Organic electronic transmission and/or positive hole countercheck material, and synthesizing method and purpose thereof

A hole-blocking material and organic electron technology, applied in the field of polyaryl-substituted pyridine derivatives and their synthesis, can solve the problems of changing luminescence properties, further improvement of stability, and poor device performance.

Active Publication Date: 2009-04-22
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-three (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 Π—Π overlapping), it is easy to form exciplexes 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 positive hole countercheck material, and synthesizing method and purpose thereof
  • Organic electronic transmission and/or positive hole countercheck material, and synthesizing method and purpose thereof
  • Organic electronic transmission and/or positive hole countercheck material, and synthesizing method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0059] Embodiment 1.1, the preparation of 4-bis (2-(4,6-diphenyl-5-trifluoromethylpyridine)) benzene (BDTPB)

[0060]

[0061] 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%;

[0062] The second step: under the condition of nitrogen protection, add the product of the first step, p-benzophenone and benzaldehyde (2:1:2 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%.

[0063] m / z: 672.20 (100.0%), 673.20 (46.2%), 674.21 (10.2%), 675.21 (1.5%). ...

Embodiment 21

[0073] Embodiment 2.1, the preparation of 4-bis(2-(6-phenyl-4-p-tolyl-5-trifluoromethylpyridine)) benzene (BPTTPB)

[0074]

[0075] 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%;

[0076] The second step: under the condition of nitrogen protection, add the product of the first step, p-benzodiphenone and p-tolualdehyde (2:1:2 molar ratio) into the three-necked bottle, and then add an 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 55%.

[0077] m / z: 700.23 (100.0%), 701.23 (48.3%), 702.24 (11.2%), 703.24 (1...

Embodiment 36

[0078] Embodiment 3.6, the preparation of 6'-(1,4-phenylene) bis(2,4-diphenylpyridinenitrile) (PBDNN)

[0079]

[0080]The first step: take 4-(2-bromoacetyl)benzonitrile and pyridine as raw materials with a molar ratio of 1, stir at room temperature for 7 hours, filter, and wash with a large amount of water to obtain the corresponding pyridinium bromide, with a yield of about 85%;

[0081] The second step: under the condition of nitrogen protection, add the product of the first step, p-benzophenone and benzaldehyde (2:1:2 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%.

[0082] 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 electron transmission / hole blocking materials for organic electroluminescent devices, and particularly relates to a polyaryl-substituted pyridine derivative used in the organic electron transmission materials and / or the organic hole blocking materials, a synthetic method thereof as well as the usage of the polyaryl-substituted pyridine derivative material for preparing an organic electroluminescent device. By a molecular design, a plurality of large substituents with rigid structures are introduced, which causes an exciplex not to easily form in the derivative, inhibits the crystallization course thereof, improves the film forming thereof and improves the charge transfer property thereof; meanwhile, the breakage of the molecular coplanarity causes a blue shift of the emission peak of the derivative, thus achieving the purpose of improving the performance of the device. The polyaryl-substituted pyridine derivative comprises the structure.

Description

technical field [0001] 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 [0002] 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 technologies emerging in recent years: plasma display, field emission display and organic electroluminescent display (OLED), all make up for the shortcomings of cathode ray tube (CRT) and liquid crystal display (LCD) to a certain extent. Among them, OLED has a series of advantages such as self-illumination, low-voltage DC dr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/00H01L51/54H01L51/50H01L51/30H01L51/46C07D213/53C07D213/78C07D405/14C09K11/06
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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