WO2012014466A1 - フェナントロリン化合物、該化合物よりなる電子輸送材料、及び該化合物を含んでなる有機薄膜太陽電池 - Google Patents
フェナントロリン化合物、該化合物よりなる電子輸送材料、及び該化合物を含んでなる有機薄膜太陽電池 Download PDFInfo
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- WO2012014466A1 WO2012014466A1 PCT/JP2011/004246 JP2011004246W WO2012014466A1 WO 2012014466 A1 WO2012014466 A1 WO 2012014466A1 JP 2011004246 W JP2011004246 W JP 2011004246W WO 2012014466 A1 WO2012014466 A1 WO 2012014466A1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
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- 125000002347 octyl 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])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [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])O* 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical group N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- GQUJEMVIKWQAEH-UHFFFAOYSA-N titanium(III) oxide Chemical compound O=[Ti]O[Ti]=O GQUJEMVIKWQAEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- 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
- H10K85/60—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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2004—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte
- H01G9/2009—Solid electrolytes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2068—Panels or arrays of photoelectrochemical cells, e.g. photovoltaic modules based on photoelectrochemical cells
- H01G9/2072—Panels or arrays of photoelectrochemical cells, e.g. photovoltaic modules based on photoelectrochemical cells comprising two or more photoelectrodes sensible to different parts of the solar spectrum, e.g. tandem cells
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- 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
- H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
-
- 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
- H10K30/353—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 comprising blocking layers, e.g. exciton blocking layers
-
- 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
- H10K30/40—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising a p-i-n structure, e.g. having a perovskite absorber between p-type and n-type charge transport layers
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- Y02E10/542—Dye sensitized solar 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
- 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
Definitions
- the present invention relates to a novel phenanthroline compound, an electron transport material containing the compound, an organic thin film solar cell material, and an organic thin film solar cell and a stacked organic thin film solar cell using the same.
- An organic solar cell basically includes an n layer that transports electrons and a p layer that transports holes.
- An n-layer that uses a monomolecular adsorption of a sensitizing dye such as ruthenium dye on the surface of an inorganic semiconductor such as titania, and an electrolyte solution that uses an electrolyte solution as a p-layer is called a dye-sensitized solar cell (so-called Gretzel cell).
- Gretzel cell dye-sensitized solar cell
- organic thin-film solar cells consisting of organic thin films in both the n-layer and p-layer are all solid, so there are no drawbacks such as liquid leakage, they are easy to manufacture, and they do not use ruthenium, which is a rare metal. Attracted attention and researched energetically.
- Patent Document 1 discloses an organic thin-film solar cell composed of copper phthalocyanine (CuPc) as a p-layer, peryleneimides (PTCBI) as an n-layer, and a nitrogen-containing heterocyclic compound (basocproin: BCP) as an exciton blocking layer. It is disclosed.
- CuPc copper phthalocyanine
- PTCBI peryleneimides
- BCP nitrogen-containing heterocyclic compound
- the conversion efficiency is improved by inserting an i layer (a mixed layer of p material and n material) between the p layer and the n layer.
- the materials used at this time were still phthalocyanines, peryleneimides and BCP.
- the conversion efficiency was further improved by the stack cell configuration in which a number of p / i / n layers were stacked.
- the material system at this time was phthalocyanines, fullerene C 60 , bathocuproine (BCP). )Met.
- a conductive polymer is used as a p material (material constituting the p layer), and a fullerene C 60 compound is used as the n material (material constituting the n layer).
- the so-called bulk heterostructure has been mainly studied in which microlayer separation is induced by mixing and heat treatment to increase the heterointerface between the p material and the n material, thereby improving the conversion efficiency.
- material system that has been used is mostly soluble polythiophene compounds called P3HT as p material was soluble C 60 compounds called PCBM as an n material.
- Patent Document 2 discloses an organic thin-film solar cell using a phenanthroline derivative represented by the following formula as an exciton blocking layer. Paying attention to the fact that this phenanthroline derivative has an energy gap similar to that of BCP, it has been used for an exciton blocking layer.
- Patent Document 3 discloses an electron transporting laminated film using a perylenetetracarboxylic imide represented by the following formula, but there is no mention of use for an organic thin film solar cell.
- the operation process of an organic solar cell consists of (1) light absorption and exciton generation, (2) exciton diffusion, (3) charge separation, (4) charge transfer, and (5) electromotive force generation.
- organic substances generally have poor electron transport properties.
- improvement of the electron extraction efficiency from the organic layer to the cathode is also an issue. By solving such a problem, an organic thin-film solar cell with high conversion efficiency can be obtained.
- An object of the present invention is to provide an organic thin film solar cell material having high electron transport properties, a small energy barrier with an electrode, and exhibiting high efficiency photoelectric conversion characteristics when used in an organic thin film solar cell.
- the present inventors have conducted intensive research, and compounds having an electron-withdrawing phthalic anhydride skeleton, phthalimide skeleton, naphthalic anhydride skeleton or naphthalimide skeleton, and a phenanthroline skeleton are high.
- the present invention has been completed by finding that it has an electron transport property, has a small energy barrier with an electrode, and exhibits high efficiency photoelectric conversion characteristics when used in an organic thin film solar cell.
- an apparatus comprising the following compound, electron transport material, organic thin film solar cell material, organic thin film solar cell, stacked organic thin film solar cell, and organic thin film solar cell or stacked organic thin film solar cell.
- L is a single bond or a divalent group, and is bonded at any one of the 6-position, 8-position and 9-position indicated by * of 1,10-phenanthroline.
- Rg is a substituted or unsubstituted benzene ring or naphthalene ring.
- X is an oxygen atom or N—R 4 (where R 4 is a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted carbon number of 2 -40 alkenyl group, substituted or unsubstituted alkynyl group having 2 to 40 carbon atoms, substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, substituted or unsubstituted hetero ring having 5 to 40 ring atoms An aryl group, a substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 40 ring carbon atoms).
- R 11 to R 20 are each a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms, substituted or unsubstituted An alkynyl group having 2 to 40 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms, a substituted or unsubstituted carbon number An alkoxy group having 1 to 40 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 40 ring carbon atoms, a substituted or unsubstituted arylamino group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted carbon atom having 1 carbon atom ⁇ 40 al
- a is an integer from 0 to 4
- b is an integer from 0 to 3
- c is an integer from 0 to 2
- d is an integer from 0 to 2
- e is 0 or 1
- f is an integer from 0 to 2
- g is from 0 to An integer of 2
- h is an integer of 0 to 2
- i is an integer of 0 to 2
- j is an integer of 0 or 1.
- An organic thin-film solar cell in which an organic layer containing the compound according to 1 or 2 is disposed between a pair of electrodes. 6). 6. The organic thin-film solar cell according to 5 above, wherein the organic layer is a buffer layer on the cathode side. 7. 3. A stacked organic thin film solar cell, wherein the buffer layer in contact with the intermediate electrode of the stacked organic thin film solar cell in which a plurality of organic solar cell single cells are stacked contains the compound according to 1 or 2 above. 8). 8. An apparatus comprising the organic thin film solar cell according to 5 or 6 or the stacked organic thin film solar cell according to 7 above.
- the phenanthroline compound of the novel specific structure which shows a highly efficient photoelectric conversion characteristic when it uses as an organic thin film solar cell material can be provided.
- a novel electron transport material and organic thin film solar cell material can be provided.
- stacked organic thin film solar cell from which a highly efficient photoelectric conversion characteristic is acquired can be provided.
- the compound of the present invention has a structure represented by the following formula (1).
- L is a single bond or a divalent group, and is bonded at any one of the 6-position, 8-position and 9-position indicated by * of 1,10-phenanthroline.
- Rg is a substituted or unsubstituted benzene ring or naphthalene ring.
- X is an oxygen atom or N—R 4 .
