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Luminescent material and preparation method thereof and organic light emitting diode using same

A technology for 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, and achieve the effects of high decomposition temperature, high yield, and molecular weight determination.

Inactive Publication Date: 2016-09-28
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 same
  • Luminescent material and preparation method thereof and organic light emitting diode using same
  • Luminescent material and preparation method thereof and organic light emitting diode using same

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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 p-bromophenol with 2-fluoro-4-bromobenzonitrile to obtain

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

[0055] In a 250ml three-neck flask, slowly add 0.73g (30mmol) NaH into 20ml of dry dimethylformamide (DMF) dissolved with 4.6g (25mmol) of p-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 ...

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. 0.65 g of white solid product was obtained, the yield was 61%. 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. 0.76 g of white solid product was obtained, the yield was 65%. Molecular formula: C 37 h 26 N 2 o 2 ; M / S=530.2; Theoretical value: 530.61, elemental analysis: 530.20 (100.0%), 531.20 (40.8%), 532.21 (7.9%), 533.21 (1.2%).

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Abstract

The invention provides a luminescent material and a preparation method thereof and an organic light emitting diode using the same. The luminescent material provided by the invention has a single structure, determined molecular weight, relatively good solubility and film forming property while the film form is stable; and with very 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-molecule organic light emitting diode. In the preparation method of the luminescent material provided by the invention, p-bromophenol and 2-fluoro-4-bromobenzonitrile are used as start raw materials, an intermediate of the luminescent material is obtained through a series of simple reactions, and finally, the luminescent material is obtained through Ullman reaction or Suzuki reaction; and the steps are simple, and the yield is high. In the organic light emitting diode provided by the invention, a luminescent layer contains the luminescent material and has relatively high luminescent 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
CPCC07D311/86C07D405/14C07D417/14C09K11/06C09K2211/1088C09K2211/1037C09K2211/1029C09K2211/1014C09K2211/1007H10K85/636H10K85/631H10K85/6574H10K85/6572H10K85/657C07D405/04C07D405/10C07D417/10
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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