CN103258961B - There is the fullerene derivate application in solar cells of two hydrophobic group - Google Patents

There is the fullerene derivate application in solar cells of two hydrophobic group Download PDF

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CN103258961B
CN103258961B CN201210572385.XA CN201210572385A CN103258961B CN 103258961 B CN103258961 B CN 103258961B CN 201210572385 A CN201210572385 A CN 201210572385A CN 103258961 B CN103258961 B CN 103258961B
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fullerene derivate
hydrophobic group
solar cells
application
active layer
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CN103258961A (en
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屠迎锋
李耀文
张盼
李超
朱秀林
杨晓明
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Suzhou University
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Abstract

The invention discloses the fullerene derivate application in solar cells with two hydrophobic group, comprise the following steps: step 1) arranges an electronic barrier layer on clean electro-conductive glass; Step 2) with conjugated polymer or conjugation organic molecule for donor material, there is the fullerene derivate of two hydrophobic group as acceptor material, the mixed solution of preparation donor material and acceptor material, arranges an active layer film on electronic barrier layer under utilizing the processing method room temperature of solution spin coating; Step 3) arranges one deck electrode on active layer film, namely obtains organic polymer heterojunction solar battery.The present invention can obtain there is long-range order, nanoscale is separated, the ideal structure solar cell active layer of continuous transmission channel, greatly improve electricity conversion and simplify technique prepared by device, eliminate that device is oxidizable in reprocessing, the risk of degraded.

Description

There is the fullerene derivate application in solar cells of two hydrophobic group
Technical field
The invention belongs to photovoltaic material field, be specifically related to the fullerene derivate application in solar cells with two hydrophobic group.
Background technology
Solar energy, as inexhaustible, nexhaustible reproducible green energy resource, becomes the focus of scientific circles of various countries research.Wherein, solar cell solar energy being converted to electric energy becomes one of research topic the most popular in the world today.Organic solar batteries (OSCs) is a kind of good very promising selection obtaining clean solar energy capable of circulation.Compare with inorganic semiconductor, organic material has a lot of advantages: raw material sources are extensive, handling ease, can large area film forming, easily carries out physical modification, low price, the features such as technique is simple.Therefore be expected to prepare on a large scale low cost, frivolous, rollable, the solar cell that can use flexibly.The organic photoelectric pond early stage of development be the active layer of one-component is clipped in there is different work functions electrode in the middle of, but this form makes energy conversion efficiency very low because electric charge produces little and unbalanced Charger transfer.1995, people's reported first such as Yu will be by gathering (2-methoxyl group-5-(2-ethyl hexyl oxy)-1,4-phenylene ethylene) (MEH-PPV) and the blended bulk heterojunction solar cell (Bulk-Heterojunction BHJ) preparing active layer of fullerene derivate PCBM, this work proposes the concept of bulk heterojunction solar cell first.By this method, absorption region in active layer is from the distance of only having a few nanometer to acceptor material interface, and this just substantially increases quantum efficiency, and the formation of this co-continuous network creates two tracks, respectively to body region transfer hole, at acceptor regions metastatic electron.But due to the unformed state of polymer donor material ubiquity, poorly soluble and with acceptor material (such as, the feature such as PCBM) compatibility is poor, in the blended active layer obtained by solution spin coating processing method, there is large scale state of aggregation (not having continuous print electronics, hole transport passage), to be seriously separated etc. and to be unfavorable for the surface topography of exciton dissociation, transmission in majority.And effective exciton diffusion length is only 10-20 nanometer in blended active layer, exciton is just quenched to body and acceptor interface place not arriving, even if the exciton be separated also can cannot be transferred to corresponding electrode because the isolated island structure of large scale state of aggregation occurs, finally also can be quenched.For giving acceptor material blended active layer surface topography ubiquity the problems referred to above at present, existing