- R 4 represents a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms, a substituted or unsubstituted carbon number 2 to 40 alkynyl groups, substituted or unsubstituted aryl groups having 6 to 40 ring carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 40 ring atoms, substituted or unsubstituted alkoxy groups having 1 to 40 carbon atoms Or a substituted or unsubstituted aryloxy group having 6 to 40 ring carbon atoms.
- R 4 is preferably an alkyl group having 1 to 40 carbon atoms.
- the compound represented by the formula (1) of the present invention is characterized in that it contains a skeleton structure selected from a phthalic anhydride skeleton, a phthalimide skeleton, a naphthalic anhydride skeleton, and a naphthalimide skeleton in the molecule. Including skeleton and naphthalimide skeleton. Since the compound of the present invention has these skeleton structures, it has high electron transport properties and a small energy barrier with respect to the electrode. Therefore, when the compound of the present invention is used for an organic thin film solar cell, an organic thin film solar cell exhibiting highly efficient photoelectric conversion characteristics can be obtained.
- L is a divalent group, a substituted or unsubstituted arylene group having 6 to 40 ring carbon atoms, specifically, a group in which two hydrogen atoms are removed from a benzene ring or the like, Substituted or unsubstituted heteroarylene groups having 5 to 40 ring atoms, specifically, pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, thiophene ring, furan ring, isoxazole ring, oxadiazole ring and A group in which two hydrogen atoms have been removed from a thiazole ring, etc., and further a compound having a quinoid structure, specifically, a group in which two hydrogen atoms have been removed from a benzoquinone skeleton, tetracyanoquinodimethane skeleton, etc.
- L is more preferably a single bond or an arylene group.
- conversion efficiency is improved by directly connecting phthalimide, which can increase Jsc (short circuit current density), which has high electron transport properties, and phenanthroline skeleton, which has high FF (form factor), to satisfy both performances. This is preferable.
- an arylene group such as a phenylene group is preferable because ⁇ conjugation is widened, which increases electron transportability and contributes to improvement in conversion efficiency.
- a phenylene group is preferable.
- the compound of the present invention represented by the formula (1) is preferably a compound represented by the following formula (2) or formula (3).
- X is the same group as X in the formula (1)
- L is a single bond or any group represented by the following formulas (L1) to (L12), and 1,10-phenanthroline It is bonded at any one of the 6th, 8th, and 9th positions indicated by *.
- each of R 11 to R 20 is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms, a substituted or unsubstituted group.
- a is an integer from 0 to 4
- b is an integer from 0 to 3
- c is an integer from 0 to 2
- d is an integer from 0 to 2
- e is 0 or 1
- f is an integer from 0 to 2
- g is from 0 to An integer of 2
- h is an integer of 0 to 2
- i is an integer of 0 to 2
- j is an integer of 0 or 1.
- the substituted or unsubstituted alkyl group having 1 to 40 carbon atoms of R 4 and R 11 to R 20 may be linear, branched or cyclic. Specific examples include, for example, methyl group, ethyl group, 1-propyl group, 2-propyl group, 1-butyl group, 2-butyl group, sec-butyl group, tert-butyl group, various pentyl groups, various Hexyl group, various octyl groups, various decyl groups, various dodecyl groups, 2-ethylhexyl group, 3,7-dimethyloctyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group , Norbornyl group, trifluoromethyl group, trichloromethyl group, benzyl group, ⁇ , ⁇ -dimethylbenzyl group, 2-phenylethyl group
- a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms is preferable from the viewpoint of availability of raw materials, and a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, and a cyclohexyl group are preferable. Etc. are more preferable.
- Preferred is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. The presence of an alkyl group in this range is preferable because solubility in a solvent is improved and coating properties are improved when an organic thin film solar cell is produced using a wet method.
- Examples of the substituent of the alkyl group include a fluorine atom, a chlorine atom, a bromine atom, a halogen atom such as an iodine atom, and an aryl group such as a phenyl group.
- the aryl group includes a methyl group, an ethyl group, and a propyl group. It may be further substituted with an alkyl group having 1 to 5 carbon atoms such as a group.
- the substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms of R 4 and R 11 to R 20 may be linear, branched or cyclic. Specific examples thereof include, for example, vinyl group, propenyl group, butenyl group, oleyl group, eicosapentaenyl group, docosahexaenyl group, styryl group, 2,2-diphenylvinyl group, 1,2,2-tril. Examples thereof include a phenyl vinyl group and a 2-phenyl-2-propenyl group.
- a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms is preferable, and a vinyl group, a styryl group, a 2,2-diphenylvinyl group, and the like are more preferable.
- the substituent of the alkenyl group include an aryl group such as a phenyl group, and the aryl group is further substituted with an alkyl group having 1 to 5 carbon atoms such as a methyl group, an ethyl group, or a propyl group. Also good.
- the substituted or unsubstituted alkynyl group having 2 to 40 carbon atoms of R 4 and R 11 to R 20 may be linear, branched or cyclic. Specific examples thereof include ethenyl group, propynyl group, 2-phenylethenyl group and the like. Of these, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms is preferable, and an ethenyl group, a 2-phenylethenyl group, and the like are more preferable from the viewpoint of availability of raw materials.
- Examples of the substituent of the alkynyl group include an aryl group such as a phenyl group, and the aryl group is further substituted with an alkyl group having 1 to 5 carbon atoms such as a methyl group, an ethyl group, or a propyl group. Also good.
- substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms of R 4 and R 11 to R 20 include, for example, a phenyl group, a 2-tolyl group, a 4-tolyl group, and 4-trifluoromethyl.
- Phenyl group 4-methoxyphenyl group, 4-cyanophenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, terphenylyl group, 3,5-diphenylphenyl group, 3,4-diphenylphenyl group, penta Phenylphenyl group, 4- (2,2-diphenylvinyl) phenyl group, 4- (1,2,2-triphenylvinyl) phenyl group, fluorenyl group, 1-naphthyl group, 2-naphthyl group, 9-anthryl group 2-anthryl group, 9-phenanthryl group, 1-pyrenyl group, chrycenyl group, naphthacenyl group, coronyl group and the like.
- a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is preferable from the viewpoint of availability of raw materials, and is preferably a phenyl group, a 4-biphenylyl group, a 1-naphthyl group, a 2-naphthyl group. And a 9-phenanthryl group and the like are more preferable.
- the substituent of the aryl group include an aryl group such as a phenyl group, and the aryl group is further substituted with an alkyl group having 1 to 5 carbon atoms such as a methyl group, an ethyl group, or a propyl group. Also good.
- the bond position in the case of a nitrogen-containing azole type heterocycle must be bonded not only with carbon but also with nitrogen. Can do.
- Examples thereof include, for example, furanyl group, thiophenyl group, pyrrolyl group, imidazolyl group, benzimidazolyl group, pyrazolyl group, benzpyrazolyl group, triazolyl group, oxadiazolyl group, pyridyl group, pyrazyl group, triazyl group, quinolyl group, Examples include a benzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, a dibenzothiophenyl group, and a carbazolyl group.
- a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms is preferable, and a furanyl group, a thiophenyl group, a pyridyl group, a carbazolyl group, and the like are more preferable from the viewpoint of availability of raw materials.
- the substituent of the heteroaryl group include an aryl group such as a phenyl group, and the aryl group is further substituted with an alkyl group having 1 to 5 carbon atoms such as a methyl group, an ethyl group, or a propyl group. May be.
- the substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms of R 4 and R 11 to R 20 may be linear, branched or cyclic, and specific examples thereof include, for example, a methoxy group Ethoxy group, 1-propyloxy group, 2-propyloxy group, 1-butyloxy group, 2-butyloxy group, sec-butyloxy group, tert-butyloxy group, various pentyloxy groups, various hexyloxy groups, various Octyloxy group, various decyloxy groups, various dodecyloxy groups, 2-ethylhexyloxy group, 3,7-dimethyloctyloxy group, cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group, 1-adamantyloxy group, 2 -Adamantyloxy group, norbornyloxy group, trifluoromethoxy group, ben Examples thereof include a diroxy group, an ⁇ ,
- a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms is preferable, and a methoxy group, an ethoxy group, a ter-butyloxy group, and the like are more preferable.
