Bipolar small-molecular luminescent material based on heteroaromatic ring-fused-3-S,S-dioxodibenzothiophene unit, and preparation method and application thereof

A technology of dioxydibenzothiophene and light-emitting materials, which is applied in the directions of light-emitting materials, electrical components, chemical instruments and methods, etc., achieves the effects of simple preparation process, improved material device efficiency, and good electron and hole transport performance.

Inactive Publication Date: 2017-07-04
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a bipolar small molecule luminescent material based on aromatic heterocyclo-3-S, S-dioxodibenzothiophene unit in view of the problems faced by organic light-emitting diodes (OLEDs) at present.

Method used

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  • Bipolar small-molecular luminescent material based on heteroaromatic ring-fused-3-S,S-dioxodibenzothiophene unit, and preparation method and application thereof
  • Bipolar small-molecular luminescent material based on heteroaromatic ring-fused-3-S,S-dioxodibenzothiophene unit, and preparation method and application thereof
  • Bipolar small-molecular luminescent material based on heteroaromatic ring-fused-3-S,S-dioxodibenzothiophene unit, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Methyl 1-bromo-2-quinoxalinecarboxylate

[0037] Under an argon atmosphere, add 1-bromo-2-quinoxalinecarboxylic acid (10g, 39.83mmol) into a two-necked flask, add 100mL of methanol, then add concentrated sulfuric acid (39.06mg, 398.29umol) dropwise, and heat to 110 °C, reacted for 18h. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the solution was concentrated, a white solid crude product was obtained, which was purified by silica gel column chromatography (petroleum ether / dichloromethane=3 / 1, v / v was selected as the eluent), and the product was placed in the refrigerator for a long time to obtain a white solid with a yield of 85%. . 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product. The chemical reaction equation is as follows:

[0038]

Embodiment 2

[0040] Methyl 1-boronate-2-quinoxalinecarboxylate

[0041]Under argon atmosphere, the compound 1-bromo-2-quinoxalinecarboxylic acid methyl ester (10g, 37.72mmol) was dissolved in anhydrous tetrahydrofuran (THF), stirred at -78°C for 20 minutes, then added n-butyl Lithium (21.05g, 113.16mmol), stirred at -78°C for 2 hours, then added isopropoxy pinacol ester (9.66g, 150.88mmol), stirred at -78°C for 1 hour, and reacted at room temperature for 16 hours . The reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the solution was concentrated, a white solid crude product was obtained, which was purified by silica gel column chromatography (petroleum ether / dichloromethane=2 / 1, v / v was selected as the eluent), and the product was placed in the refrigerator for a long time to obtain a white solid with a yield of 75%. . 1 H NMR, 13 CNMR, MS and elemental analysis results s...

Embodiment 3

[0044] Preparation of 3-bromo-S,S-thiofluorene dioxide

[0045] (1) In a 150 mL round bottom flask, 5 g of biphenyl was dissolved in 80 mL of dichloromethane, 11.8 g of bromosuccinimide was added at room temperature, and then reacted at room temperature for 48 hours. After the reaction, the reactant was poured into water, extracted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate, evaporated to remove the solvent, and then recrystallized with petroleum ether. 5.65 g of white solid was obtained, yield 75%.

[0046] (2) Add 20g of 4,4'-dibromobiphenyl to a 150mL three-necked flask, dissolve it in 50mL of chloroform, add 11.4mL of chlorosulfonic acid dropwise, keep the reaction system below 50°C, and react for 3 hours. After the reaction, the reactant was poured into 500mL of crushed ice, and the ice was melted with Na 2 CO 3 The solution was adjusted to be neutral, and the insoluble matter was filtered out, washed with water and dried, and then ...

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Abstract

The invention discloses a bipolar small-molecular luminescent material based on a heteroaromatic ring-fused-3-S,S-dioxodibenzothiophene unit, and a preparation method and an application thereof. Through a Suzuki coupling reaction, electron donor units are connected to two sides of the heteroaromatic ring-fused-3-S,S-dioxodibenzothiophene unit to prepare the luminescent material. The bipolar small-molecular luminescent material has good solubility, film-forming property and thin film morphological stability and also has excellent electron and hole transport performances, so that the material can balance injection and transportation of carriers, more electrons and holes are effectively compounded to generate excitons, and a mixing phenomenon with the transportation layer interface between the electrons and the holes, thereby improving luminescent efficiency of a device. A luminous layer, based on the material, is free of annealing treatment during preparation of electroluminescent devices, so that the production process is simple.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and specifically relates to a bipolar small-molecule luminescent material based on an aromatic heterocycle-3-S,S-dioxodibenzothiophene unit and a preparation method and application thereof. Background technique [0002] Organic light-emitting diodes (OLEDs) have attracted widespread attention due to their high efficiency, low-voltage drive, and ease of large-area fabrication. The research on OLED began in the 1950s, and until 1987, Dr. Deng Qingyun of Kodak Company of the United States developed an OLED device with a sandwich device structure. The luminous brightness of the OLED device can reach 1000cd m under the drive of 10V DC voltage. -2 , so that OLED has achieved an epoch-making development. [0003] The OLED device consists of a cathode, an anode, and an organic layer in the middle. The organic layer generally includes an electron transport layer, a light-emitting layer, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C09K11/06H01L51/54
CPCC09K11/06C07D495/04C09K2211/1044C09K2211/1014C09K2211/1029C09K2211/1007C09K2211/1092H10K85/631H10K85/657H10K85/6572
Inventor 应磊赵森郭婷杨伟彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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