WO2015004393A1 - Procédé de fabrication d'une couche active susceptible d'émettre un courant électrique sous irradiation - Google Patents
Procédé de fabrication d'une couche active susceptible d'émettre un courant électrique sous irradiation Download PDFInfo
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- WO2015004393A1 WO2015004393A1 PCT/FR2014/051772 FR2014051772W WO2015004393A1 WO 2015004393 A1 WO2015004393 A1 WO 2015004393A1 FR 2014051772 W FR2014051772 W FR 2014051772W WO 2015004393 A1 WO2015004393 A1 WO 2015004393A1
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- WIPO (PCT)
- Prior art keywords
- ferroelectric
- crystallizing
- polymer
- active layer
- solvent
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 229920000642 polymer Polymers 0.000 claims abstract description 44
- 239000004065 semiconductor Substances 0.000 claims abstract description 22
- 239000002861 polymer material Substances 0.000 claims abstract 4
- 239000000463 material Substances 0.000 claims description 73
- 239000000203 mixture Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 17
- 230000010287 polarization Effects 0.000 claims description 15
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 claims description 11
- 230000005684 electric field Effects 0.000 claims description 10
- -1 Cyclohexaxone Chemical compound 0.000 claims description 7
- 229920001940 conductive polymer Polymers 0.000 claims description 7
- 239000011368 organic material Substances 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 238000005286 illumination Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 238000005191 phase separation Methods 0.000 claims description 5
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- 230000008020 evaporation Effects 0.000 claims description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 claims description 2
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 229930188620 butyrolactone Natural products 0.000 claims description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910003472 fullerene Inorganic materials 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 230000003381 solubilizing effect Effects 0.000 claims description 2
- 150000003577 thiophenes Chemical class 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 230000005611 electricity Effects 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 230000009466 transformation Effects 0.000 abstract 1
- 230000005621 ferroelectricity Effects 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 239000011147 inorganic material Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 238000010494 dissociation reaction Methods 0.000 description 3
- 230000005593 dissociations Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 230000001131 transforming effect Effects 0.000 description 3
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000013086 organic photovoltaic Methods 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 description 1
- XLOFNXVVMRAGLZ-UHFFFAOYSA-N 1,1-difluoroethene;1,1,2-trifluoroethene Chemical group FC(F)=C.FC=C(F)F XLOFNXVVMRAGLZ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- AYCANDRGVPTASA-UHFFFAOYSA-N 1-bromo-1,2,2-trifluoroethene Chemical group FC(F)=C(F)Br AYCANDRGVPTASA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 101000701286 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) Alkanesulfonate monooxygenase Proteins 0.000 description 1
- 101000983349 Solanum commersonii Osmotin-like protein OSML13 Proteins 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000002547 anomalous effect Effects 0.000 description 1
- 238000000089 atomic force micrograph Methods 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000037230 mobility Effects 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 229920006126 semicrystalline polymer Polymers 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical compound C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- 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
- 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
-
- 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
- H10K30/50—Photovoltaic [PV] devices
-
- 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
- H10K30/60—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation in which radiation controls flow of current through the devices, e.g. photoresistors
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- 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
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Definitions
- a method of manufacturing an active layer capable of emitting an electric current under irradiation is a method of manufacturing an active layer capable of emitting an electric current under irradiation.
- the present invention relates to the field of organic electronics for photovoltaic energy that is to say the conversion of light energy into electricity. More particularly, this invention relates to a method of manufacturing an active layer capable of emitting an electric current under irradiation associating a ferroelectric material and a semiconductive polymer for transforming light energy into electricity.
- Photovoltaic cells There are currently devices for transforming light energy into electricity, photovoltaic cells. These devices consist of a cathode, an active layer and an anode. Photovoltaic cells can be made with inorganic materials or organic materials. Photovoltaic cells made from inorganic materials are well known, their efficiency is high, more than 25% but their manufacturing cost is high because the implementation of inorganic materials is difficult. Organic materials have the advantage of being inexpensive, easy to implement, and flexible devices can be achieved with these materials. However, low yields are obtained using these materials in particular because of the way of transforming the light energy.
- the active layer of organic solar cells is generally composed of P3HT (poly (3-hexy.ththiophene)) and PCBM (methyl [6, 6] -phenyl-C61-butanoate).
- P3HT poly (3-hexy.ththiophene)
- PCBM methyl [6, 6] -phenyl-C61-butanoate
- the difference in energy level between the P3HT and the PCBM generates an internal electric field which makes it possible to dissociate the excitons created in the P3HT, the separation of the electron-hole pairs is therefore done at the P3HT-PCBM interfaces.
