CN110400880A - The application of organic free radical and its derivative in photovoltaic device - Google Patents
The application of organic free radical and its derivative in photovoltaic device Download PDFInfo
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- CN110400880A CN110400880A CN201910687246.3A CN201910687246A CN110400880A CN 110400880 A CN110400880 A CN 110400880A CN 201910687246 A CN201910687246 A CN 201910687246A CN 110400880 A CN110400880 A CN 110400880A
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- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
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- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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Abstract
The invention belongs to organic free radical photovoltaic technology field, and in particular to the application of organic free radical and its derivative in photovoltaic device.Using organic free radical and its derivative as electron acceptor material, small molecule or conjugated polymer as electron donor material, organic/polymer photovoltaics are prepared by the method that solution is processed, to generate photovoltaic effect.The method of the present invention has further widened the application of organic free radical material in the opto-electronic device, and that has broken organic free radical material applies bottleneck, can effectively expand the application of organic free radical material, play the potential photoelectric characteristic of such material.
Description
Technical field
The invention belongs to organic/polymer photovoltaic technical fields, and in particular to a kind of organic free radical and its derivative exist
Application in photovoltaic device.
Background technique
Organic photovoltaic devices are a kind of novel devices for converting solar energy into electric energy, since its is at low cost, production method
Simply, material structure mutability, light weight, can flexible large area preparation the advantages that, cause the extensive concern of scientific circles and industry.
In polymer photovoltaics, the selection of active layer material is mostly important, wherein contain organic or polymer donor material and
Acceptor material.Currently, numerous donor materials and acceptor material are found out by researcher.Meanwhile in organic/polymerization
Object field of photovoltaic devices, the optimization and innovation of photovoltaic device are to improve a kind of excellent means of device performance.In order to improve device
Stability and energy conversion efficiency, a series of acceptor material of scientific research person's extensive exploitation, wherein outstanding material has
Electron acceptor material is selected from fullerene or fullerene derivate, metal semiconductor compound quantum dot or nano wire.But
It is such acceptor material, synthesis step is cumbersome, at high cost, has limited to the development of organic photovoltaic devices to a certain extent.So
The organic photovoltaic material and system for developing novel concept and structure become a very urgent task.
Organic free radical is a kind of electronic structure unsaturated state material, has certain photoelectricity magnetic characteristic.Currently, it is organic from
It is relatively narrow by the application range of base, focus primarily upon the design of organic free radical compound or organic free radical polyalcohol material with
Synthesis phase, to limit the further exploitation and application of organic free radical material.
Summary of the invention
Organic free radical its own it is intrinsic open shell mould electronic structure, be a short of electricity subcenter, there is potential combination electricity
The ability of son.Therefore, organic free radical material can be applied in organic photovoltaic devices, realize efficient energy conversion.This hair
It is bright by using organic free radical and its derivative as the electron acceptor material of organic/polymer photovoltaics active layer, application
In photovoltaic device.
Organic/polymer photovoltaics provided by the invention, device architecture include the substrate stacked gradually, anode layer,
Anode modification layer, active layer, cathodic modification layer, cathode layer or device architecture include the substrate, cathode layer, yin stacked gradually
Pole decorative layer, active layer, anode modification layer, anode layer；Wherein acceptor material is a kind of organic free radical in the active layer
Or derivatives thereof.
Active layer in organic/polymer photovoltaics of the invention is to contain electron donor material and electron acceptor material
Bulk heteroj unction structure film layer, and active layer with a thickness of 20~1000 nanometers；Wherein electron donor material is selected from
In conjugation small organic molecule, polyvinylene class aromatic polymer, polyfluorene, polysilico fluorene, polycarbazole, polythiophene, polybenzazole carbazole, gather
Indenes fluorenes, the homopolymer of polyphenyl 1,4-Dithiapentalene or copolymer, perovskite material, inorganic-quantum-dot semiconductor or inorganic semiconductor
Nano wire；Electron acceptor material is selected from a kind of organic free radical or derivatives thereof.
