CN106876587A - A kind of organic solar batteries cathode interface material and preparation method thereof and organic solar batteries - Google Patents
A kind of organic solar batteries cathode interface material and preparation method thereof and organic solar batteries Download PDFInfo
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Abstract
It is the zinc oxide of the acid imide micromolecular compound doping containing sulfonate substituent the invention discloses a kind of organic solar batteries cathode interface material.Organic solar batteries the invention also discloses the preparation method of above-mentioned organic solar batteries cathode interface material and with organic solar batteries cathode interface material of the invention as cathode interface.The present invention can greatly improve the processing characteristics and stability of organic solar batteries；The present invention uses aqueous solution process technology, preparation process environmental protection, preparation process is simple, low manufacture cost.
Description
Technical field
The present invention relates to photoelectric material and devices field, more particularly to a kind of organic solar batteries cathode interface material and
Its preparation method and organic solar batteries.
Background technology
Polymer solar battery as a kind of low cost, can the clean energy resource processed of volume to volume, cause extensive pass
Note.It is inverted polymer solar battery to be compared with traditional polymer solar cell, with device performance and stability higher.
With developing rapidly for solar cell, unijunction solar cell energy conversion efficiency has been over 12%, this have benefited to
The development of active layer material and interface engineering.Cathode interface material between active layer and ITO is being inverted polymer solar electricity
Charge collection efficiency played an important role in pond.In recent years, polymer dielectric, such as conjugation and unconjugated polyelectrolyte
It is successfully applied in cathode interface, realizes efficient inversion polymer solar.
In general, conventional organic solar batteries are by substrate, anode (negative electrode) boundary layer, photoactive layer, negative electrode (sun
Pole) boundary layer, metal electrode stack gradually composition.Due to the PEDOT of industrialization：PSS and MoO3As anodic interface
With good performance, so developing energy conversion efficiency and stabilization of the suitable cathode interface layer for organic solar batteries
Property play vital effect (refer to the applicant's Chinese invention patent application of 2013, the patent No.：
201310088849.4, patent name：Organic/the polymer solar cells of a kind of inverted structure).
During zinc oxide is a kind of conventional cathode interface material, with it is cheap, be readily synthesized, it is nontoxic, stable and thoroughly
The advantages of lightness is high.In order to improve the performance of Zinc Oxide Interface layer, the control to zinc oxide electric conductivity and bandwidth is realized,
Zinc oxide is doped extremely important.By the donor element that adulterates, the conductance of zinc oxide can be made to get a promotion so that oxygen
Changing zinc turns into a kind of typical transparent conductive oxide.Doping zinc-oxide can be applied to luminescent device, solar cell, light wave
Lead, the field such as sensor, plate of flat liquid crystal display and infrared reflective device.
The cathode interface layer of important function due to to(for) organic solar batteries, people are preparing high-performance organic solar
Cell cathode field of interfaces has paid huge effort and has also achieved certain achievement, however, the modern industry requirement to environmental protection day
Gradually improve, the processing mode for pursuing more environmental protection is trend of the times；Additionally, in flexible sun process, due to base
Piece is polymeric material, can only processing device at low temperature, the boundary material that can be processed under development low temperature is extremely important.
The content of the invention
It is cloudy it is an object of the invention to a kind of organic solar batteries in order to overcome the disadvantages mentioned above and deficiency of prior art
Pole boundary material, improves the performance of zinc oxide, not only realizes that the aqueous solution is processed, and the stability of processing is also improved, so as to reduce
Large-scale production difficulty and cost.
The purpose of the present invention is achieved through the following technical solutions：
A kind of organic solar batteries cathode interface material, is the acid imide micromolecular compound containing sulfonate substituent
The zinc oxide of doping；
The acid imide micromolecular compound containing sulfonate substituent has following structure：
In formula, n=1,2,3, R1, R2 be independent variable substituted radical, be the alkyl of H, C1~C20, pyridine radicals, not by
Substituted aromatic radical or substituted aromatic radical.
