CN103811660A - Organic photovoltaic cell - Google Patents

Organic photovoltaic cell Download PDF

Info

Publication number
CN103811660A
CN103811660A CN201310545652.9A CN201310545652A CN103811660A CN 103811660 A CN103811660 A CN 103811660A CN 201310545652 A CN201310545652 A CN 201310545652A CN 103811660 A CN103811660 A CN 103811660A
Authority
CN
China
Prior art keywords
milliliters
mms
aryl
photovoltaic cell
grams
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201310545652.9A
Other languages
Chinese (zh)
Inventor
张翠
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LIYANG JIANGDA TECHNOLOGY TRANSFER CENTER Co Ltd
Original Assignee
LIYANG JIANGDA TECHNOLOGY TRANSFER CENTER Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LIYANG JIANGDA TECHNOLOGY TRANSFER CENTER Co Ltd filed Critical LIYANG JIANGDA TECHNOLOGY TRANSFER CENTER Co Ltd
Priority to CN201310545652.9A priority Critical patent/CN103811660A/en
Publication of CN103811660A publication Critical patent/CN103811660A/en
Pending legal-status Critical Current

Links

Images

Classifications

    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/20Carbon compounds, e.g. carbon nanotubes or fullerenes
    • H10K85/211Fullerenes, e.g. C60
    • H10K85/215Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/0803Compounds with Si-C or Si-Si linkages
    • C07F7/0805Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/0803Compounds with Si-C or Si-Si linkages
    • C07F7/081Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00Energy generation through renewable energy sources
    • Y02E10/50Photovoltaic [PV] energy
    • Y02E10/549Organic PV cells

Abstract

The invention discloses an organic photovoltaic cell, comprises a substrate, a positive pole, an active layer and a negative pole which are sequentially stacked, wherein the active layer comprises stacked electron donor material and electron acceptor material, the electron donor material is an organic compound represented by a formula (VI), and the electron acceptor material is carbon 60 and derivatives of the same or carbon 70 and derivatives of the same; the organic photovoltaic cell is high in energy conversion efficiency.

