Derivatives of fullerenes, method for their preparing and photovoltaic device

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to novel derivatives of fullerenes comprising organic amines and hydrogen atoms bound to fullerene-C60 molecule by 6,6-double bonds of the general formula: C60Hn(R1R2N)n wherein R1 means -C6H5CH2; R2 means -C6H5CH2; n = 4 (tetra-(dibenzylaminohydro)[60]fullerene); R1 means -C5H9; R2 means hydrogen atom (H); n = 3 (tri-(cyclopentylaminohydro)[60]fullerene). Also, invention relates to using derivatives of fullerenes, in particular, (tetra-(benzylaminohydro)[60]fullerene, (tetra-(dibenzylaminohydro)[60]fullerene, tri-(cyclopentylaminohydro)[60]fullerene, 2-(azahomo[60]fullereno)-5-nitropyrimidine, 1,3-dipropyl-5-[5'-(azahomo[60]fullereno)pentyl]-1,3,5-triazin-2,4,6(1H,3H,5H)-trione, O,O-dibutyl-(azahomo[60]fullereno)phosphate as acceptors of electrons in composites polymer/fullerene designated for photovoltaic cells. Also, invention relates to photovoltaic device comprising mixture of poly-conjugated polymer and abovementioned fullerene derivative or their mixture as an active layer. Also, invention relates to a method for synthesis of derivatives of fullerenes comprising aromatic amines and hydrogen atoms bound to fullerene-C60 molecule by 6,6-double bonds. Method involves interaction of C60 with the corresponding organic amine in solution, and this reaction is carried out in aromatic solvent medium in amine excess at temperature 25-70°C for 2-5 days followed by evaporation of solution and precipitation of the end product by addition of alcohol.

EFFECT: improved method of synthesis.

6 cl, 1 tbl, 2 dwg, 6 ex

 

The invention relates to compounds of carbon, namely, the derivative of fullerene, intended for use in semiconductor devices sensitive to electromagnetic radiation, particularly in photovoltaic solar cells.

It is known that a semiconductor device containing a thin layer of organic conjugated polymer poly(2-methoxy-5-(2'-ethylhexyloxy)-1,4-phenylenevinylene (MEH-PPV), placed between the metal electrode and the transparent electrode of conductive indium oxide-tin (ITO) has photosensitivity (photovoltaic effect) and can be used to convert the energy of electromagnetic radiation into electrical energy [U.S. Patent 5504323 (1996)]. It is known that the efficiency of such a photovoltaic Converter can be significantly improved by the introduction of an additional unit of the organic layer adjacent to a layer of MEH-PPV and consisting of a fullerene (e.g., With60) [U.S. patent 5331183 (1994); U.S. Patent 5454880 (1995)]. The increased efficiency is due to the fact that generated by photoexcitation of the polymer charge carriers (electrons) in the photoinduced transfer transferred to the fullerene molecule having a good acceptor properties, which, in turn, leads to a more efficient division of electricallyheated, formed at photogeneration [U.S. Patent 5331183 (1994); .Lee et al. Phys. Rev. V.48, p.15425-15433 (1993)]. Another consequence of the transfer of photoexcited electrons from the polymer to the fullerene is the quenching of photoluminescence of the polymer [U.S. Patent 5331183 (1994)]. Thus, the quenching of photoluminescence of the polymer may serve as an indicator of the efficiency of interaction of fullerene with the polymer.

Efficiency photvoltaics device system based on polymer/fullerene can be further enhanced if, instead of a two-layer device (film polymer - fullerene film) used a single-layer device, in which the active layer consists of a mixture of the polymer and fullerene. In this case, the interaction of polymer-fullerene occurs not only on the surface, but also in the volume of the film, which increases the number of interacting molecules and, consequently, increases the efficiency of charge separation. The composite films containing a mixture of the polymer with fullerene as an electron acceptor can be prepared by the method of irrigation from a solution containing the polymer and the fullerene in the required proportions. However, the preparation of films containing fullerene C60difficult due to the lack of high solubility60in the usual solvents. Another problem arising in the preparation of composite films of poly is EP/fullerene, morphological compatibility of the polymer and fullerene components. For efficient charge transfer to the acceptor is required, in particular, a large surface of contact between the polymer and fullerene, which is determined by the internal structure (morphology) of the composite polymer/fullerene [C.J.Brabec et al. Monatchefte fur Chemie, v.132, p.421 (2001)]. This raises the problem of finding derivatives of fullerenes with high enough, high solubility, high electron-acceptor ability (at least not worse than those With60) and is characterized by high efficiency of charge transfer in the composite polymer/fullerene.

