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Fullerene derivative containing double-benzene nucleus and preparation method and application thereof

A technology for naphthalene ring fullerenes and derivatives is applied in the fields of fullerene derivatives and their preparation and application, which can solve the problems of high synthesis temperature and limited application, and achieves simple synthesis process, high open circuit voltage, and high electron mobility. rate effect

Inactive Publication Date: 2013-02-06
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Li Yongfang and others have developed an efficient fullerene acceptor material, indene bis-addition fullerene derivative material (He, Y.J., et al., J.Am.Chem.Soc., 2010,132:1377-1382), but The synthesis temperature is relatively high, and the reaction is carried out at 200°C, which limits the application of this material

Method used

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  • Fullerene derivative containing double-benzene nucleus and preparation method and application thereof
  • Fullerene derivative containing double-benzene nucleus and preparation method and application thereof
  • Fullerene derivative containing double-benzene nucleus and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1, preparation contains naphthalene ring fullerene derivative F1

[0028] The synthetic route is as follows:

[0029]

[0030] Compound 1,2-bis(bromomethyl)naphthalene and 0.1 mmol fullerene C shown in 0.25 mmol formula II 60 Dissolve in toluene, add 0.1mmol potassium iodide and 0.05mmol 18-crown-6 ether to react at 80 ° C for 24 hours, pour the reaction solution into water, extract the aqueous phase with toluene, and dry the organic phase with anhydrous sodium sulfate. The organic solvent was removed by rotary evaporation, followed by silica gel column separation (petroleum ether:toluene=1:1.2, v / v) to obtain the powdery solid product F1 with a yield of 72%.

[0031] 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 7.19-8.58 (m, 12H), 4.12-4.78 (m, 8H).

[0032] The mass spectrum characterization of product F1 is shown in Table 1, and the measured value is close to the theoretical molecular weight; the absorption spectrum of product F1 in tetrahydrofuran is shown i...

Embodiment 2

[0035] Embodiment 2, preparation contains naphthalene ring fullerene derivative F2

[0036] The synthetic route is as follows:

[0037]

[0038] 0.1 mmol fullerene C containing 70 carbons 70 Dissolve 0.25mmol 1,2-bis(bromomethyl)naphthalene in toluene, add 0.1mmol potassium iodide, react for 2 hours at 150°C, pour the reaction solution into water, extract the aqueous phase with toluene, and wash the organic phase with anhydrous Dry over sodium sulfate, remove the organic solvent by rotary evaporation, and separate through a silica gel column (petroleum ether:toluene=1:1.5, v / v) to obtain the powdery solid product F2 with a yield of 75%.

[0039] 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 7.18-8.64 (m, 12H), 4.37-5.35 (m, 8H).

[0040] The mass spectrum characterization of product F2 is shown in Table 1, and the measured value is close to the theoretical molecular weight; the absorption spectrum of product F2 in tetrahydrofuran is shown in figure 1 , has good absorption performan...

Embodiment 3

[0041] Characterization of polymer solar cell device performance prepared by fullerene derivatives F1 and F2 prepared in embodiment 3, embodiment 1 and 2

[0042] A 25-nm thick layer of poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS) was spin-coated on cleaned indium tin oxide (ITO) conductive glass, where PEDOT : The molar ratio of PSS is 1:1, and then the fullerene derivatives and poly(3-hexylthiophene) (P3HT) prepared in Examples 1 and 2 are dissolved in o-dichloro In benzene, the total concentration of the solution is 34mg / mL, and the solution is spin-coated on the PEDOT:PSS film surface as an active layer, with a thickness of 150nm, and heat treated at 150°C for 10 minutes; metal Ca is vapor-deposited on the surface of the above-mentioned active layer, The thickness is 20nm, the metal Al is vapor-deposited on the surface of the metal Ca, the thickness is 150nm, and the organic solar cell is obtained.

[0043] The performance of the organic solar cell ...

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Abstract

The invention discloses a fullerene derivative containing double-benzene nucleus and a preparation method and an application thereof. The fullerene derivative containing double-benzene nucleus has structure shown as follows, has good solubility, high lowest unoccupied molecular orbital (LUMO) energy level, and high electron mobility. The fullerene derivative containing double-benzene nucleus can be applied to fields of organic solar batteries, organic field-effect transistors and organic photoconductor and the like.

Description

technical field [0001] The invention relates to a fullerene derivative containing a naphthalene ring, a preparation method and application thereof, and belongs to the field of fullerene derivatives and the preparation and application thereof. Background technique [0002] Fullerenes and their derivatives are widely used in electronic devices such as organic solar cells, organic field effect transistors, and organic photoconductors. Among them, fullerene C 60 The derivative [6,6]-benzene-carbon 61-butyric acid methyl ester (PCBM) is a commonly used acceptor material in organic solar cells (Yu, G., et al., Science, 1995,270:1789-1791 ). A series of fullerene derivatives have been obtained through chemical modification of fullerene carbon cages, especially double-addition fullerene derivative materials have attracted extensive attention of researchers. Compared with single-addition fullerene derivatives, double-addition fullerene derivatives can effectively weaken the conjuga...

Claims

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Application Information

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IPC IPC(8): C07C13/62C07C1/26H01L51/30H01L51/46
CPCY02E10/549Y02P70/50
Inventor 王春儒孟祥悦蒋礼舒春英
Owner INST OF CHEM CHINESE ACAD OF SCI
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