Organic free radical and its derivative of the invention is carbon radicals organic material, oxygen radical organic material or nitrogen
Free radical organic material.
The structure of currently preferred free radical organic material is as follows:
Substrate is glass or transparent plastic film in polymer photovoltaics of the present invention；Anode layer mixes for indium
SnO 2 thin film, the fluorine SnO 2 thin film, the aluminium that mix zinc-oxide film, metallic silver or the gold thin film mixed；Anode modification
Layer is the homopolymer or total of the mixed film of Polyglycolic acid fibre and kayexalate (PEDOT:PSS), poly-triphenylamine
Polymers, the homopolymer of polycarbazole or copolymer, Electrochromic Molybdenum Oxide Coatings, nickel oxide film, vanadium oxide film or tungsten oxide film；Institute
Cathodic modification layer is stated to be alkali metal, alkaline-earth metal, alkali metal compound, alkaline earth metal compound composite membrane or be containing polarized
Organic/polymer material of group；The cathode layer is aluminium, silver, conductive metal oxide, graphene, Graphene derivative, carbon
Nanotube.
Organic/polymer photovoltaic of the present invention just setting device the preparation method comprises the following steps:
(1) anode layer, anode modification layer are sequentially prepared by solution processing method or vacuum vapour deposition on substrate.
(2) dissolution is blended with donor material for organic free radical or derivatives thereof in organic solvent, is processed by solution
Method obtains active layer；
(3) cathodic modification layer is prepared by solution processing method or vacuum vapour deposition on active layer.
(4) cathode layer is prepared by solution processing method or vacuum vapour deposition in cathodic modification layer, obtain it is described it is organic/
Polymer photovoltaics.
It is of the present invention it is organic/polymer photovoltaic be inverted device the preparation method comprises the following steps:
(1) cathode layer, cathodic modification layer are sequentially prepared by solution processing method or vacuum vapour deposition on substrate.
(2) dissolution is blended with donor material for organic free radical or derivatives thereof in organic solvent, is processed by solution
Method obtains active layer.
(3) anode modification layer is prepared by solution processing method or vacuum vapour deposition on active layer.
(4) anode layer is prepared by solution processing method or vacuum vapour deposition in anode modification layer, obtain it is described it is organic/
Polymer photovoltaics.
Solution processing method in the preparation method is spin coating, brushing, spraying, dip-coating, roller coating, silk-screen printing, printing
Or inkjet printing methods.
Organic solvent in preparation method of the present invention is selected from toluene, dimethylbenzene, tetrahydrofuran, methyl tetrahydro
Furans, chlorobenzene, o-dichlorohenzene, chloroform and its related derivatives.
The concentration of organic free radical or derivatives thereof material in a solvent is 1~50 milli in preparation method of the present invention
Gram every milliliter.
Donor material and acceptor material (organic free radical or derivatives thereof and donor material in preparation method of the present invention
Material in organic solvent be blended dissolution) mass ratio between 1:0.1~1:5.
Advantage for present invention and beneficial effect are: a kind of completely new Organic host materials concept is provided, and
And it is applied in body heterojunction organic photovoltaic devices.Meanwhile organic free radical material has further been widened in phototube
Application in part, that has broken organic free radical material applies bottleneck, can effectively expand the application of organic free radical material,
Play the potential photoelectric characteristic of such material.In addition, since organic free radical materials synthesis is easy, low in cost and structure is easy
In modification and diversity, to provide extensive acceptor selection for organic/polymer photovoltaics.
Detailed description of the invention
Fig. 1 is just setting device architecture schematic diagram；
Fig. 2 is inverted device structural schematic diagram；
Voltage-current density curve of Fig. 3 organic free radical material BDPA as the flip device of acceptor material；
Voltage-current density curve of Fig. 4 organic free radical material Galvinoxyl as the formal dress device of acceptor material；
Fig. 5 PBDB-T, the ultraviolet of organic free radical material Galvinoxyl and PBDB-T:Galvinoxyl blend film can
Light-exposed absorption curve figure；
The external quantum efficiency curve graph of Fig. 6 PBDB-T and organic free radical material Galvinoxyl blend film.