Description

Organic photovoltaic battery
Technical field
The present invention relates to field of photoelectric devices, relate in particular to a kind of photovoltaic cell.
Background technology
Along with the increase year by year of global energy demand, the day by day exhaustion of the disposable energy such as oil, coal, people have dropped into more concern and research to the renewable resource such as wind energy, solar energy, and wherein the photovoltaic cell based on photovoltaic effect is one of focus wherein.
At present, solar cell ripe on market is mainly the inorganic photovoltaic cell such as based single crystal silicon, polysilicon, amorphous silicon, GaAs, indium phosphide and polycrystalline film compound semiconductor, wherein, polysilicon and amorphous silicon photovoltaic battery are occupied an leading position on civilian photovoltaic cell market.Through the development of more than 50 years, the photoelectric conversion efficiency of inorganic single crystal silicon solar cell is by 6% at the beginning of invention, bringing up to current peak efficiency can reach more than 30%, but because inorganic semiconductor solar cell is very high to the requirement of material purity, and expensive, therefore its application is very limited.
1986, Kodak introduced to body and acceptor material first in same device, formed hetero-junction solar cell conversion efficiency and reached 1%, indicated that photovoltaic device prepared by organic semiconductor makes a breakthrough.Sariciftci in 1992 etc. are to MEH-PPV/C 60in the research of compound system, find that the two does not interact in ground state, but C 60the fluorescence of MEH-PPV is but had to very strong quenching effect, and propose to exist Photoinduced Electron to shift in system.People further investigate different compound systems, have proved the existence that Photoinduced Electron shifts.This process completes in several psecs, and electronics and the hole that can effectively stop optical excitation to produce occur compound again.The discovery of Photoinduced Charge fast energy transfer phenomena is the important breakthrough of polymer solar cells theoretical side, for the raising of polymer solar cells efficiency provides theoretical support.
The people such as nineteen ninety-five Yu Gang, by by electron donor material and acceptor material blend, make the solar cell of conjugated polymer MEH-PPV and carbon 60 inierpeneirating network structures, and its energy conversion efficiency reaches 2.9%.In this system, electron donor material and acceptor material form the interpenetrating networks shape structure of co-continuous, this structure has increased the two interfacial area greatly, heterojunction is disperseed more, this structure that heterojunction structure is distributed to whole active layer, in fact whole active layer is become to a large body heterojunction, thereby any position in active layer all can produce electric charge.As long as each phase material forms the continuous passage from the two interface to each self-electrode, so, can be greatly improved to the conversion efficiency of electronics by photon.The photovoltaic cell that Here it is it has often been said.
Bulk heterojunction concept produces the fault of construction that has overcome individual layer, bilayer/multilayer device.Due to electron donor and the network-like continuous phase of the each self-forming of electron acceptor, the electronics that photoinduction produces and hole respectively separately mutually in transport and be collected on corresponding electrode, photo-generated carrier is greatly reduced by again compound probability before the corresponding electrode of arrival, thereby has improved photoelectric current.Like this, bulk heterojunction structure just can significantly improve photovoltaic energy conversion efficiency.Nowadays, bulk heterojunction concept has been widely used in the solar cell based on polymer, and energy conversion efficiency can reach more than 5%, and it has tempting developing direction.Therefore, people have carried out a large amount of experiments and have found the active layer material that energy conversion efficiency is higher, expect to obtain the organic photovoltaic battery that device performance is higher.
Summary of the invention
The invention discloses a kind of organic photovoltaic battery, it has higher energy conversion efficiency, thereby has good device performance.
The photovoltaic cell that comprises electron transfer layer of the present invention comprises the substrate, anode, active layer and the negative electrode that stack gradually, wherein,
Active layer comprises the electron donor material and the electron acceptor material that are laminated, and wherein electron donor material is the organic compound that general formula (VI) represents, electron acceptor material is carbon 60 and derivative or carbon 70 and derivative thereof,
