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1,2,3-Triazole unit-based micro-molecular luminescent material and application thereof

A technology of luminescent materials and small molecules, applied in luminescent materials, electrical components, circuits, etc., can solve the problems of low exciton utilization of ordinary fluorescent materials, and achieve molecular weight determination, low sublimation temperature, and good reproducibility

Active Publication Date: 2015-12-23
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The excitons at the singlet energy level are allowed to transition back to the ground state, while the excitons at the triplet energy level are forbidden to transition back to the ground state. Therefore, the exciton utilization rate of ordinary fluorescent materials is not high.

Method used

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  • 1,2,3-Triazole unit-based micro-molecular luminescent material and application thereof
  • 1,2,3-Triazole unit-based micro-molecular luminescent material and application thereof
  • 1,2,3-Triazole unit-based micro-molecular luminescent material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] This example prepares the small molecule luminescent material P1, and its reaction is shown in the following formula:

[0027]

[0028] The specific implementation steps are: under a nitrogen atmosphere, add intermediate 1 (4,5-bis(4-bromophenyl)-2-phenyl-2H-1,2,3-triazole) to a 20mL three-necked flask ( 1.365g, 3mmol) and diphenylamine (1.268g, 7.5mmol), then add 15mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone, stir, after being completely dissolved, go to Add ethylene iodide (1.433g, 7.5mmol) potassium carbonate (2.070g, 15mmol), 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone 1,4,7 , 10,13,16-hexaoxacyclooctadecane (0.792g, 3mmol), heated to 190°C, reacted for 24 hours, cooled the reaction system to room temperature, extracted with dichloromethane, and used petroleum ether: dichloromethane = 2:1 ratio of eluent was subjected to silica gel column chromatography to obtain 806 mg of white solid with a yield of 42.67%. C 44 h 33 N 5 M / S=631.27 Theoretical v...

Embodiment 2

[0033] This example prepares the small molecule luminescent material P2, and its reaction is shown in the following formula:

[0034]

[0035] The specific implementation steps are as follows: the diphenylamine in Example 1 is replaced with equivalent 4,4'-di-tert-butyldiphenylamine, and other raw materials and steps are the same as in Example 1 to obtain 1345 mg of white solid product with a yield of 48.87%. . C 60 h 65 N 5 M / S=855.52m / z: 855.52 (100.0%), 856.53 (65.6%), 857.53 (21.2%), 858.53 (4.7%), 856.52 (1.8%), 857.52 (1.2%) C, 84.17; H, 7.65; N, 8.18.

Embodiment 3

[0037] This example prepares the small molecule luminescent material P3, and its reaction is shown in the following formula:

[0038]

[0039] The specific implementation steps are as follows: the diphenylamine in Example 1 is replaced by an equivalent amount of carbazole, and other raw materials and steps are the same as in Example 1 to obtain 872 mg of a white solid product with a yield of 46.29%. C 44 h 29 N 5 M / S=627.24 Theoretical values: 627.24 (100.0%), 628.25 (47.9%), 629.25 (11.2%), 630.25 (1.9%), 628.24 (1.8%). C, 84.19; H, 4.66; N, 11.16.

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses a 1,2,3-triazole unit-based micro-molecular luminescent material and an application thereof. The molecular weight, the pi electron conjugate degree, the intramolecular charge transfer and other properties of the material can be adjusted through adopting 1,2,3-triazole as a skeleton unit and changing the kind, the position and the quantity of units connected with the skeleton unit. The organic donor-receptor connection luminescent material can realize intramolecular charge transfer, and reduces the carrier imbalance problem of unipolar luminescent materials in order to simplify the structure of a device and improve the performances of the device. Two adjacent units connected with the triazole unit have spatial distortion due to steric hindrance, so the structural non-planarity is reduced, and the accumulation degree of the material is reduced, thereby the aggregation quenching of the material and luminescence of an exciplex are inhibited. The material can be used in evaporation organic micro-molecular electroluminescent diodes.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a small molecule luminescent material based on 1,2,3-triazole units and its application. Background technique [0002] Organic electroluminescent devices have been applied in the field of light-emitting displays. Compared with polymer luminescent materials, small molecule luminescent materials have the advantages of simple preparation, definite molecular weight, and single structure, so they have more potential to be promoted to wider commercial applications. At present, the technology of preparing multilayer devices based on evaporation or solution processing of small molecule materials is constantly developing and improving, and significant progress has been made. [0003] Significant progress has been made in the research of organic electroluminescent devices. When the organic light-emitting material is electro-excited, the theoretical rat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D249/06C07D403/14C07D401/14C07D413/14C07D417/14H01L51/54
Inventor 苏仕健赵浩彬李祥龙彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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