CN106380380A - Fullerene derivative and application of fullerene derivative in perovskite solar cells - Google Patents
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
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Abstract
A fullerene derivative and application of the fullerene derivative in perovskite solar cells belong to the field of solar cell material preparation. The structure of the fullerene derivative is as shown in the specification, wherein R1, R2, R3, R4, R5 and R6 are selected from hydrogen atom, halogen atom, oxygen atom, alkenyl group, alkynyl group, aryl group, hydroxy group, amino group, carbonyl group, carboxyl group, ester group, cyan-group, nitro group, the same or different C1-C20 alkyl groups, or the same or different C1-C20 alkyloxy groups; and ring F indicates fullerene C60, fullerene C70, fullerene C76 or fullerene C84. According to the invention, a novel derivative is synthesized. The synthetic process is simple, reaction temperature is low, and yield is high. The product has good solubility, high electron mobility and proper energy level. A prepared perovskite solar cell has high photoelectric conversion efficiency and good stability.
Description
Technical field
The present invention relates to a kind of fullerene derivate and its application in perovskite solaode, belong to solar-electricity
Pond field of material preparation.
Background technology
In recent years, a kind of based on organo-mineral complexing perovskite material as light absorbent all solid state perovskite solar energy
Battery causes the very big concern (Kim H.-S., et al., Sci.Rep.2012,2,591) of people, this kind of perovskite solar energy
Cell photoelectric conversion efficiency has reached more than 20% (Yang W.S., et al., Science 2015,348,1234), and prepares
Process is simple, processing cost is low, has become as the important research focus of photovoltaic art.
Fullerene and its derivant are widely used in perovskite solaode as electron transport material, wherein C60
Derivant [6,6]-benzene-carbon 61- methyl butyrate (PCBM) be conventional electron transport material in perovskite solaode
(Jeng J.-Y.,et al.,Adv.Mater.2013,25,3727).But PCBM is not necessarily optimal perovskite solar-electricity
Ester group contained by pond electron transport material, especially PCBM has certain hydrophilic, leads to the prepared perovskite sun
Can battery less stable in wet condition (Zhao D., et al., Angew.Chem.Int.Ed.2016,55,
8999), limit its development in terms of practical application.So needing to develop new electron transport material to prepare height
Imitate stable perovskite solar cell device.
Content of the invention
An object of the present invention is to provide a kind of fullerene derivate.
The present invention provide fullerene derivate structure as shown in formula I,
In formula I, R1、R2、R3、R4、R5And R6Selected from hydrogen atom, halogen atom, oxygen atom, thiazolinyl, alkynyl, aryl, hydroxyl
Base, amino, carbonyl, carboxyl, ester group, cyano group, nitro, identical or the C differing1-C20Alkyl or identical or non-phase
Same C1-C20Alkoxyl；Ring F represents fullerene C60, fullerene C70, fullerene C76Or fullerene C84；Described C1-C20's
Alkyl or alkoxyl are straight chain, side chain or ring-type, or wherein one or more carbon atoms can be by oxygen atom, thiazolinyl, alkynyl, virtue
Base, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano group or nitro replace, or wherein one or more hydrogen atoms can be by halogen
Atom, oxygen atom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano group or nitro replace.
The second object of the present invention there are provided a kind of preparation method of fullerene derivate shown in formula I, including such as
Lower step：(1) compound shown in formula II and rongalite carry out reaction and obtain compound shown in formula III；(2) formula
(III) compound shown in and fullerene carry out reaction and obtain final product described fullerene derivate；Described fullerene is fullerene C60, fowler
Alkene C70, fullerene C76Or fullerene C84；
In formula II, X is chlorine atom or bromine atoms.
In formula II and formula III, R1、R2、R3、R4、R5And R6It is selected from hydrogen atom, halogen atom, oxygen atom, thiazolinyl, alkynes
Base, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano group, nitro, identical or the C differing1-C20Alkyl or phase
C that is same or differing1-C20Alkoxyl.
In above-mentioned preparation method, described C1-C20Alkyl or alkoxyl be straight chain, side chain or ring-type, or wherein
One or more carbon atoms can be by oxygen atom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano group or nitre
Base replace, or wherein one or more hydrogen atoms can by halogen atom, oxygen atom, thiazolinyl, alkynyl, aryl, hydroxyl, amino,
Carbonyl, carboxyl, ester group, cyano group or nitro replace.