Figure BDA0000409226940000031
Wherein ,-A-B-represents phenylene;
P and Q represent independently: chemical bond or there is no substituting group or have one or more substituent (C 6-C 30) arlydene, described substituting group is selected from straight or branched and the saturated or undersaturated (C that there is no halogenic substituent or have halogenic substituent 1-C 30) alkyl, (C 6-C 30) aryl and halogen;
R 1represent hydrogen, (C 6-C 30) aryl;
R 2, R 3and R 4represent independently straight or branched and saturated or undersaturated (C 1-C 30) alkyl or (C 6-C 30) aryl;
R 11to R 18represent independently hydrogen, straight or branched and saturated or undersaturated (C 1-C 30) alkyl or (C 6-C 30) aryl;
R 21, R 22and R 23represent independently straight or branched and saturated or undersaturated (C 1-C 30) alkyl or (C 6-C 30) aryl; With
M is 1 or 2 integer;
Preferably, the material of substrate is glass, flexible macromolecule or metal base.
Preferably, the material of anode is metal oxide or the metal oxide that contains alloy.
Preferably, the material of negative electrode is light tight metal.
Accompanying drawing explanation
Fig. 1 is the structural representation of organic photovoltaic battery of the present invention.
Embodiment
Photovoltaic cell of the present invention comprises the substrate 1, anode 2, active layer 4 and the negative electrode 5 that stack gradually, as shown in Figure 1.
Wherein, active layer comprises the electron donor material and the electron acceptor material that are laminated, and wherein electron donor material is the organic compound that general formula (VI) represents, electron acceptor material is carbon 60 and derivative or carbon 70 and derivative thereof,
Figure BDA0000409226940000041
Wherein ,-A-B-represents phenylene;
P and Q represent independently: chemical bond or there is no substituting group or have one or more substituent (C 6-C 30) arlydene, described substituting group is selected from straight or branched and the saturated or undersaturated (C that there is no halogenic substituent or have halogenic substituent 1-C 30) alkyl, (C 6-C 30) aryl and halogen;
R 1represent hydrogen, (C 6-C 30) aryl;
R 2, R 3and R 4represent independently straight or branched and saturated or undersaturated (C 1-C 30) alkyl or (C 6-C 30) aryl;
R 11to R 18represent independently hydrogen, straight or branched and saturated or undersaturated (C 1-C 30) alkyl or (C 6-C 30) aryl;
R 21, R 22and R 23represent independently straight or branched and saturated or undersaturated (C 1-C 30) alkyl or (C 6-C 30) aryl; With
M is 1 or 2 integer;
Prerequisite is that A, B, P and Q can not be chemical bond simultaneously; If-A-B-and-P-Q-is phenylene, R 1must represent hydrogen; Do not comprise-A-B-and-P-Q-is spiral shell two fluorenylidenes, described arlydene and aryl can be further by straight or branched and saturated or undersaturated (C 1-C 30) alkyl, (C 1-C 30) alkoxyl, halogen, (C 3-C 12) cycloalkyl, phenyl, naphthyl or anthryl further replace.
In general formula (VI), R 1represent hydrogen, phenyl, naphthyl, anthryl, xenyl, phenanthryl, aphthacene base, fluorenyl, 9,9-dimethyl-fluorenes-2-base, pyrenyl, benzene anthryl (phenylenyl), fluoranthene base, trimethyl silyl, triethylsilyl, tripropyl silicyl, tri-tert silicyl, t-butyldimethylsilyl, triphenyl silicyl or phenyl dimetylsilyl; R 2, R 3and R 4represent independently methyl, ethyl, n-pro-pyl, isopropyl, isobutyl group, the tert-butyl group, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, cetyl, phenyl, naphthyl, anthryl or fluorenyl; R 11to R 18independently selected from: hydrogen, methyl, ethyl, n-pro-pyl, isopropyl, isobutyl group, the tert-butyl group, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, cetyl, phenyl, naphthyl, anthryl and fluorenyl.
In chemical formula of the present invention, if A or B do not comprise any element be and R 1or anthracene connects, or P or Q do not comprise any element and be just connected with Si or anthracene, is referred to as chemical bond; But A, B, P and Q can not be chemical bond simultaneously.If-A-B-and-P-Q-is phenylene, R 1must represent hydrogen; Do not comprise-A-B-and-P-Q-is spiral shell two fluorenylidenes.
The material of other of photovoltaic cell layer is respectively: the material of substrate 1 can be glass, plastics or metal base.Substrate 1 can be hard material, as glass or quartz, also can be flexible material, as flexible macromolecule, flexible high molecular material includes but not limited to: Polyethylene Naphthalate, polyethylene terephthalate, polyamide, polymethyl methacrylate, Merlon and/or polyurethane.Substrate 1, except above-mentioned insulating material, also can use electric conducting material, the metals such as such as titanium, aluminium, copper, nickel.
