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SO2 multi-heterocyclic structure compound and application thereof

A compound and heterocyclic technology, applied in the field of materials for organic electroluminescence, can solve the problems of high device operating voltage, few types of electron transport materials, low electron mobility, etc.

Active Publication Date: 2020-09-15
北京燕化集联光电技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the development of organic charge transport materials, there are many kinds of hole transport materials and good performance, while there are few varieties of electron transport materials and poor performance.
For example, the currently commonly used electron transport material Alq3 has a low electron mobility, which leads to a high operating voltage of the device and serious power consumption; some electron transport materials such as LG201 have a low triplet energy level. When using phosphorescent materials as the light-emitting layer, It is necessary to increase the exciton blocking layer, otherwise the efficiency will decrease; there are also some materials such as Bphen, which are easy to crystallize, resulting in a decrease in lifetime
These problems in electron transport materials are the bottlenecks affecting the development of organic electroluminescent display devices

Method used

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  • SO2 multi-heterocyclic structure compound and application thereof
  • SO2 multi-heterocyclic structure compound and application thereof
  • SO2 multi-heterocyclic structure compound and application thereof

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Experimental program
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preparation example Construction

[0046] According to the preparation method provided by the present invention, those skilled in the art can use known common means to realize, such as further selecting suitable catalysts, solvents, determining suitable reaction temperature, time, material ratio, etc., the present invention is not particularly limited to this . Unless otherwise specified, the solvents, catalysts, bases and other raw materials used in the preparation process can be synthesized through open commercial channels or methods known in the art.

[0047] Synthetic intermediates M1~M10

[0048] Synthesis of intermediate M1

[0049]

[0050] The synthetic route is as follows:

[0051]

[0052] The specific operation steps are:

[0053] (1) In a 2L three-necked flask equipped with mechanical stirring, add 4-chloro-1-fluoro-2-nitrobenzene (17.5g, 0.1mol), 2-bromo-4-chloroaniline (30.8g, 0.15mol ), stirred, protected by argon, heated up to 180°C, and kept warm for more than 30 hours. During the rea...

Embodiment 1

[0105]

[0106] The synthetic route is as follows:

[0107]

[0108] The synthesis of compound I-1 comprises the following specific steps:

[0109] Take a 2L three-necked flask, equipped with a magnetic stirrer, add M1 (43.4g, 0.1mol), phenylboronic acid (36.6g, 0.3mol), cesium carbonate (117g, 0.36mol) and 800ml of dioxane in turn after nitrogen replacement, and start stirring . After nitrogen replacement again, (2.2 g, 11 mmol) tri-tert-butylphosphine and (4.1 g, 4.5 mmol) tris(dibenzylideneacetone) dipalladium were added. After the addition, heat up to raise the temperature, control the temperature at 80-90°C for 4 hours, and cool down after the reaction. Adjust to neutral, separate the organic phase, extract, dry, perform column chromatography, and spin dry the solvent to obtain 40.3 g of light yellow solid with a yield of about 72%.

[0110] Product MS (m / e): 560.16; Elemental analysis (C 37 h 24 N 2 o 2 S): theoretical value C: 79.26%, H: 4.31%, N: 5.00%; me...

Embodiment 2

[0112]

[0113] The synthetic route is as follows:

[0114]

[0115] Synthesis of compound I-8: replace M1 with M2, replace phenylboronic acid with 3,4-dimethylphenylboronic acid, select a suitable material ratio, and other raw materials and steps are the same as in Example 1 to obtain 42.7 g of a light yellow solid. The rate is about 79%.

[0116] Product MS (m / e): 540.19; Elemental analysis (C 35 h 28 N 2 o 2 S): theoretical value C: 77.75%, H: 5.22%, N: 5.18%; measured value C: 77.49%, H: 5.00%, N: 4.96%.

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Abstract

The invention relates to the technical field of organic electroluminescent display, particularly discloses an organic material of an SO2 polyheterocyclic structure compound, and also discloses application of the organic material in an organic electroluminescent device. The SO2 polyheterocyclic structure compound provided by the invention is shown as a general formula (I), can be applied to the field of organic electroluminescence, and can be used as an electron transport material. The compound with the structure provided by the invention is applied to an OLED device, the driving voltage of thedevice can be reduced, and the light emitting efficiency of the device is improved.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence materials, and specifically discloses a novel SO 2 The multi-heterocyclic compound also discloses its application in organic electroluminescent devices. Background technique [0002] The application of organic electroluminescent (OLED) materials in information display materials, organic optoelectronic materials and other fields has great research value and bright application prospects. With the development of multimedia information technology, the performance requirements of flat panel display devices are getting higher and higher. At present, the main display technologies include plasma display devices, field emission display devices and organic electroluminescence display devices (OLEDs). Among them, OLEDs have a series of advantages such as self-luminescence, low-voltage DC drive, light and thin power saving, full curing, wide viewing angle, and rich colors. Compared with ...

Claims

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Application Information

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IPC IPC(8): C07D513/04H01L51/54H01L51/50
CPCC07D513/04H10K85/622H10K85/623H10K85/624H10K85/626H10K85/615H10K85/657H10K50/16
Inventor 梁现丽程丹丹范洪涛段陆萌杭德余曹占广班全志陈婷
Owner 北京燕化集联光电技术有限公司
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