The position of substitution of the sulfonate radical on phenyl ring is the one kind in ortho position, meta, contraposition three.
The alkyl be methyl, ethyl, propyl group, isopropyl, normal-butyl, sec-butyl, isobutyl group, the tert-butyl group, amyl group, oneself
Base, heptyl, octyl group, any one in nonyl, decyl.
The aromatic radical be phenyl, naphthyl, anthryl, phenanthryl, aphthacene base, pentacene base, triphenylamine base, pyrenyl, indenyl,
At least one in xenyl and fluorenyl.
Substitution base in substituted aromatic radical is methyl, ethyl, propyl group, isopropyl, normal-butyl, sec-butyl, isobutyl group,
At least one in the tert-butyl group, hydroxyl, sulfydryl, aliphatic radical, sulfo group, sulfino, nitro, amino, imino group, carboxyl, diazanyl.
The micromolecular compound of the imide group with sulfonate substituent has the one kind in following structure：
Acid imide micromolecular compound containing sulfonate substituent is dissolved in into zinc oxide precursor liquid solution or zinc oxide is molten
In liquid, solution is used the side of spin coating, brushing, spraying, dip-coating, roller coat, silk-screen printing, printing, inkjet printing or in-situ polymerization
Formula forms cathode interface layer on negative electrode or cathode interface layer is formed on photoactive layer；
The acid imide micromolecular compound containing sulfonate substituent is 0.1 with the mass ratio of zinc oxide:100 to
10:100。
The zinc oxide precursor liquid solution be dissolved in deionized water, organic solvent or inorganic solvent by zinc salt prepare and
Into.
A kind of organic solar batteries, including negative electrode circle that the organic solar batteries cathode interface material is prepared from
Surface layer.
Compared with prior art, the present invention has advantages below and beneficial effect：
(1) present invention uses the zinc oxide that the acid imide micromolecular compound containing sulfonate substituent adulterates as negative electrode
Boundary material so that macromolecule water-solubility is greatly promoted, processing characteristics is excellent, and Zinc oxide doped, and its electric conductivity obtains certain journey
The lifting of degree.
(2) material of the invention uses aqueous solution process technology, preparation process is simple, low manufacture cost.
(3) present invention prepare solar cell, under 100 DEG C~200 DEG C annealing temperatures energy conversion efficiency substantially close to,
Realize the possibility of stability and polymer flexibility the substrate processing of processing.
(4) solar cell prepared by the present invention, efficiency change is no more than 3% before and after 60 days, and stability is splendid.
Brief description of the drawings
Fig. 1 is the structural representation of the organic solar batteries of embodiments of the invention.
Specific embodiment
With reference to embodiment, the present invention is described in further detail, but embodiments of the present invention not limited to this.
Embodiment 1
Some with lot number ITO (tin indium oxide) Conducting Glass, specification is 15 millimeters × 15 millimeters, and the thickness of ITO is about
It it is 130 nanometers, its square resistance is about 20 ohms/squares.Acetone, micron level semiconductor special purpose detergent, deionization are used successively
Ultrasonically treated 10 minutes of water, isopropanol cleaning ITO substrate surfaces, are subsequently placed into and stand 4 hours at 80 DEG C in constant temperature oven and dry.
It is placed in after drying on sol evenning machine (KW-4A types), then on the ITO of drying, instil the small molecule chemical combination containing imide group
Thing, or be the polymer-doped zinc oxide precursor or burnett's solution containing imide group, through high speed spin coating (600-
6000 revs/min), rear 100-200 degrees Centigrades 5-60 minutes, the thickness of the cathode interface layer of acquisition is at 0.1-100 nanometers.
Cathode interface layer can by the micromolecular compound containing imide group, or be also to contain the polymer-doped of imide group
Zinc oxide precursor or burnett's solution using brushing, spraying, dip-coating, roller coat, silk-screen printing, printing, inkjet printing or original
The mode of position polymerization forms cathode interface layer on negative electrode.