The material of anode 2 is metal oxide or the metal oxide that contains alloy (doped), preferential oxidation indium tin (ITO), tin oxide, fluorine doped tin oxide etc.Anode can form by any traditional method, such as vapour deposition, sputter etc.
The material of negative electrode 5 is preferably light tight metal, such as Al, Ca/Al, Mg/Al, Mg/Ag, Cu, Au etc.The method of manufacturing negative electrode 5 can be vapour deposition method deposition etc.
The manufacture method of photovoltaic cell of the present invention comprises each layer for preparing active layer and stack gradually photovoltaic cell.
The embodiment that wherein prepares active layer material is exemplified below:
Example 1: the preparation of active layer electron donor material (102) comprises the steps:
1, the preparation of compound (201)
In flask, add 1,2-dibromobenzene (100.0 grams, 423.9 mMs), 2-naphthalene boronic acids (80.2 grams, 466.3 mMs), toluene (1000 milliliters) and tetrakis triphenylphosphine palladium (Pd (PPh 3) 4) (24.5 grams, 21.2 mMs), under argon gas atmosphere, stir this mixture.Then in mixture, drip wet chemical (300 milliliters), the mixture of formation heats 4 hours under stirring and counterflow condition.By adding distilled water (2000 milliliters) will react quencher, extract this reactant mixture with ethyl acetate (1000 milliliters).Organic extract anhydrous magnesium sulfate drying, filters and reduces pressure down concentrated.By silica gel chromatography (ethyl acetate: hexane=1:50), and the acquisition bromo-2-of 1-(2-naphthyl) benzene (63.59 grams, 224.7 mMs, productive rate: 53.0%).
In the round-bottomed flask of 1 liter, add (42.0 grams of the bromo-2-of 1-(2-naphthyl) benzene, 148.5 mMs) and oxolane (1000 milliliters), drip positive BuLi (1.6M hexane solution) (89.0 milliliters, 222.5 mMs) in-78 ℃ to this flask.At same temperature, stir this mixture after 1 hour, in reactant mixture, drip trimethylborate (24.8 milliliters, 222.5 mMs), temperature is increased to room temperature.Stir this reactant mixture 12 hours, in the time that reaction completes, add 1M hydrochloric acid solution (500 milliliters), the mixture that stirring forms 5 hours.The organic extract anhydrous magnesium sulfate drying obtaining with distilled water (500 milliliters) and ethyl acetate (600 milliliters) extraction, filters and reduces pressure down concentrated.From ethyl acetate (80 milliliters) and methyl alcohol (600 milliliters) recrystallization, and acquisition compound (201) (27.28 grams, 110.0 mMs, productive rate: 74.1%).
2, the preparation of compound (202)
In 500 milliliters of round-bottomed flasks, add (27.28 grams of compounds (201), 110.0 mMs), 9-bromine anthracene (28.16 grams, 88.0 mMs), toluene (500 milliliters) and tetrakis triphenylphosphine palladium (Pd (PPh 3) 4) (2.45 grams, 2.05 mMs), under argon gas atmosphere, stir this mixture.Then in this mixture, drip wet chemical (100 milliliters), the mixture of formation heats 4 hours under stirring and counterflow condition.In the time completing reaction, in reactant mixture, add distilled water (600 milliliters), then use ethyl acetate (400 milliliters) extraction.Organic extract anhydrous magnesium sulfate drying, filters and reduces pressure down concentrated.By silica gel chromatography (carrene: hexane=1:15), and acquisition compound (202) (25.20 grams, 66.32 mMs, productive rate: 75.4%).
3, the preparation of compound (203)
In 500 milliliters of round-bottomed flasks, add (35.20 grams of compounds (202), 92.62 mMs), (18.13 grams of N-bromine succinimides, 101.9 mMs) and carrene (500 milliliters), this mixture under room temperature, stirred 12 hours.In the time completing reaction, decompression is lower to desolventizing.From carrene (100 milliliters) and hexane (500 milliliters) recrystallization, and acquisition compound (203) (34.51 grams, 75.33 mMs, productive rate: 81.3%).
4, the preparation of compound (204)
In 500 milliliters of round-bottomed flasks, add (42.56 grams of compounds (203), 92.62 mMs) and oxolane (1000 milliliters), drip positive BuLi (1.6M hexane solution) (55.57 milliliters, 138.9 mMs) in-78 ℃ to this flask.At same temperature, stir this mixture 1 hour, in reactant mixture, drip trimethylborate (15.49 milliliters, 138.9 mMs), temperature is increased to room temperature.Stir this reactant mixture 12 hours, in the time that reaction completes, add 1M hydrochloric acid solution (500 milliliters), the mixture that stirring forms 5 hours.The organic extract anhydrous magnesium sulfate drying obtaining with distilled water (500 milliliters) and ethyl acetate (400 milliliters) extraction, filters and reduces pressure down concentrated.From ethyl acetate (50 milliliters) and methyl alcohol (600 milliliters) recrystallization, and acquisition compound (204) (30.43 grams, 71.78 mMs, productive rate: 77.5%).
5, the preparation of compound (102)