Specific embodiment
Organic/polymer photovoltaics proposed by the invention are illustrated below with reference to embodiment, the present invention is not
It is limited to this example.
Embodiment 1 just setting type it is organic/preparations of polymer photovoltaics
By ITO electro-conductive glass, square resistance~20 ohm-sq rice is precut into 15 millimeters × 15 millimeters square pieces.Successively
With acetone, micron level semiconductor special purpose detergent, deionized water, isopropanol ultrasonic cleaning, nitrogen purging is placed on constant temperature oven
It is spare.Before use, the net piece of ITO is in oxygen plasma etch instrument with plasma bombardment 10 minutes.In anode ITO electro-conductive glass
On, with PEDOT:PSS aqueous dispersions (about 1.3-1.7% is purchased from Xi'an Polymer Light Technology Co., Ltd.) for anode modification
Layer, by sol evenning machine (KW-4A) high speed (3200 rpms of revolving speed) spin coating, thickness is determined by solution concentration and revolving speed, with spy
Stylus surface contourgraph (Bruker company Dektak-XT type) actual measurement monitoring.After film forming, drive away solvent in constant-temperature vacuum baking oven
Remaining, post bake.By conjugated polymer donor material PBDB-T (poly- [(2,6- (bis- (5- (2- ethylhexyl) thiophene -2- of 4,8-
Base)-benzo [1,2-b:4,5-b'] Dithiophene]-(5,5- (1', 3 '-two -2- thiophene -5', 7 '-bis- (2- ethylhexyl) benzos
[1', 2 '-c:4', 5 '-c'] Dithiophene -4,8- diketone)], purchase in 1-Materials company) after weighing, turn in clean bottle
Enter nitrogen protection film forming special gloves case (Vigor company), dissolved in chlorobenzene, then with organic free radical acceptor material
Galvinoxyl (ten thousand oxygroup free radical of jar (unit of capacitance), purchase in TCI company) is blended, and certain mixed solution than column is mixed into
(15 milligrams every milliliter of total concentration).Mixed with polymers layer optimum thickness is 60 nanometers.Film thickness Bruker company Dektak-XT type
The measurement of probe-type surface profiler.In the glove box for having nitrogen protection, on the ITO slide that spin coating has PEDOT:PSS layers
Face spin coating (2500 rpms of revolving speed) one layer of polymeric PBDB-T and the Galvinoxyl (quality of PBDB-T and Galvinoxyl
Than the blend films for 1:0.5) as active layer, be then dissolved in methanol solvate PFN-Br (it is poly- [(9,9- bis- (3'- (N,
N- dimethyl)-methyl ammonium-propyl) -2,7- fluorenes) -2,7- (9,9- dioctyl)] dibrominated ammonium, purchase Yu Shuolun organic photoelectric section
Skill Co., Ltd) solution (0.5 milligram every milliliter of concentration) is produced on active layer as cathodic modification layer by way of spin coating.
Silver electrode is vaporized on vacuum degree in vacuum coating equipment and reaches 3 × 10-4It is completed when Pa or less.Plated film rate and each layer electricity
The thickness of pole is monitored in real time by quartz vibrator film thickness monitor (STM-100 type, Sycon company).All preparation process are mentioning
For being carried out in the glove box of nitrogen inert atmosphere.Final obtain has ITO/PEDOT:PSS (40 nanometers)/PBDB-T:
The formal dress type photovoltaic device of Galvinoxyl (60 nanometers)/PFN-Br (5 nanometers)/Ag (100 nanometers).The current-voltage of device
Characteristic is measured by PVIV-94023A Current Voltage source-measuring system and a corrected silicon photo diode.
Fig. 4 is the voltage-current density curve graph of PBDB-T:Galvinoxyl blend film in optimal conditions, from figure
It can be seen that best open-circuit voltage is 0.674 volt, current density is 0.867 milliampere every square centimeter.