The oxidation that the cathode interface layer material is adulterated using the acid imide micromolecular compound containing sulfonate substituent
Zinc, these materials have proven to be a kind of excellent electron transport material, can provide ohm to high-work-function metal or ITO
Contact.Micromolecular compound containing imide group, or before being the polymer-doped zinc oxide containing imide group
The preparation for driving body or burnett's solution is to complete to be placed in being stirred on mixing platform in atmosphere.
The molecule has following structure：
In formula：N=1,2,3, R1, R2 be independent variable substituted radical, can be H, C1~C20 alkyl, alkoxy, pyrrole
Piperidinyl, commutable aromatic radical；
Sulfonate radical-SO3The position of substitution of H on phenyl ring is：One kind in ortho position, meta, contraposition three；
Then on substrate/negative electrode as obtained in the above method/cathode interface layer, active layer is prepared.Typical active layer
By polymer donor material and electron acceptor material.The electron donor material is conjugated polymer or organic molecule (as simultaneously
Benzene class, phthalein cyanogen class, thiophene oligomer).The electron acceptor material be can be C60, C60 derivative (as [6,6]-phenyl-
61-methyl butyrates of C (PC61BM)), derivative ([6,6]-phenyl-C71-methyl butyrate (PC of C70, C7071BM)), body shape or
One kind of person's particulate inorganic semi-conducting material (e.g., zinc oxide, titanium dioxide, cadmium sulfide, cadmium telluride etc.).Above-mentioned donor material
It is respectively placed in clean sample bottle with acceptor material, solution is configured to conventional organic solvent (such as chlorobenzene, toluene etc.) dissolving, is put
Put and stirred on heating stirring platform, fully obtain settled solution after dissolving.Then according to a certain percentage by polymeric donor
Material and electron acceptor material mix, and are placed on heating stirring platform and stir.The preparation of photoactive layer is by substrate/the moon
Pole/upper coated polymer donor material of cathode interface layer and the solution of electron acceptor material mixing are obtained.Therefore, first by glass
Substrate/negative electrode/cathode interface layer by the negative-pressure adsorption of mechanical pump generation on sol evenning machine, instillation polymer donor material and electricity
After sub- acceptor material mixing is molten, through high speed spin coating, (600-6000 revs/min) is obtained；Photoactive layer can also be by electron donor material
Formed with electron acceptor material lamination.In general, it is desirable to which obtained photoactive layer thickness is at 20-500 nanometers, and preferred film is thick
Spend is 70-200 nanometers.Thickness is mixed by adjusting the rotating speed and control polymer donor material and electron acceptor material of sol evenning machine
The concentration of solution is closed to control.In preparation process, the thickness of gained film is by surface profiler (Teriek companies Alpha-
Tencor500 types) actual observation record.
Then, device is transferred in Vacuum Deposition chamber, opens mechanical pump and molecular pump, when vacuum reaches 3 × 10 in plating chamber- 4After Pa, start evaporation aluminium film (100 nanometers) as extraction electrode.In the case where being necessary, also in evaporation metal electrode
Preceding evaporation metal oxide (such as molybdenum oxide) film, constitutes compound negative electrode.As the case may be, or from other air
The metal of good stability, such as gold, silver etc. are used as electrode.In order that arriving above-mentioned vacuum thermal evaporation metallic film process, the life of film
The rate of settling long and total deposit thickness are controlled by the thermal power for applying, and by quartz crystal oscillator film thickness monitor (STM-100
Type, the manufacture of Sycon companies) monitor in real time.The uv-visible absorption spectroscopy of photoactive layer or polymer-electronics donor material
Measured by HP8453A type diode array formula ultraviolet-visible spectrophotometers, the wave-length coverage 190 nanometers~1100 of test is received
Rice.
