Spiro[fluorene-9,9'-xanthene]-based small organic molecule hole transport material as well as preparation method and application thereof

A hole transport material, xanthene technology, applied in the field of solar cell materials, can solve the problems of low photoelectric conversion efficiency of all-inorganic perovskite, and achieve the advantages of improving photoelectric conversion efficiency and current density, low cost, and improved stability. Effect

Pending Publication Date: 2021-01-22
NANCHANG HANGKONG UNIVERSITY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] Aiming at the problem of low photoelectric conversion efficiency of all-inorganic perovskites in the prior art, the purpose of the present invention is to provide a kind of oligothiophene derivatives with good hydrophobicity and organic solubility. Transmission material, used in perovskite solar cells, has matching energy levels, can absorb red light, and can greatly improve the current density and photoelectric conversion efficiency of perovskite solar cells

Method used

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  • Spiro[fluorene-9,9'-xanthene]-based small organic molecule hole transport material as well as preparation method and application thereof
  • Spiro[fluorene-9,9'-xanthene]-based small organic molecule hole transport material as well as preparation method and application thereof
  • Spiro[fluorene-9,9'-xanthene]-based small organic molecule hole transport material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of small organic molecule hole transport material SFX-THIO1 based on spiro[fluorene-9,9′-xanthene]:

[0027]

[0028] 2,2′,7,7′-Tetrabromospiro[fluorene-9,9′-oxanthene](1)

[0029] Under nitrogen protection, 4-bromophenol (17.3g, 100mmol), 2,7-dibromo-9-fluorenone (3.38g, 10mmol) and methanesulfonic acid d=1.48g / ml, 2.6ml, 3.84g , 40mmol) into a 250ml double-necked flask, nitrogen pumped three times with a double-row tube, then heated and stirred at 150°C for 24 hours, the reaction was cooled to room temperature, and 100ml of methanol solution was slowly added to the mixture, until the white After the crystals were precipitated, they were filtered and washed with a large amount of methanol to obtain white crystals of Compound 1, 5.9 g (yield 91%).

[0030] 1 H NMR (500MHZ, CDCl 3 )δ:8.00(d,2H),7.69(d,2H),7.48(d,2H),7.43(s,2H),7.30(d,2H),6.53(s,2H). 13 C NMR: 151.49, 137.21, 135.20, 134.42, 133.31, 131.14, 130.60, 122.53, 120.29, 116.70.

[0031] 2-Hexy...

Embodiment 2

[0041] Synthesis of small organic molecule hole transport material SFX-THIO2 based on spiro[fluorene-9,9′-xanthene]:

[0042]

[0043] 2,2′,7,7′-Tetrabromospiro[fluorene-9,9′-oxanthene](1)

[0044] Under nitrogen protection, 4-bromophenol (17.3g, 100mmol), 2,7-dibromo-9-fluorenone (3.38g, 10mmol) and methanesulfonic acid (d=1.48g / ml, 2.6ml, 3.84 g, 40mmol) was added to a 250ml double-necked flask, nitrogen pumping was carried out three times with a double-row pipe, and then heated and stirred at 150°C for 24 hours, the reaction was cooled to room temperature, and 100ml of methanol solution was slowly added to the mixture, and the After the white crystals were precipitated, they were filtered and washed with a large amount of methanol to obtain 5.9 g of white crystals of compound 1 (yield 91%).

[0045] 1 H NMR (500MHZ, CDCl 3 )δ:8.00(d,2H),7.69(d,2H),7.48(d,2H),7.43(s,2H),7.30(d,2H),6.53(s,2H). 13 C NMR: 151.49, 137.21, 135.20, 134.42, 133.31, 131.14, 130.60, 122.53, 12...

Embodiment 3

[0056] Synthesis of small organic molecule hole transport material SFX-THIO2 based on spiro[fluorene-9,9′-xanthene]:

[0057]

[0058] 2,2′,7,7′-Tetrabromospiro[fluorene-9,9′-oxanthene](1)

[0059] Under nitrogen protection, 4-bromophenol (17.3g, 100mmol), 2,7-dibromo-9-fluorenone (3.38g, 10mmol) and methanesulfonic acid (d=1.48g / ml, 2.6ml, 3.84 g, 40mmol) was added to a 250ml double-necked flask, nitrogen pumping was carried out three times with a double-row pipe, and then heated and stirred at 150°C for 24 hours, the reaction was cooled to room temperature, and 100ml of methanol solution was slowly added to the mixture, and the After the white crystals were precipitated, they were filtered and washed with a large amount of methanol to obtain 5.9 g of white crystals of compound 1 (yield 91%).

[0060] 2-Hexyl-5-(5-(thiophene-2-yl)thiophene-2-yl)thiophene (6)

[0061] Under the condition of nitrogen protection, 16g of 2,5-bis(thiophene-2-yl)thiophene and 200mL of anhydrou...

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Abstract

The invention discloses an organic small molecule hole transport material based on spiro[fluorene-9,9'-xanthene]-based and a preparation method and application thereof, and the organic small moleculehole transport material takes spiro[fluorene-9,9'-xanthene] as a core, and has good amorphous form and excellent dissolving property; besides, different numbers of thiophene groups are added into sidechains, so that the material is endowed with more excellent physical and photoelectric properties through the characteristics of high electron density, excellent carrier transport capacity, controllable optical and electrochemical properties and the like; in addition, due to modification of a terminal alkyl chain, the dissolvability is improved, the film-forming property of the material is facilitated, and the material is easier to process; meanwhile, the synthesis is simple, raw materials are easy to obtain, and cost is low. The organic small molecule hole transport material is applied to anall-inorganic perovskite solar cell, and the cell efficiency of the organic small molecule hole transport material is higher than the original cell efficiency, which shows that the organic small molecule hole transport material has practical significance for improving the efficiency of the all-inorganic perovskite solar cell.

Description

technical field [0001] The invention relates to the technical field of solar cell materials, in particular to a small organic molecule hole transport material based on spiro[fluorene-9,9'-xanthene] and its preparation method and application. Background technique [0002] Since Professor Tsutomu Miyasaka of Toin University of Yokohama first reported perovskite solar cells in 2009, through the improvement of materials and the optimization of device structure, the research of perovskite solar cells has made a major breakthrough, which is currently the closest to commercialization. Third generation solar cells. In the perovskite solar cell structure, the hole transport material is very important and is one of the key factors affecting the performance of the cell. Among them, the small molecule HTMS has been widely used in high-efficiency perovskite solar cells due to its key role in charge carrier transport and charge recombination retardation. So far, the amorphous organic sp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14H01L51/42H01L51/46
CPCC07D409/14H10K85/655H10K85/6574H10K30/151Y02E10/549
Inventor 张余宝宫动飞阳敏任福梦
Owner NANCHANG HANGKONG UNIVERSITY
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