- the substituent of the alkoxy group include a fluorine atom, a chlorine atom, a bromine atom, a halogen atom such as an iodine atom, and an aryl group such as a phenyl group.
- the aryl group includes a methyl group, an ethyl group, and a propyl group. It may be further substituted with an alkyl group having 1 to 5 carbon atoms such as a group.
- substituted or unsubstituted aryloxy group having 6 to 40 ring carbon atoms of R 4 and R 11 to R 20 include a group in which the aryl group is represented by a nitrogen atom or L1 to L12 through oxygen
- bonded with is mentioned.
- a phenoxy group, a naphthoxy group, a phenanthryloxy group, and the like are preferable from the viewpoint of availability of raw materials.
- Examples of the substituent of the aryloxy group include an aryl group such as a phenyl group, and the aryl group is further substituted with an alkyl group having 1 to 5 carbon atoms such as a methyl group, an ethyl group, or a propyl group. May be.
- the substituted or unsubstituted arylamino group having 6 to 40 ring carbon atoms of R 11 to R 20 may be any group as long as at least one of the substituents bonded to the amino group is a substituted or unsubstituted aryl group.
- phenylamino group methylphenylamino group, diphenylamino group, di-p-tolylamino group, dim-tolylamino group, phenylm-tolylamino group, phenyl-1-naphthylamino group, phenyl-2-naphthylamino group, Examples thereof include a phenyl (sec-butylphenyl) amino group, a phenyl t-butylamino group, a bis (4-methoxyphenyl) amino group, and a phenyl-4-carbazolylphenylamino group.
- a diphenylamino group, a ditolylamino group, a bis (4-methoxyphenyl) amino group, and the like are preferable from the viewpoint of availability of raw materials.
- the substituent of the arylamino group include an aryl group such as a phenyl group, and the aryl group is further substituted with an alkyl group having 1 to 5 carbon atoms such as a methyl group, an ethyl group, or a propyl group. May be.
- the substituted or unsubstituted alkylamino group having 1 to 40 carbon atoms of R 11 to R 20 may be any group in which at least one of the substituents bonded to the nitrogen atom of the amino group is a substituted or unsubstituted alkyl group.
- these groups may be the same as or different from each other, and may be bonded to each other to form a ring.
- methylamino group dimethylamino group, methylethylamino group, diethylamino group, bis (2-hydroxyethyl) amino group, bis (2-methoxyethyl) amino group, piperidino group, morpholino group, etc.
- a dimethylamino group, a diethylamino group, a piperidino group and the like are preferable from the viewpoint of availability of raw materials.
- Examples of the substituent of the alkylamino group include an aryl group such as a phenyl group, and the aryl group is further substituted with an alkyl group having 1 to 5 carbon atoms such as a methyl group, an ethyl group, or a propyl group. May be.
- Rg in Formula (1) is a substituted or unsubstituted benzene ring or naphthalene ring.
- substituent for Rg include the same groups as R 11 to R 20 described above. Specifically, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms, a substituted or unsubstituted carbon group having 2 to 40 carbon atoms.
- examples of a preferable compound represented by the above formula (2) having a phthalimide skeleton include compounds having the following structures.
- examples of a more preferable compound represented by the above formula (2) having a phthalimide skeleton include compounds having the following structures.
- preferred compounds represented by the above formula (3) having a naphthalimide skeleton are the above (2-A) to (2-L), in place of the N-methylphthalimide skeleton, Examples thereof include compounds having an N-methylnaphthalimide skeleton bonded to a bonding group or a phenanthroline skeleton at the 4-position.
- Y represents a halogen element such as chlorine, bromine and iodine, or a pseudohalogen substituent such as a trifluoromethanesulfonyloxy group, a nonafluorobutanesulfonyloxy group, a methanesulfonyloxy group and a p-toluenesulfonyloxy group.
- a halogen element such as chlorine, bromine and iodine
- a pseudohalogen substituent such as a trifluoromethanesulfonyloxy group, a nonafluorobutanesulfonyloxy group, a methanesulfonyloxy group and a p-toluenesulfonyloxy group.
- M represents boronic acid groups such as —B (OH) 2 , pinacolatoboryl group, catecholboryl group and ester reagents thereof, organotin reagents such as Sn (Bu) 4 , and organosilicon reagents such as —Si (OH) 3.
- Represents a typical metal group represented by The typical metal group may be bonded to phthalic anhydride (Reaction Formula 1), or may be bonded to the phenanthroline compound via the bridging group L (Reaction Formula 2).
- Conditions for reacting these binding units having pseudohalogen substituents with reagents having typical metal groups include Kumada-Tamao coupling (Grignard reagent), Negishi coupling (organozinc reagent), Suzuki-Miyaura coupling (boron). Reagents, such as Kosugi, Ueda, Stille coupling (organotin reagent), Hiyama coupling (organosilicon reagent), etc. can be used.
- the compound represented by the above formula (3) can be produced by the same synthetic route as described below. (Y and M in the formula are the same as in the case of using the above phthalic anhydride.)
- metal catalyst examples include divalent palladium such as palladium chloride, palladium acetate, dichlorobis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) paradidium, tris (dibenzylideneacetone) dipalladium, and the like.
- Divalent nickel such as zerovalent palladium, nickel chloride, dichlorobis (triphenylphosphine) nickel, dichloro (1,3-bisdiphenylphosphinopropane) nickel, tetrakis (triphenylphosphine) nickel, tetracarbonylnickel, bis (cyclo 0-valent nickel such as octadiene) nickel.
- a ligand can be added to these metal catalysts.
- ligands that can be used in this case include pyridines such as 2,2′-bipyridine and 1,10-phenanthroline, triphenylphosphine, tri (o-tolyl) phosphine, tri (2-furyl) phosphine, Tricyclohexylphosphine, tri (t-butyl) phosphine, 2-di-t-butylphosphinobiphenyl (JohnPhos), 2-di-t-butylphosphino-2'-dimethylaminobiphenyl (DavePhos), 2-dicyclohexylphosphino- Monodentate phosphines such as 2 ′, 4 ′, 6′-triisopropyl-1,1′-biphenyl (XPhos), 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl (SPhos
- the electron transport material and the organic thin film solar cell material of the present invention are characterized by containing the compound of the present invention.
- the electron transport material and the organic thin-film solar cell material of the present invention may be the compound of the present invention alone or may contain the compound of the present invention and other components.
- the member of the organic thin film solar cell comprising the organic thin film solar cell material of the present invention may be formed of the material of the present invention alone or may be formed of a mixture of the material of the present invention and other components. .
- the organic thin film solar cell using the material of the present invention exhibits high efficiency conversion characteristics.
- the organic thin film solar cell of the present invention is characterized in that an organic layer containing the compound of the present invention is disposed between a pair of electrodes.
- the “organic layer” means a layer containing an organic compound in a solar cell.
- the compound of this invention should just be contained in at least 1 layer of the 1 or more organic layer which comprises a battery.
- the member containing the compound of this invention may contain the other component collectively.
- the organic layer containing the compound of the present invention is preferably a cathode-side buffer layer.
- the cell structure of the organic thin film solar cell of the present invention is not particularly limited as long as it includes an organic layer containing the above compound between a pair of electrodes. Specifically, a structure having the following element configuration on a stable insulating substrate can be given.
- the lower electrode corresponds to the anode and the upper electrode corresponds to the cathode.