main ameliorative way has: (1), according to solvent evaporates dynamics influence factor, selects different solvents, such as different boiling, mixed solvent, additive etc.; (2) device carries out reprocessing, as physical methods such as solvent annealing, thermal annealings; (3) by carrying out molecular structure alteration to active layer material, improve to acceptor material dissolubility and compatibility between the two.These methods for obtaining long-range order, intercellular tight is piled up, homogeneous, nanoscale is separated desired activities layer pattern have extraordinary effect, can greatly improve mobility and the solar cell device efficiency of active layer.But the physical property difference (as dissolubility, compatibility, phase transition temperature, crystallinity etc.) possessed due to different active layer material, topography optimization is carried out by selecting the means of different solvents and reprocessing in said method, there is optimal conditions complexity, narrow application range, pattern be difficult to the shortcomings such as control, the method of thermal annealing also can cause the aging acceleration of device, reduce the life-span of device, and be not suitable for broad area device, especially the preparation of flexible device.Then loaded down with trivial details building-up process be can cause because of the modification criterion do not determined by the method for molecular structure alteration, thus preparation cost and the cycle of material increased.Owing to being difficult to find a kind of method that technique is simple, applied widely, controllability is high to control active layer surface topography, although result in a large amount of novel solar battery material to be in recent years in the news, device efficiency also has steady lifting, but the present situation that the report of real high-photoelectric transformation efficiency is little.Therefore development is a kind of does not carry out the reprocessings such as thermal annealing by solution spin coating, and the method that more efficiently active layer surface topography controls and optimizes, will the matter of utmost importance of organic polymer bulk heterojunction solar cell development be become.The two hydrophobicity fullerene derivates synthesized by above method can substitute PCBM effectively, become fullerene acceptor material of new generation.
Summary of the invention
For solving the problem, the object of this invention is to provide the fullerene derivate application in solar cells with two hydrophobic group, replacing PCBM, being applied in bulk heterojunction solar cell.
For realizing above-mentioned technical purpose, reach above-mentioned technique effect, the present invention is achieved through the following technical solutions:
There is the fullerene derivate application in solar cells of two hydrophobic group, comprise the following steps:
Step 1) arranges an electronic barrier layer on clean electro-conductive glass;
Step 2) with conjugated polymer or conjugation organic molecule for donor material, there is the fullerene derivate of two hydrophobic group as acceptor material, the mixed solution of preparation donor material and acceptor material, arranges an active layer film on electronic barrier layer under utilizing the processing method room temperature of solution spin coating;
Step 3) arranges one deck electrode on active layer film, namely obtains organic polymer heterojunction solar battery.
Further, the tri-alkoxy benzene hydrophobic group that the methanofullerene hydrophobic group that described fullerene derivate comprises benzene replacement is connected with by flexible spacer group, simultaneously at the fullerene [6 that methylene replaces, 6] fluorine phenyl carrying out diverse location and number replaces, and its structural formula is as follows:
in formula, R is C nh 2n+1, n is 4-20, and fluorine replaces point three classes a: R 1=H, R 2=H, R 3=F, R 4=H R 5=H; R 1=H, R 2=F, R 3=F, R 4=F, R 5=H; R 1=F, R 2=F, R 3=F, R 4=F, R 5=F, wherein, fullerene is not confined to C 60, also can be C 70and C 80.
Further, described fullerene derivate is unbodied, can not form large scale and assemble, have excellent thermal stability.
Further, described fullerene derivate is owing to introducing end alkyl chain, the dissolubility had in organic solvent.
Further, the interaction that the tri-alkoxy benzene of described fullerene derivate end group can have with donor material, can induce poly-3 hexyl thiophene P3HT crystallizations, the degree of crystallinity of P3HT is improved, and conjugacy strengthens, and is formed and is similar to P3HT/ [6.6]-C after annealing 60the fibrous ordered lamellar structure of P3HT in-phenylbutyric acid methyl esters PCBM, can obtain the bulk heterojunction active layer surface topography with co-continuous transmission channel of long-range order.
