Azabenzene modified organic compound and application thereof

An organic compound, azabenzene technology, applied in organic chemistry, electrical solid state devices, semiconductor devices, etc., can solve different problems and achieve the effect of maintaining film stability, distribution balance, and high film stability

Pending Publication Date: 2020-07-03
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Azabenzene modified organic compound and application thereof
  • Azabenzene modified organic compound and application thereof
  • Azabenzene modified organic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0069] Preparation of Intermediate I:

[0070]

[0071] In a 250mL three-necked flask, feed nitrogen, add 0.04mol of raw material A-1, 150mL of THF, 0.05mol of raw material B-1, 0.0004mol of tetrakis(triphenylphosphine) palladium, stir well, and then add 0.06mol of K 2 CO 3 Aqueous solution (2M), heated to 80 ° C, reflux reaction for 10 hours, sampling plate, reaction complete, naturally cooled, extracted with 200mL dichloromethane, separated layers, the extract was dried with anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated, Purified by silica gel column to obtain intermediate C-1; HPLC purity 99.6%, yield 80.4%. Elemental analysis structure (molecular formula C 9 h 5 Cl 2 N 3 ): theoretical value C, 47.82; H, 2.23; Cl, ​​31.36; N, 18.59; test value: C, 47.81; H, 2.23; Cl, ​​31.36; N, 18.60. ESI-MS(m / z)(M + ): The theoretical value is 224.99, and the measured value is 225.10.

[0072]

[0073] In a 250mL three-necked flask, nitrogen gas...

Embodiment 1

[0086]

[0087] In a 250mL three-necked flask, nitrogen gas was introduced, 0.01mol of raw material J-1, 150mL of THF, 0.015mol of intermediate I-1, 0.0001mol of tetrakis(triphenylphosphine) palladium were added, stirred evenly, and then 0.02mol of K 2 CO 3 Aqueous solution (2M), heated to 80 ° C, reflux reaction for 15 hours, sampling point plate, complete reaction, natural cooling, extracted with 200mL dichloromethane, separated layers, dried the extract with anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated, The target compound 1 was obtained by using petroleum ether as the eluent and purifying on a silica gel column; the HPLC purity was 99.1%, and the yield was 76.8%. Elemental analysis structure (molecular formula C 48 h 30 N 4 O): theoretical value C, 84.93; H, 4.45; N, 8.25; O, 2.36; tested value: C, 84.91; H, 4.46; N, 8.23; ESI-MS(m / z)(M + ): The theoretical value is 678.24, and the measured value is 678.25.

Embodiment 2

[0089]

[0090] Compound 1 was prepared according to the synthesis method of compound 93, except that intermediate I-1 was replaced by intermediate I-2, and the purity of target compound 1 was 99.3%, and the yield was 78.1%. Elemental analysis structure (molecular formula C 42 h 28 N 2 ): theoretical value C, 89.97; H, 5.03; N, 5.00; test value: C, 89.96; H, 5.05; N, 5.01. ESI-MS(m / z)(M + ): The theoretical value is 560.23, and the measured value is 560.21.

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PUM

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Abstract

The invention discloses an azabenzene modified organic compound and application thereof, and belongs to the technical field of semiconductors, wherein the structure of the azabenzene modified organiccompound is represented by a general formula (I). The invention also discloses application of the organic compound. The organic compound provided by the invention has good thermal stability, high glass transition temperature and appropriate HOMO energy level. A device adopting the organic compound provided by the invention can effectively improve the photoelectric property of an OLED device and prolong the service life of the OLED device through structural optimization.

Description

technical field [0001] The invention relates to an organic compound modified by azabenzene and application thereof, belonging to the technical field of semiconductors. Background technique [0002] Organic electroluminescent device technology can be used to manufacture new display products and new lighting products. It is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitting device, and the positive and negative charges in the organic layer functional material film are acted on by the electric fiel...

Claims

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Application Information

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IPC IPC(8): C07D213/06C07D213/127C07D213/16C07D213/22C07D239/26C07D251/24C07D401/04C07D401/10C07D401/14C07D403/04C07D403/10C07D405/04C07D413/04C07D413/10C07D471/04H01L51/54
CPCC07D239/26C07D213/16C07D251/24C07D405/04C07D403/04C07D401/04C07D403/10C07D213/127C07D213/06C07D471/04C07D401/14C07D213/22C07D413/10C07D401/10C07D413/04H10K85/626H10K85/615H10K85/654H10K85/6574H10K85/6572H10K85/657
Inventor 李崇谢丹丹王芳张兆超
Owner JIANGSU SUNERA TECH CO LTD
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