Check patentability & draft patents in minutes with Patsnap Eureka AI!

Indolo[3, 2, 1-jk]carbazole derivative, preparation method and application thereof, and electronic device

A carbazole derivative, 1-jk technology, applied in the direction of electric solid-state devices, electrical components, semiconductor devices, etc., can solve the problems of high cost, increased business cost, complex synthesis and purification steps, etc., to reduce costs and reduce production Effect of cost, high thermal stability

Inactive Publication Date: 2019-09-20
SUZHOU UNIV
View PDF2 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these commonly used hole-transporting materials usually have relatively complicated synthesis and purification steps and high costs, which increase commercial costs.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Indolo[3, 2, 1-jk]carbazole derivative, preparation method and application thereof, and electronic device
  • Indolo[3, 2, 1-jk]carbazole derivative, preparation method and application thereof, and electronic device
  • Indolo[3, 2, 1-jk]carbazole derivative, preparation method and application thereof, and electronic device

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0044] The present invention also provides a method for preparing the indolo[3,2,1-jk]carbazole derivatives, comprising the following steps:

[0045] Compounds according to the present invention can be prepared by synthetic procedures known to those of ordinary skill in the art, such as bromination, Suzuki coupling, Hartwig-Buchwald coupling, and the like.

[0046] The synthesis of compounds of the present invention usually starts from indolo[3,2,1-jk]carbazole derivatives functionalized at positions 2, 5 and 11, followed by metal-catalyzed coupling reactions such as Suzuki coupling or cloth Hartwig-Buchwald coupling introduces 3 R groups.

[0047] In a preferred embodiment of the present invention, the phenyltricarbazole spiro derivative is a halogen functional compound and the R group is derived from a boronic acid derivative functional compound.

[0048] In the second preferred embodiment of the present invention, the indolo[3,2,1-jk]carbazole derivative is a halogen-funct...

Embodiment 1

[0068] The structural formula and synthetic route of compound 1-21 are shown in the figure below:

[0069]

[0070] In a 100mL two-necked flask, add 0.5g (1.1mmol) M3, 1.4g (4.0mmol) 4,4'-dimethoxy-4"-triphenylamine borate, 1.7g (16.0mmol) sodium carbonate, 40mL toluene, 6.4 mL of ethanol, 8 mL of water. After the mixture was bubbled with nitrogen for 30 minutes, 0.06 g (0.05 mmol) of tetrakis (triphenylphosphine) palladium catalyst was added, and heated and stirred overnight at 106 ° C. After the reaction was cooled to room temperature, the mixture Dilute with water (50mL) and ethyl acetate (50mL). Then extract the aqueous layer with ethyl acetate 100mL×3. After the organic phase is dried with anhydrous sodium sulfate, it is spin-dried to remove the solvent to obtain a crude product. Use petroleum ether: ethyl acetate =4:1 (volume ratio) was used as an eluent solvent to carry out separation and purification on a silica gel column to obtain 1.20 g of a green solid with a yi...

Embodiment 2

[0072] The structural formulas and synthetic routes of compounds 1-9 are shown in the figure below:

[0073]

[0074] In a 250mL two-necked flask, 1.1g (2.3mmol) M3, 1.9g (8.2mmol) 4,4'-dimethoxy-diphenylamine, 0.8g (8.2mmol) sodium tert-butoxide, 0.1g (0.3mmol) ) tri-tert-butylphosphine tetrafluoroborate, 0.27g (0.3mmol) tris(dibenzylideneacetone) dipalladium, after degassing the reaction system, under the protection of nitrogen, add 150mL toluene, stir and heat to 106°C for 12 hours . After the reaction was complete, the system was cooled to room temperature, filtered under reduced pressure, and the filter residue was washed with a large amount of dichloromethane, and the filtrate was concentrated to obtain a crude product, which was eluted with petroleum ether:ethyl acetate=3:1 (volume ratio) The reagent was separated and purified on a silica gel column to obtain 1.9 g of 1-9 with a yield of 92%. MS (MALDI-TOF): m / z 922.3 [M+]. Elemental analysis calculated value C 6...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to an indolo[3, 2, 1-jk]carbazole derivative, a preparation method and application thereof, and an electronic device. The indolo[3, 2, 1-jk]carbazole derivative has a hole mobility up to 6.5*10<-4>cm<2>V<-1>S<-1>, also can be applied as a hole transport material in solar cell devices, and can effectively inhibit energy consumption and improve the energy conversion efficiency, device life, electric current density, filling factor, threshold voltage and other performance of solar cell devices.

Description

technical field [0001] The invention relates to an indolo[3,2,1-jk]carbazole derivative, its preparation method, application and electronic device, and belongs to the technical field of organic photoelectric materials. Background technique [0002] Since 2009, perovskite solar cells (PeSCs) have attracted much attention and developed rapidly due to their wide and strong absorption bands, long exciton diffusion distances, and high photoelectric conversion efficiencies. At present, the energy conversion efficiency of perovskite solar cells based on the solution method has exceeded 23% and the stable working time in the atmospheric environment has exceeded 1000 hours. These results fully demonstrate the great potential of perovskite solar cells. [0003] The structure of a perovskite battery mainly includes an active layer (perovskite layer), a hole transport layer, and an electron transport layer. The hole transport layer plays a role in extracting and transporting holes and ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D487/06C09K11/06H01L51/42H01L51/46
CPCC07D487/06C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037H10K85/636H10K85/631H10K85/6572H10K85/657H10K30/10Y02E10/549
Inventor 廖良生蒋佐权朱向东
Owner SUZHOU UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com