CN105742503A - Thiophene-modified novel organic photovoltaic cell and preparation method thereof - Google Patents
Thiophene-modified novel organic photovoltaic cell and preparation method thereof Download PDFInfo
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- CN105742503A CN105742503A CN201610286637.0A CN201610286637A CN105742503A CN 105742503 A CN105742503 A CN 105742503A CN 201610286637 A CN201610286637 A CN 201610286637A CN 105742503 A CN105742503 A CN 105742503A
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- H—ELECTRICITY
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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
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- 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
Abstract
The invention provides a thiophene-modified novel organic photovoltaic cell which comprises the components of (1) a substrate, (2), a cathode interface layer, (3), a vacuum impregnation layer, (4), a thiophene-modified novel organic photovoltaic material derivative layer, (5), an electron transmission layer and (6), an anode, wherein the substrate, the cathode interface layer, the vacuum impregnation layer, the thiophene-modified novel organic photovoltaic material derivative layer, the electron transmission layer and the anode are successively arranged. The thiophene-modified novel organic photovoltaic cell has advantages of high material mobility, high conversion rate, high material stability, high durability and long cell service life.
Description
Technical field
The invention belongs to photovoltaic material field, modify novel organic photovoltaic battery, the preparation method further relating to this photovoltaic material particularly to a kind of thiophene.
Background technology
Along with the becoming increasingly conspicuous of energy scarcity and environmental issue in global range, the utilization of regenerative resource causes to be paid attention to widely.Photovoltaic generation is as a kind of important regenerative resource form, and it is one of generation mode of technology on the largest scaleization exploit condition and commercialized development prospect in current regenerative resource, increasingly receives the concern of people.In in the past few decades, the manufacturing industry scale of solar panel expands rapidly.2013, the rate of increase of U.S.'s solar energy industry was up to 116%, leading in technical field of new energies.U.S.'s solar energy power generating project " star of solar energy " installed capacity reaches 1.5 ten thousand kW；Japan's SANYO solar energy Noah's ark generated output reaches 630kW, annual generating 530,000 kWh；Domestic landscape flower Review Garden, the world, Shenzhen grid-connected photovoltaic system installed capacity built up reaches 1MW, comes into operation at present.
Photovoltaic effect the earliest is that EdmundBequerel found in 1839, and 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 solaode 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 and puts into the research and development in this field.The fast of its development speed also has benefited from its exclusive advantage and characteristic, for instance: it is all better that organic material synthesis cost is low, 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 causing that energy conversion rate is low；The stability of material and durability are good not, and battery life is short.
Summary of the invention
Technical problem: in order to solve the defect of prior art, the invention provides the thiophene novel organic photovoltaic material of modification of a kind of energy transformation ratio height, good stability, good endurance.
Technical scheme: a kind of thiophene provided by the invention modifies novel organic photovoltaic material, its structural formula such as formula (I) or formula
(II) shown in:
Wherein, R1 and R2 independently be the straight or branched alkane of H or 1-5 carbon atom.
Present invention also offers the preparation method that above-mentioned thiophene modifies novel 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 alkali condition, compound (3) reacts 8-12h, molecule inner ring condensation in 340-350 DEG C, obtains compound (4)；
Wherein, R1 and R2 independently be the straight or branched alkane of H or 1-5 carbon atom；
(3) under TFA catalyst, DDQ oxidant exist, compound (2) and compound (3) room temperature reaction 8-12h, obtain the compound shown in formula (I)；
Wherein, R1 and R2 independently be the straight or branched alkane of H or 1-5 carbon atom.
Wherein, in step (1), compound (1) and POCl3Mol ratio be 1:(2-3)；In step (3), the mol ratio of compound (2) and compound (4) is (1-1.2): 1.
Present invention also offers a kind of thiophene and modify novel organic photovoltaic material, its structural formula such as formula (III) or shown in formula (IV):
Present invention also offers the preparation method that above-mentioned thiophene modifies novel 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 alkali condition, compound (3-3) reacts 8-12h, molecule inner ring condensation in 340-350 DEG C, obtains compound (4-3)；
(3) under TFA catalyst, DDQ oxidant exist, compound (2) and compound (4-3) room temperature reaction 8-12h, obtain the compound shown in formula (III) and formula (IV)；
Wherein, in step (1), compound (1) and POCl3Mol ratio be 1:(2-3)；In step (3), the mol ratio of compound (2) and compound (4-3) is (1-1.2): 1.