Further, after introducing fluorine atom, the interaction between described fullerene derivate can be strengthened, form orderly molecular structure, improve light abstraction width, improve short circuit current.
Further, step 2) described in donor material be selected from: P3HT, poly-(2-(5-(5,6--bis-octyloxy-4-thiophene-benzo [c] [1,2,5] thiadiazoles-7-thiophene-9-octyl group-9H-carbazole) or polythiophene also [3,4-b] thiophene benzene 1,4-Dithiapentalene.
Further, step 2) described in donor material and acceptor material mixed solution in, the mass ratio of donor material and acceptor material is 1: 0.5 ~ 1: 6, and the concentration of the mixed solution of described donor material and acceptor material is 5 ~ 40 mg/ml.
Further, step 2) described in solution spin coating processing method in, rotating speed is 600 ~ 4000rpm, and the thickness of described active layer film is 100 ~ 200 nanometers.
Further, electrode described in step 3) is magnesium/silver, calcium/aluminium or lithium fluoride/aluminium electrode.
The invention has the beneficial effects as follows:
1, the fullerene derivate containing two hydrophobic group that the present invention adopts, relative to PCBM, due to the introducing of long oxyalkyl chain, has better dissolubility;
2, the fullerene derivate containing two hydrophobic group that the present invention adopts is unbodied relative to PCBM, large gathering can not be formed in film forming procedure, thus effectively can improve interfacial area, improve the life-span of light-generated excitons, improve the quantity of charge carrier, therefore improve the efficiency of organic solar batteries;
3, the fullerene derivate containing two hydrophobic group that the present invention adopts can induce P3HT crystallization effectively, improves the degree of crystallinity of P3HT, causes short circuit current significantly to raise, thus greatly improve solar battery efficiency under unannealed condition;
4, the fullerene derivate containing two hydrophobic group that adopts of the present invention and P3HT blended after, when without any reprocessing, long-range order can be obtained, nanoscale is separated, the ideal structure solar cell active layer of continuous transmission channel, greatly improve electricity conversion and simplify technique prepared by device, eliminate that device is oxidizable in reprocessing, the risk of degraded.
Above-mentioned explanation is only the general introduction of technical solution of the present invention, in order to better understand technological means of the present invention, and can be implemented according to the content of specification, coordinates accompanying drawing to be described in detail as follows below with preferred embodiment of the present invention.The specific embodiment of the present invention is provided in detail by following examples and accompanying drawing thereof.
Accompanying drawing explanation
Fig. 1 is P3HT/PCBB-C 8's 1hNMR collection of illustrative plates, wherein [6.6]-C 60-phenylbutyric acid-3,4,5-tri-octyloxy benzyl ester is abbreviated as PCBB-C 8;
Fig. 2 is P3HT/PCBB-C 8, the UV, visible light collection of illustrative plates of film after P3HT/PCBM and P3HT/PCBM annealing;
Fig. 3 is P3HT/PCBB-C 8the heterojunction solar battery current-voltage curve of active layer;
Fig. 4 is P3HT/ PCBB-C 8the heterojunction solar battery external quantum efficiency curve of active layer.
Embodiment
Below with reference to the accompanying drawings and in conjunction with the embodiments, describe the present invention in detail.
A kind of preparation method of the fullerene derivate containing two hydrophobic group specifically comprises the following steps:
(1) Gallic Acid methyl esters and alkyl halide are reacted under weakly alkaline environment, obtain 3,4,5-tri-alkoxy methyl benzoate, described alkyl halide to be carbon chain lengths be 4 ~ 20 monosubstituted halogenated hydrocarbons;
(2) in anhydrous tetrahydrofuran solution, with lithium aluminium hydride reduction (LiAlH 4) reduction 3,4,5-tri-alkoxy benzoic acid obtains 3,4,5-tri-alkoxy phenmethylol;
(3) be hydrolyzed under acetic acid/hydrochloric acid effect by literature method PCBM, PCBM and obtain [6.6]-C 60-phenylbutyric acid (PCBA).
