Terphenyl bridged double-benzimidazoles compound as well as synthesis method and application thereof

A bibenzimidazole and terphenyl bridge technology, applied in the field of optoelectronic materials, can solve the problems of insufficient stability and poor color purity of blue light materials, achieve the effect of improving electron transport ability and luminescent performance, and changing chemical characteristics

Inactive Publication Date: 2010-06-30
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, blue light materials also have the disadvantages of insufficient stability (heat and electric field) and poor color purity

Method used

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  • Terphenyl bridged double-benzimidazoles compound as well as synthesis method and application thereof
  • Terphenyl bridged double-benzimidazoles compound as well as synthesis method and application thereof
  • Terphenyl bridged double-benzimidazoles compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the synthesis of 4,4 "-dicyano-p-terphenyl

[0029] Add 3.23g (22mmol) of 4-cyanophenylboronic acid, 2.36g (10mmol) of p-dibromobenzene, 9.32g (88mmol) of anhydrous sodium carbonate, and 0.462 g (0.66mmol) and 50mL tetrahydrofuran, heated to 50-65°C, and reacted at this temperature for 20 hours. Remove tetrahydrofuran under reduced pressure, add 30mL of dichloromethane to dissolve, wash with water, and separate layers. After the organic layer is dried over anhydrous sodium sulfate, part of the dichloromethane is concentrated, the temperature is lowered to precipitate a white solid, and the white crystal powder is obtained by suction filtration and drying. 4,4" -Dicyano-p-terphenyl 2.03g, yield 72.4%, melting point 288-290°C.

Embodiment 2

[0030] Embodiment 2: the synthesis of 2'-methyl-4,4 "-dicyano-p-terphenyl

[0031] Add 3.38g (23mmol) of 4-cyanophenylboronic acid, 2.50g (10mmol) of 2,5-dibromotoluene, 12.12g (88mmol) of anhydrous potassium carbonate, bis(triphenylphosphine) dichloro Palladium chloride 0.462g (0.66mmol) and 50mL tetrahydrofuran were heated up to 50-65°C and reacted at this temperature for 15 hours. Remove tetrahydrofuran under reduced pressure, add 30 mL of dichloromethane to dissolve, wash with water, separate layers, dry the oil layer over anhydrous sodium sulfate, concentrate part of the dichloromethane, cool down to precipitate white crystals. After suction filtration and drying, 2.26 g of white crystal 2'-methyl-4,4"-dicyano-p-terphenyl was obtained, with a yield of 76.8% and a melting point of 254-255°C. 1 H NMR (CDCl 3 , 500MHz): δ7.77-7.70(m, 6H), 7.52-7.45(m, 4H), 7.31(d, 1H), 2.34(s, 3H); 13 C NMR (CDCl 3 , 300MHz): δ145.98, 145.02, 140.44, 139.20, 136.05, 132.69, 132.14, 130.3...

Embodiment 3

[0032] Embodiment 3: 2'-nitro-4,4 "-the synthesis of dicyano-p-terphenyl

[0033] Add 2.94g (20mmol) of 4-cyanophenylboronic acid, 2.81g (10mmol) of 2-nitro-1,4-dibromobenzene, 9.32g (88mmol) of anhydrous sodium carbonate, tetrakis (triphenyl phosphine) palladium 0.762g (0.66mmol), and 50mL tetrahydrofuran, the temperature was raised to 55-65°C, and the reaction was carried out at this temperature for 18 hours. Tetrahydrofuran was removed under reduced pressure, dissolved in 30 mL of dichloromethane, washed with water, and separated into layers. The organic layer was dried over anhydrous sodium sulfate, concentrated, and the temperature was lowered to precipitate pale yellow crystals. After suction filtration and drying, 2.23 g of yellow crystal powder 2'-nitro-4,4"-dicyano-p-terphenyl was obtained, with a yield of 68.8% and a melting point of 235-237°C.

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Abstract

The invention provides a terphenyl bridged double-benzimidazoles compound as well as a synthesis method and application thereof. The invention takes cyanophoric phenyloboricacid and aromatic dibromide (such as 1,4-dibromo-benzene, 2-fluorine-1, 4-dibromo-benzene, 2,5-dibromo-toluene) as raw materials; under the catalysis of organic palladium and inorganic base, a series of terphenyl compounds with di-cyan can be synthesized by the Suzuki coupling reaction; and then a series of terphenyl bridged double-benzimidazoles compounds can be obtained by adding 1 time of di-cyano-terphenyl compounds and 2-2.4 times of o-phenylenediamine compounds, taking polyphosphoric acid as the catalyst and carrying out the condensation reaction for 6-24 hours under 180-240 degrees C.. The compound can be applied to the fields such as light emitting devices, photovoltaic cells, organic light-emitting diodes and the like as the organic blue-light material or the electron transport material.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. Specifically, it relates to a terphenyl bridged bisbenzimidazole compound, a synthesis method and an application. The compound has light-emitting and electron-transport properties, and can be used as an organic light-emitting blue light material or an electron-transport material in the fields of light-emitting devices, photovoltaic cells, organic light-emitting diodes, and the like. technical background [0002] Organic light-emitting diode display device (Organic light-emitting diode, OLED) will become a new generation of light source and flat panel due to its many excellent advantages such as rich colors, active light emission, small size, thin thickness, wide viewing angle, low energy consumption and fast response speed. A strong contender for the display. To achieve full-color display, red, green and blue light-emitting materials are required, among which blue light material...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/20C09K11/06H01L51/50H01L51/54
Inventor 朱红军罗中华常进宋广亮姜鹏吴涛
Owner NANJING UNIV OF TECH
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