Present invention also offers a kind of thiophene and modify the material derived thing of novel organic photovoltaic, its structural formula such as formula (V) or shown in formula (VI):
Present invention also offers the preparation method that above-mentioned thiophene modifies the material derived thing of novel organic photovoltaic; comprise the following steps: under argon shield; under triethylamine, tetrakis triphenylphosphine palladium exist; compound (III) and CuI85-90 DEG C of reaction 24-26h, obtain compound (V)；Under argon shield, under triethylamine, tetrakis triphenylphosphine palladium exist, compound (IV) and CuI85-90 DEG C react 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 thiophene and modify the material derived thing of novel organic photovoltaic, its structural formula such as formula (V) or shown in formula (VI):
Present invention also offers the preparation method that above-mentioned thiophene modifies the material derived thing of novel organic photovoltaic; comprise the following steps: under argon shield; under triethylamine, tetrakis triphenylphosphine palladium exist; compound (III) and CuI85-90 DEG C of reaction 24-26h, obtain compound (V)；Under argon shield, under triethylamine, tetrakis triphenylphosphine palladium exist, compound (IV) and CuI85-90 DEG C react 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 thiophene and modify novel organic photovoltaic battery, include successively:
(1) substrate；
(2) cathode interface layer；
(3) vacuum implanted layer；
(4) thiophene modifies the material derived nitride layer of novel organic photovoltaic；
(5) electron transfer layer；
(6) anode；
Wherein, described thiophene is modified shown in structural formula such as formula (I) or the formula (II) of novel organic photovoltaic material:
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 is hydroquinone, 2,6-di-tert-butyl-4-methy phenols, and the content of described antioxidant accounts for the 0.04-0.06% of active layer quality.
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 that a kind of thiophene modifies novel 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, 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, prepare thiophene by spin-coating method or vapour deposition method and modify the material derived nitride layer of novel organic photovoltaic；
(4) modify the material derived nitride layer surface of novel organic photovoltaic at thiophene, prepared the Cr of sulfur doping 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: thiophene provided by the invention modifies novel organic photovoltaic material mobility high-energy conversion ratio height, the good stability of material, good endurance, and battery life is long.
Detailed description of the invention
Embodiment 1
Thiophene modifies novel organic photovoltaic material, adopts following methods to prepare:
(1) in DMF solvent, 2mol compound (1) and 4molPOCl3Room temperature reaction 1.5h, obtains compound (2)；
MS (m/z): 249.07；
(2), under alkali condition, 1.5mol compound (3-1) reacts 8h, molecule inner ring condensation in 350 DEG C, obtains compound (4-1)；
MS (m/z): 224.04；
(3) under TFA catalyst, DDQ oxidant exist, 1mol compound (2) and 1mol compound (4-1) room temperature reaction 8h, obtain compound (I-1) and compound (II-1)；
MS (m/z): 878.20.
Embodiment 2
Thiophene modifies novel organic photovoltaic material, adopts following methods to prepare:
(1) in DMF solvent, 2mol compound (1) and 6molPOCl3Room temperature reaction 0.5h, obtains compound (2)；
MS (m/z): 249.07；
(2), under alkali condition, 1.5mol compound (3-2) reacts 12h, molecule inner ring condensation in 340 DEG C, obtains compound (4-2)；
MS (m/z): 280.10；
(3) under TFA catalyst, DDQ oxidant exist, 1mol compound (2) and 1mol compound (4-2) room temperature reaction 12h, obtain compound (I-2) and compound (II-2).
MS (m/z): 962.30.
Embodiment 3
Thiophene modifies novel organic photovoltaic material, adopts following methods to prepare:
(1) in DMF solvent, 2mol compound (1) and 5molPOCl3Room temperature reaction 1h, obtains compound (2)；
MS (m/z): 249.07；
(2), under alkali condition, 1.5mol compound (3-3) reacts 10h, molecule inner ring condensation in 345 DEG C, obtains compound (4-3)；
MS (m/z): 210.03；
(3) under TFA catalyst, DDQ oxidant exist, 1.1mol compound (2) and 1mol compound (4-3) room temperature reaction 10h, obtain compound (III) and compound (IV).
MS (m/z): 850.17.
Embodiment 4
Thiophene modifies the preparation of the material derived thing of novel organic photovoltaic; comprise the following steps: under argon shield; under triethylamine, tetrakis triphenylphosphine palladium exist; 1mol compound (III) and 2molCuI90 DEG C of reaction 24h, obtain compound (V) and compound (VI).
MS (m/z): 978.03.
Embodiment 5
Thiophene modifies the preparation of the material derived thing of novel organic photovoltaic; comprise the following steps: under argon shield; under triethylamine, tetrakis triphenylphosphine palladium exist, 1mol compound (III) and 3molCuI85 DEG C react 26h, obtain compound (IV).
