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Indeno [1, 2-b] indole derivative as well as preparation method and application thereof

A derivative, 2-b technology, applied in chemical instruments and methods, semiconductor/solid-state device manufacturing, electrical components, etc.

Pending Publication Date: 2021-09-10
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In the prior art, the patent document with the authorized announcement number CN107251259B and the publication date of March 01, 2016 discloses a composition and a light-emitting element using the composition. However, the composition provided in the patent application document, and Devices made of this organic EL material still have limitations in the characteristics of the organic EL material

Method used

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  • Indeno [1, 2-b] indole derivative as well as preparation method and application thereof
  • Indeno [1, 2-b] indole derivative as well as preparation method and application thereof
  • Indeno [1, 2-b] indole derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] A preparation method of indeno[1,2-b]indole derivatives, comprising the steps of:

[0043]

[0044] Dissolve 2-iodoaniline (10g, 45.6mmol) 4a in DMF (50mL), then add potassium carbonate (25.2g, 182.6mmol) and iodomethane (25.9g, 182.6mmol), and stir at 90°C for 24 hours After the reaction was completed, it was extracted with the second organic solvent ethyl acetate, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and spin-dried to obtain 5a8.4965g by column chromatography, with a yield of 75%.

[0045] Take 5a (5g, 20.2mmol) in a flask, add 50mL triethylamine, under inert gas conditions, add PdCl 2 (PPh 3 ) 2 (0.14g, 0.2mmol) and CuI (0.0381g, 0.2mmol), after stirring for five minutes, add ethynyltrimethylsilane (2.385g, 24.3mmol), continue to react at room temperature for 12 hours, after the reaction, add saturated The reaction was quenched with ammonium chloride solution, extracted with the second organic solv...

Embodiment 2

[0054] A preparation method of indeno[1,2-b]indole derivatives, comprising the steps of:

[0055]

[0056] Weigh 8a (5g, 46.7mmol) and N-bromosuccinimide (16.6g, 46.7mmol) in a flask, add 100mL of the fourth organic solvent dichloromethane, stir at 0°C for 2 hours, and wait for the reaction to complete Afterwards, cool to room temperature, transfer the reaction solution into a 125mL separatory funnel, add 25mL of the fourth organic solvent dichloromethane and 25mL water for extraction, and extract the aqueous phase three times with the fourth organic solvent dichloromethane, and finally use saturated chlorinated The organic layer was washed with sodium solution, filtered with anhydrous sodium sulfate, and the solvent was spin-dried, and the second organic solvent ethyl acetate:petroleum ether=1:20 was used as the eluent, and the product 9a was separated by column chromatography to obtain 8.126g. The yield was 93%.

[0057] Weigh 9a (5g, 26.9mmol) and dissolve it in 70mL of...

Embodiment 3

[0065] A preparation method of indeno[1,2-b]indole derivatives, comprising the steps of:

[0066]

[0067] Put 10b (0.6g, 1.7mmol) in a flask, add 10mL triethylamine, stir for three minutes under inert gas, then add PdCl 2 (PPh 3 ) 2 (0.012g, 0.0168mmol) and CuI (0.003g, 0.0168mmol), then slowly added 7a (0.25g, 1.7mmol), reacted at room temperature for 12 hours, after the reaction was completed, quenched by adding saturated aqueous ammonium chloride, The second organic solvent was extracted with ethyl acetate, and finally the organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and spin-dried to dry the solvent, and the yellow oily substance 2c was obtained by column chromatography.

[0068] The structure verification results are as follows: 1 H NMR (400MHz, CDCl 3 )δ7.62(d, J=2.0Hz, 1H), 7.53(dd, J=7.6, 1.7Hz, 1H), 7.48(d, J=8.3Hz, 1H), 7.31-7.24(m, 2H), 6.95-6.88(m,2H),3.00(s,6H); 13 C NMR (100MHz, CDCl 3 ...

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PUM

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Abstract

The invention discloses an indeno [1, 2-b] indole derivative as well as a preparation method and application thereof, and the preparation method comprises the following steps: mixing a 2-((2-halogen phenyl) ethynyl)-N, N-dimethylaniline derivative (II), 2-diazo-2-phenyl methyl acetate (III), a metal palladium catalyst, a diphosphorus ligand, an acid-base neutralization additive and a first organic solvent, and carrying out a coupling reaction to realize preparation of the indeno [1, 2-b] indole derivative (I) . The preparation method provided by the invention has the advantages of mild reaction conditions, simple preparation method, high yield and the like, and the prepared product can be used for preparing organic light-emitting devices and ligands.

Description

technical field [0001] The invention relates to an indeno[1,2-b]indole derivative, a preparation method and application thereof, and belongs to the technical field of luminescent materials. Background technique [0002] With the development of information technology, electroluminescence has become a research hotspot today. Organic electroluminescent devices are self-luminous devices. After decades of development, as the necessary characteristics of organic EL materials, compared with liquid crystal devices, organic EL When the component is in use, the component has the characteristics of high brightness, high efficiency, low voltage drive, long life, and easier to read. It has fully realized red, blue, and green light emission, and the application field has also expanded from small molecules to macromolecules and metal complexes. and other fields. [0003] In the prior art, the patent document with the authorized announcement number CN107251259B and the publication date of ...

Claims

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Application Information

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IPC IPC(8): C07D209/56C07D487/04C09K11/06H01L51/50H01L51/54
CPCC07D209/56C07D487/04C09K11/06C09K2211/1029C09K2211/1044H10K85/6572H10K50/11
Inventor 鲁梅史一安苏达山·德纳斯梁玲丽
Owner CHANGZHOU UNIV