In 500 milliliters of round-bottomed flasks, add (30.43 grams of compounds (204), 71.78 mMs), compound (205) (30.43 grams, 57.42 mMs), toluene (500 milliliters) and tetrakis triphenylphosphine palladium (Pd (PPh 3) 4) (4.15 grams, 3.59 mMs), under argon gas atmosphere, stir this mixture.Then drip therein wet chemical (200 milliliters), the mixture of formation heats 4 hours under stirring and counterflow condition.In the time completing reaction, in reactant mixture, add distilled water (600 milliliters), then use ethyl acetate (500 milliliters) extraction.The organic extract anhydrous magnesium sulfate drying obtaining, filters and reduces pressure down concentrated.By silica gel chromatography (carrene: hexane=1:10) with from hexane recrystallization, and acquisition compound (102) (35.78 grams, 43.11 mMs, productive rate: 75.1%), be light yellow product.
1H?NMR(400MHz,CDCl 3):=7.94(d,1H),7.92(d,1H),7.89(s,1H),7.84(s,1H),7.79(s,1H),7.75(d,1H),7.68-7.65(m,7H),7.61(d,1H),7.56-7.53(m,9H),7.38-7.35(m,9H),7.33-7.27(m,8H),1.65(s,6H)
MS/FAB C 63h 46si830.34 (measured value).(831.12 calculated value)
Example 2: the preparation of active layer electron donor material (103) comprises the steps
1, the preparation of compound (206)
In 1 liter of round-bottomed flask, add 1, (100 grams of 2-dibromobenzenes, 423.9 mM), 2-(9,9 '-dimethyl) fluorenes boric acid (111.0 grams, 466.3 mMs), toluene (1000 milliliters) and tetrakis triphenylphosphine palladium (Pd (PPh 3) 4) (24.5 grams, 21.2 mMs), under argon gas atmosphere, stir this mixture.Then in mixture, drip wet chemical (300 milliliters), the mixture of formation heats 4 hours under stirring and counterflow condition.In the time completing reaction, in reactant mixture, add distilled water (1500 milliliters), then use ethyl acetate (800 milliliters) extraction.The organic extract anhydrous magnesium sulfate drying obtaining, filters and reduces pressure down concentrated.By silica gel chromatography (ethyl acetate: hexane=1:30), obtain product, the bromo-2-of 1-(9,9 '-dimethyl) fluorenyl benzene (75.52 grams, 217.0 mMs, productive rate: 51.2%).
In 1 liter of round-bottomed flask, add the bromo-2-(9 of 1-, 9 '-dimethyl) (51.68 grams of fluorenyl benzene, 148.5 mMs) and oxolane (1000 milliliters), drip positive BuLi (1.6M hexane solution) (89.0 milliliters, 222.5 mMs) in-78 ℃ to this flask.At same temperature, stir this mixture 1 hour, in reactant mixture, drip trimethylborate (24.8 milliliters, 222.5 mMs), temperature is increased to room temperature.Stir this reactant mixture 12 hours, in the time that reaction completes, add therein 1M hydrochloric acid solution (500 milliliters, stir the mixture 5 hours forming.The organic extract anhydrous magnesium sulfate drying obtaining with distilled water (500 milliliters) and ethyl acetate (400 milliliters) extraction, filters and reduces pressure down concentrated.From ethyl acetate (50 milliliters) and methyl alcohol (600 milliliters) recrystallization, and acquisition compound (206) (29.31 grams, 93.34 mMs, productive rate: 62.9%).
2, the preparation of compound (207)
In 500 milliliters of round-bottomed flasks, add (34.54 grams of compounds (206), 110.0 mMs), (28.16 grams of 9-bromine anthracenes, 88.0 mMs), toluene (500 milliliters) and tetrakis triphenylphosphine palladium (Pd (PPh 3) 4) (2.45 grams, 2.05 mMs), under argon gas atmosphere, stir this mixture.Then drip therein wet chemical (100 milliliters), the mixture of formation heats 4 hours under stirring and counterflow condition.In the time completing reaction, in reactant mixture, add distilled water (500 milliliters), then use ethyl acetate (500 milliliters) extraction.The organic extract anhydrous magnesium sulfate drying obtaining, filters and reduces pressure down concentrated.By silica gel chromatography (carrene: hexane=1:15), and acquisition compound (207) (32.34 grams, 72.51 mMs, productive rate: 82.4%).
3, the preparation of compound (208)
In 500 milliliters of round-bottomed flasks, add (41.44 grams of compounds (207), 92.62 mMs), (18.13 grams of N-bromine succinimides, 101.9 mMs) and carrene (250 milliliters), this mixture under room temperature, stirred 12 hours.In the time completing reaction, decompression is lower to desolventizing.From carrene (150 milliliters) and hexane (800 milliliters) recrystallization, and acquisition compound (208) (30.52 grams, 58.24 mMs, productive rate: 62.9%).
4, the preparation of compound (209)
