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Carbazole compound containing thianthrene and diphenylethlene structures and preparation of carbazole compound

A technology of diphenylethylene and thiaanthracene tetroxide, which is applied in chemical instruments and methods, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve the problems of non-luminescence, luminescence, quenching, etc., and achieve high luminous efficiency and easy operation Good performance and thermal stability

Inactive Publication Date: 2017-11-24
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, TADF materials and other traditional materials also face a problem, that is, when they are used as thin films, due to the strong intermolecular π-π stacking and exciton recombination and non-radiative attenuation, they are usually in the solid state. No or very weak light emission, this phenomenon is called aggregation-induced quenching (ACQ)

Method used

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  • Carbazole compound containing thianthrene and diphenylethlene structures and preparation of carbazole compound
  • Carbazole compound containing thianthrene and diphenylethlene structures and preparation of carbazole compound
  • Carbazole compound containing thianthrene and diphenylethlene structures and preparation of carbazole compound

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Embodiment 1

[0033] Example 1. The preparation of 9-ethyl-3-(1,2-diphenylvinyl)-6-(5,5,10,10-tetraoxythianthracenyl)carbazole, the steps are as follows:

[0034] (1) Synthesis of 9-ethyl-6-bromo-3-carbazolylbenzophenone;

[0035] In a 250 mL vessel with a stirrer, add 9-ethyl-3-bromo-carbazole (3.57 g, 13.03 mmol), benzoyl chloride (1.8 mL, 2.19 g, 15.64 mmol) and 60 mL of CH 2 Cl 2; then under nitrogen atmosphere, aluminum chloride (1.82g, 13.67mmol) was slowly added to the above mixture; the reaction was maintained at 40°C for 6 hours; after cooling to room temperature, the mixture was poured into 200mL of cold water and washed with 50mL of CH 2 Cl 2 Extracted 3 times; the organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated; the crude product was purified by silica gel column chromatography using petroleum ether / dichloromethane as eluent to give 9-ethyl-6-bromo - 4.0 g of 3-carbazolylbenzophenone, the yield is 81%.

[0036] (2) ...

Embodiment 2

[0045] Embodiment 2. Structure, preparation and performance of organic electroluminescent devices:

[0046] The device we prepared is a blue-green organic electroluminescent device, and the device structure is: ITO / NPB (thickness 50nm) / CPB (thickness 50nm) / compound DPECTT (thickness 50nm) / Bphen (thickness 20nm) / LiF (thickness 0.5nm) / Al (thickness 150nm), wherein, NPB is used as a hole transport material; CPB is used as an electron blocking material; 9-ethyl-3-(1,2-diphenylvinyl)-6-(5,5,10, 10-Tetraoxythianthranyl)carbazole (compound DPECTT) was used as the light-emitting layer; Bphen was used as the electron-transporting layer.

[0047] The preparation steps of the device: clean the ITO glass, first scrub the ITO glass with acetone, then rinse it with water, then ultrasonically clean it with a cleaning solution, and then ultrasonically clean it with water; dry the cleaned substrate with nitrogen, and finally use ultraviolet- Ozone treatment to fully clean the surface; accord...

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Abstract

The invention provides a carbazole compound containing thianthrene and diphenylethlene structures. The carbazole compound is particularly 9-ethyl-3-(1,2-diphenylvinyl)-6-(5,5,10,10-thianthrene)carbazole. The preparation method comprises the following steps: firstly, preparing 9-ethyl-3-(1,2-diphenylvinyl)-6-carbazole boric acid and 2-bromine-5,5,10,10-thianthrene; and then enabling reaction between 9-ethyl-3-(1,2-diphenylvinyl)-6-carbazole boric acid and 2-bromine-5,5,10,10-thianthrene to obtain 9-ethyl-3-(1,2-diphenylvinyl)-6-(5,5,10,10-thianthrene)carbazole. The carbazole compound has favorable heat stability, electrochemical stability, charge transfer performance and luminescence property and can serve as a blue-green organic electroluminescence material.

Description

technical field [0001] The invention relates to a heterocyclic compound containing carbon, hydrogen, nitrogen, sulfur and oxygen, specifically a carbazole compound containing thianthrene tetraoxide and diphenylethylene structure and a preparation method thereof, and the compound as an organic electroluminescence application of materials. Background technique [0002] Over the past few decades, significant progress has been made in the optimization of solid-state organic fluorescent materials for the fabrication of high-efficiency OLEDs. However, the maximum internal quantum efficiency (IQE) of classical OLEDs is theoretically limited to 25%, and the non-emitting triplet excitons account for 75%, which greatly limits the development of OLEDs. To take full advantage of triplet and singlet excitonic luminescence, Adachi et al. proposed a better method called thermally activated delayed fluorescence (TADF). The principle is to upconvert triplet excitons to singlet states throu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/04C09K11/06H01L51/54
CPCC09K11/06C07D409/04C09K2211/1029C09K2211/1092H10K85/6576H10K85/6572
Inventor 董秀清施和平张鑫磊王淑娟程芳琴
Owner SHANXI UNIV
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