WO2009125647A1 - 電子供与性有機材料、光起電力素子用材料および光起電力素子 - Google Patents
電子供与性有機材料、光起電力素子用材料および光起電力素子 Download PDFInfo
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- WO2009125647A1 WO2009125647A1 PCT/JP2009/054836 JP2009054836W WO2009125647A1 WO 2009125647 A1 WO2009125647 A1 WO 2009125647A1 JP 2009054836 W JP2009054836 W JP 2009054836W WO 2009125647 A1 WO2009125647 A1 WO 2009125647A1
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- WIPO (PCT)
- Prior art keywords
- compound
- electron
- group
- added
- benzothiadiazole
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- 239000011368 organic material Substances 0.000 title claims abstract description 89
- 239000000463 material Substances 0.000 title claims description 36
- -1 benzothiadiazole compound Chemical class 0.000 claims abstract description 53
- 238000004770 highest occupied molecular orbital Methods 0.000 claims abstract description 53
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims abstract description 37
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical group C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000005549 heteroarylene group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910003472 fullerene Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 43
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- 239000000126 substance Substances 0.000 description 93
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
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- 239000008096 xylene Substances 0.000 description 1
Images
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
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- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
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- 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
- H10K85/115—Polyfluorene; Derivatives thereof
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- 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 an electron donating organic material, a material for a photovoltaic device, and a photovoltaic device using the same.
- Solar cells are attracting attention as environmentally friendly electrical energy sources.
- inorganic materials such as single crystal silicon, polycrystalline silicon, amorphous silicon, and compound semiconductors are used as semiconductor materials for photovoltaic elements of solar cells.
- solar cells manufactured using inorganic semiconductors have not been widely used in ordinary households because of high costs compared with power generation methods such as thermal power generation and nuclear power generation.
- the high cost factor is mainly in the process of manufacturing a semiconductor thin film under vacuum and high temperature. Therefore, in order to simplify the manufacturing process, an organic solar cell using an organic semiconductor such as a conjugated polymer or an organic crystal or an organic dye as a semiconductor material has been studied.
- organic solar cells using organic semiconductors such as conjugated polymers have the biggest problem of low photoelectric conversion efficiency compared to conventional solar cells using inorganic semiconductors, and have not yet been put into practical use. .
- the following three points are mainly cited as the reason why the photoelectric conversion efficiency of an organic solar cell using a conventional conjugated polymer is low.
- the solar light absorption efficiency is low.
- a bound state called exciton is formed in which electrons and holes generated by sunlight are difficult to separate.
- traps for capturing carriers (electrons and holes) are easily formed, the generated carriers are easily captured by the traps, and the mobility of carriers is low. That is, a semiconductor material generally requires a high mobility ⁇ for a carrier of the material, but a conjugated polymer has a problem that the mobility ⁇ is lower than that of a conventional inorganic crystal semiconductor or amorphous silicon.
- the photoelectric conversion elements using organic semiconductors known so far can be generally classified into the following element configurations at present.
- a Schottky type that joins an electron-donating organic material (p-type organic semiconductor) and a metal having a low work function, and an electron-accepting organic material (n-type organic semiconductor) and an electron-donating organic material (p-type organic semiconductor).
- Heterojunction type In these elements, only the organic layer (about several molecular layers) at the junction contributes to the photocurrent generation, so that the photoelectric conversion efficiency is low, and its improvement is a problem.
- Non-Patent Document 1 As a method for improving photoelectric conversion efficiency, a bulk heterojunction in which an electron-accepting organic material (n-type organic semiconductor) and an electron-donating organic material (p-type organic semiconductor) are mixed to increase the bonding surface contributing to photoelectric conversion
- n-type organic semiconductor an electron-accepting organic material
- p-type organic semiconductor an electron-donating organic material
- C 60 carbon nanotube
- An object of this invention is to provide a photovoltaic device with high photoelectric conversion efficiency.
- the present invention includes (a) a benzothiadiazole skeleton and an oligothiophene skeleton, (b) a band gap (Eg) of 1.8 eV or less, and (c) a highest occupied molecular orbital (HOMO) level ⁇
- the electron donating organic material has a ratio of 1: 1 to 1: 2 (excluding 1: 1), and the number of thiophene rings contained in one oligothiophene skeleton is 3 or more and 12 or less These are materials for photovoltaic elements and photovoltaic elements using the same.
- a photovoltaic device having a high photoelectric conversion efficiency and having both a high short-circuit current density (Isc) and a high open-circuit voltage (Voc).
- the electron donating organic material of the present invention includes (a) a benzothiadiazole skeleton and an oligothiophene skeleton, (b) a band gap (Eg) of 1.8 eV or less, and (c) the highest occupied molecular orbital (HOMO). )
- a benzothiadiazole compound having a level of ⁇ 4.8 eV or less is included.
- the electron-donating organic material of the present invention can be used for photovoltaic device materials, organic electroluminescent device materials, organic transistor materials, wavelength conversion device materials, organic laser materials, and the like. It can be preferably used as an element material.
- the benzothiadiazole compound used for the electron donating organic material of the present invention will be described.
- the benzothiadiazole compound used in the present invention includes (a) a benzothiadiazole skeleton and an oligothiophene skeleton.
- the oligothiophene skeleton refers to a skeleton in which 3 or more and 12 or less thiophene rings are connected by a conjugated bond.
- the number of thiophene rings contained in one oligothiophene skeleton is 3 or more, the light absorption wavelength region of the benzothiadiazole compound can be further widened. For this reason, a high short circuit current (Isc) can be obtained in the photovoltaic device. 4 or more are more preferable.
- the number of thiophene rings contained in one oligothiophene skeleton is 12 or less, the highest occupied molecular orbital (HOMO) level of the benzothiadiazole compound can be deepened. For this reason, a high open circuit voltage (Voc) can be obtained in the photovoltaic device. More preferably, 8 or less.
- the benzothiadiazole compound used in the present invention has (b) a band gap (Eg) of 1.8 eV or less.
- the band gap is the energy difference between the highest occupied molecular orbital (HOMO) level and the lowest unoccupied molecular orbital (LUMO) level.
- HOMO highest occupied molecular orbital
- LUMO lowest unoccupied molecular orbital
- the band gap is preferably 1.8 eV or less and 0.8 eV or more, more preferably 1.8 eV or less and 1.2 eV or more, and more preferably 1.8 eV or less and 1.4 eV or more. More preferably, it is 1.8 eV or less and 1.6 eV or more.
- the band gap of the benzothiadiazole compound is determined from the light absorption edge of the thin film formed from the benzothiadiazole compound using the following formula.
- Eg (eV) 1240 / light absorption edge wavelength of thin film (nm)
- the method for forming the thin film used here is not particularly limited.
- the thin film is dissolved in an organic solvent such as chloroform, tetrahydrofuran, or chlorobenzene, and the thin film is formed on the glass substrate by a wet coating method such as spin coating.
- the thickness of the thin film is preferably in the range of 5 nm to 500 nm, since the absorbance is too low if too thin, and the absorbance may be too high if it is too thick. More preferably.
