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Preparation method and application of 2,1,3-benzoselenadiazole derivative

A technology of benzoselenodiazole and its derivatives, applied in the field of organic light-emitting materials, to achieve the effect of improving luminescent performance and avoiding quenching of aggregated states

Inactive Publication Date: 2017-06-13
JIANGXI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, 2,1,3-benzoselenadiazole derivatives modified with tetraphenylethylene (TPE) and / or triphenylamine groups (TPA) and having AIE properties have not been reported in the literature.

Method used

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  • Preparation method and application of 2,1,3-benzoselenadiazole derivative
  • Preparation method and application of 2,1,3-benzoselenadiazole derivative
  • Preparation method and application of 2,1,3-benzoselenadiazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of 4,7-bis(1,2,2-triphenylethenyl)phenyl)-(2,1,3)-benzoselenodiazole(TPE-Se-TPE)

[0026]

[0027] 340mg (1.0mmol) 4,7-dibromo-(2,1,3)-benzoselenoadiazole, 1.145g (2.5mmol) 4-(1,2,2-tristyryl)-phenylboronic acid Pinacol ester, 10mL 2.0M potassium carbonate aqueous solution, and 50mL THF were added to a 100mL three-neck flask, and after 30 minutes of exhaust, 143mg Pd(PPh 3 ) 4 added to the reaction system. Stir and reflux for 24 hours to stop the reaction and cool to room temperature. The cooled reaction solution was poured into 40 mL of distilled water, extracted twice with DCM, and the obtained organic layer was washed with anhydrous MgSO 4 dry. The crude product was separated and purified by column chromatography (petroleum ether:dichloromethane=10:1) to obtain 565 mg of a yellow solid product (yield: 67%).1 H NMR (400MHz, CDCl 3 ,TMS)δ(ppm): 7.68~7.66(d, J=8.28Hz, 4H), 7.56(s, 2H), 7.19~7.16(d, J=8.32Hz, 4H), 7.13~7.09(m, 26H ),7.06~7.04(m,4H). 1...

Embodiment 2

[0030] 4-(N,N-diphenylamino)phenyl-7-(1,2,2-triphenylethenyl)phenyl-(2,1,3)-benzoselenadiazole (TPA-Se -TPE) synthesis

[0031]

[0032] (1) Synthesis of 4-bromo-7-(N,N-diphenylamino)phenyl-(2,1,3)-benzoselenadiazole

[0033] 1.12g (3.0mmol) 4,7-dibromo-(2,1,3)-benzoselenoadiazole, 1.11g (3.0mmol) 4-(diphenylamino) phenylboronic acid pinacol ester and 15mL Add 2.0M potassium carbonate aqueous solution and 70mL THF into a 100mL three-neck flask, exhaust for 0.5h, and 172mg Pd(PPh 3 ) 4 added to the reaction system. Stir and reflux for 24 hours to stop the reaction and cool to room temperature. The cooled reaction solution was poured into 60 mL of distilled water, extracted twice with DCM, and the obtained organic layer was washed with anhydrous MgSO 4 dry. The crude product was separated and purified by column chromatography (petroleum ether:dichloromethane=20:1) to obtain 894 mg of a yellow solid product (yield: 59%). 1 H NMR (400MHz, CDCl 3 ,TMS)δ(ppm): 7.96~7.94(d...

Embodiment 3

[0038] Synthesis of 4,7-bis(N,N-diphenylamino)phenyl)-(2,1,3)-benzoselenoadiazole(TPA-Se-TPA)

[0039]

[0040] 340mg (1.0mmol) 4,7-dibromo-(2,1,3)-benzoselenadiazole, 928mg (2.5mmol) 4-(diphenylamino) phenylboronic acid pinacol ester and 10mL 2.0M Potassium carbonate aqueous solution and 60mL THF were added to a 100mL three-necked flask, and exhausted for 30 minutes, 143mg Pd(PPh 3 ) 4 added to the reaction system. Stir and reflux for 24 hours to stop the reaction and cool to room temperature. The cooled reaction solution was poured into 50 mL of distilled water, and then extracted twice with DCM, and the obtained organic layer was washed with anhydrous MgSO 4 dry. The crude product was separated and purified by column chromatography (petroleum ether:dichloromethane=15:1) to obtain 509 mg of a yellow solid product (yield: 76%). 1 H NMR (400MHz, CDCl 3 ,TMS)δ(ppm): 7.80~7.78(d, J=8.64Hz, 4H), 7.59(s, 2H), 7.31~7.27(t, J=7.86Hz, 8H), 7.21~7.18(m, 12H ),7.07~7.04(t,J=7...

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Abstract

The invention discloses a preparation method and application of 2,1,3-benzoselenadiazole derivative. The derivative is TPE-Se-TPE, TPA-Se-TPE or TPA-Se-TPA, i.e., tetraphenyl ethylene (TPE) and / or triphenylamine group (TPA) are respectively introduced on a 4 position and a 7 position of the 2,1,3-benzoselenadiazole derivative. The prepared 2,1,3-benzoselenadiazole derivative has the advantages that the phenomena of aggregation and quenching can be effectively avoided, the properties of aggregation, induction and luminescence are achieved, and the luminescence efficiency of the material can be obviously enhanced, so that the 2,1,3-benzoselenadiazole derivative can be applied to an organic electroluminescence device as a luminescent layer.

Description

technical field [0001] The invention discloses a 2,1,3-benzoselenodiazole derivative with aggregation-induced luminescence properties, mainly relates to its preparation and application in organic electroluminescent devices, and specifically belongs to the technical field of organic luminescent materials. Background technique [0002] Organic light-emitting materials have become a hot research topic for researchers due to their wide application in many fields such as organic electronic light-emitting devices, specific molecular recognition and tracking, and photochemical sensors. Most organic fluorescent materials have good luminescent performance in dilute solution, but in the aggregated state, especially in the crystalline state, the fluorescence will be significantly weakened or even quenched. This is because as the concentration of the fluorescent compound increases, the interaction between the fluorescent compound molecules increases, and it is easy to form an excimer of...

Claims

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Application Information

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IPC IPC(8): C07D293/12C09K11/06H01L51/54
CPCC09K11/06C07D293/12C09K2211/1014C09K2211/1007C09K2211/1055H10K85/631H10K85/657
Inventor 梁爱辉陈意黄贵
Owner JIANGXI NORMAL UNIVERSITY
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