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Synthetic method and application of diphenyl sulfone derivatives

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

Inactive Publication Date: 2015-06-17
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 and application of diphenyl sulfone derivatives
  • Synthetic method and application of diphenyl sulfone derivatives
  • Synthetic method and application of diphenyl sulfone derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Embodiment 1: 4,4'-dicarbazolyl diphenyl sulfone ( 1 )Synthesis

[0012] 4,4'-Difluorodiphenylsulfone (0.69g, 2.7mmol), potassium carbonate (2.25g, 16.3mmol), carbazole (0.99g, 5.9mmol), DMSO 8ml, heated at reflux at 150°C for 12h. Cooled to room temperature and poured into 200ml of water to precipitate a large amount of solid, stirred for 0.5h, filtered with suction to obtain a white solid, and purified by column chromatography to obtain 1.26g of a white solid, with a yield of 85%. 1 H NMR (CDCl 3 , 300MHz): δppm 8.28 (d, 4H J=8.1), 8.14 (d, 4H J=7.8Hz), 7.84 (d, 4H J=7.8Hz), 7.51-7.31 (m, 13H).

[0013]

Embodiment 2

[0014] Embodiment 2: 4,4'-dicarbazolyl diphenyl sulfone ( 2 )Synthesis

[0015] 4,4'-difluorodiphenyl sulfone (0.34g, 1.3mmol), potassium carbonate (1.11g, 8.0mmol), carboline (0.49g, 2.9mmol), DMSO 8ml, heated to reflux at 150°C for 12h. Cool to room temperature and pour into 200ml of water to precipitate a large amount of solid, stir for 0.5h, filter with suction to obtain a brown solid, and purify by column chromatography to obtain 0.59g of a white solid, with a yield of 82%. 1 H NMR (CDCl 3 , 300MHz): δppm8.49-8.43(m, 4H), 8.29(d, 4H, J=8.4Hz), 8.14(d, 2H J=7.8Hz), 7.95(d, 4H J=8.4Hz), 7.62 -7.51 (m, 4H), 7.43-7.30 (m, 4H).

[0016]

Embodiment 3

[0017] Embodiment 3: 4,4'-two (1,2,3,4-tetrahydrocarbazol) base diphenyl sulfone ( 3 )Synthesis

[0018] 4,4'-difluorodiphenylsulfone (0.67g, 2.6mmol), potassium carbonate (1.96g, 8.0mmol), 1,2,3,4-tetrahydrocarbazole (0.99g, 5.8mmol), DMSO 8ml , Heating 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 brown solid, and purified by column chromatography to obtain 1.21g of a white solid, with a yield of 83%. 1 H NMR (CDCl 3 , 300MHz): δppm 8.14 (d, 4H J = 8.4Hz), 7.59-7.50 (m, 6H), 7.30 (t, 2H J = 4.5Hz), 7.15 (t, 4H J = 3.7Hz).

[0019]

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Abstract

The invention discloses a one-step synthetic method for diphenyl sulfone series compounds, wherein the method has the advantages of cheap and easily available raw materials, no need for a noble metal catalyst, simple and convenient operation, mild reaction conditions, low production cost, high yield and convenience in commercialization. The invention relates to the field of organic electroluminescent materials, specifically to a material having bipolar carrier transport performance and synthesized by using the one-step method, and application of the material as an electrophosphorescent main body in the field of electroluminescence. The material with the bipolar carrier transport performance contains different donor units with hole transport performance and a diphenyl sulfone unit with electron transmission performance. The compounds provided by the invention comprise 4,4'-dicarboline diphenyl sulfone, 4,4'-di(1,2,3,4-tetrahydro-carbazole)diphenyl sulfone, 4,4'-di(7-azaindole)diphenyl sulfone and 4,4'-diindolyl diphenyl sulfone.

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): C07D209/86C07D519/00C07D209/08H01L51/54H01L51/00
Inventor 陶友田王芳芳汤超黄维
Owner NANJING UNIV OF TECH
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