In above-mentioned preparation method, the temperature of the described reaction of step (2) can be 60 DEG C -150 DEG C, concretely 60 DEG C or
150℃；The time of described reaction can be 2 hours -20 hours, concretely 2 hours or 20 hours.
The third object of the present invention is to provide purposes derived from fullerene as described above, above-mentioned fullerene derivate material
It is soluble in and common are machine solvent, there is higher electron mobility, the fullerene derivate of suitable energy level, the therefore present invention
Perovskite solaode can be applied to as electron transfer layer.
The invention has the advantages that：(1) method that the present invention provides has synthesized a kind of new fullerene and has derived
Thing, building-up process is simple, and reaction temperature is low, and has higher yield；(2) fullerene derivate that the present invention provides has
Preferably dissolubility, higher electron mobility and suitable energy level, the perovskite solar cell photoelectric conversion effect being prepared into
Rate is higher, good stability, is the very promising photovoltaic material of one kind.
Brief description
Fig. 1 is the structural representation of perovskite solar cell device in the embodiment of the present invention 3, electron transfer layer therein
For described fullerene derivate.
Fig. 2 is the I-V curve of the perovskite solaode of the embodiment of the present invention 3 preparation.
Fig. 3 is the stability test result (humidity 30%, air) of perovskite solaode.
Specific embodiment
Experimental technique used in following embodiments if no special instructions, is conventional method.
Material used, reagent etc. in following embodiments, if no special instructions, all commercially obtain.
Embodiment 1, prepare fullerene derivate F1
Synthetic route is as follows：
1. 1,2- bis- (bromomethyl) benzene of 0.25mmol and 1mmol rongalite are dissolved in N, N- dimethyl formyl
In amine (DMF), add 0.03mmol tetrabutyl ammonium bromide (TBAB), after reacting 5 hours under ice bath, reaction solution is poured into water
In, use dichloromethane aqueous phase extracted, organic faciess anhydrous sodium sulfate drying, revolving removes organic solvent, cross silica gel post separation, obtain
It is compound shown in formula (1) to oil product, yield is 80%.
2. by the fullerene C of 0.1mmol60It is dissolved in toluene with compound shown in 0.15mmol formula (1), at 85 DEG C, reaction 12 is little
Shi Hou, reaction solution is poured into water, and uses toluene aqueous phase extracted, organic faciess anhydrous sodium sulfate drying, revolving removes organic molten
Agent, crosses silica gel post separation (petroleum ether：Toluene=1：1.2, v/v), obtain pulverulent solids product F1, yield is 75%.
1H NMR(400MHz,CDCl3):δ(ppm)7.13-7.85(m,4H),4.75(m,2H),4.32(m,2H).
The mass spectral characteristi of product F1 is shown in Table 1, and measured value is close with theoretical molecular.
The MALDI-TOF mass spectrometry results of the fullerene derivate F1-F2 of table 1 embodiment 1-2 preparation
Embodiment 2, prepare fullerene derivate F2
Synthetic route is as follows：
1. 10mmol catechol, 25mmol n-amyl bromide are dissolved in butanone, add 35mmol potassium carbonate and 0.1mmol tetra-
Butylammonium bromide, after reacting 20 hours, reaction solution is poured into water at 90 DEG C, uses dichloromethane aqueous phase extracted, and organic faciess are used
Anhydrous sodium sulfate drying, revolving removes organic solvent, crosses silica gel post separation, obtains oil product and be 1,2- bis- n-pentyloxy
Benzene, yield is 75%.
1H NMR(400MHz,CDCl3):δ(ppm)6.88(s,4H),3.96(t,4H),1.88(m,4H),1.71-1.82
(m,8H),0.98(t,6H).
2. by 4mmol 1,2- bis- n-pentyloxy benzene and 10mmol formaldehyde are dissolved in acetic acid, add the acetic acid of 15mmol hydrogen bromide
Solution (mass fraction of contained hydrogen bromide is 33%), after reacting 12 hours, reaction solution is placed in -4 DEG C of refrigerators under room temperature,
Have insoluble matter to separate out, filter white solid is 1,2- bis- bromomethyl -4,5- bis- n-pentyloxy benzene, yield is 60%.
1H NMR(400MHz,CDCl3):δ(ppm)6.83(s,2H),4.62(s,4H),4.00(t,4H),1.82(m,
4H),1.35-1.49(m,8H),0.93(t,6H).