It is known that photoinduced charge transfer from the polymer to the fullerene leads to quenching of photoluminescence of the polymer [U.S. Patent 5331183 (1194); L.Smilowitz et al., Phys. Rew. v.B47, 13835 (1193)]. The presence of properties quenching of photoluminescence of the polymer is a necessary condition for the application of the fullerene derivative as the electron acceptor in the composite system polymer/fullerene [N.S.Sariciftci, Materials Today, Sept.2004, p.36]. Therefore, the efficiency of charge transfer in composites of polymer/fullerene can be measured by the intensity of photoluminescence of the polymer concentration of the fullerene in the composite. In the absence of spatial difficulties to contact fullerene molecules with molecules of the polymer increases Konz is Tracii fullerene will lead to a reduction in luminescence intensity.

Closest to the proposed invention is a photovoltaic device containing as an active layer of a mixture (compound) of conjugated polymer poly(2-methoxy-5-(2'-ethylhexyloxy)-1,4-phenylenevinylene (MEH-PPV) and fullerene derivative methyl ester [6,6]-phenyl-C61-butyric acid (RSVM) in the ratio 1:4, is placed between the electrodes of the ITO and aluminum [F.L.Zhang et al. Synthetic Metals v.137, p.1401 (2003)]. A disadvantage of this device is that used it fullerene derivative RSWM has less than a high electron-acceptor ability than With60: first redox potential, specific for this connection according to the electrochemical measurements, 0.09 In more negative than the potential60measured in the same conditions [C.J.Brabec et al. Thin Solid Films v.403-404, p.368 (2002)].

The present invention is the synthesis of new soluble derivatives of fullerenes, characterized by high efficiency of interaction with the photoexcited polymer having a higher electron-acceptor ability compared to the s60and the creation of photovoltaic devices based on derivatives of fullerenes with the specified properties.

The problem is solved in that the proposed photovoltaic device includes a wound is described derivatives of fullerenes, containing organic amines and hydrogen atoms attached to the molecule of fullerene C60for 6,6-double bonds, the General formula

C60Hn(R1R2N)n,

where R1=C6H5CH2, R2=C6H5CH2n=4 (Tetra(dibenzylamino-hydro)[60]fullerene), for example,

or R1=C5H9, R2=N, n=3 (three(cyclopentylamine-hydro)[60]fullerene), for example,

The problem is solved also by the fact that the proposed photovoltaic device comprises a fullerene derivative of the formula C60H4(C6H5CH2NH4(Tetra(dibenzylamino-hydro)[60]fullerene), for example,

The problem is solved also by the fact that the proposed photovoltaic device includes asagumo[60]fullerene containing a nitrogen atom attached to the fullerene C605.6-open communication, with the nitrogen atom attached to one of the radicals:

- 5-nitropyrimidin;

- 1,3-dipropyl-5-(5'-pentyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)Trion

- O,O-dibutylester

2-(asagumo[60]fullerene)-5-nitropyrimidin

1,3-dipropyl-5-[5'-(asagumo[60]fullerene)pentyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-Trion, where All=CH2/sub> CH-CH2

O,O-dibutil(asagumo[60]fullerene)phosphate

The problem is solved also by the fact that in the method of obtaining derivatives of fullerenes containing organic amines and hydrogen atoms attached to the molecule of fullerene C60for 6,6-double bonds, the reaction of interaction With60with an appropriate organic amine is carried out in an aromatic solvent with an excess of amine and at a temperature of 25-70°C for 2-5 days, then the solution is evaporated and planted the product by the addition of alcohol. At the same time as an aromatic solvent, preferably toluene take, and as the alcohol preferably take methanol.

The problem is solved also by the fact that the proposed photovoltaic device comprises as an active layer of a mixture of conjugated polymer and derivatives of fullerenes, and as derivatives of fullerenes it contains substances or mixtures thereof, selected from the group:

Tetra(benzylamino-hydro)[60]fullerene,

Tetra(dibenzylamino-hydro)[60]fullerene,

Three(cyclopentylamine-hydro)[60]fullerene,

2-(asagumo[60]fullerene)-5-nitropyrimidin,

1,3-dipropyl-5-[5'-(asagumo[60]fullerene)pentyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-Trion,

O,O-dibutil(asagumo[60]fullerene)phosphate.