Organic solar energy cell structure of the invention is obtained by above-mentioned steps, from the bottom to top successively by substrate 1, ITO2, the moon
Pole boundary layer 3, photoactive layer 4 and anode layer 5 are folded to constitute (Fig. 1).
The radiant illumination of the AM1.5G measurement standards commonly used in laboratory is 1000 watts/square metre.When using solar simulation light
When carrying out polymer solar cells performance test, first have to be determined with normal cell the irradiation level of the whether compound AM1.5G of light source.
Standard silicon solar cell is by calibration：Under AM1.5G standard spectrums, i.e. the light irradiation of the radiant illumination of 1000 watts/square metre
Under, the short circuit current for obtaining is 125 milliamperes.After determining irradiation intensity, you can device is tested.Carried out with solar simulation light
Solar cell performance test, can easily draw the energy conversion efficiency of solar simulation light, and its computational methods can directly by fixed
Justice is obtained：
Wherein PMAXIt is peak power output (unit：Milliwatt), PinIt is radiant illumination (unit：Milliwatt/square centimeter), S is
Effective area (the unit of device：Square centimeter).Measure the apparatus such as table 1 of polymer body heterojunction solar cell performance
It is shown.
The present embodiment of table 1 is used to be set
The zinc oxide conduct that the acid imide micromolecular compound containing sulfonate substituent adulterates is prepared to the present invention below
Organic solar batteries cathode interface is contrasted with existing zinc oxide as the performance of organic solar batteries cathode interface
Experiment：
Experiment 1：
Sample 1：Using device architecture as shown in Figure 1, from N, N '-two (2,6- diisopropyl benzene) -1,6,7,12- tetra-
Ben Yang Ji perylenes -3,4:9,10- tetrasulfonic acid base acid imides (hereinafter referred to as PBI-SO3H) doping zinc oxide as cathode interface layer,
Deionized water dissolves PBI-SO as process solvent3H, boundary layer heat treatment temperature is 200 degrees Celsius, and polyphenyl 1,4-Dithiapentalene derives
Thing material (PTB7) is used as electron donor material, the derivative of carbon 70-[6,6]-phenyl-C71-methyl butyrate (PC71BM) it is electronics
Acceptor material, prepares the organic solar batteries of inverted structure, and device architecture is：ITO/ZnO:PBI-SO3H/PTB7:PC71BM/
MoO3The inverted structure of/Al；Wherein PBI-SO3H has following structure：
Comparative sample 1a：Using device architecture as shown in Figure 1, from PBI-SO3The zinc oxide of H doping is used as negative electrode circle
Used as cathode interface layer, (volume ratio is from 0.1 for the mixed solution of EGME and monoethanolamine for surface layer：100 to 10：100) conduct
Solvent dissolves PBI-SO3H, boundary layer heat treatment temperature is 200 degrees Celsius, polyphenyl 1,4-Dithiapentalene derivant material (PTB7) conduct
Electron donor material, the derivative of carbon 70-[6,6]-phenyl-C71-methyl butyrate (PC71BM) it is electron acceptor material, prepares and be inverted
The organic solar batteries of structure, device architecture is ITO/ZnO:PBI-SO3H/PTB7:PC71BM/MoO3The inversion device of/Al.
Comparative sample 1b：Using device architecture as shown in Figure 1, from zinc oxide (EGME and monoethanolamine it is mixed
Close solution dissolving) used as cathode interface layer, polyphenyl 1,4-Dithiapentalene derivant material (PTB7) is spread out as electron donor material, carbon 70
Biology-[6,6]-phenyl-C71-methyl butyrate (PC71BM) it is electron acceptor material, prepares the organic solar electricity of inverted structure
Pond, device architecture is ITO/ZnO/PTB7:PC71BM/MoO3The inversion device of/Al.