- CT intramolecular charge transfer
- the benzothiadiazole compound used in the present invention has a deepest highest occupied molecular orbital (HOMO) level, specifically, ⁇ 4.8 eV or less as described in (c). is there.
- HOMO highest occupied molecular orbital
- the open-circuit voltage (Voc) of the photovoltaic element decreases, and the photoelectric conversion efficiency decreases.
- the highest occupied molecular orbital (HOMO) level is too low, electrons and holes generated by exciton charge separation may recombine and disappear on the electron-accepting organic material side.
- the highest occupied molecular orbital (HOMO) level is preferably ⁇ 4.8 eV or less and ⁇ 6.5 eV or more, more preferably ⁇ 4.8 eV or less and ⁇ 6.1 eV or more, and ⁇ 4 It is more preferably -8 eV or less and ⁇ 5.5 eV or more, and further preferably ⁇ 4.8 eV or less and ⁇ 5.3 eV or more.
- the highest occupied molecular orbital (HOMO) level of the benzothiadiazole compound is obtained by forming a thin film from the benzothiadiazole compound and measuring the photoelectron spectrum.
- the method for forming the thin film used here is not particularly limited, but the above-described method can be usually used.
- the thickness of the thin film is preferably in the range of 5 nm to 500 nm because the thickness of the thin film is affected by the underlying substrate, and if it is too thick, the film thickness may be uneven and may hinder measurement. More preferably, it is in the range of 10 nm to 200 nm. Note that “ ⁇ 4.8 eV or less” means that the absolute value is 4.8 or more, such as ⁇ 4.9 eV and ⁇ 5.0 eV.
- the ratio of the benzothiadiazole skeleton that is an electron-withdrawing group to the oligothiophene skeleton that is an electron-donating group is preferably 1: 1 to 1: 2 (excluding 1: 1), Further, the number of thiophene rings contained in one oligothiophene skeleton is preferably 12 or less.
- the benzothiadiazole skeleton has a linking position of 4,7. Is preferred. Specifically, 2,1,3-benzothiadiazole-4,7-diyl is preferable.
- the connecting position of the thiophene ring is preferably the 2,5-position (carbon adjacent to the sulfur atom contained in the thiophene ring).
- the oligothiophene skeleton is preferably oligo (thiophene-2,5-diyl).
- a compound having a structure represented by the following general formula (1) is preferable. Compared to the case where the benzothiadiazole skeleton and the oligothiophene skeleton are randomly arranged, the general arrangement of the oligothiophene skeleton-benzothiadiazole skeleton-oligothiophene skeleton, as shown in the general formula (1), Light absorption efficiency is improved.
- R 1 to R 18 may be the same or different and are selected from hydrogen, an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, and a halogen.
- A represents a divalent arylene group having a 6-membered ring structure or a divalent heteroarylene group having a 6-membered ring structure.
- m is 0 or 1.
- n represents a range of 1 to 1000.
- the alkyl group is, for example, a saturated fat such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group.
- the alkyl group may be linear, branched or cyclic, and may be unsubstituted or substituted. Examples of the substituent when substituted include an alkoxy group, an aryl group, a heteroaryl group, and a halogen described later.
- the number of carbon atoms of the alkyl group is preferably 2 or more from the viewpoint of processability, and preferably 20 or less in order to further increase the light absorption efficiency.
- the alkoxy group represents an aliphatic hydrocarbon group via an ether bond such as a methoxy group, an ethoxy group, a propoxy group, or a butoxy group.
- the aliphatic hydrocarbon group may be unsubstituted or substituted.
- the number of carbon atoms of the alkoxy group is preferably 2 or more from the viewpoint of processability, and is preferably 20 or less in order to further increase the light absorption efficiency.
- substituent in the case of substitution include an aryl group, heteroaryl group, and halogen described later.
- the aryl group represents an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, an anthryl group, a terphenyl group, a pyrenyl group, a fluorenyl group, and a perylenyl group.
- the aryl group may be unsubstituted or substituted.
- the number of carbon atoms of the aryl group is preferably 6 or more, and preferably 30 or less from the viewpoint of processability. Examples of the substituent when substituted include an alkyl group, a heteroaryl group described later, and a halogen.
- the heteroaryl group includes, for example, thienyl group, furyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, oxazolyl group, pyridyl group, pyrazyl group, pyrimidyl group, quinolinyl group, isoquinolyl group, quinoxalyl group, acridinyl group, indolyl group.
- a heteroaromatic group having an atom other than carbon such as a group, a carbazolyl group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzodithiophene group, a silole group, a benzosilole group, and a dibenzosilole group;
- the heteroaryl group may be unsubstituted or substituted. Examples of the substituent when substituted include an alkyl group, an aryl group, and a halogen described later.
- halogen is fluorine, chlorine, bromine or iodine.
- the divalent arylene group having a 6-membered ring structure represents a divalent (two bonding sites) aromatic hydrocarbon group.
- the arylene group may be unsubstituted or substituted. Examples of the substituent when substituted include an alkyl group, a heteroaryl group, and a halogen.
- Preferable specific examples of the divalent arylene group having a 6-membered ring structure include a phenylene group, a naphthylene group, a biphenylene group, a phenanthrylene group, an anthrylene group, a terphenylene group, a pyrenylene group, a fluorenylene group, and a peryleneylene group.
- the divalent heteroarylene group having a 6-membered ring structure refers to a divalent heteroaromatic ring group having a 6-membered ring structure.
- the heteroarylene group may be unsubstituted or substituted. Examples of the substituent when substituted include an alkyl group, an aryl group, and a halogen.
- the divalent heteroarylene group having a 6-membered ring structure include a pyridylene group, a pyrazylene group, a quinolinylene group, an isoquinolylene group, a quinoxalylene group, an acridinylene group, an indolylene group, a carbazolylene group, a benzofuran group, a dibenzofuran group, Examples thereof include a benzothiophene group, a dibenzothiophene group, a benzodithiophene group, a benzosilol group, and a dibenzosilole group.
- R 1 to R 18 in the compound represented by the general formula (1) are preferably hydrogen, an alkyl group, or an alkoxy group from the viewpoint of ensuring ease of synthesis and solubility.
- n represents the degree of polymerization of the benzothiadiazole compound and is in the range of 1 to 1000.
- the benzothiadiazole compound is preferably soluble in a solvent.
- n is preferably 1 or more and 500 or less.
- the degree of polymerization can be determined from the weight average molecular weight.
- the weight average molecular weight can be determined by measuring using GPC (gel permeation chromatography) and converting to a polystyrene standard sample.
- at least one of R 1 to R 18 is preferably an alkyl group or an alkoxy group.
- n in the general formula (1) is 1 or more and less than 10, it is more preferable that R 1 to R 18 have 1 to 8 alkyl groups or alkoxy groups.
- R 1 to R 18 have 1 to 8 alkyl groups or alkoxy groups.
- n in the general formula (1) is 10 or more, it is more preferable that 4 or more alkyl groups or alkoxy groups among R 1 to R 18 are present.
