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Organic luminescent material with thermally induced delayed fluorescence performance, preparation method and application thereof

A technology of thermally induced delayed fluorescence and luminescent materials, which is applied in the fields of luminescent materials, fluorescence/phosphorescence, and material analysis through optical means. High fluorescence quantum yield, good solubility effect

Active Publication Date: 2021-09-21
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Generally speaking, some of the existing organic light-emitting materials with thermally induced delayed fluorescence performance still have deficiencies. For example, organic electroluminescent devices based on TADF materials as the object generally have complex device structures, rapid efficiency decay, and unstable phenomena. In the actual application process, the device preparation procedure is simplified, the device efficiency is stabilized, and higher requirements are put forward for the design of luminescent materials.

Method used

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  • Organic luminescent material with thermally induced delayed fluorescence performance, preparation method and application thereof
  • Organic luminescent material with thermally induced delayed fluorescence performance, preparation method and application thereof
  • Organic luminescent material with thermally induced delayed fluorescence performance, preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0060] (1) Synthesis of intermediate 2,6-dibromo-cyclofluorenone dithiophene, the synthetic route is as follows:

[0061]

[0062] Add 3,3-dibromo-2,2-bithiophene (2.55g, 7.87mmol) into a 200ml Zelanque bottle, pump it through three times, add 50ml of ether, put it into a low-temperature box that has been precooled to -78°C, and slowly add n-Butyllithium (8.04ml, 18.89 mmol), after 2 hours of reaction, 100ml of dimethylcarbamoyl chloride was added, stirred overnight to room temperature, quenched with ice water, extracted with ether, dried over anhydrous sodium sulfate, separated by silica gel column chromatography, Chloromethane / petroleum ether (v:v)=1:1 is used as eluent, the product is dark purple powder, yield: 68%, elemental analysis theoretical value C 9 h 4 OS 2 (%): C 56.23, H 2.10, O 8.32. Found values: C 56.28, H 2.08, O 8.28;

[0063] Add the dark purple powder cyclofluorenone dithiophene and N-bromosuccinimide obtained above with a molar ratio of 1:2 into an o...

Embodiment 2

[0074]

[0075] Select 2,6-dibromo-cyclofluorenone dithiophene (2.50g, 7.14mmol), carbazole (1.19g, 7.14mmol), cuprous iodide (0.10g, 0.53mmol), potassium carbonate (2.20g, 15.9 mmol), 18-crown-6 (0.14g, 0.54 mmol), 3ml o-dichlorobenzene, put into a 150ml round bottom flask, reflux at 190°C for 48 hours, quenched with 10ml saturated aqueous sodium chloride solution, extracted with dichloromethane, no Dry over sodium sulfate, separate by silica gel column chromatography, dichloromethane / petroleum ether (v:v) = 1:1 as eluent, yield: 68%, elemental analysis theoretical value C 21 h 10 BrNOS 2 (%): C 57.81, H 2.31, N 3.21. Found values: C 57.78, H 2.37, N 3.32.

Embodiment 3

[0077]

[0078] Putting 2,6-dibromo-cyclofluorenone dithiophene and carbazole into the reaction at a molar ratio of 1:2, a double-sided carbazole-substituted cyclofluorenone dithiophene can be synthesized with a yield of 86% and a theoretical value of C 33 h 18 N 2 OS 2 (%): C 75.84, H 3.47, N 5.36. Found values: C 75.78, H 3.52, N 5.43.

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Abstract

The invention discloses an organic luminescent material with thermally-induced delayed fluorescence performance and its preparation method and application, belonging to the technical field of organic luminescent materials. Combined with the acceptor unit, a bipolar organic small molecule luminescent material is formed. The organic luminescent material with thermally delayed fluorescence performance prepared by the present invention is a D-A structure (Donor-Acceptor type) containing cyclofluorenone dithiophene unit, has good hole / electron transport performance, high fluorescence quantum High yield, can be widely used in the field of organic electroluminescent devices, anti-counterfeiting, chemical and biological detection, biological imaging and other fields; the cyclofluorenone dithiophene intermediate prepared by the present invention has good solubility in the organic phase and can be used in evaporation devices , is also suitable for spin-coated devices.

Description

technical field [0001] The invention relates to the technical field of organic light-emitting materials, in particular to a bipolar organic light-emitting material with thermally induced delayed fluorescence performance based on cyclofluorenone dithiophene as a skeleton, a preparation method and application thereof. Background technique [0002] Organic light-emitting diodes (OLEDs) have great application prospects in the fields of display and lighting due to the advantages of ultra-thin, light weight, low energy consumption, active light emission, wide viewing angle, and fast response. more and more people's attention. [0003] In the past 30 years, the vast number of scientific researchers have never stopped exploring organic optoelectronic functional materials with high exciton utilization. In 1998, Forrest et al. discovered electrophosphorescence by using metal complexes, and phosphorescent objects based on heavy metal complexes The material has been developed rapidly (...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04C07F9/6561C09K11/06H01L51/50H01L51/54G01N21/64
CPCC07D495/04C07F9/6561C09K11/06G01N21/6428C09K2211/1007C09K2211/1029C09K2211/1092C09K2211/1037G01N2021/6432H10K85/654H10K85/6576H10K85/657H10K85/6572H10K50/11
Inventor 余玲李世军
Owner HANGZHOU NORMAL UNIVERSITY