MS (m/z): 978.03.
Embodiment 6
Thiophene modifies novel 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 is hydroquinone, 2,6-di-tert-butyl-4-methy phenols, and the content of described antioxidant accounts for the 0.04-0.06% of active layer quality
(4) thiophene modifies the material derived nitride layer of novel organic photovoltaic；
(5) Cr of sulfur doping2O3Thin film；
(6) aluminum electrode；
The thiophene of embodiment 1 to 5 is modified novel organic photovoltaic material and is used for the thiophene modification material derived nitride layer of novel organic photovoltaic, prepare a collection of organic photovoltaic battery, test battery performance, in Table 1.
Table 1 battery performance
Wherein, matched group adopts fullerene to substitute thiophene and modifies the material derived nitride layer of novel organic photovoltaic.
Stability test:
Above-mentioned battery is heated five days, tests battery performance, in Table 2.
Table 2 battery performance
Wherein, matched group adopts fullerene to substitute thiophene and modifies the material derived nitride layer of novel 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, 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, prepare thiophene by spin-coating method or vapour deposition method and modify the material derived nitride layer of novel organic photovoltaic；
(4) modify the material derived nitride layer surface of novel organic photovoltaic at thiophene, prepared the Cr of sulfur doping 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. a thiophene modifies novel organic photovoltaic battery, it is characterised in that: include successively:
(1) substrate；
(2) cathode interface layer；
(3) vacuum implanted layer；
(4) thiophene modifies the material derived nitride layer of novel organic photovoltaic；
(5) electron transfer layer；
(6) anode；
Wherein, described thiophene is modified shown in structural formula such as formula (I) or the formula (II) of novel organic photovoltaic material:
Wherein, R is the straight or branched alkane of H or 1-3 carbon atom.
2. a kind of thiophene according to claim 1 modifies novel organic photovoltaic battery, it is characterised in that: described substrate is europium doped-glass substrate.
3. a kind of thiophene according to claim 1 modifies novel organic photovoltaic battery, it is characterised in that: described cathode interface layer is the ito thin film of La doped.
4. a kind of thiophene according to claim 1 modifies novel organic photovoltaic battery, it is characterised in that: described vacuum implanted layer is the PEDOT:PSS layer of doping antioxidant；Described antioxidant is hydroquinone, 2,6-di-tert-butyl-4-methy phenols, and the content of described antioxidant accounts for the 0.04-0.06% of active layer quality.
5. a kind of thiophene according to claim 1 modifies novel organic photovoltaic battery, it is characterised in that: described electron transfer layer is the Cr of sulfur doping2O3Thin film.
6. a kind of thiophene according to claim 1 modifies novel organic photovoltaic battery, it is characterised in that: described anode is aluminum electrode.
7. the preparation method that a kind of thiophene described in claim 1 modifies novel organic photovoltaic battery, 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, prepare thiophene by spin-coating method or vapour deposition method and modify the material derived nitride layer of novel organic photovoltaic；
(4) modify the material derived nitride layer surface of novel organic photovoltaic at thiophene, prepared the Cr of sulfur doping 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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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05102506A (en) * | 1991-10-03 | 1993-04-23 | Ricoh Co Ltd | Photovoltaic element |
| CN103374004A (en) * | 2013-07-02 | 2013-10-30 | 华南理工大学 | Amide porphyrin derivative and preparation method thereof |
| CN103554517A (en) * | 2013-11-15 | 2014-02-05 | 烟台澳土复合材料有限公司 | Novel efficient PPV (Poly-Phenylene Vinylene)-based organic photovoltaic material and preparation method thereof |
| CN103665328A (en) * | 2012-09-25 | 2014-03-26 | 海洋王照明科技股份有限公司 | Polymer semiconductor material containing alkylene fluorene and anthracene and preparation method and application thereof |
-
2016
- 2016-05-03 CN CN201610286637.0A patent/CN105742503A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05102506A (en) * | 1991-10-03 | 1993-04-23 | Ricoh Co Ltd | Photovoltaic element |
| CN103665328A (en) * | 2012-09-25 | 2014-03-26 | 海洋王照明科技股份有限公司 | Polymer semiconductor material containing alkylene fluorene and anthracene and preparation method and application thereof |
| CN103374004A (en) * | 2013-07-02 | 2013-10-30 | 华南理工大学 | Amide porphyrin derivative and preparation method thereof |
| CN103554517A (en) * | 2013-11-15 | 2014-02-05 | 烟台澳土复合材料有限公司 | Novel efficient PPV (Poly-Phenylene Vinylene)-based organic photovoltaic material and preparation method thereof |
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Application publication date: 20160706 |