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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 problems such as device efficiency limitations, achieve high decomposition temperature, improve performance, and stabilize the shape of thin films

Inactive Publication Date: 2016-12-07
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 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, react m-bromothiophenol 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 into 20ml of dry dimethylformamide (DMF) dissolved with 4.7g (25mmol) m-bromothiophenol, and then dropwise add 5g (25mmol) of NaH dissolved therein ) 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), ...

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. 0.65 g of white solid product was obtained, the yield was 60%. Molecular formula: C 37 h 22 N 2 OS; M / Z=542.15; Theoretical values: 542.15 (100.0%), 543.15 (40.3%), 544.15 (8.7%), 544.14 (4.5%), 545.14 (1.8%), 543.14 (1.5%), 545.16 (1.0 %); elemental analysis: C, 81.89; H, 4.09; N, 5.16; O, 2.95; S, 5.91.

Embodiment 2

[0080] Embodiment 2: intermediate Reaction with 9,9-dimethylacridine to obtain 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) of 9,9-dimethylacridine, add 0.3g sodium tert-butyl alkoxide under stirring, then add 20mg tris(dibenzylideneacetone) dipalladium (Pd2(dba)3), and then Add 0.3ml of 10% tri-tert-butylphosphine n-hexane solution, heat to reflux, and react 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, with a yield of 54%. Molecular formula: C 43 h 34 N 2 OS; M / Z=626.24; Theoretical values: 626.24 (100.0%), 627.24 (48.1%), 628.25 (10.8%), 628.23 (4.5%), 629.24 (2.2%), 629.25 (1.8%); Elemental analysis: C, 82.40; H, 5.57; N, 4.47; O, 2.55; S, 5.12.

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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 has a single structure and definite molecular weight and is higher in solubility and film-forming property, and the form of a thin film is stable; with extremely high decomposition temperature and relatively low sublimation temperature, the luminescent material can be easily sublimated into a high-purity luminescent material and can be applied to a small-molecular organic light emitting diode. According to the preparation method of the luminescent material, m-bromine thiophenol and 2-fluorine-4-benzonitrile bromide serving as start raw materials are subjected to a series of simple reactions to obtain a middle body of the luminescent material, and finally the middle body is subjected to a Ullmann reaction or a Suzuki reaction to obtain the luminescent material; the steps are simple, and the yield is high. According to the organic light emitting diode provided by the invention, a light emitting layer contains the luminescent material, so that the organic light emitting diode is higher in light emitting 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): C09K11/06C07D409/14C07D335/16C07D417/14H01L51/50H01L51/54H10K99/00
CPCC07D335/16C07D409/14C07D417/14C09K11/06C09K2211/1029C09K2211/1037C09K2211/1092H10K85/656H10K85/6576H10K85/6572H10K85/657H10K50/11C07D409/04C07D409/10C07D417/10H10K85/631
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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