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Organic small molecular photoelectric functional material, and preparation method thereof

A technology of optoelectronic functional materials and small molecules, which can be used in luminescent materials, photovoltaic power generation, organic chemistry, etc. It can solve the problems of low photoelectric conversion efficiency of organic solar cells, and achieve the effects of strong absorption, improved solubility, and large open circuit voltage.

Active Publication Date: 2015-11-04
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the photoelectric conversion efficiency of organic solar cells based on porphyrin and its derivatives is very low

Method used

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  • Organic small molecular photoelectric functional material, and preparation method thereof
  • Organic small molecular photoelectric functional material, and preparation method thereof
  • Organic small molecular photoelectric functional material, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1C16

[0036] The synthesis of embodiment 1C16TPTRD

[0037] Step 1: Synthesis of 15,15-bis(5-(2-hexyldecyl)thiophene)porphyrin

[0038]

[0039] In a 1000mL two-necked round bottom flask, add 5-(2-hexyldecyl)thiophene-2-carbaldehyde (1.632g, 4.86mmol), bipyrromethane (700mg, 4.86mmol) and 500mL of dichloromethane, and ventilate with nitrogen 30 minutes, then add 0.25mL of trifluoroacetic acid, stir the reaction at room temperature for 12 hours, then add 1.8g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), continue The reaction was stirred for 12 hours, and then 5 mL of triethylamine was added to quench the reaction. After the reaction, the crude product was obtained by column chromatography on silica gel / (dichloromethane as eluent) and spin-dried, and then recrystallized by chloroform / methanol to obtain a dark red solid. 1 H NMR (300MHz, CDCl 3 )δ10.27(s,2H),9.35(q,8H),7.74(d,2H),7.20(d,2H),3.09(d,4H),1.93(m,2H),1.61-1.25(m ,48H), 0.95-0.82(m,12H),-2.96(s,2H).

[0040] S...

Embodiment 2

[0058] Synthesis of Example 2 C16TPPRD

[0059]

[0060] Under the protection of argon, 5,15-bis(acetylene)-10,20-bis(3,5-bis(dodecyloxy)benzene)zinc porphyrin (262mg ,0.2mmol), 4-bromobenzene-2-(3-ethyl)rhodanine (196.2mg, 0.6mmol), anhydrous toluene (10mL), triethylamine (5mL), cuprous iodide (8mg, 0.04 mmol) and tetrakis(triphenylphosphine)palladium (24mg, 0,02mmol), protected from light, stirred and reacted at 80°C for three days. After the reaction was completed, it was cooled to room temperature, washed with water, extracted with toluene, dried over anhydrous sodium sulfate, spin-dried, and passed through a column to obtain a purple-black solid. Mass(MALDI-TOF): Obs.1806.3; Calcd.for C 108 h 134 N 6 o 6 S 4 Zn, 1805.9.

Embodiment 3

[0061] The synthesis of embodiment 3PorEFDPP

[0062]

[0063] Under the protection of argon, 5,15-bis(acetylene)-10,20-bis(3,5-bis(dodecyloxy)benzene)zinc porphyrin (262mg , 0.2mmol), monobromobisfuropyrrolopyrrole diketone (342mg, 0.6mmol), anhydrous toluene (10mL), triethylamine (5mL), cuprous iodide (8mg, 0.04mmol) and tetrakis (tri Phenylphosphine)palladium (24mg, 0,02mmol), protected from light, stirred and reacted at 80°C for three days. After the reaction was completed, it was cooled to room temperature, washed with water, extracted with toluene, dried over anhydrous sodium sulfate, spin-dried, and passed through a column to obtain a purple-black solid. Mass(MALDI-TOF): Obs.2013.6; Calcd.for C 124 h 156 N 8 o 8 S 2 Zn, 2013.2.

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PUM

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Abstract

The invention discloses an organic small molecular photoelectric functional material. The organic small molecular photoelectric functional material containing porphyrin units and different dye units is prepared via selection of a plurality of dyes, and taking acetylenic bonds or aromatic ring or heterocyclic aromatic as bridges. According to a preparation method, the organic small molecular photoelectric functional material is prepared via Suzuki coupling reaction or Sonogashira coupling reaction. The organic small molecular photoelectric functional material possesses excellent processability, and appropriate energy band structures, and is high in energy conversion efficiency.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to an organic small molecule photoelectric functional material and a preparation method thereof. Background technique [0002] Solar energy has the characteristics of cleanness and extensive resources, and is considered to be the preferred resource to replace petrochemical resources. The development and utilization of solar energy has attracted more and more attention from human beings. However, the energy density of solar energy is low, and it is not easy to use it directly. It needs to be converted into other energy sources to make better use of it. In the effective use of solar energy, the use of photovoltaic cells to convert solar energy into electrical energy is one of the fastest-growing and most dynamic research fields in recent years. [0003] Solution-processable organic solar cells have potential advantages such as low cost, easy processing (such as spin-coa...

Claims

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Application Information

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IPC IPC(8): C07D487/22C07D519/00C09K11/06H01L51/46
CPCC09K11/06C07D487/22C07D519/00C09K2211/1037C09K2211/1029C09K2211/1088C09K2211/1096C09K2211/1092H10K85/655H10K85/656H10K30/00H10K85/6572Y02E10/549
Inventor 彭小彬高珂梁天祥杨冰琳肖练钢李立胜曹镛
Owner SOUTH CHINA UNIV OF TECH
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