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Luminescent material and the preparation method thereof and organic luminous diode using the luminescent material

A technology of light-emitting diodes and light-emitting materials, applied in the fields of light-emitting materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of device efficiency limitation, etc., and achieve high decomposition temperature, high yield, good solubility and film-forming properties. Effect

Inactive Publication Date: 2017-01-11
TCL CHINA STAR OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the efficiency of devices based on traditional organic fluorescent materials is greatly limited because they can only utilize 25% of singlet excitons.

Method used

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  • Luminescent material and the preparation method thereof and organic luminous diode using the luminescent material
  • Luminescent material and the preparation method thereof and organic luminous diode using the luminescent material
  • Luminescent material and the preparation method thereof and organic luminous diode using the luminescent material

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preparation example Construction

[0048] see figure 1 , the present invention also provides a method for preparing the above-mentioned luminescent material, comprising the following steps:

[0049] Step 1, prepare intermediate

[0050] The intermediate The synthetic route of is:

[0051]

[0052]

[0053] Specifically, the step 1 includes:

[0054] Step 11, m-bromophenol reacts with 2-fluoro-4-bromobenzonitrile to obtain

[0055] The concrete implementation steps of described step 11 are:

[0056]In a 250ml three-necked flask, slowly add 0.73g (30mmol) NaH to 20ml of dry dimethylformamide (DMF) dissolved with 4.6g (25mmol) m-bromophenol, and then dropwise add 5g (25mmol) of 2 -Fluoro-4-bromobenzonitrile in 20 ml of dry dimethylformamide. Under the protection of nitrogen, heat and reflux the reaction for 20h. After the reaction is completed, it is cooled to room temperature. The reaction solution is poured into 50ml of 1M NaOH solution, extracted with dichloromethane (DCM), the solvent is remov...

Embodiment 1

[0077] Embodiment 1: intermediate Reaction with carbazole to obtain The reaction formula is as follows:

[0078]

[0079] The specific implementation steps are:

[0080] Under nitrogen protection, add 100ml toluene, 0.72g (2mmol) intermediate to the three-necked flask 0.67g (4mmol) carbazole, add 0.3g sodium tert-butyl alkoxide under stirring, then add 20mg tris(dibenzylideneacetone) dipalladium (Pd2(dba)3), then add 0.3ml 10% tri-tert-butyl Phosphine-n-hexane solution, heated to reflux, and reacted overnight. Cool down, extract the organic phase with dichloromethane, spin dry, and pass through the column. 0.68 g of a white solid product was obtained, and the yield was 65%. Molecular formula: C 37 h 22 N 2 o 2 ; M / Z=526.17; Theoretical values: 526.17 (100.0%), 527.17 (41.1%), 528.17 (8.5%), 529.18 (1.2%); Elemental analysis: C, 84.39; H, 4.21; N, 5.32; O ,6.08.

Embodiment 2

[0081] Embodiment 2: intermediate Reaction with diphenylamine by Ullmann The reaction formula is as follows:

[0082]

[0083] The specific implementation steps are:

[0084] Under nitrogen protection, add 100ml toluene, 0.72g (2mmol) intermediate to the three-necked flask 0.84g (4mmol) diphenylamine, add 0.3g sodium tert-butyl alkoxide under stirring, then add 20mg tris(dibenzylideneacetone) dipalladium (Pd2(dba)3), then add 0.3ml 10% tri-tert-butyl Phosphine-n-hexane solution, heated to reflux, and reacted overnight. Cool down, extract the organic phase with dichloromethane, spin dry, and pass through the column. 0.59 g of a white solid product was obtained, with a yield of 56%. Molecular formula: C 37 h 26 N 2 o 2 ; M / Z=530.20; Theoretical value: 530.20 (100.0%), 531.20 (40.8%), 532.21 (7.9%), 533.21 (1.2%); Elemental analysis: C, 83.75; H, 4.94; N, 5.28; O ,6.03.

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Abstract

The invention provides a luminescent material and the preparation method thereof and organic luminous diode using the luminescent material. The luminescent material has a single structure, definitive molecular weight, as well as favorable solubility and film forming property; the film formed has stable conformation; besides, the luminescent material also has a very high decomposition temperature and a comparatively low sublimation temperature, and can be easily sublimated to high-purity luminescent material, so the luminescent material can be used in small molecule organic luminous diodes. The luminescent material is prepared with m-bromophenol and 2-Fluoro-4-bromobenzonitrile as the starting material; intermediate of the luminescent material can be obtained through a series of simple reactions, and finally the luminescent material can be obtained through Ullmann reaction or Suzuki reaction. The preparation method is simple in step, but high in productivity. Luminescent layer of the organic luminous diode provided in the invention contains the luminescent material, which ensures a higher luminous efficiency and stability.

Description

technical field [0001] The invention relates to the field of display technology, in particular to a luminescent material, a preparation method thereof and an organic light emitting diode using the luminescent material. Background technique [0002] Organic Light-Emitting Diode (OLED, Organic Light-Emitting Diode) display, also known as organic electroluminescent display, is a new type of flat panel display device, due to its simple preparation process, low cost, low power consumption, high luminance, Wide range of working temperature, light and thin size, fast response speed, easy to realize color display and large-screen display, easy to realize matching with integrated circuit driver, easy to realize flexible display, etc., so it has broad application prospects. [0003] OLED displays use organic light-emitting diodes to emit light, so improving the efficiency and lifespan of organic light-emitting diodes is extremely important. So far, organic light-emitting diodes have ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/86C07D405/14C07D417/14C09K11/06H01L51/54
CPCC07D311/86C07D405/14C07D417/14C09K11/06C09K2211/1029C09K2211/1088C09K2211/1037H10K85/631H10K85/6574H10K85/6572H10K85/657H10K85/633H10K50/11
Inventor 李先杰吴元均苏仕健李云川
Owner TCL CHINA STAR OPTOELECTRONICS TECH CO LTD
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