- the yields of the photovoltaic organic cells are low, in particular because of excessive recombination of the excitons, it is therefore necessary to find another way of dissociating the excitons to increase the yield of the photovoltaic organic cells.
- the P (VDF-TrFe) film can also be deposited between the two donor and acceptor materials of the active layer as described by Yang et al in their article entitled “Tuning the energy level of equilibrium between donor and acceptor with ferroelectric dipole efficiency in bilayer organic photovoltaic cells ", Advanced Materials, 2012, 24, 1455-1460.
- the photovoltaic current is not induced solely by ferroelectricity because there is concomitant of a donor / acceptor system.
- WO2010131254 discloses a method of manufacturing photovoltaic cells based on a mixture of ferroelectric and semiconductor materials. However, this process comprises many steps of manufacturing the active layer very difficult to apply to industry and large scale. In addition, no figure in this document can prove the operation of this device and therefore the feasibility thereof.
- compositions of organic semiconductor materials and ferroelectric polymers cited in this demand are unlikely to lead to a notable photovoltaic effect.
- polymers such as PVDF and PTrFE are ferroelectric only after a physical treatment such as stretching which is difficult to imagine in the compositions and associated morphologies described in this application.
- the Applicant has observed that the electric field generated by a material capable of crystallizing in ferroelectric form is sufficient to dissociate the excitons for particular compositions, typically major quantities of material capable of crystallizing in ferroelectric form associated with a method of simplified application. These compositions only involve a material capable of crystallizing under ferroelectric form a semi-conducting polymer in an unexpected morphology cylinder type semi ⁇ conductive polymer and provide excellent efficiency of photovoltaic conversion.
- the invention relates to a method for manufacturing a device comprising the following steps: Preparation of a solution comprising at least one solvent, a material or a mixture of materials capable of crystallizing in ferroelectric form and at least one semi-crystalline polymer conductive, these compounds being miscible in the said solvent for concentrations of less than 10% by mass, preferably less than 5%, the material or materials capable of crystallizing in ferroelectric form on the one hand and the conductive polymer or polymers on the other hand not being miscible with each other, Spinning, Dr.
- Blade or any other technique of this solution on a conductive electrode evaporation of the solvent, such that a phase separation between the material (s) capable of crystallizing in ferroelectric form on the one hand and the semiconductor polymer (s) on the other hand establishes a morphology.
- any material or mixture of materials capable of crystallizing in ferroelectric form can be used in the invention.
- the material or mixture of materials capable of crystallizing in ferroelectric form are organic materials, and preferably polymers. It can also be a material capable of crystallizing in ferroelectric form and of another material not necessarily capable of crystallizing in ferroelectric form when taken alone, but on condition that the mixture of the two materials is capable of crystallizing in the form of ferroelectric.
- polymers or mixtures of polymers containing the monomeric entities of vinylidene difluoride and trifluoroethylene, vinylidene difluoride and trifluoroethylene, vinylidene difluoride and hexafluoropropylene optionally added with a third monomer chosen from the following monomers: trifluoroethylene, tetrafluoroethylene, fluoride vinyl, perfluoroalkylvinylethers such as perfluoromethylvinyl ether, dichloroethylene, vinyl chloride, chloro trifluoroethylene, perfluoro (methyl vinyl ether), bromotrifluoroethylene, tetra fluoro propene, hexafluoropropylene.
- a third monomer chosen from the following monomers: trifluoroethylene, tetrafluoroethylene, fluoride vinyl, perfluoroalkylvinylethers such as perfluoromethylvinyl ether, dichloroethylene, vinyl chloride, chloro tri
- Odd polyamides such as PA7, PA9, PAA, PA13 may also be used as well as their mixtures.
- VDF-TrFe a copolymer of vinylidene with trifluoroethylene P
- the semiconductor material is an organic material, and more particularly a polymer.
- the conductive polymer may be an electron donor or acceptor. It can also be a mixture of semiconductor polymers.
- the semiconductive polymer is preferably chosen from polymers containing fluorene, thiophene, phenylenes, phenylenes, phenylene vinylidene, fullerenes, pyrilenes, carbazole derivatives derived from thiophenes such as benzodithiophene or cyclopentadithiophene, derived from fluorene, pyrrole and furan.
- the conductive polymer is poly- (3-hexylthiophene) P3HT.
- the mobilities of the semiconductor polymer are between 10 -7 cm W 1 and 10 4 cm 2 / V -1 s -1 .
- the invention also relates to a device comprising (a) a conductive electrode, (b) a second conductive electrode, (c) an active layer comprising a material capable of crystallizing in ferroelectric form and a semiconductor material, which separates from and the other two electrodes.
