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Organic small-molecule efficient room-temperature phosphorescent material on basis of aryl imide, and preparation and application of organic small-molecule efficient room-temperature phosphorescent material

An aromatic amine and reaction technology, which is applied in the field of organic luminescence and its anti-counterfeiting, can solve the problems of difficult mass preparation, few molecular species, long synthesis steps, etc., and achieves the effects of cheap raw materials, high luminous efficiency, and simple synthesis method.

Active Publication Date: 2019-05-10
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Up to now, although there have been some reports on room temperature phosphorescence (RTP) materials and their applications in anti-counterfeiting, the reported RTP materials generally have problems such as long synthesis steps, heavy metal content, low preparation efficiency, and difficulty in large-scale preparation. There are very few types, mainly concentrated in halogen-based, precious metals, etc.

Method used

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  • Organic small-molecule efficient room-temperature phosphorescent material on basis of aryl imide, and preparation and application of organic small-molecule efficient room-temperature phosphorescent material
  • Organic small-molecule efficient room-temperature phosphorescent material on basis of aryl imide, and preparation and application of organic small-molecule efficient room-temperature phosphorescent material
  • Organic small-molecule efficient room-temperature phosphorescent material on basis of aryl imide, and preparation and application of organic small-molecule efficient room-temperature phosphorescent material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The reaction equation is as follows:

[0037]

[0038] The specific steps of the reaction are as follows:

[0039] A mixture of compound formula A-1 and compound formula B-1 in glacial acetic acid was refluxed for 4 hours. The solid was separated from the mixture (the reaction liquid was cooled to room temperature, and the precipitate was filtered), and the product formula I-1 was obtained.

[0040] The H NMR spectrum of the compound shown in formula Ⅰ-1 is as follows: figure 1 As shown, the characterization data are as follows:

[0041] 1 H NMR (300MHz, Chloroform-d) δ7.98 (d, J=7.7Hz, 2H), 7.70–7.51 (m, 8H), 7.36–7.23 (m, 4H), 7.20–7.12 (m, 2H), HR-MS(APCI)m / z calcd for C 26 h 16 N 2 o 2 [M+H] + 389.12, found 389.13.

[0042] From the above detection results, it can be seen that the structure of the compound represented by formula I-1 is correct.

Embodiment 2

[0044] The reaction equation is as follows:

[0045]

[0046] The specific steps of the reaction are as follows:

[0047] A mixture of compound formula A-1 and compound formula B-1 in glacial acetic acid was refluxed for 4 hours. The solid was separated from the mixture (the reaction liquid was cooled to room temperature, and the precipitate was filtered), and the product formula I-2 was obtained.

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Abstract

The invention discloses an organic small-molecule efficient room-temperature phosphorescent material on the basis of aryl imide, and preparation and application of the organic small-molecule efficientroom-temperature phosphorescent material. A structural formula of the organic small-molecule efficient room-temperature phosphorescent material is shown as a formula I. An R in the formula I represents a substituent group or a plurality of substituent groups and is selected from at least one of H, aliphatic alkyl, aryl, hetero-aryl and halogen, and the substituent groups are connected onto benzene rings; an R1, an R2, an R3, an R4 and an R5 in the formula I are independently selected from electron-rich aromatic amine substituent groups, H and halogen but cannot simultaneously be the electron-rich aromatic amine substituent groups, the H and the halogen, and each electron-rich aromatic amine substituent group comprises at least one part of nitrogen. The organic small-molecule efficient room-temperature phosphorescent material, the preparation and the application have the advantages that phthalimide derivatives have the room-temperature phosphorescent properties, are high in fluorescentquantum yield and good in stability, and derivatization of the phthalimide derivatives can be facilitated; synthesis methods are simple, raw materials are low in cost, products are high in yield, andthe organic small-molecule efficient room-temperature phosphorescent material can be prepared on a large scale; the carbazole-substituted phthalimide derivatives are high in luminous efficiency and have super-long afterglow and scribbling functions, and the like.

Description

technical field [0001] The invention relates to a room-temperature phosphorescent material and its preparation and application, in particular to an organic small molecule high-efficiency room-temperature phosphorescent material based on aramid and its preparation and application, belonging to the field of organic luminescence and its anti-counterfeiting. Background technique [0002] Phosphorescent emission is one of the characteristics of molecular excited states. Since the triplet state of organic molecules has a long lifetime and allows long-distance migration of excitons, it has broad application prospects in optoelectronic fields such as photovoltaic devices, photocatalytic reactions, display and lighting systems, molecular sensing, and bioimaging. However, due to the harsh conditions (low temperature, absence of oxygen) usually required for the phosphorescence of organic compounds, the development of this field has been relatively slow. In recent years, scientists hav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06
Inventor 陈传峰张亮
Owner INST OF CHEM CHINESE ACAD OF SCI
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