Polyceptor-structure small molecule compound and preparing method and application thereof

A technology of small molecular compounds and compounds, applied in semiconductor/solid-state device manufacturing, organic chemistry, electric solid-state devices, etc., can solve the problems of small-molecule photovoltaic materials that are rarely reported, and achieve improved planar configuration and high photoelectric conversion efficiency Effect

Inactive Publication Date: 2016-02-10
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its application in small molecule photovoltaic materials is rarely reported

Method used

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  • Polyceptor-structure small molecule compound and preparing method and application thereof
  • Polyceptor-structure small molecule compound and preparing method and application thereof
  • Polyceptor-structure small molecule compound and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1 provides the synthesis of a photovoltaic multi-acceptor structure small molecule compound with an M-1 structure,

[0058]

[0059] Concrete synthetic route is:

[0060]

[0061] The specific steps are:

[0062] (1) (5-(2,5-bis((2-butyloctyl)oxy)-4-(thiophen-2-yl)phenyl)thiophen-2-yl)trimethyltin (compound 2 )Synthesis:

[0063] Add 2,2'-(2,5-bis((2-butyloctyl)oxy)-1,4-phenylene)dithiophene (compound 1) (1.53g, 2.5 mmol) and 40mL of anhydrous tetrahydrofuran were stirred and dissolved; the solution was cooled to -78°C in a nitrogen atmosphere, and a n-hexane solution of n-butyllithium (2.4M, 1.04mL, 2.5mmol) was slowly added dropwise, and reacted at this temperature for 1 Hours; then rise to room temperature and react for 1 hour; cool to -78°C, add trimethyltin chloride in tetrahydrofuran solution (1.0M, 2.5mL, 2.5mmol) in one go, react for 1 hour; rise to room temperature and react for 3 hours After that, pour into water to quench;

[0064] After...

Embodiment 2

[0085] Embodiment 2 provides the synthesis of a photovoltaic multi-acceptor structure small molecule compound with M-2 structure,

[0086]

[0087] Concrete synthetic route is:

[0088]

[0089] The specific steps are:

[0090] (1) Synthesize (5-(2,5-bis((2-butyloctyl)oxy)-4-(thiophen-2-yl)phenyl)thiophene-2- according to Example 1 step (1) base) trimethyltin (compound 2)

[0091] (2) 4-(5-(2,5-bis((2-butyloctyl)oxy)-4-(thiophen-2-yl)phenyl)thiophen-2-yl)-7-bromo- Synthesis of 5,6-fluorobenzene[c][1,2,5]thiadiazole (Compound 5):

[0092] Add compound 2 (3.87g, 5mmol), 4,7-dibromo-5,6-difluorobenzo[c][1,2,5]thiadiazole (1.65g, 5mmol) into a dry 250mL three-necked flask , 120mL THF, and Pd(PPh 3 ) Cl 2 (105mg, 0.15mmol); Stir to dissolve, use a vacuum pump to pump nitrogen gas 3 times; heat up to 70°C for 24 hours; cool to room temperature and spin evaporate directly, and rinse with dichloromethane:petroleum ether (1:5) Pass through a silica gel column to obtain an ...

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Abstract

The invention relates to a polyceptor-structure small molecule compound. The compound is of the structure as shown in the formula I or formula II. In the formula I or formula II, A is an electrondrawing group containing carbonyl, cyanogroup, ester group and acylamino, and D and D' are respectively selected from any one kind of aromatic group containing thiophene. The compound is of a conjugated structure based on 5,6-difluoro benz-[c][1,2,5] thiadiazole. Conjugation between A and D is achieved through carbon-carbon double bonds to generate an intense charge transfer effect. Meanwhile, sulphur atoms containing nitrogen atoms, fluorine atoms and a thiophene ring are weak in interaction, so that the planar structure of a molecule can be improved greatly, and photoelectric converting efficiency as high as 9.34% and fill factors higher than 0.7 can be obtained.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and relates to a small molecular compound with a multi-acceptor structure, a preparation method and an application, in particular to a compound containing 5,6-difluorobenzo[c][1,2,5]thiadiazole Small organic molecules with multi-acceptor conjugated structures, preparation methods and applications in the field of organic photovoltaic technology. Background technique [0002] Organic solar cells have received widespread attention because of their advantages such as simple preparation process, low cost, light weight, and flexibility. .(b) Molecular Design of Photovoltaic Materials for Polymer Solar Cells: Toward Suitable Electronic Energy Levels and Broad Absorption. Yongfang Li*, Accouts of Chemical Research, 2012, 45, 723-733.). In the research of organic photovoltaic materials, small molecule materials have been widely studied due to their advantages of clear chemical structure, hi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14H01L51/46
CPCC07D417/14H10K85/657H10K30/00Y02E10/549
Inventor 魏志祥袁柳
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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