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Anthracene electroluminescence material containing cavity transmission group and preparation method thereof

A technology of electroluminescent material and hole transport group, applied in the direction of luminescent material, electroluminescent light source, electric light source, etc. Convenience, simple equipment, high-purity effect

Inactive Publication Date: 2008-03-19
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Organic small molecule compounds have the advantages of easy adjustment of chemical structure, high carrier mobility, high compound purity, and relatively pure color light. However, since most organic small molecule electroluminescent materials are unipolar, they only have One of the properties of electron transport and hole transport, and there are few small organic molecules with equal hole and electron transport properties
If such a unipolar organic compound is used as a light-emitting material for a single-layer device, it will lead to quenching of carrier transport and reduce the luminous efficiency and brightness of the device.

Method used

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  • Anthracene electroluminescence material containing cavity transmission group and preparation method thereof
  • Anthracene electroluminescence material containing cavity transmission group and preparation method thereof
  • Anthracene electroluminescence material containing cavity transmission group and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] In a 100mL single-mouth round flat-bottomed flask, add 2.55ml (11mmol) trisubstituted isopropyl borate, 2.791g (10mmol) monochlorotriphenylamine, 0.288g (12mmol) magnesium powder, 50mL of potassium hydroxide dried Tetrahydrofuran and a little iodine are used as initiators, and a reflux condenser is installed. Ultrasonic radiation is performed for 30 minutes in an ultrasonic reactor at 40°C and 175W ultrasonic power. After the reaction is completed, adjust the reaction solution to slightly acidic with 2mol / L hydrochloric acid, and stir for a while. Finally, the organic layer was separated, and a white precipitate was deposited. The aqueous layer was extracted twice with 30 mL of diethyl ether, the combined organic layers were washed with water, dried, and the solvent was removed by rotary evaporation to obtain a crude product, which was purified by recrystallization from water. The yield was 63%, 1 H-NMR (d 6 -DMSO, ppm) δ: 7.12-6.84 (m, 6H, meta carbon hydrogen of N i...

Embodiment 2

[0018] In a 100mL single-mouth round flat-bottomed flask, add 2.78ml (10mmol) trisubstituted isopropyl borate, 2.791g (10mmol) monochlorotriphenylamine, 0.36g (15mmol) magnesium powder, 50mL dried potassium hydroxide Tetrahydrofuran and a little iodine are used as initiators, and a reflux condenser is installed. Ultrasonic radiation is performed for 30 minutes in an ultrasonic reactor at 30°C and 200W ultrasonic power. After the reaction is completed, the reaction solution is slightly acidic with 2mol / L hydrochloric acid, and stirred for a while. Finally, the organic layer was separated, and a white precipitate was deposited. The aqueous layer was extracted twice with 30 mL of diethyl ether, the combined organic layers were washed with water, dried, and the solvent was removed by rotary evaporation to obtain a crude product, which was purified by recrystallization from water. The yield was 49%, 1 H-NMR (d 6 -DMSO, ppm) δ: 7.12-6.84 (m, 6H, meta carbon hydrogen of N in triphe...

Embodiment 3

[0021] According to the method of Example 1, monosubstituted triphenylamine boronic acid (II) was prepared.

[0022] In a 100mL three-necked flask, add 0.112g (0.5mmol) anhydrous palladium carbonate, 0.665g (2.5mmol) triphenylphosphine, 8.4g (25.0mmol) 9,10-di-bromoanthracene, 4.0g (50mmol) acetic acid Sodium, 15.91g (50mmol) of monosubstituted triphenylamine boronic acid, 50mL of anhydrous toluene, under nitrogen protection, heated to 90°C and stirred for 48h. After the reaction was completed, it was cooled to room temperature, and the reactant was poured into ice water, and a yellow-white precipitate was deposited. Filter, dry, dissolve with absolute ethanol, filter and dry to obtain a single yellow solid, separate the single yellow solid by column chromatography (eluent: petroleum ether: ethyl acetate = 8:1), and obtain a single yellow solid crystallization, product The rate is about 26.3%. 1 H-NMR (d 6 -DMSO, ppm) δ: 7.86-7.55 (hydrocarbon on anthracycline), δ: 7.32-6.9...

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Abstract

An anthracene electroluminescent material with hole-transporting moieties is 9,10-di-(4'-N, N-diphenyl-benzenamine)anthracene organic compound, the preparation method of which includes the following steps: (1) under ultrasound irradiation, chloro triphenylamine, triisopropyl borate ester and magnesium powder in THF are initiated by molecular iodine to react for 20-40 min, and then hydrolyzed under acidic condition to obtain mono-substituted triphenylamine boric acid; (2) using palladium acetate as catalyst and triphenyl phosphine as ligands, mono-substituted triphenylamine boric acid and 9, 10-dibromo-anthracene in toluene are under alkaline condition to obtain the luminescent material. The invention bring typical hole-transporting moieties triphenylamine into anthracene luminophor, thereby to break through conventional simple modification to anthracene main body material compound, and realize a greater extent regulation of electroluminescent material carrier transmission property, so as to provide novel electroluminescent material for realization of high quantum yield and electron mobility of the light-emitting device.

Description

technical field [0001] The invention relates to a luminescent material, in particular to an anthracene electroluminescent material containing a hole transport group and a preparation method thereof. Background technique [0002] With the rapid development of material science, information science, and life science in the 21st century, photonic-electronic materials, which are interdisciplinary points, have attracted widespread attention. Organic electroluminescence (Organic electroluminescence) materials that respond to signals with light information in photonic-electronic materials have been widely used in fields such as optical information display, aerospace instruments, military fields, life systems, safety detection, and medical diagnosis. develop. Anthracene is the earliest researched organic small molecule electroluminescence material, Pope et al. Luminescence was observed when a DC voltage of 400V was applied to both sides of a 20μm anthracene single wafer. Afterwards...

Claims

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Application Information

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IPC IPC(8): C09K11/06H05B33/14
Inventor 冯丽恒王晓菊陈兆斌
Owner SHANXI UNIV
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