- HOMO highest occupied molecular orbital
- the skeleton of A in the general formula (1) is not particularly limited. Specifically, m-phenyl, p-phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, anthran, pyrene, benzothiophene, Examples include dibenzothiophene, indole, carbazole, fluorene, dibenzosilole and the like. Among these, fluorene and dibenzosilole are preferable from the viewpoint of ensuring solubility because two soluble substituents such as an alkyl group can be easily introduced. Moreover, the above-mentioned fluorene and dibenzosilol can obtain favorable photoelectric conversion efficiency compared with other skeletons. In addition to the above-described solubility, this is presumed to be due to the fact that it is easy to form a preferred morphology as a photovoltaic device, such as carrier path formation by nano-level phase separation.
- Examples of the benzothiadiazole compound having the structure represented by the general formula (1) include the following structures.
- n is in the range of 1 to 1000.
- the benzothiadiazole compound having the structure represented by the general formula (1) is synthesized by a method similar to the method described in, for example, Macromolecules 2000, 33, 9277-9288. can do.
- 5,5′-dibromo-2,2′-bithiophene and a 3-alkylthiophene-2-boronic acid derivative are reacted by a Suzuki coupling method using a palladium catalyst, and the resulting quarterthiophene compound is lithiated.
- boronate esterification, and the resulting product and dibromobenzothiadiazole are further reacted by a Suzuki coupling method using a palladium catalyst.
- the electron donating organic material of the present invention may be composed of only the benzothiadiazole compound or may contain other compounds.
- the content of the benzothiadiazole compound contained in the electron donating organic material is preferably in the range of 1 to 100% by weight, and more preferably in the range of 10 to 100% by weight.
- examples of other compounds include polythiophene polymers, poly-p-phenylene vinylene polymers, poly-p-phenylene polymers, polyfluorene polymers, polypyrrole polymers, polyaniline polymers, polyacetylene polymers.
- Conjugated polymers such as polymers, polythienylene vinylene polymers, phthalocyanine derivatives such as H 2 phthalocyanine (H 2 Pc), copper phthalocyanine (CuPc), zinc phthalocyanine (ZnPc), porphyrin derivatives, N, N′- Diphenyl-N, N′-di (3-methylphenyl) -4,4′-diphenyl-1,1′-diamine (TPD), N, N′-dinaphthyl-N, N′-diphenyl-4,4 ′ -Triarylamine derivatives such as diphenyl-1,1'-diamine (NPD), 4,4'-di (carbazol-9-yl) bif Carbazole derivatives such as sulfonyl (CBP), oligothiophene derivatives (terthiophene, quarter thiophene, sexithiophene, octyl thiophene etc
- the above benzothiadiazole compound exhibits electron donating properties (p-type semiconductor properties). Therefore, in order to obtain higher photoelectric conversion efficiency when used in a photovoltaic device, it is preferable to combine with an electron-accepting organic material (n-type organic semiconductor).
- the material for a photovoltaic device of the present invention includes an electron donating organic material containing the benzothiadiazole compound and an electron accepting organic material.
- the electron-accepting organic material used in the present invention is an organic material exhibiting n-type semiconductor characteristics, such as 1,4,5,8-naphthalene tetracarboxyl dianhydride (NTCDA), 3,4,9,10- Perylenetetracarboxylic dianhydride (PTCDA), 3,4,9,10-perylenetetracarboxylic bisbenzimidazole (PTCBI), N, N′-dioctyl-3,4,9,10-naphthyltetracarboxydiimide (PTCDI) -C8H), 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (PBD), 2,5-di (1-naphthyl) -1,3 , 4-oxadiazole (BND) derivatives such as 3- (4-biphenylyl) -4-phenyl-5- (4-t- Triazole derivative
- fullerene compounds are preferably used because of their high charge separation speed and electron transfer speed.
- C 70 derivatives such as the PC 70 BM because excellent light absorption characteristics, it is possible to obtain a relatively high photoelectric conversion efficiency, more preferred.
- the content ratio (weight fraction) of the electron-donating organic material and the electron-accepting organic material of the present invention is not particularly limited, but an electron-donating organic material: an electron-accepting organic material Is preferably in the range of 1 to 99:99 to 1, more preferably in the range of 10 to 90:90 to 10, still more preferably in the range of 20 to 60:80 to 40. .
- the electron donating organic material and the electron accepting organic material of the present invention are preferably used as a mixture.
- the photovoltaic element material forms a single organic semiconductor layer
- the above-described content ratios of the electron-donating organic material and the electron-accepting organic material of the present invention contained in the single layer are included.
- the organic semiconductor layer has a laminated structure of two or more layers, it means the content ratio of the electron donating organic material and the electron accepting organic material of the present invention in the whole organic semiconductor layer.
- the method for removing impurities from the above-described benzothiadiazole compound, the electron-donating organic material containing the compound, and the electron-accepting organic material is not particularly limited, but column chromatography, recrystallization, sublimation, A precipitation method, a Soxhlet extraction method, a molecular weight fractionation method by GPC (gel permeation chromatography), a filtration method, an ion exchange method, a chelate method and the like can be used.
- a column chromatography method, a recrystallization method, and a sublimation method are preferably used for purification of a low molecular organic material.
- a reprecipitation method, a Soxhlet extraction method, or a molecular weight fractionation method by GPC is preferably used when removing low molecular weight components.
- GPC gel permeation chromatography
- a reprecipitation method, a chelate method, or an ion exchange method is preferably used. A plurality of these methods may be combined.
- the photovoltaic device of the present invention has at least a positive electrode and a negative electrode, and includes the photovoltaic device material of the present invention between them.
- FIG. 1 is a schematic view showing an example of the photovoltaic element of the present invention.
- reference numeral 1 is a substrate
- reference numeral 2 is a positive electrode
- reference numeral 3 is an organic semiconductor layer containing the photovoltaic element material of the present invention
- reference numeral 4 is a negative electrode.
- the organic semiconductor layer 3 contains the photovoltaic element material of the present invention. That is, the electron donating organic material and the electron accepting organic material of the present invention are included. These materials may be mixed or laminated. When mixed, the electron-donating organic material and the electron-accepting organic material of the present invention are compatible or phase-separated at the molecular level. The domain size of this phase separation structure is not particularly limited, but is usually 1 nm or more and 50 nm or less. When laminated, the layer having an electron-donating organic material exhibiting p-type semiconductor characteristics is preferably on the positive electrode side, and the layer having an electron-accepting organic material exhibiting n-type semiconductor characteristics is preferably on the negative electrode side.
- FIG. 5 denotes a layer having a benzothiadiazole compound having a structure represented by the general formula (1)
- reference numeral 6 denotes a layer having an electron-accepting organic material.
- the organic semiconductor layer preferably has a thickness of 5 nm to 500 nm, more preferably 30 nm to 300 nm.
- the layer having the electron donating organic material of the present invention preferably has a thickness of 1 nm to 400 nm, more preferably 15 nm to 150 nm.
- the organic semiconductor layer 3 may contain the benzothiadiazole compound of the present invention and an electron-donating organic material (p-type organic semiconductor) other than the electron-accepting organic material.
- an electron-donating organic material p-type organic semiconductor
- Examples of the electron donating organic material (p-type organic semiconductor) used here include those exemplified above as other compounds of the electron donating organic material.