- Lower electrode / p layer / n layer / upper electrode (2) Lower electrode / buffer layer / p layer / n layer / upper electrode (3) Lower electrode / p layer / n layer / buffer layer / upper electrode (4 ) Lower electrode / buffer layer / p layer / n layer / buffer layer / upper electrode (5) Lower electrode / buffer layer / p layer / i layer (or mixed layer of p and n materials) / n layer / buffer layer / Upper electrode (6) Lower electrode / p layer / n layer / buffer layer / intermediate electrode / buffer layer / p layer / n layer / buffer layer / upper electrode (7) lower electrode / buffer layer / p layer / n layer / buffer Layer / intermediate electrode / buffer layer / p layer / n layer / buffer layer / upper electrode (8) lower electrode / buffer layer / p layer / i layer (or mixed layer of p and n materials) / n
- the compounds of the present invention are preferably used in the buffer layers of the device configurations (2) to (8), particularly the buffer layer in contact with the cathode side buffer layer or the intermediate electrode, and the device configurations (3) to (8) It is preferable to use the compound of the present invention in the buffer layer, particularly the buffer layer in contact with the cathode side buffer layer or the intermediate electrode.
- each component will be briefly described.
- Lower electrode and upper electrode The material of the lower electrode and the upper electrode is not particularly limited, and a known conductive material can be used.
- a metal such as tin-doped indium oxide (ITO), gold (Au), osmium (Os), palladium (Pd) can be used as the electrode connected to the p layer, and silver as the electrode connected to the n layer.
- Metals such as (Ag), aluminum (Al), indium (In), calcium (Ca), platinum (Pt) lithium (Li), and binary metal systems such as Mg: Ag, Mg: In, and Al: Li are used. it can.
- a metal having a small work function or a metal system is preferable.
- the organic thin film solar cell is sufficiently transparent in the sunlight spectrum.
- the transparent electrode is formed using a known conductive material so that predetermined translucency can be secured by a method such as vapor deposition or sputtering.
- the light transmittance of the electrode on the light receiving surface is preferably 10% or more.
- one of the electrode portions includes a metal having a high work function, and the other includes a metal having a low work function.
- the material of the n layer is not particularly limited, but a compound having a function as an electron acceptor is preferable. If organic compounds, for example, fullerene compounds such as C 60, carbon nanotube, perylene compounds, polycyclic quinone, and quinacridone, the polymeric CN- poly (phenylene - vinylene), MEH-CN-PPV, -CN group or CF 3 group-containing polymers and poly (fluorene) compounds, and the like. A material having a high electron mobility is preferable, and a material having a low electron affinity is preferable. Thus, a sufficient open-circuit voltage can be realized by combining materials having a small electron affinity as the n layer.
- fullerene compounds such as C 60, carbon nanotube, perylene compounds, polycyclic quinone, and quinacridone
- the inorganic semiconductor compound of an n-type characteristic can be mentioned.
- doping semiconductors and compound semiconductors such as n-Si, GaAs, CdS, PbS, CdSe, InP, Nb 2 O 5 , WO 3 and Fe 2 O 3 , titanium dioxide (TiO 2 ), monoxide
- titanium oxide such as titanium (TiO) and dititanium trioxide (Ti 2 O 3 )
- conductive oxides such as zinc oxide (ZnO) and tin oxide (SnO 2 ). You may use combining more than a seed. Preference is given to using titanium oxide, particularly preferably titanium dioxide.
- the material of the p layer is not particularly limited, but a compound having a function as a hole acceptor is preferable.
- organic compounds include N, N′-bis (3-tolyl) -N, N′-diphenylbenzidine (mTPD), N, N′-dinaphthyl-N, N′-diphenylbenzidine (NPD) and 4 , 4 ′, 4 ′′ -tris (phenyl-3-tolylamino) triphenylamine (MTDATA) and the like, phthalocyanine (Pc), copper phthalocyanine (CuPc), zinc phthalocyanine (ZnPc) and titanyl phthalocyanine ( Phthalocyanines such as TiOPc), porphyrins typified by octaethylporphyrin (OEP), platinum octaethylporphyrin (PtOEP) and zinc tetraphenylporphyrin (ZnTPP),
- the i layer may be formed by mixing with the p layer compound or the n layer compound, or the compound of the present invention may be used alone as the i layer. In that case, any of the above exemplary compounds may be used for the p layer or the n layer.
- Buffer layer In general, organic thin film solar cells often have a thin total film thickness, and therefore, the upper electrode and the lower electrode are short-circuited, and the yield of cell fabrication often decreases. In such a case, it is preferable to prevent this by laminating a buffer layer. Since the compound of the present invention has a high electron transport property and a small energy barrier with the electrode, it is preferably used for a buffer layer, particularly a buffer layer on the cathode side. Moreover, when the organic thin-film solar cell of this invention is a laminated type, it is preferable to use the compound of this invention for the buffer layer which touches an intermediate electrode.
- a compound having sufficiently high carrier mobility is preferable so that the short-circuit current does not decrease even when the film thickness is increased.
- the low molecular compound include aromatic cyclic acid anhydrides represented by NTCDA shown below.
- the polymer compound include poly (3,4-ethylenedioxy) thiophene shown below: Examples thereof include known conductive polymers represented by polystyrene sulfonate (PEDOT: PSS) and polyaniline: camphorsulfonic acid (PANI: CSA).
- the inorganic semiconductor compounds exemplified as the material of the n layer may be used as the material of the buffer layer.
- the inorganic semiconductor compound CdTe, p-Si, SiC, GaAs, NiO, WO 3 and V 2 O 5 can be used.
- Substrate preferably has mechanical and thermal strength and transparency.
- a glass substrate and a transparent resin film.
- Transparent resin films include polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone.
- the laminated organic thin film solar cell is called a tandem solar cell, and has at least two power generation layers (organic solar cell single cells) and at least one intermediate electrode between a pair of electrodes.
- a transparent anode such as ITO is disposed on a transparent substrate
- a front cell composed of p layer / i layer / n layer is formed thereon, and p is formed on the intermediate electrode disposed thereon.
- a back cell composed of layer / i layer / n layer is formed, and a cathode is formed thereon.
- the description of the upper electrode, the lower electrode, the p layer, the n layer, the i layer, and the buffer layer constituting the stacked organic thin film solar cell is the same as described above.
- the laminated organic thin film solar cell of the present invention preferably contains the compound of the present invention in a buffer layer in contact with the intermediate electrode.
- Intermediate Electrode By forming an electron-hole recombination zone with the intermediate electrode, individual photoelectric conversion units of the stacked element can be separated. This layer serves to prevent the formation of a reverse heterojunction between the n layer of the front photoelectric conversion unit (front cell) and the p layer of the rear photoelectric conversion unit (back cell). The layer between the individual photoelectric conversion units provides a zone where electrons entering from the front photoelectric conversion unit and holes from the rear photoelectric conversion unit recombine. Efficient recombination of electrons entering from the front photoelectric conversion unit and holes from the rear photoelectric conversion unit is necessary when a photo-induced current is to occur in the stacked device.
- the material for forming the electron-hole recombination zone by the intermediate electrode is not particularly limited, and the material for forming the upper electrode and the lower electrode can be used.
- the electron-hole recombination zone with the intermediate electrode comprises a thin metal layer.
- the metal layer must be sufficiently thin and translucent so that light can reach the back photoelectric conversion unit (s).
- the thickness of the metal layer is preferably less than about 20 mm. It is particularly preferable that the metal film has a thickness of about 5 mm.
- These very thin metal films ( ⁇ 5cm) are not continuous films but rather are composed of isolated metal nanoparticles. Surprisingly, this very thin metal layer is not continuous, but it is still effective as an electron-hole recombination layer.
- Preferred metals used for this layer include Ag, Li, LiF, Al, Ti and Sn. Of these, Ag is particularly preferable.
- each layer of the organic thin film solar cell and laminated organic thin film solar cell of the present invention a dry film forming method such as vacuum deposition, sputtering, plasma and ion plating, spin coating, dip coating, casting Wet film forming methods such as roll coating, flow coating, and ink jet can be applied.
- the thickness of each layer is not particularly limited, but is set to an appropriate thickness. Since it is generally known that the exciton diffusion length of an organic thin film is short, if the film thickness is too thick, the exciton is deactivated before reaching the heterointerface, resulting in low photoelectric conversion efficiency.