Fig. 5 is the ultraviolet-visible absorption curve of PBDB-T, Galvinoxyl and PBDB-T:Galvinoxyl blend film
Scheme, the maximum absorption peak of PBDB-T can be learnt in figure in 620 nanometers, the maximum absorption peak of Galvinoxyl is at 435 nanometers
Place, and there are the characteristic absorption peak of a Galvinoxyl, PBDB-T:Galvinoxyl blend films at 830 nanometers to 900 nanometers
Ultraviolet absorption curve figure can see the characteristic absorption peak of apparent PBDB-T and Galvinoxyl.
Fig. 6 is the external quantum efficiency curve graph of PBDB-T:Galvinoxyl blend film at optimum conditions, and what is integrated is short
Road current value and actual measurement short-circuit current value coincide well, and maximum external quantum efficiency value is 7.5%.
2 inversion type of embodiment is organic/preparations of polymer photovoltaics
By ITO electro-conductive glass, square resistance~20 ohm-sq rice is precut into 15 millimeters × 15 millimeters square pieces.Successively
With acetone, micron level semiconductor special purpose detergent, deionized water, isopropanol ultrasonic cleaning, nitrogen purging is placed on constant temperature oven
It is spare.Before use, the net piece of ITO is in oxygen plasma etch instrument with plasma bombardment 15 minutes.Prepare ITO/ZnO's first
Composite cathode layer (ITO/ZnO): one layer of zinc acetate solution (concentration of spin coating (3000 rpms of revolving speed) on ITO electro-conductive glass
100 milligrams every milliliter), it is handled 1 hour in 200 degrees Centigrades, one layer of zinc oxide film is formed, as cathodic modification layer.
After conjugated polymer donor material PBDB-T is weighed in clean bottle, it is transferred to nitrogen protection film forming special gloves case
(Vigor company), dissolves in chlorobenzene, then with the organic free radical acceptor material BDPA (bis- diphenylene-beta-phenyls of alpha, gamma-
Allyl radical is purchased in Sigma-Aldrich company) it is blended, it is mixed into certain mixed solution (total solution than column
20 milligrams every milliliter of concentration).Mixed with polymers layer optimum thickness is 80~100 nanometers.Film thickness (Bruker company Dektak-
XT type) measurement of probe-type surface profiler.In the glove box for having nitrogen protection, revolved on spin coating has ITO/ZnO slide
Apply the mixture of (3500 rpms of revolving speed) one layer of polymeric PBDB-T and BDPA (mass ratio of PBDB-T and BDPA are 1:1)
Film layer.Molybdenum oxide and silver electrode are vaporized on vacuum degree in vacuum coating equipment and reach 3 × 10-4It is completed when Pa or less.Plated film rate with
The thickness of each layer electrode is monitored in real time by quartz vibrator film thickness monitor (STM-100 type, Sycon company).Finally had
ITO/ZnO (30 nanometers)/PBDB-T:BDP A (65 nanometers)/MoO3The inversion type photovoltaic of (10 nanometers)/Ag (100 nanometers) structure
Device.All preparation process carry out in the glove box for providing nitrogen inert atmosphere.
The I-E characteristic of device, by PVIV-94023A Current Voltage source-measuring system and a corrected silicon
Optical diode measures.
Fig. 3 is not do by 80 degrees Celsius of thermal anneal process and hot place under PBDB-T:BDPA film optium concentration and ratio
The voltage-current density curve graph for managing device, it is bright to can be seen from the chart that the device current density after Overheating Treatment has
Aobvious rising, from 0.307 milliampere it is every square centimeter rise to 0.723 milliampere it is every square centimeter.
Comparative example 1 and embodiment 2
It is used as electron acceptor using 1,1- diphenyl -2- picryl hydrazine free radical is (commercially available), conjugated polymer is given as electronics
Body material, the body heterojunction polymer photovoltaics of preparation and 2 identity unit structure of embodiment 1 and embodiment, finds no
Photovoltaic effect.
Example below is illustrated photovoltaic device proposed by the invention with characteristic, but the present invention be not limited to it is listed
Example.
