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A kind of phenanthroline organic small molecule cathode interface material and preparation method thereof

A cathode interface, phenanthroline technology, applied in organic chemistry, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve the problems of high processing cost, crystalline silicon hardness, high melting point, application limitations, etc. function, good light transmittance, and the effect of improving photoelectric conversion efficiency

Active Publication Date: 2022-03-29
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, relatively mature photovoltaic cells are mainly made of inorganic single / polycrystalline silicon thin film materials, and have been commercialized, but their energy conversion efficiency has reached more than 20%, which has entered the bottleneck, and because of the high hardness and melting point of crystalline silicon, the processing cost is high. , the application is very limited

Method used

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  • A kind of phenanthroline organic small molecule cathode interface material and preparation method thereof
  • A kind of phenanthroline organic small molecule cathode interface material and preparation method thereof
  • A kind of phenanthroline organic small molecule cathode interface material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Synthesis of N,N'-bis(5-phenanthroline)-3,4,9,10-perylimide

[0037]

[0038] In a 250mL two-necked round bottom flask, add 3,4,9,10-perylenetetracarboxylic dianhydride (1g, 2.55mmol), 5-amino-1,10-phenanthroline (2g, 10.24mmol), 80g imidazole and zinc acetate (93mg, 0.51mmol), blown with nitrogen for 10 minutes, heated to 160°C and stirred for 6 hours. After the reaction, a sufficient amount of water was added to precipitate, and the filter residue was obtained by filtration, washed with 2 wt % sodium hydroxide solution, and finally recrystallized with dimethyl sulfoxide to obtain a dark red solid. Mass(MALDI-TOF): Obs.747.07; Calcd.For C 48 h 22 N 6 o 4 ,746.74.

[0039] (2) Synthesis of N,N'-bis(5-phenanthroline)-3,4,9,10-perylimide dicarbobromide ion

[0040]

[0041] In an argon atmosphere, N,N'-bis(5-phenanthroline)-3,4,9,10-perylimide (207mg, 0.28mmol) was added to a 50ml two-necked round-bottomed flask, and then 15ml1, 2-Dibromoethane, protected...

Embodiment 2

[0047] (1) Synthesis of N,N'-bis(5-phenanthroline)-1,4,5,8-naphthalimide

[0048]

[0049] In a 250mL two-neck round bottom flask, add 1,4,5,8-naphthalene tetracarboxylic dianhydride (379mg, 1.41mmol), 5-amino-1,10-phenanthroline (827g, 4.24mmol) and 25g imidazole , Then add 50ml of pyridine and stir to dissolve, blow with nitrogen for 10 minutes, heat to 130°C and stir for 8h. After the reaction, the reaction solution was poured into 300ml of glacial acetic acid and stirred for 1 h, then enough water was added to continue stirring for 1 h, the solid was obtained by filtration, and then recrystallized with dimethyl sulfoxide to obtain a light gray solid. Mass(MALDI-TOF): Obs.623.23; Calcd.For C 38 h 18 N 6 o 4 ,622.60.

[0050] (2) Synthesis of N,N'-bis(5-phenanthroline)-1,4,5,8-naphthalimide dicarbobromide ion

[0051]

[0052] In an argon atmosphere, add N,N'-bis(5-phenanthroline)-1,4,5,8-naphthalimide (100mg, 0.16mmol) into a 50ml two-necked round-bottomed flask...

Embodiment 3

[0058] Synthesis of N,N'-bis(5-phenanthroline)-3,4,9,10-perylimide tricarbonyl bromide

[0059]

[0060] In an argon atmosphere, N,N'-bis(5-phenanthroline)-3,4,9,10-perylimide (207mg, 0.28mmol) was added to a 50ml two-necked round-bottomed flask, and then 15ml1, 3-Dibromopropane, protected from light, heated up to 150°C, and reacted for 6h. After the reaction was completed, a sufficient amount of tetrahydrofuran was added to precipitate a solid, and then recrystallized with dimethyl sulfoxide to obtain a dark red solid. Mass(MALDI-TOF): Obs.1151.43; Calcd.ForC 52 h 30 Br 4 N 6 o 4 ,1150.52.

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PUM

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Abstract

The invention discloses a phenanthroline organic small molecule cathode interface material and a preparation method thereof. The material takes an N-type conjugated acid anhydride group as the core, connects phenanthroline groups at both ends of the conjugated ring, and uses 2 ‑6 carbon terminal dibrominated linear alkanes to ionize it, and then perform anion exchange with an ion exchange resin. The method uses N-type conjugated anhydride groups as raw materials, first reacts with 5-amino-1,10-phenanthroline, then reacts with 2-6 carbon-terminal dibrominated straight-chain alkanes, and finally passes ion The exchange resin is exchanged for anions to obtain phenanthroline organic small molecule cathode interface materials with different ions. The phenanthroline organic small molecule cathode interface material of the present invention improves the π-π stacking between molecules of the material in the film-forming state, thereby improving the electron transport performance; improving the solubility of the material in polar solvents, and utilizing the present invention The invented material can further improve the photoelectric conversion efficiency of solar cells.

Description

technical field [0001] The invention relates to the field of cathode interface materials, in particular to a phenanthroline organic small molecule cathode interface material and a preparation method thereof. Background technique [0002] With the development of society and economy, energy consumption is increasing, and traditional fossil energy is increasingly exhausted. The development of renewable energy has become an important research topic for current researchers. As a kind of green energy, solar energy is inexhaustible and inexhaustible. It is one of the new energy sources developed and utilized by scientists from all over the world. The use of photovoltaic cells to convert solar energy into electrical energy has become one of the most effective technologies for utilizing solar energy. In 1954, Bell researchers in the United States successfully developed silicon solar cells for the first time, which set off a trend in photoelectric conversion research. At present, re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00H01L51/46
CPCY02E10/549
Inventor 彭小彬周莹黄思雨祝蓓邓科
Owner SOUTH CHINA UNIV OF TECH
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