- the photovoltaic device of the present invention it is preferable that either the positive electrode 2 or the negative electrode 4 has light transmittance.
- the light transmittance of the electrode is not particularly limited as long as incident light reaches the organic semiconductor layer 3 and an electromotive force is generated.
- the light transmittance in the present invention is a value obtained by [transmitted light intensity (W / m 2 ) / incident light intensity (W / m 2 )] ⁇ 100 (%).
- the thickness of the electrode may be in a range having light transparency and conductivity, and is preferably 20 nm to 300 nm, although it varies depending on the electrode material.
- the other electrode is not necessarily light-transmitting as long as it has conductivity, and the thickness is not particularly limited.
- the electrode material it is preferable to use a conductive material having a high work function for one electrode and a conductive material having a low work function for the other electrode.
- An electrode using a conductive material having a large work function is a positive electrode.
- Conductive materials with a large work function include metals such as gold, platinum, chromium and nickel, transparent metal oxides such as indium and tin, composite metal oxides (indium tin oxide (ITO), indium Zinc oxide (IZO) or the like is preferably used.
- the conductive material used for the positive electrode 2 is preferably one that is in ohmic contact with the organic semiconductor layer 3. Furthermore, when a hole transport layer described later is used, it is preferable that the conductive material used for the positive electrode 2 is in ohmic contact with the hole transport layer.
- An electrode using a conductive material having a small work function is a negative electrode, and as the conductive material having a small work function, alkali metal or alkaline earth metal, specifically lithium, magnesium, or calcium is used. Tin, silver, and aluminum are also preferably used. Furthermore, an electrode made of an alloy made of the above metal or a laminate of the above metal is also preferably used. Further, it is possible to improve the extraction current by introducing a metal fluoride such as lithium fluoride or cesium fluoride into the interface between the negative electrode 4 and the electron transport layer.
- the conductive material used for the negative electrode 4 is preferably one that is in ohmic contact with the organic semiconductor layer 3. Furthermore, when an electron transport layer described later is used, it is preferable that the conductive material used for the negative electrode 4 is in ohmic contact with the electron transport layer.
- the substrate 1 is a substrate on which an electrode material and an organic semiconductor layer can be laminated according to the type and application of the photoelectric conversion material, for example, inorganic materials such as alkali-free glass and quartz glass, polyester, polycarbonate, polyolefin, polyamide, polyimide, polyphenylene A film or plate produced by an arbitrary method from an organic material such as sulfide, polyparaxylene, epoxy resin or fluorine resin can be used.
- each substrate described above has a light transmittance of about 80%.
- a hole transport layer may be provided between the positive electrode 2 and the organic semiconductor layer 3.
- the material for forming the hole transport layer include conductive polymers such as polythiophene polymers, poly-p-phenylene vinylene polymers, polyfluorene polymers, phthalocyanine derivatives (H 2 Pc, CuPc, ZnPc, etc.) ), Low molecular organic compounds exhibiting p-type semiconductor properties such as porphyrin derivatives are preferably used.
- PEDOT polyethylenedioxythiophene
- PEDOT polyethylenedioxythiophene
- PEDOT polyethylenedioxythiophene
- PEDOT polystyrene sulfonate
- the thickness of the hole transport layer is preferably 5 nm to 600 nm, more preferably 30 nm to 200 nm.
- an electron transport layer may be provided between the organic semiconductor layer 3 and the negative electrode 4.
- the material for forming the electron transport layer is not particularly limited, but the above-described electron-accepting organic materials (NTCDA, PTCDA, PTCDI-C8H, oxazole derivatives, triazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, fullerene compounds, Organic materials exhibiting n-type semiconductor properties such as CNT and CN-PPV are preferably used.
- the thickness of the electron transport layer is preferably 5 nm to 600 nm, more preferably 30 nm to 200 nm.
- the photovoltaic device of the present invention may form a series junction by laminating (tandem) two or more organic semiconductor layers via one or more intermediate electrodes.
- a laminated structure of substrate / positive electrode / first organic semiconductor layer / intermediate electrode / second organic semiconductor layer / negative electrode can be given.
- the open circuit voltage can be improved.
- the hole transport layer described above may be provided between the positive electrode and the first organic semiconductor layer and between the intermediate electrode and the second organic semiconductor layer.
- the above-described hole transport layer may be provided between the first organic semiconductor layer and the intermediate electrode and between the second organic semiconductor layer and the negative electrode.
- At least one layer of the organic semiconductor layer contains the photovoltaic device material of the present invention, and the other layer does not reduce the short-circuit current. It preferably contains an electron donating organic material having a different band gap.
- electron-donating organic materials include the above-mentioned polythiophene polymers, poly-p-phenylene vinylene polymers, poly-p-phenylene polymers, polyfluorene polymers, polypyrrole polymers, polyaniline.
- Conjugated polymers such as polymer, polyacetylene polymer, polythienylene vinylene polymer, phthalocyanine derivatives such as H 2 phthalocyanine (H 2 Pc), copper phthalocyanine (CuPc), zinc phthalocyanine (ZnPc), porphyrin Derivatives, N, N′-diphenyl-N, N′-di (3-methylphenyl) -4,4′-diphenyl-1,1′-diamine (TPD), N, N′-dinaphthyl-N, N ′ -Triarylamine derivatives such as diphenyl-4,4'-diphenyl-1,1'-diamine (NPD), 4,4'-di (cal Tetrazole-9-yl) carbazole derivatives such as biphenyl (CBP), oligothiophene derivatives (terthiophene, quarter thiophene, sexithiophene include low molecular organic compound of
- the material for the intermediate electrode used here is preferably a material having high conductivity, for example, the above-mentioned metals such as gold, platinum, chromium, nickel, lithium, magnesium, calcium, tin, silver, aluminum, and transparent Metal oxides such as indium and tin, composite metal oxides (indium tin oxide (ITO), indium zinc oxide (IZO), etc.), alloys composed of the above metals and laminates of the above metals, polyethylene Examples include dioxythiophene (PEDOT) and those obtained by adding polystyrene sulfonate (PSS) to PEDOT.
- the intermediate electrode preferably has a light transmission property, but even a material such as a metal having a low light transmission property can often ensure a sufficient light transmission property by reducing the film thickness.
- a transparent electrode such as ITO (corresponding to a positive electrode in this case) is formed on the substrate by sputtering or the like.
- a photovoltaic device material containing the benzothiadiazole compound of the present invention and an electron-accepting organic material is dissolved in a solvent to form a solution, which is applied on the transparent electrode to form an organic semiconductor layer.
- the solvent used at this time is preferably an organic solvent, for example, methanol, ethanol, butanol, toluene, xylene, o-chlorophenol, acetone, ethyl acetate, ethylene glycol, tetrahydrofuran, dichloromethane, chloroform, dichloroethane, chlorobenzene, dichlorobenzene, Examples include chlorobenzene, chloronaphthalene, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, and ⁇ -butyrolactone. Two or more of these may be used.
- organic solvent for example, methanol, ethanol, butanol, toluene, xylene, o-chlorophenol, acetone, ethyl acetate, ethylene glycol, tetrahydrofuran, dichloromethane, chloroform, dichloroethane, chlorobenzene, dichlorobenzene
- the photoelectric conversion efficiency can be further improved by containing a fluorous solvent (an organic solvent having one or more fluorine atoms in the molecule).
