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A class of star-shaped electroluminescent materials based on phenanthroimidazole unit and its preparation method and application

An electroluminescent material and phenanthroimidazole technology, which is applied in the directions of luminescent materials, chemical instruments and methods, circuits, etc., can solve the problems of few star-shaped electroluminescent materials, the types of materials are still scarce, and the performance needs to be improved. Facilitates the relationship between structure and performance, is conducive to industrial scale-up production, and improves the effect of electroluminescence performance

Active Publication Date: 2021-03-30
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few studies on star-shaped electroluminescent materials with localized hybrid charge transfer state performance. Both the type and quantity of materials are extremely rare, and the performance needs to be improved.

Method used

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  • A class of star-shaped electroluminescent materials based on phenanthroimidazole unit and its preparation method and application
  • A class of star-shaped electroluminescent materials based on phenanthroimidazole unit and its preparation method and application
  • A class of star-shaped electroluminescent materials based on phenanthroimidazole unit and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: Preparation of star-shaped electroluminescent material SP1

[0052] (1) Preparation of 2-(4-bromophenyl)-1-(4-tert-butylphenyl)-1H-phenanthrene[9,10-d]imidazole

[0053] Under argon atmosphere, 9,10-phenanthrenequinone (10.8g, 20mmol), 4-tert-butylaniline (14.9g, 100mmol), p-bromobenzaldehyde (3.68g, 20mmol), ammonium acetate (6.16g, 80mmol ) was dissolved in 150mL acetic acid, and reacted at 120°C for 12 hours. After stopping the reaction, quench the reaction with water, spin to dry the solvent, extract with dichloromethane and dry with anhydrous magnesium sulfate. After the solution is concentrated, a khaki liquid is obtained, which is purified by silica gel column chromatography, and a mixed solvent of petroleum ether and dichloromethane is used. (Volume ratio 4:1) was used as eluent to obtain a white solid with a yield of 82%. 1 HNMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and the chemical r...

Embodiment 2～11

[0073] Examples 2-11: Preparation of star-shaped electroluminescent materials SP2-SP12

[0074] Similarly, on the basis of Example 1, the raw materials in step (3) are replaced, and other conditions are not changed, so that different star-shaped electroluminescent materials can be obtained, the raw materials before replacement, the raw materials after replacement , the product obtained after replacement and the productive rate are shown in table 3 below:

[0075] In the step (3) of table 3 embodiment 1, gained product structure and productive rate after raw material replacement

[0076]

[0077]

[0078]

[0079]

[0080]

[0081] In Table 3, the raw materials that cannot be purchased directly from the market are prepared by the following methods:

[0082] Preparation of 1,6-bis(2,6-dibromophenoxy)hexane: 2,6-dibromophenol (1.25 g, 5.0 mmol) and 1,6-dibromohexane under argon atmosphere (0.48g, 2.0mmol), sodium hydroxide (0.8g, 20mmol) and 60mL of toluene were ad...

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Abstract

The invention discloses a class of star-shaped electroluminescent material based on phenanthroimidazole units, a preparation method and application thereof. The structure of the star electroluminescent material based on the phenanthroimidazole unit is one of the following structures. The star-shaped electroluminescent material of the present invention has localized hybrid charge transfer state performance, and can effectively utilize triplet state excitons to improve the utilization rate of excitons and improve the electroluminescent performance of devices; the present invention The star-shaped electroluminescent material has a large degree of conjugation and strong rigidity, which can not only improve the thermal stability of the material, but also increase the radiation transition rate of the material and improve its luminous efficiency; the star-shaped electroluminescent material SP of the present invention has a relatively high It has large molecular weight and good solubility, and can be prepared by solution processing technology to prepare large-area flexible display devices. There is great development potential and prospect in the field of organic electronic display.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and specifically relates to a class of star-shaped electroluminescence materials based on phenanthroimidazole units, a preparation method and application thereof. Background technique [0002] Organic Light-Emitting Diodes (OLEDs) have unique advantages such as fast response, wide viewing angle, rich colors, light and thin volume, self-illumination, bendable, rollable and even foldable, and are known as the most potential third-generation display. Technology has great application prospects in electronic products such as smartphones, TVs, tablet computers, VR (virtual reality, head-mounted display devices) and wearable smart devices. [0003] In OLED devices, light-emitting materials are the core. During the working process of OLED devices, electrons and holes recombine to generate excitons, and the internal quantum efficiency of fluorescent material devices that only utilize 25% o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/02C07D403/14C07D409/14C07D487/22C09K11/06H01L51/54
CPCC07D403/14C07D235/02C07D487/22C07D409/14C09K11/06C09K2211/1044C09K2211/1029C09K2211/1074C09K2211/1092C09K2211/1059H10K85/624H10K85/655H10K85/615H10K85/6572
Inventor 马於光胡德华应磊郭婷
Owner SOUTH CHINA UNIV OF TECH
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