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Terphenyl bridged-bis-benzimidazole quaternary ammonium compound, synthetic method and application thereof

A bisbenzimidazole and terphenyl bridge technology, applied in the field of optoelectronic materials, can solve problems such as increased manufacturing cost, poor solubility, and inability to use cost spin coating film-forming methods, and achieves improved application performance, improved solubility, and improved Effect of Carrier Transport Ability and Fluorescence Quantum Efficiency

Inactive Publication Date: 2010-10-06
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Make purification, characterization, use of these products difficult (Heil H, Buesing A, Stoessel P, et al. WO2006131192, 2006)
In addition, due to the poor solubility of these materials, the low-cost spin-coating film-forming method cannot be used in device manufacturing, but vacuum evaporation film-forming can only be used, which greatly increases the manufacturing cost of OLEDs and becomes an important factor restricting the development of OLEDs. factor

Method used

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  • Terphenyl bridged-bis-benzimidazole quaternary ammonium compound, synthetic method and application thereof
  • Terphenyl bridged-bis-benzimidazole quaternary ammonium compound, synthetic method and application thereof
  • Terphenyl bridged-bis-benzimidazole quaternary ammonium compound, synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: [1,1'; 4',1"]-terphenyl-4,4"-bis(1,3-dimethyl-2-benzimidazolium ammonium bromide) 1a

[0031] In a 100mL autoclave with magnetic stirring, put 2.31g (5mmol) of 4,4"-bis-benzimidazolyl-p-terphenyl, 40ml of dimethylformamide, 1.06g (10mmol) of anhydrous sodium carbonate, and 4.72g of methyl bromide (50mmol), close the autoclave, heat up to 80-100°C, react at this temperature for 12 hours, cool to 60°C, vacuum out excess methyl bromide and solvent dimethylformamide, add 50mL chloroform to the kettle to dissolve , filtered out the insoluble matter, concentrated chloroform under reduced pressure to obtain a yellow crude product, and the crude product was subjected to column chromatography (dichloromethane / methanol 8:1) to obtain 2.85 g of a pure product with a yield of 83.7% and a melting point greater than 350°C. 1 H NMR (DMSO-d 6 , 300MHz): δ8.25-8.21(m, 8H), 8.06(d, 8H), 7.81-7.78(m, 4H), 4.09(S, 12H). 13 C NMR (DMSO-d 6 , 300MHz): δ149.68, 143.15, 138.37, 1...

Embodiment 2

[0032] Example 2: [1,1'; 4',1"]-terphenyl-4,4"-bis(1,3-diethyl-2-benzimidazolium bromide) 1b

[0033] In a 100mL autoclave with magnetic stirring, put 2.31g (5mmol) of 4,4"-bis-benzimidazolyl-p-terphenyl, 40mL of dimethylformamide, 1.38g (10mmol) of anhydrous potassium carbonate, bromoethane 3.27g (30mmol), in a closed autoclave, heat up to 110-125°C, react at this temperature for 18 hours, cool to 70°C, vacuum out excess bromoethane and solvent dimethylformamide, and pour into the autoclave Add 50 mL of chloroform to dissolve, filter out the insoluble matter, concentrate the chloroform under reduced pressure to obtain a pale yellow crude product, and recrystallize from acetonitrile to obtain 2.8 g of the pure product, with a yield of 75.6%. The melting point is 267-269°C. 1 H NMR (DMSO-d 6 , 300MHz): δ8.25-8.21(m, 8H), 8.06(d, 8H), 7.80-7.77(m, 4H), 4.36(q, 8H), 1.40(t, 12H). 13 C NMR (DMSO-d 6 , 300MHz): δ149.59, 143.25, 138.40, 130.82, 130.80, 127.78, 127.61, 126.59, 120...

Embodiment 3

[0034] Example 3: [1,1'; 4',1"]-terphenyl-4,4"-bis(1,3-dibutyl-2-benzimidazolium ammonium bromide) 1c

[0035] In a 100mL autoclave with magnetic stirring, put 2.31g (5mmol) of 4,4"-bis-benzimidazolyl-p-terphenyl, 50mL of methanol, 1.06g (10mmol) of anhydrous sodium carbonate, and 5.48g of 1-bromobutane (40mmol), close the autoclave, heat up to 100-120°C, react at this temperature for 10 hours, cool to 60°C, vacuum out excess 1-bromobutane and solvent methanol, add 50mL chloroform to the kettle to dissolve , filtered out insoluble matter, and concentrated chloroform under reduced pressure to obtain a yellow crude product, which was separated by column chromatography to obtain 2.6 g of pure product, with a yield of 61.3% and a melting point of 304-306°C.

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Abstract

The invention provides an organic luminescent material, i.e. a terphenyl bridged-bis-benzimidazole quaternary ammonium compound, a preparation method and application thereof. The preparation method comprises the following steps: taking inorganic base as an acid-binding agent, and leading one time of a terphenyl bridged-bis-benzimidazole compound and 4-12 times of halogenated hydrocarbon or halogenated alkene (such as methyl iodide, bromoethane and allyl bromide) in an organic solvent to react for 6-18 hours to obtain a series of the terphenyl bridged-bis-benzimidazole quaternary ammonium compounds. The compound can be used as the organic luminescent material and applied to the fields such as a luminescent device, a photocell, an organic light-emitting diode, a bio-fluorescent probe or a novel fluorescent tracer for a water treatment agent and the like.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. Specifically, it relates to a terphenyl bridged bisbenzimidazole quaternary ammonium compound, a synthesis method and an application. The compound has good solubility and luminescent properties, and can be used as an organic blue light luminescent material in the fields of light emitting devices, photocells, organic light emitting diodes, biological fluorescent probes or fluorescent tracers for new water treatment agents. technical background [0002] Organic light-emitting diode display device (Organic light-emitting diode, OLED) is a dual-carrier injection display, compared with traditional display technology, it has ultra-light, ultra-thin, wide viewing angle, high-definition, low temperature resistance, and shock resistance. Well wait for a series of advantages. It will become a strong contender for a new generation of light sources and flat panel displays. The most importa...

Claims

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Application Information

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IPC IPC(8): C07D235/20C09K11/06G01N21/64
Inventor 朱红军罗中华常进吴涛宋广亮姜鹏
Owner NANJING UNIV OF TECH
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