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Bispyridyl benzimidazole compounds and synthesis method thereof

A technology of bispyridylbenzimidazole and pyridylbenzimidazole, which is applied in the field of bispyridylbenzimidazole compounds and their synthesis, can solve problems such as the lack of blue light materials, hindering cathode electron injection, and restricting the development of organic full-color displays. , to achieve the effect of high product yield and simple operation

Inactive Publication Date: 2011-08-17
SUIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, people have discovered some green and red light materials with excellent electroluminescent properties, but blue light materials with excellent properties have been very scarce.
This is because blue light-emitting materials have a wide band gap, which hinders the injection of cathode electrons, and the lack of blue light-emitting materials has restricted the development of organic full-color displays in a sense.

Method used

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  • Bispyridyl benzimidazole compounds and synthesis method thereof
  • Bispyridyl benzimidazole compounds and synthesis method thereof
  • Bispyridyl benzimidazole compounds and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: the preparation of 2-(2-pyridine)-benzimidazole

[0020] Add 4.92g (40mmol) of 2-pyridinecarboxylic acid, 4.32g (40mmol) of o-phenylenediamine and about 15mL of polyphosphoric acid into a 50mL beaker. 4 times, about 1.5 min each time, and then pour the obtained dark green solution into ice water, and a blue precipitate is formed. After filtering, the obtained precipitate was dispersed in water, and the pH value was adjusted to about 9 to obtain a white precipitate. Dissolve the precipitate in ethanol solution, add activated carbon for decolorization, and then recrystallize in a mixed solvent of V (ethanol): V (water) = 1:3 to obtain 2-pyridinebenzimidazole with a yield of 88%.

[0021] The preparation method of 2-(3-pyridine)-benzimidazole and 2-(4-pyridine)-benzimidazole compound is exactly the same as that of Example 1, and the yields are 85% and 80% respectively.

Embodiment 2

[0022] Example 2: Preparation of 1,1'-(1,4-butyl)bis[2-(3-pyridine)benzimidazole] (Compound 1 for short)

[0023] In a dry and clean 100mL flask, add 7.8g (40 mmol) of 2-(3 pyridyl) benzimidazole and 2.4g (60 mmol) of sodium hydroxide, then add 30 mL of DMF, and raise the temperature to 60 o C, after stirring for about 30 min, add 4.32 g (20 mmol) of 1,4-dibromobutane, continue to raise the temperature to 80 ° C, react for 8 h, remove most of the DMF solvent from the product under reduced pressure, pour into 400 mL of ice water, a light yellow solid was formed, and the resulting precipitate was recrystallized in a mixed solvent of V (methanol): V (water) = 1:3 after filtration to obtain a light yellow crystal of compound 1 with a yield of 75 %. Elemental Analysis C 28 h 24 N 6 (Mr = 444.53) C, 75.65; H, 5.44; N, 18.91. Actual value: C, 75.72; H, 5.39; N, 18.84. IR (cm -1 ): 3389(ms), 3061(ms), 2956(s), 1948(ws), 1899(ws), 1603(s), 1569(s), 1509(ms), 1451(s), 1421(s ),...

Embodiment 3

[0024] Example 3: Preparation of 1,1'-(1,6-hexyl)bis[2-(3-pyridine)benzimidazole] (Compound 2 for short)

[0025] Compound 2 was synthesized according to the preparation method of compound 1, except that 1,4-dibromobutane was replaced by 1,6-dibromohexane, and the reaction time was increased from 8h to 10h to obtain brown compound 2 with a yield of 72 %. Elemental Analysis C 30 h 28 N 6 (Mr =472.568) C, 76.24; H, 5.97; N, 17.79. Actual value: C, 75.99; H, 5.89;N, 17.86. IR (cm -1 ): 3378(ms), 3058(ms), 2936(s), 1886(ms), 1596(s), 1565(ms), 1507(ms), 1463(s), 1431(s), 1382(s ), 1363(s), 1332(s), 1275(s), 1252(s), 1194(s), 1158(s), 1108(s), 1082(s), 1011(s), 986(s) ), 924(s), 829(s), 757(ms), 701(s), 626(s), 579(s), 428(ms).

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Abstract

The invention provides bispyridyl benzimidazole compounds and a synthesis method thereof. The method comprises the following steps of: synthesizing three monopyridyl benzimidazoles by taking pyridinecarboxylic acid and o-phenylenediamine as raw materials by a microwave radiation method; and reacting the three monopyridyl benzimidazoles and a dihaloalkane compound in N,N'-dimethylformamide (DMF) reaction medium under middle temperature water bath conditions by using inorganic base as an acid binding agent for 8 to 12 hours to obtain a series of bispyridyl benzimidazole compounds. The method iseasy to operate; moreover, the yield is high, and the product has high purity, and is easy to crystallize. The compounds have steady fluorescence emission properties at normal temperature, and can beused as blue luminescent materials with steady chemical properties. The invention fills in the gap of the research on flexible bispyridyl benzimidazole compounds at home and abroad at present, and also injects new vitality into the field of organic luminescent materials.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, and in particular relates to a bispyridylbenzimidazole compound and a synthesis method. Background technique [0002] Benzimidazole compounds have a wide range of biological activities and are widely used in high-performance composite materials, electronic chemicals, metal anti-corrosion, photosensitive materials, biology, medicine and other fields, especially it has good fluorescence quantum efficiency and electrical properties , has shown unique properties in the fields of electron transport materials, fluorescent tracers, nonlinear optical materials, fluorescent whitening agents, and multifunctional luminescent materials. At present, people have discovered some green and red light materials with excellent electroluminescent properties, but blue light materials with excellent properties have been very scarce. This is because the blue light-emitting material has a wide ban...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C09K11/06
Inventor 刘海燕乔秀丽孙红梅赵大伟王广慧迟云超
Owner SUIHUA UNIV
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