Under the simulated solar light irradiation of the AM 1.5G of 1000 watts/square metre, test sample 1 and comparative sample 1a, 1b
Performance is as shown in the table：
The performance parameter of the sample 1 of table 2 and comparative sample 1
From the above results：With water-soluble PBI-SO3The zinc oxide of H doping is obtained as cathode interface layer in water phase
Efficiency with nonaqueous phase dissolve compared with, or with pure zinc oxide as cathode interface layer in water phase obtain efficiency compared with, energy
Transformation efficiency increases.
Experiment 2：
Sample 2：Using device architecture as shown in Figure 1, PBI-SO is selected3The zinc oxide of H doping goes as cathode interface layer
Ionized water as solvent, 200 degrees Celsius of boundary layer heat treatment temperature, polyphenyl 1,4-Dithiapentalene derivant material (PTB7) is used as electronics
Donor material, the derivative of carbon 70-[6,6]-phenyl-C71-methyl butyrate (PC71BM) it is electron acceptor material, prepares inverted structure
Organic solar batteries, device architecture is：ITO/ZnO:PBI-SO3H/PTB7:PC71BM/MoO3The inverted structure of/Al；
Comparative sample 2a, comparative sample 2b：Using device architecture as shown in Figure 1, boundary layer heat treatment temperature is taken the photograph for 150
Family name's degree, 100 degrees Celsius, preparation method is identical with sample 2 with device architecture.
Under the simulated solar light irradiation of the AM 1.5G of 1000 watts/square metre, the performance of test sample 2 and comparative sample 2
It is as shown in the table：
The performance parameter of the sample 2 of table 3 and comparative sample 2
From the above results：With PBI-SO3H doping zinc oxide, boundary layer under different heat treatment conditions, as
The organic solar batteries of the inverted structure of cathode interface layer, energy conversion efficiency is held essentially constant, in 150 degrees celsius
Lower energy conversion efficiency highest, is adapted to low temperature process.
Experiment 3
Sample 2 and comparative sample 2a in 2 will be tested to deposit 60 days at room temperature in atmosphere, performance comparison experiment is done.
Under the simulated solar light irradiation of the AM 1.5G of 1000 watts/square metre, the performance of test sample 3 and comparative sample 3
It is as shown in the table：
The performance parameter of the sample 2 of table 4 and comparative sample 2
From the above results：With PBI-SO3H doping zinc oxide as cathode interface layer inverted structure it is organic too
Positive energy battery, for a long time, efficiency still keeps basicly stable to room temperature preservation in atmosphere, declines not substantially, various performance parameters
Keep substantially constant.
Embodiment 2
Sample 3：Using device architecture as shown in Figure 1, from N, the phenoxy group of N '-(1- phenethyls) -1,6,7,12- tetra-
Perylene -3,4:9,10- tetrasulfonic acid base acid imides (hereinafter referred to as PBI-SO3H-2) doping zinc oxide as cathode interface layer, go from
Sub- water dissolves PBI-SO as process solvent3H-2, boundary layer heat treatment temperature is 200 degrees Celsius, polyphenyl 1,4-Dithiapentalene derivative
Material (PTB7) is used as electron donor material, the derivative of carbon 70-[6,6]-phenyl-C71-methyl butyrate (PC71BM) for electronics is received
Body material, prepares the organic solar batteries of inverted structure, and device architecture is：ITO/ZnO:PBI-SO3H-2/PTB7:PC71BM/
MoO3The inverted structure of/Al；Wherein PBI-SO3H-2 has following structure
The performance parameter of the sample 3 of table 5 and comparative sample 3
From the above results：With water-soluble PBI-SO3The zinc oxide of H-2 doping is obtained as cathode interface layer in water phase
Efficiency with nonaqueous phase dissolve compared with, or with pure zinc oxide as cathode interface layer in water phase obtain efficiency compared with, energy
Amount transformation efficiency increases.