(4) by [6.6]-C 60-phenylbutyric acid (PCBA) and 3,4,5-tri-alkoxy phenmethylols react, with N, N-lutidines (DMAP), p-methyl benzenesulfonic acid (PTSA), N, N-diisopropylamide (DIPC) is catalyst, esterification occurs and obtains end product, be containing C 60fullerene compound.
In technique scheme, the even number of described halogenated hydrocarbons to be alkyl chain be 4-20.
There is the fullerene derivate application in solar cells of two hydrophobic group, comprise the following steps:
Step 1) arranges an electronic barrier layer on clean electro-conductive glass;
Step 2) with conjugated polymer or conjugation organic molecule for donor material, there is the fullerene derivate of two hydrophobic group as acceptor material, the mixed solution of preparation donor material and acceptor material, arranges an active layer film on electronic barrier layer under utilizing the processing method room temperature of solution spin coating;
Step 3) arranges one deck electrode on active layer film, namely obtains organic polymer heterojunction solar battery.
Further, the tri-alkoxy benzene hydrophobic group that the methanofullerene hydrophobic group that described fullerene derivate comprises benzene replacement is connected with by flexible spacer group, simultaneously at the fullerene [6 that methylene replaces, 6] fluorine phenyl carrying out diverse location and number replaces, and its structural formula is as follows:
in formula, R is C nh 2n+1, n is 4-20, and fluorine replaces point three classes a: R 1=H, R 2=H, R 3=F, R 4=H R 5=H; R 1=H, R 2=F, R 3=F, R 4=F, R 5=H; R 1=F, R 2=F, R 3=F, R 4=F, R 5=F, wherein, fullerene is not confined to C 60, also can be C 70and C 80.
Further, described fullerene derivate is unbodied, can not form large scale and assemble, have excellent thermal stability.
Further, described fullerene derivate is owing to introducing end alkyl chain, the dissolubility had in organic solvent.
Further, the interaction that the tri-alkoxy benzene of described fullerene derivate end group can have with donor material, can induce the crystallization of poly-3 hexyl thiophenes (P3HT), the degree of crystallinity of P3HT is improved, conjugacy strengthens, and is formed and is similar to rear P3HT/ [the 6.6]-C of annealing 60the fibrous ordered lamellar structure of P3HT in-phenylbutyric acid methyl esters (PCBM), can obtain the bulk heterojunction active layer surface topography with co-continuous transmission channel of long-range order.
Further, after introducing fluorine atom, the interaction between described fullerene derivate can be strengthened, form orderly molecular structure, improve light abstraction width, improve short circuit current.
Further, step 2) described in donor material be selected from: P3HT, poly-(2-(5-(5,6--bis-octyloxy-4-thiophene-benzo [c] [1,2,5] thiadiazoles-7-thiophene-9-octyl group-9H-carbazole) or polythiophene also [3,4-b] thiophene benzene 1,4-Dithiapentalene.
Further, step 2) described in donor material and acceptor material mixed solution in, the mass ratio of donor material and acceptor material is 1: 0.5 ~ 1: 6, and the concentration of the mixed solution of described donor material and acceptor material is 5 ~ 40 mg/ml.
Further, step 2) described in solution spin coating processing method in, rotating speed is 600 ~ 4000rpm, and the thickness of described active layer film is 100 ~ 200 nanometers.
Further, electrode described in step 3) is magnesium/silver, calcium/aluminium or lithium fluoride/aluminium electrode.
Embodiment one:
(1) by quartz glass plate chloroform, acetone, the wiping of isopropyl alcohol cotton balls, to be then put in baking oven 100 DEG C of heat dryings 25 minutes, removing isopropyl alcohol.