The invention is illustrated by the following examples:

PR is measures 1. Synthesis of Tetra(benzylamino-hydro)[60]fullerene. Toluene solution (50 ml)containing60(20 mg, 0.028 mmol) and 5-fold excess of benzylamine (16.6 mg, 0.14 mmol) were placed in a glass flask. The mixture in an argon atmosphere, a temperature of 30°stirred 3 days. The completeness of the reaction was monitored by thin layer chromatography. The mixture was filtered, the solvent and the amine was partially removed in vacuo, and then the mixture was treated with methanol. Precipitated precipitate was centrifuged, washed several times with methanol, dried in vacuum. The yield of dry product 19.7 mg (80%). Elemental analysis, found (%): C, 91.56; H, 3.12; N, 5.02. With88H36N4. Calculated (%): C, 91.98; H, 3.14; N, 4.88.

Example 2. Synthesis of Tetra(dibenzylamino-hydro)[60]fullerene.

Toluene solution (100 ml)containing60(93.60 mg, 0.13 mmol) and 5-fold excess of dibenzylamine (97.5 mg, 0.65 mmol) were placed in a glass flask. Mixture at a temperature of 27°With was stirred for 4 days in an atmosphere of air. The completeness of the reaction was monitored by thin layer chromatography. The mixture was filtered, the solvent and the amine was partially removed in vacuo, and then the mixture was treated with methanol. Precipitated precipitate was centrifuged, washed several times with methanol, dried in vacuum. The yield of dry product 96 mg (56%). Elemental analysis, found (%): C, 92.76; H, 3.69; N, 3.69. With116H60N4. Calculated (%): C, 92.1; H, 3.98; N, 3.71.

Example 3. The synthesis of three(philopotamidae-hydro)[60]fullerene.

Toluene solution (50 ml)containing60(20 mg, 0.028 mmol) and 5-fold excess of cyclopentylamine (11.9 mg, 0.14 mmol) were placed in a glass flask. The mixture in an argon atmosphere, a temperature of 25°With was stirred for 4 days. The completeness of the reaction was monitored by thin layer chromatography. The mixture was filtered, the solvent and the amine was partially removed in vacuo, and then the mixture was treated with methanol. Precipitated precipitate was centrifuged, washed several times with methanol, dried in vacuum. The yield of dry product 16 mg (75%). Elemental analysis, found (%): C, 92.94; H, 3.36; N, 4.36. C75H33N3. Calculated (%): C, 92.31; H, 3.38; N, 4.31.

Example 4. Evaluation of electron-acceptor ability of fullerene derivatives by electrochemical data.

As a measure of electron-acceptor ability of fullerene derivatives taken the first potential oxidation-reduction measured using cyclic voltammetry in a mixture of o-dichlorobenzene/acetonitrile using a glassy carbon electrode and the supporting electrolyte is 0.1 M Bu4NBF4relative to the reference electrode in 0.01 M Ag/AgNO3. For comparison, the same method of the first measured potential of the oxidation-reduction of fullerene C60. The difference between the peak values of the first pot is dzialow oxidation-reduction derivative of fullerene and 60shown in the table.

ConnectionΔE,C.
Tetra(benzylamino-hydro)[60]fullerene0,08
Tetra(dibenzylamino-hydro)[60]fullerene0,01
three(cyclopentylamine-hydro)[60]fullerene0,08
2-(asagumo[b]fullerene)-5-nitropyrimidin0,08
1,3-dipropyl-5-[5'-(asagumo[60]fullerene)pentyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-Trion0,08
O,O-dibutil(asagumo [60] fullerene)phosphate0,11

The table shows that all derivatives With superior60on electron-acceptor ability, because they have less negative potentials oxidation-reduction.

Example 5. Determination of efficiency of interaction of polymer-fullerene on the quenching of photoluminescence of the polymer.

Prepared solutions containing the polymer MEH-PPV and a derivative of fullerene in different proportions by mixing solutions of the polymer and derivatives of fullerenes in toluene. From the obtained solutions by the method of irrigation was preparing a film on the glass. This has resulted in films containing the polymer and fullerene derivative when the mass ratio of polymer: fullerene=100:1, 50:1, 20:1, 10:1, 5:1 and 1:1, as well as films of pure polim the RA. We measured the photoluminescence spectra of the films using PC 1000 spectrometer with excitation light with a wavelength of 450 nm, i.e. in the absorption band of the polymer. The optical density at 450 nm for all films was greater than 1, that is, the film absorbed more than 90% of light energy. The geometrical arrangement of the films relative to the radiation source and the inlet of the spectrometer in all cases equally. The resulting curves of the intensity of photoluminescence of polymer concentration fullerene derivative in the mixture. The results are presented in figure 1. Denote experimental points:

+ - Tetra(benzylamino-hydro)[60]fullerene,

• - Tetra(dibenzylamino-hydro)[60]fullerene,

about three(cyclopentylamine-hydro)[60]fullerene,

x - 2-(asagumo[60]fullerene)-5-nitropyrimidin,

Δ - 1,3-dipropyl-5-[5'-(asagumo[60]fullerene)pentyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-Trion,

□ - O,O-dibutil(asagumo[60]fullerene)phosphate.