Embodiment 3
Using device architecture as shown in Figure 1, PBI-SO is selected3The zinc oxide of H doping, doping concentration mass ratio is
0.1%th, 1%, 2%, used as cathode interface layer, deionized water is used as solvent, 200 degrees Celsius of boundary layer heat treatment temperature, polyphenyl
1,4-Dithiapentalene derivant material (PTB7) is used as electron donor material, the derivative of carbon 70-[6,6]-phenyl-C71-methyl butyrate
(PC71BM) it is electron acceptor material, prepares the organic solar batteries of inverted structure, device architecture is：ITO/ZnO:PBI-
SO3H/PTB7:PC71BM/MoO3The inverted structure of/Al；
The performance parameter of the sample 1 of table 6 and comparative sample 1
From the above results：With water-soluble PBI-SO3The zinc oxide of H doping is used as cathode interface layer, PBI-SO3H adulterates
From 0.1% to 2%, energy conversion efficiency increases ratio, and optimum doping ratio is near 1%.
Above-described embodiment is the present invention preferably implementation method, but embodiments of the present invention are not by the embodiment
Limitation, it is other it is any without departing from Spirit Essence of the invention and the change, modification, replacement made under principle, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (9)
1. a kind of organic solar batteries cathode interface material, it is characterised in that be that the acid imide containing sulfonate substituent is small
The zinc oxide of molecular compound doping；
The acid imide micromolecular compound containing sulfonate substituent has following structure：
In formula, n=1,2,3, R1, R2 be independent variable substituted radical, be the alkyl of H, C1~C20, pyridine radicals, unsubstituted
Aromatic radical or substituted aromatic radical.
2. organic solar batteries cathode interface material according to claim 1, it is characterised in that the sulfonate radical is in benzene
The position of substitution on ring is ortho position, meta, the one kind aligned in three.
3. organic solar batteries cathode interface material according to claim 1, it is characterised in that the alkyl is first
Base, ethyl, propyl group, isopropyl, normal-butyl, sec-butyl, isobutyl group, the tert-butyl group, amyl group, hexyl, heptyl, octyl group, nonyl, decyl
In any one.
4. organic solar batteries cathode interface material according to claim 1, it is characterised in that the aromatic radical is benzene
In base, naphthyl, anthryl, phenanthryl, aphthacene base, pentacene base, triphenylamine base, pyrenyl, indenyl, xenyl and fluorenyl at least one
Kind.
5. the organic solar batteries cathode interface material according to claim 1 or 4, it is characterised in that substituted virtue
Substitution base in perfume base is methyl, ethyl, propyl group, isopropyl, normal-butyl, sec-butyl, isobutyl group, the tert-butyl group, hydroxyl, sulfydryl,
At least one in aliphatic radical, sulfo group, sulfino, nitro, amino, imino group, carboxyl, diazanyl.
6. organic solar batteries cathode interface material according to claim 1, it is characterised in that the band sulfonate radical takes
The micromolecular compound of the imide group of Dai Ji has the one kind in following structure：
7. the preparation method of the organic solar batteries cathode interface material described in claim 1, it is characterised in that sulfonic acid will be contained
The acid imide micromolecular compound of root substitution base is dissolved in zinc oxide precursor liquid solution or burnett's solution, by solution using rotation
The mode of painting, brushing, spraying, dip-coating, roller coat, silk-screen printing, printing, inkjet printing or in-situ polymerization forms negative electrode on negative electrode
Boundary layer forms cathode interface layer on photoactive layer；
The acid imide micromolecular compound containing sulfonate substituent is 0.1 with the mass ratio of zinc oxide:100 to 10:
100。
8. the preparation method of organic solar batteries cathode interface material according to claim 7, it is characterised in that described
Zinc oxide precursor liquid solution is dissolved in deionized water, organic solvent or inorganic solvent by zinc salt and is prepared from.
9. a kind of organic solar batteries, it is characterised in that including the organic solar electricity as described in any one of claim 1~6
The cathode interface layer that pool cathode boundary material is prepared from.
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