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Organic compound based on azabenzene and benzoheterocycle, and preparation method and application of organic compound

A technology of organic compounds and benzoheterocycles, which is applied in the fields of organic chemistry, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the problems affecting the angular distribution of OLED radiation spectrum and complex manufacturing process, etc., so as to improve the light extraction efficiency Effect

Inactive Publication Date: 2020-08-25
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first two structures will affect the angular distribution of the radiation spectrum of the OLED. The third structure is complicated to manufacture, and the process of using a surface covering layer is simple, and the luminous efficiency is increased by more than 30%, which is particularly concerned by people.

Method used

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  • Organic compound based on azabenzene and benzoheterocycle, and preparation method and application of organic compound
  • Organic compound based on azabenzene and benzoheterocycle, and preparation method and application of organic compound
  • Organic compound based on azabenzene and benzoheterocycle, and preparation method and application of organic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: the synthesis of compound 1:

[0068]

[0069] In a 250mL three-necked flask, nitrogen gas was introduced, 0.02mol of raw material A-1, 150ml of DMF, 0.024mol of raw material B-1 and 0.0002mol of palladium acetate were added, stirred, and then 0.03mol of K 3 PO 4 The aqueous solution was heated to 130°C, refluxed for 10 hours, sampled and plated, and the reaction was complete. Natural cooling, adding water, filtering the mixture and drying in a vacuum oven, the resulting residue was purified by silica gel column to obtain compound intermediate M-1;

[0070] In a 250mL three-necked flask, nitrogen gas was introduced, 0.01mol of intermediate M-1, 150ml of DMF, 0.03mol of raw material C-1 and 0.0002mol of palladium acetate were added, stirred, and then 0.03mol of K 3 PO 4 Aqueous solution, heated to 130°C, refluxed for 24 hours, sampled and plated, the reaction was complete. Cool naturally, add water, filter the mixture and dry in a vacuum oven, and th...

Embodiment 2

[0071] Embodiment 2: the synthesis of compound 5:

[0072]

[0073] Prepared by the synthetic method of compound 1 in embodiment 1, difference is to replace raw material A-1 with raw material A-2, raw material C-2 replaces raw material C-1; Elemental analysis structure (molecular formula C 50 h 35 N 3 o 2 S 2 ): Theoretical value: C, 77.59; H, 4.56; N, 5.43; O, 4.13; S, 8.28; HPLC-MS: The molecular weight of the material is 773.22, and the measured molecular weight is 773.95.

Embodiment 3

[0074] Embodiment 3: the synthesis of compound 9:

[0075]

[0076] Prepare by the synthetic method of compound 1 in embodiment 1, difference is to replace raw material C-1 with raw material C-3; Elemental analysis structure (molecular formula C 53 h 40 N 2 S 4 ): theoretical value: C, 76.41; H, 4.84; N, 3.36; S, 15.39; test value C, 76.41; H, 4.85; N, 3.36; HPLC-MS: The molecular weight of the material is 832.21, and the measured molecular weight is 832.22.

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Abstract

The invention discloses an organic compound based on azabenzene and benzoheterocycle, and a preparation method and application of the organic compound, belonging to the technical field of semiconductors. The structure of the compound provided by the invention is as shown in a general formula (1) which is described in the specification. The invention also discloses application of the organic compound. The structure of the compound contains an azabenzene structure, so the compound has high glass transition temperature and molecular thermal stability, is low in absorption and high in refractive index in the field of visible light, and can effectively improve the light extraction efficiency of an OLED device after being applied to a CPL layer of the OLED device. The compound disclosed by the invention also has a deep HOMO energy level and high electron mobility; and the compound can be used as a hole blocking / electron transport layer material of the OLED device, and can effectively block holes or energy from being transmitted from a light emitting layer to one side of an electron layer, thereby improving the recombination efficiency of the holes and electrons in the light emitting layer, and thus, the light emitting efficiency and the service life of the OLED device are improved.

Description

technical field [0001] The invention relates to an organic compound based on azabenzene and a benzoheterocycle, a preparation method and an application thereof, and belongs to the technical field of semiconductors. Background technique [0002] At present, OLED (Organic Light Emission Diodes) display technology has been applied in smart phones, tablet computers and other fields, and will further expand to large-size applications such as TVs. However, due to the huge gap between the external quantum efficiency and internal quantum efficiency of OLEDs, the development of OLEDs is greatly restricted. Therefore, how to improve the light extraction efficiency of OLEDs has become a research hotspot. Total reflection will occur at the interface between the ITO film and the glass substrate and the interface between the glass substrate and the air, and the light emitted to the front of the OLED device to the external space accounts for about 20% of the total EL of the organic materi...

Claims

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Application Information

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IPC IPC(8): C07D405/14C07D411/14C07D409/14C07D413/14C07D417/14C07D419/14C09K11/06H01L51/50H01L51/52H01L51/54
CPCC07D405/14C07D411/14C07D409/14C07D413/14C07D417/14C07D419/14C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1048C09K2211/1051C09K2211/1059C09K2211/1088C09K2211/1092H10K85/6565H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/18H10K50/16H10K50/85
Inventor 徐浩杰陈海峰李崇王芳张兆超
Owner JIANGSU SUNERA TECH CO LTD
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