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Benzene-substituted phenothiazine unit-based luminescent material, intermediate thereof and organic photoelectric device made by luminescent material

A technology of phenophenothiazine and light-emitting materials, which is applied in light-emitting materials, electric solid devices, semiconductor devices, etc., can solve the problems of limited organic small molecule light-emitting materials, and achieve rich performance, high decomposition temperature, and low sublimation temperature Effect

Active Publication Date: 2015-01-21
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] So far, organic light-emitting diodes have made great progress. Scientists have proposed various theories to explain the mechanism of light emission, but so far, organic small molecule light-emitting materials with simple structure, good performance, and commercialization requirements Still very limited, the development of new luminescent materials is still of great significance

Method used

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  • Benzene-substituted phenothiazine unit-based luminescent material, intermediate thereof and organic photoelectric device made by luminescent material
  • Benzene-substituted phenothiazine unit-based luminescent material, intermediate thereof and organic photoelectric device made by luminescent material
  • Benzene-substituted phenothiazine unit-based luminescent material, intermediate thereof and organic photoelectric device made by luminescent material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation of intermediates of formula 1 and formula 2:

[0044] Add 3.98g (20mmol) of phenothiazine, 12.24g of iodobenzene (60mmol, 3equ) and 1.27g (20mmol) of copper powder into a 100ml three-neck flask, heat to 200°C and react for 12 hours. Unnecessary iodobenzene removes unreacted iodobenzene, obtains 4.9g product by the method of column chromatography, productive rate 89%, C 18 h 13 NS m / z = 275.08. Theoretical value: 275.08 (100.0%), 276.08 (20.4%), 277.07 (4.5%), 277.08 (2.0%) (note: the numerical percentage in brackets represents the corresponding estimated value of the corresponding mass-to-charge ratio m / z taking into account the isotope effect Ratio); Elemental analysis: C, 78.51%; H, 4.76%; N, 5.09%; S, 11.64%, the obtained product was confirmed as 9-phenylphenothiazine.

[0045] Under ice-cooling, in a 100ml three-necked flask, add the obtained 9-phenylphenothiazine (2.75g, 10mmol), add 30ml of chloroform as a solvent, add dropwise 3.2g of bromine water...

Embodiment 2

[0048] Preparation of intermediates of formula 3:

[0049]Add phenothiazine 3.98g (20mmol) and 6.26g p-bromoiodobenzene (22mmol, 1.1equ) and 1.27g cuprous iodide in 100ml three-necked flask, add solvent nitrogen nitrogen dimethyl formamide 100ml, heat to 200 ℃ of reaction for 24 hours, the reaction was completed, cooled, extracted with dichloromethane, obtained 2.47g product by the method of column chromatography, productive rate 35%, C 18 h 12 BrNS m / z = 352.99. Theoretical: 352.99 (100.0%), 354.99 (99.3%), 353.99 (20.4%), 355.99 (20.0%), 354.98 (4.5%), 356.98 (4.4%), 356.99 (2.1%), 355.98 (1.2%) ; Elemental analysis: C, 61.03%; H, 3.41%; Br, 22.55%; N, 3.95%; S, 9.05%.

[0050] Take 12.0 g of the above product and add it to 50 ml of dichloromethane and 25 ml of acetic acid, add 2.0 ml of hydrogen peroxide, and react overnight at 80 ° C. After the reaction is completed, the temperature is lowered, extracted with dichloromethane, and 32.12 g of the intermediate is obtained ...

Embodiment 3

[0053] Preparation of organic small molecule light-emitting materials based on benzophenothiazine units with structural formula P1:

[0054] Under nitrogen atmosphere, in 100ml flask, add the intermediate (0.93g, 2mmol) with structural formula 1 that embodiment 1 obtains, 15ml N,N-dimethylpropenyl urea, cuprous iodide (0.20g) potassium carbonate (0.700g) carbazole (0.701g, 1.05equ), 18-crown-6 (0.20g), nitrogen gas for 5min, 160°C temperature for 24h, the reaction was completed, then dichloromethane extraction, liquid separation, combined organic phase , dried with anhydrous magnesium sulfate, filtered with suction, and the resulting filtrate was desolventized under reduced pressure, dried in vacuo; column separation, with petroleum ether: dichloromethane = 2: 1 (volume ratio) through the column to obtain a white solid 0.71g , yield 56%, molecular formula: C 42 h 27 N 3 o 2 S, m / z=637.18. Theoretical value: 637.18 (100.0%), 638.19 (45.8%), 639.19 (11.0%), 639.18 (5.0%), 6...

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Abstract

The invention belongs to the technical field of photoelectric material, and concretely relates to a benzene-substituted phenothiazine unit-based luminescent material, an intermediate thereof and an organic photoelectric device made by the luminescent material. The luminescent material takes phenothiazine as an initial reaction raw material, the intermediate is prepared through an Ullmann reaction, and a target compound is obtained through the Ullmann reaction or a Suzuki reaction. The material has the advantages of single structure and definite molecular weight; has high decomposition temperature and low sublimation temperature, and the luminescent material with high purity cab can be easily obtained through sublimation. The material has good luminescence performance as a luminescent layer of the organic photoelectric device and can be used for an organic micromolecule light emitting diode.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, and in particular relates to a luminescent material based on a benzophenothiazine unit, an intermediate thereof, and an organic photoelectric device prepared from the luminescent material. Background technique [0002] In order to improve the efficiency and lifespan of organic optoelectronic devices, compared with polymers, light-emitting small molecules can obtain higher device efficiency due to fewer preparation steps, stable structure, and convenient purification, so that they may be commercially applied. Using small molecules to obtain red, green and blue three-color luminescent materials and fabricate flexible devices has attracted great attention and made great progress because of its incomparable advantages over inorganic materials. [0003] So far, organic light-emitting small molecules with phenylphenothiazine oxide as the core have rarely been reported. Based on this, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D417/14C07D417/04C07D417/10C07D279/34H01L51/50H01L51/54
Inventor 苏仕健李云川蔡欣佚谢高瞻刘欣彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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