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4,7 substituted-1,10-phenanthroline derivative and preparation method thereof

A technology of o-phenanthroline and its derivatives, applied in 4 fields, can solve the problems of low luminous efficiency, complex preparation process, high energy consumption, etc., and achieve remarkable technological progress

Inactive Publication Date: 2015-09-30
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention provides a 4,7-substituted-1,10-phenanthroline derivative and a preparation method thereof, the 4,7-substituted-1,10-phenanthroline derivative and a preparation method thereof Solve the technical problems of complex preparation process, low luminous efficiency and high energy consumption of organic electroluminescent materials in the prior art

Method used

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  • 4,7 substituted-1,10-phenanthroline derivative and preparation method thereof
  • 4,7 substituted-1,10-phenanthroline derivative and preparation method thereof
  • 4,7 substituted-1,10-phenanthroline derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 Preparation of Compound K1

[0025]

[0026] Get McBurney's acid (5.05g, 7.3mmol), 50ml of trimethyl orthoformate in a 100ml round-bottomed flask, mix them and reflux at 106°C for two hours while stirring. After the reflux was completed, the solution was yellow-red. After the solution was cooled, the weighed (1.625 g, 1.8 mmol) o-phenylenediamine was added. And continue to reflux for one hour. After the reflux was completed, the solution was evaporated to dryness with a rotary evaporator, and a yellow solid was precipitated until there was no liquid in the bottle. The solid was washed three times with absolute ethanol (50 ml), and suction filtered to obtain a light yellow powder. Afterwards, it was recrystallized with ethanol to obtain 4.5 g of white needle crystal product M1. Yield: 78%, mp>209°C, Rf=0.56 (ethyl acetate), 1H NMR (DMSO) δ1.66 (s, 12H), 7.42 (d, 4H), 7.61 (d, 4H), 8.26 ( d, 2H), 11.32(d, 2H).

[0027] Take M1 (0.416g, 1mmol) and reflux ...

Embodiment 2

[0030] Example 2 Preparation of Compound K2

[0031]

[0032]Get M3 (0.0338g, 0.1mmol), benzimidazole (0.0296g, 0.25mmol), salt of wormwood (0.069g, 0.5mmol), 2mlDMF joins in the 50ml round-bottomed flask, gets an appropriate amount of copper iodide as catalyst, in React at 135°C for 24h. During the experiment, under nitrogen protection, the reaction solution was extracted with 100ml of dichloromethane and washed with water 6 times, DMF was removed, dried by rotary evaporation, and column chromatography gave 0.04568g of a light yellow powder product. Yield: 85%, Mass Spectrum: m / z=413.3[M]+; NMR: 1H NMR (CDCl3) δ7.21 (d, 2H) 7.34 (t, 2H) 7, 42 (t, 2H) 7.67 (s , 2H) 7.83 (d, 2H) 7.98 (d, 2H) 8.24 (s, 2H) 9.49 (d, 2H).

Embodiment 3

[0033] Example 3 Preparation of Compound K3

[0034]

[0035] Take M3 (0.12g, 0.4mmol), pyrazole (0.055g, 0.8mmol), potassium carbonate (0.11g, 1mmol), and 4ml of DMF into a 50ml round bottom flask, take an appropriate amount of copper iodide as a catalyst, Under reaction 24h. During the experiment, under the protection of nitrogen, the reaction solution was extracted with 100ml of dichloromethane and washed 6 times with water, DMF was removed, dried by rotary evaporation, and 0.056g of a light yellow powder product was obtained by column chromatography. Yield: 55%, Mass Spectrum: m / z=313.3[M]+; NMR: 1H NMR (CDCl3) δ6.67 (s, 2H) 7.76 (d, 2H) 7.96 (d, 2H) 8.02 (d, 2H) )8.32(s,2H)9.32(d,2H)

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Abstract

The invention relates to a 4,7 substituted-1,10-phenanthroline derivative and a preparation method thereof. The 4,7 substituted-1,10-phenanthroline derivative is characterized in that the general formula thereof is as shown in the description, wherein R1 benzimidazole imidazole group, benzotriazole group, imidazole group, pyrazol group, carbazole group, indazole group or indol group. The invention further discloses the preparation method of the 4,7 substituted-1,10-phenanthroline derivative. The 4,7 substituted-1,10-phenanthroline derivative is prepared by taking o-phenylenediamine as the raw material, performing thermal cyclization, substitution and the like to synthesize 1,10-phenanthroline rigid backbone with halogen at 4,7 sites, and introducing the groups with the carrier-transporting property through C-N coupled reaction to synthesize the novel 4,7 substituted-1,10-phenanthroline derivative. According to the 4,7 substituted-1,10-phenanthroline derivative and the preparation method thereof, provided by the invention, a strong photon absorbing ability in an ultraviolet-visible light area is achieved, the weak solution of the derivative can emit strong fluorescence, the emission peak is within 450 nm-500 nm, therefore, the derivative can be applied to the field of organic electroluminescence materials.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to an organic electroluminescent material, specifically a 4,7-substituted-1,10-phenanthroline derivative and a preparation method thereof. Background technique [0002] Organic electroluminescence (OLED) has been extensively studied in the fields of flat panel display and solid-state lighting because of its active luminescence, all-solid-state, low-voltage drive, fast response, wide viewing angle, and high efficiency. Compared with traditional display devices (CRT, LCD), OLED can effectively reduce energy consumption, which fully embodies the low-carbon economy advocated by the country and the development concept of building a resource-saving and environment-friendly society. [0003] In recent years, countries such as the United States, the United Kingdom, Japan, Germany, the Netherlands, and Sweden have been very active in research in this area, and have continuously d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C09K11/06
CPCC07D471/04C09K11/06C09K2211/1044
Inventor 刘清雷王伟王为
Owner SHANGHAI INST OF TECH
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