WO2015029432A1 - Élément de conversion photoélectrique - Google Patents

Élément de conversion photoélectrique Download PDF

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WO2015029432A1
WO2015029432A1 PCT/JP2014/004410 JP2014004410W WO2015029432A1 WO 2015029432 A1 WO2015029432 A1 WO 2015029432A1 JP 2014004410 W JP2014004410 W JP 2014004410W WO 2015029432 A1 WO2015029432 A1 WO 2015029432A1
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photoelectric conversion
carbon number
organic semiconductor
long chain
electrode
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Japanese (ja)
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隆志 岡部
池田　哲
格 尾坂
和男 瀧宮
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Ｊｘ日鉱日石エネルギー株式会社
独立行政法人理化学研究所
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    • 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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    • C08G61/122—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
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    • 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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    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3246—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing nitrogen and sulfur as heteroatoms
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    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/36—Oligomers, i.e. comprising up to 10 repeat units
    • C08G2261/364—Oligomers, i.e. comprising up to 10 repeat units containing hetero atoms
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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    • C08G2261/90—Applications
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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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    • 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
    • H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
    • 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 photoelectric conversion element that converts light energy into electric energy by photoelectric conversion.
  • Organic solar cells are considered to be promising next-generation solar cells because they are flexible and can be expected to have a large area, light weight, and a simple and inexpensive manufacturing method. At present, significant improvement in conversion efficiency is an important issue for practical application of organic solar cells.
  • Patent Document 1 discloses a p-type organic semiconductor material having a naphthobisthiadiazole (NTz) skeleton as a donor material.
  • the present invention has been made in view of these problems, and an object thereof is to provide a technique capable of improving the photoelectric conversion efficiency of a photoelectric conversion element including an organic semiconductor.
  • the photoelectric conversion element includes a photoelectric conversion layer, an electron extraction electrode provided on one main surface side of the photoelectric conversion layer, a hole extraction electrode provided on the other main surface side of the photoelectric conversion layer, And the photoelectric conversion layer has an organic semiconductor having a thiazolothiazole skeleton and a naphthobisthiadiazole skeleton represented by the following formula.
  • R 1 and R 2 are linear alkyl groups or branched alkyl groups, and the difference between the long chain carbon number of R 1 and the long chain carbon number of R 2 is within 3 And an alkyl group having a longer long-chain carbon number among R 1 and R 2 (if the long-chain carbon number is the same, either the larger total carbon number or the total carbon number is the same).
  • the total carbon number of is 15 or less.
  • the difference between the long chain carbon number of R 1 and the long chain carbon number of R 2 may be zero. Further, both R 1 and R 2 may be 2-butyloctyl.
  • the photoelectric conversion efficiency of a photoelectric conversion element containing an organic semiconductor can be improved.
  • FIG. 1 is a schematic cross-sectional view showing a configuration of a photoelectric conversion element 10 according to an embodiment.
  • the photoelectric conversion element 10 of this Embodiment is an organic thin film solar cell which has a photoelectric converting layer containing an organic semiconductor.
  • the photoelectric conversion element 10 includes a substrate 20, a first electrode 30, a hole transport layer 40, a photoelectric conversion layer 50, an electron transport layer 60, and a second electrode 70.
  • the first electrode 30 is a positive electrode and is electrically connected to a photoelectric conversion layer 50 described later.
  • the first electrode 30 is located on the light-receiving surface side of the photoelectric conversion layer 50, ITO (Indium Tin Oxide) , SnO 2, FTO (Fluorine doped Tin Oxide), ZnO, AZO (Aluminum doped Zinc Oxide), IZO It is made of a conductive metal oxide such as (Indium doped Zinc Oxide) or a thin metal film such as gold, silver, copper, or aluminum, or a transparent conductive film such as a mesh or stripe.
  • the first electrode 30 is formed on the light-transmitting substrate 20 so as not to disturb the light receiving performance.
  • the substrate 20 may be colorless or colored glass, meshed glass, glass block, or the like, or may be colorless or colored resin having transparency.
  • resins include polyesters such as polyethylene terephthalate, polyamide, polysulfone, polyether sulfone, polyether ether ketone, polyphenylene sulfide, polycarbonate, polyimide, polymethyl methacrylate, polystyrene, cellulose triacetate, and polymethylpentene. Etc.