- a device comprising (a) a conductive transparent electrode, (b) a conductive metal electrode, (c) an active layer comprising a material capable of crystallizing in ferroelectric form and a semiconductor material, which separates on both sides the two electrodes
- the device comprising (a) a conductive transparent electrode, (b) a conductive electrode, (c) an active layer comprising a material capable of crystallizing in ferroelectric form and a semiconductor material, which separates on both sides the two electrodes, the material capable of crystallizing in ferroelectric form being polarized by mechanical deformation and / or by applying an electric field greater than the coercive field, and even more preferably by applying an electric field greater than the field coercive, to the electrodes of the device.
- transparent electrode an electrode whose transmittance is greater than 60% and preferably greater than 80%, for a thickness of the 100 nm electrode, the transmittance being measured at 555 nm using a spectrophotometer, for example a spectrophotometer lambda 19 from Perkin Elmer.
- conductive electrode is meant an electrode whose conductivity is between 10 and 10 9 S / cm.
- compositions constituting the active layer are chosen so that the proportion of material or materials capable of crystallizing in ferroelectric form is greater than 20% by mass relative to the total material capable of crystallizing in ferroelectric form and semiconductor polymer, and of preferably greater than 50%, and more preferably between 70 and 95%.
- the solvent necessary for the preparation of a solution comprising at least one solvent, a material or a mixture of materials capable of crystallizing in ferroelectric form and at least one semiconductive polymer, these compounds being miscible in the said solvent for concentrations of less than 10% by weight, it is one or more polar and / or aromatic solvents capable of solubilizing the ferroelectric polymer and the semiconductive polymer.
- the solvents will be chosen from the following: tetrahydrofuran, methyl ethyl ketone, dimethylformamide, N, dimethylacetamide,
- Cyclohexaxone Diaceton Alcohol, Diisobutyl Ketone, Butyrolactone, Isophorone, 1, 2-dimethoxyethane, chloroform, dichlorobenzene, ortho-dichlorobenzene.
- the preparation of the active layer is conducted in such a way that a phase separation of the two materials constituting the active layer results in a morphology where a material is dispersed in the other material on a scale below the ym, or has a co- continuity of the two materials to a scale below the ym.
- the types of morphologies mentioned above may also include the presence of a thin layer of the material or materials capable of crystallizing in ferroelectric form of less than 40 nm in contact with one or both electrodes.
- the preparation of the active layer is carried out in such a way that a phase separation of the two materials constituting the active layer leads to a morphology of the cylinder type of the semiconductor polymer after evaporation of the solvent.
- additives to the ferroelectric material provides an additional advantage because it makes it possible to limit the electric field necessary for the polarization essential for the operation of these devices.
- plasticizers are preferred, among which mention may be made of branched or linear phthalates, such as di-n-octyl, dibutyl, -2-ethylhexyl, di-ethylhexyl, di-isononyl and di-isodecyl phatalates.
- plasticizers can be used alone or in combination.
- additives will be introduced in proportions ranging from 0.01 to 95% and preferably from 0.01 to 40% and more preferably from 0.1 to 10% relative to the sum of the mixture of materials capable of crystallizing in ferroelectric form.
- These devices may have a remanent polarization following the polarization of the material capable of crystallizing in ferroelectric form. These devices are capable of producing an electric current under illumination.
- the conductive and preferably transparent electrode may be of organic or metallic nature. It can be composed of carbon nanotubes. It may be composed of semiconductive polymer such as PEDOT-PSS (poly (3,4-ethylenedioxythiophene) -poly (styrene sulfonate)).
- PEDOT-PSS poly (3,4-ethylenedioxythiophene) -poly (styrene sulfonate)
- the devices resulting from the process of the invention are used in temperature ranges below the Curie temperature of the material or materials capable of crystallizing in ferroelectric form considered.
- these devices have a remanent polarization following the polarization of the material capable of crystallizing in ferroelectric form.
- ITO electrode indium tin oxide
- an active layer comprising 90% by weight of P (VDF-TrFe) and 10% by weight of P3HT deposited by spin-coating on the ITO electrode from a 3% by weight solution of the two polymers in THF. a LiF / Al electrode.
- AFM and TEM images illustrate the morphology obtained ( Figure 1 and Figure 2). It shows the cylindrical distribution of the minority polymer (P3HT) (circles of Figure 1 (a)), and dark spots within the active layer ( Figure 2). illumination a current increase of about summer observed ( Figure 3 and Figure 4).
