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

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

Pending Publication Date: 2016-12-07
TCL CHINA STAR OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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

[0057] see figure 1 , the present invention also provides a method for preparing the above-mentioned luminescent material, comprising the following steps:

[0058] Step 1, prepare intermediate

[0059] The intermediate The synthetic route of is:

[0060]

[0061] Specifically, the step 1 includes:

[0062] Step 11, react m-bromothiophenol with 2-fluoro-4-bromobenzonitrile to obtain

[0063] The concrete implementation steps of described step 11 are:

[0064] 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

[0090] Embodiment 1: intermediate Compound P6 was obtained by Ullmann reaction with carbazole.

[0091] The synthetic route of described compound P6 is as follows:

[0092]

[0093] The concrete implementation steps of described embodiment 1 are:

[0094] 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. 0.77 g of white solid product was obtained, the yield was 67%. Molecular formula: C 37 h 22 N 2 o 3 S; M / Z=574.14; Theoretical values: 574.14 (100.0%), 575.14 (40.4%), 576.14 (9.2%), 576.13 (4.5%), 577.13 (1.8%), 575.13 (1.5%), 577.15 (1.0 %); elemental analysis: C, 77.33; H,...

Embodiment 2

[0096] Embodiment 2: intermediate Compound P10 was obtained by Ullmann reaction with 9,9-dimethylacridine.

[0097] The synthetic route of the compound P10 is as follows:

[0098]

[0099] The concrete implementation steps of described embodiment 2 are:

[0100] Under nitrogen protection, add 100ml toluene, 0.72g (2mmol) intermediate to the three-necked flask 0.84g (4mmol) 9,9-dimethylacridine, add 0.3g sodium tert-butyl alkoxide under stirring, then add 20mg tris(dibenzylideneacetone) dipalladium (Pd2(dba)3), then add 0.3ml of 10% tri-tert-butylphosphine-n-hexane solution was heated to reflux and reacted overnight. Cool down, extract the organic phase with dichloromethane, spin dry, and pass through the column. 0.78 g of white solid was obtained, yield 62%. Molecular formula: C 43 h 34 N 2 o 3S; M / Z=658.23; Theoretical values: 658.23 (100.0%), 659.23 (48.2%), 660.24 (10.8%), 660.22 (4.5%), 661.23 (2.2%), 661.24 (2.0%), 660.23 (1.3 %); elemental analysis: C, 78....

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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 has the advantages of single structure, definite molecular weight, relatively good solubility and film-forming property, and stable thin film morphology; the luminescent material has quite high decomposition temperature and relatively low sublimation temperature, is easily sublimated into a luminescent material with high purity, and can be applied to the small-molecular organic light emitting diode. According to the preparation method of the luminescent material, m-bromothiophenol and 2-fluoro-4-bromobenzonitrile are used as starting raw materials, an intermediate of the luminescent material is obtained through a series of simple reactions, and finally, the luminescent material is obtained through an Ullmann reaction or a Suzuki reaction; the steps are simple, and the yield is high. A luminescent layer of the organic light emitting diode contains the luminescent material and has relatively high 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): C07D409/14C07D335/16C07D417/14C09K11/06H01L51/54
CPCC07D335/16C07D409/14C07D417/14C09K11/06C09K2211/1092C09K2211/1037C09K2211/1029C09K2211/1007H10K85/631H10K85/636H10K85/6576H10K85/657H10K85/6572H10K50/11C09K2211/1018H10K2101/10
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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