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P-phenyl diether dithienyl organic photoelectric compound and preparing method and application thereof

A technology of hydroquinone dithiophene and p-phenylene ether, which is applied in the field of p-phenylene dithiophene organic photoelectric compounds and its preparation, can solve the problems of difficult synthesis, restrictions on the commercialization of organic solar cells, and high cost, and achieve good results. Planarity and conjugation degree, simple structure, strong electron donating ability

Active Publication Date: 2016-10-12
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

((d) Yongsheng Chen*, Xiangjian Wan, and Guankui Long. High Performance Photovoltaic Applications Using Solution-Processed Small Molecules[J]. Accouts of Chemical Research, 2013, 46, 2645-2655.) Such fused ring units are difficult to synthesize , The disadvantage of high cost, which limits the commercialization of organic solar cells

Method used

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  • P-phenyl diether dithienyl organic photoelectric compound and preparing method and application thereof
  • P-phenyl diether dithienyl organic photoelectric compound and preparing method and application thereof
  • P-phenyl diether dithienyl organic photoelectric compound and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Synthesis of Example 1 Compound 2a

[0075]

[0076] 2-(Trimethyltin)-thiophene (10.19 g, 41.26 mmol) and compound la (6.00 g, 13.75 mmol) were dissolved in redistilled toluene (70 ml). Add catalyst Pd(PPh 3 ) 4 (795 mg,) and the solution was degassed three times. At 100°C, stirred and refluxed for 48h, concentrated by rotary evaporation, and petroleum ether / ethyl acetate (9:1) was used as eluent to pass through the column to obtain compound 2a as a light yellow solid (4.3g, 9.71mmol, yield: 71%). 1 H NMR (400MHz, Chloroform-d) δ7.53 (dd, J = 3.7, 1.2Hz, 2H), 7.33 (dd, J = 5.1, 1.2Hz, 2H), 7.25 (s, 2H), 7.09 (dd, J=5.2,3.7Hz,2H),4.08(t,J=6.6Hz,4H),1.96–1.83(m,4H),1.58–1.47(m,4H),1.42–1.32(m,9H),0.91 (td, J=5.8, 4.8, 2.9Hz, 6H).

Embodiment 2

[0077] Synthesis of Example 2 Compound 2b

[0078]

[0079] The synthetic method of compound 2b is the same as that of 2a in Example 1, the only difference is that compound 1a is replaced by 1b, and the amount of compound 1b is (8.00g, 16.25mmol), to obtain compound 2b (12.10g, 24.58mmol, yield Yield: 82%), white powder. 1 HNMR (400MHz, Chloroform-d): δ7.54 (dd, J = 3.6, 1.1Hz, 2H), 7.34 (dt, J = 5.2, 1.0Hz, 2H), 7.12–7.08 (m, 2H), 4.08 ( t,J=6.5Hz,4H), 1.96–1.85(m,4H), 1.59–1.47(m,4H), 1.44–1.22(m,18H), 0.90(t,J=6.6Hz,6H).

Embodiment 3

[0080] Example 3 Synthesis of compound CNO2TPDT

[0081]

[0082] Including the following steps:

[0083] (1) Synthesis of compound 3a

[0084] Compound 2a (4.00 g, 9.04 mmol) was dissolved in anhydrous THF (90 ml) at -78°C under the protection of argon. Then n-BuLi (22.6mmol, 9.4ml, 2.4M in THF) was added dropwise. After stirring at -78°C for 1 hour, the liquid nitrogen acetone bath was removed and stirred at room temperature for 1 hour. Then the solution was cooled to -78°C, trimethyltin chloride (27.12mmol, 13.56ml, 2.0M THF solution) was added dropwise, and the reaction was carried out at -78°C for 1 hour. The cooling bath was then removed and stirred overnight at room temperature. After quenching with water, it was extracted with petroleum ether. The organic phase was washed with water and washed with anhydrous MgSO 4 dry. Concentrated and rotary evaporated to obtain compound 3a (3.50g, 4.56mmol, yield: 50%), which was a light green solid containing a certain am...

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Abstract

The invention provides a p-phenyl diether dithienyl organic photoelectric compound and a preparing method and application thereof. The p-phenyl diether dithienyl organic photoelectric compound has a structure which is shown in a formula (IV) in the description. The organic photoelectric compound can be applied to preparation of various kinds of devices like solar cells, organic field effect transistor and organic light emitting diodes. The p-phenyl diether dithienyl organic photoelectric compound has weak interaction force between oxygen atoms on a benzene ring and sulphur atoms on a thiophene ring and can well improve the planarity and the conjugation of molecules. The photoelectric converting efficiency of the p-phenyl diether dithienyl organic photoelectric compound can reach 6.64%, the short-circuit current can reach 12.74mA cm<-2>, and the fill factor can reach 67.6%.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to a p-phenylenediethdithiophene organic photoelectric compound, its preparation method and application. Background technique [0002] Organic solar cells have the advantages of simple process, low cost, low energy density, and can be fabricated into flexible devices, so they have attracted extensive attention ((a) Günes S, Neugebauer H, Sariciftci N S. Conjugated polymer-based organic solar cells[J] .ChemRev,2007,107(4):1324-38.(b)Krebs F C, M, Norrman K, et al. A complete process for production of flexible large area polymer solar cells entirely using screen printing—first public demonstration [J]. SolEnergy Mater Sol Cells, 2009, 93(4): 422-41.). Organic solar cells are mainly divided into polymer organic solar cells and small molecule organic solar cells. Among them, the small molecule organic battery has the advantages of definite molecular structure, high puri...

Claims

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Application Information

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IPC IPC(8): C07D333/16C07D333/24C07D417/14C07D409/14H01L51/54H01L51/46
CPCC07D333/16C07D333/24C07D409/14C07D417/14H10K85/655H10K85/656Y02E10/549
Inventor 魏志祥赵俊珏吕琨房进
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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