Polymer photovoltaics performance of table 1 Galvinoxyl and BDPA as active layer acceptor material
Just setting device A structure: (100 receive ITO/PEDOT:PSS/PBDB-T:Galvinoxyl (60 nanometers)/PFN-Br/Ag
Rice)
Invert device B1 structure: ITO/ZnO/PBDB-T:BDPA (100 nanometers)/MoO3/ Ag (65 nanometers) (not thermal annealing
Processing)
Invert device B2 structure: ITO/ZnO/PBDB-T:BDPA (100 nanometers)/MoO3/ Ag (65 nanometers) (move back by 80 DEG C of heat
Fire processing)
It is found by table 1, oxygen radical compound Galvinoxyl and carbon radicals BDPA can be used as effective electronics
Acceptor material is applied in polymer photovoltaics, and apparent photovoltaic effect occurs.Therefore, such organic free radical and its derivative
Application of the object in photoelectric field is further expanded, and provides solid base for the exploitation and application of the following organic free radical
Plinth, meanwhile, also the design and development for organic/Polymer photovoltaic materials in the future provides more selections.
Claims (10)
1. a kind of application of organic free radical and its derivative in photovoltaic device, which is characterized in that the organic free radical and
Its derivative is used as the electron acceptor material of organic/polymer photovoltaics active layer；The active layer is with electron donor
The film layer of the bulk heteroj unction structure of material and electron acceptor material, and active layer with a thickness of 20~1000 nanometers.
2. the application of organic free radical according to claim 1 and its derivative in photovoltaic device, which is characterized in that institute
It states organic free radical and its derivative is carbon radicals organic material, oxygen radical organic material or the organic material of nitrogen free radical
Material.
3. the application of organic free radical according to claim 1 and its derivative in photovoltaic device, which is characterized in that institute
Electron donor material is stated to be selected from conjugation small organic molecule, polyvinylene class aromatic polymer, polyfluorene, polysilico fluorene, polycarbazole, gather
Thiophene, polybenzazole carbazole, polyindene fluorenes, the homopolymer of polyphenyl 1,4-Dithiapentalene or copolymer, perovskite material, inorganic-quantum-dot half
Conductor or inorganic semiconductor nano wire.
4. the application of organic free radical according to claim 1 and its derivative in photovoltaic device, which is characterized in that institute
State substrate, anode layer, anode modification layer, active layer, cathodic modification that organic/polymer photovoltaics structure is followed successively by stacking
Layer, cathode layer or device architecture are followed successively by substrate, cathode layer, cathodic modification layer, active layer, anode modification layer, the sun of stacking
Pole layer.
5. the application of organic free radical according to claim 4 and its derivative in photovoltaic device, it is characterised in that: institute
Stating substrate is glass or transparent plastic film；The anode layer is that the tin oxide that SnO 2 thin film, the fluorine that indium mixes mix is thin
Zinc-oxide film, metallic silver or the gold thin film that film, aluminium mix；The anode modification layer is Polyglycolic acid fibre and polyphenyl second
The mixed film of alkene sodium sulfonate (PEDOT:PSS), the homopolymer of poly-triphenylamine or copolymer, the homopolymer of polycarbazole or copolymerization
Object, Electrochromic Molybdenum Oxide Coatings, nickel oxide film, vanadium oxide film or tungsten oxide film；The cathodic modification layer is alkali metal, alkaline earth
Metal, alkali metal compound, alkaline earth metal compound composite membrane are organic/polymer material containing polar group；Institute
Stating cathode layer is aluminium, silver, conductive metal oxide, graphene, Graphene derivative, carbon nanotube.