3. the 1,2- bis- bromomethyl -4,5- two n-pentyloxy benzene of 0.25mmol and 1mmol rongalite are dissolved in
In DMF (DMF), add 0.03mmol tetrabutyl ammonium bromide (TBAB), after reacting 6 hours under ice bath, will be anti-
Answer solution to be poured into water, use dichloromethane aqueous phase extracted, organic faciess anhydrous sodium sulfate drying, revolving removes organic solvent, mistake
Silica gel post separation, obtains oil product and is compound shown in formula (2), and yield is 65%.
4. by the fullerene C of 0.1mmol60It is dissolved in toluene with compound shown in 0.15mmol formula (2), at 85 DEG C, reaction 2 is little
Shi Hou, reaction solution is poured into water, and uses toluene aqueous phase extracted, organic faciess anhydrous sodium sulfate drying, revolving removes organic molten
Agent, crosses silica gel post separation, obtains pulverulent solids product F2, and yield is 70%.
1H NMR(400MHz,CDCl3):δ(ppm)7.21(s,2H),4.72(s,2H),4.33(s,2H),4.16(t,
4H),1.90-1.94(m,4H),1.52-1.56(m,4H),1.44-1.47(m,4H),0.97(t,6H).13C NMR(400MHz,
CDCl3):δ(ppm)148.51,148.19,146.75,145.59,145.44,145.04,144.82,143.78,141.59,
141.32,130.06,111.50,111.26,77.25,77.03,76.82,67.99,65.33,65.10,65.02,64.70,
64.60,56.21,45.05,44.80.
The mass spectral characteristi of product F2 is shown in Table 1, and measured value is close with theoretical molecular.
Embodiment 3, fullerene derivate F1 and F2 of embodiment 1-2 preparation prepare the perovskite sun as electron transfer layer
Can battery device and its performance characterization
Fig. 1 shows fullerene derivate of the present invention as the perovskite solar cell device knot of electron transfer layer
Structure, including：Transparent conductive substrate, hole transmission layer, calcium titanium ore bed, electron transfer layer, metal electrode.Preparation process is as follows：
(1) cleaning of electro-conductive glass：Continuous deionized water, acetone, isopropanol are cleaned by ultrasonic and UV ozone processes 20
Minute.
(2) preparation of nickel oxide hole transmission layer：Nickel acetylacetonate is dissolved in ethanol, is subsequently adding equimolar ratio
Diethanolamine, obtains nickel oxide precursor aqueous solution, is spun and coated on electro-conductive glass, 500 degree of heat treatments of in the air 30 minutes.
(3) preparation of calcium titanium ore bed：By iodine methylamine and lead iodide in molar ratio 1:1 mixing is dissolved in the mixing of DMF and DMSO
In solvent, obtain the perovskite solution that concentration is 1M.Perovskite is spun in FTO/NiO substrate and 95 DEG C of annealing 30min shapes
Become calcium titanium ore bed.
(4) preparation of electron transfer layer：Fullerene derivate F1, F2 or PCBM of synthesis are dissolved in chlorobenzene, by it
It is spin-coated on formation electron transfer layer above calcium titanium ore bed.
(5) device is moved into vacuum evaporation chamber, vacuum evaporation argent, prepared perovskite solar cell device.
The performance of the perovskite solaode of above-mentioned preparation as shown in table 2 (all tests all record under 1 sun,
100mw/cm2), the photovoltaic device I-V curve of fullerene derivate F1 and F2 preparation is shown in Fig. 2.
The perovskite solar cell properties of fullerene derivate F1 and F2 of table 2 embodiment 1 and 2 preparation
Can be drawn by the above results, the fullerene derivate that the present invention provides is as perovskite solaode electric transmission
Layer has higher photoelectric transformation efficiency, is a kind of very promising material.
Meanwhile, the perovskite solaode of most important F2 preparation has excellent stability, under the conditions of humidity 30%,
After in the air is placed 30 days, device efficiency remains the 70% of initial value；The perovskite solar cell device of PCBM preparation exists
After placing 30 days under same humidity, device efficiency substantially reduces, and is the 20% of initial value, as shown in Figure 3.The perovskite of F2 preparation
Solaode greatly improves to the stability of humidity, and the alkyl chain stemming primarily from F2 has hydrophobic interaction.
