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Organic electron transport and/or hole blocking material and its synthesis method and use

A hole-blocking material and organic electron technology, applied in chemical instruments and methods, light-emitting materials, organic chemistry, etc., can solve the problems of changes in light-emitting properties, further improvement of stability, and poor device performance.

Active Publication Date: 2014-10-15
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 electron transport and/or hole blocking material and its synthesis method and use
  • Organic electron transport and/or hole blocking material and its synthesis method and use
  • Organic electron transport and/or hole blocking material and its synthesis method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0056] Embodiment 1.1, the 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 Bromide, the yield is about 90%;

[0058] The second step: under the condition of nitrogen protection, the product of the first step, terephthalaldehyde and p-methylacetophenone (molar ratio is 2:1:2) are added in the three-necked flask, and then an appropriate amount of glacial acetic acid is added and ammonium acetate, stirred vigorously, kept the temperature at 120°C to 140°C, refluxed for 24 hours, filtered out the product, and subjected to column chromatography or recrystallization to obtain the high-purity target product with a yield of about 50%.

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

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, and pyridine as a raw material, stir at room temperature for 12 hours, filter, and wash with a large amount of water to obtain the corresponding pyridine Bromide, the yield is about 90%;

[0072] The second step: under the condition of nitrogen protection, the product of the first step, terephthalaldehyde and p-phenylacetophenone (molar ratio is 2:1:2) are added in the three-necked flask, and then an appropriate amount of glacial acetic acid is added and ammonium acetate, stirred vigorously, kept the temperature at 120°C to 140°C, refluxed for 24 hours, filtered out the product, and subjected to column chromatography or recrystallization to obtain the high-purity target product with a yield of about 55%.

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

Embodiment 34

[0074]Embodiment 3.4, the preparation of 4'-(1,4-phenylene) bis(2-phenyl-6-p-tolylpyridinecarbonitrile) (PBPTNN)

[0075] The first step: get 4-(2-bromoacetyl) benzonitrile with a molar ratio of 1, pyridine is a raw material, stir at room temperature for 10 hours, filter, and wash with a large amount of water to obtain the corresponding pyridinium bromide, with a yield of about 85%;

[0076] The second step: under the condition of nitrogen protection, the product of the first step, terephthalaldehyde and p-methylacetophenone (molar ratio is 2:1:2) are added in the three-necked flask, and then an appropriate amount of glacial acetic acid is added and ammonium acetate, stirred vigorously, kept the temperature at 120°C to 140°C, refluxed for 24 hours, filtered out the product, and subjected to column chromatography or recrystallization to obtain the high-purity target product with a yield of about 60%.

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

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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 application [0002] This application is a divisional application of a Chinese invention patent application with the application number 200710176009.8 and the filing date of October 17, 2007, entitled "Organic Electron Transport and / or Hole Blocking Materials and Their Synthesis Method and Application". technical field [0003] The invention belongs to the field of organic electron transport / hole blocking materials in organic electroluminescent devices, in particular to a class of polyaryl-substituted pyridine derivatives and a synthesis method thereof for organic electron transport and / or hole blocking materials, and The use of the polyaryl-substituted pyridine derivative material in the preparation of organic electroluminescent devices. Background technique [0004] With the development of multimedia technology and the advent of the information society, the performance requirements of flat panel displays are getting higher and higher. Three new display tech...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/26C07D213/85C07D213/80C07D213/84C07D405/14C07D213/30C09K11/06H01L51/54H01L51/56
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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