- fluorous solvents include benzotrifluoride, hexafluorobenzene, 1,1,1,3,3,3-hexafluoro-2-propanol, perfluorotoluene, perfluorodecalin, 2-fluorobenzotrifluoride, 3-fluorobenzo Trifluoride, 4-fluorobenzotrifluoride, fluorobenzene, pentafluorobenzene, 1,2,4-trifluorobenzene, 1,2,5-trifluorobenzene, 1,2-difluorobenzene, 1,3-difluorobenzene 1,4-difluorobenzene, 2H, 3H-decafluoropentane, perfluorononane, perfluorooctane, perfluoroheptane, perfluoro
- the content of the fluorous solvent is preferably 0.01 to 20% by volume, more preferably 0.1 to 5% by volume with respect to the total amount of the organic solvent. Further, it is preferably 0.01 to 30% by weight, more preferably 0.4 to 4% by weight with respect to the total amount of organic solvent.
- the electron-donating organic material and the electron-accepting organic material of the present invention are added to the solvent in a desired ratio. Then, the solution is dissolved using a method such as heating, stirring, and ultrasonic irradiation to form a solution, which is applied on the transparent electrode.
- the photoelectric conversion efficiency of the photovoltaic element can be improved by using a mixture of two or more solvents. This is presumably because the electron-donating organic material and the electron-accepting organic material undergo phase separation at the nano level, and a carrier path that forms a path for electrons and holes is formed.
- an optimal combination can be selected depending on the types of the electron donating organic material and the electron accepting organic material to be used.
- chloroform and chlorobenzene are mentioned as preferable solvents to be combined among the above.
- the electron-donating organic material is applied by applying a solution of the electron-donating organic material of the present invention. After forming the layer, a solution of the electron-accepting organic material is applied to form the layer.
- the electron-donating organic material and the electron-accepting organic material of the present invention are low molecular weight substances having a molecular weight of about 1000 or less, it is also possible to form a layer using a vapor deposition method.
- the formation method may be selected according to the characteristics of the organic semiconductor layer to be obtained, such as film thickness control and orientation control.
- the electron donating organic material of the present invention and the electron accepting organic material have a concentration of 1 to 20 g / l (the electron donating organic material, the electron accepting organic material, and the solvent of the present invention).
- the weight of the electron-donating organic material and the electron-accepting organic material of the present invention with respect to the volume of the solution containing hydrogen is preferable.
- the formed organic semiconductor layer may be subjected to an annealing treatment under reduced pressure or in an inert atmosphere (in a nitrogen or argon atmosphere).
- a preferable temperature for the annealing treatment is 40 ° C to 300 ° C, more preferably 50 ° C to 200 ° C. Further, by performing the annealing process, the effective area where the stacked layers permeate and contact each other at the interface increases, and the short-circuit current can be increased. This annealing treatment may be performed after the formation of the negative electrode.
- a metal electrode such as Al (corresponding to a negative electrode in this case) is formed on the organic semiconductor layer by vacuum deposition or sputtering.
- the metal electrode is vacuum-deposited using a low molecular organic material for the electron transport layer, it is preferable that the metal electrode is continuously formed while maintaining the vacuum.
- a desired p-type organic semiconductor material such as PEDOT
- PEDOT p-type organic semiconductor material
- the solvent is removed using a vacuum thermostat or a hot plate to form a hole transport layer.
- a vacuum vapor deposition method using a vacuum vapor deposition machine.
- a desired n-type organic semiconductor material (fullerene derivative, etc.) is applied onto the organic semiconductor layer by spin coating, bar coating, blade casting, or spraying. After coating with, for example, a solvent is removed using a vacuum thermostat or a hot plate to form an electron transport layer.
- a vacuum deposition method using a vacuum deposition machine.
- the positive electrode or the negative electrode Before forming the organic semiconductor layer, the positive electrode or the negative electrode may be pretreated with the above-mentioned fluorous solvent, and the photoelectric conversion efficiency can be further improved. Further, when a hole transport layer or an electron transport layer is provided between the positive electrode or the negative electrode and the organic semiconductor layer, the hole transport layer or the electron transport layer may be pretreated with a fluorous solvent.
- the pretreatment method is not particularly limited as long as the electrode is in direct contact with the fluorous solvent, and examples thereof include a method of applying a fluorous solvent on the electrode and a method of exposing the electrode to a vapor of a fluorous compound. . Examples of the method for applying the fluorous solvent include spin coating, blade coating, slit die coating, screen printing coating, bar coater coating, dip pulling method, ink jet method, and spray method.
- ITO indium tin oxide
- PEDOT polyethylene dioxythiophene
- PSS polystyrene sulfonate
- PC 70 BM phenyl C71 butyric acid methyl ester
- LiF lithium fluoride
- Eg band gap HOMO: highest occupied molecular orbital
- Isc short circuit current density
- Voc Open-circuit voltage
- FF Fill factor ⁇ : Photoelectric conversion efficiency
- an FT-NMR apparatus JEOL JNM-EX270 manufactured by JEOL Ltd.
- the average molecular weight (number average molecular weight, weight average molecular weight) was calculated by an absolute calibration curve method using a GPC apparatus (manufactured by TOSOH Co., Ltd., to which chloroform was fed, high-speed GPC apparatus HLC-8220 GPC).
- the light absorption edge wavelength is an ultraviolet-visible absorption spectrum (measurement wavelength) of a thin film formed on a glass with a thickness of about 60 nm using a U-3010 spectrophotometer manufactured by Hitachi, Ltd. (Range: 300-900 nm).
- the band gap (Eg) was calculated from the light absorption edge wavelength by the above formula.
- the thin film was formed by spin coating using chloroform as a solvent.
- the highest occupied molecular orbital (HOMO) level is the surface analysis device (in-air ultraviolet photoelectron spectrometer AC-1 type, manufactured by Riken Kikai Co., Ltd.) for thin films formed on ITO glass with a thickness of about 60 nm. ).
- the thin film was formed by spin coating using chloroform as a solvent.
- Synthesis example 1 Compound A-1 was synthesized by the method shown in Formula 1.
- Compound A-1 had a light absorption edge wavelength of 727 nm, a band gap (Eg) of 1.71 eV, and a highest occupied molecular orbital (HOMO) level of ⁇ 4.90 eV.
- Synthesis example 2 Compound A-2 was synthesized by the method shown in Formula 2.
- Synthesis example 5 Compound A-5 was synthesized by the method shown in Formula 5.
- the obtained solid was dissolved in 300 ml of chloroform, passed through a silica gel short column (eluent: chloroform), concentrated to dryness, and washed with methanol and hexane in this order to obtain 320 mg of compound B-2.
- the weight average molecular weight was 593233, the number average molecular weight was 54251, and the degree of polymerization n was 317.7.
- the light absorption edge wavelength was 661 nm, the band gap (Eg) was 1.87 eV, and the highest occupied molecular orbital (HOMO) level was ⁇ 5.37 eV.
