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Organic electronic transmission and/or hole barrier materials, synthesis method 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 changes in luminescent properties, stability to be further improved, and poor device performance

Active Publication Date: 2014-08-20
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 materials, synthesis method and use thereof
  • Organic electronic transmission and/or hole barrier materials, synthesis method and use thereof
  • Organic electronic transmission and/or hole barrier materials, synthesis method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0056] Embodiment 1.1, the preparation of 4-bis(2-(4,6-diphenyl-5-trifluoromethylpyridine))benzene (BDTPB)

[0057]

[0058] 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 10 hours, filter, and wash with a large amount of water to obtain the corresponding pyridine Bromide, the yield is about 90%;

[0059] The second step: under the condition of nitrogen protection, add the product of the first step, p-benzophenone and benzaldehyde (2:1:2 in molar ratio) into the three-necked bottle, and then add appropriate amount of glacial acetic acid 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%.

[0060] m / z: 672.20 (100.0%), 673.20 (46.2%), 674.21 (10.2%), 675.21 (1.5%). ...

Embodiment 21

[0070] Example 2.1, Preparation of 4-bis(2-(6-phenyl-4-p-tolyl-5-trifluoromethylpyridine))benzene (BPTTPB)

[0071]

[0072] 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 8 hours, filter, and wash with a large amount of water to obtain the corresponding pyridine Bromide, the yield is about 90%;

[0073] The second step: under the condition of nitrogen protection, the product of the first step, p-benzenediphenone and p-tolualdehyde (2:1:2 in molar ratio) 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%.

[0074] m / z: 700.23 (100.0%), 701.23 (48.3%), 702.24 (11.2%), 703....

Embodiment 36

[0075] Embodiment 3.6, the preparation of 6'-(1,4-phenylene) bis(2,4-diphenylpyridinenitrile) (PBDNN)

[0076]

[0077]The first step: take 4-(2-bromoacetyl) benzonitrile and pyridine with a molar ratio of 1 as raw materials, stir at room temperature for 7 hours, filter, and wash with a large amount of water to obtain the corresponding pyridinium bromide salt with a yield of about 85%;

[0078] The second step: under the condition of nitrogen protection, add the product of the first step, p-benzophenone and benzaldehyde (2:1:2 in molar ratio) into the three-necked bottle, and then add appropriate amount of glacial acetic acid 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%.

[0079] m / z: 586.22 (100.0%), 587.22 (45.7%), 588.22 (10.7%), 589.23 (1.5%), 587.21 (1.5...

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Abstract

The invention belongs to the field of organic electronic transmission and / or hole barrier materials in organic electroluminescent devices, in particular relates to polyaryl substituted pyridine derivatives for the organic electronic transmission and / or hole barrier materials, a synthetic method thereof, and use for preparing the organic electroluminescent devices by using the polyaryl substituted pyridine derivatives. Through molecular design in the invention, large substituent groups with rigid structures are introduced so that exciplexes can not be easily formed by the material, the course of crystallization of the material is inhibited, the film formation of the material is improved, and the charge transmission performance of the material is increased. Synchronously, the emission peak of the material has blue shift due to the damage of molecular coplanarity so that the purpose of improving the performances of the devices is achieved. The polyaryl substituted pyridine derivatives of the invention have the following structure.

Description

[0001] related application [0002] This application is a divisional application of a Chinese invention patent application with the application number 200710176008.3 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): C07D401/10C09K11/06H01L51/05H01L51/30H01L51/42H01L51/46H01L51/50H01L51/54H01L51/00
CPCY02E10/549
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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