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Organic small molecular photoelectric functional material adopting 3-benzoylpyridine as receptor unit as well as preparation method and application thereof

A technology of benzoylpyridine and photoelectric functional materials, which is applied in the fields of organic chemistry, silicon organic compounds, chemical instruments and methods, etc., and can solve the problems of stability, weak interaction, and low molecular level orientation of light-emitting materials that affect the anti-intersystem crossing rate and other problems, to avoid the reduction of radiation rate, the horizontal orientation of macromolecules, and the effect of improving horizontal molecular orientation

Active Publication Date: 2018-12-21
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the materials reported above are all traditional benzophenones or aromatic amines coupled to the nitrogen remote receptors. The donor-receptor interaction is weak, there is no intramolecular hydrogen bond, and the molecular level orientation is low, which seriously affects the anti-intersystem crossing rate. and the stability of the luminescent material

Method used

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  • Organic small molecular photoelectric functional material adopting 3-benzoylpyridine as receptor unit as well as preparation method and application thereof
  • Organic small molecular photoelectric functional material adopting 3-benzoylpyridine as receptor unit as well as preparation method and application thereof
  • Organic small molecular photoelectric functional material adopting 3-benzoylpyridine as receptor unit as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The reaction formula of compound P1 is as follows:

[0030]

[0031] Concrete reaction steps are as follows:

[0032] (6-bromopyridin-3-yl) (phenyl) ketone (1.5mmol, 390mg), carbazole (1.6mmol, 270mg), cuprous iodide (0.075mmol, 18mg), 1,10-phenanthro Phenyl (0.075mmol, 11mg) and anhydrous sodium carbonate (3mmol, 415mg) were sequentially added to the reaction flask. After the nitrogen gas was replaced three times, 10 mL of p-xylene was added through a syringe. Reflux reaction at 150° C. for 24 hours under nitrogen atmosphere. After the reaction, the system was returned to room temperature, extracted and washed with dichloromethane and saturated brine. The organic phase was recovered and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Then the crude product was separated and purified by column chromatography, the eluent was petroleum ether / dichloromethane 3:1, and the compound P1 product was finally obtained with ...

Embodiment 2

[0034] The reaction formula of compound P2 is as follows:

[0035]

[0036] Concrete reaction steps are as follows:

[0037] Compared with Example 1, the difference is that carbazole is replaced by an equivalent amount of diphenylamine, other raw materials and steps are the same as in Example 1, and the compound P2 product is finally obtained with a yield of 75%. Product Molecular Formula: C 24 h 18 N 2O; molecular weight m / z: 350.16; elemental analysis results: C, 82.26; H, 5.18; N, 7.99; O, 4.57.

Embodiment 3

[0039] The reaction formula of compound P3 is as follows:

[0040]

[0041] Concrete reaction steps are as follows:

[0042] Compared with Example 1, the difference is that carbazole is replaced by an equivalent amount of phenoxazine, and other raw materials and steps are the same as in Example 1, and the compound P3 product is finally obtained with a yield of 73%. Product Molecular Formula: C 24 h 16 N 2 o 2 ; Molecular weight m / z: 365.16; Elemental analysis results: C, 79.11; H, 4.43; N, 7.69; O, 8.78.

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Abstract

The invention discloses an organic small molecular photoelectric functional material adopting 3-benzoylpyridine as a receptor unit, which mainly depends on hydrogen-bond interaction of nitrogen in benzoylpyridine, can effectively avoid the deficiency of low radiation rate caused by large torsion angle, thereby improving the horizontal molecular orientation, and realizing the structure simplification of devices and performance of the devices and prolonging the service life. By controlling the type and size of a donor connecting unit, the intrinsic characteristics of the material such as a molecular weight, a conjugated length, charge transfer and the like can be effectively adjusted. The invention also discloses a preparation method and application of the organic small molecular photoelectric functional material. The organic small molecular photoelectric functional material adopting 3-benzoylpyridine as the receptor unit has the advantages that the radiation rate coefficient is high, the quantum efficiency is high, the current carrier transport performance is high, the color is adjustable when being used as a luminescent layer of an organic electroluminescent device, high efficiencyand stability can be realized, the service life is long, and the like.

Description

technical field [0001] The invention relates to the technical field of materials for organic photoelectric devices, in particular to organic small molecule photoelectric functional materials based on 3-benzoylpyridine as an acceptor unit and its preparation method and application. Background technique [0002] Organic electroluminescent (OLED) devices have great application prospects in the fields of flat panel displays and solid light sources. In order to improve the efficiency and lifespan of organic optoelectronic devices, compared with polymer light-emitting materials, organic small molecules have the advantages of simple preparation, stable structure, and convenient purification, so that higher device efficiency can be obtained, so that they are close to commercial applications. At present, based on the development of small molecules, red, green and blue three-color luminescent materials can be obtained and multilayer flexible devices can be prepared, which has attracte...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D401/14C07D413/04C07D417/04C07D213/74C07D491/107C07D495/10C07F7/08H01L51/54
CPCC07D213/74C07D401/04C07D401/14C07D413/04C07D417/04C07D491/107C07D495/10C07F7/0816C07F7/083H10K85/657H10K85/6572
Inventor 苏仕健王良迎蔡欣佚乔振洋李梦柯
Owner SOUTH CHINA UNIV OF TECH
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