- Synthesis example 8 Compound B-3 was synthesized by the method shown in Formula 8.
- the obtained solution was added to concentrated hydrochloric acid / methanol (10 ml / 200 ml), and the produced solid was collected by filtration and washed with methanol, acetone, water and acetone in this order.
- the obtained solid was Soxhlet washed with acetone for 3 hours and then dissolved in chloroform. After concentration to dryness, washing with methanol gave 104 mg of compound A-8.
- the weight average molecular weight was 65060, the number average molecular weight was 15961, and the polymerization degree n was 37.3.
- the light absorption edge wavelength was 720 nm, the band gap (Eg) was 1.72 eV, and the highest occupied molecular orbital (HOMO) level was -5.00 eV.
- the obtained solid was dissolved in 100 ml of chloroform, passed through a silica gel short column (eluent: chloroform), concentrated and dried, and then washed with hot acetone and methanol in this order to obtain 100 mg of compound A-8.
- the weight average molecular weight was 38843, the number average molecular weight was 22526, and the polymerization degree n was 23.6.
- the light absorption edge wavelength was 718 nm, the band gap (Eg) was 1.73 eV, and the highest occupied molecular orbital (HOMO) level was ⁇ 5.13 eV.
- Example 1 Add 1 mg of the above A-1 and 4 mg of PC 70 BM (Science Laboratories) into a sample bottle containing 0.25 ml of chlorobenzene, and use an ultrasonic cleaner (US-2 manufactured by Inoue Seieido Co., Ltd.) The solution A was obtained by ultrasonic irradiation for 30 minutes in an output of 120 W).
- a glass substrate on which an ITO transparent conductive layer serving as a positive electrode having a thickness of 120 nm was deposited by sputtering was cut into 38 mm ⁇ 46 mm, and then ITO was patterned into a 38 mm ⁇ 13 mm rectangular shape by photolithography.
- the obtained substrate was subjected to ultrasonic cleaning for 10 minutes with an alkali cleaning solution (“Semico Clean” EL56 (trade name), manufactured by Furuuchi Chemical Co., Ltd.), and then washed with ultrapure water.
- an alkali cleaning solution (“Semico Clean” EL56 (trade name), manufactured by Furuuchi Chemical Co., Ltd.
- a PEDOT: PSS aqueous solution (0.8% by weight of PEDOT, 0.5% by weight of PPS) serving as a hole transport layer was formed on the substrate to a thickness of 60 nm by spin coating. did.
- the above solution A was dropped onto the PEDOT: PSS layer, and an organic semiconductor layer having a thickness of 100 nm was formed by spin coating.
- the substrate on which the organic semiconductor layer is formed and the cathode mask are placed in a vacuum vapor deposition apparatus, and the vacuum in the apparatus is exhausted again until the vacuum level becomes 1 ⁇ 10 ⁇ 3 Pa or less, and the negative electrode is formed by resistance heating.
- An aluminum layer was deposited to a thickness of 80 nm. As described above, a photovoltaic device having an area where the stripe-shaped ITO layer intersects with the aluminum layer was 5 mm ⁇ 5 mm was produced.
- the positive and negative electrodes of the photovoltaic device thus fabricated were connected to a picoammeter / voltage source 4140B manufactured by Hewlett-Packard Co., and simulated sunlight (from Yamashita Denso Co., Ltd., simplified) from the ITO layer side in the atmosphere.
- the short-circuit current density (value of the current density when the applied voltage is 0 V) is 6.37 mA / cm 2
- the open circuit voltage value of the applied voltage when the current density is 0
- the fill factor (FF) was 0.313
- the photoelectric conversion efficiency calculated from these values was 1.82%.
- the fill factor and photoelectric conversion efficiency were calculated by the following equations.
- Example 2 A photovoltaic device was prepared in the same manner as in Example 1 except that A-3 was used in place of A-1, and current-voltage characteristics were measured.
- the short-circuit current density at this time was 6.12 mA / cm 2
- the open-circuit voltage was 0.810 V
- the fill factor (FF) was 0.346
- the photoelectric conversion efficiency calculated from these values was 1.72%. .
- Example 3 A photovoltaic device was produced in the same manner as in Example 1 except that A-4 was used instead of A-1, and current-voltage characteristics were measured. At this time, the short-circuit current density was 7.71 mA / cm 2 , the open-circuit voltage was 0.842 V, the fill factor (FF) was 0.418, and the photoelectric conversion efficiency calculated from these values was 2.72%. .
- Comparative Example 1 A photovoltaic device was produced in the same manner as in Example 1 except that B-1 (weight average molecular weight: 2630, number average molecular weight: 1604, polymerization degree n: 3.8) was used instead of A-1. Then, the current-voltage characteristics were measured. At this time, the short-circuit current density was 3.57 mA / cm 2 , the open-circuit voltage was 0.900 V, the fill factor (FF) was 0.280, and the photoelectric conversion efficiency calculated from these values was 0.90%. .
- B-1 weight average molecular weight: 2630, number average molecular weight: 1604, polymerization degree n: 3.8
- Comparative Example 2 A photovoltaic device was produced in the same manner as in Example 1 except that B-2 was used in place of A-1, and current-voltage characteristics were measured.
- the short-circuit current density at this time was 4.52 mA / cm 2
- the open-circuit voltage was 0.920 V
- the fill factor (FF) was 0.282
- the photoelectric conversion efficiency calculated from these values was 1.17%. .
- Comparative Example 3 A photovoltaic device was produced in the same manner as in Example 1 except that B-3 was used in place of A-1, and current-voltage characteristics were measured.
- the short-circuit current density at this time was 4.58 mA / cm 2
- the open-circuit voltage was 0.820 V
- the fill factor (FF) was 0.266
- the photoelectric conversion efficiency calculated from these values was 1.00%. .
- Example 4 A photovoltaic device was prepared in exactly the same manner as in Example 3 except that a chlorobenzene / benzotrifluoride (trifluoromethylbenzene) mixed solution (0.2475 ml / 0.0025 ml) was used instead of 0.25 ml of chlorobenzene, Current-voltage characteristics were measured. The short-circuit current density at this time was 7.84 mA / cm 2 , the open-circuit voltage was 0.870 V, the fill factor (FF) was 0.438, and the photoelectric conversion efficiency calculated from these values was 2.99%. .
- Example 5 A photovoltaic device was prepared in the same manner as in Example 4 except that lithium fluoride was deposited to a thickness of 0.1 nm before depositing the aluminum layer serving as the negative electrode, and current-voltage characteristics were measured. At this time, the short-circuit current density was 8.44 mA / cm 2 , the open-circuit voltage was 0.870 V, the fill factor (FF) was 0.430, and the photoelectric conversion efficiency calculated from these values was 3.16%. .
- Example 6 Except for using a mixed solution of chlorobenzene / chloroform (0.0834 ml / 0.3333 ml) instead of a mixed solution of chlorobenzene / benzotrifluoride (trifluoromethylbenzene) (0.2475 ml / 0.0025 ml), the same as Example 5 Thus, a photovoltaic device was produced, and current-voltage characteristics were measured. At this time, the short-circuit current density was 8.72 mA / cm 2 , the open-circuit voltage was 0.860 V, the fill factor (FF) was 0.466, and the photoelectric conversion efficiency calculated from these values was 3.49%. .