6. the application of organic free radical according to claim 4 and its derivative in photovoltaic device, it is characterised in that: institute
Stating the preparation methods of organic/polymer photovoltaics, steps are as follows:
(1) anode layer, anode modification layer are sequentially prepared by solution processing method or vacuum vapour deposition on substrate；
(2) dissolution is blended with donor material for organic free radical or derivatives thereof in organic solvent, passes through Solution processing techniques
Obtain active layer；
(3) cathodic modification layer is prepared by solution processing method or vacuum vapour deposition on active layer；
(4) cathode layer is prepared by solution processing method or vacuum vapour deposition in cathodic modification layer, obtains the organic/polymerization
Object photovoltaic device；Or
(1) cathode layer, cathodic modification layer are sequentially prepared by solution processing method or vacuum vapour deposition on substrate；
(2) dissolution is blended with donor material for organic free radical and its derivative in organic solvent, passes through Solution processing techniques
Obtain active layer；
(3) anode modification layer is prepared by solution processing method or vacuum vapour deposition on active layer；
(4) anode layer is prepared by solution processing method or vacuum vapour deposition in anode modification layer, obtains the organic/polymerization
Object photovoltaic device.
7. the application of organic free radical according to claim 6 and its derivative in photovoltaic device, it is characterised in that: institute
The solution processing method stated is spin coating, brushing, spraying, dip-coating, roller coating, silk-screen printing, printing or inkjet printing methods.
8. the application of organic free radical according to claim 6 and its derivative in photovoltaic device, it is characterised in that: institute
The organic solvent stated is selected from toluene, dimethylbenzene, tetrahydrofuran, methyltetrahydrofuran, chlorobenzene, o-dichlorohenzene, chloroform, and
Its related derivatives.
9. the application of organic free radical according to claim 6 and its derivative in photovoltaic device, it is characterised in that: institute
The concentration of organic free radical stated or derivatives thereof material in a solvent is between 1~50 milligram every milliliter.
10. the application of organic free radical according to claim 6 and its derivative in photovoltaic device, it is characterised in that:
The mass ratio of the donor material and organic free radical or derivatives thereof material is between 1:0.1~1:5.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111628089A (en) * | 2020-05-29 | 2020-09-04 | 华中科技大学 | Free radical polymer capable of modifying carrier transport layer and application thereof |
| CN113130766A (en) * | 2021-04-13 | 2021-07-16 | 苏州大学 | Organic/polymer solar cell and active layer thereof |
| CN113193128A (en) * | 2021-05-24 | 2021-07-30 | 电子科技大学 | Perovskite solar cell with interface modification layer and preparation method thereof |
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| US20130199601A1 (en) * | 2008-10-08 | 2013-08-08 | ZeevValentine Vardeny | Organic Spintronic Devices and Methods for Making the Same |
| CN104576931A (en) * | 2015-01-12 | 2015-04-29 | 华南理工大学 | Organic/polymer solar battery device and preparation method thereof |
| CN105355791A (en) * | 2015-11-01 | 2016-02-24 | 华南理工大学 | Water/alcohol-soluble non-conjugated polymer interface material, organic solar cell device and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130199601A1 (en) * | 2008-10-08 | 2013-08-08 | ZeevValentine Vardeny | Organic Spintronic Devices and Methods for Making the Same |
| CN104576931A (en) * | 2015-01-12 | 2015-04-29 | 华南理工大学 | Organic/polymer solar battery device and preparation method thereof |
| CN105355791A (en) * | 2015-11-01 | 2016-02-24 | 华南理工大学 | Water/alcohol-soluble non-conjugated polymer interface material, organic solar cell device and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111628089A (en) * | 2020-05-29 | 2020-09-04 | 华中科技大学 | Free radical polymer capable of modifying carrier transport layer and application thereof |
| CN111628089B (en) * | 2020-05-29 | 2022-06-14 | 华中科技大学 | Free radical polymer capable of modifying carrier transport layer and application thereof |
| CN113130766A (en) * | 2021-04-13 | 2021-07-16 | 苏州大学 | Organic/polymer solar cell and active layer thereof |
| CN113130766B (en) * | 2021-04-13 | 2022-12-30 | 苏州大学 | Organic/polymer solar cell and active layer thereof |
| CN113193128A (en) * | 2021-05-24 | 2021-07-30 | 电子科技大学 | Perovskite solar cell with interface modification layer and preparation method thereof |
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