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Organic luminescent material with high exciton utilization rate and preparation method and application thereof

A technology of luminescent materials and utilization rate, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of few red thermal exciton fluorescent materials, the performance needs to be improved, the number of materials is scarce, etc., to achieve a single molecular structure. Clear, commercial application, excellent thermal stability

Pending Publication Date: 2022-05-13
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still few studies on red thermal exciton fluorescent materials with localized hybrid charge transfer state properties. Both the types and quantities of materials are extremely rare, and the performance needs to be improved.

Method used

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  • Organic luminescent material with high exciton utilization rate and preparation method and application thereof
  • Organic luminescent material with high exciton utilization rate and preparation method and application thereof
  • Organic luminescent material with high exciton utilization rate and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Embodiment 1: Preparation of red thermal exciton fluorescent material SQ1'

[0085] (1) Preparation of compound M3'

[0086] Under argon atmosphere, 9,10-phenanthrenequinone (4.16g, 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 M3', and the chemical reaction equation of the preparation process is as follo...

Embodiment 2～5

[0122] Examples 2-5: Preparation of organic luminescent materials SQ2'-SQ5' with high exciton utilization

[0123] Similarly, on the basis of Example 1, the raw materials in step (5) are replaced, and other conditions are not changed, so that different red thermal exciton fluorescent 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 6 below:

[0124] In the step (3) of the embodiment 1 of table 6, the obtained product structure and the productive rate after the replacement of raw materials

[0125]

[0126]

Embodiment 6～9

[0127] The preparation of embodiment 6~9 compound SQ6'~SQ9'

[0128] Under argon atmosphere, compound M10'(1.38g, 2.5mmol) and compound M11'(0.69g, 2.5mmol) were dissolved in 10mL n-butanol and 10mL toluene solution, reacted at 100°C for 24h, after stopping the reaction, quenched with water The reaction was quenched, extracted with dichloromethane and dried with anhydrous magnesium sulfate. After the solution was concentrated, a khaki liquid was obtained, which was purified by silica gel column chromatography, and a mixed solvent of petroleum ether and dichloromethane (volume ratio 2:1) was used for eluting agent, a red solid SQ6' was obtained with a yield of 45%. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product SQ6', and the chemical reaction equation of the preparation process is as follows:

[0129]

[0130] Similarly, on the basis of Example 6, by replacing the raw materials in it, and without changing other con...

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Abstract

The invention discloses an organic light-emitting material with a high exciton utilization rate and a preparation method and application thereof. The material has an enol resonance structure as shown in the following formula (I) or (II): the organic light-emitting material contains a strong electron-deficient unit squaric acid, is large in structural conjugation degree and strong in rigidity, has the characteristic of local hybrid charge transfer state luminescence, can effectively utilize triplet state excitons through anti-gap crossing to improve the utilization rate of the excitons, and can be used for preparing the organic light-emitting material. The electroluminescent performance of the device is improved; the compound has relatively large molecular weight and good solubility, can be used for preparing a large-area flexible display device by adopting a solution processing technology, and has huge development potential and prospect in the field of organic electronic display.

Description

technical field [0001] The invention relates to the field of organic photoelectric technology, in particular to an organic luminescent material with high exciton utilization rate and its preparation method and application. 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-luminescence, and bendable, rollable and even foldable, and are known as the most promising third-generation Display technology has great application prospects in electronic products such as smart phones, TVs, tablet computers, virtual reality, head-mounted display devices, and wearable smart devices. [0003] OLED devices have a wide range of materials for the light-emitting layer and can achieve full-color display. Better performance and lower cost can meet the requirements of higher performance and greater information capacity of display equipment in today's information age. In th...

Claims

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Application Information

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IPC IPC(8): C07D235/02C07D403/10C07D413/10C07D417/10C07D401/10C07D233/61C09K11/06H01L51/54
CPCC07D235/02C07D403/10C07D413/10C07D417/10C07D401/10C07D233/61C09K11/06C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044H10K85/654H10K85/657H10K85/6572
Inventor 李应成崔晶孙旭阳陈雪张培斌
Owner CHINA PETROLEUM & CHEM CORP
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