  • the hole transport layer 40 is provided in a region between the first electrode 30 and the photoelectric conversion layer 50.
  • the hole transport layer 40 has a function of easily moving holes from the photoelectric conversion layer 50 to the first electrode 30.
  • the hole transport layer 40 may have a function of making it difficult for electrons to move from the photoelectric conversion layer 50 to the first electrode 30.
  • the hole transport layer 40 includes, for example, conductive polymers such as PEDOT (polythiophene) / PSS (polystyrenesulfonate), polypyrrole, polyaniline, polyfuran, polypyridine, polycarbazole, Inorganic compounds such as MoO 3 and WO 3 , organic semiconductor molecules such as phthalocyanine and porphyrin, and derivatives and transition metal complexes thereof, charge transfer agents such as triphenylamine compounds and hydrazine compounds, and tetrariafulvalene (TTF) Formed of a material having a high hole mobility such as a simple charge transfer complex.
  • the thickness of the hole transport layer is not particularly limited, but is preferably 10 to 100 nm, and more preferably 20 to 60 nm.
  • the photoelectric conversion layer 50 of the present embodiment is a bulk heterojunction layer, and is formed by mixing a p-type organic semiconductor having electron donating properties and an n-type organic semiconductor having electron accepting properties at a nano level.
  • a p-type organic semiconductor an organic semiconductor (electron donor molecule) having a structure having a thiazolothiazole naphthobisthiadiazole (TzTz-NTz) skeleton represented by the following formula is used.
  • R 1 and R 2 are a linear alkyl group or an alkyl group having a branched chain.
  • the difference between the long chain carbon number of R 1 and the long chain carbon number of R 2 is 3 or less (Condition 1), and the longer long carbon number of R 1 and R 2 (long chain carbon number) In the case where the total number of carbon atoms is the same or the total number of carbon atoms is the same), the total carbon number of the alkyl group is 15 or less (condition 2).
  • the difference between the long chain carbon number of R 1 and the long chain carbon number of R 2 is most preferably 0.
  • the average weight molecular weight of the organic semiconductor represented by the above formula is preferably 5,000 to 500,000, and more preferably 10,000 to 150,000.
  • N in the formula is larger than 1, and is preferably a number with an average weight molecular weight of the organic semiconductor of 5,000 to 500,000.
  • linear alkyl group R 1 and R 2 examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, among which butyl, hexyl Octyl, decyl, dodecyl and tetradecyl are preferred.
  • R 1 and R 2 of the alkyl group having a branched chain 2-ethylhexyl (EH, long-chain carbon number 6 (C6), total carbon number 8), 2-butylhexyl (BH, long-chain carbon number 6 (C6)) , Total carbon number 10), 2-ethyloctyl (EO, long chain carbon number 8 (C8), total carbon number 10), 2-butyloctyl (BO, long chain carbon number 8 (C8), total carbon number 12) 2-hexyloctyl (HO, long chain carbon number 8 (C8), total carbon number 14), 4-ethylhexyl (EH, long chain carbon number 6 (C6), total carbon number 8), 4-ethyloctyl (EO) , Long chain carbon number 8 (C8), total carbon number 10), 4-octylpentyl (OP, long chain carbon number 8 (C8), total carbon number 13), 2-heptyloctyl (long chain carbon number 8 (C8 ), Total carbon number 15)
  • R 1 and R 2 are linear alkyl groups, the number of long-chain carbons and the total number of carbons are the same.
  • n-type organic semiconductor examples include fullerene, [60] PCBM (phenyl C61 butyric acid methyl ester), bis [60] PCBM, ICMA (monoindenyl C60), ICBA (bisindenyl C60) and [70] PCBM (phenyl C71).
  • Fullerene derivatives such as methyl butyrate
  • carbon nanotubes carbon materials such as chemically modified carbon nanotubes, condensed ring aromatic compounds (naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives, fluoranthene Derivatives), 5- to 7-membered heterocyclic compounds containing nitrogen, oxygen, and sulfur atoms (eg, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, quinoxaline, quinazoline, phthalazine, Norin, isoquinoline, pteridine, acridine, phenazine, phenanthroline, tetrazole, pyrazole, imidazole, thiazole, oxazole, indazole, benzimidazole, benzotriazole, benzoxazole, benzo
  • the film thickness of the photoelectric conversion layer 50 is not particularly limited, but is 5 to 1000 nm, preferably 30 to 500 nm, more preferably 50 to 400 nm, and still more preferably 80 to 300 nm.
