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Organic light-emitting material with room-temperature phosphorescence performance and preparation method and application thereof

A luminescent material, room temperature phosphorescence technology, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of low room temperature phosphorescence quantum yield, limited material types, and no room temperature phosphorescence performance of phosphorescent materials.

Active Publication Date: 2021-05-28
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The room-temperature phosphorescence performance of phosphorescent materials is not pointed out in the above inventions, and the raw materials for preparing phosphorescent materials are expensive and rare heavy metal materials, such as heavy metal iridium ligands
[0009] Generally speaking, there are still many deficiencies in this kind of organic light-emitting materials with room temperature phosphorescent properties, such as the types of materials are still relatively limited, and there is no clear basis for molecular design , most of the room temperature phosphorescent quantum yields are not high, therefore, the existing technology, including materials, still needs to be further improved

Method used

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  • Organic light-emitting material with room-temperature phosphorescence performance and preparation method and application thereof
  • Organic light-emitting material with room-temperature phosphorescence performance and preparation method and application thereof
  • Organic light-emitting material with room-temperature phosphorescence performance and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] (1) Synthesis of intermediate 4,4'-diiodo-diphenylsulfone, the synthetic route is as follows:

[0051]

[0052] Add iodobenzene (7.0g, 34.3mmol) and chlorosulfonic acid (12.3g, 105.6mmol) into a 250ml round-bottomed flask and react at 50°C for 3 hours. After the reaction, pour the mixture into an ice-water bath and stir thoroughly, and filter Finally, the water layer was removed, the organic layer was washed with water, dried over anhydrous sodium sulfate, and separated by silica gel column chromatography, dichloromethane:petroleum ether=1:1 was used as eluent to obtain 5.96g of yellow-white solid, yield: 74%, The structure is identified as: 4,4'-diiodo-diphenyl sulfone, the theoretical value of elemental analysis is C 12 h 8 I 2 o 2 S (%): C 30.66, H 1.72, O 6.81; found values: C 30.56, H 1.78, O 6.78.

[0053] (2) Synthesis of intermediate 4-iodo-4'-carbazolyl diphenyl sulfone, the synthetic route is as follows:

[0054]

[0055] Select 4,4'-diiodo-diphenyl...

Embodiment 2

[0061] The synthesis of embodiment 2 target product, synthetic route is as follows:

[0062]

[0063] Add 4-iodo-4'-carbazolyldiphenylsulfone (2.00g, 3.93mmol), cuprous cyanide (0.42g, 4.72mmol), 15ml of N,N-dimethylformamide, and add 100ml of round bottom The flask was refluxed overnight, cooled to room temperature, poured into 2ml of ferric chloride hydrochloric acid solution, stirred for half an hour, quenched with 10ml of saturated aqueous sodium chloride solution, extracted with dichloromethane, dried over anhydrous sodium sulfate, and separated by silica gel column chromatography. Dichloromethane is used as eluting agent, the product is white powder, productive rate: 87%, elemental analysis theoretical value C 25 h 16 N 2 o 2 S (%): C 73.51, H 3.95, N 6.86, found values: C 73.38, H 4.05, N 6.92.

[0064] Such as figure 1 As shown, the fluorescence emission peak of the target product in Example 2 in n-hexane is 368nm, and the low-temperature phosphorescence peak i...

Embodiment 3

[0066] (1) Synthesis of intermediate 4-iodo-4'-phenothiazinyl diphenyl sulfone, the synthetic route is as follows:

[0067]

[0068] 4,4'-diiodo-diphenylsulfone (1.50g, 3.19mmol), phenothiazine (0.70g, 3.50mmol), sodium tert-butoxide (0.55g, 5.71mmol), palladium acetate (0.025g, 0.11mmol), tri-tert-butylphosphine tetrafluoroborate (0.095g, 0.33mmol), 50ml of toluene, put into a 100ml round bottom flask, reflux at 110°C for 48 hours, quenched with 10ml of saturated aqueous sodium chloride solution, dichloromethane Extracted, dried over anhydrous sodium sulfate, separated by silica gel column chromatography, dichloromethane / petroleum ether (v:v) = 3:2 as eluent, yield: 72%, elemental analysis theoretical value C 24 h 16 IN 5 o 2 S 2 (%): C 53.24, H 2.98, N 2.59, found values: C 53.36, H 2.78, N 2.47.

[0069] At the same time, the intermediate 4-iodo-4'-phenothiazinyldiphenylsulfone is also one of the target products.

[0070] (2) Synthesis of the target product of embo...

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Abstract

The invention discloses an organic light-emitting material with room-temperature phosphorescence performance and a preparation method and application thereof, and belongs to the technical field of organic light-emitting materials. The organic light-emitting material takes diphenyl sulfone as a framework, and is connected with different donor units and acceptor units, and the bipolar small organic molecule luminescent material containing the asymmetric donor-diphenyl sulfone-acceptor or hydrogen group is formed. The novel organic light-emitting material is an asymmetric D-A type (Donor-Acceptor type) containing the diphenyl sulfone unit, has a high triplet state energy level, good hole / electron transport performance and high fluorescence quantum yield, can be widely applied to the field of organic electroluminescent devices, and has broad application prospects. The strong room-temperature phosphorescence property enables the material to be also suitable for the fields of anti-counterfeiting, chemical and biological detection, biological imaging and the like.

Description

technical field [0001] The invention relates to the technical field of organic luminescent materials, in particular to a bipolar organic luminescent material with an asymmetric structure based on diphenyl sulfone as a skeleton and a preparation method and application thereof. Background technique [0002] In the field of luminescence, compared with inorganic materials, the research of organic materials has been paid more and more attention by people. Because of the wide variety of organic compounds, good adjustability, rich colors, high color purity, and relatively flexible molecular design, organic photoelectric functions Materials continue to receive extensive attention in theoretical research and practical applications such as biosensing, display lighting, and data storage. [0003] Since Forrest et al. discovered electrophosphorescence using metal complexes in 1998, phosphorescent guest materials based on heavy metal complexes have developed rapidly (Highly efficient pho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D417/12C07D219/02C09K11/06H01L51/54
CPCC07D209/86C07D417/12C07D219/02C09K11/06C09K2211/1029C09K2211/1037H10K85/657H10K85/6572H10K50/11Y02E10/549
Inventor 余玲李世军
Owner HANGZHOU NORMAL UNIVERSITY