(2) under room temperature condition, by conjugated polymer P3HT and PCBB-C 8, PC 60bM is dissolved in the solution being mixed with 10 mg/ml in its good solvent chlorobenzene (CB) respectively, stirs 6 ~ 10 hours, to ensure that conjugated polymer fully dissolves, at the P3HT/PCBB-C that room temperature will prepare under the mixing speed of 200 ~ 1200rpm 8chlorobenzene solution is with the rotating speed of 1100rpm, and P3HT/PCBM chlorobenzene solution is spin-coated on quartz glass plate with the rotating speed of 800rpm.
(3) wherein a slice P3HT/PCBM that step (2) prepares is transferred in glove box, with the annealing temperature 10 minutes of 145 DEG C in thermal station, namely prepare the film tested for ultravioletvisible absorption (Uv-vis absorption).
Fig. 1 is P3HT/PCBB-C 8's 1hNMR collection of illustrative plates.
Shown in Figure 2, P3HT/PCBB-C 8under unannealed condition, have obvious red shift compared to P3HT/PCBM, resonance absorption band also broadens, and P3HT/PCBB-C is described 8in P3HT degree of crystallinity be significantly improved, conjugacy strengthen, define the structure of long-range order.
Embodiment two: with PCBB-C 8for acceptor material, be equivalent to replace PCBM.
(1) by ito glass chloroform, acetone, the wiping of isopropyl alcohol cotton balls, then with rotating speed 3000rpm spin coating, obtain the PEDOT:PSS layer that a layer thickness is 40 nanometers, using as electronic barrier layer, to be then put in thermal station 125 DEG C of heat dryings 25 minutes, removing moisture.
(2) according to the step (2) of embodiment one by P3HT/PCBB-C 8be dissolved in chlorobenzene solution with P3HT/PCBM, be mixed with 10 mg/ml solution. the P3HT/PCBB-C will prepared again 8chlorobenzene solution is with the rotating speed of 1100rpm, and P3HT/PCBM chlorobenzene solution is spin-coated on the ito glass sheet modified with the rotating speed of 800rpm, obtain the active layer that thickness is about 150 nanometers.
(3) wherein a slice P3HT/PCBM that step (2) prepares to be transferred in glove box in thermal station with the annealing temperature 10 minutes of 145 DEG C.
(4) last, after solvent volatilizees completely, be the lithium fluoride of 0.8 nanometer and the aluminium electrode of 100 nanometers by method evaporation a layer thickness of vacuum evaporation, namely prepare organic polymer heterojunction solar battery.P3HT/PCBB-C 8as shown in Figure 3, external quantum efficiency curve as shown in Figure 4 for current-voltage curve.
Organic polymer heterojunction solar battery performance in comparing embodiment two, obtains table 1.
Table 1: utilize PCBB-C respectively 8be that (light intensity is 100mW/cm for the organic polymer heterojunction solar battery Performance comparision of acceptor material with PCBM 2measure under AM 1.5 white light illumination condition)
Active layer J sc(mA/cm 2) Voc(V) FF PCE(%)
P3HT/PCBM 1.99 0.70 0.34 0.47
P3HT/PCBM-annealing 8.81 0.55 0.62 2.98
P3HT/PCBB-C8 8.42 0.56 0.49 2.32
Table 1
As shown in Table 1: apply prepared by method of the present invention with PCBB-C 8for the organic polymer heterojunction solar battery of acceptor material, under the condition without any reprocessing, its energy conversion efficiency reaches 2.32%, and short circuit current is 8.42mA/cm 2, obtain than the device efficiency adopting PCBM to be acceptor material to prepare according to the same terms and short circuit current and increase substantially, close to by the reprocessed device efficiency of annealing, compare in detail in table 1.Research shows: application the present invention not only can make exciton be separated fully to acceptor material interface containing the organic polymer heterojunction solar battery of fullerene derivate prepared by acceptor material of two hydrophobic group, and can effectively be collected, significant raising is obtained relative to the device prepared under taking PCBM as acceptor material condition of the same race, close to the device efficiency by annealing reprocessing at the device photoelectric transformation efficiency do not obtained by any reprocessing.Therefore, utilize method of the present invention not only can prepare high performance polymer solar cell, and the great technique simplifying device and prepare.
