Tricarbazole-aromatic amine derivative cavity transmission material and preparation method and application thereof

A technology of aromatic amine derivatives and hole transport materials, which can be used in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., can solve the problems of poor performance, complex preparation of hole transport materials, high cost, etc., and achieve high yield High, cheap reaction raw materials, easy separation effect

Inactive Publication Date: 2018-11-13
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a trioxacarbazole-aromatic amine derivative hole transport material and its preparation method and application, so as to solve the problems of complex preparation, high cost or poor performance of the hole transport material

Method used

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  • Tricarbazole-aromatic amine derivative cavity transmission material and preparation method and application thereof
  • Tricarbazole-aromatic amine derivative cavity transmission material and preparation method and application thereof
  • Tricarbazole-aromatic amine derivative cavity transmission material and preparation method and application thereof

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preparation example Construction

[0039] A kind of preparation method of tricarbazole-aromatic amine derivative hole transport material of the present invention, comprises the following steps:

[0040] Preparation of compound I: Dissolve compound II, palladium catalyst, any Ar1-Ar6 monoboronic acid or secondary amine and base in toluene under nitrogen protection and light-shielding conditions, and react at a temperature of 60-120°C for 8-72 hours. After the reaction was completed, compound I was purified by column chromatography;

[0041] Wherein, the structure of compound II is shown in formula 3:

[0042]

[0043] Wherein, the mol ratio of compound II and any one of Ar1-Ar6 monoboronic acid or secondary amine is 1:3~1:6; One of them, the molar ratio to Compound II is 0.09:1~0.15:1; the base is potassium carbonate aqueous solution or potassium tert-butoxide, and the molar ratio to Compound II is 4:1~6:1; Compound II The mass volume ratio to toluene is: 15-25 mL of toluene solvent is added for every 500 m...

Embodiment 1

[0048]

[0049] Reaction condition one: under the protection of nitrogen, put 6-bromoindol-2-one (212.0mg, 1.0mmol), potassium carbonate (276mg, 2mmol), tetrabutylammonium bromide (33mg, 0.1mmol) in bis Mouth reaction bottle. Seal the reaction device, change the nitrogen three times, and insert the nitrogen balloon. Inject 22mL of tetrahydrofuran, stir at 85°C for 30min, then slowly inject 2mL of bromohexane, and keep stirring at 80°C for 8h. After the reaction was slowly cooled to room temperature, it was poured into ice water to quench, the organic phase was extracted with dichloromethane, washed three times with deionized water, and the organic phase was dried with anhydrous magnesium sulfate. After suction filtration, the organic phase was concentrated under vacuum to obtain a crude product, which was purified by column chromatography (eluent: dichloromethane (DCM) / petroleum ether (PE) = 1:1) to obtain white waxy solid compound 1 - Hexyl-6-bromo-indolinone (167 mg), y...

Embodiment 2

[0054]

[0055] Reaction condition 1: Put the compound 1-hexyl-6-bromo-indolinone (10g, 33mmol) in a double-necked reaction flask, seal the reaction device, inject 40mL of phosphorus oxychloride, and keep stirring at 100°C for 8h. After the reaction was slowly cooled to room temperature, it was quenched by pouring into ice water, adjusting the Ph to neutral, and suction filtering to obtain a solid crude product, natural. Purification by column chromatography (eluent: DCM / PE=1:10) gave compound II (1.86 mg) as a white solid with a yield of 20.3%.

[0056] Reaction condition 2: Put the compound 1-hexyl-6-bromo-indolinone (10 g, 33 mmol) in a double-necked reaction flask, seal the reaction device, inject 80 mL of phosphorus oxychloride, and keep stirring at 100° C. for 8 h. After the reaction was slowly cooled to room temperature, it was quenched by pouring into ice water, adjusting the Ph to neutral, and suction filtering to obtain a solid crude product, natural. Purified by...

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Abstract

The invention discloses a tricarbazole-aromatic amine derivative cavity transmission material and a preparation method and application thereof. The tricarbazole-aromatic amine derivative cavity transmission material is a star-like micromolecule compound which uses tricarbazole as the core and uses aromatic amide derivative as a modifying group; a formula structure is shown in a formula I in the attached figure, wherein R is selected from one of C1 to C30 straight and branched alkyl or alkyl chains. The tricarbazole-aromatic amine derivative cavity transmission material has the advantages thatthe synthesis route is simple and short, the price of the reaction raw materials is low, the reaction process is easy to control, the separation is easy, the purity is high, and the yield rate is high; the cavity transfer rate is higher, and the dissolving property is good; especially, when the cavity transmission material is applied to a rovskite solar battery, the excellent photoelectric conversion efficiency is obtained; the novel cavity transmission material with excellent property and low cost can be applied to organic electroluminescent devices, organic solar batteries, perovskite solarbatteries or organic field effect transistor devices, and the important application potential is realized.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, and in particular relates to a tricarbazole-aromatic amine derivative hole transport material and its preparation method and application. Background technique [0002] Efficient hole transport materials can not only greatly improve the efficiency of organic photoelectric devices, but also ensure long-term stable operation of the devices. For example, in the field of perovskite solar cells, hole transport materials play a dual role of transporting holes and blocking electrons, which can avoid the recombination of photogenerated electron-hole pairs inside the cell; at the same time, the hydrophobic characteristics of organic hole transport materials can Preventing the perovskite from being attacked by moisture greatly improves the stability of the device. 2,2',7,7'-Tetrakis[N,N-bis(4-methoxyphenyl)amino]-9,9'-spirobifluorene is the most widely used high-efficiency perovskite solar ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/14H01L51/05H01L51/42H01L51/50
CPCC07D487/14H10K85/657H10K10/46H10K30/00H10K50/15Y02E10/549
Inventor 赖文勇孟成李祥春黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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