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Luminescent material and preparation method thereof and organic light-emitting diode using luminescent material

A technology of light-emitting diodes and light-emitting materials, which is 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 the effects of high decomposition temperature, high yield, and improved performance.

Inactive Publication Date: 2017-01-04
TCL CHINA STAR OPTOELECTRONICS TECH CO LTD
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  • Abstract
  • Description
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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 preparation method thereof and organic light-emitting diode using luminescent material
  • Luminescent material and preparation method thereof and organic light-emitting diode using luminescent material
  • Luminescent material and preparation method thereof and organic light-emitting diode using 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] Specifically, the step 1 includes:

[0053] Step 11, m-bromophenol reacts with 2-fluoro-4-bromobenzonitrile to obtain

[0054] The concrete implementation steps of described step 11 are:

[0055]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 removed under red...

Embodiment 1

[0076] Embodiment 1: intermediate Reaction with carbazole to obtain The reaction formula is as follows:

[0077]

[0078] The specific implementation steps are:

[0079] 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. 0.63 g of white solid product was obtained, the yield was 60%. 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

[0080] Embodiment 2: intermediate Reaction with diphenylamine by Ullmann The reaction formula is as follows:

[0081]

[0082] The specific implementation steps are:

[0083] 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. 0.55 g of white solid product was obtained, yield 52%. 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 a preparation method thereof and an organic light-emitting diode using the luminescent material. The luminescent material is single in structure and certain in luminescent material, is good in dissolvability and film-forming ability, and is stable in film shape. The luminescent material is high in decomposition temperature and low in sublimation temperature, can easily sublimate to a luminescent material with high purity, and can be applied to a micromolecule organic light-emitting diode. The preparation method comprises: taking 3-bromophenol and 2-fluoro-4-bromobenzonitrile as initial raw materials, carrying out a series simple reactions to obtain an intermediate of the luminescent material, and carrying out an Ullmann reaction or a Suzuki reaction to obtain the luminescent material. The method is simple in steps and high in yield. A luminescent layer of the organic light-emitting diode contains the luminescent material, and the organic light-emitting diode is high in 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): C07D405/14C07D311/86C07D417/14C09K11/06H01L51/54H10K99/00
CPCC07D311/86C07D405/14C07D417/14C09K11/06C09K2211/1029C09K2211/1088C09K2211/1037H10K85/657H10K85/6574H10K85/6572C07D405/04C09K2211/1018H10K85/636H10K50/11
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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