In the round-bottomed flask of 500 milliliters, add (48.53 grams of compounds (208), 92.62 mMs) and oxolane (800 milliliters), drip positive BuLi (1.6M hexane solution) (55.57 milliliters, 138.9 mMs) in-78 ℃ to this flask.At same temperature, stir this mixture 1 hour, in reactant mixture, drip trimethylborate (15.49 milliliters, 138.9 mMs), temperature is increased to room temperature.Stir this reactant mixture 12 hours, in the time that reaction completes, add therein 1M hydrochloric acid solution (400 milliliters), the mixture that stirring forms 5 hours.The organic extract anhydrous magnesium sulfate drying obtaining with distilled water (500 milliliters) and ethyl acetate (500 milliliters) extraction, filters and reduces pressure down concentrated.From ethyl acetate (100 milliliters) and methyl alcohol (800 milliliters) recrystallization, and acquisition compound (209) (32.33 grams, 65.98 mMs, productive rate: 71.2%).
5, the preparation of compound (103)
In 500 milliliters of round-bottomed flasks, add (35.17 grams of compounds (209), 71.78 mMs), compound (205) (30.43 grams, 57.42 mMs), toluene (600 milliliters) and tetrakis triphenylphosphine palladium (Pd (PPh 3) 4) (4.15 grams, 3.59 mMs), under argon gas atmosphere, stir this mixture.Then drip therein wet chemical (100 milliliters), the mixture of formation heats 4 hours under stirring and counterflow condition.When completing when reaction, in reactant mixture, add distilled water (500 milliliters, then use ethyl acetate (500 milliliters) extraction.The organic extract anhydrous magnesium sulfate drying obtaining, filters and reduces pressure down concentrated.By silica gel chromatography (carrene: hexane=1:10) with from hexane recrystallization, and acquisition compound (103) (31.76 grams, 35.45 mMs, productive rate: 61.7%), be faint yellow product.
1H?NMR(400MHz,CDCl 3):δ=7.94(d,1H),7.90(d,2H),7.84-7.82(m,2H),7.78(s,2H),7.68-7.65(m,5H),7.62(d,2H),7.57-7.54(m,9H),7.38-7.34(m,10H),7.33-7.27(m,7H),1.67(s,6H),1.66(s,6H)
MS/FAB C 69h 52si896.38 (measured value).(897.23 calculated value)
The embodiment that stacks gradually each layer of photovoltaic cell is as follows:
Some with lot number ITO Conducting Glass, specification is 15 millimeters × 15 millimeters, and the thickness of ITO is about 130 nanometers, and its square resistance is about 20 ohm/.Use successively acetone, micron order semiconductor special purpose detergent, deionized water, 10 minutes clean ITO substrate surfaces of the ultrasonic processing of isopropyl alcohol, put into subsequently and at 80 ℃ of constant temperature ovens, leave standstill 4 hours and dry.
ITO substrate after oven dry is used oxygen plasma treatment 4 minutes, remove organic attachment film and the organic pollution of ITO surface attachment, subsequently the substrate being made by said method proceeded to anhydrous and oxygen-free, be full of the special gloves case (manufacture of VAC company of the U.S.) of high pure nitrogen.Under this glove box inert atmosphere, polymer donor material and electron acceptor material are placed in respectively to clean sample bottle, with conventional organic solvent (as chlorobenzene, toluene etc.) dissolve and be mixed with solution, be placed on heating and stir on mixing platform, obtain clear filtrate with 0.45 micron of polytetrafluoroethylene (PTFE) membrane filtration.Then according to a certain percentage polymer donor material and electron acceptor material are mixed, be placed on heating mixing platform and stir.
Subsequently, device is proceeded in Vacuum Deposition chamber, open mechanical pump and molecular pump, when reaching 3 × 10 in plating chamber -4after the high vacuum of Pa, start AM aluminum metallization film (100 nanometer) as extraction electrode.By mask frame, each electrode and active layer are made to the pattern designing.The light-emitting zone of device is defined as 0.15 square centimeter by mask and the mutual region covering of ITO.
Solar cell is energy conversion device, solar energy is converted to electric energy, thus the mensuration of any solar cell device performance parameter, finally all will be take sunlight as testing standard.In laboratory, the radiant illumination of conventional AM1.5G measurement standard is 100 milliwatt/square centimeters.In the time carrying out polymer solar cells performance test with solar simulation light, first determine the whether irradiance of compound AM1.5G of light source with standard cell.Standard silicon solar cell is through calibration: under AM1.5G standard spectrum, when the irradiation of 100 milliwatt/square centimeter radiant illuminations, the short circuit current obtaining is 125 milliamperes.Determine after irradiance, can test device.
Compared with prior art, the active layer material of this employing can improve the performance of photovoltaic cell device, especially energy conversion efficiency.
Certainly; the present invention also can have other various embodiments; in the situation that not deviating from spirit of the present invention and essence thereof; those of ordinary skill in the art are when making according to the present invention various corresponding changes and distortion, but these corresponding changes and distortion all should belong to the protection range of the appended claim of the present invention.

