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Amino modified fullerene derivative, and preparation method and application thereof

A technology for fullerene derivatives and fullerenes, which can be used in the preparation of amino compounds by condensation/addition reactions, semiconductor/solid-state device manufacturing, photovoltaic power generation, etc. and other problems, to achieve the effect of simple synthesis method and improved stability

Active Publication Date: 2015-01-07
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the reported fullerenes have many and complicated synthesis steps and are not suitable for purification. These reasons all result in high costs and are not conducive to their real application.

Method used

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  • Amino modified fullerene derivative, and preparation method and application thereof
  • Amino modified fullerene derivative, and preparation method and application thereof
  • Amino modified fullerene derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1, preparation of N, N-methyl-1,3-diaminopropane addition of C60 fullerene (ie DMAPA-C60) shown in formula III

[0053] Under a nitrogen atmosphere, C60 fullerene (100 mg, 0.138 mmol) was mixed with the primary amine derivative N, N-methyl-1, 3-diaminopropane (R 1 for -CH 2 CH 2 CH 2 -, R 2 for -CH 3 ) (5.00g, 48.9mmol) was dissolved in toluene solution (5.0mL), heated to reflux for nitrogen-hydrogen addition reaction for 12 hours. Cool to room temperature and remove low boiling point solvents on a rotary evaporator. Add n-hexane for precipitation, and filter to collect the precipitate to obtain the light yellow target polymer. Yield 80%.

[0054] Depend on figure 1 It can be seen from the infrared spectrum that the characteristic peaks of the addition substituent and the characteristic peaks of the fullerene carbon cage appear in the final product.

[0055] figure 2 The cyclic voltammogram of DMAPA-C60 shows that the lowest empty orbital energy level...

Embodiment 2

[0062] Embodiment 2, the preparation of N shown in formula IV, the C60 fullerene (that is DMAEA-C60) of N-dimethylethylenediamine addition

[0063] Under a nitrogen gas atmosphere, C60 fullerene (100mg, 0.138mmol) was mixed with the primary amine derivative N,N-methylethylenediamine (R 1 for -CH 2 CH 2 -, R 2 for -CH 3 ) (4.31g, 48.9mmol) was dissolved in toluene solution (5.0mL), heated to reflux for nitrogen-hydrogen addition reaction for 12 hours. Cool to room temperature and remove low boiling point solvents on a rotary evaporator. After adding n-hexane, the light yellow target polymer was obtained after filtration. Yield 80%.

[0064] The structure confirmation results of the product are as follows:

[0065] 1 H NMR (400MHz, CDCl 3 ), δ (ppm): 4.2-1.8 (br, 20H), 1.26-1.24 (br, 4H), 1.21-1.19 (br, 24H).

[0066] Elemental analysis (C, N) showed m to be 4.

[0067] It can be seen from the above that the product has a correct structure and is a compound shown in f...

Embodiment 3

[0068] Example 3, the preparation of N, N-diethylethylenediamine-added C60 fullerene (that is, DEAPA-C60) shown in formula V

[0069] Under a nitrogen atmosphere, C60 fullerene (100mg, 0.138mmol) was mixed with the primary amine derivative N,N-ethylethylenediamine (R 1 for -CH 2 CH 2 -, R 2 for -CH 2 CH 3 ) (5.68g, 48.9mol) was dissolved in toluene solution (5.0mL), heated to reflux for nitrogen-hydrogen addition reaction for 12 hours. Cool to room temperature and remove low boiling point solvents on a rotary evaporator. Add n-hexane for precipitation, and filter to collect the precipitate to obtain the light yellow target polymer. Yield 80%.

[0070] From the NMR and infrared detection results of the product, it can be seen that the product has a correct structure and is a compound shown in formula V, and elemental analysis (C, N) shows that m is 4.

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Abstract

The invention discloses an amino modified fullerene derivative, and a preparation method and an application of the amino modified fullerene derivative. The derivative is represented by the formula I, in the formula I, R1 and R2 both are C1-C10 alkyl, m is 1 to 50; the synthetic method of the amino modified fullerene derivative is simple; and the work function of a high-work-function metal electrode can be effectively regulated and controlled, therefore the high-work-function metal is likely to be used as an electrode; in the photovoltaic field, the performance of a modification layer in which Ca is replaced by the fullerene derivative is slightly higher than the performance of a Ca / Al device, therefore the amino modified fullerene derivative has significant application value.

Description

technical field [0001] The invention relates to an amino-modified fullerene derivative, a preparation method and application thereof. Background technique [0002] In the field of organic semiconductors, in order to improve electron injection or collection, metals with low work function such as Ca / Al are usually used as cathodes. However, these low work function metals are unstable in the air and easily react with water and oxygen in the air. In addition, these metals need to be vacuum evaporated, which is not conducive to the realization of full solution processing of organic semiconductor devices, so people began to look for organic electron buffer layer materials that can realize solution processing to replace low work function Ca. (H.-L.Yip, A.K.Y.Jen , Energy Environ. Sci. 2012, 5, 5994). In addition, the outstanding advantage of organic electronic buffer materials is the strong controllability of chemical structure (F. Huang, H. Wu, Y. Cao, Chem. Soc. Rev. 2010, 39, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/41C07C209/60H01L51/46
CPCY02E10/549
Inventor 张志国王吉政李永舫
Owner INST OF CHEM CHINESE ACAD OF SCI