- the normal film thickness is suitably in the range of 1 nm to 10 ⁇ m, but more preferably in the range of 5 nm to 0.2 ⁇ m.
- a known resistance heating method is preferable, and for forming the mixed layer, for example, a film forming method by simultaneous vapor deposition from a plurality of evaporation sources is preferable. More preferably, the substrate temperature is controlled during film formation.
- a material for forming each layer is dissolved or dispersed in an appropriate solvent to prepare a light-emitting organic solution to form a thin film, and any solvent can be used.
- halogenated hydrocarbon solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, tetrachloroethane, trichloroethane, chlorobenzene, dichlorobenzene and chlorotoluene
- ether solvents such as dibutyl ether, tetrahydrofuran, dioxane and anisole, methanol and the like
- Alcohol solvents such as ethanol, propanol, butanol, pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve and ethylene glycol
- hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, hexane, octane, decane and tetralin
- ester solvents such as ethyl acetate, butyl
- an appropriate resin or additive may be used for improving the film formability and preventing pinholes in the film.
- Usable resins include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate and cellulose, and copolymers thereof, poly-N-vinyl. Examples thereof include photoconductive resins such as carbazole and polysilane, and conductive resins such as polythiophene and polypyrrole.
- the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.
- an integrated module in which these are integrated can be shown. Specifically, it can be used for watches, mobile phones, mobile personal computers, and the like.
- Examples 5-8 A glass substrate with an ITO transparent electrode having a thickness of 25 mm ⁇ 75 mm ⁇ 0.7 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
- a glass substrate with a transparent electrode line after cleaning is mounted on a substrate holder of a vacuum deposition apparatus, and a film having a film thickness of 30 nm is first covered on the surface on the side where the transparent electrode line as the lower electrode is formed so as to cover the transparent electrode.
- CuPc structural formula is described below
- C 60 having a structural formula described below
- C 60 with a film thickness of 60 nm was formed thereon at 1 ⁇ / s by resistance heating vapor deposition.
- any one of the compounds (2-A), (2-B), (2-D), and (2-G) synthesized in Examples 1 to 4 was deposited by resistance heating evaporation. The film was formed at 10 nm and 1 cm / s. Finally, metal Al was deposited in a thickness of 80 nm continuously as a counter electrode to form an organic thin film solar cell. The area was 0.05 cm 2 .
- Table 1 shows the measurement results of open circuit voltage (Voc), short circuit current density (Jsc), fill factor (FF), and photoelectric conversion efficiency ( ⁇ ) derived from the following formula.
- Voc open circuit voltage
- Jsc short-circuit current density
- FF fill factor
- ⁇ photoelectric conversion efficiency
- Comparative Example 1 An organic solar cell was produced in the same manner as in Example 5 except that the compound (2-A) was not used in Example 5.
- the IV characteristics of the organic solar cell thus fabricated were measured under AM1.5 conditions (light intensity 100 mW / cm 2 ).
- Table 1 shows the open-circuit voltage (Voc), the short-circuit current density (Jsc), the fill factor (FF), and the photoelectric conversion efficiency ( ⁇ ).
- Comparative Example 2 A device was fabricated in the same manner as in Example 5 except that the compound (2-A) was changed to BCP in Example 5.
- the IV characteristics of the organic solar cell thus fabricated were measured under AM1.5 conditions (light intensity 100 mW / cm 2 ).
- Table 1 shows the open-circuit voltage (Voc), the short-circuit current density (Jsc), the fill factor (FF), and the photoelectric conversion efficiency ( ⁇ ).
- Example 9 A glass substrate with an ITO transparent electrode having a thickness of 25 mm ⁇ 75 mm ⁇ 0.7 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
- a glass substrate with a transparent electrode line after cleaning is mounted on a substrate holder of a vacuum deposition apparatus, and a film having a film thickness of 30 nm is first covered on the surface on the side where the transparent electrode line as the lower electrode is formed so as to cover the transparent electrode.
- Compound 1 (compound described in WO2010 / 013520A1; the structural formula is described below) was formed into a film at 1 ⁇ / s by resistance heating vapor deposition.
- a C 70 film having a film thickness of 60 nm (the structural formula is described below) was formed thereon at 1 ⁇ ⁇ / s by resistance heating vapor deposition.
- the compound (2-D) synthesized in Example 3 was formed to a thickness of 5 nm and 1 5 / s by resistance heating evaporation. Subsequently, Ag was deposited by resistance heating vapor deposition to form an intermediate electrode having a thickness of 0.5 nm, and MoO 3 was subsequently deposited by resistance heating deposition to obtain a buffer layer having a thickness of 5 nm. Thereon thickness 20nm Compound 1, finally deposited in this order as the C 70 a thickness 10nm thickness 20nm and BCP, a metal Al was thickness 80nm deposited as a counter electrode in succession, an organic thin film A solar cell was formed. The area was 0.05 cm 2 .
- the IV characteristics of the produced organic thin-film solar cell were measured under AM1.5 conditions (light intensity 100 mW / cm 2 ).
- Table 2 shows open circuit voltage (Voc), short circuit current density (Jsc), fill factor (FF), and photoelectric conversion efficiency ( ⁇ ).
- Comparative Example 3 An organic solar cell was produced in the same manner as in Example 5 except that the compound (2-D) was not used in Example 5.
- the IV characteristics of the organic solar cell thus fabricated were measured under AM1.5 conditions (light intensity 100 mW / cm 2 ).
- Table 2 shows open circuit voltage (Voc), short circuit current density (Jsc), fill factor (FF), and photoelectric conversion efficiency ( ⁇ ).
- the compound of the present invention is useful as an electron transport material and an organic thin film solar cell material.
- ADVANTAGE OF THE INVENTION According to this invention, the organic thin film solar cell which shows a highly efficient photoelectric conversion characteristic can be provided.