- FF fill factor
- Example 7 A photovoltaic device was prepared in the same manner as in Example 1 except that A-6 was used instead of A-1, and current-voltage characteristics were measured. At this time, the short-circuit current density was 6.13 mA / cm 2 , the open circuit voltage was 0.910 V, and the fill factor (FF) was 0.360, and the photoelectric conversion efficiency calculated from these values was 2.00%. .
- Example 8 A photovoltaic device was produced in the same manner as in Example 1 except that A-7 was used instead of A-1, and current-voltage characteristics were measured. At this time, the short-circuit current density was 7.54 mA / cm 2 , the open-circuit voltage was 0.810 V, the fill factor (FF) was 0.400, and the photoelectric conversion efficiency calculated from these values was 2.44%. .
- Example 9 A photovoltaic device was produced in the same manner as in Example 1 except that A-8 was used in place of A-1, and current-voltage characteristics were measured. At this time, the short-circuit current density was 6.40 mA / cm 2 , the open-circuit voltage was 0.859 V, the fill factor (FF) was 0.413, and the photoelectric conversion efficiency calculated from these values was 2.27%. .
- Example 10 A chlorobenzene / chloroform / benzotrifluoride (trifluoromethylbenzene) mixed solution (0.0825 ml / 0.33 ml / 0.0042 ml) was used instead of the chlorobenzene / chloroform mixed solution (0.0834 ml / 0.3333 ml).
- a photovoltaic device was produced in exactly the same manner as in Example 6, and the current-voltage characteristics were measured. At this time, the short-circuit current density was 8.50 mA / cm 2 , the open-circuit voltage was 0.880 V, the fill factor (FF) was 0.490, and the photoelectric conversion efficiency calculated from these values was 3.67%. .
- Example 11 Before forming the organic semiconductor layer, a photovoltaic device was produced in the same manner as in Example 6 except that benzotrifluoride (trifluoromethylbenzene) was spin-coated on the PEDOT: PSS layer. Characteristics were measured. At this time, the short-circuit current density was 8.30 mA / cm 2 , the open-circuit voltage was 0.890 V, the fill factor (FF) was 0.500, and the photoelectric conversion efficiency calculated from these values was 3.69%. .
- benzotrifluoride trifluoromethylbenzene
- the photovoltaic element using the electron donating organic material of the present invention can be applied to various photoelectric conversion elements utilizing a photoelectric conversion function, an optical rectification function, and the like.
- photovoltaic cells such as solar cells
- electronic elements such as optical sensors, optical switches, and phototransistors
- optical recording materials such as optical memories
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Abstract
Description
J.J.M.Halls、C.A.Walsh、N.C.Greenham、E.A.Marseglla、R.H.Frirnd、S.C.Moratti、A.B.Homes著、「ネイチャー(Nature)」、1995年、376号、498頁 E.Kymakis、G.A.J.Amaratunga著、「アプライド フィジクス レターズ(Applied Physics Letters)」(米国)、2002年、80巻、112頁 G.Yu、J.Gao、J.C.Hummelen、F.Wudl、A.J.Heeger著、「サイエンス(Science)」、1995年、270巻、1789頁 E.Bundgaard、F.C.Krebs著、「ソーラー エナジー マテリアルズ アンド ソーラー セル(Solar Energy Materials & Solar Cells)」、2007年、91巻、954頁 X.Li、W.Zeng、Y.Zhang、Q.Hou、W.Yang、Y.Cao著、「ヨーロピアン ポリマー ジャーナル(European Polymer Journal)」、2005年、41巻、2923頁 E.Bundgaard、F.C.Krebs著、「マクロモレキュルズ(Macromolecules)」、2006年、39巻、2823頁
2 正極
3 有機半導体層
4 負極
5 一般式(1)で表される構造を有するベンゾチアジアゾール化合物を有する層
6 電子受容性有機材料を有する層
ここで用いる薄膜の形成方法は特に限定されるものではないが、通常、クロロホルム、テトラヒドロフラン、クロロベンゼンなどの有機溶媒に溶解させて、スピンコートなどのウェットコーティング法によりガラス基板上に薄膜を形成する。薄膜の厚さは、薄すぎると吸光度が低すぎ、厚すぎると吸光度が高すぎて測定に支障を来たす場合があるため、通常、5nm~500nmの範囲であることが好ましく、10nm~200nmの範囲であることがさらに好ましい。
ITO:インジウム錫酸化物
PEDOT:ポリエチレンジオキシチオフェン
PSS:ポリスチレンスルホネート
PC70BM:フェニル C71 ブチリックアシッドメチルエステル
LiF:フッ化リチウム
Eg:バンドギャップ
HOMO:最高被占分子軌道
Isc:短絡電流密度
Voc:開放電圧
FF:フィルファクター
η:光電変換効率
なお、1H-NMR測定にはFT-NMR装置((株)日本電子製JEOL JNM-EX270)を用いた。また、平均分子量(数平均分子量、重量平均分子量)はGPC装置(クロロホルムを送液したTOSOH社製、高速GPC装置HLC-8220GPC)を用い、絶対検量線法によって算出した。重合度nは以下の式で算出した。
重合度n=[(重量平均分子量)/(モノマー1ユニットの分子量)]
また、光吸収端波長は、ガラス上に約60nmの厚さに形成した薄膜について、日立製作所(株)製のU-3010型分光光度計を用いて測定した薄膜の紫外可視吸収スペクトル(測定波長範囲:300~900nm)から得た。バンドギャップ(Eg)は上述した式により、光吸収端波長から算出した。なお、薄膜はクロロホルムを溶媒に用いてスピンコート法により形成した。
化合物A-1を式1に示す方法で合成した。