The foregoing is only the preferred embodiment of invention, be not limited to the present invention, for a person skilled in the art, the present invention can have various modifications and variations.Within the spirit and principles in the present invention all, any amendment done, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.

Claims (9)

1. there is the fullerene derivate application in solar cells of two hydrophobic group, it is characterized in that, comprise the following steps:
Step 1) arranges an electronic barrier layer on clean electro-conductive glass;
Step 2) with conjugated polymer or conjugation organic molecule for donor material, there is the fullerene derivate of two hydrophobic group as acceptor material, the mixed solution of preparation donor material and acceptor material, arranges an active layer film on electronic barrier layer under utilizing the processing method room temperature of solution spin coating;
Step 3) arranges one deck electrode on active layer film, namely obtains organic polymer heterojunction solar battery;
The tri-alkoxy benzene hydrophobic group that the methanofullerene hydrophobic group that described fullerene derivate comprises benzene replacement is connected with by flexible spacer group, simultaneously at the fullerene [6 that methylene replaces, 6] fluorine phenyl carrying out diverse location and number replaces, and its structural formula is as figure below:
in formula, R is C nh 2n+1, n is 4-20, and fluorine replaces point three classes a: R 1=H, R 2=H, R 3=F, R 4=H R 5=H; R 1=H, R 2=F, R 3=F, R 4=F, R 5=H; R 1=F, R 2=F, R 3=F, R 4=F, R 5=F, wherein, fullerene is not confined to C60, C70 or C80.
2. the fullerene derivate application in solar cells with two hydrophobic group according to claim 1, is characterized in that: described fullerene derivate is unbodied, can not form large scale and assemble, have excellent thermal stability.
3. the fullerene derivate application in solar cells with two hydrophobic group according to claim 1, is characterized in that: described fullerene derivate is owing to introducing end alkyl chain, the dissolubility had in organic solvent.
4. the fullerene derivate application in solar cells with two hydrophobic group according to claim 1, it is characterized in that: the interaction that the tri-alkoxy benzene of described fullerene derivate end group can have with donor material, poly-3 hexyl thiophene crystallizations can be induced, formed and be similar to rear P3HT/ [the 6.6]-C of annealing 60the fibrous ordered lamellar structure of P3HT in-phenylbutyric acid methyl esters, can obtain the bulk heterojunction active layer surface topography with co-continuous transmission channel of long-range order.
5. the fullerene derivate application in solar cells with two hydrophobic group according to claim 1, it is characterized in that: after introducing fluorine atom, the interaction between described fullerene derivate can be strengthened, form orderly molecular structure, improve light abstraction width, improve short circuit current.
6. the fullerene derivate application in solar cells with two hydrophobic group according to claim 1, it is characterized in that: step 2) described in donor material be selected from: P3HT, poly-(2-(5-(5,6--bis-octyloxy-4-thiophene-benzo [c] [1,2,5] thiadiazoles-7-thiophene-9-octyl group-9H-carbazole) or polythiophene also [3,4-b] thiophene benzene 1,4-Dithiapentalene.
7. the fullerene derivate application in solar cells with two hydrophobic group according to claim 1, it is characterized in that: step 2) described in donor material and acceptor material mixed solution in, the mass ratio of donor material and acceptor material is 1: 0.5 ~ 1: 6, and the concentration of the mixed solution of described donor material and acceptor material is 5 ~ 40 mg/ml.
8. the fullerene derivate application in solar cells with two hydrophobic group according to claim 1, it is characterized in that: step 2) described in solution spin coating processing method in, rotating speed is 600 ~ 4000rpm, and the thickness of described active layer film is 100 ~ 200 nanometers.
9. the fullerene derivate application in solar cells with two hydrophobic group according to claim 1, is characterized in that: electrode described in step 3) is magnesium/silver, calcium/aluminium or lithium fluoride/aluminium electrode.
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