Claims (4)

1. an organic photovoltaic battery, comprises the substrate, anode, active layer and the negative electrode that stack gradually, it is characterized in that,
Active layer comprises the electron donor material and the electron acceptor material that are laminated, and wherein electron donor material is the organic compound that general formula (VI) represents, electron acceptor material is carbon 60 and derivative or carbon 70 and derivative thereof,
Figure FDA0000409226930000011
Wherein ,-A-B-represents phenylene;
P and Q represent independently: chemical bond or there is no substituting group or have one or more substituent (C 6-C 30) arlydene, described substituting group is selected from straight or branched and the saturated or undersaturated (C that there is no halogenic substituent or have halogenic substituent 1-C 30) alkyl, (C 6-C 30) aryl and halogen;
R 1represent hydrogen, (C 6-C 30) aryl;
R 2, R 3and R 4represent independently straight or branched and saturated or undersaturated (C 1-C 30) alkyl or (C 6-C 30) aryl;
R 11to R 18represent independently hydrogen, straight or branched and saturated or undersaturated (C 1-C 30) alkyl or (C 6-C 30) aryl;
R 21, R 22and R 23represent independently straight or branched and saturated or undersaturated (C 1-C 30) alkyl or (C 6-C 30) aryl; With
M is 1 or 2 integer.
2. photovoltaic cell as claimed in claim 1, is characterized in that, the material of substrate is glass, flexible macromolecule or metal base.
3. photovoltaic cell as claimed in claim 1, is characterized in that, the material of anode is metal oxide or the metal oxide that contains alloy.
4. photovoltaic cell as claimed in claim 1, is characterized in that, the material of negative electrode is light tight metal.
CN201310545652.9A 2013-11-06 2013-11-06 Organic photovoltaic cell Pending CN103811660A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201310545652.9A CN103811660A (en) 2013-11-06 2013-11-06 Organic photovoltaic cell