  • the electron transport layer 60 is provided in a region between the second electrode 70 and the photoelectric conversion layer 50.
  • the electron transport layer 60 has a function of easily moving electrons from the photoelectric conversion layer 50 to the second electrode 70. Further, the electron transport layer 60 may have a function of making it difficult for holes to move from the photoelectric conversion layer 50 to the second electrode 70.
  • the electron transport layer 60 is formed of a material having a high electron mobility. The material to be used is not particularly limited as long as it meets the object of the present invention.
  • organic semiconductor molecules such as phenanthroline, bathocuproin, and perylene
  • organic substances such as derivatives and transition metal complexes thereof, LiF, CsF, CsO , Cs 2 CO 3 , TiOx (x is an arbitrary number of 0 to 2), inorganic compounds such as ZnO, and metals such as Ca and Ba.
  • the thickness of the electron transport layer 60 is not particularly limited, but is preferably 0.1 to 100 nm, for example, and more preferably 1 to 60 nm.
  • the second electrode 70 is a negative electrode (electron extraction electrode) and is electrically connected to the photoelectric conversion layer 50 on the side opposite to the light receiving surface of the photoelectric conversion layer 50.
  • the material of the second electrode 70 is not particularly limited as long as it has conductivity, but a metal such as gold, platinum, silver, copper, aluminum, magnesium, lithium, potassium, or a carbon electrode may be used. it can.
  • the second electrode 70 can be formed by a known method such as a vacuum deposition method, an electron beam vacuum deposition method, a sputtering method, or applying metal fine particles dispersed in a solvent and volatilizing and removing the solvent.
  • the photoelectric conversion element 10 can incorporate a means for blocking ultraviolet rays.
  • the means for blocking the ultraviolet rays is not particularly limited as long as the element can be blocked from the ultraviolet rays, but examples include an ultraviolet absorbing layer, an ultraviolet reflecting layer, and a wavelength conversion layer for converting ultraviolet rays to another wavelength.
  • the position for providing the means for blocking ultraviolet rays is not particularly limited as long as the element can be blocked from ultraviolet rays, but a layer having an ultraviolet blocking function as described above is provided on the substrate surface on the light irradiation side, or a film having an ultraviolet blocking function is pasted.
  • a substrate with an ultraviolet blocking function as the light irradiation side substrate, or provide a layer having an ultraviolet blocking function between the light irradiation side substrate and the transparent conductive film.
  • a sealing material provided with an ultraviolet blocking function.
  • the wavelength region of the ultraviolet ray to be blocked is not particularly limited, but the transmittance is 10 in the wavelength region of 330 nm or less, preferably 350 nm or less, more preferably 370 nm or less, more preferably 390 nm or less, and more preferably 400 nm or less. % Or less, preferably 1% or less, more preferably 0.1% or less.
  • the photoelectric conversion element 10 According to the photoelectric conversion element 10 according to the present embodiment, it is possible to improve the photoelectric conversion efficiency.
  • the precipitate was filtered, washed with methanol and hexane using a Soxhlet extractor, and then extracted with chloroform.
  • the chloroform solution was concentrated and then reprecipitated with methanol to obtain the organic semiconductor (P1) (62 mg, 95%) used in Example 1 as a dark purple solid.
  • the number average molecular weight of the organic semiconductor (P1) was 31000, and the weight average molecular weight was 71000.
  • the organic semiconductor (P2) used in Example 2 was prepared in the same manner as the synthesis of the organic semiconductor (P1) except that the compound 3 was used for the compound 1.
  • the number average molecular weight of the obtained organic semiconductor (P2) was 48,000, and the weight average molecular weight was 108,000.
  • the organic semiconductor (P3) used in Comparative Example 1 was prepared in the same manner as the synthesis of the organic semiconductor (P1) except that Compound 4 was used for Compound 2.
  • the obtained organic semiconductor (P3) had a number average molecular weight of 25,000 and a weight average molecular weight of 54,000.