Claims (5)
1. a fullerene derivant is it is characterised in that have following structure：
Wherein, R1、R2、R3、R4、R5And R6Selected from hydrogen atom, halogen atom, oxygen atom, thiazolinyl, alkynyl, aryl, hydroxyl, amino,
Carbonyl, carboxyl, ester group, cyano group, nitro, identical or the C differing1-C20Alkyl or identical or the C differing1-
C20Alkoxyl, ring F represents fullerene C60, fullerene C70, fullerene C76Or fullerene C84.
2. a fullerene derivant according to claim 1 it is characterised in that：Described C1-C20Alkyl or C1-C20's
Alkoxyl be straight chain, side chain or ring-type, or wherein one or more carbon atoms by oxygen atom, thiazolinyl, alkynyl, aryl, hydroxyl,
Amino, carbonyl, carboxyl, ester group, cyano group or nitro replace, or wherein one or more hydrogen atoms are former by halogen atom, oxygen
Son, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano group or nitro replace.
3. prepare the method for fullerene derivate as claimed in claim 1 it is characterised in that comprising the steps：
(1) compound shown in formula II and rongalite carry out reaction and obtain compound shown in formula III；
(2) compound shown in formula III and fullerene carry out reaction and obtain final product described fullerene derivate, the described reaction of step (2)
Temperature is 80 DEG C -150 DEG C；The time of described reaction is 2 hours -24 hours；Described fullerene is fullerene C60, fullerene C70、
Fullerene C76Or fullerene C84；
In formula II, X is chlorine atom or bromine atoms.
In formula II and formula III, R1、R2、R3、R4、R5And R6Be selected from hydrogen atom, halogen atom, oxygen atom, thiazolinyl, alkynyl,
Aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano group, nitro, identical or the C differing1-C20Alkyl or identical
Or the C that differs1-C20Alkoxyl.
4. method according to claim 3 it is characterised in that：Described C1-C20Alkyl or C1-C20Alkoxyl be straight
Chain, side chain or ring-type, or wherein one or more carbon atoms by oxygen atom, thiazolinyl, alkynyl, aryl, hydroxyl, amino, carbonyl,
Carboxyl, ester group, cyano group or nitro replace, or wherein one or more hydrogen atoms are by halogen atom, oxygen atom, thiazolinyl, alkynes
Base, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano group or nitro replace.
5. a fullerene derivant according to claim 1 and 2 it is characterised in that：Described fullerene derivate application
In perovskite solaode.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109698280A (en) * | 2018-12-26 | 2019-04-30 | 苏州大学 | Application of the fullerene methylene derivatives I in perovskite solar battery, perovskite solar battery and preparation method thereof |
| CN115279722A (en) * | 2020-01-23 | 2022-11-01 | 国立大学法人东海国立大学机构 | Fullerene derivative, method for producing fullerene derivative, vapor-deposited material, film, and electronic device |
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| US5763719A (en) * | 1993-01-20 | 1998-06-09 | Hoechst Ag | Thermally stable fullerene derivatives and process for producing the same |
| US20120004476A1 (en) * | 2009-01-29 | 2012-01-05 | Korea Research Institute Of Chemical Technology | Fullerene Derivatives and Organic Electronic Device Comprising the Same |
| CN102391078A (en) * | 2011-09-01 | 2012-03-28 | 中国科学院化学研究所 | Benzene ring-contained fullerene derivative and preparation method and use thereof |
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2016
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| US5763719A (en) * | 1993-01-20 | 1998-06-09 | Hoechst Ag | Thermally stable fullerene derivatives and process for producing the same |
| US20120004476A1 (en) * | 2009-01-29 | 2012-01-05 | Korea Research Institute Of Chemical Technology | Fullerene Derivatives and Organic Electronic Device Comprising the Same |
| CN102391078A (en) * | 2011-09-01 | 2012-03-28 | 中国科学院化学研究所 | Benzene ring-contained fullerene derivative and preparation method and use thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109698280A (en) * | 2018-12-26 | 2019-04-30 | 苏州大学 | Application of the fullerene methylene derivatives I in perovskite solar battery, perovskite solar battery and preparation method thereof |
| CN109698280B (en) * | 2018-12-26 | 2022-10-04 | 苏州大学 | Application of fullerene methylene derivative I in perovskite solar cell, perovskite solar cell and preparation method of perovskite solar cell |
| CN115279722A (en) * | 2020-01-23 | 2022-11-01 | 国立大学法人东海国立大学机构 | Fullerene derivative, method for producing fullerene derivative, vapor-deposited material, film, and electronic device |
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