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Electroluminescent materials based on carbazole five-membered heterocycle units as well as preparation method and application of electroluminescent materials

A technology of electroluminescent materials and five-membered heterocycles, applied in the directions of luminescent materials, chemical instruments and methods, circuits, etc., can solve the problems of high price of OLED products, low utilization rate of materials, expensive equipment and other problems, and achieve high efficiency. The effect of stabilizing light-emitting device performance, easy chemical modification, improving fluorescence quantum yield and hole transport ability

Active Publication Date: 2018-07-20
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the vacuum evaporation process is used to prepare OLED devices, and the equipment is expensive.
Low material utilization rate (~20%) keeps the price of OLED products high

Method used

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  • Electroluminescent materials based on carbazole five-membered heterocycle units as well as preparation method and application of electroluminescent materials
  • Electroluminescent materials based on carbazole five-membered heterocycle units as well as preparation method and application of electroluminescent materials
  • Electroluminescent materials based on carbazole five-membered heterocycle units as well as preparation method and application of electroluminescent materials

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0074] 1. Preparation of carbazolo five-membered heterocyclic unit

[0075] (1) Synthesis of monomer M1

[0076] Preparation of ethylfuran-3-carboxylate: In a 500mL three-necked flask, dissolve furan-3-carboxylic acid (11.2g, 0.1mol) in 200mL of methanol, and add 20mL of concentrated sulfuric acid dropwise to the reaction solution. After stirring for 12 hours, stop the reaction, quench the reaction with water, extract with dichloromethane and dry with anhydrous magnesium sulfate. After the solution is concentrated, a yellow liquid is obtained, which is purified by silica gel column chromatography. The mixed solvent of petroleum ether / dichloromethane (5 / 1, v / v) was the eluent, and the yield was 73%. 1 H NMR, 13 C NMR, MS and elemental analysis results show that the compound obtained is the target product, and the chemical reaction equation of the preparation process is as follows:

[0077]

[0078] Preparation of ethyl 2-(tributyltin)furan-3-carboxylate: Under argon atmos...

Embodiment example 1

[0102] Implementation Case 1: Synthesis of Compound D1

[0103] Under argon atmosphere, in a 100mL three-necked flask, add monomer M1 (1.32g, 2.4mol), diphenylamine (0.85g, 5.0mmol), sodium tert-butyl alkoxide (1.84g, 19.2mmol), palladium acetate ( 27mg, 0.12mmol) and 50mL toluene. Heat and stir to 85° C., add 0.24 ml of 1 mol / L tri-tert-butylphosphine toluene solution, and react for 12 hours. After stopping the reaction, the solvent was concentrated, and the crude product was purified by column chromatography, using a mixed solvent of petroleum ether and dichloromethane (4 / 1, v / v) as the eluent, and finally an emerald green solid was obtained. 1 H NMR, 13 C NMR, MS and elemental analysis results show that the compound obtained is the target product D1, and the chemical reaction equation of the preparation process is as follows:

[0104]

[0105] The differential scanning calorimetry (DSC) curve of compound D1 is as follows figure 1 shown. It can be seen from the figur...

Embodiment example 2

[0106] Implementation Case 2: Synthesis of Compound D2

[0107] The chemical reaction equation of the preparation process is as follows:

[0108]

[0109] Under argon atmosphere, in a 100mL three-necked flask, add monomer M2 (1.32g, 2.4mol), diphenylamine (0.85g, 5.0mmol), sodium tert-butyl alkoxide (1.84g, 19.2mmol), palladium acetate (27mg , 0.12mmol) and 50mL toluene. Heat and stir to 85° C., add 0.24 ml of 1 mol / L tri-tert-butylphosphine toluene solution, and react for 12 hours. After stopping the reaction, the solvent was concentrated, and the crude product was purified by column chromatography, using a mixed solvent of petroleum ether and dichloromethane (4 / 1, v / v) as the eluent, to obtain an off-white solid. 1 H NMR, 13 The results of C NMR, MS and elemental analysis showed that the obtained compound was the target product D2. The ultraviolet-visible absorption spectrum of compound D2 in the thin film state is as follows: figure 2 shown by figure 2 It can be ...

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Abstract

The invention belongs to the technical field of organic photoelectricity and discloses electroluminescent materials based on carbazole five-membered heterocycle units as well as a preparation method and an application of the electroluminescent materials. The materials have the chemical structural formula shown in the description, wherein X is O, S, Se, Te or N-R; R is the same or different and isC1-20 straight-chain, branched or cyclic alkyl or alkoxy, C2-20 straight-chain, branched or cyclic alkenyl, straight-chain, branched or cyclic alkynyl, straight-chain, branched or cyclic alkyl carbonyl, aryl or heteroaryl, aralkyl or heteroaryl alkyl, aryloxy or heteroaryloxy, aryl alkoxy or heteroaryl alkoxy with 4-20 annular atoms, triphenylamine or derivatives thereof, carbazole and derivativesthereof, phenoxazine and derivatives thereof, phenothiazine and derivatives thereof, pyridine and derivatives thereof, oxadiazole and derivatives thereof and benzimidazole and derivatives thereof; Arl-Ar8 are one of conjugated or non-conjugated structural units.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to a class of electroluminescent materials based on carbazolo five-membered heterocyclic ring units, a preparation method and application thereof. Background technique [0002] Organic light-emitting diode (OLED) displays use organic materials as light-emitting materials. The material structure is easy to modify and improve, and the selection range is wide; the driving voltage is low, only 3-12V DC voltage is required; self-illumination, no backlight is required; wide viewing angle , can be close to 180°; the response speed is fast, up to 1 μs; in addition, it has the advantages of light weight, ultra-thin, large size, flexible panel, and easy molding and processing. Due to the many advantages of OLED displays, it has attracted extensive attention from the scientific and industrial circles. Since Kodak Corporation of the United States developed OLED devic...

Claims

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Application Information

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IPC IPC(8): C07D491/153C07D495/14C09K11/06H01L51/54
CPCC09K11/06C07D491/153C07D495/14C09K2211/1044C09K2211/1029C09K2211/1088C09K2211/1092H10K85/636H10K85/615H10K85/657H10K85/6572
Inventor 应磊胡黎文黄飞曹镛
Owner 东莞伏安光电科技有限公司
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