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Thermally-activated delay fluorescent material and organic electroluminescence device

A technology for thermally activated delayed and fluorescent materials, applied in the field of thermally activated delayed fluorescent materials and organic electroluminescent devices, can solve problems such as difficult scale preparation, low preparation efficiency, long synthesis steps, etc., and achieve high scientific research value and application value , The effect of cheap raw materials and low driving voltage

Inactive Publication Date: 2017-07-21
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of the above analysis, the present invention aims to provide a novel thermally activated delayed fluorescent material with a 4,5-substituted phthalimide structure to solve the problem of low quantum efficiency and high price of traditional OLED light-emitting materials. However, the existing TADF materials have problems such as long synthesis steps, low preparation efficiency, and difficulty in large-scale preparation.

Method used

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  • Thermally-activated delay fluorescent material and organic electroluminescence device
  • Thermally-activated delay fluorescent material and organic electroluminescence device
  • Thermally-activated delay fluorescent material and organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The reaction formula is as follows:

[0040]

[0041] The specific steps of the reaction are as follows:

[0042] In a 5000mL round bottom flask, add 600g of A 1 , 364g of aniline and 2000mL of glacial acetic acid, heated and refluxed at 130°C for 4 hours, distilled off 1000mL of glacial acetic acid after the reaction system was cooled to room temperature, then placed the remaining reaction system at 4°C for low-temperature recrystallization, and filtered to obtain crude Product, then recrystallized with a small amount of glacial acetic acid to obtain 720g of white needle-like crystals. The white crystal is compound B 1 , the yield was 85%.

[0043] The compound B 1 The structure detection results are as follows:

[0044]1 H NMR (300MHz, CDCl 3 )δ7.76(t,J=7.3Hz,2H),7.55–7.47(m,2H),7.46–7.38(m,3H). 13 C NMR (126MHz, CDCl 3 )δ165.2, 155.8, 155.6, 153.7, 153.6, 131.3, 129.2, 128.62, 128.58, 128.5, 128.4, 126.4, 113.8, 113.7, 113.63, 113.56, 113.5, 113.4. 19 F N...

Embodiment 2

[0047] The reaction formula is as follows:

[0048]

[0049] The specific steps of the reaction are as follows:

[0050] Under argon protection, add 1.72g of 60% sodium hydride and 20mL of anhydrous tetrahydrofuran to a 200mL reactor equipped with a reflux device to obtain the first mixed solution; dissolve 6.0g of carbazole in 20mL of anhydrous Tetrahydrofuran, get the second mixed solution; 4.66g A 1 Dissolve in 20mL of anhydrous tetrahydrofuran to obtain the third mixed solution; slowly add the first mixed solution to the second mixed solution, stir until there are no bubbles, then add the third mixed solution, and then raise the temperature to 40°C and stirred for 4 hours to obtain the fourth mixed solution; the fourth mixed solution was cooled to room temperature, and a large amount of water and dichloromethane were added thereto for extraction, and the extracted organic phase was dried with anhydrous sodium sulfate and filtered. Then the organic liquid phase was rem...

Embodiment 3

[0054] The reaction formula is as follows:

[0055]

[0056] Under argon protection, 1.72g of 60% sodium hydride and 20mL of anhydrous tetrahydrofuran were added to a 200mL reactor equipped with a reflux device to obtain the first mixed solution; 10.0g of 4,5-bis(3 ,6-Di-tert-butyl)carbazole was dissolved in 20mL of anhydrous tetrahydrofuran to obtain the second mixed solution; 4.66g A1 was dissolved in 20mL of anhydrous tetrahydrofuran to obtain the third mixed solution; the first mixed solution was slowly added into the second mixed solution, stir until there are no bubbles, then add the third mixed solution, then raise the temperature to 25°C and stir for 4 hours to obtain the fourth mixed solution; cool the fourth mixed solution to room temperature, A large amount of water and dichloromethane were added thereto for extraction, the extracted organic phase was dried with anhydrous sodium sulfate, filtered, and then the organic liquid phase was distilled off to obtain a cr...

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Abstract

The invention relates to a thermally-activated delay fluorescent material. The thermally-activated delay fluorescent material is a 4,5-position substituted phthalimide derivative, R1 is an electron-rich aromatic amine substituent group containing at least one nitrogen, amino nitrogen of the electron-rich aromatic amine substituent group is connected with phthalimide, and R2 is any one of saturated aliphatic group, unsaturated aliphatic group, aryl and hetero aryl. The 4,5-position substituted phthalimide derivative has the advantages of having thermally-activated delay property, high fluorescence quantum yield and easy derivatization characteristics and the advantages of good stability and the like. A preparation method of the thermally-activated delay fluorescent material is simple in synthesis, the raw materials are cheap, the product yield is high, and the material can be prepared in a large-scale mode. The invention provides an organic electroluminescence device. The organic electroluminescence device has the advantages of high efficiency, low driving voltage, long service life, stable light emitting and the like. The thermally-activated delay fluorescent material provided with a 4,5-position substituted phthalimide structure and the organic electroluminescence device based on the material have a very good application prospect.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a thermally activated delayed fluorescent material and an organic electroluminescent device with a phthalimide structure substituted at 4 and 5 positions. Background technique [0002] Organic light-emitting diodes (OLEDs) have great application prospects in the fields of flat panel displays and solid-state light sources because of their advantages such as full solid state, self-luminescence, wide viewing angle, fast response, low driving voltage, and low power consumption. At present, although the research on OLED has made significant progress, the traditional OLED light-emitting materials mainly include fluorescent materials and phosphorescent materials: the first generation OLED based on fluorescent emitting materials only uses singlet excitons to emit light, and its internal quantum The efficiency (IQE) is only 25%; the second-generation OLED is based on th...

Claims

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Application Information

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IPC IPC(8): C07D209/48C07D209/86C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D209/48C07D209/86C09K2211/1029C09K2211/1007H10K85/6572H10K50/11
Inventor 李猛陈传峰
Owner INST OF CHEM CHINESE ACAD OF SCI
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