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Abstract
Description
このような背景の中で、有機太陽電池は、安価で原材料不足の懸念もないことから、シリコン系太陽電池に次ぐ次世代の太陽電池として注目を集めている。
n層としてチタニア等の無機半導体表面にルテニウム色素等の増感色素を単分子吸着させたものを用い、p層として電解質溶液を用いたものは、色素増感太陽電池(所謂グレッツェルセル)と呼ばれ、光電変換効率の高さから、1991年以降精力的に研究されてきたが、溶液を用いるため、長時間の使用に際して液漏れする等の欠点を有していた。そこでこのような欠点を克服するため、電解質溶液を固体化して全固体型の色素増感太陽電池を模索する研究も最近なされているが、多孔質チタニアの細孔に有機物をしみ込ませる技術は難易度が高く、再現性よく高変換効率が発現できるセルは完成していないのが現状である。
上記目的を達成するため、本発明者らは鋭意研究を行い、電子求引性を示す無水フタル酸骨格、フタルイミド骨格、無水ナフタル酸骨格又はナフタルイミド骨格と、フェナントロリン骨格とを有する化合物が、高い電子輸送性をもち、電極とのエネルギー障壁が小さく、有機薄膜太陽電池に用いたときに高効率の光電変換特性を示すことを見出し、本発明を完成させた。
1.下記式(1)で表される化合物。
Rgは、置換もしくは無置換の、ベンゼン環又はナフタレン環である。
Xは、酸素原子、又はN-R4(ここで、R4は、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~40のアルキル基、置換もしくは無置換の炭素数2~40のアルケニル基、置換もしくは無置換の炭素数2~40のアルキニル基、置換もしくは無置換の環形成炭素数6~40のアリール基、置換もしくは無置換の環形成原子数5~40のヘテロアリール基、置換もしくは無置換の炭素数1~40のアルコキシ基、又は置換もしくは無置換の環形成炭素数6~40のアリールオキシ基である。)である。]
2.前記式(1)で表される化合物が、下記式(2)又は式(3)で表わされる化合物である上記1に記載の化合物。
aは0~4の整数、bは0~3の整数,cは0~2の整数、dは0~2の整数、eは0又は1、fは0~2の整数、gは0~2の整数、hは0~2の整数、iは0~2の整数、及びjは0又は1の整数である。
a~d及びf~iが2以上の場合、2以上のR11~R14、R16~R19はそれぞれ同一でも異なっていてもよい。)]
3.上記1又は2に記載の化合物を含有する電子輸送材料。
4.上記1又は2に記載の化合物を含有する有機薄膜太陽電池用材料。
5.一対の電極の間に上記1又は2に記載の化合物を含む有機層が配置された有機薄膜太陽電池。
6.前記有機層が陰極側のバッファー層である上記5に記載の有機薄膜太陽電池。
7.複数の有機太陽電池単セルを積層した積層型有機薄膜太陽電池の中間電極に接するバッファー層が上記1又は2に記載の化合物を含有する積層型有機薄膜太陽電池。
8.上記5又は6に記載の有機薄膜太陽電池又は上記7に記載の積層型有機薄膜太陽電池を具備する装置。
本発明によれば、新規な電子輸送材料及び有機薄膜太陽電池用材料が提供できる。
本発明によれば、高効率な光電変換特性が得られる有機薄膜太陽電池及び積層型有機薄膜太陽電池が提供できる。
Rgは、置換もしくは無置換の、ベンゼン環又はナフタレン環である。
R4は、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~40のアルキル基、置換もしくは無置換の炭素数2~40のアルケニル基、置換もしくは無置換の炭素数2~40のアルキニル基、置換もしくは無置換の環形成炭素数6~40のアリール基、置換もしくは無置換の環形成原子数5~40のヘテロアリール基、置換もしくは無置換の炭素数1~40のアルコキシ基、又は置換もしくは無置換の環形成炭素数6~40のアリールオキシ基である。R4は、好ましくは、炭素数1~40のアルキル基である。
本発明の化合物は、これらの骨格構造を有するため、高い電子輸送性を有し、電極とのエネルギー障壁が小さい。従って、本発明の化合物を有機薄膜太陽電池に用いると、高効率の光電変換特性を示す有機薄膜太陽電池が得られる。
本発明の化合物は、上記のような架橋基Lを有することで、電荷輸送性が向上する。
Lは、さらに好ましくは単結合又はアリーレン基である。単結合の場合は、Jsc(短絡電流密度)を高めることができる、電子輸送性が大きいフタルイミドと、FF(形状因子)が高いフェナントロリン骨格を直接連結することで両方の性能を満たすので変換効率向上の点で好ましい。また,フェニレン基のようなアリーレン基の場合は、π共役が広がるため電子輸送性が増し、変換効率の向上に寄与するので好ましい。アリーレン基としてはフェニレン基が好ましい。
a~d、f~iが2以上の場合、2以上のR11~R14、R16~R19はそれぞれ同一でも異なっていてもよい。
a~jは、好ましくは、0である。
好適には、置換もしくは無置換の炭素数1~20のアルキル基である。この範囲のアルキル基が存在すると、湿式法を用いて有機薄膜太陽電池を製造する場合に、溶剤への溶解性が向上し、塗布性が向上するので好ましい。
上記アルキル基の置換基としては、例えば、フッ素原子、塩素原子、臭素原子、ヨウ素原子のようなハロゲン原子、フェニル基のようなアリール基が挙げられ、当該アリール基はメチル基、エチル基、プロピル基等の炭素数1~5のアルキル基でさらに置換されていてもよい。
上記アルケニル基の置換基としては、例えば、フェニル基のようなアリール基が挙げられ、当該アリール基はメチル基、エチル基、プロピル基等の炭素数1~5のアルキル基でさらに置換されていてもよい。
上記アルキニル基の置換基としては、例えば、フェニル基のようなアリール基が挙げられ、当該アリール基はメチル基、エチル基、プロピル基等の炭素数1~5のアルキル基でさらに置換されていてもよい。
上記アリール基の置換基としては、例えば、フェニル基のようなアリール基が挙げられ、当該アリール基はメチル基、エチル基、プロピル基等の炭素数1~5のアルキル基でさらに置換されていてもよい。
上記ヘテロアリール基の置換基としては、例えば、フェニル基のようなアリール基が挙げられ、当該アリール基はメチル基、エチル基、プロピル基等の炭素数1~5のアルキル基でさらに置換されていてもよい。
上記アルコキシ基の置換基としては、例えば、フッ素原子、塩素原子、臭素原子、ヨウ素原子のようなハロゲン原子、フェニル基のようなアリール基が挙げられ、当該アリール基はメチル基、エチル基、プロピル基等の炭素数1~5のアルキル基でさらに置換されていてもよい。
上記アリールオキシ基の置換基としては、例えば、フェニル基のようなアリール基が挙げられ、当該アリール基はメチル基、エチル基、プロピル基等の炭素数1~5のアルキル基でさらに置換されていてもよい。
上記アリールアミノ基の置換基としては、例えば、フェニル基のようなアリール基が挙げられ、当該アリール基はメチル基、エチル基、プロピル基等の炭素数1~5のアルキル基でさらに置換されていてもよい。
上記アルキルアミノ基の置換基としては、例えば、フェニル基のようなアリール基が挙げられ、当該アリール基はメチル基、エチル基、プロピル基等の炭素数1~5のアルキル基でさらに置換されていてもよい。
本発明の電子輸送材料及び有機薄膜太陽電池用材料は、本発明の化合物を含有することを特徴とする。
本発明の電子輸送材料及び有機薄膜太陽電池用材料は、本発明の化合物単独であってもよいし、本発明の化合物と他の成分を含有していてもよい。
本発明の有機薄膜太陽電池用材料からなる有機薄膜太陽電池の部材は、本発明の材料単独から形成されていてもよいし、本発明の材料と他の成分の混合物から形成されていてもよい。
本発明の材料を用いる有機薄膜太陽電池は、高効率の変換特性を示す。
本発明の有機薄膜太陽電池では、電池を構成する1以上の有機層の少なくとも1層に本発明の化合物を含有していればよい。また、本発明の化合物を含有する部材は、他の成分を併せて含んでいてもよい。本発明の化合物を含まない部材や混合材料については、有機薄膜太陽電池で使用される公知の部材や材料を使用することができる。
本発明の化合物を含む有機層は、陰極側のバッファー層であることが好ましい。
(1)下部電極/p層/n層/上部電極
(2)下部電極/バッファー層/p層/n層/上部電極
(3)下部電極/p層/n層/バッファー層/上部電極
(4)下部電極/バッファー層/p層/n層/バッファー層/上部電極
(5)下部電極/バッファー層/p層/i層(又はp材料とn材料の混合層)/n層/バッファー層/上部電極
(6)下部電極/p層/n層/バッファー層/中間電極/バッファー層/p層/n層/バッファー層/上部電極
(7)下部電極/バッファー層/p層/n層/バッファー層/中間電極/バッファー層/p層/n層/バッファー層/上部電極
