Green synthetic method of indole carbazole compounds for organic electroluminescent materials

An electroluminescent material, indolocarbazole technology, applied in the direction of organic chemistry, etc., can solve the problems of high cost, difficult to obtain diindolylmethane, etc., and achieve the effects of less impurities, easily available price, and high yield

Active Publication Date: 2017-03-08
西安欧得光电材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] Panesar, Harmanpreet Kaur et al, Synthesis and DNA binding profile of N-mono-and N,N'-disstituted indolo[3,2-b]carbazoles, Organic & Biomolecular Chemistry, 13(10), 2879-2883; 2015 on the synthesis of compound 3 According to the report, the method is as follows, and the starting material 2,3-diindolylmethane is not easy to get, and the cost is higher

Method used

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  • Green synthetic method of indole carbazole compounds for organic electroluminescent materials
  • Green synthetic method of indole carbazole compounds for organic electroluminescent materials
  • Green synthetic method of indole carbazole compounds for organic electroluminescent materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 500ml of decahydronaphthalene, 22.4g of 1,2-cyclohexanedione, and 57.6g of phenylhydrazine hydrochloride into a 1L three-neck flask, heat to control the temperature (190°C±2), stop the reaction after 30 minutes, and solvent recovery cycle used in the reaction process. After cooling down to room temperature, a large amount of products were precipitated, filtered to obtain 47.2 g of (1) 11,12-dihydroindolo[2,3-a]carbazole in the form of khaki powder, melting point: 367-375°C (yield: 92.1 %, HPLC=99.7%).

[0023] 1 HNMR (400MHz, DMSO-d6) δ11.36 (2H, s), 8.16 (2H, d), 7.92 (2H, s), 7.73 (2H, d), 7.51 (2H, m), 7.26 (2H, m )

Embodiment 2

[0025] Add 500ml of diphenyl ether, 622.4g of 1,3-cyclohexanedi, 57.6g of phenylhydrazine hydrochloride into a 1L three-necked flask, heat to control the temperature (190°C±2), stop the reaction after 30 minutes, and recover the solvent for recycling in the reaction process. After cooling down to room temperature, a large amount of products precipitated, filtered to obtain (2) 5,12-dihydroindolo[3,2-a]carbazole 46.3g (MS: 128,256) off-white powder. Melting point: 298-305°C (Yield: 90.3%, HPLC=99.5%). 1 H NMR (400 MHz, DMSO-d6) δ 11.06 (2H, s), 8.26 (3H, d), 7.81 (2H, d), 7.62 (2H, m), 7.23 (3H, m).

Embodiment 3

[0027] Add 250ml of decahydronaphthalene, 250ml of diphenyl ether, 22.4g of 1,4-cyclohexanedione, and 57.6g of phenylhydrazine hydrochloride into a 1L three-necked flask, heat to control the temperature (190°C±2), and stop after 30 minutes. Reaction, solvent recovery and recycling for the reaction process. When the temperature was lowered to room temperature, a large amount of products were precipitated. After filtration, 47.1 g of (3) 5,11-dihydroindolo[3,2-b]carbazole was obtained as off-white powder (91.9% yield, HPLC=99.7%).

[0028] 1 HNMR (400 MHz, DMSO-d6) δ 11.03 (2H, s), 8.21 (2H, d), 7.46 (2H, d), 7.36 (2H, t), 7.12 (2H, t).

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Abstract

The invention provides a green synthetic method of indole carbazole compounds for organic electroluminescent materials. The green synthetic material includes that ring adipic ketone compounds and phenylhydrazine hydrochloride are taken as raw materials reacting in one of decalin, diethylbenzene and diphenyl ether or every two mixed solvent and nonpolar solvent with boiling point exceeding 150DEG C, and the indole carbazole compounds are obtained after rapid reaction; after reaction is completed, a reaction system is cooled to indoor temperature to have products separated out, and only filtration is needed to obtain highly-purified indole carbazole compounds. With the method, the raw materials are easy to obtain and low in cost, the indole carbazole compounds can be obtained after rapid reaction without any acid and alkali and catalyst effect, high purity, less impurity and high yield are achieved, only cooling is needed in post treatment, and the highly-purified indole carbazole compounds can be obtained by filtration; easiness in operation is achieved, and the solvent can be recycled without treatment and cyclically used in the reaction process; discharge of wastewater and effluent of acid and alkali and the like is avoided, and green production is realized.

Description

technical field [0001] The invention relates to a green synthesis method of indolecarbazole, an organic electroluminescent material. Background technique [0002] Indolecarbazole has been used more and more in the development of new optoelectronic materials in recent years. Indolecarbazole can be used to prepare organic nonlinear optics (NLO) materials, organic electroluminescent (OLED) materials, photorefractive variable materials, dual-functional systems containing indolecarbazole chromophores, photorefractive small molecule glasses containing indolecarbazole, etc. [0003] There are many synthetic methods for indolecarbazole, and there are many reported documents: Banerji, Avijit et al, Chemistry Letters, 34(11), 1500-1501; 2005 reported compound 1 (11,12-dihydroindolo[ 2,3-a] carbazole) synthetic method, using 3-formaldehyde indole as a starting material, after coupling to obtain 2,2'-biindole dicarbaldehyde, and then reacting with hydrazine in tetrahydrofuran to obtain...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 任莺歌姜虎子袁汀刘英锋
Owner 西安欧得光电材料有限公司
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