In all cases, increasing the concentration of the fullerene derivative is a decrease in the intensity of photoluminescence of the polymer. In some cases, the luminescence is completely extinguished already at concentrations of polymer 10-20%. This testifies to the effective transfer of photoexcited electrons from polymer to fullerene derivative, which is a necessary condition for effective work fotov leicestera device.

Example 6. Photovoltaic device.

On a glass substrate coated with a layer of ITO, was applied film containing a mixture of the polymer poly(2-methoxy-5-(2'-ethylhexyloxy)-1,4-phenylenevinylene (MYUNG-PPV) and 2-(esagonofree)-5-nitropyrimidine when the content of the fullerene 0, 10, 50, and 75 wt.%. Films were deposited by method of irrigation solution in chlorobenzene containing MEH-PPV and 2-(atheromatosis)-5-nitropyrimidin in appropriate ratios. Next, the composite film was dried by heating in vacuum. The thickness of the films was 100-150 nm. The obtained film was applied to the contact of the aluminum by evaporation in a vacuum. The contact area was about 20 mm2. The current-voltage characteristics of the photovoltaic cells were measured in high vacuum (~10-5Torr) in the dark and when illuminated by light in the wavelength range from 400 to 650 nm. The incident power was 17 mW/cm2. The dependence of the photocurrent (the difference between the current when illuminated and dark current) of the electric field on the sample is shown in Figure 2. It is seen that increasing the concentration of fullerene leads to a significant increase in the photocurrent. So, for the sample containing 75% 2-(atheromatosis)-5-nitropyrimidine, characterized by the increase of the short circuit photocurrent by more than 2 orders of magnitude compared with the sample containing pure on the emer.

Thus, the proposed solution allows you to create photovoltaic devices based compositions "conjugated polymer/fullerene derivative, where derivatives of fullerene effectively interact with the polymer and have a higher electron-acceptor ability in comparison with the original fullerene C60. If this describes two new amino derivatives of fullerene and a method for the synthesis of amino derivatives of fullerene.

1. Derivatives of fullerenes containing organic amines and hydrogen atoms attached to the molecule of fullerene C60for 6,6-double bonds, the General formula

C60Hn(R1R2N)n,

where R1- C6H5CH2, R2-C6H5CH2n=4 (Tetra(dibenzylamino-hydro)[60]fullerene);

R1- C5H9, R2-H, n=3 (three(cyclopentylamine-hydro)[60]fullerene).

2. Use of derivatives of fullerenes:

(Tetra(benzylamino-hydro)[60]fullerene,

(Tetra(dibenzylamino-hydro)[60] fullerene,

three(cyclopentylamine-hydro)[60]fullerene,

2-(asagumo[60]fullerene)-5-nitropyrimidin,

1,3-dipropyl-5-[5'-(asagumo[60]fullerene)pentyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-Trion,

Oh,Oh-dibutil(asagumo[60]fullerene)phosphate

as electron acceptor in composites floor the measures/fullerene, designed for photovoltaic cells.

3. The method of obtaining derivatives of fullerenes containing organic amines and hydrogen atoms attached to the molecule of fullerene C60for 6,6-dual relations, including interaction With60with an appropriate organic amine in solution, characterized in that the reaction is carried out in an aromatic solvent with an excess of amine and at a temperature of 25-70°C for 2-5 days, then the solution is evaporated and planted the product by the addition of alcohol.

4. The method of obtaining derivatives of fullerenes according to claim 3, characterized in that the aromatic solvent is toluene take.

5. The method of obtaining derivatives of fullerenes according to claim 4, characterized in that as the alcohol take methanol.

5. Photovoltaic device containing as the active layer of the mixture of conjugated polymer and derivatives of fullerenes, characterized in that as the derivatives of fullerenes it contains substances or mixtures thereof, selected from the group:

Tetra(benzylamino-hydro)[60]fullerene,

Tetra(dibenzylamino-hydro)[60]fullerene,

three(cyclopentylamine-hydro)[b]fullerene,

2-(asagumo[60]fullerene)-5-nitropyrimidin,

1,3-dipropyl-5-[5'-(asagumo[60]fullerene)pentyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-Trion,

O,O-dibutil(asagumo[60]fullerene)phosphate.



 

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