(8)下部電極/バッファー層/p層/i層(又はp材料とn材料の混合層)/n層/バッファー層/中間電極/バッファー層/p層/i層(又はp材料とn材料の混合層)/n層/バッファー層/上部電極
以下、各構成部材について簡単に説明する。
下部電極、上部電極の材料は特に制限はなく、公知の導電性材料を使用できる。例えば、p層と接続する電極としては、錫ドープ酸化インジウム(ITO)や金(Au)、オスミウム(Os)、パラジウム(Pd)等の金属が使用でき、n層と接続する電極としては、銀(Ag)、アルミニウム(Al)、インジウム(In)、カルシウム(Ca)、白金(Pt)リチウム(Li)等の金属やMg:Ag、Mg:InやAl:Li等の二成分金属系が使用できる。n層と接続する電極としては、仕事関数の小さい金属あるいは金属系が好ましい。
n層の材料は特に限定されないが、電子受容体としての機能を有する化合物が好ましい。有機化合物であれば、例えば、C60等のフラーレン化合物、カーボンナノチューブ、ペリレン化合物、多環キノン及びキナクリドン等、高分子系ではCN-ポリ(フェニレン-ビニレン)、MEH-CN-PPV、-CN基又はCF3基含有ポリマー及びポリ(フルオレン)化合物等を挙げることができる。電子の移動度が高い材料が好ましく、さらに電子親和力が小さい材料が好ましい。このように電子親和力の小さい材料をn層として組み合わせることで充分な開放端電圧を実現することができる。
一般に、有機薄膜太陽電池は総膜厚が薄いことが多く、そのため上部電極と下部電極が短絡し、セル作製の歩留まりが低下することが多い。このような場合には、バッファー層を積層することによってこれを防止することが好ましい。
本発明の化合物は、電子輸送性が高く、電極とのエネルギー障壁が小さいため、バッファー層、特に陰極側のバッファー層に用いることが好ましい。
また、本発明の有機薄膜太陽電池が積層型である場合、中間電極に接するバッファー層に本発明の化合物を用いることが好ましい。
本発明の化合物以外のバッファー層に好ましい化合物としては、膜厚を厚くしても短絡電流が低下しないようにキャリア移動度が充分に高い化合物が好ましい。低分子化合物であれば、例えば、下記に示すNTCDAに代表される芳香族環状酸無水物等が挙げられ、高分子化合物であれば、下記に示すポリ(3,4-エチレンジオキシ)チオフェン:ポリスチレンスルホネート(PEDOT:PSS)及びポリアニリン:カンファースルホン酸(PANI:CSA)等に代表される公知の導電性高分子等が挙げられる。
基板は、機械的、熱的強度を有し、透明性を有するものが好ましい。例えば、ガラス基板及び透明性樹脂フィルムがある。透明性樹脂フィルムとしては、ポリエチレン、エチレン-酢酸ビニル共重合体、エチレン-ビニルアルコール共重合体、ポリプロピレン、ポリスチレン、ポリメチルメタアクリレート、ポリ塩化ビニル、ポリビニルアルコール、ポリビニルブチラール、ナイロン、ポリエーテルエーテルケトン、ポリサルホン、ポリエーテルサルフォン、テトラフルオロエチレン-パーフルオロアルキルビニルエーテル共重合体、ポリビニルフルオライド、テトラフルオロエチレン-エチレン共重合体、テトラフルオロエチレン-ヘキサフルオロプロピレン共重合体、ポリクロロトリフルオロエチレン、ポリビニリデンフルオライド、ポリエステル、ポリカーボネート、ポリウレタン、ポリイミド、ポリエーテルイミド、ポリイミド及びポリプロピレン等が挙げられる。
積層型有機薄膜太陽電池はタンデム構造太陽電池と呼ばれるもので、一対の電極の間に少なくとも2つの発電層(有機太陽電池単セル)と少なくとも1つの中間電極を有する。典型的な構造では、透明基板上にITO等の透明陽極が設置され、その上にp層/i層/n層からなるフロントセルが形成され、その上に設置された中間電極上に、p層/i層/n層からなるバックセルが形成され、その上に陰極が形成される。このような多層構造の採用により、変換効率の向上を図ることができる。
積層型有機薄膜太陽電池を構成する上部電極、下部電極、p層、n層、i層及びバッファー層の説明は前記と同様である。
本発明の積層型有機薄膜太陽電池は、中間電極に接するバッファー層に本発明の化合物を含有することが好ましい。
中間電極によって、電子-正孔再結合ゾーンを形成することにより積層型素子の個々の光電変換ユニットを分離することができる。この層は前方の光電変換ユニット(フロントセル)のn層と後方の光電変換ユニット(バックセル)のp層の間の逆ヘテロ接合の形成を防ぐ役目をする。個々の光電変換ユニットの間の層は、前方の光電変換ユニットから入る電子と後方の光電変換ユニットからの正孔が再結合するゾーンを提供する。前方の光電変換ユニットから入る電子と後方の光電変換ユニットからの正孔の効率的な再結合は、光誘起電流を積層型素子で起こそうとする場合に必要である。
金属層は、光が後方の(複数の)光電変換ユニットに到達できるように、十分薄くて半透明でなければならない。この目的のために、金属層の厚さは約20Åより薄いことが好ましい。金属膜が約5Å程度の厚さであると特に好ましい。これらの極めて薄い金属膜(~5Å)は連続膜でなく、むしろ孤立した金属ナノ粒子からなると考えられている。驚くべきことに、この極めて薄い金属層は連続ではないが、それは依然として電子-正孔再結合層として有効である。この層に用いられる好ましい金属には、Ag、Li、LiF、Al、Ti及びSnが含まれる。このうちAgが特に好ましい。
本発明の有機薄膜太陽電池や積層型有機薄膜太陽電池の各層の形成には、真空蒸着、スパッタリング、プラズマ及びイオンプレーティング等の乾式成膜法やスピンコーティング、ディップコート、キャスティング、ロールコート、フローコーティング及びインクジェット等の湿式成膜法を適用することができる。
各層の膜厚は特に限定されないが、適切な膜厚に設定する。一般に有機薄膜の励起子拡散長は短いことが知られているため、膜厚が厚すぎると励起子がヘテロ界面に到達する前に失活してしまうため光電変換効率が低くなる。膜厚が薄すぎるとピンホール等が発生してしまうため、充分なダイオード特性が得られないため、変換効率が低下する。通常の膜厚は1nmから10μmの範囲が適しているが、5nmから0.2μmの範囲がさらに好ましい。
湿式成膜法の場合、各層を形成する材料を、適切な溶媒に溶解又は分散させて発光性有機溶液を調製し、薄膜を形成するが、任意の溶媒を使用できる。例えば、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素、テトラクロロエタン、トリクロロエタン、クロロベンゼン、ジクロロベンゼン及びクロロトルエン等のハロゲン系炭化水素系溶媒や、ジブチルエーテル、テトラヒドロフラン、ジオキサン及びアニソール等のエーテル系溶媒、メタノールやエタノール、プロパノール、ブタノール、ペンタノール、ヘキサノール、シクロヘキサノール、メチルセロソルブ、エチルセロソルブ及びエチレングリコール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、エチルベンゼン、ヘキサン、オクタン、デカン及びテトラリン等の炭化水素系溶媒、並びに酢酸エチル、酢酸ブチル及び酢酸アミル等のエステル系溶媒等が挙げられる。なかでも、炭化水素系溶媒及びエーテル系溶媒が好ましい。また、これらの溶媒は単独で使用しても複数混合して用いてもよい。尚、使用可能な溶媒は、これらに限定されるものではない。
また、添加剤としては、酸化防止剤、紫外線吸収剤及び可塑剤等が挙げられる。
窒素雰囲気下、4-ブロモ-無水フタル酸(15g,66.1mmol)、メチルアミン(40% in H2O)(8.26mL,99.1mmol)、酢酸ナトリウム(8.67g,106mmol)に酢酸(100mL)を加えて6時間加熱撹拌還流した。反応混合物に水(200mL)を加え、沈殿物を濾別して白色固体(15.2g,96%)を得た。
この固体の核磁気共鳴測定(1H-NMR)の結果を以下に示す。
1H-NMR(400MHz,CDCl3,TMS)δ:3.18(s,3H),7.71(d,J8.0,1H),7.84(d,J8.0,1H),7.98(s,1H).
窒素雰囲気下、中間体A1(10g,41.7mmol)、ビス(ピナコラト)ジボロン(13g,50.0mmol)、1,1’-ビス(ジフェニルホスフィノ)フェロセン]パラジウム(II)ジクロリド ジクロロメタン錯体(0.65g,0.80mmol)、酢酸カリウム(30g,305mmol)、1,4-ジオキサン100mL)を加えて80℃で12時間撹拌した。反応混合物に酢酸エチル(300mL)、水(50mL)を加え、有機層を分取、無水硫酸マグネシウムで乾燥、溶媒留去して白色固体を得た。これをカラムクロマトグラフィ(シリカゲル/ヘキサン:酢酸エチル=3:1)で精製して白色固体(8.0g,67%)を得た。
1H-NMR(400MHz,CDCl3,TMS)δ:1.37(s,12H),3.18(s,3H),7.82(d,J8.0,1H),8.14(d,J8.0,1H),8.27(s,1H).
