CN105914297A - Organic photovoltaic cell and a preparation method thereof - Google Patents
Organic photovoltaic cell and a preparation method thereof Download PDFInfo
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- CN105914297A CN105914297A CN201610271039.6A CN201610271039A CN105914297A CN 105914297 A CN105914297 A CN 105914297A CN 201610271039 A CN201610271039 A CN 201610271039A CN 105914297 A CN105914297 A CN 105914297A
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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Abstract
The present invention provides an organic photovoltaic material comprising a substrate, a cathode interface layer, a vacuum injection layer, an organic photovoltaic material derivative layer, electron transporting layer and an anode. The invention also provides a preparation method for the mentioned material. The organic photovoltaic cell provided by the invention has high mobility, a high energy conversion rate, good material stability, good durability and a long battery life.
Description
Technical field
The invention belongs to photovoltaic material field, particularly to a kind of organic photovoltaic battery, further relate to the system of this photovoltaic cell
Preparation Method.
Background technology
Along with the becoming increasingly conspicuous of energy scarcity and environmental issue in global range, the utilization of regenerative resource causes widely
Pay attention to.Photovoltaic generation is as a kind of important regenerative resource form, and it is technology on the largest scaleization in current regenerative resource
One of generation mode of exploit condition and commercialized development prospect, is increasingly paid close attention to by people.In Guo Qujishinian, the sun
The manufacturing industry scale of energy cell panel expands rapidly.2013, the rate of increase of U.S.'s solar energy industry was up to 116%, at new forms of energy
In technical field leading.U.S.'s solar energy power generating project " star of solar energy " installed capacity reaches 1.5 ten thousand kW；Japan
SANYO solar energy Noah's ark generated output reaches 630kW, annual generating 530,000 kWh；The domestic world, Shenzhen landscape flower built up is won
Garden grid-connected photovoltaic system installed capacity of looking at reaches 1MW, the most comes into operation.
Photovoltaic effect the earliest is that Edmund Bequerel found in 1839, after more than 100 year (1954), along with
The development of silicon semiconductor industry, first solaode that can be used for actual power just comes out in AT&T Labs.This is too
Sun energy battery is based on the p-n junction of silicon semiconductor, and electricity conversion is 6%.
Organic solar batteries is as a kind of novel battery, with the feature that it is exclusive, constantly attracts more people
Put into the research and development in this field.The fast of its development speed also has benefited from its exclusive advantage and characteristic, such as:
It is preferable that organic material synthesizes low cost, function is prone to modulation, pliability and film property；The course of processing is relatively easy, can low temperature
Operation, element manufacturing cost is relatively low；Large area manufacture can be realized, flexible substrate, environmental friendliness, light portable etc. can be used.
Certain existing organic solar material still has many shortcomings: material transition rate is low, high bulk resistor, thus causes energy conversion rate
Low；The stability of material and durability are the best, and battery life is short.
Summary of the invention
Technical problem: in order to solve the defect of prior art, the invention provides a kind of energy transformation ratio height, stability
Good, the organic photovoltaic battery of good endurance.
Technical scheme: shown in a kind of organic photovoltaic material that the present invention provides, its structural formula such as formula (I) or formula (II):
Wherein, R1 and the R2 straight or branched alkane for H or 1-5 carbon atom independently.
Present invention also offers the preparation method of above-mentioned organic photovoltaic material, comprise the following steps:
(1) in DMF solvent, compound (1) and POCl3Room temperature reaction 0.5-1.5h, obtains compound (2)；
(2), under the conditions of alkalescence, compound (3) reacts 8-12h, molecule inner ring condensation in 340-350 DEG C, obtains compound (4)；
Wherein, R1 and the R2 straight or branched alkane for H or 1-5 carbon atom independently；
(3) in the presence of TFA catalyst, DDQ oxidant, compound (2) and compound (4) room temperature reaction 8-12h, obtain formula
(I) compound shown in；
Wherein, R1 and the R2 straight or branched alkane for H or 1-5 carbon atom independently.
Wherein, in step (1), compound (1) and POCl3Mol ratio be 1:(2-3)；In step (3), compound (2)
It is (1-1.2) with the mol ratio of compound (4): 1.
