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Synthetic method of N, N-diaryl-2-bromine-6-naphthylamine and application thereof

A synthesis method, diaryl technology, applied in the application of organic semiconductor materials, the field of synthesis of N,N-diaryl-2-bromo-6-naphthylamine, can solve the difficulty of aromatic amine synthesis, comprehensive production Problems such as low rate and low yield

Active Publication Date: 2015-11-11
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, the synthesis and preparation of N,N-diaryl-2-bromo-6-naphthylamine mainly utilizes N,N-diarylamine and 6-bromo-2-naphthol or 2,6- The coupling reaction of dibromonaphthalene occurs, and the synthesis of diarylamines in this method requires the C-N coupling reaction between aromatic amines and aromatic amines containing monoamino groups to obtain, while some aromatic amines containing monoamino groups are difficult to synthesize and produce The rate is low, resulting in a low overall yield

Method used

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  • Synthetic method of N, N-diaryl-2-bromine-6-naphthylamine and application thereof
  • Synthetic method of N, N-diaryl-2-bromine-6-naphthylamine and application thereof
  • Synthetic method of N, N-diaryl-2-bromine-6-naphthylamine and application thereof

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Embodiment 1

[0080] The N,N-diaryl-2-bromo-6-naphthylamine (DT-DPP(FNN-A) of this embodiment 2) synthetic method, comprising the following steps:

[0081] Synthesis of step one compound 6-bromo-2-naphthylamine (1)

[0082] After dissolving tunic acid (15g, 67.2mmol) in glacial acetic acid at 70°C, liquid bromine (21.47g, 134mmol) was added dropwise and reacted at constant temperature for 2h. Then the temperature was lowered to 60°C, tin powder (8g, 67.4mmol) and concentrated hydrochloric acid (95ml) were added carefully, and the reaction was refluxed for 3h. After the reaction, the glacial acetic acid was distilled off under reduced pressure, and the residue was neutralized with NaOH solution until the solution was weakly alkaline, and extracted with dichloromethane. The organic phase was dried and filtered over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel column chromatography and recrystall...

Embodiment 2

[0104] The N,N-diaryl-2-bromo-6-naphthylamine (DT-DPP(FFNN-A) of this embodiment 2 ) synthetic method, using 2-bromofluorene as a raw material to synthesize 2-fluoro-7-bromofluorene through a new synthetic route, and using this unit to synthesize a new type of organic photoelectric material DT-DPP (FFNN-A) with a route similar to Example 1 2 ,Specific steps are as follows:

[0105] Synthesis of step 1 compound 2-nitro-7-bromofluorene (1)

[0106] 2-Bromofluorene (7g, 28.6mmol) was dissolved in 40mL of glacial acetic acid, heated to 60°C, and 20mL of concentrated nitric acid / glacial acetic acid (3:1, v / v) was added dropwise under vigorous stirring. After constant temperature reaction for 1.5 h, it was cooled to room temperature and extracted with dichloromethane / water. The organic phase was dried and filtered with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by recrystallization to obtain 7.4 g ...

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Abstract

The invention discloses a synthetic method of N, N-diaryl-2-bromine-6-naphthylamine. The synthetic method comprises the step of carrying out C-N coupled reaction on halogenated arene and a 6-bromine-2-naphthylamine unit to obtain an N, N-diaryl-2-bromine-6-naphthylamine unit. The invention also discloses application of N, N-diaryl-2-bromine-6-naphthylamine, namely, N, N-diaryl-2-bromine-6-naphthylamine provided by the invention is adopted as the raw material to prepare an organic semiconductor material; compared with the conventional synthetic method, the synthetic method of N, N-diaryl-2-bromine-6-naphthylamine provided by the invention is simple in synthetic route and high in comprehensive yield; the organic semiconductor material which contains a diaryl naphthyl amine functional unit and is prepared from N, N-diaryl-2-bromine-6-naphthylamine provided by the invention is relatively high in hole mobility and thin film morphology stability.

Description

technical field [0001] The invention relates to a preparation method of organic semiconductor materials, in particular to a synthesis method of N,N-diaryl-2-bromo-6-naphthylamine and its application in organic semiconductor materials. Background technique [0002] In recent years, organic semiconductor materials have developed rapidly in the fields of organic light-emitting diodes (OLEDs), organic thin-film transistors (OFETs), organic thin-film solar cells (OPVs), dye-sensitized cells (DSSCs), and have important application prospects. The development of synthesis and preparation technology of organic semiconductor materials is very important. [0003] N,N-diaryl-2-bromo-6-naphthylamine, as the precursor of strong electron donating unit, can be applied to the preparation of organic optoelectronic materials with excellent hole transport ability. Its three-dimensional structure is beneficial to promote the solubility of molecules and the morphology stability of thin films. I...

Claims

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Application Information

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IPC IPC(8): C07C209/10C07C211/61C07D487/04H01L51/54H01L51/00
Inventor 朱旭辉夏炎王历平张春晖谭婉怡
Owner SOUTH CHINA UNIV OF TECH
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