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Organic electronic transmission and/or hole-barrier material, synthesis method thereof and use thereof

A technology of hole-blocking materials and organic electronics, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve problems such as poor device performance, further improvement in stability, and changes in luminescent properties

Active Publication Date: 2011-02-02
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 1,3,5-tris(N-phenyl-2-benzimidazole)benzene ( TPBI) is an electron transport / hole blocking material widely used in electroluminescent devices, but its stability in the device needs to be further improved
However, due to its strong intramolecular interactions (such as ∏-∏ overlap), exciplexes are easily formed in the film, which changes its luminescent properties
Therefore, the device performance is poor
So far rarely used in organic electroluminescent devices

Method used

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  • Organic electronic transmission and/or hole-barrier material, synthesis method thereof and use thereof
  • Organic electronic transmission and/or hole-barrier material, synthesis method thereof and use thereof
  • Organic electronic transmission and/or hole-barrier material, synthesis method thereof and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0056] Example 1.1, Preparation of 4-bis(4-(2-phenyl-6-p-tolyl-3-trifluoromethylpyridine))benzene (BPTTPB)

[0057] The first step: take 2-bromo-1-(4-trifluoromethylphenyl) ethanone and pyridine with a molar ratio of 1 as raw materials, stir at room temperature for 11 hours, filter, and wash with a large amount of water to obtain the corresponding pyridine Bromine salt, about 90% yield;

[0058] The second step: under the condition of nitrogen protection, add the first step product, terephthalaldehyde and p-methylacetophenone (mol ratio is 2:1:2) into the three-necked flask, then add an appropriate amount of glacial acetic acid and ammonium acetate, stirring vigorously, maintaining the temperature at 120°C to 140°C, refluxing for 24 hours, filtering out the product, and obtaining the high-purity target product with a yield of about 50% by column chromatography or recrystallization.

[0059] m / z: 700.23 (100.0%), 701.23 (48.3%), 702.24 (11.2%), 703.24 (1.8%).

[0060] Prepa...

Embodiment 21

[0069] Example 2.1, Preparation of 4-bis(4-(6-(4-biphenyl)-2-phenyl-3-trifluoromethylpyridine))benzene (BBPTPB)

[0070]

[0071] The first step: take 2-bromo-1-(4-trifluoromethylphenyl)ethanone with a molar ratio of 1, pyridine is a raw material, stir at room temperature for 12 hours, filter, wash with a large amount of water, and obtain the corresponding pyridine Bromine salt, about 90% yield;

[0072] The second step: under the condition of nitrogen protection, add the first step product, terephthalaldehyde and p-phenylacetophenone (mol ratio is 2: 1: 2) into the three-necked flask, then add an appropriate amount of glacial acetic acid and ammonium acetate, stirring vigorously, keeping the temperature at 120 ℃ ~ 140 ℃, refluxing for 24 hours, filtering out the product, and obtaining the high-purity target product with a yield of about 55% by column chromatography or recrystallization.

[0073] m / z: 824.26 (100.0%), 825.27 (58.8%), 826.27 (17.0%), 827.27 (3.3%).

Embodiment 34

[0074]Example 3. Preparation of 4,4'-(1,4-phenylene)bis(2-phenyl-6-p-tolylpicolinitrile) (PBPTNN)

[0075] The first step: take 4-(2-bromoacetyl) benzonitrile with a molar ratio of 1, and pyridine is a raw material, stirred at room temperature for 10 hours, filtered, washed with a large amount of water, and the corresponding pyridinium bromide was obtained, and the yield was about 85%;

[0076] The second step: under the condition of nitrogen protection, add the first step product, terephthalaldehyde and p-methylacetophenone (mol ratio is 2:1:2) into the three-necked flask, then add an appropriate amount of glacial acetic acid and ammonium acetate, stirring vigorously, maintaining the temperature at 120°C to 140°C, refluxing for 24 hours, filtering out the product, and obtaining the high-purity target product with a yield of about 60% by column chromatography or recrystallization.

[0077] m / z: 614.25 (100.0%), 615.25 (47.9%), 616.25 (11.8%), 617.26 (1.7%), 615.24 (1.5%). ...

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Abstract

The invention belongs to the field of organic electronic transmission and / or cavity barrier materials in organic electroluminescence devices and particularly relates to polyarylate substituted pyridine derivates of the organic electronic transmission and / or hole-barrier material, a synthesis method thereof and use of the polyarylate substituted pyridine derivate material in manufacturing of organic electroluminescence device. In the invention, some large substitutes with a rigid structure are introduced by cellular design, so that exciplex is difficult to generate, a crystallization process is restrained, the film forming property is improved, and charge transmission performance is improved; meanwhile, the destruction of molecular coplanarity causes emission peak hypochromatic shift, so that the device performance is improved. The polyarylate substituted pyridine derivates of the invention have a structure below.

Description

[0001] Related applications [0002] This application is a divisional application of a Chinese invention patent application with the application number of 200710176009.8 and the filing date of October 17, 2007, entitled "Organic Electron Transport and / or Hole Blocking Materials and Synthetic Methods and Uses thereof". technical field [0003] The invention belongs to the field of organic electron transport / hole blocking materials in organic electroluminescent devices, and particularly relates to a class of polyaryl-substituted pyridine derivatives used for organic electron transport and / or hole blocking materials and a synthesis method thereof, and Use of such polyaryl-substituted pyridine derivative materials in preparing organic electroluminescent devices. Background technique [0004] With the development of multimedia technology and the advent of the information society, the requirements for the performance of flat panel displays are getting higher and higher. Three eme...

Claims

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Application Information

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IPC IPC(8): C07D213/80C07D213/85C07D213/30C09K11/06H01L51/54C07D213/26C07D213/84H01L51/56C07D405/14
Inventor 汪鹏飞李娜刘卫敏李述汤
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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