Present invention also offers a kind of organic photovoltaic material, shown in its structural formula such as formula (III):
Present invention also offers the preparation method of above-mentioned organic photovoltaic material, comprise the following steps:
(1) in DMF solvent, compound (1) and POCl3Room temperature reaction 0.5-1.5h, obtains compound (2)；
(2), under the conditions of alkalescence, compound (3-3) reacts 8-12h, molecule inner ring condensation in 340-350 DEG C, obtains compound (4-
3)；
(3) in the presence of TFA catalyst, DDQ oxidant, compound (2) and compound (4-3) room temperature reaction 8-12h,
Compound shown in formula (III)；
Wherein, in step (1), compound (1) and POCl3Mol ratio be 1:(2-3)；In step (3), compound (2)
It is (1-1.2) with the mol ratio of compound (4-3): 1.
Present invention also offers a kind of material derived thing of organic photovoltaic, shown in its structural formula such as formula (II):
Present invention also offers the preparation method of the material derived thing of above-mentioned organic photovoltaic, comprise the following steps: protect at argon
Protecting down, in the presence of triethylamine, tetrakis triphenylphosphine palladium, compound (III) and CuI 85-90 DEG C react 24-26h, obtaining
Compound (IV).
Preferably, the mol ratio of compound (III) and CuI is 1:(2-3).
Present invention also offers a kind of material derived thing of organic photovoltaic, shown in its structural formula such as formula (V) or formula (VI):
Present invention also offers the preparation method of the material derived thing of above-mentioned organic photovoltaic, comprise the following steps: protect at argon
Protecting down, in the presence of triethylamine, tetrakis triphenylphosphine palladium, compound (III) and CuI 85-90 DEG C react 24-26h, obtaining
Compound (V)；Under argon shield, in the presence of triethylamine, tetrakis triphenylphosphine palladium, compound (IV) and CuI 85-90 DEG C are anti-
Answer 24-26h, obtain compound (VI).
Preferably, the mol ratio of compound (IIII) or compound (IV) and CuI is 1:(2-3).
Present invention also offers a kind of organic photovoltaic battery, include successively:
(1) substrate；
(2) cathode interface layer；
(3) vacuum implanted layer；
(4) the material derived nitride layer of organic photovoltaic；
(5) electron transfer layer；
(6) anode；
Wherein, structural formula such as formula (I) or the formula (II) of described organic photovoltaic material are shown:
Wherein, R is the straight or branched alkane of H or 1-3 carbon atom.
As preferably, described substrate is europium doped-glass substrate.
Preferred as another kind, described cathode interface layer is the ito thin film of La doped.
Preferred as another kind, described vacuum implanted layer is the PEDOT:PSS layer of doping antioxidant；Described antioxidant
For hydroquinone, 2,6-di-tert-butyl-4-methy phenol, the content of described antioxidant accounts for the 0.04-of active layer quality
0.06%.
Preferred as another kind, described electron transfer layer is the Cr of sulfur doping2O3Thin film.
Preferred as another kind, described anode is aluminum electrode.
Present invention also offers the preparation method of a kind of organic photovoltaic battery, comprise the following steps:
(1) at europium doped-glass substrate surface, the ito thin film of La doped is prepared by spin-coating method or vapour deposition method；
(2) on the ito thin film surface of La doped, by spin-coating method or the PEDOT of vapour deposition method preparation doping antioxidant:
PSS layer；
(3) on the PEDOT:PSS layer surface of doping antioxidant, organic photovoltaic material is prepared by spin-coating method or vapour deposition method
Derivative layer；
(4) on organic photovoltaic material derived nitride layer surface, the Cr of sulfur doping is prepared by spin-coating method or vapour deposition method2O3Thin film；
(5) at the Cr of sulfur doping2O3Film surface, prepares aluminum electrode by vapour deposition method.
Beneficial effect: the organic photovoltaic material mobility high-energy conversion ratio that the present invention provides is high, the stablizing of material
Good, the good endurance of property, battery life is long.