  • the organic semiconductor (P4) used in Comparative Example 2 was prepared in the same manner as the synthesis of the organic semiconductor (P2) except that Compound 5 was used for Compound 2.
  • the number average molecular weight of the obtained organic semiconductor (P4) was 27000, and the weight average molecular weight was 53000.
  • the organic semiconductor (P5) used in Comparative Example 3 was prepared in the same manner as the synthesis of the organic semiconductor (P1) except that Compound 5 was used for Compound 2.
  • the number average molecular weight of the obtained organic semiconductor (P5) was 29000, and the weight average molecular weight was 54,000.
  • Table 1 shows combinations of R 1 and R 2 of each organic semiconductor used in Examples 1 and 2 and Comparative Examples 1 to 3.
  • DT means 2-decyltetradecyl (long chain carbon number 14 (C14), total carbon number 24), and HD means 2-hexyldecyl (long chain carbon number 10 (C10), total carbon number) 16).
  • Example 1 The element structure of the photoelectric conversion element of Example 1 is as follows. Element structure: Transparent electrode (ITO) / hole transport layer (PEDOT: PSS film) / photoelectric conversion layer / electron transport layer (Ca) / counter electrode (Al)
  • PCBM and p-type organic semiconductor (P1) are added to a chlorobenzene solvent at a mass ratio of 1: 2 to prepare a 10% by mass coating solution, and this coating solution is placed on the hole transport layer at 500 rpm ( 30 seconds). Thereafter, drying was performed to form a photoelectric conversion layer having a thickness of about 200 nm.
  • the film thickness is further about 100 nm by a vacuum deposition method.
  • a counter electrode was formed by depositing Al.
  • Photoelectric conversion elements of Example 2 and Comparative Examples 1 to 3 were produced in the same manner as Example 1 except that the above-described organic semiconductors (P2) to (P5) were used as p-type organic semiconductors.
  • the electron transport layer 60 is provided between the photoelectric conversion layer 50 and the second electrode 70, and the positive electrode is provided between the photoelectric conversion layer 50 and the first electrode 30.
  • the hole transport layer 40 is provided, the position of the hole transport layer 40 and the position of the electron transport layer 60 can be interchanged.
  • the electron transport layer 60 is provided in a region between the first electrode 30 and the photoelectric conversion layer 50, and the hole transport layer 40 is provided in a region between the second electrode 70 and the photoelectric conversion layer 50.
  • the first electrode 30 is a cathode
  • the second electrode 70 is an anode.
  • either one or both of the hole transport layer 40 and the electron transport layer 60 may be omitted.
  • the present invention can be used for a photoelectric conversion element.

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Abstract

L'invention concerne un élément de conversion photoélectrique (10) qui a une structure dans laquelle une couche de transport de trous (40), une couche de conversion (50) photoélectrique et une couche de transport d'électrons (60) sont prises en sandwich entre une première électrode (30) et une seconde électrode (70). La couche de conversion (50) photoélectrique consiste en une couche d'hétérojonction en volume, et un fullerène ou un dérivé de fullerène est utilisé en tant que semi-conducteur organique de type n. Un semi-conducteur organique représenté par la formule (1) est utilisé en tant que semi-conducteur organique de type p. Dans la formule, R1 et R2 représentent chacun un groupe alkyle linéaire ou un groupe alkyle comportant une chaîne ramifiée ; la différence entre le nombre d'atomes de carbone dans la chaîne longue de R1 et le nombre d'atomes de carbone dans la chaîne longue de R2 est inférieure ou égale à 3 ; et le nombre total d'atomes de carbone dans le groupe alkyle de R1 ou de R2, qui comporte plus d'atomes de carbone dans la chaîne longue (dans le cas où R1 et R2 comportent le même nombre d'atomes de carbone dans la chaîne longue, celui comportant le plus d'atomes de carbone au total ; et dans les cas où R1 et R2 comportent le même nombre d'atomes de carbone au total, soit R1, soit R2) est inférieur ou égal à 15.
PCT/JP2014/004410 2013-08-30 2014-08-27 Élément de conversion photoélectrique WO2015029432A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018123207A1 (fr) 2016-12-27 2018-07-05 国立大学法人大阪大学 Dérivé de naphthobischalcogénadiazole et son procédé de production

Citations (4)

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