Organic electroluminescence material containing quinacridone and preparation method thereof

A quinacridone and luminescent material technology, applied in the field of organic electroluminescent materials, to achieve the effects of improving solubility, high luminous efficiency and high yield

Active Publication Date: 2018-02-16
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, existing materials still have application problems, such as lifespan, brightness, and efficiency. How to develop materials with excellent performance is the top priority.

Method used

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  • Organic electroluminescence material containing quinacridone and preparation method thereof
  • Organic electroluminescence material containing quinacridone and preparation method thereof
  • Organic electroluminescence material containing quinacridone and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Synthesis of Example 1 Compound 001

[0023]

[0024] Under nitrogen protection system, weigh 1.5mmol of bromobenzene, add 300ml of freshly distilled tetrahydrofuran solution, add 1.2mmol of n-butyllithium dropwise at -78°C, react for two hours, then add dropwise 200ml of tetrahydrofuran solution Dissolved 1 mmol of 5,12-diphenyl-5,12-dihydroquinoline[2,3-b]acridine-7,14-dione, after the dropwise addition, react at room temperature for 9 hours under nitrogen protection conditions, Add 100ml of 1M dilute hydrochloric acid, extract 3 times with 100ml of diethyl ether, separate the liquid, concentrate, and recrystallize with dichloromethane:petroleum ether=1:3 to obtain a light yellow 0.80mmol intermediate, which is added to 300ml of concentrated sulfuric acid, at room temperature After reacting for 9 hours, hydrolysis, extraction, liquid separation, and recrystallization, 0.75 mmol of a light yellow final product was obtained with a yield of 75% and a purity of more th...

Embodiment 2

[0025] Synthesis of Example 2 Compound 002

[0026]

[0027] Under nitrogen protection system, weigh 1.6mmol of 2-bromonaphthalene, add 300ml of freshly steamed tetrahydrofuran solution, and add 1.2mmol of n-butyllithium dropwise at -78°C, react for two hours, then add 200ml of 1 mmol of 5,12-diphenyl-5,12-dihydroquinoline[2,3-b]acridine-7,14-dione dissolved in tetrahydrofuran solution, after the dropwise addition, react at room temperature under nitrogen protection conditions 9 After 1 hour, add 100ml of 1M dilute hydrochloric acid, extract 3 times with 100ml of diethyl ether, separate liquid, concentrate, and recrystallize with dichloromethane:petroleum ether=1:3 to obtain a pale yellow 0.82mmol intermediate, which is added to 300ml of concentrated sulfuric acid , reacted at room temperature for 9 hours, after hydrolysis, extraction, liquid separation, and recrystallization, 0.76 mmol of a light yellow final product was obtained with a yield of 76% and a purity of more th...

Embodiment 3

[0028] Synthesis of Example 3 Compound 003

[0029]

[0030] Under nitrogen protection system, weigh 1.7mmol of hexane bromide, add 300ml of freshly distilled tetrahydrofuran solution, and add 1.2mmol of n-butyllithium dropwise at -78°C, react for two hours, and then add 200ml of tetrahydrofuran solution dropwise. 1 mmol of 5,12-diphenyl-5,12-dihydroquinoline[2,3-b]acridine-7,14-dione dissolved in the solution, after the dropwise addition, react at room temperature for 9 hours under nitrogen protection , add 100ml of 1M dilute hydrochloric acid, extract 3 times with 100ml of diethyl ether, separate liquid, concentrate, recrystallize with dichloromethane:petroleum ether=1:3, obtain light yellow 0.82mmol intermediate, add the intermediate to 300ml concentrated sulfuric acid, After reacting at room temperature for 9 hours, after hydrolysis, extraction, liquid separation and recrystallization, 0.73 mmol of a light yellow final product was obtained with a yield of 73% and a puri...

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Abstract

The invention provides an organic electroluminescent material containing quinacridone, which is 5,12-diphenyl-5,12-dihydroquinolin[2,3-b]acridine-7,14-dione Based on this, different substituents are introduced to increase the plane conjugation of the molecular structure, improve the solubility of this type of organic light-emitting material, and make it easier to prepare. By strictly controlling the reaction temperature, reaction time and other conditions, the product At the same time, due to the introduction of different substituents, this type of organic luminescent material can change the electronic transition, so that its luminous peak position can be adjusted. The material can emit red light and has high luminous efficiency. It is made of the material of the present invention. The red light device can meet the needs of industrial production.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to organic electroluminescent materials, which contain novel polycyclic derivatives. Background technique [0002] Organic electroluminescent technology is the latest generation of flat-panel display technology, which can be used for flat-panel displays and lighting sources. At present, commercial flat-panel displays have been put into the market. Due to its own absolute advantages, the lighting source will soon be industrialized. The electroluminescent device has an all-solid structure, and the organic electroluminescent material is the core and basis of the device. The development of new materials is the driving force behind the continuous progress of electroluminescent technology. The preparation of original materials and device optimization are also research hotspots in the organic electroluminescent industry. [0003] At present, the development of OLED (organi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D471/04H01L51/54
CPCC09B15/00C09B48/00C09K11/06H10K85/657
Inventor 王钊姜晓晨胡晓明陈明赵明
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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