Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Organic hole transport material taking phenanthroimidazole as parent nucleus and application thereof

A hole transport material, phenanthroimidazole technology, applied in the field of solar cells, can solve the problems of the application of perovskite cells with upright structure

Active Publication Date: 2020-10-23
TIANJIN UNIVERSITY OF TECHNOLOGY
View PDF5 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] One of the objectives of the present invention is to solve the problem that organic hole transport materials cannot be used in both positive structure perovskite batteries and reverse structure perovskite batteries, and provide a class of organic hole transport materials with phenanthroimidazole as the core ;

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
  • Organic hole transport material taking phenanthroimidazole as parent nucleus and application thereof
  • Organic hole transport material taking phenanthroimidazole as parent nucleus and application thereof
  • Organic hole transport material taking phenanthroimidazole as parent nucleus and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthetic route of organic hole transport material PI-1 with phenanthrimidazole as the core:

[0039]

[0040] 1) Synthesis of dibromophenanthrimidazole derivative VI

[0041] Add 3,6-dibromophenanthrenequinone (1010mg, 2.74mmol), p-aniline (410mg, 3.29mmol), 4-di-p-methoxyanilinobenzaldehyde (915.55mg, 2.74mmol) and Ammonium acetate (2120mg, 27.48mmol), acetic acid (35ml) as solvent, reflux for 24 hours under nitrogen protection, quench with water, wash with suction, and separate by column chromatography to obtain crude dibromophenanthrimidazole derivative VI , Directly vote the next step.

[0042] 2) Synthesis of organic hole transport material PI-1 with phenanthroimidazole as the core

[0043] 300mg of dibromophenanthrimidazole derivative VI (300mg, 0.51mmol), 4,4’-dimethoxydiphenylamine (350mg, 1.53mmol), Pd 2 (dba) 3 (30mg, 0.06mmol), ligand Xphos (31mg, 0.12mmol) and base t-BuONa (245mg, 2.04mmol), 20mL anhydrous toluene as solvent. The resulting solution was refluxed a...

Embodiment 2

[0047] The synthetic route of the organic hole transport material PI-2 with phenanthrimidazole as the core:

[0048]

[0049] 1) The synthesis of dibromophenanthrimidazole derivative VI is the same as in Example 1

[0050] 2) Synthesis of organic hole transport material PI-2 with phenanthrimidazole as the core

[0051] Add (314mg, 0.4mmol) bromophenanthrimidazole derivative VI, 4-borate-4', 4'-dimethoxytriphenylamine (437mg, 1mmol), Pd(PPh 3 ) 4 (89.2mg, 0.08mmol), add 15ml of ethylene glycol dimethyl ether (DME) as solvent, in N 2 Stir for 5 minutes under atmosphere. Subsequently, 415 mg of potassium carbonate was weighed, and the solution obtained by adding 3 ml of water was added dropwise to the mixture. Continue heating to reflux for 13 hours. It was quenched with water, washed with suction, and finally separated by column chromatography to obtain 321 mg of the organic hole transport material PI-2 with phenanthrimidazole as the core, with a yield of 65.2%.

Embodiment 3

[0053] The synthetic route of the organic hole transport material PI-3 with phenanthrimidazole as the core:

[0054]

[0055] 1) The synthesis of dibromophenanthrimidazole derivative VI is the same as in Example 1

[0056] 2) Synthesis of organic hole transport material PI-3 with phenanthroimidazole as the core

[0057] Add dibromophenanthrimidazole derivative VI (100mg, 0.13mmol), 4,4’-dimethylthiodiphenylamine (100mg, 0.38mmol), Pd to the reaction flask in sequence 2 (dba) 3 (7mg, 0.008mmol), ligand Xphos (8mg, 0.0016mmol) and base t-BuONa (60mg, 0.06mmol), 10mL anhydrous toluene as solvent. The resulting solution was refluxed and stirred for 12 hours under the protection of nitrogen. Cool, add water to quench the reaction, extract, separate and dry the crude product, and distill under reduced pressure to remove the solvent. Finally, 125 mg of the organic hole transport material PI-3 with phenanthrimidazole as the core was obtained by column chromatography, and the yield was 84%....

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

PropertyMeasurementUnit
Glass transition temperatureaaaaaaaaaa
Open circuit voltageaaaaaaaaaa
Short circuit current densityaaaaaaaaaa
Login to View More

Abstract

The invention discloses an organic hole transport material taking phenanthroimidazole as a parent nucleus and application thereof. The compound takes triarylamine or carbazole as an electron donatingunit, takes imidazole with the characteristics of an electron donor and an electron acceptor as a parent nucleus, and has a structure shown in a structural formula (PI). The molecule is easy to synthesize and simple in process. The molecules have good thermal stability, have the characteristics of both electron donors and electron acceptors, and can effectively balance charge transfer. The molecules have the characteristics of Lewis base, and the prepared hole film has good morphological stability, can effectively passivate the interface of a perovskite layer and a hole transport layer, and can generate effective transfer of intramolecular holes. The compound can be used as a hole transport material in a perovskite solar cell, is applied to a positive structure perovskite solar cell and anegative structure perovskite solar cell, and shows excellent photoelectric conversion performance.

Description

Technical field [0001] The invention belongs to the technical field of solar cells, and relates to a phenanthroimidazole-based compound and its application, and specifically, to a preparation method and application of an organic small molecule using phenanthrimidazole as a core. Background technique [0002] Solar cells are one of the main technologies for using solar energy. Perovskite solar cells (JACS, 2009, 131(17): 6050.) are the third-generation solar cells. Since their inception, they have been used in the development of clean and green energy due to their easy preparation, low cost, and high-efficiency photoelectric conversion efficiency. And environmental protection field, showing strong commercial application prospects. [0003] At present, perovskite solar cells are classified according to their structures, which are mainly divided into upright structure perovskite solar cells (n-i-p) and inverted perovskite solar cells (p-i-n). At present, hole transport materials sui...

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): C07D235/02C07D403/14C07D409/14H01L51/42H01L51/46
CPCC07D235/02C07D403/14C07D409/14H10K85/655H10K85/636H10K85/6572H10K30/00Y02E10/549
Inventor 薛松程杨宗雪平罗明岑荣浩
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com