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201310545652.9A CN103811660A (en) 2013-11-06 2013-11-06 Organic photovoltaic cell

Publications (1)

Publication Number Publication Date
CN103811660A true CN103811660A (en) 2014-05-21

Family

ID=50708130

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201310545652.9A Pending CN103811660A (en) 2013-11-06 2013-11-06 Organic photovoltaic cell

Country Status (1)

Country Link
CN (1) CN103811660A (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101730731A (en) * 2007-05-21 2010-06-09 葛来西雅帝史派有限公司 Organic electroluminescent compounds and organic light emitting diode using the same
US20120298981A1 (en) * 2010-01-29 2012-11-29 Merck Patent Gmbh Styrene-based copolymers, in particular for use in optoelectronic components
CN102969449A (en) * 2012-11-20 2013-03-13 溧阳市生产力促进中心 Solar cell comprising electron transfer layer

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101730731A (en) * 2007-05-21 2010-06-09 葛来西雅帝史派有限公司 Organic electroluminescent compounds and organic light emitting diode using the same
US20120298981A1 (en) * 2010-01-29 2012-11-29 Merck Patent Gmbh Styrene-based copolymers, in particular for use in optoelectronic components
CN102969449A (en) * 2012-11-20 2013-03-13 溧阳市生产力促进中心 Solar cell comprising electron transfer layer

Similar Documents

Publication Publication Date Title
Xie et al. Efficient and stable low-bandgap perovskite solar cells enabled by a CsPbBr3-cluster assisted bottom-up crystallization approach
Berry et al. Perovskite photovoltaics: the path to a printable terawatt-scale technology
JP6271643B2 (en) Electronic devices including organic semiconductors
Yan et al. Choline chloride-modified SnO2 achieving high output voltage in MAPbI3 perovskite solar cells
Wang et al. A simple molecular structure of ortho-derived perylene diimide diploid for non-fullerene organic solar cells with efficiency over 8%
Li et al. Efficient lead acetate sourced planar heterojunction perovskite solar cells with enhanced substrate coverage via one-step spin-coating
WO2012068733A1 (en) Conjugated polymer containing isoindigo units, preparation method and use thereof
JP2016164128A (en) Organic compound, organic material thin film, photoelectric conversion layer, solution for forming photoelectric conversion layer, and photoelectric conversion element
CN108864415B (en) Organic n-type semiconductor polymer material based on naphthalimide-selenophene and preparation method and application thereof
Wu et al. Two-stage melt processing of phase-pure selenium for printable triple-mesoscopic solar cells
JP2011165963A (en) Organic dye and organic thin-film solar cell
CN110156616B (en) Synthesis method of doping-free hole transport material based on fluorene ethylene bridged aromatic ring nucleus and application of doping-free hole transport material in perovskite battery
CN108192083B (en) Conjugated polymer containing trifluoromethyl as well as preparation method and application thereof
CN114349771B (en) Hexabenzocoronene-based non-fullerene acceptor material and preparation and application thereof
JP2008091380A (en) Organic photoelectric conversion element
CN102969449A (en) Solar cell comprising electron transfer layer
Steponaitis et al. Enamine-based hole transporting materials for vacuum-deposited perovskite solar cells
CN103811660A (en) Organic photovoltaic cell
CN111171046B (en) Doping-free hole transport material based on tetrathienopyrrole and synthetic method and application thereof
Wang et al. Soluble hexamethyl-substituted subphthalocyanine as a dopant-free hole transport material for planar perovskite solar cells
CN103635482B (en) Purposes in cobalt complex active layer in preparing photovoltaic cell and corresponding photovoltaic cell
WO2016060181A1 (en) Solar cell
CN103811659A (en) Organic photovoltaic cell with hole transporting layer
CN103811661A (en) Organic photovoltaic cell with electron-transporting layer
CN103811657A (en) Organic photovoltaic cell with electron-transporting layer and hole-transporting layer

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20140521

WD01 Invention patent application deemed withdrawn after publication