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Organic compound with symmetrical iso-substituted aza-spirobifluorene structure and application thereof

An organic compound, azaspiro technology, applied in the field of organic electroluminescent elements, can solve the problems of insufficient carrier transport and thermal stability, improve the glass transition temperature and thermal stability, and is not easy to crystallize Good effect of chemical and film forming

Pending Publication Date: 2021-03-23
CHANGZHOU TRONLY EARLY OPTOELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The main purpose of the present invention is to provide an organic compound with a symmetrical heterosubstituted azaspirobifluorene structure to solve the problem of insufficient performance of spirobifluorene derivatives in the prior art in terms of carrier transport and thermal stability

Method used

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  • Organic compound with symmetrical iso-substituted aza-spirobifluorene structure and application thereof
  • Organic compound with symmetrical iso-substituted aza-spirobifluorene structure and application thereof
  • Organic compound with symmetrical iso-substituted aza-spirobifluorene structure and application thereof

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preparation example Construction

[0053] The preparation process of the above organic electroluminescent element can be used:

[0054] Method 1, by means of sublimation method to apply one or more layers, where the degree of vacuum in the vacuum sublimation device should usually be less than 10 -5 Mbar, preferably less than 10 -6 The primary pressure of mbar is deposited, in order to ensure the life of the device, it is also preferred to be less than 10 -7 The primary pressure of millibar.

[0055] Second, one or more layers are applied by OVPD (organic gas deposition) method or by means of carrier gas sublimation, thereby at 10 -5 Application of materials under pressure of mbar to 1 bar. Specific embodiments of this method are OVJP (organic vapor print) method, and the material is applied directly through the nozzle.

[0056] Method 3, by spin coating, or by means of any desired printing method such as screen printing, flexographic printing, nozzle printing or lithographic printing, particularly preferably LITI (...

preparation Embodiment 1-1

[0094]

[0095] Synthetic steps:

[0096] The experimental unit was sufficiently dried, and D1 22.8 g (40 mmol) and N-phenylnaphthalene-1-amine 9.6 g (44 mmol) were added to 500 ml of four-mouth flask, and then 300 ml of dry and degassed toluene were added. 5.8 g (60 mmol) tert-butanol sodium, 0.75 g (0.8 mmol) PD 2 (DBA) 3 The catalyst was raised to 80 ° C, slowly added 2 ml of a concentration of 10% to a tetra-t-butylphosphine / toluene solution, and then heated to 100-105 ° C, and the reaction was 6 h. At the end of the reaction, cooled to room temperature, diluted with toluene, pad 200-300 silica gel filtration, the filtrate was evaporated to the solvent, resulting in a crude product, and the crude toluene and n-hexane mixed solvent were recrystallized, resulting in 23.1 g Object 1-1, yield It was 71%, and the purity of HPLC was 99.71%, and finally the vacuum sublimated twice, HPLC purity was 99.99%; MS [M + H] + = 758.42.

preparation Embodiment 1-2

[0098]

[0099] The compounds 1-4 were prepared using the same synthesis of compound 1-1, and the N-phenyl-[1,1'-biphenyl] -3-amine is used in the use of N-phenyl-[1,1'-biphenyl-1-amine. . The yield was 67%, HPLC purity was 99.56%, and finally the vacuum sublimation was purified twice, HPLC purity was 99.99%; MS [M + H] + = 784.42.

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Abstract

The invention provides an organic compound with a symmetrical iso-substituted aza-spirobifluorene structure and application thereof. The organic compound with a symmetrical iso-substituted aza-spirobifluorene structure has a structure shown as a formula (1). According to the compound, aza-spirobifluorene is taken as a main body, and different arylamine groups are introduced into symmetrical positions, so that the glass-transition temperature and the thermal stability of the compound are improved. Meanwhile, the compound has relatively high carrier transport capability. The compound is suitablefor a fluorescent or phosphorescent OLED, especially a phosphorescent OLED device, can be used as a matrix material of a hole injection layer, a hole transport layer, an electron blocking layer or alight emitting layer, and is helpful for improving the efficiency and prolonging the service life of the device. In addition, synthesis and purification of the compound are simple, crystallization isnot prone to occurring during evaporation, and the film-forming property is good.

Description

Technical field [0001] The present invention relates to the field of organic electroluminescent elements, in particular, to an organic compound having a symmetrical differential nitrogen thief dihydrazine structure. Background technique [0002] An organic electroluminescent element (OLED) typically has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Here, the organic material layer typically includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. The device performance of OLED is closely related to the physical chemical nature of these organic materials. These functional materials have strong selectivity and require reasonable matching to achieve optimized device performance. At present, the organic compounds developing different functions are still the focus of research, and the deve...

Claims

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Application Information

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IPC IPC(8): C07D221/20C07D405/12C07D409/12C07D417/04H01L51/50H01L51/54
CPCC07D221/20C07D405/12C07D409/12C07D417/04H10K85/615H10K85/626H10K85/657H10K85/6574H10K85/6576H10K85/6572H10K50/00
Inventor 蒋建兴孙霞王仁宗孙杰
Owner CHANGZHOU TRONLY EARLY OPTOELECTRONICS MATERIAL CO LTD
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