Organic electron transport and/or cavitation block material and synthesis method and application 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 changes in luminescent properties, stability to be further improved, and poor device performance

Active Publication Date: 2013-01-23
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 cavitation block material and synthesis method and application thereof
  • Organic electron transport and/or cavitation block material and synthesis method and application thereof
  • Organic electron transport and/or cavitation block material and synthesis method and application thereof

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 bottle, and then an appropriate amount of glacial acetic acid is added and ammonium acetate, stirring vigorously, keeping the temperature at 120°C to 140°C, refluxing for 24 hours, filtering the product, and obtaining the target product with high purity through column chromatography or recrystallization, 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, stirring vigorously, keeping the temperature at 120°C to 140°C, refluxing for 24 hours, filtering out the product, and obtaining the high-purity target product through column chromatography or recrystallization, with a yield of about 55%.

[0073] m / z: 824.26 (100.0%), 825.27 (58.8%), 826....

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 electron transport or cavitation block materials in organic electroluminescent devices, and more particularly relates to a multiaryl-substituted replace pyridine derivative for an organic electron transport and / or cavitation block material and a synthesis method thereof, and application thereof for preparing the organic electroluminescent devices. Theinvention can ensure that a plurality of big substituents with rigid structures are introduced to avoid forming exciplexes through molecular design; the crystallization course is limited; the film forming property is improved; the charge transmission performance is enhanced; and the blue shift of the emission peak simultaneously appears because of the destroy of molecular coplanarity to reach thepurpose of improving device performance. The multiaryl-substituted replace pyridine derivative comprises the following structures.

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): C07D213/30C07D213/26C07D213/85C07D213/80C07D213/803C07D405/14C09K11/06H01L51/00H01L51/54H01L51/50H01L51/30H01L51/46
CPCY02E10/50Y02E10/549
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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