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Synthetic method for pyridine derivatives and application of derivatives

A pyridine and bonding technology, applied in electrical components, circuits, organic chemistry, etc., can solve the problems of concentration quenching triplet-triplet annihilation effect, reducing device luminous efficiency and brightness, etc.

Inactive Publication Date: 2014-11-19
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the long excited state lifetime of the electrophosphorescent material itself, there are serious concentration quenching and triplet-triplet annihilation effects, which greatly reduce the luminous efficiency and brightness of the device.

Method used

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  • Synthetic method for pyridine derivatives and application of derivatives
  • Synthetic method for pyridine derivatives and application of derivatives
  • Synthetic method for pyridine derivatives and application of derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Embodiment 1: 2,4-dicarbazolylpyridine ( 1 )Synthesis

[0012] 2,4-Difluoropyridine (0.30g, 2.6mmol), potassium carbonate (2.2g, 15.6mmol), carbazole (0.96g, 5.7mmol), DMSO 10ml, heated to reflux at 150°C for 12h. Cooled to room temperature and poured into 200ml of water to precipitate a large amount of solid and stirred for 0.5h, suction filtered to obtain a white solid, purified by column chromatography to obtain 1.01g of white solid, yield 88%. 1 H NMR (CDCl 3 , 300MHz): δppm8.97 (d, 1H J = 5.4), 8.15 (t, 4H, J = 7.5Hz), 7.95 (d, 3H J = 7.5Hz), 7.68 (d, 3HJ = 8.1Hz), 7.49 (t, 4H J = 8.1 Hz), 7.36 (t, 4H J = 7.2 Hz).

[0013]

Embodiment 2

[0014] Embodiment 2: 2,3-dicarbazolylpyridine ( 2 )Synthesis

[0015] 2,3-Difluoropyridine (0.3g, 2.6mmol), the others were the same as in Example 1, and purified by column chromatography to obtain 0.91g of white solid with a yield of 85%. 1 H NMR (CDCl 3 , 300MHz): δppm8.87(d, 1HJ=3.6), 8.23(d, 1H, J=7.8Hz), 7.83-7.76(m, 4H), 7.66(t, 1HJ=7.5Hz), 7.27(t , 2H.J=6.6Hz), 7.09-6.99 (m, 10H).

[0016]

Embodiment 3

[0017] Embodiment 3: 2,3,5,6-tetracarbazolylpyridine ( 3 )Synthesis

[0018] 2,3,5,6-Tetrafluoropyridine (0.3g, 2.0mmol), the others were the same as Example 1, purified by column chromatography to obtain 1.3g of white solid, yield 90%. 1 H NMR (CDCl 3 , 300MHz): δppm8.76(s, 1H), 7.88-7.80(m, 8H), 7.52(d, 4H J=6.0), 7.27(t, 4HJ=3.3Hz), 7.14-7.10(m, 14H) , 7.09-7.00 (m, 4H).

[0019]

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Abstract

The invention develops a method, which adopts cheap and easily-available raw materials, is free of a noble metal catalyst, is simple and convenient to operate, gentle in reaction condition, low in production cost, high in yield and convenient for commercialization, for synthesizing pyridine and carbazole-series compounds by virtue of a one-step process, relates to the field of organic electroluminescence materials, and particularly relates to a material synthesized by virtue of the one-step process and provided with bipolar carrier transmission performance as well as an application of the material as an electroluminescent phosphor to the electroluminescence field. The material provided with the bipolar carrier transmission performance not only contains a carbazole unit with hole transport performance, but also contains a pyridine unit with electron transport performance; and the compounds are 2,4-dicarbazolyl pyridine, 2,3- dicarbazolyl pyridine, 2,3,5,6-tetracarbazolyl pyridine and 2, 3, 4, 6- tetracarbazolyl pyridine respectively.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to one-step synthesis of a material with bipolar carrier transport performance and its application in the field of electroluminescence as an electrophosphorescent main body. technical background [0002] 1997 reported the first organic electrophosphorescent device using organic transition metal complexes as light emitters in "Nature", and found that electrophosphorescent materials can simultaneously use singlet and triplet excitons to emit light, and its theoretical internal quantum efficiency can reach 100%, has attracted a lot of attention and research. In recent years, organic light-emitting diodes (OLEDs) based on phosphorescent materials have attracted much attention due to their outstanding advantages such as small size, light weight, flexibility, high luminous efficiency, and fast response. However, due to the long excited state lifetime of the electroph...

Claims

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Application Information

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IPC IPC(8): C07D401/14H01L51/54
CPCC07D401/14H10K85/654
Inventor 陶友田黄维汤超王芳芳
Owner NANJING UNIV OF TECH
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