Detailed description of the invention
Embodiment 1
Organic photovoltaic material, uses following methods to prepare:
(1) in DMF solvent, 2mol compound (1) and 4mol POCl3Room temperature reaction 1.5h, obtains compound (2)；
MS (m/z): 199.05；
(2), under the conditions of alkalescence, 1.5mol compound (3-1) reacts 8h, molecule inner ring condensation in 350 DEG C, obtains compound (4-
1)；
MS (m/z): 196.10；
(3) in the presence of TFA catalyst, DDQ oxidant, 1mol compound (2) and 1mol compound (4-1) room temperature reaction
8h, obtains compound (I-1) and compound (II-1)；
MS (m/z): 722.29.
Embodiment 2
Organic photovoltaic material, uses following methods to prepare:
(1) in DMF solvent, 2mol compound (1) and 6mol POCl3Room temperature reaction 0.5h, obtains compound (2)；
MS (m/z): 199.05；
(2), under the conditions of alkalescence, 1.5mol compound (3-2) reacts 12h, molecule inner ring condensation in 340 DEG C, obtains compound (4-
2)；
MS (m/z): 224.13；
(3) in the presence of TFA catalyst, DDQ oxidant, 1mol compound (2) and 1mol compound (4-2) room temperature reaction
12h, obtains compound (I-2) and compound (II-2).
MS (m/z): 778.35.
Embodiment 3
Organic photovoltaic material, uses following methods to prepare:
(1) in DMF solvent, 2mol compound (1) and 5mol POCl3Room temperature reaction 1h, obtains compound (2)；
MS (m/z): 199.05；
(2), under the conditions of alkalescence, 1.5mol compound (3) reacts 10h, molecule inner ring condensation in 345 DEG C, obtains compound (4)；
MS (m/z): 154.05；
(3) in the presence of TFA catalyst, DDQ oxidant, 1.1mol compound (2) and 1mol compound (4-3) room temperature are anti-
Answer 10h, obtain compound (I-3) and compound (II-3).
MS (m/z): 638.20.
Embodiment 4
The preparation of the material derived thing of organic photovoltaic, comprises the following steps: under argon shield, at triethylamine, four (triphenyls
Phosphine) in the presence of palladium, 1mol compound (III) and 2mol CuI 90 DEG C react 24h, obtain compound (IV).
MS (m/z): 764.06.
Embodiment 5
The preparation of the material derived thing of organic photovoltaic, comprises the following steps: under argon shield, at triethylamine, four (triphenyls
Phosphine) in the presence of palladium, 1mol compound (III) and 3mol CuI 85 DEG C react 26h, obtain compound (IV).
MS (m/z): 764.06.
Embodiment 6
Organic photovoltaic battery, includes successively:
(1) europium doped-glass substrate；
(2) ito thin film of La doped；
(3) the PEDOT:PSS layer of doping antioxidant；Wherein antioxidant be hydroquinone, 2,6-di-t-butyl-4-first
Base phenol, the content of described antioxidant accounts for the 0.04-0.06% of active layer quality
(4) the material derived nitride layer of organic photovoltaic；
(5) Cr of sulfur doping2O3Thin film；
(6) aluminum electrode；
The organic photovoltaic material of embodiment 1 to 5 is used for the material derived nitride layer of organic photovoltaic, prepares a collection of organic photovoltaic electricity
Pond, tests battery performance, is shown in Table 1.
Table 1 battery performance
Wherein, matched group uses fullerene to substitute the material derived nitride layer of organic photovoltaic.
Stability test:
Above-mentioned battery is heated five days, tests battery performance, be shown in Table 2.
Table 2 battery performance
Wherein, matched group uses fullerene to substitute the material derived nitride layer of organic photovoltaic.
The preparation method of above-mentioned organic photovoltaic battery, comprises the following steps:
(1) at europium doped-glass substrate surface, the ito thin film of La doped is prepared by spin-coating method or vapour deposition method；
(2) on the ito thin film surface of La doped, by spin-coating method or the PEDOT of vapour deposition method preparation doping antioxidant:
PSS layer；
(3) on the PEDOT:PSS layer surface of doping antioxidant, organic photovoltaic material is prepared by spin-coating method or vapour deposition method
Derivative layer；
(4) on organic photovoltaic material derived nitride layer surface, the Cr of sulfur doping is prepared by spin-coating method or vapour deposition method2O3Thin film；
(5) at the Cr of sulfur doping2O3Film surface, prepares aluminum electrode by vapour deposition method.