1H-NMR(CDCl3,ppm):8.00(s,2H)、7.84(s,2H)、7.20-7.15(m,8H)、7.04(d,2H)、6.95(d,2H)、2.88(t,4H)、2.79(t,4H)、1.77-1.29(m,48H)、0.88(m,12H)
化合物A-1の光吸収端波長は727nm、バンドギャップ(Eg)は1.71eV、最高被占分子軌道(HOMO)準位は-4.90eVであった。
化合物A-2を式2に示す方法で合成した。
化合物A-3を式3に示す方法で合成した。
化合物A-4を式4に示す方法で合成した。
化合物A-5を式5に示す方法で合成した。
化合物A-6を式6に示す方法で合成した。
化合物B-2を式7に示す方法で合成した。
化合物B-3を式8に示す方法で合成した。
化合物A-7を式9に示す方法で合成した。
1H-NMR(CDCl3,ppm):8.04(s,2H)、7.84(s,2H)、7.21-7.01(m,10H)、3.85(t,4H)、3.74-3.60(m,20H)、3.47(t,8H)、3.19(t,4H)、3.03(t,4H)、1.61-1.51(m,8H)、1.44-1.26(m,8H)、0.91(m,12H) 。
化合物A-8を式10に示す方法で合成した。
上記A-1の1mgとPC70BM(サイエンスラボラトリーズ社製)4mgをクロロベンゼン0.25mlの入ったサンプル瓶の中に加え、超音波洗浄機((株)井内盛栄堂製US-2(商品名)、出力120W)中で30分間超音波照射することにより溶液Aを得た。
フィルファクター=JVmax/(短絡電流密度×開放電圧)
(ここで、JVmaxは、印加電圧が0Vから開放電圧値の間で電流密度と印加電圧の積が最大となる点における電流密度と印加電圧の積の値である。)
光電変換効率=[(短絡電流密度×開放電圧×フィルファクター)/擬似太陽光強度(100mW/cm2)]×100(%)
以下の実施例と比較例におけるフィルファクターと光電変換効率も全て上式により算出した。
A-1の代わりに上記A-3を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流-電圧特性を測定した。この時の短絡電流密度は6.12mA/cm2、開放電圧は0.810V、フィルファクター(FF)は0.346であり、これらの値から算出した光電変換効率は1.72%であった。
A-1の代わりに上記A-4を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流-電圧特性を測定した。この時の短絡電流密度は7.71mA/cm2、開放電圧は0.842V、フィルファクター(FF)は0.418であり、これらの値から算出した光電変換効率は2.72%であった。
A-1の代わりに下記B-1(重量平均分子量:2630、数平均分子量:1604、重合度n:3.8)を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流-電圧特性を測定した。この時の短絡電流密度は3.57mA/cm2、開放電圧は0.900V、フィルファクター(FF)は0.280であり、これらの値から算出した光電変換効率は0.90%であった。
A-1の代わりに上記B-2を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流-電圧特性を測定した。この時の短絡電流密度は4.52mA/cm2、開放電圧は0.920V、フィルファクター(FF)は0.282であり、これらの値から算出した光電変換効率は1.17%であった。
A-1の代わりに上記B-3を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流-電圧特性を測定した。この時の短絡電流密度は4.58mA/cm2、開放電圧は0.820V、フィルファクター(FF)は0.266であり、これらの値から算出した光電変換効率は1.00%であった。
クロロベンゼン0.25mlの代わりにクロロベンゼン/ベンゾトリフルオリド(トリフルオロメチルベンゼン)混合溶液(0.2475ml/0.0025ml)を用いた他は実施例3と全く同様にして光起電力素子を作製し、電流-電圧特性を測定した。この時の短絡電流密度は7.84mA/cm2、開放電圧は0.870V、フィルファクター(FF)は0.438であり、これらの値から算出した光電変換効率は2.99%であった。
負極となるアルミニウム層を蒸着する前にフッ化リチウムを0.1nmの厚さに蒸着した他は実施例4と全く同様にして光起電力素子を作製し、電流-電圧特性を測定した。この時の短絡電流密度は8.44mA/cm2、開放電圧は0.870V、フィルファクター(FF)は0.430であり、これらの値から算出した光電変換効率は3.16%であった。
クロロベンゼン/ベンゾトリフルオリド(トリフルオロメチルベンゼン)混合溶液(0.2475ml/0.0025ml)の代わりにクロロベンゼン/クロロホルム混合溶液(0.0834ml/0.3333ml)を用いた他は実施例5と全く同様にして光起電力素子を作製し、電流-電圧特性を測定した。この時の短絡電流密度は8.72mA/cm2、開放電圧は0.860V、フィルファクター(FF)は0.466であり、これらの値から算出した光電変換効率は3.49%であった。
A-1の代わりに上記A-6を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流-電圧特性を測定した。この時の短絡電流密度は6.13mA/cm2、開放電圧は0.910V、フィルファクター(FF)は0.360であり、これらの値から算出した光電変換効率は2.00%であった。
A-1の代わりに上記A-7を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流-電圧特性を測定した。この時の短絡電流密度は7.54mA/cm2、開放電圧は0.810V、フィルファクター(FF)は0.400であり、これらの値から算出した光電変換効率は2.44%であった。
A-1の代わりに上記A-8を用いた他は実施例1と全く同様にして光起電力素子を作製し、電流-電圧特性を測定した。この時の短絡電流密度は6.40mA/cm2、開放電圧は0.859V、フィルファクター(FF)は0.413であり、これらの値から算出した光電変換効率は2.27%であった。
クロロベンゼン/クロロホルム混合溶液(0.0834ml/0.3333ml)の代わりにクロロベンゼン/クロロホルム/ベンゾトリフルオリド(トリフルオロメチルベンゼン)混合溶液(0.0825ml/0.33ml/0.0042ml)を用いた他は実施例6と全く同様にして光起電力素子を作製し、電流-電圧特性を測定した。この時の短絡電流密度は8.50mA/cm2、開放電圧は0.880V、フィルファクター(FF)は0.490であり、これらの値から算出した光電変換効率は3.67%であった。
有機半導体層を形成する前に、PEDOT:PSS層の上にベンゾトリフルオリド(トリフルオロメチルベンゼン)をスピンコートした他は実施例6と全く同様にして光起電力素子を作製し、電流-電圧特性を測定した。この時の短絡電流密度は8.30mA/cm2、開放電圧は0.890V、フィルファクター(FF)は0.500であり、これらの値から算出した光電変換効率は3.69%であった。
Claims (6)
- (a)ベンゾチアジアゾール骨格とオリゴチオフェン骨格とを含み、(b)バンドギャップ(Eg)が1.8eV以下であり、(c)最高被占分子軌道(HOMO)準位が-4.8eV以下であるベンゾチアジアゾール化合物を含む電子供与性有機材料であって、前記ベンゾチアジアゾール化合物が、ベンゾチアジアゾール骨格とオリゴチオフェン骨格が交互に共有結合したものであり、ベンゾチアジアゾール骨格:オリゴチオフェン骨格の比が1:1~1:2の範囲(ただし、1:1は除く)であり、1つのオリゴチオフェン骨格に含まれるチオフェン環の数が3個以上12個以下である電子供与性有機材料。
- 前記ベンゾチアジアゾール化合物のベンゾチアジアゾール骨格が2,1,3-ベンゾチアジアゾール-4,7-ジイルであり、オリゴチオフェン骨格がオリゴ(チオフェン-2,5-ジイル)である請求項1記載の電子供与性有機材料。
- 電子受容性有機材料および請求項1~3いずれかに記載の電子供与性有機材料を含む光起電力素子用材料。
- 電子受容性有機材料がフラーレン化合物である請求項4記載の光起電力素子用材料。
- 少なくとも正極と負極を有する光起電力素子であって、負極と正極の間に請求項4または5記載の光起電力素子用材料を含む光起電力素子。
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Also Published As
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TW201002755A (en) | 2010-01-16 |
EP2266982A4 (en) | 2012-05-02 |
EP2266982B1 (en) | 2013-09-04 |
KR101548764B1 (ko) | 2015-08-31 |
KR20100130623A (ko) | 2010-12-13 |
US8558108B2 (en) | 2013-10-15 |
CN101998955A (zh) | 2011-03-30 |
US20110023964A1 (en) | 2011-02-03 |
EP2266982A1 (en) | 2010-12-29 |
JPWO2009125647A1 (ja) | 2011-08-04 |
CN101998955B (zh) | 2014-05-14 |
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