窒素雰囲気下、中間体A2(1.6g、5.6mmol)、2-クロロフェナントロリン(0.8g、3.7mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0)(0.1g、0.11mmol)、炭酸セシウム(3.0g、9.3mmol)1,2-ジメトキシエタン(37mL)を加えて80℃で6時間撹拌した。反応混合物に水(50mL)を加え、沈殿物を濾別して黄色固体(化合物(2-A);0.76g、60%)を得た。
1H-NMR(400MHz,CDCl3,TMS)δ:3.25(s,3H),7.70(d,J8.0,1H),8.03(d,J8.0,1H),8.18(d,J8.0,1H),8.30(d,J8.0,1H),8.41(d,J8.0,1H),8.69(s,1H),8.83(d,J8.0,1H),9.26(d,J8.0,1H).
1H-NMR(400MHz,CDCl3,TMS)δ:3.24(s,3H),7.69(d,J8.0,1H),7.90(s,1H),8.03(d,J8.0,1H),8.13(d,J8.0,1H),8.26-8.31(m,2H),8.50(d,J8.0,1H),9.24(d,J8.0,1H),9.46(d,J8.0,1H).
1H-NMR(400MHz,CDCl3,TMS)δ:3.23(s,3H),7.66(d,J8.0,2H),7.81-7.87(m,4H),7.94(d,J8.0,2H),8.02(d,J8.0,1H),8.18(d,J8.0,2H),8.28(d,J8.0,1H),8.36(d,J8.0,1H),8.50d,J8.0,2H),9.26(d,J8.0,1H).
1H-NMR(400MHz,CDCl3,TMS)δ:3.23(s,3H),7.64-7.75(m,3H),7.84(d,J8.0,2H),7.94(d,J8.0,1H),8.08(d,J8.0,1H),8.16-8.20(m,2H),8.28(d,J8.0,1H),8.36-8.39(m,2H),8.58(s,1H)9.23(d,J8.0,1H).
25mm×75mm×0.7mm厚のITO透明電極付きガラス基板をイソプロピルアルコール中で5分間超音波洗浄した後、30分間UVオゾン洗浄を実施した。洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず下部電極である透明電極ラインが形成されている側の面上に、透明電極を覆うようにして膜厚30nmのCuPc(下記に構造式を記載する)を抵抗加熱蒸着により、1Å/sで成膜した。続けてその上に膜厚60nmのC60(下記に構造式を記載する)を抵抗加熱蒸着により1Å/sで成膜した。
Jsc:短絡電流密度
FF:曲線因子
Pin:入射光エネルギー
実施例5において化合物(2-A)を用いないこと以外は実施例5と同様に有機太陽電池を作製した。このように作製された有機太陽電池をAM1.5条件下(光強度100mW/cm2)でI-V特性を測定した。開放端電圧(Voc)、短絡電流密度(Jsc)、曲線因子(FF)及び光電変換効率(η)を表1に示す。
実施例5において化合物(2-A)をBCPに変更した以外は実施例5と同様にして素子を作製した。このように作製された有機太陽電池をAM1.5条件下(光強度100mW/cm2)でI-V特性を測定した。開放端電圧(Voc)、短絡電流密度(Jsc)、曲線因子(FF)及び光電変換効率(η)を表1に示す。
25mm×75mm×0.7mm厚のITO透明電極付きガラス基板をイソプロピルアルコール中で5分間超音波洗浄した後、30分間UVオゾン洗浄を実施した。洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず下部電極である透明電極ラインが形成されている側の面上に、透明電極を覆うようにして膜厚30nmの化合物1(WO2010/013520A1号公報に記載された化合物;下記に構造式を記載する)を抵抗加熱蒸着により、1Å/sで成膜した。続けてその上に膜厚60nmのC70(下記に構造式を記載する)を抵抗加熱蒸着により1Å/sで成膜した。
実施例5において化合物(2-D)を用いないこと以外は実施例5と同様に有機太陽電池を作製した。このように作製された有機太陽電池をAM1.5条件下(光強度100mW/cm2)でI-V特性を測定した。開放端電圧(Voc)、短絡電流密度(Jsc)、曲線因子(FF)及び光電変換効率(η)を表2に示す。
本発明によれば、高効率の光電変換特性を示す有機薄膜太陽電池を提供できる。
この明細書に記載の文献の内容を全てここに援用する。
Claims (8)
- 下記式(1)で表される化合物。
Rgは、置換もしくは無置換の、ベンゼン環又はナフタレン環である。
Xは、酸素原子、又はN-R4(ここで、R4は、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~40のアルキル基、置換もしくは無置換の炭素数2~40のアルケニル基、置換もしくは無置換の炭素数2~40のアルキニル基、置換もしくは無置換の環形成炭素数6~40のアリール基、置換もしくは無置換の環形成原子数5~40のヘテロアリール基、置換もしくは無置換の炭素数1~40のアルコキシ基、又は置換もしくは無置換の環形成炭素数6~40のアリールオキシ基である。)である。] - 前記式(1)で表される化合物が、下記式(2)又は式(3)で表わされる化合物である請求項1に記載の化合物。
aは0~4の整数、bは0~3の整数,cは0~2の整数、dは0~2の整数、eは0又は1、fは0~2の整数、gは0~2の整数、hは0~2の整数、iは0~2の整数、及びjは0又は1の整数である。
a~d及びf~iが2以上の場合、2以上のR11~R14、R16~R19はそれぞれ同一でも異なっていてもよい。)] - 請求項1又は2に記載の化合物を含有する電子輸送材料。
- 請求項1又は2に記載の化合物を含有する有機薄膜太陽電池用材料。
- 陽極と陰極の間に請求項1又は2に記載の化合物を含む有機層が配置された有機薄膜太陽電池。
- 前記有機層が陰極側のバッファー層である請求項5に記載の有機薄膜太陽電池。
- 複数の有機太陽電池単セルを積層した積層型有機薄膜太陽電池の中間電極に接するバッファー層が請求項1又は2に記載の化合物を含有する積層型有機薄膜太陽電池。
- 請求項5又は6に記載の有機薄膜太陽電池又は請求項7に記載の積層型有機薄膜太陽電池を具備する装置。
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KR1020137002133A KR20130098289A (ko) | 2010-07-28 | 2011-07-27 | 페난트롤린 화합물, 상기 화합물로 이루어지는 전자 수송 재료, 및 상기 화합물을 포함하여 이루어지는 유기 박막 태양 전지 |
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JP2021082719A (ja) * | 2019-11-20 | 2021-05-27 | 東洋インキScホールディングス株式会社 | 熱電変換材料及び熱電変換素子 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2013187482A1 (ja) * | 2012-06-15 | 2013-12-19 | コニカミノルタ株式会社 | タンデム型有機光電変換素子およびこれを用いた太陽電池 |
JPWO2013187482A1 (ja) * | 2012-06-15 | 2016-02-08 | コニカミノルタ株式会社 | タンデム型有機光電変換素子およびこれを用いた太陽電池 |
JP2021082719A (ja) * | 2019-11-20 | 2021-05-27 | 東洋インキScホールディングス株式会社 | 熱電変換材料及び熱電変換素子 |
JP7400384B2 (ja) | 2019-11-20 | 2023-12-19 | 東洋インキScホールディングス株式会社 | 熱電変換材料及び熱電変換素子 |
Also Published As
Publication number | Publication date |
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EP2599780A4 (en) | 2014-01-22 |
KR20130098289A (ko) | 2013-09-04 |
JP2012025716A (ja) | 2012-02-09 |
JP5657298B2 (ja) | 2015-01-21 |
US20130180590A1 (en) | 2013-07-18 |
EP2599780A1 (en) | 2013-06-05 |
CN102958929A (zh) | 2013-03-06 |
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