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
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US14/904,331 US20160141534A1 (en) | 2013-07-11 | 2014-07-10 | Method for producing an active layer capable of emitting an electric current under irradiation |
CN201480049600.5A CN105518893A (zh) | 2013-07-11 | 2014-07-10 | 用于制造在辐照下能够发出电流的活性层的方法 |
EP14747092.6A EP3020078A1 (fr) | 2013-07-11 | 2014-07-10 | Procédé de fabrication d'une couche active susceptible d'émettre un courant électrique sous irradiation |
SG11201600190XA SG11201600190XA (en) | 2013-07-11 | 2014-07-10 | Method for producing an active layer capable of emitting an electric current under irradiation |
JP2016524878A JP2016525793A (ja) | 2013-07-11 | 2014-07-10 | 光照射下で電流を放出可能な活性層の製造方法 |
KR1020167003533A KR20160032159A (ko) | 2013-07-11 | 2014-07-10 | 조명하에서 전류를 방출할 수 있는 활성층의 제조 방법 |
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FR13.56832 | 2013-07-11 | ||
FR1356832A FR3008548B1 (fr) | 2013-07-11 | 2013-07-11 | Procede de fabrication d'une couche active susceptible d'emettre un courant electrique sous irradiation |
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US (1) | US20160141534A1 (fr) |
EP (1) | EP3020078A1 (fr) |
JP (1) | JP2016525793A (fr) |
KR (1) | KR20160032159A (fr) |
CN (1) | CN105518893A (fr) |
FR (1) | FR3008548B1 (fr) |
SG (1) | SG11201600190XA (fr) |
WO (1) | WO2015004393A1 (fr) |
Cited By (3)
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CN104868048A (zh) * | 2015-05-13 | 2015-08-26 | 重庆科技学院 | 一种光致伸缩复合膜及其制作的光驱动器 |
WO2018065356A1 (fr) * | 2016-10-05 | 2018-04-12 | Merck Patent Gmbh | Composés semi-conducteurs organiques |
WO2018065352A1 (fr) * | 2016-10-05 | 2018-04-12 | Merck Patent Gmbh | Photodétecteur organique |
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CN105453662B (zh) | 2013-07-12 | 2021-06-11 | 康维达无线有限责任公司 | 用于支持休眠节点的邻居发现 |
EP3367455B1 (fr) * | 2017-02-24 | 2023-12-13 | Centre National de la Recherche Scientifique (CNRS) | Méthode de fabrication d'un dispositif optoélectronique multicolore comprenant plusieurs materiaux photoactifs |
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JP5326686B2 (ja) * | 2009-03-10 | 2013-10-30 | ダイキン工業株式会社 | 異常高温検出用素子を備える異常高温検出用装置 |
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2013
- 2013-07-11 FR FR1356832A patent/FR3008548B1/fr not_active Expired - Fee Related
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- 2014-07-10 WO PCT/FR2014/051772 patent/WO2015004393A1/fr active Application Filing
- 2014-07-10 SG SG11201600190XA patent/SG11201600190XA/en unknown
- 2014-07-10 KR KR1020167003533A patent/KR20160032159A/ko not_active Application Discontinuation
- 2014-07-10 EP EP14747092.6A patent/EP3020078A1/fr not_active Withdrawn
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EP1995736A1 (fr) * | 2007-05-22 | 2008-11-26 | Rijksuniversiteit Groningen | Dispositif ferroélectrique et barrière dýinjection modulable |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104868048A (zh) * | 2015-05-13 | 2015-08-26 | 重庆科技学院 | 一种光致伸缩复合膜及其制作的光驱动器 |
CN104868048B (zh) * | 2015-05-13 | 2018-02-02 | 重庆科技学院 | 一种光致伸缩复合膜及其制作的光驱动器 |
WO2018065356A1 (fr) * | 2016-10-05 | 2018-04-12 | Merck Patent Gmbh | Composés semi-conducteurs organiques |
WO2018065352A1 (fr) * | 2016-10-05 | 2018-04-12 | Merck Patent Gmbh | Photodétecteur organique |
US11183637B2 (en) | 2016-10-05 | 2021-11-23 | Raynergy Tek Incorporation | Organic photodetector |
US11196005B2 (en) | 2016-10-05 | 2021-12-07 | Raynergy Tek Incorporation | Organic semiconducting compounds |
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US20160141534A1 (en) | 2016-05-19 |
KR20160032159A (ko) | 2016-03-23 |
EP3020078A1 (fr) | 2016-05-18 |
CN105518893A (zh) | 2016-04-20 |
SG11201600190XA (en) | 2016-02-26 |
JP2016525793A (ja) | 2016-08-25 |
FR3008548B1 (fr) | 2016-12-09 |
FR3008548A1 (fr) | 2015-01-16 |
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