Luminescent materials based on thioxanthene-fluorene spiral structures and organic optoelectronic devices adopting the materials as luminescent layers

A technology for luminescent materials and optoelectronic devices, applied in luminescent materials, electrical solid devices, electrical components, etc., can solve the problems of organic light-emitting small molecules that are rarely reported, and achieve improved carrier transport characteristics, good reproducibility, and material structure single effect

Active Publication Date: 2015-01-07
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, although there have been many reports on light-emitting materials for organic electroluminescent devices, there are few reports on small organic light-emitting molecules with a thioxanthene-fluorene spiro structure as the core.

Method used

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  • Luminescent materials based on thioxanthene-fluorene spiral structures and organic optoelectronic devices adopting the materials as luminescent layers
  • Luminescent materials based on thioxanthene-fluorene spiral structures and organic optoelectronic devices adopting the materials as luminescent layers
  • Luminescent materials based on thioxanthene-fluorene spiral structures and organic optoelectronic devices adopting the materials as luminescent layers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The preparation of intermediate 1 of this embodiment:

[0040] Add 4.66g (20mmol, 10equ) of 2-bromobiphenyl to the low-temperature reaction flask, dissolve it with 60mlTHF, and protect it with nitrogen gas. After sealing the device, add liquid nitrogen to cool to -78°C, and drop 8.0ml (2.5 M) Butyllithium, keep warm for 40min, then add 0.7g 3,7-dibromothioxanthone THF solution at one time, then react at room temperature overnight, the reaction is complete, remove THF with rotary evaporator, dichloromethane extraction, column separation The isolated product h1 was obtained, 20ml of acetic acid and an appropriate amount of hydrochloric acid were added to the isolated product, under nitrogen protection, stirred overnight at 80°C, and 10.83g of white solid intermediate 1 was obtained by column separation, with a yield of 82%. 1H NMR (400MHz, CDCl 3 , ppm): 7.86-7.82 (d, 2H), 7.50-7.54 (s, 2H), 7.25-7.40 (m, 4H), 7.02-7.05 (m, 4H), 6-95-7.00 (dd, 2H) . The reaction equati...

Embodiment 2

[0048] The preparation of intermediate 2 of this embodiment:

[0049]Dissolve 1.5 g of the intermediate 1 obtained in Example 1 with 30 ml of dichloromethane, add 12 ml of acetic acid and 3.0 ml of 30% hydrogen peroxide, and react overnight at 80° C. After the reaction is complete, extract with dichloromethane, dry over anhydrous magnesium sulfate, and the solid Sample loading, petroleum ether:dichloromethane=2:1 (volume ratio) was passed through the column, and 1.23 g of white solid intermediate 2 was isolated with a yield of 80%. 1H NMR (400MHz, CDCl 3 , ppm): 7.86-7.82 (d, 2H), 7.64-7.68 (dd, 2H), 7.50-7.54 (s, 2H), 7.38-7.43 (m, 4H), 7.25-7.40 (m, 4H). The reaction equation is as follows:

[0050]

Embodiment 3

[0052] The preparation of intermediate 3 of this embodiment:

[0053] Add 4.66g (20mmol, 10equ) of 2-bromobiphenyl to the low-temperature reaction flask, dissolve it with 60mlTHF, and protect it with nitrogen gas. After sealing the device, add liquid nitrogen to cool to -78°C, and drop 8.0ml (2.5 M) Butyllithium, keep warm for 40min, then add 0.582g of 3-bromothioxanthone THF solution at one time, then react overnight at room temperature, the reaction is complete, remove THF with rotary evaporator, extract with dichloromethane, column separation to obtain product h2 , adding 20ml of acetic acid and appropriate amount of hydrochloric acid to the product h2, under nitrogen protection, stirring at 80°C overnight, and column separation to obtain 0.65g of white solid intermediate product 3, with a yield of 76%. C 25 h 15 BrS M / S=426.01,, theoretical value: 428.01 (100.0%), 426.01 (99.0%), 429.01 (28.2%), 427.01 (27.7%), 428.00 (4.5%), 430.00 (4.4%), 430.01 (3.7 %), 431.00 (1.2%)...

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Abstract

The invention belongs to the technical field of photoelectric materials, and particularly relates to luminescent materials based on thioxanthene-fluorene spiral structures and organic photoelectric devices adopting the materials as luminescent layers. The luminescent materials adopts the thioxanthene-fluorene spiral structures as skeleton units. Intermediates are prepared through Ullmann reactions, and then the target compounds are obtained through Ullmann reactions or Suzuki reactions. The materials are single in structure and definite in molecular weight. The spiral structures of the materials can adjust an intermolecular accumulation manner, thus effectively inhibiting exciplex luminescence. The materials have deep meaning for development of high-effect devices. The organic photoelectric devices adopting the materials as the luminescent layers have good luminescent properties and can be used for small organic molecule light emitting diodes.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, and in particular relates to a luminescent material based on a thioxanthene-fluorene spiro structure and an organic photoelectric device using the material as a luminescent layer. Background technique [0002] In order to improve the efficiency and lifetime of organic electroluminescent devices, compared with polymers, light-emitting small molecules are more likely to be commercialized due to fewer preparation steps, stable structures, and no disadvantages of polydispersity. The preparation of multilayer devices by evaporation or solution processing of small molecules has received great attention and great progress has been made. [0003] So far, although there have been many reports on light-emitting materials for organic electroluminescent devices, there are few reports on small organic light-emitting molecules with a thioxanthene-fluorene spiro structure as the core. Based on ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D409/14C07D409/04C07D335/04C07D417/14C07D417/04C07D409/10C07D417/10H01L51/54
Inventor 苏仕健李云川谢高瞻彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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