence and dibenzothiophene sulfone, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc.

Inactive Publication Date: 2015-07-01
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, not all molecules synthesized by this method have high-efficiency light-emitting properties

Method used

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  • Aggregation-induced emissive blue-ray molecule by construction of dibenzothiophene sulfone unit as well as preparation method and application of aggregation-induced emissive blue-ray molecule
  • Aggregation-induced emissive blue-ray molecule by construction of dibenzothiophene sulfone unit as well as preparation method and application of aggregation-induced emissive blue-ray molecule
  • Aggregation-induced emissive blue-ray molecule by construction of dibenzothiophene sulfone unit as well as preparation method and application of aggregation-induced emissive blue-ray molecule

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add compound 3,7-dibromodibenzothiophene sulfone (100 mg, 0.27 mmol), boronic acid 1 (306 mg, 0.67 mmol), potassium carbonate (740 mg, 5.4 mmol) and a catalytic amount of Pd in ​​a Schlenk tube under nitrogen atmosphere. (PPh 3 ) 4 , and then added toluene (8 mL), ethanol (1.5 mL) and deoxygenated water (3.3 mL), stirred at 90° C. for 24 hours to fully react. After the reaction was completed, the product was cooled to room temperature, extracted with toluene, and the organic phase was collected and washed with anhydrous Na 2 SO 4 Dry to obtain crude product. Using petroleum ether and dichloromethane (v / v, 2 / 1) as eluents, the product was separated and purified by silica gel column chromatography, and dried in vacuo to obtain a green solid (205 mg, yield 87%), which was used with 1 H NMR, 13 C NMR, MS and EA characterize the structure, confirming that the green solid has the structure shown in formula (I).

[0027] 1 H NMR (300MHz, CDCl 3 )δ(ppm):7.98(s,2H),7.81(...

Embodiment 2

[0030] Add compound 3,7-dibromodibenzothiophene sulfone (100 mg, 0.27 mmol), boronic acid 2 (315 mg, 0.67 mmol), potassium carbonate (740 mg, 5.4 mmol) and a catalytic amount of Pd in ​​a Schlenk tube under nitrogen atmosphere. (PPh 3 ) 4 , and then added toluene (8 mL), ethanol (1.5 mL) and deoxygenated water (3.3 mL), stirred at 90° C. for 24 hours to fully react. After the reaction was completed, the product was cooled to room temperature, extracted with toluene, and the organic phase was collected and washed with anhydrous Na 2 SO 4 Dry to obtain crude product. Using petroleum ether and dichloromethane (v / v, 2 / 1) as the eluent, the product was separated and purified by silica gel column chromatography, and dried in vacuo to obtain a light green powder (183 mg, yield 75%), which was mixed with 1 H NMR, 13 The structure was characterized by C NMR, MS and EA, which confirmed that the light green powder had the structure shown in formula (II).

[0031] 1 H NMR (300MHz, ...

Embodiment 3

[0034] Add compound 3,7-dibromodibenzothiophene sulfone (100 mg, 0.27 mmol), boronic acid 3 (306 mg, 0.67 mmol), potassium carbonate (740 mg, 5.4 mmol) and a catalytic amount of Pd in ​​a Schlenk tube under nitrogen atmosphere. (PPh 3 ) 4 , and then added toluene (8 mL), ethanol (1.5 mL) and deoxygenated water (3.3 mL), stirred at 90° C. for 24 hours to fully react. After the reaction was completed, the product was cooled to room temperature, extracted with toluene, and the organic phase was collected and washed with anhydrous Na 2 SO 4 Dry to obtain crude product. Using petroleum ether and dichloromethane (v / v, 2 / 1) as the eluent, the product was separated and purified by silica gel column chromatography, and dried in vacuo to obtain a white powder (194 mg, yield 82%), which was used with 1 H NMR, 13 The structure was characterized by C NMR, MS and EA, and it was confirmed that the white powder had the structure shown in formula (III).

[0035] 1 H NMR (300MHz, CDCl 3 )...

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Abstract

The invention discloses an aggregation-induced emissive blue-ray molecule by construction of dibenzothiophene sulfone unit as well as a preparation method and application of the aggregation-induced emissive blue-ray molecule. Starting from 3,7-di-brominated dibenzothiophene sulfone, tetraphenyl ethylene units with different replace sites are introduced by means of a one-step Suzuki reaction to finally obtain the target compound. Controllable adjustment of emission colors can be realized by fine control of the structure and adopting different connecting sites and the method for adjusting conjugated degree. The aggregation-induced emissive blue-ray molecule has excellent thermal stability, has relatively high solid-state fluorescence quantum yield and blue-ray emission, and can be used as a blue-ray organic emissive diode luminescent layer material. In the blue-ray molecule, the blue-green light emission color has the coordinates of (0.19, 0.36) and current efficiency of 8.7cd / A, and the blue light emission color has coordinates of (0.17, 0.28) and current efficiency of 6.2cd / A.

Description

technical field [0001] The invention relates to a dibenzothiophene sulfone unit constructing an aggregation-induced luminescence blue light molecule, a preparation method thereof, and an application as a light-emitting layer material of a blue light organic light-emitting diode. Background technique [0002] In the 1980s, since Dr. Deng Qingyun of Kodak Company first invented the organic light-emitting diode with multilayer structure, the research work of high-efficiency organic electroluminescent materials has entered a new era. In order to realize full-color display and solid-state lighting, red, green and blue light materials with high efficiency, stability and high color purity are indispensable. After more than 20 years of development, red and green light-emitting materials have been able to meet the needs of commercialization, but blue-light materials with excellent performance are still scarce, because the large energy gap of blue-light-emitting materials has a large ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D333/76H01L51/54H01L51/00
Inventor 李振占学军李倩倩
Owner WUHAN UNIV
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