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Preparation and application of organoboron phosphorescent material with ultra-long lasting luminescent performance

A technology of luminescent properties and phosphorescent materials, applied in the field of preparation of organoboron phosphorescent materials, can solve the problems of low luminescent quantum efficiency, oxygen collision quenching, short life, etc., and achieve high luminescent quantum efficiency, simple synthesis method and good stability. Effect

Active Publication Date: 2019-11-08
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Pure organic compounds have the advantages of flexibility and easy processing, but pure organic ultra-long room temperature phosphorescence materials are rarely reported, because it is relatively difficult to generate ultra-long room temperature phosphorescence from pure organic molecules. The main reasons are: low intersystem crossing rate, triplet excitation state to the singlet ground state (phosphorescence) is spin-forbidden, and the resulting triplet excited state is extremely prone to non-radiative relaxation and quenching by oxygen collisions
As a result, organic long-lasting materials have short lifetimes and low luminous quantum efficiency, which greatly limits the application of materials. Therefore, it is very urgent to design and synthesize long-lived and high-efficiency long-lasting materials.

Method used

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  • Preparation and application of organoboron phosphorescent material with ultra-long lasting luminescent performance
  • Preparation and application of organoboron phosphorescent material with ultra-long lasting luminescent performance
  • Preparation and application of organoboron phosphorescent material with ultra-long lasting luminescent performance

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The structural formula of the target product: .

[0031] Synthesis of organoboron phosphorescent materials:

[0032] Step 1. Weigh 1.00 g of carbazole and 1.25 g of 9,9-diphenylacridine into a single-necked bottle, vacuum three times with nitrogen blowing, nitrogen protection, add 20 mL of freshly steamed toluene solution and stir to dissolve.

[0033] Step 2: Vacuum the one-necked bottle with nitrogen three times, under the protection of nitrogen, dissolve 0.58 mL of malonyl chloride in 10 mL of freshly steamed toluene solution, stir for 5 minutes, then add the reaction system in step 1 dropwise into the malonyl chloride toluene solution, stirred for two hours, extracted with water and dichloromethane, collected the organic phase, added silica gel powder and spin-dried, and purified by column chromatography to obtain the intermediate product, the eluent used was dichloromethane:petroleum Ether is 1:4.

[0034] Step 3, dry the intermediate product, vacuumize and blo...

Embodiment 2

[0036] The structural formula of the target product: .

[0037] Synthesis of organoboron phosphorescent materials:

[0038] Step 1. Weigh 1.00 g of carbazole and 1.02 g of diphenylamine into a single-necked bottle, vacuum three times to blow nitrogen, and protect with nitrogen, add 20 mL of freshly steamed toluene solution and stir to dissolve.

[0039] Step 2: Vacuum the one-necked bottle with nitrogen three times, under the protection of nitrogen, dissolve 0.58 mL of malonyl chloride in 10 mL of freshly steamed toluene solution, stir for 5 minutes, then add the reaction system in step 1 dropwise into the malonyl chloride toluene solution, stirred for two hours, extracted with water and dichloromethane, collected the organic phase, added silica gel powder and spin-dried, and purified by column chromatography to obtain the intermediate product, the eluent used was dichloromethane:petroleum Ether is 1:4.

[0040] Step 3: Dry the intermediate product, vacuumize and blow nitr...

Embodiment 3

[0042] The structural formula of the target product: .

[0043] Synthesis of organoboron phosphorescent materials:

[0044] Step 1. Weigh 1.25 g of 9,9-diphenylacridine and 1.02 g of diphenylamine into a single-necked bottle, vacuum three times with nitrogen blowing, nitrogen protection, add 20 mL of freshly steamed toluene solution and stir to dissolve.

[0045] Step 2: Vacuum the one-necked bottle with nitrogen three times, under the protection of nitrogen, dissolve 0.58 mL of malonyl chloride in 10 mL of freshly steamed toluene solution, stir for 5 minutes, then add the reaction system in step 1 dropwise into the malonyl chloride toluene solution, stirred for two hours, extracted with water and dichloromethane, collected the organic phase, added silica gel powder and spin-dried, and purified by column chromatography to obtain the intermediate product, the eluent used was dichloromethane:petroleum Ether is 1:4.

[0046] Step 3: Dry the intermediate product, vacuumize and...

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Abstract

The invention discloses preparation and application of an organoboron phosphorescent material with the ultra-long lasting luminescent performance. By molecular design, electron-absorbing group difluoro boron and various donor groups are introduced in molecular, and the organoboron phosphorescent material with the ultra-long lasting luminescent performance is synthesized. The organic long lasting material has the advantages that the costs of raw materials are low, synthesis is easy and convenient, lasting luminescence for several seconds is achieved after an excitation source is closed, and thefluorescence quantum efficiency is high. Wide potential application value of the material is achieved in the fields such as anti-fake, bioimaging and photoelectric materials, and the organoboron phosphorescent material is expected to be applied to the fields such as anti-fake and organic light-emitting devices.

Description

Technical field: [0001] The invention belongs to the technical field of organic afterglow luminescent materials, and in particular relates to the preparation and application of an organic boron phosphorescent material with ultra-long afterglow luminescent performance. Background technique: [0002] Long afterglow is stable and long-lasting room temperature phosphorescence, which lasts for several seconds, minutes or even hours after the excitation light source is removed. Materials with this feature could find applications in displays, emergency signs, sensors, bioimaging, and anti-counterfeiting. Although ultra-long room temperature phosphorescence has a long history, it is mainly limited to inorganic substances containing heavy metals. Given the drawbacks of phosphors, such as the toxicity of heavy metals, expensive metal components, and harsh preparation conditions, attention has turned to long-lasting materials of pure organic compounds. [0003] Room-temperature phosp...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06
CPCC07F5/022C09K11/06C09K2211/188
Inventor 陶冶唐乐乐陈润锋李欢欢
Owner NANJING UNIV OF POSTS & TELECOMM
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