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N-type organic interface material and preparation method and application thereof

An interface material and organic technology, applied in organic chemistry, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve problems such as insufficient electron transport capacity and poor solubility, achieve excellent thermal stability, and improve electron transport performance. Effect

Active Publication Date: 2021-11-05
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Excellent photoelectric characteristics can be achieved by optimizing the device structure and implementation conditions, which can overcome technical problems such as insufficient electron transport ability and poor solubility of organic semiconductor materials

Method used

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  • N-type organic interface material and preparation method and application thereof
  • N-type organic interface material and preparation method and application thereof
  • N-type organic interface material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0041] Preparation of Material IX Compound:

[0042]

[0043] 1-Bromo-N,N'-bis(undecyl)perylene-3,4,9,10-tetracarboxylic acid diimide (1.15g, 1.5mmol) and 4-(3-(1-imidazole Base) propylaminomethyl) phenylboronic acid pinacol ester (1.53g, 4.5mmol) and TBAB (0.28g, 0.86mmol) were put into a 100mL two-necked reaction flask, the nitrogen gas was replaced three times, and then added to the reaction flask Pd(PPh 3 ) 4 (0.5g, 0.43mmol) and it was sealed, and the nitrogen gas was changed three times. Inject 45 mL of deoxygenated toluene and 2 mol / L of K into the reaction flask 2 CO 3 15 mL of the solution was reacted at 95°C for 24h. After the reaction was completed, the reaction was quenched with water, cooled to room temperature, extracted with dichloromethane, suction filtered, column chromatography, and dried to obtain the target product material IX (0.36 g, yield 21.4%).

Embodiment 1-2

[0045] Preparation of Material XVII Compounds:

[0046]

[0047] 1,7-dibromo-N,N'-bis(undecyl)perylene-3,4,9,10-tetracarboxylic acid diimide (0.9g, 1mmol), 4-(3-(1 -imidazolyl) propylaminomethyl) phenylboronic acid pinacol ester (1.3g, 12mmol), tetrabutylammonium bromide (TBAB) (0.27g, 0.8mmol) are put into the two-necked bottle of 150mL, it is used Rubber stopper seal, replacement N 2 three times. Then quickly add Pd(PPh 3 ) 4 Catalyst (0.49mg, 0.43mmol), and then replace N 2three times. Finally, bubbled deoxygenated toluene (40 mL) and 2M K 2 CO 3 Aqueous solutions (15 mL) were injected into reaction flasks respectively, and reacted at 95° C. for 24 h. After the reaction, extract 3 times with DCM solvent and saturated NaCl solution, the separated organic layer was washed with MgSO 4 Suction filtration after drying and the crude product obtained after concentrating the solution were separated and purified by column chromatography (eluent PE:DCM=4:1), and dried in ...

Embodiment 1-3

[0049] Preparation of Material XXV Compounds:

[0050]

[0051] 1,5,7-tribromo-N,N'-bis(undecyl)perylene-3,4,9,10-tetracarboxylic acid diimide (0.47g, 0.5mmol) and 4-(3 -(1-imidazolyl) propylaminomethyl) phenylboronic acid pinacol ester (0.51g, 1.5mmol) and TBAB (0.09g, 0.28mmol) were put into a 100mL two-necked reaction flask, and the nitrogen gas was changed three times, and then Add Pd(PPh 3 ) 4 (0.5g, 0.43mmol) and it was sealed, and the nitrogen gas was changed three times. Inject 45 mL of deoxygenated toluene and 2 mol / L of K into the reaction flask 2 CO 3 15 mL of the solution was reacted at 95°C for 24 hours. After the reaction was completed, the reaction was quenched with water, cooled to room temperature, extracted with dichloromethane, suction filtered, column chromatography, and dried to obtain the target product material XXV (0.45 g, yield 33.4%).

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Abstract

The invention discloses an n-type organic interface material as well as a preparation method and application thereof. Perylene diimide is taken as a core unit, a flexible alkyl chain is connected to a nitrogen site, and an alkyl chain containing a hydrogen bond and an amphiphilic group is taken as a side chain, so that the amphiphilic n-type organic interface material is obtained. The n-type organic interface material based on perylene bisimide is obtained by taking perylene bisimide as a center and introducing an amphiphilic group to a bay position or a shoulder position of perylene bisimide. The material improves the electron transport performance, solves the problem of poor solubility of an electron transport layer material in a polar solvent, can be used as an electron transport layer material or an interface modification material, and is widely applied to high-stability and high-efficiency organic photoelectric devices.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials and applications, and in particular relates to an n-type organic interface material and its preparation method and application. Background technique [0002] High-efficiency n-type interface materials can not only greatly improve the efficiency of organic optoelectronic devices, but also ensure long-term stable operation of the devices. For example, in the field of organic solar cells, n-type interface materials play a dual role of transporting electrons and blocking holes, which can prevent photogenerated electron-hole pairs from recombining inside the cell. In recent years, organic optoelectronic functional materials have developed very rapidly. One of the key factors to realize the improvement of organic solar cell device performance is to obtain efficient and balanced carrier injection and transport. [0003] The study found that among many non-fullerene materials, perylene d...

Claims

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Application Information

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IPC IPC(8): C07D471/06C07F9/6561H01L51/50H01L51/42H01L51/54H01L51/46
CPCC07D471/06C07F9/6561H10K30/20H10K85/6572H10K50/16Y02E10/549
Inventor 赖文勇闵洁李祥春刘芳
Owner NANJING UNIV OF POSTS & TELECOMM
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