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Preparation and mechanism research of efficient phosphorescent pure organic long-afterglow material

A high-efficiency phosphorescence, long-term technology, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., to achieve the effects of cheap raw materials, high quantum efficiency, and long afterglow life.

Inactive Publication Date: 2018-06-05
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, few researches have specifically studied which halogen bonds play an important role in enhancing phosphorescence efficiency.

Method used

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  • Preparation and mechanism research of efficient phosphorescent pure organic long-afterglow material
  • Preparation and mechanism research of efficient phosphorescent pure organic long-afterglow material
  • Preparation and mechanism research of efficient phosphorescent pure organic long-afterglow material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The synthesis process of pure organic long afterglow materials:

[0034] Weigh 5 g (29.9 mmol) of carbazole in a 250 mL flask, fill it with nitrogen three times, add 100 mL of distilled tetrahydrofuran solution, stir in an ice-water bath, slowly add 22.4 mL of n-butyllithium (concentration: 1.6 mol / L) dropwise, Stir in an ice-water bath for one hour. In another 250mL two-necked flask, add 5.5g (29.9mmol) of trichlorotriazine, fill with nitrogen three times, add 50mL of distilled tetrahydrofuran solution, and stir in an ice-water bath. Water bath reaction for four hours. The obtained mixed solution was suction-filtered, washed with acetone, dried, and used as the raw material for the second step reaction. The reaction product is named triazine monocarbazole starting material.

[0035] Weigh 0.823g (4.76mmol) of p-bromophenol and 0.254g (6.344mmol, solid content: 60%) of sodium hydride in a 50mL flask, put it in an ice-water bath, slowly add distilled tetrahydrofuran s...

Embodiment 2

[0037] Take by weighing m-bromophenol 0.823g (4.76mmol), sodium hydride 0.254g (6.344mmol, solid content is 60%) in the flask of 50mL, put into the ice-water bath, slowly drop the distilled tetrahydrofuran solution, stir, have A large number of bubbles are generated, the solution is light brown, and becomes clear after 30 minutes. Weigh 0.5g (1.586mmol) of triazine monocarbazole raw material into a 100mL flask, add 60mL tetrahydrofuran, stir, and add the p-bromophenol mixed solution into triazine monocarbazole The azole was refluxed and stirred for two hours. Spin-dried, petroleum ether: dichloromethane = 4:1, separated by chromatographic column, and synthesized pure organic long-lasting material to obtain a white solid m-BrTCz (0.63g, yield rate 67.0%), the structural characterization is as follows: 1 H NMR(d-DMSO):8.13(d,2H),8.07(d,2H),7.77(t,2H),7.68(d,2H),7.55(t,2H),7.45(tt,2H), 7.36(t,2H),7.19(t,2H); 13 C NMR (CDCl3): δ172.89, 165.73, 152.62, 138.48, 130.98, 129.53, 127...

Embodiment 3

[0039] Weigh 0.823g (4.76mmol) of o-bromophenol, 0.254g (6.344mmol, solid content: 60%) of sodium hydride in a 50mL flask, put it in an ice-water bath, slowly add distilled tetrahydrofuran solution dropwise, stir, and A large number of bubbles are generated, the solution is light brown, and becomes clear after 30 minutes. Weigh 0.5g (1.586mmol) of triazine monocarbazole raw material into a 100mL flask, add 60mL tetrahydrofuran, stir, and add the p-bromophenol mixed solution into triazine monocarbazole The azole was refluxed and stirred for two hours. Spin-dried, petroleum ether: dichloromethane = 4:1, separated by chromatographic column, and synthesized pure organic long-lasting material to obtain a white solid o-BrTCz (0.53g, yield 57.1%), the structural characterization is as follows: 1 H NMR(d-DMSO):8.10(d,2H),7.91(d,2H),7.78(d,2H),7.63(d,4H),7.43~7.47(m,2H),7.32(t,2H ), 7.07(t,2H). 13 C NMR (CDCl 3 ): δ172.57, 165.65, 149.84, 138.54, 133.82, 128.97, 127.64, 126.83, 126....

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Abstract

The invention belongs to the field of pure organic long-afterglow materials and in particular relates to preparation and mechanism research of an efficient phosphorescent pure organic long-afterglow material. The material has the characteristics that (1) the material is synthesized by two steps, the raw materials are cheap and the synthetic method is simple; (2) the synthesized material is long inafterglow service life and high in quantum efficiency; and (3) a policy of improving the phosphorescent quantum efficiency is provided as different halogen bonds are formed by isomerization. The material provided by the invention has a huge potential in the fields of organic electroluminescence devices and counterfeiting prevention. It can be expected that the organic light-emitting materials area type of novel long-afterglow materials with huge commercialized potential.

Description

technical field [0001] The invention belongs to the field of pure organic long afterglow materials, specifically relates to a class of pure organic long afterglow materials with high phosphorescence efficiency, and relates to the research on the mechanism of high phosphorescence efficiency of such materials. Background technique [0002] In recent years, pure organic phosphorescent materials have attracted much attention due to their long luminescence lifetime, large Stokes shift, rich excitonic properties, low cost, and diverse molecular designs. However, pure organic phosphorescence is very inefficient at room temperature due to weak orbital coupling between singlet and triplet states and nonradiative transitions due to molecular vibrations or perturbations. The low efficiency of pure organic phosphorescent materials severely limits its practical application. Summarizing the reported literature, it is concluded that there are two main conditions to enhance room temperatur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04C09K11/06
CPCC09K11/06C07D403/04C09K2211/1059
Inventor 安众福黄维史慧芳蔡素芝
Owner NANJING UNIV OF TECH
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