Wherein in prior art, spin-coating method or vapour deposition method all can realize the purpose of the present invention.
Claims (7)
1. an organic photovoltaic battery, it is characterised in that: include successively:
(1) substrate；
(2) cathode interface layer；
(3) vacuum implanted layer；
(4) the material derived nitride layer of organic photovoltaic；
(5) electron transfer layer；
(6) anode；
Wherein, structural formula such as formula (I) or the formula (II) of described organic photovoltaic material are shown:
Wherein, R is the straight or branched alkane of H or 1-3 carbon atom.
A kind of organic photovoltaic battery the most according to claim 1, it is characterised in that: described substrate is europium doped-glass base
The end.
A kind of organic photovoltaic battery the most according to claim 1, it is characterised in that: described cathode interface layer is La doped
Ito thin film.
A kind of organic photovoltaic battery the most according to claim 1, it is characterised in that: described vacuum implanted layer is doping antioxygen
The PEDOT:PSS layer of agent；Described antioxidant be hydroquinone, 2,6-di-tert-butyl-4-methy phenol, described antioxidant
Content account for the 0.04-0.06% of active layer quality.
A kind of organic photovoltaic battery the most according to claim 1, it is characterised in that: described electron transfer layer is sulfur doping
Cr2O3Thin film.
A kind of organic photovoltaic battery the most according to claim 1, it is characterised in that: described anode is aluminum electrode.
7. the preparation method of a kind of organic photovoltaic battery described in claim 1, it is characterised in that: comprise the following steps:
(1) at europium doped-glass substrate surface, the ito thin film of La doped is prepared by spin-coating method or vapour deposition method；
(2) on the ito thin film surface of La doped, the PEDOT:PSS layer of doping antioxidant is prepared by spin-coating method or vapour deposition method；
(3) on the PEDOT:PSS layer surface of doping antioxidant, organic photovoltaic is prepared by spin-coating method or vapour deposition method material derived
Nitride layer；
(4) on organic photovoltaic material derived nitride layer surface, the Cr of sulfur doping is prepared by spin-coating method or vapour deposition method2O3Thin film；
(5) at the Cr of sulfur doping2O3Film surface, prepares aluminum electrode by vapour deposition method.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110400876A (en) * | 2018-04-25 | 2019-11-01 | 杭州纤纳光电科技有限公司 | A kind of perovskite thin film and its preparation method and application adulterating antioxidant |
| CN111384275A (en) * | 2018-12-29 | 2020-07-07 | Tcl集团股份有限公司 | Thin film, preparation method thereof and light-emitting diode |
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| CN103333185A (en) * | 2013-05-04 | 2013-10-02 | 福州大学 | Organic solar cell material with wide spectrum absorption |
| WO2014025435A2 (en) * | 2012-05-15 | 2014-02-13 | Forrest Stephen R | Dipyrrin based materials for photovoltaics, compounds capable of undergoing symmetry breaking intramolecular charge transfer in a polarizing medium and organic photovoltaic devices comprising the same |
| CN105308768A (en) * | 2013-02-21 | 2016-02-03 | 赫里亚泰克有限责任公司 | Optoelectronic component |
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2016
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| CN102453229A (en) * | 2010-10-19 | 2012-05-16 | 海洋王照明科技股份有限公司 | Metalloporphyrin-thienopyrazine organic semiconductor material, preparation method thereof and application thereof |
| WO2014025435A2 (en) * | 2012-05-15 | 2014-02-13 | Forrest Stephen R | Dipyrrin based materials for photovoltaics, compounds capable of undergoing symmetry breaking intramolecular charge transfer in a polarizing medium and organic photovoltaic devices comprising the same |
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| CN110400876A (en) * | 2018-04-25 | 2019-11-01 | 杭州纤纳光电科技有限公司 | A kind of perovskite thin film and its preparation method and application adulterating antioxidant |
| CN111384275A (en) * | 2018-12-29 | 2020-07-07 | Tcl集团股份有限公司 | Thin film, preparation method thereof and light-emitting diode |
| CN111384275B (en) * | 2018-12-29 | 2021-08-10 | Tcl科技集团股份有限公司 | Thin film, preparation method thereof and light-emitting diode |
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